What was your most awkward sexual experience Sup Forums?

What was your most awkward sexual experience Sup Forums?

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>be me earlier this year
>get cheated on by ex gf
>fucked up mentally but decide to start dating a month later because fuck it
>get a date with former neighbor girl that gave me her number a year or two ago
>first date goes well, second date she invites me over to her place
>we end up getting naked
>she's smoking hot
>i can't get it up because i keep thinking about ex gf
>laugh nervously
>"this doesn't usually happen"
>i'm only able to get it in like three times for 10 seconds at a time
>end up having to get her off with my hands

we kinda stopped talking after that lol

lol who is that

Yikes. Had the same thing happen recently with my gf. She was begging to be fucked and I just couldn't get it hard at that moment. Ruined the moment for her.

I fucked a really chubby chick under a ping pong table during a party. She was decently cool and made it really obvious she liked me but was not very attractive. The party was winding down and my 1st-10th choice girls to try to fuck had left. I literally looked her in the eyes and said "fuck it, lets go i guess" which hurt her less than it should. There was a big tablecloth over the pong table so it wouldn't get ruined so we climbed underneath it and she started stripping. She had big tits but like manhole cover sized nips. I was using one of those free condoms that the college hands out and it was like ziploc bag thick so I couldn't feel shit and neither could she. While we were fucking the rest of the people left or went upstairs so it was dead silent except for the loud grocery bag crunching noise from the condom. I lied and said I came and left her naked under the table while I went to the bathroom and finished myself off.

Sad thing was she told her friends I was amazing in bed and she came over and over (she very clearly didn't)

>Her false testimonial did give me a boost with her friends for a bit tho

>Making out with a girl
>Get handsy, get her undressed
>Start eating her out
>Despite getting no signals from her, decide that we should 69
>Basically shove my dick in her mouth and force her to blow me until completion
>Don't even keep going on her
>She told me after that she considered leaving me then and there, but gave me a second chance
>Days later
>We decide to have sex, but I'm a virgin and haven't told her yet
>Get so nervous that I lose my erection
>To the point where it is gone forever and does not return for hours
Honestly, I don't know why she ever stayed with me.

When I was in my late 40's and newly divorced, I met a cute 24-yr-old and we started chatting a bit. I like crazy & I like tattoos and she had plenty of both. So after the initial awkwardness, we're finally going to do the deed. She strips down and shows me her masterpiece of a tat, which is a HUGE cross on her back. Like across her shoulder blades all the way down to the tramp stamp area. It has wreaths and flowers and shit, and reads "RIP Granddaddy" and has her dead grandfather's birth & death dates. Literally almost covered her entire back, amazing work, beautiful tat......HOWEVER.....she wanted to get fucked from behind, so I'm trying to do my best work while looking at this memorial to dead Grandpa. It's pretty bad, but not THAT awkward yet, because I'm maintaining focus, asking her if she's my whore, etc. etc. (You know, all the good stuff you do in that position). So I'm hanging in there and can tell she's getting close with the moans and whatnot, and right at the moment of truth, she yells out, "YES, YES, FUCK ME LIKE MY DADDY SHOULD HAVE!" She came, but I lost all rigidity and just laid next to her, while considering going into the ministry or becoming a monk. After she recovered, she offered to finish me "any way I'd like", but I declined and said I wanted the first time to simply be "all about her". After that experience, I ghosted HARD. The last I stalked her, she's gained about 40 pounds and is with a morbidly obese guy. I wish them well.....and I thank Grandpa for his service. I've had shit on my dick from anal, and shit on my dick when anal wasn't even involved. I've been walked in on by ex's and current's on my side and the girl's. I had a gun pulled on my while I was plowing a girl once. But I consider ^ that shit to be my most awkward sexual experience.

More of this chick?

