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File: 1478035826747.jpg (198.08 KB, 414x672, 11bbcaff8a5d2c2c229eef6097c639…)

No. 139342

Have you had any truly funny/embarrassing/awkward sexual encounters? Post your laughable sexual "conquests" here!

The encounter that spurred the idea >>40169

No. 139343

>>139342
I'm not sure if this is the kinda story you were looking for, but I might as well share to get things going. The first time I had sex with my bf I was very nervous. I had horrible nausea but figured that must have been normal and that it'll go away after a while. Well, we get naked and are about to go at it and I dunno what happened next. My entire body just starts to tremble and I'm really hot all of a sudden and sweating. It's like that eminem song, my knees weak, palms sweaty, etc. He asks if everything is fine and if I'm comfortable, I say yes even though I'm not. I didn't want to ruin this moment so I tried to ignore my body's feelings. He tries sticking it in and I dunno why but the sickness just accelerates and I throw up right there. I had to sit down for about an hour to stop the shaking and sickness and all that. We tried again about a month later and it went fine. I'm not sure why my body reacted that way the first time and not the second time. I dunno, maybe my mind got more used to the idea.

No. 139344

Several. Here's one that comes to mind.

I was out with my friends doing a pub crawl and we ran into a group of guys doing the same so we decided to join up. There was this hot bad boy type of guy there who was fit and flirting outrageously with me the entire night. Eventually towards the end of the crawl we decide to stumble back to his hotel room. He's telling me all manners of dirty things he plans on doing to me on the way there while kissing my neck and holding my waist. I'm getting excited af. When we get there he picks me up and tosses me on the bed.

> =3 Pomf


Practically rips my panties off and gets his pants off with some pretty good dex for a drunk guy. He hands me the condom and I start putting it on his dick (was average length but pretty good thickness) and he starts pumping my hand while I'm doing it. Kind of made it a bitch to get on. So I finally get it on there and he falls on top of me, we're making out and his hips are thrusting like crazy but I wasn't penetrated or anything. I realized he's fucking his goddamn bed. I tried to move his dick to the target but he just wouldn't stop thrusting and he was lying so heavily on top of me I couldn't move him. Eventually I just give up and lie there and he cums about 5 minutes later then rolls over and passes out. I just got dressed and left after that. Never saw the bedfucker again.

No. 139345

>>139343
Hahah aw, that sucks anon, but still pretty funny! I threw up right after giving head once, trying to explain it was unrelated was awkward, to say the least.

>>139344
>bedfucker
HAHA oh man, i love this. I was the anon requesting this thread and it's already funny as hell. I have some stories of my own, but they will have to wait till tomorrow. Thanks for sharing, ladies!

No. 139346

The first sexual encounter I had was me giving a guy a handjob. I jumped back when he came because it surprised me and it hit him in the face. That also was the last sexual encounter with a man I had because I realized I don't like dick and love the pussy

No. 139347

File: 1478097063688.png (126.34 KB, 365x382, 1466702868315.png)

>had a crush on this guy for a couple of months
>we were friends so I was low key about it and never said anything
>one night hang out with him and some other friends
>we drink and I say I want to go home around 1AM
>this friend invites me to his place
>"s-sure"
>think nothing is gonna happen as my self-esteem was trash and thought he was way out of my league
>we arrive at his place, eat lunch and decide to play some vidya
>after a while we start cuddling
>all is going well
>he asks if I want to fuck
>hell yeah (I actually said "sure)
>we kiss and stuff
>he gets naked
>penis is decent sized
>he puts it in
>freezes
>doesn't move
>I try to move, he says "don't"
>says he doesn't want it anymore
>asks if I can suck him
>cum in literally 20s
>okay
>I sleep until morning (buses or trains don't work until 6AM)
>try talking to him again
>he never replies

Is it worth mentioning he browsed /a/ at the time?

No. 139348

>>139347
I don't get it. What the fuck happened? Why didn't he want to fuck anymore?

No. 139349

>>139348
Remembered his waifu.

