How to Make a Cheater: Prologue

[MugWump]

Sometimes, when examining my many, many poor life choices, I’ve wondered; how do you make a cheater? We can’t just be born like this, something has to have *happened*, y’know? So this post, while including some cheating, is not just about my cheating, so much as about how I became the cheater I am today. An origin story, of sorts. The grand setup for the inevitable punchline. A Prelude.

 

I think it starts with having to keep your formative sexual awakening a secret. I grew up in a very Catholic family, in a very small, close-minded town. Not ideal when you accidentally catch the premier of Queer as Folk on late night tv while alone and finally figure out exactly *how* different you are to all the other boys. Sure, you have no idea what rimming is either after seeing that scene, only that it looked really fucking enjoyable, and 14 year old you wants to find out all about it as soon as bloody possible. You have to sit on this excruciating secret for a whole year, until your school collides with a Scottish school on a field trip to Sweden, and a boy named Martin who’s just a bit more savvy than you clocks who you really are, and sneaks you out of your dorm to drink stolen vodka and share a first, electrifying kiss. It’s beautiful, but then you go home, and you can’t tell anyone about it. Martin keeps in touch for a while, but Scotland is a long way away, and soon enough it’s just you again. (Put a pin in Martin though, he’ll be back.)

 

From that point on, until I left home a few years later, my only experience of a "relationship" was two weeks of hand holding and chaste kisses with Craig over in the next town. He was incredibly cute, but we were 15 and dumb, and it didn’t last. Again,  don’t forget Craig, he’ll be back as well. Anyway, in short, I had no idea what romance was beyond sneaky kisses and holding hands when no one was looking. Every moment of awakening was a guilty secret. It taught me to hide quite well, and hiding was, unfortunately, therefore inextricably linked to arousal.

 

While romance was short, sex, on the other hand, was plentiful once it started. I was a reasonably cute teen with a very nice butt if I do say so myself, and I had been legal for all of a month before I went to my best friend’s birthday party, where her 21 year old cousin Stephen was home from uni and chaperoning the chaos. He didn’t do a great job though, as he snuck a slightly inebriated me out before midnight, drove me to the aptly named Cherry Lane, and finally gave me what I’d been craving. He was taller and bigger than me, and quite buff, with a shaved head and what I thought was a sexy gap in his front teeth. I don’t remember any panic as he pulled me into the back seat and forced his cock down my throat, just the tremendous pressure of my horniness, like if I didn’t have sex that night I would literally die. I gagged on his sizable cock a lot (I’m still sadly shit at deepthroating), but I guess eventually it was wet enough for his liking. He pulled my jeans off, slapped some of his own spit on my hole, and then sat me down on his dick like I was a human fleshlight. Funnily, I don’t remember it hurting at all; evidently I needed this, and his wet dick just slid right in to the hilt as my eyes rolled back in my head. They never taught sex ed in my Catholic school beyond "this is how babies are made", so I never even thought to ask for a condom, and I don’t think I would have wanted one anyway; I wanted to feel every last thing, and he bounced me on his dick like I weighed nothing. He never asked if I was ok, or if it hurt, or if I wanted this, he just used my tight, fresh hole to please his dick, and as a man’s cum flooded into me for the first time I absolutely drenched him in return. I was spent, I was euphoric, and ten minutes later I’d been thrown out of the car three streets away from the party so we wouldn’t be seen returning together. I walked back, hole aching and dripping cum, and spent the rest of the night being pointedly ignored by him. The dirty feeling of being used and the intense sexual arousal of the encounter would pretty much be a staple of my sex life from then on. Stephen would sneak me out in much the same manner whenever he was in town over the next years, and it was always the same; no small talk, he would roughly use my hole to dump his load, and I would have to walk home. It wasn’t until well after I’d seen him for the last time that I found out about his girlfriend and kid.

 

The other encounter of note before I left my hometown was a pair in London, Aiden and Rob. It was only a couple of months after my original encounter with Stephen, and I had been desperate for more. I met them online, a 24-year old couple, who also did some work with a now-defunct porn studio. I thought they were crazy hot, and I lied about my experience trying to get them to meet me until they finally invited me over. 

