Story name: My boyfriend made the switch
My boyfriend was perfect for my college thesis final. He already enjoyed wearing panties 24/7 and nightgowns every night. I think he secretly wants to be a woman, but he never admitted that.
So here are the people in my story…
Me, Cathy, the girlfriend doing my college thesis
My boyfriend of several years - Terry
Sue, my lesbian “friend”. Sue lives across the hall in our apartment complex.
Hi, my name is Cathy and I am in my final year of college and need to do my thesis on hypnoses. I have a great boyfriend Terry. We have lived together our college years and are good for each other. I also have my best, best girlfriend next door in our apartment complex. Sue is more than a best friend and Terry is ok with my close relationship with her.
I have always had a dream or fantasy, a desire to feminize a man. Not sure why but it turns me on to think about a pretty man. Luckily Terry does crossdress as he likes to wear nightgowns to bed and around the apartment and he wears very feminine lacey panties 24/7. So I think he would like to be feminized more. I like that and buy him those pretty clothes all the time.
So here is my plan. Since I have to do a final thesis for school, I thought I would see if Terry would help me. I asked him if I could hypnosis him and do my “test” to see if I learned my stuff and turn in this “test” in for my thesis. He said sure, he was mostly willing.
So we started…
I came home from school Monday and we sat down to review my thesis plan. I told him my thesis was based on hypnotic trance and how I could control a person in that state.
I told Terry I would “tell” his mind to wear women’s clothes, much like the nightgowns he wears at night with me. That he would be happy and accepting of wearing these clothes. I did not want to give more information just then.
He seemed very willing and ready. He jokingly said he was wearing nightgowns and panties now, how much different could it be?
I told Terry that he would listen to tapes for several nights and then to work on the thesis we would travel 2 hours down the road to Albany, NY and stay at a hotel to get away from the distractions of our daily life. He thought that would be fun.
I gave him the earphones and ipad and he was sound asleep that first night listening to my program.
In that tape I had soft commands instructing him that he will follow my requests without question. He would love and do what I asked and he would be the happiest person.
The following morning I tested the theory. It worked, he did everything I asked including kissing my toes, which in the past he hated. Wow, this is working. I will get an A on my thesis.
Again Tuesday, Wednesday and Thursday night he listened to the messages. By Friday he was putty in my hands.
We packed up our stuff and drove off to Albany for our get-away weekend.
We checked in to the hotel and I said lets go out for dinner. I called him over and whispered in is ear the “magic words” to set off the weekend. I said, “Terry, you are so beautiful”.
He seemed to snap tall and looked at me and gave me a big sexy kiss. I knew he was under my full control now.
I told him to get a shower and I would layout his clothes on the bed. Told him they are the clothes he will wear tonight. He smiled and said, sure!
Now comes the true test. To see if the taped messages really worked.
I put a soft cup Playtex Cross Your Heart bra, a B cup bra and a white thin feminine sweater on the bed with his normal panties and man pants, socks.
I sat in the chair watching TV reading the paper as Terry came out of the bathroom. Like magic he went directly to the clothes on the bed and proceeded to put the bra and panties on. Like he has done this every day. No problem putting on these very feminine items.
I was so excited to see he had no problems doing this, like it was natural for him to wear “his” bra. I could hardly hold back my excitement.
He had trouble hooking the bra so I jumped up to help him.
“Here Terry let me hook that for you. To bad you have some gapping in your cups, you must have lost some weight, dear. Can I fill that out your cups with something, so your cups look pretty and full!
To my amazement he said sure, it does look strange not filled out. I knew he couldn’t fill out his cups, but he does have some breasts, more so than any man I have seen. There was some padding in the bra cups but he needed a little extra help. I brought little pads or insert to fill out his cups.
I placed them in his cups. He smiled and thanked me. I could not believe how easily he was taking to my hypoxic commands. This was too easy.
He slipped on the white tight sweater and as I wanted the bra shouting out.
He did get a little nervous saying, “Cathy don’t you think this sweater is to tight and it shows my bra. Maybe I should wear my t-shirt.”
I jumped right back saying, “no sweetie, you look very nice and I loved it. Looks very pretty. Besides we don’t wear t-shirts under our pretty sweaters, you know that”. Wow, that was all he needed to hear, that I loved it. He said, “ok, then I will go like this if you think so”.
