(This is an different story for me, but one that underlies those who waited for others to give them direction or make decisions for them. Hopefully in time each of us accepts who we are and learns to live with oneself.)
Bob was fairly good looking, but between having fine features, shyness and being a little socially awkward, keeping relationships did not come easy. So when Nora his latest interest said yes to a proposal; Bob was quite happy and Nora was indeed the love of his life. He had one thing he had not shared, but decided instead of sharing to make it a concern of the past.
Nora loved Bob, especially his sensitivity; liking that he wasn’t quite like other guys she had dated. This would work with her plans. She learned he liked her wearing soft silky things; it seemed to be a turn on. She was due for another fitting of her wedding gown, and invited Bob, not her maid of honor, to go with her. There was more than a tinge on interest on his part, but what he felt he didn’t think he could share.
The Bridal shop did most of their bridal gowns by special requests for well to do customers. It took them over an hour and half to travel to the bridal salon. After a short wait Nora was taken back and for another another hour and a half as she was refitted for her wedding gown alterations.
After they were all done, Bob was invited back. While Bob tried to be subtle about his interests everyone was watching and encouraging him to look, touch and enjoy this feminine sanctuary. He thought their smiles had to do with appreciating their work. All but the designer and one helper had left, when he was told Nora wanted him measured for a fitting. He told them he had already selected where he was getting his tux and the style he wanted.
They laughed and shared you need to get use to pleasing your bride. Nora too laughed. The head woman asked him to strip down and gave him a thong like panty to put on, “If you would please stuff yourself in that little pocket it will help.” His embarrassment was growing, but she patted my on the ass and shared, “We’ve seen grown men before.” He had undressed and placed on the thong as she suggested, but was delaying coming out. “My young lady,” she said as she opened the door and took his hand, “don’t be shy and take too much time. I am doing this as a favor, and though it tickles my fancy, there is nothing in it unless there would be a sale.”
“Yes, you are in a dress shop and I am sorry to offend you but we women are seen as part of mankind in society and one of the guys all of the time. Now, let’s get you measured young lady. Did you ever think you would wear satin so pretty and fine? GO ahead and touch it, you might as well enjoy it.” She brought my hand to it and had me touch and acknowledge how nice it felt. “You can keep it for some time when you two are alone.” She took more measurements than had ever been taken of me before.
“Here put this panty on over the other.” Bob started to complain, but was interrupted. “Nora is this, what you would like or not?” Nora indicated yes and he gave in. “Very pretty, now sit down and let Michele put on your leggings.” They were stockings that snapped to straps connecting the new panty. “Now back up and close your eyes for Nora’s surprise. Raise you arms and let me hold one so you won’t lose your balance. Now step in here, nice and now the other leg. Good we will pull it up and fasten it but keep your eyes clothes. One more touch and the look will be almost complete.” Bob wasn’t sure what he was stepping into but it felt eloquent. Now a hair piece was being put on. Nora had wanted me to let my hair grow longer for the wedding but a hair piece was needed to see how it would look in three months. “Well before you open your eyes tell me how does it feel?”
“Apart from the hair piece it feels very nice, but Nora I’m afraid it isn’t very manly.”
“You are right about that, now open your eyes.”
He couldn’t believe it, he was in a bridesmaid gown, how could he have dressed in all of this and not realized it, and said as much to Nora and the women. “Brenda dear, have you not always wanted to do something like this?”
“Brenda. Why Brenda and what do you mean? This isn’t even one of the gowns for our wedding.”
Nora said, “I was told if it was true; you wouldn’t deny it but ask other questions and sidetrack the conversation”
“What do you mean?”
“Well, if you didn’t want to be a girl, you would be very angry and I would probably now owe for a spoiled gown. But instead you have been feeling how nice the gown really is and I am happy for you.”
Bess had him raised each foot and he was now in heels. “Come here young lady and we will complete the look. He was seated on a stool and a small sheet draped around my neck and shoulders. Make-up was being applied and the wig was being combed out. It took another half hour to do his face. “No, please not earrings, please.” Again the words fell on deaf ears, but he could not deny cooperating.
“Mary, undo the back of her gown for a moment.” She did, and at the same time Bess pulled out the top and put in… No it can’t be, but it was. The gown was again done up.
She pulled off the sheet and there in front of me in a long mirror was the young woman they had just dressed and made-up. “My Nora, you were right there is a beautiful young lady there, and I just hope you do not mind how nice she looks.”
“I am sorry Brenda, but I saw you twirl with one of my dresses and I know you have been into my clothes. I had to do this or you would run away and deny it… I don’t want to lose you but neither do I want to live a lie.”
Mary took him over to a table and chairs and started to do his nails, when he started to pull away. “Don’t worry, just relax we have just the color to go with your lips.” She filed, buffed his fingers and then started with a bright deep cranberry red. Gone for the moment was any sign of Bob. Nora spoke up, “I will tell you the truth, I am not fully comfortable with you as a woman, but you are very pretty and I cannot deny seeing a beautiful girl who looks very happy.” She gave him a small kiss on the cheek. She touched his cheek, it was tender very tender and loving.
“Nora, I am sorry.” He said with a voice voluntarily raised a little in pitch.
“Would you mind wearing another outfit for our trip home?”
Bess led him back to the changing room with a warm smile on her face. “You are a lucky person to have someone so caring. Please, I encourage you to take some time to find the person she uncovered.”
She gave him a long skirt, a blouse and sweater top as she opened the door. She undid the back of the gown and pulled it over his head. He said, “I can’t.” But after the door closed he realized they were not leaving me many options. His clothes were missing and instead of returning them he was given a needed bra and slip.
When he changed and stepped out Nora handed him a purse. He asked why I needed it. She said, “Your wallet, keys and make-up are in there.” Nora showed him a check for just under a thousand dollars as she handed him a gown to take to the car. She was going to drive home, as he was having trouble just getting into the car. “I suggest you sit down first and swing your legs in next.” While he did not feel very graceful, it did work. Bess closed the door for him, as she said good-bye.
They had traveled about fifty minutes, when Nora signaled for a left turn. When he asked why, she smiled and shared, “We need to eat, and I thought you would rather do it here instead of closer to home.”
He shared, "There's was no way I'm leaving this car."
“I am sorry,” she said, “but if I can go this far; you won’t embarrass me by staying out in the car.” She came around, opened the door and helped him to my feet. “Here, you almost forgot your purse.” He was surprised as no one gave them a second look going in or when they were seated. “Have a good meal, ladies.”
“Yes, I know all they see are women; should I correct them? I suggest you raise your pitch just a little and speak softly.” The crab, vegetable and salad I ordered were different for me. “So are we watching our figure?” He hoped if a stare could burn she would stop, but it only made her conversation a bit more humorous.
He was glad as they were near the end of their meal and could soon be leaving. When the waiter asked if there was anything more, she asked him, “Could you bring an after dinner drink while we went to freshen up.” It was not a suggestion, but a request for Bob, Brenda, to get up and go with her. She reminded him, “You will need to be seated and back together before you can come out to the mirror. He was surprised how easy things went. Tucking himself back into the gaff took an effort but was done easily enough. After washing and drying his hands he touched up his make-up and lipstick without thought, much to the joy of Nora. “Let me fix your hair if you don’t mind. Otherwise you are quite the lady.”
When they got back to the table two Grasshoppers were there and they were a nice change and a good end to the meal. When the check came she pushed it to me. “What should I do, I would have to sign it Bob or Robert?”
“You have at least three face saving possibilities, choose one and be a good girl about it. That does include leaving a nice tip.” While they were waiting for it to be brought back, two men approached their table for a dance. “I wouldn’t mind,” shared Nora, “but I would have to warn you my friend is very shy and may be a little awkward until she relaxes.”
“I will take the risk, if you don’t mind,” as one offered his hand. Nora leaned in and whispered, “Your face looks good but don’t rub it next to him.” They had about three dances when Nora tapped me and shared we had to leave. John dared to lean and give him a goodnight kiss which he returned. John gave Brenda a piece of paper, saying, “We would like to see you two again.” He suggested the following Friday for dinner and dancing. They picked up their purses and were leaving as Nora shared “I so hoped it would be fun.”
