FTM = female to male
This is someone who was born biologically female, but identifies as male. In this case, the trans guy I hooked up with already had top surgery, meaning a flat chest, but retained original plumbing, meaning a pussy. My story is 100% true and I am a cis guy. This happened at the end of 2018.
I’m a dude who fucks with other dudes about 95% of the time, but I’m most definitely bisexual. I confirmed this a few years ago in a threesome with a girl and a guy and the handful of repeated encounters with them have only solidified it. I’m in my mid 20s, 5’8, brown hair, with a build that’s somewhere between average and slim.
I’ve been in an open relationship for some time now and it’s the deepest and most sincere love I’ve felt in my life to this point. I love what we have and our main policy is just to be truthful. We both download Grindr once in a while, but he’s less keen on meeting strangers than I am. I’ve calmed down significantly since we’ve been together, but I’ve had phases in my past where I was promiscuous.
I’d been curious about experiencing sex with someone who identifies as FTM for a while when it finally happened. I’m sure satisfying my craving to try to pussy had something to do with it. I figured I like guys and I really like pussy, so it would probably click.
Pussy is just very different from ass in my opinion. I’ll never forget when I first got to slide into one; my eyes rolled back in my head and I immediately realized I had been missing out my whole life. I feel masculine and kind of primal when I’m pounding pussy. I will say though that it’s very hard for me not to cum as opposed to when I’m fucking a guy in the ass, where I never have an issue with stamina or prematurity.
Anyway, onto the good stuff. I’m from a small town and I was shocked to say the least when I opened Grindr one day and saw a profile with “FTM” as the header just a few miles away. I was instantly interested and began to message him. He lived about an hour away and was just visiting. He wasn’t free then, but gave me a day when he would be back a couple weeks later. I made it a point to download the app again on that day. Lo and behold, there he was.
It’s not like me to meet up with someone without seeing a face, but I gave him the benefit of the doubt. He insisted on discretion and I figured that was due to being trans in a southern rural US town. It was actually because he has a girlfriend. Karma may catch up to me, but I looked past it.
It’s quite a unique adrenaline-filled feeling when you’re meeting up with a stranger for sex. Some of you reading this probably know exactly what I’m talking about. It’s suspenseful. It was amplified for me in this case because I was trying something new, and again, I didn’t even see a face before driving across town. I was directed to enter through the back of the house, essentially the basement. It was late morning, but like most sane people, I contemplated the likelihood of getting tortured, murdered, robbed, or some combination of the three. I was relieved and delighted when he opened the door. We’ll call him Alex.
He was probably equally or more nervous than I was. I was pleasantly surprised at his appearance. I figured he would be passable, but he had a nice beard and a decent body. He wasn’t slim, but definitely not fat either.
He shut the door behind me. I don’t remember if we made small talk, but I think we asked each other a couple basic questions. There was a couch nearby and I placed my jacket and shoes next to it. He sat down and I asked if he wanted to suck my dick. Alex asked me if it was clean and if I was clean; he didn’t seem enthused about giving me oral. I pulled out my half chub and put it in his face. I think he half heartedly sucked it for a few moments. When I gathered that he wasn’t into it, I told him to take off his pants.
I think the one picture he did send was of his pussy. It had been a long time since the aforementioned threesomes and I was craving pussy badly. I wanted to see it and I wanted to feel it. He slid off his pants and underwear, sitting on the couch with his pussy completely exposed. I reached down and felt his clit. It was big, I’m assuming from being on T for a while. I felt around and he was very wet. I stuck a finger or two in, just a little bit. Very soon after that, I had him on his back with his legs spread and I slapped my throbbing 7 inch cock on his pussy lips. I was ridiculously hard at this point. I teased the clit and continued to rub my dick around the lips. I think the head was just about to slip in when he asked if I brought a condom. I did.
I’m not very experienced with them, but I managed to open the package and slip it on. I slowly inserted myself and it was instant ecstasy. I built up a good rhythm, trying my damndest not to cum. After just a few minutes, he said he wanted to ride me. I should have delayed considering how close I already was to blowing my load, but I obliged. He got up, I sat down, and with his back to me, he sat on my cock. It was too much. I think I may have issued warning, but it was too late. I pushed him off me and ripped off the condom to ejaculate. He almost seemed to panic about where my cum was going to go, so I came in my hand and he promptly grabbed a paper towel. Not sexy at all, but I would later learn that I was only the second guy to fuck him ever, so he’s inexperienced in that department.
We sat back down and he played with himself. In the post-nut haze, I realized I needed to try to get him off. A gentleman doesn’t just leave someone hanging. He asked how long before I could go another round and I sheepishly told him it might be a bit. I continued to stroke in hopes it would come back to life and I used my other hand to finger and tease his pussy. Eventually, I got at least semi-hard and I was able to stick it back in, raw this time. It didn’t take long for him to climax, flicking at his clit while I had some of my cock inside him.
I left shortly thereafter feeling confused, a little guilty because I would have to tell my guy at home what I did and deal with the emotional fallout, and exasperated. The experience as a whole felt weird to me and I wasn’t sure I wanted to do it again or that I even liked pussy anymore. The odor wasn’t strong, but it was only the second pussy I’d experienced and I wasn’t sure if I was into his smell and taste. I went on to my part time job, albeit fifteen minutes late, and continued on with my day.
We hooked up a few more times and I may write about those as well because the sex got exponentially better after this initial encounter. I think when we met up again, a lot of the nerves were gone as we had some idea of what to expect from each other. When I got over the weird feelings that followed, I decided I needed that pussy again and I especially needed to eat it like I meant it.
DM me for a brief video I took during our second encounter. And I may just post here about it in the near future.
Source: reddit.com/r/gonewildstories/comments/ct32yg/my_hookup_with_a_trans_guy_ftm
I hope we get to hear about the next encounters.