What's the worst sex you ever had and what made it #1 on your bad list?

Easy. The very first time. Worst. All awkward and clumsy .. but then again I’m a medical marvel having only slept with two people in my whole life.. so what do I know?

My worst sex experience is…being a teenager with raging hormones. At this age, everything is sexual, only with the actual satisfying bits indefinately suspended.

The second guy I ever had sex with. It was jackrabbit sex, like that Sex and the City episode…BAM BAM BAM BAM BAM BAM BAM!!

I was young, so of course I didn’t say anything. Thankfully we only lasted three months.

Guy who was too vapid to tell me he was too vapid to want to do it, let me
get in his bed and then nothing happened. Waste of my valuable time.

I dated a girl who was a major nympho, however didn’t actually seem to enjoy sex. I wasn’t worried in the ego sense but definitely wondered what was up. This one time during sex she stared crying hysterically (which has to be one of the most awkward situations) and later told me she had been molested as a child. It all made sense. The sex was bad though. It always seemed totally forced. She’d make me pull the car over, public bathrooms, etc. This would have been cool if she was into it but something always seemed off. I’m really not insensitive, I just wish she would have told me what was up in the beginning instead of weirding me out.

@peedub: She might not have told you if she hadn’t put herself through those faux sexual experiences first. Because she might not have exactly known.
I like you, I trust you, and I don’t even know what you look like. I believe that if I had a hidden problem I might be tempted to take it to you even if I were unaware of it. Know what I mean? Maybe you were the catalyst for some hard, hard realizations, just because you were safe enough.
Just a thought.

well…. my parents came home…. when i was 22… they said they’d be in Oklahoma!!

@susanc That’s a good point. I thought we were close enough, having been friends for many years prior. She’s also extremely intelligent and, at least I thought, knows herself well. But yeah, maybe she was unaware to some extent.

I felt bad and it was hard because, often, there was nothing I could do to cheer her up or ‘make things better.’

When the goat kicked me. Got me right in the nads!

@peedub, were you wearing that particular bear mask when you tried to cheer her up?
no, really, it wasn’t up to you, honey

I had sex with a woman once and wondered half way through if she still had a pulse. It was sort of like having sex with a mannequin that was alive but unresponsive. Leading up to the sex, she seemed like a pretty normal lady. Once was more than enough with this person. The worse part was, for her anyway, my performance being great and her getting nothing from it.

@Sakata. Your story in your question’s details had me laughing my ass off. Hammerfist to the forehead, wow. And she liked it too! Crazy.

@Bluefreedom, that made me think of the Twilight Zone episode, “After Hours.”

@susanc Actually, I was wearing something like this. I think I really freaked her out.

@AlfredaPrufrock. Great episode too and quite creepy. Good comparison.

The first time always sucks – The second time even worse, she was on top and very drunk and barfed on me.

@antimatter. That must have been terrible. I can’t stand the sight or smell of vomit. I would have lost it.

It cured me from sex for a few weeks

Ah man, let me first explain that I really enjoy kissing and cuddling. Apparently, my joy from those actions led to a girl thinking I was into her when I really just wanted to have a little make out session. Well, it started leading to things and the kicker was, she had a boyfriend. About two minutes into the deed, her boyfriend was all I could think about because I’m not the type that could cheat on someone and so I was just thinking how he would feel over this. It only lasted about 3 minutes and we both wished it had never happened.

@Sakata- Hammerfist, as in you bopped her head down like of those crazy games at Chuck E Cheese? Did she stick around for more your antics? Head bouncing of the floor really paints a picture, but then again, so does all that Beam.

I’ve never understood the whole biting thing, bear head or not.

@peedub. Are you talking about the Whack-A-Mole game? I’m trying to draw some kind of comparison while trying not to fall out of my seat laughing!!

@Bluefreedom Haha! yes! I was just wondering what it was called, thanks.

Essentially those little creepers are trying to bite you. You have send them back into their holes.

