My Boyfriend’s Love

I love lingerie and I love lingerie on my boyfriends even more. This is a story of fulfilling my fantasy with my current boyfriend Trey.

We are both out of college, 21 years old, very much in love with each other. But I have a good “feeling” that Trey has a huge feminine side to him. I love that about him and it makes me more attracted to him, plus it excites me since I like my boys wearing lingerie. What really turns me on is when we BOTH wear matching lingerie.

Since I love bras and panties so much, I have tons of matching sets. Trey comes with me often to Victoria Secret and women’s stores to shopping. He seems very interested in my purchases and we have lots of fun shopping together.

So I thought I would try a test I have used on my other boyfriends. Seeing if they like the soft feeling of wearing a pretty feminine nightgown. This has worked many times before and a good test to see if he will wear a dress in the future, my real goal. I am surprise at how many men love wearing the soft clothes of women’s. Of course I have to make them understand it is ok to wear women’s clothes, to relax and feel the pleasure a night gown can give them. I must have special powers since all my past boyfriends still wear a pretty nightgown every night and more. I trained them well.

One night I offered Trey a matching full-length silk nightgown, just like what I was wearing. Saying we could be matching and it would make him feel so good. He slipped it on with much pleasure it seemed. I was in luck, he liked softness, and our night of sex was unreal. Ever since he has worn the nightgown each night and now I have him in matching panties.

So I started my next step, getting him in to a bra 24/7. By the way, I have “brain washed” two of my past boyfriends into wearing a bra and girdle 24/7, seems like for the rest of their life. I get so turned on when I see them and their bras are showing. They have such cute figures and for some odd reason they love wearing feminine underwear. They think it is so natural to have a bustline. They don’t seem to care that their bras show through their tops, or that they show feminine bustline, they seem proud of their figure. I love it!

Ok, back to Trey, so I got him a soft pink lacey camisole top to start with. I offered this during the summer for sleeping and matching pink lacey panties. He loves it. The first night he commented on my cool it was, and if it made me happy, he would wear it even during the day.

That was my foot in the door. I kissed and cuddled him, melted him into my control and said, “Trey, why don’t you wear it all the time if it feels so good?”

Bingo, I could tell he was excited with the idea. He was shy at first with the idea but I made him feel at ease and told him how much he would love it. We could be matching camisoles all day long then.

It worked; we bought several more camisoles and matching panties. No more man t-shirts, gone, just pretty soft camisoles for him. This was working too well.

He got very comfortable wearing his camisoles everyday. He did not try to hide them under his shirts and clothes. Did not seem to brother him. No one noticed or said a thing about the straps or lace that showed through his shirts. Even his sister who knew right away he was wearing a camisole.

Kim knew and approved. She said to me that his new “outfit” makes him a better man, more in touch with his feelings.

Next came the bra, the big move.

We went to the mall, Victoria Secret and I was buying me a bra set. My girlfriend Tammy works here and Trey is good friends with her to. Trey and I shopped around looking at all the pretty lingerie. I had him give me his feelings on a new padded lacey bra that I liked for me. He seemed all excited and told me how much he liked it. Never saw this excitement before.

As I was trying on the new bra, Tammy popped into the dressing room. “Cathy, is Trey wearing a camisoles top under his shirt”? I told her and she got such a big smile from my answer. I told her I want to buy him a bra and see if he will wear it. Tammy perked right up saying, “just like what you have done to your other boyfriends. That sounds like to much fun. I might try it on my boyfriend. We will have to get together and you can tell me how to get them to wear a bra 24/7”.

As we left the dressing room we both saw Trey looking around the store, touching bras on the rack. He seemed so at home in this girly store, like it’s his store to. We both looked at each other with a big smile, like we got him right where we want him, Trey’s next venture into femininity.

I pulled him off to the side and said, “Trey, you really like this bra and panty set don’t you.” His response blew me away; he said, “I really like this pretty bra, could I buy one for me?”

Bingo, that was it. I said, “of course dear, we can be matching. Would be so special, you and I having matching bras”. I thought he was going to jump up and down with so much excitement.

I whispered in Trey’s ear, “Sweetie, this is going to be so much fun. I love you so much”. Well, I thought he was going to be putty in my hands. He melted and I knew I had him right where I wanted him.

I grabbed his hand and took him saying, “lets get you measured for our pretty bras, Trey”. He pulled back saying, “Cathy, what do you mean measured? I can’t be measure here in Victoria Secret”.

“Trey, you have to be measured, how else will you know what size bra you wear? Besides Tammy is here and she can measure you in private.” I could tell Trey was now very nervous.

