Biggest Sex Opportunity Youve Passed Up?

Years ago I worked security at a mall when I was abou 19-20. I started hanging out with this gorgeous blonde who looked like a younger Elle McPherson. She was only 16 and worked at the census taking place in the mall. Anyways I ended up taking her to a Janet Jackson concert and after was with her alone but I wasn't experienced at all at that time so I was more gentlemanly then than I am now and let her off with a kiss.

I found out later talking to her that she would have had sex with me had I pursued it that night.

It's a good thing you didn't mrrock, that would be statutory rape.

I had ano acquaintance in my friend circle in my early 20s who was a solid 8, maybe a 9 when she hit the gym regularly. She was an ex sorority girl and loved to drink.

Long story short, I drove her drunk ass home one night. She wanted me to come in. I wanted her to remember it if we hooked up. So I made an excuse and hugged her goodnight.

This is one of those girls who probably never had sex sober. I think she felt both judged and rejected by me. If we'd fucked it would have been fun, and although she was too drunk to drive, she wasn't blacking out or anything.

I played it safe, but in hindsight it was probably the wrong call.

Mine happens to be strip club related. About 15 years ago went with my buddy on my first SC visit. Got my first ever lap dance with a beautiful curvy brunette. Still think she was a 7-8 in recollection, but at that time she was the hottest chick I'd ever seen naked. Got a couple dances and I know she realized she had complete control over me, what with my mouth gaping open and the drool trickling out. When she was done she asks me, "do you wanna come over and watch Legally Blonde with me?" I didn't know what to think. All kinds of thoughts ran through my mind. Maybe even that it was some kind of elaborate prostitution sting. Didn't think she might actually want to fuck me as I had little confidence with women at the time, and the concept of P4P was alien to my young mind. The next words out of my mouth were, "No, I have to get home and get my beauty sleep." WTF you pussy! was all I could think to myself. She smiled and said okay and I went back to tell my buddy, who immediately called bullshit on me. Never again have I had a girl offer to leave the club with me after a couple of dances. Still not sure if she wanted to do P4P, could sense my naivety to the whole situation and had a boyfriend waiting at her apartment to roll me, or if she just legitimately wanted to fuck. Have regretted not finding out ever since. But the memory of her standing naked in front of me, back-lit by the club's lights, asking me to come home with her is burned forever into my brain. True story.

Once, during our annual major downtown Detroit fireworks that I've attended for years, I ran into this blonde barmaid I knew from a blues bar. She was very, very drunk and had become separated from her group. I liked her a lot, she was nice, she was gorgeous so I walked her back to my car after the fireworks. We came way too close to getting mugged, but fortunately as we rounded a corner, there were a group of people and the muggers disappeared. She told me where she lived and we started off. The little head took control and I diverted towards my house, she got upset and told me to take her home. I was not going to have sex with her against her will, so I drove her home. Sigh.

Back in my 20's I went to my favorite watering hole and ran into two girls that I knew very well. I also knew the husband of one and the boy friend of the other. They were celebrating the birthday of the single one. So I joined them and bought them drinks and more drinks. An hour or so later the married one went home leaving me with the birthday girl. She was a nurse and out of the blue says " I see all of these babies in the nursery at the hospital. Doesn't anyone do it for fun anymore?"

You'd have to be pretty stupid to not recognize that as a hint but since I knew her boy friend so well, I didn't want to screw of that friendship. So I let the whole thing slide..

A couple of days later I found out that she had split from her boy friend and that her female friend had left the two of us alone at the bar so that we could get it on.

I can think of 3, all from when I was in high school and college.

1. In college, a hot girl that I was friends with for a long time basically threw herself at me, but I was on mushrooms and didn't act on it. I was trying to hook up with her friend, but it wasn't working out. So the hot girl came back to my room and was really drunk trying to convince me that she was much better in bed than her friend and I should forget about her friend. If I was just drunk and not shrooming, I would have torn her clothes off. Don't do drugs.

2. I went to a formal with a girl who I never dated or hooked up with. A week before the formal, I started dating another girl. I had a huge crush on the formal girl for several years, before I knew her and never thought I would have a shot with her. At the formal, she asked me to go home with her and spend the night at her place. I said no, because I wanted to be faithful to my new gf. I can't believe I didn't go home with her. This was the girl of my dreams in high school and I passed her up. The downside of fidelity. Wish I could get a mulligan on that one.

