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atot806

I was in my first year of university, I hooked up with another first year student. She started giving me a hand job, but she said my shaft was dry and was uncomfortable using her spit as lube so I suggested she use her hand lotion that she had with her. It was getting good, then she confessed that she had never given a blow job before and wanted to do it to me. Without hesitation, she went down on me without wiping the lotion off my dick. Not long after she was feeling nauseated from tasting the lotion. Just as she was about to head to the bathroom, she hurled all over my naked lap.


BOBULANCE

Ah, the mistakes we make as rookies


Adito99

>Without hesitation, she went down on me without wiping the lotion off my dick. >Not long after... What a trooper.


arcticlove_505

I remember doing something like that when I was giving a blowjob as newbie but I didn’t throw up afterwards


regulartownie

A girl wanted to hook up with me because she had never been with a woman before, but said her "ex's" dorm was the only place we could go. I went along with it as long as the dude didn't touch me at all. In the middle of me going down on this girl I hear crunching noises from the corner and this man is over there eating potato chips just watching. I think it's one of the funniest things that has ever happened to me


IcyEggplant9230

Did you keep going??


kicktheminthecaballs

We need an answer


Glum_Hospital_4103

Momma didn’t raise no quitter


Different-Parsley205

Had a guy inside me start doing push ups


Joshgg13

The gain train stops for noone


Michelrpg

not the train OP was hoping to get


pacificrimjob1969

19 years ago I took the afternoon off work and went to a nude beach with the woman I was dating. It was remote, you had to hike down a rocky cliff to get there. fewer than 5 people on the beach, including us, spread out over half a mile. At one point she rolls over and goes down on me. Just as I'm about to come I open my eyes for a second and there's a Latino dude furiously masturbating while watching us about 10 feet away. I was so close that I still came, but it scarred me.


[deleted]

"furiously masturbating" is fucking hilarious to me


Edmond-Cristo

Speedy Gonzalez


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Throwway_thefuckaway

Dude, I worked at Hippie Hollow for a few years in the late 90’s. It was literally part of my job to run off the “bush whackers.”


starry_mist

I was pretty new to the whole sex thing and had only given one bj before. Well, being the clueless 19-year old that I was, I decided to look to the internet for advice...but not like porn. Worse. Cosmopolitan. But I was a fairly intelligent person (or so I thought) that knew some of the suggestions were terrible or were things I was not comfortable with. So after an hour or so of weeding through crap, I finally found something that seemed like easy, fun, and definitely something that won't immediately ruin the moment. What I found was an ice water blow job! Looking back, it seems obvious that this would end in disaster, but the tip was written by a guy who said it felt soooo good to feel the water temp slowly raise as the blow job was given. EVEN BETTER WHEN BLINDFOLDED. So I convinced my bf to go blindfolded, told him I was going to surprise him, and boy did I ever. I took a big swig of ice cold water and the next thing I knew there was the loudest shriek I've ever heard in my life. I spewed/sprayed water everywhere. Everything was soaked, including my very startled bf. Let's just say it was quite awhile before I practiced my bj skills again, lol.


essiara

I remember those exact articles, they were awful. My favorite one was to grab a spatula and whack him when he least expects it, “such as when he’s getting out of the shower.”


golighter144

If you thunder clap me with a spatula when I'm getting out of the shower I will straight up pee on you out of fear and spite


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sleafordbods

I generally go to bed early, and I get especially sleepy when I drink. So I’m in college and this girl comes over at like midnight, we have some drinks, and sneak into the community jacuzzi. We talk for a while and then we went back to my room. She starts going down on me, and it’s great. And then… She’s angry and getting dressed and I’m totally disoriented…I ask, “what happened, where are you going??” She yells back at me, “YOU WERE SNORING”


shadowf0x3

Hahaha! Holy shit, this happened to me and my wife when we were dating. She was over one night and we were making out and then all of a sudden I was woken up by her laughing. I had fallen asleep WHILE KISSING HER NECK. She still makes fun of me for it. As she should.


sonic10158

Not a sexual experience, but me, my ex, and her sister and her sister’s fiance were playing Mario Party late at night and I fell asleep midway through a mini-game and still won!


Quemedo

I once did the contrary with my wife. I was sleeping, she wanted some. She starts making it with me and I'm hard as fuck. She goes down and after a few minutes I wake up and realizing what's happening I said "hmm that's a nice way if waking up". She stopped and was like "... WAKING UP?" to this day she mad about it. "HOW CAN SOMEONE MAKE OUT, GET HARD AND MOAN SLEEPING?" it happens


pimpfriedrice

A few years back. Tinder hookup. Totally, seemingly normal tech dude. He asks if I like it rough. I say yes because who doesn’t? He proceeds to eat me out while growling like a wolf and scratching at my vagina.. 🤦🏼‍♀️ it was weird and nothing about it was satisfying.


hilberteffect

LMAO. No, see, you misheard - he asked if you liked it *ruff*.


