A NEW LIFE FOR ME
A DREAM COME TRUE
By Terry Hansay
I hang out with my old college buddy Bob two three times a year, and this time unexpectedly he invited me to stay with him in his huge, near-empty family mansion. Good thing because I lost my job and had no money. He was an only child, his father was dead, and his mother preferred living in the south of France when not traveling with wealthy friends.
“You can have any one of its bedrooms rent and cost free. You’d do me a favor living here, Paul. It’s lonely.”
How could I say no? I moved in, and I must say, after a few weeks it felt right. His staff would serve us dinner, coffee in a large sitting room, and sometimes we’d chat or watch a game on the tube together, and sometimes we’d just sit and read.
One day as we sat reading Bob looked up and said, “Paul, do you like living here rent and cost free?”
I looked over to him from my magazine. “Sure,” I said uncertainly. “Who wouldn’t?”
“Well, you know my mother is coming here soon and I need a favor from you. We need to show her I am a straight up kind of guy. I can’t let her see us living together in this huge house all alone. I don’t want her to think I’m gay.”
“Bob, why in the world would she think that? And even if you were, why would she care? What difference would it make?”
“It’s a long story. The short form of it is, she’s a little bit homophobic. She had a brother who was gay, and very unhappy about it, he never found the right kind of loving partner. So from early on she’s been worried that I might be like her brother, or something.”
Odd. Still, I had to ask him, “What do you want from me? It’s your Mother, you’re the one who has to deal with her!”
He stared at me a moment. “She wrote into her living trust that I have to be a straight ‘stand up guy’ to inherit from her, someone who means to have kids to move along the family name…. bla, bla, bla… and all that! She means it, too! And now she’s coming to visit, and here are you, and here we are living together like a gay domestic couple. What’s she going to think?”
I could see his problem. “So? I can move out and live somewhere else while she’s visiting you.”
“No, I need an even bigger favor from you, buddy.”
He had me baffled. “What would that be?”
He took a deep breath. “I need you to be my girlfriend when Mom visits. To show her once and for all that I am not gay.”
I was baffled. “Bob what do you mean me be your girlfriend? How can I be your girlfriend?” I asked.
“Paul look at you, you look like a girl now, sort of. You have long hair, you’re short and skinny, and you’ve got facial features any girl would die for. With a little help you could be a drop dead beautiful girl”.
Was he out of his mind? “Bob I can’t do that,” I said slowly. “People will know I’m a man. And I have no suitable clothes, nor any desire to be a girl.”
“Paul, I need this favor, and you need money. It’s only for a couple of weeks while Mom visits. I will pay for everything, plus get you help in making you into the most beautiful girl in the world, so no one will ever know you are Paul.”
He was serious! “Can I think about it?” I asked. Then I added, “This is so strange!”
“Paul don’t think long, because I have Sally coming over at 3pm today to get you started. You either do this for me, or you’ll have to leave. I can’t have my Mom see that there’s a man here living with me. No way!”
“Bob, who is Sally?”
“She’s a girl who will help you switch your look and demeanor to womanhood”.
“Bob, this is way too much, I need to think about this!”.
I went up to my bedroom and looked into the mirror. Yeh, I do look like a girl. It’s a strange thing to ask anyone though. I had been thinking in the past that I might try crossdressing, see what it would be like to be a girl. One of my friends is a crossdresser, and he’s been pushing me to crossdress for a long time. And I have had a deep down fantasy to crossdress since I was a kid. Out of curiosity, mostly.
Just then Bob came into the room and held out a check to me. I was blown away. He said this should help me make up my mind. I saw it was made out for $50,000.
I stared at him, I knew Bob was desperate! I asked him why he couldn’t “rent” a real girl for his Mom’s visit.
“Paul, I want someone I can trust. Not some girl off the street. You are my very close friend. I am not asking you to kill someone, just to pretend to be my girlfriend for a little bit. How hard can that be? You might even like it, plus you will make $50,000.”
I hesitated another moment. Did he say I might like it? We’d been friends a long time but not his girlfriend. This money was incredible though. Might be worth wearing a costume for a month. Finally I replied, “All right, I’ll do it. But I will need help. I don’t want anyone to think I’m a man and get embarrassed!”
I couldn’t believe it, but Bob immediately came over to me and gave me the biggest bear hug. As if I was his girl already! Then he said, “We will have so much fun. You will be the most beautiful girl. We will really fake Mom out. Sally will be here this afternoon to help us, and I have hired a decorator to remodel what will become our bedroom. After all, a girl needs a dressing table and a walk in closet for all her new pretty clothes, her shoes, and her other girly stuff.”
He’d obviously been thinking about this! I said nothing.
“We need to pick you a girly name now. What name do you like for yourself?” Bob asked.
“Well, I’ve always liked Mary,” I said. That was the first girly name that came to mind.
“Paul, I think you have been dreaming of this day before! You already had a name picked out? So sweet! Ok, Mary it is. We are going to have so much fun, aren’t we Mary!?” Bob said.
I just smiled, thinking he is really into this. Very strange! He held out the check again, and I took it.
Sally showed up right on time. She was about 35-36 and a very beautiful woman, very shapely and dressed very classily. Her figure looked like a girl from the 50’s, with a pointed bustline and shapely hips. I felt attracted to her immediately.
We talked for an hour or so, she seemed so into this transformation, even excited. She informed us she would live here for 6-7 days to help my transformation. She seemed very intent to change me into this trophy girl Bob wanted for his Mom.
I got nervous when she said I had to take pills to calm me down, to relax my demeanor. I told her I was fine, but she insisted I take these pills every 6 hours. Bob looked at me like this was all part of the deal, as if he were saying take them, they won’t hurt you.
Sally had a way about her that I could not say no. I did not like taking pills. But I did and she was right, I did feel different. Much more relaxed. Weaker, it seemed.
After dinner Sally laid out the plan for my transformation. “We will start our training in the morning and go shopping for your new clothes,” she said.
She then looked at Bob and said, “It would be best while we are gone tomorrow shopping that you clean out Paul’s manly clothes from the house. It’s best Paul does not handle that; he might freak out dumping his own clothes. After all, he will not need them any longer.”
My brain got nervous, thinking that I will need my male clothes back when his Mom leaves. But for some reason I could not get mad about Bob moving out my clothes. These pills must really be working on me.
Sally also told Bob she wanted to work with his decorator on feminizing their bedroom. “We have to make it look like Mary’s had her influence here in the mansion.” Bob agreed and said, “Whatever you want, just let me know.”
I thought this was moving way too fast.
Sally grabbed my hand and took me upstairs, saying, “Mary, lets get you ready for bed dear. You will find this part of your new life much different. After all, we have to make you feel and act very feminine now, much different from being a man!”
She took me to another bedroom, a very feminine room, one of the ten bedrooms Bob had in his huge mansion. Then took a nightgown out of a dresser and told me to strip out of my man clothes. Telling me that this will be the last time I will need those boy clothes.
What did she mean by “the last time”? But for some reason I did as she asked without hesitation. She also handed me matching panties and a girdle.
I asked why I had to wear a girdle. It looked tight.
“Mary, I have found girls like you have accidents down there and get their nightgowns all soiled. So your new girdle will keep you under control from now on. You will like your new control down there and you WILL get use to it, trust me dear”.
She was right, the girdle was tight, and it did work. I did NOT get excited down there. My little guy could not move. Meanwhile the nightgown was so soft, so nice. I stared in the mirror…. I was dreaming how girly I looked already, with my long hair.
“Mary, you look wonderful. Your transformation will be so easy, your long full hair and small body is perfect for your transformation, girl! You will make a wonderful girl for Bob”.
Did she say a wonderful girl FOR Bob? What did that mean? I kept staring in the mirror. What was wrong with me?
Sally grabbed my hand, and took me into this huge bathroom to “teach me my new nightly feminine wash up duties” as she said. To keep my skin “so, so pretty,” she said.
Once it was done she told me to jump into bed, and gave me a book, “How to Cross-dress and Be the Best Girl Ever for your Man.” She told me this will be my daily reading and will help me understand my new life.
‘My new life,’ yeh for a couple of weeks,’ I thought. But again I was so relaxed I accepted the book with a smile and jumped into bed. I was so relaxed, and felt so nice in this soft nightgown. I was thinking this might be easy, being a girl. Plus I have $50,000 now.
I’d started looking through the book when Sally started undressing right in front of me. Wow, she was gorgeous! I thought. Her lingerie was so beautiful and yes she was wearing all retro foundations. That was why she looked so different.
She saw me admiring her lingerie as she undressed. “Mary, do you like my lingerie? Bob would like you to have this look. You know, the retro look? You may not know that his mother is a beauty queen from the 50’s. She too loves retro fashions”.
I couldn’t take my eyes off her bra. Wow, she was a full figured girl, and her bustline looked very pointed in the cone bra. For some reason I liked her bra and told her so.
“Good, Mary, because this IS your new look tomorrow when we go shopping. Bob wants you to have all the best clothes, to look your absolute best for his mom,” Sally said.
Sally slipped on her retro nightgown with a full bra to help support her beautiful breasts. She looked gorgeous in her nightgown as she sat at the dressing table brushing out her long beautiful hair.
“Mary, I will teach you all about this during the next many days. I am sure you will come to love your new feminine ways. Trust me, it is so much fun being a retro girl,” Sally said.
Then she got into the twin bed next to me. Yes, here in the same room as me. I felt a little nervous, sleeping in the same room with this gorgeous woman. But I decided, if she is ok with it, sleeping with me, then I guess I am ok with her in my bedroom. But it was a good thing I had on this girdle, keeping the boys under control. She knew what she was doing when she put me in this girdle.
The next morning came quickly; I guess those meds really relaxed me to sleep.
At breakfast, still in my nightgown, Bob smiled as Sally talked about our shopping day. He told us, “Girls, have a fun day, buy what ever you need to make my Mary beautiful.”
Bob went off to work and Sally took me back up to “our” bedroom. I just stood there waiting for her “command,” that seemed like the thing to do. She smiled and said, “Mary, I bought some women’s clothes to get you out, to start our shopping spree. We are going to have so much fun spending Bob money, aren’t we sweetie.”
Sally told me to leave on my panties and girdle and handed me a bra. I got nervous trying to put on the bra. She giggled and helped me, saying I would soon get the hang of hooking my bra everyday.
Sally told me this t-shirt bra has padded cups to hide girl’s nipples. She inserted what she calls fake breasts into the cups. Wow, really had a shape now and the bra felt so strange, so tight around my chest, I didn’t like the feeling nor the look.
“Sally, do I have to wear a bra now and have these mountains on my chest? Bob’s Mom would be here for a week or more. This bra is so tight, feels funny”.
“Mary, every girl wants a shapely figure and your new figure starts with your bustline. You will adjust to your new feelings, your new figure, and your new clothes. Remember, you have to look pretty and your figure is first and foremost in your beauty treatment.”
She gave me a tight fitting sweater, very feminine looking and women’s pants. “Mary don’t get use to the woman’s pants, you will not be wearing pants ever again.”
I looked in the mirror, and yes, already I could not tell if I was a man or a girl. “Sally my bra is showing through this white sweater, I can’t go out like this”.
“Mary you look wonderful. You look fine, very girly looking.” I don’t want to look girly. What am I doing?
Sally was pleased as she pulled me out of the house for our shopping trip. She seemed so excited about my transformation!
“Sally I feel very funny wearing this bra and girdle. How come these bra straps keep falling down?”
Sally giggled saying, “Mary, that is just one of the many pleasures of being a woman. You are learning. When Betty fits you for your bras today, she will get your size right and your straps will not fall down, plus you wouldn’t need all that padding in your cups. That is why we girls get professional measured for our foundations. We need a perfect fit for our figures and our men!”
I had no idea what she was talking about. What does men have to do with all this bra talk? What are foundations? All I could do is smile and think what did I get myself into?”
Our first shopping stop was to a store that said “Transformation Salon.” When we first walking in, it looked like a beauty salon. The owner, Betty, took us into the back room. I was nervous as she was saying how happy she was to help me become the woman I wanted to be.
The woman I want to be, did she say that? For some reason again today, I could not “fight” the things these women were saying to me. Strange.
Betty told me to undress and she would measure me for my new clothes. Sally had to help me, I was so nervous underdressing in front of her. Betty giggled, saying, “Dear, don’t worry, we are all girls here and I am here to help you.”
Betty looked at Sally and asked her what Mary’s husband wanted as her measurements.
I looked up, thinking, did she say my husband? What is up with that?
Sally popped right up, saying Bob was not Mary’s husband. But he would like his girlfriend to have a full curved figure, like his Mom’s.
Betty smiled and said, “Bob’s mother is very attractive and has a great figure. I can give Mary the same figure.” Sally looked at me and told me to relax, all will be ok, Betty knows her lingerie.
Next thing I knew Betty was gluing huge breasts on my chest. I tried to resist, thinking they are way too big, but Sally said they were perfect. Betty put some makeup on the edges of the fake boobs and by the time she was done, I had beautiful breasts that looked like they were all mine. Both women proclaimed they were a perfect size and commented on how pretty I looked, and what a lucky girl I was to have such a nice figure.
Wow, next came a retro pointed bra. Betty announced it was a 36C with a little padding to help shape the cups. I thought I was going to faint when I looked down at the huge mountains on my chest. Looking in the mirror, seeing me in this ultra feminine lacey bra, my reflection shouting all girl, my body so feminine and curvy, I realized I didn’t look at all like a man anymore.
I felt weak, and they knew it as they guided me to sit down. Just walking seemed totally different with these mountains on my chest. I keep looking at them, holding them up like they are heavy.
Sally giggled saying, “Mary don’t worry, you don’t have to hold them, your breasts will not fall off. They are now yours and you will get used to your new girly curves.”
Betty gave me some water as Sally pulled more pills out of her purse, telling me to take them, that these will help. I did as she commanded -- what was happening to me?
I overheard them talk about my matching panty girdle and garter belt for this bra. Betty was back in a second with more lingerie. These women were taking over and I was getting tons of lingerie. Then Betty began bringing out clothes. I just sat or stood there trying on clothes.
Sally then said it was time to go. I thought I was going to faint again. Sally handed me this very lacey 1950’s retro dress and told me to “slip it on”. With fear in my eyes, she said, “Yes, Mary you will wear dresses and high heels now. You can handle it! You look beautiful and it’s time to make the full transformation.”
I hesitated, but with Betty’s help she handed me this gorgeous pink lacy full slip and with a big smile told me to slip it on. Then she slipped the dress on over my head, over my pointed bra, slip, and retro girdle, and I was now wearing nylons. She zipped the dress up my back and turned me around as she tied a big satin pink bow just under my bustline, accenting my boobs even more. I was numb, I could hardly move.
Betty gave me a kiss on the cheek saying, “Mary you look stunning, you will make a beautiful girl, please come back and shop soon.”
Sally then gave me a purse; I looked at her like what is this for? “Silly girl, you have to carry a purse now, all the time. It’s what ‘us’ girls do! Let’s go home and I will teach you what us girls put in our purses. This will be so much fun, sweetie!”
I couldn’t stand. I fell to a chair and started to cry.
Sally put her arm around me trying to comfort me. “Mary you will get use to your new clothes. I will help you adjust to your new feminine ways. You are doing such a good job, I know Bob will be very proud of you”.
I looked up to say, “Why would Bob be proud of me? Why am I wearing all these tight girly clothes when his Mom won’t be coming in for two more weeks? At this rate I will be in this bra and girdle for a month. I’m not sure THAT was part of our deal”.
“Mary I’m here to help you develop your feminine ways. Your girly persona will take all of the two weeks to learn. We have to practice; there’s a lot to learn. Plus you want to make sure you are 100% girl when Bob’s Mom comes for her visit, don’t you? Here, take these pills too, with water, they’ll help you.”
I took them.
“Now we need to step out into the salon and get your face fixed up, and then I think you will feel better, more like a girl. A little makeup on us girls does wonders, wait and see. I know you’ll be so excited when you see your new face!
“Also girl, not sure why you don’t have Bob’s favorite perfume on!? You need to smell like the beautiful girl you will soon be!”
Off I stumbled in my new heels. All the ladies in the salon were smiling. They knew I was a man.
Betty led me over to a chair. I could not resist, and relaxed into it. “Mary, now just sit back and let us make you more beautiful.”
I could not believe I was letting these women do this to me. What did I agree to, why, why, why? I could hardly move in these clothes and I was real nervous.
Some other girl all giggly worked on my face and another one did my fingernails. Was I dead, I just sat there? I could not move. They were transforming me right before my eyes.
One girl wanted to shape my eyebrows. What? My eyebrows? Luckily Betty said no, that he would have a full facelift soon. Not sure what that was, but I was glad it wasn’t today.
I looked down, seeing my finger nails turning bright red. Plus they did something to make them longer. How can that happen?
