A fuck you defintely should have had

[Sheana_V]

This was one of the things that made me realize non-monogamy wasn't for me. I had been crushing on this rocker guy (a bassist in a local band) for several years.

I was at a party with him, and we were chatting and drinking. During that conversation, there was clear sexual chemistry between us and he told me he was leaving town for LA next week. There was a definite hint of "this is your only chance" and I'm sure I could have taken him into a bedroom.

However, my boyfriend came over and started acting possessive toward me. I left the party with my boyfriend and the two of us broke up soon afterwards.

I still sometimes fantasize about how that night could have gone.

 

[Texastuffbbc]

A co-worker but it was one of those award trips with spouses. I had a plan for the next meeting but the company downsized and we both left on our own. Lost contact.

 

[justdamhorny]

Have there been occasions when you know you missed out on a fuck that you really, really should have had? When a fuck was almost certainly there for the taking but you let it pass by and as soon as you did, you knew that, years after, you were going to wish you'd done things differently. Haven't we all experienced that?

All I will say is Yes!!!

me too.

 

[DarkrSide]

Former coworker... both attracted to each other.... realized it too late... shared a sweet kiss but we had talked about wanting more.... Some of our conversations (at the Friendliest Place On Earth) were pretty dirty...

 

[tigger_lover]

someone from my teenage years, he went out with my sister and best friend, we have reconnected in later years, but oh what fun it would have been

 

[Fingerfuxs]

There are several that have knocked at my door in the middle of the night , in the moment lust seekers. I can think of a few I regret not answering that knock on my door. There are also a few I’m so glad I didn’t .

 

[benj1980]

a few years ago a gorgeous short haired small framed girl I knew vaguely knocked on my door at midnight. my friends had said I was in at the time as my girlfriend was on holiday with her parents. she made it clear she wanted fucking there and then. I knew I shouldn't and I knew she had a boyfriend too, but that just made me want her more. after a little persuasion she told me she was going upstairs to my bedroom where it was up to me if I followed. well nobody could refuse that so I promised myself a little fun wouldn't hurt but no fucking. She was naked apart from some tiny panties when I got there and my cock sprung to life immediately. her tiny tits were such a change to my girlfriend's huge teenage buds but her nipples were rock hard and made up for her lack of size. after some instant rough kissing i went straight for them and licked them deliciously like some forbidden fruit knowing her boyfriend had been there no doubt within the day. she cupped my balls immediately leaving me in no doubt she wanted me rather than him. i had no patience then and just had to feel her pussy...knowing that a feel was still not really cheating in my mind. she let out such a perfect groan as I worked my finger inside her....followed instantly by my cock. I was helpless to push into her fresh wet lips.....I got partially inside and then imagined of all things my girlfriend. my conscience was torn but my angelic side won and I pulled out....one of my biggest regrets. She understood and continued to go down on me finishing me off perfectly in her mouth, but years later I still rue the day I didn't cum inside her. we still see each other now and again and are both married and I'd love to think she feels the same

 

[Crownvic]

someone from my teenage years, he went out with my sister and best friend, we have reconnected in later years, but oh what fun it would have been

Had an encounter a few years back at a class reunion...someone told me she had a crush..from high school..never saw that one coming

 

[Sinstories]

Have one of those, always regretted not, but in many ways glad I didn't.

Girl I knew in college. She had a boyfriend who was gone for the semester (funny story, he ended up marrying my cousin...turns out both of them saw his earnings potential. Both married men who are rich lawyers, had kids, got divorced after fucking everything that walked and are now struggling to pay the bills now that the kids have left the house and the alimony is over). We had messed around a bit, made out and such but nothing serious.

She called me one evening and said she thought someone was peeping outside the window of her apartment. I wasn't far so I jumped in my truck and went, even then wondering if it was a story... Checked outside the window, who knows.. then hung out to keep her company. Started messing around, ended up in her bed, just down to our underwear. She looks at me and says "are you hungry?"

Well, I am kind of clueless and totally missed it. Said no, cause I didn't want food at the moment, and things cooled quickly and before long I'm on my way home.

Not long after found out that I wasn't the first of the guys I knew, nor the last, which I knew, and she had a thing. She would never fuck a guy unless he ate her out first. So, while I regret it in some ways, in others I'm glad not to have been just another one to eat and cum.

 

[Trident69]

Neighbor same age as me when we were late teens.
Once at a family wedding i passed on one and still regret it.

 

[newhere2learn]

A couple that spring to mind; firstly when I was at college I was in a steady relationship with a girl who was quite frigid and reserved sexually. Same point a work and college colleague made it blatantly obvious that she wanted to fuck me senseless. She was tall, curvy, an amazing kisser. Sexually confident and advanced for her age.

Due to loyalties and being with the steady girl, I declined. We broke up anyway a month later.

Looking back, I should've gone for it, the tall girl was just radiating sex appeal.



