Throughout the remainder of my high school years, I was pretty much a cross dresser. I tried not to be too open about it in scchool. Even though I wore girls clothes to class, I avoided ever wearing anything obvious. Most people knew, however, and rumors circulated about me being gay. I didn’t really feel any interest in guys, but I often wondered myself if I might be gay just because it seemed like the obvious conclusion from how I liked to dress.
I didn’t have any girlfriends or boyfriends in high school, and looking back I think I would have described myself as sexually ambiguous.
At home I wore much more feminine clothes that I did at school. My first nightgown was a hand-me-down from my older sister. It was gray and not particularly feminine, but I enjoyed wearing it because I had seen my sister wear it for a long time and I associated it with her. Then one year for Christmas my mother gave me a very nice and very feminine nightgown along with a big fluffy pink robe. And they quickly became my outfit of choice if I was just hanging around the house.
When I hit 18 and went off to college on the other side of the country, I owned virtually no mens clothing whatsoever. Instead of appreciating my independence by dressing more openly as a woman, I did the opposite. I tried really hard to be “normal” and I started wearing more and more men’s clothes. Soon, I was dressing like a man except for panties.
I missed all my women’s clothes. I kept them in a bag in my closet and would occasionally take them out and dress up. Then I met a guy on campus who was also a cross dresser and be quickly became friends. We would go shopping together and dress up together, and we had a lot of fun. Eventually one day, after modeling panties for each other, we kissed. A few kisses turned into oral sex. And suddenly I had a boyfriend.
He and I were both bottoms, and we didn’t have much anal sex, but we had a fun relationship with more blowjobs than I knew what to do with. He was sexually active with several other guys and I was embarrassed to admit that I had lost my virginity to him. My jealous of the fact that we weren’t exclusive is what broke us up after about six months.
After having just been in a relationship with a man, I started to accept the idea that I was gay. I continued to really limit my cross dressing. I had a friend who was a bisexual woman who had just ended a relationship with another woman and she and I commiserated about our relationships. Soon we realized we had feelings for each other. Even though she knew I had been in a relationship with a man, I wanted her to see me as straight and I went out and bought some mens underwear specifically because I presumed we would eventually have sex.
We not only had sex, we got married a few years later.
And I gave up cross dressing in exchange for a happy heterosexual life with her.
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