The Missed Opportunities Thread
 

From an idea in the bucket list thread https://forum.oneclickchicks.com/sho...d.php?t=222877

I would like a time machine to do all the dirty things i could have but didnt when i was young.

As Omega88 added:

So true. The 'if only" list is too long - missed opportunities, not seen / realized until too late opportunities, doing the "right" thing vs what really wanted to do, etc. etc. "They" say you regret the things you didn't do more than the things you did.

So post here things that you somehow missed out on and know they would have happened, and would build your own Tardis if you thought you could go back for a do over.

I can start.

1) A gf kept hinting that she wanted me to pee on her, but i was determined to make her actually say it and ask to be peeed on but she never did, and i never got to do it.

2) A gf asked me to shave her pussy, i was worried about accidentally nicking her and putting it out of commission for the weekend and i just wanted to spend it banging all day so i said no. I have wanted to do that ever since. Even asked her last time i saw her, about 10 years later, she refused.

im sure theres others, im old, memory takes a while.

1. Old girlfriend wanted me to take nude photos of her. I was embarrassed that the (pre digital era) developers would get to see her tits and pussy so I only took photos of her in her bra and panties. I still have these, but would much prefer to have ones of 19 year old pussy and tits.
2. That time I was in a bar with my female flatmate I'd screwed once and she spotted my wife (then just a girl I'd slept with a few times) and the flatmate told me she was going to talk my (now) wife into coming back for a threesome. I stopped her. WTF!
3. The various holidays I've either not been on where my wife and some of the other girls have gone topless, or the holidays I've been on with female friends, friends wives, MIL etc where ive not pushed the topless cause.
4. The new year's eve round another couples place where at midnight my wife exclaimed that her and the other wife should make out for me and the other husbands enjoyment, and I stopped her.
5. That time my wife did make out with the same girl in a nightclub when the other girl was single and I wasn't around at the time, and when I found them later and they told me what they'd been up to, I was too drunk to get them to carry on where they'd left off and they thought I was mad with them.
6. All those girls that were clearly gagging for it when I look back at it now (one girl called Bryony even said I needed to go back to her flat now and screw her hard!) but I didn't realise or was too timid.
7. I'm sure there have been times where I could have engineered the situation to fulfil my wife's desire to be spitroasted followed by DP whilst she's eating another woman's pussy.

I'm sure there are more....

So many, these days if it's in the moment I'll go all in, but years back it was different, so I'll start off with some short ones.

I turned down a threesome with my fwb and a friend. We were all drunk, and they were eating each other out etc. I watched then fell into a drunken sleep, they woke me by sucking me but I was too far gone. I wasn't interested, just wanted to sleep. I've fucked both seperately, but never together, and I never got another chance.

Same friend was a bit freaky, we did all sorts of crazy stuff over a short period. One of them was that she wanted to get fucked in the ass in public. I never obliged at the time but I'm sure some lucky guy did. (My friend ended up marrying her)

There was a got single foreign mom I worked with that I'd hang out with on occasion. We'd smoke some weed and drink, play games, watch tv, talk etc at her place. She had a banging body and one night she pretty much unzipped me and started blowing me. I was pretty wasted so I felt her up a bit and then put a stop to it, not wanting to cheat. The way things turned out I really should have fucked her. I did get a topless shot from her but yeah, still pretty bummed.

The list is long but one comes to mind. Back when I was a legal teen working at a restaurant, there was a bus girl (also legal) who was known to be easy. She was being very friendly towards me while I was waiting to use the pay phone to call for a ride home. The opportunity was right there but I didn't go for it. As they say, to know then what I know now...

Way back when, I was engaged to another woman who would ultimately not end up being my wife. She was a senior in college and had a LOT of hot friends. One in particular I was very fond of, and would flirt with her a lot. My fiancé was well aware, and would tease me all the time about my crush on her.

One night we were at this party, going pretty hard. A lot of her friends were there, including this one. We all drank a lot. At the end of the night my fiancé and her friend crashed in a spare bedroom. I found them, and decided to lay down in between them. They were both in light PJs, that didn't leave much to the imagination.

Never in a million years did I think this other girl was attracted to me at all, never mind be interested in anything. I "accidently" bumped up against her a few time, catching fleeting touches of her ass and tits. But ended up putting my arm around my fiancé like a good guy, and went to sleep.

