Molly's First Time

When I was a teenager, I was dealing with a lot of conflicting emotions. Mainly, I really, really would have liked to dress like a girl.

I was a geeky boy, full of conflicting emotions. Sometimes I just wanted to try on a pair of panties, sometimes I wanted to sign up for full sex change surgery. There was no way I could tell anyone this.

It was the early 1990s and information on gender was hard to come by. I once waited several months to come by a copy of Caroline Cosey's autobiography. Then I immediately threw it away for fear of my parents finding it. I'd fantasize situations where I'd be 'forced' to play a female role, the hospital screw up where I'd get a sex change by mistake, the weird disease where I'd have to take massive dose of estrogen, the sneaky girlfriend who slipped hormones in my food, having to stand in for my (imaginary) older sister at her wedding. The list goes on.

But in 1992, the Internet came to my house in the form of a dial-up BBS (bulletin board system). For the first time in my life I could communicate anonymously and talk to people who maybe understood where I was coming from. At the age of 17, I came out to the local electronic world (the dial-up BBS only served one community).

Soon my prayers were answered in the form of a woman who was very sympathetic to my feelings. She said there was nothing wrong with what I was experiencing and if I was interested, she'd be happy to dress me.

Wow!

It wasn't long before I visited her house. She was a nice woman of about 30. After she sent her preschool son into the other room, she told me I'd make a wonderful girl and she'd be happy to help me on my journey. She offered to buy me clothes, take me shopping and provide opportunities to spend time as a female. She even let me try on some of her pantyhose. It was what I'd always dreamed of.

Except that her husband was there, too. And he watched us the whole time. He complimented me too, but in a way that made me feel very uncomfortable.

Afterward, they both e-mailed me. The woman mentioned how her husband was crushing on me (she was fine with this). Her husband was much more graphic about what he'd like to do to me. In retrospect, I'm lucky that didn't end badly. I never visited them again.

Also on the BBS, a friend mentioned (to my male persona) that some girl at his school was trying to find a date who'd be willing to go to homecoming in drag. I immediately told him to tell her I'd be interested (you know, as a joke). Two days later, I met a real life girl whom I hit it off with and told my friend not to bother.

The next year I was in college. I had freedom and privacy. Still I was too scared to contact an LGBT group. I just couldn't risk being found out. But the BBS’s came through for me again when I was contacted by a local crossdresser who told me about a local group for men who liked to dress in drag. He offered to take me along to the next meeting and to help me dress up. I went for it.

Chris was an extremely nice guy who made a very convincing woman. While I wouldn't shave my legs for the experience, Chris worked around that with dark hose. He did a phenomenal job with press-on nails, a wig, clip-on earrings, etc. He spent so much time on my appearance that he didn't have time to dress himself, so he escorted me “in drab.” as he put it. Going to a meeting (in a hotel conference center) on the arm of a man in his 20’s certainly gave me some interesting and exciting feelings.

It was thrilling at the age of 18, to be the youngest in a room full of gender-variant people. I was introduced as Molly (after my long time crush, Molly Ringwald). More than one person subtly asked if I was a genetic female.

A couple of months later I visited Chris again and this time we both went to the meeting en femme. I think Chris might have been romantically interested in me, but I may be flattering myself. In either case, he was a perfect gentleman and lady. Chris also introduced me to crossdressing fiction, which then was only available in printed form. Chris really opened my eyes to a lot of new experiences and I wish I could thank her again.

Sorry I do not have any pictures of Molly. She was a cute girl and I miss her.


I invite all femulators to share your first crossdressing experience. Try to recall that moment the first time you tried on a woman’s garment and began the process of unveiling and exploring your feminine self. To entice you to share your first time story, I will give away a free copy of my e-book Fantasia Fair Diaries to all whose stories I use in Femulate.

Wearing Nicholas.

Erik Handoko, male model