Betty told the makeup girls not to do too much on me, and eventually proclaimed I was done. “He’s just a beginner, after all,” she said. They then opened a large mirror and I saw myself. Wow, who is this girl, she’s pretty!? Sally put her arms around me, proclaiming how beautiful I looked and how proud she was of me. “Mary this is so much fun, you have no idea the pleasure you are giving me”!
Giving her pleasure? Who is this girl? What am I doing? Who’s the girl in the mirror? How could this be happening to me? Why do these ladies like turning me into a woman?
Betty was all excited, saying “We will see you tomorrow for your hair appointment, right Mary?” I couldn’t even think about that. I could hardly walk. Sally held me up as we walked back to the car.
“Mary take small steps and swing your arms more. Twist you hands out so your palms are facing out. Think about your hips swaying. Smile like you are enjoying your new life. All this will give you a very feminine walk and demeanor which you need to master quickly”.
Sally opened the car door for me saying, “Mary turn around and sit into the car seat first, swing both legs up together, keep your legs together and place your hands on your lap, on your dress together. Do all this slowly, being your first time. Not easy moving around in your new clothes but you will learn sweetie.”
I did ok, but I was numb with everything that has happened today. Sally knew I was having a hard time handling all my new ‘functions’!
When we got back to the house both Bob and the maids were waiting for us. Bob was amazed by my appearance. “Mary, you look terrific, I love the outfit, my Mother will be very pleased,” he said. “Sally, you did wonders with him the first day. This is going to be so much fun. Mary, I hope you like how Sally is helping you become my beautiful girlfriend. Remember, you did agree to be my “best” girlfriend while my Mother visits,” Bob continued.
He came over and hugged me. I felt like a girl, and almost liked being hugged by this strong man. This was so strange.
Bob whispered in my ear, “Mary, you look and smell so good, so feminine, so pretty you could fool anyone, even my Mother. We are gong to have so much fun now that you ARE my girl!”
I was numb, hearing him call me “his girl” and telling me I looked pretty, now aware that I was going to be like this for a month. What did I get myself into?
Bob then got all excited, saying he’d bought me some special presents and that we should go upstairs and open them. Sally got excited, and they dragged me upstairs. I could not move fast in this girdle and dress, and the heels were hurting.
We got to my bedroom, where there were several boxes on the bed. It looked like Christmas with all the boxes.
I opened them, one after another, all silky lingerie, beautiful lingerie, all for a princess as Bob was saying. He was so excited, saying he had bought them just for his girl.
I looked at him thinking, “Just for HIS girl”… I’m his girl?
The nightgowns, slips, and panties were all from Victoria’s Secrets and Saks Department store. All so lacey, so feminine I was getting excited just from touching them. Wow, what was coming over me?
Sally said that we would be going to Victoria’s Secrets tomorrow for more shopping, so if they don’t fit we can return them.
I was so beat and Sally knew it. She ushered Bob out of the room and told me to undress and slip on one of my new nightgowns for a nap.
I couldn’t believe how long it took to get out of my dress, slip, girdle, nylons and garter belt. Sally smiled and said I would get used to my dressing or undressing ordeals, something us girls all get used to. It takes us girls a lot to be beautiful.
I looked down and saw my breasts. They looked like my own, and they weighed on my chest like my own. Sally smiled while handing me the nightgown, saying, “Here Mary, this nightgown has supportive cups to help you, they will make you feel supported, the support you now need,” as she giggled.
She was right, the cups in the nightgown did help. They felt better than no support for my new boobies, I thought. Off I went to sleep, beat and drained from the full day of girly shopping.
Sally woke me up for dinner. She said that Bob had bought me a beautiful dress and he would like me to wear for dinner tonight at 7.
Wow, was this a date, what was up with this?
After a shower she handed me a 50’s bra and matching panties and retro girdle with garters.
I said, “Sally do I have to wear a bra tonight? No one will be here. Can’t I go braless and no girdle or dress? That old fashion bra makes me look like I have two torpedoes on my chest! His Mom is not here yet!”
I saw a stern look come over Sally’s face as she stepped into my face saying, “Mary you made a deal with Bob, you have to be the most beautiful girl you can be NOW, you are being paid well and you have a deal. You have to be the woman in Bob’s vision, you agreed. Plus woman do not go braless, you need the support of a pretty bra and it will give you the figure we want you to have. Now put on this pretty bra and lets get started. It takes time to make us pretty and a little extra time with you”.
I was so intimidated; I took the bra and slipped it on. I guess not right since she scolded me saying, “Mary you know better, Betty taught you this afternoon how to put a bra on at the store, now bend over and adjust your breasts into the cups. Stick your hand inside the cups and adjust your girls into the cups. Your bra will be more shapely and fill out the cups even better.”
I am thinking, “my girls,” is this girly talk? Who are my girls? Well, I did the adjustment and wow, yes, the cups did fill out better but they are still so pointed! I don’t know why girls or men like this look, it seems so un-natural. Why would Bob’s and his Mother like this look? Is she that old fashioned?
This time Sally handed me what she called an open-ended panty girdle and a separate waist cincher. She said these would help my curves in this dress. What did I know?
I asked her what is an open-ended girdle? “Mary this will help you keep your knees together when you sit. Girls have to keep their legs together, be lady-like when sitting. This girdle will help you remember to keep your legs together.”
I did notice that it made me take smaller steps as I walked over to the makeup table.
Sally did my makeup and hair. I liked being pampered and Sally knew it. I was shocked to see all the makeup she put on my face, so I asked why.
“Mary, tonight you’re attending a southern dinner party. Bob thought you would like it.”
“Party, are their other people coming to dinner?” I asked.
“No, no just the two of you for dinner. Although just between us girls, I know he is planning a “coming out” party for you. You know, to introduce you to his friends so they won’t blow the cover when his Mom’s here.”
Fear struck me as Sally tried to reassure me all would be ok. She will be right by my side and no one will ever know I was once Paul.
How could she and Bob make me so different so fast? It’s like they got rid of Paul and now they have Mary as their play toy. Problem is I am beginning to like this new life, maybe.
“Now Mary calm down, enjoy the ‘process,’ enjoy your womanhood, relax, and let me pamper you.” She combed out my long hair and spun it up on top of my head. It felt strange up there. She put a pink bow and little flowers in my hair, very feminine looking I thought.
I looked so different with makeup on, I was amazed at my new look. Felt funny on my face. Sally said I would get use to makeup, will never leave home without my new look.
Sally proclaimed my beauty, how pretty I looked, and added that the gown will be the ‘topping off’ of my new look. Then slipped a full slip on me, and another different kind of slip, she called this second slip a ‘petticoat’ to help fill out the dress. Wow, this petticoat looked like a dress.
Next came the dress, an old-fashioned dress I thought. It wrapped around my chest and narrow waist, and because of the petticoat really flared out at my feet. Sally tugged and zipped the back up. Looking in the mirror, I saw my figure was gorgeous. I think I was getting turned on, I looked so good as a girl.
Then she tightened a huge lacy bow around my waist, proclaiming that my pretty transformation was complete, except for my high heels and some jewelry and perfume.
We both looked in the full-length mirror as she got all excited and said, “Mary you are a vision of loveliness! I have done such a good job, Bob will be so pleased!”
I am thinking, why will Bob be pleased? What am I missing here?
“Here, Mary, slip on your heels and let me take some pictures. You are such a beautiful girl now. I just love your sweet red lips… that lipstick is the best so exciting. You should be so proud of yourself!” Sally said.
Again I felt weak, had to sit down. All this stuff was happening too quickly.
“Sally can I tell you something? I told you I have tried crossdressing a little before and I liked it. But, I really like wearing high heels and have been wearing heels in private”.
“Mary, I knew that, you walk in heels well. I see the excitement in your face as you slip them on. You are doing wonderful”.
Sally handed me my purse and said, “Lets get downstairs, can’t keep your new boyfriend waiting!”
I thought, keep him waiting, who is he, my date?
I looked at her, saying, “My clothes are too tight, I can’t move, it’s all too tight. Do I really need all this stuff on? Why do I have to carry a purse in the house?”
“Mary, I am trying to train you in your new feminine ways. This is what us girls wear; we want you to look your prettiest ALL the time! This dress requires these pretty foundations. Just thank your lucky stars that you are not living back in 1950 when girls wore these foundations every day, when they were fashionable and everyone loved their look and shape. You are lucky I didn’t put you in a corset tonight, but that is next sweetie! Now get your pretty little tight ass off that chair and lets go downstairs and enjoy the evening.”
Downstairs in the formal dining room, there stood Bob in his formal tux. I was blown away at how good he looked. What was I thinking, why was I staring at him?
He came over and greeted me like I was his long time girlfriend. Wow, he is really playing the part too. He hugged me a long time. I felt the passion flowing through our bodies. What was going on? Why do I feel this excitement?
I saw Sally in the corner smiling with two thumbs up, proclaiming her pleasure at our union.
Bob held me back, looking at me, telling me how gorgeous I looked and that I will make the BEST girlfriend for him and his Mom.
He escorted me over to the dining room and held my chair like perfect gentleman.
I was still in another world from the passion of his hug. Where did that hug come from, I kept wondering. I was putty in his strong arms, I thought. These clothes or the pills are making me helpless -- I can’t think for myself.
Bob kept talking about how pretty I looked. That my southern classic gown was so pretty, that he just loves the look. He kept thanking me for doing this for him. He kept giving me wine and I kept drinking it. I knew how to handle that, I thought. I had to get drunk, I thought.
During dinner Bob kept telling me how pleased Sally was with my acceptance of becoming his girlfriend. He was hoping I would accept the 1950 retro look since it was his favorite look and he loves his girlfriends when they wear those pretty fashions, as he said.
Just then I thought, did I hear him say, ‘his girlfriends’? He likes them in these tight girdles and pointed bras? He thinks I’m his girl? How can I be his girl?
Then I thought about my shopping spree today, and what I am wearing. Yeh, maybe I am his girl for a month, that’s the deal, for his Mom’s sake.
After dinner we went into the living room. I’d had too much wine, and felt so relaxed I didn’t even mind when he sat right next to me on the couch.
He started talking about how we will have to be like husband and wife, since my Mom knows my girlfriend lives with me. So he talked about marriage.
I heard that word marriage and got real nervous. What is he talking about? He kept saying he would have to treat me like his wife, his girl, and that he hopes kissing me will not freak me out.
I didn’t know how to answer him. I only knew I was feeling so placid, so relaxed, probably because of the pills Sally keeps giving me, that all of a sudden, not sure what came over me, I hugged him and gave him a huge kiss on the lips. What could be wrong about that? I was enjoying this and we both knew it.
He was the perfect boyfriend and returned the kiss. I fell back in the couch with such pleasure on my face, saying, “Bob I am not sure what came over me. We are two men kissing like we were boyfriend and girlfriend. These clothes and pills are making me do strange things!”
Bob hugged me quickly back saying, “Mary you are my girlfriend now. You are so beautiful inside and out. Just look at you! You ARE are my girl!”
We had more wine, more kissing. He even tried to unhook my bra. I giggled, saying, “Good luck with that one, this dress and bra are built like a fort -- you won’t get in.”
We both laughed as he suggested we go upstairs to his room.
I got nervous but he grabbed my hand and led me upstairs. I could not resist. He took me into his bedroom. There on the bed a gorgeous pink lacey full-length nightgown. He held it up, asking me if I liked it. “Mary come over here and try it on. I think you will look gorgeous in this. I bought it just for you!” Bob said.
What was going on? He wanted me to strip down and put on this nightgown right in front of him? I looked around. Sally was not here. Nearby I saw a beautiful makeup table, and further back I saw a walk-in closet had tons of dresses hanging in it, with high heels all over.
“Bob what are all those dresses for? Who are they for?” I asked.
“Why you silly, when my Mom comes this will be OUR bedroom of course. Mom thinks we live together and with Sally’s help I bought all those clothes for you. This will be our bedroom. I thought you knew.”
“I am going to sleep with you in that bed?” I asked.
“Paul, of course. What’s wrong with that, you are my girlfriend, did you forget?”
“Bob I can’t do that, I can’t sleep with you! I am having some very strange feelings for you! This can’t be happening!” I ran out of the room and ran immediately into Sally in the hallway.
“What’s wrong, Mary?” Sally asked. “Did Bob say something? You look all red in the face.”
“No, he was a perfect gentleman. It’s me. I can’t undress in front of him. And how can I sleep with him in that bedroom?”
“Oh, Mary, come here, you need a hug. Calm down and lets go back to our room and talk this through”.
Back in our bedroom I started to cry, saying dinner was so nice and our talk on the coach afterward was a real changing point for me.
“Tell me Mary, what do you mean by ‘changing point’?” she asked.
“Well, Bob was so nice. We both clicked. I really felt like his girlfriend in the living room. I really thought I could do this for him, you know play his girl when his Mom comes to visit. We even talked about my dress and foundations on how I was adjusting to them, how much he likes this 50’s look.”
“Then all of sudden he said we will have to act like husband and wife when his Mom is here. She expects us to marry I think. Sally what is up with that? I can’t marry him! I am a man. Why did he tell his Mom we might marry?”
“Mary calm down, he’s only telling his Mom that to make sure she’s accepting of his lifestyle. He has to convince her he will get married some day, that’s all. Bob knows you are a man and that you are his best friend. Keep focused on the mission here. He needs to convince his Mom he is straight and will marry someday,” Sally said.
Sally explained that I would have to sleep in the same room with Bob when his Mom gets here. She would help me adjust to this, and maybe the doctor could help.
“Doctor, what doctor?” I asked.
“Tomorrow we have to see a doctor to help your voice. You have to sound more like a lady you know, and there is a doctor who can do this.”
Fear struck me as I said, “I can’t change my voice. I am a man”.
Sally said, “Mary don’t worry, the medicine only lasts 3-4 weeks and you will be back to normal after that. Besides, look at yourself, do you look like a man now? Relax, this will complete your transformation and make you a sweet talking girl.”
I was so weak and drained. Sally helped me undress and get washed up for bed. She is so nice I thought, so sweet.
The next morning Bob was at breakfast when I came down. He rose and apologized if he’d said something wrong last night. He hugged me saying, “Mary I might have rushed you too quick with our game. I am sorry. You are being such a good sport and I really appreciate you helping me with my Mom. I will be gone a couple of days now, but will be back Saturday. If you need anything Sally and the house maids will help plus here is your own cell phone, so you can call me anytime.”
I got all weak and giggly, just like a girl I thought, and hugged him back saying I might have gotten too emotional last night. I am really trying but I need time to adjust to all that is happening to me.
I looked at the cell phone. Wow it was a real girly one, all pink and very small, plus it had Bob’s photo on the screen. We had breakfast. All was ok now. Bob left for his trip and Sally dragged me upstairs to get ready for our day. Getting dressed took so much longer now. “I’m not sure I like this but what can I do?” I said to Sally.
Sally smiled and said, “Mary, you are learning”.
I showered and Sally gave me that 50’s bra and girdle again. “Sally do I have to wear this pointed bra? It makes me uncomfortable, and anyhow girls don’t wear these bras now days”.
“Mary, Bob likes this look and asked that you get used to wearing these kinds of foundations. Woman wore these kinds of bras for years. Maybe if you are a good girl today at the doctors we can go shopping for a more modern bra. You can wear it while Bob is out of town -- he would never know,” Sally added with a smile.
With that I put on the 50’s bra, I did the bend over and adjust my “girls” in the cups like Sally taught me. Sally proclaimed I was getting good at that, with a big smile.
Sally then handed me a very feminine sweater. With fear in my eyes I said, “Sally I can’t wear a tight sweater. My boobs will stick out with these cones, they will look awful!”
“Do you want to try on one of my bras? We are close in size,” Sally said.
“Oh, could I?” It just came out of my mouth! Here I was begging her to wear her bra, what is up with this? With pleasure she took out one of her bras and told me to slip it on. It was a t-shirt bra and had a little padding to cover her large nipples, as she explained.
Wow, it was tight, and the extra padding made me even bigger. I really didn’t need padding.
Something was wrong. I liked the bra, but looking down my breasts, my glued on breasts, I saw they were coming out of the tops of the cups.
“These cups are too small,” Sally said. But I thought it looked better than my pointed bra cups, so I pleaded with her to let me wear the bra.
Listen to me, begging her to wear her bra! What is wrong with me?
Sally said the bra fit well. I thought too tight, but then what did I know? She slipped the sweater over my head. Even though my breasts were more rounded, I still have a very very curvy figure. With a big smile, Sally cupped my breasts with both her hands and assured me I had a very nice figure in her bra.
I looked in the mirror; where I could see the bra lines under this white thin sweater. I looked at Sally and said, “I can’t wear this sweater, I can see my bra under it. People will know I am wearing a bra! Help!”
“Mary, first off, you have a C cup boobs, people know you have breasts even without a bra. People expect you to wear a bra with those large breasts. Moreover, you need support; you have no choice but to wear a bra now and for a long time to come. Don’t worry if your lingerie shows through your tops. It just your new underwear! Sometimes it’s a very sexy look”.