No, I sat at the kitchen table and waited on my buddy to get done fucking “crazy chick’s” roommate. When they came out they saw me sitting at the table (pretty much gone at that point) and the roommate said, “You look like shit. What, did she fuck your brains out?” Her insensitivity toward her crazy-ass friend pissed me off for some reason so I snapped on her.
I looked at my watch and said, “No she didn’t ‘fuck my brains out.’ I’ve been up for 73 hours straight with nothing but alcohol and nicotine to keep me running. I’m tired. I’m drunk. I’m hungry. I’m pissed off. I’m leaving.” I grabbed my jug of Jim Beam (sure it was HUGE but it’s got a handle so that makes it portable, right?) and walked out.

By “hammerfist” I mean: Make a fist. Swing your hand in a downward, chopping motion. The meaty part of your hand on the side of your pinky finger should strike your intended target which was, in my case, a girls forehead.

Haha, what a story.

That’s what I imagined. I call it a BOP on the head.

@antimatter You win.

@emt333 That was a joke, right? Right?

Back than it was not funny but now when telling that story I crack up every time.

More people need to share. Hell, make something up if ya have to. Not like anyone’s gonna know.

lol

@emt333, you don’t have to explain, but you did volunteer it. It’s hard to know how to take it without knowing if you were, say, a 7-year-old girl or a 17-year-old boy with a 10-year-old cousin. Big difference.

Well like the third time i ever had sex my mom walked in on me which was very awkward for sure. she told us to meet her downstairs “to talk”. my gf started crying and i wasnt sure if i was supposed to finish up or what. lol

but even more awkward than that i think wasn’t even my own sexual encounter but of from a friend of mine. I had just been friends with this guy a few months when I was 15 (and a virgin at that point. id had blowjobs and whatnot but i was still pretty sexually inexperienced) and i was went over his house to meet up with him, walked in the front door (he had a very open house), and went up to his room where the door was closed.

i knocked, he said come in, and he is fucking this chick….in the ass. it gets weirder though. he tells me to check out her tits and i’m like yeaaah they’re real nice. and he tells me to feel them and shes like agreeing with him that i should touch them so i grab on them for a second agree they are very nice tits and leave the room to wait downstairs in his tv room….now THAT SHIT was awkkwaaarrrrddd lmao

ps. the same dude used to take pics and videos his girlfriends and other girls and show them to me all the time. he became and still is one of my best friends hahahaha.

I was 19 and had been dating this guy for a bit. We went to his apartment one night and got busy. At first, I couldn’t tell if he was actually in me. He was so small. Unnaturally small. When he was about to finish, he started screaming like Mariah Carey. I was so embarrassed because I knew that when I had to leave his room, I would face his roommates. I guess they were used to his singing though.

alcohol + sex = “tellar experience.”

Glad to know that least that hasn’t changed in the last 30 years…

worst sex i ever had was with the rabid badger that had herpes

One time me and some guy were on a sink and we ended up breaking it and the pipes bursted and we got all wet.

@adri027 that sounds hot what are you complaining about?

The worst thing I can think of (and this absolutely pales in comparison to everyone else’s) is one time we were we were alone in the house, and we were in the middle of things, both really enjoying it, everything was quite pleasurable, when my roommate comes home having a fight with someone on the phone. We could hear her slam the front door, and each of her stomping footsteps, and all her shouts and sobs. I guess she thought she was alone in the house too. I still don’t know what she was so upset about that day, but I’m still pissed. After that it wasn’t the same. We were trying to be quiet, we just kept hearing her voice – it completely killed the mood. I can’t remember if we even finished.

It was my sophomore year in college and we went on a road trip to the University of Tennessee, which was home to many of my friends from high school. A couple of these old friends were in a fraternity that was throwing their annual “pimps and hoes” party. I love theme parties so I got a little excited and started drinking way too early. There was a badass hip hop band shaking things up, enticing everyone to start an all out bump and grind fest. I join in and find myself on the dance floor making out with this chick from high school that I never really noticed until that night (it was probably the dark heavy eye shadow and black leather that did it.) We leave the party and stumble back to her dorm room. She had some “molly” which I was not a stranger to and I had some grass, so we smoked, popped, and got naked. It was up until this point one of the greatest nights of my life and amazingly, as shitfaced as I was, this night is a bizarre yet vivid memory that was soundtracked by the Rusted Root song Send Me On My Way which she must have had on repeat. The music was so powerful and we started going at it to the beat of the song. We went through a couple of the standard positions and somehow got to the point where she decided to stick her finger in my ass without giving me fair warning and I was (and still am) very inexperienced in this department so my natural reflexes took over and I shit all over her chest. There wasn’t much that came out, but it was enough that embarrassed me and sent me scurrying to the bathroom to clean up. I grabbed two towels, wiped real quickly and went back out with the other one for her. When I walked out, still naked, I see her on the bed standing tall on her knees rubbing my shit all over her chest with her head laid back making this incredibly memorable moan. Being as wasted as I was my true instincts luckily kicked in and I grabbed my pimp coat and got out of there. I haven’t seen her since, but this fall is my ten year reunion and I’m kind of hoping to see her.

