ITT: Awkward sexual experiences

ITT: Awkward sexual experiences.

I'll start.

>Be me, britfag.
>Talking to girl on tinder for a few days, just the usual flirting and shit.
>Pretty cute face, in the pics that I saw she was a little chubby but not obese or anything.
>Conversation naturally turns towards sex, turns out she's into the same stuff.
>Skype for a bit, never saw more than her face, didn't think much to it at the time.
>Arrange to meet up.
>Day eventually arrives, catch train and wander the mile or so towards her flat.
>MFW stops answering texts when i'm like 200 yards away from the door.
>After 10 minutes, get a text saying she's sending a flatmate to open the door for me, since she can't be bothered.
>Get into flat eventually, quickly ushered into a room by mystery girl.
>Realise it's her, it's the girl.
>OhFuck.jpg

Cont. 1/5

Other urls found in this thread:

javsex.net/watch-movie-1pondo-092415-159-aoi-shirosaki.html
en.wikipedia.org/wiki/Play_(BDSM)
twitter.com/NSFWRedditGif

>Sit on bed awkwardly, trying not to make it clear I'm surprised.
>Turns out she's still quite nice to talk to, but looks completely different in person.
>Lie on bed next to her, faces quite close to each other as we talk.
>Her phone goes off, she moves over and looks at it.
>Minutes pass, girl is still scrolling through her facebook feed for some reason.
>Be 15 mins later, about to get up and leave.
>Puts phone down, starts talking about kissing.
>Weigh up my options: Either go through with it for another notch in the bedpost, or leave and humilate the poor girl.
>Fuck it, kiss her.
>She barely moved her mouth, pull away thinking she was joking or something.
>Turns out, nah, completely serious.
>It's really weird, worry that she'll think I'm the weird one.
>Feels super wet between her legs. Guess I'll just go for it.

Cont. 2/5

go on

>10 minutes of fingering later, figure twice for her is enough for it to be my turn.
>Carry on kissing, move her hand to my crotch.
>She fumbles with belt clasp for solid minute before I do it myself.
>Girl grabs limp penis.
>Looks me in the eyes with a 'Yeah you like that don't you?' sort of smile.
>Starts jerking me off, but just the base, so basically pointless.
>Puts it in her mouth and sort of moves it around a bit.
>Get maybe a semi.
>Another 10 minutes later, begin to get worried I'm taking too long to cum.
>Tensing like crazy, calling forth ancestral spirits to help me fucking nut.
>In an effort to not seem entirely autistic, start fingering her again and just do it myself.
>Finally come on her, since she asked me to.
>Girl starts complaining and shouting about rapidly cooling jizz.
>SquealLikeApig.WAV
>Forced to clean up.
>"So user, you wanna...?"

Cont. 3/5

Why would you continue after that? Jesus.

also, bump

more more

A mixture of self-loathing and pity. Anyway.

>Somehow get a semi again, put on condom.
>Looks dumb as fuck but whatever.
>Have some fairly normal but decent doggy style sex.
>Girl comes, I come shortly afterwards and pull out.
>Fall beside her, panting.
>Make a joke about how she'd never know that was my first time (It wasn't)
>Looks at me and says it definitely wasn't my first, asks how many people I'd actually slept with.
>Tell her she's my 4th, she looks shocked.
>"Don't look at me like that, it wasn't *that* good"
>"No no user, just that's nothing compared to me."
>For fuck's sake.
>"oh haha how many for you then?"
>Puzzled expression as she calculates the number.
>37.
>Thirty fucking seven.
>Must've spent all her SeXP on some other useless skill tree, instead of one to actually be any fucking good at it.

Cont. 4/5

>or leave and humilate the poor girl.

she totally deserved it.

Yeah, but which bit makes you say that in particular?

sauce

javsex.net/watch-movie-1pondo-092415-159-aoi-shirosaki.html

I just stopped reading at the quoted "poor girl".

I dunno, I'd feel pretty shitty if a girl just upped and left.

>Awkwardly clean up and have some idle conversation.
>Somehow ends up rating me a 'solid 8' out loud (Not really but it's nice she would say that)
>"What would you rate me user?"
>Most awkward conversation of my life and least convincing response of "oh like, definitely an 8 too yea" follows.
>Gets her phone out again whilst we're talking, begins swiping on tinder.
>FuckThis.gif
>Tell her it was about time I left anyway
>Be walking through the city with her to the train station.
>Pass fancy new clinic
>Comment about since it was for students, the only thing they'd do would be constant STD tests.
>"I wouldn't know haha."
>Sudden bolt of fear as I realise she probably hasn't gotten tested, ever.
>TFW I put it in her mouth.
>TFW 37.
>TFW stings when I pee.
>TFW

nobody asked for that

>Tensin like crazy

oh dear...

oh, you poor delicate PTSD fagits

>>TFW I put it in her mouth.
>>TFW 37.
>>TFW stings when I pee.
>>TFW

confirmed -- you totally deserved it.