“Sally I don’t want to be sexy, and what do you mean I will need to wear a bra for a ‘long’ time? My deal with Bob is only while his Mother is here on her visit.”
Sally was thinking something, her big smile showed that. But what was she thinking?
I thought it best to shift topics a little. “Sally I like your bra but I’m not sure I should be wearing it. Can I buy my own”?
“Mary we are sisters now, sisters share clothes. As for you buying more, we will see. You need to be a good girl today at the doctors and do everything she says. Plus Bob is not a fan of t-shirt bras, you know he love that retro look!”
I really preferred this softer cup bra to the pointed bras. I assured her I would be good and not cry today at the doc’s.
Sally did my hair and makeup, this time using much less makeup than last night. She put me in a pencil skirt as she called it. I could hardly move in it, but she said that was normal, I would get used to the fit.
“Sally why do I have to wear so much makeup around my eyes? Can’t I do without the brown shadow above my eyes? It hurts. Plus my eye lashes seem longer”.
“Mary you will get used to your makeup. A girl does not leave her bedroom without her makeup on. Your eyes are beautiful with your makeup.”
As we were checking ourselves in the mirror she told me I was missing something, and asked me what.
I was stumped. So, she giggled and said, “We have to get you some earrings today, and first get your pretty little ears pierced”.
I grabbed both my ears saying, “That will be so permanent! That will mark me forever!” She smiled and said, “Yes!” … and off we went to the doctor’s.
I was nervous, but the doctor assured me that the effect is temporary and would adjust my voice to sound more like a woman’s. The process will not hurt, she said, and will make my ‘new’ life easier; because people will not think I ever had a man’s voice.
I signed the forms as they began the process. It was easy, requiring me to take three different syrups. She told me not to talk for 3-4 hours and should take a prescribed medicine each night before bed. I now had to stay in their recovery room for one hour, but Sally would stay with me.
I downed the medicine. As Sally said, I was a real sweetheart.
I fell asleep in the recovery room. When I woke up I found I had a pacifier in my mouth and that it was taped to my face. I could not open my mouth. Sally saw my fear and explained all was ok, this was normal and I just had to leave it in for 2-3 hours. She went on to say I was such a good girl; we would go buy me one of those t-shirt bras I was wearing, with matching panties and girdle. My eyes lit up. She knew she had me under her control now.
I felt really strange having this pacifier in my mouth. Everyone knew it was a baby pacifier, but then what could I do? Off we went to Victoria’s Secret for my own t-shirt bra. I was not happy going there, since it was such a girly store, but I really didn’t want to wear those 50’s pointed bras and this might be a way out of wearing them.
The sales clerk took us right over to the full figure bra section. Sally explained I just had an operation and had to suck the pacifier.
She told the clerk that I should be measured, and fear struck my bones hearing this, but with the pacifier in my mouth I could not say a word. Me, measured for a bra? Out in public? Before I knew what was going on, the clerk had the measuring tape around my chest and announced I was a 36C. Wow that was fast, I thought, and it didn’t even hurt.
Sally bought a very beautiful set -- bra, girdle, panties and garter belt. I tried to mumble that I wanted more than one bra, but she said no, I was lucky Bob was buying me even one of these t-shirt bras.
I was thinking, what does Bob have to do with this? Then thinking back, realized that he was the one paying for all my new clothes.
Sally took me through the mall then, my high heels clicking down the hallway with my very pink VS bag telling everyone I had bought some sexy lingerie at VS.
I kept looking down at my chest. My bra was still shouting out through this sweater. Everyone could see my bra through this tight sweater. I was so embarrassed. Sally said, “Mary, don’t worry, you look very nice, that sweater fits you perfect. Stop looking at your chest.”
We stopped and looked at dresses. She told me that Bob had already bought me many and that he likes buying dresses. That he will be taking me dress shopping next week when he is back in town.
As I was walking I was dreaming, hearing my heels click, feeling my hips move side to side, swinging my purse, thinking how nice this all feels, when Sally pulled me into a booth in the center mall area. Yes, it was an ear-piecing booth. She sat me down and the clerk drilled my holes not for one earring in each ear but for two. Here I was within seconds sporting beautiful feminine earrings, shouting to the world I was all girl here. They felt funny dangling by my neck, but strangely made me feel different. We bought several pairs of earring big flashy earrings. I thought these will cause a lot of attention, but then that is what Sally wants I think.
Sally announced she had a makeover planned for both of us at a local spa. She said it would relax us both and end our day. We drove close to home and walked into the beautiful spa. I could not believe how nice it was, and of course for women only. Not sure I should be here, but looking at me in a mirror, I saw I was ALL woman!
We were ushered into a room and told to remove all our clothes except for bras and panties, and told to put on a very soft feminine robe. I looked at Sally, and she said, “Its ok sweetie, this is how us girls do it, enjoy, I’ll be with you in the same room”.
Here we were, as she says, like sisters, in the same matched bras and panties, so girly in these very comfortable robes. I thought I was in heaven and Sally knew of my pleasure.
All of sudden I worried about what happens if they ask me to take off my robe -- my boys were all excited down there! I gestured to Sally to convey my concern.
She giggled and said, “Mary they are well aware of YOUR boys, this is a salon for cross dressers, they love this kind of treatment, you are in good hands. Nothing to be embarrassed about, we are all girls here. Plus the employees here are all men even though they don’t look like men at all, know what I mean, dear!”
Two girls came in, they looked like girls, telling us to put the robes on the chair and relax on the tables. Wow, I was nervous, but if they were men no one would ever know it. They looked so girly and so feminine. My masseuse saw my nervousness, and helped me with my robe saying, “Mary, don’t be embarrassed, we all have spots on our bodies we are not happy with, including me”.
All this broke the ice. I jumped up on the table, it was so nice, so warm and comfortable. The rub down she (or is she a he) gave me was out of the world, so relaxing!
“Mary may I unhook your pretty bra? I think I have the same Victoria Secret Angel bra, just in love with this pretty bra and how it shapes my little breasts”.
Without thinking, I said yes. It felt so strange having my bra un-hooked. I wondered what would happen next.
She massaged my back with warm oils, felt so so good. She then re-hooking my bra asking me to roll over.
She asked me twice to roll over, I was nervous. Sally looked over at me saying, “Go ahead Mary, you can do it, we are all sisters remember.” For some reason every time I hear Sally say the word ‘sisters,’ I relax and do exactly what she says. Plus the word makes me feel so warm and feminine.
At her command, I rolled over. I knew my boy was “standing right up” but then what could I do?
My masseuse was not embarrassed and said, “Mary, would you like me to ‘relax’ your little guy so he doesn’t get in the way?”
What the heck did that mean? I looked quickly at Sally, she saw my concern. She nodded her head, telling me to go ahead, “That is what sisters do”.
Hearing the word sister again, I nodded my own head, since the pacifier wouldn’t let me really talk.
Just then I felt a warm soft glove pulling down my panties as a hand gently held my stiff guy. She dropped some warm oil on her glove and rubbed my little guy gently. Within seconds I was spurting, and then my guy was limp. She leaned down and licked all my juices off my belly.
I was blown away seeing her lick me. I looked at Sally, and she gave me a look that said it’s ok, relax. I could not say a word since I still had the pacifier in my mouth.
The problem was that it all this felt so good. This was a part of life I had never experienced and it was so so nice!
My masseuse massaged my legs and upper body, getting to my bra. She asked to unhook my bra and again I looked to Sally, who nodded yes. Off it came.
My masseuse knew I had glued on breasts and worked around them. Then she or he said my body makeup was coming off around my right breast and shall she re-apply body makeup to fix? I shook my head yes. Wow, this was so strange, I was really embarrassed.
After an hour of this pampering we got dressed. I was so weak, so relaxed, as Sally basically walked me out to the car for home.
Sally said we needed to take a nap when we get home, and have a later dinner. “We can take out your pacifier around 7-8pm tonight and then we can have dinner,” she said.
We both went up to our room and fell on the beds for a nap. I could really get used to all this pampering and attention!
We woke up around 7pm. Sally said, “Lets relax tonight, Bob is out of town and we don’t have to get all dolled up.” I wasn’t sure what she meant, so I just listened.
Sally said, “Get into this lounge outfit, and lets go downstairs.”
As I began to take my bra off, Sally jumped at me saying, “Oh no girl, leave your bra on, you need the support plus you need to get used to wearing your pretty bras”.
I pointed to my girdle. She smiled, and said “Yes, you can take off your girdle but leave on your panties.” I looked at her with a face of … ‘of course leave on my panties, I knew that!’
The lounge set was very feminine, soft, and very thin. It had a nightgown-type slip and a robe, but it was so thin I could still see my bra and panties. She then handed me cute slippers with little heels, so feminine I thought!
We went downstairs; wow walking without a girdle or pencil skirt was again very different. I felt free -- no tight girdle holding me.
It was time to take out my pacifier. She warned me not to talk until I took one more medicine, which she handed me. Down it went. I was nervous to hear how this whole voice thing went today.
Sure enough, my voice was very, very girly. I said, “How do I sound Sally, did the operation work?” It was high and soft and gentle!
Sally smiled and said, “Your new voice sounds lovely, a perfect ladies’ voice now. So sweet!”
I was not sure I was happy or sad. Where was my manhood going? Wherever… it was leaving me.
I was shy at first when talking. It was hard getting use to my new feminine voice… coming out of MY mouth. But Sally encouraged me to talk, to get use to my new voice, my sweet voice as she calls it.
We had a wonderful dinner, just the two of us. I felt so good with Sally; I was thinking she was my sister.
We talked about the voice operation and for sure about the spa salon and our massages. Sally wanted to know what I was thinking about the masseuse handling my little guy.
I got all shy; Sally said that magic word “sisters” and that seemed to open me right up into the conversation she wanted to hear.
“Sally this conversation just between the two of us sisters, right”?
“Mary, its just us girls, we’re having a girls’ night. Don’t be embarrassed to talk girly things. You will find it so much fun, what us girls do, so just relax,” Sally said.
“Well, Sally, I got excited when he… wait a minute. Was my masseuse a guy or a girl? He looked like a very pretty girl.”
“Mary, I told you they are all crossdressers, all males dressed as girls. They want to be girls, couldn’t you tell? He was so nice, so feminine, he was a sweetheart.”
“Yes, he was a sweetheart. Do they live full time as girls, like all the time, in girl clothes? That must be strange for them”.
“Mary, think about it. You are wearing girl clothes now all the time, and I think you like it. These men will live their whole lives as women; they want to be soft and feminine. It’s ok that they want this way of life. Now tell me about your feelings when he helped you relax your little guy”.
“Ok, well, I did like it. His hands with that warm oil in the soft glove felt so nice, so soft. As you saw I could hardly hold my pleasure, it came right out. I was so embarrassed, I thought it would spray all over him”.
“Mary, what did you think when he was licking up your love juice?”
“Sally what is love juice… oh, you mean what came out of my little guy. Well, that was so strange, I didn’t know what to think. I was so relaxed I couldn’t stop him. He looked like he so enjoyed that part. I didn’t know what to think, it happened so fast.”
“Mary, you will learn that the love juice men have is sexual for us. You will want to pleasure your man the way your masseuse did you, and you’ll enjoy those sensations too.
“Really, that is strange. I am not sure I could handle that”, I said.
“Mary, your feminine emotions will all come in due time. It is so much fun, I think you will love it.”
“Sally can I ask you a personal question? Will Bob want me to ‘play’ with him down there like that? I’m not sure I could handle that”.
“Mary don’t worry about that, you are a long way from pleasuring Bob that way or any other man.”
I wasn’t sure what Sally meant by that. After all I was only doing this dress-up thing for 3-4 weeks I thought.
We headed up to bed, both saying what a fun night we’d had just talking. I told her I was ok with my new voice as long as my man voice comes back. I’d really gotten used to my new voice tonight, with all our girly talk.
Sally hugged me, saying how much she loved me and that I will do just fine in my new world.
Wow, not sure where that came from again, “my new world.”
Our next day started off slow. With Bob out of town, Sally was real laid back. We lounged around the house until ten-ish when she said, “Today let’s go for a swim!”
“Swim?” I said. “I don’t have a suit.”
“Mary, don’t worry your pretty little head about that -- we have a suit for you.
“But first,” she said, “Let’s sit on the couch and talk. Mary, we need to discuss what happens when Bob’s mother gets here. Now would be a good time to talk about that.”
Oh boy what does that mean?
“Mary you do know you are playing Bob’s girl, his girlfriend right? You have to play the role all the way. His Mom thinks you are the girl for him, you know, the one he might marry, so you have to be very loving with him, very attentive, you know? His girl.”
“Sally I hope he knows there is no way I can marry him. This idea is ONLY for the time Mom is here, right?”
“Yes, of course Mary, but you have to play the part, that is part of the deal.” Sally made that perfectly clear. “So, with that said, you know you will be sleeping and basically living together -- you are his ‘steady’ girl. Bob has re-done his own bedroom to include you. You have a beautiful makeup table, a walk-in closet with tons of pretty clothes, high heels, jewelry to die for, all kinds of things I would die for. You’re a lucky girl with everything a girl would dream to have. Now lets dig out a swim suit you can use.”
I didn’t say much, I think I knew all this, but for some reason I was becoming ok with this girlfriend stuff. Must be those pills in me.
We walked into Bob bedroom. Wow what a room – huge! And yes one end was a girl’s end. Why would he do this for just a visit from his Mom? Sally took me into the huge closet, she was so excited. It was as if a girl had lived here for years, tons of clothes, shoes, blouses, skirts, everything that a girl would dream of.
“Mary isn’t this to die for? Don’t you especially just love the shoe rack -- you have a pair of heels for every day of the year here, you are one lucky girl, sweetie”.
I sat down on a very plush couch, weak with confusion. What was going on here? “Sally why me, why didn’t he just hire you to be his ‘girl’ for his Mom’s visit? You have all the clothes, all the girly things, all the know how to be a girl! You are a girl!”?
“Mary, relax, Bob knows what he’s doing. He knew you needed the money and I was not available anyhow. I have to leave the day before his Mom gets here”.
Fear struck me… “Sally why are you leaving? I can’t do this without you!”
“Mary you will be fine. I will be with you another 6 days and will teach you everything you need to know. You’ll have fun. Relax, for now we are sisters.”
When she mentioned ‘sisters,’ a calm came over me. It was strange, but that word really did help me relax and accept my new life, as Sally calls it.
I was blown way at all the girly clothes Bob had for me already. Sally pulled out some of the many drawers and brought out a bathing suit and said. “Lets go for a dip!”
The suit was a one-piece bathing suit, very 50’s looking, again with point cups. I was concerned my fake breasts would come un-glued and fall out in the pool. Sally assured me the glue would hold, and giggled saying not much of anything would come loose there.
“Mary bend over like putting on your bras, and adjust your breasts into those cups, same as putting on a bra dear.”
Wow, looking in the mirror, my shape was real! I was still adjusting to having what I called mountains on my chest. It seemed so strange, the bounce and weight. I was thinking, why do girls have big breasts?
She handed me a pair of fashionable sandals with small heels for the poolside, and a pool bag, saying all my “pool stuff” is in the bag, so now lets go swimming.
At the pool she reminded me not to get my head wet. “Us girls don’t get our hair wet, it wouldn’t be becoming. You always need to look pretty in case Bob comes home.”
That was no fun, but I guess I was learning girly tricks like that.
Sally popped out of her bag all the stuff we needed paint our nails, saying, “Mary, lets have some fun and re-do our nails. I see you don’t have your toenails painted yet. How did we miss that? That’s not very becoming a girl like you, dear.”
She showed me the tricks needed to keep my nails pretty. We were having so much fun, being so girly by the pool. “Mary, look at me! Tell me the truth, you like being Bob’s girl don’t you?”
I was taken off guard, but found myself saying with such joy, “Yes Sally I am enjoying this new way of life as you call it. I like being pampered, I like all the attention. You have taught me well, no one would know I’m a man, and I am ahead $50,000, and also helping my best friend with his Mom. So yes, I like being a girl for a couple of weeks”!
“Oh, Mary I am so happy for you. I think you make a perfect girl, a perfect girlfriend for Bob. Bob has told me how happy he is that you are adjusting to your new way of life. He is so excited, and eager to present you to his Mother”.
What did she say, ‘Present me to his Mother’? What am I, his wife? I thought.
We had a fun morning. After lunch Sally wanted to teach me more makeup tricks, so we went upstairs to our bedroom and she had me practice many times “making up my face” as she calls it.
Later in the day she announced we have a hair appointment, that Bob thought I would enjoy having a more feminine hairstyle and a perm to add more body to my hair. What the heck did she just say? I don’t know, I just say ok with a smile.