No. 139350

>>139348
Sounds like he knew he was going to cum any second so he tried to play it off like he didn't feel like fucking anymore to save face.

No. 139351

>>139348
>he puts it in
>freezes
>doesn't move
>I try to move, he says "don't"

As soon as he put it in he was already about to cum. If he moved he probably would have cummed embarrassingly early.

No. 139352

>>139348
Fuck if I know. He was terrible, for sure, but nothing learning couldn't solve.

No. 139353

File: 1478179606662.jpg (221.04 KB, 1024x1024, 1464338765300.jpg)

>>139351
i feel you, anon.
i've had two different guys cum in one stroke on separate occasions.

No. 139354

>>139345
Glad I could entertain!

>>139347
Your tale has reminded me of a past conquest, Mooseknuckle.

There was a pretty popular guy in college that everyone called Mooseknuckle because had a huge cock and balls and would always whip them out for laughs at parties. He was decent looking, a typical football scholarship stud, and nice though a bit arrogant.

One weekend I was over at his dorm for a party. There were four different rooms that people were wandering around. In his room he was watching movies and I was hanging out too. At some point everyone eventually left so it was just the two of us. He pops in another movie (it was Reindeer Games) and sits next to me on the bed I was on. He puts his arm around me and brings me for cuddling. At this time I was in a bit of disbelief since he's never really flirted with me before.

>Does he like me?

>Are we going to fuck?
>Holy shit how am I going to take that dick?

We eventually start making out and he's just groping me all over. I can feel his dick getting hard and I'm panicking a little, but am also really excited. After a bit he gets up and locks the door and starts taking his clothes off.

>Fuck yeah


I take mine off too and he grabs a condom from his dresser and sits back on the bed. After he gets it on I straddle him and we kiss again as I slowly ease myself onto him. I barely get the head in and he grabs me close to him and shudders.

>Oh, hell no.


He had cum instantly. Disappointed I get off and just flop on the bed. He says that never happens and that he can go again if we just wait a minute. So we make out some more and he tries to finger me. He's clumsy af and has huge fingers so it just hurt. I took his had away before I dried up too much and just keep kissing him. He's rubbing his dick trying to get it hard again but it only gets semi. Then he slaps it against my vulva and I look at him like wtf? "Y-you like that right? It's hot isn't it?" At this point I knew it was futile and just said I was tired and not in the mood anymore. "O-Ok." We go back to watching the awful movie.

Later on there's a scene were Ben Affleck is fighting with Charlize Theron and I guess they banged earlier because he says, "I've had betters sex in prison!" I couldn't help myself, I side-eyed Mooseknuckle and said, "Me too." Poor guy looked as red as a tomato.

We never talked about the incident again and there were no further attempts at hooking up.

No. 139355

File: 1478181207915.jpg (150.26 KB, 789x689, 1452435394007.jpg)

>>139353
You know, anon, I did this when I met someone I wanted to fug.

I cybered with them before fugging irl. So that I could see how long they take fapping. Usually the ones that take 30min or more fapping are decent fuckers. If they cum in 10~15min of cybering I know they are fast jizzers. Usually at +20min you can ask for a dick pic just to confirm the boner is still alive. Worked like a charm.

No. 139356

Slept with a guy once when I was 19 who cried during the entire thing before declaring it was because he was so overwhelmed with love for me. He was a one night stand and stuck with it as he was hot. Awkwardness ensued when I tried console and reassure him but also let him know he can't possibly be in love with a girl he met 4 hours beforehand and got his name completely wrong

No. 139357

File: 1478185086354.jpg (59.47 KB, 560x600, 1453950033470.jpg)

>>139355
I can't believe I never thought of this before. (coming from a former camwhore, at that)
Bless U anon.

No. 139358

>>139357
You are welcome, bless you, anon.

No. 139359

I lost my virginity while on my period.
I was 18 and had not yet had sex with my bf and on Valentine's day we decided to fuckin DO it. I told him my period started but he said it was okay. I felt really awkward about it though. At one point he was like "you're so wet" and I stupidly replied "it's blood."

