Post story or short cliffs about the most memorable (good or bad) moments of your sexual history

In high school I used to fuck a girl whose brother would go on ro start a band and be accused of rape by multiple women.

Girl I dated a long time ago left a voicemail while she was getting fucked by someone else. Was so pissed but jacked off to it later. Would be really pissed now that I'm not still dating her and being kept caged and cucked except that she is in jail

I spent two months camping in a remote cabin with my best friend in college. His younger brother was with us, and was a total femboy. Both his brother and I fucked and creampied him multiple times a day for those two months, and I still think about it when I cum in my GF.

When my hs gf told me to fuck her without a condom, felt so good I couldn't move without cummin and then I nutted on the first pull back

memories of my what?

> being kept caged and cucked except that she is in jail

"who's caged now, bitch?"

damn did you keep going?

lol that's pretty good. I mean i wish I had my cuck fetish back then, i'd've put a ring on it. Current gf is very vanilla but not in jail

>literally fake and gay

Someone I know was asked to babysit his 5 and 7 year old nieces some evenings at his sister house. He was 13 years old and only had to watch them for about 3 hours while their parents went out for dinner/date on Friday's.

It was only the 2nd time he babysat them when he made up a game that they all played. The goal of the game was to get both of the girls to take off their clothes everytime he found them during hide and seek until they were naked. He won.

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>dating a girl that was pretty fucking hot
>she loved me unconditionally
>always have this thing for fatter chicks
>never fucked a fat girl
>not like SBWW, just wanna fuck a regular old BBW
>There's this common friend of ours she's exact body type meets my ideal BBW criteria
>So horny one night after girlfriend went home, i text BBW
>Straight up say "you're really hot, i want to fuck you"
>Girl does not hesitate, just says "im picking you up and this is happening"
>I'm waiting outside, my heart it racing for the fact that I'm going to cheat on my girlfriend with a girl who'd be considered a major downgrade in everyone's eyes, and we're doing this right now
>I'm literally shaking from being nervous and exhilarated for how wrong this is
>She picks me up
>Parks behind the place she works
>gets on top of me making out
>she's so much heavier than im used to and that turns me more
>so much warmer
>feel up her massive tits and take off her bra
>she pulls off her shirt
>sucking on her massive ttis, biggest pair ive ever had at this point
>she leans over so i can pull her leggings off
>ass so big and plump
>cute soft belly
>she sits back down with my cock entering her
>so wet
>barely moves
>i instantly cum
>hardest orgasm to this date
>i am embarrassed
>"umm wtf? did you just cum?"
>"just a little, it's fine, keep going"
>im trying to keep it together but its too intense, way too sensitive. feel like im going to piss or pass out
>i ask her to give me just a second
>she just stops moving and i suck on her tits some more
>dick wants to cum again
>she moves her hips slightly and again, just cum whatever little bit there was left in me
>im spent
>she gets off me and starts getting dressed clearly disappointed
>drops me back off home
>wake up to angry texts from gf
>the BBW messaged her on facebook and told her we had sex and i came inside her and she's worried and thought she should know

Lost hottest gf of my life in exchange for the hardest orgasm of my life.

Same fag. One more memory

>2009ish
>obsessed with squirting porn
>girl im seeing at the time gets weirdly jealous
>tells me she's trying to learn to squirt
>sends me pics of her masturbating on toilet and "squirting" (send a video text in 2009 was a disaster)
>for some reason I knew she was lying and this was just her pissing
>halloween rolls around and we go to an all night party
>we get fucking wrecked
>5am, we decide to leave, walking to car and she has to piss
>she just squats and pisses in her costume
>this turns me on for reasons still unbeknownst to me
>i am fingering her piss soaked pussy all the way home
>lay on the carpet of her bedroom
>make her sit on my face
>tell her to piss in my mouth
>after she gets over being piss shy, she unleashes a torrent of piss i wasnt ready for
>trying to drink it but its so much so fast i can only swallow down so much with the rest overflowing from my mouth and running down my face onto the floor
>im am in awe and turned on beyond belief
>she sits on my cock reverse cowgirl and rides me until i cum
>take a shower together and passout
>im burping her piss
>next morning we have to clean her carpet because the entire room reekd of piss

That would have actually been a very hot experience for me. I don't get nearly enough piss play action.