We went to Betty’s, the hair salon in the lingerie store, the same salon we were at before. Betty knew what we wanted -- plans seem to have been made for me before I got here.
I got a little nervous asking Betty if this new hairstyle would be permanent? I told her I would be back to being Paul in 3-4 weeks. She laughed and said with a giggle, “Mary when you are ready to return to Paul I will help you with your hairstyle. But for now, everyone will like this new feminine cut, dear”.
I wasn’t sure what she meant by “everyone,” but I said, “Let’s go for it!”
Two hours later, there I stood, looking totally different. I had little shorter hair cut, styled with bangs, curls every where, and blonde highlights framing my face. Everyone in the salon commented on how cute I looked, that it was just the right cut for my cute face and new look.
I didn’t know what to think, staring in the mirror. Both Betty and Sally put their arms around me, saying again how cute I looked, and adding that Bob will just adore my new hairstyle.
I thought, there it is again… everything to please Bob. Why does Bob need to “approve” everything? What was going on with him?
Plus I am not sure I want to look this “cute”. I’d never been called cute before.
I tried to leave, but Sally reminded me we had to buy a corset and nylons. A corset? Now what, what is that?
Betty grabbed my hand and took me into the back room. She looked at my card; my measurements were on the card. She then giggled as she left the room, saying, “I have just the corset of your dreams, Mary.”
She came back with this long-looking girdle, and “pushed” me into it. Again, yes, those pointed cups. I looked at the cones, and Sally popped in…. “Yes, Mary pointed cups again -- you know Bob likes these, these curves”.
I was too weak to fight it and I could hardly breathe. The ladies said I would get used to the tight corset, and made a few suggestions about how to breathe. They both proclaimed the corset a perfect fit. What did I know? It seemed to me way too tight. Plus the corset really really made my chest stand out. I tried to take it off, but Sally said told me to leave on the corset and wear it home.
Off we went. I could hardly move or sit in the car. Sally giggled, saying I would get used to my new foundation. “Isn’t being a woman so much fun, Mary?” she said.
I looked at her with a weak smile. I could hardly talk in this tight corset. ‘So much fun’ I said!
We got home and she said it was time get into our loungewear and relax. I liked that idea.
She was helping me out of my new corset when I asked her, “Sally, since neither Bob nor his Mother are here now, can’t I put on my Paul clothes, and can’t you treat me as Paul tonight? These tight clothes and makeup and these mountains on my chest are killing me. Who would know if I was Paul for one night?”
“Mary look in the mirror. Do you look like a Paul? Really? Your nails are long and pink, your hair is so feminine, I wish I had your hairstyle, and your boobies are huge. And no I don’t have the solvent to un-glue your nice boobies, only Bob does. Besides I thought you were liking your feminine side?”
“Sally I guess you are right. I am adjusting to my feminine side but I could use a night off,” I told her.
“Mary, I am in the same boat. I too sometimes think it’s hard being an attractive woman, with all the tight clothes and makeup, and hair treatments. But this is the life we were given.”
“Well Sally, this is not the life I was given,” I said.
“Yes, Mary, but you did agree to be Bob’s girl, so now you have to live a new life for a while. So you better get used to it, try to enjoy the softer side of life. You’ll love this lounge set -- slip it on and let’s go have dinner, you silly girl”.
As we were walking downstairs, Sally asked me if I had taken my pills at noon today. I lied and said yes, but I am not sure she believed me. She replied, maybe we will have to double up on them tonight.
That evening there was more talk about “being a girl or how to be a girl.” “How much do I need to learn?” I asked Sally. We’d painted our nails, and it seemed like we were doing this a lot. Though I felt it was having a calming effect on me.
“Mary, tomorrow night Bob is coming home. He called and asked if you would like to go out for dinner with him”?
Fear struck my bones. “Sally is this a date? Is he asking me out on a date? This is all so strange!”
“Mary you have to get over this feeling. You are being paid to be his girlfriend and girlfriends date their boyfriends. They go out on dates, they go out for dinner. Lighten up, it’s just dinner! You are ready for this, and he will be a perfect gentleman, trust me. Look at me we are sisters. Would sisters be wrong?”
“Well, Sally if you think I am ready, ok, I will go out for dinner with Bob”.
“Good girl, Mary, I will tell him. We will need all day to get you ready for tomorrow’s dinner. He wants us to go to Saks for a new dress he picked out for you, and all the other accessories he picked out, like jewelry, heels, a purse, everything. This is so exciting, shopping with his money! Don’t you think so Mary?”.
“Yeh, I guess, but why should he pick out my clothes?” I asked her.
“Silly, he is paying, he is your boyfriend. Be thankful he takes such an interest in your fashion, and that he wants you to have all the best. You are a lucky girl!” Sally said.
I thought, yeh, what a lucky girl I am?
The next day was a busy one. I could not understand all the fuss to go out for dinner. I tried to wear my Victoria Secret t-shirt bra and panties set, but Sally said no, I had to wear a cone bra, as I call them. She said that kind of bra would provide the best fit for my new dress today at Saks.
How did she know what bra would be best for a dress Bob picked out? Did she help him buy the dress? Looks like I will be wearing a cone bra for weeks, now that Bob is coming home.
We did only a little makeup and hair fussing as she said I have a hair appointment at Bettys at 1pm to get all “gussied up” for my dinner date.
What does that mean?
We did the mirror check as she has taught me every girl does before leaving the house. She reminded me to grab my purse; I have a hard time remembering that it seems. Hey, I’m new to all this feminine stuff!
At Saks department store we were treated like queens. Why? They brought us up to a private dressing room that was bigger than my house. Girls waited on us with breakfast, coffee, and even champagne. A girl assistant tried to help me undress. I looked at Sally, asking “Is this ok, is it normal for her to do all this for me?” She waved me on, saying, “It’s ok. Go have fun, I’ll see you in a minute in your new dress.”
I was so embarrassed, undressing in front of this stranger! She was very sweet. It was a good thing I had on my super tight full-length girdle, to hide and control my little guy.
The assistant smiled, telling me what a lovely brassiere and girdle set I was wearing. She wanted to know where I bought them. I didn’t know what to say, but all of a sudden out of my mouth I said, “My boyfriend bought them for me. Aren’t they just so so pretty? And they shape my figure so nice, don’t you think so?”
Where the heck did that come from? Wow, I must be really nervous.
She giggled and said I was a lucky girl to have a boyfriend that would buy me such pretty clothes, as she zipped up my dress.
I turned around, examining the ultra feminine, Southern Belle dress in a mirror. It showed every curve I had. The dress was stunning.
“Oh, dear, this dress was made for you. You look gorgeous. Your boyfriend has very good taste. I sure hope you appreciate him. You are a lucky girl.”
What did she say… I should appreciate my boyfriend? I was a lucky girl? My head was spinning.
I looked in the mirror and yes, this dress was gorgeous. It was pink and white and lacey, hugging my body at every curve. Full length, with a scoop neck and puffed sleeves and a very big pretty bow in front. Very old fashioned, very southern. I looked like a Southern Bell, she told me.
I slipped on my heels and walked out to show Sally. Her excitement showed her pleasure at how good the dress looked on me. I knew she liked it as she ran to hug me.
“Oh Mary, you look stunning, just a lovely girl. I know Bob will not be able to keep his eyes off you. What do you think?”
“Well, it’s hard to walk in this tight dress. I can only move my feet 5-6 inches at a time. But I love the color and all the lace. The bow is pretty big, but I guess it makes the dress,” I told Sally.
“Mary I am so glad YOU like the dress. That is a big step forward in helping you accept your new femininity. Don’t worry about walking, we will practice walking this afternoon. Remember, you will have to wear the corset Bob bought you too. The corset will help you walk with grace.”
I had to sit down, I was weak. What is walking with grace? The girls taught me how to seat while wearing this tight dress. What a process that was. This is all too much, I thought.
The clerks brought me water and then all the other stuff Bob had picked out for me. Heels, purse, nylons, and then a man walked up carrying an armful of boxes. What the heck was this all about?
He started opening the beautiful boxes. One after another contained gorgeous jewelry. Necklaces, earrings, a beautiful flower pin, and then the big “present of femininity,” a huge … what looked likes a diamond ring! What was this?
All the girls in the room were drooling, excited to see all this jewelry, wishing it were theirs.
Sally said, “Mary you are such a lucky girl. You have to try all of it on. They will make the dress!”
I was numb, so the staff with Sally’s help put on the jewelry on me. I told them no ring, I couldn’t handle a ring from Bob!
Then I stood up, looking in the mirror. Wow, I was blown away. The jewelry sparkled, made my whole appearance. Sally knew from my big smile that I liked what I saw.
I was so weak I couldn’t move. We stayed there another hour. It seems they had to tailor the waistline more to me to make it fit even tighter. The seamstress suggested a corset and Sally popped in saying, “Mary already has a beautiful corset, one that she will wear tonight on her date. I should have had her wear the corset today. Sorry!”
There was that “date” word again.
The staff packaged up the dress and all the other purchases, including the jewelry. They suggested we stop home and drop it off before our hair appointment. The jewelry was very very expensive -- we wouldn’t want to leave in the car, the assistant suggested.
Sally pushed us along, saying that she’d changed our hair appointment so we could stop in our massage salon first.
“Mary, I think you need to relax, and your ‘friend’ at the Spa is available for a quick massage to calm you down and relax you,” Sally said.
“Trust me, I am relaxed now, not that I wouldn’t like his massage again.”
“Mary don’t look so embarrassed, you liked his massage the other day didn’t you? Oh, you are embarrassed about what he did with his little white glove to your little guy, aren’t you? But you told me you liked that. You know Bob goes there all the time!” Sally said.
“Oh Sally do you think Bob has ‘that’ done to him?”
“Mary, he might, so what? You enjoyed it, why shouldn’t Bob?”.
“Sally do you think Bob will ask me to do ‘that’ to him? I can’t, I’m a man! How could I do that? I didn’t sign up to give Bob sexual favors, you know!”.
“Mary, don’t worry, Bob will NOT ask you to do that. That’ll be up to you! Whatever you feel comfortable doing will be up to you”.
I thought, she really didn’t answer my question.
We got to the spa and again my masseuse was waiting. He does such a good job. He used his white glove treatment. I just loved it, the oil felt so warm and comforting. I really liked everything he did to me. He makes me feel so girly. Funny I feel like that!
He commented on how much he liked my new voice, and told me how sweet I sound now. He said he was thinking about doing that too!
I got all red in the face. So embarrassed! I was thinking… is this person really a guy? She looks so girly one can’t tell, much like me I thought.
After I was done, I walked out into the waiting room where Sally was on her cell phone, saying, “Yes, Paul is doing just fine. He will be ready for you, for dinner tonight. Here he comes, goodbye!”
I quizzed her who was on the cell phone. She said it was Bob checking up on his date for tonight’s dinner. She looked at me with a big smile saying, “Isn’t that sweet of him, Mary?”
In the car Sally turned to ask me, “Did you like this massage as much as your first time?”
“Sally if you are asking did he give me the white glove treatment, he did, and yes, it was fantastic again.”
“Mary, best you refer to your masseuse as a girl. I think they would like to be a girl, don’t you?
“Mary you are a lucky girl, take advantage of all this, you are living a dream,” Sally said.
I just smiled back and said “Yes.” We were now off to the hairdresser now.
We got to Betty’s and even she knew about my special dress and jewelry. Bob must have laid out a huge master plan for me, and everyone was in on it.
I just sat there while two or three ladies worked on me. My makeup was done perfectly. My hair was styled perfect. I’m not sure why, but Sally gave me a double set of pills this time at the salon, telling me I’ll need them for later tonight, that they’ll keep me very happy!
Wow, was I getting more and more drugs! Then again I’m already drugged, look at me….
Betty gave me a peck on the cheek, giggling and saying, “Mary have a wonderful time tonight. You are one gorgeous girl, and you are ready! Let your guard down, play your girlfriend part, and enjoy Bob’s gentlemanly hospitality. You will love it!”
I was in another world with all those pills in me, not sure what Betty really was saying, but yes, I was feeling very feminine, very soft, very girly, and Sally knew it. I think Bob and Sally had me right where they wanted me.
Back at home, Sally said that I’d have an hour to practice walking and sitting in my new dress. We went upstairs where the maid had all my new clothes ready.
Sally helped me into my new corset we got the other day from Betty’s. Before slipping on the dress she wanted me to put on nylons and attach them to garters. I slipped on the dress, found it really hard to squeeze into the tight, shapely dress. She gave me my heels, brand new 4” heels. I looked at Sally like, I can’t wear these, they are too high! She paid no attention.
Not much choice, so soon we were off walking down the hallway. I could only take baby steps, it seemed. We practiced sitting, keeping my legs together and placing my hands on my lap in a very feminine way. Sally wanted me to show off my long colorful fingernails and diamond bracelet. Between the 4” high heels, tight dress, and corset I was not doing well. Plus she made me carry a purse and insisted I manage it gracefully. We even practiced ascending and descending the long, formal staircase. She said I would need to come down the steps gracefully, slowly, letting Bob wait for me at the bottom. “Let him look at how beautifully you walk slowly down the stairs tonight,” she said.
After many trials, up and down the stairs, Sally announced we were done and that I needed to take a short nap before we began to get ready for dinner.
I fell asleep quickly, I was beat. It seemed only minutes later that Sally and the maid were waking me up, shuffling me off to the shower, telling me not to get my face or hair wet.
While Sally was touching up my makeup I asked her if Bob was home yet. She smiled and said yes, he’s in his bedroom getting ready too.
I was thinking, he has nothing to get ready. I on the other hand I have lots of girly stuff to do. How do girls do it, I thought?
I wasn’t sure why the maid was here with us, but Sally kept her busy. She opened a new pair of nylons as Sally told me to feel them, that they were the best money can buy, that they cost over $300. I slipped them on carefully, and yes they were very soft, and looked beautiful on my newly shaved legs. While I was hooking them to my garters, Sally giggled saying, “Your legs are perfect, very shapely, I would die for legs like yours! Don’t you just love the black seam down the back of your legs? Such an old time pretty look! Bob will love this!”
She then gave me something new, telling me it was a full body slip that would hide any bumps.
Not sure whether it was another girdle, but before I knew it she and the maid had it over my head and were stretching it over my curves. Wow, it did make my figure smooth, and I felt it, very smooth and tight fitting, enhancing every curve. Another girly feeling I thought. Next came the dress. With the body slip on, the dress slid right into place. It fit like a glove and hugged every curve I had.
“Sally do I have to wear this body slip? Isn’t the corset enough?” I said.
“Don’t whimper, it’s not becoming for a girl, I know what is best for my Mary. You are a vision of loveliness. Bob will be so pleased,” Sally replied.
Sally then tied the big lacey bow in front right under my bustline, which really accented my chest. My chest became the focal point of my dress, it seemed.
Sally told me to slip on my heels and stand in front of the mirrors. Of course I did, without hesitation. I thought I was going to cry when I saw how beautiful this girl was before me. It was me, but how could I look so good as a woman?
How could I look so good as a girl in so few days?
Sally must have taken 10-15 photos, telling me to turn this way, turn that way, smile, don’t smile, give her a sexy look, give her a happy look. She took many photos as she said I could be a model.
And then asked the maid to leave. Suddenly she seemed so serious. Again she told me how beautiful I was, but she had one more request. She pulled out that ring box, opened it up, and there was that same huge diamond ring shining back at me. The ring I’d seen today at Saks that Bob had picked out just for me.
“Mary please, please please slip this ring on your finger. Bob loves it so much. He picked it out just for you. It is so special to him. I think you will like it on your pretty hand. It will sparkle so much! Be my sister and wear this for me!”
Not sure what came over me, maybe that ‘sister’ word again, but I slowly took out the ring and slipped onto my left hand ring finger. I was blown away by how beautiful it was. I just loved it tonight, but didn’t want to admit it. How could I, a man, like this gift from another man? A diamond ring no less?
Sally gave me a big hug, saying, “Let’s get going -- we don’t want to keep your boyfriend waiting too long sweetie.”
As we’d rehearsed, I made my entrance down the formal spiral staircase, Bob waiting at the bottom. He looked so happy! So handsome!
Sally had to give me a nudge to start my descent down the stairs toward him. We had practiced walking down these stairs in this tight dress, so I was ready, and was walking down very gracefully. I was nervous, and heard Sally behind me repeating, slow down, be graceful!
Bob put out his hand and my hand connected with his. His eyes lit up, seeing his ring on my finger, although he didn’t say anything about it.
“Mary you look gorgeous, I hope you like the dress I picked out for you. You make it look so pretty, you are so graceful in your walk. We will have such a good time tonight, thank you so much for doing this impersonation for my Mother,” Bob said.
“Bob I have been learning a lot these past days. I hope I can pull this off with your Mom. Being a woman is so different, there’s so much to remember and do”, I said.
Bob looked so pleased as he said, “ I love your new voice, I knew the treatment would work, you sound very lady like. Now lets go to dinner, your chariot is waiting my dear!”
