Tell us about a time you fucked someone unexpectedly that was out of your league! Pics are always welcomed!

Tell us about a time you fucked someone unexpectedly that was out of your league! Pics are always welcomed!

>me 25
>friends neighbor was a hot 42yo divorced school teacher, we drewled over her.
>nervous fag went over to talk to her after she finished jogging.
>took her I ran and she asked if I coukd help her build distance.
>went jogging go inside for water and shit on couch talking.
>Tell her i got to go she reaches over and kisses me then places hand on cock.
>eat pussy and ass, sucks dick, fuck her several times and she got back with her lawyer husband.

I live in a Universitary Residence (idk if that is correctly expressed). Once we were at a party which was organised inside. Then we ran out of beer, and she complained about it. I said "hey there's more in my room) so we went to my room, and one thing led to the other and we ended up fucking :D. That was the time I lost my virginity tho, so not great sex, but not disgusting at all.

I once got a pity fuck by a billionaires daughter at a wedding reception . She was 50 I was 19...

It was horrible... I'm still broke...

I'd be even more broke if I name drop since she's probably sue me into oblivion.

well sounds awesome to me

Lol

Any pics

My current GF is miles above my league and has low self esteem so she settles for me. If she felt better about herself she should probably dump my ass for someone better

Maybe she likes your dick and personality?

>If she felt better about herself she should probably dump my ass for someone better

I am sorry to tell you, but you are the one having the actual self esteem issues
Better not show that or she will actually leave you sooner than you think

>be me like 17
>became really close with my neighbor, we used to party together. solid 9/10
>she started texting me late at night to come on my porch, we'd talk for hours
>came home one night from a party, drunk as fuck
>she was on her porch and ran over to me, gave me a hug, she was drinking too
>we chat for awhile, like usual.
>don't remember exactly what happened, but we started getting flirty as hell with each other/making out
>it's about to go down
>we went to the side of my house, near the fence. her back was facing me, and she pulled her pants down, showing me her ass. she said, "i'll do anything". anal popped into my mind, but didn't bring it up
>she lays down in the grass, and I follow, get on top of her
>stuck my dick, thrusted thrice, nutted immediately. said "shit, i just came"
>"reaally??"
>absolute shame/embarrassment
>she left like 3 minutes later
>we still talked, but not close like we were
>haven't talked to her in years

now that i'm a little older, if i nut early, i'll keep going, and not say a fucking word.

>senior year
>girl I have been trying to fuck for 3 years
>at a frat party
>she finally gets super drunk and starts grinding on me
>we kiss
>she tells me to follow her
>leads me to her car
>by the time she starts riding me I am so horny
>I cum in less than a minute


FML

worse feeling ever, amirite? that "i'll do anything" while i was rubbing and looking at that bare ass had me about to cum too. girls don't realize they can make us cum by touching us/saying things. kek

Oh she knows about it I take meds for depression after all. I think she tolerates it cuz she’s the same way

nothing like shitting on the couch, talking

Happens to the best of them, that's why you buy dick pills to make you last longer

Lol, writing this while wife is in the same room

>drewled

she "tolerates" it? mate.

Do you have a fucking story or are you going to pin point evrything wrong in the thread?

>friends with right girl in college
>we got drunk at a party, started getting flirty, and go back to my place
>no condoms but i said i'd pull out
>in her state she thinks that's a good plan >when the time came, so did i
>she's so warm and soft and wet that muh dick doesn't wanna leave
when she realized what was happening she seemed to sober up pretty quickly. she was pissed but luckily no periods were missed.

i laughed. fucking drewled

I used to believe there were women "out of my league", then I realized: there's no such thing. No bitch is out of anybody's league unless you're a beta cuck, but then guess what? There's a market for that shit too!

Idk and idgaf. I've banged 11/10's and regularly get with 6/10's. Unless you are completely retarded its easy and only gets easier as you get older.

39 and living the life you squares couldn't imagine. Feels pretty fucking good.

>protip: most females, no matter what they fucking tell you, are addicts for almost anything. Sex, booze, rock and roll, poppers, pop, etc. Never believe.

