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.
.

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.

The one I fucked said she was 24 but her driver's license said she was 19. Have to say she had a nice tight pussy so cumming in her was pretty fast

Known the guy 46 years...
 

Fuck two of his ex-wives before the were his exs and his two daughters by the second wive, the oldest was 19 when I fucked her, a few years after that I ran into the younger sister working and did her too. The guy is a dick. The 19y/o persued me she even called her mom to ask if she should, mom told her I was worth the fuck.

A long time ago I lived by a guy who was a total ass hole twoard his wife. Me and her ended up fucking once in my garage. They had a 22 yo daughter, but never did nothing with her. In the above case I had no regrets of fucking his wife that one time, it was very enjoyable.

no regret, just dangerous
 

LOL I didn't regret this but it wasn't a good idea. When I was younger I dated a fiery little redhead named Tracy for 6 or 7 months. She was a total sex maniac, all she wanted to do was fuck. In her pussy, in her ass, outdoors, in a car, where ever, she didn't care as long as she got some dick. She loved to drink and watch porn videos while being fucked silly. We finally split up and she moved away and we lost touch.

A couple of years later I ran into her older sister Kathy and we spent sometime catching up and she mentioned that Tracy is now living in a large city about 2 hours away. I gave her my number and asked her to give it to Tracy next time she talked to her. Two days later I get a call from Tracy asking if I want to come to her apartment and have a couple of drinks and talk about the old days. I grabbed a bottle of her favorite liquor and headed to her place thinking alright - I am going to get some tonight! When I get there she is the same bubbly little Tracy looking good in a pair of tight jeans and a tight sweater. We fixed ourselves drinks and sat on the couch to talk.

Well right away she starts talking about this guy she just started dating, she is staying faithful to him, he works nights, he just got out of prison on an assault and battery charge, he is the jealous type, she doesn't want me to get the wrong idea, we can't have sex because she is seeing him now. Blah, Blah, Blah. I reassure her that I am just there to see an old friend, we can have a couple of drinks together no harm in that, blah, blah, blah. Meanwhile I am thinking great, a two hour drive down here, and then two hours back tonight, and I don't even get a handjob!

We have a few drinks, and I said well I have a long drive ahead of me, I better start heading home. She said wait a minute, jumps off the couch and disappears into her bedroom. A few minutes later she reappears wearing a lacy, filmy white lingerie, parades around the living room showing herself off, and said I just wanted to show you my fuck-me outfit. Next thing I know, we are on the living room floor fucking the shit out of each other. We are using various positions, we are all over the furniture, on the floor, we kept drinking and fucking until we both passed out on the floor of her living room.

Next thing I know, she is shaking me awake. Tracy said you better put your jeans on, it is about 7 o'clock and my boyfriend likes to stop by my apartment on his way home from work. LOL all I can think about at that moment is the violent ex-con walking in and finding me naked on the floor wrapped up in his naked girlfriend - I jumped up, threw my jeans on and ran out the door with the rest of my clothes in my arms saying I had some errands to run and I better get going. We did manage to hook up a few times after that but usually when Tracy was between boyfriends.

Lol not quite like your experience, but I sort of had a similar kind of one once when I was 17. I had a older friend who had a friend named Connie, she was 36. Her husband was doing six months in the county jail. Anyway this older friend of mine ended up taking me and her along with his girlfriend on a drive. It didn't take ol Connie long to start flirting with me in the backseat, I eventually got the nerve to stick my hand down her pants. A few hours later when we ended up at her house she got naked, I ended up fucking the shit out of her. She was the first older woman I had been with. After we was done fucking, I was told by her how violent her husband was and that I had not better let out what we did. I seen her husband after he was released, we was at a party they was having for him. The guy was frail and looked like he couldn't whip his way out of a wet paper bag and even had a squeaky voice, I was laughing real hard to myself. I actually got the impression he was maybe someone's b*tch in the can. Lol

Some guy I met at a party and went back to his place, halfway through we hear his girlfriend come home, dude didn't tell me he was in a relationship and well yeah not so good that beatch was crazy

In my young single days a few married and engaged women in my social circle and a work colleague.
It was probably a bit risky and out of character for me but I didn't care at the time.
I felt no guilt then or since as I figured that if they were the people in a relationship it was up to them to make the moral judgements.
Although I know I shouldn't have fucked married or engaged women, it did teach me a bit about life and people as I always had this idea as a teenager, that all women wanted was to get married and have kids and it was just some of the guys that fucked around. I soon learned that anyone could have the potential to stray if the circumstances were right so I remembered that when I got married.

