The First Time I Ever Cheated Sex Story

#Cheating #Teen

By Lisa W.

I was 13 and had a boyfriend but he was not the first guy I had sex with.

If it sounds like the story of the first time I ever had sex was that I was being a slut, maybe you’re right. I didn’t see it like that, it seemed like a huge mistake but it happened and I let it happen so I can’t blame anybody but myself. So maybe I’m a slut who just doesn’t want to admit it.

My boyfriend and I had been “boyfriend and girlfriend” since probably the 4th grade. We were sure we were getting married one day, etc., it was just a done deal, really. We were the same age and “had feelings” (sexual) when we were about 12 or turning 13 or so but although he tried to get me to do things with him, I had been taught that you’re supposed to say no to all that, even if you wanted to. So I did. He was frustrated, I could tell. I was frustrated myself.

My point is that I was not a cold prude with no sexual feelings. When I was 12, I was rubbing myself one time (which I had been doing quite a bit) when I got the bright idea that a hairbrush handle looked like the perfect sex aid. I did it carefully the first couple of times, but of course, I ended up accidentally busting my own cherry with a stupid hairbrush. I bet there have been millions of cherries busted with a hairbrush handle throughout history. That’s how I did it, anyway, and I bet I’m not the first.

On with the story. My female best friend had a brother. He was 15. He had been at my house plenty of times but only a couple of times without her. He really had no reason to be there without her. One day, my folks were gone. I don’t remember where. At my grandparents for some reason or another, I believe. This guy came to my house. His sister was not with him. He just walked in like he owned the place. He was pretty harmless so I didn’t think anything of it.

He was making small talk and it was no big deal. He asked me if we could go watch TV in the basement (a finished basement, not a basement full of cobwebs and skeletons). I really wasn’t that interested but I had nothing better to do so I said yeah. There were 2 couches, 2 recliners, and a daybed. I sat in one of the recliners and he flopped down on the daybed and started flipping through channels. Still making small talk. At one point, he said something and I looked over at him. I hadn’t noticed it before but now I certainly did, he was looking at me like a wolf looks at raw meat.

Maybe that was my imagination but he was definitely up to at least a little something, not just hanging around for no reason at all. I was pretty sure I had an idea what that was. Sure enough, a minute later he called my name and patted the daybed and said “You could sit over here.” “Nah, I’m good”, I said.

Then he said he had something important to tell me “Yeah, I bet you do”, I was thinking. You can see, as I clearly can looking back, that I knew at this point that he was up to some shenanigans and I was fairly aware of the nature of those shenanigans. At the time, I kind of pretended to myself that I didn’t know that, though.

I had no idea just how far things would go, but I was pretty sure I knew how far he was hoping they’d go. So he was insisting that I come over there where he was. I resisted for a minute then begrudgingly walked over and sat down on the edge of the daybed. He started telling me he had been “noticing” me, that guys had needs, etc. and that surely I knew what he was getting at. I told him no way on earth was anything like that happening. Period. Then he told me I had misunderstood what he meant.

So I told him to please clarify what he meant, if I was so clueless about it. He asked me to instead tell him what I thought he meant. “Have sex or at least me masturbate you or something”, I blurted out. He said oh no, he meant nothing like that at all. He just meant that I could “help him.” That’s how he phrased it.

I told him that I had just explained that “helping him” was what I had just said I wasn’t going to do. He said he had to just show me because I apparently still didn’t understand that he wasn’t asking me to do anything at all. I just looked at him. “Lie right here”, he said. He was pissing me off. I decided that I was going to go along with what he said then the second he DID suggest that I suck him or whatever he had in mind, I was out of there.

I lay on my back beside him on the daybed. He started rubbing his dick through his sweatpants. I started to get up. He said “Did I ask you to do anything? I told you I wasn’t going to. You’re just determined that you know what I’m thinking when you don’t.” I had to admit to myself that he had not even touched me or asked me to do anything, so maybe I should go easy on the accusations, even if I wasn’t exactly making accusations. Out loud, anyway. Technically, he had been right and I was wrong, and I didn’t like that. I wanted him to do something so that I could prove I had been right all along, and so far he hadn’t given me the ammo to do that. So I lay back down.

He resumed rubbing his dick, which I had noticed appeared to be hard in his sweats. “See there?”, he said, “That’s it.” I just looked at the ceiling and tried to ignore him. But I saw out of the corner of my eye (as well as feeling the daybed move) that he pushed his sweats down some and now was jerking his bare cock. He still hadn’t touched me or tried to get me to touch it, so I felt like I couldn’t say anything just yet. But I was positive it wouldn’t be long.

Instead, he quietly said “Can I do it on your leg?” (I had on shorts) I thought he meant to rub it on my leg so I gave him a stern “No.” He must have read my thought because he said “I don’t mean touch it, I mean when I start to…you know…do it.” I told him I didn’t care. He resumed jerking it, seemingly satisfied to hear that. I don’t know why I told him he could, I just didn’t see the harm in it and I really didn’t care one way or the other, like I had said.

He jerked it for about 5 minutes and nothing had happened yet. He said that he couldn’t seem to do it. Something was missing, he said. I didn’t even want to speculate on what he was about to suggest so I just waited for him to say it. All he said was, though, “Can you scoot closer?” I said “No.” Then he said, “Well, can I scoot closer to you?” I said I didn’t care. So he did. But he still wasn’t touching me.

