I think it was the late 90's I discovered online chatting and I was so excited about it. While I often looked at pornographic pictures and movies I have to say what really turned me on was reading erotica. I liked it more because I was able to use my own imagination and my own mind to see what was going on as I read, I was able to add in little extra details, embellish where I thought it was needed. It is harder to do that when looking at pictures or watching a movie, you see everything there is. So when I found online sex chatting I was thrilled about it. This was also before I found out about transsexual women and realized there was such a thing. I think it was a couple years later that I found transsexual women online, around 2000, maybe 2001. But that is another post, so back to online chatting. So I logged in as myself and tried to find a woman to chat with. Now being a guy it was hard to get women to want to chat, or to get them from leaving the chat. I was very descriptive and I think the was not what they were looking for, I wanted a story, set up a scene, establish what people were wearing, but it seemed most women just did not care about that, they really did not seem to be that into it, or interested and I found I did most of the typing. There were also many more guys online then women. And I always had to hunt down the women to chat with them, and normally it took a while to find one that would actually talk. I tried different web sites, different names, different approach lines. But it did not seem to be working. I am not sure what made me think about this .. but one night I was horny after trying to start several chats and failing that I logged off and logged back on as a women. I told myself that I would just type what I wished the girl would do to me, it was not gay, I was not doing this to the guy, I was thinking about what the girl would do to me. I instantly got several PMs about wanting to chat. I have to say my heart was beating fast and I was excited.
So I spent that night talking with guys about sucking them off and being fucked by them. The guys liked my descriptions, my focus on detail. The guys seemed to like how I chatted and talked with them. They liked me setting up a scene for them, tell them what I was wearing. I also did not realize it at first .. but I was not really thinking about what I wanted a girl to do to me, I was actually picturing myself as the girl doing this to them. But once I realized it it really did not bother me because I was turned on by it. So I kept talking with guys night after night and being the girl. I went online and read and watched videos about giving blow jobs so I could better describe what I was doing to them. I watched porn to research the girl so I could better chat online with guys about being fucked. I also figured out that many guys would not ask about anal sex, but if I brought it up they would jump at it. So I started shifting away from talking about vaginal sex to anal sex .. and fingering my butt while talking with them. I also created a special email account as a girl so I could email people when they wanted to keep in touch or try to coordinate chatting. I scraped the net for pictures of girls I could send to guys and say I was here. I need girls that had different photo shoots so I could have different outfits to send and pretend it was me. I wanted ones that did not look like there were done in a photo studio, and having some naked pictures was also great to send along (a favorite was Divinity18 also known as Jayden, I think she was underage when she started posting pictures, but she never showed her nipples, most of the pictures she had clothes on but she always stripped but covered her breasts, so you only got side or bottom or top boob view, never nipple or full naked breasts ... guys online seemed to really like this. I actually paid for her web site so I could get her pictures to use online and say I was her! Here are some online pictures of her to link1 link2 link3 link4 I have over 4,000 pictures of her). I created different personalities to go with the different girls in the pictures. I had one girl that was young, petite and slutty, one that was and older milf with large breasts, I sometimes pretended I was a trophy wife looking to cheat on my husband, or an athletic girl in college, or a black girl, or Asian, or Hispanic. It got to the point where I needed to keep notes on which girl I was with which guy, which pictures I was wending to who. I was way more popular as a woman online chatting by a billion times than I was as a guy trying to chat with girls.
Now this was shortly after college, and I was kind of between my crossdressing times. I did not have my sister's old clothes and had not yet started to buy my own women's clothing. But this pushed me into it, I went out and bought some clothes to wear while chatting with guys about being a girl. I would dress up so I could explain to them what I had on (I always altered how I explained it to fit my mood .. but if I said I had a dress on I did have some kind of dress on, if I said I had a skirt and blouse I would have a skirt and blouse on for real) and slowly strip while chatting with them before jerking off myself.
A couple years later when I found out about transsexual women I quickly shifted my online persona to be a transsexual woman. Back then there were some nights I would have trouble finding a guy that wanted to talk with a transsexual woman and I would just change names and be a normal girl for that night. Now a days I never had trouble finding guys to talk with as a transsexual woman. I still chat online a good amount, I go through times where I chat more and others where I chat less. I even sometimes join gay chat channels as just be a sissy boy in a dress, but most of the time I play the transsexual woman that I wish I was.
XOXOXO
Vicky
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