Worst Sexual Experience

[PlayboyMegan]

What was your worst CONSENSUAL sexual experience? I need them dirty deets people!!!

 

[Worship Jaclyn]

I'm glad (though sad you had to) put in the consensual part. I was like, eek this is going to be half depressing half hilarious. Good thinking

Mine was easily in high school. I had just gone through my first breakup and was just slutting it up quite a bit. I had just discovered I was attractive and just discovered alcohol. Such terrible timing for those things to happen at the same time. Anywayyy. I was fooling around with this guy who had wanted me for years. He was older, muscular, had tattoos, always wore wife beaters. He was just a badass looking guy. He still is, even now so it wasn't just in my baby head. We were making out and he pulled down my shirt to squeeze my nipple. I mean I was drunk but I think this was only going on for a couple minutes. I put my hand down his pants to feel this limp little thing, I mean little, and cum everywhere. It took me a minute to realize that it was cum. This hot, awesome guy just came from seeing my tit. I can't imagine the look on my face. I just got up, wiped my hand on my own pants and left. Surely it was his worst experience too.

 

[PlayboyMegan]

So I had sex with this guy and we were both really drunk. He had a hard time getting it up and insisted on using a condom. I hate condoms so it was doomed from the beginning. Not to mention, he was not "packing" down there and I'm a size queen. While I was blowing him, he stuck his index finger in my ass, dry. ( :shock: that was my face) Then he randomly started 69ing me and he was humping my face way too hard. He finally got hard and couldn't put the condom on. After like 10 attempts, it went on. He fucked me missionary and immediately started choking me with no warning. No worries, it only lasted a few pumps... :roll: Then he ended it by saying, "you are the hottest girl I've ever fucked."
We woke up the next day and I was the most hungover I had ever been in my life. I must have puked over 12 times. His toilet was brown with pee and pubic hair on it which did not help the situation. When I drink, the next day my stomach is extremely upset (I think I have an allergy to alcohol). Sooooo I clogged up the toilet... I told him and he was like, "don't worry, I'll fix it!" I was like, "NOOO!!! Don't you come in here!!! Just tell me how to do it and I will." So I got it unclogged. The whole event was a mess.

 

[Worship Jaclyn]

I just realized this wasn't in models only. Sorry. I suppose I could have gone without saying that I was young at the time.

 

[Rose]

Ooh boy.... I'll just pick one. :?

I don't even know where to begin. This one was probably in the top 5, though I'm not sure if it's the absolute worst or not. Dude was uncut (nothing wrong with that) and didn't wash.... I was stoned out of my mind and probably also seriously doped up on pain meds given when this occurred, and probably also still fairly fresh from surgery. He had a massive penis, just massive. I swear to gosh it reached his knees, and he was gangly and scrawny as all get out. Didn't bathe, his hair always looked like it was making its own hair gel, at least he brushed his teeth. He didn't have any problems getting it up, never did, but he had the worst aim ever. I actually ended up getting stitches because of this guy, no joke. His aim was so bad he actually ripped my taint. He just barged into my taint like it was a wide open hallway and not an incredibly fragile piece of skin that hurts super bad when punched with a massive weiner.

I was already bleeding from coming off the depo shot so I didn't realize how bad the situation was until I got home. I was having a bad flare up and needed to go to the er anyways, so it was convenient to get the stitches at the same time and was over quickly. For his credit, he had a great work ethic, was a safe driver, played the drums and bass well, and wasn't a bad person. He was just...oblivious and careless in the bedroom and had terrible personal hygiene.

 

[Worship Jaclyn]

He didn't have any problems getting it up, never did, but he had the worst aim ever. I actually ended up getting stitches because of this guy, no joke. His aim was so bad he actually ripped my taint. He just barged into my taint like it was a wide open hallway and not an incredibly fragile piece of skin that hurts super bad when punched with a massive weiner.