3. I was married at the time and on vacation by myself, visiting friends. I went out one night and met this hot Asian girl 15 years younger than me who was on tripping on Ecstacy. She was friends with my friends. We get in a cab to go to a new club and the girl climbed on to my lap and was all over me. She kept hugging me and wanted me to kiss her. Finally, she was like, "what, you don't like me?" Her friend said 'look at the ring on his finger, he's married'. Again, the price of fidelity. The worst part is that I wound up getting divorced a year or two later, because my ex cheated on me. Had I known, I would have torn that Asian girls clothes off and fucked her all night.

Man, I wish I could go back in time. 3 huge blown opportunities. Fuuuuccccckkkk!!!

Correction: 2 were from h.s. & college. The 3rd was when I was married in my 30's.

I was a college student and a friend had his girl friend's sister down for the weekend. She was 17 and awed by the college atmosphere. She & I hit it off, kissing, touching, drinking, kissing more, touching more, drinking lots more; into my bedroom, clothes coming off, exploring each others' bodies, drinking more & more; she took my rock hard member in her mouth.... And I passed out. She was gone when I awoke in the morning, but before leaving for home she told her sister she was real disappointed cuz she really wanted to fuck me. She ended up marrying another friend of mine and I'd occasionally see her and kick myself for a missed opportunity.

Drunk girls (which I won't do, since I feel they can't give consent) and crying virgins (yes, many of them do cry). Missed opportunities, sure, but I don't regret passing them up.

There's a couple that I do regret passing up. (1) Milf and her milf-y friend (10 years older than me) that I carried through college statistics class, and offered a "romp in the sack" for payment for services rendered at the end. I declined; instead, I made them take me out to the sports bar on their dime. To their credit. they wore some awesome loose-women-cougar-clothing and we had a blast partying. It was her and 2 of her friends with me. She paid for everything.

(2) High school teacher. 35 y.o milf, Russian. Also often wore stockings, high heels, and shorts skirts -or- dockers with golf/polo shirts -- so it was one extreme or the other. It was practically stereotypical or cliche. she was always touching me in inappropriate ways. I kind of thought she was just "friendly" until my mom pointed it out to me one day, "Dominic, I think she's kind of into you, in a weird inappropriate way. Ew! I think she wants to date my son!" Which against all odds of raging 17yo teenage boy hormones, I somehow failed to tap that ass. (It's because, ew, my Mom's involved in it now, so, ew, like 'NO.') Boy was I dumb. Should have tapped that.

I vividly remember the scene from that day. It was an after school band rehearsal. I saw my cheerleader girlfriend come into the band room, I followed her into the band locker room, gave her her birthday gift (since I didn't want to wait until later), she kissed me, I twirled her around, kissed, lifted her, kissed, like most teenagers do (if she's spinner). The teacher came in there and told us that was inappropriate for a school setting. We finished and went back.

While in the practice area, I was eating my dinner (McDs French fries) and offered the teacher some, since she was sitting so close next to me. Then she are starts rubbing squeezing my thigh and arm telling me, 'no.' "I can't eat those if I want to keep my nice-looking legs, and I need these legs to attract a man." She's wearing black hose, a short black shirt, and black heels. While she says that, she uses her other hand to slowly pull up her skirt about an inch or so along her thighs, so I'll notice. I responded, "What are you worried about? Your legs look great!"

Meantime, like an oblivious lunk, I eat my fries and slup my soda and say to myself, Interesting. I wonder why she's telling me about her dating life. I'd write out the rest of the dialog but it makes me seem like an oblivious idiot. Assuming I'm reading the situation right. Maybe she just got off on the sexual tension? Maybe she was crazy? Who knows.

Then there was the other time when she asked me to sort uniforms with her after school. She actually waited until I got out of wrestling practice. While in the back store room, she started: "Do you ever worry that we'll get locked in and we'll be stuck back here?" While tossing of bunch uniforms on an existing un-sorted pile, she finshed with: "we might have to sleep in her, LOL." Being a lunk I thought, boy that would suck. That pile of clothes sure looks uncomfortable.