Second one that springs to mind was when I moved back home after university. Tall, curvy, blonde girl was chatting to me via Facebook. Few nights in pubs we bumped into each other. She was stunning. I remembered her from school, she was bland and really quiet.

Anyway she offered it on a plate a few times, but I was always sober and driving and she was absolutely shit faced drunk. I just knew she'd not remember the next morning or deeply regret it.

She's still about, blatantly got self esteem issues and jumps from LT boyfriend to boyfriend.

Physically, she's amazing and I wish I'd gone for it. But like I say, she was ways borderline out cold drink every time ... Despite being draped all over me, I was moral.

 

[Rockymtnman]

Just missed out on an old FWB who was in town for the weekend. I was out of town unfortunately.

 

[Foolhen]

The first girl I dated, back when I was young and naive. She wasn't overly attractive, but she had a tight body with a most amazing round ass that I'd fantasized about for years. We would make out in my bedroom for hours, never getting naked, but she allowed me to slip my fingers under her shorts and touch her pubic hair and fiddle with her pussy. I never tried to take it any further than once lifting up her shirt and seeing her lovely pointed breasts with no bra before she jerked it back down again. She later went out with a friend of mine and told him that she has always wanted me to take her virginity, but I hadn't taken the initiative. After that I always wished that I had because even though I heard that she turned out to be very boring in bed, I would have fulfilled a great fantasy to sink my cock into her and slap my balls against that beautiful ass.

 

[Man_oh_Man]

Woman I used to work who I just assumed I had no shot with because she was 10 years older than me. She made it VERY clear later that I absolutely could have and should have, but the moment had passed

Back in college there was a woman on my floor with a KILLER body who I just thought was WAY out of my league. Found out years later she though I was way out of her league. We were both stupid on that one.

 

[craig7091]

My friends girlfriend, we both not married then yet, was pretty drunk one night, we kissed and fooled around. At one point I was standing in the middle with her to my left and my now wife to the right, she had her hand in my jeans stroking my cock and my hand was in her ass, to my left my wife knew nothing.

 

[craig7091]

My friends girlfriend, we both not married then yet, was pretty drunk one night, we kissed and fooled around. At one point I was standing in the middle with her to my left and my now wife to the right, she had her hand in my jeans stroking my cock and my hand was in her ass, to my left my wife knew nothing.

She fucked one of our other friends, so I'm pretty sure right time and right place I would have fuckef her

 

[13Fantasies]

Multiple times.

One came around again though and was rectified. Not enough of them though

 

[cheekygirl75]

Several at least... I was super shy & had no idea that someone would want to have sex with me. Looking back, I missed signals from several people & who knows how many more?

 

[GoingBackToBed]

Many. But in hindsight it was for the best.

 

[Strixaluco]

I was a teen and on a camp, and on the last night I ended up making out rather heavily with one boy. How I wish we had had a condom (the lack of one was why we didn't do anything more), and that he would have been my first (in reality I lost my virginity one month prior, and it was nothing to remember). I took me 10 years to experience anything as hot as that make-out session, and to find out what sex can really be like at its best. Still haven't come across another man that can make me cream my panties by licking my years.

 

[blueeyedgirl69]

My Exes Best Friend right after we broke up... He is a fine specimen.. too bad he moved away.

 

[LusciousLoralie]

This guy I matched with on Feeld. He was in his early 50's, big dick, dadbod, and over a foot taller than me . I had every intention of letting him fuck my brains out but there was some family drama going on at the time and it distracted me from messaging him. Once I went back on the app to try to schedule a meetup, I saw that he had disconnected our chat ☹

 

[Seadog777]

My friends sister and her friend flat told me to my face they wanted a threesome with me.

I was in a newish relationship with my now wife, so I turned them down and told them that my little brother had only had sex one time in his life.

So I ended up giving my little brother the best night of his life.

 

[Windman1]

I used to travel a lot and work at remote sites. There was a woman on a site that was younger than me and had a body to die for. Initially I was quite attracted to her and she began to show interest in me as well. The problem was the more I got to know her the less attractive she became. I got to where I just couldn’t get past our personality differences. To look at her I could want her in a heart beat. Then she would open her mouth and confirm our incompatibility.

Damn, she was hot to look at. And she made it known she liked me and had a healthy attitude toward sex. I just couldn’t get excited about her the more I got to know her. I do think about that body occasionally though.
Sigh! Damn standards.

 

[7inchglory]

I get pulled a lot by women. It's happened to me at one too many events that it's not a one off, I need more than 2 hands to start keeping track. There was one party where there were 3 women who pulled me in one night: One who was single and wanted to hook up with me in the spare washroom at a house party, one who had a boyfriend who would have killed me if he found out, and one girl who literally was molesting me while I was almost black out drunk at the end of the night. I don't know why I wasn't feeling it that night, because the first two was when I was relatively sober.. but thinking back on it, any of those 3 would have been a fun time that I probably would never regret.