When our grandmother walked in

>failed freshman science b/c stoned
>pulled it together over the next three years
>forgot to make up the requirement
>took frosh science sr year
>fat frosh girl in class is cute in the right light
>ask her if she can tutor me
>show up at her house after school and face fuck her and leave
>never talk to her again
>until
>final exam
>I need to cheat
>Make eye contact
>she slips me answers
>I face fuck her after the exam in the boiler room
>she has jizz in her sweater
>Principal asks is this jizz
>she points at me
>Mr Haydens office
>Locks the door
>Pulls his dick out
>Face fucks me
>Vomit
>shit in my pants
>Later we got married

Pic related looks kind of like my younger half sister. Not exactly like her, but similar enough for me to see her in this girls face.

>be 35 yrs old nyc live in gf leaves
>meet 19 yr old bartender
>everytime we fuck i jizz in a second
>she keeps meeting me
>I keep jizzing
>I'm humiliated and determined to fuck her right
>keepjizzing toofast
>One day she tells me she has MS
>never call her again

I was so mad at my ex that I was just completely apathetic about everything. I was laying face down in bed and he proceeded to try to have sex with me. I was just wondering what the hell he was doing trying to fuck me when I was pissed so I refused to go along with it. He ended up not being able to penetrate me because I didn’t move and he felt incredibly embarrassed afterwards I guess.

I came the instant she reached into my underwear to pull my dick out.

I've posted this one on here before but I picked up this weird ass south american exchange student late at a scuzzy college bar one night. We were going back to her place to keep drinking but when she saw her roommates car she said I couldn't come in or she would freak out. It was at this big apartment complex so we sat down behind some bushes and started drunkenly making out and undressing and some shit. Turned out we were right in front of a basement apartment window and some fat dude came into the room and turned on the light. He saw her blowing me with her big brown tiddies out and immediately took his dick out and started jacking it (guess he didn't think we saw him).

We got dressed and decided to sneak into her house (I had to go through the window and fucked up the screen) and we went back to going at it. I didn't have a condom so I'm rawdogging this bitch I met like 2 hours before and she pulls out her laptop and pulls up this enourmous folder of porn and starts showing it to me. She would pull up a video and tell me what I liked about it and what she didn't. I started to sober up and this shit was getting weird. I asked if I could cum inside her and she said no and she hated the feel of cum and that we should finish in the dry jacuzzi tub so I could shoot and not make a mess or get it on her.

I finally manage to cum and she says that she wants to cuddle all night and go on a date the next day. Maybe she was a virgin and didn't know the proper one night stand protocol, who knows. As soon as she dozes off I take off out the front door. Literally sprinting and running across yards and shit. I felt bad after but we didn't exchange numbers (don't even think she got my name) so that was the end of that

>Cue months of STD tests (thank god I was clean)
>Take care of your dick boys

You married mr.hayden?

Girlfriend cheated on me while doing a play in another state. Only told me when I got there to visit her and see the play. I say we should break up but might as well fuck all weekend. She agrees. I decide to hate-fuck her in the ass. She's cryiing but props her ass into place to let me have at it. Can't get it up. Pretend I've taken the high road.

>Her false testimonial did give me a boost with her friends for a bit tho
Nice

MS?

Recently me a girl with a Freddy Kruger tat on her lower back. No not a gf and did not fuck her "though she was a little redhead cutie". I really really wanted to ask if any boyfriends had ever had a problem fucking her from behind while looking Freddy Kruger in the eyes.

It's a short story...

My gf told a friend that I liked getting fisted in the ass. Friend asks to see that. GF demonstrates. Humiliating, but also not as fuck.

> break up with gf
> huge fight
> she gets physical
> restrain her
> both angry horny
> start fucking and shit talking
> she gets on top and I'm pounding as hard as I can
> cum in her because she hates that
> she grabs my throat
> pulls off me and scoots up
> shoots my own jizz all over my chest
> calls me a piece of shit for making her cum
> proceeds to snapchat pics of her fucking another dude in the coming weeks
> I'm low-key jealous
> stops by on the weekend for some of her thing's
> borderline rape her
> she starts dating the new guy
> never see each other again

She was a total fucking psycho.. but that pussy was fire.

A monkey scrotum.

Muscular Dystrophy

my left hand got jealous of my right hand.
what a shitshow.

