Missed Opportunities

[chuckfinly]

Many opportunities missed over the years. Some I have no regrets, some I regret, and some I am not sure. I was not nearly as adventuresome in my early days as I would be if I were single now.

My first missed opportunity that I clearly remember would have been my first time. I think I am glad I passed on it for a variety of reasons ranging from it would have been weird to my first time (the next summer) was with an amazing older (5 years older) woman who had a summer fling with me. In any case, it was my third cousin who was my age and wanted in the worst way to hook up with me. I was hung out a lot with her (male) twin brother at the time and was spending the night at their house. I remember I was hanging out with her in her room just before bed time. I cannot remember why I did not go out to feed the animals with her brother but we were laying on top of her bed watching Walker Texas Ranger and she said she was going to get comfortable for bed. She stood up and started stripping. I was being a gentleman and turned away. She told me I did not have to do that and then made is super weird by saying, "Your know third cousins can marry in California? I looked it up." I told her, "Well these cousins are not marrying." She said something like "oh whatever" and put on some PJ's. She tried to snuggle up to me but I kept moving over and she finally gave up. She was smoking hot but I could not get past the cousin thing.

I remember another time years later when a chick at the fire academy followed me into a supply room, blocked the door, pulled her shirt off, and threw herself at me. I pushed her away because I was worried about being caught and the professional implications. She was also smoking hot and I should have hooked up at least once.

I have had countless girls flirt with me since I have been married but never strayed. I guess a Harley riding, truck driving, real cowboy/rancher and firefighter in top physical condition with a ring on his finger is attractive to women.

Maybe I will share some other stories later but I am too tired and this is turning into one of those super long posts that annoy me.

[Gnome72141]

Two I forgot about from a few years ago:

1) My neighbor has a hot tub. She is single, super sporty. Very weird, but nice to look at. She invited me over into the hot tub one afternoon. As I was climbing in, she said, "The jets on this side are the best, so if you want to cuddle up with me and share a jet, that's fine with me." It was so completely unexpected that I freaked out a bit and sat totally opposite her. I used the hot tub with her a few times after that, and we always sat opposite from each other from then on. (I wouldn't have messed around with her, but cuddling sure as heck would have been nice!) I told my wife about what the neighbor said, and my wife rolled her eyes and told me that I need to grow a pair some day because I avoid this type of thing way too often. (But that is also probably why my wife trusts me so much.)

2) Same neighbor was walking her dog. She took her outer shirt off because she was hot, and she had on a pj tank top and was clearly braless. She realized it right away and put her top back on and said, "oops, that's why I was wearing a second top, I forgot that I didn't have a bra on." What I wanted to say was, "There is nothing wrong with that. I think it's fine to have your other top off," but instead I said...nothing. I probably had a weird look on my face. It would have been nice to chat with her for 20 minutes with her outer top off.

[Str8m8]

I can be fairly oblivious to female subtlety so I'm sure that I've missed out on more than I'd like to think about.

One time stands out though as a complete forehead slapping "DOH!" moment when I realized some time later what I'd missed out on.

When I was 21 or so, I was living with the girl I was seeing at the time. We had great sex all the time, and I know she told her friends I was a good lay because they brought it up to me a few times. But one Friday night during the summer, I'd just worked a 16 hour day in the roasting heat and was utterly exhausted, I got home and she had a friend that I'd only met once or twice over and the two of them were sitting on the back deck having drinks and waiting for me. I told them I was starving and ordered some takeout. They grabbed me a beer, I sat between them and we small talked for a bit. The whole time her and her friend were giving each other weird (to my oblivious ass at the time) looks and her friend kept getting closer and closer me, until delivery showed up and went to the front to get it. I pretty much wolfed down some food and guzzled another beer, told them I was going to go shower and hit the hay. Still more looks between them and at me until I got up and went upstairs. My gf told me the next day that I'd crashed pretty hard and that she'd tried to wake me up for sex, but I was dead to the world. We broke up a few weeks after that over some dumb argument or something.

A year or so after that, me and buddies were drinking and BSing, and somehow the topic of exes that were great fucks came up. And with hindsight being 20/20, as I thought about her, that insignificant unremarkable night popped into my head, and the clues all clicked. I am 99% positive that if I had been a little more perceptive, I would have gotten a threesome that night.

[wonderbill]

This missed opportunity was not my fault: While in college I dated a girl who modeled nude for the art classes at the college. She was more into me than I was into her, and eventually we broke up when she realized that situation. We remained friends, and one day she told me about my "missed opportunity." She had a girl friend who was also a nude art model. As a birthday surprise for me, she asked her friend if she would hide in my dorm room closet fully nude and surprise me when I got back from class. Her friend agreed to this and it was all set but for one detail: My roommate (who was somewhat of a prude) refused to cooperate. He wouldn't let the art model into our dorm room. So I view that as a missed opportunity. Who knows what would have happened when this girl would have surprised me if things has gone according to plan!

