Dude, I never should have slept with you

Hey, Mother Theresa. You do realize, that if you slept with her she is cheating, not you, right?

Anyone with a pulse can name opportunities to hook up that were bungled. My regrets are more of the sympathetic nature. There was at least one girl that I really cared about, but knew we didn't have the chemistry to make it last. I still keep in touch with her and we had the following exchange a couple of days ago:

Misanthropic: Happy Birthday, a bit late. And Merry Christmas. Also, Happy New Year, Happy Valentines day, and Happy St. Patty's day. There, I'm set for a few months.

Barbara: That's about all of the holidays you ever managed to spend with me anyway.



Ouch.

 

It's funny how we look back on ourselves when we were younger and think of how much sex we could have been having if we only knew then what we know now.

There's a movie where some character addresses that, I'm trying to think of it.

 

Haha, I found it.

The part I'm talking about is at 1:16

<a class="postlink" href="http://www.youtube.com/watch?v=u0kF24ceZMI" onclick="window.open(this.href);return false;">http://www.youtube.com/watch?v=u0kF24ceZMI</a>

 

I always thought it was bullshit that people say if they were young again they'd do things differently. Odds are, because of your psychological makeup, you'd do it very similarly to the way you did it before.

 

Ehh, I guess I regret that all the girls I always seem to get attracted to girls who are in relationships. One girl I was friends with in high school who I developed a massive crush on, but she had a boyfriend (who was a complete douche I might add) so I just acted like a pussy and kept tormenting myself by being her friend when I should have just stopped associating with her. She was a year ahead of me so she was in college while I was a senior in high school. She invited me to some party at her school which was only like 30 minutes away and she straight up told me she wanted to fuck me and had wanted to for years and that she broke up with her boyfriend like a month ago. I get there and it turns out she's dating some other guy so I just left because I wouldn't want to be the other guy.

Then there was some chick I worked with at a part time job before I left for basic. She was the smartest, but then again neither am I, but she was funny and cool to hang out with and amazingly hot to boot. She had a boyfriend (who also was a complete asshole) who ended up proposing to her and she accepted. She was still trying to get with me, and it got to the point where I played dumb and didn't make a move for so long she, like the other girl, straight up told me she wanted to fuck and at which point I had to say no because I didn't want to be the other guy.

Looking back with what I know now, sometimes I think I should have just had sex with them because they probably just found it elsewhere outside of their relationships, but then I think about how I was cheated on and how shitty that felt so I'm glad it wasn't me that did that to other people.

I've only slept with 4 girls and regret one of them. I hooked up with this girl in Korea after she started dating a guy I was kind of friends with but I had no idea. I felt terrible afterwards because he was a really genuinely nice guy who had just gone through a divorce where he found out his wife was cheating and his kid wasn't really his kid. I didn't have the balls to tell him. Mostly I regret being a pussy and not talking to more women which is something I'm still trying to change.

 

I think you're missing the "if I knew then, what I know now . . ." aspect of being 18 again. At least for me, if I had the self confidence and drive back then that I have now, I would have had a very different high school and college experience.

On focus, I had to go with the fact that I didn't aggressively pursue the semi-crazy girl I was hooking up with in my hometown who said that one of our mutual female friends wanted to join in next time. I had honestly just lost my virginity to this girl and hindsight 20-20 I think the concept of a threesome was so overwhelming that I actually came up with excuses to avoid dealing with it.

This falls under the things that almost 36 year old DannyMac wants to beat the shit out of 19 year old DannyMac for being such a pussy about it.

 

I definitely have some regrets about guys I had sex with, but I feel like my biggest regret is taking so long to take responsibility for my own sexual pleasure. I was too young/dumb/timid to speak up about what I liked or wanted, or even to touch myself. Wtf. I think I'd been sexually active for 2 years before I actually had an orgasm during sex. Thinking about that now bums me out so much.

