A tomboyish girl and me and our first time together (mf) | 2016

I lost my virginity to a pretty tomboyish girl. She was short, not much taller than five feet, and she had short black hair and small breasts and not much of an ass. She never wore a dress and I never saw her with any makeup on and she wore way more black hoodies than any girl should really have any right to. She was still pretty damn cute though.

She was one of these girls who can't stand the thought of spending an evening home alone. She was a musician and she had dozens of friends and she was always out at some band practice or other, or meeting people for movies or drinks or things like that. It was always impossible for her to find a free evening so really we only saw each other like once a month or something.

When we did finally see each other, we'd sit down somewhere quiet just the two of us and drink a couple of bottles of wine really late into the night. We'd talk and talk and we'd both spill our guts talking about people and friends and relationships and love and sex. I don't know about her, but what with the late nights and the wine and all the emotional outpouring, I usually walked around in a daze for at least a couple of days afterwards.

I wouldn't say I was smitten or anything like that but I really liked the girl. But when someone can't find more than a day a month to squeeze you into their busy schedule you figure any kind of romance is out of the question. So I did my best to be the cool calm and collected confidant but let's be honest, my poker face sucks. Especially with girls. So she probably knew something was up.

She's the one who made the first move. It was in the fall of our first year in college and we were sitting on the couch in her new apartment. We were getting a bit buzzed and the second bottle of wine was almost empty when she just came out and told me she didn't want to be a virgin anymore. I mean I forget what she said exactly and I'm sure she didn't just say it directly like that but it was pretty clear what she meant. And at first I wondered why out of all the people she knew and all the guys she hung out with she had chosen me for her first time. It's not like we were dating exactly. But when a girl like that says a thing like this to a guy like me, well... if the guy like me knows what's good for him he just shuts up and he doesn't go about asking a thousand stupid questions about it. You can blame those teenage hormones if you want but really let's be honest. Even today I probably wouldn't act any different. There's always time for talk afterwards.

Now you'll forgive me if I don't go into every single detail of the awkward mating dance of two young virgins who are pretty drunk on a bottle of wine each. I'm not going to go all National Geographic on you and I'll spare you that part. Let's just say there was some touching and then some hugging and then a bit of very stiff kissing and then some walking together to the bedroom where she turned off all the lights to make sure neither one of us could see a damn thing of the other. I mean it was so dark in there I couldn't see my own dick, if you'll excuse my language.

We ended up doing it four times. Thank God because again, let's be honest here and let's not make a bigger deal of it than it has to be, but the first time sucked. We did it twice that night and then twice again the morning after. Hey, I was young and we took our time so I had the stamina for it. Anyway I was so excited I could probably have done it ten times more no freaking problem.

As I said the first time wasn't that great. Being both virgins I guess that shouldn't come as any surprise. She lied down under the covers and waited for me to join her. (To this day I have no idea why she thought she needed those covers, the heaters were on and it wasn't cold or anything and as I said I couldn't see two feet in front of me anyway, but she lied down under the covers anyway) I was so nervous I was shaking a bit and I had a real hard time getting it up. She wasn't much help and mostly she just lied there, as if for her it was just about waiting for me to do that thing to her that guys do to girls sometimes, you know? Like she didn't really have much part or responsibility in any of it. But I'm sure she must have been pretty nervous too so I'm not complaining or anything. It's just that it felt like it was all on me. Which kind of made me even more nervous than I already was, as if that's what I needed. But again, don't think I'm complaining about it because I'm telling you I'm really not. I was pretty psyched about the whole thing and I felt pretty damn lucky to be there with this girl in the first place so really it's all good. Anyway. I lied down on top of her and we kissed a bit and after a little bit of that I was hard enough for attempt number one.

Man, just finding the right hole in that pitch black bedroom of hers wasn't easy. Turns out that hole is a lot higher than I'd envisioned it for some reason. What do you know. Anyway she had to tell me I was trying to head down the wrong path if you know what I mean. I mean I know you're not idiots so I'm sure you do. It's not that I thought of myself as a great lover or anything, I mean I knew I was no Ron Jeremy or anything, but even then, that was pretty humbling. So by the time I found the right spot for it, it had gone soft again.