Cathy called over Tammy, whispered in her ear. Tammy’s big smiled me she was all set.

Tammy was all giggly and said, “Trey, lets measure you for that pretty training bra YOU want. Don’t worry, I know you love this lingerie and I love you wearing it too, like Cathy loves you wearing a bra”.

Before I could say anything she had the tape measure around me saying I needed a 34 bra. Cathy popped in saying, “Tammy lets start him off with an A cup and get him use to that for now”. The girls were all excited as I went to the dressing room to try on my new bra.

Both girls were right behind me, pushing me into the girl’s dressing room. “Slip the pretty bra over your shoulders Trey, I will clip the back, Cathy said. Tammy pulled on the straps, push “things” around. Wow, I had a bustline, a little bustline but clearly a shape. Both girls were excited.

I was excited to, something was mellowing me out and the bra felt good. I slipped on the camisole. Both girls gave their approval and said this was just “my look”.

As I tried to take off the camisole and bra, both girls jumped in saying, leave your new bra on dear, you can wear it home.

I looked puzzled and nervous. Cathy hugged me saying, “you will be fine, no one will know you are wearing a bra now”.

What did she say, “wearing a bra now”? Did she want me to wear a bra in public? Cathy hugged me saying, “Don’t worry dear, no one will know you are wearing a pretty bra. Remember we are match now, isn’t that fun?”

Tammy gave me a big hug saying I looked great. I looked in the big mirror and yes, I could see some straps and a hint of a bustline. Cathy grabbed my hand and said I looked fine, lets go before I could think about my new look.

Off we went through the mall to our car. No one looked at me strange. I actual felt good. The bra and camisole gave me a good feeling, very comfortable. Cathy knew of my acceptance and seemed very pleased.

As we approached our car, she snapped my bra strap joking about it say, “we are matching now Trey, I love your new look”.

I quickly looked at Cathy, like don’t ever snap my bra out in public. I thought to myself it felt fun, like my little secret. This might be fun I thought.

Then I am thinking she said, “my new look, what new look? Do I look different, do I look like a girl on my chest?”

Got home and I said I would be going out to cut the grass and proceeded upstairs to change. Cathy said, “Trey, remember, leaving your bra on. You told me you would try wearing your pretty bra 24/7”.

I said, “when did I say that and how can I wear a bra while cutting the grass in my thin t-shirts. Cathy jumped back saying, “Trey you promised and don’t worry about your t-shirts, no one is outside to see you anyhow”.

Deep down I liked wearing this VS bra. I was having fun but didn’t like wearing a bra in public. But I guess if I promised her, I better leave my new bra on.

Went to cut the grass in my new bra and t-shirt, thin t-shirt at that. Just then my sister Kim shows up. I was done. I knew she could see all the straps under my shirt. She came up and gave me a big hug saying, “Trey you are so sweet, wish I had a boyfriend like you”. With a big smile, she snapped my bra strap and said, “You are sweet Trey.”

Why am I getting my bra snapped so much? I was relieved at her acceptance of me wearing a bra.

Why do so many women want me to wear a bra?

“Hi Kim, come inside, got lots to tell you”, Cathy said. Kim was all excited and asked Cathy how she got her brother into a bra, he looks so cute. His chest has small bumps, so dainty”.

Cathy was all giggly and said, “your brother is a real sweetheart. I think he likes his pretty new Victoria Secret bras and panties. We even had Tammy at VS measure him. He was putty in our hands. Kim was intensely listening how she got him to this point wearing lingerie.

Cathy said, “he is wearing his first training bra now, a 34A, padded bra of course. Kim was all smiles. Cathy went on to say, “my next move will be put him into a B cup bra with inserts in time.”

Won’t he show more of a bustline with a B cup, Kim asked? With a very girly giggle Cathy said, “yes, but by then he will fully accept his fate of wear a bra and will like what a bra can do for his figure development. He will love having a pretty bustline when I am done with him. He will want to show to the world, be proud of his new figure!

I had one boyfriend couple of years ago that I got him up to C cup bra and he was proud of his shape. He had no cares showing the world he had a girly bustline. I even had him in a pointed 50’s retro bra. Very old fashion, but he loves it, still today I see him walking the streets with a big smile. He walks with his shoulders back, chest out and wears the tights sweaters, saying look at me, I have a big bustline”.

Just then the back door opened and in walked Trey all sweaty from the heat and cutting the grass. Now you could really see his new bra, like a wet t-shirt. We made no mention of it and went on girly talking. Trey could see that both Cathy and Kim were deep into girl talk. He grabbed some water and went to clean up.