He was not sure if he sat down properly or not, he only remembered he was in the seat and wondering what all happened. “My, were you a little forward tonight. I don’t remember any kiss on the first night.”
“He kissed me what was I to do?”
“A nice girl, reserved like you should only give a cheek to be kissed if not disappointed him.”
“What was the statement I hope, it would be fun?”
“He suggested we come back next week and they would host us for dinner?”
“And so you thought that would be nice?”
“Well yes, I thought it might be the only time someone bought Brenda a dinner. It would be the first time, wouldn’t it? And I thought if you knew enough to shave you could get a little closer.”
“Nora that is not funny and we are engaged anyway.”
“So you are, and you’re a guy as well. Neither stopped you from looking like a woman, dancing with a guy and giving him a goodnight kiss.” They were on the road as he began to cry. “Brenda, I didn’t mean to hurt your feelings. Do you always get a little more sensitive when dressed like that?” She changed her tone and they were quickly caught up in a conversation. Before long they were home and carrying his gown into his condo. “I hope no one saw us.”
“Well if they did they saw two women carrying a gown in and I was the only one quite recognizable. Let me help you out of some of your clothes and then we can have some more fun.”
He began to take things off and threw them wherever, but Nora stopped him. “If you want to dress as a girl, you should treat those clothes like a girl. She gave him a lesson in hanging and putting things away. Then took him in the bathroom and showed him how to remove his make-up. She took out two pins for the wig and took it off and found a nice vase to put it over.
“Hold up the gown and dance with it.” He hesitated but gave in when he was certain not to win. He sat down to take of his stockings and things but Nora pounced on him. “You are my little miss, right now so let’s enjoy.” When he protested he had gone far enough, she replied, “If you don’t want to be my bitch, I suggest you be nice.” She had smoothly slid over him and she wooed at him and purred in his ear as she nibbled. “You are hot young lady. I am going to enjoy you. Grrr…” Her hands were now under my panties, pulling him up against her, as she went into a rhythmic motion. She played with him for the longest while, and then she was straddling him and taking him inside. She paced it so both climaxed at the same time. He never remembered it feeling so good. He was nuzzling her neck when she coaxed me down to her breasts and after her next orgasm, pushed him down between her legs. “Oouu Brenda that is so nice.” As her next orgasm was coming she held him firmly in on her. He relaxed and enjoyed pleasing her. He couldn’t remember what all happened or how long it went on but he knew he fell to sleep joyfully as did she.
They did have fun.
When they woke up it was Saturday morning when the doorbell rang. Nora said, “Hurry up put on my robe and come out.” He heard her saying, “Yes, it was like I suspected and I want to thank you for suggesting what we did.”
“Leann, Nora, why didn’t you tell me?”
“Relax Brenda, I thought you weren’t going to say anything. You are in stockings and my robe, what should I say?”
Leann spoke, “I must say however, you look different but I see potential.” He headed back to the room but was cut-off by Nora. Nora went and got the wig and placed it properly on him. They all sat and talked over coffee. They were all surprised how normal the conversation flowed.
“So can I go with you next week,” Leann asked?
He tried to share there would be not next week, no next time. Instead he found himself getting dressed as Brenda to shop for clothes. They made him up really well and had fun taking him shopping. He had to try on at least three items as they shopped through five stores. He paid for the first three skirts and tops, but Nora bought my panties, bras and lingerie. He didn’t realize all that extras that extras could include or costs, but was finding out.
When they we back at his home tried sharing all the girl clothes would ruin their wedding budget she hushed his part of the conversation. He was sent to sort, put away his clothes and then shower.
Leann spoke up “You should have let me shower as you two have me all hot and moist.”
Jokingly Nora shared, “You can go and jump him if that is what you really want.” Bob was already in his room sorting and putting things away.
“Can I do what I really want?” Bob was venturing back to ask about hanging something up, when he overheard them, he just stopped out of sight to listen.
“You can’t have him or her.”
“How about having you? I got a bit hot, here feel me?” She took Nora’s hand and slipped it down her panties. Nora looked up as LeAnn gently kissed her. Nora brought her hand out of LeAnn’s panties but ended up putting them around her. The gentle kiss went deep and long. “What if Bob finishes his shower and discovers us?”
“Shush we have time.” He watched for awhile before he went and took his shower. When he got out and dressed there was a note, they had gone to LeAnn’s.
“When Nora came over the next day, he shared he had seen them. “We know we just wanted you to know how it feels.”
“Why should I know how it feels, knowing you two made out?”
The week passed and things seemed to be back to normal. He got off Friday a few hours early, but found a note to shave and get dressed. She had placed a nice skirt and blouse outfit out, which he hoped was for her. He was in the shower when she came in and asked if I was shaving.
She turned off the shower, checked him and told him to coat his legs and arms with this gel. He now remembered the outfit was one they bought last Saturday. She checked to make sure he had gotten all the hair. “Oouu you feel nice. Scoot, there are a few areas I need to get with a razor.” She did his underarms and a few other areas he missed. She took care of the hair on the sides near his ears, which caused me to wonder about the previous time out.
“Put your gaff on before your panties?
“Why can’t I just wear that as my panty?”
“Because we don’t want to make it too easy for him to realize you want..,” she laughed.
When he suggested it wouldn’t mind if he was easy. She laughed and said “You might eat your words” and as she laughed some more. He was still clueless of why it was so funny. She had me lay back as she glued his faux breasts on this time and used a toner to work and cover the seam. “You are going to look hot tonight. I hope you will relax and enjoy yourself.”
She now showered and was getting herself ready. She definitely looked better than him, but not as special as she might. When he spoke up she shared, “You can enjoy me later. I didn’t need to please our dates.” When he suggested he didn’t either she asked if he wanted John to see him as a guy or as a woman. And suggested it would be easier to please him as his girl. He wondered, ‘How come I am always on the short end of these exchanges?’ She gave him a light touch of perfume and told him to touch the lobes of his ears. She gave him a nice dangling pair of earrings. Then suggested he make sure he had all he wanted in his purse.
She started the car but wanted him to drive tonight and so he did. “How’s driving with heels, love?”
“Just a small bit more difficult than walking in them.”
“Driving is like walking, the practice helps you to get better. I must say, the practice dressing like a girl is not hurting you either. May I suggest we take off next week from going out with these guys?” He was not sure to answer so he kept quiet. “How do you like your experience dating guys and being out as a woman?... How long have you been doing this, anyway? Does your mother know?”
“Are you going to just ask questions? Tonight wasn’t my idea remember.”
“Well from the looks of it you came up with the idea long before me. Now, are you enjoying it?”
“Nora, I am surprised how well you have me looking. I had decided not to do it again ever since we became engaged.”
“I agree you are looking very good, I just helped. It looks like your decision didn’t hold, did it? Brenda will you please enjoy tonight, promise me you will, Brenda?”
He hesitated but knew it was important somehow to Nora, “I will.”
“Okay here we are, 100% girl. Enjoy yourself and shake a little booty,” With that he couldn’t help but get out and put a little swing to his steps. John and Steve saw them coming and came as gentlemen to help them. John gave Brenda a small kiss that landed on her ear. ‘Why did I like it, and that my hand was small and feminine in his?’
John asked and so Brenda let him order. They had a light red wine with their salad. John order lobster tail and stir fried vegetables over rice for Brenda. Something she would not have ordered or had ever before eaten. When Brenda grabbed for the wrong utensil John nicely showed her which to use. He took a small fork full, dipped it in butter and fed it to me. Wow, I was in girl mode and surprisingly enjoying it. My hand was on his and it felt good. I looked to Nora and she winked. “It’s nice isn’t it?”
“O yes it tastes very good?”
“I didn’t mean the lobster silly; I meant being pampered by a man. You seem to enjoy it, I am glad.”
John spoke up “If you don’t like me doing that…”
“No that is very sweet and I liked it more than…” Brenda leaned over and gave him a small kiss. She was blushing as she went back to eating. The conversation was light and she began talking more with Steve and Nora as well as with John. She scooted closer to John, supposedly for a better conversation, but Nora was a little jealous.