Ouch!!! My husband has to be right up against me before he can go in. He used to be like an inch away from me and just dart in and I hated it so I can't even imagine what this guy did. Fuck no. I don't like in and out. I just like in and inner.. or something. Eeek. Reading that made my pussy Hurt :icon-cry:

 

[Ambers Troll]

Am glad you said consensual, was intending to post a whole other experience.

For me it was always that time you failed to perform for embarrassing worst moments, but think I can outdo embarrassing ...look up Haematospermia if you want a scary experience as a man.

 

[LacieLaPlante]

One of the sexiest guys I've ever been with was also the most unfortunate in bed. He had no idea where or what a clit was, or how to touch it. He rubbed my nipple rapidly like a clit. God forbid he try to use his mouth anywhere, I'd be afraid he'd bite me.

 

[Ambers Troll]

One of the sexiest guys I've ever been with was also the most unfortunate in bed. He had no idea where or what a clit was, or how to touch it. He rubbed my nipple rapidly like a clit. God forbid he try to use his mouth anywhere, I'd be afraid he'd bite me.

Goes to show how much sex is learnt... we need someone to teach us how to do it at some point. Sounds like you missed an opportunity there L.

 

[eyeteach]

Finally a game I get to play!

I had just started dating this girl who had a 8 year old son. Before I met her had you asked me if I would ever date a girl with kids I would have selfishly said no; well, she changed all that. Not long after we started seeing each other she invited me one Thursday night for a movie night complete with dinner, I'm all for it! Her son didn't have to go to school the next day ( a weather day or some shit) and she didn't work on Friday's so she and I kinda planned some alone time together after Junior went to bed. Finally she gets him to sleep and off to her bedroom on the other side of the house she and I go. Now she had a tendency to get loud during sex, something I did NOT mind in the least. I stopped by the bathroom closet and got a couple of towels to place at the bottom of the door to try to "soundproof" her door. She took a pillow and placed it over the a/c vent to muffle any sounds and finally we did get room and soundproofed as we could get it...looking back, we should've checked for animals because sometime earlier that night her cat snuck into her room and hid under the bed.

Finally though we get down to bidness. Now I thought this girl was the prettiest thing I'd ever seen in my life (honestly, she could fit in with any model on this forum; beautiful, beautiful girl.). We're both nekkid and I decide it's time I rock her world with my infamous oral skills (I heard y'all laughing, don't pretend you didn't.). I ease off the edge of her bed to the floor, she flexes her knees and spreads her lips and I'm about to go down on her when I felt something trying to rip my nuts off. I let out a loud "GODDAMNIT!" and the fucking cat streaks across her room and jumps into her closet. She jumps up, looks up at me and said, "Dont yell! What's wrong?" I look down and saw streams of blood from my balls flowing down to my ankles. I said, "The goddamn cat tried to de-nut me!" She collapsed back on the bed and starts laughing to beat all hell...it wasn't funny to me. I'm standing there pissed off, wasting a good hard, looking like I need a tampon and she can't catch her breath from laughing. Well FUUUUUUCK this...I go down on her anyway, get her to climax, walk over to the door and grab one of the towels stuffed under the door to wipe the blood away.

Later that night, the next morning at @ 4:30 or so actually, we're still going at it. All of a sudden she pushes me off her and says, "Wait, I hear something..." Sure enough it's floorboards creaking and then we heard the sound of her door knob clicking open. I hide under the comforter and she feigns sleep when her son peaks his head un her door and says, "Mama...mama, where are you going?" She lifts her head off her pillow and ask him what he means and why is he up at that early hour. He tells her "You said that you were coming, where are you going?" it takes all I have not to throw that comforter off and ball up laughing. I let out a smirch of a giggle then feel something try to cave my ribs in, now I can't breath muchness laugh after that elbow she caught me with. She puts her robe on and leads the lad back to his bedroom, sits with Jim until he falls asleep and then comes back to rejoin me. She enters the room, sits on the bed and asks if I want to finish. I told her we'd do it again another night when there's not as much excitement and she agreed to that. I got dressed, kissed her goodbye and snuck out of her house.