A couple of these women had something in common in that they had only one boyfriend and married young and probably felt they were missing out. Another I had dated briefly but never fucked said she figured something would probably happen between us at some stage and wanted to do it whilst she only engaged as she would feel guilty after she was married.
Unlike some of the posters here, I knew all of their partners and they were all Ok, one or two were friends.
I sounds as though I wasn't a nice guy to have around but I never really pursued any of these women, they all came on to me and it seemed rude to refuse.

Worked with a girl that happen to some years ago. She was dating this one guy and didn't know he was married. Him and her ended up back at his place after he thought his wife had went to work. Turned out his wife was already suspicious about him. She ended up storming in on them while they were doing the deed. His wife pulled a gun on her and chased her outside and down the street. She said that she didn't know what happen between him and her afterward...she wasn't about to find out.

Damn lol that sucks! she basically went streaking down the street scared for her life, goes to show you can't really know what to expect from people you date lol

The 19 year old
 

It has been years, I run into the 19y/o from time to time, now she is marred and got two kids. The first time we ran into each other after our tryst, she was with the guy she later marred, she took me aside and apologize for our hook up telling me she just did it because she was mad at her dad, it would never happen again, and it hasn't. She was some what rude about it and did not what the guy to find out. but later run-ins have been more cordial and now she just acts like the daughter of an old friend. Don't know if he knows about me and both his Exs or the other daughter but he does know about her. He and I only see one another about once a year and he has never really said anything.

For sure lol

My high school best friend. Sex was great, we didn't cheat on anyone,she wasn't crazy or anything and everything was legal... but...

Things change a lot after having sex with someone; specially someone as close as your best friend. We could spend hours talking about anything, but after having sex, the sexual tension was so high that we ended up fucking every single time.

It sounds good in theory, but in practice; sometimes you need an innocent friendship to talk about stupid things and not turning everything into sex.

a girl
 

yhjsxzmhfm dfzngx

The counselor's daughter
 

In high school I worked for the school district so I was around the school at many strange hours, doing work that couldn't be done while school was in session.

One Saturday the boys counselor's daughter was also there, decorating for a some event that evening. She was flat and skinny but had a pretty face and a
nice round ass. I stopped to chat for a bit and for some reason the talk got quite personal in various ways. We fucked several times in several places and neither
of us got done what we had originally came there to do.

We wound up becoming very good FWB and could always rely on each other for some emotional comfort and satisfying sex when things weren't going well
in our life. The only thing was I couldn't look her dad in the eye after that first Saturday though. I'm think he figured things out but he never said anything to either of us.

a stagist girl
 

she went in my office for learn the work, after 3 months I fucked her for the first time on her table in the office. I fucked her many times in 3 and half years, expecially in the first year she was my regular lover (I was married). Then she left my office, I'm happy I never accepted her request to divorce, but I feel really guilty. Well, now a little less, since my wife had a lover for 4 years

I got a student job at the country club rec center, just hanging out to supervise HS age kids if the wanted to play pool, ping pong or whatever. It was an easy job because hardly anyone ever showed up, just paid study time for me. One night three teen girls came in, they hung out, played pool, the oldest one, who was about my age, came over and talked with me, she was flirty, I figured she was just showing off for her friends. But they had this rich b*tch attitude and I was the hired help.

The next night, just as I was getting ready to lock up, she showed up by herself, she wanted me to play pool with her. Now I am not much of a pool player, but she had a role she wanted to play, so I went along. Her short skirt and teasing and we had sex on a chair.

A few days later the director called me in and fired me without much explanation. Rumor was that I took part in an orgy with some of the member's daughters. She wasn't hot, there was no orgy, and I lost a revenue source. I guess I was lucky, by today's standards I would have been labeled a sexual predator.

Caught a guy that worked for me screwing a Dennys waitress at the terminal office, but didn't fire him. It was a good thing no one else seen him. Yes, the world sure has changed.

Hahaha....buddy I hear you. I sure as hell should of never fucked my first on !!!!

Thats so true, we have all been there

College roommate's girlfriend
 

My college roommate was dating a "girl next door". Not a head turner, but athletic, toned and really nice - she was friends with everyone. Her and I got along great - never once was there anything sexual between us. Up until one night.

We all had been partying quite hard. It was early morning and I returned to our room, but ended up walking in on them as she was naked and in a cowgirl pose. I had never seen her bare small-ish tits before, so it was a combination of sheer excitement and total embarrassment for me. I quickly apologized, turned around and walked out.