I told my mom the first story (French fries), and she clarified it for me. She's into you. She regrets missing out not dating someone like you in High School, was her guess. Once Mom told me that, other weird times, like the uniform story suddenly made more sense. Now you see why I'm on TUSCL and go to SCs. Women fkn confuse me sometimes.

I regret not at least trying to tap that. It's totally cliché and no one here is going to believe this. I don't blame you. After all, everything here is a work of fiction!

Damnit. and I proofread it, too! ^^It should have been "short black SKIRT, not shirt. She wore a puffy white blouse. Everything else was black.

@larryfisherman Actually that WAS a big reason I didn't pursue it! Even though she was hot as hell I kept seeing 16 in neon letters over her head and thinking "16 will get you 30"!

One of mine actually had a happy ending: The summer after freshman year of college was a straight for my group of friends that went back home. There was about 15 - 20 of us that threw a house party almost every night...obviously this leads to hookups. One of my longtime friends was the slut of the group (though there were contenders), but never hooked up within the group. We had never really fooled around before.

We both passed out in the same bed after one party and one thing to another and we started making out and things started progressing. After a bit, I tell her I want to slow down because I like her too much. Truth is, I had major whiskey dick. She gets really pissed off, makes a booty call and a guy swings by a little later to pick her up.

I didn't actually get to fuck her for almost another year...when we were dating. Now, we're married. To this day, my wife says I am the only guy with the balls to have turned her down and that's what got her to start liking me. Little does she know I really did want to fuck her but it was really just whiskey dick stopping me from getting it up.

Dominic, I feel ya.

I often say to myself, if I had the knowledge I do today back in high school, I would have had so much more fun.

Many years ago in the early '70s, I saw a lovely young woman hitchhiking on the highway after midnight. Her car had broken down and she asked for a ride home. She was around my age and back then, safety was not the issue it is today. She hopped in and I headed to her home.

Some conversation as to where I was headed at that time. I told her I was going to meet some friends for late night bowling (true). Anyway, we get to her home. She asks if I wished to come in for a drink. I declined.

Was sex likely? No idea, but certainly seemed it might have been.

I'll finish by saying this was before my SC days and shortly after I married.

Other than early on, think high school days, I can't think of many misses. But one comes to mind.

About 8 years ago, before I started chasing strippers, I stopped in a small town I normally didn't have to stay in. Lodging there was limited and less than 4-star for sure. I'm walking down the hall nearly to my room when a girl, maybe 30 years old, comes out of a room two doors down. She was good looking, tno outstanding, just an average looking girl, blonde, I'd say a 7 in looks. As we pass she says "Wow, your good looking". Instead of offering her the chance for a romp I just said "thank you".

I was very tired from traveling, but later on thought, you idiot, could have had a piece of ass. Oh, well.

Was at a free street concert years ago. Davy Jones from the Monkees was the performer. An attractive women came and stood next to me for probably 45 minutes. I didn't think I was in her league so while I I was still deciding whether to talk to her another guy worked his way to us and after a few minutes he started to talking to her. They ended up leaving together. I'm pretty sure she was there to get picked up. My PL life started early

tuscl.net

Here's mine. I hung around gawking at her, thinking I was being silly but too high to realize she must have noticed my ogling...she disappeared on my fourth walk by...

Here's a good one.

In college I was at a frat party where the girls got zip tied to a guy and went room to room doing a shot. I got one of the hottest girls from the visiting sorority. We hit it off well and went on a date that weekend. Got to 2nd base and things were going the right way for potential girlfriend instead of one night stand. I had a rule, if a girl fucked me on the first date, she wasn't girlfriend material and this girl passed the test. I was excited because she was gorgeous and cool.

The next weekend her sorority had a party with another frat. She called and said to meet her downtown afterwards. Some how wires got crossed and we didn't meet up. I get home at 2am and she had called my apartment (this is before cell phones were common) leaving a message that she wanted to see me. I lived way off campus and was drunk so there was no safe way to get to her. I knew it was a booty call but I didn't call back because I actually wanted to date her too. I called her the next day and we agreed to go on a date a few days later as we both already had plans that Saturday night.

She went to another frat party, ending up blowing some guy who had a girlfriend at a rival sorority of hers, and that girl had a brother from another fraternity that was rivals with the frat of the guy that got blown.

That night a huge fight broke out between both frats (who were next door to each other) and the girl was labeled a slut because it all started over a blowjob this girl gave. It was so bad she either dropped out or transferred at the end of the semester.