I got drunk with a fairly close friend that i had the hots for, but was way out of my league and we hooked up.

Sex was bad, caught feels anyway, and eventually all but stopped talking to her to spare my own sanity

0/10, do not recommend,

Solid advice.

More pics!

have no nudes or anything unfortunately. it turned out to be a one-night stand

girl to left looks weird, like her head is bigger than it should be

>eat pussy and ass, sucks dick, fuck her several times and she got back with her lawyer husband.
>and she got back with her lawyer husband.
>back with her lawyer husband.

Well done if she runs back to her old lover - YOU SUCK
Whats the deal? Small dick?

Are you retarded? Who the fuck would want to keep a girl that cheats on her husband?

Found the beta virgin.
>if i fuck a girl, she should leave her husband, and be my gf!
That's not how life works kid

think it's just how she's standing. she's a hottie. here they are again

Even more weird. Please leave it with 2 pics im not interested in that freak.

fair enough

dude, look at her head. compare it to the girl next to her. lmao

even in the thumbnail that shit looks like a parachute

kek fair enough. she wasn't the one i was interested in anyway.

She's not bad at all, I'd definitely hit that/date. And she's prob outta my league, tbh. Just cherry picking bc I'm on the interwebz. Don't take it serious m8.

no seriousness was taken. it's all good, just wish i could've fucked big-head's friend again

>be me
>22 yo
>travelling in new zealand for work
>met qt NZ girl on tinder
>flirted for a couple of days, exchanged pix
>everyone went out for drinks (last night in wellington)
>phone was on 6% battery
>had no reception cause in foreign country
>had to tether to friend's personal hotspot
>all the while trying to organise where to meet this babe
>finally organise to meet in car park outside her apartment
>phone dies 2 mins after
>relief
>go to bar, get hammered with her, good times, laughing etc.
>start walking back to my hotel
>not really sure wtf we are doing
>me: "i need to piss"
>wtf my hotel is like right here?
>she agrees to go up to my room
>eat pussy like a champ
>smash
>good times
>everythingwentbetterthanexpected.jpg

i only fuck out of my league. i could definiately have more sex if i was less discerning but im pretty proud/surprised by the caliber of chicks i can pull

Fucking yuck, you ate her out after jogging, no shower?
That's just unhygienic

she isn't that hot, but still out of my league... I am pretty much a total autist-nerd. A friend of mine latches into this dumb slut and gets proof of her infidelity. Ends up she is a sub-slut, he doms her while hubby is deployed. He wants more dirt on her, expects there is plenty on her computer, so he invites me over to her place and has me try to find shit on her computer (found lots of pics and some vids including her sucking a dog). My payment is to keep some stuff, and he has her suck and fuck me blindfolded. Pretty pathetic, but was best I have ever had.

I’ll take whatever you got

>Be me 21 years old
>Working in a local hospital
>Notice really hot childrens nurse. Irish, blonde, blue eyes beautiful to look at, huge tits too. Perfect body, an easy 10/10
>Got talking to her, making suggestive but humorous flirty jokes
>Get on really well, similar sense of humor etc
>Things got very intense for a while until i thought fuck it im gonna make my move, you only live once
>Turns out she's really kinky and loves to talk utter filth
>Got loads of nudes etc (no sadly don't have them anymore, did post them here in a pics you shouldnt share thread a few years back now)

>Find out shes married and pregnant. Didnt stop me
>We used to meet on the stairwell and get up to stuff, eventually fucked her bareback and loaded her puffy pregnant pussy up with cum in a patient changing room area
>Was so horny only lasted minutes, but man shit was so worth it
>still jerk it thinking about her

Oh, someone's definitely getting fucked by Chad in this relationship.

That lovely musky stench

...

