Have you ever had sex with someone you shouldn't have?

[Bill3250]

Of course....a few one night stands who wanted to make it a lifetime affair. Friends lovers/wives. A few others I'll bother listing. But I have never regretted any of them.

 

[Livelygent]

Have you ever made that mistake? Screwing someone, knowing it is wrong but you couldn't control it.

Once in my late teens or very early twenties, I did go to bed with and screw my brother's wife, and got caught.
This memory comes back from time to time to haunt me. Naturally I enjoyed the sex, but I feel that I let my brother down. That is where the guilt comes in today.

 

[Rhosyn]

Have you ever made that mistake? Screwing someone, knowing it is wrong but you couldn't control it.

I once fucked my best friend at the times ex boyfriend. Even though they were broken up for sometime it still was horrible because they still talked and were trying to work things out. I eventually told her years later and all she asked was " Wasn't it good" and sort of giggled.

 

[blackdragonfly]

I hate to say it but Idk how many people I have slept with to begin with but majority of em were ones I wanted (yes I am a bit of a slut). The last woman I was with was just down right horrid. She was hot, but had NO clue how to lick pussy (even though she bragged and begged me for months).

 

[mryanne58]

Not yet, but . . .

 

[like2pleez]

OH yes! too many too tell.

 

[WrittenInStars]

i often have in-oppropriate thoughts about friend that id LOVE to have sex with . . . although I think unless we were all drunk that would ever happen . . . bu it doesnt stop me thinking about it im getting rather excited thinking about it now :S

 

[BignBI]

The one I regret was when I was younger and it wasn't that I didn't enjoy it but it was that the person was a much older babysitter and it was wrong for him to do it and he was not attractive to me but young people are impressionable so he took advantage of that situation. It has helped me come to terms with my bisexuality and my wife has accepted me and now fucks me in the mouth and ass with a strap on. So it all worked out in the end I guess.

 

[BosozokuX]

1) My last ex who was 10 years younger than me (I was 28 she was 18) and my best friends cousin. She turned out to have a huge perkocet/xanex problem.

Oh, and he also caught us in the act. Me, balls deep in her, pulling her hair with her bent over with panties crammed in her mouth, creaming all over my dick, moaning like god was banging her. (i'm not god, she was just loud and theatracical)

2) Some random guy I met on AOL years ago. I rode his dick like a horse and kicked him out after I came. Thank god I made him wear a condom.

3) Some chick I met on Craigs for no strings fun. She got attached (after one night) and wouldnt leave me alone. After finally getting rid of her, I hooked up with her a few more times just cause I was lonely and it was a good lay.

4) Somebody on the other side of a glory hole. I was horny, alittle drunk and totally convinced (probably by the shemale porn playing on the screen) I was geting sucked off by some hot ass shemale. I didn't wear a condom and shit myself until the blood test came back.

 

[Tornia]

There was a girl and her bf that I had on a one night stand. At the time it was great, but I just couldn't get rid of them for ages afterwards. I supposed I should take it as a compliment, but to be honest it was just a nuisance x

 

[BentSecrets]

Have you ever made that mistake? Screwing someone, knowing it is wrong but you couldn't control it.

Yeah, I did. I met this *wonderful* girl (well, OK, she SEEMED wonderful at the time) and we went back to her place and started getting friendly. Halfway through she told me she had herpes, though she'd not had an outbreak in over a year because she took her meds religiously. She was crying and upset and I felt so bad for her (she got it from a cheating boyfriend) I ended up going down on her. For three days in a row I serviced her orally, never asked for anything in return, and on the fourth day I finally fucked her (she'd been asking for days), bareback per her request.

I'd been trying to sort out ways to break it off, because I didn't want to hurt her, but I couldn't see any other way. Luckily the next day I was in a terrible car accident, hit at 70MPH and hospitalized. Made it easier to break it off with her because I couldn't really move well or do anything, and since we'd only dated for less than a week it didn't seem fair to ask anything more of her anyway. Easy out (well, OK, it wasn't easy, it hurt like fuck and still does regularly), I guess.

It's a shame, really. She had a gorgeous body, a smart brain and a sweet personality. What her ex did to her was totally fucked up, because it really cut down her chances of finding somebody. On top of that I was paranoid for months and kept getting tested every 2-3 weeks (expensive!), but a year after I finally figured I was in the clear, and the doctor agreed.

 

[BentSecrets]

Yes. I am haunted by both how guilty I sometimes feel and also how horny the memory makes me feel; a real rock and a hard place. I actually thought about talking to a professional but then thought about it. No way. I will feel regret and horniness always about this. No one can change that.

I'm in that space, except of course, I DO talk to a professional about it. She's pretty awesome, and insists I shouldn't feel guilty about most of them because hell, you gotta sort out what you want somehow. I feel guilty mostly about the ones my partners at the time didn't know about. Still...that's part of the turn on, too.

 

[Sniper 1]

I fucked around with a good friend one night after too much to drink. She is a lesbian and wanted to try a guy to see what it was like. We were both totally wasted and fucked like crazy (oral, vaginal, anal, you name it).

It ruined the friendship. We were both really tense around each other after that. Within a year we drifted apart and haven't spoken now in 20 years or more.