I had the reverse happen to me. We fucked for hours and I could not cum. She gave up and laid down.

James J

Yes

Multiple sclerosis ya dip

My sides

Pics please

Girl passed out while making out with me and pulling my hand to her crotch. Accused me of raping her when she woke up while i was fingering her.

I am still very angry about this. She actually had me so fucked up about it that i tried to hang myself

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"Our" grandmother. Sister or cousin lol

This was year's ago bruh, I don't have pics on this phone.

>HOuse party
>everybody crashes out all over the house
>wake up with my dick in a fat girl
>jump out of the bed and tell her to fuck off and kill herself
>drive home drunk
>DUI

It happens bro. Don't let it weigh on you. Best thing to do is relax, try again and prove your worth - if you are afforded another opportunity that is. Happened to me when I was dating my second (my current) wife. Hadn't been with a different woman for like 15 years. Been with my current wife now for 10 years - had many years of great sex after that.

>Be me
>Break up with live in girlfriend of 3 years
>We still have 6mo on the lease and I can't find a place to move into mid semester
>We keep living together but just avoid each other
>She goes home ~4 days a week
>I start bringing skanks home when she's not around
>Ex was hot but was religious so was a dead fish in bed
>Meet this girl at school
>Black curly hair, killer body but small tits
>She's a freak in bed
>Inexperienced but wants to try everything
>She's over pretty much every night my ex is gone
>Starts asking questions about her
>especially during sex
>I think it was a dominance thing since I was with her instead of trying to get ex back
>Starts to ask to see pics, asks what she was like in bed, etc
>one night she says she has to go to the bathroom and comes back in just bra/panty lingerie
>she asks if I like it, it looks familar
>I like it because it's the one I bought my ex
>she went into her room and found it and put it on
>she says "fuck me in (ex's name's) panties
>pulls them to the side and fucks me raw (she wasn't on the pill so we usually use condoms)
>won't climb off so I cum inside her
>she pulls the red lacy panties back into place and wears them the rest of the night
>they are SOAKED in cum
>In the A.M. catch her scrape off enough dried cum so it isn't super noticible
>she says something about how the next time she wears them my ex and the whoever she is going to fuck will have our cum on them/in them
>Smirks, kisses me then gets dressed and goes home
>found out later she was "borrowing" my ex's panties and wearing them then putting them back in her drawer
>Hot, but it led to some really awkward conversations and situations
>I miss that girl

Two come to mind.

One was a time I had sex with a virgin and while I was fucking her she said it hurt too much and that she wanted to take it in her ass instead, made no sense to me then or now. I fuck her ass and pull out to come on her ass and when I look down I see her covered in blood and my condomed dick covered in blood and my pubic hair matted with blood. I go to her bathroom and throw up in her sink.

2nd time was I had a friend in high school who was starting to come out as full lesbian after being bi. We watched a movie at my place and during the movie she rubs my dick and asks if I want a blowjob. I am confused because I know she is gay and we had never really done anything. She starts and stops after about 10 minutes and says that she’s not into it. I ask her to go 1 minute more and when she does I face fuck her for a good 15 minutes and cum in her mouth. Surprisingly she swallows. We don’t hang out really at all after that except once when I gave her a ride home because she was drunk and ended up lifting up her skirt for a view of her ass while she was gone.

Sick bitch.. I likey.

Yeah, bitches should be considerate of the guys who have to fuck them when they get tattoos on their back. Selfish cunts, I tell ya.

You did rape her, once she passed out all consent was gone

Yeah, never fuck multiple girls in a friend group. You really hurt the fat one and then all the rest turn on you and it bites you in the ass later

>I fucked 2 of her much better looking friends
>Since they were better looking I asked them to stay the night and fucked them before bed, dealt with the cuddle and the clingyness afterwards, fucked them again in the A.M. and took them to breakfast after
>Chubby girl was pissed because she didn't get the same treatment
>She was lucky I could get it up once
>felt bad after

I was fucking my long term GF at the time around 15 years ago she was bipolar and BDP the 9 yards, railing her doggy style she burst out in tears and says this reminds her of how she was raped just sobbing so I kept going even harder till I finished, she really was a monster relationship ended when she finally killed herself with my 9mm in the bathroom while I was eating taco bell

how many seconds do you have to pull your finger out of a consenting girl after she passes out?