No. 139360

Not sure if this counts, the sex was fine, but when I was in the "honeymoon period" with my bf we decided to go outside, on the side of a hotel, we were staying in. I didn't know it because I was horny but it was actually the hotel's little dog park. We went out, had sex, and on the way in I stepped on a massive dog crap and didn't notice until I had gotten back to the room, well after I smeared poop absolutely everywhere. It had been wet outside too.

No. 139361

>>139359
I feel like virginity stories are low hanging fruit. They're all awkward.

No. 139362

>>139355
I really admire that kind of calculation. Are you sure you're not Vulcan, anon?

No. 139363

>>139362
I'm just a pervert. I'm settled down for a 10/10 fuck/looks/personality nowadays though. Who or what is Vulcan?

No. 139364

>>139363
Vulcans, like the race from Star Trek

No. 139365

>>139364
It amuses me how people are amazed with simple math. Statistics is high school level stuff. But no, I didn't even know the name of that race to begin with.

No. 139366

>>139365
what are you even going on about?

No. 139367

>>139366
Read the thread.

No. 139368

>>139367
yeah, I did. mathematics have nothing to do with what's being talked about.

No. 139369

It was just a compliment…

No. 139370

>>139368
Anon mentioned the calculation, is there something else I am not aware of?

No. 139371

>>139370
Calculation as in an assessment, not 2+2=5

No. 139372

I'm the anon who posted her story in the host thread, but I thought I would share some of my other failed (on their part) sexual encounters.

I have so many of these, I don't know where to start. I'll just write a short one for now since I'm supposed to be doing homework. This is one of the less cringey stories I have.

I met this guy at one of the parties usually held after my freinds' lives. We spent the whole night talking, and he seemed pretty cool and was super super handsome, but I had a boyfriend at that time, so it didn't go any further than that.
My boyfriend broke up with me shortly after that, so I went on a date with this guy cause free food and alcohol rock.
We got pretty drunk, so I invited him back to my apartment for some good old-fashioned adult fun. It was not fun.
First, he couldn't kiss to save his life, bless his heart. No tongue, yet somehow it was super slobbery and he managed to get saliva on my forehead. So I pushed his head down to my neck so he could kiss that instead of putting my face through saliva torture.
He was pretty okay at fingering and handling my breasts so at least that felt okay. But, he was getting boring, and I wasn't into it, so I decided to take control and give him a blowjob because anything was gonna be better than him trying to kiss me again.
So, I pulled down his pants, took off his underwear, pushed him onto my bed, and started giving him a pre-blowjob handjob. I got two pumps in, and he came in my hair and even got some on my wall. I made him clean it up and told him to leave because it might have been climactic for him, but it was depressingly anticlimactic for me.

I didn't see him again, but he still texts me sometimes and asks if I want to go out with him.

No. 139373

>>139372
>Mr. Beans gets a date

No. 139374

File: 1478532088138.jpg (114.27 KB, 640x640, 1430343752716.jpg)

>>139372
>he managed to get saliva on my forehead

Are you sure it wasn't snot?

No. 139375

>>139374
As far as I'm concerned, it probably could have been both. He was a very leaky person

No. 139376

>>139375
Ew, anon. Praying for you.

No. 139377

My most awkward sexual encounter was with a guy I'd been dating a couple weeks but hadn't yet slept with because he had issues sleeping with someone who wasn't his girlfriend.
So we were getting down to business, and he pulls off his underwear to show this semi flaccid 4 inch dick and I'm lying there like ??? He tries to put inside me (he didn't, he fucked my ass crack thinking it was my vagina) and got all of three pumps before he stops moving. He was totally silent throughout this and I was lying there confused wondering if he finally realised that he wasn't inside me or if he came. He then tries to play it off, asking me if "I needed him to finish me off". I made him leave my house and we broke up 2 days later.

No. 139378

>>139347
>>139353
Cute~
Did you ask if they wanted to go again? Comforting guys who cum too fast is a fetish of mine.