He jerked for a couple more minutes and still nothing. Then he said “Don’t get mad, but can I ask you to do something? Just put your leg over me so I can do it, you know, between your legs. Don’t worry, that’s all.” I threw my leg over him, acting like I was disgusted. Now he was jerking it right at the crotch of my shorts. Amazingly, another few minutes and he still didn’t cum. However, what did happen just then was that I was realizing there was a bare hard dick, the head of it barely two inches from my pussy, and I kind of liked the idea.

I wished there was some way to rub myself without him seeing me. But there wasn’t so I didn’t. I sure as heck wasn’t going to do that in front of him, but I kind of wanted to. Just then he said, sounding a little defeated, that he was a little nervous and didn’t think he was going to be able to do it but I was a good sport for letting him try. I’m not sure if he was clever enough to have planned that or what, but now I felt, for some reason, that I hadn’t even helped the guy at all, and he had failed at something. Possibly because of something I did. I felt bad a little bit. No idea why.

Then he seemed to have one last idea. He said “You can say no, and I wouldn’t blame you, but could I rub it, like, actually, against you? On the outside of your shorts?” Earlier I would have instantly said no, but now that we had come so far (lol), if that’s all he wanted to do, so be it. I said sure.

That was a very bad idea. Now he was jerking it more vigorously, and instead of trying to avoid touching me and making me freak out, he was rubbing the head of his dick against my pussy like he owned it. I had already said ok, so I just let him do it. It felt wonderful, in fact. And I seriously entertained the idea of jamming my hand down my shorts and rubbing one out myself. I kind of hoped for magic of some kind to cause my shorts to temporarily melt away and he “accidentally” slip it inside. I could pretend not to notice, I thought.

He put his hand up to his mouth and spit on it and resumed, but now he was doing kind of a “fucking” motion but my shorts were preventing any actual fucking so I didn’t tell him to stop. Suddenly he said, “Can I look at it? For just a second?” I knew exactly what he meant and said no, but either he didn’t hear me or pretended not to and pulled the leg of my shorts open slightly and peeked inside. “That’s beautiful!”, he said. Very corny. I pretended he hadn’t just done that and didn’t acknowledge what he said.

Again something happened that I wasn’t sure whether he had planned it or not. He had gone back to jerking his dick and thrusting his hips again but now, inside the leg of my shorts he had pulled open, I could feel the bare head of his dick hitting the bare side of my pussy. No panties. I hadn’t planned that, and he didn’t know it. Well, he did now but he hadn’t before he looked. His dick felt wet and I knew I was. Instead of jumping up, I found myself silently coaching his dick thrusts to go just a little more to one side. Just a little more. I realized what I was hoping for but I hoped for it anyway.

Then I felt the head pop in briefly. I loved it but I acted like I hadn’t noticed. He stopped and acted shocked. “Sorry!”, he said. I didn’t say anything. “Oh my God! Sorry!”, he repeated. I still didn’t say anything. He took that as permission. Probably rightfully so. I was pretty sure I had just inadvertantly given it so it wasn’t as though he had misunderstood. He stopped his frantic, silly thrusting and just guided his dick right into me like it was an everyday occurrence. I closed my eyes. I thought I should be saying no, but I didn’t want to so I didn’t. No justification for letting a guy, my friend’s brother no less, who was not my boyfriend by the way, put his dick in me. I just didn’t say anything.

He stuck it in as far as he could then slowly withdrew it, then back in again. I thought I might have an orgasm before long, it felt so good. Of course, my silence sounded to him like I meant “Do whatever you please” so he was getting braver. He put his hand under my shirt as he fucked me faster. I just lay there. He squeezed my breast gently at first then more roughly. Still, I didn’t say anything.

Then he threw all caution to the wind and got on top of me. He told me to lift my legs. I did. Then he started pounding. It felt like it was going in twice as deep as before even though I knew it was only a little more. I loved it. I caught myself thrusting my hips to meet his thrusts. I hadn’t meant to, but I was doing it so no use stopping now.

Like I should have guessed, but didn’t, all this heaven wasn’t going to last long. After only about 2 minutes, he said “Lift your shirt. I’m going to do it on your stomach.” I did, and he did. It seemed like a lot of cum but how much more or less than normal, I had no idea.

Like all guys that just fucked a girl that they were pretty sure they shouldn’t have, he started saying how it actually hadn’t been his idea, thanks all the same, but we shouldn’t have done that. I was furious. Instead of pointing out all the ways it was his idea, I just told him never to come to my house or speak to me again. He left. I was furious but still glad we had fucked, which made no sense. I wished my boyfriend was there.

Frustratingly, my boyfriend (of course I didn’t have the nerve to tell him what happened) didn’t try to have sex with me for about 3 weeks after that. He had tried many times, but now that I wanted him to, he wouldn’t. I was hoping he would that very night, and I would have done it. Every day when I was at his house or he was at mine, I hoped he’d suggest it. I sure wasn’t going to, because I thought that would seem suspicious.

Of course, when he finally did, I played hard-to-get, at least a little, and told him I’d give him a handjob but nothing else. The next time I agreed to a blowjob, then when we fucked for the first time, I could quit pretending and we did it a lot after that.

So anyway, that’s how I had sex for the first time, somewhat in a slutty manner, but it all turned out ok.

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By Lisa W.
#Cheating #Teen