Missed Opportunities

[Blue Tony]

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!

[Shihoin]

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.

[shnowballs]

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.

[Gnome72141]

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.

[SixPointFive]

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

[indym]

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 :-)

[piecenick]

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.

[outbog1]

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.

[raysallx]

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.

[Erii]

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.