Hello readers, hope you enjoy this story. I am 32 years old guy and live near bay area in California. I have had a thing for Transsexuals since long but have not been fortunate enough to meet one. This story is a work of fiction and inspired by some of my fantasies. I might commit some grammatical and factual errors and I apologize for those in advance but I hope you enjoy the story.
I somehow got attracted to transsexuals a lot and was hooked onto TS porn big time. I really wanted to get to know and get close to some TS but could not find a way to do that. I decided to try my luck on one of the famous websites and published a post to find a TS friend under platonic section. After the post went live, I kept checking my emails every 20-30 minutes for first few days only to find spam. I did not loose hope and kept renewing the post every now and then. I did receive few responses from real people during the process but our conversations did not go a long way and I was to be blamed for almost all of the mess ups. Part of the problem was the specific asks I had. I wanted to get acquainted with a real TS in a non sexual way and on top of that I wanted to keep it discrete. And as you can tell, both of these requirements usually do not go well together. I eventually lost hope and stopped renewing the post.
Couple weeks later, I randomly went back to the site and put up the same post again. Next day I saw a response to the new post in my email. I was excited to see one unread message but did not have very high hopes because of previous experiences. That email was from Kim and to my surprise the email was better than I could have ever hoped and got me on my toes before I could finish reading it. It was a very detailed and very nicely written email unlike many of the single liners I received previously. From the response I knew that this sender was a very sensible and a very sweet human. We then exchanged a lot of emails over next few days discussing general stuff, our lives, the area, music, hiking trails etc. The whole conversation was a lot of fun and the excitement was obvious from the responses I was getting.
I started feeling very comfortable talking about anything and then exchanged phone numbers for texting. We then started texting on regular basis and sharing pretty much all the interesting daily activities. After about 5-6 weeks of chatting we decided to exchange pictures to be able to put faces to names. The moment I saw Kim's pic I could not believe if that was a real pic. But we kept sharing pictures on regular basis thereafter and was convinced that the pictures were real. Kim's appearance was stunning, she could have easily given tough competition to many of the models with her great looks. She was tall, slim, busty at right places with a very innocent and feminine face. If I had run into her in public somewhere before knowing her, I would not have been able to tell if she was a TS.
Since the day I knew how Kim looked I started getting aroused while thinking about her and while talking to her. However our conversations were completely non sexual and the thought of loosing a friend kept me from sharing these newly developed feelings with her. I started requesting her pictures every now and then and used those to build my wild imaginations. I was not able to resist my urges any further and started complementing her beauty and pictures in a very flirtatious way. Fortunately for me, she took those very nicely and laughed out most of those.
Kim lived near San Francisco and is about 50 miles from where I lived. I gradually insisted her to meet up sometime to which she agreed after being a little reluctant. She has a lot of friends and a BF about which I got to know recently so her weekends were usually busy. It took us couple of weeks to align our schedules together and meet up in a bar in SF on a Friday night. We finalized the plan on Wednesday and I started having butterflies in my stomach thinking about the same. Finally on the day we confirmed the plan and Kim shared the location of the bar with a text message. I looked up that bar online and found out that the bar was LGBT friendly. I was a little scared since I had never been in LGBT bar before but I was very much excited to see Kim.
Finally the time came, I got back from work a little earlier than usual and had a nice shower before leaving. I drove to SF, parked my car on the street and headed towards the bar. As was decided, I met Kim at the entrance of the bar/club and was amazed to see how hot she looked. As soon as she saw me walking, she started walking towards me with a huge smile and arms extended for a hug. We met with a very quick hug and greetings. Kim was almost as tall as me with her heels on. She was wearing a full length black dress with low neck exposing her cleavage and cuts on the sides of dress along the length of her legs. Without much delay she took my hand and we walked towards the bar. There were about 6-7 guys and girls in front of us waiting to get into the bar/club. Kim stood in the line behind them and I stood behind Kim. I could not stop myself from looking at her hour glass figure and her nice round ass while standing behind her. We were in the line for about a minute or so and had usual talks about traffic etc.
We then entered the club, headed straight towards the bar and sat next to each other. They had nice and loud music inside and I noticed two guy strippers dancing on the stage with girls and guys around them. That was the only difference I could feel in this club from regular clubs. Both of us got our drinks and then started chatting. While chatting with her, my eyes kept slipping to her cleavage every now and then. Talking to her in person was very different than texting and I was pretending to be all decent and was not comfortable flirting at all.