Bob escorted me out to a huge limousine with not one chauffeur but two. We were off to a night that made me nervous to anticipate. But I remembered Sally telling me not to worry, how she had pumped me full of so many pills that I should be feeling so relaxed that nothing could worry me.
Bob kept staring at me, making small talk. I knew he could not take his eyes off me. All of sudden he said, “Mary I have a surprise for you. How would you like to have dinner at my beach house tonight? I think you would really like it.”
I was really so relaxed, I just nodded my head yes.
We pulled up to what seemed to be a huge mansion on a cliff overlooking the shore as Bob said, “Here we are Mary, wait until you see the ocean view.”
I was blown away. The house, the mansion was gorgeous. How could anyone own two huge beautiful mansions like this? I never knew he owned this second place. It was decorated so well, and it was so capacious! The living room windows looked out over the moon lit ocean -- it was paradise. I pinched myself to see if I was really here. I had no idea that my friend had all this money.
Two maids greeted us with impeccable manners bringing Bob’s favorite drink on a silver platter. Then we were ushered onto a patio over looking the ocean, where there were lit candles. This place was very romantic. Why is he treating me like this?
I could not take my eyes off the ocean view -- the whole setting was magnificent. A maid came in to say dinner would be served in 20 minutes. Am I dreaming this? This is a dream world, I thought. Who lives like this?
Bob looked at me and said, “Mary are you ok, you are so quiet. Do you like my cottage?’
I opened up, telling him how much I loved his cottage. We sat down and I think I said the most stupid thing to my friend…
“Bob why did you pick me for this game with your Mother? You could have picked hundreds of real girls to play your girlfriend, hundreds!”
He took both my hands and looked me in my eyes, saying, “Mary, you are my best friend. We have known each other for years. You understand me the best. I needed someone I could trust with my Mother. She is very special to me and I need to keep her happy. I knew you could help me, and looking at you tonight I know I was right. You make the most beautiful girl I have ever laid eyes on. You are one perfect lady inside and out.
For some reason I was so happy, hearing what he had just said to me. I think I am enjoying this new world as Sally said I would. As she said, all I have to do is let myself go and enjoy Bob’s hospitality, his charm.
I grasped Bob’s hands and looked him straight in his blue eyes, saying, “I am your best friend and I will help you. Sally has prepared me well and I know I can help with your Mom. I will need your help even more but I hope I can do this for you Bob”.
He gave me such a big hug I felt a huge feminine emotion come over me. These feminine feelings make my body feel so excited, so soft and warm! I for a moment wanted to kiss Bob, but I didn’t.
Luckily the maid came in to say that dinner was served, and that broke the high emotion I was feeling.
Dinner was on another porch again over looking the ocean, candle lit. Just a beautiful table setting, fresh flowers everywhere and there was even romantic music playing.
During dinner Bob convinced me I was doing everything I needed to transform me into a beautiful woman, and that anything I needed I was to ask for.
He asked if Sally was helpful. I said I could not have done this transformation without her -- she was just a total help.
Bob then talked about our living arrangements and asked if I was ok with it. He said it was important that we had the same bedroom, since his Mother believed I had been living in his house for over six months. Naturally she would think I was sleeping with my boyfriend.
I understood, and said, “Bob we have been friends for years. We have been camping and hunting and even went on a vacation cruise together, and shared the same bedroom. I will try to handle living with you now this different way. I am shy about dressing in these clothes but Sally has helped me. She and I have slept in the same room while you were gone. She told me this would help me, since you wanted me to sleep with you. I understand all that, but I will need your help with my shyness.
“Mary, don’t you worry, I will give you all your space. I do so appreciate all you are doing for me! I will close my eyes while you dress if you like. We will treat this relationship as strictly platonic.”
What did he say ‘platonic’? How could I be sexually involved with him? Wow, this is new. But for some reason, maybe the pills, I brushed off that idea and grabbed his hands (again), saying, “I will handle this, Bob. I will be your perfect girlfriend, for you and your Mom.”
With the many drinks, the beautiful mansion, and the candle-lit dinner, I was in heaven. I felt so good, so relaxed. I thought if this is the way women feel with a man, I can handle this even with all this makeup on and tight corsets.
We had a lovely dinner. It was such a relaxing night, overlooking the ocean.
Just then Bob stood up and came over to me and popped the moves on me. He put his big strong arms around my waist and pulled me closer. I felt a surge of emotion running through me but I actually liked it. He felt so good next to me. He knew I was comfortable as he held me in such a tender way. I liked this, but why?
Bob then suggested we go upstairs and get out of our formal clothes and take a walk on the beach. I melted with excitement, thinking I could at last get out of this corset and these heels, and walk on that beautiful sandy beach as the sun set.
He was such a gentlemen as he led me upstairs. Half way up I realized I had no clothes to change into out here at the cottage. Maybe I can wear his clothes?
“Bob, I have no clothes to change into, can I wear your clothes?”
“Oh Mary you silly girl, my clothes will not fit you now. Wait until you see the clothes I have for you upstairs”.
Back in “our” bedroom, I was blown away again. There were all the clothes any girl would want or need. Looks like my closet back at his house in the city! How could this be, how did all these clothes get here?
“Mary, I think there are some shorts and tops in this drawer over here. And if you want to get out of your pretty corset, there are bras and girdle over there.”
How did he know I had on my corset? We started undressing, I was nervous but Bob was a gentleman. “Mary, don’t worry, I will look the other way as you undress”.
I knew I could not get out of the dress and corset alone – I’d needed Sally to help me into them. I sheepishly asked Bob for help.
Like a puppy dog, Bob bounced right over to my side with a big big smile, saying, “Of course dear, I would love to help you. My my my that is a lovely corset you have on, it does such wonders for your girly curvy figure and lovely dress”.
I got embarrassed as my breasts fell out of the loosened corset. Bob didn’t seem to mind as he said, “Mary, look in that drawer over there,” as he pointed. “I think there is one of your favorite bras and girdle in there you can wear tonight”.
Sure enough there was the pink bra set Sally and I had bought at Victoria’s Secrets the other day. The t-shirt padded bra right next to the dozens of retro cone bras Bob so dearly loved. I hesitated, thinking I could please him by wear one of those cone bras I have worn all week. But since he’d brought my VS bra set out to the “cottage,” maybe he wants me to wear that set? Maybe he likes both kinds of bras?
I grabbed the VS bra and girdle. As I was putting on the bra Bob was staring, enjoying my every move. I thought, he really really likes bras, look at him drooling over this pink t-shirt bra.
“Bob, I don’t know how girls hook these bras everyday. I still don’t have the knack down yet. Sally tells me I will learn and get used to hooking my bras as if I’ve been doing it all my life”.
“Mary, do you want my help?” It almost sounded as if he was begging me to let him touch my bra and hook my bra. I got nervous changing into my girdle the VS pink girdle, so I told Bob I needed to use the bathroom and went into the bathroom to slip on my girdle. I remember Sally telling me to always wear a girdle, all the time!
This VS girdle had no garters and felt good. I checked myself in the mirror -- my bra and girdle looked so nice I thought and my makeup was still ok. But I needed lipstick, I thought. Look at me, checking out my face, I thought. Such a girl! Just then I saw my pill bottles on the sink. I better take my pills, as I heard Sally say inside my head…. Take your pills. Boy, I must really be programed by her.
Walking back into the bedroom, Bob handed me short shorts and a beautiful sexy top. Wow, this top really set off my curves. Good thing I had on this t-shirt bra.
Bob smiled, saying how nice I looked, but I knew he would have wanted me to wear his retro bra. As I looked down and in the mirror, I thought, I might like the retro bras better than this t-shirt bra. Wow, what was going through my brain. Liking the retro bra better?
He handed me cute little sandals and said, “Quick, lets get outside.”
It was such a magical moment. All of a sudden I realized Bob was holding my hand and I’d only just realized it. Problem was it felt so nice, so right. My brain is really messed up I thought.
We walked the beach for the longest time, hand in hand. I thought, if this is the way girls feel, I can handle this for a couple of weeks.
On our way back to the “cottage” I tripped and fell. Bob scooped me off the sand so lovingly. He held me in his arms, asking if I was ok. Looking into his eyes I thought I wanted to kiss him and wow, I was wishing he would kiss me. He didn’t but did drop to his knees to check my legs, holding and massaging them, asking if I was ok. How sweet he was. How could I resist him?
Walking back slowly I was thinking how we both are ‘into’ this new deal. He is treating me so much like his girl and I am falling deep into my mindset of his pampered girlfriend.
Back at the cottage we had another drink by moonlight on the deck.
It was getting late as I said, “Shouldn’t we be getting back into the city?”
With a shy face, Bob said, “Mary, I thought we would stay here tonight. Wouldn’t you like to wake up as the sunrises? It’s so beautiful here in the morning!”
I melted, thinking of course I would love that. Who wouldn’t?
“I have a nightgown for you, in fact the same one you have worn the past several nights with Sally.” Of course he did, he has everything here for me! What a lucky guy or girl I am, I thought.
I did my usual nighttime wash up just the way Sally taught me. Bob was in bed long before me as he stared, watching me get ready for bed.
“Mary, you certainly have learned all the tricks of being a pretty woman. Looks like Sally has taught you well. I am so thankful you are helping me with my Mom and such”.
“Yes, Bob, this is my new a bedtime routine. I never thought I could handle all this. But for some reason I am getting used to the nightly beauty treatment.”
I slipped into bed in my long length, bra cupped nightgown. I loved the way it felt, so soft and comfortable to sleep in. I was wondering if Bob would snuggle on over to me and hold me. Wow, I was actually thinking, actually wanting him to hold me. We’d had such a picture perfect night here, I was really brainwashed.
He was a gentleman as he held my hand under the sheets, saying, “Mary thank you so much for being my girl”.
I got all emotional, saying, “Bob how could I not help my best friend!?”
The sun was rising as we lay in bed. The view out his window was spectacular. As I opened my eyes I found Bob right next to me holding me like a baby. I was not sure what to think or do.
We both admired the sunrise as Bob said, “Lets go downstairs and have breakfast on the deck. It is so beautiful out there this time of day.” He handed me a matching robe and heeled slippers and said, “Let’s go sweetie!”
Did he call me sweetie? Wow, he is really playing the game too. For some reason I liked the word. Made me feel good, strange.
As second nature was working inside my head, I stopped by the full-length mirror to check my look. Bob said, “Don’t worry, Mary, you look wonderful, you always do!”
As we were walking downstairs I thought, how could I not like being a woman for him. All this pampering, all these beautiful clothes, and such a good friend being so nice to me. I melted at his every suggestion.
He was right, the sunrise was spectacular. And as we sat down, there was the maid serving us breakfast. How great is this?
“Well, Mary, what would you like to do today? I do not have to go in to work, so the day is yours. Would you like to walk the beach, go for a boat ride, go shopping? You name it, it’s your day.”
I hesitated. I didn’t know what to say, things were happening so fast.
“Mary lets walk the beach this morning, have lunch at my country club down the road, and then stop back in the city at Saks. You will need a special cocktail dress for my Mother’s homecoming party”.
“Bob, wait, your country club? Your friends? Do you really think I am ready to meet your friends? And what is this homecoming party for your Mom you are talking about?”
“Mary, you are so ready, you are so girly, and you pass so well, even my maid thought you were so beautiful. Yes, each time my mother comes into town I give her a little party. For her friends you know. It’s small party and you will be just fine.”
“Bob I sure hope you know what you’re doing. I don’t have Sally here to get me all made up for your country club today.”
“Don’t worry your pretty little head, you’ll be fine. If you need help getting dressed or with your makeup my maids can help.”
Back upstairs, Bob handed me a bathing suit, a one-piece suit and yes, very retro, with pointed cups and a little skirt around the bottom to cover up my little guy. Thank heavens the skirt would also hide my little bum down there.
Again I watched as Bob stared at me while I was wiggling into my suit. He really enjoys watching me dress and undress, I thought.
This bathing suit was something new for me. It almost felt like my corset but not as tight. I liked it, even the pointed bra cups.
Like a little girl, I twirled around, asking Bob if he liked my suit. “Oh, Mary I do love your figure, you are one pretty girl. I bought you the cutest swimsuit just for you. I am so glad you like it.”
My brain was on cloud nine, I was so happy. Every thought flowing through my brain seemed feminine, so girly. Will I ever remember how to be Paul?
Out on the beach the staff had set up two lounge chairs in the sand and a tent with a table full of fruit and Bloody Mary’s, Bob’s favorite beach side drink as he said.
The ocean air was so inviting, and the comfort of the beach was so relaxing… Again I thought I was in heaven.
All of a sudden Bob reached over with his hand and took my hand, looking at me, saying, “Isn’t this the most beautiful place you have ever seen? I just love it here, especially with you here now”.
“Bob I do love it here, but I am confused”.
“Mary what are you confused about? Talk to me, you can ask me anything.”
“Ok, then. I think I understand why I am doing this for your Mother. But your maids here and those back in the city look sort of similar. It’s a little strange. Tell me, are they men”?
“Mary, I do have a little secret. I will tell you but please don’t freak out, try to understand my thinking. I am gay. I do not date nor want girls living with me. Yes, my maids are men, they are crossdressers like you. They willingly work for me, and I take care of their feminine needs as you can see. I do not have sex with them, they just work for me. They live in my houses, I pay them well, and I take care of them, and yes, as you saw they do dress as I desire, the old fashioned 1950’s ways.”
“Mary, please talk to me, don’t be shy. I don’t want you to do anything that you don’t want to do. I respect you too much for you to do anything you don’t want to do.”
Oh boy this is so strange. “Bob, I thought the maids looked too perfect. Yet they seem so happy. And I’ve sometimes wondered if you had gay feelings after all, I’ve known you forever. So what does your mother think of all this? Does she know?”
“Mary, my mother does NOT know and she can’t. If she finds out I am gay I will be cut out of all my money. And out of her will. All this will be gone! My inheritance will be gone!”
“Bob, don’t worry, your secret is my secret. I am glad you leveled with me”.
I had tons of questions flying in my head. I told Bob I needed to close my eyes and listen to the ocean, but I really needed to figure out all this stuff. Does he want me as his gay lover? Will he make his moves on me? After all, we are already sleeping together. Boy I wish Sally were here now, I need her!
After about an hour I was ok. I knew I needed to digest this more, and maybe Sally could help me back in the city. I pretended to wake up looking at Bob. He was staring at me as I smiled and asked if everything was all right?
“Of course everything is all right, Mary, as long as YOU are happy!”
I smiled again, thinking how could I not help him, keep his secret, he is a perfect gentleman, and before I learned this new information I had already told myself I loved this new feminine life of mine.
“Bob, thank you for telling me all this. I am still in with your plan, I will help you any way I can. You are so sweet, I’m not sure how any girl could resist you.”
“Thank you so much Mary, I was worried you would freak out. You are such a good friend I’m not sure how I can ever repay you.”
All of a sudden my brain said to me, what he can do for me? I am so happy at this place, with Bob and all this beautiful stuff. I am just happy he has shown me this other side of the world, the women’s side.
But I couldn’t tell him that.
Bob grabbed my hand and with a big smile and said, “Why don’t you go get ready for lunch at the club. I have some work to do in the study and I’ll be up later to change”.
I went into the house. Seeing the two maids in the kitchen, I think I smiled, but in my brain I tried to undress them to see if they were crossdressers. They looked so sweet. They too were dressed in the retro maid fashions.
Upstairs in our bedroom, the bed was already made, everything was picked up, and a beautiful outfit was laid out on the bed for me. I thought, Bob even has these maids programmed to pick out my clothes. Right next to a sexy little sundress was Bob’s favorite retro bra for me. I got the message -- this is the bra he wants me to wear today.
I started the feminine drill Sally taught me. First a shower, then I shaved my legs and under my arms, and then I slipped on my panty and girdle. Then came the retro bra. Wow, these bras are pointed, but for some reason I was liking them more and more. I stood admiring myself in the mirror when the door opened and in came Bob.
With a big smile on his face, he said, “I hope you like the outfit I picked out for you. You do look stunning in your pretty bra and matching girdle”.
Suddenly he came from behind and put his arms around me and gave me a kiss on the neck. He whispered in my ear, “Paul, thank you so so so much for helping me!”
I wasn’t sure what came over me but I turned to jelly. I wanted to turn around and kiss him. Wow, his magic was working on me.
He disappeared into his bathroom (we each have our own) to get showered and dressed.
I sat down and started my makeup routine while admiring my reflection in the mirrors. Thinking all the while, this bra is very nice, so pretty and so supportive. I can see why Bob likes his girls in them. These bras are very feminine and very retro looking.
Done dressing, checking myself in the mirror, wow another dress showing all my curves! Bob said I look great, and assured me all his friends will just love me. I grabbed my purse (it was almost second nature now, carrying a purse), and off we went to his country club.