No. 139379

Honestly not as entertaining as most of these stories but I feel inclined to share my awkward story.
>used to live in la and worked in entertainment
>nye party with drake and josh
>met really hot out of towner saxophone player
So getting close to midnight and I was at a happy drunken point and wet outside with my new saxophone playing friend for a hit. He was an amazing kisser so I was excited, we decided to go into the parking garage for privacy and wanted to go down on him. For some reason a blowjob at midnight sounded like a fun story. Get down to unzip and had the mispleasure of seeing the worst pencil dick ever. It was literally as thin as my thumb and like 5 inches so it looked like a freaky E.T finger. He was cute so decided to just go for it. He horribly jerked like a chihuahua humping a pillow and would not cum. It was so bad and I was down there for like a good 15 minutes that a few of my friends came down and started cheering me on. At that point I said fuck it. Told my friends to go back up and that I would hurry it up. So I hurriedly jerked him off with my hand and he came pitifully on the wall and the noise he made was just even more off putting off possible.
Not to mention when I walked back in, dissatisfied and kind of annoyed, 2 of my friends collected condoms and threw it on my like confetti at midnight. Cute but not cute.
After that I've been traumatized of pencil dicks. Every boyfriend after I just hope and prey it never looks like saxophone guy's.

No. 139380

when I was like… 16 or 17 I cut class with my then boyfriend and went to "the woods" to fool around. (aka as close to sex as you can get without being naked and actually bumping uglies)

I ended up giving him a hand job with blistex as lube… then the cops came.

I'm not proud at all

No. 139381

>mfw when the first dick I ever saw irl was eight inches and pretty girthy

I pray for saxophone guy anon, that sounds terrible.
I have a bad lesbian story though

>Get wine drunk af with a female friend

>start making out and playing with her boobs, which has happened before
>she has a boyfriend this time though, but I'm too drunk to care and so is she
>Finger her
>Go to eat her out
>tastes…. Mouldy?
>Is- Is that how vagina should taste
>FirstTimeEatingpussyIDK.jpg
>Go back to fingering her until she cums
>Bitch just left, didn't even try to get into my pants.

I finished myself off, and then the next day all of our mutuals told me she had told her boyfriend I had raped her after he found out from her what happened the night before. Needless to say, we are no longer friends.

No. 139382

I was dragged to a frat boy party and ended up meeting a cute guy. We were both feeling it so we drove to a store to buy condoms & arizona drink thing (lol). Once we got to a hotel room he immediately starts chugging the drink and starts to strip. Average sized dick but he had really saggy balls. Anyways were both into it and he burps on my face. We laugh it off and change position. Like 3 minutes later he took probably one of the loudest farts I've ever heard while still being in me. I bust out laughing and he ended up saying " fuck i wanna die ". We stopped and got dressed. I tried to comfort him but he was just so embarrassed. I never heard or seen him again. Sorry for shitty story but I cannot ever forget that night.

No. 139383

>>139379

I've had a similar experience a few months ago and I hold your same sentiments about future fucks. I shudder everytime I get flashbacks. It was less about how small he was, and more about how awkward he made it.

No. 139384

>>139382
Aww poor guy. I'm sure it was embarrassing for him but it's no big deal. Too bad he couldn't just keep laughing about it. One time I was having drunken sex with a bf and he had the terrible toots and literally farted each time he thrust. We were so drunk it was hilarious and I just laughed my ass off while he thrust and tooted away until he came. We both had some giggles afterwards and I will never forget it.

No. 139385

Holy shit I never thought I'd tell this story to random strangers, but ayy lmao whatever

So I had a really horrible controlling ex boyfriend that makes this entire story funnier.

So we're making out, start having sex in missionary whatever then we switch it up to 69 with him on top of me. It's all going fine then I open my eyes.

In the light of my dorm room, perfectly silhouetted, multiple lumps of shit wiggling around in his ass hair. I was immediately turned off, sat up, and told him to go into the bathroom and check his butt. He chose to stick his hand into his butt while still in MY bed, started complaining, went to the bathroom to wash up, came back to bed and went to sleep without another word.

That is the story of why me and my friends now refer to him as poop-butt.

