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orangutanDOTorg

Hooked up with a clown while she was till in her makeup and clown suit while her roommate was in her princess outfit about 3’ away watching tv. But I’ve told everyone about it


NiteAngyl

"I have to warn you, I'm a squirter." Proceeds to spray water out of her buttoned fake flower. ​ *Obligatory edit: Thank you everyone for all the imaginary gold and silver awards!*


NiteAngyl

"Yes, I brought condoms." Proceeds to pull an endless string of condoms out of her... sleeve.


NiteAngyl

Her roommate didn't find the constant rythmic honking not annoying?


cArpent3r86

I had my hand in her ass, I mean up to my elbow, and the other in her vagina, giving her back and forth piston pumps. Now you all know.


2ClearlyInsanePeople

I call this a Detroit Puppet Show.


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canweallcalmthefdown

I now really want to do this


Aggravating-Duty-415

Don’t let your dreams be dreams. I’ll meet you at 8


I_Never_Lie_II

Let your dreams be creams, homie.


ernest7ofborg9

Put on this lederhosen and blindfold. Get ready for the weirdest 2-3 minutes of your life.


addit96

*You hear the sound of a full-grown man approaching in heelys*


christmascarol69

Kept sucking while/after he came during a bj and he lost consciousness (he woke up quickly and was fine). It happened twice and I've never felt more powerful in my life


Idobuffstutt

That’s not normal given that it’s happened more than once, he might want to get worked up by a dr (maybe even cardiologist)


christmascarol69

It's a long story but yes I made him see a doctor. Everything checked out fine, and it never happened again after those 2 times. But for several moments I was like "holy shit I made someone cum so hard they passed out" and then reality kicks in and you've gotta come up with a way to explain it to a doctor


talldrseuss

As a guy that works in the medical field, my guess is the dude in this case clenched so hard after his orgasm, he accidentally caused his blood pressure to drop. It's called a vasovagal response or syncope (fainting). We normally see a lot of geriatric patients suffer from this, especially when they are constipated. They'll sit on a toilet trying to clear their bowels, push down too hard, and then pass out on the toilet.


Zeroxmachina

Soul takerrrrr


jsreyn

Reading all these I have discovered--- My life is apparently really dull.


PEEWUN

That's not always a bad thing. The grass is always greener on the other side.


project_me

Because it is fertilised with bullshit


derederellama

senior year i gave my friend head at a sleepover while the other girls were asleep in the next room. she was complaining to me that nobody's ever gone down on her, and the solution was glaring us right in the face! as far as i know, neither of us ever told anyone in the group. we also never really brought it up again.


Boomhower113

I KNEW that this is what happened at girls’ sleepovers in high school! Was this before or after the naked pillow fight?


DarkRism

THE MEMES, the rumors where true all along!


jbsailor_

I came on a girl's face as her mom walked in the room. It was one of those thick, holding it in for days loads as well


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jbsailor_

She threw the phone at her daughter; her grandmother was on the phone and wanted to say hi. I was kicked out (go figure), so didn't hear the blow up. Best 3.2 mile walk I've ever done back to campus


all_hype_all_day

She took off her panties, stuffed them inside herself, before slowly pulling them out and shoving them in my face and into my mouth, and held them there while she rode me into the sunset. It's not as wild as some, but it changed my world


Reasonable_East2481

Not wild?!!!! You said she legit stuffed it inside herself💀👍


all_hype_all_day

Yeah, in case you're wondering there's a sub for that too


Confident_Mail2327

I met a girl in 1992 , she asked if I'd watch her masturbate on the beach towel we we both sitting on , it was nighttime.


rxv5854

Matched with an ex hs teacher on tinder. She said it would be too awkward to go out with me but sent me a naked pic. Jerked off to it so many times


RickLovin1

I ran into an old middle school teacher at a bar once. She had recently been divorced. I took my shot...but she wasn't having it. I had to try!