Steve spoke up and Nora was back to talking with him and did not notice when the John took Brenda to dance. When they came back Nora suggested they go to the women’s room. We had to wash before we used the toilet as well as after because of the butter and lobster. Brenda checked and fixed her make-up. “You should use your lip-gloss; you have very pretty lips,” another woman shared. I told her thanks, checked my purse and gave it a try. She was right that it looked very nice.
John seemed to notice and approved of my appearance when we got back. He led us to the dance floor and we enjoyed ourselves as the time flew by. We would sit and visit and dance a little more. I lost track of Nora and found myself being excited by John. He asked if we could walk and so we stepped outside. He was coming on stronger, and while I tried not to encourage him. I did like his kisses and attention. He turned to me gave me a warm kiss and his hands were on by ass pulling me closer. I pulled back, “I am sorry but I can’t.” He took me by the hand and we walked. He calmly asked, “Do you mean you do not want me or you can’t?”
Brenda with tears in her eyes, “I am surprised to say, I would love to have you but I just can’t.” We walked back in and my eyes were tearing. Nora took me aside and asked what the matter was. We went to the bar for a moment to talk alone. As Brenda, I confessed how good I felt as a girl and that John came on to me. “But I shared with him I couldn’t and we came back in. I’m sorry Nora, we need to leave.”
“Need to leave because you don’t trust yourself?” Brenda looked up into Nora’s eyes and she knew. “Remember last week when you saw LeAnn and me, and I said there will come a time? Young lady, from what Steve has said John is bisexual and he likes you very much. Steve says he doesn’t love lightly.”
“But, Nora how about you and me, I can't just do that.”
“I think it is something Brenda has wanted, and until you take him or another guy, it is likely to be a matter of time. I plan to love you tomorrow and the days after that. But I have already wrestled with this and to be truthful, I am happy for Brenda.”
“But I am scared.”
“You are a girl doing it for her first time, I suspect not only are you a little scared to do it, you are also a little scared it might not happen." She handed me a handkerchief and smiled. “Let’s go to the girl’s room and powder up.” Brenda squeezed her hand and went with her. I was being brave until I saw Nora was a little scared for her as well. “Take me a minute or two and he may be gone or he may still be there. We will live with it either way.”
“Thanks Nora, you are really sweet.”
I had to redo my makeup so it wasn’t a problem, it took me a couple of minutes. When I went out he was standing to receive me. He took me to the dance floor and now hugged me so I could feel the warmth of his love. When we sat down again, John discretely put his hand on my leg, and I parted them ever so discretely. It felt good to feel the warmth of his hand. Brenda had dreamt about it, but was not sure if she would like it.
Nora and Steve were back from their dance and Nora shared she was going back to her apartment alone. But she hoped Brenda would have a good evening. I was now heating up thinking of John going into me. I wanted to say ‘no’ and get up and go with Nora, but I wanted him even more.
Nora felt a need to be her big sister and took me back to the bar for a quiet discussion. It was mostly Brenda listening as she talked. “Remember while you have a boy’s body, you are a girl tonight. Keep your gaff on. Don’t be afraid to ask him to be gentle as he can. He probably is a big boy, try to enjoy him. Don’t be surprised if it hurts a little or you have an orgasm without responding like a guy.” Clean yourself, if he comes in your mouth. You should suck him clean and enjoy it. After he has been in you clean yourself, but what you do from there is your own business.” Neither of us could believe we were having this conversation. “The spare bedroom is made up for you, you are not to use our room?”
“Nora, were you planning this?”
“No, but whether it was tonight or another night I want for Brenda to experience it so you can move on. Don’t worry; my plan is to get in you, myself. I enjoyed last week.” We walked back and she gave me a parting kiss on the cheek.
Steve excused himself as well. John put an order in for a bottle of champagne to go and we went out to dance once more. It was only 12:30 when they got back to my place. John opened the champagne for a toast, “To a girl’s first love.” His hand was on my leg and he soon had me hot. With the second glass, Brenda got up and to turn down the bed and to change into a nice negligee. I could not believe, I just went over to him and straddled him. I was ready for hot and sassy love. Really Brenda and Bob and both wanted him.
I undid his shirt and his pants. I felt him before when we were dancing, but it was now that I realized how big he was. Nice and thick and long, my butt was reeling in anticipation. It was a few moments before I slid off his legs and between the sheets. As I pulled him out he grew in my hand. As my lips descended on the head of his cock, he started to become hard and harder. I kissed and licked him. It was neither dirty nor gross; it felt warm, soft as well as hard and somehow inviting. He was talking to me, more as an expression of caring than saying anything in particular.
He noticed I was trying to see how much of him I could handle. I heard him suggest breathing through my nose. I did but at first I still gagged. Hear him saying it was not important, but we were both impressed when I tried again and took him in deeper. I came back up to catch my breath and I liked his smile. Once again I started on with some fun as I caressed him; all the while I was trying to relax. I was taking him in again; I passed the desire to gag.
I could feel him in my throat, but I could also see I still did not have all of him me. I was taking him deeper and the throbbing of his cock was getting both of us excited. I was at the base of his cock and I needed to come back up.
He took me in his arms and carried me to the bed. “It should be easier and more enjoyable here.” He was right I was able to move my body and position myself. He said I didn’t need to. “But do you like it,” I asked? I was taking him in again, slowly taking in a little more and more. I was now all the way to the base and we were both moving up and down the shaft. He grew even a little thicker, breathing was a bit harder but the rush took over, I could feel my desire wanting his cum. His cock was throbbing and I went back up a little ways as he was cumming, it was hot and thick. I was seeking to swallow as well as breathe. I had him in my mouth and my mouth was filling faster than I could swallow.
No, I could have swallowed faster but I want to enjoy it. It was oozing down his shaft, but I would get that. He was still throbbing and he was still coming as I first lifted my mouth. But I was back enjoying him. He finished as I continued to lick and to clean him up. I excused myself and went and gargled. I knew he would appreciate that. We kissed and rolled around a little but then he was ready again. We took more time to play as he said he wanted to treat me as well. He finger my anal opening and put an oil or gel on it. He had me lubricate his cock.
He found hmy opening and guided the head of his cock but he needed to push to even get his head in me. He kissed my eyelids and said “You will be fine, just focus on your joy. Do you want me?” I hugged and moved to receive him. It was hard but my legs were wrapping around him. “Oh, oh.” My joy was beginning as he was moving inside. Stretching yes, but the joy was rising. He was pretty far in when he started to pull out and push in. We were soon both pumping in rhythm, I couldn’t feel my own penis respond, but I was feeling something greater building. I was moaning but it was all pleasure and I orgasmed first and my body was rejoicing as he burst inside of me. It was warm and we both were kissing the other hot and heavy.
We lay there, enjoying the company of the other. He had rolled off of me. It was an hour when I got up and cleaned myself off again in the bathroom. I brought a warm washcloth and washed him off this time. He asked if I wanted to go to sleep, I shook my head and smiled.
He was again between my legs and I needed to relax again. It stung a little bit even he could tell. “You have probably torn a little bit. You'll feel better.” He was entering me and we continued to enjoyed our time. He took his time and I had an orgasm, and he whispered love in my ears. He was now building, but so was I, he quickened his motion and was pushing harder and deeper until he came again and I held him in as tight as I could hoping it to last as long as possible. When he came out, he got up and washed himself and came back with a cloth to clean me. He was gentle and caring.
It hit Brenda. ‘I’m a man being made love to by another man. I shouldn’t like it, like I do.” We caressed, rolled in bed, chatted until I finally fell to sleep. It was 8:30 or so when we woke and he did me once more. When I went into the shower he soon joined me and we washed each other. I came in his hand and was like a giddy girl. I got out before he could rear-end me.
I was dry and walking away, when he lubed my butt and I closed my eyes in joyful anticipation of him entering me again. Something was happening and I opened my eyes to see. Nora had come in and there i was as Brenda in the door way with John. My heart began to sink, but Nora wasn’t repulsed or mad. Nora said, “And I was thinking I wasn’t going to get to see Brenda in action.”
“I’m sorry Nora; I didn’t think you would be over so soon.”
