How to be a Cheater: Boyfriend the First

[MugWump]

Carrying on from the prologue, the set-up, the birth of this here cheater, let’s move onward into first boyfriend territory proper.

In the beginning the cheating was definitely a trickle rather than a flood; I saw Aiden and Rob whenever I passed near theirs, and there were a few furtive encounters closer to home with other students and the occasional hookup from the local gay bar. Every time I was wracked with guilt, and promised myself I wouldn’t do it again, but a curious pattern emerged; the more risky the sex got, the hotter it was. If Tim was nearby, or if the person knew people we knew, just about anything that made it a worse idea got me rock hard. I rarely ever used protection when I got fucked, and that really kept me awake at night, lying next to my loving boyfriend with a stranger’s load buried in my guts, wondering if this was going to be the time I’d caught something. My only solace there was that Tim and I were still using protection at this point, so anything that came of it would come to me alone.

 

One thing I wasn’t doing at all, and had never really done, was topping. Yes, I’d had my dick in people, including Tim, but it had never done much for me; I was too self-conscious, too clumsy, I couldn’t find a rhythm or motion that got either of us anywhere. Every time I tried, I’d inevitably panic and get the flop, so I just ended up bottoming 99% of the time. That was going to change pretty soon…

 

I’d taken Tim back to my hometown to meet the parents (who disapproved) and my old friends (who approved), and while we were there I decided to take him to the only gay club within thirty miles, over in the next town. I’d gone a lot with a fake ID before I’d left for uni, and it was still the same seedy, battered, run down little concrete block it always was (and still is, I think). The drinks were cheap, the music was fun (and always ended with Dolly Parton), and the crowd was nice enough. I saw a few familiar, plutonic, faces, and we were having a great time until we ran into Craig and his boyfriend David.

 

Now, I had last seen Craig when we were 15 and were nervously holding hands on a park bench. He’d been sweet enough but I’d never felt like he actually liked me that much, and I hadn’t really paid much mind to him since then. A few years makes all the difference though, and Craig at 18 made my dick jump to attention. What had been gawky was now lean, where there had been softness there were now cheekbones I could cut my hand on, where there had been awkwardness there was now a calm cool I desperately, desperately coveted. He seemed surprisingly pleased to see me, and we introduced our boyfriends, and spent the rest of the night together as a group, drinking and dancing and playing pool. David was a tall, muscular, brooding guy, and he was sweet enough but it didn’t seem like there was all that much going on behind the eyes, y’know? Still, he was really hot, and, I jealously thought, several weight classes above me in looks. 

 

It was about 1am when it happened, and we were all quite drunk, Tim was being distracted by a lively hen party who’d taken a shine to him, and I had excused myself to the bathroom, going to the one tucked away upstairs to avoid the queue at the main one. I was just about to shut the cubicle door when a hand caught it, and Craig slipped in behind me. We looked at each other, both standing perfectly still in that breath-catching moment before you do the deed; I don’t know who moved first but suddenly our tongues were in each other’s mouths and our hands were everywhere and I was so terrified and horny that I didn’t even notice my belt coming away in his hands. Someone in there must have heard me moan as he dropped to his knees and took my whole throbbing cock in his mouth to the hilt, but I didn’t give a shit at that point. I cursed at him when he stopped and stood up, job unfinished, and he just looked me in the eye and said "I want more of that", before leaving me there, pants round my ankles with a raging hardon in some grubby club toilet.

 

I returned to the boyfriends expecting disaster, but turns out Craig has a poker face like no other. The evening finished without incident, we swapped numbers, and away we went. I tried to forget it, until I got a text the next morning; "Meet me later?". Luckily, Tim was heading back to uni that day, while I had planned to stay several more, so I put him on a train that afternoon and headed to Craig’s town, anxious and aroused in equal measure.

 

The Where turned out to be a problem; we were both staying with our parents, both too broke for a hotel, neither of us owned a car… so he convinced me to take a walk in the nearby woods. I pointedly didn’t ask about David, and he pointedly didn’t ask about Tim, and we walked in mostly silence until he took my hand and guided me off the path, into a little muddy clearing, and before I knew it my jeans were round my ankles and the head of my dick was hitting Craig’s tonsils. This boy knew what he came here for, and right then I felt like I was just along for the ride. I moaned quietly as he got my dick good and wet, before he stood up abruptly. “Sit down", he commanded, and I do, even though the mud and leaves are now all over my clothes and bare ass. Craig has taken off his shorts, and without ceremony straddles me, spits on his hand, applies it to his hole and my still wet dick, and with a grunt takes every inch of me in one go. Now, I’m not a small guy, so I was kinda impressed, but also it felt fucking amazing, like a warm velvet glove around my cock. He’s soon sliding up and down me, and as I grab his hips I finally find that top rhythm that had eluded me for years. The mud is seeping into everything, but I don’t give a shit, I just needed my dick to be as far inside this guy as possible. Not content with being ridden like a prize race horse, I roll us both over, dick still firmly inside him, until he’s the one on his back in the mud. As his legs wrap around me we stop for a moment and just look at each other, and as I start to thrust into him again I lean down for our first kiss of the encounter.