For some reason I was very calm, in control, and I even enjoyed his lunch friends. No one was the wiser about my cover up, and Bob was the perfect attentive boyfriend.
When I had to use the bathroom, I stood up and like magic the other two girls at the table stood up too, saying they had to power the faces too. Oh, no, they are following me!
I told myself, calm down, walk straight, and make sure I go into the ladies room.
Inside the ladies room was a real experience. What a lush’s room, so pretty, and decorated with flowers everywhere. As we were all at this huge mirror “powdering our faces” Ami said me, “So Mary, where did you meet the most eligible bachelor in the city?”
Oh boy, sounds like Ami wants Bob and I took him from her. Now what? Where is Sally when I need her?
“Ami, we met in college, and I’m just passing through town.” I left the bathroom quickly and avoided more questions.
After lunch Bob said, “Lets get back to the city and stop for your special party dress”. I asked about my formal dress from last night and all that beautiful jewelry back at the cottage.
“Mary don’t worry about that, if you need any of those things, the staff will drive them into the city and bring them to you.”
While driving back to the city, Bob made small talk. He wanted to know if his lady friends talked my ear off in the ladies room. I said, no, just girl talk, you know! I told Bob I thought I held my own talking the girly line.
Bob reached over to me and patted my leg, saying what a great job I was doing. No one would ever know I was a man. I guess I was thankful for that. I didn’t want anyone thinking I’m Paul, not when I’m dressed like this.
Back at Saks, the staff laid down the red carpet as Bob walked in. Anything Bob asked for was their pleasure. Bob had me try on several dresses before HE picked the cocktail dress for me. I felt so pampered. I was getting used to the fact that he was in charge and controlled everything. I liked this, being taking care of!
He settled on a very feminine lacey short cocktail dress. Again a dress that showed off every one of my curves. Not only a dress but also shoes, and he wanted special nylons. He described the nylons as “those retro silky nylons with the stripe up the back”. They were soft, gorgeous, and they cost $185.00. He bought me three pair.
As we left the dress salon, Bob wanted to take me upstairs to the lingerie department. He thought they have the most beautiful women’s lingerie anywhere.
He was right, their lingerie salon was huge, and so so nice. A lady came “running” up to Bob saying, “Hi Mr. Smith welcome back, what can we help you with today?”
Everyone in the Saks store seems to know my Bob. As if he owns the place. Maybe he does!
I stopped and closed my eyes, thinking, did I just think “my Bob”? Wow, where did that come from?
“Susie, I wanted to bring my girlfriend up here to show her all the beautiful lingerie you have, and maybe even let her pick out something new today”.
“Mr. Smith you are so sweet,” and as she looked at me she said, “Mary you are one lucky girl to have Mr. Smith as your boyfriend!”
How did she know my name? Then again, it sounds as if Bob shops here often. As I looked around, there in a corner were the retro fashions, including bras and girdles like those I was wearing now. So this is where he bought all my retro lingerie!
Susie smiled and said, “Of course Mr. Smith, right over here. We have some pretty new bras in that I am sure you and she will like. She led us right to the Retro fashion corner. How did I know that?
Susie suggested it might be good if she took me into the dressing room to update her records of my measurements, since she had not done that yet. Within seconds I found myself being taken into the back room. Susie was so excited to finally meet me.
It was just she and I as she asked me to raise my arms. She had the tape measure around my chest in seconds. I remember how I’d been measured at Victoria’s Secrets, and marveled that my artificial breasts seemed undetectable. She announced 36C-24-36 and told me how wonderful I looked now in my retro fashions.
“Susie, how did Bob know what size bras and other things to buy me”?
“Mary, we helped Bob a couple of weeks ago as he explained your body type and size. We are good here in the Saks lingerie salon. Looks like your foundations fit you just right. You do fill out your cups nicely, don’t you dear?”
“Susie, does Bob buy other girls lingerie here?”
“Oh, no I never saw him in here before maybe 5-6 weeks ago, when he was talking about you and buying all your beautiful lingerie, dear.”
I think Susie wanted to change the subject as she took me out into the store to show me the “new shipment” of retro fashions. Bob was already there checking out the display. Wow, Bob is really into lingerie I thought.
“Mr. Smith, we confirmed Mary’s measurements, her figure is just as you said. She has a lovely figure and her foundations fit her perfectly. Can I show you both some of our newest retro fashions, they just came in yesterday?”
I have to admit these retro fashions -- bras, slips and garter belts -- are really beautiful. So much lacy and pretty feminine colors. Bob pulled off the display a ¾ length bra set saying, “Mary look at this set, so pretty, here is your size, would you like to try it on, it is so you Mary.”
Before I could answer, Susie had me back in the dressing room with that new lingerie set, saying, “Mary you will just love this new bra. It has a little padding under the cups to give you more lift and separation. It’ll give you such a sweet curvy figure. Here let me help you sweetie!”
I thought to myself, great, just what I don’t need, more lift, more curves, and why do so many people call me sweetie?
She helped me into this strange bra. It was long and yes, it was very supportive. “Mary this ¾ length bra fits your figure perfectly. Bob will love it!” There is that Bob approval thing again. Why does he have to like everything?
“Mary, would you like me to have Bob come in here to see your new purchase?”
I told her, “No I like the set, and I will take it!” Wow, did I just buy my first bra? She quickly asked me if I would like the complete set, slip, garter belt, full and half-slip and camisole?
I smiled and said, “Yes, of course, a girl has to be matching, right?”
I couldn’t believe I said that -- where did that come from, out of my mouth?
Not sure why, I told Susie I would wear the bra home.
As we walked out of the dressing room I saw Susie giving Bob two thumbs up. What did that mean?
Bob came over to me, whispering in my ear, “Mary you look so pretty in that new lingerie. I am so happy you told Suzie you would buy the full set!”
Susie wrapped everything up as she said, “Mr. Smith would you like your girlfriend’s lingerie delivered to your home or will you take it now?”
What, they deliver? And how did she know I was living with him?
I just smiled as Bob said we would take Mary’s lovely unmentionables with us now.
As we were walking out, I asked Bob, “Did she know I am a man?”
“Mary you did great, you are the perfect girl now. You played the game perfectly, thank you”!
On our ride home I asked Bob why he likes this old fashion clothing look.
“Mary, I have always liked a full figure woman, their shapely look. There is just something about their demeanor, the presence of a pretty retro figure. My Mom wears these bras, and she is such a classy lady. I sure hope you can like your lingerie and enjoy wearing the same pretty fashions”.
“Yes Bob, Sally has got me accustomed to the look. I am still having a hard time with such large breasts on my chest. But I am getting used to them and their bounce and how they really cause attention while walking in public”.
“Mary, thank you, you are so sweet”!, Bob said.
Back home Sally was waiting for us. Like girlfriends, she pulled me out to the porch, saying to Bob, “Mary and I have to have some girl talk.”
“Ok girl tell me about your slumber party last night with Bob, and I see he took you lingerie shopping, and you still have his ring on. Oh Mary tell me all!”
“Oh, Sally so much happened, where do I start?” I went through everything. She was smiling like she knew it all.
“Sally did you know that all his maids are crossdressers? They are all men! I knew Bob was a little gay but this is way out there. They look like perfect girls and act the same -- someone taught those men very well”.
Sally raised her hand, smiling, saying, “I taught them, they are my girls, I manage them for Bob. Aren’t they just perfect? Why do you think I was able to change you so quickly?”
Oh, no, the thought ran through my brain… will she change me to a maid?
Just then she hugged me, saying, “Mary don’t worry, neither Bob nor I want to change you into his maid. Remember, I work for Bob and Bob is gay.
“Good because I have no desire to work here as a maid,” I said.
I told Sally about today’s luncheon at the country club and then going to Saks for a cocktail dress.
“Mary do I detect a bit of excitement in your voice about all the fun things that have happened in the last 24 hours?”
“Yes, Sally, I have to admit I did have fun. Being pampered and taken care of is such a nice feeling, so different for me. I have no worries; Bob takes such good care of me. Here, look at the new retro lingerie he bought me at Saks. That is one beautiful store, especially when you have a boyfriend buying your clothes for you. Wait until you see the cocktail dress Bob bought me for his Mom’s party. It is gorgeous!!!
“Mary calm down, I think you had fun sweetie! Lets go upstairs and get you ready for dinner.”
A couple more days passed as Sally taught me more and more girly things, as I call them. I had a hard time walking “like a girl” as Sally says. I had problems getting my arms moving right, but Sally showed me ways to carry them so they seemed, like the rest of me, delicate. She taught me whole new sets of feminine words to use when expressing myself. Took a lot of getting use to, but I learned them. Learning all the body parts that girl’s shave is amazing. I had a hard time shaving under my arms, but I final got it. I couldn’t believe girls shave around…well, like around my little guy. That was scary and not at all easy. Girls go through a lot to be pretty!
Tuesday Sally took me to the gym for a workout. As a man (in the past) I loved the gym, and went all the time. Well, how did I know this was NOT just any gym? It was a gym just for girls. Plus it looked like it was inside the same building as the doctor I’d seen, strange.
Sally dressed me up in a sports bra and girdle and leotards. I looked so girly in a tight fitting pink flowered outfit! I even had pink sneakers.
I felt so self-conscious in this all women’s gym with 20-30 other girls in the class. And the exercises we did were for women only, trust me. Never had I seen or done such movements at my men’s gym. Women are built so differently.
I got real embarrassed moving around and feeling my breasts bounce all over. I looked to see if the other girls were watching me bounce, or noticing that I was not very graceful.
No one was watching me. I was just one of the girls in the gym. Sally told me how proud she was of me, “Mary you are one of the girls here!” I wanted to believe it.
Tuesday night we all had dinner together. Bob and Sally told me the plan for the balance of the week before Mom gets here Friday.
I got nervous when Sally said it was time for me to move into Bob’s bedroom. I thought I needed more time to get adjusted with him, and said something to that effect.
“Mary you slept with Bob out at his beach house and I know you knew this was coming,” Sally said.
Bob added, “You will do fine. It will be like you are camping with me like you’ve done before with me, plus I will be a perfect gentleman.”
I nodded my head. I was too nervous to talk, but I knew I had to do this. It was all part of the deal.
“Mary, remember, Thursday I will be leaving, so you will be the woman of the house. Bob’s Mom mustn’t find two girls in the house,” Sally giggled.
Bob reached over the table and grabbed my hand, smiling, saying to me, “Mary, all will work out. You have been such a princess! I will be here to help you. I think you will enjoy the next two weeks”.
I smiled, saying, “Bob I am ready.” I then jokingly said, “But I might need more of those pills to help me”.
Both Bob and Sally giggled, saying, “Mary don’t worry, we have tons of those pills for you, don’t worry your sweet little head.”
So that night, I moved into Bob’s bedroom. I went to bed early to avoid getting undressed in front of him. I slipped into bed before he came up. All went well. I was surprised how well I was doing.
The next day Sally decided to leave earlier. I thought I was going to cry as she hugged me saying, “Paul, you have done wonders. You will do just fine girl. No one will know you are a man. You are one perfect lady. It was fun working with you, sweetie”.
Bob was off at work and I had the whole mansion to myself. Well, with the two maids. Still, I felt strange about them.
I thought since both Sally and Bob are gone, it might be fun to get out of these clothes and wear some men’s clothes for once, Bob’s clothes. Back up in “our” bedroom I found his clothes, got out of my nightgown, and tried on his pants.
Oh no, I couldn’t close the pants, my hips were different. Why were my hips so big? Then I forgot I could not take off my C cup breasts, that Bob has the solvent to the glue. I tried one of Bob’s shirts, but they wouldn’t button either. I was so defeated; I put my nightgown back on and sat at the makeup table almost crying.
I thought, well, if I can’t be a man, I might as well take advantage of my “new life” as Sally calls it. I put more lipstick on and changed into my retro bathing suit and went to the pool to be waited on by the maids. Why not, I thought! Pamper myself!
I laid by the pool the whole morning, it was so nice. The maids waited on me, brought me whatever I needed.
I thought now is the time to quiz one of them why she or he was here.
“Anne, could I talk to you? Could you sit with me?”
She had no problem opening up to me why she “works” at Bob’s mansion and why he is a crossdresser.
“Mary, I have been a crossdresser since I was 9 or 10. My parents wanted a girl, you know the story. They sent me to the Institute to be trained as a girl. From there Bob offered me a job here. I just love working for him and the pay is fantastic. I sure hope you are ok with me being your maid and helping you. I must say you have done wonders, changing into his beautiful girlfriend. You are lucky to have Bob as boyfriend.”
“Anne, do you really like your retro look, this fashion Bob has us in”?
“Mary, I love the look, I love my figure in these foundations. I love everything about the retro bras, girdles, and so on. Between you and me, there are tons of men out there that love this look too. I see Bob has you in his favorite kinds of foundations too, his look! He is so sweet!”
Wow, this all too much. She really wants to be a girl and has found a job doing just that.
She hugged me, saying, “Mary, thank you for not mocking us and being so kind to us. We are here to help you. We love our job!”
I was blown away hearing her/him talk about how happy they are here. They are such sweet girls or maids, and I feel they will be my friends as I pull off my deal with Bob.
I had lunch out by the pool, while watching the pool boy at work cleaning the pool. He was checking me out every minute. It was such fun, this boy making eyes at me. I guess I passed the test, if this kid makes eyes at me I must really look like a hot girl, I told myself.
While Anne was picking up my dishes from lunch I whispered in her ear, “That pool boy, why does he keep looking at me?”
“Mary is he harmless, he knows a good looking girl and he’s looking at both of us. Go ahead and flirt with him, I do!”
I didn’t flirt with him. But for some reason I was a little girly giddy knowing he was flirting with me. I guess I really do pass as a girl.
The day passed quickly as I laid in the sun at Bob’s gorgeous pool.
While I was upstairs getting ready for Bob, I noticed I was now “branded” with a girly tan. I had tan strap marks from the swimsuit on my body from being at the pool all afternoon. I was branded a girl! Strange, I just giggled and found my new tan marks fun!
Bob came home early. I was dressed and “ready for him.” We sat by the pool having wine and talking about his Mother and what I should watch out for. It sounded like his mom is really the head of this family, very strong willed.
Just then the phone ran, Anne (the maid) brought Bob the phone. Bob looked at me with a very serious face after answering the phone.
“Mary this is for you, bad news,” he said.
Who knew I was here? What bad news?
“Hello, this is Mary…. Paul! No this is Paul, I have a cold and a problem with my voice. What’s wrong Steve? What did you say? My trailer and car have burned to the ground, say that again? What happened? Is there anything left? Oh, no, what do I do? I think I am going to cry! Ok, Steve, let me think about this, I’ll call you back! Are you sure everything is gone? That’s all I had in the world! Ok, Steve thanks for calling, goodbye.”
Bob looked at me with such sympathy as I told him my trailer home and car burned, that everything I own is gone. What do I do? I started crying, I was so emotional. Everything I own is gone, I said. I am homeless, I told Bob.
Bob came over to me with a big hug saying, “Mary, just thank heavens you were not in the trailer home when it burned. You are safe here. Mary, you can stay here as long as you want. You are not homeless.”
I looked up at Bob. We were hugging, and I felt so safe in his arms. I whimpered, saying, “Bob you are so sweet, thank you for offering. I don’t know what I will do.”
“Well, Mary, you will be with me for another couple of weeks. We can figure this out together. If you need my lawyer, my guy can go to your trailer park and figure out what went wrong and close things out there. I will send him”.
“Bob thank you so much, you are so sweet.” There was that “sweet” word again. This word is in my sentences a lot lately. I went upstairs to collect my thoughts.
I couldn’t believe how emotional I was. Just like a girl. These pills are really affecting my brain.
Twenty minutes later, Bob knocked on our bedroom door and popped in, asking if I was ok. “Mary why don’t you freshen up your makeup and join me for dinner out by the pool. It’s a beautiful night by the pool side, we will have a nice evening, maybe even take a dip in the hot tub or pool later”.
How could I resist his hospitality, his kindness, his love. Wow, did I think he loves me? Well, I needed love after hearing this bad news, so I went downstairs and let him take care of me, again. Not before I popped my nightly dosage of pills. I knew the pills would help me. I wanted the pills to help me. They relax me so much. I am addicted to these little pink pills.
The big day came Mother was coming today. Bob was nervous and I was the one calming him down. Go figure!
We both went to the airport in the limo to pick her up. She was exactly as Bob said she would be. She came off that plane looking very high-class, dressed elegantly to the nines. She was beautiful. Her clothes were the tailored and showed off her curves like no other woman. Everything from her hairstyle to jewelry declared her a very classy confidant woman.
Also so sweet. She hugged both of us like long lost family. I’d been nervous she might somehow recognize me as Paul, but I’d never met her and obviously I didn’t look like Paul now in this dress, hairdo and makeup!
