Maybe I was lonely. Maybe I needed to find myself. Maybe I needed to express myself. I was definitely horny! I was out of grad school. I had a good job in a small rural area. A small house to myself on a lake. I was in my late 20's and in a pretty good place physically and financially. Mentally and emotionally were questionable. For the first time in my life, I was somewhat free to be me, but I had made some bad strategic decisions. I was living in a rural religious conservative area, and I desperately needed to let my feminine side out and cross-dress. Part of me wanted to transition and live full time as a woman. Part of me wanted to live most of the time as a woman. Part of me was really enjoying making good money as a man. But for the first time I had privacy to dress when I wanted and the money to afford kink and clothing.
I lived in a very very small house, but it was on a dead-end road on a lake. 85% of the days of the year, I had no neighbors. Summer holiday weekends I would probably have neighbors on either side of me. Any other time the road and slough of the lake were so private I could parade outside naked, and no one would notice. I loved the privacy, and it was the first time in my life that I lived without roomies. It gave me a lot of freedom to experience all of my suppressed kinky desires. But I was doing them alone and that became old very quickly.
The internet was about 5 years old where I lived. I am sure it started earlier, but I had fist used email about 5 years before at Uni. I had just discovered chatrooms and was wandering around chatrooms for the local area. This chat server was set up so you could enter an existing room or create a room. There were lots of rooms with a crowd and I had been through many when I created a room called "educated, nice and transgender." It was slow to start but soon I got a few people coming in and out. Most were dirty old men and the pattern got old very quickly.
"ASL?" (Age, Sex Location?)
"Wanna fuck?"
Etc. etc. etc.
When they could not get to the fucking part in four of five sentences they got mean, rude and abusive. One did not though. The conversation was actually real. She wanted to know about me. She was not begging to meet in 10 minutes for sex. After about 15 minutes of chatting, I started ignoring all the men sending rude chats and moved to chat with Melissa. She was literate, humorous, chatty, kind, and fun. I enjoyed talking to her about a little of a lot. In the end I knew a little about her and she knew a little about me. She definitely knew that I was transgender and very inexperienced at it. She worked in a mall at a makeup counter and apparently really wanted me to come sees her at work for a makeover. She also knew I loved BDSM and really enjoyed being submissive.
This was amazing to me. I had never considered going to a makeover counter at a mall, but I also knew that the mall was far enough away from where I lived that the likelihood of seeing someone, I knew was very unlikely. I really wanted to meet a woman who not only was happy with me dressing as a woman but wanted to help. The fact that she probably knew how to help me was a dream come true. Before I knew it, I had agreed to come meet her a few days later at her makeup counter for a little bit of makeup help and to meet each other. We chatted each evening for a few days and by the day we were to meet there was no question that I was going.
I had a newfound courage about this. In the past I had hidden all of my kinks and especially cross-dressing from everyone including the public. Now I was going to drive to a mall and meet a woman at a makeup counter for makeup advice and hopefully more. This was in the days before video chats, and we had not shared pictures.
I walked into the mall, and I was a lot more confident and bolder than I had ever been. Normally, I would never even spend much time around the makeup counters, but here, for some reason, I did not care. Sure, I was nervous, and I was aware of every person around me, sure that they were about to see me at a makeup counter doing God knows what, but I did not really care. No one knew me and I was about to meet a woman who already knew I was a crossdresser. This was an amazing concept to me.
I got to the counter, that she worked at, and I looked around. There was only one woman at this counter, and she smiled at me when she saw me. I am ashamed to admit I was disappointed, but I was. She was not my type. I have a pretty broad type and I don't need a very specific look to attract me. She didn't fit. I was tall for a woman at 5'10 and 175lbs but I was in great shape for a guy. Melissa was shorter at about 5'8" and well above 275 lbs. I had dated overweight women but never anyone heavier than I was. I may be prejudiced about what I like and don't like but I am not rude or mean. I came here to meet melissa and get a makeover and that is what I was going to do so I smiled, said hello, and introduced myself.
She was just like she was online. She was literate, humorous, chatty, kind, and fun. I was sitting in the chair by the counter and after a few minutes and we were having a very fun time as we chatted, and she discussed makeup and what she wanted to try with me. I was dressed as a boy, so this was a little disconcerting, but I was so excited to be at a makeup counter and have someone interested in putting makeup on me that I ignored everything around me except her. There were not a lot of customers, but I did notice ladies at the other makeup counters when I had walked in. After a few minutes I was noticing no one except Melissa.
By the end it had been two hours and we had tried and cleaned off multiple different makeup patterns. She was so cool. I walked away from the counter with a lot of makeup in a bag and a lot of money spent. I was also very torn in my emotions. I wanted this so badly, but I was not really attracted to melissa physically. I enjoyed being around her so much and I really loved the fact that she accepted me as me. I could not wait to dress in front of her, but I was terrified of the fact that she probably wanted a lot more from me romantically than I would be able to give. I should have stopped right here but this was the first woman who had met me knowing I was a cross-dresser and I thought she wanted to keep seeing me and help me with this.
I was right. We kept chatting the next few nights and I loved it. I had dated women who knew I dressed but they always found out after we started dating and this led to mixed results. I really wanted this. We chatted in our own private rooms over the next several nights. She was inquisitive and I opened up and told her every fetish and every kinky thing I ever wanted to do. She knew about cross-dressing, but I told her about bondage, my long nail fetish, my cast and brace fetish, my humiliation fetish, and few others. She did not reject me, ridicule me, or make me feel bad about anything. I loved it. I had always been so terrified about sharing all of my weird sexual needs. She seemed fine with it and made me feel so comfortable sharing with her. She also seemed to like the idea of being the dominant partner in a relationship. I did not blink a few weeks later when she told me, rather than asked me that we were going out. I accepted, but I am not really sure that was necessary.
