Awkward Sexual Experiences

[skate_bored]

TL;DR I laughed very hard during a funny threesome. Sorry this was very long and not super awkward, but it was a very abnormal and awkward experience overall for me.

this is why we're here. awesome story

[Nosferatu]

^That is a very open and committed relationship you have with your friend. I couldn't do it. Are your dicks the same size or something? I could see that creating weird vibes among many other things.

[get gnarly]

^That is a very open and committed relationship you have with your friend. I couldn't do it. Are your dicks the same size or something? I could see that creating weird vibes among many other things.

We're really close. And it only happens with chicks neither of us are interested in. Coincidentally, our dicks are virtually the same size length/girth which makes it a non-issue.

The only other thread worthy threesome tid bit is that the first one we had together, I had fucked the girl earlier in the night and couldn't get hard for the whole thing. Luckily the chick was cool and didn't get offended/turned off so we made it happen again and tore it up.

[wallieD]

Expand Quote

^That is a very open and committed relationship you have with your friend. I couldn't do it. Are your dicks the same size or something? I could see that creating weird vibes among many other things.

[close]

We're really close. And it only happens with chicks neither of us are interested in. Coincidentally, our dicks are virtually the same size length/girth which makes it a non-issue.

The only other thread worthy threesome tid bit is that the first one we had together, I had fucked the girl earlier in the night and couldn't get hard for the whole thing. Luckily the chick was cool and didn't get offended/turned off so we made it happen again and tore it up.

[get gnarly]

Hahahahaahahahaha basically

[shark tits]

ha, those were great 'get gnarly'. i had a dear friend of mine who passed away, we used to travel to london bridge on occasion. we used to observe 'naked hour' from 1-2 anytime we had female company over. about a decade plus 2 yrs [one skor?] he came home w/ a bird and our friend 'gay joe'. the bird was halfass jerking me off on the couch but 'stencel' took over for her til i made him quit seconds later.
'i'm more punk than you handsome jack' he'd say in his yogi bear cadence. gay joe leered and offered his foul services.
for anyways, i go to bed w/ a hard on and am working on it when the girl comes into the room. i relinquish control and she finishes for me then orders 'don't put that away yet, boy'.
did i mention she was 15, maybe 16? accepting a handjob is one thing but i'm no statuatory rapist so i encouraged her 'go sit on stencel's face, he'll be stoked.'.
she did so i joined them 10 or so refractory minutes later. i smacked her ass and cajoled another handjob outta the deal. fast forward a few yrs and she gets off stencel's dick and goes to the bathroom.
'what are you laughing at, handsome jack?'
'you got sloppy seconds'
'no, i got first and thirds' he deadpanned back at me. then we laughed about all the jiz leaking out of her.
due to her girth/ethnicity we nicknamed her 'the gordito burrito'.
during one eiffel tower our balls touched and i retracted while stencel blocked the backdoor. 'sorry you're not as punck as i am' he shamed me like he'd done 4 yrs prior.
she informed us 'i've known you this long, you guys are my best friends'.
i thought it was sad.
stencel told her 'thanks for being so friendly.'
god i miss him!

[Carrolls Chesthairs]

Expand Quote

^That is a very open and committed relationship you have with your friend. I couldn't do it. Are your dicks the same size or something? I could see that creating weird vibes among many other things.

[close]

We're really close.

[dirtyweemidden]