 

"I’ve wanted to do this for years", he whispers as I slowly thrust into him. I had to laugh right there, rolling in the mud with my bare dick balls-deep in this guy who I hadn’t seen in years, who I hadn’t even thought was into me in the first place, both of us with loving, unknowing partners waiting for us, finding out I could have been doing this years ago. "You’re kidding me right?" I chuckle. He moans as a slow, long thrust hits his spot. "It might not have been as fun I guess", and the gleam in his eye as he says this tells me this isn’t his first rodeo cheating on David. We’re face to face, my weight holding him down, and as another thrust makes his eyes roll back I feel a sense of power I’d never felt during sex before. "We’re going to do this again." I say, and it’s not a question, and he must have felt the power dynamic shifting too because he just nods his head and whispers "Fuck me".

 

Years of being railed finally pays off, and I go through every stroke and pace that every decent fuck has used on me. Long, deep strokes like Tim, insanely hard, fast thrusts like Aiden, gentle, intimate ones like Rob, bouncing, furious ones like Stephen and every other one I can replicate. Craig is gasping and holding on to me for dear life, and I’m getting pretty close when he freezes.

 

"Shit, someone’s coming", and now I’m being quiet I can hear the voices too. We’re quite concealed from the path, but not that far from it, and the man and woman sound like they’re literally right on top of our spot. I shift a bit, still rock hard inside him, and he can’t help but let out a quiet moan. I clamp a hand over his mouth and whisper for him to be quiet, and as he nods I feel his dick twitch against my abs and see in his eyes that he is fucking *loving* this. The voices are starting to move past, but I keep my hand firmly over his mouth as I start to move inside him again, feeling his tight hole clench my dick whenever I hit a certain point. I keep him there, pinned down and gagged, silently fucking him until I’m sure we’re alone again, at which point I violently pull out of him (secretly enjoying his muffled cry from under my hand 😈), and forcefully turn him over.

 

I’d never actually seen his butt before, and it was a fucking beautiful, perky thing, even covered in leaves and mud. I pull him to his knees, spit onto his waiting hole, and, a little awkwardly since my legs are still very much tangled in my jeans, mount him in one long, rough motion. The chain was well and truly off now, and I went at him like my life depended on it; his t-shirt started to rip as I used it to pull him back onto my thrusts, and I could see that the hand gripping his waist was starting to leave marks. I could tell he was jerking underneath me, and I could feel the pressure building in my own loins as I reached forward and pulled him upright by his sandy blonde hair. I kissed his neck, hard, to which he pulled away enough to turn and look at me, "If you give me a fucking love bite I’ll never let you cum in me again". "Again?" I ask him, slowing my thrusts for a moment. He smiles and raises a crooked eyebrow, "You weren’t gonna pull out, were you?". Fuck me but this guy is driving me absolutely wild, I don’t even have a response to that, so I just hold his head facing me and look him in the eyes as I pick up the pace again. He’s in fucking heaven from the expression on his face, and it isn’t long until he lets out a moan and starts shooting ropes over the forest floor. Feeling his hole clench as he orgasms sends me over the edge, and I lean into him, one hand pushing his face forward and down into the mud while the other pulls his hips up. I cum harder than I’ve ever cum from being fucked, it feels like I’m shooting my soul straight into his guts, and I moan so loud I’m sure someone somewhere heard it. We collapse into a muddy, sweaty, spunky pile and lie there catching our breath.

 

"I take it we’re not going to talk about the boyfriends", I say, to which he murmurs a "Fuck no". I turn to look at him, "You know, that’s the first time I’ve ever really fucked anyone", a confession which gets a genuine look of surprise from him. "No fucking way?!". I grin; that look tells me I did well, "Yup. Any feedback?".

 

"You need to practise. A lot. With me. Then you might be ok. Maybe."

 

"Bastard. I’ll be back in two weeks, pencil me in,” I laugh, and with that we start pulling ourselves together. Everything is a mess, but we clean ourselves up as best we can and head home. There are other stories about Craig I could tell here, but that first time blowing my load inside someone, man it was something else. I was now and forever officially 50/50 vers.

 

Oh, and when I finally got to cum inside Tim months later? I told him he was the first like I hadn’t already been painting Craig’s insides at every opportunity. Poor guy. 😂

 

Hope you enjoyed this rather detailed story, any comments, critiques, or feedback is welcome! Til next time!