 

I don't regret sleeping with any of the people I've slept with, even if the sex wasn't great, or the aftermath wasn't great. There are two guys I kind of should regret, but one of the stories is so hilarious that I'm glad it happened after all, and the other one was a guy that ended up being married and then turned into a huge asshole when I didn't want to keep sleeping with him thanks to that fact he forgot to mention beforehand. But I just can't seem to get too worked up over it. In the grand scheme of things, a few nasty texts don't end up being that big of a deal.

So, I think my biggest regret was a missed opportunity. I was visiting my friends in Boston, and we were going to this huge monthly gay dance party. An old friend of one of the friends was visiting and going to be joining us, and before he got to their apartment, he let us know that he had gotten out of the military a month or two earlier and was gay, and since Don't Ask Don't Tell had been repealed a few days before this, this was probably going to be an exciting night for him. He gets there, and he's super hot. We're all getting ready together and drinking, and he's awesome and being very flirtatious, but I kept assuming it was just the flirty-for-flirty's sake thing that gay guys sometimes do, or since he had been mostly in the closet until very recently that he just hadn't shaken the habit yet, or something.

Anyway, smash cut to the bar when he starts kissing me. I pull back, told him our friend had said he was gay. He says that if he's anything, he's bi. We continue making out for a while, and it is really, really good. And it's a huge ego boost for me because it's the first chance he could get to be openly and proudly anything-but-straight and there are a hundred gorgeous gay guys all tripping over themselves for even a glimmer of hope of being able to give him a blowjob in the bathroom and here he is with his hand up my dress. I was even perfectly fine with the option of being the last girl he slept with before realizing that he was fully gay. It would have been worth it. He asks me to go back to our friends' place. I go to tell the friend who I'm staying with that I"m leaving, he goes to tell them that we're leaving. Now, I hadn't had the greatest year that year and wasn't in the greatest of mental/emotional states, so then all of a sudden, while I was trying to find my friend, I started having a panic attack for no reason whatsoever and ran outside and hailed a cab and left without telling anyone. As soon as it passed, I immediately regretted it and was so pissed at myself. Years later I still feel that way. Whenever I go through my pictures and see the one I have of him I get disappointed all over again.

 

About four or five years ago I hooked up with a chick a couple of times and then pulled the pin on the relationship that was forming due to a couple of messed up things going on in life that I was struggling to deal with and a misread cue from her. I later found out that she was completely hooked on me and I missed out massively.

I regret this one most of all because the shit I was going through turned out to be a complete shitfight and not worth the time and effort I put into it and she was a pretty awesome chick.

 

Years ago I was out a shitty bar and let myself get picked up by a not very attractive fairly large woman who had to be ten years older than I was. We're walking back to her place and pass by a pile of trash someone had put out on the curb and she rummaged through it for a while until she found something she liked and carried it home.

When we get back to her dirty apartment I ducked into the bathroom and take a leak. When I get out she's sitting on the couch wearing a torn up white nightgown and eating out of a bowl of tuna salad.

I ducked out of there, but I sort of wish I could tell the story that I banged the tuna fish garbage woman.

 

I'm deeply offended by the title of this thread.

 

I can't say I have any major regrets in regards to past partners, although I do wish I had been slightly more discerning in my younger years.

The one I wish I could undo would be the guy who told me he was seeing someone after we had sex. He then proceeded to go apeshit on me when I wouldn't return his texts ("WE JUST FUCKED TWO DAYS AGO AND NOW YOU WON'T EVEN TALK TO ME?!?!?!?"). I know they weren't actually dating, but I am just not at all down with being the other lady in any circumstance.

I also had some terrible rebound sex two breakups ago that was pretty cringeworthy. His penis was crooked and there was no possible angle that would work. He also frequently asked to put it in my butt, as if that would make things any better.

And the guy who didn't know what the word "residential" meant. But he had an eight-pack and was good in bed, so I let that slide for a while.