Fwb wanted to try a devil's three way.
My buddy was down for it.
We fucked her raw, throat, pussy, ass.
Treated her like trash because that's what she was into with me.
After he leaves she breaks into tears.
She didn't enjoy it when he was being rough but went along with it anyways.
Says she only likes it when I'm that way because she loves me.
Try to gently break it to her that I could never love a girl like her.
She thinks it's because we're better friend's, but nah.. It's because she's a filthy slut.

She's a slut find her on FB send her a dick pic you know she will reply man all crazies do

this happens to me a lot. my wife likes to do lots of different positions and cums super quick so makes me stop a lot (she's spent after one orgasm). That means anytime I'm close we end up stopping and I have to start from square one again.

>feels bad man

Long story short

In college, not much sexual experience. Me, another guy and two girls naked and ready to go. Been drinking/nervous so couldn't get hard. Eventually got a semi and found my way inside the pussy. Came in about 90 seconds.

Oh, what could/should have been.

I had a girl pass out on me like that.
I fucked her anyways. When she cried rape I told her "prove it" because I wasn't rough with her and she was wet as fuck anyhow. No evidence of force used.

Happens when i am drunk i just cannot cum. Had an ex who would get all annoyed by it.

As soon as she passes out user, go read reddit rape stories lots of grimey you are lucky as fuck you didnt get cops called

Nah man.. I don't want it, and neither do you. She has doubled in girth since then.
She hit the age 30 wall at Mach 2 at least.

my brother. and no, i'm not a girl.

Watch out for drunk women unless you are 100% know lots will consent to sex forget do to drugs and call it rape even long term bfs seen it happened

Boy your name better not be Evan and her name better not be Jackie

My chick is fine with me pounding away if she blacks out lots arent though lol I did it to one chick who said "if it was anyone else but you I would say you raped me but I like your big dick" I shoved it in her when she was sleeping lol she did enjoy it to after a few minutes when she woke up

Master of Science

>"though she was a little redhead cutie"
Why the fuck is this in quotes?

Not him but I'm 36 and a while back someone posted naked pics of my x from when I was 20 damn she hit the wall wanted to vomit

Nice cover up for raping her bruh

That's when you go hardcore anal and fuck her brutally

Holy fuck I thought I was on /r9k/ I was wondering wtf is going on

Dude I'd rail that girl hard and tell her to call me daddy. Idgaf.

I've woken a girl friend up with my tongue before.. she started to bucking her hips before coming around. Then she put a hand on my head and pushed me back to see who it was before saying "if you're going to do it, do it right and use your fingers too." I happily obliged.. but after she came and I got on top of her with my dick out, she fucking cockblocked me.

So did he have a bigger dick then you? And also she liked it you fag she is saying that because she feels guilty do it again she loves it

That's fucked up man, should have said fuck it and pushed it in

fucking got me at the end ther lol

I had something kind of similar.
>Girl I loved and had been pursuing for years
>She would make out with me but would always leave before it became more
>like 20-30 times
>Finally kind of give up
>Decide to treat her like just a friend while I go after other, easier college girls
>Night before one of my biggest finals
>Studying super late
>She calls and is shithoused
>She tried to drive home shitfaced and hit a curb
>her dad will kill her if he sees the flat tire
>She says she's almost at my house
>Still love her so I say I'll help
>Change tire
>Tell her she can't drive home because still drunk
>She gets all lovey
>Wants to cuddle while I study
>I'm dead sober but say OK
>While cuddling she keeps trying to kiss me
>Professes her love for me
>Keeps reaching into my PJ's and pulling my dick out
>Afraid to let her because she drunk
>Don't want to get me too'd
>She's getting desperate
>gets completely naked and keeps doing the same stuff
>She's a tiny spinner but had the sexiest tiny tits I've ever seen
>literally killing me not to fuck her
>She's begging for it
>I can't take it
>Haven't studied at all and its 4am and my final is at 6
>Go to take a shower
>It's a master bath so there is no lock on the door
>I'm washing my hair and feel something touching my dick
>rinse soap out of my eyes
>she's on her knees sucking me in the shower
>I tell her I can't because she's drunk so she stands up and gets face to face to kiss me
>on her tip toes trying to weasel my dick between her legs
>She finally passes out
>I leave her in my bed and go fail my final
>She's gone when I get home
>She won't answer her phone for weeks
>Constantly worried she'll say she was raped
>Finally sends me a huge text saying she was wrong and loved me but couldn't face me after making me fail my final and making me fix her car and trying to rape me
>I did nothing wrong but still paid the price