My state of mind seemed to change pretty quickly as alcohol started to hit. Because of loud music there, every time I had to say something to her, I used to go very close to her ear with my face down looking deep inside her cleavage and would at times try to touch her face with mine or would try to touch my lips with her ears. This kept going on for a while and after few drinks I asked Kim to get on the dance floor. She immediately agreed and carried her drink to the floor while I followed her with one of my hands on her shoulder.
I am very bad at dancing but over the years have figured out that you do not need to know a lot of dance moves in clubs. As soon as we got to the floor, Kim turned and faced me with a huge smile on her face and we started feeling the music and move our bodies. My shyness was gradually disappearing and was making a lot more eye contact with her. I gradually went closer to her and held her with both my hands around her waist with very soft grip. I did not feel any resistance and moved further close to her. Our bodies were now very frequently touching and I was super hard the entire time. I am sure she would have felt my hard-on as it did brush against her body many times.
The drinks and music was getting me high and I was feeling very light after being on the floor for few minutes. I was not thinking a lot by that time and moved my hands from her waist to her upper back. My hands felt the perfect and well defined curve just above her waist while they were moving up behind her back. I slowly pulled her closer and went to kiss her lips but she dodged the kiss. With her chin sitting on my shoulder, I heard her laughing and in then saying "I like you honey but I have a boyfriend". I was very nervous at that time and my hold on her went very weak. To my surprise she wrapped her hands around me and gave me a nice tight hug and kept dancing like that for next 15-20 seconds. That gesture of her helped me get out of the nervousness and embarrassment I was feeling at that time. I could feel her boobs against my chest tight but was still loosing the hardness I had for the entire time.
She then broke the hug and held my face in her hands to plant a soft kiss on my cheek. She then held both my hands in hers and we danced for a while like that. I was still looking in her eyes and her boobs with lust. She suddenly left my hands, turned around, stepped back and came closer. She then again held my hands and wrapped them around her stomach with her hands on top holding them tight. I again made another move and started rubbing my hands on her stomach and on the side to feel her hourglass figure. I gradually kept moving closer to her and in no time I felt her nice round ass brushing against my crotch. Before I knew I was really hard once again and hugged her tight with my face next to her ear. I am sure she would have been ticklish with my breathing on her ear and neck as was suggested by her reflex movements to move a little away.
With her dance moves her ass was shaking and was teasing my hard dick. I was getting more and more excited and horny with every passing moment. I kissed her ears and neck at times while I kept feeling her body with my hands. I tried moving my hands up multiple times to feel her big boobs but she would quickly grab my arms and bring them down. I started dry humping her ass while I was pretending to dance along. She seemed to be enjoying that as well as she was moving her hips in tandem. This whole episode had gotten me super excited and I needed just 4-5 with hand to cum. I was hugging her very tight and she was moving her ass really well. My cock was placed right between her crack facing up and with her ass grinding my cock I was trying really hard not to cum in my pants. She then pulled her face back and held my head from behind to pull it forward. She immediately started licking and kissing my cheek. She kept moving her ass up and down on my cock. I heard her soft moans while she was rubbing my cheek with hers. Then she pulled my face further forward and started kissing my ear. At one point I felt her tongue moving inside my ear and that was the point of no return and I ended up shooting a huge load in my pants. I think I kept shooting for few seconds and Kim must have gotten an idea from my grunts.
Under any other situation I would have felt very uncomfortable after ejaculating in my pants but for some reason I was feeling really relaxed and satisfied at that time. I told Kim in ear that I need to use restroom and left immediately to clean myself. There was a huge mess inside my pants and I did the best I could to clean myself up. It took me good 5-10 minutes and few toilet rolls in attempt to dry myself down there. After cleaning up, I went back to the floor where Kim was waiting for me on the side. I was a little embarrassed while walking towards her but she hugged me as soon as I got near her. While in the hug she said she is sorry if she had disappointed me but I told her that I am having the time of my life and thanked her for seeing me. We then went back to the bar and had few more drinks that night.
Hope you enjoyed the story and please let me know if you have any positive or negative feedback at crypticguy143@gmail.com. I have lot of additional ideas to build stories on in continuation with this one but will decide based on the feedback. Hope to hear from you guys soon..