The Very Worst Sex You've Ever Had

Sex is usually great, but sometimes it ruins your whole life. Here are some stories about that.

Most of the time sex is a lot of fun. In fact, it's the kind of fun that you relentlessly base every single evening around for a good chunk of your life, which clearly counts for something in the fun ratings. Sometimes, however, it stinks. And that can be for a multitude of reasons. Here are a few of them.

Illustrations by Sam Taylor. Follow him on Twitter @sptsam or visit his website at samtaylorillustrator.com.


When I was a teenager, the thought of getting caught mid-coitus by my parents – or anyone's parents, for that matter – filled me with more fear than anything. But I didn't want to miss out on the action, so my formative years were filled with lots of heavy petting in adventurous locations.

But there was one house party that put me off sex outside the bedroom forever. The Bacardi Breezers were flowing, everyone was horny, someone was already getting fingered behind the DFS sofa. So my then boyfriend and I, in search of a secluded spot to get sexy, decided to sneak off into the back garden. We found a pitch black cubby space behind the shed, so I got on my knees and down to work. After about five minutes, his polite groans suddenly turned into yelps of unsureness. And then came the sudden wetness. I remember thinking, 'Well, that didn't feel like semen and it definitely didn't taste like semen, and why is he panting so much? Oh god, it actually kinda really tastes like.... blood.' I had broken his banjo string. My (gentle yet skilfull) blowjob technique had ripped his hood away from his peen and he was now pissing blood everywhere. Like, everywhere – on my face, on the shed, on the ornamental water feature – everywhere.

By the time we'd both stopped freaking out and realised what had happened, he needed to get to a bathroom ASAP before he passed out on the lawn with his dick out. In the shock of the moment, I totally forgot I was drenched in blood and casually flung open the patio doors to take the only route to the toilet, i.e. back through the entire house party. Have you ever walked through a crowd of drunk teenagers with blood and pre-cum all over your face? Start praying that you never have to.


After going our separate ways for uni, my puppy love girlfriend and I decided to meet up and see how we’d changed as human beings over the past couple of years. She was curious to see if I’d stopped being such a prick, while I wanted to know if she’d learned any new sexual positions.

After getting formalities like drinks and emotional blackmail out of the way, we ended up back at my place, peeling away items of clothing and licking the booze off each other’s breath. Sadly, I couldn't have foreseen what was about to happen. Pulling off her thong, it seemed like someone had cracked open a can of fermented Baltic herring. The stench was so strong that all my hair fell out and a pack of stray cats started clawing at my window. I don’t know if she was playing dumb or she'd lost her sense of smell snorting cheap cocaine, but she seemed completely oblivious to the fact that her lady bits were making my eyes water. Not that it stopped me from going down on her.

In retrospect, that was a terrible, terrible idea. I woke up the next morning feeling like I’d been exhumed. I ached all over, was drenched in a cold sweat, had a 39-degree fever and my throat felt drier than a cream cracker in a furnace. Antibiotics treated the viral throat infection, but catching an illness that wasn't an STD directly from a vagina has irreparably damaged my love of going down on girls and makes everyone I tell that story to retch in their mouths a little bit, which is kind of upsetting. 


I’ve had a lot of nicknames over the years – "Gator Joe", "Düdemeïster", "Pussyman" (I could never tell if that one was positive or not), but much like the herpes sores, they all faded away over time, except for Popeye. That one’s an albatross around my neck that I’ve never been allowed to forget.

About seven years ago, I was dating a girl from a good, Catholic family, and after about six weeks without even a glimpse of anything her end, it began to dawn on me that I was trying to break into the Fort Knox of chastity, meaning our sexual relationship mostly revolved around her awkward handjobs.  

Anyway, we were getting intimate one Friday night and the tedious routine was taking even longer than usual. I could tell she was getting disheartened so I suggested she slip me a finger and fish around for my G-spot. Normally this would be out of the question, but she decided to spoil me that day, so I hoisted my feet up on the mattress while she knelt on the floor, fingering me with one hand and jerking it with the other. This horribly unfortunate alignment of face and genitals directed the ensuing orgasm into my own face, with a stream of baby batter hitting me square in the eye. Popeye’s signature jingle has followed me around like a cum stain on my character ever since.


I'd hooked up with this girl at a party in Peckham and she took me back to her house where we carried on with what we'd started. She'd just moved there and, from what I'd gathered, so had her meek, timid mother and wildly overprotective Cockney father. Obviously that meant very little at the time, as I was far more concerned with rolling around on her cellophane-covered bed.  

Maybe I should have paid a little more attention, because a sudden smashing and crashing soundtracked what looked like Reggie Kray's dad – complete with old man vest, quiff, denim jacket, a BIG fucking dog and, bizarrely, a box of tools – bursting into the room and screaming at a naked me. I immediately started trying to remonstrate, but there aren't many effective tactics when it comes to talking your way out of being caught fucking an angry man's daughter, so I made a run for it instead. 

Being drunk, I obviously tripped about three steps into my escape and felt, first, the chomp of the dog's teeth on my ankle and second, the tip of psycho Del Boy's boots so hard into my nude balls that it felt like he'd passed over every clichéd threat and actually succeeded in kicking me so hard that my balls found themselves lodged in my throat.

I jumped up, still completely starkers, and made a mad dash for the front door, with the dog gnashing dangerously close to my balls and the dad splitting his screams of anger between me and his daughter. I spent what seemed like days huddled naked behind a bush in the front garden, trying to gently throw stones at the window I hoped belonged to the girl, before she hurriedly threw my clothes at me, leaving me to trudge home, ankle bleeding, pride battered and balls feeling like they'd been epilated, stomped on (they had) and deep fried. Moral of the story: if you enjoy having sex with the daughters of angry men, buy a cup.


So my story is short, sweet, icky and sticky. My then boyfriend and I had been out for a friend's birthday, which involved too much absinthe and lots of blunts on a roof overlooking Greenwich Park. It was a beautiful evening spent amongst our closest friends and we thought it only fitting to round it off with some drunk, sloppy sex when we got home.

As far as I remember, we were going at it for a good hour or so – nothing crazy, mostly missionary, a bit of me on top and certainly no anal. When he eventually finished up, my boyfriend pulled out and let out the most disgusted noise I've ever heard, which isn't exactly the first thing you want to hear after having sex.

Somehow, his dick, the majority of his stomach and the whole of my back was covered in shit, like saturated in the stuff. We were far too drunk to do anything about it at the time, so to round off an excruciating hangover the next morning, the entire bed and most of our bodies were coated in a thin layer of faeces. To this day neither of us have any idea how it happened, but my best guess is a poltergeist who specialises in explosive diarrhoea from a height.

Illustrations by Sam Taylor. Follow him on Twitter @sptsam or visit his website at samtaylorillustrator.com.

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