This was in late October and I never saw or heard from her again, and she was gone by the time the semester was over which was around the 1st week in December. I sure as hell wasn't going to call her and she never called me.

Just to think, had I accepted the booty call that whole situation probably would have never happened. On the other hand if I did hook up with her, and she ended up blowing a guy the next night, I would have looked like a fool.

I was in a 10 year relationship, during that time there were some many opportunities for other pussy. I stayed faithful to my girl though. Now that we are broken up, I wish I would have seized on some of the other opportunities!

Yeah, women think alike on this one, when you are in a relationship or married, they get the vibe that you must be the man !! I've turned down opportunities like that cuz it didn't feel right at the time.

Too many to count. I was so naive when I was young.

Most recent was last night. I had been working long hours at the computer all day and my wrist was sore from carpal tunnel syndrome.

In college I passed up too many wonderful opportunities to count or remember ... I remember being super choosey in a way I definitely wouldn't be today.

Taking it back to strip clubs, one early nightshift I saw an amazing stripper on her way to the club, she recognized me, and asked me if I wanted to take her drinking. Well, the two of us partied like monsters for 2-3 hours, drinking, flirting, having fun. When I finally walked her back to the club, she comes out of the dressing, grabs my hand, and says, "that was so fun. Come with me, let me give you a blow job." The implication was crystal clear -- she wasn't charging me, she was feeling the love. I turned her down because, unlike the enlightened Subraman before you, this was back when I made my big mistake of crushing for real on a stripper, and I didn't want my crush stripper to get mad at me, so I turned down the partygirl stripper for the free BJ. Partygirl stripper was way hotter than crush stripper, btw. My penis was so angry with me that it trolled me on twitter for months.

Happy ending! Shortly thereafter the stripper who I had the inappropriate crush on basically quit and ended things, I became VERY close with partygirl, we eventually became FWB ... and she was incredible

Probably more missed opportunities than I realize or care to admit but here's 1 of 3 that I will post.

About 2 or 3 years after high school I ended going on a few dates with a girl I had an off again and on again crush on. Turns out she felt the same but it never worked out during high school. So, after a few dates we were in her basement watching a movie and start to go at it, making out, groping and all. All of the sudden she pulls my pants down and was about to ride me. I stop her. Yeah, I can’t believe I did even as I write this. But at the time my reasoning was we didn’t have a condom and although she was on the pill (she said and I believed her) I still was uncomfortable. I mention we didn’t have a condom but quickly changed the subject because I felt she might think the condom issue was because I thought she was dirty. I said some stupid shit about sex being an issue with me and my ex (“I always wanting it and she didn’t”) so I wanted to discuss it first and was just taken by surprise or whatever and that I definitely wanted to have sex soon. Well, I thought we were all good and I was happy as shit, thinking we were going to bone the next time we were together .In fact I asked her to come over my house the next day. I was ready with the rubbers and so exited because I thought I cared for her and we could work out long tem. Well, she was a no show. And for weeks I could never get her on the phone (not everyone had cells back then). I being stupid could not understand what the hell happened. Some time went by like a few years and we see each other at a bar and talk, She apologized for how things ended. When I questioned on why she said I made her feel like a slut when I refused sex with her. For a few years I told myself I made the right decision but that thinking changed over time and I wished we fucked.

#2 of 3 Another time, I met a girl in Montreal who was 18 or 19 and I was 23 . She was really into me and we kept in touch and spoke often for a few months. She always asked me to drive up (I live in the northeast) Now I know I could have gone up there and for sure had sex with her. She was attractive enough but I felt she was too young and too into me and it would lead her on especially since she was a virgin. She had little bit of baggage and I didn’t want to take advantage of her. I don’t regret it on hand for the reasons I describe but I still consider it a missed opportunity for at least a blowjob (and she had fantastic lips).

