The Missed Opportunities Thread

[helloyo2120]

1. A close female friend had spilled whipped cream on her chest. I said I'd get it and went in to lick it off, to my surprise she put her shoulders back, to let me, so I went ahead and did it. I told her, jokingly we should check and see if any got on her nipple. To my surprise she pulled her shirt down and exposed her nipple. So I put a little whipped cream on it, and said "you want me to get it?" She said sure, so I sucked her nipple. When I finished, she said "there's a little more you missed." I said "Did I actually miss some or did it just feel good?" She said "Maybe a little bit of both" so I sucked some more. She took out her other boob and I sucked that too. And like a fool, I stopped there. She totally wanted me to keep going, I never had sex with her and that may have been my only shot. I was young and foolish lol.

2. A very pretty girl was quite infatuated with me and my then-girlfriend. Both her and my gf got naked, we were partying just the 3 of us, but she was getting plastered drunk. She was drinking a lot, I believe in an effort to excuse her actions later. She was flirty all night, but by the time she got around to hinting (all but outright saying I want a threesome) I was waayyy too uncomfortable with how drunk she was to go through with it, and I told her as much. I said that we shouldn't do any penetration because she was too drunk and I'd feel like I was taking advantage. She called me a pussy and left. Call it the noble thing to do, but a missed opportunity, it certainly was. I to this day have never had a 3some... there was my chance.

[pball2295]

When I was about 25, my then girlfriend and I lived with another couple in an apartment who was married (and even younger than us). She was pretty cute. A giant rack. Twice when they got drunk, they both nervously confessed to me that they wanted me to fuck her - the wife. He clearly had major cuck fantasies, and I think they remembered my girlfriend alluded to the fact that I had a big dick a few times.

I was too faithful to my then girlfriend..who understandably thought the whole thing was very weird. (They also would have swung with us 100%, but she was very much not into it).

If I could turn the clock back...I'd wait until my girlfriend went out on a girl's night with her friends. Then I'd invite the couple out to the living room, push the hubby onto the couch, cut off wifey's clothes with a pair of scissors, lay her on top of him and absolutely destroy her pussy. I'd kiss her on the lips, wrap his arms around her body, and let him feel his wife's body shake as she climaxed.

[outbog1]

A while back before I met my second wife I dated the hottest girl around for 2 weeks,she was 5'3" about 110 lbs,jet black hair,B tits,dark skinned Itailian,we made out all week I could do amost anything with her except fuck her,I was sucking on her dark tits on the first date and playing with her pussy on the outside of her panties,it was so close,she kept saying tomorrow we'll fuck,,we both worked full time and only had a few nights for each other,I stayed at her house once,separate beds,I got up in the morning after we played and necked half the night,she had on a very sheer nighty,I had on just underpant with a massive woody,she took a shower and I ran down to the corner store for 2 coffee's,,,why the hell didn't I take out my woody and get a blow job,,,,that night we met and danced kissed went back to her house and she dumped me---She was a gold digger,married a guy 20 years older a bank president,took him for everything and I found out it was her 6th marriage...I lucked out.

[jsnd]

On a college exchange trip to somewhere in france we had one night free in the nearby town. Of course drinking and playing pool at the local bar was the order of the night. Just before it became my turn to play the barmans gf came in and wondered who all these odd english people were and began talking to me. It was my turn on the table pretty soon after and i said, hey, talk to my buddy Bob instead.
Next morning Bob gets dropped off at the college after being taken home by her back to their place.

[piecenick]

I was the assistant director of a play my college drama class was doing. My biggest responsibility was making sure everyone knew their lines. The lead was this girl who was chosen more for looks than talent, she also had a hard time memorizing her lines. I told her we’d get together after class so I could coach her, she suggested her house not far off campus. We set a time that night.

When I got there she had on a tight shirt with no bra and shorts, very hot. Part of her role was a deep kiss with the male lead, while rehearsing her lines I said we could skip the kiss, but she insisted. This one kiss turned into a make out session, hands were roaming, I was under her shirt pulling on her nipples while she moaned.