Resigned to sleeping on one of the couches downstairs in our common rooms, I knew that my semi-hard cock wasn't getting any action this night. Oh, well.

After getting as comfortable as I could on the couch, I started to fall asleep. The frat house party was over and quiet. A few minutes later, my roommate wandered in and crashed in the couch next to me. I asked what was going on. He mumbled that he was too drunk to get hard and just needed sleep. He quickly fell into a slumber.

I lay there, knowing that his hot girl was in our room and was probably horny and unsatisfied. I wish I could say I struggled a long time with this dilemma, but I was crazy at this point and I snuck back upstairs. Plus, I was even more devious. I quickly took a shower, which was just next door to our room and barely wrapped a towel around myself. I made sure my ass was mostly uncovered and my dick was thick and full, but not upright.

I walked back into the room, hoping that she was still there, but also maybe hoping a little that she was gone and I could just safely masturbate myself to sleep. But, she was there.

My roomie's bed was near the door, positioned perpendicular to mine, which was along the wall and above my desk. As I walked in, with the towel just hanging between my midsection and the bed, she was startled and sat up quickly, holding the sheet to her neck. I feigned surprise and said something like, "I thought you were gone." I turned partially away and headed towards my dresser knowing she could clearly see my ass. I heard her roll over. Damn!

I took my time putting on my boxers and could see she wasn't watching. Damn damn!

I crawled into my loft bed and laid there. Nothing. Minutes ticked by. There was no way I was going to sleep. Not with my cock in charge. I finally resolved myself to jerking off in the bathroom. So, I got up and headed there. Once there, I sat on the toilet lid and grabbed a Penthouse from under the sink. After stroking a while, I found my mind wandering to the chick in my room and how inconvenient it was sitting on that toilet. Screw it. I decided to jerk off (quietly, I thought) in my own bed.

So, I walked stark naked back to room with the porn mag. I walked passed her bed in the darkness with my full hard-on on display. Not sure if she was even awake though. I crawled into bed and laid there on top of the covers and clicked on my reading light. She couldn't see me from her bed, but the dim light was noticeable. I started stroking while looking at the photos and found that this was really exotic and I was definitely headed for a major orgasm.

That's when she stirred.

I stopped, my hand in place, eyes wide open, and froze as I saw her swing her bare legs out of bed below me beyond my feet. Was she leaving? But, then I saw her hand reach up and take a hold of the handle I use to pull myself up into the loft. My cock jumped! Three seconds later, her face appeared near my feet at the bottom of my mattress. My aching rigid cock, still fully gripped, was only a couple feet from her face. No secrets now!

She didn't even flinch.

She said something like, "Can't sleep, eh?" I acted a little embarrassed and answered, "No way, not until I... you know..." After a short glance at my penis, she continued to climb up and proceeded to nudge me over to make room. "Neither can I."

She had a white T-shirt on, but not for long. The magazine dropped to the side and I had my tongue in her mouth as soon as I could reach. It was no more than a minute before we were fucking, licking and sucking like crazy. I was sooo ready for her. Apparently, she was ready, too. I remember that she came hard and loudly while I was eating her pussy whilst I came in her mouth and she swallowed it all. She even wiped her chin and licked that up, too.

Minutes later, we were on the couch in our room for a second round, in the dark, fucking again and I came a second time while deep inside. The only negative about this rabid encounter was finding my condom ripped after pulling out. She said she was on the pill, but still freaked us out a little.

She fell asleep on my roomie's bed and I crawled back up to my loft. A few hours later, as the morning light spilled into the room, I could see her naked body lying on the bed below and couldn't resist to jerk myself off while watching her sleep. At this point, I was finally fully spent and could move on.

She continued to date my roommate for the remaining two years of college, with us reverting to our usual friendship. Not a word ever spoken about our drunken and crazy encounter. Not even at their wedding, which I attended. She wore white, which she should have, but I kept thinking about her licking my cum off of her lips. I kissed those same lips at her wedding. Haven't seen them in years now, since we both moved away.

It was a great fuck. No doubt. But, I shouldn't have done it.

Hot story

Myself.
You've been there too.
Most are unintentional; or backfires, or best laid plans turn to crap, bad timing, or stupidity.
Usually when/where least expected, often with maximum repercussion.
Around people who have no sympathy or pity.
Around the spouse.
You know the feeling.
It's universal.

Cue "The Cars" ??
 

Great story. You could ask your friend "What ever happened to Jenny?" without getting into your past with her...