Long story short: I came for the pussy, I left with shredded balls and crack ribs.

 

[Rose]

One of the sexiest guys I've ever been with was also the most unfortunate in bed. He had no idea where or what a clit was, or how to touch it. He rubbed my nipple rapidly like a clit. God forbid he try to use his mouth anywhere, I'd be afraid he'd bite me.

Goes to show how much sex is learnt... we need someone to teach us how to do it at some point. Sounds like you missed an opportunity there L.

That's rude and presumptuous to assume that. Not everyone is teachable, especially when it comes to sex.

 

[Picnic]

A failed threesome. That's all I'm going to say. It failed pretty horribly.

 

[eyeteach]

A failed threesome. That's all I'm going to say. It failed pretty horribly.

Megan specifically said "dirty deets" so spill 'em my Twisted Sister!

 

[Picnic]

A failed threesome. That's all I'm going to say. It failed pretty horribly.

Megan specifically said "dirty deets" so spill 'em my Twisted Sister!

The third party was not interested in me, whereas I had become pretty romantically/emotionally interested by that point.

 

[eyeteach]

A failed threesome. That's all I'm going to say. It failed pretty horribly.

Megan specifically said "dirty deets" so spill 'em my Twisted Sister!

The third party was not interested in me, whereas I had become pretty romantically/emotionally interested by that point.

As we say down, well bless your heart! That really sucks, I'm sorry about that. :icon-cry:

 

[Picnic]

A failed threesome. That's all I'm going to say. It failed pretty horribly.

Megan specifically said "dirty deets" so spill 'em my Twisted Sister!

The third party was not interested in me, whereas I had become pretty romantically/emotionally interested by that point.

As we say down, well bless your heart! That really sucks, I'm sorry about that. :icon-cry:

You live, you learn! It may have been shitty, but I've had a ton of really awesome sexual experiences too, sooo...you gotta have a balance, right? :thumbleft:

 

[eyeteach]

A failed threesome. That's all I'm going to say. It failed pretty horribly.

If it's any consolation, my first and only 3-some involved the girl in my earlier post. Just she, and I,and...unfortunately, she. Turns out she was bipolar, schizophrenic and had multiple personalities. She could really turn against me, or anyone else, in a nanosecond.

 

[LacieLaPlante]

One of the sexiest guys I've ever been with was also the most unfortunate in bed. He had no idea where or what a clit was, or how to touch it. He rubbed my nipple rapidly like a clit. God forbid he try to use his mouth anywhere, I'd be afraid he'd bite me.

Goes to show how much sex is learnt... we need someone to teach us how to do it at some point. Sounds like you missed an opportunity there L.

I was young and much more shy about sex at this point (I was 19!). I felt like I would be hurting his feelings and make things awkward between us. Every guy I had been with was older than I and had known what to do. He was my first younger man and when I stress how I attractive he was.. I mean I really thought he was out of my league at this point in time and didn't want to offend him.

 

[Kunra9]

Wow so many to choose from. I'vehad plenty of bad moments and most were my fault lol.

Probably the funniest...

I went out with some friends to a local bar. Met up with a girl I had been pursuing for quite some time. We drink, we dance, things are escalating nicely. We make out at the bar a bit and then she suggests we go to my place. When we get to my house we start attacking each other. Heavy making out, lots of grabbing, clothes are starting to come off, etc.

She suggests we do a couple of shots which we do and then continue.

Then, suddenly, she says she has to go home. Just mid-make out. I am pretty wasted at this point, and of course try to convince her to stay but she is out the door in 10 seconds.

So there I am, half naked, very drunk, very horny at about 5am. So logically I take out my phone and text a girl that's been chasing me whom I have no interest in, but I'm positive will come over and satisfy my need.

She comes over about 30 minutes later, we make out a bit but she says she is on the way to work so we don't have sex. She suggests coming back on her lunch and my drunk ass says sure. I pass out she goes to work.

