So first, about me: I’m a 23-year-old trans girl, I started living full time as a female two (and a half) years ago. Before that, I spent about two years on aggressive hormone therapy (which I am still on today). I’m 5’8, blonde hair, blue eyes, 130 pounds, perky B cup breasts, and a really big heart-shaped ass that stretches out my skirts and that I’m told looks exceptionally feminine.
Up to only a few months ago, I was dating females. Granted, it was harder for me to make sexual connections after I began to transition and have a more feminine appearance of my own, but there really are plenty of females out there who like to play around with trans girls.
I’ve always fantasized about men. As early as middle school, even as I was only just beginning to scrape the surface of my sexuality and gender, many of my masturbation fantasies involved me being in a feminine role and doing things for men. The thing is, the men in my fantasies had always been sort of generic. I was masturbating to the **idea** of a man finding me attractive and having sex with me as if I were a girl. I never really tried to imagine a face or a type of body. Just the fact of a guy wanting me and putting his cock inside me.
When I met guys in real life, I had never been attracted. When I thought about **actually** hooking up with a real guy, a **specific** guy, I’d always felt sort of weirded out and gross. Somehow, last weekend, that changed for me.
I went out with friends to a dance club (not a gender specific place, just lots of electronic dance music!) that Friday and started off dancing mostly with my friends. Had on a tight skirt and a shirt that showed off my belly. As often is the case, I started dancing with groups of strange girls who I hoped might find me attractive and be interested in making out or something. Later in the night, though, I started dancing with this guy. Really tall, probably 6 foot. Dark hair, green (I think!) eyes, kind of lanky, but still in good shape if that makes sense. The way he looked at me when he approached did something new. I felt a fluttery feeling and felt sort of warm everywhere as he smiled and looked me up and down. I do like feeling attractive, and he had that immediate effect. What I found, though, was that as he was making me feel attractive…he was also making me feel attracted **to** him.
We danced several songs and he’d started to get behind me and dance up on me a little and I’d started wiggling my butt back against him. I was just being sort of playful about it and trying to have a good time, but was surprised when I found that I was getting into it and was starting to feel turned on as we got into a good rhythm and started pressing against each other. He leaned down and spoke in a deep voice into my ear to ask me if I wanted to come sit at his table. I felt like there was some other weird girl inside of me who quickly nodded yes for me, but that was my answer. He took my hand and led me to a long table where he was sitting with lots of his friends. His name was Nick, and he introduced me to a few people and we made light conversation. It was a little too loud to talk in depth and I guess he was sensing that and asked if I’d follow him to a better place. I did, and we sat at this little bar in a part of the club where it was quieter, and where we were alone.
He asked all about me, wanted to know how long I’d lived in the city, if I was going to school or working, what my favorite Netflix show was–all the basics. I learned that he was some kind of an engineer, that he was 32, and he told me all about this Netflix series that I let run into one ear and out the other because by this point, I was pretty tipsy and was amazed at how much I was enjoying just looking into his eyes and sharing smiles. I don’t even remember the name of the show, okay? He started touching my upper arm and then my wrist, and then my knee. We got up and did a slow dance and he held me really close and rubbed my back a lot. At one point I looked up and he tried to kiss me and I quickly shied away. At this point, all I’m thinking is that he doesn’t know something about me that might be a huge deal-breaker and he might even be upset if I let it go as far as a kiss.
When we sat back down, I told him that I was trans, told him about realizing my gender identity in my teen years and transitioning. He asked lots of questions, but he was really cool about it and though he withdrew a bit at first, by the end of the conversation, his hand was back on the part of my thigh just above my knee, now gently rubbing me there. Things got more personal. I told him about how I’d only ever dated girls, had never so much as kissed a guy. In fact, that he was the first guy, I was pretty sure, who’d ever put his hand on my knee for any length of time. Doing my best to recall the conversation:
“You’re feeling the attraction, though. Right?”
I felt myself blushing. “Yes, and it’s a really strange feeling. But yes.”
“I’m feeling it too, and I could see how nervous you were getting, but it doesn’t change anything for me.”
“Why not?” I asked, not sure I believed him.
“Should it?”