Have you noticed the squirt from girls who really are having an orgasm basically tastes and smells like watered down pee?

That's why I will never not believe that SQUIRT IS PEE!

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L A R P

Yeah, when I found a girl that did squirt, the squirt smelled like coffee a few hours after her and i got coffee, so I quickly figured out, yeah, squirt is piss.

As far as piss play, my wife and I went down the rabbit hole for a while. I would text her pictures of me drinking a ton of water from the water cooler at work before i left to come home and she'd be giddy knowing i was going to have a full fresh bladder to empty into her mouth.

I miss when she'd piss in my mouth, we stopped when I took it too far and pissed in her ass and she couldn't hold it in and a torrent of shit piss mix erupted from her ass and all over the bedroom, she never wanted to do any piss play ever again after that.

Every time I've piss played it was always in an environment that supported the mess (i.e. the bathtub or shower).

I like both pissing on and being pissed on. I can drink some pee IF it's really watered down and not the rank dark yellow flavor.

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I've posted this before but its still been on mind lately and seems related. I'm not too shabby but i have not had an unexpected win like this since.
I was just barely 18 and with family on vacation, met a 40something married woman and had the best fuck of my life.
it's been a bit and she has no idea but i still "cyber-stalk" her online - she had even given me a fake name but i saw her real one on an ID badge for her conference.

>Be me, just turned 18, dont want to go with family on vacation but its been planned for awhile, disneyland and all the surrounding crap
>have paper still to finish for school so one morning everyone goes off and i take the morning to finish it
>on my laptop in cafe downstairs and this woman just comes up and sits by me and asks if im writing a book, being cute
>shes super nice and i think she works there at first, she's dressed how i would envision an executive woman to dress
>she explains she's there with her company for a conference (not going to doxx but a bio-tech company)
>she was super flirty, makes joke about wanting to see my id, and asked if i felt like vaping some weed with her in her room and of course i fucking did
>she jokes in elevator that "people probably think im your mom"
>get to her room, we smoke, she turns it to 11 suddenly and essentially jumps on me, frantically undressing me and herself and fucks my brains out
>we chat, she tells me about some drama with her family and son who was my age which feels surreal and hot
>we fuck again, i'm even able to catch glimpses of myself in the mirror with this woman lightyears out of my league bent over the bed and i feel amazing
>then i go back to working on my paper, never see her again, this was all before 11am
>look her up afterwards like a pervert but never contact her and no intention of fucking with her life

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Was she cheating on her husband with you or divorced at he time?

I've never had a cougar. I've never been with a woman who wasn't the same age as me or much younger. I need to experience that some day.

She was married, yeah. While talking after the first fuck she implied that this - her fucking around - wasn't a first for her but i did not press her for details or anything. i was still basking in the afterglow, a bit high, and wanting to fuck more.

Most memorable had to be with a girl from school at a friend's house. My neighbor, a girl, was dating both a girl and guy from school. The other girl, Sam, was kind of meek and going along with it because of low self-esteem. Made it clear she wanted nothing to do with the guy, this short pudgy dude named Anthony, but he'd become obsessed with her because she was a virgin. Tried pressuring the neighbor girl, Amy, to get her to let him hit. One weekend, Sam was staying over at Amy's and Anthony called, begging to come down there to have sex with Sam. Was willing to walk all the way there, though he lived across town and realistically he'd never make it. Was still enough to spook Sam so she texted me. Not sure what to do because she was worried that she'd fold just to please Amy if he somehow managed to get there.

Part of me had just kind of had enough of the situation. Amy was manipulative, Anthony was a creep, and Sam was being just an absolute doormat and taking none of the advice I gave her. So, I walked down the street, walked into Amy's and told her to text him back. Tell him I was there. He hated my guts so that was likely to dissuade him. I didn't go down there for nothing, though. Figured if Sam wasn't a virgin anymore Anthony would have no interest. I brought this up to them and got two different responses. Sam was just kind of dumbfounded and Amy was all for it. >TBC

>continued
Really, Amy just wanted to see her gf take a dick it didn't matter which. Basically reasoned that since she was going to be a push over and do nothing it was going to be him or me that did this and I was the lesser of two evils. No real resistance, in fact once we got to the foreplay she was really responsive. Barely touched her abd she was just drenched. Sex itself was nice, took her initially in missionary and moved around some during. Her fluids were that kind of thick, clumped consistency and didn't help it was mixed with a little blood from popping her open. Finished in mating press and once the haze wore off I had to go into the bathroom across the hall to wash my dick off.