They must have clocked straight away that I wasn’t being honest about some things, but like I said, I was cute, so it wasn’t long before I was naked on the couch, Rob’s dick in my mouth, and Aiden spreading my legs, finally introducing me to the joys of rimming. I honestly thought I was going to die of pleasure, and I was so horny that when Aiden started to position himself between my legs, I again didn’t care about the lack of condom. Given the size of him, however, what I should have cared about was the lack of lube. My lies came back to bite me though, as I had told him that I had taken a lot of dick, and that the deeper and rougher it was the better, and so he pushed his massive cock into me with only spit and precum, smirking when I cried out. "I thought you said you liked it deep?"

 

"Not *that* deep!" I gasped, desperately putting my hands on his thighs, trying to stop him going further. Now, I *know* the next thing that happened was a shitty thing to do to dumb horny kid, I *know* I should have been more mad about it, but goddamit if it doesn’t still make me rock hard; he bats my hands away, says "Bit late now, you’ll be fine" and proceeds to fuck me like a steam train. No going slow and gentle, no easing up to grab the lube, just straight to pounding my hole like he wants to come out the other side. Rob grabs my head and forces his dick down my throat, and I just have to hold on for dear life as they take turns throwing me around the room. It finally ends when I’m on the lounge floor, on my back and legs spread, Rob has just cum down my throat, and Aiden is somehow going even harder. He tells me he’s going to cum, and I beg him to pull out (I’d started to educate myself a little since Stephen), to which he simply grunts "No", and fires his load into me so hard I can feel his dick pulsing. I’m ashamed to say that pushed me right over the edge, and I had to rinse my own cum out of my hair before limping home.

 

I saw them many more times over the next couple of years, and even if I tried to bring out the condoms they would always manage to send me home dripping cum, feeling used and abused, and honestly I fucking loved it. Anyway, I also need you to stick a pin in Aiden and Rob for now, because, naturally, they are going to come up again.

 

So, that’s the gist of my formative sexual years, and honestly I think it’s pretty obvious where my cheating fetish came from. I’ll see you in the next part for first boyfriends, first betrayals, and a lot of dick. Ciao!

Edited January 24 by drscorpio

[hotguynkansas]

fuck yeah!  more, more, more!

[Willing]

On 1/24/2026 at 6:23 AM, MugWump said:

Sometimes, when examining my many, many poor life choices, I’ve wondered; how do you make a cheater? We can’t just be born like this, something has to have *happened*, y’know? So this post, while including some cheating, is not just about my cheating, so much as about how I became the cheater I am today. An origin story, of sorts. The grand setup for the inevitable punchline. A Prelude.

 

I think it starts with having to keep your formative sexual awakening a secret. I grew up in a very Catholic family, in a very small, close-minded town. Not ideal when you accidentally catch the premier of Queer as Folk on late night tv while alone and finally figure out exactly *how* different you are to all the other boys. Sure, you have no idea what rimming is either after seeing that scene, only that it looked really fucking enjoyable, and 14 year old you wants to find out all about it as soon as bloody possible. You have to sit on this excruciating secret for a whole year, until your school collides with a Scottish school on a field trip to Sweden, and a boy named Martin who’s just a bit more savvy than you clocks who you really are, and sneaks you out of your dorm to drink stolen vodka and share a first, electrifying kiss. It’s beautiful, but then you go home, and you can’t tell anyone about it. Martin keeps in touch for a while, but Scotland is a long way away, and soon enough it’s just you again. (Put a pin in Martin though, he’ll be back.)

 

From that point on, until I left home a few years later, my only experience of a "relationship" was two weeks of hand holding and chaste kisses with Craig over in the next town. He was incredibly cute, but we were 15 and dumb, and it didn’t last. Again,  don’t forget Craig, he’ll be back as well. Anyway, in short, I had no idea what romance was beyond sneaky kisses and holding hands when no one was looking. Every moment of awakening was a guilty secret. It taught me to hide quite well, and hiding was, unfortunately, therefore inextricably linked to arousal.

