I met a very attractive girl “Kim” at a convention. After spending much of the day with her, I asked her out to dinner. She accepted and we met at a well-known eating establishment. The dinner went well and we got to know each other a little better. To my surprise she only lived an hour from me which was in the city. We then went to an upscale bar for a few drinks before parting ways for the evening. I was very attracted to Kim but only gave her a little kiss because she seemed a little stand-offish. I did not want to push the matter or my luck at this point. The convention was ending the next day and I only spent a few hours with Kim before she had to leave. I asked if I could see her again since she lived so close to me. Acting sheepish she finally gave me the name and address of the night club she frequented in the city. She told me I could find her there on most weekends working the bar.
Once home I waited three weeks before managing to get away for the weekend. I headed to the city and found the night club down town. I was a little taken back by the night club because I knew the clientele they catered to was not the people I hung with. I was a bit hesitant to go in but knew this was a chance to see Kim even if she was working. I walked in to find a lot of people and it was only around eight PM.. I finally managed to work my way up to the bar. I asked the bartender as I ordered a drink, if Kim was working? He informed me she was working the bar in the back so I slowly made my way through the crowd to the back. I could see Kim working the bar but it was slammed with people trying to get a drink so I waited for half an hour before making my way up to get a drink. Kim was happy to see me but did not have time to talk so we set a time to meet after the club closed.
Kim showed up for coffee where we had arranged to meet. We talked for an hour and a half when she got up to leave. I told her I had a room if she cared to join me for the night? She hesitated a bit before finally declined my offer. She did give me her address and I was to stop by around one in the afternoon the next day if I was still in the city. Of Corse I stayed in the city so I could hookup with Kim the next day. I arrived right at 1:00 pm. just as she asked. We had a very nice afternoon together but I still was not able to get as close to her as I was hoping but I was not going to give up. Upon leaving I did manage to get a hug and a nice kiss from Kim.
We continued to see each other a few times a month to go out and eat, but mostly called and text each other. Slowly I seemed to get closer to her as she let her guard down more. I figured she had been hurt bad at some point in a relationship and I did not want to ask or re-fan the flames of old memories. At some point I told her I was interested in more of a relationship than just going out to eat. She softened up more as time went on and after many months of dating I managed to make some moves on her. She gave in one night and to my surprise when I reached into her panties she had a cock. This shocked me and I had no idea how to handle it as I pulled away from Kim. She told me she tried several times to tell me but just couldn’t. Then she started to cry and I was at a loss as to what to do. I ended up hugging her but was still surprised by what just happened. Eventually we both regained our composure and we talked about it. I finally became okay with it and asked if I could see her cock? When she removed her panties her big cock sprang out. I say “big cock” because Kim had a bigger cock than I had.
We stayed up almost all night and I did get over it after much talking , then she introduced me to her cock. This was the first time I ever touched another cock and I found it to be very interesting seeing it erect when she was naked. I even managed to get an erection with out trying. I guess I was turned on by the beauty of Kim, I don’t really know. We spent the next day together and talked a lot. When we parted for the week I looked it up on the internet to better understand things. We continued to see each other and over time I asked Kim why she chose the shemale life since she had a bigger cock than mine. She told me she never felt like a man only a sissy and wanted to be a girl. She asked if I ever thought about being a girl but I told her no I had not. Over time I thought about it more and more and decided to get more details off the internet. When we met the next time I told her I did some research on the internet. Kim asked what I thought about it? I told her I figured it was the right choice for her situation. Kim asked, what about your situation? I didn’t know what she meant and asked what she trying to say?
You have a small penis and I can’t imagine you didn’t look into it on the internet while researching my choice of life style. So what are you feeling and do you want to talk about it? I could tell Kim had been thinking about our situation by what she had said. I still asked her what she thought. Kim flat out told me I should become a sissy and see if becoming a girl would be something I would want to become. Starting out as a sissy would be the first step and with my small cock it only seems natural I should chose such a life change. I was some what shocked Kim would say this to me. Kim took my hand and we sat and talked about it. I told her this was all to fast and I had to think things over. A week went by before we talked again, this time she came over to my place. We didn’t talk about it until a few hours had passed then Kim asked if I had given the sissy life more thought? I told her I had and I even looked it up on line. So what do you think now she asked. I still didn’t know I told her.
Kim explained why she thought I should consider becoming a sissy and she would help me. I told her I was not interested but over time she did persuade me and over time, slowly turned me into a sissy. What could I say, the past year I had been dating a shemale and sucking her cock so I guess it probably started then. I also have a smaller cock than real men and certainly smaller than Kim’s which she kept pointing out. Kim also pointed out my slender build and almost a girly figure, I would transition easily. So over time I did slowly become a sissy .
Long hair, long fingernails, lots of makeup practice, practice walking sexy, and the list goes on and on. After eighteen months of living as Jamie, Kim introduced me to a few men that like sissies. I look like a girl more than a sissy boy, but until I get my breasts I am called a sissy. I have been a sissy for some time and I actually met a guy who has taken an interest in me as a girl. He is encouraging me to get my breasts done, so I know that will be happing soon. I feel good about myself and feel more comfortable being a girl than I ever did trying to be a man. I am looking forward to my new breasts so I am not called a sissy anymore.
“SM” Sissy Maker