ha, those were great 'get gnarly'. i had a dear friend of mine who passed away, we used to travel to london bridge on occasion. we used to observe 'naked hour' from 1-2 anytime we had female company over. about a decade plus 2 yrs [one skor?] he came home w/ a bird and our friend 'gay joe'. the bird was halfass jerking me off on the couch but 'stencel' took over for her til i made him quit seconds later.
'i'm more punk than you handsome jack' he'd say in his yogi bear cadence. gay joe leered and offered his foul services.
for anyways, i go to bed w/ a hard on and am working on it when the girl comes into the room. i relinquish control and she finishes for me then orders 'don't put that away yet, boy'.
did i mention she was 15, maybe 16? accepting a handjob is one thing but i'm no statuatory rapist so i encouraged her 'go sit on stencel's face, he'll be stoked.'.
she did so i joined them 10 or so refractory minutes later. i smacked her ass and cajoled another handjob outta the deal. fast forward a few yrs and she gets off stencel's dick and goes to the bathroom.
'what are you laughing at, handsome jack?'
'you got sloppy seconds'
'no, i got first and thirds' he deadpanned back at me. then we laughed about all the jiz leaking out of her.
due to her girth/ethnicity we nicknamed her 'the gordito burrito'.
during one eiffel tower our balls touched and i retracted while stencel blocked the backdoor. 'sorry you're not as punck as i am' he shamed me like he'd done 4 yrs prior.
she informed us 'i've known you this long, you guys are my best friends'.
i thought it was sad.
stencel told her 'thanks for being so friendly.'
god i miss him!

not sure why but I feel really dirty just reading this... youre a creepy son of a butthole sniffer

[JB]

sharktits, i wish you would write a book.

[ill_Murray]

There we were, sitting in a circle, taking shots of what smelled like rubbing alcohol in the freshmen dorms.  It was a pretty decent amount of alcohol into the night when my friend Ashely (who I had no previous sexual encounters with) looked at me, cast all romance aside and simply blurted out, "Wanna fuck?" 

We make a hasty retreat down the hall back to my room and make it over to my bed.  Little to no foreplay ensued as I began the game of pin the tail on the donkey with her vagina and my dick almost fully clothed.  My inner dialogue raced along, as I finally pushed it home, "Thisisgreatohyeahfeelssogoodfuckyeswaitwaitwaitouchowpain," only to be cut short by a burning/stinging sensation on my dick which I immediately withdrew.  I sat back and much to my chagrin I saw a string coming out...

I had just...stuck my dick...while she...

The mental pictures of Uteran walls shedding their lining coupled with the alcohol and all the movement was enough to send a pretty heavy rain of my daily intake all over my floor. 

She was actually pretty cool about it and we laughed about it but at the time I was not too stoked.

[ice nine]

she thought she could have sex while having a tampon in? is that even possible?

[ill_Murray]

she thought she could have sex while having a tampon in? is that even possible?

Couldn't really get it in, I was too drunk to notice at first and I guess she had been wasted enough to forget it was in there in the first place. 

[shark tits]

shoulda pulled it out w/ your teeth like casper and told her she had 'mad flavor' as you get your detroit red wings.

[ill_Murray]

shoulda pulled it out w/ your teeth like casper and told her she had 'mad flavor' as you get your detroit red wings.

We all make mistakes

[Donkey Lips]

she thought she could have sex while having a tampon in? is that even possible?

I was friends with a girl in college that did this twice in the same night. She apparently forgot she had a tampon in, whored out at a party and found a guy who obviously didn't care about the road block...because he just rammed his dick in and pushed it in further. She didn't notice. When they were done, she went home and got booty called by another dude, who came over and proceeded to push the cork further into the bottle. The next day she was telling my girlfriend about it and crying that she was going to die. I laughed my way out of the room. A week later I asked my lady what ever happened with that situation. She said Jana said it "fell out" a few days later. Chicks, man.

[jimi420]

I've been on a 4 month dry spell lately and I've resolved to not jerk off until after I Fuck again, so I've been hella desperate. This girl who stood me up on Valentine's Day 2 years ago hit me up earlier this week to hang out. I don't think anything of it, we never got too far anyway so I pick her up and take her to this spot I always go to to question my life and all that shit. I put on some Drake and The Weeknd (girl's in my generation will Fuck anything if either of those two are playing), and we start making out and getting handsy, when all of a sudden a security guard shows up. I'm freaking because my tags are 2 months expired, but he just tells us that that's his weed smoking spot and another, less chill, security guard is on his way to trade shifts. We leave and she says "well, let's go somewhere more comfortable" so she tells me to go back to her spot. We get there and pop in Joe Dirt, and she starts drinking some Henne, I don't because I don't want to get caught drunk driving a car with expired tags. She gets plastered, like slurry, sloppy. She then starts slowly masturbating, then goes harder and faster until it's violent. She closes her eyes and starts growling, like guttural, deep growls. Mind you I'm still kinda just kickin it next to her on the couch. This goes on for ten minutes, and I notice she's fingering herself so hard she's bleeding. Idk what to do, so while she continues to masturbate with her eyes close I slowly slide out of her apartment, and just leave. She texted me the next day and apologizes but I've learned that girls like that still probably cause you bodily harm, and I'm not into that shit anymore

[JB]

jimi's stories are the best stories.

that one was gold! holy shit.

