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39 People Share Best/Worst Sexual Encounters and It's a Rollercoaster of Cringe

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Posted by mattstaff
  • 1
    Hair - Best: Dated a girl in my mid-20's. She was a MILF with big, fake boobs. We had very little in common and she was an emotional train wreck and we didn't last very long. She was an absolute freak in the sheets.
    Via Cheezburger
  • 2
    Text - Worst Girlfriend spent the night we woke up early in the morning and she was riding me... all fine and good right? She hops off and instantly went down on me under the sheets even better right? WRONG! I must have ripped something inside(she wasnt a virgin) because she was bleeding every where but we didnt realize because she went under the sheets.....she came up and blood was EVERYWHERE ALL OVER HER HANDS HER FACE HER CHEST THE WALLS MY DICK THE BLANKETS E VERY WHERE
    Via _
  • 3
    Text - Worst: First time for both her and I, we had no bloody idea what we're doing, fluids everywhere. Best: on Holliday, got asked out for drinks by a women who was about 15+ years my senior in Colorado USA, declined and explained that I was not 21, she just strait up asked if I wanted to fuck, being a single warm blooded male I stuttered out my best yes I could. Had a very fun night.
    Via _
  • 4
    Text - Worst: I met a freak with a bug eye named pam when I was 19. She was in her early 50s. We were both homeless bums. About 10 min in and her son comes over from a different camp and picks a fight with a guy that was down on the river with us having a psychotic episode. When he found out that I was banging his mom and not the stranger he decided it would be better if he were still mad at the stranger.
    Via _
  • 5
    Text - I suppose this qualifies as a best and a worst. When I was in my early 20s and relatively inexperienced, I had a chance to get with a woman in her early 40s. A MILF, to be precise. We met at the gym and she showed interest fairly quickly. I overcame my anxiety and asked her for drinks. As the story goes, we ended up back at her place a couple hours later. She gets on top and starts riding me like I'm the last dick she'll ever take. I could hardly breathe, it was so intense. Well, as luck
    Via _
  • 6
    Text - ugh. the worst? i took off his disappointing tighty whities to reveal what appeared to be a mushroom in a moss patch. at some point he said "mount me"... which killed any enthusiasm i had left. he laid in the masonry position and i did my best but not being able to even feel him was confusing and embarrassing. he laid there for a good 15 minutes, motionless and expressionless till i faked an orgasm, lied and said i was too sensitive to continue and then got dressed. he said he'd give me a
    Via _
  • 7
    Text - Oh shit, my worst has to be when my ex tore off my clit hood It was pretty heated, he was fingerblasting hard and fast until he went to put his fingers in but missed the hole and his sharp nails caught my hood and tore it off. It was legit dangling off, bleeding. I was screaming in agony. It turned purple and then black. I was 15 at the time and had to show my mum that it was dangling off. She found it both disgusting and hysterical.
    Via _
  • 8
    Text - Worst?: fat girl at party(right out of high school) kept hitting on me while I was drunk. Was able to deny her all night despite how drunk i was getting. Passed out drunk on the floor, woke up to her raping me. 6.5/10, would get raped again. P.S Not condoning rape, just sharing my experience
    Via _
  • 9
    Text - A one night stand with a friend's ex She started texting me while horny and I agreed to drive roughly an hour to come visit for guaranteed sex. What she doesn't tell me is we A. have to be quiet because of sleeping roomates B. there is no air conditioning, it is 98 outside, about 110 inside. So there we were, not particularly attracted to each other, each just wanting to get our rocks off, essentially, but it was just so. Damned. Hot. Dripping sweat everywhere, not wanting to move kind of
    Via _
  • 10
    Text - Best: I was fairly active in High School starting at 14 but, was unable to finish. At the age of 19, I had like a 10 minute window to get to work and offered my then girlfriend a spot on my staff. We had had sex before. This time was different. Something clicked. I came after about 2 minutes. I had never felt anything like that in my entire life. I was glowing like a pregnant woman when I got to work. Worst: I don't know if I've ever had bad sex. I really enjoy it. No one has ever smelled