>in college
>me and gf break up
>bummed out, depressed
>go out with group of friends
>Some leave to go to another bar
>I stay behind with one friend
>9/10, brunette, very pretty face, big perky tits
>Always been close friends at school
>We leave to go meet others at the next bar
>She grabs my hand
>Pulls me into an alley
>Pulls out tits
>Pulls up skirt
>"I need you to fuck me right here"
>fuck, bj,
>Cum biggest load of my life
>she can't hold it all in her mouth
>mfw when the alley had a security cam
>go meet friends
>mfw she has cum stain on her blouse

We live in different cities but we still fuck every time we see each other. five years later

>Be me, law school
>Mergers and Acquisitions
>Senile professor who babbles and makes no sense
>Really tough material
>Sit next to much younger hottie
>She was a Spanish and History major, knows nothing
>Loan her my own Economics of Banking textbook
>Tutor her in banking and econ.
>Start fucking
>Let her cheat off my take home-final exam
>TFW when she beats me by one point to win “award” for best grade in the class
>Abruptly dumps me after class ends
>Totally happy with ROI

How was she in bed?

my memory may be clouded with alcohol and time, but she's the one girl i wish i could get more of. sliding it into her was...goddamn. she's bliss

>be 26
>been going to swinger and kink parties for about a year with wife
>meet older couple
>husband is maybe 60, wife looks about the same
>he asks if we could swap
>his wife looks stunning for her age - slim, tits are small but not too saggy, nipple piercings, bald pussy
>she climbs on top of me and starts grinding me
>condoms are usually mandatory but her and her husband were OK with bareback since we were regulars
>as she's riding she starts doing kegels and I cum almost instantly
>pull out and make out while her husband is busy going down on my wife
>find out she was actually 70

>be 21
>hot girl at party
>work up the nerve to talk to her
>expect to be rejected
>she talks to me
>Turns out we have a lot in common exchange numbers
>spend night talking and flirting
>she leaves
>ruined chance
>she texts me next day something like "thanks for not trying to take advantage of me when i was drunk"
>asks me out
>great first date
>fuck on 2nd date

pic related

Shit sounds so fuckin' cash, John.

nudes?

I used to have some on my old phones. This was 6 years ago. Only thing i have are the modeling pics she emailed me.

fucking sexy

hell yeah. she was totally out of my league.

Nice one. I love chicks with a little cushion like that. They're built for sex.

wish you had the nudes. How was that pussy?

It was great. She prefered it in her ass tho

damn what a slut. got a better view of that ass?

pic related

nope. I wish tho :(

damn, she's begging someone to pull off those bottoms

>met girl at some party
>we got drunk
>we fucked like rabbits
>shit was cash

Always the same stories I bet 95% of this thread is bs and copypasta

tfw reading this still being a pathetic virgin

> be me
>around 16 years old
>not the most handsome chap, kinda short too
>there was a girl in my class 9/10 beautiful figure and hardly wore any makeup, a true beauty
>we are at a party
>we start talking a lot and we laugh and I get the feeling she's into me
>literally didnt talk to eachother after the party
>fast forward two weeks
>we both meet at a bus stop, completely alone
>have a deep convo, turns out someone in her family died and she didn't attend school for a while, none of her friends are willing to talk to her
>imalwayshereforyou.gif
>she sits on my lap and starts grinding me a bit, bear in mind this is in public
>dick is diamonds but suddenly I notice something
>she has scars on her arms and when I ask her about it she literally broke and got tears in her eyes
>tells me she's been depressed for a few months now and no one knows
>I ofcourse help her and talk to her about it everyday
>We get REALLY close in the next months and eventually get into a relationship
>she is much happier and more confident these days
>tfw people never understood how I got such a hot gf
> I was her first EVERYTHING (kiss, sex, bf) for some reason lol
>had the maddest sex, she was super kinky, would sit on my face, loved gagging on dick and could ride like no other.
>was into roleplay, bondage, and loved getting dominated as well as being dominant
>Pretty sure we had sex on the beach once and people noticed but that story is for another day
>eventually we got into a big fight i cant remember what about.
>we have sex one last time
>I'm telling you that was the best sex of my life. Angry sex >>>>>
>we break up
>still see her from time to time, she's still single but at least she isn't depressed anymore
>tfw I helped a girl with depression
>tfw thats probably the hottest girl im ever banging

at least your not a cuck

Addicted to poppers kek! I guess there's always one.

Those are some nice titts, got more?

...

this guy has to be some kind of retarded to get his wife fucked for sex with 70yo kek

Good shit bro.
What’s the kinkiest thing she’s into?

