A fuck you defintely should have had

[HumpDayHoratio]

Worked at a Dept Store in college. We get a new check-out girl. She was tall, blond, always wore short skits with leggings as was the style at the time, and to top it off she drove a ‘66 Mustang convertible! We started to meet after work, going to coffee shops and the like. I had a LTGF going to school in a town about an hour and a half away, she was unattached at the moment.

I really enjoyed my time with this girl but there was one problem. Her best friend was an absolute STUNNER! I couldn’t get past it. When we spent time all together, she was all I could think about. She was out of my league, attached (BF was a stud), but I just couldn’t get past it.

Up until this time, we had only exchanged a kiss or two. One night she drops by when I had decided to stay in and just chill out. My roommate was out of town and my GF hadn’t come up for this weekend (although she was known to just pop in unannounced) So it was the perfect setup.

Call me stupid (it fits!), young and naïve, or just all the conflicting emotions of the GF down south and this girls bestie, I just couldn’t pull the trigger.

One of my biggest ”What If’s” I left on the table.

Because of this, I didn’t leave many on the table afterwards.


Except for my landlord after I was married. She was tall, Hispanic, had style in spades and saucy as they come. She would pop in from time to time to check up on our apartment (it was a converted mansion) so she was very familiar with my wife and I.

We were at a large party one night and there is Elena. She was very drunk and chats and jokes with us. As the night wears on we bump into each other several times and I‘d get her drinks. My wife had wandered off but was in eyesight of both of us. We were standing a little to close, in that sexual spark type of close. She leans in and whispers how do I like being married. I respond with a typical response, and then she blurts out “that‘s cool, I LOVE a challenge!” She then gives me the look. You know that look. The ball is in your court look. The let’s make plans look. The I’m yours for the taking look.

Out of respect for my wife and honestly I was trying to change my bar hopping, butterfly chasing ways, I politely declined or maybe I just stood there dumbfounded. I honestly don’t remember.

She was a few years older than me, a true man eater so to speak. I don’t regret it but I sure do wonder sometimes.

 

[Wifejen86]

I was at a nightclub with friends. I was pretty drunk dancing on the dance floor when someone started grinding up behind me. I glanced over my shoulder to see it was my best friends lesbian sister. She was kissing my neck and running her hands all over my belly and breast. I was so turned on but also worried what people would think. I've never been with a woman before but having her touch my body like that had me dripping wet. Eventually I moved away not because I wanted to but because I was worried what my friends would say. My friends lesbian sister sent me a fb message the next day saying "let me know when your ready to be dyked". I'm so tempted

 

[Strixaluco]

I was at a nightclub with friends. I was pretty drunk dancing on the dance floor when someone started grinding up behind me. I glanced over my shoulder to see it was my best friends lesbian sister. She was kissing my neck and running her hands all over my belly and breast. I was so turned on but also worried what people would think. I've never been with a woman before but having her touch my body like that had me dripping wet. Eventually I moved away not because I wanted to but because I was worried what my friends would say. My friends lesbian sister sent me a fb message the next day saying "let me know when your ready to be dyked". I'm so tempted

Sounds like you should. Besides, your friends accept her, they will accept you.

 

[Wifejen86]

Sounds like you should. Besides, your friends accept her, they will accept you.

It was more to do with I'm married with a family more then my friends accepting me.

 

[Strixaluco]

It was more to do with I'm married with a family more then my friends accepting me.

Oh well that's totally different then.

 

[English_guy_bkk]

Don't laugh. But a truck driver, she was absolutely gorgeous She was blonde and used to come for deliveries daily. I was working in a foam factory at the time, in the goods out section. (My boss always brought chese slice sandwiches and offered to swap)
A few times during the winter she would say her lorry needed a push! Looking back it may have been some code.
So...Linda if you're reading this .

 

[Wageslave]

I was at a nightclub with friends. I was pretty drunk dancing on the dance floor when someone started grinding up behind me. I glanced over my shoulder to see it was my best friends lesbian sister. She was kissing my neck and running her hands all over my belly and breast. I was so turned on but also worried what people would think. I've never been with a woman before but having her touch my body like that had me dripping wet. Eventually I moved away not because I wanted to but because I was worried what my friends would say. My friends lesbian sister sent me a fb message the next day saying "let me know when your ready to be dyked". I'm so tempted

Go for it - it may be the best thing you've ever experienced

 

[ChestyLaRoux]

Old bestfriend from jr. high. She moved for high school, but we started hanging out in college. We were both dating guys, and I show up to her place. She shoves me against the car, drunk as fuck and gives me a basement soaking kiss. She full on says her plan was to get me there, get me drunk and fuck. Well--I couldn't reach my boyfriend, and I wouldn't do anything without his sign off.
Find out when I get home the next day that his response would have been to film it for him.

# R E G E R T S

 

[tristianc]

Yes, wrote a story about it here except changed the ending so that sex actually took place. Not a day goes by where I wonder what it would have been like if I was willing to follow through.

