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ITT: awkward sex stories i met my current girlfriend from my
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ITT: awkward sex stories

i met my current girlfriend from my sisters work, she is super hot and ive always considered her to be out of my league.

>be me
>a little over a month ago
>we are dating at this point but we havent had sex just yet
>casually making out one night
>i usually touch her boobs and rub my hands around but i never tried to force sex on her
>she pulls me over so i am on top of her making out
>things start getting pretty heavy
>both have removed our shirts
>she reaches down and starts unbuttoning my pants
>at this point my dick is as hard as a fucking diamond

let me explain, she is 5'4 and has a small framed body, i am 5'11 and i have about a 6.5 inch dick, its really girthy and has alot of veins, so i figured i would fucking destroy her tiny body.

anyway,
>she takes my pants off
>i struggle to take hers off, but eventually i get them off
>rubbing her vagina through her panties
>decide to go for it
>i hastily rip off her panties
>she takes my underwear off with the speed of jesus on cocaine
>rubbing her clit
>just as i go to stick it in, she is obviously tensing up
>vagina is so tight i cant get it in more than half an inch
>no lube around
>she is dripping wet, but the more i try to force it in she keeps making a painful face
>i stop for a minute,
>dick goes completely soft and nothing can get it back up
>i feel like a fucking moron
>immediately start apologizing
>put clothes back on
>we fall asleep

so yeah, that was the story of how i failed at fucking my current girlfriend the first time.
>>
/thread
>>
>>675405463
post her nudes you fucking faggot
>>
>>675405671
i have some on my phone, let me get on here on my iphone and ill post them
>>
>>675405859
based anon
>>
i got one, but im on pain killers so it may take a bit to type and there will definitely be errors. i apologize in advance.
>>
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>having sex with my black gf
>in the heat of the moment
>call her "my prize negress"
>she leaves and never calls again
>mfw
>>
I'm on mobile so fuck your green text.

Once upon a time 17 year old me was hooking up with the hottest and cutest girl I've ever seen to date. Long story short I got her over to my place and she was really into sex so it didn't take long. As things get hot and sweaty I tell her to get ontop of me. For the record my dick is above average and she wasn't the best at riding, coupled with the fact that I choke hold my cock when I jerk it didn't make climax an easy thing to achieve. So as it were I tensed up as she was bouncing on my cock screaming in pleasure and tbh the sight of it was enough to make me cum despite it not being the greatest sex.

Long story short I got a cramp mid bounce from tensing up and the pain was enough for me to shove her off the bed and grab my leg in pain making a monstrously disgusting face and sound as she was on the ground trying to figure out wtf happened
>>
>>675406192
I cant find this fucking thread on my phone to post the nudes
>>
>>675406795
There is a search feature you stupid little shit
>>
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>>675406795
keep working based anon you will find it
>>
>>675406653

I called my black FWB my "nigger whore" once and it really turned her on. Things got real interesting in our relationship after that.
>>
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>>675406970
Found it, anyway here is the nude pic, she's nude in the picture you just can't see any tits
>>
>>675405463
>ITT: awkward sex stories

>ITT: showing off about having a girlfriend and a big penis

You're pretty pathetic, you know?
>>
>>675407511
>6.5
>big

ive never considered my penis to be "big"
>>
>>675406597
>be me, 18
>GF starts getting frisky
>start making out
>me sitting on the side of the bed, her in my lap
>fastforward
>naked in same position (side of bed, lap etc)
>she used to have really bad scoliosis, so she has a titanium rod in her spine, so she cant really move her hips independently from everything else, so when she rides, she sorta just moves her entire body up and down
>she gets into this shit, goes way too far up and i slip out of her pussy, and promptly into her asshole
>never done anal before, neither of us are really interested in it
>hurtsbadman
>hurt her a lot more, because 7 inches of dick in a virgin asshole
>unbeknownst to me, she has some sort of weird involuntary reaction when she is subjected to immense pain in a short amount of time
>she fucking falls face first on her bed
>i laugh for a little cause i didnt know what was happening
>she starts having a fucking seizure right there
>i roll her over because shes face down and would have suffocated because of her bedsheets
>at the same time, her legs extended, launching her body off the bed and halfway across the room
>with a huge boner i run over and hold her until she wakes up
>no sex for the rest of the week
still careful about riding a year later
>>
> meet this hot chick at work
> start texting
> go to her house one night
> fuck
> cum in under 4 minutes
> sheaintimpressed.png
> leave anyway
> keep texting
> get another night with her
> go down on her then fuck show her my best moves
> she's happy
> later we start 69
> both getting into it
> involuntary pre-orgasm spasm
> end up kicking her off the bed
> she is on the floor in agony
> wtf

She saw the funny side that was six years ago. We're married now
>>
>>675407112
90% sure left is my old manager
>>
>>675407618
Do you consider anything about yourself to be worthwhile?