As I was leaving the kitchen, Cathy said, “I put out some fresh clothes for you on our bed, Trey”. When I got up there I could see another bra exactly like I had on. She must have bought several bras for me, they were my size, not hers.

I got the message, after cleaning up I slipped on a new bra and the shirt she laid out for me. Clearly you could see the bra under my shirt. I was nervous with that, but I just went ahead and got dressed.

Back down in the living room both Cathy and Kim saw me walk in and they both did a high five with a huge smile. I asked what that was for. They both giggled saying it was a girly bet and we both won.

Kim gave me a hug saying she had to leave, not before snapping my bra. I asked her not to do that, felt uncomfortable. She smiled saying, “get use to it brother, you use to do it to me all the time”!

After Kim left, Cathy gave me a big hug saying, “Trey I am so proud of you putting your bra on after changing. We are still matching and that is a real turn on”.

All I heard was her words, “your bra”. What do I have myself into here?

Cathy told me that Betty Smith was coming over now to help me get comfortable with our new fantasy. I asked what for. Cathy explained she could help us with total acceptance of you wearing pretty lingerie.

“I thought I was ok, look at me wearing the bra now for you”, I said. Cathy said she will “seal the deal” and make it much easier for me, trust her.

I thought, “much easier for her”? What does she need to make more easier?

An hour later in walked Betty. What a nice lady. She made me feel so relaxed. She explained she was going to talk me through my acceptance “feeling good” as she explained it. What is feeling good I thought?

Betty told me to help the system, she asked me to take two pills. Not sure why, but I took them. Within minutes I was so relaxed, they could have dressed me in a wedding dress and I would have cared.

Betty stared into my eyes relaxing me, gaining my confidence. I think she was hypnotizing me. I think I fell asleep, not sure.

Next thing I knew I was awake, sitting there as Betty and Cathy were talking. Betty asked me how I felt and told me she was all done and everything went fine.

I asked what went fine? Both Cathy and Betty smiled as said, “I was a perfect patience and I was all set.” I was confused but not mad they were not telling me anything.

Betty hugged me saying, “all will be fine, enjoy your new life Trey”, as she left.

What new life I thought?

Cathy hugged me saying, “lets go cook dinner together. We are going to have so much fun Trey”.

We fixed dinner. I thought to myself I never fix dinner, what is going on here. After dinner Cathy asked me to clean up and without a question I was washing dishes. I never use to wash dishes; I did hate it, but not now. What was going on?

When I was done, Cathy took my hand and led me upstairs to her dressing table and sat me down. She smiled and said lets see how some pretty makeup will look on my baby.

I just sat there; I did not say a thing as she put makeup on me. It was like she was controlling me. I could not resist.

Deep down I wanted to stop her, but for some reason I just smiled and said, “That looks nice Cathy”.

Cathy gave me a huge kiss and a hug saying I was so sweet and how much she loves me. That made me feel good and she knew it.

The next morning she announced we needed to go shopping for more lingerie. For some reason I did not resist, I seemed fine and excited about that. Cathy even put a little makeup on me and I did not say a word.

Off we went shopping to Macy’s department store. Yes, I was wearing a bra, matching of course with Cathy and it was showing through my shirt. I had no problem with the bra showing and for all to see it under my shirt. Cathy had the same shirt on and I saw her bra to. I thought it very natural my bra was showing through my shirt.

Walking into the lingerie department, the young sales girl was confused with my presence. Cathy asked the clerk if they carried 50’s retro bras. I was confused about kind of bra that was but then what did I know about all this girly talk.

The clerk smiled and said, sure right this way. Cathy spotted right away the bra she wanted and grabbed a pretty pink lacy bra. I thought to myself this bra is a big one, look at those pointed cups. Cathy asked if we could use the dressing room, pulling me with her. The clerk smiled and said of course right this way.

Cathy instructed me to strip down and try this new pretty bra on. I was confused; I thought the bra was for her since it was much bigger than my little bras. But for some reason, I did what I was told. It was like she was controlling me and I did exactly what she wanted all the time now.

I slipped the bra on, wow, was it bigger. I was scared and Cathy saw my face. She told me not to worry; it is a very pretty bra for me Cathy said. The cups were not filled in at all as she called in the clerk asking for inserts. The clerk saw me in the retro bra and smiled saying of course we have insert, I will be right back.

What were inserts? I found out quickly, she must have had them right outside the door. Cathy pushed them into my cups and boy did they get heavy on my chest. Both my girlfriend and the clerk announced the inserts fit perfectly.

They were happy, so I guess I was too. I smiled and said, “yes, they do look nice”. I over heard the clerk ask Cathy, “where did you find this guy? He is so sweet, I want one”.