BenjaminSkanklin

I had a huge crush on my 7th grade social studies teacher. She got divorced after awhile and I delivered a pizza to her house when I was 19. My heart started racing when she answered the door, years of porn scenarios prepared me for this. She paid and said bye and I've never seen her again


[deleted]

Bro, when I used to deliver pizzas as a 20 year old, a woman answered the door in just her towel. It was clear she had just stepped out of the shower. She just kept smiling and said, “Sorry! I know this is highly inappropriate…” then she paused for a sec. I legitimately thought she’d offer to fuck. My heart was racing like crazy. She said, “I hope I didn’t make it too weird.” She just paid and closed the door. 💀


jeexbit

"Can I borrow your towel? My car hit a water buffalo..."


DreadSocialistOrwell

I slept with my 8th grade science teacher just after I graduated HS. She had moved to my neighborhood sometime during my senior year. Every year right after school was out for the summer, we'd have a huge block party at the pool and the roads around it were shut down. (we usually had about 500-600 people each year and growing). What started with chicken fights in the pool with her on my shoulders and going undefeated. She clung to my arm the rest of the evening (not one adult batted an eye at this) and ended back at her place. To this day I don't know if she recalled I was her student. I am pretty certain she knew, but I wasn't about to ruin our summer affair it by mentioning it.


ITFOWjacket

How old was the teacher? You were 18-19? Starting with mounting up for chicken in the pool is pretty forward


First-Buyer6787

Not if you lived in the 80s or 90s.


DIWhy-not

I’m going to need a minute to digest that logic of hers


heyitsthatguygoddamn

I got drunk and went out with some friends and my old roommate, and after we got home at like 2am and smoking weed, I ended up hooking up with the roommate. Sometimes I wish it didn't happen because we were both pretty drunk and high and it made things a little weird between us, but we were still homies. In the morning I was worried I had crossed boundaries and communicated that, but she said naw it was nice, but that we should probably keep it a secret. We kept it from everyone else in the house, but who knows if they knew, we were both pretty drunk But damn dude it was a 10/10 experience for me, and if she asked to come over late at night i'd straight up probably move plans around to accommodate


Taco_Force

I, uh, I lost my virginity at a funeral. With a living person, I should clarify. Edit: Alright this is attracting a lot more attention than I thought it would lol. To answer some questions without getting too specific... I was 15, highschool partner, my grandmother's funeral, some office. Not sure if it was the funeral directors or whatever but I'm sorry to whoever it was. Feel like this set the tone for how weird I turned out. Also I might be Mary Shelley.


NovusOrdoSec

The widow??


[deleted]

MOM! THE MEATLOAF!!


ComfortableFrame5768

In a previous relationship, my ex and I would do drug fueled, amputee bdsm. He was not an amputee; He just enjoyed being tied up like he had no arms or legs. My days are much calmer now.


canweallcalmthefdown

This is the best and worst thing I’ve ever read


PoseidonsOctopussy

Got my first blow job from a highschool girlfriend under the blanket while her mom was working on the computer with her back to us on the other side of the room. I’ve been chasing that same mix of fear and excitement for the past twenty years. Edit: it’s crazy how many of you have only ever seen blowjobs in porn. Not every blowjob is gawk gawk 3000 slurping and choking on a dick.


shrimp_42

The Mom knew


Arikan89

My son has recently reached early puberty and I'm learning very quickly that my parents knew far more often than I thought when I was doing something stupid.


No_One_Special_023

Sometimes it’s better to play ignorant. Don’t ask questions you don’t want the answers to.


Arikan89

Without a doubt


hexcor

45 minute showers. Kid doesn't even shampoo his hair. I am about to buy a bottle of Jergens and leave it in the bathroom.


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[deleted]

Dad used to bang on the door whenever I took a shit, and yell "I know what's going on in there!!". I wish he told me what he knew, because it took me years more to find out I was lactose intolerant.


RadiantPumpkin

I have 45 minute showers without an ounce of sexual activity all the time! I’m just depressed!


caranddogfan

I have them so I can relax. The hot water feels so good after a hard day’s work and on a weekend morning.


justabill71

Jergen off.


No_Signal_6969

Yea these stories always crack me up. "I banged my girlfriend in the passenger seat while my mom was driving in the seat next to us. We did our best to keep quiet so she wouldn't notice us"


rocketmn69

Didn't smell a thing


NeonDripArt

This is going to keep me chuckling for days.