I am woken several hours later as she is crawling in bed with me. I am much more sober and extremely hung over. She starts trying to get me up but my body and brain are just not having iit . now that I'm sober I remember that I'm not attracted to her. I tell her I'm feeling too hungover but she insists. She is using her hand, her mouth, dry humping and I am barely managing half chub. After about 20 minutes of work, he finally comes around, we slap on a condom, she climbs on top....

And I proceed to prematurely ejaculate like it's my first time. Literally less than 10 seconds.

Then, when I go to the bathroom to clean up, hangover really kicks in and I start vomiting.

By the time I finish and clean up, she has left. I was really embarrassed and felt pretty awful.

The silver lining... Because I performed so horribly, she never showed interest in me again.
She did however tell many of her friends that I was a one pump chump though, which sucked.

 

[RubyDimples]

Over five years ago I had a knack of getting involved with the wrong kind of people and always got introduced to the wrong kind of men. One drunken night at a friends boyfriends apt, I was introduced to a man named Mark and I had decided we were going to get down! We started in the kitchen and I noticed immediately he had no concept of how to please a woman. I know everyone has their kinks and we are all different..but rubbing hard on a barely stimulated pussy is like a pussy indian burn! I try to rationalize his lack of knowledge about female anatomy and proceed to the bedroom. He had a great physique, nice cock, and the possibility of good sex was still looming in my mind. Of course with hardly any stimulation on his part, he decides lets abruptly penetrate and pray for a lubricated pussy. NOT! Long story short I eventually had to tell him to stop and that didn't satisfy his ego much. He left like an asshole and I laid there like what a selfish prick!

 

[Brad]

I can only think of one time. A girl and I had skipped high school and spent the day partying with another female friend. We left her off at her house and we were walking back to school when we decided to have sex in a wooded area as we were both pretty horny. I was so damn drunk that I couldn't have hit it even if I had a map. I finally mumbled that I was just too drunk and we both put our pants back on and continued on our way. Thankfully she understood but it was pretty embarrassing for me.

 

[AllisonWilder]

Okay, I met this guy at a friends house while we were all drinking and we made our way upstairs to hook up. Furiously making out and clothes are coming off and he stops to first ask me what my name is and then a few minutes later to ask if I was 18. It got super awkward after that but he was way out of my league, much older (31 to my 18) and had hella awesome tattoos so I just went with it. He laid me on my stomach and started to fuck me, except it was like, pump..pump....pause.....................................pump......pump.....pause and so on. I remember thinking that he must have passed out and I'd try to get up and then he'd start again. I was ridiculously shy and awkward so this kind of just went on and on and on for a while, easily 30 minutes. He didn't cum, pulled out, rolled over on his back and just laid there for what felt like ages saying nothing at all so I got up, got dressed and rejoined my friends. He was still laying naked on the bed when I left a couple hours later. :lol: :lol:

 

[AuroraKnight]

It seems like all the guys we think are out of our league are the common worst experiences lol

Mr. Malice and I have a nontraditional relationship, so I hope this isn't super hard to follow.

One weekend, shortly after high school graduation (well Mr. Malice's graduation I had dropped out) we had a couple friends over to hang out (one guy and one lady) and after a bit of drinking we decided to play truth or dare and one thing led to another and the guy friend and I ended up fucking on my couch, piss drunk, it took him forever to get the condom on, and when he finally did, he lasted maybe 30 seconds. We ended up cuddling on the couch for a bit (because we didn't want to interrupt Mr. Malice and the lady friend) it was ridiculously awkward, and Mr. Malice thinks it's funny to bring up. So yeah nontraditional relationship+alcohol+single friends= awkward, mostly bad sex.

To make my first statement make sense, at the school I went to, the drama kids were hot shit/on a higher level than the jocks, and guy friend was a drama kid. So yeah, the common consensus is the people we think are out of our league, probably aren't what we expect them to be.

 

[LilLitaRose]

God it's a mashup between my first time and this one guy whom it was good until.
SO I'LL TELL BOTH!