She declared she was so excited to be here visiting. Bob introduced me as his girlfriend. All was going so well. We got home and the maid staff got her settled in her west wing bedroom.
She joined me back by the pool after she unpacked. Bob was in his office, so it was just the two of us “girls” doing girly talk as I call it.
“Call me Maggie,” she said right off. I nodded. She started right in talking.
“Mary, I see we share the same love of 1950’s fashion. I love your wardrobe and your retro figure. I enjoy the retro look myself as you can see. That’s what women wore when I was a little girl, and I couldn’t wait to grow up myself and wear those dresses. Back then women were real women. They were pampered by their men and men couldn’t keep their hands off us. It was such a fun time”.
Looking at her, I saw her fashions were indeed from that decade, but she looked so with it, so classy!
Bob re-joined us as Maggie said, “Bob how about the three of us have a candlelight dinner by the pool tonight at sunset?” Of course Bob said agreed and instructed a maid to prepare dinner accordingly. I wasn’t sure what that might mean, if anything.
Maggie excused herself to go upstairs and take a nap; her trip had been very tiring, she said.
“Well, Mary what do you think. Isn’t my mom a sweetheart? I sure hope you can get to know her this visit”, Bob said.
I just smiled and said I would do my best. I need to lie down too. Bob told me tonight’s dinner would be formal. He suggested I wear the full-length red dress he’d bought me. I knew that one, it had to be worn with the corset. Wow, I did not want to get poured into that tight corset to display my curves in that dress. I knew Bob liked lots of dinner makeup, heavier looking nighttime makeup. I thought I’d better get started now so I’d be ready. After all it does take longer to dress as a woman, I giggled to myself.
Time went fast. I’d pulled on the corset but couldn’t lace it up. Where was Sally when I needed her? I was thinking now what will I do? I can’t lace my corset up. Should I call the maid?
Just then my “boyfriend” walked into our bedroom. He saw my dilemma and offered to lace me up. I was saved; but it felt strange having him get me dressed. He knew just what to do though, and he was very sweet and gentle. He didn’t lace me too tight.
I then sat on the makeup chair to put on my nylons and hook them to the garters. Bob got a real kick out of watching my every move. He stared as I said, “These nylons you bought me at Saks are really beautiful, Bob. So soft, I love wearing them”.
What the heck just came out of my mouth, “I love wearing nylons”? Wow, this must be the girly talk Sally taught me. These words come out of my mouth so easy now. But I saw Bob’s eyes light up when I said that. I thought he was going to come over and kiss me, but he didn’t.
He stuck around and helped me zip up my dress. I did my mirror check, smiled and said, “I look perfect, and do you think your Mother will approve?”
Bob grabbed my corseted waist, pulled me close to him, and said, “You look so pretty, so gorgeous, I am so glad you are my girlfriend. My Mother will adore your dress and you of course. Lets go downstairs and have fun”.
He was right; his Mom loved my retro dress. She too had a retro dress on. Like me she was supported by a corset and a retro bra, I could tell. She told me how beautiful I looked and that Bob was a lucky man to have such a pretty girlfriend.
All of a sudden, my body walked over to Bob and gave him a “smooch kiss” on the cheek as I said, “Maggie, he IS a sweetheart, isn’t he, I know I have a great catch here”.
Where the heck did that come from? Did Sally program my brain to say that? I sounded like Bob’s wife or lover.
Dinner went well. I tried to keep my mouth shut. Mom really did all the talking, obviously she was a talker.
Over the next couple of days we “bonded” well. She is really a very nice lady, I found. She had no idea I was a man. Bob was happy, I was happy. This “game” was working and I was having lots of fun.
Later in the week she asked me out for a “girls’ shopping spree”. It felt strange, but I liked the idea and said I would love to go shopping with her.
The next day at breakfast it was just Maggie and I, Bob had already gone to the office. She told me the plans she already has made.
Our first stop would be Saks Department store. She wanted to find a dress for Saturday night’s friends party Bob was having for her. She wanted to buy me a new dress too.
Then she said she’d be meeting two of her close girlfriends at the country club for lunch. After lunch we would do a makeover at her favorite boutique salon. After the salon date she wanted to do High Tea back at the country club, if we had time. It sounded like a full day.
As we were walking upstairs to get ready she said to me, “Mary the ladies at the club will all be dressed in their retro fashions. We make these luncheons an old fashion southern belle fashion event and we all try to outdo each other’s fashions.”
“Also Mary, you should wear your pretty retro bra, I want to have you try on some new lingerie at Saks. I got a call from Suzie and she has some special bras put aside for us. I know how much you like your retro look!”.
She knows Suzie at Saks? How could that be? And why do I “have to” wear a certain bra?
I smiled, thinking that I was hoping to wear my Victoria’s Secrets t-shirt bra. But, well, back into the pointed bra. I was really getting use to that retro shape so it was not a problem.
Off we went to Saks. She was so excited to go girly shopping, saying, “This is something I did with Bob. I was surprised how much he liked dress shopping.”
Bob went shopping for dresses with his Mom? I will have to ask him about that.
Here I was back in the beautiful Saks dress shop again. Of course the staff knew Maggie and again they tripped all over us in finding the perfect cocktail dresses. I liked all the pampering.
While I was in the dressing room slipping on my fifth dress, in popped Maggie. I got so embarrassed standing there in my long-line panty girdle and retro bra.
“Mary, don’t be embarrassed, don’t be shy, we are all girls here. I came in to help you with that dress, it might be just the dress for your cute figure,” Maggie said.
As she was slipping the dress over my head, she said, “Stop and take off your dress dear, your bra needs adjusting.”
Fear struck my brain, what is she talking about? I sure hope she did not figure out I have fake breasts.
“Mary, look, your cups are baggy, you are not filling out your cups, and that will make the dress look odd. Can you bend over and see if your girls can fill out your cups better?”
I was in shock at how personal she was getting. I didn’t know what to say so I just bent over to adjust my breasts into the cups better. I knew what she was talking about. Sally taught me “the bend” to have my breasts fill out the cups each morning when getting dressed. Funny, my fake breasts had always filled out the cups before. What was wrong now?
I couldn’t get the one breast to fill the cup. Maggie came over to me and said, “Here let me help you dear.”
Wow, she was right in there, handling my breasts, pulling them up, and trying to fill out the pointed cup. She is going to figure out I have fake breasts and then our secret will be blown. Bob will be so mad.
Somehow she fixed my cups and the bagging disappeared. She smiled and said, “Now that looks much better. You have such a pretty figure Mary; you should always be supported like that. Such a pretty bra!”
“Mary, my breasts don’t fill out my cups well either. So my foundation fitter gave me little pads to fill out my cups to give me a better shape. You might want to try a little padding sweetie”.
I just smiled, thinking I don’t need more padding, I have enough curves.
She slipped the dress over my head, adjusting it, then said, “Mary this is the dress for you, it’s perfect, I just love your pretty bustline in that sexy dress, sold”.
I guess this is the one, as long as SHE likes it, I thought. Did she say sexy dress? Sexy?
Leaving the dress shop she whispered in my ear, “Mary now I have a treat for you, sweetie, upstairs in the lingerie salon”.
I could only imagine what, as we walked upstairs hand in hand. I liked this lady!
Not sure why, but I actually got excited about going to the bra and girdle department again. Bob had taken me there the other day and it was a beautiful department. We walked hand in hand as our high heels clicked, announcing here are two women ready to shop. I was having so much fun. Of course Suzie knew Maggie.
Suzie ushered us to the back room for a private fitting as she held up this gorgeous all-in-one girdle. It was gorgeous, garters and all. It was pink and white and lace all over. Yes, the cups were retro with lots of lace and a little bow between the cups. For some reason I loved that little bow between the cups, a real mark of femininity. Maggie was so excited; calling it the most comfortable girdle she has ever worn, as she twirled around saying, “See I have that exact all-in-one on now. Isn’t it perfect? Mary try it on and then we can be matching girls!”
Matching, that sounds strange but a little fun. Is this what girl’s do on their shopping sprees? Suzie quickly got me undressed and I pulled on this new looking girdle, in the back room of course. Didn’t want those ladies seeing my little guy. I was a little nervous since there was a little bump down there with this kind of all-in-one girdle. I was worried they would make me out as a man down there.
I tried to hide my little bump by holding my full slip in hand covering that area. It worked, I was fine.
Maggie was so excited as Suzie said, “Mary, your new foundation fits you perfectly. Such a pretty shape it gives you, so sweetie”.
I liked it too as I told Maggie how nice if felt. Not sure why, but I grabbed my breasts saying, “Do you think there is enough support in the cups?”
I was blown away I had said that! Not sure where that came from. Both ladies giggled and said together, “Mary you look great, your breasts are beautifully supported in those cups”.
“I will take it!” I announced with a huge smile. As I was walking back into the private dressing room Maggie said, “Mary leave your new all-in-one on, we want to be matching the remainder of the day, dear.”
As we were leaving Saks, I had a warm and feminine feeling. My body moved differently in this all-in-one girdle. My hips moved with a soft swaying and my boobies felt different. A nice different I thought.
I was really bonding with Bob’s mom, and it’s because I am a woman, or trying to be one. I liked this new feeling!
We then went to lunch at the country club with her lady friends. They never stopped talking about fashion, kids, cooking, everything, it was fun. They all talked about the 1940’s or 1950’s as if they wanted to go back to that time when ladies dressed as ladies and men took care of their women much better than they do today. It sounded like it was more fun back then, to dress and be so feminine. One lady said she’d never worn anything but dresses and high heels. Back then ladies were ladies and men appreciated them.
All the ladies were all so sweet, saying how cute I looked and how lucky I was “catching” Bob as my boyfriend. I just smiled, thinking they might be right; he is a “catch”! The same word I’d used to describe him to his mother earlier.
After lunch we headed to Maggie’s salon and spa. This was a new salon, also very nice, for women only. I was wondering if they had crossdressers here too giving massages, like where Sally took me last week.
Maggie took me right into the hair salon area, saying “We have an appointment for a makeover.” What is a hair makeover?
The owner Melissa told us to slip out of our pretty dresses and put on the robes in the dressing rooms. I was getting used to this dressing room routine.
As I was leaving the dressing room I saw my reflection in the mirror, I could see my all-in-one girdle through this thin feminine robe. I thought, “So what, this is an all-women’s salon. They all wear bras of some sort here, right?”.
Melissa said I was going to have my hair done first and that Maggie had an exciting idea for me. “Mary, would you like to go blonde? Remember, blondes have more fun, they say!”
A girl sitting next to me, a blonde, also giggled saying, “Yes they do and I know from first hand experiences. Go for it girl, you will love it. Your hair is perfect for a full body perm cut and color. You will look so so sexy!” she said.
“Maggie, will Bob like me as a blonde?”
“Yes, Mary he will, I already asked, he wants what ever you would like.”
Not sure what came over me, I said, “Yes, lets go for it, make me sexy!”
After clipping and combing, coloring, washing, and drying, it was my turn to see my new look. I was blown away. This girl in front of me in the mirror was gorgeous, with super hair color, very pretty color shaped around my face to make my face so feminine! Soft, it just framed my face beautifully. I loved it, I told the girls.
Maggie hugged me saying, “Bob will love your new hairstyle too, so sweet looking. You are beautiful.”
I am not sure I heard Maggie say it was Bob’s idea, but then again he does seem to control my life nowadays. But I loved the look, and the blond color, so different, so sassy! I even thought, would Bob like it? Let’s get home and show him! I was shocked that I was thinking about what Bob would like. Those pills must really, really be working me.
“Mary isn’t this fun, a girls day out having fun spending your man’s money? Don’t you just love being a girlfriend?!” Maggie said.
Interesting she should say that, because I was feeling very good about be treated as a woman! Even in this uncomfortable all-in-one girdle, I was enjoying this feminine world.
We left the salon, heading home in the limo. Maggie never stopped talking all the way home. She was so excited with my new look she wanted to get home and skip the High Tea at the club. She was saying she was hoping Bob would be home by now so he can see his “new” girl’s look. “He will love your new hairstyle and color, plus your new figure with you all-in-one foundation.”
My whole demeanor was changing with this hairstyle, coloring, and my figure-changing foundation. I was feeling good and I walked a sassy feminine walk.
Maggie was saying that she wears her all-in-one girdle all the time because it gives her a great figure and it replaces three foundations -- her bra, girdle and garter belt. She tried to convince me to wear my all-in-on everyday. I was not sure of that, but I was on such a high I told her, sure!
She was so excited with my answer she hugged me, saying, “Mary you are the best, such a sweet girl. There aren’t many girls nowadays who wear the retro look and would go shopping with their boyfriend’s mother to buy these retro fashions”.
We got home and as expected, Bob loved my new hairstyle and color. He was even more excited that I had bonded with his mother all day.
Time flew by. It seems like Maggie and I did even more things together “for the girls” than with Bob. Maybe Bob planned it that way? Either way I was having fun. We were at the last day of Mom’s visit when I heard ambulance sirens outside my bedroom window. Sure enough, they were parked out front. Oh no, who got hurt?! I ran downstairs and saw the paramedics working on Maggie near the pool outside.
Luckily she was giggling, saying she fell by the pool, slipped, and thinks she broke her leg. The ambulance got her to the hospital. I rode with them, I was very concerned. I called Bob and he met us at the hospital.
The doctor said, “Yes, your mother broke her leg in two places. She will be fine but we will have to cast her full leg. She will need a lot of help getting around with a full leg cast. And she will need to stay the night here in the hospital.”
We stayed with her until late night and then told her we would return in the morning.
Back home I got Bob some dinner, and felt just like a wife, preparing his food and consoling him, saying all will be fine with his Mom. “Bob luckily you have a staff here that can help her while she recovers.”
He looked up at me with his big blue eyes. Something was wrong. “Mary,” he said. “My mom can’t leave our house for 6-8 week now. She needs to recover here with US.”
My head popped up, saying, “With us? Me here another 6-8 weeks”?
“Yes, Mary, you need to stay on and be my girlfriend another 6-8 weeks while she is here. Remember our agreement, you would be my girl while she is here? She needs you, I need you here. Please, please, please Mary!”
I didn’t let on to Bob, but I wanted to stay, I wanted to be Bob’s girlfriend. I was all excited about staying and helping Maggie out, about being Bob’s girl. I had no home to go back to anyhow. No job, no car, nothing.
I went over to Bob and said, “Honey, I would love to stay here with you and your mom. Whatever you need I will be here for you and her. I have bonded so much with you Bob, I really feel as though I AM your girlfriend. I hope you feel the same about me?”
Bob rose from his chair and hugged me like no other hug. He took his strong hands and caressed my face, bring me closer as he kissed me on the lips with such passion. I was putty in his warm soft hands. I loved it. He felt so right. I knew then we were in love, though not sure if boy to boy or boy to girl. Didn’t matter, I was on fire, and I knew this was right for me. I wanted to be his girl so bad.
The night was so right! He saw my new all-in-one girdle and couldn’t keep his hands off me. Caressing me felt so right, so nice. “Mary I love this new all-in-one girdle! I love the shape it gives you,” he said.
“Bob, your mother bought this for me at Saks on our girls’ day out, and she has the same girdle. She was so excited we were wearing matching girdles. Your Mom is so sweet”.
I did my nightly duties cleaning my face and such. Bob was waiting in bed all excited it seemed. I put on a very sexy short baby doll padded cupped nightgown. Brand new, he had never seen it before. With the little panties and my breasts supported in this retro nightie, Bob’s eyes were popping out. I could not believe I could get him that excited.
I got into bed and then the fireworks started. He cuddled me so softly, tenderly, and I was in heaven. We both got so excited; both our little guys were standing right up.
Bob brought out from under his pillow that magic glove my masseuse had used at the salon when I went there. I knew what I had to do. Bob’s eyes were asking and I knew I wanted to serve him.
The soft white glove fit my hand and he dripped warm oil on the glove. My hand felt so good as I was smiling, preparing him for our first night of lovemaking.
It did not take long to release his love juices and give him such pleasure. He planted another huge kiss on me with such passion.
He then held me and asked if he could satisfy me now? I gave him a kiss back, he knew I was ready. All he did was gently guide his manly hands over my little guy and I could not control myself, I was gone, released, done, such pleasure.
I felt so good. How could this feeling be coming over me? I love my new sensations, my new loving making. I thought I was going to cry with pleasure.
We both fell back on our pillows in such passion. Just then Bob rolled over and put his strong arms around me saying, “Mary, you are so wonderful, can you be my girl the rest of my life?”
I was so far gone, I could not control my thoughts and said, “I do love you Bob, I would love to be your girl forever”.
We slept the night in each other arms. It felt so right.
Early in the morning the sunshine was coming in our room. Our room looked like heaven, it was so beautiful. Bob was lying there as I stared at him in bed, thinking…. How did I get to be in love with my best friend? How can I love another man? All this is so strange but feels so right! How is this happening to me?
