A man wants to feel male genitalia in him and creates a dating profile. Then he meets TS girl Jessica, the best of both worlds.


I was at a party once. Well, I’ve spent more nights at those parties than I can count, but that’s the life of a student. But this particular night of partying led to a most exciting adventure. For your information, the story contains some surprising plot twists, so not everyone will like this. But back to the party. As I said before, student parties are held whenever possible, and this party was no different than any other. This time, however, the party was held in my friends’ communal apartment, which was a couple of hundred square meters, so there was plenty of space and people.

TS Girl Jessica was beautiful

The evening had gotten off to a good start and people were getting nicely into the swing of punch and their own drinks, even though it was only eight o’clock. Around that time, four beautiful women appeared, three of whom I already knew. The fourth was a real bombshell: Jessica, an exchange student. There was nothing romantic or dramatic about our first meeting. Having just come from taking a piss, I hadn’t bothered to zip up and the girls were giggling about it. I just didn’t get it and the beauty of this girl: a short yellow tennis skirt; fishnet pantyhose; a yellow top that fit her breasts just right; and a rock denim jacket on top; beautiful dark eyes; and lovely black hair with a pink streak dyed into it. Unbelievable, I thought.

After an initial vomit, I staggered into the kitchen for a drink of encouragement. Of course, being a polite man, I brought the ladies mugs of pineapple-flavored punch, which wasn’t much of a taste, but it did the job. After a few cups, the girls started giggling quite a bit, and I got to get to know Jessica a little better.

Things progressed nicely and my somewhat clumsy English flirting must have started to work, as Jessica was happy to sit on my lap due to lack of space. I got to stroke her lovely thighs and caress her graceful neck. Soon we were kissing. The way she squirmed in my lap, she must have felt my cock hardening against her delicious ass. I moved my hand up her thigh, but just as I was about to reach under her skirt, Jessica took my hand and shook her head. Then she went off in search of the toilet but bummed to tease me so that I could catch a glimpse of her lovely bum under her yellow skirt. My mates had of course seen what was going on and, after a mild bitching, ushered me after the blonde beauty upstairs to the second toilet in the house. You see, the downstairs toilet was in heavy use as the punch started coming out of the guy after guy.

As if by stealth, I snuck upstairs and smiled at my friend, who was already in full swing with a blonde in the second bedroom upstairs. Of course, I didn’t interrupt my friend’s moment of happiness but crept towards the toilet, where a light was shining through the loophole. The lock had been due to be ripped off a few months earlier – and yes, that too involved partying and hard student life – so I was able to peep my crush through the tiny hole.

I was very surprised to see Jessica pissing standing up and not sitting down, as I might have expected. Next, my eyes fell on a cock held by delicate Asian fingers. Jessica had a cock! I was quite surprised to see it, but after the initial shock, the situation started to excite me to no end, because I’ve always had a thing for boys too, and I’ve been dreaming of shemale girls since I was a teenager. Incredible but true, now I had the most beautiful woman in the world at the same time, who wasn’t a woman at all.

It took me a moment to contemplate the new situation, and then I heard the toilet being flushed. Before I knew it, the door opened, and it plopped me on my ass on the floor. Jessica seemed at least as stunned as I was, and then began a rigorous questioning of what I had been doing. I grimaced and shushed the girl and cranked us into the bathroom to talk.

Jessica started crying and apologized for not telling me. Understandably, telling her something like that right off the bat wasn’t easy. I comforted her and while stroking her I whispered in her ear my excitement at what I saw. Then I wiped her tears and kissed her gently. After a gentle kiss, things got pretty lustful, and I grabbed the blonde TS girl in my arms on the toilet seat.

Jessica bit my neck and her dainty hands descended on my jeans to feel my stiffening cock. I squeezed her lovely ass and moved my hand to the front to rub the top of her panties. I felt Jessica’s shemale cock harden. It was the most arousing sight in the world to see a six-inch cock growing under a yellow tennis skirt. I started to jerk off, while Jessica dug my own out of my jeans. She took both in her hand and rubbed them against each other and jerked them both off. I watched the girl in fascination and kissed alternately the breasts, alternately the red lips.

Suddenly, the door to the bathroom banged violently, and my friends ripped the door open, laughing. The toilet was directly in front of the door, so they didn’t have time to see anything critical. The boys shrieked in triumph at having been interrupted and ordered us to the bar when the punch was gone. Luckily, they left us alone relatively immediately and we had time to put our peckers away and clean ourselves up. Of course, we didn’t go to any more bars, but as the drunken man left for the city center, we hopped on the first bus that took us to my place on the other side of town.

It was around 11 pm when we got to my place. We couldn’t resist touching each other for a moment. We kissed frantically at the door, and in the elevator, I pulled out Jessica’s cock and jerked it. Once inside the apartment, we started to throw off our clothes, and soon I saw this lovely blonde TS girl completely undressed. I don’t know how it’s possible but Jessica was perfect. Lovely erect breasts, not too big, not too small, and definitely not silicone. A lovely ass and a suitably sized shemale cock, which was being wanked by dainty fingers.

Jessica came in front of me and knelt down, looking at me with her big eyes. All the time looking at me, she took my hard cock in her mouth and started sucking it with the most skill. My arousal was heightened by the sight of Jessica jerking his own cock while his little mouth chirped my bigger cock. It wasn’t long before I announced I was going to cum, and I did. The girl swallowed the first spray of cum, and the last couple she got on her pretty face.

I was understandably groaning from the wonderful blowjob, but Jessica hadn’t had her needs satisfied yet. As we lay on the couch, she moved my hand to her cock and asked me to jerk off. But I wanted more and took Jessica’s hardening cock in my mouth. It tasted incredible, and the salty flicks of his cock turned me on even more. As I sucked, Jessica turned so that she could get under me. We were in the 69 position, and her beautiful red lips caressed my balls. It felt heavenly as the little tongue sought my asshole and licked me as deep as it could. Soon I felt a saliva-slicked finger sink into my butt and knew what Jessica had in mind. I stopped sucking cock and asked the beautiful blonde TS girl to fuck me.

I had some lubricant in the drawer of the computer desk, so we came to the side of the desk. I sat down on the table and kissed the lovely blonde TS girl while she lubricated her hard, throbbing cock. He spread the lubricant on my buttocks and fingered me a little. He looked deep into my eyes and began to push his hard cock into my tight anus. She got it inside me and I felt heavenly. My cock was already standing up like a spear, and Jessica was jerking it off while pushing all the way into me. When his cock was up to its hump in my little ass, the fucking began. Slowly but surely, the beautiful blonde TS girl began to push her lovely big cock up my ass and we kissed all the while. We both gasped, and I felt Jessica’s cock stiffen even more, and with a squeal, she shot her load deep into my ass.

The blonde TS girl pulled away from me and knelt down to lick my cum out of my ass. Now she got her tongue all the way in and nibbled on my sensitive ass for a minute or two. This felt absolutely heavenly and certainly didn’t make my new boner go down. But we couldn’t do anymore at that point. Both of us were getting pretty worn out, even if my cock still wanted attention.

We went to bed naked on my dorm bed. I knew the next few weeks were going to be heavenly.

The author explains: This is what it’s like this time. Well, for the first time, I was going to write an even longer story because you could write a book about what Jessica and I were up to. If there’s any interest in this kind of stuff (and believe me, even much more perverted), please give me some feedback. Now I’m off to bowl with a delicious blonde TS girl… 🙂

Brunette TS Jessica