Embarrassing sex-related stories

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Master_of_Oldskool

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Sep 5, 2008
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Fellow Escapists, please gather around for Story-time with Oldskool, as I share the interesting (to me), thrilling (also to me), uncomfortable (to most of the population), and almost certainly fictional tale of...

It all began with a family vacation to North Carolina. Being one of the older children, I was trusted to go off on my own so long as I didn't do anything illegal. Walking along the beach one night, I happened across a bonfire surrounded by merry Southern revelers, and North Carolina being that sort of state, they invited me for a drink, which I happily took. Several times, in fact. As the night went on, I began chatting up a truly stunning redhead who seemed to be pretty into me. Being at this point too inebriated to form a creative or coherent description, all I could think was that she looked like Lily Cole. I reasoned that if I could just drink a bit more, I might unlock the sort of Hemingway-cum-Byron poetic genius that only comes to drunks. Long story short, I blacked out. When I came to in the morning, I found myself stark naked, entangled with said redhead. As I mentioned, she looked like Lily Cole the night before. But now, in the cold light of sobriety- my God.

She still looked like Lily Cole.

There was a minor hangup there, though.

You see, when she was drunk, she though I looked like Kurt Cobain.

I really, really don't.

So, she started to freak out- and so did I, because I didn't recognize the place and I assumed there were male relatives nearby who would be very interested to know I'd just plowed their daughter/sister/cousin/whatever. After she got a few articles of clothing on, though, I noticed that she was going for the window. "What are you doing?" I asked. "This is your house, isn't it?"

"No" she says. "This is your house.

I look around. And I realize with stark horror:

This is my little cousin's room.

By some brilliant freak coincidence he'd gone to bed with my aunt and uncle that night, so we weren't caught.

Perhaps the saddest part of the story is this: I may or may not have actually had sex with the girl.
 

Bara_no_Hime

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Sep 15, 2010
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SckizoBoy said:
Bara_no_Hime said:
?! I swear I've never read the same story twice from you! =P
**looks innocent**

Why would I tell the same story twice? Wouldn't that be redundant?

Anyway - I've been sexually active for 15 years now - I've had a lot of time to build up some fun and interesting stories.

Oh, here's one that didn't happen to me, but to a friend of mine.

She and this guy were hooking up for the first time. They'd finished once and were warming up for round two with some foreplay when the guy's roommate walked in on them.

The guy she was having sex with freaked out and pulled up the blanket to cover himself, incidentally knocking her out of the bed. She fell, naked, on the floor while he hid under his blanket.

It was around then, amidst the laughter of the guy's roomate, that she picked up her clothing and the shattered remains of her dignity and left.

The guy later tried to apologize for knocking her off the bed, exposing her to his roommate, and generally being a giant douche. He wanted her to forgive him and go out with him again.

Needless to say, she did not forgive the guy - and with good reason. I knew him too, and he was pretty much an asshole.
 

Bara_no_Hime

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Gizmo said:
Flamezdudes said:
Why would you have anal sex in a tent full of family members? o_O
Things just happen, also we were average teenagers and just wanted to have sex constantly.
I at least hope you had some good lube with you. Yikes!

I mean, I like anal as much as the next girl (or more), but... yikes! That doesn't sound like a very comfortable position to experiment from.
 

Gizmo

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Bara_no_Hime said:
Gizmo said:
Flamezdudes said:
Why would you have anal sex in a tent full of family members? o_O
Things just happen, also we were average teenagers and just wanted to have sex constantly.
I at least hope you had some good lube with you. Yikes!

I mean, I like anal as much as the next girl (or more), but... yikes! That doesn't sound like a very comfortable position to experiment from.
Let's just say I wish that I had more.
 

Jaeke

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Feb 25, 2010
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Hehehe, 69 comments on the homepage.
Sorry, just had to throw that out.
I'm underaged so no stories from me.
 

Griffolion

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Aug 18, 2009
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Well, this one time (not at band camp), for one reason or another, I wasn't able to last particularly long. Long story short, it all became incredibly funny when FOTC's "Business Time" song came on.

If you want the bit that made it funny, just fast forward to 2:45


Needless to say, she called me "intense" the whole night...
 

mattttherman3

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Dec 16, 2008
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I am legitimately surprised that this thread hasn't been shut down. Anyway, not really embarassing as it is funny, my sister would always randomly open my bedroom door, several times she almost caught me wanking, well one day I decided f this and was naked and she burst in the room right while I was in the middle. She has never burst into my room unanounced since.
 

