5 months ago in June, I was in a annual chalet meet-up with my secondary school classmates. We played poker card games and agreed to have a special forfeit whereby the loser girl had to go braless for 24hours and the loser guy had to wear a bra for the next 24hours. Obviously, we were for the game as we wanted the girls to strip of their bras.

Unfortunately, it was not my day and I lose the final game. I did not want to spoil everyone's mood so I agreed to the forfeit and one of the chio bu ah lian took out her black lacy bra and threw it to me. The rest of the guys and girls quickly held me and stripped of my shirt and dressed me in the bra. But the bra was rather small size for my chest width and I felt damm tight and I complained and said, " Don't play lah. I treat you all to a meal, wear bra very stupid leh " But my friends die die wanted me to wear bra and make me malu. I suggested a 2nd round of the game to see another person kanna but my friends purposely wanted to sabo me and said it was dinner time and they wanted to dine out and no BBQ pit was booked.
Reluctantly, I wore my black Tshirt with Gina's black bra underneath and went out with them. I was so afraid passerbys would look at me but suprisingly nobody really took notice of me. Probably because we were walking in group. We went to a nearby coffeeshop and ordered alot of beer. That night I drunk alot of beer and really felt quite drunk. I did not know why but I felt horny wearing Gina's bra and I kept secretly looking at Gina who was also drunk.
We took a cab and returned to the chalet and I collapsed onto the bed with Gina's bra on. The next morning, my friends woke me up by snapping the bra strap and I was quite pissed off and took of the bra on the spot. Some of the friends complained, " Haven 24 hours leh." But who really cares, it was so uncomfortable and tight.
I asked Gina if she wanted the bra back and she scolded me saying that I was too big size and I overstretched her bra and her bra was spoilt. So I told her I would pay her and she said she wanted a new one and told me to go and buy for her. So I asked her if she wants she goes with me as I would not know her size. Actually was an excuse because I just wanted to go out with Gina. Suprisingly, she agreed.
The next weekend, I met Gina at Centerpoint Robinsons.
I was wondering her boyfriend, who was a butch would be damm angry should she see me with Gina shopping for Gina's bra. Gina told me her size was a 75B and i was probably 85 or what so I spoilt her bra. Anyway, the triumph bras were like buy 2 get 1 free but still were damm expensive cause 1 costed $29.90. Gina said she subsidies $10 and told me to buy 2 for her and I could have the free bra . So I replied her, " For what I want a bra! " And she jokingly said, " Then you give me the free one also if not buy for your sister loh." Actually I could not be bothered what she was talking about as I wanted to tell her something else. I spoke, " Gina, I like you for some time already." She was like very shocked and quickly replied, " Haha, I only like my steady. You go wear a bra, I par tor with you loh." Oh yah, her steady was a butch which meant she was a lesbian and she only liked woman. But I did not know why and I replied, " Wear loh, for you I don mind."
The next thing i knew was she took one more 85A pink bra and dragged me into the fitting room. I was like so malu but I looked around and saw the salesgirl was talking to another customer so i was slightly more relieved. In the fitting room, she closed the door, stared at me and said, " Wear loh! Show me! " I was like kind of confused but I told myself I must prove to Gina I would do anything for her and I tried the bra. Suprisingly, it felt more comfortable compared to the last time because the under bust size was larger. However, the cups were not fully filled, obviously I had no breasts.
After we left the fitting room and I paid for all the 3 bras and left the store. For around 10minutes, Gina remained silent throughout and suddenly she said, " If you want to be my steady, you go change into the bra now." She sounded serious now and I wanted to prove my love for her and I took the bra, went to the Gents and changed into the bra. It was not very obvious as I was wearing a dark long sleeve Tshirt but I was still afraid people could see that I wore a bra then.
I went out of the Gents and told Gina, " See, I will do anything for you." Gina then broke into laughter and tears, exclaiming, " Why are you so stupid! Ask you wear you wear." I just replied, " Because I love you."
For the next few weeks, Gina agreed to come out with me on single dates but each time she would check if I was wearing the pink bra I bought with her. I did not question her doubt about why she would have this pervertic mentallity to date a guy and makes him wear a bra. Anyway, I was happy to be with Gina.
One day, Gina said she had something for me. She bought from Watsons this Activa breast enlargement cream and pills and wanted me to use it. I was like " Crazy ar! You want to turn me into a transsexual or what! " Gina explained the bras would fit better if i had breasts, just small breasts will do, not very big ones. I told her it was impossible and she threatened to break up with me and she said she would stop seeing the butch if I promised her. I think i was love-blinded and I actually agreed to doing it.
Gina would then call me up everday to check if I was on the pills and using the cream and massager and wearing the bras i bought for her everytime I leave my house. After 2months, I actually had small breasts growing and I had a size of 80A. At first the chest was soring and my nipples were very itchy and pain. Wearing a bra would make that area more relax and comfortable. At times, I did not know should I feel happy or sad when I look at my breasts. Now I could not take off my top in the public, not even at home and not to say swimming. As promised, Gina broke up with the butch and went into a full time relationship with me.
However, the worst thing came when she told me she wanted to break up with me last month. She said she like real man and I was a man with breasts and she would not want me. This was purely excuse. I found out from her friends she got to know a new guy. How could she do this to me. She made me into a guy with breasts and she breaks up with me. Why was I so stupid?

Another upset came 3 weeks ago when my sister felt something wrong with my body and caught me wearing bras. I explained the whole situation to her and she felt disgusted but promised to keep this matter undisclosed to my parents provided I throw the bras away.
I could not bear to do so. Those bras were bought together with Gina. So I packed them into a box and locked it in my cupboard. However, nowadays when I wear thin-cloth shirts out, my nipples seems to be very protruding and my breasts or the fats tends to sways around when I walk fast. I seems to feel uncomfortable without wearing a bra now. I don't know what I have turned into now. I have surrendered back to wearing the bras 2 days ago. I feel uncomfortable without wearing bras now, my breasts requires support. Sometimes I think should I become a transsexual or what. I think people on the street knows I am a guy and can see I wears a bra. How am I to face my family and friends now?
