I’m going to start out by talking about how I started down this path of woman’s wear. At first, I was not like this, but was told later on that when I was between one to four years old my sister put me into a swimsuit or one of her old leotards that she’d outgrown. I thought swimsuits were the same, a one-piece that covered everything up.
At five, I started to notice that I was wearing a girl’s swimsuit and rebelled. I had just shorts, and this was how I went to the public pool until I turned eight. I started going through puberty early, I didn’t know what was going on as my breasts also began to grow and be sensitive. I began to realize that I was different around 10. My breasts were developing, and I started getting looks in the locker room during gym class from the other boys.
I wore tee-shirts until I was told that I couldn’t in the pool. If I wanted to swim, I had to lose the shirt. I reluctantly did. The gym couch asked a girl in the class to get a swimsuit my size and hand it to me. I was making everyone uncomfortable swimming topless. Many of the girls weren’t happy that I had breasts and could let them free, and the boys were distracted because there were breasts bouncing around out in the open. I was told that if I wanted to swim I had to wear this swimsuit.
I protested, asking to just wear a tee-shirt, but I caved in when told it was that or not at all. I had to ask for help in how to put it on—it had a racer back. A girl showed me how to put it on. I got it on, it was a little tight, and I did have to ask a girl l to help me fix the straps right. After I came out there was a cross of laughing and clapping from the rest of the class. There were catcalls from the guys and the girls giggled. I felt humiliated by the experience, feeling that I was getting teased and mocked by the school.
After swim class was over, I took the swimsuit off and threw it in with the towels. “Good riddance,” I thought. I went home and did not want to talk about what happened at school. At the next swim class I went to change and in the locker was that swimsuit hanging. A note instructed me to not put the swimsuit in with the towels and to remember to hang it up in the locker or I’d get detention. If I didn’t wear it I couldn’t join the class and I’d get a failing grade.
I didn’t have a choice so I put it back on. This time after the smirks and comments, I got more use to wearing it out in public. I remembered that when I was younger my sister had me in a suit like this, but it had straps that tied around the neck. I started to feel more comfortable in that swimsuit at school. The next Friday the girl that helped me fix the straps asked if I wanted to come over to a party at her house on Saturday. I told her ok. I liked her and thought it would be great to go to her house and hang out.
When I arrived at her house, she wanted to know if I brought my swimsuit with me. I hadn’t, and she apologized for forgetting to tell me it was a pool party. I told her I would go home and get my shorts and come back. She said not to worry that they had extra swimsuits that I could wear for the party. She led me into the pool house to change, handing me a box of swimsuits of different styles, saying I could wear whatever one I liked and then come join the party.
I opened the box to find 20 girls swimsuits of different colors and styles. But no shorts. I stuck my head out and asked where the shorts were and she said that I wear a one piece at school. She said we were the same size and those were her extra swimsuits. Put one on and come join the party! I decided to wear a plain black suit; it had a skirt covering the bottom and was easy to put on. Reluctantly, I joined the party that was 99% girls that had on their swimsuits.
Ii got excited a few times and didn’t want to leave the pool or be seen “wink wink.” For the most part, I had fun as the day passed. As the others started to leave, I got up to get dressed and she told to wait and stay a little longer. There was a sleepover and a few others were staying because Sunday was her birthday. I got asked to stay and called for permission and got it. Well, this night changed my life and turned it toward where it is today and how I see clothing as a whole. She and her girlfriends had plans for me, and they wanted to try some stuff on me.
It turned out her parents did not know I was a boy, and she didn’t tell them. I was just her friend Bobby, though they thought I was her friend Bobbi. This was the night Bobbi was born.
Look out for part two where you find out what changed my life as it is today.