Cimerax

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Jan 10, 2010
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I've done things that some would call "nasty."
And you know what? I'm not ashamed of ANY of it! Of course, I'm not planning to share, because there may be conservatives reading.
 

Elementary - Dear Watson

RIP Eleuthera, I will miss you
Nov 9, 2010
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My advice to everone is that romantic, sexual baths are not at all a good idea.

So, it was all planned... I'd got bubble bath, and candles and everything, and we were home alone! Started off great, dinner, film that got us in the mood (no, not that type of film... but Cruel Intentions is not far off in places!) and then we headed up...

I ran the bath, in between us undressing in a kind of passionate fury, but in my eagerness didn't remember that I personally like my baths and showers a fair bit hotter than most people...

The bath started off ok, I guess... Wasn't quite sure what we were meant to do once we were in that cramped space, but we rolled with it and it was ok... but then she kinda looked a bit tired... I opened the window, realising that it was like a sauna in there, but it didnt help, seconds later she passed out with heat exhaustion...

So there I am, naked and soapy, lifting another slippery naked soapy person out of the bath, and onto a towel on the floor, putting her in the damn recovery position, and finally trying to cool her down as much as possible... not easy with underfloor heating...

Damn mood pretty much ruined for the night...! :/
 

Bara_no_Hime

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Elementary - Dear Watson said:
My advice to everone is that romantic, sexual baths are not at all a good idea.
I ran the bath, in between us undressing in a kind of passionate fury, but in my eagerness didn't remember that I personally like my baths and showers a fair bit hotter than most people...

So there I am, naked and soapy, lifting another slippery naked soapy person out of the bath, and onto a towel on the floor, putting her in the damn recovery position, and finally trying to cool her down as much as possible... not easy with underfloor heating...

Damn mood pretty much ruined for the night...! :/
Wow. That sucks.

For more roominess, try a hotel with a jacuzzi suite. Those tubs are (typically) larger and better suited for that sort of thing.

Also, let your sig other draw the water, perhaps? ^^;;

Also - bring some bath-safe lube if you plan on underwater penetration. Most lube (natural and store bought water-based) tends to wash away, which can cause problems.

Honestly, the easiest way to go about it is foreplay above the belt in the tub, everything else on the bed afterwards. As sexy as I find the idea of underwater sex, it's kind of difficult to actually make work without a lot of preparation and forethought.
 
Apr 28, 2008
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Well, my story isn't about the sex per-say, but after it. It was at her house, and being alone in her house and teenagers and whatnot, we started having sex. Well, her friends came over and apparently started watching us from the window. We didn't pull down the blinds before we started for some reason. Anyway, her window did face into the backyard, where people rarely walk through, but it's a quick way from a friend of her's house to hers. After it was all said and done, we got dressed, they knocked on the door, came in, and started "critiquing" our performance. One of her friends (who really doesn't like me) also said how "cute" my penis looked.

>_<

But according to them, I'm "not bad". So there's that!
 

SadisticBrownie

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May 9, 2011
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I was 17, with my laptop in the bathroom, doing what 17-year old boys do in bathrooms. My mum comes down, asks what the noise is (she thought I was listening to music). I, being an idiot, forwent the escape route and denied any noise. Then I was stuck with the issue of getting my laptop back to my room, past my mum. I eventually decided to hide it in the washing basket, and then proceeded to quickly return to my room, planning to retrieve it later.
After about ten minutes, she came in with the laptop, set it down, and we had a very awkward moment. Thankfully, she's never mentioned it since.
In terms of actual sex, not much except being really drunk and fingering a girl in the middle of a crowded nightclub on holiday, with lots of people watching. Though to be fair, we were far from the only ones doing stuff like that, I'm pretty sure there were two people having actual sex against a wall.
 

Elementary - Dear Watson

RIP Eleuthera, I will miss you
Nov 9, 2010
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Bara_no_Hime said:
Wow. That sucks.

For more roominess, try a hotel with a jacuzzi suite. Those tubs are (typically) larger and better suited for that sort of thing.

Also, let your sig other draw the water, perhaps? ^^;;

Also - bring some bath-safe lube if you plan on underwater penetration. Most lube (natural and store bought water-based) tends to wash away, which can cause problems.

Honestly, the easiest way to go about it is foreplay above the belt in the tub, everything else on the bed afterwards. As sexy as I find the idea of underwater sex, it's kind of difficult to actually make work without a lot of preparation and forethought.
:p I lagh on it now... and we broke up recently, but never tried it again... in fact I think that was the last bath I actually had...! I have only showered since...!