Cathy instructed me to leave the new bra on and put my shirt on. Putting my shirt on was hard, was a very tight fit. Got it on, looking in the mirror was a real “picture”. Here was a guy with a bustline most girls we die for. What is wrong with this picture?

But so some reason I was ok with the new look. I looked at Cathy and said, “wow this looks a lot different than my other bra. Will this be my new bra I asked her?

Cathy smiled and said yes, from time to time you will look very nice in this new look. I hope you like it, looks very pretty on you.

I asked if she would wear a bra like this too so that we could be matching. She giggled and said no, this was just for me, my new look.

So, I walked out of the store in my new pointed bustline. For some reason again, I felt almost normal, like this was the bra men wore and it was perfectly natural for a man to have this pointed bustline.

I watch other people we passed. Most people could care less I had a shapely chest. Some teenage girls giggled and pointed at me, but for the most part I was fine with my new look. Cathy was as happy, seeing me in this large bra and very projected bustline.

My walk was way different though in this bra. My chest was heavy and bouncing around. I adjusted my bra straps, a new feeling having this straps all over tugging on me. I looked at Cathy and she knew my thoughts. “Trey, don’t worry you look fine. A little bounce is a very sweet look. You will get use to it and you will like it”, Cathy said.

Not sure I would get use to this bounce or look, but for some reason I did not resist her.

We stopped by Victoria Secret and it was like Cathy was showing me off to Tammy. She called Tammy over and Tammy just looked at me saying, “Trey, you look so sweet, love the new look”.

I keep thinking what is my new look. I did not think there was anything really different with my look, just a bigger chest. But Tammy kept saying she thought I looked great, so sweet.

We bought more of my other 34A padded bra, ones we bought the other day for me. My training bras as Cathy call them. Still didn’t know what training bra meant, but I didn’t care. I liked those bras better than this pointed retro bra.

As we were driving home, Cathy announced we would be stopping by my sisters Kim’s place. Not sure why, but they seemed to become real good friend lately.

As we opened the door to Kim’s apartment, Kim eye just bugged out. Before Kim could say a word, Cathy popped right up saying, “Kim don’t you just love Trey’s new figure? Isn’t his bustline so soft and feminine?”

Kim got the message and said, “Yes Trey I love your new look. I have always wanted to have a 50’s shape like that. It is so cute.”

I felt even more relaxed since my sister likes this new look to.

I popped up saying, “I like the 50’s look too, but I think I will need different shirts to wear with this kind of bra. This shirt is too tight and not comfortable.”

Both girls seemed excited as they both said, “Let go shopping tomorrow for a couple of tops that will fit your new look. You will need blouses with darts in them, even some cute sweaters.”

I was confused thinking what are darts, but I didn’t ask.

Kim invited us in for dinner and we had a fun night. Kim could not get over my new bra and the look. She even asked me to take my shirt off so she could see the retro bra. “Didn’t know they sold those bras anymore”, she said. She was amazed to see I had gel inserts in my cups, really filling out the cups. I thought it natural to have inserts, how else could I shape the bra? But then what do I know, I thought.

As we were leave, both Cathy and Kim gave each other a high five again, like this was there new signal they did good. I think they were thinking how well they help me with my bra selection. What did I know?

The days and weeks went on, every day I now wore a bra and panty. Plus she got me started on wearing a girdle and nylons. She said it is all part of what men do and wear and I bought it. I thought it was what men wear, these feminine things.

So I would think nothing of going out into the public, going about my normal day, even went to work in my bra, wear tight clothes, show off my bustline and thinking nothing of it, like every other man does the same thing.

Not sure why but Cathy thought I should only wear my VS t-shirts bra to work, not the retro bra. There are mostly girls at my insurance office so they thought nothing of me showing up every day in my bra. They thought I looked better and was really much nicer now that I was wearing a bra. Could not figure that out, but hey, they were nicer to me. I was now treated better and like one of the girls now.

One day I wore my retro bra to work. Wow, did that cause a lot of attention. All the girls swarmed around me asking where I found that bra and if I like wearing it. I could not believe the attention I was getting over this 50’s look. I was enjoying the attention all day long.

One of the girls, Pam asked if she could see the bra. I started unbuttoning my shirt and she stopped me saying, “no not here silly, follow me were it is more private”.

She took my hand and led me into the women’s bathroom. That made me very uncomfortable, but I could not stop her. In we went, I undressed and showed her the bra.

Pam seemed very excited, loves the bra and saw I had inserts in my cups. She thought that was fun, but suggested I get a different pair, ones that glue to my body for a more secure feeling.

Her husband wears them and he says they really feel like real breasts. I looked at Pam saying, “Your husband wears a bra and forms?”