 

While romance was short, sex, on the other hand, was plentiful once it started. I was a reasonably cute teen with a very nice butt if I do say so myself, and I had been legal for all of a month before I went to my best friend’s birthday party, where her 21 year old cousin Stephen was home from uni and chaperoning the chaos. He didn’t do a great job though, as he snuck a slightly inebriated me out before midnight, drove me to the aptly named Cherry Lane, and finally gave me what I’d been craving. He was taller and bigger than me, and quite buff, with a shaved head and what I thought was a sexy gap in his front teeth. I don’t remember any panic as he pulled me into the back seat and forced his cock down my throat, just the tremendous pressure of my horniness, like if I didn’t have sex that night I would literally die. I gagged on his sizable cock a lot (I’m still sadly shit at deepthroating), but I guess eventually it was wet enough for his liking. He pulled my jeans off, slapped some of his own spit on my hole, and then sat me down on his dick like I was a human fleshlight. Funnily, I don’t remember it hurting at all; evidently I needed this, and his wet dick just slid right in to the hilt as my eyes rolled back in my head. They never taught sex ed in my Catholic school beyond "this is how babies are made", so I never even thought to ask for a condom, and I don’t think I would have wanted one anyway; I wanted to feel every last thing, and he bounced me on his dick like I weighed nothing. He never asked if I was ok, or if it hurt, or if I wanted this, he just used my tight, fresh hole to please his dick, and as a man’s cum flooded into me for the first time I absolutely drenched him in return. I was spent, I was euphoric, and ten minutes later I’d been thrown out of the car three streets away from the party so we wouldn’t be seen returning together. I walked back, hole aching and dripping cum, and spent the rest of the night being pointedly ignored by him. The dirty feeling of being used and the intense sexual arousal of the encounter would pretty much be a staple of my sex life from then on. Stephen would sneak me out in much the same manner whenever he was in town over the next years, and it was always the same; no small talk, he would roughly use my hole to dump his load, and I would have to walk home. It wasn’t until well after I’d seen him for the last time that I found out about his girlfriend and kid.

 

The other encounter of note before I left my hometown was a pair in London, Aiden and Rob. It was only a couple of months after my original encounter with Stephen, and I had been desperate for more. I met them online, a 24-year old couple, who also did some work with a now-defunct porn studio. I thought they were crazy hot, and I lied about my experience trying to get them to meet me until they finally invited me over. 

They must have clocked straight away that I wasn’t being honest about some things, but like I said, I was cute, so it wasn’t long before I was naked on the couch, Rob’s dick in my mouth, and Aiden spreading my legs, finally introducing me to the joys of rimming. I honestly thought I was going to die of pleasure, and I was so horny that when Aiden started to position himself between my legs, I again didn’t care about the lack of condom. Given the size of him, however, what I should have cared about was the lack of lube. My lies came back to bite me though, as I had told him that I had taken a lot of dick, and that the deeper and rougher it was the better, and so he pushed his massive cock into me with only spit and precum, smirking when I cried out. "I thought you said you liked it deep?"

 

"Not *that* deep!" I gasped, desperately putting my hands on his thighs, trying to stop him going further. Now, I *know* the next thing that happened was a shitty thing to do to dumb horny kid, I *know* I should have been more mad about it, but goddamit if it doesn’t still make me rock hard; he bats my hands away, says "Bit late now, you’ll be fine" and proceeds to fuck me like a steam train. No going slow and gentle, no easing up to grab the lube, just straight to pounding my hole like he wants to come out the other side. Rob grabs my head and forces his dick down my throat, and I just have to hold on for dear life as they take turns throwing me around the room. It finally ends when I’m on the lounge floor, on my back and legs spread, Rob has just cum down my throat, and Aiden is somehow going even harder. He tells me he’s going to cum, and I beg him to pull out (I’d started to educate myself a little since Stephen), to which he simply grunts "No", and fires his load into me so hard I can feel his dick pulsing. I’m ashamed to say that pushed me right over the edge, and I had to rinse my own cum out of my hair before limping home.

 

I saw them many more times over the next couple of years, and even if I tried to bring out the condoms they would always manage to send me home dripping cum, feeling used and abused, and honestly I fucking loved it. Anyway, I also need you to stick a pin in Aiden and Rob for now, because, naturally, they are going to come up again.

 

So, that’s the gist of my formative sexual years, and honestly I think it’s pretty obvious where my cheating fetish came from. I’ll see you in the next part for first boyfriends, first betrayals, and a lot of dick. Ciao!

I would cheat on my wife with a man/ men.

[streetmonkey]

Fuckin love this thanks mugwump. Eager to hear more. 

