Missed Opportunities
 

Has anyone turned down a chance of a sexual encounter and regretted it?

When I was about 18 a friend and I used to go into a pub in the north of England to play pool. Both of us took a fancy to the barmaid and I plucked up the courage and asked her out.

We went for a few beers and eventually headed back to her flat. At the time I had a goatee beard and she said she was not that keen on it. I explained I had not had it long and was undecided myself.

She then said if I shaved it off she would give me a blow job whilst I did it.

After some discussion I said no as I wanted to keep it. Nothing else happened on the night and I did not see her again.

I think I said no as I was a relatively shy teenager and her direct offer spooked me.

However I still think about it and wonder if I had said yes how steady my hand on the razor blade would have been!

A MMF threesome with my roommate and our nympho co-worker.

She came over to our place, we started drinking; and the next thing I knew her panties were off and my roommate was jerking her off. And when I was called upon to come join them; I chickened out. I thought an MMF situation was a "little bit gay." Yeah that was stupid.
Sensing my reluctance, our nympho co-worker got shy and decided to leave. I got a good ribbing from my roommate. He tried to invite her again but she declined stating that "Shihoin just isn't ready." Shame on me.

I had a similar but even worse miss: I turned down a FFM threesome!

It was first year of uni and I was going out with my first long-term GF. She was also the girl I'd lost my virginity with.

She was living in student residence with three other girls, one of whom was an older exchange student from the US. I think this lady was at least a third year, as opposed to my GF and the others all being first years. She was a bit of a rocker, I think she modeled her look on Gwen Stefani from No Doubt (this was the late 90s.). She also wasn't shy. She told them all she was a lesbian when they first met her but, later in the first term, revealed that she also liked guys too - by bringing home a random one and having such loud sex with him that she woke up everyone! She also got her clit pierced that term and kept her housemates informed about how it had been done, how painful it was in the immediate aftermath and how much fun it eventually became...

Cutting to the chase, some time in the Spring of that year my girlfriend told me that she and the American had been up late the night before, chatting and sharing a bottle of wine. Our relationship got discussed and the other girl ultimately told my gf that she thought I was cute and, if we ever wanted to try out a threesome, she was offering herself!

Unlike the lady I am now married to, that girlfriend never expressed any interested in other girls. However, we were first years and she basically said "Why not?" and that she'd be willing to try it out.

And I, being a paranoid 18 year old worried about everything sex-related, was the one who said "No, I wouldn't be comfortable with that." :-(

To say I've regretted it ever since would be an understatement.

Missed opportunities? Pretty much every day of my life until I was about 26 years old, sadly. I could write about 100 of them here, easily, but I would have to dig deep into chapters of my life that I had buried!

I was raised as a super prude by my paranoid parents (to the point that I saw my sister's boobs down her pj top and my mom grounded us both for a week--my sister for not wearing a bra to bed, and me for looking).

I missed out on playing strip poker with 6 hot girls of my best friend (female). I was the only guy. I got scared and left the house.

I missed out on a FFM threesome with two women who were lesbian but wanted to prove that they weren't.

Missed out on plenty FFM threesomes in college because I was super scared.

All kinds of things. Then I met my wife who HAD done all that stuff plus a million more things and was done with it all by the time we met. I wanted to do the opposite and START it all. So instead I just live through her stories. :)

Idiot Oblivious
 

Not sure if this counts, but about 18 years ago I was working away from home but returned for Xmas. My parents had moved house a few days before Xmas, about 60 or 70 miles away from where we grew up. We shared Xmas Day with friends of theirs who had made a similar house move a few months previously. As Xmas Day progressed, it dawned on me that I needed to be back "home" on Boxing Day morning for a football match. The daughter of the couple we were spending Xmas Day with also needed to return home that night and graciously offered me a lift at about 9/10pm.

During the hour long ride, we chatted about the day and our plans for the rest of the holidays. I was planning to do the rounds of friends/family before heading back down south for work. As we approached our destination I was having no luck getting in touch with my mate - I was staying at his for a few days and we were heading to the football the next day. As we got nearer and nearer to "home" my driver had a great idea - why not ditch my mate for tonight, come back to hers and just "crash" there. She had plenty of food and booze, we could relax on the sofa and watch a movie.

