Many people ask about my first time “dressing”. The problem is that I cannot separate my first time as a cross-dresser from my first real sexual experience with a man. I first met Robert in the summer of 1997. He was in a Transgender chat room on AOL. I had gone in there mostly out of curiosity and to chat with people who were in the lifestyle to see what attracted them.
I had always felt oddly attracted to cross-dressing but aside from a few abortive attempts on Halloween had never actually done it. I tried to follow along the group chat for several minutes and then jumped in with a few inane questions that were politely answered. I noticed the feeling of comradery amongst the members immediately and felt welcome so I began to hang out there chatting with the other members about many things over several days. After a few days one of the members asked to private message me, and I said yes.
He introduced himself as Robert, and we began chatting about various things, our topics ranged from the serious, Transgender Issues, to the mundane, the Red Sox chances at the pennant. We hit it off immediately and chatted for several hours until I needed to leave for work. We continued this pattern for several weeks and became surprisingly close friends, during this time my interest in cross-dressing continued to grow to the point where I tried my wife’s make up and even purchased a couple of skirts and blouses, kept well hidden. We avoided talking about cross-dressing in any personal way until he asked me after a long build up if I had tried it. I steeled myself for rejection but then admitted that I had.
Robert stopped typing for a while, after about five minutes I pretty hesitantly asked if he was still there. He answered by asking me how I had dressed, and how it felt. I guess the anonymity of a chat room made me a bit bold because I told him, describing the skirt and blouse in detail, telling how the heels felt and the way the panties held me. I told him how I had shaved my legs and how the nylons felt so very smooth and soft. Anyway I have rambled on enough if anyone wants to hear more I’ll gladly share what else happened. Now will you share yours?
I had always felt oddly attracted to cross-dressing but aside from a few abortive attempts on Halloween had never actually done it. I tried to follow along the group chat for several minutes and then jumped in with a few inane questions that were politely answered. I noticed the feeling of comradery amongst the members immediately and felt welcome so I began to hang out there chatting with the other members about many things over several days. After a few days one of the members asked to private message me, and I said yes.
He introduced himself as Robert, and we began chatting about various things, our topics ranged from the serious, Transgender Issues, to the mundane, the Red Sox chances at the pennant. We hit it off immediately and chatted for several hours until I needed to leave for work. We continued this pattern for several weeks and became surprisingly close friends, during this time my interest in cross-dressing continued to grow to the point where I tried my wife’s make up and even purchased a couple of skirts and blouses, kept well hidden. We avoided talking about cross-dressing in any personal way until he asked me after a long build up if I had tried it. I steeled myself for rejection but then admitted that I had.
Robert stopped typing for a while, after about five minutes I pretty hesitantly asked if he was still there. He answered by asking me how I had dressed, and how it felt. I guess the anonymity of a chat room made me a bit bold because I told him, describing the skirt and blouse in detail, telling how the heels felt and the way the panties held me. I told him how I had shaved my legs and how the nylons felt so very smooth and soft. Anyway I have rambled on enough if anyone wants to hear more I’ll gladly share what else happened. Now will you share yours?
and that's cool since I used to buy her clothes for her, all the time. Being a Bi guy was fun. Being a Bi Crossdressing guy? FUNNER! TOne of the best parts of crossdressing? I can get a glimpse into the mind of something I am not, the opposite sex. I will never be a transexual candidate. I don't believe I have the fortitude to walk that road. I crossdress because it appeals to the natural duality in my self. Since I was a very young adult, I did actually lead 2 lives. My everyday one, with my family and friends. And my professional life, which required me to lie to my family and friends about what I was actually doing while in the military. To me, crossdressing isn't only something that pleases me personally, it is also a "skill" that could come in handy in the world of "Intelligence Collection". I are a spook. Always will be. It is in my nature. Another thing about CD? I like the people that do it! I like SOME girly stuff. So do they. It's all a matter of "devotion" I guess. My wife said she wanted me to dress "full time". (yes, she is Bi too!) I told her to put the pipe down! 
