Missed Opportunities

[Captain Carter]

was waiting for my gf and her parents and her brother to come back from vacation. I was tasked with unbolting the back fence so the dad could reverse the caravan into the garden. Which I did. It was a hot summers day and we had no idea when they would be back and by we I meant the brothers gf. She was no help as she just got a towel out and watched and stripped to sunbath. We chilled as we waited and I went to get a shower. I didn’t close the door and the brothers gf peeked in and said did I need a hand or two. But as I was going to answer we heard voices.

[mallynb]

Many years ago my best friend had a chance to fuck my at the time ex wife. My wife that I have posted photos of my early posts titled 80s girl.

This took place in the mid 90s my wife and I divorced after 15 years, but she came back a couple of years later.
She did outside sales and one of her customers was my best friend from high school.
He owned a company that used her products.

Myself and my friend were both very busily and did not cross paths much. He always liked my wife’s and girl friends growing up. We would joke about swapping in a kidding way. He was always fond of my wife and thought was hot.

I occasionally wondered if the her ever fucked her when we were divorced. My wife knew about my friend and his cock a few years earlier from a girl friend she fixed him up with he fucked. Also from past stories I shared with my wife.

His cock was known to be extremely long, I remember my wife was intrigued by the stories.
Many years passed my wife finished her life with me another 15 years before passing.

Just in the past year I thought did her ever fuck her, but would he tell me the truth. We got together to do guy stuff and started talking about my wife and what he thought about her.

I made it very clear when we were divorced if anyone had the opportunity to fuck her, I would be very happy he did.
I told him she knew about his cock and hoped he let her experience it.

I also shared with him in those days she always wore skirts with thigh hose only and never wore panties. My friend was so bummed he missed out and did not either take or get the chance.
He admitted he would have loved to fuck her and missed his chance.

I never shared any hot photos of her with him but asked him would you like to see what you missed. He said what do you mean. I showed him a photo of her topless and he said wow I would have loved to have some of that.

[samalama]

Probably the biggest miss of all time was with the woman in these photos. We were both RA's at University together and had closed out the building for the spring. Got with another male and female RA still at school and ended up going around midnight to a local pond to go swimming. Got down to our underclothes and went in the water, and while pushing for the two girls to go topless, they pushed back and said if we dropped it all, they would. The other guy with me hesitated and the moment was lost. Would have loved to have gotten with her 30 years ago.. still looking great today.

[chasses]

I was on vacation with a woman who was just a friend, she'd never indicated attraction to me or such. I'd gone to to visit her in southeast Asian, where she'd moved to from the U.S. and we took an overnight trip together to a resort nearby. We'd traveled as friends before, so again, nothing explicitly sexual implied in doing so. We even shared a room but she kept her boundaries.

However, things got close to fun when she suggested we go to the resort spa together. We walked over and I confessed I'd never gotten a massage and spa (facial, body scrub, etc) treatment before, when she suggested we get a full package. I said I was nervous and would we share a treatment room together. She was like "uh, well, you know you're generally naked, right?" I did know that but expressed surprised and then was like "oh well, I don't care too much about that sort of thing." She hesitated and then was like "well okay, why not"

I was so excited except when we got to the spa, turns out they had no two-person treatment rooms (presumably meant for couples) available at the moment. I had to hide my disappointment. It kills me to know what could have been....

[puge.bogart]

Long time ago, my friends and I went to climb a mountain. It was easy and we got back in the afternoon. We decided to shower before going home.

There were two showers beside each other and we including other climbers fall in line. My friend who is a single mom entered first. She is cute, slim and wears glasses. Not my type but wouldn't pass an opportunity to see her naked. It was my turn and I entered the second shower, I notice immediately that there was a gap located in front. Corner of the wooden divider and concrete wall of the shower. It was 2-3 inches wide gap maybe 6 inches in height. It was level towards my belly. She knew I was the one who entered and ask if I had shampoo. I gave my shampoo through that gap and even saw her hand. While giving it, all my thoughts was if I can get peek through that gap. I did not want to risk it so I gave up the idea.

Later on, one of my friend (a girl too) said there was a small gap in shower located around the thigh level in the center of the wooden divider. A person can peek but not much can be seen as it was very small and at least the person angle should align with it. The girl I mentioned said she saw it too as she was being careful. She smiled at me while saying it. It got me thinking if she was trying to say that maybe I saw her naked or either she saw me naked. I was too focus on the gap in front that is why I didn't see the other one.

[Domino2010]

I have posted before about a barge holiday with my mate , the missed opportunity was when my wife see my mate complete nude when he got out the shower on the boat and she got to see his cock . That night she was extremely wet/horny thinking about it and wanted a 3 some (something we had been talking about for a while ) with my mate but she couldn’t pluck up the courage to go to his compartment as she felt she might get rejected so nothing happened 😢. Many a time since then I think about that time and think what might have been !

[SixPointFive]

I often think back to that night in my first year at Uni. I had a great friend whom I was totally besotted by. I confessed this to her after a few months and whilst she took it well, she told me she didn't feel the say way (and she had a fiancé). We stayed friends (it developed into FWB by the end of Uni) and she used to try and set me up with some of her housemates/friends.

There was one girl, Helen who was known as a bit of a goer - she was a man-eater and wasn't ashamed of it at all. On this night, I was out with my friend and her housemates. She introduced my to Helen who took an instant shine (deciding I'd be the next notch on her bedpost). We drank, chatted and made out in the night club. After a while she invited me back to hers but despite my offer to leave there and then, she said she wanted to enjoy the rest of the night first.

As the next couple of hour progressed, I started to get cold feet. I was 18yo and still a virgin, albeit with plenty of non penetrative experience. I also started thinking more about my mate and how I'd not want to lose my virginity to a friend of hers in case it ruled out anything happening between us in the future.

We stayed connected with the wider group and all agreed "one more drink then home". At that point, I excused myself and went to the bathroom, but as I descended the stairs towards the toilets, I took a sharp right and walked out of the club and went home, losing my nerve about what was an absolute guarantee of sex with this lively young women.

I DO wonder what might have happened, I'm sure she would have taught me more than a few things that night and it might have increased my confidence around women (something I didn't really find until the post-uni days), but then again it could have been a total disaster and killed my chances with my friend. All in all, it should have been worth the risk and boy did she have an amazing arse.....

Took another year, but I eventually hooked up with my mate and we had a few stolen nights together, but could never get it together to be available at the same time. Another missed opportunity maybe. We are still (social media) friends, but there's always that wistful thought in my head about what might have been....with both ladies