At this point I should say 2 things. Firstly, Abbey (my driver) was super hot and I had always had a fancy for her. Secondly I am (or was) the ultimate Captain Oblivious in these situations. I had no inkling that she was offering me anything other than a sofa to sleep on

So, as the journey continued I was adamant that I had to get to my mate's house as "that was the plan" and continually shunned her offer of a bed for the night

Eventually we got to my mate's house, I was able to hammer down the door and wake him from his post-xmas meal slumber and he let me in.

It was only after I received the coldest of hugs and the thinnest of smiles from Abbey that I realised what she'd been offering. She screeched off in her car, clearing snubbed and angry whilst my mate apologised that he had no booze in the house and no bed in his spare room.

It haunts me now what I passed up. Even just one night of lust with Abbey would have been worth 1000 football matches.

Needless to say she never offered me a lift anywhere again :(

One of my missed opportunities was a friend's sister and one of her girlfriends. I was around 20 at the time, and my friend's sister was 18. My buddy and I hung out a lot during high school, so I knew his sister since she was 14, and I never thought of her as anything as my friend's little sister.

Anyway, I had a nice apartment with a pool and token-operated tanning bed. Both girls bugged me about using the tanning bed, and I told them I'd pick up tokens, and they could swing by to get them whenever they wanted to go. My apartment complex was gated, and the tanning bed was available 24/7 to residents.

This was in the early 90s, and while cell phones were certainly available, most didn't have them. I was not totally surprised that they showed up without a call, but I wasn't expecting them to knock on my door at 10 PM in the middle of the week, either. My friend's sister told me the reason for their visit, and I went to get the tokens, but they both sat down in no hurry go. I liked them well enough, so I wasn't trying to rush them out the door, but at the same time, I was not fawning over them, either. We essentially made small talk and watched whatever program was on the TV.

The sister's girlfriend wasn't overly attractive (not ugly by any means, though), and she was definitely the bolder of the two. I don't recall exactly how she brought the subject up but somehow mentioned that they would be tanning in the nude and something to the effect of being naked together while the other was in the tanning bed/waiting for their turn. Clearly, the idea being that they would both go into the tanning bed room together. My current 40ish self would have been all over that comment, but my 20-year-old self didn't take the bait. I said something along the lines of one of them could stay with me until the other was done, and the bolder friend countered with the idea that I could come along and keep the other person company until it was their turn. So the stupid 20 year old me immediately jumped to the conclusion that meant both of sitting on the floor in the hallway outside the tanning bed room. All I could think of was that I didn't want to get dressed ( I was in boxers and a t-shirt) and go sit in the hallway, making small talk for 30-45 minutes for both of them to get done.

My reply was something along the lines of that is ok, I'll just hang out here. Bold friend again tried to convince me to come along, and my friend's sister just kind of nervously smiled. Not a I don't want this to happen kind of awkward smile, but more of a partially embarrassed and partially excited smile. Stupidly, I stuck to my no answer.

Thinking about it now, it is a little funny that the idea of being alone with me made them a little nervous, but doing it together was ok. Who knows what would have happened if I went along, but I'm guessing I would have been in the tanning room with two naked 18-year-olds and with a little leadership on my part, a lot more fun. At the time, I was getting laid as much as I wanted (20-year-old logic), but the 40-year-old me knows you never pass up a chance like that haha.

A bit of a side note, my friend's sister would pop over to visit from time to time by herself, and she got a bit bolder changing clothes in front of me (another story). I'm sure she wanted me to make a move, but at the time, she was still in my mind, my friend's little sister. Now, the idea of it being my friend's little sister would have made it even better :-)

All time dumbass
 

This takes place way back. A buddy of mine was supposed to meet me at a bar for a few beers, I got there first and while waiting, the bartender held up the phone and called out my name, it was my buddy, he couldn't make it. I decided to have a couple anyway, sitting there watching a game when this older lady, guessing now 35, started chatting with me. I'm kind of shy, so she was the one initiating the conversation, but she had the ditzy kind of fun girl aura.