Nick said he’d never been with a trans girl before, but that it was something he’d thought about when he’d seen certain news stories and things on the internet. It had sparked his curiosity and he’d read up a little bit and decided that he was open to dating any woman he found to be attractive–cis or trans. When we did another slow dance, when I felt the moment happening again, I looked up. This time, we kissed, and I felt hot tingles all over.
I told my friends that I was leaving, he did the same. We walked out to the parking lot holding hands and it felt perfectly natural to me. At least as natural as it could feel with my knees feeling like jelly and my tummy doing summersaults. We went to a café and I had pie while he drank a coffee. We kissed some more and hugged and talked about the dogs he used to have and how he missed them and wanted to get dogs again, but couldn’t because of the policy at his apartment. Before long, I was following his taillights back to that apartment.
When we got there, I couldn’t believe myself when I took his address and told him I needed to go and get some “girl things” really quick, but that I would definitely **definitely** be right back. He seemed a little doubtful and pouty about that, I think he assumed I was going to ditch. I found that to be cute. I felt like I was watching the actions of that other weird girl who was suddenly living inside of me when I drove to a CVS I’d spotted and bought a small amount of personal lubricant and tucked it in my purse. I didn’t know if I would really be open to letting it go that far, but on the drive to his place, I’d somehow decided I wanted the option.
We had a big hug when I knocked on his door. We curled up on his couch and watched a couple of episodes of True Blood while we drank a lot more and leaned into each other and held hands and felt around on my thighs. Somewhere into the third episode, we were kissing again and then we were making out. He said he didn’t want us to go any further than what I was comfortable with, but suggested that we just snuggle up in his bedroom and crash out. He said it would be wonderful if he could just put an arm around me and hold me close while we slept.
So we did something like that. I told him I needed a shower before bed, really more concerned with cleaning myself in certain places and lubing up–just in case. I asked for a big shirt from his closet and came back to the bedroom wearing it and a thong only, freshly showered. Snuggling up felt incredible and natural and easy. We did pass out pretty quick but woke up probably less than an hour later and started making out again, now laying in the dark.
He laid on top of me in just his boxers and was grinding his throbbing cock next to mine, which was laying completely flaccid. He got around to grinding his cock around on top of mine, and he asked me if I get hard when I get turned on. I told him that because of the hormones I’m on, it’s very difficult for me to get an erection, and that I usually don’t. That seemed to excite him, as his grinding got rougher and more insistent at that point. He asked me what I liked to do, sexually, and I told him that I mostly have anal orgasms. He got more excited still.
We rolled around in the bed and he started playing with my butt, groping and squeezing it, gradually working up to sliding his finger down between my cheeks. He found pretty quickly that I had lubed myself and started pushing his finger down into my butthole while I moaned into his ear. He asked me if I’d ever played with anal toys and I told him that I had. He asked me if I’d lubed myself up for him, and I gave a very soft “yes” which sounded a little bit like a whimper. This made him groan with his lips pressing into my neck and then he started kneading my ass heavily, spreading my cheeks open, rubbing his finger around my butthole.
I was purring like a kitten, squirming around while he played with my ass, kissing him eagerly. I took off the shirt and he started sucking on my breasts and started to play with them, too, kneading and squeezing them, gently pinching my nipples. I was moaning and whimpering openly at this point, I’m pretty sure. He asked me if I wanted to take my panties off too, and I slipped them off without answering. His boxers came off and he was on top of me. He hiked my leg up and slipped his head down between my ass cheeks and started to tease around my hole, which was on fire.
“Do you want this?” he asked.
“Please,” I moaned.
He pushed into me. We took it slow as he worked his way deeper and deeper in and in a minute or two, he was fucking me. Slow and steady at first, but then hard and fast. I wrapped my legs around his lower back and he pushed my arms up above my head as he pistoned into me like a machine. We started kissing and I started cumming. I squirted all over my belly and soaked us both, hearing myself whimper his name. That seemed to drive him on, and he started groaning and grunting and was fighting for air as he worked up into a really fast pace.
“Gonna cum,” he moaned.
“Yes, please!” I confirmed.
He didn’t waste any time and about ten seconds later I felt his river open up into me, filling my ass up with his hot cum. That sensation made me mewl and whimper and nearly cum again. It was an incredible sensation and I didn’t want it to stop. I wanted him to just keep pumping and pumping until it was gushing out of my ears. He did stop, though, and we curled back up a bit later and drifted off again.