If so, you're wrong.
>>
>>675407710
>run over with huge boner

Fucking kek
>>
>>675408001
I just told you I don't have a big dick and you are still ass hurt
>>
>>675407877
her name is carley somthing i used to have her facebook some anon posted her here i dont know her personally i want to say carley cates?
>>
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>>675408001
You sound like you have a tiny dick bro.
I'm not op but here's mine
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>>675408128
Not OP, but you sound like a pretty sad waste of time. Just sayin'.
>>
>>675408034
not even kidding man, no idea how i kept a boner while i was so panicked
>>
>>675407710
That was exciting the whole way through. Glad she didn't break your dick.
>>
>>675407511
The fact that you said he was showing off about having a girlfriend says a lot about you, anon.
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>>675408160
nah nevermind. her name was jessica, and lives in new orleans
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>>675407618
Here's another
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>>675408001
And another
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>>675408417
thought she did. didnt know it went in her ass until she told me. all i felt was my dick get pressed on/bent. it was the first time wed had sex in a few days, so it was diamonds, to make things worse
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>>675407504
hnnnnnnnnnnnnnnnnnng
>>
>>675407511
>showing off about having a girlfriend

I'm guessing you've never had one?
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>>675408001
Here's a picture of me taking a selfie with the flash after I just woke up
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>>675408887
OP here, that is not me.
>>
On mobile. No green text.

Go to skanky girls house. We are making out. Got her shirt off and still making out. She's got my pants down playing with my dick. Her roomie I didn't know about comes walking in and sees what's going on. She sets on the bed and starts sucking me while I'm making out with the other. I cum in a few minutes time. Pretty embarrassing.
>>
>>675408798
I don't start a thread about it when I do
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>>675409092
IF you do, anon.

IF
>>
>>675408887

nice fuckin dirt stash u got goin there dumbass
>>
>>675408515
nice scullcandy crushers, they sound nice?
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>>675409258
Im a dirty little fucker who's barely hit puberty. Let me have my sanchez
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>>675409246
Right now I don't. In the past I have. I've never started a thread with an "awkward" story about my dick being "oh too fucking big"
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>>675407511
>showing off about having a girlfriend and a huge dick
>6.5
>showing off
>girlfriend
>>
>>675409274
Actually I'm crazy surprised at the quality, the bass features fucking stupid, if I wanted my head to shake like that I'd fuck my ear with a vibrator but other then that I'd reccomend, price is a lil high tho
>>
>>675409497
Dude clearly you are mad because someone said they have a bigger package than you. If OP was trying to show off with this story, then he is just as pathetic as you.
>>
>>675409497
It's not that I have a big dick, which I don't think I do. It's that she has a tiny body and a small vagina
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>>675408231
>>675408515
>>675408705

>I love that all you faggots have the need to show each other your dicks. If only there was an app where faggots like you could meet other faggots in your local area...
>>
>>675409735
There's nothing awkward about OPs story. Awkward stories are about embarrassing things.
>>
>>675410065
How is it not embarrassing? I was about to fuck the hottest chick and my dick got soft
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>>675410044
I catfish dudes all the time bro. I actually convinced some guy I lost my legs and he was still trying to fuck my long after.

Fucking fags amirite
>>
>>675410251
I'm guessing these guys have micro benis's and go soft on the regular??
>>
>>675410416
yeah, but obviously im showing off about my megahuge 6.5 inch penis
>>
>>675409071
>>675406765
>tfw you can greentext
>tfw /b/ to stupid to realize
>>
>>675410251
Sorry I doubted you. Sounds like you have a bunch of hangups about sex. Just have fun with your girl and don't worry so much about your "performance", man. You'll only make her get stressed if you worry about stuff like this.
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>>675410588
fucking shit man
you have a slightly above average size penis
show off

topkek
>>
>>675410825
Yeah because I'm going to use fucking meme arrows on mobile
>>
>>675410891
oh yeah and i have a girlfriend, which is a rare thing for people to have.

i am a fucking show off
>>
>>675410831
Fuck you faggot, you don't get away with being a twat just because you got attacked and now you can't handle it so you go and play nice.

