My first time with a trans woman [MT]

Awhile ago, while swiping through tinder, I matched with a trans girl. I didn’t notice at first because I wasn’t reading profiles and she was very attractive. Let’s say her name was Katie. After we matched, I went back to her profile where she mentions she’s trans. I hadn’t previously considered meeting up with a trans girl, as I figured it wouldn’t be my thing, or I couldn’t get past the obvious hurdles. However, Katie was a looker. Five foot six or so, slim, gorgeous blonde hair, big soulful eyes, pale skin. She had several photos of her wearing cute dresses on her profile.

While I’m mulling over whether to shoot my shot, she sends me a message saying that my facial hair is cute. I’m about 6’1″, athletic swimmer type build, and naturally tan, but I’m horrible at talking to women so her messaging me first was greatly appreciated.

We hit it off after that, I ask for her number, and we text back and forth. The next day, I work up the courage to ask her if she’d like to meet up, and Katie says yes! She invites me over to her place after she makes sure that I’m fine with her being trans, which I assure her is no problem. I did tell Katie that I’d never been with a trans girl before, but she assured me that it was no problem and if I was open to it we could just hang out and see where it goes.

So the time comes and I’m shaking like a leaf. I go to her place and she lets me in, and to my relief she’s even more attractive in person. She’s wearing an adorable little sundress that I couldn’t take my eyes off of. She has a nice place too, a well-kept apartment with a friendly cat. I start to play with the cat because I’m still pretty nervous.

Eventually we sit down on the couch and start to chat, and she puts her hand on my thigh. I ask if I can kiss her and she agrees. She tastes wonderful, and is a fantastic kisser. She moves her hand over to my hard cock and gives it a playful squeeze, and I moan while kissing her. She pulls back from me, hand still on my cock over my pants, and asks again if I’m okay with going forward. I felt a little bad. Here was this absolute knockout making sure I’m okay with being with her.

Of course, I agree, and she unbuttons my pants and pulls out my cock. I’m pretty average, about 6.5 on a good day. Katie gracefully slips off the couch and positions herself between my knees and proceeds to give me by far the best blowjob of my life. It’s all I can do to keep from cumming in her mouth. I’m holding on for dear life. I mention to her between my moans that she was going to make me cum if she kept it up, and she stops and looks up at me before removing her panties and standing up. I see that she’s hard and it turns me on even more. She sits in my lap and continues to kiss me. As she’s kissing me, I see her reach for a bottle of lube. Katie pours a little out and rubs some on my cock as she’s kissing me. She pulls back again and raises her hips. She’s still wearing the sundress, and I can see her hard cock underneath it.

She lowers herself onto my cock. I had zero concerns at this point. I remember thinking before I showed up if I would chicken out if it came to this, but now I was way beyond that. I couldn’t wait to be inside Katie.

Katie takes the length of me inside her, and doesn’t move for awhile as I guess she’s getting used to me being inside her. She’s so tight, it feels amazing even just being inside her while she’s motionless. After a little bit, she begins making small movements with her hips back and forth. I’m in heaven. Eventually she begins to move more, riding me on her couch. I clumsily grab her cock, then think twice and ask if she’s alright with that. Katie whispers “of course” and gives me a smile. She asks if I would like to relocate to the bedroom and I happily agree.

My head is spinning. This is already the best sex I’ve ever had. Katie lies on her back on the bed and motions me over. I push myself back inside of her. I begin to kiss her and start picking up the pace. She tells me she’s about to cum, but she wants me to stop after she cums. At this point I’m back inside my own head and I get nervous and I feel like I’m not going to cum with her, so I agree and after she finishes I pull out. Breathless, she asks if I came but I tell her no, that I think I’m a little nervous. Katie says she understands and while she’s kind of coming back to earth, we lie on her bed and kiss.

After about fifteen minutes, she’s hard again. She offers to fuck me. Now I’m way out of my element. I’ve never done anal, no toys or anything, but I agree and tell her so. She says not to worry at all, that I’m going to love it. I lie on my back and she gets between my legs and lubes up her cock. It’s smaller than mine, probably about 5 inches. She lubes herself up and begins to press into me. I can feel her enter inside me. It doesn’t hurt and she’s gentle, and presses herself all the way in before holding for a minute or so. She leans in close to my face and we kiss. I’m rock hard.

Katie begins to move her hips, sliding in and out of me. After awhile I get used to it and it starts to feel amazing. I ask if it’s okay if I get on all fours. I get into position and she presses herself back into me and picks up the pace. I fully cannot believe this is how our first time together is going but I’m having a fantastic time. Katie reaches for my cock and starts stroking me, and I explode almost instantly. I cum harder than I’ve ever come before by orders of magnitude. She pulls out of me and says “That’s why I asked for you to pull out after I came. It’s really intense” and gives me a silly smile.

I just lie there for a bit and we cuddle. I was honestly relieved that I didn’t feel any shame and thought I was being stupid earlier for being so nervous about it. We clean up and make plans to meet again.

I know it’s easy to lie on the internet but this is really how it went. We met up several times afterwards, which I’d be happy to write about if this goes over well. Thanks for reading!

Source: reddit.com/r/gonewildstories/comments/11l21eg/my_first_time_with_a_trans_woman_mt