But a hotel does sound like a better idea... I haven't stayed in one of those for years! :S

OT: I have another story... not so much funny, as just a bit weird, and I wonder if anyone else can relate...

I move a lot in my sleep, and I will often talk, and sometimes sit up and arrange pillows, or what ever is in arms reach...

On more than one occasion I have woken up in the early hours of the morning, mid-sex... and then after finishing, and being totally confused, learnt each time that I had initiated it! Seems that on occasion I had wandering hands in my sleep, and had... well... to much detail for here, but you get the picture!

Anyone else had sleep sex which wasn't drink related?
 

Elementary - Dear Watson

RIP Eleuthera, I will miss you
Nov 9, 2010
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SadisticBrownie said:
In terms of actual sex, not much except being really drunk and fingering a girl in the middle of a crowded nightclub on holiday, with lots of people watching. Though to be fair, we were far from the only ones doing stuff like that, I'm pretty sure there were two people having actual sex against a wall.
By any chance you arn't one of the inspirations for the Inbetweeners are you!? :p

Reminds me of a mate of mine... the first time he ever fingered a girl was in the sea...! :O
 
Apr 28, 2008
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Elementary - Dear Watson said:
OT: I have another story... not so much funny, as just a bit weird, and I wonder if anyone else can relate...

I move a lot in my sleep, and I will often talk, and sometimes sit up and arrange pillows, or what ever is in arms reach...

On more than one occasion I have woken up in the early hours of the morning, mid-sex... and then after finishing, and being totally confused, learnt each time that I had initiated it! Seems that on occasion I had wandering hands in my sleep, and had... well... to much detail for here, but you get the picture!

Anyone else had sleep sex which wasn't drink related?
Well, I once accidentally walked in on a friend having sleep-sex. Apparently he did what you did, she was riding him, I walked in and she freaked, and he started snoring. Seems she didn't realize it either XD

I just started laughing, and she shouted at me to get out.
 

Vault101

I'm in your mind fuzz
Sep 26, 2010
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ElPatron said:
Vault101 said:
back in highschool bunch of freinds asked if I had "hooked up with a guy yet"....

...I had not...
Achievement unlocked! You would be much more preferable than a girl with several "miles" in the odometer.
I kind of get what your saying...but I dont like the Idea that "virginity" is some big special "asset" girls have....kind of goes back to the days where women were property


ForgottenPr0digy said:
[snip [quote/]

well that's a good thing you didn't end up like those other girls who got pregnant and dropped out of high school
haha..well to be fair I dont know anyone who got pregnant and droped out, the Idea of toungue wrestling with some guy just didnt make much sense to me

also watching bad movies because the main guy in it was "hawt!"...its like "this movie is awful...WHY are you watching it?...is this like porn to you guys? are you getting off it to this? seriously I DONT GET IT"
 

RanD00M

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Oct 26, 2008
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canadamus_prime said:
Loop Stricken said:
Relish in Chaos said:
What are your most embarrassing sex-related stories?
That I haven't had any yet.

ZING!
That I'm 30 years old and I haven't had any yet. :|
That officially qualifies you for wizardry. Or it would have had you honed your skills, but alas you are now forever a mortal.
 

Elementary - Dear Watson

RIP Eleuthera, I will miss you
Nov 9, 2010
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Irridium said:
Well, I once accidentally walked in on a friend having sleep-sex. Apparently he did what you did, she was riding him, I walked in and she freaked, and he started snoring. Seems she didn't realize it either XD

I just started laughing, and she shouted at me to get out.
Haha! That's pretty funny! I like the fact he was still completly gone, even with all the ruckus! :p

I'm so active in my sleep that I would wake up after getting out of bed, and putting on a condom, completly by myself, in my sleep! :S
 

Loop Stricken

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Jun 17, 2009
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hazabaza1 said:
Loop Stricken said:
hazabaza1 said:
BlindTom said:
I once impregnated a female and then made her get an abortion. WHOOPS.
Fist bump.
OT: Well this was this one time I [sub]cried myself to sleep[/sub] [sub][sub]because I'm so lonely [/sub][/sub][sub][sub][sub]ohgodwhydoesnobodyloveme[/sub][/sub][/sub]
This thread was going so well and you had to go and remind me!

Q_Q
I would suggest that we cry one another to sleep but I like the mystique that we have going on here.
Ah, rejected again.