Then for some stupid reason I lost my horniness, I got this vision of her not knowing her lines and screwing up the play. I promised her we’d finish later, if she got her lines down. But by the time we got finished we were not in the mood. Never got another chance.

[Soupdragon]

A friend of mine who I always quite fancied was at a house party with me. For some reason the party was mid-week and I had work the next day so I wasn't drinking. Despite going as a larger group it was just me and Annie left by midnight, though there were still quite a few other people we didn't know at the party so we stuck together. By 3am it was just me, Annie and the party host who we knew, so we helped clean up and I offered to give Annie a lift home. She was discussing all the way home about how she's house sitting for her parents while they're away, and how lonely it is... none subtle hints that for some reason flew right over my head at the time! I think it was just the fact I was very tired and had to be up again for work in about 4 hours time.

Anyway, I pulled up outside her house, she hugged me and said goodbye but before opening the door she tapped my knee a couple of times and said 'do you want to come in?'.

'YES! Definitely,' is what I should have said. But what I actually said was, 'no thanks, I best get home myself'.

'Oh, ok then', she said, sounding slightly disappointed.

The next second or two seemed to last for a lot longer, but I remember her putting her hands round the back of her jeans - at the time I thought she may have just been pulling them up, it was the era of low rise jeans (which I think definitely need to make a come back) - and then she adjusted her bra through her top. She opened the car door, rotated on the seat 90 degrees so her back was to me, leant forward but at the same time pushed her ass back, revealing quite a lot of bum crack and her thong, the top of which was now slightly below the top of her crack. Like I said, all this happened in a couple of seconds, but it all seemed to be in slow motion!

Then she got out of the car, turned round and bent over so she could see me again, and also giving me a wonderful view down her loose fitting top, not only of her slightly oversized bra but her nipples as well. 'Are you sure you don't want to come in?' She asked, again. She knew exactly what she was doing and what she was showing me.

Once again, the right thing to say would have been 'YES!!'. But for some still unknown reason I said 'no, I really need to get home'. She quickly said her goodbyes and walked up her drive.

WHAT THE FUCK WAS I THINKING?!

-=-=-=-=-=-=-=-=-=-=-

A few years ago I matched with a girl on Tinder. We got along well in our initial chats and eventually arranged to meet up and go for something to eat. Unfortunately when we phoned up to book a table at the restaurant they were fully booked. So I said never mind, just come to mine, we'll order a takeaway and watch a few films. She agreed and came round that evening. Halfway through the film she started fidgeting slightly. I asked if she was ok. 'Oh I'm fine, quite embarrassing really. I went to Victorias Secret yesterday for some new underwear and it's quite uncomfortable'.

Now, what I should have done was ask her about it. She's obviously not that embarrassed to tell me about her underwear so she's obviously wanting a bit of fun too. But no. I can't remember exactly what I said but it was something along the lines of 'oh bummer, you won't be able to take it back will you?'. Instant mood kill!

She wasn't to be deterred though. Later on I mentioned that there was a draught coming under the door and asked her if she could feel it. I know exactly how to set the romance going She asked 'do you not think we'd be more comfortable watching this in the bedroom?' And, once again, for some unknown reason I said 'nah, it'll be fine, it's not that bad'.

Not too long after she said she needed to get off home as she had an early start the next day so we said our goodbyes and she left. Surprisingly, never saw her again!

I was telling my mate about it a week or so later and how I was completely oblivious to her quite obvious advances. He started laughing, and asked if she was called Kate. 'Err, yeah, how do you know?' Turns out he also matched with her a month or so before, took her home after going out for a meal and actually watched a movie in bed with her. She was showing him her 'new' Victorias Secret underwear under her jeans and he, like me, was completely oblivious to what she was doing!

Poor Kate!

[jho.n3]

Well dude, Not sure about her being a colleague. But she is craving for a good fuck. Indian girls can't get more forward than that. She has given you all the signals and she is itching for it. Just teach her how to enjoy herself and she will be ever thankful to you.

