Who have you fucked that you shouldnt have ?

[StudMan69]

My best friend's mom. She was still married and it just happened one night at a halloween party. One of the very few times that I had drank at the time and honestly it was some of the best sex I've ever had. It was taboo and risky and oh so fun. Then it happened again and again. Then she'd show up at the mall and then my games. It became too much, she'd leave naked photos for me to find and panties she'd buy at the mall. I started spending less time with my friend and eventually we just grew apart all together. I ended up moving. I'm older now so when she found me online I was able to look back at the fun we had rather than the weird stuff. She still thought about our time and would recite what we specifically did, that was hot to hear.

[Curiouscouple2469]

Originally Posted by DiegoJames

I think you're absolutely desperate to lose your virginity, and while it's often quick and unsatisfying, it's satisfying enough to want more. And lots of it!

I lost my virginity to a good looking girl, but after that it was for quite some time a case of 'anything will do'. I'm talking about the ages of say, 17-19. Yes, some half-decent ones in there, but more than my share of fright-nights!

The ones less experienced than me at that age could sometimes be less than satisfying, simply through their own inexperience and sometimes fear of getting pregnant (even with condoms involved), fear of oral, fear of whatever. Sometimes, there was the odd one who was willing to go to bed, sometimes even for the sake of getting rid of their own virginity, but who lacked any sort of personality. They could look great, but couldn't buy a personality at the charisma counter in Woolworths. Some of them could be seen as 'I really shouldn't have...'

But one stands out, when I got drunk one night and one girl who had a fancy for me, and I'd known for a long time but never fancied myself hauled me back to her flat. I, in my drunkenness, thought I was just going to crash on her sofa. She was still a teenager, plain looking and maybe the best part of 20st in weight (280lbs, American friends).

Now, I was really pissed (in the British sense of the word...I mean I was very, very drunk!) and she started undressing me. I honestly believed my boots and jeans were coming off to make me more comfortable under a duvet on her sofa

Anyway, I'm naked and getting aroused by her hand job, blow job actions rather than any conscious decision of my own, but now aware what she was doing. Well, guys, as the philosopher says, 'a stiff prick has no conscience'.

Fuck it...just do it!

I roll onto her and I'm in, when suddenly I realise that the whiff of body odour I once got off her in a pub wasn't just an unfortunate incident at the end of a hot day, but routine. She didn't do washing under her arms, didn't do deodorant

I'm fucking a very fat, exceptionally smelly woman!

I gagged and gagged at the horrific smell. I mean, it was rank!!!!

I don't care how drunk I was, when she asked me to go down on her I was still sober enough to imagine it would be no different down there and mumbled the words 'I just want to fuck you' at her, even though I now didn't, and sober never would have.

I should have said 'sorry, I'm too drunk to perform', left and maybe slept under a tree in a park or something, but by now it was 'well, any and every hole is your goal', (we all like to crank the numbers up at that age, don't we?) so I finished off, rolled off her and thankfully fell asleep. When I awoke in the morning -on the sofa, she went to her own bed- it was like the entire flat had taken on the aroma of her armpits (and fanny -UK meaning of the word again) and I gagged again before managing to dress, stumble into the morning sun and promptly throw up at the kerb.

And that, fellas, is the stand-out one that I really really shouldn't have...

I think I knew this girl…. Lol

She was actually a good friend that I knew for some time had a crush on me
One drunken night we just seemed to get into it and one thing led to another but as we started to strip each other’s close off, this hot chubby redhead I had always wondered about, I suddenly became aware of an odour I could not ignore no matter how drunk I was and my hard-on dropped like a deflating bicycle tire…. It was embarrassing as I couldn’t talk my way out of it but there was no way I was getting into it…, she tried sucking me off, jerking old floppy but eventually said “well that wasn’t the way I always envisioned this going when I’ve dreamed of being with you…”

I said “ya sorry way too much to drink” and bowed out. But had to spend the night as I was too drunk to drive.

Pretty awkward morning after. But I felt like a schmuck as she was such a sweetheart “and a great personality” but I just couldn’t do it.

[Hornyinde]

Originally Posted by WoodyWoodWood

Depends on how you define "shouldn't" have:-

1. Best Friends Girlfriend
2. Wife's youngest Aunt (five years older than me)
3. Friends Mother
4. A female friend the night before my wedding

Where should I start?

All sound good to me. Maybe telling the details of each one would help us decide.

[ripstar1]

She was several years older than me and it was over a year until they got hitched.

He was out of town for an extended time for work. I had agreed to keep his yard mowed etc. One day I was mowing and it was hot and humid. I was sweaty as a dog so I thought I'd take a dip in his pool to refresh. I had to do the pool work anyway.

I checked to see she was not there. I stripped down and went in the pool (privacy fenced). I didn't have a towel so I figured I'd "drip-dry" while cleaning the filter, balancing the chems.

The water was just too tempting when I was done work so I got in again and swam around getting refreshed. The next thing I knew his fiance was standing there holding a towel. She said, "Don't you need one of these?" I smiled and agreed. She said that I would have to come and get it.