> Meet girl, friend of a friend. 7/10 but pretty cool
> Drinking and hanging out
> Start kissing. Fumbling. Move to bed
> More kissing and groping. She's completely passive
> playing with her tits. start rubbing her crotch through her pants. She's not putting her hands on me at all.
> She's still kissing back though, so she's clearly interested.
> Put hands in pants. Insert finger....what's that?
> oh-its-a-tampon.jpg
> Remove finger. dafaq? She didn't say anything about being on the rag
> Confused about next steps, ask "what do you want to do tonight?"
> "play with me"
> lolwat?
> "play with me"
> "What does that mean?"
> "play with me"
> Kiss and grope more, until I forget about tampon.
> Take off pants, start trying to get my dick in there
> Oh right, tampon.
> "I guess we can't have sex tonight, plus I didn't bring a condom. What should we do instead?"
> "play with me"
> "WHAT DOES THAT MEAN?"
> "play with me"
> SRLSY WHAT DAFAQ DOES THAT MEAN?
> Losing my shit.
> It's the only thing she says. Repeats it over and over again
> How many times? It's over 9000!
> Is this real life?
> She's not using her hands still, isn't acting like she wants to blow me. I'm not playing with her tampon anymore
> Not even in the mood at this point.
> Eventually, give up. Go to couch. Sleep.

Weirdest night of my life. I wish I had some kind of clue about what she wanted. Sometimes booze makes it easier, sometimes the booze just makes things weird.

No one cares, post pics or fuck off OP

She probably wanted you to be her Daddy. Chicks into age play are fucking weird.

en.wikipedia.org/wiki/Play_(BDSM)

my LEGO trains always tell me "play with me". Pic totally related. YAY!!!!!!

> Be me, 18. virgin as fuck
> Decide to see hooker about some business
> Call the agency. Have one "girl" left
> How old?
> "42"
> fuck it, send her over
> She shows up. well, it's a woman.
> Talk money first. Pay her 100$
> Oh, and she needs cab fare.
> She gets undressed. Puts condom on me. Starts blowing.
> totally-unerotic.jpg
> It's been a long day, so she asks me to rub her shoulders.
> Why isn't she paying me? At least she can feel what I'm doing.
> Gets on bed, starts doing doggy
> can't feel shit. She's loose. First time with condom.
> At least I can see her dirty immigrant asshole. Oh wait, that's not a good thing
> She rolls over, start doing the missionary
> Can't see her asshole, but now I can see her face, so....no improvement
> Pump for a while but it ain't happening
> "Not gonna make it with this equipment"
> Just be done with it.
> It's only been 20 minutes. Paid for an hour, but don't want more.
> She leaves.
> Now I'm a real man.

I've gotten the clap to before pal. They give you some pills you take, don't have sex for a while then it's gone.

Got one for you fags

>be me 17
>dating gf for 2-3 months
>go to her house for big BBQ her parents are throwing
>10-15 people there mostly her fam playing horseshoes and drinking eating hotdogs you typical Amerifat shit
>gf decides she is ready to fuck finally
>almost blow load from excitement
>go downstairs there is a sliding glass door leading from hallway to outside a little bit away from her fam
>close sliding door and curtains
>being retarded teenagers we decide to fuck on a futon in the hallway in front of sliding glass door
>she takes shorts and panties off climbs on top of me throws blanket over us leaves shirt on
>finally shove it in that wet tight hole
>hurts for her she is virgin
>2 min in hear sliding glass door open
>why the fuck didn't we lock it
>it's her dad he sees us immediately drops in opened bud light can on ground
>gf sits up blanket still cover my p in her v
>screams out "we are just laying here!"
>father says sorry while basically sprinting out door
>surprisingly lets me keep going after
>mfw that was 8 years ago and we are now engaged
>mfw my father in law witnessed me deflower his daughter

>Now I'm a real man

Fucking kek

Hey guys! Who likes a flaccid penis? Srs Do I have Phimosis? This is as far as I can pull the foreskin back.

...

Fuck off.

Keep trying everyday, user. Each time until it hurts.

Eventually you would be able to uncover your glans completely.

I was expecting this to be a joke about a talking dolls with a string for the longest time.