“Well neither did I, and I thought if you were here, you would still be in bed and I could get what I needed and out without disturbing you. I am sorry, kind of.”
“What do you mean kind of?”
“Well you got to see me with LeAnn, part of me wouldn’t mind peeking and seeing you two together. The smile on your face showed joy, I am glad, I just wish I got to see you two more together.”
John, “You came a moment too soon; I was just going to try to make her smile bigger.”
“Don’t let me stop you, but I hope you wouldn’t mind my peeking?” John turned Brenda around and lifted her in a warm hug.
“Would you like to swallow me or me in you?”
“I wouldn’t mind seeing both,” Nora broke in.
“Yes, I know you would like your silky gaff back on. Put it on, you might want your negligee on as well. You can close the door a little but please not all the way.”
John took Brenda by the hand. “John, I don’t know if I can?”
“It is not like you need to get aroused, and we can take some time snuggling up and kissing.” I put on the gaff and got out a clean negligee and put it on. The mood was turning warm again. I thought it would be hard, but for some reason I began to concentrate on John and liked the thought of him becoming aroused. He was big as I took his head; I was enjoying myself even more. He was fully in my mouth and I was taking him deeper. I began to gag but drew back. Now I was swallowing him again and enjoying as I went further.
I thought I heard Nora gasp as I took him deep down my throat. Now I was moving him in and out and bringing him into rhythm. His cock was throbbing and we were taking our time as I eased up on him twice. He was getting closer as I went into an orgasm. From Nora’s delight, she recognized what was happening.
John was now bursting in me as I was swallowing and drawing back. He was cuming hot and furious. I was enjoying him but feeling bad about enjoying him so much. I had to make a big swallow as he was still cuming and my mouth was full. I sucked him again and again, and then cleaned his shaft. He pulled me up to rest on his shoulder.
I didn’t want him too but he was kissing me and sharing his own cum. He was playing and arousing my feelings. Time passed quickly as I felt him lube my butt. He rolled me onto my back and was between my legs. I lifted up my butt to receive him. Again I heard a muffled gasp from Nora as she saw his size getting ready to enter me. His pushing his head in me caused my eyes to water. He asked if he should stop. I reached around his neck and raised my head to kiss him, “Speak nice to me.”
He was well up within me as we began pumping. It felt good and I was again going into an orgasm as he took his time. But now he was building, getting faster and pounding my butt hard and deep. He was not as gentle but I was enjoying him as he burst inside of me and kept pumping.
His gush of sperm was great and hot I could feel it fill butt. He was kissing me as he pulled himself out. He rolled off and drew me too him. TWe were lying there and I was not sure what to do with Nora watching, but Nora broke the ice. She came over and hugged us saying, “This has to be unorthodox, but I swear I don’t know when I enjoyed something so much. I am proud to be your fiancé young lady.” She picked Brenda up in a hug and she kissed me warmly. “I am going to leave you two to each other, but I had to let you know I was happy for you.”
“How can she be happy for me,” I thought. I feel like I am in love with two people. John drew her back to him and held me. John shared his thoughts aloud with me. “I am not sure, but she’s a sharp woman, I am sure she has too know it’s more than physical. She still loves you and thinks you still love her too.”
It was now noon when Brenda began to move again, I was trying to roll out of bed, when John took hold of me from behind.
“I don’t want too.”
“Sorry but it’s too late I need you.” He was pulling me onto him. I couldn’t believe that I was becoming a boy’s sex toy and my butt was filling up with him again. It was now well into the afternoon, as John had showered and was leaving my place. I got up, showered and was dressed and cleaning the house. It was yet early evening when Nora came back. We greeted each other with a hug. “I like you outfit.”
“I like yours even more Nora.”
“Well I am glad you are still in girl mode. We need to talk.” As Brenda knew she was right but she didn’t know what to say. “I love you Bob/Brenda, I hope you will still marry me and that I am your big love, but I am not blind.”
“Nora, I love you too, but I didn’t know I could enjoy being with a guy as I did.”
“Do you still love me?”
“I hope you know I do, loving you is so natural, and as you say you are my big love. I want to be Bob and I am willing to be Brenda with you. But I am not sure… I don’t know what I would do if John came on to me again.”
“Well you best know if it’s another guy or another gal, I won’t be happy, but I won’t be surprised if I need to share you with John.”
“What do you mean?”
“Bob, too much of you is Brenda, to stifle that. What would you say if I were to share you with him once a month?”
“Yea and how does one go about that? Are you going to call him up and say ‘Have I got a deal for you?'"
“No, I thought in two weeks we would go out to eat and visit with him then. I would tell him, with the wedding and keeping Brenda in nice skirts, I need some help. You just get your pretty face made up and let’s get something to eat. We can talk about those things another day.”
While they did not have intercourse, they did have a very enjoyable time in bed that night. She kidded him about being sore and walking funny. “You know LeAnn has wanted to bed me for a long time.” She hadn’t realized that LeAnn was a lesbian, because she’s married. Nora had never given into her, until LeAnn realized Nora was attracted to Brenda.
It didn’t seem to matter, since he was Bob most of the time. Nora and Bob were making out better than before. Nora liked enjoying her in so many ways. Especially when she would give a hint to what she would like and he would embellish it from there. She would put out a pair of jeans, blouse and apron and suggest he prepare dinner and say she needed a certain outfit washed and ironed. Friday they went out as Bob and Nora and danced up a storm. I even felt somehow more relaxed and graceful dancing now.
Sunday they went shopping; Nora was looking at a beautiful skirt and asked my opinion. It was a very nice skirt and I told her so, “but I don’t think it is you. I don’t know if it’s the color or what but get it if it’s what you would like.”
Nora smile and said out loud, “I was thinking about it for you, and I think the color will look good on you.” A woman nearby giggled. Nora put the skirt up next to me as she asked the woman, “Don’t you think he would look good in this? He has pretty legs.”
Laughingly, the woman agree and shared, “I saw white cream satin blouse that would top it off.”
“Should we go with this or do you want to try it on here?” Nora turned asked the woman if she remembered where the blouse she suggested was. We went and found it. The woman was laughing to herself as she walked away. Later Nora told Bob that the woman asked Nora if he did in fact wear women’s clothing for her.
The woman shared she wouldn’t mind bedding her husband in a skirt. Nora suggested, “After you get him to enjoy it for sex, then you have some leverage to get him to wear it more.”
That week went fast and when he got home on Friday Nora had my new outfit lying out on the bed, in Brenda’s room. She had gotten me a new powder blue gaff, so I put it on first. The new skirt was three inches shorter than anything I had yet worn. “I can’t go out in this.”
“You can and you will. You will look hot and turn heads in it?” We were both ready but had sat down when the doorbell rang and LeAnn came in. “Turn around Brenda, you look real fine girl." “Thanks, I think.”
“Don’t worry about me, Honey, Nora already warned me not to touch. You look hot too Nora, very nice indeed.”
“How about I suggest she’s off limits too?”
“It will depend on you.” We pulled up to the Forbidden Garden. We were shown to a table for six, where Bill, Steve and a woman named Megan joined us. Brenda hoped Megan was there for LeAnn, and Steve was there to keep Nora company. Brenda did not want to see John to come on her as soon as he did. Her panties were getting warm as she tried scooting closer to Nora. “You dress hot and we came here to the Garden, now don’t tell me you don’t want John. He fits in you so well.” Everyone smiled as she urged me to be a good girl. She shyly looked at John and smiled. LeAnn got up and changed seats with Nora. John invited me to dance and he was already hard as well as looking quite nice. Luckily only I knew his condition. When we finished dancing and sat back down, Nora asked me, “If you had to choose tonight which one of us you would keep and which you wouldn’t see again; which one of us would you choose?”
“Nora I wouldn’t want to hurt either of you, but you are the one I want to marry.”
“John, I know she loves you too, but I am not willing for her to be with someone who is sleeping around. If you two are to be together once or more a month, I need to know you are clean and you will be helping financially. Bob being Brenda is more expensive to keep and her clothes and things are more expensive.”