    Via _
  • 11
    Text - I used to live on a small indian reservation which at night regularly had hitchhikers and I would occasionally pick people up. one night a drunk grandma was hitching, so I figured she seemed safe. then she started flirting with me a little. its clear she is a little tipsy. she wasn't attractive, not like insanely ugly, but not 18 (old indian grandma, so not to be rude, but not super sexual of a person). a little back story: i am 18, virgin and ready to explode. for some reason I ask her i
    Via _
  • 12
    Text - So I was going to keep this one to myself, but the internet seems like a good place to share. This happened to me very recently. I was in amsterdamn. I didn't really have much intention to pay for sex when I was in the red light district but as I was wondering around I found myself very curious. Not having the courage I carried on to indulge in amsterdamns other ammenoties. Many hours have now passed and I have smoked a fair share of weed and eaten mushrooms. Many beers later I found myse
    Via _
  • 13
    Text - I'll give you a funny one: my girlfriend and I went to Venice beach years ago and parked for the day in one of those ticketed parking lots. We walk around, have dinner, get horny and head back to the car. I tell her I can't wait for the long trip home so we squeeze in the backseat of my coupe. She starts giving me her best oral presentation and I'm basically playing lookout as the sun goes down and there's still some light out Eventually I just say fuck it and put my head back to enjoy it
    Via _
  • 14
    Text - Best and Worst: A while back I broke up with a girl I had dated for about 2 years in high school and two out. After the break up I was pretty depressed but more horny than a damn bearded dragon. I've always had a thing for black girls so I did my best to hook up with one of only two in my town. Surprisingly she said yes and it wasn't long after we found ourselves in her bedroom. The blowjob was toe curling and her pussy was even better... until she pulled out a goddamn 10-inch strap on an
    Via _
  • 15
    Text - My friend is a gay man and he met this awesome guy who he really clicked with. He was a funny, funny man...the type of person who makes a room light up. My friend said the chemistry was incredible and when the time came for them to get intimate, the guy revealed what he was packin' and it was the width of a coke can. My friend said 'Uh nope!" and the guy just broke down....said he never got to have sex because of his dickus giganticus....men just noped the fuck out of the situation as soo
    Via _
  • 16
    Text - Worst: so I met this girl on tinder, she looked like a freak (crazy hair colors, piercings all over, tattoos, and was a "model"(let some dude take sexy pics of her)). I invited her over to my place to Netflix and chill or whatever. So, things start getting hot and heavy, and we start touching each other and ripping each other's clothes off. Once I got my shirt off, I knew I wasn't having fun anymore. This chick, this motherfucker, bites my nipple so fucking hard that it starts bleeding. I
    Via _
  • 17
    Text - Best: Finally meeting my ex in person(long distance relationship). We said we weren't going to fool around the first night we met, but after a few glasses of wine, all those months of anticipation were WAYYY too much to handle. Definitely the most enjoyable discovery of bodies I've had. Worst: Does not going through with it count? Random party, girl I had been talking to for about a week. She got white girl wasted while I was pretty clear-headed. Just as the tip came in, I had this moment
    Via _
  • 18
    Text - Worst that I can remember. Was having sex with my ex on the couch. l was seated and she was straddling me facing me. Thing is our couch was a hide-a-bed and I'd slid down so that my ass was pretty close the the edge. As she kept rocking back and forth, the cushion under my ass kept shifting, too. Before long the positions lined up just the wrong way and my balls slid off the front of the cushion and when we rocked forward again they got caught between the front of the cushion and the fron
    Via _
  • 19
    Text - Best: Girl i was FWB with, looked and fucked like a pornstar, was unbelievable. Cant believe i fucked that up tbh haha Worst: Almost getting drowned by a girl who was a SQUIRTER in 69 position without prior warning on the flood that was to embark on e.