He definitely had a projection of a perky shapely bustline. It was clear he was man wearing a bra under his feminine sweater. He had a very shapely chest, almost a pointed figure like in the 1950’s. The padding was working. I loved it and he did too!
We walked out of the room through the lobby like there was nothing different or strange that he was wearing a bra. No one made a comment. He had people staring as he was picking at his bra straps.
I jokingly told him to stop playing with his bra straps. He said the bra was too tight and was not comfortable. I told him tomorrow we would get him measure for a new bra. That he probably was developing a bigger bustline and needed a larger bra but for now stop playing with your bra. He seemed embarrassed but stopped adjusting his straps.
The hypnotic trance was working well, he listened to me. This is going to be such fun.
Dinner was un-eventful. I had fun telling him to sit up tall and be proud of his figure. He would smile and throw his shoulders back like he agreed, projecting his bustline like a proud girl would do.
I was surprised at how much he liked talking about bras and his love for vintage bras, like the cone bras of the 1950s. Wow, I made a mental note of that. He would look so cutie in a pointed bra, as a man. I thought since this is going so well, lets take him to the mall now, tonight and see how he reacts in Victoria Secret, a real women’s store.
I could not believe how calm and at ease he was walking in public clearly showing a bra on his chest. Here was a man, walking tall with a cutie bustline saying I am all girl up here on my chest. My hypnotic commands were really working.
He was very different at Victoria Secret. He seemed to get nervous with all the pink feminine clothes. He got flustered so I walked him out of the store and calmed him down. I would have to think about this before tomorrow. I wanted to come back to VS Saturday and have him measure for a padded bra, to see how he would reacted to being measured.
We did some window shopping and I changed the direction saying I was interested in looking for a dress. He seemed to like that and calmed down as we strolled through the mall.
We didn’t try on any dresses or buy dresses but we did talk about what he thought of different styles and colors. I was surprised at how into the conversation he was and seemed to enjoy all the feminine talk.
I couldn’t believe, he was walking in public, strutting with a very perky bustline, bra showing thought his sweater and having no problems with all this. People looked at him, he just smiled back and moved on like there was nothing wrong.
This was my first phase of my thesis and it was working great.
Back at the hotel, he undressed like any normal girl would. A natural thing he did nightly. I asked him how he liked the inserts in “his” bra. Saying it did fill out his cups beautifully.
He agreed but said he was uncomfortable with them. He admitted he also did not like the gapping in the cups and the inserts helped filled out his cups.
I asked him if he would like to wear that same bra tomorrow when they go bra shopping for him?
This was a test. I held my breath as he thought a second and he said, “sure, this Playtex bra is ok and gives me a nice figure.
He then asked me if we could find a bra that did not need the inserts. He actual said, “Maybe I am wearing the wrong size bra”.
Where is he getting all this from? Maybe he was a woman in his former life. This is getting to good, I thought.
I was blown away. I could not believe how accepting Terry is with my hypnotic commands.
That night I gave him a tape or a message to help him accept going into Victoria Secrets. Hope it works.
The next morning was fun. I put out on the bed a very feminine flowery thin blouse with lacey and puffy sleeves, tight fitting to show his figure and clearly the bra under the blouse.
He did question how feminine and thin it was. I said it was the new style and looked very nice on him and I wanted him to wear it and feel good wearing it.
Like magic he was ok with his new look. Off we went to the mall back to Victoria Secret to get him measure, the big test of my hypnotic messages.
Again he got the stares but he handled his new look well, strutting through the mall like there was nothing unusual wearing his feminine top.
I pulled him aside before walking into VS saying to him, “Terry, I think you need to be properly measured for a pretty bra since I think you are wearing the wrong size bra. Your cups are not full and you are wearing inserts. Lets go into VS and get measured. That would make me very happy”.
Terry looked at me with a big smile and said, “Cathy I was hoping you would say that. These pads in my bra feel funny and if you think I should get measured, then I want to please you”.
I was blown away. He is putty in my hands. He is so relaxed now, as compared to last night, walking into VS, even knowing he is going to get measured for a bra.