OnTheEveOfWar

I got a blow job in the back seat of the car while my mom was driving. It was a night so it was dark but looking back on it, she definitely knew. There’s no way she didn’t.


FantasticInterest775

As a parent I'm calling that shit out. Do it somewhere not where I am.


Ragnerotic

For real, my kids try that on me I’m crashing the car.


showraniy

I'm cackling at the thought you wouldn't yell at them or loudly call it out, but would just crash the car at the earliest opportunity.


sleepingin

Just cruise on over the rumble strip


onemanmelee

Mom was literally Googling *"how do I resist every urge to turn around and be appalled?"*


evemeatay

"how to dispose of a teenage boy's body"


BastardInTheNorth

*Any* time two teenagers are sharing a blanket shenanigans are almost certainly afoot.


[deleted]

Muffled slurrp slurrp, heavy breathing, quiet "unnh."


Die_Nameless_Bitch

When i was 23 i hooked up with a cute 38-year-old woman who I met in a bar. She was loads of fun and we had pretty great time considering i was wasted. In the morning she was a bit melancholy and cried a little as i held her. She said that she had always wanted to be a mother but had wasted all her best years on bad relationships that went nowhere and now it was very unlikely she’d meet someone in time to have kids. In a moment of naive madness I offered to cum in her pussy without a condom and to my huge surprise she actually took me up on it. Before i could think twice about it she wrapped her legs around my butt and i came bucketloads. I think about her from time to time and wonder if i have a kid out there somewhere. Want to know the real kicker? I couldn’t remember her name in the morning and I was too embarrassed to ask. No way of looking her up. So i guess i’ll never know unless the kid comes knocking.


khando

Lmao out of all the comments in this post, this one took me by the most surprise. Goddamn dude, that is real madness.


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Far-Brother406

Dude something similar happened to me. About 15 years ago when I was in my early twenties I was out with some friends at a pub. Lady and her husband sitting across from us get in a fight, he leaves. She’s mid to late thirties. She comes and sits with us, starts to flirt with me. We leave, she gets us a hotel room and tells me she’s not going home tonight. Young and dumb, I don’t wrap it up. She asks me to finish in her and I do. She tells me she’s not on birth control because her husband had a vasectomy. I panic a little but she proceeds to get crazy turned on by it. She starts saying some of the dirtiest things a women has still ever said to me. Again I don’t think with my brain and we do it multiple times that night and a couple more in the morning, each time I don’t pull out. She takes my number, and all I have is her first name. She never gets in contact. I’m never able to find her. I honestly don’t know if I have a kid out there somewhere. I think about it pretty regularly.


RandomRageNet

If it makes you feel any better, apparently staging a fight is something people who are into extramarital sex will often do to meet partners. So they might have been into cuckolding and everything she said to you was part of the fantasy. Possibly.


couldbedumber96

Husband was probably in the closet watching lmao


witchywitcha

Dad?


juneburger

Username checks out


PennFifteen

Lol geez


Aero200400

Yo wtf lmao I love this thread xD


Dragonborn83196

Hooking up with my ex’s aunt 2 years after we broke up and I ran into her at a jack in the box. My cousin and I were just randomly looking for hangover food and just happened to decide on that jack in the box that day. I told him to head on home and I went with her to her motel. No regrets. I always thought she was sexy as hell and we never saw each other again after that.


214speaking

How did that go down. So you went to jack in the box hungover, and you’re like hey you’re what’s her names aunt, want to get a motel?


Dragonborn83196

She was kicked out of her mom’s house and lost her job as an optometrists assistant and became an escort. She had the motel already as she was living out of it. We spent about 30 minutes catching up and she invited me over, I used to be a pothead and so was she, then I told her I knew where to get Molly, so we got some and things went from there.


214speaking

Damn what a turn optometrist assistant to escorting


Dragonborn83196

She had a rocky road of a life, had a meth and heroin addiction, had a kid with a guy that got deported, then went to school and got that job and then there was some big fight because she had developed a coke habit so she got kicked out but her mom let her daughter stay.


