Embarrassing sex-related stories

Relish in Chaos

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What are your most embarrassing sex-related stories? They can be about masturbation or anything. I remember a while ago, I found this website or something that was entertaining to read through the cringeworthy and sympathetic, yet hilarious stories, so I thought it'd be nice for people to share.
 

Sassafrass

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Aug 24, 2009
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I once had sex with a porpoise. Or was it a dolphin?
Eh, either way, one blow hole is the same as the next to me.
[sup][sup]Broken reference man awaaaaaaaaay![/sup][/sup]
 

Jonluw

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May 23, 2010
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I don't think I have anything extraordinary. Just the usual drunken shenanigans.

Well, there was this one time I got drunk and allegedly made out with this girl I know for two hours straight (When someone told me this afterwards, I was baffled as I was convinced it was something like 10 minutes, max).
It culminated in an attempted fuck that was interrupted by some security guards or something knocking on our door.
Not that we were doing well to begin with, considering how drunk we both were.

I can't remember a lot of details from it.
I do remember, though, that I hadn't been anticipating getting any action, so I hadn't cut my nails or trimmed my pubes recently. I'm sort of hoping she doesn't remember much either.

Other than that? Hmm...
I once read on the internet that a decent way to measure your penis girth is to compare it to a toilet paper roll. As in the cardboard tube that the paper is fixed to; not the entire roll.
Allegedly, a penis of average girth fits very neatly inside a toilet paper roll.
I was all like "What? But those tubes are fairly roomy. There's no way my dick'd take up all that space. I need to investigate." So I went to the toilet and picked up an empty roll of toilet paper, promptly stuck my penis in there and started to conjure an erection.
To my surprise, it fit very tightly.
Then it sort of dawned on me that I was standing in the bathroom half naked, looking pleased, with a cardboard tube fixed to my erect member. The tube wasn't coming off either.
A few seconds after that realization struck me, the cardboard tube tore open and freed me.
Then I went on with my day.

Oh, and you're now going to wonder in the back of your head for the next while how your dick compares to a toilet paper roll. You're welcome.
 

Suicidejim

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Jul 1, 2011
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Various incidents of having just tied up/handcuffed/otherwise severely bound my girlfriend and then someone knocks at the door. The scramble that follows is terrifying to experience, but kind of funny afterwards (aside from my girlfriend's muted growls of murderous rage).
 

DugMachine

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Came home freaking smashed one night and had the bright idea of instead of jerkin it like usual I had sex with a jar of grape jelly (not gonna lie felt good as hell) but next thing I know it was 3 in the afternoon and I was super hungry. Go to kitchen and start making a PB&J sandwich and half way through my sandwich realize wtf I did last night.

Inb4 I get banned for posting that lmao, but its true :/ AIN'T GOT NO SHAME
 

A Weary Exile

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Aug 24, 2009
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Not really a "Story" but my girlfriend can leave hickeys on me that linger for days (And does. Frequently.) yet I can't give her a single mark that stays for more than a day. I swear she has skin like a Rhino. D:
 

DugMachine

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SmashLovesTitanQuest said:
DugMachine said:
Came home freaking smashed one night and had the bright idea of instead of jerkin it like usual I had sex with a jar of grape jelly (not gonna lie felt good as hell) but next thing I know it was 3 in the afternoon and I was super hungry. Go to kitchen and start making a PB&J sandwich and half way through my sandwich realize wtf I did last night.

Inb4 I get banned for posting that lmao, but its true :/ AIN'T GOT NO SHAME
Holy shit man. Thats hilarious. Did you finish into the jar?

I honestly have no clue it was just a blur but I stopped eating that sammich and went about my day with shame and avoided eye contact with anybody for 2 or 3 days lol.
 

DevilWithaHalo

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Mar 22, 2011
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Most of mine involve various injuries, so not really embarrassing per say.

However, a friend of mine had a room mate, and this is all he told me before I said I didn't want any more info... "...get your dick out of the VCR!"
 

Diddy_Mao

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Jan 14, 2009
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During my Freshman year of high school my drama teacher got me a minor role of with a local theatre company production of Oliver Twist.

It's opening night and I'm nervous as shit because I just KNOW I'm going to get out on stage to deliver my lines and do something cataclysmically embarrassing. I'm going to throw up on an actress or trip over my own two feet or just stand dumbfounded like a gawping idiot while the play grinds to a screeching halt. If I had ever been sure of anything in my life it was the fact that I was going to be the downfall of this entire production and by proxy the entire company.

My girlfriend, who had been allowed backstage to help with my makeup decided that the best remedy for my jangled nerves would be to go down on me.

While I certainly don't wish to impugn her enthusiastic efforts, that particular act has never produced "quick results" and as a result she was still in mid act as my queue to come on stage rapidly approached.

Moments later, there's me delivering my lines to a decent sized audience, sporting what I can only imagine is a poorly concealed hard on.
 

Flamezdudes

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Diddy_Mao said:
During my Freshman year of high school my drama teacher got me a minor role of with a local theatre company production of Oliver Twist.

It's opening night and I'm nervous as shit because I just KNOW I'm going to get out on stage to deliver my lines and do something cataclysmically embarrassing. I'm going to throw up on an actress or trip over my own two feet or just stand dumbfounded like a gawping idiot while the play grinds to a screeching halt. If I had ever been sure of anything in my life it was the fact that I was going to be the downfall of this entire production and by proxy the entire company.

My girlfriend, who had been allowed backstage to help with my makeup decided that the best remedy for my jangled nerves would be to go down on me.

While I certainly don't wish to impugn her enthusiastic efforts, that particular act has never produced "quick results" and as a result she was still in mid act as my queue to come on stage rapidly approached.

Moments later, there's me delivering my lines to a decent sized audience, sporting what I can only imagine is a poorly concealed hard on.
Oh good god that must of been embarrassing.

However... That was dutiful of your girlfriend! XD
 

BlueberryMUNCH

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Apr 15, 2010
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There are a few, but one that stands out is her mother walking in while we were...doing...things.
yeeeaaaaah that was awkward, but really funny at the same time, ah dear.

Tell you what though, those times when she can't finish the job is just...stressful and just awful haha.
 

Valdus

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I remember once having sex with my GF and a roommate knocking loudly on the wall shouting "For god's sake at least wait 5 minutes till I'm out of here!". It was only then that we realised how thin the walls were...it sounded like he was in the same room talking to us.
 

Nimcha

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Getting caught in the girls' bathroom in highschool was quite emberrassing. But also still quite funny, I've never seen someone leave a room that fast looking so scared. :p