Here's another, though it's not the sex that's awkward: A good friend of mine had a daughter who grew up REALLY nicely. She was 19, typical college girl, got herself a little tattoo and some new piercings to show her newfound independence, all that shit. She was back home for some holiday or someting, and texted me one night. She was leaving a baby-sitting gig, nothing to do in the small town, and we met up. I ended up fucking the shit out of her, she said she'd always had a crush, blah blah.

Kinda weird, kinda slimy on my part I guess, but it happens, whatever.

The next week when she was gone, my friend asked to meet after work for a drink. I'm like, "oh shit he knows and is gonna want to kick my ass!" NOPE.....I sat there for 3 hours with my buddy who is worried that his darling little girl is going wild and making bad decisions and turning into a slut, and I had to comfort him through all that shit while remembering I was balls-deep in her 4 days ago. That was fucked up.

It worked out ok. She married some fucktard her own age and she has like 6 kids now and is super-religious. My buddy is happy, I have the memories, but that moment was awkward af.

Uhm what the fuck i hope thats not true.

>killed herself with my 9mm in the bathroom while I was eating taco bell
Well that was abrupt

>be me, summer after hs about to leave for college
>meet smoke show and end up having a summer fling. Things are going great but I hold off on relationship bc college.
>she tries using sex to keep me interested. But she likes being in control
>I too like being in control
>we do this awkward back and forth of who's on top and who is leading.
>both of us getting a little frustrated and agitated but keep fucking.
>all the back and forth means added time my peepee was not in a warm place. And it decides to go limp..
>she starts crying and then hits me and yelling "what kind of pussy doesnt want to fuck a hot chick"
>she storms off and leaves
>that was the end of that summer fling. Told all her friends I couldn't keep it up.
>she got super fat now so that's something.

So a year ago I went on Grindr and found a passable sub trap to fuck, she wanted to be abused and liked it rough, her dick was locked up and couldn't get hard not that I would ever touch it, long story short choked her till she passed out, made her bussy bleed face fucked her till she threw up twice slapped her face till she had bruising slapped her hands till she cried, ripped hair out pissed in her mouth and face, called her a faggot and ugly spit on her made her eat my shit hit her ass so hard it will be black and blue was great for me I think she hated it she did say stop but being drunk and she wanted to be dominated I said fuck it never got a txt back either and she took her profile off she did cry most of the time though

>twisted my dick while riding me
>I made the face of a person dying
>thought that I liked that and did it again to me
>I almost started crying
>did end up crying
>she bursts out laughing

Was a one nighter with a classmate.
Looking at her after that felt like torture.
Other than that..not much