@tennesseejac Awesome. But why did you leave??

I would be freaked out as well if some one gets an orgasm from my shit!

With woman like that today it’s the finger up your ass, tomorrow it’s something else…

@tennesseejac. That is certainly one of the most intriguing yet disturbing experiences I’ve heard yet about an unusual sexual situation. Wow.

yeah, shit and sex dont mix for me.
plus, she wasnt the best looking girl, i would like to think i would have had the same reaction even if she was a “10”

Yeah, I totally agree, but you coulda cleaned her up, and probably would have gotten real interesting from there…..

@tb1570 I think you got some crazy ideas about sex. I think sex should be joy full experience for both parties to enjoy.

@tennesseejac My eyebrows are in the air! I’ve heard of weird, but that’s pretty over the top!

Sex with a friend whom I could not really see as a girlfriend. We tried to make things work, but when it came down to sex, it just felt wrong. She was a beautiful girl, had an amazing body and did everything right in theory, but to me it just felt like something we simply shouldn’t be doing.
I dated another friend some months later and that was really amazing sex. So it’s just a question of “clicking” I guess.

First time. We weren’t sure when his parents were going to get home, so we did it in the bathroom – thinking the first one dressed would be able to run out and pretend they weren’t in there, and the slowest to dress would just be “in the bathroom,” ya know? Genius alibi.

There’s no really comfortable way to do this in a bathroom, so we tried the ever popular “over the tub” position. Being young and inexperienced and very eager, he got behind and… let’s just say that tab A went into the wrong slot. The very, very wrong slot. When you’re not prepared for that (and trust me, I wasn’t), the pain can be overwhelming.

And also overwhelming is the pain response, which in this case involved me lashing back at him, chipping his tooth.

Yea. It was pretty bad.

When my boyfriend dislocated his shoulder in the midst of our fun and I had to take him to the hospital with his shirt off, in the middle of the night. (He was doing pushups, we said.)

…well you were not lying, juniper. He really was doing pushups ;)

I thought I was interested; I’d been doing the human version of doggy butt sniffing for months. I don’t know what she finally agreed. She had this loft bed, and we were trying to do the deed (I think, without foreplay, since she didn’t seem to want to kiss), but she just lay there like a dead fish. I had a girlfriend, and was feeling a little like I shouldn’t be doing this. So, for the only first time of the night that I remember, I went soft, apologized, put on my clothes and left.

Of course, my first time is a close second.

Um. Why are we answering this question?

My almost-first. I didn’t want him to be my first becuase I didn’t like him. But I was going to go through with it, after his clumsy fumbling, his awful kissing and his inconsideration of me as a person outside the bedroom, because, dammit, someone at the age I was at the time HAD to have a boyfriend, no matter what, and SHOULD HAVE done it already.

Unfortunately for him, my body said, “no.” I clamped shut.

My real first time a few years later I wish on everyone, even though we ended up breaking up too – and he was years younger than me! :)

She stopped to listen to then answer a phone call from her exboyfriend.

He was so pretty that when he got into a dark room he looked like a girl. Freaked me out. Poor guy. I was very young and I just freaked and said, “I can’t do this,” No explination. One of those regrets for being mean.

Stories like these make me never want to have sex again. I do not want to be that girl. God, there’s so much judging to do when it comes to sex.

@onesecondregrets: that’s a really good point. It makes sex seem like a sport or a game. The thing is, sex must be learned, somehow. Maybe people feel like at the beginning of the relationship, it might not even be a relationship yet, so facility with sex is important. Maybe no one really wants to teach someone else how to do it. (I once declined a chance to deflower a partner. I’d done it once, and really didn’t want to do it again. Later on, after someone else did the deed, we had some good times!) It seems to me that if the feelings are there, then the sex is fine.