I don't know what brought it up, I think a cop show, but she asked me if I had ever been in handcuffs, I thought she meant had I been arrested, no, of course not. She laughed and said, the fun kind of handcuffs, I had heard of BDSM, mostly from Playboy cartoons, but I tried to act worldly and said "everyone talks about the leather, but no one does anything about it", playing off the old Mark Twain quote. BTW, that line has lead to a lot of fun in my life, use it.

She invited "why don't we have a beer at my apartment and I'll show you the ropes", another big laugh.

She lives in a huge apartment complex, but we finally get there, I'll skip the preliminaries, but it didn't take too long before she was naked, blindfolded and tied to the posts on her bed, I had a little whip she gave me, fun times. Then she said I need your cock, put on a condom.

Oh shit, I forgot them in my car, I asked if she had one, but I got this "what kind of girl do you think I am vibe", go figure. I tell her I'll be right back, she says "hurry". I was smart enough to leave the door unlocked since I didn't have a key, I run down to my car, grab two or three, and start heading back. Then it dawns on me, I have no idea what her apartment number is or where it is, there are dozens of possibilities. I wander around for a while looking for visual clues, I can't just start looking for an unlocked door, I'll be in handcuffs for real. So I just leave.

That bar was one of our hangouts, but I avoided it for weeks, fearing I'd run into a very angry kinky lady. But eventually I returned and there she was. I walked up to her to apologize and explain, but she kissed me and said that was the hottest thing she had ever experienced.

Thinking Back
 

Many Many times I wish I did something different,My first wife would float around in the pool nude all the time,Eric our teen aged lawn mower kid from down the road walked in on her just once and seen her -she jumped up from a lounge chair and covered up ,my missed opportunity was I should have called up Eric when she was in the pool to ride his bike up,park out front and go to the upper bedroom and look straight down into the pool,bring a camera also,,,,,,,Another time our neightbor John was outside walking around,an elderly guy,I had a video of my first wife floating in the pool and john was out near the stockade fence walking around,pool door is was always open,I should have gone out and said to John,garden lookes nice I'm going in the pool and turned around and ran over to the side door,dropping my towel ,going to the bedroom window with the video camera and john would have walked in and seen her lying on her float,,
Another was Tanya wanted to date me but I had a hot girlfriend,Tanya brought up her son one day to swim,me and Tanya were on the porch and Tanay said said this is embarrassing but my room mate wanted to know how you are hung,I laughed and said would you like to see,she said yes and pretended to be embarrassed-she wasn't,,we went into the livingroom and I dropped my shorts and she checked me out,I said it's your turn,Tanya took off her bathin suit,not a very pretty lady nude,after a while they were leaving and I said I have a date and have to shower,I said to Tanya to came into the bedroom before she leaves,I was drying off when she came in so I was facing her with the towel and half a woody just cause she was watching me,I walked around nude with her in the bedroom and took out my clothes,my missed oppotunity is that I should have had her dry me off and give me a hand job ,no way in hell I would have fucked her.

Didn't go for seconds
 

Back when I was in grad school I worked at the college newspaper and there was a lusty woman who worked with me. She was chubby, had big boobs/ass and although not so pretty, I was still interested. But she also had a boyfriend so our relationship was merely cordial.

One day after the end of the term was was on campus to check my final grades. I was leaving the campus when I heard someone shout my name from a half block away. It was Sheri H., the woman from the newspaper. She came over and suggested to go to a nearby wine bar to celebrate the end of the school year. Well one carafe of wine became two and three and before we knew it, we were both a bit buzzed and hours had passed. She suggested we go to my place, but first we had to stop at her place so she could put in her diaphragm!

When we got to my place, there was no pretense, we went straight to the bedroom and my nose was buried into her lusty, musty cleavage before she could take her bra off. She had an amazing body and within 2 minutes of entering my apartment I was inside her, pumping uncontrollably. She was the first woman who ever talked dirty to me, saying “Fuck me you fucker!” over and over and over. I was very impressed. This went on for a long time. It was very late and due to the excessive amount of wine we fell asleep together with me still on top and inside of her. I woke up an hour or so later and continued pumping her until she awoke and we finished things off.

