Who have you fucked that you shouldnt have ?
 

In my case it was my first wifes cousin. Me and the wife was separated at the time and her cousin always had a thing for me. Me and her ended up fucking twice, both times were bareback and I shot off in her. A month later she was running around telling everyone one she was knocked up by me and that we planned on getting married, it was bs of course, she wasn't pregnant at all and I had no plans of wedding her. She was suppose to keep things between us, but coudnt keep her mouth shut. Eventually it all subsided and past, but she was one that I shouldn't have fucked at all. A couple of years after me and the first wife divorced her cousin tried to get me to fuck her again, I told her to go piss of that time...the last experience was bad enough with her.

Cue "The Cars"
 

During my last year of college, my best friend dated a girl named ,uh, Jenny. SO, "Jenny" was always flirty with me, and when we said hi, I got kissed on the lips, not the cheek.
About six months after I graduated and moved back to my home town, Jenny moved up here, for a job. She and "John" had broken up, but as I found out, hooked up again later. Anyway, after a few half hearted attempts at hanging out and not screwing each other's brains out, we did. She was a pretty good looking woman, blonde, with a nice round ass, and pencil eraser nipples on medium to small tits. Having sex was great for both of us, but I felt a little guilty then, and have ever since. I never see her anymore, but he is still one of my best friends. To this day, I don't know if he knows, and it has affected our friendship, from my side at least. So as much as I liked doing her, I wish I hadn't.

So sorry Pete..........
 

I really, really regret screwing the ex of my best buddy from HS. He and I drifted apart and went our separate ways after HS and being in the service, but he was always in the area and still friendly.

I had sort of dated his ex long before he even met her and she was just a tease.

After they were divorced, she and I met by accident and we set up a "fuck date". We knew it would be just that. I wanted to finally fuck her, and I think she may have been on a revenge (fuck all his buddies?) campaign. So we both had an agenda.

So we did it, it was quite an unimpressive affair. One and done. Accomplished our goals I guess...

I think our tryst got back to him, I can only hope it didn't. Things other people said made me think he knew about me banging her. I suppose it was possible she even told him as part of a revenge tactic. But at the time of our "date", only pussy was on my mind.... it overrules all sense of decency.

Logic would say that they were divorced so who cares.... but a old buddy's lady? etc. etc. And, in retrospect, I realized he was a sensitive guy in matters of the heart. Shortly after that he just disappeared and started a whole new life elsewhere. Recently I found out he died of natural causes last year. That really made me feel guilty.
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a girl
 

shouldn't have
 

When I was 26 I fucked a store manager from a woman's boutique clothing store that I had met 2 days before. She was Asian, young, cute and hot. I took her back to my place and fucked her that night. When she went to the bathroom I checked her purse that was open to see if the name she gave me was her real name. I found out it was her real name and she was on the pill and also had condoms in her purse. I fucked her bareback but pulled out when I came. Made me wonder if she was into one night stands and if I caught anything from her because I did not use a condom.
Never saw her again.

A coworker long ago
 

As I've mentioned in some other stories, my wife and I met at a grocery store we worked at while in college. There were a large number of us late teen and early twenty somethings working there so it was always a good time, with someone throwing a party just about every other week or so.

A couple of months before my wife and I started dating I was at one of these parties. A girl from work, Jill was there. She had a reputation of sleeping around with many of the guys from work, with 4 of my friends having claimed to. We had always been friendly while talking but I wouldn't even call it flirting. Looks wise I'd say she was just above average, dirty blonde, smallish boobs and a slightly large rear end.

Anyway that night at the party she had ridden with a couple who proceeded to get drunk and then ditched her at the party. Being the nice guy I am I agrees to give her a ride home. On the drive there for the first time she openly started to flirt with me, basically coming out and asking me why we hadn't fucked yet. I spewed some crap about just having broke up with a longtime girlfriend blah blah blah.

Next thing I know she is leaning over and nibbling on my ear and rubbing my rapidly hardening cock. We got to her place and my little head talked the big head into following her inside. Luckily I did have a condom. The sex was nothing remarkable. After we were done we chatted for a little bit then I headed home.

The next morning I woke up and was thinking man I can't believe I slept with her. Actually felt a little dirty. Next time I saw her at work and she was back to our non flirty talks which was more than fine with me. Then she quit shortly after.

Sorry to hear he past. It was about the same with me on her cousin, I was thinking of the pussy. What a mistake she was though !

I had a similar experience with a walmart cashier once, but wasn't afraid of getting anything from her. I used a condom on her. She was married.

Shouldn't have is something of a moving target: it depends, I suppose on what standards we apply. I have fucked women who were off limits, and I suppose you could say I shouldn't have, but I've done it so much that I don't know that I see it that way.

On the other hand, there were a couple of occasions, now years ago, when it was flat out dangerous, and not with the risk. In both cases, I'm talking about barebacking wh*r*s. Why I did it is, I suppose, obvious: I let sex control my brain. In neither case was it spectacular sex and in both cases I worked about it enough that it was not worth it. Shouldn't have done it.

Years ago I took a part time job working at a local hospital in the ER. I worked with a couple where the husband was an RN and the wife was an LPN going to school to also get her RN License. She was a definite hottie, dark skin, smallish tits and an awesome body. She was also a huge flirt and tease at work. There were rumors she had fucked half the guys in both EMS and the Police Department. Her husband was a super nice guy, do anything for anybody type. I got along with him and thought he was a good guy. At the time they had one child who was about 5 years old. They were both in their mid twenties.

I saw her a lot on my regular job when she was doing clinicals at another hospital and she always was a big flirt and things began getting heavier once I took the part time job with her. We had a lot of physical contact whenever possible. On one occasion we stepped into a small x-ray room closet and I ended up getting her bottoms down and she bent over a counter with me playing with her pussy and ass but with me still fully dressed.

One night her husband was already done with his shift and home and she had worked late. She called me and asked me to come drive her home so her husband would not have to wake their son up. I was out on my other job and went and picked her up at the hospital. On the way home she suggested I stop along the way to "talk" and I against better judgment did. We began kissing and our hands wandered and soon I had her bra and top off and had her scrubs down off her hips. I was still telling myself to stop but once she had my cock out all common sense was gone. I grabbed a condom and she said no, she was allergic to latex (which I knew from her gloves at work) and to just fuck her. The little head was in full control by that time and I fucked her up against the car bareback. She was incredibly tight and moved like crazy driving me crazy. She definitely loved to fuck and we ended up fucking twice that night with me unloading deep inside her both times.

We both got dressed and she assured me she was on the pill but that her husband didn't know since he wanted another baby. We stopped and grabbed some food at an all night place and I took her home. Her husband was waiting for her when we arrived and I felt terrible as he thanked me for driving her home and making sure she was ok. He never said anything to me afterward and I ended up fucking her several more times before I was transferred to another district and we moved. I always felt terrible about fucking her behind her husband's back but she was insanely hot and I could not hold back. I actually fucked her one time in an empty exam room while her husband was on shift outside.