Nora took him to the dance floor where they talked as they danced. It did not readily dawn on him that they were dancing as two women. “Brenda, this is not about money and the decision to be with him is yours. I love you and you are mine, but if I need to share you with someone, I need to know we are both safe. You need to know your decisions can only be yours.”
“I might suggest or even state for you to do something but you doing it, it is your decision. John already looks hot for you; you can either put some ice down his pants or go and have a good time.” They shared as kiss as they left the dance floor, but alas it was as friends lightly on the cheek. LeAnn took Nora and John took Brenda by the hand.
They went to a show featuring a noted singer. It was nice to be doing something together. Nora spotted that John was one of several guys getting the singer’s attention. Nora encouraged, “Brenda you hold onto to John,” stating, “I think you are up to the task.” Brenda and John grabbed a suite at a near by inn and the others were on their own.
Then we went looking for a nightspot to finish our night. We went out dancing, it was a gay bar and I felt like I was at a meat market and I was the meat. I had to concentrate on John which was enjoyable enough. Quite a few customers knew John and spoke how nice it was to see him with someone again. They visited with him about me as Brenda becoming his love interest. His hands were under the table going between my legs and arousing me and kept it up causing Brenda cum in her panties. But it was Brenda’s mess, and John was happy with himself cause he was in control.
When We went back to our room, I showered and was looking fine for bed. I used a douche at John’s request. After I was clean and dry I put on a sexy negligee and went back out to him. I tried straddling John on top but it was taking too long and found it uncomfortable going down over him. I rolled off and pulled him around on top. He spent some time nibbling my nipples and though we were now all boy, I enjoyed his attention and felt it was quite romantic.
He then lubricated my butt and his cock while it was still nice and snug he was moving nicely in and out. The sensation was greatly heightened. They had fun as he went in her several times night.
It was about one thirty in the morning when John kicked me out of bed and threw me a wrap-around to put on. We went to the beach and in the water where he lifted me and eased himself into me. It felt nice to hold onto his muscular shoulders. When We got back on the beach I felt a strong desire to swallow him. He tried to resist me, but when I went to my knees he was becoming a big boy. He was just cuming when we were rudely interrupted.
It was an officer from the beach patrol who was ready to take them in as he was being pressured to break couples like us up and get them off their beaches. I asked if there was anything I could do to talk him out of it. Asking the officer if he ever had a nice boy. John quickly said, he would go to the court first.
I saw something in the response of the officer and pursued it. I knew if Bob made the news for this my wedding would be in trouble. The officer shared he hadn’t had sex in over five months. “My wife would be comfortable if I was regular size and unfortunately I am not.”
“John take a walk, if he’s going to take someone in, one is enough.” He took a few steps to see what the officer would do. Then I took the officer by the hand and suggested we walk. “Would you like me to swallow you or would you like to do me?” Brenda was surprised how easily he responded when I touched his zipper. “You are one horny officer aren’t you?” He laughed and when I felt how big as well as clean he was. I knew he wanted me and I now wanted him. I asked if there was a place more secluded and he showed me a spot between a boat and lifeguard chair lying down.
I threw my wrap to the ground. He apologized and said “No offense but I am not interested in a guy.” But as I undid his belt and unzipped his pants, he did not stop me. I quickly saw why his wife might want to heal more first. He would be at least as long as John. Seemingly he had already cum once while we were talking, but I made no mention of it. I had him lie down and turn ever so slightly.
He was still talking as Brenda, I began focusing his cock which was still growing as I caressed his head. He was a bit thicker than John and it took me two tries to get past the gag reflux. He was going into bliss and as I took him deeper inside of me. It felt like he was at least six inches down my throat. I knew I didn’t need to but I wanted all of him. When I backed out he was a bit disappointed. I kissed him on the lips and told him “it’s not over.”
I was swallowing him again, and in a short time I swallowed him whole and was now beginning to bring him to release. I worked through my own body shaking and when he came it was a very good sensation. He more than filled my mouth but was no way near as much as I regularly got from John. I couldn’t quite describe how but he tasted different from John as well.
When we got up and he was all back together I put the wrap on and we began to walk back. He wanted to pay me and was remorseful about cheating on his wife. I wouldn’t take any money but asked, “Would you treat our walk and conversation as due warning about my actions.” He thanked me as we went their separate ways.
John was up when I returned. We both felt bad, and I was unwilling to talk about what happened. I just cuddled up in his arms and went to sleep. The next day I put on my breasts forms and on my wig. We had some fun up in our room before leaving to get a bite to eat and return home.
Nora greeted me as I came through the door and I knew things were different with Nora but Nora wasn’t sharing. I tried to go to our room and change but was told, “If you want to change back you have to go to Brenda’s old room.
She then told Brenda, “We’re going on a ten day cruise but you’re going with me as Brenda.”
“Nora, I need to be Bob more if we are getting married.” She calmed down and asked if I would marry her. I quickly said yes. She spoke again, “Brenda will you marry me?” When I realized she was proposing to Brenda as well, I was shaking as I hugged her. She pulled back and shared one more time.
“Brenda I need to know if you will marry me?” Nora held out Brenda’s left hand as she put an engagement ring on it. We kissed as she took me as Brenda to bed in our redone room. Nora was having Brenda start on a diet with vitamin supplements the next day. Unknown to Brenda she had set up a job interview for her with a company that was trying to buy her away from her present employer.
Nora waited until 9:00 to tell me they were expecting me as Brenda. Nora had a 10:30 salon appointment for me with a 1:30 interview. “They won’t want me, Nora.” She began to cry. Nora explained how she had copied and documented the portfolio she had made up for them and the ideas Bob/Brenda had envisioned. And they knew they could not move on them without my help and plan to implement them.
At Nora’s suggestion, I checked my email account and found out I had already been fired by my employer. There was a statement that they had found out I was talking to the other company. I was furious at my company and was afraid I wasn’t going to get another company to hire me as the economy was tight.
We pulled up to Nora’s salon and when we went in Nora took over; “Bridgette, I have a young woman with a job interview and she needs a confidence builder.”
“Come in Brenda, I will take good care of you. It looks like you have recently become engaged, when did this happen?” When she told me yesterday, “Well see that and now a job interview and I suspect you have a new job just around the bend.”
When I told of my upcoming cruise and she saw my short hair. She spoke up, “So how do you like the change? You’re Nora’s love aren’t you? Wow, you got a special woman.” Life was changing too fast, Nora came in with a cup of coffee and the three of us chatted. Having my hair done was quite a treat for Brenda, a fantasy come true. Bridgette added extensions as well as permed my hair. A manicurist did my nails While I was under the dryer.
I was surprised to be on my way out of the Salon and on my way to the interview by 12:30. I want a light lunch but settled for half a tuna sandwich as I went over my portfolio for the interview. “Take one thing at a time dear and I will take you out when you get done.”
I went in for the interview and shared my product and promotion strategy and they were indeed interested. The associate to the CEO was in on the interview and I was offered the job on the spot. I even received my request of bringing my secretary and to choose the three associates to work underneath me. Her salary was to be $125,000 with benefits and expense accounts above that.
“One last request would be to know the bonus and me and my associates will get if this brings the profit I anticipate.” They offered the company’s going rate of 3%. I requested 7% since they would likely be getting new clients, they would not likely get otherwise. They agreed on a 5% bonus which was fine with everyone. It was agreed and would be in writing by the time I was walking out at 4:30 p.m.
I called my secretary Maggie that I wanted to hire her away but asked first that she was get my files that were already secured away for him. She would also downloaded as much of her own information as possible. I would not be officially hiring her until Friday and she should not quit until sometime Thursday afternoon. That's if she was not fired beforehand. We both suspected it would just be a matter of days before she was let go or reassigned. I shared she would be officially working for Brenda Miller, but that she would realize the connection real soon.
Maggie laughed and then asked “I just have one major question, Bob. How long will your company keep Bob after they find out about Brenda?”
Bob laughed and told her, “They hired Brenda and not Bob.”
It was 4:15 p.m. when Nora arrived and she was glad to wait twenty minutes as the news was good, very good. Brenda was very pleased to see her. “We need to go shopping quickly and get you some clothes for a cruise and then some for your work wardrobe as well as at home.” Nora’s lips were sweet and our times together were becoming more precious. “We leave on a cruise next Thursday and will be gone until the following Sunday.”
“But Nora, we have saved for our wedding and there is not enough money right now for all we're doing.”
“Brenda, I love you, and we will marry but not until we know who you are and whom I am marrying. We will have fun on our journey and especially when we stop at ports. We will need two dresses for formal evenings and much for our pleasure and relaxation.” We spent till 7:30 shopping, changed and went to a late dinner.
Nora allowed me only now and then to be a man and only when she said.
She was seeking to see if she could find happiness with both of Bob and Brenda. Nora had a vibrating penis to use as a man with me. As Bob it was humbling, as Brenda it was pleasing each time Nora entered me. We both had multiple orgasms. Nora was being pleased more than Bob alone could give, but which of them would she choose. We went on our cruise to enjoy and explore.
I was faithful in taking my vitamins and didn’t associate it with the change of feelings that tantalized me. My breasts were coming to life and Nora was having my sperm harvested for future use just in case. What Nora did not acknowledge was she needed a man’s love more than I was giving her. Nora was excusing herself more and finding herself going elsewhere for the pleasure of a man. It was the third night out when Nora came to bed with another man, knowing as Brenda, I would either be asleep or act as I was.
She did eventually send the men away and we made love in the time that followed. I lost myself in seeking to please Nora, and enjoyed myself quite a lot in doing so.
Nora was helping me each day to select my clothes and learn to do make-up and hair. She taught me the fine points of the little things and how significant they can be to one’s appearance or show the pretense that may or may not be driving one’s character. I was coming to like wrapped skirts for casual wear, especially with a swim suit. Nora showed me how to wear it conservatively and yet with a tease of suggestion.
It was interesting how the eyes of men and women would look, but generally for different reasons. Once out of the clear blue a good looking woman came up to me as we were sitting on deck in some lounge chairs. She used the cap of a perfume to scent my wrists and asked my opinion. The fragrance was nice, not over powering yet it withstood the salt air breeze.
Nora spoke, “I wonder if she knows whom she is inviting to follow her?” I looked at Nora wondering if she was suggesting I find-out. When I walked over to her, she asked me to stay put for a moment. She walked back and spoke to Nora. Nora smile, laughed and nodded her head with affirmation.
Then the two of us strolled the decks for over an hour before arriving at the woman’s cabin. Our breasts were similar in shape and size, but hers were real and more responsive. It was with her touch to my shoulders and back where she took control. She was there to harvest more of Bob’s sperm and she did a good job that afternoon and later in the evening.
Nora came the next morning, said there was an agreement. The woman would have me another day after Jamaica to harvest more sperm. Our first formal was the night before arriving at Jamaica. My hair was in need of another salon appointment due to the ocean as did Nora’s. So we both had appointments at one of the ships salons. It was fun for me to be one of the women and to be immersed in their world. Most of the hairdos she looked at were for when my hair was longer and did not have the humidity of the ocean to compete with. The beautician and I found a good choice and it looked more naturally cute. It would also be easy to manage.
I was getting subconscious about the growing sensitivity of my breasts, but Nora assured me it was merely a side effect of the adhesive, the false breasts as well as my own fantasy. It consoled me and allowed me to imagine I was changing but without consequences. While we did eat and dance together we were often interrupted on the dance floor. Nora had me wear a feminine napkin to help conceal me if a guy danced closely.
“Brenda, remember that you know how to please a guy without losing your skirt.” I was offended but I relaxed when Nora assured me saying “I’m going to bed you later tonight so don’t get your panties out of shape.” When we ended up dancing with two friends Nora felt it important that Tim should choose Brenda for whom she really was. When he was of a mind not to back out, Nora suggested Brenda and Tim go back to the cabin for him to experience whether I could please him or not.
I was both surprised and hurt but I agreed. I was not so surprise Tim enjoyed himself. While he was nicely endowed, he was not as big as the two I previously had. I found his cock to be very responsive. I felt his sexuality was in question even when he went into me and enjoyed himself. I planned to do him orally and was between his legs to do so but when he relaxed I followed an urge to go into him.
He cried but neither said no nor did he try to stop me. When we woke in the morning, I was back between his legs and this time they were wrapping my body. I gave him a pair of my panties to wear as we went ashore at Jamaica. Nora and I separated from them and Nora was amused to hear of my exploits with Tim. She too had a good time with Jeff but did not share too much.
We saw Tim in one of the boutiques and talked him into getting his ears pierced. While Nora had looked at the unisex section, the pair she handed over was fine jewelry and a bit more feminine. He was caught by surprise when he paid over $100 for them. She told him “We didn’t want you to easily throw them away, but we assured him they in fact looked good on him. He was to be surprised when more than one woman took interest in the new him.
I and Tim visited later and he shared being in touch with his feminine side could help him to be a better man. When she interrupted him and Jeff at their cabin he owned up that he was not losing his interest in men. It was interesting at the Virgin Islands the four of them went to a GLBT bar and had a good time dancing with one another. More surprising was there were well over 30 people we recognized from the ship.
Brenda suspected half were straight venturing to see how they fit in. One gal took a liking to Nora and pre-occupied the remainder of their evening. I went this night as a girly boy and found more interest than I could handle. The guys were gyrating as we were packed in tight on slow dances as well as nibbling and giving hot moist kissed.
slept alone that night as Nora did not return to the cabin and she decided not to go to bed with anyone else. It was two days later when one stop had a specialty clinic and Nora took me to visit a doctor about sex reassignment surgery. Nora thought I was leaning that way and we agreed to explore the idea though I was once again a bit hurt. It was interesting to hear of the procedures and the staff was warm as well as professional. Nora shared she had a growing interest in Jeff as well as another friend at home.
She said it was not serious, but her interest in her finance’ was growing to be more with me as Brenda and helping me to become more feminine. We were back at ship when I discovered she had new medicine for me to use. I learned from the discussion at the clinic it was safe to use the medication for a month or two and to revert back to my old self. What Nora was not yet acknowledging was I had already been using something and the feelings and changes were real.
Nora and I were having a great time being the best of friends. I was actually caring more about Nora now in ways that I previously was taking for granted. I was hearing her in ways i had long failed to acknowledge. i was not sure about the future of Our romance but i felt our love was growing richer and deeper than I had ever considered.
Just a gentle kiss and being held in her arms meant more than it had. Nora stirred a passion and could bring me to a climax that I didn’t even know was possible. But I was afraid the longer I was Brenda the more I would continue to want to be her. I spent another day with Marie before we would begin back to Florida. Maria commented that my sperm was in good condition and properly preserved. I asked if I crossed over if Maria could use my sperm to help others. Marie suggested I might need a source of sperm myself.
Two nights from port and we had our second formal and I had not realized that Nora had brought my bridesmaid formal. It felt great and looked even better. I felt like Cinderella going to a ball. The captain invited us to sit at his table. A noted football athlete was on the cruise and also a guest at the Captain’s table. I was getting nervous as we shared a few dances and his interest was continuing to grow. I was being swept up with emotion as we danced out onto the deck. We walked around for awhile and I lost track of where we were, as he took me into his room.
I was scared nervous about what he might do when he discovers I'm a male underneath. But he would kiss me whenever I tried to speak and his touch and some wine brought down my defenses. I felt the clasp at the top of the gown detach, but had not realized my gown was ready to come off until it began to slip to the floor. When I turned to pick up the gown he hugged me from behind. “Tim said you were a surprising lady and I guess he is right.”
”What else did Tim tell you?”
“He shared if I relaxed, it could be a very beautiful time. While this is new to me, somehow I am interested in you enough to give it a try.” I put my gown up on a hanger and turned and looked him in the eye and began to undo his shirt then his pants as I continued to watch his eyes. I rubbed him as I undid his zipper. I laughed and wondered how I kept finding myself with well gifted men.
I spoke about how I would like to do him before taking him into me. I suggested some foreplay and continued to undress him. “My, my did you and Tim compare yourselves?” Joel asked me how they compared, “Not necessarily in my favor, but you are quite the man.” He smiled as I knew he would be pleased. I was please as well.