>Date girl for 2 years
>Epic sex
>One day she asks me to not ask questions
>Ok, go on
>Fuck me and hit me harder than you think I can handle
>harder
>HARDER
>Tears drop and she does that breathing crying thing
>Calls me daddy
>She comes hard and loud
>Happens every other week
>mfw

I don't know and i don't want to. She got off, I got off.

Maybe you guys need some more pics? Thanks for your input, I genuinely need to figure this out.

...

That is an actual great story of youthful indiscretion with a happy ending. Congratulations user.

gtfo cancerdick

I was disappointed when it wasn't

Now that I re-read it, me too

>be me last week
>meet 8/10 on tinder
>talk to her a lot for a week
>talk leads to other talks
>talking about fucking A LOT
>she asks if i'll get drunk with her
>ok
>she invites me over to her place
>ok
>she mentions it'll just be us
>nut
fast forward to weekend
>show up
>not awkward at all seeing her
>get drunk
>end up laying down together in her bed
>she starts flirting hard
>i go in for the kill
>she wont even kiss me
>mad.jpeg
>get up and leave her
>haven't talked since lol

This story isn't real

I bagged some Asian chick and she ended up having an STI got that shit taken care of at a local clinic just one pill and a shot and I was good to go in a week. But now I use condoms and never eat girls out or kiss them once they have sucked my dick.

>hooked up with a 30 something lady
>6.5/10
>gave one of the best blowjobs in my whole life
>"user you can put it in my dirty hole"
>diamonds.jpg
>fucked her ass like there is no tomorrow
>cums and pulls out
>condom is covered with brown stuff

shit i am never doing that again

>having a threesome with a friend of mine and this slutty south american girl we know
>we're all quite good friends and have known each other for a while so not really awkward
>started off slow but slowly getting more into it, changing position easily and getting more intense
>at one point we're doing doggy and i'm fucking her from behind while she blows my m8
>i eventually bust in her and move to the sofa for a bit to smoke
>my friend stays on the bedd and the girl gets on and starts riding him
>at one point he shouts like ''what the fuck?!?'' and starts spazzing out telling the girl to get off
>apparently since she got on top of him all of cum i'd just blasted inside her oozed out all over his dick and balls
>we laugh about it now but at the time he was pretty upset

>masturbate
>bust nut
>clean up and resum life
mfw when virgin

>Pick up girl at bar
>bring her to my fancy hotel room
>she insists she wants to fuck on the armchair near the front door
>i'mokwiththis.jpg
>she's riding my cock reverse cowgirl
>datass.png
>she's really into it, moans and screams
>something is off, i can tell by the way she moves, she never watches me
>move my head to the left
>mfw she is watching herself in the mirror
>mfw she's watching in her own eyes
>mfw she starts dirty talking to herself
>mfw she calls herself a dirty slut.
>she comes clamping hard on my cock while shouting at the mirror how she's just a bitch in heat
>she just says thanks and leaves me there without making me cum

how is this awkward?

Haha that reminds me of a similar story!

>be 16
>every weekend go to best friends house because his parents are cool and dont care if we smoke weed and drink
>smoke weed and drink every weekend
>bring our girlfriends most of the time
>this time its me and 2 friends, and our 3 girls
>we all decide its time to fuck
>have to figure out who gets where...
>i am able to win and stay in the party room out in the garage.
>best friend whose house it is goes to his bedroom
>other friend goes to thier nice new camper attached to friends dads truck

>start gettin hot and heavy with my gf, we have been dating for a while, so nothing new
>after foreplay finally get it in, right as I do..
>the fucking door opens
>friends dad, stares at me on the couch fucking this bitch, drops his beer.
>i yell out "were not fucking" ... like what the fuck else are we doing, he sees my dick in her lol.
>he leaves, i finish as fast as possible, make her get dressed and go yell at friend.
>he told me his dad wouldnt be home for 2 more hours.. he was wong...
Shoulda picked the camper...

I'd fucking "rape" the bitch. I need to nut too.

wait wut

my friends dad was like this too. Except he said "if you ever want to bring a chick to my house and fuck her. Just call me and I'll go to the bar for a few hours". That man is a legend to me.

I think it's because you're like fucking 13 and your foreskin is still atttached to your penis. Doesn't like that tight at all

What a great guy. Hope I'm cool like that.