[skate_bored]

great story. but i still would have jerked off on her.

[Gray Imp Sausage Metal]

Long story short: Once I was hooking up with this girl and we were at that point where pants were off and foreplay was going down. She was on top, clothes were off, and my dick was between her butt cheeks. No condom was on yet or anything and out of nowhere she just goes for it - puts my dick in her butt. It was weird because she'd apparently gone into the bathroom to lube her butthole right before all of this.

that's actually pretty cool (apart from the raw dog part)

[saucy ragu]

Expand Quote

Long story short: Once I was hooking up with this girl and we were at that point where pants were off and foreplay was going down. She was on top, clothes were off, and my dick was between her butt cheeks. No condom was on yet or anything and out of nowhere she just goes for it - puts my dick in her butt. It was weird because she'd apparently gone into the bathroom to lube her butthole right before all of this.

[close]

that's actually pretty cool (apart from the raw dog part)

[Jared]

shoulda pulled it out w/ your teeth like casper and told her she had 'mad flavor' as you get your detroit red wings.

Just read this midway through a bowl of tomato soup and can't figure out if I want to finish it or not.

[Justis]

Just now this bitch threw up sucking my dick

[jimi420]

Just now this bitch threw up sucking my dick

Did she suck the puke off? That's the only proper thing for her to do

[Justis]

Expand Quote

Just now this bitch threw up sucking my dick

[close]

Did she suck the puke off? That's the only proper thing for her to do

Lmao she did and then I busted in her face. Smoked a reluctant blunt afterwards as well

[Rumpleforeskin]

girls like that still probably cause you bodily harm, and I'm not into that shit anymore

Hahahahahahahaha, Jimi is the one that needs to write a book..  "My Erotic Life"

[doublesteveburger]

I just remembered today of a funny time I experienced so I thought I'd share. I was fucking my ex-girlfriend once while fucked up on oxycodone so my mind was kind of elsewhere. She was talkin dirty into my ear and whispered something along the lines of 'i love it when you're inside me' and in my numbed out fucked up stupor I mirrored her words and whispered into her ear, 'i want you inside me so bad'. We both kinda stopped, laughed hysterically then I proceeded to cum on her face.



Also, my cat licked my asshole once while I was fucking this girl. It was probably more awkward for the cat.




 

[Matze]

^^this could be me.

[lickcakes]

the first time i had sex with my boyfriend at the time, i accidentally peed on him

i got gag reflex from sucking another guy's dick and threw up on him

[ChewyPoo]

2 weeks ago I recieved the dolmio grin with my new gf in one of our first experiences

[tobey]

the only awkward thing i can think of or that really happened to me when i was 18. I had a fuck buddy at the time and we would always get drunk and text each other like wanna meet up? So one night we did and instead our usual spot (my car) she sneaked me in to her bed room. Now this girl gives the worst head like i could never cum while getting head but she just didn't know how to satisfy a man. So we were fooling around and i started to go down on her, to show her up on how to really satisfy someone. Now i never gave head to a girl before but i watched a lot of girl girl porn so i wanted to give it a try. She gave me 1 second of trying and just said she felt awkward and she said she wanted to give me head, i just said na thats alright and i kind of begged her to let me go down on her but she kept on saying no. That was a pretty awkward

Just recently when i hooked up with my first tinder girl ever she was in my bed and getting undressed so i started to undo her jeans and kind of making my way down there and she just said "um what are you doing" i said "im about to give you head" and she said no. I was really bummed and then the sex wasnt that good either so i was super bummed.

Do girls my age not like getting their pussy eaten out?