I [TF] lost my virginity to a one night stand [F]

And it was absolutely incredible. Just, awesome, wow. I had had a bad weekend and was sitting in bed, thinking about something new I could try, so I got on this LGBT+ friendly app called Taimi. I figured, hey, I won’t match with anyone but maybe a chaser or two, but I probably won’t get harassed.

So no, yeah, no, I got a good amount of matches, a few decent convos, mostly guys, which was fine. But I match with this girl, we start talking, talking about exes, she asks me how the sex was with my last long term girlfriend (well, only one, but is all goooood). I tell her, yeah, no, her family’s is extremely conservative, did not do sex, am 23 year old virgin actually.

And I mean from there it got NSFW quickly. She was just really open about sex, and not in a creepy or uncomfortable way at all. I tell her I really want to experience it, see what it’s like to be that intimate with another person. Then we’re like trading pics, video, sexting, never done any of this before.

So somewhere along here one of us suggests meeting up, I agree. She said we could meet up in a couple days, I tell her I could get a hotel, it’s a few hour drive for me. Then that night I’m sitting up, wondering WTF just happened, should I actually do this? Like, am I gonna regret it?

I ask a mentor, and another friend who I go to for gospel advice (yeah, I’m religious, very. Really really), and they surprise me, they don’t really tell me not to do it at all. I’m like, yeah, I really wanna do this, have this experience.

So yeah, I did it, I went. In the back of my head I really thought there would be nobody there and I’d have to get mad at myself for getting catfishes. No, she meets me there. She looked even better in person, don’t care what conventional standards are or what anybody else would think, to me she was HOT. Damn, she was really hot.

We bought a little food, drove to the hotel, talked about sex, talked a little about life. The sex? Oh god, it was a fuckin’ exhilarating experience. It was so surreal, being that close to another human. She was such a good teacher too and was just awesome about everything. She road me, took my cherry so to speak, after we did a lot of deep tongue (also first time). She had me try doggy, being on top of her, we tried spooning, we did 69, we did some standing position, got a hickey, she gave me fellatio. I’m not gonna lie, I freaking sucked. I tried to give her oral and finger her as I’ve heard lesbian friends say is best. Really did want to make her cum before I did.

She said that she came, and it was really cute. Maybe she “faked it”, but hell, I’ll give her the benefit of the doubt. Not that I don’t believe her, I just know I sucked, heh. She had the idea to take a nap in between the sex, and I’m not gonna lie, that was probably the best damn part. I’ve always wanted to sleep with somebody, see what it was like. She little spooned me and actually legit fell asleep, I couldn’t believe it. Oh man it was awesome. After she woke up we did a bunch of cuddling… really nasty cuddling. It was so intimate and so fucking awesome. She ended up riding me until I came. Not a mind blowing orgasm, but it was more than good enough.

It was two whole hours! I thought it was more like 30 minutes tops. I mean, there was awkwardness. I could barely keep my thingy in (eh’ it’s honestly tiny, but I won’t have it for all that long, so it’s just fine), and it took a bit of coaxing for me to climax, but I don’t think there was anything too wrong with that for a first time. She also said she wanted to record a little bit, and to let me in raw (I’m sterile due to hormones, but I wanted to be super safe). I wasn’t comfortable with that so I just told her no, it was just fine.

We ended up getting pizza afterwards, I drove her home, texted a little bit afterwards, let her know it was incredible, sorry for sucking though. I suffer from horrible clinical depression, but I texted all of my friends, told them what awesome, unique individuals they are, and how much they mean to me. I went into a Zoom call and somebody told me right away I looked happy, like happier than they’ve ever seen me.

I absolutely do not regret how I lost my virginity, at all. Not sorry. If you’re reading this, are in a similar position that I was… if you want to do it, GO FOR IT. Sex is an incredible, intimate experience not like anything else. If you read this novella to the end, thank you! You are one individual, priceless person, and every day above ground is a damn good one.

Edit: Oh, I also got to play the Rolling Stones in my car with her. May sound silly to you… but, just fucking awesome.

Source: reddit.com/r/gonewildstories/comments/ii680w/i_tf_lost_my_virginity_to_a_one_night_stand_f