Pretty fresh out of school, I was pretty naive in peripherals of human sexuality. As the college progressed, I have been with two girls but nothing ridiculous. College was the time when I liked to go out with my buddies, and we’d drink and there was the occasional recreational use of ummm,…let’s say party favors. Obviously, in this age of technology, I resort to my fair share of online pornography as a young man could handle. It was just a matter of time before I got bored of normal porn, started looking out for something out of the ordinary when I stumbled across girls with something extra between their legs. Here were beautiful looking women, juiced up with feminity but instead of a pretty little innie, there were these cocks hanging between their legs. At first, I thought I was bi-curious but when I tried looking at gay porn, it somehow didn’t suit me but I was still fascinated and hooked to Tgirls ever since. That’s where this story started.
So I would look at these pretty girls in porn from time to time, jack off, and wonder what it would be like to be with one actually. I even made an alternate account on Reddit to look at some real beauties as I started to learn that porn is way far from realities. A couple of years went by and I now worked at a big MNC in a better city now where I saw the opportunity to get back into the dating game. The Tgirl porn phase was getting even stronger when I am between genetic girls that I date and I started to become even more fixated.
I had just joined an online dating site which was more hookup based than usual dating sites. There would be all kinds of gatherings, all kinds of sexuality getting thrown around, to be honest, I was a lurker there for a while. I succeeded in getting a few dates but all of them turned out to be quite boring. Well, at one night, I am going through profiles of random people and that’s where I found this beauty. Her profile briefly reads a 26-year-old woman with a little surprise for almost everyone. Her name reads Jessica. Furthermore, her profile screams funny, articulate, and obviously, quite sexual. I went through her picture directory and I can’t get enough of her soft body and pretty cock, both hard and soft. Her pictures also revealed her to be a bit of a pothead and which was great for me.
I was still quite nervous to strike up a conversation for quite obvious reasons. Still, I started with boring pleasantries but she immediately replied, and that strike up our conversation. We exchanged our phone numbers after a couple of days so at least I crossed the trust phase. We just jumped to normal chatting instead of the platform. This went on for a couple of weeks and surprisingly, we didn’t involve or even talk about sexual stuff yet. Finally, at the end of the second week, we agreed to have a date together the coming weekend at her place as she lives on her own and I share my apartment. I thought the hotel might be a good place to meet for the first time but she insisted to be at her place.
Not gonna lie, pounding in my heart was starting to hurt my ribs, or at least that’s what it felt like. I cleaned myself that evening, ran down the street to get some beer, wine, and flowers, and off I go. Her place was about an hour from mine which means I have to do a bit of driving. The whole drive my stomach was flipping and my mind is racing. Finally, I pulled up to her apartment, she lived on the 8th floor, as I reached the elevator, I was already sweating and ruining my shirt. The floor welcomed me with cold air as I knocked on her door. She answers the door wearing a white full-sleeved crop top, a plain black short skirt, a black garter which I am guessing with matching fishnets, a black choker, and a gorgeous smile. She welcomes me inside, giving me a warm hug, although my worried self prevents me from truly embracing this beautiful creature standing before me. I gave her the flowers and she chuckles a bit at the site of beer and wine, saying that she doesn’t drink, but she certainly appreciates the thought. Well, it doesn’t take me long to crack open the beer, and I’m actually a little thankful she doesn’t drink, because I’m thinking I’m gonna have to polish this 6 pack off and rest my nerves!
The first half an hour into our conversation on her dinner table, I was down three bottles of beer with the horrible meal she made, but now I appreciate the gesture. She already told me about her cooking skills so I wasn’t that surprised. Jess (She preferred Jess over Jessica) is very inviting, very cool, relaxed, and terrific in every way, but I just can’t shake the nerves. It gets even worse when the conversation steers toward a sexual nature. She is very feminine, pale as one can possibly be with a very petite body, probably stands tall at 5’6″ tall, she has perfect A cups, lovely and curly long black hair, framing her beautiful eyes and lips. Her fingers and toes perfectly manicured, all of this perfectly fitting her personality.
We sat on her couch after dinner. Me chugging on my 5th bottle and she pulled out a bong from under the table. Bong pretty much did everything for me and thank god, she was good with newbies and carried on the conversation. I don’t remember what we were talking about that ended up with my lips on hers but it did quite swiftly. Before I know it, my hands were on the back of her head. Her lips were the plumpest and juiciest I have ever felt on mine, running like she was craving this as much as myself. I realized she wanted more when she pushed me back on the couch to adjust herself between my legs. Her lips tracing the outline of my raging boner from outside my pants, which just made me desperate. Interestingly, she never broke her eye contact with me, calming my nerves as somehow she sensed my nervousness and wanted me to calm them.
She backed off and asked me if I needed a smoke. I say sure, as maybe that will help me out nerves-wise. She reached to the bong and she fixes herself up as a giant cloud of smoke wafts through her room and then gets everything ready for my toke. I inhale nice and slow and blow out an equally huge cloud. And WHAM!!! All of a sudden I am NOT nervous anymore.
All of a sudden, I lay back down as she unbuckled my belt and unzip my pants. She pulls down my pants and reaches the fly in my boxers. She relieved my semi boner from restrains and start stroking it, keeping the eye contact and that gorgeous smile. She lowered her jaw and finally takes my cock inside her mouth. Immediately, I felt growing in her mouth. The feeling is incredible, and watching this beautiful girl wrap her lips around my cock is about more than I can handle. Her head starts bobbing up and down which I had to take control of by getting hold of her head or I will lose the fuel for the night so soon. This is when I realized that I am missing out on feeling her body.
