Best sex you never had

Here's one that I don't think has come up on the boards before. What's the best sexual experience you could (or might) have had but didn't for some reason (bad luck, bad timing, moral qualms, etc.)?

Here's mine: A few years ago I went to my five-year college reunion. An incredibly hot girl---who I never would have thought I had a chance with---started talking to me, and told me that she had been nursing a crush on me ever since freshman year. After a few drinks, she made it VERY clear that she now intended to make up for lost time. She wanted to get it on in the bathroom (the reunion was being held in a restaurant), but I kept putting her off, mostly because she had said she was married.

After the restaurant closed, she didn't have a ride and was pretty drunk, so I drove her home. She wanted me to come in with her, because her husband was out of town---when I refused, she wanted to give me a blow job in the car. I turned that down too, watched her go inside, and drove away.

Of course, now a day doesn't go by that I don't wonder whether I should have gone through with it (despite the husband). It would have been so easy to stop along the way in a dark place when I was driving her home---she lived way out in the burbs---and bend her over the trunk and give it to her good. Well, I'll never know, I guess (unless she shows up at the next reunion).

You regret it because you didn't do it, but if you had gone ahead and done it you would probably be feeling other regrets right now based on the fact that she's married. So basically you were in a lose/lose situation, but in one you get laid and one you don't.

Gee, thanks for putting it all in perspective and giving me something new to be depressed about.

In High School I could have had a threesome with my girlfriend and a girl from her crew team who was about the craziest sex fiend I've ever met. Chalk it up to teenage insecurity that I did not go through with it.

Any time

Oy. Can't begin to say. I stupidly or cleverly turned down a number of proposals...

First one that pops to mind was ms. K. who went to the Math & Science boarding school that I did. K. was a japanese-caucasian girl with lovely skin, exotic eyes, and curves that were the favorite topic of conversation in the boys dorm. After one dance she warned that my bones might get jumped if I kept wearing my shirt open like that. I made a joke about having a headache and blew her off. Felt stupid about that one for years.

Years later I was paid a visit by R., a friend who I share with Mr. Niel Gaiman. She might have been the inspiration for a certain goth girl character in his work. I played chivalrous and gave her my bed, taking the couch downstairs despite her protests. Years later she still asks my why I didn't share the bed with her. I was idiotically chivalrous back then. That's still a happy circumstance, however. Though she's states away and I haven't seen her in a year, she dubs herself the head of my harem in conversation. Maybe something will come of this one yet.

A few years back I was leaving Atlanta, heartbroken, and landed in LA. A celeb friend of mine there tried to hook me up with C. Aguillera. I sometimes wonder what would have happened if I hadn't blown that one off, too. She seems a more decent girl than the media likes to make her out to be.

In college, there was this really cute girl who made her interest in me well known. She told me right off the bat that she was bi and thet she'd mot likely bring another girl with her when we hung out. I was intimidated and chickened out. That was young Cash....and I'd punch Young Cash in the face now, if I could.

either
A. close female friend i kinda had this FWB thing going with. wanted me to be her first, and i didnt feel right about it. partially because i lived in another state, and i thought her first should be someone who wasnt leaving in a couple days. i didnt think i deserved it, i thought she could do better than me, many many reasons.

she ended up losing it to some scumbag who used her. i wish i had, if for no other reason, that at least then she could remember the guy she lost her virginity to as being someone who cared for her deeply.

or

B. girl i was VERY infatuated with but waited too long to pursue. i didnt so much end up in the friends category as much as she had some serious emotional problems. we were together every day and very affectionate up to the point of anything actually happening, and shed stop it. but shed sleep with people whom she had no emotional attachment to. i finally asked her one day why she couldnt be with me and she said, "i cant date you because i trust you." at the time, that made no sense to me, but years later i actually understood that. she really did have feelings for me but didnt want to risk losing that. and me, like an asshole, i eventually turned my back on her. all the girls i dated and i dont think much of them now, but her, i never touched, but here 8 years later, i still wonder sometimes. she really made an impact on me.