We walk in and he even said to the clerk, “I think I am wear the wrong size bra, can you measure me?” She was very professional and wrapped the tape measure around Terry like it was just another girl being measured.
I looked around and there were many teenage girls giggling, starring at Terry, but he was fine with all, like he has done this a thousand times before and there was nothing wrong with him being measured.
He even opened his blouse and showed the sales girl the cups and took the inserts out to show the clerk how the cups were gapping. She told him he should not wear a bra like that, that it’s got to be uncomfortable.
She smiled and said she has just the pretty bra to help him with that. The bra was an “Angel Air” push up bra, a very padded cup. I thought wow this will really give him a bustline, hope he can handle this.
The clerk lead him back to the dressing room, no resistance, he just walked with her. I walked into the room with him and helped him fit his new bra and to make sure he was ok emotionally. I thought this would be a huge step for him, a real test of my hypnotic program.
Slipped on the bra like he has done this before, he had his new bra on in seconds and saying how nice it fits and there is no gapping in the cups. He was so excited about the full cups. I was amazed at his excitement.
I could also tell the clerk was very amused and having fun fitting him.
I thought to myself, this is too much fun. I am really getting turned on and my boyfriend loves it as much as I am. How great is this. I think I have a new shopping partner.
Just then my cell phone rang it was Sue my next-door neighbor. I told her I was in VS dressing room with Terry as he was trying on bras. I whispered in the phone that he was loving this and he is being so good. Terry looked nervous as I was telling her but I told Terry it was ok and he needs to relax. I told Sue this was way to easy and my thesis is going real well, I told her I would call her back tonight.
Terry asked if he could wear his Angel bra now. Yes, of course you can dear, I told him to leave the bra on, and we now need to look for matching panties.
The clerk had a big smile saying, “Terry, I guess you like the bra. Can I show you the matching panties too?” Terry followed her to the counter and they picked out the matching panties. He seemed so excited.
I was watching him from a distance as he talked with the clerk. He looked so sweet in his feminine blouse. He seemed so happy and comfortable in this store. Clearly I could see his pretty new Angel bra, it gave him a more projected bustline than the Playtex bra. I was happy with that. I have my man right where I want him.
Terry asked the clerk why they call this bra an Angel Air bra. She held up one of the bras and showed him the small air bag inside the bra saying this is how we fill out your figure to give you a pretty shape. She said between the padded cups and the small air pockets, you have a very shapely figure. She asked him if he liked his Angel shape.
Terry smiled and giggled and said “yes, I like this bra very much. Now I don’t have to wear those insert in my bra.”
Terry liked his Angel bra so much he asked to buy two. With a big smile I said, “of course Terry”. He was all giggly and excited he was buying such feminine lingerie and so was I.
We bought his bras and panties, he walked out carrying his little pink VS bag. Here he was a man, wear a feminine blouse showing his new Angel bra, carrying a pink bag saying to everyone in the mall “I shopped at a girly store and I am wearing a VS Angel bra, don’t I look good?”.
I took him around the mall looking at all the feminine stores I could find. Seeing how he responded in each. I was amazed how easy or comfortable he was. In a teen dress store, I held up a skimp short lacey dress saying to him, “Terry wouldn’t it be fun if we each bought this dress and we could be twins in matching dresses. Wouldn’t you just love it?”
This was the first time I heard him resisting feminine clothing. He didn’t want to dress like a girl he said. What? So I pulled him aside and whispered in his ear, “Terry you are so beautiful”. Terry look at me, like he was changing his worlds, zoning out as a big smile came over his face.
Then I said to him, “Terry, wouldn’t you like a dress like this, maybe we could both wear the same dress and be twins”.
Like magic he smiled and said, “sure if that would make you happy, I would love a dress like that. But would I need high heels for that kind of dress?”
Oh, Wow this was working out so good I thought. But I have to figure out why from time to time he looses his hypnotic trance and I have to re-set the trance. I gave him a big kiss and said maybe tomorrow we can stop at my dress shop at home and look for a dress that would fit us better.
We went back to the hotel and had dinner at the hotel. After dinner we walked in the gift shop and Terry was looking for the longest time at earrings. I walked up to him and whispered in his ear, “Terry, would you like to wear them, they are so pretty?”