You're insecure AND a pussy
>>
>>675405463
>ex-gf was kinda bi in high school and we would party with a friend.
>during spin the bottle game all drunk, gf told me to take friend to other room and do what I would to gf.
>liked friend, butjust wanted back at g/f so took friend to other room and kissed some
>next turn told g/f to take friend to other room and do what she wanted me to do
>10 minutes hard cock waiting.
>tfw both came back and told me it was no fun without cock.
>threesome.jpg

>two years later, g/f, friend and I at wedding and g/f tells me to take friend to room and fuck.
>friend is pretty and into it, but .....
>tfw when we watch the sun come up and she asks me if I came.
>not really.jpg, but it was fun. You?
>same here
>lets go get breakfast then.
>>
>>675411220
Fuck you man; I thought OP was enough of a loser to post a story that's not really awkward, so I called him on it.

Now I realise he's so much of a loser he can't even be intimate with someone he's trying to fuck, so I'm no longer mad and just sad for him.
>>
>>675411126
im the anon who wrote the accidental anal story

surprised i wasnt accused of showing off for having a GF and an above average penis
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>>675407840
keeper
>>
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>>675411458
>says having gf is showing off
>calls OP sad
>TFW
>>
>>675411458
are you the type of guy that everyone makes fun of on here? do you have a neckbeard and wear a fedora? i feel like you are
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>>675411458
>says a 6.5 inch dick is big
>telling people i have a girlfriend is showing off
>says im sad
>>
>>675407511
You don't get out much do you anon
>>
First girl with to sleep with me
>Goin deep goin hard
>want to cum inside but don't want to be rude
>"should I..."
>"noo slam your dick in me"
>fall out
>helicopter effect
>cum all over the place
>her face, stomach, myself, her hoody across the room

Also one time she said to me
>Explode inside me

And I may be mistaken but I swear to god it was followed by

>K-pshhh

will try and think of moar
>>
>be 17
>dating 19yo coworker
>been dating about two weeks. No sex shes a virgin
>making out in car between college classes
>she says anon wanna skip class and go to my brothers house. Hes not home
>fuckyiss.png
>get to house, making out on couch
>i pull her skirt up andpanties off
>eat her out til orgasm
>she says to lay back and she will return the favor
>she leaves and returns with a washcloth
>cum in this when you are ready
>my first blowjob commences
>super excited but its just awful
>teeth scraping, no hand action
>10 mins in im nowhere close
>shes looking tired
>I grab washcloth and say anon im about to cum
>she pulls off
>I fake nutting
So yeah.....I faked an orgasm during my first blowjob
>>
>>675413648
I have other awkward sex stories with this chick....even though we did have some amazing sex over a couple of years. Really miss this chick at times.
Will share if anyone wants them
>>
>>675413648
can i ask how a male fakes an orgasm
>>
I've got 2 stories, the second one is much better

How I lost my vcard
>best friends with 9/10
>perfect girl
>she attacked me last week and we hooked up
>got to 3rd base the first time
>go to the Grove after being with her fam all day
>walk around, talk, look at stars
> she says "hey can we try something?"
> "okay"
>"can we talk with your dick inside me"
>"?"
> "not really sex, just laying back and relaxing while your inside me"
> "okay, I'm gonna wear a condom though"
>"okay"
> I get on a condom, and we go down beneath a big tree
> after I put the condom on, she starts havi g second thoughts
> "I already put it on, we gotta go through with it"
>"okay"
>she starts taking her pants off
>it's the beginning of January in SF, it's about 40 degrees out
>we're both bundled up in coats and beanies but I manage to get inside her
>inevitably we start having sex for about 30 minutes
> it was pretty terrible
> eventually I stop and we both laugh about it
>both go home
>realize I just lost my vcard to my best friend
The next story is way more awkward, don't have these pretyped
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>>675410287

Impressive.
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>>675414944
Proof btw
>>
>>675414524
>one week later
>I pick her up and we are trying to decide where to go
>she says fort funston
> after making out for a little, we drive to fort funston to duck for the second time
>getting out of the car, I can see from her sweats she's wet
> like ridiculously wet, it look like she'd peed herself
>we walk to the top of this old fort with a blanket
>at the top we lay it out, and she says to strip
>worst fucking idea, we should've stayed in the car
>we both strip down and its freezing cold and windy
>naked, we start making out, and I try to put the condom on
> km only semi hard, not enough to put it on
>after trying literally everything to get me up, we give up
> I felt terrible about it, and I told her
>she understood it was just the cold
>she held me in her warmness for a while