She walked kind of bow legged for the next two days, one at home and one at school though by the second it was less noticable. It became a regular thing but that first time, there was just something about it. It wasn't planned and just felt like a heat of the moment thing. Her being so tiny, too, had my dick in a borderline vice but the slickness helped a good deal.

Tl:dr faggot

Okay, nigger.

a threesome with two sisters , never it was gonna end that way , i was basically friendzoned by one them when i told her i liked her...

I’ve got a few.
I fucked a dude’s wife while he was passed out on the couch 10 feet away from us.
Had sex with a Chinese girl that barely spoke English. Memorable part in that was I can tell when she started having an orgasm which lasted for about 2 minutes, and she pulled me out afterwards just to show me her squirt. I was so happy with myself I just stuck my squirt covered dick in her mouth.
I do have a haunting experience of pulling my dick out of a girls ass and it had shit on it. Luckily I was wearing a condom that time though

Started having morning sex in a spoon position with the girl I brought home from the dive bar the night before. Im about to cum so I say where can I cum Im not wearing a rubber. She doesnt answer so I ask again and she says “ youre in my ass”. I fired my load up her ass immediately after hearing that. First time I got to fuck a girl in the ass. Those were the days. Now Im married and have sex like 3 times a year

>Now Im married and have sex like 3 times a year
My feels for you, Yea Forumsro!
Why don't you get a side piece?

>get a side piece
By not fucking you, this is exactly what your wife is giving you permission to do even if she doesn't know she's telling you to do it.

I'm a side piece for my best friend whose been in a mostly sexless marriage since his first kid was born. That was almost 10 years ago. They have 2 kids now. She got fat. Doesn't care about her appearance or him anymore. She only cares about spoiling the 2 kids.

He told me a few months ago she hadn't had sex with a single time in 1 1/2 years. I knew she hadn't been putting out much for a long time but hearing that it became clear why he's been coming over to my apartment almost every Friday (and sometimes comes back Saturday evening too) for many years now.

Of course, it's all on the down low. We messed around as kids and learned the ropes experimenting during way too many sleepovers in our early teens. We never got caught and never told anyone.

It needs to stay that way. His wife doesn't like him drinking (mormon) so that's his excuse for chilling with me. The official line is we start drinking, order some food, keep drinking, watch a few movies, keep drinking, he stops drinking to take an hour or two to sober up and then goes home to his sexless marriage.

What we actually do is start drinking, order some food, make out, maybe suck some dick until the food arrives, eat, drink and cocks out, then get back to pre food activities.

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You live in st Paul Minnesota

>she was 17, I was 19, we decided to fuck. After a couple of minutes of heavy petting I bend her over, pull down her panties and drop my pants. All seems good, seeing her like that gives me a raging boner. She's on the pill - hormonal issues, she needs to be on the pill , this gets me even harder, I'm gonna fill her up. But my dick can't fucking go in. What the fuck is going on? I know I'm not aiming wrong, I can see her pussy clearly, but I can't get inside her. I use my finger to pinpoint the hole, it's there, I fucking knew it, I'm not just pushing against her pubic bone or something. Cock still doesn't get in. Try to make a joke about how the hell did she fuck with her ex, she laughs if off but the fucking frustration builds up. I'm hard as a rock, she's ready to go, I can see the fucking hole but my dick can't go on further. I try to guide it a bit upwards, downwards, try to move it around, maybe the fucking force field gives in. I'm getting more frustrated and my erection starts to go down. Now, I can't tell how many minutes I tried, time seems to pass slowly when you're going through embarrassing shit, but the chick is a sport and pulls her panties up, tells me to lie down and starts sucking me off. She deepthroats me, can't tell how much I lasted, but I do remember this: the moment I start to cum and I see her lips moving up and down my shaft, with some trails of cum behind it fuckin hits me. I didn't use any lube, spit or anything. She was dry because of the pill and I was failing to get it in because of that.