Not that it matter but that song was by Tommy Tutone, not The Cars... the best known phone number in the world... ;)

About 10 years ago I was at my cousin's house drinking beer and hanging out. Just my cousin, his BBW wife and myself. About 6 beers in she got up and popped a XXX DVD in. My defenses were down and hell, it was interesting. A few minutes in my cousin said, "You wanna fuck my wife?" She smiled and I finally got a clue that they'd planned this. But I figured what the hell.

I followed them to their bedroom and watched her strip and get on all fours. My cousin said, "God she's wet!" and slipped into her from behind while I watched. I was still sort of in shock at the whole deal but I'm a guy, right? I was rock hard watching her body move as he pumped into her. I opened my jeans and started rubbing the belly of my cock slowly while I watched. In less than a minute she looked at me and said, "Bring me that." I stepped in front of her and lowered my pants. I pushed my very rigid cock down to her lips and she sucked me in like spaghetti. It was incredible, the HORNY energy flowing thru my entire body. But for some reason I couldn't look my cousin in the eye while he fucked his wife and she sucked me.

Before he could cum he pulled out and said, "Fuck her." I pulled out of her mouth and moved around to stand behind her. She was soaked and wide open. I grabbed two handfuls of ass and slid into her. She hadn't made a lot of noise with my cousin but now she moaned with each stroke.

I'd love to tell you I fucked her for an hour til she begged me to stop. Truth is, I lasted maybe 5 minutes. Lol.

On several occasions after this event I'd go by and she'd blow me. But we never went to the extremes we hit the first night again.

I shouldn't have done it. It made me uncomfortable around him for a long time. It was hotter than the hinges on the gates of hell. But maybe I shouldn't have.

My ex-fiancee, apparently. :/

Future "Aunt"
 

I may have told this before, but I couldn't find it here.

My uncle who is only a few years older than me was engaged to this Italian gal and they lived together. Slightly overweight with d-cup or more boobs - massively hairy pussy. She had a reputation as easy - I knew guys who had fucked her. They had a house with a pool. He worked out-of-state quite a bit. I would go by and mow lawn, fit stuff, wash her car etc.

I stopped by one day to mow their lawn. He was out of town and she wasn't home either. I finished mowing and was sweaty as could be. I decided to take a naked dip in the pool to cool off and be refreshed. I had a change of clothes, but no towel with me. I got out of the pool and decided to brush the pool and check the chemicals while I dried off.

I'm doing my thing nude on the pool deck when she "future aunt" walks out on the pool deck with a big smile and laughing commenting on coming home and finding a naked man on her patio. Well no need to cover up at this point so I joked it off and shook my dick at her and it started to get hard. She walks back in the house and comes out with two towels.

Without saying a word she strips down and says lets take a swim together. We both got in and were chatting about things in general - nothing sexual. After a while she swims up to me and hugs me and wraps her legs around me. She makes a comment about rewarding her pool boy for good work. She start rubbing her pussy tightly against my cock and makes a comment about how I must be enjoying this.

She slips my cock in her and we go at it for a while, but without the natural lubricant it was slowing down our progress toward O's. She suggested we get out and try this out of the pool. She hike herself up on the deck with her legs still in the pool. I came up between her legs and commented about how hairy she was. She says - it still tastes good.

So here I am eating the pussy of her right on pool deck. I told her I thought we shouldn't be doing this, but my cock was really needing the release. I got out of the pool and we fucked on a lounger until she came and I was about ready to. She told me to not cum in her and tell her when I was ready. Right now I said and pulled out. She slid down the lounger and I fucked her face from above until I came.

We got back in the pool to cool off and agreed that this shouldn't go beyond us. All well and good until her girlfriend walks out onto the pool deck as we are getting out still fully nude. No threesome then, but I fucked the friend sometime later. The "future aunt" did give me a couple more blow jobs when I came over to work other times, but it stopped when they got hitched.

My uncle divorced her after catching her cheating a couple times.

My best friend growing up. One drunken afternoon turned into a drunken evening back at mine. It was weird and functional. It answered the question immediately for us as to whether our friendship would ever be more than that

House party
 

It was the summer after I graduated from college. My GF from college and I broke up after graduation, after dating all 4 years, and I was anxious to get back in the game. A few close calls, but there was one girl in my big circle of friends I was really hot for. I had dated her a couple times but she was playing it slow after coming off a break-up also.