He smiled and did not say anything, but I knew he liked them. I did not push this since it wasn’t in my plan right now.
Back in our room, before he got out of his new VS Angel bra he showed me the fit and asked if he could make the air bags bigger. I smiled and said maybe since that helps us girls fill out our figure. You know, the little bags fill in the gapping in your cups. Gives you a nice round full bustline. I told him how pretty he looked in his new bra. He seemed pleased.
He agreed and asked if he could wear his new bra all night. I didn’t know what to say, so I said sure, if he loves it that much.
Sunday morning we got up, showered and this time I did not put out his bra and blouse. I wanted to see what he would dress in by himself after his shower.
I was disappointed to see he “tried” to put his old man clothes on. Of course I stopped him by whispering in his ear “Terry, you are so beautiful”. Then I told him he must wear his new pretty bra everyday, all the time.
He looked at me with a strange look. I was concerned he had lost my hypnotic trance. All of a sudden he smiled and said, “Cathy, I am not sure what got into me. I know I have to wear my bra. I need to support my little breasts, dah.”
He smiled and put his Victoria Secret bra on with great pleasure. He seemed so happy as I handed him a new top. This feminine top was a white sweater, low cut, shaped beautifully, showing off his bra and pretty figure.
He looked down with such pleasure, running his hands over his chest expressing such pleasure and acceptance of his figure. He looked up at me asking if he looked good.
I knew he was back in my control.
We packed up and drove back home. Back in our town we stopped at my dress store, “Betty’s Shape and Dress Shop”. Soon it might be Terry’s new store. I wanted to get matching dresses so we could dress as twins. This should be interesting test I thought.
I didn’t know how far I could push Terry into wearing a dress but I was going to try.
Here was Terry walking into a dress shop with a very pretty top on clearly showing his bra underneath and sporting a very girlish bustline. He walked like he was proud of his figure and had no cares in the world, almost like he was excited to be in a women’s dress shop shopping.
Betty greeted us, she knew we would be coming and knew about my college thesis project. She loved guiding men into our feminine world.
Betty showed us many dresses and we both had fun trying them on. Terry was a real trooper and seemed to have fun trying on matching lacey dresses.
I was surprised at how carefree Terry was undressing in front of Betty. Good thing I had Terry in a panty girdle, held in his little guy. Betty said many times, “Don’t worry Terry, we are all girls here”. I was surprised that Terry didn’t get nervous being called a girl, it was amazing.
We finally agreed on a very tight form fitting shapely dress for both of us. We looked very feminine but Terry still clearly looked like a man in a dress. But he loved it, wanted to buy two dresses.
Betty also suggested a Spanx garment that would shape him from head to toe. I was so surprised how he accepted this tight fitting shapewear. But he did, so much so, he wanted to wear it home.
Betty whispered in my ear, “Cathy this is way to easy. He really is accepting your thesis. Can I have the thesis for my husband?”
We also bought two more panty girdles for him with the garters. He was in 7th heaven, so excited saying he wanted to get home and model all his new clothes from the weekends shopping trip.
This was working way to well. I will get a A on my thesis.
Just then I remembered that I would have to bring Terry into my class and show my other classmates and professor how this thesis worked out. This will be fun.
As we were walking into our apartment, Sue popped her head out her door asking if all was ok. I gave her the two thumbs up and said, “here Sue look at Terry’s new sweater, isn’t it pretty?” Terry twirled around and modeled his new look with a big smile. Sue looked pleased and told him how pretty he looked. His response, “Thank you Sue, I do feel pretty.”
Sue helped us bring our new clothes upstairs to the apartment and offered to bring dinner over if Terry would model his new clothes.
I said sure, and asked him if he would model his new clothes for Sue and me. He smiled and agreed, seemed so happy.
Terry had no problem modeling his new bras and his new dress for Sue. I whispered in Sue ear, “I think we got him, he is playing right into our plan”.
Terry went up to get ready for bed and Sue and I talked.
“Sue, this weekend went very well. You should have seen him in Victoria Secret getting measured for a bra. The girl was cracking up but so professional and Terry just took it like it was the natural thing for him to do, getting measured for a bra. Don’t you just love is perky breasts? He is wearing that Angel bra. He was so cutie asking why his new bra has little air bags in the cups. He seemed to like how the padded bra rounded out his bustline. Such a girly girl.
He has no fears of dressing like a pretty woman, at least his top half, in public. You saw how he was when we came home. He was so proud of his figure, showing it off to everyone and his bra was so out there. I bought him that top to make him real aware of his bra and figure. He loves his bra so much he wore it all night! Didn’t you just love the top?
Sue was so excited saying he looked so lovely and happy.
I continued to tell Sue about our weekend. We stopped in the hotel gift shop and I thought he was going to buy earrings. He is melting right into our plan. He has become so sweet and such a good lover, now that I tell him what to do. He is very submissive.
My hypnotic messages, the whole plan worked great. I think we have Terry right where we want him and he loves it too.
“So when do we get him into wearing a dress full time?, Sue asked. “Well, from what I learned in school, I need to take this phase slow. He needs to get very comfortable with this phase first, then we can move on. I gave Sue a big hug saying, “Sue don’t worry, we will all be living together soon, one big happy family and we will have our happy husband or housewife for all our housework”.
Over the next couple of weeks I had Terry in his bra everyday. I helped him tone it down for work with a camisole and loose fitting shirts. But if one looked hard you could see his pretty bra, not the padded ones but for sure an outline of his bra.
There was one morning he came downstairs ready for work without a bra on. I check every day, feeling his back and check for that girly bump, bra strap. With a little fear I looked into his eyes asking why he did not have his bra on this morning.
He could not answer me, he tried to answer but nothing came out. I was worried, is his brain mixed up. I then whispered in his ear, “Terry, you are so beautiful”.
Like magic he smiled as I said, “Terry, best you go back upstairs and put on your bra, you will be late for work and you know you need your bra for support of your breasts”.
He marched right back upstairs and put his Playtex bra on. He looks so cutie.
I made a mental note that I should be giving him his command each morning so that we don’t run into this problem. I would hate for him to figure out he shouldn’t be wearing a bra when he is at work. That would not be good.
Most times I am surprised at how natural he is in dressing and just wanting to wear “his” bra as he calls it. I knew he was into crossdressing but this is way too good.
Sue was bugging me to push him further. I wanted to “guide” him slowly into his new life of femininity. He was doing well.
Sue and I took him shopping, all those feminine things you do shopping. I was getting Terry use to Sue tagging along. She even helps him pick out some nightgowns. He seemed ok with her and her direction.
On one of the shopping trips, Sue pulled me aside saying lets take him to the makeup store. I agreed and we guided him into the very feminine makeup store. Tons of women were in the store shopping, not one man.
He walked right in like he has been here before. We took him to the lipstick counter and got a clerk to help us. We didn’t push it but we asked Terry’s opinion of colors and texture lipsticks.
Finally I looked at him saying, “Terry, would you like to wear this pretty shade of red with the lip gloss on your lips? I think it would look very sweet on you, please try it”.
Like magic Terry had a huge smiles and said he would love to try that pretty color. Sue and I looked at each other and knew he was moving forward, we had him right where we wanted.
Terry tried on the lipstick and gloss. The color even had some bright sprinkles, really sparkled on his lips.
We all said how nice it looked, made his lips look so pretty.
Terry seemed so happy, like a giggly little girl. He looked at the clerk and said he would buy two.
Wow, my plan is work.
To my wonder, Terry left on the lipstick and we moved on to another store. His lips were shouting, “here I am all girl, don’t I look pretty”.
The weekend was upon us and Sue and I both agreed now is the time. Saturday morning Terry was in a good mood so I moved it for the second phase.
I told him the magic word to reinforce my next move, “Terry you look so beautiful”.
He looked confused saying, “I only have on nightgown on, how could I look so beautiful?’
I told him I just had to say that, that I was so proud of him.
Sue was with us in my apartment as I brought Terry in from the kitchen. He was now doing all the cooking and doing a fabulous job, he loved it.
“Terry, lets have some fun today while we are home all day. When you go up to shower and change why don’t you put on “your” pretty dress we bought several weeks ago. You know the matching dresses we bought at Betty’s. We can be twins today”.
Again, his huge smile as he said, “That sounds like fun. I was wondering when we were going to wear our matching dresses together”.