Yeah friends dad is really cool, i was like a second son to him. And he didnt care, it was friday so he just wanted to get wasted and play guitar hero, but i delayed his plans haha

>be me 6 years ago
>25 yo
>not virgin but not getting much play either
>cum too quick always and have complex about it
>start dating a chubby 6/10
>good personality and qt
>2 weeks go by, taking it slow but she's way into me
>the time comes
>making out in my bed
>start feelin dem titties
>hand moving lower
>start rubbing pussy
>get inside her panties and find the clit with my finger
>30 seconds later she shivers and cums
>wat
>roll over and she pulls my pants off
>sucks my cock for 30 seconds and I cum
>we cuddle all night after that
>last month was our 2nd wedding anniversary
>now have 3.5 months old son

Found my fast cum soul mate lads

Fuck i want going to respond but dont listen to this guy.

Just do some stretching exercises by pulling the skin, but make sure it doesnt hurt as that might scar it. Do this for 20 minutes every shower with hot water. After a while of this practice pulling it back while fully erect to get an even stretch. Only took me like a month

Forgot to mention she trimmed down and is now 8/10

That makes no sense. You fucked her in the ass, what'd you think was gunna happen?

really enjoyed that, great story

This.

Unless she got an enema. Expect to be packing at least a little fudge. And thank the Lord if you don't.

Sir, my highest regards and congratulations.

Wife and I are your black 'n white opposite. We go for 20 minutes bare minimum with a casual fling... holding record is 150 minutes give or take. Married 16 years.

Finding the right one is golden.

...

Thanks bro, congrats to you too

Tbh I don't much care myself. I don't like shit, but it doesn't make sense, to me, to get all worked up about shit on my dick when I'm fucking some bitch in the ass.

>Must've spent all her SeXP on some other useless skill tree, instead of one to actually be any fucking good at it.

Fucking golden OP, thanks for the belly laugh

another

>having threesome with different friend
>girl is some romanian girl we know
she's on her side im behind her friend is in front getting head
>at one point i look at my friend and he's just got his phone out and he's recording the whole thing
>not sure what to do so i smile and throw up a gang sign ironically
>friend shows video to multiple friends and girls
>not sure if i'm cool or not

Where do you live with all this diversity

>imagine having feelings and human emotions, what a snowflake SJW

the netherlands

Somebody screencap this story. This is prety gud

she's scrolling through her facebook feed while you're there

same actually, i know quite a few eastern euros now that i think of it

one more

>me and friend from first story are at his playing super smash on the game cube
>sister of one of my friends messages me
>shes kinda punky/gothy looking, lot of piercings and a dread
>we'd hooked up once before, shes like 23 i was 17 and friend was 16
>i invite her over and she comes over with a friend who leaves at one point
>we're in bed watching something on the laptop and i tell her to go under the sheets
>she goes under and starts giving us head
>at one point she's giving my friend head and for some reason i dont know why i just get out of bed and go to the game cube
>start playing smash
>probably cause i couldn't get hard
>she peeks up over at the blankets and asks what i'm doing
>say im just playing smash
>mood is sort of ruined
>friend joins me and plays smash
>girl sits in bed confused and starts getting pissed
>me and friend sort of ignoring her and getting into smash
>girl leaves angrily
>still regret it to this day

there are loads, specially in groningen

Tha k you been looko g for that 4 a while

didn't know being a shitty parent was cool

Im in eindhoven. The universities here attract a lot fortunately

anythings better than dutch girls am i right

waveshines > girls any day user great choice

haha yeah. Currently with a nice indian girl

>Be me
>21, virgin
>Get drunk at school one night
>Decide to order pizza
>See group of libtards
>Except one girl mexican looks normal
>Solid 7/beergoggles
>flat chest but the ass was fat
>I ask if they wanna go halfsies on pizza
>´Sure whats ur name´
>Make idle chat
>Devolves into sex experiences
>Got none, lie about bdsm
>Mexican likes hair being pulled
>Liquidcourage.jpg
>Rub back of head and pull like in the movies
>She moans
>Hard.avi
>Ask if she wants to go back to dorm
>We walk through the front because beer
>Male dorm crowded
>Nobody cares about girl
>Weird.webm
>Go to room, nobodies in
>Start kissing
Cont

>She wants anal like 7 minutes into it
>Diamonds.jpg
>She pulls her pants down before pussy shown
>A bit hair but still damn
>Grab lotion from under bed
>Lube ass and cock up
>Slides in decently tight
>She spreads her ass as pound for >10 minutes
>Supersoaker cumming in her ass
>She said she came
>Goes to bathroom
>Doors open
>Whips tiny cock out
>Vomit
>Black out

Mfw Turns out that she had a thin mustache and was known to be on hormones. Now everyone thinks im a faggot.