[raysallx]

My wife and I attended the wedding of her friend’s daughter. One of the guests was this single, full-figured, blonde woman wearing a red dress. Her breasts were massive and the cut of her dress displayed LOTS of cleavage. LOTS. It was so impressive that I was sort of intimidated, and also didn’t want to be caught staring by my wife. Unfortunately during the reception we were seated where I couldn’t get a good look at her. We heard the bridal party was going to meet at a bar after the reception, but my wife was tired, so we left.

The next day my wife talked to her friend (the mother of the bride) who told her the party at the bar got wild. It turns out that when everyone was drunk Miss Cleavage allowed guys and some women to motorboat her cleavage! The friend said there was a line and some guys even got seconds. WTF? I also found out later that this Miss Cleavage was into midget porn. I’m not into that, but I thought it was kind of an exotic, kinky touch.

[Blue Tony]

Originally Posted by raysallx

The next day my wife talked to her friend (the mother of the bride) who told her the party at the bar got wild. It turns out that when everyone was drunk Miss Cleavage allowed guys and some women to motorboat her cleavage! The friend said there was a line and some guys even got seconds. WTF? I also found out later that this Miss Cleavage was into midget porn. I’m not into that, but I thought it was kind of an exotic, kinky touch.

Intrigued how the subject of midget porn would crop up in conversation...

[raysallx]

Originally Posted by Blue Tony

Intrigued how the subject of midget porn would crop up in conversation...

Good question. I ended up carpooling to work with the mother of the bride and she used to be roommates with Miss Cleavage. She told me she found it on her computer. Too bad I didn't end up carpooling with Miss Cleavage, but that's not the way life works.

[Marathon666]

Haven’t logged on in a while but my wife and I recently reconnected with her old friend and something came up that I felt inclined to share. Almost as if reliving and sharing it will somehow correct reality and the opportunity will not have been missed.

My wife and I started dating in our 20s but we had been acquainted long before that. We were in the same circle of friends and partied together regularly. She had a friend who would come visit occasionally from out of state and all our guy friends were obsessed with her. My wife is very pretty. Definitely the hottest of the girls in our friends group. She’s blonde with big boobs and a thick butt. Her friend actually looks similar and they were often mistaken for sisters.

Fast forward to the other night. Her friend is a nurse and is married with two kids. But she was in the city near us for some kind of convention. Rather than stay there she opted to spend a few nights with us. In the evenings we’d have dinner and reminisce. One particular evening from our younger days came up and sort of rocked my world. We had been a couple years out of high school. It was the standard evening of gathering at one persons house with drinking games and music and stuff as we were not yet 21 and couldn’t go to bars. The party went late into the night and eventually it was time to wrap it up. I lived in walking distance nearby and so did my now wife. Again we weren’t even dating then. As we left simultaneously, her friend asked if I wanted to come with them. Now, I don’t even know why or even HOW I said no but I did. Must’ve had to work. It turned out after we parted ways they snuck into the pool at her apartment complex and went skinny dipping. They said they swam and suddenly heard a gate open and someone yelling at them. They hopped out and gathered their clothes and ran to her apartment. Once inside they stayed nude all night and got into a game of dares of making each other run outside and do certain activities. Cartwheels, running to the street and back. Etc.

So as they waxed nostalgic about this funny and sexy night, I chimed in with “yeah, but if I had gone with you, that probably wouldn’t have happened.” Without missing a beat they both completely shot that down. “We absolutely WOULD have still done all that” Her friend went so far as to say that they would have probably gotten competitive as they both thought I was cute and been even more risqué to impress me. My wife piped in with “I wonder which of us would’ve fucked him” and her friend says “probably both of us”. They both laughed and so did I… as I died inside.

There I was sleeping the night away, so I could be rested for my shitty restaurant job, and a five minute walk away, two beautiful 20 year old naked blonde girls were having the time of their life and I could’ve been there.

[Nono242]

I had many missed opportunities some about in another thread. One of my earliest was when I was in highschool a girl from my class we were close and looking back I believe she probably was interested in me but the I was too green to probably pick up on that. Everyday I would walk her home or somedays she would be by my house either to hang out. She used to basically be throwing herself at me if Im sitting in a chair she will sit in my lap. Sometimes she would randomly jumping hug with legs wrapped around. One day we was playing truth or dare first she dared me to kiss her. My dares was something small and she told me she was up for anything then she took one of hand placed it on her breast and the other on her ass. Then she asked me how much I like her and Im going to tell oh I like you very much for a friend. I told this to a girl that used to sit with me with her legs spread open and always pressing her body against me. 🤦🤦🤦

[raysallx]

During my college years I used to work on construction crews. At one point there was a very attractive young woman working with us. She was married to a guy on the crew. He was very handsome, but must have been a dud in the sack because she turned her attention to me. When it was hot out she would go braless as we worked, and her boobs were not small.

One day she finagled a reason to ride with me to pick up another truck. Halfway there we had our hands on each others thighs. But because she was married, and I was young and stupid, I never took it farther. When the crew broke up she even mailed me a medallion of some kind to remember her by. When you are young you think there will endless opportunities like this. Not true, seize the day my brothers!