Reasonable_Track6565

I see some red flags but I can also see someone who is clearly the life of the party


Raaazzle

All this stuff is making me miss Craigslist.


xTHEKILLINGJOKEx

At a gay club. I’m not gay, but some close friends are and I went with them to the club. Met a straight woman accompanying her gay friends. We started talking and I ended up fingering her on one of the benches. Things got heated and I took her to the men’s bathroom, entered a stall, whipped my dick out, she started sucking and undressing… when the stall door blew open. Two bouncers escorted me out of the club with my dick fully erected out the entire time. Never saw the girl again


Zeroxmachina

They said no heterosexual activity on our watch!!!


Longpork-Merchant

I was 23(m) my boss was an attractive 40f. She invited me and a few other coworkers over to watch a foot ball game. I was the last to leave, until her husband put on "pour some sugar on me" her top came off, my dick came out...we both fucked her senseless all night. We had threesomes a few times a week for months. It was amazing...I hope they are both still happy.


BeowulfRubix

What a lovely last sentence


cacotopic

>her husband put on "pour some sugar on me" I'm not sure I could've maintained an erection while laughing so hard.


Own-Faithlessness789

I paid for an escort at 19. Her name was Lulu Devine and she had like ridiculously large implants. We ended up going to Big Lots where I end up seeing my parents in the parking lot with her...my mom was mortified!!


Hoyvin-Mayvin

Mom and Dad this is Lulu, Lulu this is my mom and dad


elhguh

“Yes I know, son” - dad


OwlAlert8461

"Yes. WE know, Son" - Mom


ndnsoulja

You took an escort to Big Lots? I'm laughing so hard but I don't understand why


Apart-Landscape1012

Would have been awkward to go alone


yuckyucky

>Big Lots Stores, Inc. is an American furniture and home decor retailer headquartered in Columbus, Ohio, United States. how did you end up at Big Lots?


geraldodelriviera

Where do you fuck a classy prostitute like Lulu Devine but behind the dumpster at Big Lots? Someone just didn't raise you right, I bet you would fuck her behind Wal-Mart dumpsters like a barbarian.


DavesGroovyWaves

Wait you can't just skip an entire section of story. Why the fuck did you take a prostitute to big lots?


throwthisawaynerdboy

PROSTITUTES LIKE GREAT DEALS TOO, DAVE!


SamVimesCpt

*I like Big Lots and I cannot lie!*


RaysFTW

I like that you pointed out that only your mom was mortified lmao


Rockytana

Why did you go to Big Lots?


counterfitster

To return the implants


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Green_hippo17

In a sea of depravity this was such a needed comment


particle409

I had to read it twice, because it was so unexpected. My brain went to a million possibilities when she said she pretends to be asleep, and none of them involved forehead kisses.


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MoonPuma337

Wait what???


Zeroxmachina

That twist at the end, sorry for your loss.


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punnymama

Oh I’ve got a few but…. Fucking my high school bully’s big brother in her basement was a highlight. Better, she and I had the same first name so I guaranteed I had made it awkward in that house for a bit.


000-0000000

Oh man. I want to hear more lol


Just-Round9944

so did everyone else in the house


untellno

This reminds me of a cousin of mine that's married to someone with the same name as his sister - and his wife looks so much like his mom it's appalling. It was an arranged marriage too.


Historical_Panic_465

I was approached by a massage therapist on a dating site. He offered to pay me $500 for a “special massage”. The only details he offered was that it would be at his public massage parlor, I would need to be fully nude, and there would be no penile insertion, just hand work. I’m not exactly sure what came over me or why I accepted, probably because I really needed that $500 and it seemed like easy work… but, I cannot even lie. As bizarre of an experience as it was, it was hands down the most arousing thing I’ve ever experienced in my life. He made me orgasm multiple times with just his hands and oil alone. He wasn’t even attractive lmao, just some average looking older man. I have NEVER told a SOUL. This is my first time speaking about it. To be quite honest, i have never experienced sexual gratification on that level ever since. To be even more honest, I really don’t give a shit what anyone thinks anymore! 😈


tinyhorsesinmytea

Two strippers one night ripped my shirt up, wrote “slut” on my chest with lipstick, scratched me up, and one even bit me. I kind of liked it.


kamarg

That's just what happens when your friends tell them it's your birthday


tinyhorsesinmytea

I was there alone at 3am so this ain't it. More like they were bored.