I was surprised later to learn Jeff had brought Tim tonight to the dance as Ty. Us girls would get together before leaving the ship. But tonight she was with Joel and prepared to enjoy their time together. Seemingly Joel was use to a woman doing him orally but he was having trouble relaxing for another guy. “Oouu, are you embarrassed by being turned on by a girly man?” He was lengthening and hardening as Ty was licking his growing stick and fondling his balls.
It was when she found how sensitive the inside of his legs were, he was putty in her hands. He was ready to cum just from the erotic response of his legs. She took his head and enjoyed him but it did not work for long. It would be the second time that would bring him to paradise. She was surprised when she began to become aroused and more so when Joel allowed her to do him. He was surprised how much he liked her cuming inside him.
She was enjoying being on top but she kissed and asked to change positions. But she was surprised when he asked her to wait and do him again. She went to wash up and called Ty to come in and do Joel. Joel was surprised but not disappointed.
I called it a night and went to bed alone. Nora came in but was not alone and they snuck in her bed. She insisted to Jeff if he kept quiet that they would not wake me. She was quite certain if I was asleep she could not be wakened and she felt even if I did I probably would be amused.
She was right that I would not give things away, but wrong on the part of being amused. I waited till Jeff fell to sleep before I dressed and was leaving to go on deck. Nora asked, “How was it to be the onlooker?” I still loved and do love her but my heart was breaking as I accepted the relationship changing. I looked a fright and the hour made for strange friends.
A woman, I little more than recognized having seen her here and there on the ship, and we got into a conversation. She took pity and helped me brush my hair and to redo my makeup and nails. I listened to her story and she seemed quite intrigued about telling her story. She told me about a young teenage boy in her town who was like me, she could not tell if he was trying to be punk or just did not know how to dress like the girl he wanted to be.
She asked me if she dared to ask if he needed help. “I am not quite sure how you would go about it but if I were such a boy, I would wonder if I died and had gone to heaven.” We exchanged phone numbers and email information. It was ten days after the trip when I would receive a call that she and the boy, enjoyed her new look and were going shopping with her as she and I talked about. It was his mother who was at first offended, but she was now with them shopping.
The cruise was not all good moments and a few people were offended and some were enraged, but only a few times did it hurt and offend me very much. I was taken with my changes with Nora as a learning curve. I felt deep down Nora was going through a lot as well. It was 6:30 before she went back to their room. Jeff spoke up and presupposed I was surprised in seeing him. I gently let him down sharing I was awake when they returned to the cabin. He thought I was joking but I left allowing Nora to tell him if needed.
I called Tim and asked to have breakfast with him or Ty. He suggested an early lunch instead and I could choose to come back to his cabin if I preferred to see Ty. I was glad to meet him at his cabin before we went to lunch. Ty was trying to dress as a woman but needed to learn the philosophy ‘less was more’. It is not to say someone can’t choose to be a drag queen as some do. But Ty was trying too hard to be an attractive girl. After a short conversation, I learned someone else got him ready the night before. So this time I showed him a little but had him learn by doing. I did touch up his job some. I chuckled at the idea that I had anything to show others.
We ate a good meal and did a little power shopping before heading back to his cabin. I stopped at my cabin and got a smaller set of boobs to wear and fastened the regular pair to Ty. I like the change, it was a transforming moment for a cross dresser to feel and see oneself with breasts. Ty was enjoying herself and I was enjoying my own blossoming too much that it changed my desire to bed Tim.
Later I called Nora and we shared some mid-day drinks and conversation. It was a great unwinding of feelings with little attempt to reach any neat conclusions. It was just to be friends and sharing their journeys together was something special.
Nora said she would love to turn the clock back and to stay in love with just Bob. She joked that she enjoyed seeing Brenda as her bridesmaid. Brenda suggested it could be possible if she was open to it sometime down the road. She reminded her she had already made out with the woman who would be her maid of honor. She joked that she would have to bed three more bridesmaids to be impartial. They both laughed and continued to enjoy the remainder of our conversation.
Our arrival at home had some surprising revelations. While Nora gained five pounds they were barely noticeable and not bad for such a cruise. I however had lost four pounds which appeared to be related as much to my changing body than dieting. While I had filled out a little in the hips and my breasts, face, waist, legs and muscles were going down in mass.
While it might not be great for some women being down to a 27” waist, it was very nice for Brenda. The change however was shocking to what was left of my male ego. I wanted somehow to look better as a woman without sacrificing my masculine appearance. I considered quitting my use of the stronger medicines, but I had actually sent in a new order as we left ship. The body and my hair were changing as well. When I checked Brenda’s banking accounts I found financial need was not my biggest concern as a $50,000 bonus had been deposited to my accounts for Brenda.
I called and arranged a luncheon meeting with Maggie and would have interviews with nine applicants for the three associates. Maggie came over that evening, not wanting to wait to see the new Brenda. She was pleased and shared that she hoped it would be as nice or even better to work for her.
Maggie had communicated with three of Brenda’s clients about how Brenda could serve them and the products and services she could offer them. She suggested before we met the next day, I should request 5% discounts or rebates for customers coming to the company.
Maggie’s communication was in lieu of their former employer sending a letter to undercut her reputation. Maggie not only failed to send those letters, but altered the list to code to diminish and disrupt such letters in the future. Companies were told by company communications they could continue their association with the company and that their products and service should continue to meet their expectations. Clients did not know who they would be dealing with but hoped it would be to their satisfaction. Those who received communications, the communications were speaking poorly of Bob and then Maggie. Clients found them offensive since Bob had not spoken ill of the company.
Nora too had good news from her employers. I guess absence in her situation made the hearts grow fonder. They had finally given a long awaited raise and merit bonus. We had a mutual admiration society for one another. Nora agreed with Megan’s suggestions, though l was missing Bob. I was leaning toward selling my condo and looking for another place, to make a new start.
Nora and I spent the two days before returning to work to change my work wardrobe. While there were many skirts and slack suits, ordinary and boring they were not what I looked for. There were more colors and numerous styles to select from for Brenda. It was hard to limit my selection, but Nora and Maggie both reminded me that my hips and bust continue to change. “It would be a shame to purchase things you might not be able to wear."
I was the first but not the last of the executives to be hired by the Johnston Corporation as my hiring ignited new growth. Maggie quickly went from secretary to Office and Section Associate. I had to work to keep Maggie from being snatched away. I quickly confirmed two of the associates I wanted, and Maggie helped me to see the value of a young woman, recently a new mother. I saw drawbacks to hiring her, but Maggie helped me to see her abilities, initiative as well as how our commitment to her would likely bring dividends in the long term. Terri would work her first two months from a home office and meet with us every other Monday and Friday. While the male associates never caught on and the company quickly caught on about me; Terri and Maggie not only saw my transformations, they were willing to go out of their way to be helpful.
Terri chuckled whenever she found me holding her baby girl. Once while I was holding Molly and the women talked at some length; they did not realize that Molly was trying to nurse through my blouse and bra. Luckily the suit had a jacket I wore with it the remainder of that afternoon. “I think Molly is saying you will make a nice mommy.”
Within three weeks of being back we had 12 clients contract to change over their business with us. It was a strong upswing but aa manageable stretch for Johnston’s to accommodate the new business. A sluggish economy it made its growth look very healthy to present and future investor’s.
While, I could to buy a new sporty car on my own, I heeded Terri’s advice and wore one of my short and snug fitting suits to look at cars. The car I chose was not the one Bob would have selected. I would have gotten a more expensive car but it would have sent the wrong message to the sales associates of our clients. I was surprise to realize on how game savvy I was quickly becoming in a whole new way.
It was our fourth Friday back that Nora and I returned to the Forbidden Garden. I was surprised that John was with a different bunch of guys. But he quickly broke away and came to visit at our table. I had been to the salon on Wednesday and had no trouble sporting a very feminine look. We danced and talked and he quickly knew I was jealous of the attention he was receiving from the other men. He confessed that after two weeks of cold showers he had begun to look around. He said Fridays were his only night at the Garden, in hope that I would return. Guys had not been high on his list since meeting me.
I said good night while still at the Garden. I wanted to spend time with Nora, but did make a dinner engagement the following Thursday. Nora and I danced the remainder of the night with each's hands slipping down the back of the other, each enjoyed feel and squeeze of the other. We returned to Nora’s apartment and slipped into bed together. She wanted to be Bob with Nora once in awhile, but Nora for now preferred arousing my breasts and bringing me to experience multiple-orgasms.
The following night we ate at my place and I thought I were settling in for an intimate evening. Then the doorbell rang and I discovered Nora had invited John; Nora wanted to watch us make love again. I willingly went to get ready and hoping Nora would leave before John and I settled in together, not knowing what Nora desired. John loved my breasts and how they now responded to his touch. His cock was nice to feel against my body. Once he was inside I could feel the throbbing mass of his cock as he sunk inside me. It was like a warm rod going up inside me and it was stirring many more feelings and emotions of passion than we previously experienced.
The next day I was over Terri’s for dinner and to visit about some of her clients. But it was Terri’s response to the joy on my face that started our longest discussion. Terri used her need to change and nurse Molly on her breasts, as an excuse for us to be alone in conversation. “You were fucked last night weren’t you?”
“What makes you say that?”
“You look like I feel after Max was especially good in pleasing me.”
“You don’t need to get descriptive.”
“Well, look who has missed out on the sultry talk of us gals. I should just go ahead and baptize you by immersion.” Without my agreement she took off my top and my other clothes as she felt needed and showed me how a woman’s body responds to sexual arousal. She even had me touch the rim and inside of her vagina to feel her hot juices flowing. “I hope you fully change over some time. I enjoy sharing times like this with you but I wouldn’t want Max to find out what you have between my legs.”
She was right I was not yet use to women talking like this. It was however helpful and I liked getting a very irreverent talk about the birds and the bees. I was again embarrassed when Terri told her husband what they had been doing. It was not like she just blabbed it out, but to my embarrassment he insisted on a bigger explanation.
Max questioned me how his wife could be making so much while working out of her home. ‘Why are you so surprised? If you or another man made her sales you would not be so surprised by what they would make as a bonus.” He acknowledge that was true, but he also knew most companies would not do it for a woman.
“It must have to do with her working under another woman. Are you glad she does?” This was their second child and I was hoping not to lose Terri to just taking care of her growing family. “I’m holding off a trip I want to make for another three months, so Terri and Maggie can run our section while I am away.
On Thursday and Friday, I was taking my first business trip to Atlanta and onto Chicago. It would be my first trip alone as Brenda. I was both excited as well as nervous. I went and picked out two more outfits for my travel wardrobe. My hips had continued to grow and my bust was now pushing my B cups to being very full, much to my delight. While I used a push up bra to give noticeable cleavage, I was no longer using extra padding.
I had been to my GYN doctor, who agreed that we should be scheduling my first reassignment surgery for mid September. It would give me time to continue my psychological transition as well.
I had just gotten back to my home when Terri called saying she did not know where else call but she needed to get to the hospital and wondered if I could come and help with Molly. She was taking Molly with her to the hospital and I agreed to find them there and pick up both Molly and her safety seat.
It was twenty minutes after they got to the hospital that I arrived. It was Terri’s grandmother who was in critical condition. She got to see Molly but Terri would be there all night as her mother would not be able to get back until the following day. Terri gave me keys to her house and I took Molly to their home. Molly was unsettled and was not willing to be easily settled down. Terri had but one bottle of breast milk and had not informed me that she was out of formula.
Later Molly’s tears flowed after the first bottle was used early evening, and her cry and tears were now getting worse. When Molly tried to nurse through my blouse and bra again; she became enraged when I pulled her away. I did not like the idea but I unbuttoned my blouse and undid one side of my bra as Molly quickly hooked up to my breast. I didn’t expect she got anything but glad she was content for a few minutes. Molly looked up at me and smiled as her hands were on my breast.
She was again getting restless until I took off her top and tried her on the other breast. Again Molly sucked and was content and then fell asleep. I was very content to hold her in her arms and allowed her to sleep there. Three hours quickly passed when the phone rang and Molly woke up. Terri was calling to ask if it was alright that she stayed at the hospital. Her Aunt would be coming in sometime so she could come home. When I offered to stay the night with Molly she was very happy. I checked Molly’s diaper and changed her and gave her a bath as I had seen Terri do before. I was getting into being an aunt.
I noticed my breasts were swollen and slightly more sensitive. As I held Molly, Molly became discontent again until I undid her blouse and put her back on a breast. This time however I could feel Molly sucking from my breasts, and even notice milk around her mouth. She nursed about seven minutes and then changed breasts and I was pleasantly surprised that that I could see a difference in the fullness of my breasts. When Molly was done, I was able to wipe my breasts and nipples clean, as well as burp Molly.
Then we enjoyed one another for another hour and I put Molly down for the night. There was a small bed in Molly’s room and I decided to sleep there to make sure I heard Molly if she stirred. It was early in the morning about 5:30 when Molly stirred again. I checked and changed Molly’s diaper, before long I put her back on a breast to nurse. She was on the second breast, when a light flashed on and I discovered Terri was home with her husband.
Her grandmother had become stable and Terri and Max had come home. I worried thinking Terri would be upset, but Terri had already wondered what I would do since she realized there was no formula. She knew Molly was very fussy. She was delighted to see that my breasts had quickly come into milk. Max could not help but stare at my enlarged nipples as I took Molly off to burp. Terri laughed as she fitted me with one of her nursing bras. Her bra had been too wet to wear home, but Terri put me back to bed in Molly’s room as she would not allow me to leave until she fully woke up.
Meeting John for dinner was very welcomed after I was rested and got through the day. We went to a good Italian restaurant and enjoyed a good meal. He took me out to dance and we were having a good time when another gentleman broke in requesting a dance with me. It was a slow dance and though I was initially upset; I was moved and a bit disarmed when I looked into his eyes. I was also disappointed when I saw John asking another guy for a dance.
I was happy the guy did not say yes, but my feelings were already hurt. Brian apologized for cutting in, but shared he had watched me for the last 30 minutes. While he saw himself as straight, he found himself strongly attracted to me. We shared a second dance, and then he escorted me back to my table. When John got upset with me for taking a second dance, I said I knew he asked another guy to dance with him. When he continued to be upset; I picked up my purse and walked away. I finally went to the woman’s room to fix up my make-up before calling for a ride.
Brian interrupted and asked if I would stay and dance. When I told him I thought it was important to leave, he asked permission to take me home. I told him “Quit playing around…” Brian put his finger over my lips and replaced it with a kiss. I stayed for another half hour of dancing then Brian gave me a ride home. I invited him in and ended up inviting him to bed. I pushed him into making love with me, expecting he would walk away. Both of us were delighted he followed me to bed. Brian loved the response of my breasts and I like how I responded with Brian; and yes I enjoyed how very sensitive, responsive and sensual my body was feeling.
Brian even enjoyed going into me. But instead of taking him in my mouth, I coaxed him to lie down with me and after he became aroused I rolled him over and lubricated his butt. He asked me not to do him, but when I asked him to raise his butt he complied. Even as my penis was just entering a joyful smile came over him. They both enjoyed as I was moving in him. He was responding by his cock becoming erect again and ejaculating. I had an orgasm as I came inside of him and relaxed lying down on him.
I but was not sure I was yet ready to give up my male appendage; thinking I enjoyed doing men too much. It was 7:30 the next morning when I found myself waking to the mist of a light perfume. Brian was just waking too. I held a negligee out for Brian which he tearfully received and got into when Nora came over. Nora had come over to speak to me about John. I asked Nora outside and I told her to go home as she closed and locked the door.
Brianna made love with me and while she messed her panties. I had Brian take off the negligee, clean up and now Brian entered me as the man. He lubricated my bottom, then Brian and I took time to enjoy and please each other both before and after he entered me and we made love much of the day.
It was a weekend that marked me for the years to come. While I felt my love for Brian, Brianna was the person I was looking for. She did something different for me. I held true to taking time to becoming a woman and finding myself.
Nora brought out the best in me, but we both moved on!
The End of this Story
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