The next morning we ended up in the bathtub together and she started giving me a fantastic underwater BJ, coming up for air with a halo of matted hair around her face and mascara running down her cheeks. She looked like a crazed BJ monster!. It took a while but she wouldn’t stop. We hung out for a bit afterwards and then both left for work. Silly me, nowadays I would have called in sick and fucked her all day. But when you are young you think things like this are going to happen often.

The really sad part of this tale is that this woman called me up a few weeks/months later and invited me to her apartment for dinner. I declined saying that I was seeing someone else (I was fucking a woman in my apartment building, but we were hardly an item). So stupid. This was before the days of fuck buddies; I felt I had to "date" a woman in order to fuck her. Many times I've fantasized about how things would have gone at that dinner. Nowadays I would tell her to answer the door nude and we'd get to dinner eventually.

As someone else said above, not sure this counts. But the time I first met my wife, looking back on it now from a number of years away, was a bit of a crazy time.
I had just split up with a long time girlfriend and was a bit heartbroken. I thought I was a bit of a loser in love, but actually in hindsight this was the only time in my life where i was "beating them off with a stick" as we used to say (note - no sticks were involved!).

I met my wife in a bar and i ended up going back to her place and, although there was no penetration, we pretty much did everything else you can think of. This happened quite a few more times over the next few weeks and months. Around the same time I started dating this other girl. She wasnt a keeper I knew. But my god she was hot. Now I know you all feel, like I do, that your wife is the most beautiful woman in the world, but this girl everyone wanted a piece of. She turned heads.
I also had a goodbye fuck from the ex. A few more girls too (two of which sort of at the same time... sort of, not really a threesome, its complicated).
However, there was this other girl. A friend of a friend who we kept hanging out with. Now she was one you should not sleep with. Especially as a few mates had been there before. But I was low, she wanted me, and pursued me into bed with her. Now this girl was fully aware I used to disappear back to my now wifes place. So half way through blowing me she takes my cock out her mouth and asks if I'm thinking of my now wife.
I was a bit shocked. But she kept saying her name. Asking me if she did this to me, to which I said yes. She then asked me, while hevwas riding my cock, what my wifes pussy tasted like. I said nice and asked why she wanted to know. And she said shed been fantasizing about my wifes pussy and wanted to taste it, would I like to see her lick my wifes pussy etc. Etc. I obviously said I would and pretty much blew my load straight away.

So after we finished, this girl said she was serious, and i should ask my wife if she wanted a threesome.
It was the only time I had sex with this girl, but we kept hanging around together, and she kept mentioning this proposed threesome. Once we were in a bar and I was talking to this girl and we saw my now wife. This girl started walking over to my wife saying shed "make it happen".
.. and I actively stopped her. I put my hand on her shoulder and told her not to.

What a massive prick I am, or was. Because back then my wife was all over me, and was desperate for something to happen between us. Well, it did, but she wanted more. And she had an adventurous side to her that meant I'm not entirely sure she would have said no to it.

Now I'm aware the above might make me seem a jerk with this messing about with lots of girls at the same time. But my wife was dating and screwing other people at this time as well, and we both agreed to make it serious between us some time later, and we are happily married many years later.
But I still remember that night in that shitty bar and what might have been. The thought of seeing a couple of girls licking each others pussys while I fucked each of them from behind, and then marrying one of them, is a fucking hot, missed opportunity.

dinner and a show
 

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.

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

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.)

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.

Me too, but alas...
 

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! :)

Too many
 

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.

Another one
 

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.

invitation to a hot tub
 

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.

Wow!
 

Cockblocked by your driver? Wow. :mad:

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!

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.

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.

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.

Missed opportunity but not my fault
 

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!

Motorboat
 

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.

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

porn
 

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.

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.

Many missed opportunities
 

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. 🤦🤦🤦

Work Woman
 

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!