It’s like anything else. People ride tricycles before ten-speeds. I think these might just be stories about how we fell off the tricycle and skinned our knees.

Good writing flows from the heart like a dance as well, but people still need to learn how by keeping journals, editing, etc.

@antimatter “Joyful” is a relative term. But, for the record, I was not speaking of my personal tastes. Although I have no problems w/ many forms of “kinkiness,” fecal matter has never entered in to my sexual realm! I was merely implying that that could’ve been one of those once in a lifetime experiences! And, if you’ll notice, I did say “clean her up!”

Lastly, my first time was absolutely wonderful! Is that really so unusual??

Daloon, I couldn’t agree with you more on that last line. When you don’t have feelings for someone, or care about them.. you are 10x more likely to judge them with sex, rather than accept their bad sex-qualities. I mean I’ve had sex with people I don’t have feelings for and those experiences could easily be one of these stories, y’know? But then there are people I’ve been in relationships with and I think about being judged 10x less with those people (when concerning sex) than the ones that were mainly based on just sex. Trust is a big ish when it comes down to it I guess. Or something. Who knows. I just know my views on sex these days make me feel 1) like a prude 2) like I’m 50 years behind the time 3) boring as fuck 4) something is wrong with me. But I can’t help it.

@onesecondregrets I don’t think you should let your feelings affect the way you feel about yourself. And I certainly would be willing to bet that many more people agree w/ you, and daloon, and ME!, than the modern media and “entertainment” industries might have you believe! Lastly, not that you’re seeking validation or sympathy, but I think it’s also worth noting that many, many guys are looking for women like you, and are not at all turned on by what seems to be the prevelant sexual attitudes these days!

The sex was good, but the location was bad… we had a hotel room and there was a baby next door that wouldn’t stop crying. Talk about a mood killer.

I had a guy stop about two minutes in and say “I have to get going. I have to get up in the morning.” This was the second time we tried to have sex… the first time, he tried and failed twice.

I hooked up once with a guy whose junk – NO JOKE – resembled a pencil. It was a normal length, but it was unnaturally skinny. It freaked me out A LOT.

I have a few..

the first that comes to mind is back when I was 18 and I hooked up with a client, who, incidentally, I’d never met in person before. Stupid. I can’t really say what I’d like to without being judged, but the easiest way to put it is that the texture of his hair, which didn’t end with his head, was so nasty. SO SO NASTY. I get grossed out by excessive body hair anyway, but this was like steel wool all over me. All. Over.

Another is right after my last breakup, and I was vulnerable and depressed… I met someone, we hooked up. First, he laid on top of me and he was a big guy, and I had to fight to breathe. Then, after it was done, he said, “Do you know anybody with HIV?” and I said no, and I said “well, you do now.” I’d never been so terrified in my life… I literally threw my clothes on and ran out of his house. I called him 2 weeks later to tell him I’d been tested and that it was positive… it felt good, I have to be honest.

Then, during the same breakup, I hooked up with a guy I worked with.. we were really good friends, and not only was he fat, which didn’t bother me, but he was small. Combined with his weight, it was… um… hard to get to. And he couldn’t keep it hard! You know something… there’s a lot I can’t do. Sex is definitely not on that list. I’m good at it. I pulled out all my tricks. UGH. We were never the same after that.

@tb1570…Haha, just knowing that 2 other people share similiar ideas about it is comforting, so thank you. My last comments kind of hint at seeking validation, that I’m not crazy so it’s okay. And your last comment- actually your whole response definitely made me feel a little more at ease and less weird for feeling the way I do about sex. So overall, thank you haha. :).

@evelyns_pet_zebra Wait a minute…. You had sex with a goat????

@emt333 well it killed the mood so it sucked.

@onesecondregrets My pleasure.

@onesecondregrets and @tb1570: Clearly there are a lot of people who engage in sex almost as sport. I’m sure this has happened throughout history—one tends to think of the ancient Romans this way.