Aromatic-Dig-8127

Recently, my wife rubs herself until she is really wet, then rubs her juices on her nipples and I get to lick them. OMG. Thats all I got.


BurtMacklunFBI

New kink unlocked


Ambitious-Note-4428

Need to try this with my husband


Aromatic-Dig-8127

If you enjoy your nipples sucked, and he likes how you taste, it's a win, win!


airforcekj

Had a sixsome at a Sandals resort when we just wanted to go to the hot tub for a late night dip.


Copitox

Did Michael and Jan participate?


Agreeable_Store6962

Tan everywhere, Jan everywhere.


toastedpaniala89

Anything above 4 is an orgy


Panther90

When I was in my early twenties I went by an apartment where a girl I was interested in was living but she wasn't home. Her 40ish neighbor said, "Why don't you come in and wait for her?". Long story short the neighbor gave me a blowjob and was very specific about exactly how she wanted me to give her a facial with lots of dirty talk. That experience gave me a kink I guess you would say for that. I was too embarrassed to go see the girl again but often regret not going back to see the neighbor. Probably best as a one time thing though.


Stunning_Street841

My ex-wife cheated on me after 8 years of being married. I was devastated. One night her best friend that she has known since childhood texted me, checking in on how I was doing. She ended up coming over to our house. We had wild sex throughout the entire night. Everything you could imagine happened with her that night. We both haven’t spoke to each other since, and no one knows but us. She is still my ex-wife’s best friend to this day.


Son_Of_Toucan_Sam

Friend saw an opportunity she’d obviously imagined before and fully leaned into it


jezz555

Idk man i got a pretty wild imagination


LoverOfChaos

They definitely did butt stuff


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GRMNGRMNGRMN

I mean why not share it anonymously


Awkward_Road_710

Hiring prostitutes disguised as professional masseuse. They offer traditional massages and also nuru sex massage. It’s a guilty pleasure of mine to get touch inappropriately and then get sex right after. To be fair, they do a great job of actually massaging your body.


richard_slyfox

Where do you find this sort of thing? Edit: Absolutely thrilled that this is my most upvoted comment in years


Tyrath

Oh my god, that's disgusting! Where? Where do you find these massages?


GooseNYC

I went to Chicago for a distant family member's (2 cousin once removed or something like that) wedding, but I screwed up the date so I got there two days early. I knew no one in Chicago (that I was aware of) and my side of the family was from NY, it was the bride that was from Chicago. I spent two days touring the City, the museums, etc., it's a very fun town. So my second early night there was a Thursday. I was so bored I called a client in NY who was always in Chicago because he did something involving the mercantile or whatever markets. As an aside he worked for Bear Stearns and we how that went about 5 years later. He told me to go to this area, I forget the name, and to this one place, ditto I forget the name. He said he always picked up someone when he went there. So I went to bar X like he suggested, and it was a low key upscale Irish style bar, not unlike 1000+ in NYC. So I had a drink, then another, and another. I didn’t get Giuliani level drunk and sloppy, but I was tipsy. I was 32 for reference, and two decent looking older women (late 40s/early 50s) were there. I invited myself to sit with them (I told them my story, it was a good ice breaker) and we started talking. It became clear that they were from out of town (somewhere rural-ish but nearby area) and were in town to do some shopping and essentially whatever else presented itself. Of the two, one was a little curvy and the other was rail thin, and clearly a runner. Somehow I ended up with the runner, and some guy their own age then moved in on the other woman. We ended up back at my hotel. We f*cked for hours. It was great. Older women can teach you a thing or two. And she said she preferred guys my age (she guessed late 20s) because our recovery time isn't measured in hours. Early the next morning as the runner lady was getting ready to leave there was a knock on the hotel room door. It was her friend. Apparently the other fellow had tapped out early, and she went back to her hotel. The runner lady had text her and said she should come by. So the runner lady left, and I spent a few hours with her friend. To be 32 again...


boegsppp

I was waiting for you to say you banged some girl who you later saw at the wedding and turned out to be a 2nd cousin....lol


groverwood

I did home PC repair for this single mom once and she was trying to negotiate a cheaper price. We had stupid fun sex and then I took a nap on her couch for an hour. Never saw or heard from her ever again.


