Missed Opportunities

[hbctrapper]

I had a lot of missed opportunities in college, but the one that I remember the most even though it isn't the most extreme was a time at summer camp. I had been dating one of the counselors since the previous summer and that night I was in her cabin which she shared with one other female staffer. That girl knew what we were up to so she said she was going to take a very long shower. As soon as the water was on, my dick was in my gf's mouth and clothes were coming off.

Eventually she was on her knees and against the wall while I leaned against it. It was dark in the room and I noticed a pinhole of light in the thing wall. I looked closer at it and saw it was a large nail hole in the thin wall paneling that separated the bedroom from the bathroom in this cheap cabin. Then I noticed that with my head against the wall I could see through the hole into the bathroom right at the shower stall.

I could make out her roommate barely though the translucent shower curtain. I could make her arms through a small gap in the curtain as she adjusted the water, maybe I saw quick glimpse of her breasts. For several minutes I kept looking before quickly looking down at my girlfriend sucking my dick. I knew she would eventually have to step out and dry off and I would get a look at her fully while I was getting a very good blowjob.

As the water cut off I was getting ready to look back in, but my girlfriend stopped sucking and told me that she loved me and needed me to cum quick. At that point I felt a little guilty so I looked down and came very quickly due to all the excitement.

[nigbo]

Plenty in my biker days. Chicks were always hanging about in the biker cafes and asking for a ride and often offering a ride for a ride. Trouble is I was very fussy who I rode. Could kick myself now

[Gnome72141]

Originally Posted by hbctrapper

I knew she would eventually have to step out and dry off and I would get a look at her fully while I was getting a very good blowjob.

As the water cut off I was getting ready to look back in, but my girlfriend stopped sucking and told me that she loved me and needed me to cum quick. At that point I felt a little guilty so I looked down and came very quickly due to all the excitement.

I can relate! I basically unofficially lived with my then-gf in college and her three female roommates. So many times I almost saw them changing, almost saw them coming out of the shower, almost...almost...almost. But while my then-gf loved when her roommates regularly saw me naked, I wasn't allowed to see her roommates naked in return (although they expressed themselves that they wouldn't have cared at all). So, I missed out on those "almost" times because just as I was about to position myself to see something, my then-gf would come around the corner or be nearby, etc.

The worst was when the most attractive roommate was going to put on her pjs. I was in one of the bedrooms with her and my then-gf. The roommate took off her top and was in a lime green bra. But as she unhooked her bra (while facing me), my then-gf took a pillow and put it over my face, pushing me back onto the bed and held it there until the roommate had her pj top on. A moment later, my then-gf told me that the roommate had the best-looking breasts she had ever seen and it was too bad that I had missed them. (There is a lot more awful backstory with that ex-gf, but I try to remember only the good times.)

[Massguy70]

Originally Posted by nigbo

Plenty in my biker days. Chicks were always hanging about in the biker cafes and asking for a ride and often offering a ride for a ride. Trouble is I was very fussy who I rode. Could kick myself now

A good friend had a bike when we were in our 20s. He told me girls would pretty much like up to go for a ride. We were hanging at the same place one night. He told me to watch how the night went. He was right. A number of randoms would talk to him for a few minutes then either he's offer to take them for a ride or they'd ask. I got a motorcycle license but never bought a bike. That was one of my missed opportunities.

[nectcouple]

I've been riding motorcycles since before my teens and can attest to to the almost magical attraction some women have to them. Currently I'm 62 and ride a 2020 Goldwing. Yup, I'm an old man on an old man bike, lol! It still attracts the ladies who want a ride, but its rare that my wife will give up her seat to anyone else and that's ok with me!

[Summer120]

I have far too many that I look back on from time to time and think “Damn why didn’t you!?”. Much of it was in my years from 18-mid twenties it seems.

One that I recall was with a female best friend for many many years. We had amazing sexual encounters randomly throughout our friendship, but nothing serious. She had her own townhome and wagon and we would pile in friends for nights on the town filled with booze, and always end up back at her home for after partying. Sometimes random people would sleepover in any space available.

One morning I woke up from passing out on the couch and made my way through the house to wake a few friends up or see who was leftover. As I made my way to her room at the front of the house to say bye and use her restroom, I entered the room only to find her in bed laying naked with one of the usual guys in our group of friends. He had just ended a long relationship with one of our mutual female friends and that was his first single night out.

Standing in the doorway, we all smiled knowing what happened there, and I said “I’m gonna get going, and use your pisser first” they were both giggling from what appeared to be the after sex rush and were wiggling their feet around and smiling when the guy goes “hurry up so you can hop in here.” Now I didn’t at all question any gay vs straight issues in my head, we are both straight, but I was questioning the people in the house possibly hearing or knowing and didn’t want them to know. I can’t believe I really was worried for strangers in the house finding out.

She just giggled as I made my way to the bathroom and starting peeing as we app were talking to put the night together a bit. As I was done and leaving, he again said “Hey, you’re not climbing in here?” I replied that I had to go and was leaving.

I kick myself now because she clearly never said no to the offer. She clearly kept smiling through it all. She was a great friend, we’ve had amazing sex, and it probably would have been a great experience for her, and I, because of how close we were as friends. We over the years shared so many sexual stories, and that possibly could have been the best story we shared... together.

[raysallx]

Here's another one I recall. When I was in my 20's I met a couple of Canadian girls on the ferry between Brindisi and Corfu. Once we got to Corfu, they wanted to go to the nude beach and I said, "Hell ya!" We spent the afternoon comparing who had the tannest ass, drinking beer, etc. Good times. That evening the three of us decided to share a room. They were both hot enough that I couldn't decide which one I wanted first. Then...my stomach started gurgling. I remembered eating some spaghetti with meat sauce at the beach earlier. So instead of taking turns on my Canadian friends, I spent the night in the toilet, crapping my brains out. It was one of those Greek rooms built out of cinderblocks, with no rugs or hangings to deaden the acoustics. I was quite embarrassing. Sadly, I never had such an opportunity again.

[andyt29]

Something about the above post jogged my memory of a time that I was at the bar with a few friends. It was at or near closing time and we were chatting up a couple more local girls. Problem was there were two of them and three of us. If this were porn, it wouldn't have been a problem but it clearly was. Especially since our driver was the odd man out. The girls clearly had a few fun things in mind for two of us, specifically "hey, come back to our place and we can sit in the hot tub and have a few more drinks". But our driver wasn't having it. He was done with the bar and wanted to go home. We finally convinced him to go back to their place for a bit. Sure enough there was a hot tub and more drinks. It even went so far as "it's ok if you don't have bathing suits just wear your underwear". Things were close, oh so close when my buddy driver who declined to even get in the hot tub started threatening to leave us.

If we weren't so far from home (or if someone had invented Uber decades ago), oh the things that could have happened.

[nectcouple]

Originally Posted by andyt29

Things were close, oh so close when my buddy driver who declined to even get in the hot tub started threatening to leave us.

Cockblocked by your driver? Wow.

[andyt29]

Originally Posted by nectcouple

Cockblocked by your driver? Wow.

yeah, in his defense it was a 45-60 min drive home, and being the sober guy at the end of the night is necessary but not fun. His other point was that the girls weren't even that good looking which was probably true but at that age (or any really) when a person you just met invites you back to their hot tub you go!