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!

 

[MugWump]

It was around the six month mark that Tim finally took me upstairs at a house party, drunkenly told me he loved me, and pulled me down onto his fat, raw dick for the first time. Honestly, he was a pretty amazing fuck back then, and that first night bare he took me so hard I could barely walk without leaking cum the next day. We took a trip to the clinic, and once we both got a clean slate (phew) he was all over me. It seemed like trust and love sent his sex drive through the roof because that boy would want to fuck any and everywhere, including some places that nearly got us into trouble. What I’m saying is that, as six months turned into a year, I’d found myself in a caring, stable relationship with a wild, exciting sex life. I should have been content. Instead I started… devolving. 

 

I’d continued seeing Aiden/Rob and Craig when I could, but they were far away and my time to travel was limited. There’d been a couple more odd fumbles with people at the uni, but nothing wild. I had, however, made friends with a small group of guys around my age (with one fag hag naturally) that were my own thing; I’d go out with them to the local gay bar/club without Tim or my straight friends, and it was with this group I really started to go off the rails.

 

Trigger warnings for people getting drugged (one of them being me) in this one.

 

So the original, core of this little group were me, a guy called David I’d met online, and his friend and defender the sweet but mental Elise. He was 20, tall, and beautiful in a 90’s tv heartthrob kinda way, but I, a very mature 19 by now, wasn’t really interested in him. Y’see, David was sweet, and David was nice, and David enjoyed hanging with me, but David was always chronically shy, and, if I’m honest, kinda dull sometimes. But still, I liked hanging with him, and seeing guys flock to him wherever we went was kinda fun. We were good friends for quite awhile, before, and even after, what we both referred to as "The Incident".

 

The Incident started on a Friday out at our local gay club. It always got pretty packed in there, being a big student city and all, and tonight was no different. Now I didn’t drink alcohol very much at this point, being both poor and kinda afraid of drunk me. David, on the other hand, enjoyed a cocktail, and would get pretty drunk on out nights out, after which I’d normally be the one to safely walk him home and pit him in his bed. This time he’d ordered a massive, strong, super-sour cocktail from the bar and was having trouble finishing it, and after he offered me a sip I told him I’d help him with it, because I’m actually incapable of turning down anything sour. So we stood at the bar, chatting, taking sips, having a dance, saying hi to people we knew, and just generally enjoying our night. Once the drink was gone there were a couple more songs before closing time, so we headed out to the dance floor to finish the night on a high.

 

Ooh and a high it was. The dancing felt great, the music sounded great, and we were making out with anyone who wanted it. But by the time we staggered outside we were completely gone, and I don’t remember anything of what must’ve been an hour or more getting home. When I come to, I’m in my single bed, butt-naked, big-spooning an equally naked David. My head is super cloudy, but my dick is rock hard, and pressing against David’s juicy butt. I’m kinda hesitant about moving; part of me knows this is my friend that I’m not even that into, and that I have no idea how we ended up like this, while the other part of me is baying for blood. I settle for nuzzling into the back of his neck and trying to ignore my dick, at which point he must have come to as well, because he starts to gently move his butt against my raging boner.

 

Well that was all the waving red flag the beast in me needed, and I wrap one arm around him and pull him towards me. I coat two of my fingers on the other hand with spit, and without us saying a word to each other I move to finger his warm, tight hole. The dawn light is peaking through the window enough for us to see, and I lean up so I can look at him properly while my fingers work their magic; he really is rather handsome, eyes closed as he gently moans, back arching his lean, hairy body, and whatever is in the driving seat instead of me knows that I’m going to have this guy right now.

 

It’s at this point that David finally turns to me, and even in the dim light his eyes look like saucers. We just keep staring at each other as he reaches up a hand to spit on it, before moving it slowly down to my throbbing cock. Whatever’s got a hold of me, it makes his warm, wet hand closing around my dick feel like fireworks going off on my skin: I’m literally tingling all over as he rubs his spit over my head and shaft, and my fingers dig even deeper into him, forcing out a long moan as they hit his spot. Even the sounds he’s making are giving me pleasurable shivers now, and I pull my fingers out to run my hand over his beautiful ass and muscular thighs. He takes that opportunity to guide the head of my dick to his warm, waiting hole, and we both gasp as my thick head wetly pops inside him. 

 

We pause here; we can feel something is awkward and weird and wrong here, but we’re both wide-eyed and completely dazed, and so, so fucking horny. My whole body feels electric as my hand gently pulls on his hip, sliding him back onto me so very slowly. He groans once I’m fully inside him, and we stay like that for some time, looking at each other before I start to gently move my hips into him.

 

It’s that moment when I foggily remember that I’ve never taken anyone but my boyfriend to this bed, where my housemates and friends are all only a few thin walls away. The panicked thought awakens a sudden urgency in me, and I move David around until I’m on top of him, his long legs up on my shoulders, and thrust my whole length into him. He cries out for me to go slow and I ssh him, and that’s the only time we speak to each other for the whole encounter. We don’t even kiss, it seems too intimate, so we just look into each other’s eyes as I bend him in half and rail him with an energy I shouldn’t have had at that hour. The rhythm stays intense and the sound of my balls slapping against his butt cheeks and my headboard banging against the wall is only interrupted by the grunts and moans coming from the two of us. Suddenly, I feel his hands tighten their grip on my arms, and looking down I see him cumming over his hairy chest without having even touched his cock. Without asking I hold him down for a few thrusts more before unloading what feels like a gallon of jizz inside him. We collapse next to each other, whatever possessed us seems to evaporate, and seconds later we’re fast asleep.

 

The wake up the next morning was… awkward. He tells me he’s never been fucked like that, or even fucked bare before, and he doesn’t know what came over him, and I can only apologize for ruining his ass and filling him up, saying I’d felt really strange too, like I’d been super drunk which seemed impossible on half a cocktail. It stayed awkward for a few weeks until a friend told us how someone had tried to spike their drink at the same club we’d, and the puzzle clicked into place. We met up for lunch, and hashed things out, and agreed that wouldn’t make a report or tell anyone, which in hindsight was a terrible thing to do, but at the time was a utter relief that I wouldn’t have to tell Tim about everything. David and I stayed friends for years, and even though we occasionally joked about that night we never repeated it. However, David wasn’t the only one in that friend group that brought me spiraling towards trouble…

 

Thanks again for reading, see you next time (I hope). And always, comments, questions, and feedback are totally welcome, I love the attention 😂

Edited 20 hours ago by MugWump