    Via _
  • 20
    Text - Best: impulse sex with a friend in the chemistry building of university. 12 sec of absolute joy Worst: on my birthday with now ex-gf. Neither of us wanted to do it coz our relationship at that time had degraded a lot. But she felt like she needed to make an effort and I did not want to have an argument 10 min after waking up on my 22nd bd. 12 second of awkwardly faked pleasure
    Via _
  • 21
    Text - Met a guy who said he hadn't had sex in 7 years, we got along pretty well so I told him I'd give him a pity fuck. He gets it out and it's like 2, 3 inches maximum. I ask him if he's ready, thinking maybe he's nervous and a grower, not a shower. Turns out he's hard, shit. He puts a condom on, and it was legit baggy. Let's just say, the fingering filled me up more than the actual sex. I feel bad about it still, but he was happy, that was my intention so that's what mattered. Also, doing tha
    Via _
  • 22
    Text - Worst: My college boyfriend and I had been dating for about two weeks. He was a virgin and I knew that. I had only had one other sexual partner and admittedly was not good at sex either, very self conscious. Because he was a virgin I was less self conscious. He was very very nervous and also very sweaty. I ended up having to stop him because his sweat dripped into my mouth and eyes. We're married now and are both MUCH better. He's still sweaty, but I love him. Best: We were housesitting f
    Via _
  • 23
    Text - Worst: Guy was 25, admitted he was a virgin casually while nearly being undressed Didn't judge him. Didn't judge him at all Then he proceeded to get undressed. He had the tiniest dick. Started to feel really really bad for this guy honestly. But we still shared the bed, tried to make his first time worth it. Wasn't good for me at all, he went down on there between my legs at one point like a fatty on a free buffet, but you know, it was his first time, we managed. Then the next morning he
    Via _
  • 24
    Text - Best: Role playing with an ex. I was the prison guard having to do a cavity search on her only using my mouth and cock Vigorously had sex until we both had multiple orgasms. She could barely walk and took her a few minutes to recover. Worst: My friend introduced me to a girl he knew. Took her home and we start getting frisky. I begin to make my way down to perform cunnilingus, when I'm hit in the face with the worst smell ever. I fake her out and start kissing her body making my way back
    Via _
  • 25
    Text - When I was back in AZ there was this girl who I use to be FWB with. Things already started to get weird because after a while she started drinking wayyyyyy too much when we hung out. So this one night we're both drinking, but not smashed by any means and we start fooling around. We're about to start to go at it both undressed and she just completely changes her expression. She starts to cry and the only word she says is please. I ask her whats wrong? What happened? Is that anything I can
    Via _
  • 26
    Text - Best: With a former classmate, nearly ten years after graduating and it was rushed, rough, and awesome. Worst: Found out that he lived with his mom so we had sex while parked along a deserted road. Well, attempted to but his truck was rather small for both of us so he opened the passenger door and long story short.. I fell out head first.. Edit- This is my highest voted up comment.. thanks?
    Via _
  • 27
    Text - Best: I was hooking up with a girl who would orgasm if I went all the way in. I could hold it there or just do my own thing and she would go bonkers. It was literally the easiest sex. Worst: Met a girl on the beach. Took her back to my place. When all the clothes were off she was on bottom and I was on top. Her legs deathgripped my torso. So hard that when I thrusted she moved back and when I pulled back she'd thrust forward. This meant that there was absolutely no friction going on down
    Via _
  • 28
    Text - best Coworker, she was down for anything and everything, she was a squirter too. Big fan of bdsm, it was always exciting. worst - girl had a weird blowjob technique, used teeth and more or less swished my dick around in her mouth.
    Via _
  • 29
    Text - Best: This one time I lasted at least 15 to 20 seconds. I'm not sure the circumstances that led to the uncharacteristic length of intercourse and I haven't been able to recreate it since, but I remember my wife saying it was "not too bad" before she finished herself off, took a piss and then went back to reading her Dave Eggers novel. I took that as a win Worst: Every other time ever.