What I didn't notice at the time was that behind the towel she was holding she was wearing only a bra and thong. Being in a panic I said well maybe i'll swim around some more first giving me time to think this out. Well, she finally laid the towel on a table and said how about if I join you..

Off came her underwear and in the pool she came. She made no doubt what she wanted and came over to me and immediately reached for my cock which immediately started to get hard. It didn't take long before my cock was in her mouth underwater.

She pulled me toward the steps and out on the patio we went. I ate her pussy for a while and ended up fucking. She had a nice body and was a good fuck.

But it was too much of a guilt trip. He returned shortly after that so it never happened again.

[SlyBry2010]

DiegoJames reminded me of my first lay- definitely not good and shouldn't have. But as we say, gotta get that first one done any way you can.

My best friend Brian had a cousin in the Marines and was deployed somewhere for like a year (back in the 1970s). His wife was Cindy, a pudgy Latino who already had a small child when she came into our lives. The rest of the family knew she was out of control so they sent her to live with Brian's family (we lived adjacent to a Navy base).

Right away, she was out most nights to the EM club dancing and drinking and hanging out with the sailors and Marines. She was horny and probably felt trapped in her life. I was always around Brian's house, it was like my second home. She finally noticed me and started coming on- wanting me to fuck her. One night she stayed home and most everyone else was in bed or whatever. She drug me into Brian's brother's room and we started making out. She was nothing to look at and, as mentioned, kind of roly-poly. Didn't stop me from coming to attention. She absolutely didn't want me going down on her and it wasn't hard to figure out why. She was kind of smelly and slimy. So I fingered her a bit even though I had no idea of what I was doing, but she didn't seem to mind. I sucked on her smallish titties and she liked that.

Then she pushed me back and took my cock in her mouth. I learned her quirk right then- she really didn't know how to give a blow job - her idea of sucking cock was to try and push her tongue into the peehole. Instantly that was not comfortable, in fact it hurt. I told her as much and she got kind of defensive- "Most guys like it." She kept trying. I ended up pushing her away, but not before she accidently gave my cock a decent swab with her tongue. I about came just from that one bit. But that wasn't her style and it wasn't repeated.

She laid back and pulled me on top of her and guided my cock into her squishy pussy. I was going slow because I had read somewhere that women liked that. She tolerated it for a couple of minutes and finally said, "Why are you going so slow? Fuck me already!"

So I started pumping harder and faster and she moaned a bit. Honestly it didn't feel like all that much but with the speed and some small amount of friction in about five minutes I was ready to cum. She had warned me earlier that she wasn't on the pill and said I needed to pull out when I came. So I gave her a few more good pumps and I knew it was time- I just pulled backwards until I slid out of her pussy and dumped my load on the sheets between her legs.

Pretty certain she did not cum but I decided that I wasn't too worried about it. We made out for about ten minutes or so and she tried that damn tongue technique on me again until I pushed her off saying, "No more of that!"

I laid back and made her get on top of me. She sat up and guided my cock into her again. For some reason I got stuck just a little ways in her sloppy pussy. She wiggled around until I was in the right spot and sank down on me. THAT actually felt pretty good. She started going up and down but very quickly I found out that she was too lazy to continue and wanted me to get back on top of her. Same thing, I pumped for another few minutes and damn if I wasn't ready to cum again. Another repeat of the "pull out and dump" and I was done. I got up and went and took a shower (Oh, god, now I smelled bad and needed to wash) in the hall bathroom. Got dressed, talked with Cindy another couple of minutes and then went home. She tried to convince me of a repeat a few times after that but even though I was new to the scene, I knew it HAD to be better that what I experienced.

I think she laid a couple of other guys in our circle, as well as the Marine detachment and whomever else she could get a hold of. In a few months, her husband came back from his deployment- I even met him once and shook his hand. I sort of felt bad but then realized it was "e pluribus unum" with her. She returned to their hometown and I never heard from or saw her ever again. My friend Brian and I had a tacit agreement to never speak of her.

A handful of months later and I had found my first real girlfriend, and right off the bat it was a hundred times better. In fact, I decided that the one encounter with the bride of the Marine Corps was NOT my first time.

[WoodyWoodWood]

Many years ago, when I was single again after splitting up from my first wife, I bumped into Jane, my best friends girlfriend, while out in a local club. I was pussy hunting, and since I knew her, I thought that might get me an easy way in with one of the other girls in her group.

However it didn't work out that way and come the end of the night I found myself alone with Jane, and we shared a taxi home. However when we got to her home, she asked if I fancied a nightcap, so we stumbled into her house. We were both a little worse for wear, and all I can say is that one thing led to another, and before long we were snogging on the couch.

Hands started roaming, clothes started to undo themselves and fall of, and eventually we were at it like rabbits on the sofa. You all know how it goes. Anyway after we had done the deed we dressed and I went home.

A few days later she called me and we went out a couple more times, with both encounters ending up with sex - either at hers, or mine, but it began playing on my mind, shagging my friends girlfriend, so the next time she rang me I got all righteous and told her that I wouldn't be seeing her again.

Then I told my friend that I'd seen her out at the club in town, with another man, and suggested that he might want to look for someone that would be faithful to him.

He dumped her a few days later.......