First time, I was really into the idea of sex. Like, I knew I wanted it and was tired of waiting. Well, cue to the boyfriend and I unable to find my sister's stash of condoms. So I, being the brilliant person I was, (I was young and naive, I will not say the age), suggested a ziplock bag. He then whined about it hurting him, and told me to turn the seam inside out. We had sex, (didn't even finish cause it was my first time and I was on top and didn't know what I was doing). Afterwards he cried cause he didn't get to cum and said his first time was ruined. (Uh. Okay. What about me?).
Good until
Well, this guy I was kind of attracted to, but not really. We knew each other through mutual friends, and I didn't expect things to lead to sex. Well, we get to the sex and he's able to lift me up and do all sorts of things because he's physically that strong.
We're getting near the end and he goes, "Oh mommy! Pinch my nipples".
This was my face "O_O""""" " I just sat there until he finished. That was totally awkward...

So yeah, those are the worst sex I've had. XD Now I want good sex.

 

[Kokoro]

Where do I begin?

Honestly, the top ones would have to be the two times I've escorted. The first time was with a man older than my own dad. Just, ew. I'm not into older men. The second time was when I was in LA and was trying to make a quick $100. The guy was drunk as fuck and was only inside of me for maybe one thrust. I just put my hand over his penis to make it feel like He was fucking me. I made 100 bucks in 5 minutes. Yeah, I kind of scammed him and I feel kind of bad about it now. But I was in a bad possition and I needed money to go back home.

As far as other times. There was the one time I had sex with my fake agent and the other girl he brough with him because we were all super turnt. That wasn't too fun. There was also the time I took someone's virginity at a party. I kind of wish I had the judgement not to do it, but honestly I don't remember instigating anything because we were both so drunk (I think it was a joint effort. It was consensual nonetheless) also because nobody should loose their virginity at a party while under the influence. Needless to say, I broke his heart when. I told him that I didn't want to date him afterwards. He still continues to pursue me to this day. What made the situation worse was that right before we had sex, his cousin came in and told the dude how great I am at sex and how he picked the right girl to loose his virginity with (we have a history). Its awkward when you've had sex with a pair of cousins and they both still want you.

 

[motherbrain]

I've had sooo much bad, awkward sex I don't know where to start.

1) I fucked my old room mate and he was biting my nipple so hard it started bleeding. He was also uncircumsized and I'd never been with a guy like that before... he could tell and was like, telling me how to touch him. LOL It was so awkward. I think we were both excited about the fantasy, both going through breakups at the time, and then halfway through we were just like "yeah this is a bad idea."

2) I used to be a barista and this super hipster guy from the Apple store across the street would come in all the time and we became friends. We ended up sleeping together over quite some time and he had the smallest dick I've ever seen. Ever. I could barely feel it. I was polite and told him I just wanted to be friends but he wouldn't take that. He nagged me constantly for a reason, and even was like "I was fucking you so hard I have no idea how you didn't like it" :? I ended up telling him the truth, now we hate each other. He's one of the biggest assholes I've ever met in my life.

3) My best guy friend and I were wasted at a con and fucked in my car. He has a really hairy body and ended up getting SO SWEATY he was dripping all over me and his chest hair was like a wet carpet slapping against me. It was so fucking gross!

There's much more. This is all that comes to mind right now, though.
I will surely be updating again soon.

 

[AllisonWilder]

1) I fucked my old room mate and he was biting my nipple so hard it started bleeding. He was also uncircumsized and I'd never been with a guy like that before... he could tell and was like, telling me how to touch him. LOL It was so awkward. I think we were both excited about the fantasy, both going through breakups at the time, and then halfway through we were just like "yeah this is a bad idea."

For some reason this nipple story jogged my memory!