>be a year and a half ago
>got a friend request and a message from old friend from high school that i hadn't seen in years
>i always had a huge crush on her, we hung out all the time but i got friend zoned
>she talks about how she passed my house earlier and thought of me
>talked casually for a while and then things got flirty
>arrange for her to come hang out at my house to catch up (i live alone in my own house, btw)
>she shows up, hasn't changed a bit, physically
>9.5/10 blonde, green eyes, petite tits, cardiobunny with perfect ass and toned af
>all my virgin high school masturbatory memories flashing before me
>we drink some wine and talk for hours
>she's completely changed as a person
>hardcore born again christian (she was kind of a slutty anarchist back in high school)
>still really flirty, so we eventually start fooling around on my bed
>no sex, but hardcore makeouts and grinding
>after fooling around she talks about how her last relationship, her bf was hardcore religious like her
>vowed not to have sex before marriage
>tell her im an atheist, and that's gonna be a problem
>says she always liked me in high school, and isn't that adamant on the no sex and wants to make it work
>is VERY specific in telling me it's not going to happen any time soon though
>idgaf, i used to be in love with this chick, she's still model hot, and now she's "a good christian girl"
>think i found the jackpot, and bear with the no sex as we dated

cont...

ew lost your virginity to a dude

Felt so good though

umm it is never gone faggot, just managed. How many pussies have you ruined for the rest of us thinking it was gone. FUCK!

>be me
>21 y/o lad
>chick I like to probe is into some nasty stuff
>Start banging the breast carrier
"Call me dirty names user"
>First thing comes to mind is slut
"You're a dirty slut"
>She likes it, continue calling names
>mid sex now
>"What is your name, you slut"
"Sabrina"
>stop having the sex
>everything is quite
>mfw mom joke

>fast forward 3 FUCKING MONTHS
>nothing but make out sessions and over the clothes rubbing/grinding
>she's fucking perfect, but it's starting to not be worth it anymore
>she can tell i'm becoming irritated whenever she stops my advances
>try to act ok with it for a little longer to make it work, since i may never get this lucky again
>one night she goes out with a friend to a country bar to go get shitfaced and dance while i stay home
>wake up to a text at 2:AM
>10 missed texts: babyyyyy, baaaaaby, are you awake?, baaaaaabeeee etc.
>i call her, and she's clearly drunk as balls
>she asks to come sleep over
>realize this is my chance
>she stumbles in to my house and gets into bed
>we make out for a bit, and for the first time, she licks her hand and puts it down my boxers
>starts talking dirty to me, acting like a little slut
>never seen her like this before in my life, completely different person
>go to finger her, and she tells me she's on the rag
>heart drops instantly, but then is resuscitated when she takes my boxers off and starts blowing me
>ball sucking, face rubbing, no gag reflex, the works
>no idea what got into her, but was loving every second of it
>it was like one of those cock worship porn videos, glorious
>i cum, she swallows, and we both pass out
>next morning i wake her up because i have to work
>immediately starts crying as soon as she opens her eyes
>says it was too soon, she feels like a sinner and she shouldn't of done it
>hints at me that it's my fault for taking advantage
>it's kind of true, so i apologize to try to make it work, and say i'll wait
>as the next few weeks go by, we get less and less intimate
>to the point where she rarely even kisses me because she's afraid she'll get too horny
>after 4 months and a single blowjob, i tell her im breaking up with her
>she starts crying again, and apologizing, but i'm done, so i just tell her to leave

So much wasted time, but at least i got the best blowjob of my life

What's wrong with dutch girls? amerifag here, always heard that they're bombshells

Seems like it would just become boring after awhile.

Sauce on that gif?

wat?

Why wouldnt christians be allowed to give blowjobs the fucks wrong with her?

>lose virginity
seriously, there is no more to be said than that. It was awkward as shit, and I went into it knowing it would be the most awkward experience of my life and it still was even worse than I thought it would be

If you weren't a virgin you'd know that just isn't true. Go back and take middle school health again faggot, if you're not in it right now.

Nice picture btw, I see you saved it from a clickbait article.

dont try to pull out anal beads like you would try to start a lawn mower

Holy kek.
You only make that mistake once, I'll tell ya. Did the same shit with a buttplug back in high school.

She was just a crazy religious nut, dude.

I'm glad I left her, it was the right decision but my penis still regrets it.
Whenever I see her pics or am reminded of her, I cringe on the inside thinking about that ass and what could have been.

Fml. I still kind of feel like a badass breaking up with a chick as hot as she was, though. Just an old notch in my belt, now.

post a pic

> yfw