 

[DJNC321]

I let a friends dad fuck me in the ass while in HS. He did this over a period of three months.

It ended when his wife walked in on us while he was unloading in my ass. While she was feaking out, he pulled out and I just stayed in a bent over position dripping cum on her new sofa.

Looking back on it was pretty funny but at the time I was pretty shook up.

 

[gothic_nymph]

In Collage I screwed my roommates boyfriend. and he went stalker on me... Couldn't get rid of him...

 

[GaySage]

.....

 

[PaperAutumn]

Several of my past girlfriends have been a mistake. So, yeah, not that interesting of a story. I just tend to date uggos and psychos and regret it later.

 

[theedebster]

Regets?

As a teenager I was very promiscuious. I was the Queen of giving handjobs and blowjobs to the point I had to move away from town after I graduated from high school. I live in NYC now and over the years I have crossed paths with former recipients of my favors. It has always caused me a lot of anxiety because my past seems to always jeopardize my career.

 

[Bill3250]

I let a friends dad fuck me in the ass while in HS. He did this over a period of three months.

It ended when his wife walked in on us while he was unloading in my ass. While she was feaking out, he pulled out and I just stayed in a bent over position dripping cum on her new sofa.

Looking back on it was pretty funny but at the time I was pretty shook up.

I wish I had an older guy to fuck me when I was in high school, at least someone who know what the fuck he was doing. As it was, must of the guys I sucked off and let fuck me knew less than I did about sex. I guess after the man's wife walked in on you two he stopped fucking you.

 

[Skeebo11]

I have actually........

My 21 year old niece (Not by blood, by marriage). Brought her out to a bar at our cabin one night. She got roaring drunk. I had to have the bartender cut her off. Actually I was pretty drunk myself

Go back to the cabin, and there was a tent pitched near the lake and a note on the door to the cabin that read something like "John, Teri, cabin is full so we set up a tent down near the lake, please sleep there"

So I pour her into her sleeping bag and I get into mine. It was hot out so I had the covers off sleeping on my back. I come to, from a passed out state to her laying next to me with her head on my chest, rubbing my cock through my underwear. The tent is pitch dark as it was a moonless night.

At that point I am really out of it and I am thinking this is my wife getting frisky. She inches down and takes my cock out and starts giving me head. After several minutes of this, I roll her onto her back and take her pants off and go down on her. I start to lick her pussy and she is moaning and cums.

She rolls me onto my back (I still am thinking this is my wife) and completes a great blowjob, and I cum in her mouth.

She crawls up my body and sits her pussy on my cock. (This is now where I realize this is not my wife). I start to rub her tits, and realize that these particular tits are much firmer than my wifes tits, and her legs are firmer too!

At that instant, I realize 'Holy crap' this is my niece. I have always treated her like my own daughter, being a father figure to her since her dad left when she was young.

She is bouncing up and down on my cock and I am freaking out inside. So I let her continue until she cums, and then I roll her over on her back, and she passes out again. I got her underwear back on, put her pants on again, and roll over and try to get some sleep.

'Would she remember what happened the next morning' was going through my head, so I did not get a wink of sleep the rest of the night.

I rolled out of the tent early, and walked over to the dock and started fishing. She rolled out of the tent with a raging hangover, and proceeded to walk down the dock towards me. As she is approaching, I am thinking I am a dead man, she will think I took advantage of her, how could I do this to her etc.

Luckily she did not remember a thing of what happened only hours earlier.

I feel like a total a-hole that I did not figure out that it was my niece fucking me before anything happened.

It was a very tense situation standing on that dock, questioning her about the nights events.

I regret that night in my mind bigtime. However if I was a single guy and 20 years younger, that would have been quite a night. My niece is model material, and a wonderful young woman.

Completely true story, and not one that I am proud of actually.........

 

[zex95966]

once.

I feel kinda guilty but me being the horny bastard i am, the good outweighs the bad...

 

[spraybomb13]

my buddy called me once and said he had a girl he wanted me to meet. i had been drinking, and was bored, so i ended up at his place.
i walked in and this girl was sitting on the floor with a mostly empty bottle of jack daniels. i asked where my frind was, and she didn't reply, just stood up and started to kiss me while her hands roamed all over me. since i was buzzing, i got instantly hard and returned the favor. soon we were naked on the floor and i was eating her pussy while she sucked my cock. i put her up on the couch and began to fuck her hard, but this is where it got "weird"

she started speaking in third person...saying "becky likes that" and " becky likes it harder"....i admit, i liked it, but it was also weird. then she started calling me "walter" which wasn't my name, and to be truthful, i never knew hers either.

being called a different name, was a turn off, so i fucked her hard till i came (inside her, no rubber) i told her i had to piss, and when i got back, she was passed out. i bolted!!

my buddy called me the next day, and i told him what had happened. he laughed, and told me she had gotten out of an institution that day!!

i felt horrible, and that was the only "one night stand" i ever had...



he did say that she always asked where walter was!!!

 

[bi golly]

I saw the title and realized my answer would be "all of them".

 

[tonyblair]

Apart from the entire population of the UK?

 

[delugewriter]

I have the opposite problem - not screwing someone that I should have (using too much self-control maybe?)

Ditto there... Sweet dear god, ditto!