    Via _
  • 30
    Text - Best: When you were passed out at that drinking party and you pissed all over those Elliot Ness CDs Worst: When you were passed out at that drinking party and you pissed all over those Elliot Ness CDs
    Via _
  • 31
    Text - My ex boyfriend. Took my virginity, was a one pump chump and going down on me felt like he was literally eating me out. He was my first sexual encounter so I genuinely thought this was what normal sex was like. Fast forward 2 years later I broke up with him and had a one night stand with my now new boyfriend of 3 years and thought "OH MY GOD, THIS IS WHAT I'VE BEEN MISSING OUT ON, WHAT HAVE I BEEN DOING ALL MY LIFE"
    Via _
  • 32
    Text - Best: Dated a girl in my mid-20's. She was a MILF with big, fake boobs. We had very little in common and she was an emotional train wreck and we didn't last very long. She was an absolute freak in the sheets. Nothing I tried was off-limits. The word "no" was not in her vocabulary when the bedroom door shut. She would go along with any action or roleplay I tried no matter how nasty. It was like having a personal fembot. It's been almost 8 years and she's still in my spank bank. Worst: Got
    Via _
  • 33
    Text - Had a one night stand with an acquaintance a couple years ago, we were both very drunk and he didn't finish and we fell asleep. Woke up in the middle of the night to him having a wank against my ass. I didn't know what the fuck to do and kinda just lay there in shock. He came, I pretended I was asleep to avoid any awkwardness and proceeded to leave the house about 15 minutes later without waking him up. It was weird, have had minimal one night stands since.
    Via _
  • 34
    Text - Worst is this guy I met at a bar my last night living in New York. When we started getting down and dirty he went down on me for about ten seconds and just did these weird kind of licks all over between my legs, pretty much totally avoiding where he needed to actually be. Once he came up from that he gave me about three pumps, came, and flopped down next to me breathing like we'd just had some all night fuckfest. Get ready for this. First he rolled over and asked me how many times I came.
    Via _
  • 35
    Text - Worst: First time with my then-boyfriend, we were in a very dark room. I went down on him and he seemed to enjoy when I was using a fair bit of suction on him, so I kept doing it. Approximately 20 minutes-ish later, as he was almost about to orgasm, I started tasting blood. Like, it was coating my mouth bloody-blood I panicked and told him I tasted blood. He turned the bedside lamp on and saw that my entire lower-face and his shaft was covered in blood. He started freaking out, lost his e
    Via _
  • 36
    Text - Best: First time my wife and I ever came simultaneously Worst: I hooked up with a girl at a friend's wedding. I was going slow and kind of working it in when she says "just go in as far as you can". So I press my pelvis against hers, she trembles, holds me there a second, and then lets out a tiny gasp and then goes noticeably limp. She then says "What, you can't cum?" "...What?" "Did you not get off?" .. Well, we just started and-" As she is kicking me off of her "Well, I guess I just kno
    Via _
  • 37
    Text - Worst: the guy who sucked at foreplay. Was in a relationship with him for a year and spent a lot of time faking orgasms. He was my first, so I didn't know any better. Best: the first time my husband and I had sex after he got the "all clear" after his vasectomy. Never having to worry about getting pregnant again was priceless.
    Via _
  • 38
    Text - Worst: He had talked himself up so much (that should have been my first clue), and then come time to actually have sexy times he had the worst breath I've ever smelled, he had horrible body odor (even though he'd just taken a shower), he kissed like he was an oxygen mask (whole mouth over almost my nose and mouth and he kept licking me), then he couldn't get it up to fuck me, and when he finally managed to get it up, he apparently started thinking about his ex girlfriend and started sobbi
    Via _
  • 39
    Text - Girl had a shallow vagina, and sex was awful so I decide to at least go down on her. We had just ate sushi and I guess the liquor in my belly wasn't settling right. I get down to do my business, and it is hands down the stinkiest stank I've ever smelled. I hold my breath and dive in (the gentleman's move). It smells so bad, and the sushi/whisky combo was so unsettling, I threw up in my mouth, quietly spit it onto the floor under her bed, and kept on going... Edit: Wow, thank you for the g
    Via _
  • 40
    Text - I went back to a guys house who was a friend of a friend. We were both drunk, stuff starts happened and we are alternating oral, general foreplay stuff. Suddenly he gets up, runs to the bathroom, I assume he is going to be sick but a moment later I hear sobbing. I walk in and he is bent double in the middle of the room crying his eyes out, I ask him what's up and he goes: "I'm fat, I'm ugly, nobody likes me" Went from crappy sex to suicide watch in ten seconds.
    Via _

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