I'm not a cuck. We've both had sex with other people, and sometimes we just go to these parties to have sex with each other in front of others.

And my wife didn't even have sex with the 70yo's husband

>my wife
>have sex

What are you getting at?

giving me head or fucking in public. She fucked like a pornstar.

odds are she fucked the photographer

We were never bf/gf but i was one of the guys she fucked lol

unreal, instagram?

I once was passed out drunk on the sidewalk in front of my friends house in cape canaveral FL and this blonde chick walked up to me and kicked me to wake me up. She said damn your cute, i said your pretty cute yourself, i got some weed at my apartment next door and boom 10 minutes later i was having sex. easiest i ever got laid. she was like a 7 body and 5 face. in that same apartment a year later i was throwing a party and had like 5 people come over there was this 15 year old hot ass girl that was there waiting for my friend chris a mechanic to show up. when he did she seemed turned off by him and started sittin on my lap n making out with me n he left. so did a few other people by thenn it was just me her and my friend derrick and i fucked her brains out on my couch. some of the best pussy ive ever had she went out front afterwrds and i walked out and found her squated down moaning in pain and she said you wanna know why i fucked you? i said why n she said cuz you had clean nails and chris' were all dirty lol how cool is that for a reason to get laid. I was like 21 at the time

Dont know it. it was years ago. Before everyone had one. you find it let me know lol

Stop youve violated the law pay the courts or serve your sentence!

>went clubbing with a friend
>friend can pretty much get any girl he wants, never shares tho
>two hours into the party he picks up this blonde cutie
>acts all shy and cute, but has an amazing ass and just looks absolutely gorgeous
>we go to his place
>i try to set up a movie and order some food while drunk as fuck
>come back to the living room to him making out with her and stripping her slowly
>i decided to take a shower and change my clothes, and wait for the food until they finish
>im getting ready for the shower, can hear them starting to fuck in the bedroom.
>i go to the bathroom, 2 mins later the girl comes in to wash her face
>"oh, looks like I forgot about you. You'd also like to have some fun, don't you?"
>pulls down the towel I had around my waist before I could say anything
>we get in the shower and fuck for like 20 mins
>was kinda awkward tho, but we were both drunk so it was ok
>came in her mouth and she even swallowed it. Fuck she was good..
>we got out and watched avatar while eating sushi
>my friend and her were still chatting 2 weeks after that, but then she got back with her boyfriend or something
>dont think he still knows we fucked in the shower that night

>be 14
>a literal beta shit
>join this facebook of teens who like percy jackson, idk
>lurking and see 8/10 grill
>decide to stop being a little bitch and messege her
>betterthanexpected.jpg
>summer break arrives
>the group sets up a meeting in a local park
>we've been talking about sex and stuff, i was obviously lying to sound cool
>arrive at park, about 50 kids with the cringy orange t-shirts, she's the only one wearing purple
>at some point she takes me to the side
>she says she has a gift for me
>confusion.png
>we start making out
>she starts to willy my nilly in the middle of the park
>holyshitwtf.gif
>we go back to my house
>wearethechampions.mp4
>i lose my virginity
>mfw

If you name drop I’ll tell the name of the billionaires daughter I fucked. No lie

>only gets easier as you get older.
Yes.
The older you get the more experience and confidence.
Plus you can afford shit 20 yr olds cant
so easy to fuck young girls
I had a buddy who went back to college and took freshmen classes.
He was rolling in pussy.

I did fuck this one girl unexpectedly, but she isn't really out of my league.
So I was 16 years old and me and her were just chilling at her place, we were fooling around, but not much, since she had a boyfriend.
Fast forward to some early hours of that night, she's jerking me off and I get really horny, decide to eat her out (still not thinking of sex)
She pushes me away after a bit and just sits on my dick. We end up having some meh sex, since I wasn't expecting any of this, therefore I wasn't really horny and I didn't have much motivation.. Life I guess.
Since then we've fucked a bunch of times and it was good, and fun.