 

Only thing I can think of growing up is passing on going home with a young lady who blew me in the backseat of a car, while I was wearing a Batman costume. And we can hardly call that a regret since I still got a blow job. I think I got rather lucky in that regard. I took any and all offers, and aside from some shitty sex here and there, I don't have any sexual regrets.

Now, more recently, with the memory still fresh in mind, my wife and I tag-teamed a cute little cake decorator we both work with. My wife set the whole thing up, I happily jumped on board, and now I can't even look her in the eyes at work anymore. It's awful. The sex was great, but it ruined what had the potential to be a solid work relationship, and turned it into a game of who can look away the fastest.

I will likely regret this one, quite deeply.

 

I know I've written about this before, but what the hell...

How about 2 years of sexual regret?

In the mid '80's playing in a bar band, ages 21-23. I'd give anything to have a do over of those 2 years with a clearer, more focused mind set. It was a 2 year long train wreck.

Basically our job was to go to some shit hole town and serve as entertainment for the locals for 5 nights. We weren't polished, or attractive, or even good. What we were was drunk, loud, and somewhat entertaining. We rolled into town and threw a party for a few nights and off we went to the next town.

We were basically a novelty...something new and different. And quite honestly the stories you've probably heard about drunk girls throwing themselves at musicians doesn't even come close to the reality. It's un-fucking real.

I honestly can't put a number to the number of girls I had sexual contact with during that time, it was a lot.

What I can describe is the aftermath, at least what I experienced.

First of all I became very jaded, I and my band mates were horrible people. We did things with these girls that normal folks wouldn't even dream of, and the girls went willingly along with every fucked up idea we could come up. Ever seen a girl fuck herself with a trout? I have. As I got older I realized that was someone's daughter, sister, niece, etc...and now she's a mother and quite possibly a grandmother. That shit keeps me awake at night sometimes, which I guess proves that I do still have a soul.

The second and possibly the worst fallout of those two years was that sex became very impersonal. It was just something to pass the time. The act lost all meaning. It wasn't a showing of love, affection, or even just lust. It became mechanical.

My ex that I was with through most of my 30's had a very high sex drive. Me? I'd rather watch a ballgame, go work on my car, whatever. I like to think that without those two years of fucked up shit that I participated in and witnessed I would've had a normal sex life, but I could be wrong.

I do know with some folks an experience like mine leads to wanting more sex and weirder shit, but it had the opposite effect on me.

It's amazing how different things look in the rear view mirror.

 

Can you elaborate and maybe tell us a few more stories. I'm getting a little aroused.

 

So who had a whole trout on hand?


I don't see a band carrying whole trouts around so the groupie must have brought it. Was this her groupie talent? Fucking seafood?


Let's see her fuck a flounder and I'll be impressed.

 

My biggest regret? That one's easy. I should be married right now. Instead, I haven't talked to her in three years.

 

I may have had long hair and wore make up, but I was still a redneck. I'd been fishing earlier that day and had 5 or 6 nice Brookies in the cooler that I planned to grill up. SOMEONE had the bright idea to grab a Brookie and have it talk to her pussy because they smelled so much alike...you know..."Mom? Is that you? I can smell you in there." One thing led to another and she fucked my trout. Or my trout fucked her. Whatever.

If I'd been a truly horrible person I would've cooked it up and had her eat it afterwards, but thankfully I think i ended up wandering off to the other motel room where the party was still going on.

I don't think I had sex with her later, at least I hope I didn't. I really don't know. All I really remember is watching the trout go in her lady parts and finding it simultaneously hilarious and disturbing.

I don't even know if I ever grilled up any of the trout. Now that I think about it, we didn't actually carry a grill with us. Not that that fact would've prevented me from starting a fire with some half baked plan of cooking fish.

My memories from that time are not exactly coherent or cohesive. They're more like random, scary snapshots that jump out when I least expect them.

 

I regret not fucking a girl with a trout.

This is why this site is so fucking awesome.