Sounds gay af

>You live in st Paul Minnesota
No, I am in the pacific northwest.

It is very gay as fuck. It's faggot level gay as fuck.

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Does he fuck you?

2nd: we split eventually but a couple of years later we meet at a bar. We drink some beers and we start getting horny so we go to a park nearby, clearly with the intention to fuck. So we get it on and I remember she's on the pill, she has to be on the pill because it's a problem for her. So I fuck her in that park, good god I pounded that ass but I'm close to cumming now, and while a bit drunk, I'm still aware so I'm telling her that I wanna finish inside and if that's ok. While I'm pounding away she says something, I'm looking at how my dick goes in and out so I'm really paying attention, I'm sure she's on the pill and I'm fucking 10 pumps away from unleashing everything I have inside her. But she it wasn't a short answer and that makes my drunken brain wonder why so many words instead of OK. So I ask again and this time I'm hearing it: she's saying she stopped taking the pill. The alcohol just went away, I'm pulling out but the pressure is too strong now, I come the moment I exit her pussy, jizz going everywhere. Good god the disappointment in me, but at least I didn't cum inside her. We stay for a smoke, we talk some more, maybe an hour, I walk her home and take a cab. While in the cab, I start thinking about what went wrong and shit. I'm still disappointed, but I got some. So I start searching for my keys in my front pocket and then I see it: a huge fucking cum stain all over my jeans, on the left thigh. It looked like I had an egg in my front pocket and it cracked and spilled all over. And I walked around like that.

I was close.

A whole bunch. In many positions. Deep. Fast. Hard. Just the way I like it.

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Am married, same situation. Have several side pieces that know various versions of the truth. 10/10, would recommend. Pic related.

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Eh, I have a fleshlight and she still gives great head whenever I ask. Dont have the time or energy to go chasing after pussy anymore

>Discovered i was bisexual when i was 16
>One time went on a double date with my girl and my best friend and his girl
>After the movies we make out in my friend car and then drive to left our girls at home
>when my friend and i was alone in the car he said he was really horny and wanna jerk off i said “fuck me too”
>he stopped in a dark street and he just pulled out his cock and starts jerking off
>when i saw him i was aroused like really hard and pulled out my cock too and start stroking
>while i was watching him, after like 5 mins of furiously fapping he said “fuck i cant cum” and said can you give me hand
>he was joking but i said “ok ill do it if you do it to me first”
>he looked at me and grabbed my cock and give me a few strokes only and said ok is your turn
>I grabbed his cock and i like how it feels in my hand, was really hard but the skin soft and had a really thick vein from the base upto the head
>I keep jerking him off for a few minutes and said he needed some lube
>He took my hand and licked the palm and spit in it and told me to keep going
>I was already super horny and didnt stop just keep stroking his hard cock
>He said use more spit and and i spitted in my hand and keep doing it
>He suddenly said lets go on the back seat
>We go to the back seat and he removed his pants and underwear and said he really wanted a blowjob
>I said ok ill do it, but you do it to me first
>He was so horny he doesn’t hesitate and started licking and sucking just the head of my cock
>After a few seconds he said ok is your turn
>I was shaking of excitement and breathing heavily
>I was go down on him like my girl do it with me
>After a few minutes he said “fuck user you give head better than my girl”
>I was horny and proud of my head skills and told him is my first time
>He said was his first time with a guy too
>He wanna do it at the same time and we trying to do a 69 but i told him we should go to my house

Continue?

And what did Anthony say?

Wtf?

Green text the dude's wife story.

go on

He was too scared of me to actually talk to me so I had to hear it through the grapevine that he threw a hissy fit in the band room. Referred to me as various horrible things on account of my extensive facial scarring/disfigurement, but apparently Amy omitted the part where she actively encouraged it so she didn't get yelled at or anything.

More?

My ideal female looks like this chick. Small tits. Skinny. Short. Petite figure with fertile breeding curves. Tight ass. Innie belly button. Innie vagina lips. Lower back dimples, Cute face. No tattoos. Completely shaved vagina. Enjoys all the kinds of sex.