We used to rotate hosting parties among a bunch of us, and this time it was mine. I was renting a house and my roommate was out of town. The girl I was after couldn’t make the party which bummed me out. One of her friends who I hadn’t really taken notice of attended and was pretty flirty. One of the other friends (female) who had driven had drank too much so I told them they could sleep over and use my roommate’s room and mine. I would sleep on the couch. I was trying to be a good guy.

Two of the girls took my roommate’s room and this girl that was flirting took my room. Probably 2 times she said I could sleep in the room with her and I answered that I would sleep on the couch, it’s Ok. (Remember - trying to be a good guy, and I was interested in her friend who wasn’t there). After the 3rd time, it finally occurred to me she wasn’t asking me to sleep and my little head started doing the thinking. Even so, I tried to be a gentleman and just laid next to her with my underwear still on. That didn’t last long as she started rubbing my quickly erect cock over my shorts.

Next thing I know, we are fucking and she’s incredibly loud and vocal, screaming dirty talk. At the time, I don’t care, I’m finally getting laid after a couple month’s dry spell. It was kind of odd after. She’s looking through my closet and making fun of all my suits and calling me a “corporate clone” and such. I am starting to wonder what I got myself into. Then, at breakfast, I see the looks on the faces of the other two female friends (one of whom was like a sister to me). She comes over to me and says I guess I had a good time, and I do realize the two bedrooms are next to each other.

Fast forward a couple days. The girl I fuck is telling everyone we fucked, even though I hoped all three that slept over would be quiet. The girl I was after basically wouldn’t give me anything more than a “hi” after that. I try to see if I can pick things up with the one I fucked (I know, she was crazy, but I was 22 and it was pussy). Nothing. She was just sleeping her way around and I just was another proverbial “notch on her lipstick case”. She also chewed me out for not wearing a condom, I told her I thought she was on the pill. She was, but she wanted to give me grief. Good thing I didn’t catch a disease.

So, I lost the girl I was after, the one I fucked was crazy and didn’t care to date me anyway, and my good friend (the one that was like a sister) thought a little bit lower of me after that.

The best part is that about 10 months later I ended up getting back with my college GF (we lived in different states), got married and have been together for 25 years. It all worked out, but that is one that I regretted fucking.

My First Girlfriend.
 

I was nearing 18 and still a virgin. Desperate I had considerably lowered my standards.

I hooked up with this girl at a party. Plain but with an OK body. She met all the requirements on my checklist.

1. Breathing.Check.
2. Has vagina. Check.

It was a short list.

When she offered it to me. I jumped at the chance. The act was not the great, but happy that I had lost my virginity.

You know the old saying

Men use romance to get sex, where as women use sex to get romance.


She was definitely one of those women. She used the sex to trap me into relationship. I soon found myself dating the girlfriend from hell. Luckily the relationship soon became toxic and we broke up.

I have always regretted fucking her. I wish I had waited a few months until I met my next girlfriend.

Read about her here.

https://forum.oneclickchicks.com/showthread.php?t=217504

One and a Near Miss
 

Like many of these stories, a surplus of beverages was clearly to blame... [to paraphrase a certain song] Late one Saturday night in college the beer goggles were firmly in place and this girl I had never really spoken to very much but knew generally as a peripheral member of one of the social groups I hung out with seemed to be constantly in my vicinity. One thing led to another and I was back at her suite she shared with a couple other girls, each with their own bedroom. We started fooling around pretty heavily in the main room, as in pants undone and hands exploring, when her roommates burst in. Fortunately the lights were really low, and we pulled ourselves together and moved to her bedroom to continue. Things progessed rather unremarkably, and at some point in the wee hours of the night I found myself stumbling back to my apartment through the snow and near 0* F temps deeply regretting what had happened. [In my book the walk of shame does not officially start until the sky starts to get light.] I had a pretty serious GF who was in school 250+ miles away so it had been a while since there had been any female contact I rationalized. In the bright light of day things looked no better. For the next couple weeks this girl seemed to always be next to me with her "puppydog" eyes wanting to get together again. I had hoped she would get the message, but eventually had to tell her while she was a great girl, I had a serious GF in another state and that evening was a mistake.

Another year, a different school in a different state in a much warmer clime, the girl was a complete stranger late one night at a party. For some reason which escapes me to this day, I thought it was a good idea to take this girl in my car back to her apartment for some night moves, another song of the same vintage. Fortunately this time, the fog of beer lifted sufficiently - probably aided by the fact that this girl had the absolute worst breath [who knows what she had been doing previously :eek: ] and I removed myself from her place before there was any real contact. That was the closest near miss, and one that probably saved a trip to the health clinic... :rolleyes: