What is the Best or worst sexual encounter you have ever had and where was it?
IT can be absolutly any thing, and make sure u inclue details like if you were cheating etc, thanks
my best and worst sexual encounter kind of coincide, as it was my 1st time. my girlfriend (now ex girlfriend) was a little bit of well least to say slept around a little bit, and even with all the experience she still wasnt the best im sure it could have been.it was on Valintines day this year n i kinda had hoped 4 sex 2 b betta than it was so i was a little let down, she was just too loose. thats about it
Met her on aol. Got together the same night. Faked an orgasm so that she would leave my apartment. Do you really want more details . . .
I slept with a guy once who may or may not have been gay (I’m a girl). He was really attractive, and charming, so I was quite taken by him. Well, when we finally got down to business, he was like a child. He couldn’t stop giggling, he was totally childish about nudity, and he laughed at me when I tried to keep him “on task” :rolleyes:
When we finally did have sex, he thought it would be a good idea to shove his finger up my butt without warning. It ended there, and I never spoke to him again. Ewwww… Just thinking about it makes me feel dirty.
Okay, I’ll include my worst, as I hope that the best is yet to come…
During college, I had recently turned 21 and so, od ocurse, was out at the bars. I had already downed a few drinks and was up toward the front of the crowd around the stage. A cheesy (mostly)'80s cover band was playing and they had just started to play I Touch Myself. A very attractive young female in front of me backed up a little and we started to dance together. Soon she started to grind against me, and I certainly wasn’t objecting. It made for a pretty enjoyable couple of minutes, through to the end of the song (complete with several girls going on stage to compete in a fake orgasm contest in the middle).
After the song was over, this girl led me over toward the corner to an empty table. Before I realized what was happening, she had sat down and unzipped me! At this point, things were looking reall good, but then I felt something very unwanted…a bouncer had grabbed my shoulder from behind. We were told we’d have to leave. By the time I got myself tucked back in and zipped up to walk out, she had disappeared into the crowd and I couldn’t find her.
A very frustrating night!
Another worst:
In the middle of the act the guy pushed me away, grabbed both of his legs behind the knees, pulled his knees up by his head, and panted, “I dare you to lick my a------!” Sorry, but um…no? I should have stopped there, as it was all downhill from that point.
He did end up with the nickname “Doubledare”. No idea how that happened… 
Hm.
“Best”… durned if I could decide. At best, I could list “Best Sexual Experiences with Specific Women.”
Worst? Hands down, the Married Woman.
We’d met while clubhopping, once, and wound up at her place, and had a wonderful time. She’d invited me back once, too, during the day, and we’d had a wonderful time then, too, although I kind of wondered about the toys in the downstairs area, and the toolbox and drill press in the garage, the golf clubs, and so on…
…and she told me she was recently divorced. The drill press belonged to her ex; she’d gotten it in the settlement, due to its money value, and she hadn’t gotten around to selling it. She played golf. The kids were her sister’s, and she often babysat for the poor, hardworking single woman, which meant a fair number of toys tended to wind up at Auntie’s.
I was all of 22 at the time, and anxious to believe it. Didn’t bother me a bit. Swallowed it all, hook line and sinker.
Until our third rendezvous, once again at midday, in which we were thrashing amid the sheets… in the upstairs bedroom… when a car door was heard to slam, in the driveway.
“Ohmyghod, my husband’s home!”
“…what?”
“Get dressed! Get dressed! Get OUT!”
The front door slammed, and I heard a good-sized person trotting up the stairs at a brisk clip. I didn’t even stop to get my underwear on. I snatched up all my clothes and went out the upstairs window, and onto the awning. As I edged around the corner of the house, trying to get to a handy tree, I heard voices coming out the bedroom window I’d just scootled out of. As I approached the tree, I heard the window slam shut.
It occurred to me that if he suspected something was up, his next move would be to run downstairs and hunt for me from there. Possibly with a ranged weapon. I froze for a minute. If I swung down, he might well catch me flatfooted in his back yard, naked as a jaybird, holding a wad of clothes. On the other hand, if I didn’t, he’d be an idiot not to check up on the roof. Whatthehell was I gonna DO?
I jumped to the tree, grabbed a limb, almost fell, and dropped my clothes. I swung down, grabbed my clothes, and ran like hell to the back privacy fence and jumped over it, praying all the while that no one was holding a barbecue back there, or had children sitting on a swingset who would then tell Mommy and Daddy about the funny man who ran through the back yard, naked…
It was an alley. Nothing but fences and trash cans. I stopped to jump into my pants, get into my shirt, stuff my briefs in my pockets. I’d remembered my shoes, but completely forgotten my socks. Oh, well. On with the shoes, and I casually sauntered down to the end of the alley, and found my car, parked next to the Married Woman’s house, right where I’d left it.
No sign of Hubbins.
I jumped in my car and beat feet outta there…
Moral Of The Story: Incomplete coitus and mortal terror do not mix well.
Found out later she’d told me SOME truth – she did have kids, but they were with Daddy, and they weren’t exactly divorced, but in the “trial separation” phase – and she wasn’t so much worried about our safety, as she was worried about what HIS lawyer might be able to do with the knowledge that she was screwing studly young college students in THEIR house while Hubbins was supporting her financially, *and * raising their children in an apartment across town…
I declined her offer to renew the relationship. Somehow, once a woman has lied to me, I’m disinclined to get back into a position of trust again.
Even for a booty call.
All of these worst sex stories, someone’s gotta post a good one!
Here’s a story for you all. It was this past Thanksgiving at the Hyatt in a major city. Big deal, sex in a hotel, right? Well I went there to visit the doper who converted me to the SDMB actually (not how we met though). Anyways, he was staying with a group of people there so there was no way having sex in the room was an option. We were wandering around the hotel just checking things out when we found this long hallway on one of the lower levels. There were a bunch of shops down there, convience store, hair salon, etc. It was about 2am or so, and we figured there wouldn’t really be anyone down there. We started making out in the hallway, but realized we weren’t as alone as we thought. Some people must have been working really late because about three people had walked past in the last 10-15 minutes. We just stopped and then continuted after they were on their way. Eventually our hormones got the best of us and we ended up having sex right there. Not behind one of the huge fake potted plants, not in one of the doorways, right there in the hallway up against the wall! All memories of the people that had just walked by were long gone, and luckily those people were too because no one else came by, unless we were just too busy to notice. And it was really good sex, especially considering it was the first time we had sex together, and we had to do it standing in the hallway, not a very easy position. The thought of someone walking by increased the intensity I’m sure, my first time having sex in public too, gonna be hard to top that one! Then the afterthought of the security cameras positioned in every corner as we gathered ourselves and headed back upstairs. Guess the security guys had a good show that night, oops! :eek: OhFace on camera!
Not going to go into my worst, but my best was with irishfella.
It was after I had told him all the gory details of my past, we cried a lot, and then we told each other how much we were in love, and had the kind of amazing, loving sex that leaves you tired, weepy and shaking afterwards.
And that’s why I’m living with him 2 1/2 years later.
I can’t remember if it was an eye doctor’s chair or a dentist’s chair but it was one of those types of chairs…
She was an older woman (at the time younger than I am now), with a lot of knowledge and a great open sexual attitude (IMO, of course).
She liked to do it outdoors, too. Indoors, outdoors, in a bed, in a creek, on the side of a mountain, wherever.
She wanted me to do it with her in my pickup truck but I couldn’t find a good place to pull over so she just took care of herself.
I spent 3 weeks with her (and a few others) rafting through the Grand Canyon. We came out the other side a bit worse for wear but we did do it in some nice places.
She moved to Alaska shortly thereafter.
You know, I was just thinking about this event the other day.
I was visiting a gentleman I was… umm… well, I don’t know what the hell we were doing. Not important. Anyway, we were snuggled on the couch just sort of chatting. This was early in the I-don’t-know-what-we-were-doing part of the relationship, and speaking from my perspective it was hard as hell for me to keep my hands off him. I really, really, really wanted to fool around, but he was sickly at the time and obviously no one wants to fool around when they’re sickly. So finally I said “I need to go before I forget you’re sick” to which he replied “You need to go before I don’t care anymore.” Mmph.
We made it to the front door. It was getting ready to storm outside, and there was the most wonderful cool breeze, and thunder, and that electrical feeling that comes just before the bottom falls out of the sky, and we stood there for a minute in the open doorway, just admiring the weather. And then… I don’t know which one of us went for the fastenings of his pants first, but the next thing I knew I was on my knees in front of him.
Could’ve stayed there forever. ::insert misty sentimental smilie here::
My worst:
I was with my ex-girlfriend and we had only been together for a few weeks. We had consumed a few alcoholic drinks but neither of us were drunk. We wind up in my bed. We start having sex. She’s on top. A few minutes in she just stops and has this horribly pale look on her face. She says she feels sick and jumps off me and runs into the bathroom where she proceeds to vomit.
She comes back from the bathroom very apologetic. And says she want to finish. But she wants me to be on top. Not a minute in she gets the same look on her face and I have to get off her so she can run back into the bathroom and vomit some more.
At this point I’m ready to give up. I was horny as hell but she was too sick. So, I decided that we would just go to bed. She felt really bad. She said she would try again if I wanted. But I told her she didn’t have to.
She ended up finishing me off about 20 minutes later. She was a real trooper.
It sucked a little to have somebody stop right in the middle and run away from me. It was just weird. I felt bad for her mostly.
-Shaggarito
Worst?
Well, I had someone fall asleep once. That wasn’t much fun!
Best? Hmmmmm. 
Well, there was this time two weeks ago… Hurt to sit for a few days, but in a very nice way. And now, seeing him again in just a few more days to see what we can get up to this time around!
Motto: Sleep with a Doper, you’ll be glad you did. (someone needs to make that a t-shirt: I’d buy one)
Best and worst in a way.
Years ago I went to a topless bar which wasn’t too out of the ordinary for me at the time.
Normally, I DON’T buy lap dances but this one particular girl talked me into it because I was pretty drunk and pretty agreeable at the time. While she was giving me my table dance she noticed that the little soldier was standing at attention. (this because she was grinding her ass into my lap area.)
Anyway, she was like “arrre yew harrd?” (she had a german accent which only added to the turn on) to which I sheepishly responded “yeah sorry” she then told me “Don’t worry about it. I love it.” after the first lap dance was over I handed her the twenty bucks for the dance; she then starts to give me another one. To which I promptly tried to stop her but she wouldn’t let me, she said "Dis one iz for frreee.)
I’m not sure how this woman managed to pull this off, but with one fail swoop this lady undid my pants, pulled out the ol’ johnson, pulled her G-string aside and put me in her, then just went to town. The whole thing couldn’t have lasted longer than five or seven minutes but man was it HOT! Yet probably one of the sleaziest things I’ve done to date. (hence the worst part)
My best was with my wife. It was a glorious fall day, and our daughter, then 3, was at her cutest and most charming. I looked over at my wife, and suggested, “Let’s start another one tonight”. She agreed enthusiastically.
It didn’t happen that night, or for quite a while after that, but it was the best I ever had before or since.
It made me wonder if the Catholics might not be onto something…
“Is this it?.. Is this it?..”
[sub]That was the worst, in case that wasn’t clear. Thankfully.[/sub]
Finally getting to do it with the girl I chased through high school. You would think this would be a story about a great sexual encounter and that’s just what I thought when it started.
I got together with Faye 7 or 8 years after we graduated. We met at the mall by accident and she invited me over for dinner. Later, after a hot make out session and her teasing me with some very good oral (she didn’t want me to do her), we moved to the floor to finish the grand deed. OMG, when I entered her there was nothing but a void. Seriously, nothing there.
Now I’ll be the first to admit that I’m not huge, but ol “Spike” ain’t a teenie weenie either. It was like sticking my pud into a hole in basketball, or through a slit in a sheet. I couldn’t feel a thing and, believe me, this was the one and only time in 40 years this has ever happened. Anyway, I did my best and tried for a while but there wasn’t enough sensation to keep me hard. During that time she either faked an orgasm, or it was a hell of a lot better for her than it was for me. She realized I was getting soft and asked what was wrong. What? What’s wrong? All those old joke lines like, “strap a board to my ass to keep me from falling in”, came to rushing into my mind, but I lied and told her that I was just so overwhelmed at finally being with her that I couldn’t concentrate.
Having my fantasy crushed, and then not being able to finish was bad. But the clincher was her asking me not to tell any of our old classmates that we had met and had a date. WTF? When she called me a few days later she was surprised, and then angry, when I told her that I wasn’t interested in seeing her again.
My best and worst were consecutive, though on different continents, some time (er, years) apart, and, thankfully, with different women.
Worst: After a session with my (now ex-) wife, she grumbled, “I hope you enjoyed that, because I didn’t.” Not the end of our marriage, more like the last nail in the coffin.
Did I mention this was on our second anniversary?
Best: Hmmmmm. Well, there was this time two weeks ago… Hurt in some places for a few days, but in a very nice way. And now, seeing her again in just a few more days to see what we can get up to this time around!
Any similarity to any posts above is entirely intentional! 
My worst experiences didn’t involve bad sex, really. They involved bad circumstances.
It was the girl to whom I lost my virginity when I was 20. The first time was about what you’d expect for a first time, though I think it was kind of a bonus to be losing my virginity to a redhead on St. Patrick’s Day!
The trouble started the second time. I drove us way the hell up a road into the woods, where we would be gauranteed some privacy. We got busy in the front seat, and started with a hot makeout session. Things proceeded quite nicely to the point where I was still sitting behind the wheel, and she was going down on me. My first blowjob, and I was lovin’ it.
That was when the headlights and spotlight suddenly blazed through my rear window. It didn’t take long for the nice policeman to realize what was going on. He explained that he didn’t see anybody in the car (we had both been below the level of the seatback) and had to stop and check it out. Then he very politely suggested that there were more appropriate locations for engaging in “this kind of thing” and suggested that we move along. We did. Unfortunately, neither of us was in the mood anymore after that.
A couple weeks later we tried again. It was her 20th birthday. She had obtained a bottle of hooch, and we were going to do the deed at her place, because her parents were out of town. We pulled up in front of her house. There on the sidewalk out front was a young man standing next to a motorcycle. “Oh shit!” my girlfriend said, “it’s my ex-boyfriend!” It seems that a few weeks before she got together with me, she had invited him to come visit on her birthday, but he had declined. Obviously he had changed his mind, however, and there he was.
We decided to make the best of it, and invited him in (he had come all the way from out of town, and she didn’t want to just tell him to take off. They had parted on good terms, so there was no hostility.) We figured he’d hang around for a bit, then leave on his own. He didn’t. He hung around and hung around. Meanwhile, we were passing the bottle around and getting a bit drunk. After a couple hours, she and I decided we weren’t going to wait any longer for him to leave, and we headed upstairs to her room, leaving the ex sitting by himself. Yeah, tacky. But hey, we were young and horny!
The sex was great - she was pretty experienced, and we tried all sorts of things. After we finished, we found ourselves sitting naked in the middle of her bedroom floor, basking in the afterglow. Then we heard her doorknob rattle and her door swung open. She dove behind a piece of furniture, and I grabbed something to cover myself.
Her older brother, who must have come home while we were getting busy, was standing there in the doorway with a look of utter disdain on his face. He looked at her and said, “You have no class! You have NO class!” Then he left, closing the door behind him. We got dressed, and lingered a bit in her room. It was pretty clear that I should probably leave at this point. We finally worked up the nerve to go back downstairs, where her ex was still sitting where we’d left him, believe it or not. He was trying hard not to look at us. Meanwhile, her brother sat across from him glaring at both of us. We had to walk past both of them to get to the front door.
After that, she and I mutually agreed that we just weren’t meant to be.
I’m sure you can find all the titilating information you need if you check your junk e-mail.
Lockdown.