I'm no good at telling these stories, but goddamn do I miss that bitch, she was an angel, and I'll never get another one like her
>>
>>675414524
go on
>>
>>675405463
if you waited until you were married this would not have been an issue
>>
>>675414385
I'm down if u are
>>
>>675415272
KEK
>>
>>675411066
>not using meme arrows irregardless of posting platform

summer's come early
>>
>>675414521
Certainly. Cover dick with wash cloth. Act like you are nutting. Scrunch up cloth and go throw it in hamper.
>>
>>675411066
"meme arrows"
is this your first hour on this site?
>>
>>675407175
This is my fetish
>>
>>675415406
A little more backstory. We were both in college....working retail...both still lived with parents. Nowhere to go bang so we'd just fool around in our cars and eventually started having sex in our cars. We'd eventually start hooking up in her parent basement when the opportunity arose.

On cellphone. be patient 3 or 4 akward stories inbound
>>
>>675412842
what the fuck are you even talking about nigga?
>>
>>675405463
>Getting into it with gf
>Fingering the shit out of her
>She's cum multiple times
>After she cums again I pull my fingers out and go to grab her tits
>Look down
>Blood everywhere
>Dafuq
>Hand covered in blood
>Blood smeared all over her tits and stomach
>Both freeze and stare at her
>Spend the next several minutes probing her vagina trying to find what's bleeding
>Don't find it
>Proceed to fuck to shit out of her anyways
For a moment I considered just going with it
>BLOOD ORGY
>>
>>675414521
> hnnnnnnnggg
>>
>>675411066
Lol is that what they're called? Meme arrows? Good. I can google how to mobile meme arrow now thanks mate
>>
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>>675405463
kek
>>
>>675415696
only time in history its good a girl didnt swallow
>>
Two short stories
>be 17
>gf is 15
>idgaf if it's a little pedo-ish
>we've gotten to third base but never had sex
>month into relationship
>nobodies at home
>we're not even doing anything dirty
>she looks at me
>"you wanna have sex"
>okay.jpg
>we awkwardly get naked
>try to put on condom
>she laughs bc it's backwards
>I put it on
>I put it in slowly
>we've both lost our virginity in this moment
>I start slowly fucking her
>condom is too thick to cum
>never came my first time
>fucking gay as shit
>also i hit her head on the backboard on accident and we laughed mid sex

Second (better story)
>fucking her in my room
>going hard, different positions, sucking on those cute little feet
>fuck me this is awesome
>get lower and start going harder
>she's already had more than one orgasm by this point
>fourth time we fucked that day
>I pull out to cum (irresponsible underage unprotected sex is the best)
>fucking cumshot blasts me in the eye
>blast her face
>her tits
>fucking everything succumbs to my massive cumshot
>never laughed harder during an orgasm in my life
>she looks up at me and laughs her ass off too
I'm still with her
Fuck I love her
>>
>be me at 18
>reconnect with girl who had a crush on me in middle school
>plan to meet up
>we are at my friends messy apartment drinking vodka
>I take her into friends room
>start making out and heavy petting
>I tear her shorts off and start eating her pussy
>she sucks me off with dedication
>I turn her around bend her over slap her ass and penetrate
>Fuck her for a good 20 minutes
>three of my friends burst through the door
>instantly lose erection
>they left but slapped my ass before they left
>couldn't get it up after that
>we leave the room disappointed
>>
>>675407504
Her eyebrows are fantastic.
>>
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>>675416755
>Being on 4chan
>Not understanding superior ironic Meta humor
>>
>>675416329
>weve been fooling around quite a bit and she decides she wants to lose her virginity
>were in her 2002ish chevy cavalier
>young, dumb, full of cum
>penis full of blood and took over thinking for my brain
>driving around and see empty gravel parking lot behind a local resturaunt
>lets pull in here...
>start making out, finger banging her
>she orgasms and then says i want you to fuck me
>ok but hows this gonna work out
>she lays back seat and says climb over here
>pulls off jeans and spreads her legs.
>i scramble across and unbutton/unzip my shorts
>put on condom and slowly try to get it in
>she winces in pain but says keep going
>eventually get it in and she starts to enjoy it. A little blood
>we get hot and heavy
>windows fog up...were in the heat of the moment
>meanwhile employees of this resturaunt are parking around us to go to work
>guess they went inside and told manager
>we finish. Put clothes on and get ready to drive off
>manager was standing nearby and stops us
>i roll down window. Manager bro says next time get a hotel or ill call the cops
>>
>>675407504
/tips my fedora. Well played!
>>
>>675417026
Agreed man
>>
10mg cialis every other day has changed my life. Even days I forget to take it, the performance anxiety isn't there. So everything is gold.
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