So anyway I'll fast-forward a bit because this is just getting boring. But after more kissing I was hard again and a bit less nervous so I went in for attempt number two. That time I found the right spot and we had the right angle and the right position and I went in. For the first time in my life I had my dick inside a girl. Yay me. I mean I don't know about you but I thought it was pretty fucking cool.

Thing is though, as I said she was pretty nervous herself and she wasn't exactly wet and what with it being her first time and all, well... let's just say that after a handful of really awkward thrusts we called it off. That was officially my first time. I remember lying down next to her and wondering does that really count? Am I still a virgin if all I did was put my dick in and nothing else really happened? An existential question I'm sure many young men have asked themselves at some point in their lives.

Thankfully we liked each other and she was pretty cool about the whole thing. We opened the curtains so we could see the moon a bit and we finally had some light in there. And we lied down naked next to each other and talked and talked and talked. And along with the talking there was some touching. That's the part I remember most about that night, the talking and the touching. I don't know, you often hear that cliché about "exploring each other's bodies" and that's pretty lame but I guess that's what that was. My first time kissing a nipple. My first time with my hand between a girl's legs. My first taste of her sex. All those firsts were way more fun than the first time my dick went in. I don't know why I had focused so much on that part before. It kind of seemed not that important afterwards compared to everything else. But I don't want to be too hard on myself there, it's probably pretty standard for guys I would think.

And she touched me too. I was so damn ticklish she couldn't do much, but she did give me a handjob. I wasn't ticklish there. Honestly one of the worst handjobs I've ever received but that doesn't matter. Getting it from that girl on that night was still pretty damn special.

And after a while of that we had sex again. It was still pretty technical and it wasn't passionate but this time we had all the right pieces in the right places. My dick went in easily and she let out a little moan (well, really more of an Hmmmm than a moan) and soon I was thrusting and we were breathing hard and panting and working up a sweat. And I don't know if it's because I was still nervous or maybe it was some leftover of the wine but it took me a while. But still-maybe-a-virgin me was determined to actually do it this time. So after a lot of pumping and thrusting I finally came. She of course didn't come from that. I mean I'm not going to lie and say she was moaning and screaming and that we came together at the same time like it always happens in the movies. As I said it was her first time and she was pretty passive and she didn't touch herself or anything, she just stroked my back up and down a bit. And well, I was pretty damn focused on one single thing you know? And at that point I wasn't too sure exactly what else I was supposed to be touching or kissing or whatnot. So anyway, long story short, I came and she didn't. (Yeah I can hear some of you in the back over there snicker like a bunch of idiots because you're thinking it's probably not the only time that happened, right? Well fuck you too Mrs. Robinson. But yeah, fair enough, you're right. But I still think I'm not that lousy in bed.)

By then it was really late and you could kind of see the sky start to brighten a bit, so I held her in my arms and we fell asleep like that, naked and pressed tight against each other. And when I woke up about three hours later with her still in my arms like that, I really felt like I was on goddamn cloud number nine, you know what I mean? I mean I really couldn't believe my luck, waking up in this cute girl's bed with her all soft and naked and sleepy in my arms like that. I mean I don't know how else to describe it. It was just... great (some people have given me a hard time before about me calling myself a bad writer, but God I wish I could describe that moment better than by saying it's great--in short, yes I suck) And the doe-eyed sentimentalist part of me still thinks that was the highlight of that night, the waking up naked with her in my arms part. But the horny teenage boy part of me still thinks what came next was even better. Because now we really fucked.

We weren't drunk anymore and we weren't nervous anymore and we still probably were pretty tired but we were so in the moment that I don't think either one of us noticed that part. And now we had a basic idea of how to do it and so it was time to experiment a bit more. And again, I'm not going to go into every single little boring detail and I've already been droning on for a while so let me just focus on a couple of things.