>Go to a club in town
>Just chilling and spy a young hottie on the dance floor
>I was kind of in a meh mood
>my surprise when she comes up to me
>we start chatting
>both decide to go to the patio because it's quieter out there.
>pretty desolate on the patio, only a couple of other couples chatting.
>eventually left alone.
>she rubs my pants and looks over to a dark corner
>we move over there she gets on her knees
>teases my cock with her lips and then takes my shaft to the hilt.
>bobbing something furious.
>about to cum. she looks up at me with big brown eyes
>I blow my load and she swallows it all.
>then slowly puts my cock back in my pants.
>she stands up and french kisses me.
>I can still taste me on her lips.
>she lifts her skirt and say s, your turn
>I look down and see a cock bigger than mine
That's how I ended up in therapy.

>willy my nilly
Fucking kek

Looks like Las Vegas???

Ah, the good ol' "dutch switcharoo"

You sucked it didn’t you

I would, out of shame

it wasn't gonna suck itself

I am a loner, but a girl asked me out, and I dying for sex said yes. She was actually a cool person, a little SJW, but down to Earth and real. I am the type who takes things slow, and so I just talked to her for a few hours (because that's what girls like right (or that was merely my intuition at 20)) and then she spilled the beans, let's have sex. Considering I am the most sexual of sexual demons, once she said that, I got the message and started kissing her. And I also pulled her pants down a few inches unabashedly and licked her cunt. She was somewhat overweight, but had spunk and Italian genes, and her breast were slightly above average. She was one of those very uncensored type of ladies, understood sex was more than simply a way to a man's wallet, but an act of extreme pleasure. We were both hedonist. She unzipped my pants, and I decided to one-up her reluctance by grabbing her hair (a fortunate call), for she came down and deepthroated me on the spot. Now I have a 6 inch dick at epoch (not to lie), but she choked on the thing and even admitted how that was the first time that happened to her. She was also into domination before we met, as in she was paid to administer non-contact BDSM to people who enjoy the fetish. I was so happy at that acknowledgement, but somewhat doubted it's claims. But a girl usually has her tricks, and she might have played mind game, but the right ones. So I thrusted to the back of her throat until I came and reacted in orgasmic glory. She responded with some odd expression, like why are you acting so reactionary and jumpy to my blowjob. It was plain old hot. The next day I took her to a nature trail and fucked her in a meadow, came on her face, and used a sweaty sock to wipe it off her face. She said it was the most romantic sex she ever had. The terms of conditions were very low to get to her woman side, all I had to do was shaved my balls. She didn't want hairs in her mouth.

>JonathanFranzendescribeshissexlife.txt

Who is John Franz? Sucks she got cancer, and what I feel so horrible about when I found out, was I remained in my convictions against muslims invading Europe in the midst of her sickness. We are still cool though, which says something because you would normally thing a liberal leftist who posted non-stop for a month after Trump's victory would delete me, but she didn't. She got over her cancer, and is now engaged to someone else. If she never got cancer, which interrupted our relationship, I would have convinced her to have a threesome (she would definitely say yes). I was a horndog back then

>be 16 yr old me
>at a school trip
>Ive been falling for a girl in my class for a year
>me, her and about 7 others from our class are out on the beach drinking and smoking
>we then go to the club
>were all hammered and decide to go for a night swim
>we go back to the hotel
>shes in a room with 2 other girls also classmates
>me and a friend are invited
>were all on the balcony and Im a little nauseous
>she invites me to sleep in her bed
>I instantly feel better and lie next to her
>we cuddle for a bit and drunk me doesn't hesitate to touch her anywhere
>she turns back to me and we start making out
>I slip my hand in her shorts and start touching her pussy feelsgoodman.jpg
>she seems to like it and I move my hand to her tits
>she asks me to follow her
>I suddenly realize that 4 other people are sleeping in the same room
>we go to my room and we see 6 people passed out drunk on the beds and decide to go in the bathroom
>I push her to the wall and get her naked
>she wants to lay down on the floor on her back
>I put my dick into her tight pussy and start pumping like a mad man
>Im so drunk I take a long time to finish
>she cums before me and I spill my load on her stomach
>we go back to bed
>I sleep like a baby with my notavirginanymore face