Sometime in the early morning, he woke me up and asked me if we could do it again. I scampered over to my purse, lubed up while he smiled and then jumped back under the blankets. He told me to turn over and then fucked me on my belly for a long time, long enough to make me cum twice before he finally drained his balls deep between my cheeks. He fell asleep laying on top of my ass like that.
In the morning, he made eggs and bacon and coffee and we had lively conversation and lots of laughs. We kissed and hugged and I promised to call him soon.
That was a week ago.
I’d hoped to see him again this weekend, but he’s been really distant and short in his replies to my texts. I’ve never tried dating a guy before, but I know what this kind of behavior typically means with girls–not interested. I got kind of desperate this last Friday night and wrote him a squishy message saying that I had a wonderful night with him and that I keep thinking about how amazing it was and really want to see him again.
It’s been two days and that one has gone unanswered. My guess is that I was something he wanted to try, but that he’s probably decided he’d rather not have the complication of actually dating a trans girl. It’s got me pretty bummed right now, but even if things don’t work out so that I can see him again, I know it was an important experience. I couldn’t have said this before I met Nick, but now I’m definitely interested in giving guys a chance. It’s kind of like something got turned on two weeks ago that wasn’t there before. Whether it was this specific guy or it was just my time, I don’t know, but I feel my world expanding!
Source: reddit.com/r/gonewildstories/comments/arl4h8/my_first_time_having_sex_with_a_male
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Really interesting story. Hope you find a better guy next time
Guys ghost after sex with cis girls, too. Just saying that it might have nothing to do with you being trans. Thanks for sharing, hot story.
Great story. Both erotic and heartfelt. Unfortunately from all the I have read and TS girls I know it is hard to find men willing to date a MtF TS. But I wish you the best of luck.
You will definitely find your match dear
Great story, very hot
Where do you live sweetheart?
Hi. A lovely story and glad you enjoyed it! Sorry to hear he ghosted. I hope this opens up a new world of fun for you <3
Men have a habit of doing that regardless of who they’re with, male, female or trans. Socially lubricated we’re far more inclined to be beholden to our desires but not necessarily with the intention of something ongoing. It is a sad reality, some women do it as well and I’ve been with Trans women that have done it also. So I would chalk it up to a milestone/important and enjoyable experience and try not to let it get you down.
At the very least, if not for anything else, he awoke your desire and allowed you to experience something for the first time in what sounds like an enjoyable and respectful way. It could have been the total opposite and as such it sounds like you got a lot of good out of it. I hope it hasn’t scared you off from trying new things and new people, but instead helped you see you can be the woman you are, the woman you desire to be and be with who you feel like being with.
There are men out there that are straight, curious or like me, really don’t care and just want to be with whoever they’re drawn to. It’s a matter of finding someone that you both mutually find drawn to each other and want to continue down that road together. But that doesn’t mean you can’t make the most of your time whilst looking and have as many of the experiences you want whilst learning what and who you like.
Best wishes and hope you have better luck with the next guy you happen across. ?
Often when men do something new and “different” they take a while to process it and figure out if they want to do it again. After they’ve thought it through and come to terms with it they come back for more. Give him time to process it. Keep in touch with him but don’t push. Regardless, you had a good experience and opened a new world.
Good luck!
Hands-free orgasm. I’ve never been able to do that.
Don’t worry about being ghosted. Guys do that to women all the time. You had a good time, he had a good time.
Like I’d say to any woman, make a guy work for it longer and they’ll be more likely to stick around.
I bet the Netflix show was Sex Education. That show’s great.
That was a roller coaster of a ride.
From the intrigue of just meeting him to the heights of bareback on a first date to the lows of getting ghosted.
If he doesn’t get back to you I hope at least it gives you the confidence to date in more circles.
As you already know it will likely be tough for you to find a guy who’s ready for a girl like you. There’s still a ton of stigma attached. You’re going to find a lot more guys like him I’d guess.
This happens for cis women too, like someone else said.
It’ll likely be a guy that doesn’t seem to have the “I’ll give this a try” mindset.
Don’t give up hope. It is just an important conversation to have before things get serious. You will find some that’s into dating. Especially if you are as hot as you described yourself!