I pushed her back and get up to her lips ending up on mine. I forcibly take off my shirt, and my hands start roaming on her neck and open belly while my tongue entered her mouth. She welcomed it gracefully and showed it the same love it did to my cock. I had other ideas though. I pulled her top above her head, revealing what I expected, her black lacy bra and her near-perfect A cups filling it extensively. My hungry mouth reaches below her neck and starts kissing all over while my hands reach her back to unhook her bra. I threw away the bra as those perky bastards stare at me, begging for my attention. I grab one and my mouth grabs another nipple, this went alternatively for a while as her hands roam in my hairs.
Finally, I pulled her skirt up to let my hand descend down to her panties where I felt her cock for the first time while my lips keep sucking on those hardened nipples. As soon as I leave her nipples, she got the idea and got up. My eyes are glued to this beautiful woman as she wiggles out of her skirt, exposing her beautiful cock outlined out of her panties. I couldn’t wait and pulled her panties down myself for her cock to bounce down in front of my face. Her organ is perfectly shaved from her asshole to her balls, to her shaft. Smooth as a baby’s bottom. Her cock felt so smooth in my hand and as I stroke it, it slowly grows and I end up kissing its head. Her cock jumps a little bit, and she sighs as I wrap my lips around her pretty cock. My head bobs up and down on her beefy dick. And yeah, it was a beefy cock. As she got hard in my mouth, I could finally see just how big her dick was, and it was just the perfect size. She was probably about 7 inches long, nice and thick, and very rigid. I am sucking her for a good 10 minutes as I try to maintain eye contact with her. She pulled me back up to give me a final kiss before proposing to head inside the bedroom.
I was so confident from the hit of bong that I picked up in my arms and took her to the bedroom. I lay myself down and get into a nice 69 position. She is lying on top of me feeding me her meat as I feel her perfect lips slide down my cock, getting hard in her mouth. While sucking on her cock as she lies on top of me, I also get a nice view of her asshole. I instinctively move my lips and tongue to her little hole and start licking. I feel the vibration of her heavy moan as her mouth still sucks on my cock. I ask her if she likes that, and she says yes, she loves it. I keep licking her little asshole and tell her that now I want to fuck her. She happily agrees. She fidgets around in her night table and tells me to take another hit off of the good stuff before I get down to work. I happily oblige and get another heavy rush of euphoria.
Her ass really is a thing of beauty. Nice and round, perfectly smooth, and very feminine. We lube up her ass and she gets on her hands and knees, her asshole ready to be fucked. I take a nice look at us in the mirrors and the scene is truly amazing. That’s one of the nice things about her bedroom, she has several large mirrors throughout the room and we can look around and see ourselves fucking and sucking in every position, and from every angle. Very sexy I must say. Looking down at her asshole, I squirt a healthy amount of lube all over her hole and on my cock before insertion. I slowly slip my cock into her pretty little asshole. I grab her ass, standing at the end of her bed and thrust myself inside her tight asshole. I gently gave her a few thrusts which fit my cock completely inside her hole, her walls hugging it with such affection. To my surprise, she reached behind me and grip my ass, forcing me deeper and moving me faster. And boy, it doesn’t take long before I have to cum. I’m watching her head sway, and her ass meets my every thrust with a jiggle. I hunker over her and start fondling her breasts from the back and sucking on her neck as I feel my hot cum boiling in my balls. I tell her I’m about to cum and she actually pushes her ass harder against my cock, preventing me from pulling out. I feel my body quake as I heave into a tremendous orgasm. My cock explodes into her ass, pumping stream after stream of cum deep inside her hole. Wow, my head and body are spinning. Our bodies are covered in perspiration now and my cock finally slips free from her little asshole, a long string of cum dangling all the while, still keeping us connected.
I fell down in bed beside her, without cleaning herself, she grabbed my cock again and saved it from going limp. Her strokes making it starts to grow again while she told me she wants to ride me now. My cock was ready for her in no time. She got on me, adjusting just above my cock and let my cum flow out of her on my chest. She adjusted my head to her hole and slides down on it, swallowing my fat meat instantly. Her hard cock rests against my chest as she laid down on me to give me a kiss before she started jumping on me. I wanted to make her cum as hard as her asshole squeezed it out of me. I started stroking it as she rode but she had other ideas. She told me she would like me to fuck the cum out of her, which means no hands. In that case, I planted my legs on the bed and start thrusting myself inside her with the pace that sent a shiver down her which I felt on me. She threw her head back as I could see her ass making sounds of getting beaten by my balls and her cock slapping restlessly on my chest. Her hair bouncing up and down as my hand grabbed her neck and slapped her nipples aggressively. The level of pleasure went beyond the control of her balls and her cock ended up spurting a tremendously thick and slimy load on my chest. I rest my cock inside her as I grab it and gave some pleasing strokes to her cock.
As she was done, she got off my cock and lie down beside me to take my cock, soaked in my own cum inside her asshole in her mouth and started blowing it like crazy. It took literally about just 8-10 bobs before I was spurting in her mouth again. She cleaned my cock in a hurry and came to gave me a kiss. Without a word, she just backed up to me very tiredly into a spoon and make me wrap my arm around her toned waist. I tried to talk to her about what is happening but she sushed me, telling me that after sex silences are the best thing she loves to enjoy. This was the most adorable thing anyone has ever said to me. We stayed there, listening to each other’s heartbeats slow down and breath getting normal, admiring each other’s body for about two hours before falling asleep in the same position. Best first date ever!
For u/cutejess.
Source: reddit.com/r/sexystories/comments/ia5dqd/my_date_with_jess_mtffirst_trans_experiencepretty