“Yes, Trey he does and he loves it just like you do. I think you to should meet and talk. I would like to put him in this retro bra, he would look so much better than just A cup bra he wears”, Pam said.

I could not believe there was more men out there just like me wear lingerie. Pam says she knows of several men who wear a bra everyday and love it.

I told Pam I would love to meet her husband and compare notes. As I laughed, thinking this is going to be so weird.

Back home that night Cathy was excited I met another girl who’s husband wears a bra. She suggested we go out this weekend with them, maybe even shopping. For some reason I got excited knowing I might have a friend who also wore bras, thinking bras must be a natural thing to wear.

I told Cathy how Pam wanted to see my retro bra and she pulled me into the ladies room to see it. I was so embarrassed, but the other women in the bathroom had no problems with me in there. So strange I told Cathy. Cathy smiled and said it was ok, just so long as I went with another woman to the ladies room. She told me never to go in alone.

Time went on with me in my bras and panties. I thought these clothes were natural for me to wear now. I enjoyed them and for sure Cathy loves them on me.

With the retro bra, we bought me women’s blouses and I get very comfortable wearing them. Even a stretch sweater, ones that showed off my bustline a lot! Strange, but I like the look, the shape and did not think twice walking into a ladies department store buying women’s tops.

Cathy and I became good friends with my co-worker who’s husband Paul is a crossdresser. He was now getting to the point that he looked like a girl and not a man. He even wore a wig and a dress everyday. He was so happy in his new outfits, I had thought, “would I like wearing a dress like him”?

I was nervous that I thought that. What is going on in my brain? Then again I look down and seeing my chest and my bra showing through my top. Hello, I wear girl’s clothes now.

Several weeks later the four of us were out shopping as do alot. Paul wanted a new dress for a church event he and his wife were going to. We all helped him pick a dress, it took forever. We all were in this large ladies dressing room. We sat there as Paul walked in and out of the small dressing room modeling all these different dresses.

Paul seemed to be a natural at this. Modeling all these dresses. He seemed to focus on me asking me each time how I liked the dresses and how the fit was, was the shape right, the length right, good color, was the neckline too low, etc. Why me, like I knew how to fit a dress?

What am I doing here I thought. I am inside a ladies dressing room watching a man trying on dresses. He looks good and very comfortable in them. Was I jealous of him wearing a pretty dress?

All of a sudden, Paul gives Cathy a dress he tried on before, gave her a wink with a big smile and said, “this is the one”!

Then Cathy jumps up grabs my hand and drags ME, yes me into the other small dressing room and says, “Trey, I know YOU want to try this dress on. I saw your face when Paul was modeling it. Take your clothes off and try it on. It’s only us girls in here and I think it will be so pretty on you, sweetie”.

I was shaking. She was right, I wanted to try on this dress. She started unbutton my top and guiding me toward her goal, me into a dress.

I could not resist her command. I was getting so excited and Cathy saw my desire. She seemed equally as excited.

As I slipped the dress over my head, she said, “Trey this bra will not work for this dress and you will need a high waist girdle for this dress. That girdle will show off your figure much better”.

I looked into the mirror and could not believe how good I looked in the mirror. I was in love, I loved it and Cathy knew it.

Just them Paul knocks on the door and says, “Trey come out here and model your new dress”.

Did he say your new dress? Paul was just using this shopping spree to get me into this dress.

He opened the door and with a huge smile, he blurted out, “Trey you look great. That dress is you. You have to buy it”.

I looked at Cathy and she smiled saying, “Yes, Trey it is smashing on you. The dress is you, brings out your feminine side so beautifully, I love it, you must buy it”.

I am thinking, wait a minute, buy it? I don’t wear dresses.

I quickly closed the door staying in the dressing room with Cathy. I looked her in the face say, “Cathy I don’t wear dress, why should I buy it? What are you and Paul up to?”

She hugged me saying, “Trey look at you, you look divine, so sweet and I know YOU like this pretty dress. Relax and enjoy your newfound feelings. We are all here to help you and beside we are having so much fun now days that you found your true feelings. I know I am right, don’t fight it, sweetie!”

I melted in her huge hug and knew she was right. I did love this dress and all the feminine clothes I have been wearing. She knew she had me this minute.

I opened the door as Paul and Sally were smiling standing there and I announced with a big smile and happy tears running down my face, “Yes I do love this dress, I will buy it if you think it looks good on me”.

They all giggled saying, “Trey the dress is you, you look great, laughing saying, you will now need so much MORE girly things, like high heels and a strapless bra”.

We all laughed as I spun around modeling MY new dress. Cathy knew I was hooked.

The End