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My friend called me over to his house during the summer. He was frantic sounding and talking way to fast I couldn’t understand him so I just went to his house. He was awkward and not many people liked him, but to me he was like a Latino Kenny from South Park. When I got there he was visibly shaking and talking to me in a mix of Spanish and English. When he calmed down he told me he had the coolest thing to share with me but he made me promise to keep it a secret like 100 times. He tells me to be quiet and follow him and says just let what’s gonna happen happen. We walk into his moms room and his little cousin was watching tv. She’s maybe 7 or 8 and I’d only met her a few times. He walks over to her and talks to her in Spanish while pointing at me. She looks like she’s thinking then smiles and nods yes. He called me over and told me to just let her do whatever she wants. I’m super confused at this point, then she jumps off the bed and sticks her hand up my athletic shorts and starts rubbing my balls. I’m alarmed and caught off guard I look at my friend and he just nods. I’m frozen in place as my brain melted. Then I feel my shorts being pulled down but I’m looking up at the ceiling fan. Then I felt warm moist heaven around my dick. I looked down just in time to watch myself cum in her mouth. It felt like all my energy poured out through my dick and I sat down bare assed on the floor after I came. My friend then unzipped his pants and she relieved him to. She was with their family for the whole summer. And I came over almost everyday.

>me hosted a girl 19yo girl at Airbnb (i was 30+)
>she asked if i can slap her in the face
>i did
>she got horny, so i slapped her the whole time, with no warning... even public, in the store etc
> nasty sex later that night, i got a rimjob for the first time in my life
> next day her whole body looked like a mess, 50+ brushes
> i blocked her when she left
> two years later, i was casualy in the same city at hers... so i unblocket her, "remember me?"
> she agree to meet me at the hotel
> she was hungry and horny
> i forced feed her a kebab while fingering her in the bathtube.... the bath went all red because of the chili sauce...
> i blocked her again, for the second time

It was a long time coming tried to get her help she refused every time I was sitting on the couch h watching LOTR the hundredth time she threatened to kill herself I just said "go fuck off" we were fighting hear her pull it out of my drawer figured I was dead but went the other way, called 911 and ate my taco bell was relieved it was over actually I was going to break up that weekened

>On a houseboat trip with friends
>descent chick there 6/10 starts flirting with me as the days go on.
>she starts looking like a 9/10 after day 4 and in a bikini the whole time.
>everyone was sleeping on the roof, but rainstorm forced everyone inside.
>everyone is cramped together, she decides to sleep next to me
>after drinking we both settle down and she starts rubbing her butt into my hips
>get hint and pull her bottoms off and start fingering her.
>shes wetter than the lake outside, and a little loose.
>I slip my pool noodle in and I shit you not, 5 pump that ass and cum IMMEDIATELY.
>the 5 days on the boat with no jacking off took its toll.
>she turns around and says "are you fucking kidding me?"
>she jumps up and starts yelling, announces to the whole boat that I just came in 5 seconds.
>friends now call me one pump chuck. My name is Charles. Sucks doods

I probably would now, but there was the big age gap and I hadn't dated in awhile and was still coming up to speed on 20-something's and their daddy issues. I was down with wild girls and tattoos, but that was my first experience with the "choke me hard and let me call you daddy" mindset. Plus that big-assed cross on her back, it weirded me out in the moment.

The reason I stalked her was to possibly try again, but like I said, that ship has sailed and she's a ham-beast now.

I had a slightly chubby big titted redhead fiance that liked to drink a lot and pass out. I complained one time that we would be fooling around and she would fall asleep. She said "Just jack off onto my face. That's really hot anyways". I only did it a few times and she would wake up after the first or second shot and would open her mouth and take the rest and give me one or 2 cleaning sucks and then would fall back asleep

>don't know what made her like that so much
>I miss her

Man she has mental issues

>be me, 16 virgin, on date
>after movie parked on gravel road
>back seat kissing leads to massaging
>my shirt off, laying face down across gf's lap
>she massages lower back hits belt
>"why don't you unbuckle and i can massage better?"
>no_argument_from_me.jpg
>slide pants off lay down again
>gf massaging buns
>diamond
>"time to turn over, user"
>as i start to rise, gf's hand slides down my crack to my taint and balls
>instant cum while i'm rolling over but not let her know
>as i turn over but realize i'm done and my underwear is a mess
>"uh, i think its late, time to go"
>put pants on, drive her home
>do not talk about it then
>break up
>college
>see her after college
>talk...sexy talk...mention that date
>mfw she never knew--thought i was being "good"

It's fun doing shit like this

Damn I never came like that

Turns out she had pretty bad bipolar syndrome. Dodged a fat bullet but she was actually super cute.