Then there was a phase, associated with Queen Victoria, where Americans grew very prudish. To some degree, I believe we are still being influenced by that time. I’m not opposed to having multiple partners or a lot of partners. However, I do think that one should have strong connection with those partners. It’s just not what it could be, otherwise, and I hate to say it cheapens it, because I’m not one of those save sex for marriage folks, but I do think it lessens it and kind of makes it pointless. It’s mutual masturbation, which, I grant, is more fun that solo masturbation, but still it’s only about scratching an itch.

Now I haven’t always had a strong connection with a partner, but for the most part, I have. In fact, I tend to believe I love my partner, although some of that is fooling myself. I do know that when I’m happy with my sex life, I have no desire for anyone else, and when I’m really unhappy, my eye roves, and I get into trouble. I’m glad to be able to say that I became very, very happy last night!

[edit] oops, wrong question, but what the heck, it seems more appropriate here.

Daloon got laid!

@daloon – hopefully it wasn’t the worst sex ever, though! ;)

Woohoo! Nope, Laureth, it was darn good!

@tennesseejac, something tells that your partner may have found another girl and a “cup.”

@onesecondregrets It’s nice to now that this question actually helped someone in some way. Didn’t expect that to happen. Just like I didn’t expect this question to have 67 responses. I honestly thought it would be removed lol

@Sakata; No no, the mods are too full of wise for that. And the collective is apparently blissfully full of shamelessness

@Sakata…not only was it helpful to someone, but it was also the catalyst for my sex question that surprisingly hasn’t been removed either! Haha, go us.

@bluefreedom – I’m still laughing at the “wondering if she had a pulse” quip!

@cak. That was a long night, let me tell you. :o)

@blue – you couldn’t fake an acute case of Ebola….or something? That whole heat the thermometer up and fake a high temp? Bird Flu? Chicken Pox??

@daloon I don’t think anyone would argue that having sex, making love, with someone you truly care about, truly have a connection with, is heads & tails (excuse the pun) above any other form of “mutual masturbation.” Those of you who are lucky enough to be able to do so whenever you like should count your blessings.

@poofandmook with such horrible experiences, I think if I was you, I’d swear off sex. well, maybe not

@onesecondregrets Yea, I noticed. Even commented on it lol

Not sure about everyone else who’s posted but the 2 “worst sex” stories I posted in the description aren’t the only ones. Just didn’t feel like dropping ALL of ‘em on here. I’m not sure how to classify the actual worst sexual experience though.

@cak. I wasn’t that creative back then, I guess. :o)

ack! The 2nd experience I posted about, it should’ve said “He said ‘well you do now’” it doesn’t make any sense the way I wrote it. Ugh.

@scamp well, not exactly, getting kicked in the nads sort of killed the mood and made me limp for a few days. I learned that from that day forward, when the thought of goat sex turns me on, I’m only having sex with DEAD goats.

@poofandmook – That’s… I have no words. People can be mean. :|

@scamp that video you referred earlier is the second grossest thing Ive ever seen.

Well my ex gf and I broke up. And she came around one day after I finished work. Started having sex and it was so awesome and out of nowhere she started crying. It was the most awkward, embarrassing moment of my life. I didn’t know whether to stop or keep going. I stopped and put my clothes on and we ended up talking for a bit.
But picture yourself naked with a girl ontop of you, and then just lay on ur chest balling there eyes out with it all in and everything. Fucking weird .

Sometimes women cry during sex. It’s not that weird. They feel emotions very strongly and are so vulnerable and it overwhelms them, and they cry. It’s not a bad thing. It’s nothing to freak out about. Of course, I learned this the hard way. My wife is a crier. But now I take it as a sign that I’ve done something very well.

I’m just surprised that no woman or man has said something like this yet. It’s not like it’s any great secret. People cry when they are very happy as well as crying when they are very upset. Usually, all they want is to be held. We (men) don’t have to fix them. When women cry with us, sometimes it’s because they are hurt or angry, but often it’s because they feel safe and loved enough that they can be totally vulnerable.

@daloon damn…...too bad all men aren’t as insightful & understanding as you are. You’ve got it together.

@daloon You are very right. I think that I may have cried at least once. I cry very easily, even at joyous occasions. When I cried, I felt very safe and loved. It was a good cry

@daloon – i will remember that one. thanks buddy (Y)

I was dating a guy in college and he had a mirror behind his bed. One time we were in the middle of sex, and I looked up and noticed that he was looking at himself and flexing in the mirror. That was a deal-breaker and he got dumped the next day.