The way she moaned and the way she came. God that was an awesome sight. I had a finger in her and she was rubbing her clit and I was licking and sucking on her nipples when she started moaning the first time. And teenage me was thinking Fuck Yeah. And then she started giving me directions, like "like that" and "no, that way" and "no, not this spot" and then "yes, there!" and "keep sucking like that!" and then just "yes, yes, yes!" and then she wasn't even talking anymore because it was like she couldn't and she was just moaning, like this really repetitive high-pitched sound, and it never really got very loud but then she just started shaking. I mean really shaking. Like way more than I ever did when I had an orgasm. And I just thought, Damn. I mean I know it probably doesn't sound like it was anything special but for me it sure was. I mean I felt like... proud or something. Like not only did I come but she did too. Because of me. Now I'm really not a virgin anymore. Yeah, I know, it seems kind of stupid looking back at it, but that's how it was.

The second thing I still remember is taking her from behind. It sounds crass saying it like that but I guess that's what this subreddit is all about, right? I mean if it's not to talk about how we fucked then what is it for? But anyway. We had done missionary again for a bit and we decided we should try another position. By that time the sun was up and the curtains were still open and she's there on the bed on her hands and knees in that spot of sunlight on the sheets and damn... The way that sun shone on her. I mean she was young and pretty and I had the hots for her and it's still to this day one of the most goddamn sexy things I've ever seen. Yeah I didn't have any trouble getting it up that time.

By then we'd fucked quite a bit so she was all wet and my dick just went in like butter and God... I'm rubbing her butt and spreading her cheeks and grabbing her by the hips and I'm just going at it hard. Like really hard. The hardest I'd ever gone, which of course ain't saying much at that point in my life but you know what I mean. I'm pushing and I'm thrusting and she must be enjoying it too because she's doing that low little moaning whimpering thing. And she bends down to put her head on the mattress, because she wants to use her hand to touch herself and she can't stay on all fours and do that at the same time, and God... But yeah, that other old face-down-ass-up cliché. It may be a cliché but it's still fucking hot. And I've got her by the hips and I'm thrusting and thrusting and I notice that she's sweating. Like I can feel her back and her butt getting all slippery under my hands, and I can actually see some tiny beads of sweat pooling on her lower back, right in that kind of dimple there just over her butt. And I'm thinking hey, I'm the one doing all the work here and she's sweating? Fuck yeah. I mean that means she's enjoying it, right? And when she touches her clit I can actually feel her pussy clench around my dick. Like really feel her all tight around my cock. Now that was unexpected. I'd never felt that before. And I know I said before that coming at the same time is cliché, but this time I mean close enough. I guess I came first but she was so close behind that really it doesn't matter. She told me don't stop so I just kept thrusting and thrusting even though I'd already come and before I knew it she was coming too. And really I don't think I'll ever get used to the sight of a girl coming. Not to go on on another long soliloquy or anything, but all that shaking and moaning you know? I mean girls who come are just so fucking hot. (Yeah, yeah, I know, "duh!", right? I know I'm not telling you anything you don't already know but cut me some slack. That morning everything was new and exciting and I thought everything she did was the hottest thing I'd ever seen. Because it was. She could probably have puked that bottle of wine right up right there on that bed and I'd still have thought it was hot as fuck.)

So anyway that was our first time. I'm not going to go into any more details because I think that was long enough. I'm sure you get the picture by now. It's a funny thing though, because this wasn't supposed to be a story about my first time. I mean it kind of was, but that's not what I had started out to do. Really what I wanted to tell you is what went on after. The next day, the next week but mostly the next month. Because I thought that was the more interesting story. But I've gone on for long enough already so I guess I'll leave that for later.

But yeah, just because it's kind of hard for me to just leave it like that, like all unfinished like that, so let me just say that it was Saturday morning and she had a lunch date with her parents. And then Saturday night of course she had a hundred things already planned. She wasn't going to cancel any of that for me. And Sunday, well I forget what she had on Sunday but we didn't see each other that day either. It took a while before we saw each other again. And that's the story I wanted to tell. How long it took for us to finally see each other again and what happened when we finally did. But as I said, that's probably enough reminiscing for now and I'll tell you about that one next time.