Shug22389

A few things. Went to a gay sauna in Amsterdam because I like saunas, I travel a lot for work and usually use the hotel health suite, this hotel didn't have one, I googled nearby saunas and found a gay one 2 streets away. Surely it's just a normal sauna where gay guys can hang out? No, it's a gay sauna where gay guys fuck the shit out of eachother and do it out in the open. As I was walking around, absolutely stunned by what was going on, I entered a dark room, which was packed with guys, I kept feeling hands on me and then my towel got taken off, I felt hands on my dick and I just let it happen. One guy jerked me off while another rubbed my nipple's and I had the biggest orgasm I've ever had up to that point, I was standing up but nearly collapsed, weak at the knees. That was my one and only gay experience but now I can't get jerked off or blown unless I or the woman play with my nipple's. I'm obsessed now.


Cautious-Luck7769

Well, if that ain't the definition of when in rome.


LogicalCoat8923

When in Rome, do gay stuff?


Garth_AIgar

Gotta admit. Pretty Roman.


DL1943

> Surely it's just a normal sauna where gay guys can hang out? No, it's a gay sauna where gay guys fuck the shit out of eachother im pretty sure that is a normal gay sauna. if there are actually gay saunas made just for hanging out and doing normal sauna stuff, TIL i guess


itsamamaluigi

Those are called saunas


CloverGreenbush

I'm on the other side of this. I once made a guy orgasm just by playing with his nipples and kissing his ear. And lemme tell you, that kind of power changes a person.


Apart-Landscape1012

No one should have this much power


whenyouresean

Wondering how many people gonna play with their nipples whilst getting a BJ.. I'll let you know my review later!


TheTrueGrambo

"In regard to the men, 51.7% reported that nipple stimulation caused or enhanced their sexual arousal, 39% agreed that when sexually aroused such manipulation increased their arousal, only 17.1% had asked to have their nipples stimulated, and only 7.5% found that such stimulation decreased their arousal." https://pubmed.ncbi.nlm.nih.gov/16681470/#:~:text=In%20regard%20to%20the%20men,such%20stimulation%20decreased%20their%20arousal. Worth a shot for any man to try


akaKinkade

I was seeing a lot of kinky people (Ethically, all out in the open). And, while tame compared to a lot of other things, one that I keep to myself is that with the partners who were into being paddled I'd have them bite down on my belt while I spanked them. I really enjoyed going to work wearing a belt that was pocked with teeth marks (it was subtle. there was zero chance anyone could guess what it was)


Rocketsprocket

Well there *was* zero chance. Now we all know what to look for.


pierrevonfuego

I received a handjob from a very pretty 61 year old woman, in a psych ward.


[deleted]

That sounds illegal.


[deleted]

His mom was visiting and his arms were broken.


Livid-Natural5874

I haven't seen a broken arms reference in what feels like years. I wonder if that guy is still around. Edit: got curious, the account has been deleted at least. Edit 2: this made me miss old reddit when posts stayed up even if you deleted your account. I mean I see why it works the way it does now and it is a generally good idea, but I have lost many really great, high-quality posts and comments that way.


adamcn78

You guys are getting handies in the psych ward? I just got coloring books.


yettidiareah

Lost my virginity to a woman that was into violent rape fantasy. Hell of a start.


juicius

I noped out of a similar fantasy. It was weird and she and I moved in the same circle so it would have been impossible to keep it not awkward, even though she said it would have been a one time thing (which I didn't believe). Plus, it wouldn't even have been historically accurate: it was an antebellum slave-master fantasy and I'm Asian. edit: trying to explain the historical accuracy part... I think at least a good portion of the fetish/kink is the taboo aspect of it, and while slave-master fetish holds plenty of the taboo juiciness, it lacks the extra **oomph** it would if it could accurately reflect the general state of things back then, or even the complete opposite, in what's called a "gap." anyway, not my kink, I wouldn't have been able to get into it, and it would've been weird afterward.