I gave him a big kiss and told him I would be up to help him learn how to garter his stockings. He looked puzzled with that but I told him to run along and I would help him.
Like a little girl he “ran” upstairs. He was so excited.
Sue and I gave each other a high five and hugged each other saying this is going to be so much fun.
Phase two is about to begin, Terry is being such a lovable ductile boyfriend and soon to be our total housewife.
Sue and I went upstairs and Terry was sitting on the bed in his bra and matching pink panties. So cutie.
Sue and I looked at each other and just smiled.
I took out a garter belt and showed Terry. He said like it was so natural, “shall I put it on now or after I put my girdle”? We were both blown away with his response.
I hugged him saying he was so sweetie and I would hook his garter belt for him after he slipped on his girdle.
All of a sudden Terry started crying. “Oh sweetie what is wrong, don’t you want to wear nylons today”?
Terry looked me in the eyes and said I have to tell me something very personal. The tone in the room got real serious. I was nervous now, he look as white as ghost.
“Cathy when I was 14, my two sisters made me crossdress. They made me dress in their clothes. They are the ones who got me to crossdressing. I wore pretty bras and garters belts, they pushed me to wear them. Plus my Mother helped. My Mother wanted all girls living in the house.
It took me a long time to handle wearing girls clothes. They made me wear dresses, stocking, everything. I eventual took it as second nature, like it was meant for me. We became one big happy girly family. Over time I loved the soft clothes and all the attention.
All four of us had many girly shopping trips and they bought me lingerie, lots feminine clothes. I became so natural at dressing, I even liked it, but only at home.
I had no male friends, only played with my sisters and a couple of their girlfriends.
I looked at Sue and was blown away. Here I thought my hypnotic thesis was doing all this to Terry.
“Terry, sweetheart that is such a sweet story, your sisters and Mom really love you”. I am not sure why I said that but it worked. Terry let down his defenses and hugged me while saying he has more to tell us.
Terry went on by saying, “I became one of the sisters in the house. Plus my two sisters made me there slave. Don’t get me wrong I enjoyed it. Many days they had me dress them, yes, hook their bras and garters, pick out their dresses, even wash their clothes.
We were in the same bedroom so we all lived as girls, Mom said it was easier that way. We could all wear each other’s clothes.
I think they did this to keep me under control, subservient to their feminist ways. Don’t get me wrong, for some reason I enjoyed helping them dress. Many times they even let me wear their clothes, I was in heaven.
“So, I know how to hook my nylons to my garters. I hope you are ok with that”, Terry said.
Sue was all excited and quickly said, “Terry show us how you do it, you must be a pro at dressing then, that is so sweet.”
Cathy and Sue looked on with amazement, as Terry got dressed. He even found the full slip we bought him and put it on like he has done it a thousand times before. He slipped on the form fitting dress, he was a vision of loveliness. Both Cathy and Sue were very excited.
“Terry, why didn’t you tell me you loved crossdressing so much. You really beam a vision of loveliness, a glow I have never seen before. How do you feel all dressed up now?”, Cathy asked.
“Cathy, I have always wanted to dress up, my sisters taught me well. I am hooked on women’s clothes and feminine way of life. I know you used me for our college thesis, but I wanted to help you. I think your thesis or hypnotic support helped me develop my inner well being to accept dressing as a woman in public as we did in Albany. I could never have gone out in public without your help. I learned the average person does not care how I look.
Sue popped right in saying, “Terry, Cathy and I would like to be your new sisters. We would love to have you as our little sister, be one happy family, the three of us women. We can help you handle your feminine side, Cathy is very good at her hypnotic commands and half the battle is won since you love the feminine side of life. What do you say?”
Terry looked at both of us; I knew the hypnotic state came over him as he hesitated to say, “As I did with my Mom and sisters, I love you both and would love to try to be your sister, but not sure I can emotionally handle being a girl full-time. I will need a lot of help to be your full-time sister”.
Cathy was excited with my answer. She hugged me and whispered in my ear, “We will be one big happy family, you will love being our sister. We will help you become the most feminine girl ever, you all ready posses a very feminine look and your brain is already wired to make you a very pretty girl. Your Mom and sisters taught you well, sweetie. Now Sue and I will develop you into the woman you always wanted to me.
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.