I also got pink eye :(

No. 139386

>>139384
I'm imagining a steam engine pumping away powered by toots. Thanks for the giggle

No. 139387

Underage clubs are common where I live
>foam party night ages 11-17
>white T shirt night ages 11-17
>neon party ages 11-17
First year in hs half of girls in class decide to go. All meet at one girls house and pile in the center our colllective makeup and get sluttied up. Fun night everyone learns how to grind on boys and other things.
Too dark to see but some guy pulls me in to make out
>first kiss
>not a kiss
slobber everywhere his drool is running down my face and neck, pressing his open mouth against my face making kissing noises and inserts tongue.
Digs fingers into my mouth and pulls out my tongue then he bites it hard. Very hard. Then sucks my tounge incessantly with such force while still biting.
>is this normal who knows first kiss
Next day, my tongue is swollen over twice it's normal size, giant ring of bruised black around my tongue and lots of broken capillaries. Hard to speak properly for over a week.

No. 139388

>>139347
premature ejaculator. probably didn't respond to you due to his massive embarrassment. did he try to get you off at all??
>>139349
HAH

No. 139389

>>139354
I blame reindeer games.
>>139355
Clever girl.

No. 139390

>>139385
Damn anon, that's truly disgusting, i'm surprised you didn't throw up. Fucking ew

No. 139391

>fucking this 10/10 muscle bound hottie who is way out of my league
>he's all "I'm about to come"
>literally seems to develop Tourette's as he's ejaculating, starts growling, going HNG!!! and cursing with every spasm
>"ahhh SHIT"
>"f-f-FUCK DUDE"
>"YO"
>"JESUS FUCK"
>this continues as I lay there with him spasming and yelling on top of me, I'm trying not to laugh and keep moaning for him but wtf
>"Sorry I haven't come in a week"
>I let it go
>he recovers, I give him a handy cuz he's still horny
>he's coming again and jams my mouth down on his dick
>MORE TOURETTES NONSENSE
>choking on semen and laughter, tears pouring down my face
>"are you ok anon-chan"
>wheeze yes and run to the bathroom

We parted on super awkward terms the next morning.

No. 139392

>>139390
I think I was in shock. I have corpaphobia or however it's spelt so I'm pretty sure the colour drained from my face and I just dealt the best I could without losing my shit. I tried to comfort him but he just tried to make me feel bad which thankfully didn't happen.

Honestly that was where it went all down hill. He was a manipulative psychopath but in the end I had the last laugh.

No. 139393

>>139392
Hahah shit (literally). I like you anon, well put and well handled!

No. 139394

>>139391
>he's coming again and jams my mouth down on his dick
>MORE TOURETTES NONSENSE
>choking on semen and laughter, tears pouring down my face

wut

No. 139395

>discuss with this guy on a dating site for some time, he's fun and attractive
>decides to come see him
>he lives with his mom at like 22-23 but whatever, I'm horny
>it's awkward as hell but he ends up fucking me
>we don't know what to do during the day, it's obvious he doesn't want us to be seen by friends
>We eat lunch with his mom, I have to contain wanting to barf from forcing myself to eat peas
>Wanted to be polite, she probably heard me fucking his son
>was supposed to stay the next day but I want to get the fuck out by now and he's pretending to have to go see his grandma
>go home and wonder why I did all that shit

>years later

>this guy is one of the most popular youtuber of my country
>all of my what

No. 139396

hmm. my fwb and I hadn't fucked for about a week or two so when he had messaged me saying he wanted to fuck, I was excited. he doesn't care for blowjobs so we jump right into sex normally. this time though he said I was tighter than usual and had to finger me prior. we started in missionary and we were in this position for 5 minutes before he was turning me over for doggy. with him I cannot take it in doggy, he's too thick and too long lol I swear he hits my cervix, but somehow tonight was different and I wasn't crawling away as much. right when he's starting to get a good rhythm and thrusting harder he stops. he came in less than 10 minutes. he was embarrassed slightly. "um…I kinda just came. this is a new record for me…" and he throws the condom away to get a new one. he has stamina which I sorta can't stand. anyway we continue in missionary for my sake but I have to tell him to stop because the condom started hurting me. he fingers me to heaven and back and when I tell him to stop (because it feels magnificent) HE LITERALLY STOPPED, GOT DRESSED AND FUCKING LEFT. THAT WAS A TOTAL OF 18 FUCKING MINUTES.

needless to say, I was pissed.