Another college boyfriend and I had a little too much to drink, but we gave it a shot anyway. In the middle of it, literally, he fell asleep on top of me.

I’ve got at least a few other of these stories . . .

@daloon Read the beginning of my description lol

@figbash The flexing, that’s hilarious!
I also had the too much to drink and fell asleep, but luckily I was on top.

Yeah, I’ve totally been the one to fall asleep before as well. Luckily it happens pretty much exclusively in the “side-to-side” position so no one gets crushed. (I don’t know if other people call it that, we kind of made that name up). It’s extraordinarily similar to the position I like to sleep in, spooning all cuddled up, in front of him, with his arms around me. It’s just…slightly….different…

@La_chica_gomela That position is the best for a pregnant woman. It is different, but in an awesome sort of way.

It’s a tossup.. the first was a guy I randomly hooked up with years and years ago. His idea of foreplay was to scoot up and stick his penis in my face to indicate he wanted me to go down on him. He was small, too. Then, intercourse consisted of like 5 minutes of jackrabbiting and then he got up to shower. I was like.. seriously, that’s it??

The second was a woman who had like sexual ADD. She’d start doing something and just when I’d start to get into it, she’d switch to doing something completely different. No orgasms to be had here, plus it was just really weird.

Ladies, I think some of us have been trumped in the bad sex department.

I have not seen the equal for gents.

@aprilsimnel: You have provided me with hours upon hours of amusement, no lie. I am definitely going to submit some of my favorite stories….

@tennesseejac Luckily, I never saw the video, but heard enough about it to know why I didn’t want to!! Your post kind of reminded me of it tho….wow!I’d hate to know what the grossest thing is for you if that came in second… you poor guy!

evelyns_pet_zebra Please tell me you are kidding..no pun intended!

To all of those people that are worried I may have been sexually intimate with those of the goat persuasion, yes I am kidding. I have never had the opportunity to experience cross-species dating. But you know, I’ve gotten some lascivious looks from a goat or two in the past. maybe I need to open up my own petting zoo.

Hey, evelyn, don’t kid yourself.

@Jayne, nice pun.

I really think I can’t possibly choose just one. There are too many awful experiences to pick from.
Whoa, that makes me sound whorish. I’m not, I’ve just had a lot of bad sex lol

@casheroo We’ll consider you a non-whore if you tell us at least one bad experience. Promise! :)

haha.
Well, I’d say the guy that wanted me to call him daddy, and referred to himself as such while in the middle of the act..was by far, the creepiest. He also used babytalk…during sex. I kid you not.

Oh, and this one always kills me. In the middle of a threesome with two men, they start spanking each other. I then slowly realize that they probably wanted me out of the equation, but were both “straight”. Yeah, okay.

@casheroo lol I had to ask! :P

What;s wrong w/ liking being called “daddy??????”

@tb1570 it was the babytalk that was the most disturbing part, add that he wanted to be called “daddy”...the combination is what made it horrible.

@casheroo OK, baby talk and “daddy” together I can see, but there’s nothing wrong w/ “daddy” by itself, right? RIGHT?? ; )

@casheroo Good God. Just ONE of those things would have made me get out of there fast! ERK!

i was just remembering that one time a few years ago i was eating this girl out and she queefed in my face hahahaha. classic. i laugh about it now. i laughed about it then too. but she didnt…lol

A guy that was just a friend. We were in his dorm room and he started talking about how he was Jewish and had a big dick. Then he showed me. He had found out from some friends of his I was doing porn, and had even told all of his roommates that I did porn. I, however, didn’t know this. But, it turns out it was really awkward, and the headboard kept hitting the wall making it super loud, and he was very built but kept sweating (way more than usual) and breathing heavily (way more than usual) and I felt just kind of trapped. He didn’t even get off, I didn’t even let him kiss me, and when I tried to finish him with my mouth the moment was just over. he never came. And when I walked out all of his roommates (all 7 of them… they lived in a big dorm condo thing) were staring at me and high-fiving him. I’m sure he told them I was a firecracker in bed, but… not that night. I’m used to always having awesome sex that lasts forever, and is incredibly satisfying. That is the one time it has not been.