I had a ridiculous one-night stand with this dude who a few minutes in started demanding "lick my tit, suck it" ( :? ) over and over while he was fucking me. I was so thrown off that I didn't even stop him when my head started slamming my head into the headboard, I just wanted it to be over. :lol:

 

[SaffronBurke]

Relevant - gifs summing up people's first time:
http://diply.com/trendyjoe/reddit-users-submit-gifs-perfectly-sum-up-their-first/45191

 

[xoxoHunter]

My first awkward story was after a year and a half long relationship ended, and I just wanted a rebound. I had this guy friend, who I knew all too well was bad news. But younger me always believed that I could help someone become a better person yada, yada (please don't judge on past me haha). Well I drove an HOUR AND A HALF to see this guy. I got there and he was super drunk, and I don't really drink. And it was awkward because I just hung out with his family the whole time. Then around 10 at night, I had been there for about 2-3 hours, he decided that we could finally go upstairs. We had made a bet earlier in the week, and I owed him a back massage, so I offered it to him, and he took it. After a few minutes I was like "wth did he seriously fall asleep?" Yep. He fell asleep. More like, passed out from being too drunk. And there was no A/C. After laying there in the heat with no fan for hours, I had to pee. I went downstairs, and his cousins wife was on the couch, and the cousin was in the bathroom. Awkward. I didn't pee till i left the next morning. Then the next week he wanted me to come over again. But this time to his parents house (where he was living in-between leases.) Oh, this guy also has a son, who was 4 at the time. Had him while he was in high school, parents broke up a month after the little guy was born. Well he had his son that night, and he was sleeping when I got there. So we were sitting in the living room, watching football, with his son sleeping, absolutely no conversation. Again, very awkward. Eventually his mom came to get his son and put him to bed. Once that was done we headed towards his room, which was in the garage attic. FINALLY there was a little bit of conversation. Then one thing led to another, and sex happened. And he was super small. Like to the point where I couldn't even feel him inside of me... At all. I also gave him a blow job that night and he was STUNNED, "OH MY GOD. How can you do that? You're so good... I didn't know you could deep throat." In my Brain: "Honey, you're just so stinking small, you'd NEVER reach my throat.." I also got insulted by him mom later that night. His son woke up and she texted him about it and he was like, "well send him up" and her response was something along the lines of she doesn't know what he's up to with another one of his "slutty lady friends" upstairs. YAY.

The 2nd was with a guy that I had an ongoing unofficial relationship with, after it had ended. We both got super, super drunk. Ended up making out on the floor (I was on my period at the time.) But he really wanted sex. All of the sex with him prior had been SUPER awful. His kissing would even tear up my cheeks (how is that possible...?) I ended up taking out my tampon, and we had AMAZING sex. it was the best sex i'd had in a while, and the best sex I had with him. Until...dundundun.... Time for anal. Without warning. I'd never done it before and there was no lube, No nothing. OUCH. So with me being so drunk and the fact that I hadn't been thinking about my actions prior to the sex, my mind came to the realization that he was not going to want anything to do with me, and he just wanted the sex. So I started crying from being drunk and the pain of the anal :lol: But since I was so drunk, I wasn't able to stop crying. Oh, then I find out the next day that he ruined one of our best friends rags that was a gift from his girlfriend with my blood. AND HE HAD LEFT IT ON THE FUCKING COUNTER. Good lord. super awkward moments. :lol:

 

[Violet October]

The most recent "bad" experience was at one of the brothels. A totally adorable, but not sexually attractive to me, young man came in and was incredibly interested in me because we could talk about art, the cosmos, etc and decided to go for it!

It was absolutely the smallest penis I've ever seen, couldn't feel it inside of me, etc. I was on top and of course wanted to give him a good time. I could tell he was insecure about his size issue, and I wanted to make him feel good. I was on top riding him, fake moaning and being all touchy (I love being touchy-feely), when he told me he'd gotten so nervous he'd gone soft and wasn't inside of me anymore. While I was still riding and moaning. I couldn't tell the difference. I was mortified that I'd just made him feel so horrible about his size when that was the OPPOSITE of what I'd been trying to do.

He was also slightly weird. Had GREAT hair, but wouldn't take off his ballcap curing sex. Or his socks. What.