Later the next day, when we were alone, she tells me, well you missed quite an opportunity last night. I asked her what she was talking about. She told me that in their buzzed state, they talked about showing me a good time in bed if I made moves on the friend. In other words, it could have been my first 3-some. But no, I had to be the good guy!

She never let me live that down, and the opportunity never presented itself again. I ended up telling my current wife about it, and she also does not let me live it down. She brings it up now and again just to torture me! LOL

Highly Strung
 

Wifes Work Colleague. Been swiftly ditched by her 3-year-live-in Boyfriend when Uni Finished. Spotted sunbathing topless in her back-garden by an Itinerant Roof Repairer. "Gerr e'm Off!" he demanded. "You First!" she chanted. He did, his cock almost as thick as her wrist and hanging half-way to his knee. The biggest she'd ever seen! "You had better come down here!" she called. Quickly pregnant, and married, their off-spring took-after Non-Sophisticated Father! But she wanted an Educated Child! So she settled for "Careful-In-House-Big-Cock" whilst seeking a suitable, Degree Qualified, Mate for "Precise-One-Night-Stands".

We called at her house. Her Hubby being out, my wife went upstairs to entertain their toddler. I walked into the kitchen. Highly Strung was sat faking sleep, her bikini top ditched, her legs splayed wide apart. I fled when I heard my wife on the stairs, preventing me from further enhancing the situation.

Meanwhile, a New Work Colleague had arrived and a "relationship", involving the New Hubby, and Family Meals taken at Local Restraunts, speedily established. Quickly followed by a "suitable" Child !

The one that I regret to this day, I can't mention because I was under eighteen at the time. The other missed opportunities that come to mind involve my wife.

Very early on in our marriage, she offered me an FMF threesome. The third person she had in mind was one of her friends who was bisexual. As my wife is a selfless person, I thought she might have been trying to please me with something that she really didn't want to do herself. At the time, I was genuinely satisfied with our sex life just as it was, so I didn't take up the offer.

A few years later, we told a couple of close friends that our number one fantasy was to have other people watch us having sex. The lady said that they'd be more than happy to make it reality for us. However, her husband said nothing, so I suspected he wasn't as keen as his wife. Therefore, I didn't pursue it any further with them. In retrospect, I think he was probably just being cautious about too readily admitting he'd like to see my wife naked on the job, in case he looked like a perv.

Another few years further on, we became friends with a couple through our kids' football teams. They were quite sparky and we all got on together really well. One evening at the club dinner, the woman casually lifted her husband's kilt to show my wife his cock. Later, my wife told me all about it. I was quite impressed that the woman would do that. A while afterwards, we talked about the couple again. My wife said that if ever I wanted to try wife swapping, there were the ones to go for because she quite fancied the guy. Much as I liked the woman, I wasn't comfortable with us fucking other people, so I treated her comments as just another one of her risque jokes.

1. Back in college, this one girl I had known since high school asked me to go over to her dorm to watch a movie with her. She asked for a shoulder massage since I had taken a course on massages before so I was known amongst my friends for giving good ones. We were sitting there watching the movie with me giving her a massage when she turned around and asked if I could give her a back rub next. I told her yes so she proceeded to lay down on the bed. After a couple of minutes, she asked if her bra was in the way and without waiting for an answer, she took it off. As a guy who was already dating a person in a long distance situation, that already threw me off but when she took her shirt off after the bra too, I bailed. I always wondered what might have happened since the girl I was dating at the time ended up breaking my heart and I found out later on that the girl I was giving the massage to was really into me.

2. On a vacation with the long distance girlfriend from situation #1, we were approached by a girl who made it very clear that she wanted to hook up with both of us. My girl was already drunk and totally agreed to it. Needless to say, I was floating on cloud 9 as one of most guys dreams was about to come true. Then, my girl proceeded to puke on the other one when we were back in the hotel room so that but a stop to the evening...

My long-divorced mum was a heavy social drinker. he once came home so blind drunk from an office party that I had to walk her back from the taxi. I took her to her bedroom and told her to get into bed while I'd get a big glass of water and a couple of Alka-Selzers. When I came back to the bedroom she was lying naked on the bed. As I tried to put the sheet over her she put her hand behind my neck and tried to get me in with her. Took me a while to settle her down. Wanked myself silly many times after and can't help wondering what it would have been like if I had taken her up on the offer.

2 times
 

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.

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.

Hot
 

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.

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.

I’m an idiot
 

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.

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 :rolleyes: 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!

Just fuck her
 

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.

1 hr drive? Spend the night!
 

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

Make sure you document everything for posterity😜