Originally Posted by SyFoster

This is actually a current opportunity that continues to be ‘missed’, by my choice. Allow me to explain.
Although I currently work from home, and have been since March 2020, prior to this, I worked this same job at your average office building, in a cubicle. One of my coworkers, a few cubicles over, is a chick from India (born there, moved here when she was in early grade school). Although it started out very slow, we began talking a little here and there; nothing important, just work B.S., stuff like that. She was in her late 20s, and gradually a lot of her conversation was about her boyfriend-They’d been together for years, she loved him, etc; but, he was lazy, went a long period without even having a job, he didn’t want to get married, move somewhere nicer, etc. Basically, she was growing up, and he wasn’t. So she was constantly back and forth about their relationship’s future, whether or not she should break up with him.
Now as soon as I caught wind of her relationship issues, my years of experience immediately kicked in and my mind was giving me five different ways that I could work this to get some action from her. In addition to her boyfriend issues, it had not gone unnoticed by me that she was giving off signals that made it clear she was attracted to me and felt at ease with me-Playing with her hair (even having me feel and smell it when she tried new shampoo), sitting on my desk, really close to me when we talked, constantly touching my shoulder, knee, hugging me on multiple occasions, and we got to the point that we could talk about anything, including sex, details, etc.
So why am I not writing a story about me fucking her? Well, two main reasons. First of all, if this had happened when I was younger, less experienced, and hadn’t been with a lot of women, I would have pursued her by now. But being a bit older and wiser, here’s the main reason why I haven’t nailed her (yet). First of all, we work together. Whether it’s just a casual sex thing, or a relationship, if it’s with someone you work with, that rarely ends well. In addition, with all of her confusion she has about her and her boyfriend, I didn’t want to be the reason that ultimately made her end it with him (especially since I have zero desire for a relationship with her, and would merely want to fool around a bit). Let me be clear, I didn’t care if they broke up, or got married. But it wasn’t going to hinge on me. The secondary reason that has kept my dick in check is her looks. She’s barely 5 feet tall, chubby, and has absolutely no ass. Her hair is very sexy-long, sleek, jet black. And of course she has the dark brown Indian skin tone-a bonus. She also has very full lips (can’t even imagine what a great blowjob they could give). As for the negatives-again, no ass whatsoever. Chubby, which I have no problem with, but she’s on the borderline with her weight. If anything, I would describe her as cute (like a stuffed animal); not hot, not sexy, not even pretty, just cute. Now, I saved the best for last. Although her face is very cute, her best feature is her tits. They are huge! They have to be at least D-cups, maybe double Ds.
So, that’s the ongoing missed opportunity. Since we’ve been working from home, I haven’t actually seen her in over a year. But she texts me about once a month. And the latest development-She ended it with her boyfriend, they split over a month ago. I have no doubt that if I put in even the slightest amount of effort, that I could easily get things physical with her. Part of me thinks that even if we just met up somewhere, that same day I could get her to make out with me, see/feel her tits, and get a handjob. In fact, if we ever do meet up and I give myself the green light, that’s my initial, first day goal. However, at this point, she’s very low on my radar, and not really worth the effort. But even low on the radar is still on the radar. At this point, though, I’m just not interested. But I won’t rule it out.

[Sonera]

Originally Posted by SyFoster

Well, as I said, it’s a possibility. Maybe the next time she texts me I’ll see about meeting up with her. She lives an hour away from me, and at this point, isn’t worth my drive time. But if she wants to head my way, I might go for it. Will gladly post an update if anything happens.

One day you'll be forced to fuck an uglier woman, if u wanna get laid. Don't miss out.

[fuzzylover]

Originally Posted by SyFoster

Unfortunately she lives with her parents; in addition to that, her mother is hardcore strict. Not that I care, but no way I’m getting through that front door. But your statement is on track. For all I know, years from now, I’ll regret not banging the chubby Indian woman with the huge tits. I have a lot more going on right now that’s much closer to me; but whenever she texts me next, perhaps I’ll see if she’s up for heading my way.

Make sure you document everything for posterity😜