An Uncomfortable Virgin: "a Cross Dresser will not judge me..."

I had an interesting encounter a few nights ago.

About an hour and a half into a chaturbate session, a young man asked me to go PM with him. Normally, I don't do that. Being an exhibitionist (at least when in character), I just tell them "I would rather do whatever you want to do right here in front of everyone." Most men go for that and we play right in my broadcast channel.

This young man, however, insisted. He was very polite about it, so I went ahead and went into PM with him. Now, I'm not positive how chaturbate works, but I'm guessing my video was still available for everyone but my text chat was just in the PM tab. I'm not sure and I don't really care.

He brought up his cam and I watched him as he rubbed lotion on his cock and masturbated himself. He was being complimentary, telling me I turned him on, and how pretty and sexy I was. It felt good. As he went on, he mentioned that he didn't like gay men or cross dressers and he was glad I was a woman. I paused for a moment, wondering whether to tell him or not.

How did he not know? I was in the Transsexual area, which is the closest they have to a CD/TV area. I made no bones about it when someone asked, but he hadn't.

After a few minutes, I typed "well, I guess you have a decision to make. You are chatting with a guy." He typed back "I know."

That made me pause. So what was the earlier comment all about?

We kept on until he came, then he started chatting. He's in his early 20's and a virgin. He seemed embarrassed about it. He expressed some insecurity about his looks and personality. This really bothers me. I hate how we live in a world where people feel like this. This whole focus on looks and hotness and all of that is destructive, especially to insecure people. While I think it's fun to get done up (a tux and shined shoes or a skirt and heels), and try to look your best (groomed and polished and all), it shouldn't be something to compare ourselves to.

AND he wasn't a bad looking guy at all. He needed to smile more and show a little confidence, sure, but he was a good looking kid. It made me think about myself at his age. I felt the same thing. I focused on music and let that be the side of me that attracted people, because I KNEW I was pretty yucky looking. I look at photos of my younger self and I was no better or worse looking than the average guy, but I didn't feel that way.

It made me feel very protective of the guy, so I tried to talk him up. He dropped another interested comment a few minutes later. Evidently, he'd known I was a man all along but decided to go ahead because he was very shy about being a virgin but knew that he "wouldn't be judged by a cross dresser."

It would have been very easy to take offense at that, but I didn't. Maybe that's something he needed to do, maybe I offered him something helpful. Maybe it will make a difference in the long run.

Or maybe he just got off and went back to his old life.

Even if that's all I did for him, it's something...

Pics from chat sessions

It's been about 2 weeks since I posted. Since then, I've been on the chaturbate site about half a dozen times. Each session lasted for more than 3 hours, with men coming in and out of the room, keeping me curious and involved. I've started taking snapshots during the sessions and wanted to share some of them here.

I'm usually masked. Putting on the full face makeup takes a lot of time and I'm too anxious to get online. Plus, I'm not particularly pretty when made up anyway, so I think it's just not worth the time.

I bought two more wigs. With Halloween right around the corner, its easier to find wigs, makeup, and costume pieces. Both are long hair, one blond-ish, one black. They added a new feel to some of the sessions. For me at least.

The first two are from the same shoot, just feeling sexy and girl-ish.

The next time I was online, I decided to try a little more submission. I chose my black corset rather than white so the little bit of rope I was using would stand out more. I was wearing a full-body fishnet stocking underneath. I love the look.

I went offline at about 3 a.m. and tried to go to bed. But I couldn't sleep. I was very turned on and needed some relief. So, I went back online for a little while. This time, I went for a more feminine, soft look. I took a red skirt and used it as a full dress. I walked around my shooting area for a long time, trying this and that post, trying to really get into the feeling of the girl. She really did turn into quite the wanton little thing.

It was an exhausting night and I got to bed too late. I was in a bit of a fog most of the next day and caught up on sleep the next night.

My observation from that night is that the difference in hair color seems pretty significant to me - blonde versus black hair. I want to write a bit more about that, but the thoughts are only half-baked right now.