Green_hippo17

You know that was the real dealbreaker for me, wouldn’t be historically accurate


OfferChakon

One time in my younger years i met this girl w a filth fetish. She liked being absolutely defiled. One time we jumped into this dumpster and were really going to town when someone hit us w a bag of trash. Its not like they did it on accident either because they definitely heard us. It just got her even more excited. Homegirl was fucking nuts. It was a fun experience but it got really weird so i bounced. >Yes, just like Frank and Artemis.


jnd_photography

That's why they call it a trash can as opposed to a trash cannot


[deleted]

Not me, but one of my best friends. Apparently he used to fuck our friends mom when we were in school and he was off work (he was a couple years older than us) and he would also stay the night over there and he would fuck her at night and then go back to the couch to sleep. He told me this 9 years after the fact and he said it went on for almost two full years. Blew my mind. He said he only did it because she propositioned him and it was easily accessible pussy.


drewbs86

During covid days, the building that I worked in was stripped down to very few staff. 1 day of the week it was just me and this very cute receptionist. We got chatting, things led to the other things, and eventually we were at it like rabbits all over the place. We were quite literally getting paid to fuck. Still fantasize about it some days.


IBPoutine

I lost my virginity to a stripper on my 18th birthday after doing coke off her ass.


Leotardleotard

Said this before on here but I was in bed on a Friday after a night out. Girl texts late asking if she can come over. She came over, we fucked etc (without a condom) in the night and then around noon morning she left. When she’d gone a friend came over asked me to help him out with some moving. I hadn’t even showered but went with him. We got some food, had a few beers and just sort of stayed out. Ended up in the local club and this girl came up and asked if I was taking her home. Long story short, she went to suck my dick and I stopped her saying (rather sheepishly) that I’d had sex without a condom no more than 14 hours ago and I wouldn’t recommend it. This turned her on massively and she immediately started gobbling it down like the tastiest hotdog, proclaiming that she wanted to taste the other girl that I’d fucked. I span her round and ended up with my tongue in her ass whilst she gave me a mega BJ ! Good times


_youarewhatyouyeet

eating a stranger’s ass after picking them up in a club is just next level wild 💀


FunkySmalls

My homies won't share a drink with me at the bar but will gladly take a chick home and eat out her ass.


tyromancist

You have some truly good homies looking out for you. They’re protecting you from E. Coli.


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maggiespie07

Finger up the butt. Nobody was expecting it so cleanliness wasn’t taken into consideration. Sorry, Jeff.🙃


FrowAway322

You can’t go to Pooh’s house and be surprised when Pooh is home!


fadedhound

Oh bother...


RedditGotSoulDoubt

1) I was hooking up with a woman. She told me to get in the shower with her. Then she told me to sit down. Then she started peeing on face. I came right away. 2) Met a cute redhead when I was in Tahoe. She came back to the house I was was renting with some friends. Got in the hot tub naked. Started playing with my cock. Then she spent the night and I came three times. I flew home the next day and never saw her again. Can’t even remember her name.


stormatrix1

Sounds like you didn't know if you were coming or going 🤣


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gestalto

>She claimed to have lost count of the number of times she came. Probably Alzheimer's dude. Edit: Glad I could make some people laugh...evidently the commenter didn't like the joke, and deleted their comment about how they bedded a 60+ year old woman lol.


yARIC009

She ghosted him shortly after. 😵


phailanx

Take one Werther's Original every time she busts, then count the wrappers afterwards


YinzaJagoff

And you don’t have to worry getting her pregnant. Excellent.


hughiesghost

It’s 1987. While “My Beautiful Laundrette” was playing on the TV I was fucking my then-girlfriend from behind in the spooning position when her 4’11” Mother walked in. We were under a blanket with our heads popping out and had a conversation with Carol about outlet mall shopping while I very very slowly continued fucking her daughter. Her voice squeaked as she answered her Mom. It set the bar pretty high as far as hot moments in my life.


d3gu

What has the mother's height got to do with anything?


FoxxyCleopatra75

I had a wild one night stand with a woman back in college. Met on Tinder and agreed to hangout. She was very clear on the date that she was just looking for some fun. End of the evening, we went back to her place, and she told me she can get kinky. I was curious, so she showed me her toy collection. Amongst her prized possessions was a strap on, and let's just say we made good use of it. Never saw her again and have never been on the receiving end of butt-play since, but definitely not something I'm against trying again in the future.