 

[NorCalLoki]

Dropped my son off at Chuck E Cheese for a birthday party. There was a cute blonde late 30 to early 40's gal that caught my eye. we exchanged smiles right before I walked out the door and got in the car.

A few seconds later, as I was starting the car, she bounced up to the window and asked if I was single. I was honest and admitted I wasn't.

She would have looked real attractive lounging on a bed with some dark blue sheets.

 

[SPARTAN047]

Oooof, I don't think so. I had some people who tried to get me to pay them for sex or cover the whole cost of a hotel. Blocked right away.

There was a time when I booked in a room to dress up and invite someone over. It didn't work out, no one replied and two minutes after I cancelled the room so I only lost the deposit and not the full price, I got a message from someone who wanted to see me dress up.

Pretty early in my journey so it was a very infuriating missed opportunity.

There were other times when other folks dressed up on cam for me, or tried to enlist me to pay for rooms as well with them — I simply could not find the time off work to do it though and I made it clear to them though they didn't listen. I wasn't planning to drop everything just for sex even then so I wouldn't count them as 'missed opportunities'.

 

[SavannaT]

When I first got married to my present husband I got lots of dick pics flooding my in box, at the time I was disgusted but one in particular was a thick fuck stick looked like it weighed 5 pounds, the guy was a piece of shit, a creep and I think sex offender but I wish I’d gotten used by him. No matter how bruised or broken he might’ve left me, my pussy resents it wasn’t the best worst thing I ever did.

 

[gtnlynn]

I was an idiot when I was in college. Lynn and I had been dating sisnce we were 15, and I had promised her that I would not have sex with her until our wedding night. I kept that promise. What a fool! We would get close, and I would stop. One night, I had her naked, fingering her. She sperad her legs, used her fingers to open her vaginal lips and said, "I want you inside me." I started to put it in, but stopped. She never gave that invitation again, so our first sex with each other was on our wedding night. A few years later, I discovered that she was being fucked on a re

 

[cdstefi]

Oh God yes, the one and only huge regret of my life.

I was 20 or so, at university, and one of my housemates had been going out with this girl Fay, but they seemed to have cooled off (no idea why on his part, she was sex on legs). Anyway, we'd all been part of an extended friends group and this one time she came over to say hi when only I was in the house. Not with the intention of seducing me, but we had a couple of joints and were listening to music and chatting and got very very chilled, and I had the feeling that if I had the nerve I could kiss her and she'd respond and things would take their course.

But me being still a virgin and knowing she definitely wasn't (I'd heard her and Mike fucking next door enough times), and not being entirely sure what their relationship status was any more, I just didn't feel able to make the move. I was nervy enough that if I'd misconstrued and she turned me down (I know she'd have done it nicely, she was a lovely soul) I'd have been shattered.

Sure enough a week or so later she'd split up with Mike and was already going out with another mutual friend. It's always seemed like the greatest chance I ever missed and one of those where if present-day me could give back-then me a talking-to...

 

[XXVIII]

After my divorce from my first wife, an old friend from college reached out. She was trying to be a sounding board for me even though I really didn’t need one.
One day she came by the house and wanted the tour. She spent a long time in my bedroom chatting about a lot of misc topics. Nothing happened but a few months later she admitted to me that she wanted to be my friend with benefits.
That was a fuck I definitely should have had.

 

[Anihotrod11]

At office, I was leading 13 employees in my team, among them 3 were women, and among these 3 one Mrs R was petite and filled with inferiority complex.
She kept asking for one on one meetings with me , initially it didn't strike me what she was doing, once inside the meeting room, she would make it a point to brush her breasts on my shoulders, her hands would keep feeling my arm or wrist,
If I would have shown some signs on intrest in her she would have unzipped me and pushed my cock inside her wet pussy in that same meeting room

 

[HotWifeOC]

At office, I was leading 13 employees in my team, among them 3 were women, and among these 3 one Mrs R was petite and filled with inferiority complex.
She kept asking for one on one meetings with me , initially it didn't strike me what she was doing, once inside the meeting room, she would make it a point to brush her breasts on my shoulders, her hands would keep feeling my arm or wrist,
If I would have shown some signs on intrest in her she would have unzipped me and pushed my cock inside her wet pussy in that same meeting room

Yikes, that's hot

 

[mrdeeds7625]

One that I should’ve had was a married woman when I was about 25 she was 36, blonde with an absolute onion booty. She was naked in my car and we decided to make our first time special and wait til’ Christmas (this was right after Thanksgiving weekend)
Sometime between the holidays I grew a conscious and Christmas never came…neither did we.

 

[Norfolkguy49]

A former work colleague who really wanted me after I got divorced but it just never happened

 

[coffeelover5]

A sister of her's that walked in on us. Sister seemed pissed or maybe envious?

Two cousins in their prime, twins.

The girl that took my cherry 20 years earliet, I should have finger fucked her like we used to do but had a grown some weird morals back then