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All this rambling horseshit but you decide you do need that one comma in there

I was seeing this slutty girl just because I wanted to get laid so after 3 times of going out, we ended up at my place for the sex time, we made out, she took of her dress and started jacking me while I kissed her boobs then she whispered "bite them" SO I did, she suddenly stopped and said she like it real hard when it was going to be a one time only soooo I was lik "OK"
She kept insisting on me not stopping even if she asked so it became weird.
Anyway during sex she asked me to slap her, pull her hair and choke her, she kinda cried and said things like "why do you do this to me? ", or "stop and I will suck you as much as you want"

It freaked me out so I stopped she got mad and told me I wa such a pussy she wanted me to degrade her, punch her if felt like it... She wanted to feel like a rape. I got out, never ever talked again, she's getting married BTW.

>descent chick
Her?

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>As soon as she dozes off I take off out the front door. Literally sprinting and running across yards and shit.
this made me laugh so hard,thanks user

Lmao decent *

I've fucked a girl like that.
She'd come back for more every few month's once the wounds had healed.
I was drawing blood with my teeth and gut punching her hard enough to bruise my own dick through her abdomen.

>be me, 42yo, travelling salesman
>stay in a hotel in the middle of fucking nowhere
>sitting in hotels restaurant in the evening, just me and a teen girl
>she is looking at the menu in despair, cant read cuz she is from Denmark.
>ask her if i can help. She joins my table, i explain menu to her.
>we eat , then proceed to drink.
>fast forward two days. She is 17, serious daddy issues
>end up in her hotel room making out. Undress her, small titties, dark nipples, landing strip
>go down on her.
>"please user, don't make me cum!"
>wtf.jpg
>"i start crying when i cum"
>fuck it, eat her out while fingering her.
>orgasm.exe
>She instantly starts crying like her fucking puppy died.
>diamonds turn to jelly.
>get dressed, go to my room

Don't fuck teens with daddy issues.

ngl that's hot af

That's definitely pathetic.. you're supposed to fuck through the tears you retard.

It's sad but it's fucking true lol. It was just light enough and I was just drunk enough to be doing parkour shit for like a mile home because I thought she would follow me. I tore out of her room in the dark so fast that her panties (must have been laying in/on top of my jeans) ended up getting stuffed down the leg and I found them later when I went to wash my jeans.

>bet she was pissed
>They looked niceish

I can imagine why she cries when she reaches climax. I imagine it is related to a sense of guilt and tied to memories of being touched and gotten off by dad.

>same girl, another date
>parking as before but daylight
>at a grocery store
>front seat, her car, she on driver side
>massaging my back again, shirt on, pants on
>tells me to turn over
>roll over, she does my arms and pecs
>moves down and says "you look happy, user"
>puts her hand on my bulge
>start cumming and i turn my body to face the seatback
>she thinks i'm being "good" or shy
>too embarrassed to tell her i came
>(now was worried this was going to be a problem for me)
>proceed to do other things all with creamed shorts
>never talk about it again, until that same convo years later
>obviously we never had sex while dating in hs

Dry humping my gf. Both of us 10 and spunking in my shorts. Never knew I could cum till that moment.

Dang not me I chickened out, it seemed like she could said I actually raped her I shit like that, and since there wasn't that much trust I really thought it was possible for her to do that.

going to an escort which advertised herself as blowjob and anal queen, with super huge bazookas.. was already sceptic at the door when the lady was half a head taller than me, with a more smoky voice than me.. at some point i realised this used to be a dude, he even cut his dick off and had some ugly looking meat-construction instead, and after OP he seemed to not be able to hold his pee properly anymore. after that moment i went limp and was close to puking..
i tried to find out what his motives were to mutilate himself and try to understand WHY WOULD YOU, but i couldn't even get behind his barrier of "hihihi i am such a girly woman".. i stil feel very close to puking when i think about that evening..

Attached: ohboy.jpg (720x720, 68K)

Worst ITT by far, I prescribe suicide.