[NordicBtm]

Great start, can’t wait for more 🐽

[PozBearWI]

I think "cheating" is simply lying about who we really are.  And while for many our social training would suggest that's what we need to do; life becomes so much better once we aren't hiding an ugly secret, but finding a mate whose thinking aligns with ours.  

What a terrific description of what is a fairly familiar "gay self" coming of age.  Quite similar to my own start although I wonder how things would have been different had I also started as a younger teen rather than a 20 year old guy?

Edited January 30 by PozBearWI

[MugWump]

Back for part 2 of my villain origin story!
 

So, at 18 I finally got out of my hometown and away to university. I honestly couldn’t wait, I felt like the chains were off, as scary as it all was. I had a cool little room in a house with six other (straight) students, who were all sweet and awesome (we still meet once a year at least to this day), and it was my first time being openly gay. It was nerve-wracking,  and I still did some weird self-hating shit; that Catholic upbringing is hard to shake, y’know? I did, however, manage to fake being a reasonable human long enough to find my first boyfriend.

 

Tim was actually the first gay boy I met there, so maybe that’s why I dated him? Still, I feel like I really did like him; he was lanky and dorky, kind and sweet, and he knew stuff about gay life that I didn’t, and I eventually fell in love with him despite all my pent-up weirdness about being gay in general. We met on a now dead social network site, and he came over to binge Ally McBeal (showing my age), which turned into a make out session. He was actually the first guy to have me alone, on a bed, horny as hell, and to leave without any action beyond kissing. Later on when I asked him why, he said he thought I was worth waiting for. It was honestly the first time I’d been treated with any kind of respect since I’d started having sex, and it was lovely and really, really confusing.

 

We did finally get around to fucking after a few (!!) weeks, and he was actually really damn good; he had a massive cock, a pert butt, and was totally vers. It was also the first time anyone had regularly used protection with me, and we carried on with it for about six months, until he accompanied to my first ever check up. He was, in short, absolutely lovely to me.

 

I lasted just under three months before I started cheating on him.

 

It was Aiden and Rob who kicked things off. We hadn’t talked in a few months, and they invited me for a drink "next time you’re in town", which I found an excuse to be shortly after the invite.

 

The trick was convincing myself that I could go for a drink with them and it would just be that. And then that one more at theirs to "see the new place" was totally harmless. And then that lounging on the sofa together as we drank was an appropriate level of closeness. And then that a kiss was fine, nothing really, just for old times’ sake. And then that if I could just get them to wear a damn condom it wouldn’t really count…

 

I actually very nearly managed that last part. I’d told them about my new bf, said that I should be safe if I can’t be good. I was straddling Aiden on the sofa (he was the real mischief-maker of the two, if you hadn’t guessed), and the head of his giant curved dick was pressing up against my hole. Rob was sat across the room watching as he liked to do sometimes, massaging his cock as his bf ground against me. I knew where this was going, and reached for the rubbers I’d pointedly put on the table with the lube. I grab one, I have it *in my damn hand* when he pulls me down for a kiss, and as we do the head of his dick, slick with my spit and his precum just… slips inside. Honestly this guy had a heat-seeking dick when it came to my hole, it always, always found it’s mark from any angle, and this time was no different. My moan betrays me, and holding my face in his hands and looking me in the eye he slowly, so very slowly thrusts his hips up. I think he was waiting for me to stop him, but fuck knows I couldn’t now. I felt Rob’s hands on my shoulders, pulling me upright to kiss my neck, and the change in angle slid me all the way down Aiden’s throbbing dick. I honestly didn’t think of Tim at all as I started to slide up and down, just about how fucking awesome this felt, and of how hot it was to be used by someone who didn’t give a shit about me, and vice versa. 

 

I left the next morning with six loads inside me, bruises on my neck and wrists, and lovebites on my butt and thighs. I’d cum so much myself I felt sure I must be dehydrated. I staggered back to my uni town, cleaned myself up, hid from Tim for a week (I have a stinking cold, cough cough) until the lovebites healed over and thought "I won’t tell him, it was just a one time, stupid thing, it’ll never happen again"…

 

Dear reader, it did happen again. Tune in next time for more Sleazy Short Stories of a Serial Cheater!

 

Questions, comments and critiques are all welcome. ☺️

[infinite290]

oh fuck. more!