Thought I would share the story of the first time I ever cheated and the first time I got to fuck a CD. I believe this was over 10 years ago while I was still in my experimental phase. I was currently in a short relationship that would only last 6 months and this was during the superbowl.

I remember how buzzed I got at my girlfriends party. I was getting horny with all the teasing that my "PAWG" was doing. Every time we had a few seconds alone, she'd grab at my cock or put her hands in my pants. My cock was aching through out the whole game. I remember that the 49ers were playing.

Finally, the game was over and I thought that I would finally be alone with my girlfriend. I was wrong because It was mostly family that was invited over to this party. I knew my girl was gonna have to crash soon so she sent me away with my loaded cock.

Now, it was a while since I had a random encounter but I was just so horny at the time. So as soon as I got into my car I got my phone out and went to work on Craigslist looking for a like-minded individual who could help out. At this point, I've already had three to four other guys play with my cock but one thing that I haven't tried was a feminine mouth. As I was going through the m4m Section, I noticed that there was a cross dressers add in the mix. This crossdresser caught my eye because she looked so beautiful.

She had a long thin figure with black short pixie cut hair. She posed in some very sexy lingerie and looked like she could definitely pass for a woman. She called herself Petra. The way she had her chest made it look like she had B cups. I really wanted to put them in my mouth. I was lucky to find that her ad had a number to it and the location that she had was only 4 miles away.

I was engulfed with a familiar feeling of excitement and nervousness. But I knew I wanted to go through with it. Nervously, I sent a text to the number that was left in the ad. I described my situation and what I looked like. At the time I was in my early twenties with short black hair and no gut yet.

She replied back with her address and the time to come over. The best part of all of this is that it was going to be free. So I automatically rushed over without even thinking about the fact that I hadn't showered all day. That would become kind of a problem later on.

When I got to her location, I discovered that it was at an apartment complex where one of my friends lived. This made my heart race even more as I knew there was a possibility I could have been caught. I was there barely a month ago for my friends housewarming party and we got super wasted. The sexy crossdresser lived maybe four or five Apartments away from my friends. So I made sure to park outside of the complex before entering.

When I got to her front door I knocked. It took her a few minutes to answer but when she did she had a blue robe on with a different colored pixie cut wig this time. This time her hair color was red but I still didn't mind because when I saw her she was the cutest thing. I couldn't even tell that it was a guy dressed up. All I was noticing was this person's very sexy and hot figure. As she let me in through her front door I noticed that it was a studio apartment that was closed off with partition walls. She had a little corner of the room blocked off with these. Around that corner she had her bed. That's where she took me to. She guided me to her bed and sat me there. It was just a typical mattress on the floor type of situation. Her apartment was kind of bare so it looked like she barely moved in.

When she sat me down on the bed. She told me to take off all of my clothes. She told me to do it slowly and I did. As I was taking off my clothes she started to unrobe. She untied the front of her robe ribbon and Let It Drop to the floor. There she was wearing a red lace lingerie piece. You can see that her cock was nicely tucked behind and that her small tits were nice and perky. Ready to be bitten or sucked on. She saw that I had an uncut cock and she said she was a big fan of uncut people. She started to give me a show and she started grinding on me and my cock rubbing up against it. My cock was starting to pre-cum.

As she was grinding on my cock she stopped immediately and went straight down on it. She only sucked my cock for maybe one or two minutes before coming back up and told me something a little embarrassing. She told me that she noticed my penis kind of tasted like cheese meaning I didn't shower that day. I got pretty embarrassed but she said not to worry and ran out of the room. She came back with a condom this time and she wanted to go straight to fucking instead.

This was it. I had never f***** a cross-dresser before but I was about to cross a few thresholds and I was still super excited/nervous about it. After she helped me roll on the condom she jumped on the bed and got in a doggy style position. It was still the hottest thing to see as she really looked like another girl from a Vegas trip or service. And there I was about to get my dick taken care of. She lubed up her ass enough for me to slide in. It was a great feeling. At first I pushed my head through and then the rest of the shaft. She started to moan really loud and told me to f*** her hard and fast. I slowly started in but she really wanted it fast so she kept throwing her ass hard at my cock. She was thrusting backwards while I was thrusting forward so the pounding was amazing. She only had me last for about 3 or 4 minutes before I came maybe twice in her.

The first time I came in her ass I held on tight as she was still thrusting it backwards. I could feel the condom swell up with c** as she continue to thrust backwards. My cock was still hard so I stayed in for another minute and she got me again. This time after I came the first time she laid down more and I was still f****** her from behind but we were in a closer position together which made it super hot. When I came the second time she told me to hold on to her as I was coming. She was on her stomach and I was on her back I had one hand wrapped around her tits and the other arm wrapped around her stomach. I held on to her tightly as my second release came. I noticed her cock was really hard as I was coming that second time so I grabbed onto it and I started stroking as I came. It was such a hot moment but it was over so quickly.

After I finished, she only gave me a minute or two to lay there until she told me it was time to go. I didn't care if she had another appointment with someone else but f*** that was the most sexiest thing I had experienced with my first time crossdresser. I never did get to find her again but I would have loved to have a second encounter with her.

Her name was Petra...