He woke up, seeing me staring at him. He reached over and pulled me closer and planted many soft kisses on me. I melted into his arms.
We were cuddling in bed when there was a knock at the door. Bob called in the maid as she said, “Mr. Smith, your Mother’s doctor called and she is not doing well at the hospital. She needs you to come to the hospital.”
We flew out of bed. I could not believe how fast I got dressed, remembering what Maggie said yesterday, “The all-in-one corset is all three foundations in one, so it’s very quick for getting dressed.”
She was right; I was dressed in the all-in-one girdle she’d bought me and a sun dress in 20 minutes, with hair and makeup. I was getting good at dressing. Even Bob complement me for getting ready so fast.
The limo took us to the hospital. All the way there I was holding his hand, telling him all will be ok. I looked at my hand inside his hand, thinking … look at me holding another man’s hand in such a loving way. How did I ever learn such nurturing, feminine ways?
Mom was sick; the doctor was not sure what it was. Bob was mad the hospital was not taking care of her better. I calmed him down, thinking that is just how a wife would help her husband. Maggie was in good spirits but the doctor said she would have to stay another night to make sure she is stable.
I told Bob he could go to work, he had an important business meeting today he’d said. I would stay with Mom the day to keep her company.
Bob gave me such a big hug as he whispered in my ear, “Mary, you are the best. I don’t know what I would do without you, sweetie. I will come home early, so get ready cutie!”
I felt wonderful as I saw Mom hold two thumbs up. She approved.
The day went by quickly. Mom never stopped talking. Close to the end of the day she said she was fine and wanted to go home. I thought no, no, no, I wanted another night alone with Bob. Luckily the doctor said no.
I got a call saying the limo driver was downstairs waiting to take me home.
As I was hugging Maggie goodbye, she whispered in my ear, “Mary I love you, you are the best for my son. Though I know you are really Paul Johnson!”
My jaw dropped with fear, I was speechless! Bob had told me if she finds out I am Paul she will write Bob out of her will and take all his money away from him.
“Paul, it’s ok. I still love you, you are BOTH in my will,” she giggled!
With a big smile I gave her another hug saying, “Mom you are the best, and I will love your son like no other girl ever has or could”.
“Mary, go, go make my son happy, see you tomorrow! Your little secret is my secret too!”
While in the limo, I was thinking I could not believe she knew I was Paul. She’d taken me to her club with her ladies. I wondered if those ladies knew too? She’d taken me girly shopping, shopping for lingerie. Maybe she’d suspected something was strange when she pulled my breasts up into that bra at the dress shop before slipping that dress over my head? And noticed my padding, and made that remark about her own padding? She felt so close to me then!
Clearly she was happy for me as Mary. I think she wants me to marry her son and have his babies, she’d said she wanted grandchildren. Wow, did I thinking that, care for his babies?
Bob called to say he would be late and that he would love to have a candlelight dinner by the pool. As he said “Goodbye love,” he added that I should wear something sexy. I must be turning into a real girl, because his voice got my little guy stiff, excited, and I think my little one even got a little wet.
I told him his wish was my command. This was so much fun, and all I had to do was tell the maid staff to prepare Bob’s favorite dinner by the pool…. How great is that?
I went upstairs and got all dolled up. I wore his favorite pointed retro bra and girdle set. Plus those expensive nylons with the seam up the back he’d bought me. They are so sexy, I thought.
I knew he likes big feminine bows on my dresses, maybe he would like a bow in my hair? I’ll wrap myself up as a present for just him. Did I think that? Wow!
I put on sexy long earrings, the reddest glossy lipstick. For some reason I love planting a kiss on his cheek and seeing MY red lipstick on his face. Like I have branded him my guy.
With this short short dress and the high heels I would wear I’d blow his mind! Looking in the mirror, I thought I saw my garters holding up my nylons. It seemed so sexy. The heels were hot red, really sexy. When Maggie bought them for me she’d said those heels would drive men crazy, Bob will jump your bones.
I looked in the mirror and she was right. I did look hot but I didn’t want just any man to jump my bones, as she said. Just Bob to jump me!
I was weak. I sat down at my makeup table, wondering how I’d gotten to this point, being such a beautiful girl? Then something hit me as I thought, Paul you love being a girl for Bob. You love the life you have here. You love all the sensations and emotions of being his girl. You are committed to Bob as his girl, even to being his wife if he asks. Wake up, you have no home, no money, no life. Being his girl is a dream come true, and you love him, even if you are a man.
I slapped myself and said, being Bob’s girl is right for me. Now go downstairs and make sure the maids have the pool-side candlelight dinner all set for my boyfriend, soon to be my husband, and make him a happy man!
Our candlelight dinner was all I dreamed it would be. Thinking these pills had really swung my emotions to the feminine side.
Before dinner we had a heart to heart talk as I said, “Your Mother knows I am Paul”.
“Mary, I know she knows. I leveled with her. I didn’t want any secrets. She is ok with our relationship as you can tell. You have really gotten her love! I hope you approve Mary!”
“Bob, I am so happy you and your Mom talked and she is all right with our new relationship. I do want to build on our love!”
I was all over Bob before and after dinner. We had both opened up to our love and desires for each other and I was in total bliss. I got so excited with him, I thought I was going to pass out. Bob came to my rescue and calmed me down in such a gentle, sweet way. I was so happy in his arms.
The next morning we were both off to pick up Mom. Listen to me referring to her as if she were my new mother-in-law!
As we walked into her hospital room hand in hand she said, “How sweet you two look. You both have a glow about your faces. You both look so happy. I love you both!”
With that, Mom’s endorsement, Bob hugged me and gave me the biggest kiss saying, “Yes, Mom she is a special girl, isn’t she?”
Mom had to go home in an ambulance, since she could only travel in a wheel chair. Her full leg cast was huge. As a good daughter-in-law, I thought, I rode with her in the ambulance.
With just the two of us in the ambulance I held Mom’s hands saying, “I love your son very much and I thank you for accepting me into your family. I hope to make you and your son proud of me, his new girlfriend.”
“Mary, you are so sweet, I hope Bob asks you to marry him real fast, don’t want to let such a sweet girl get away”.
Tears gave me such a happy face as I hugged Mom saying, “I am so happy too, I will do my best to make you and Bob my family too!”
Back home we settled in. Luckily, Bob had an elevator in his home. Mom was determined to move around in the motorized wheel chair he bought her.
She and I met out by the pool, and of course she wanted to know everything that went on to give me such a warm loving look on my face.
As if we were high school girls, I told her everything. It seemed so right, so much fun having a girlfriend to talk with, even though she might be my mother-in-law some day.
Maggie was so excited for me. She hugged me several times, telling me I will make the perfect wife for her son, if he ever asks me. I had thought she was against Bob getting into a relationship with another man, so I asked her about that. It turned out no, not at all. She was only concerned that Bob should marry the right ‘kind’ of woman. And whatever I was when I was born didn’t matter, I was now a woman. A fifties woman! “As for children, you can always adopt,” she said. “The main thing is to be happy!”
I was. And I’m sure Bob was. As the days passed we were all one happy family. I loved helping Bob’s Mom and I really loved being Bob’s girl.
Then one morning I woke up with a rash on my chest around my fake breasts, and it hurt. Bob loves my breasts and always stares at them any chance he has. He saw the rash and my pain.
He commented that the glue was probably affecting my skin, maybe irritating it. “Mary, I will make an appointment with your doctor and she can help you today. I don’t want anything to affect your girly boobies, right sweetie?!”
I just smiled, saying it hurts.
“Bob how can you get an appointment so fast with her”, I asked.
“Mary, I have connections. I will take care of you sweetie.”
No sooner did Bob hang up the phone than he said, “Mary, we have an appointment in one hour. Go get ready, I will go with you”.
I said, “Great, but you don’t have to go with me, I am a big girl.”
“Sweetie, I want to go with you and if you are a good girl maybe we will go shopping after your appointment.”
I feel so warm every time I hear Bob taking care of me and my personal needs. He is so sweet.
As we approached the hospital, the limo driver circled under into an underground parking garage and we went inside. I looked at Bob and said, “Is this the same place Sally brought me for my breasts?”
“Mary this is a back entrance. I like this entrance better, it’s raining and I know you don’t want to get your pretty hair wet.”
He is so sweet always thinking of me!
We got up to the third floor and we ran into Sally. I was shocked to see her here, and happy too. We gave each other huge hugs. I whispered in her ear, “I think Bob and I are going to get married”.
She was so excited, giving me another hug, saying that was so great, congratulations!
“But Sally, what are you doing here? I thought you left town.”
“Mary, I left your house, not town. Never said I was leaving town. I work here, I am the Head Master here.”
I was blown away… she runs this place?
“Mary your doctor is waiting, I will connect with you later and explain everything”, she said giggling. “Now that your getting married”.
The doctor was so nice. She said what Bob thought, the glue was irritating my chest. She removed my fake boobs and applied some medicine. Wow, not having breasts on my chest, no weight there, was really strange. I’d gotten so used to the weight, the mountains as I’d first called them, now it felt equally strange not having any weight at all on my chest. I did not like it.
She said I would have to let the ointment work to calm down my skin rash.
I got all nervous saying, “I need breasts on my chest, how long will it take before I can put my breasts back on?”
“Well, Mary, it could be couple of days. I could use tape and tape your breasts so that the tape does not go near your rash. Maybe makeup could hide the tape, but I am not sure. You know Mary if this medicine does not work, you might have to have breast implants if you want breasts that badly”.
Fear stuck my face and said, “I want breasts, I need breasts. If implants are my only option, then I need the operation”.
Listen to me, no I am begging for boobies on my chest. Wow listen to me, begging for breasts.
I turned around and Bob was standing right here. He’d heard my whole plea for breasts.
“Mary don’t worry your pretty head. If you want implants you shall have implants. Your wish is my command, sweetie.”
I was so excited I hugged Bob.
“Doctor, I can’t walk out of here with no breasts, so lets tape them on me now and schedule implants for as soon as you can”.
“Ok Mary, we can give you beautiful breast implants next week Tuesday”.
I thought to myself, wow that is quick. I didn’t think they could do it that fast. Am I ready for an operation to really make me a girl? Can I do this? I did want to have real breasts. I looked at Bob, his big smile told me of his approval, his desire for me to have big real breasts. I knew I wanted to be Bob’s girl and he is obviously a breast man.
“Ok, I will do it, lets schedule the operation.”
Bob hugged me saying, “That’s my girl, you will look so beautiful, your figure will be so feminine, so girly.”
The doc taped my “old” breasts on my chest, I got dressed and we left all happy. I told the doc I would be back for the real ones! I had just signed my old life away but I was excited about my new life.
Sally was waiting for us, and said, “Mary lets get some lunch and you bring me up to date on your new life.” I loved having private girly talks with her. Girly talks with her seemed so right.
Bob went off to meeting in the building downstairs not before giving me a huge kiss, right in front of the hospital staff. If the staff didn’t know we were lovers, they knew now… the deal was sealed.
I was blown away when Sally took me back to her office on the top floor. She had her own dining room overlooking the city. Wow!
“Mary, I am so pleased you and Bob have “hooked up.” I guess I taught you well for your new life. I am so proud of you and I know you made the right choice. Bob is a wonderful man and you will make a wonderful wife”.
When I heard her say all those nice words, I started to tear up. My head was spinning.
“Sally, how did all this happen? Are all the people here boys trained to be women? This hospital seems to be only for women, and everyone here seems to know Bob.”
“Mary, this is more than a hospital. This is a special hospital, a special place that helps people. We are named after Bob’s grandmother, Margaret… the Margaret Institute.” As Sally reached to hold my hands, she said, “We help boys and men become girls or woman”.
I pulled my hands away from hers in shock and covered my face. What did she say? You change men into women? Is that what they have done to me?
“Mary look at me, what are you thinking? We don’t force any boy to be a girl. It is their choice. We help boys or men develop their own feminine demeanor and they accepted their change on your own”.
“Did Bob hire you to change me”?
“No, Bob asked me to show you YOUR feminine side. You are the one who accepted Bob’s deal to help his Mom think Bob had a girlfriend. You asked for help to become the most feminine girl possible, remember? You asked!”
I sat there thinking she was right. I had accepted all this, and Bob had just helped me. I am the one who wants to be Bob’s wife, to dress in all these feminine clothes, to be his girl! Wow, Sally is good!
“Mary I hope you are all right with all this. It will take time to sink in. But it’s all your choice. Bob has just offered you the opportunity to live a much happier life, one that I think you will like and love. I think you and Bob want this beautiful life.”
“Sally you are right, I do want this new life. It has been with your help and Bob’s that I have realized deep down I have a very strong feminine spirit, and maybe have always been a girl deep down in my brain. I should be thanking you for helping me bring out my femininity, and my love for Bob.”
We hugged as I told her I was ready for my new life.
At lunch Sally blew me away again, telling me that Bob and his mother own this Institute, that the maids in Bob’s two homes are from this school, and that he has “graduated” hundreds of boy/men into womanhood.
“Wow, who would have ever thought there would be a place that would help men become women? Thinking about the maids back home, I realized that they were perfect girls, so kind and gentle, shapely curvy women… and they are men or were.
“Sally why do Bob and his Mother like the retro fashion look? Why does he like these pointed bras and girly girdles so much?”
“Mary, I am not sure. Back in the 50’s women were different. As Bob says they were real women then, true to their calling. He always says a girls figure is her biggest asset and the shapelier a woman is the more appealing she is. He just likes shapely women and the retro fashions do just that, give you a very very curvy attractive figure”.
“Well at first I had a hard time with these mountains on my chest, my pointed breasts.”
“I know Mary, you told me many times. But I helped you learn that curves were important for your training, and of course those pills helped you adjust to your pretty figure. In fact, they’ve helped round you out in some ways without you even noticing! They’ve helped you take things as they come and enjoy them!”
“Well, now I love the retro look. I know Bob does, and I like pleasing him, but I would still wear this look even without his help now”.
“Mary you are so ready, you have learned so well what makes a man excited. And your demeanor, your 1950’s thinking, will help please your man. Trust me, he’s a puppy dog if you treat him right.”
“Mary I see you are still wearing his diamond ring, how sweet!”
“Sally I now feel very attached to his beautiful ring Bob gave me, I can’t take it off ”, I said.
“Sally do you think this Institute could help me become a ‘better’ girl for Bob?”
“Oh Mary, we most certainly can. I was hoping you would ask. I have to tell you once we start your treatments there is no turning back. Our treatments work quickly and are very permanent. Our new girls want it that way! Sign these papers and we can start now”.
“Sally what are your treatments?”
“Mary your first treatment is your weekly shots. We have developed a medicine that will not only help your body create a very feminine figure, but also your mind will think and guide you into more feminine ways. Your demeanor will be so sweet so feminine you will hardly remember being a man when we are done with you. Acting and living, as a woman will be the ONLY life you will know and you will so enjoy femininity with your man. Much like Bob’s maids at home, they are wonderful woman now, well trained, very accepting of their feminine ways”.
I was shaking as I signed the papers. I felt so good knowing my fate with Bob and womanhood would be sealed.
“Sally can I come to your school every day to learn more feminine ways?”
“Mary, of course you can. I know Bob will be very excited that you want to learn more and we at the Institute can teach you so much more”.
“What will I learn, look at me I look so good now, you taught me already?”
“Mary there is so much more, feminine hygiene, figure development, hair and makeup styling, a more girly attitude, how to love your man, shopping for all your feminine needs, living in the ladies world, so so much more we can help you with. We have been doing this for over 30 years, we are good as you have seen Bob’s maids and girls around here at our Institute. When we are done with you will not even remember you were a once a man.”
I got so excited I hugged Sally again.
“Mary lets surprise Bob and ask him to come upstairs here while we start your first shot now. I think the two of you should ‘pull the trigger together’.
“Sally what are you going to do today to me?”
“We will give you your first shot of estrogen. The estrogen will change your body and mind and make you the most feminine girl ever. You won’t have to take those pills anymore. I think Bob would love to give you your first girly shot, don’t you?”
I got all excited hearing how Sally can help me become more the girly girly I so wanted to be for Bob. Plus Bob could ‘seal the deal’ again by giving me my first permanent girly shot.
I hugged Sally with tears in my eyes saying how excited I was.
Sally grabbed my two hands asking, “Mary when do you think Bob will ask you to marry him?”
I got all red in the face, saying, “Sally, I am so excited, he says he wants to take me to the cottage, the ocean house, and have a weekend alone with me. I am hoping he’ll ask me then. I am so ready. I do so want to be his wife! I would love to be his ‘Stepford’ wife!”
“Mary you will make such a beautiful bride inside and out, a perfect 50’s wife for Bob. He is so lucky to have you! Have a wonderful life girlfriend!”
THE END and the beginning of my new life!
If you liked this post, you can leave a comment and/or a kudo!
Click the Good Story! button above to leave the author a kudo:
And please, remember to comment, too! Thanks.