I'm a manlet who only weighs 140 pounds so having a nice petite woman small and light enough for even me to manhandle would be a huge ego boost to my masculinity.

One day. I'll keep my hopes up.

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>We went to my house straight to my bedroom
>I put porn vids girls doing oral
>My friend fully stripped naked so i did the same
>He sitted in the bed legs wide open
>I kneeled and starts giving him head
>He was still hard as a rock and his glans was really shiny from all the precum of being arosued for so long
>I was soft but as soon I tasted his cock again i was super hard my cock was throbbing
>He said ok lets do the 69, he kinda obssesed with the 69 but i was enjoying more just giving him head
>was really hot tho, i layed in my back face up and he claimed on top of me put his cock dripping precum in my face and i loved the taste
>He was sucking mine and he was moaning and breathing heavily, was really hot
>After a few minutes he said was about to cum
>Told him i wanna just sucking him and he can cum in my mouth
>He said “really? Fuck user my gf never let me cum in her mouth”
>He was excited with the idea and aitted in the bed again
>I kneeled in the floor and keep sucking him he was moaning really sexy saying my name and how good i was giving head and talking dirty to me
>He said i was such a good slut and he loved to fuck my mouth
>That make me so horny and keep sucking him faster
>He said was about to cum but i didnt stopped
>He grabbed my head by the hair and make me go balls deep on him
>I was gagging and making loud slurping and choking sounds
>Then he exploded deep in my throat
>He grabbed my head and pulled me up and tongue kissed me i still have my mouth full of his cum
>Told me to lay in the bed and opened my legs
>i tought he wanted to fuck me and i layed face down ass up legs wide open
>He said no no turn around
>I turned and he claimed on top of me like cowgirl position
>Grabbed my cock and put it in his ass, he said fuck me user
>I was kinda shocked but i did it
>I put the tip inside of him and he just started ridding my cock up and down long moves he wanna feel the cock in and out all the way
Continue?

yep

>This was obviously not his first time doing anal
>After just a couple of minutes i said i was about to cum
>Asked him if was ok i can cum inside of him
>He just moaning me really sexy just keep fucking me baby
>Cummed so hard i think i was to fade out
>He told me dont put it out
>I was shaking of the intense sensation trying to keep fucking him after i cum deep inside of him
>He start riding me slow but hard untill i was rock hard again
>I honestly lose track how long i keep fucking him cause i was really hard but my cock feeled kinda numb at this point
>He started grinding his ass against me i was balls deep inside of him
>And he was grinding me faster and faster
>His cock was rock hard and throbbing, dripping a lot of precum
>Suddenly he exploded and his cum reached my chest and my face
>He stops grinding and layed on top of me tongue kissing me again then he whispered in my ear “ i wanna do this for so long user you fucked me sooo good”

Whats next is kinda messy cause when i pulled my cock out was really dirty and smelly you know, i said we should take a bath, we showered together for like an hour first we clean ourselves really good and keep tongue kissing under the hot shower, after a long make out session we go to bed and sleeped naked cuddling, i was in a relationship with him and my girl at the same time for 1 year untill he and his family moved out of town

She learned that while in a different city from you dog

I've had a lot of uber/lyft drivers subtly try to pick me up and/or let me know they were down to fuck if I was down to fuck.

The first time I noticed it I was confused for a bit as to why he kept steering the conversation towards good places around my area to meet girls, what I thought about internet dating, acting surprised over and over that I had never been married, etc.

It clicked that his use of "finding women/girls" was code for "hooking up with dudes"... And more specifically me and him fucking. Once I realized that, it was obvious he wasn't ever going to directly say that to me because he wasn't sure if I might be a fag and just not to offend me so I would give a good tip.

What was clear in his coded conversation is if I was interested, all I had to do was say something like, "The women you meet in those places are always a hassle, dating would be easy if you were bi instead of straight. I know I've thought about it." and he would have swooped in like I had laid out the red carpet for him.

It was kind of flattering but I had no interest so kept making sure my use of dating women wasn't a euphemism and actually meant I was only interested in girls and was okay with my low success rate because I also liked being a loner.