Leverage
 

Sister-in-Law was being bare-backed down Town to cover a debt. Transported her, naked save for her coat, dress and shoes, to the relevant Office. "I won't be long" she said. "It's only Short Time. You are a Man. You Know. 2 minutes. You can take me afterwards. All the way. Come inside."

I excused myself, fearful of either some "social disease", or being confronted by Divorce Proceedings, since I knew she needed a Big Cock and her Husband was stoney broke ! A shaky Marriage, held together since neither could find anyone else to put-up with them ! Regretted it ever since, 'cos I now realise that I could have used this fuck in future to seek sex on demand !

Yep, as a senior in high school (so 18), I had a FEW missed opportunities. I kicked myself then, but then I thought it was only a preview to what college would be like. Wow, was I wrong! Nothing happened in college. Nothing has happened since the end of my senior year of high school.

I have had fun things happen during the marriage to my wife, and I have posted about dozens of things in years gone by on these forums, but I am talking about pre-marriage life. So, yes, take up any chances you get! You may never get another!

Seize the night
 

There was a woman that I worked with she was a party girl. She's very beautiful and every weekend the couple of us would go out. I always was her ride being the closest so one night I went to pick her up and she wasn't ready yet so she told me to come inside. She was walking around the house in a canary yellow bra and panties not checking. So when she got ready I jokingly ask where's her clothes she answers she don't care who sees her panties. So we went to the club and her shoes popped me and her went back to the car to grab them. So while looking in the car she was bending in the car ass in the air. So she got her shoes and was putting them on and said she wanted to go the next club . So we went along the way we was talking she knew I was interested in someone else in our but they had cancelled last minute. In talking she says she wants to f@$k tonight so we made it to the club but the club closed early my people called me asking if I could come by her. So when I told everyone that I was gonna head in she says hey stay a few minutes with me and I told her I have to leave. I always think back to that night

So remembered another one. We lived in a shared house with the lads and ended up at one point with two girls living with us; one of them, G, was someone's mate who needed a room, and the other girl, C, was her mate. Anywhere they moved in and we all got on so they both became our mates too. Anyone, one day it was G's turn to do the washing up and she was feeling lazy and was trying to get a couple of the lads to do it for her instead. After pleading with them for acwhile she said as a joke that would the lads wash up if she flashed them her tits. One of my buddies took her up on her offer and so she pulled up tshirt and bra and apparently gave the all a good ten second look at her boobs.

I however was down the shop. When I got back a few minutes later my buddies were filling the sink and couldn't wait to tell me what had gone on, with G sat in the room smiling. I even fucking helped do the washing up with them, and never thought to ask for a tit flash for me!

Luckily a few weeks later G and me got very drunk and I fucked her all night, so I got to see more than just her big D cup norks. A couple of months after that I started seeing her mate C, who was far fitter, so got to see every inch of her too. But I do regret not being part if that initial boob flash with my mates.

I can't tell you how many times I missed out on things because I was in another room or doing something else that was helpful and nice for others, just to find out that my niceness resulted in me missing something. :)

Probably many times because I was just too shy or naive to see it. One specifically stands out. Friend of mine who I met over a message board invited me down to her house in NC in 2001. This wasn't too long after 9/11. But I went down and hung out with her a few days and one nice we got HAMMERED and I was a bit too hammered to make any moves.

She is beautiful. Big boobs, great personality, and I totally F'd it up. Oh well.

I missed this one, but enjoy the Memory!
 