Young Cash and Young Endlessben can both go play video games or whatever was better to do than have an awesome hot threesome. I'll go back in time and do them both rotten. Of course I'll be thrown in jail, but hey, I'm a time traveling orgy man!!!

ohhhhh...yeah, I had it. Sorry, chumps

I went on a road trip with this guy I hardly knew once to go visit a friend up north. He was a 'friend of a friend' and offered to keep me company for the 6 hour trip when none of my other friends would, but I digress. Anyway, he knew I was bi and as we were be-bopping along he mentioned he'd always wondered about being with a guy.

He was really nice looking and a lot deeper than I had originally assumed. Funny how 6 solid hours in a car with a little pot will do that to a person. We talked about it for a while and I got the impression I was being hit on, but just kinda brushed it aside. We got there, visited and drove back home that same night.... I'm weird like that. We talked some more on the way home and he made it clear enough that he'd try something with me. I chickened out basically and got to listen to him and one of my roomates making out that night cause I'd fallen asleep in her floor and woke up to the heavy panting of quiet sex. He seemed very.... adept.

*shrug* I just rolled over and went back to sleep. At least SOMEBODY was getting some.

never turned it down from someone i wanted.

Add Young Alpo to the list. Reading all these posts has reminded me I chickened out on a MFF threesome too! I guess I blocked that memory out up until now.

Baudot, however, gets the prize so far---he said no to Death!

Damn this is a story I needed to get off my chest.

About 5 years ago, I was really hung up on this girl. She was (perhaps still is?) this gorgeous latin brunette. Absolutely perfect body in my opinion. To be totally honest, her personality and mine never would have worked out, but I didn't care at the time. I was getting over someone else, and this chick was the picture of beauty to me. She had a boyfriend but for some reason was spending a lot...I mean a lot of time with me. She was still in high school...17 or 18...and I was 21.

SO on Labor Day '99, we were at a party at a buddy's trailer on a lake about 15 miles north of my hometown. I had a key to his trailer and this girl, another girl that was a mutual friend, and myself, showed up about 3 hours before anybody else. So we started partying early.

Strip poker, skinny dipping, drinking, you name it. They thumped me at strip poker, but I will never forget how she looked wearing nothing but one of my t-shirts. Anyway the strip-poker gets important later, because I was giving her shit for never getting naked.

She had something going on the next morning so I had to take her home early. When the time came, I'd just been skinny dipping again and went into a back room to get dried off and dressed. She comes back into that room while my back is turned and shuts the door. I can't remember exactly what she said now but it was something to the jist of, "OK since you didn't get me naked before, you get to try again," and she showed me the deck of cards.

Now...this isn't rocket science people. When two people are playing strip poker, you know what the goal is.

She was gorgeous. Absolutely gorgeous. From head-to-toe, perfect. I couldn't have imagined a woman being more beautiful.

...but at that moment, when I knew that if I wanted to, I could, all I could think about was the fact that she had a boyfriend. I somehow, casually suggested that she should get home quickly.

I did get a kiss that night, but I could have had so much more. On some levels I really regret not doing it.

She marries her then-boyfriend later this year.



[Edited on Mar 28, 2004 by Nocturnus]

After My ex fiance and I broke it off I spent a lot of time over at my friend rych's cause it was near my work and my house was well over an hour away. I have known him for almost 17 years now. Anyways, that being said we both know eachother very well and are quite comfortable with eachother. I started out sleeping on the couch, but his two boxers felt the need to sleep on the couch with me... eventually I ended up sleeping upstairs in his bed with him... for a long time nothing happened, until one night when we talked about it jokingly and I basically laughingly brushed it off. Now he has a kid with this old gf of his who I never thought was good enough for him and recently he has told me that one morning he woke up and couldn't imagine a day without her. So because I was stupid and scared, I gave up a shot at a great guy who has even wrote a song about me. It's funny how hind sight is 20 20 and a thing like him being 9 years older and over 5 inches shorter isn't a big deal anymore

Well, the first regret was back when I was with my second girlfriend. We were alone at my aunt's house and fooling around in the hot tub outside. We were both virgins and we had a perfect chance to amend that. But we both ended up pussying out. Tragic... would've been nice.