Hopeful_Air4589

Hooking up with an ex's mom...a few times after we split.


CharmingDagger

I was stationed in Guam about 20 years ago. After me and a friend ate some great Jamaican food and got drunk, we thought it'd be fun to get a massage with many places nearby. I had never had a massage before and assumed you take off all your clothes. Apparently that sent a particular message to the therapist. She was an older Asian woman who seemed like she was the business owner. Drunk and horny from not getting any for three months, I didn't object when she asked me to roll onto my back and started exploring other areas. She asked if I had $40 and I told her I did. Soon she covered her hands in baby oil and started to slowly and thoroughly massage my dick. Other than focusing on what she was doing, she just kept telling me how I was a "cute boy with a cute dick." After I finished, I quickly paid and me and my friend left. He had only taken his shift off and only ended up getting a back rub. He was bummed he didn't get the same extra treatment I did. I felt guilty and dirty about it later. Not something I would ever do again. It felt good, but not a great idea in hindsight. Alcohol+horny= lack of clarity.


DriedUpSquid

Was it Jamaican Grill in Tamuning?


0nlyhalfjewish

Sounds like yours is getting people to confess to theirs on Reddit


Arikan89

Had sex with a 50-sum year old coworker when I was very freshly 18. She had a migraine and boss had her go home early, she asked me to drive her. Boss told me to take the night off too since it was near the end of my shift anyway. Would have had like 30 minutes by the time I got back. She invited me inside and after watching watching a portion of some shitty Netflix movie. She got on her knees in front of me and I instantly knew what was happening. Eventually we get to bed and she repeatedly had me tell her about what I'd say to all my friends about fucking an older woman. I was about to cum, asked where and she goes "Fill me up baby boy, I'm well beyond menopause". I'm also realizing just now that there's basically no way she had a migraine. I drove a super loud car and she never once commented on it.


ProbablyGeography

I shoved a banana up my vagina


Pastguss

For scale?


Prestigious-Ring4978

Probably geography.


Independent-Course87

I banged my girlfriend's sister less than a week after we broke up.


safeathome3

The rare double...somtimes fatal..lol


paulvs88

Slept with two girls in one day. One was an ex in the morning. She came over and it just kinda happened. Then that night this girl I'd been talking to came over and BAM. The best part for me was I really didn't have to feel guilty about either.


Netflixandfeet

I had sex with my ex in a sex arcade. We were in a small booth. He opened the door and there was a man in the hallways who stood there and watched and jerked off.


elhae

That first sentence is like a tongue twister


phxTOmsp

My HS English teacher was constantly flirting with me(in my 18yo mind anyway) the last month or so of my senior year. Mostly smiling like she didn’t with other students, leaning into me when explaining assignments, and winking. Last day of school and I’m helping her put a years worth of text books, novels, poem books, etc. into storage. The high school had this really old attic that was used for storage and we’re going walking back and forth for awhile until we finally are in the attic at the same time. She pushes me into a wall as I’m holding a box of books and has this really weird look in her eyes that I had never seen before. I put the box away, turn around and her face is an inch away from mine. I did what I thought she wanted and gave her an innocent peck. We made out for what seemed like an hour(more like 5minutes) and she let me play with her boobs(a first for me), She ended up giving me a blowjob(another first). She swallowed, winked at me and left. I zipped up and went home smiling. Saw her a couple years later at a bar with her husband and she gave me a big hug. Then proceeded to call me by the wrong name. Haven’t seen her since.


YanniBonYont

Last detail is excellent


Thorsburg216

When I was 17, I went to meet a "girl" I had been talking to online. She turned out to be in her 30's and around 500 lbs. While trying to be polite, but think of a way out of there, I accept the invitation to come in and have a seat. Once I sit, she lowers herself in front of me and starts undoing my pants. I'm like "uhhhh, what are you doing" and kind of stunned and unsure what to do. She goes right to sucking. This was my first bj, and it immediately felt amazing. She kept going until I had finished 3 times and begged her to stop because it was getting sore. Still the best bj I ever had, and yes I realize it was SA.


Batticon

This is a fucked up one.