A friend recently asked me how I got interested in all this and I found myself reminiscing about my first boyfriend. Here’s what I told him:
I started meeting transvestites and gay men in the modeling and fashion industry (surprise!) and at first I was very uncomfortable around them. Maybe my fathers voice in my head yelling horrible things. But they became my best friends and I realized that I was way too caught up in the sexual possibilities every time I met someone. I slowly learned that friends could be just that, and even tried to have straight friends, which I think was a test for myself and I failed.
I also grew up with a great guy who trusted me enough to confide in me when we were teenagers. He’s a big guy, over 6 feet tall and wore flannel shirts and drank (I know-you’re laughing). So when he told me about his fetish for not only wearing women’s clothes, but being Forced to wear them and being humiliated I was baffled. Of course he didn’t come out with this all at once but eventually he told me his fantasies.
I did not get it at all and told him I’d try to help him if this was all he wanted. We talked and talked about it and one day decided to do it like a play. I would “catch him” breaking into my house and stealing my lingerie. Then get mad, threaten to call the police, and punish him by demanding that he wear some of my things if he wanted to so badly.
I was having fun with it all and then I saw the look he gave me when he took off his clothes. It was a look of such vulnerability and trust that I thought I would cry, and then he told me he loved me and I believed him. I decided I loved him too and I held him for a long time.
Then I held up a pair on my panties and saw how excited he was. He was like a kid in a candy store and we had the most amazing sex I’ve ever had in my life.
The best thing about our relationship was that I could tell him everything since he told me everything. I told him how I fantasized about the girls in gym class and a teacher at school. I told him things I’d never even thought about telling anyone else and we were in love. I learned that to be that vulnerable and honest is a rare thing and I need that.
Two years later when he went off to college we agreed to keep in touch, but we both knew it could never be the same. I spent the next 15 years looking for someone like that in a partner and it took a marriage and a divorce to see that I was settling for the closest I could get to that which was not enough.
Now I have a girlfriend I feel the same way about. We have no secrets and are very much in love. I know this hasn’t answered your question but the rest is another story.