Hanging around in my Buddy's BAR was real good for finding new girls to take out or just enjoy the end of the night! Many of my Buddy's would bring their girlfriends to the BAR and I got to meet them, have a few drinks and dances with them too!
This one evening my Buddy's girlfriend came in the BAR and was looking for him, but he never showed up so she just stayed with me and we both had plenty to drink and talk about!
She did tell me that her girlfriend dropped her off cause she thought that my Buddy / her BF would give her a ride home. Since he never showed up I told her that when she was ready to leave that I'll drive her home!
We stayed till closing time and both of us were in a playful intoxicated mood, seems like the women get more of that friskiness after so many drinks!
When we got in my car she asked if we could go for a nice ride and park someplace so we could talk more?
I said sure and wasn't really thinking about doing or trying anything with her, not at least in the beginning moments~
When we parked and started to talk, she just kept on getting closer to me. I was surprised cause soon after her moving closer she went for a lip lock and the Kissing started~ I still can remember her playful tongue in my mouth, then her hands got to move towards my crotch.
I still never tried to grope her body, but she asked me if I wanted to fuck her? My Instant response was "YES"!
The next thing I knew was she took everything from her waist down off and looking at her furry pussy along with thinking about having SEX with her made my cock hard! I hurried up to drop my bottom clothing off and she turned around facing me while inserting my cock into her sweet Pussy!
I can say it was my 1st time for having SEX with a girl and not getting started by touching any parts of her body~:o
We were starting to swap more tongue while she went up and down on my cock, then after so many times - she just Stopped and got off my Rock Solid cock!
She went to putting her clothing back on, while telling me we shouldn't be doing this and not to say anything about it to my Buddy / her BF.
I told her I won't, but I never did see her with him again nor did I ever see her again so I'm not sure if something happened or not? I seen him many times, but never talked about her or what happened to their relationship cause maybe I was better off being quiet?
But since I did hit it off with her I would have enjoyed trying to make a relation with her since I knew she enjoys having SEX or doing a Quickie that we didn't Finish!
:(

Swarthy.
 

Very highly strung, but younger, swarthy, colleague of the wife had been ditched by her 3 year live-in boyfriend on finishing Uni. So she Married an Itinerant, divorced, Builder who had the biggest cock she could find. Their son turned-out to be a "Slow-Learner", but she wanted "Intelligent Offspring". We called at her house to find her sunbathing in a bikini, my wife going upstairs to show the toddler a jig saw puzzle we'd bought. I went into the kitchen to find Swarthy feigning sleep in a chair by the table. Her bra straps were down, one tit fully displayed. I heard a noise from the lounge, returning to find someone had posted the Local Free Press Newspaper. Back in the kitchen, Swarthy had shed her bra, her briefs now around her ankles. Knees apart. Full, black bush. Flash of pink. Semi hard, I perused the scene as I heard my wife descending the stairs. If only....?

Missed out for sure-
 

Back in the day, my best friend at the time, married young to a very attractive girl. She was barely 19 when they got married. She was a complete hottie! Only a year before she was a cheerleader for her high school. They didn't have to get married, like a lot of young people, but they wanted to.

Believe me, if she wanted to marry me, I would have pulled the trigger asap! lol Even at that age she was fully developed with lovely full breasts and a great ass. He used to share nude pictures of her with me all of the time. I loved her full bush (that was very common in the mid to late 1980s) and her amazing body. I have seen photos of her with every toy under the sun stuffed in her holes. I had no idea what a horndog she was for constant sex! In fact, he couldn't keep up with her sexual needs.

The thing that I missed out on was he always wanted me to fuck her while he watched. He also wanted he and I to fuck her together with her in the doggy position. She was completely into it. They didn't know how to ask me. They were afraid of what I might think of them if they asked. :(

Later, he turned into a drunk and she left him. I was married at the time to my wife and couldn't go after her. She is still very cute and sexy. It didn't take her but a few weeks to replace my ex-friend's drunk ass. It's kind of ironic, she is fucking another guy (her new husband) but her ex isn't watching it. lol

I do still have nude photos of her from back in the day. I'm not going to share them because I don't have her permission. She probably knows that I have them. He used to tell her that he shared her nude photos with me and I kept some. She always wanted to know from him what I thought of her when I saw her nude.

I wish they would have asked! She and I are still friends and talk from time-to-time. When she was pregnant, and very horny, she said that she almost asked me to fuck her on her own. (I wasn't married at that time.) She was so horny from the hormones, and her drunk husband wouldn't touch her.

Mother in law
 

One summer my mother in law stayed with us all summer,my wife at the time told me to keep covered and never let her see you nude,I wanted to walk around the house nude with her here,I should have just done that,but a few years later my wife was moved out,her mom stopped all the time and my fantasy came true.