My second regret was about a year ago when I was hanging out with a friend of mine that I had previously dated. It was our first time hanging out again after we had broken up and it seemed tensions were running a little bit high. But I ended up actually accidentally dissolving that wiht some rather sweet (truthful) words and what followed was one of the most intense experiences I've ever had, which suddenly came to a sudden and abrupt halt when we realized we didn't have a condom. After that, we finished watching Pulp Fiction and then I left. After that night, the oppertunity has never again presented itself because now she's with someone else.

So... SHIT!!!

When I was pregnant I had great sex dreams all the time, orgasms included!
It was a nice way to wake up.

I still have them every once in a while.

time for me to get pregnant

Maybe not but it's good to know.

Oh that's easy. I turned down a menage a trois with two extremely hot girls after a dance, because I wanted to stay faithful to my long-distance girlfiend. Who dumped me about a month after I reunited with her.

The only other m-a-t offer I have had since was with some beefy chicks in their 40's.

Hey if the Governator can do it......

But seriously, guys have wet dreams when they're younger, isn't that the same thing? I mean not the same as getting pregnant, but the same as having orgasmic sex dreams.

Alpo, you should have went for it, the fact that she was married was of no concern to you, it's not you responsibilityto keep her faithful to her husband. For the record I'm not a cheater, never have never will, but I have no problem being "the other guy". If she's going to cheat she's going to cheat wether it's with me or someone else so I mite as well get mine.

Now back on topic...

I had a chance to have a 3some with my now X and her roomate, who had the perfect ass, and although my X suggested it I knew she would get all weird and at the time our relationship was going along ok so I didn;t want to rock the boat. Had I known it was all going to go to shit I would have took the opportunity.

Regrets, I have a few but here we go:

1) Well 2 regrets involved in this one. A few years ago I went out on my birthday with a good friend (even better of a friend since everone blew me off but him). The deal was if I didn't come up with something to do we were gonna go where HE wanted to go. Well he didn't get out of work til 10 so that limited the choices. I decided that we were gonna go for food and drinks. He didn't think that was acceptable, and decided we should go to a strip club. Regret A) I convinced him to go for drinks instead of going to the strip club. I should have gone to the strip club. So after a drink or 2, we went back to his house to watch movies cause I didn't feel like going home yet. He tries to make a move. Multiple times. Regret B) Stupid April puts a halt to it. he didn't even get a kiss in. I didn't want to ruin yet another friendship with sex, and I really valued his friendship. I also didn't want him to think that I did it because of the alcohol. Of course I NOW realize that with this friend it wouldn't have ruined anything at all, and I really wish I had given him the chance then. STUPID STUPID STUPID!

2) Two weeks before the previous episode, a group of us girls from work went out to see an all-male review for one of the girls 18th b-days. I hate being the oldest of the group. But a friend of hers from outside of work comes along. We were the only 2 over 21. Well the 2 of us decided that we were gonna go to a club for a little while, and we left the other girls behind. A few drinks in and we were dancing together mostly to avoid some really strange guys, but we were having fun with it. I'm gonna cut out the extraneous details here cause it really is a long story. So I ended up having to give her a ride home. We sat in front of her house for a while chatting, and complaining of out sore feet from all that dancing. So we started to give each other leg massages, slowly moving up higher, and getting closer and closer when the older sibling (can't remember whether it was a brother or sister) comes home and is waiting for her to leave the car. He/She needed the keys to the house. so close. we ended up meeting up a few other times, but something always happend with either of us to prevent anything good from happening. DAMN!! and she was HOT. damn bad timing

and those are just 2 of my stories of woe, regret and bad timing.

**edited because I need to learn how to spell after a long day.

[Edited on Mar 28, 2004 by Mylf]