No. 139397

>>139395
>this guys is one of the most popular youtubers of my country

Who was it??

No. 139398

>>139397
I'm ashamed tbh, he has a following of teens adoring him and I found his content subpar.
Never told anyone. I'm not a drama whore and don't care for attention at all.

No. 139399

>>139398
Come on, Anon, spill the beans.

No. 139400

>>139388
Nope, he never did.

No. 139401

>>139400
I'll respect that, not sure if the other anon will though. I guess him being really awkward doesn't warrant his youtube career being fucked over.

No. 139402

>>139400
I'll respect that, not sure if the other anon will though. I guess him being really awkward doesn't warrant his youtube career being fucked over.

No. 139403

>>139400
I'll respect that, not sure if the other anon will though. I guess him being really awkward doesn't warrant his youtube career being fucked over.

No. 139404

>>139395
it was jacksepticeye, wasn't it?

No. 139405

>>139401
I'm not the youtuber anon, tard.

No. 139406

The first time I had sex with two of my boyfriends, I was on my period. I warned them, I was embarrassed, but they insisted.

The first time it was when I was losing my virginity. We completely wrecked the hotel room sheets. He said, "wow, that's a lot of blood" and was legit concerned about the hotel charging him. It got on the towels and everything.

Another time was with a guy from China. The next day, he goes, "your pussy stinks". And I go, "Yeah, I told you, I have my period. It's all the blood." "I know." "????" Like that was awkward and offensive as fuck. Who says that?

No. 139407

…. when me and my boyfriend was having sex we switched to doggy style and when he spread my butt cheeks I farted in his face. And I couldn't help but laugh and because of that I kept farting. It was embarrassing af and he still brings it up every once in a while.

No. 139408

I had been talking to this guy off of tinder. He was probably 20 years older than me and we liked the same music. We decide to go to a show together.

I get to his apartment and we get started drinking before we go. I think it was bullit, tuaca, and cheap box wine? We walk to the venue and get some tall boys at the bar after a few songs. We kept drinking, but I handle alcohol pretty well.

After the show we walk back to his apartment. He's super awkward and keeps getting us shots. I had full intentions of sleeping with him, so he didn't need to liquor me up. I remember coming onto him and starting to blow him, but then I'm pretty sure I passed out.

I woke up to him sticking his dick in me. I just pretended that I was asleep still, because I was 19 and stupid. More rape-y than awkward.

No. 139409

>>139395
Was it Pewds?

No. 139410

>>139409
I thought so too, but i bet she would't have specified "in my country" if it was?

No. 139411

>>139395
cmon you cant just leave it at that. you know our thirsty asses so pls come back and tell us who it was

No. 139412

>>139400
forget that limp dick then. back to browsing /a/ where he belongs. poor anon.

No. 139413

I've thrown my shoulder out while having sex before. Bad angle, I was on the couch with her in my lap and it popped while I reached for the lube. My girlfriend at the time had to pull a Houdini and untie herself, it was really awkward.

No. 172744

you guys are sluts please die.(USER HAS BEEN PUT OUT TO PASTURE)

No. 172749

>>172744
not sure if jelly virgin or robot, either way kill yourself

No. 172750

Most awkward sexual encounter was probably giving head in a playground in the middle of the night because we were broke ass kids with nowhere else to go. An older adult couple came to the playground for god knows what reason. We stopped for a bit, them decided "fuck it", and the couple noticed us and laughed.

No. 172811

>>139404
i thought of him too for some reason

No. 172812

>>139409
Pewds didn't live with his mom at that age

No. 173177

Any time super sweaty sex happens and your bodies start making the farting sound with each thrust. Partner and I would try to ignore it and just keep going but then it would be too much and we'd have to change position after laughing for 5 minutes.



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