#3 of 3 Around the same time, met a girl closer to home that actually picked me up at a bar. She was a smoke show. We went on one date. Didn’t start well, as she was MIA. Finally 2 hours after, I hear from her and apparently was with her ex who was in the hospital. Red flag but I ignored it. The date was good and all and I kept my cool around her, even though I was still surprised she was into me because she was so hot. Come to find out, the ex BF was from my high school who I always considered to be a dick, because that’s what he was. That bit of info threw me for a loop and got into my head. Back at her place on her bed no tv or music just us on the bed. Well, normally any half sane, half intelligent straight guy would be thinking its go time. But I’m too wrapped up into my own head that this girl is out of my league and further proof to me being who her ex was. Though he was a dick, he was a jock and popular in high school. After some stupid conversation on my part I finally grew a set and tried to get things going but it was far too late.

The End (pathetic right?)

1. In college, during the period I was dating girlfriend #2, I had this evening sociology class and we had to do a group project with a presentation in front of the class. There was me, two typical college age ladies and a 30 something lady in our group. The older lady had ample tits that I would sometimes stare at in class. She had a house she lived at in the town our college was in, so we worked on our project there. This was before I ever had my own car, so I rode my bike to her house. After we were done, we were talking and I told her I had to go and ride my bike home. She then goes "I can give you a ride you will never forget". I just told her I wanted to get home and besides, my girlfriend was probably missing me. The next class, one of the other ladies then comes up to me and tells me that the 30 something likes me and would like to see me in private once. But I was just too devoted to my girlfriend then, which was ultimately stupid, because that relationship didn't last til the end of the semester. And I could have had MILF pussy before the term MILF was invented.

2. In the first year of my current job, there was a Russian (or possibly Ukrainian) lady who worked there. She was constantly coming on to me. But I had a crush on this other lady there, so I passed her up. Found out the lady I liked was really a lesbian and that the Russian lady was something of a slut. I was apparently the only guy who she never got laid with at work.

Seems to be alot of regret going on in this thread

John Smith lol

Couple more:

I met this 19 year old spinner with no tits but a great ass online and ended up taking her virginity. She lived more than an hour away, and despite the fact she would have made a fun girlfriend, I chose to get serious about a tall volleyball player I met almost the same time. Tall volleyball player was kind of boring in bed and didn't last long, and spinner moved on during the couple months I was with VB Player. This is less of a regret because I did fuck her a few times.

About a week after fucking my now wife for the first time on our second date, I went to a wedding. I didn't want to invite a girl I'd known for 2 weeks, so I went solo (lots of my friends went too).

There was a cliche single bridesmaid who was eager to get fucked who hit on my buddy first, but he was taken and steered her towards me.

She went so far as to offer me a BJ in the bathroom. Now wife and I were in the awkward " it quite serious yet" phase but it still didn't feel right. But in hindsight I should have taken the BJ and more.

It might be interesting to hear the stories about sex experiences we have had that we regret.

I suddenly remember a whole lot of instances if I could go back in time.

I remember back in my college days one day I went to a crowded class, we literally had to share arm rests we were so crowded in there. I had two girls beside me and some in front of me off to the sides so I wasn't complaining. Anyway one day I went to class kind of tired but relaxed. The girl beside me was wearing shorts. She propped her legs up beside me, so did another girl in the row in front. They were looking good. I looked off to the side and wondered if a girl over there kept looking my way. Anyway at some point later, I must have gotten too relaxed. Got an embarrassing boner that all the girls on both sides of me were looking at. Looking at me, doesn't help but girls didn't seem to care. I was embarrassed and glad to leave when class was over. Anyway at least a couple of the girls from that class were in my next class but at least it wasn't packed. One if those girls, I guess to get my attention decided to sit in front of me off to the side a little. She kept looking in between my legs obviously the whole class. I guess she was trying to let me know what she wanted. I just felt further embarrassed. In hind site, she could have really helped me out back then. If she had some free space without a bunch of roommates or suite mates. Nothing quite like all the girls in a college class staring in between your legs and at least one trying to go further. At least I wasn't in a back row. My first embarrassing thought was, the girls looking in between my legs don't help. Then one girl in my next class just stared almost all class in between my legs. I lost the boner in between classes. I think she wanted it.

I was at a hotel bar following a wedding and ran into two ladies I knew from a local club. They also had been at a wedding. After the bar closed I decided I was a little too drunk to drive and tried to get a room. No vacancy. One of the two ladies offered for me to spend the night with her for a price. She made it clear the fee was not for just the room. She was as close to a perfect 10 as a woman can get. I had the money. I was single. I turned her down. I'm still not sure why. The other woman told me I was crazy for saying no.