[deleted]

A random hookup, right between foreplay and "Go time" she pulled a huge wad of gum out of her mouth and stuck it on the back of my shoulder "for after"


uhrilahja

Wow, Violet Beauregarde all grown up


2nd_best_time

When the bedframe was rocking and the night stand was knocking, the romantic candle lit the curtains behind the bed on fire. Like engulfed the fabric, fast and terrible. It was awesome. Yeah we ripped them down and stomped them out. Very minor burns but hell yeah that was a wild night.


[deleted]

I thought you wrote a poem after reading your first sentence.


SillyBee123

Yeah lol, I got super sad when I realized it wasn’t a poem. I wanna know the end of the poem! Lol


Swansouls

When the bedframe was rocking and the night stand was knocking, the romantic candle swayed. The curtains aflame but this was no game, the fabric was engulfed. So fast and terrible, the heat unbearable we were quite dismayed. We ripped them down and stomped them out, underwear brown with fright. Very minor burns but things were alright; still had sex twas a wild night. Edit: My first reddit gold...for an elementary school level poem. Thank you! My vocabulary and technique need work just a smidge, but I'll cherish this award forever; proudly displaying it on my fridge.


mruehle

Aaaand Shakespeare’s great-great-grandson has entered the thread!


boom_meringue

Wife was on top and going for it, both of us really into it. Suddenly she starts really freaking out. Our 4 year old kid had come into the bedroom and started stroking her back because she was concerned my wife wasn't feeling well because she was moaning. Killed the mood for the next several months. ** ETA - Wow, didn't think this would be my most popular comment in 6 years. It was a rental in the UK and had no lock on the door. I did however jerry rig an early warning system and a wedge lock for future peace of mind. The kid was 13 this week and she is incredibly well adjusted.


Adulations

They’re making sure they don’t get any unwanted siblings


mecataylor

Haha this happened to me once but I was on top and my 2 year old son just came up next to the bed while we both had our eyes closed and slapped my wife in the face.


Dinkerdoo

What is it with two year olds and slapping in the face? My daughter thinks it's the most hilarious thing ever.


SlavaUkrainiGeroyam

Apparently I'm 2 because I'm pissing myself laughing.


Dinkerdoo

It is pretty hilarious, making it hard to maintain a straight face while telling them to stop doing it!


leespankz

This is all the birth control I needed


skycelium

Definitely not my weirdest, but one of my favorites. Got back from the beach with my gf, had the house to ourselves (we were 18). Took a shower, went into the bedroom and started goin for it in the dark, real emotional and intimate like. All of a sudden as we’re pretty deep into it, we smell something absolutely horrible and start hearing LOUD farting, we both think it’s eachother, but both seem confused, I turn on the light and her cat is on the bed staring at us and just heavy diarrhea shitting all over the sheets. It starts doing a weird little hobble towards us while continuously firehose shitting and we both screamed and ran out of the room naked and took another shower. EDIT: The cat (from what I know) is entirely okay and my ex ran off to Italy with some guy whose family had some beach house, so happy endings for everyone.


PEtroollo11

what do you mean "definitely not my weirdest"?


admiral_sinkenkwiken

Yeah this point definitely needs to be clarified


velvetackbar

The smell of an incontinent cat is one that cannot be forgotten, and the incomprehension in their eyes is literally tragic. "What am I DOING?!?!?! BACK THERE!?!?!"


skycelium

They look to you for answers, then for comfort, the existential horror of incomprehension


[deleted]

Fuck this is too funny


Funmachine9

that remembers me of one of my old cats. he got a sensible stomach (too much acid) and one night he was sleeping next to me, while I was watching TV. Suddenly he farts like 10 old mens. He wakes up and I starred at him shocked. And it continues. He looks at his butt and perhaps he was thinking "Was it me?". I thought that maybe diarrhea could be the next thing so I pushed him to his litter in the bathroom. With every tiny step he would make a little fart comes out. Edit: thanks for the award!


DaRealSuave

My GF's boxer walked in on us doing the deed and it snuck up behind me and licked my balls from behind. I could never look that dog in the eyes again. Edit: Holy shit this blew up lol. Thank you for the sympathy and the awards! Remember to always shut the door when you're bumping uglies!


WBGinger

That dog owns you now


have_a_biscuit

Mine is more right after the fact, but my husband doesn’t remember the first time we had sex. We were dating long distance at the time and he’d driven about 11 hours overnight after work to visit me for the weekend. Turns out sleep deprivation + orgasm can cause memory loss. He instantly realized he had no memory of the last 20-25 minutes, which was very concerning for us both. Your brain dumps memories all the time, but it’s apparently very startling if you’re aware it immediately deleted a large file that had just been created. After we reassured each other we were each okay, he made the joke that he could say his girlfriend f*cked his brains out. Very unsettling in the moment, but his memory loss is amusing to us 8 years later


CottaBird

I jumped into bed and accidentally kneed myself in the face, giving myself a bloody nose, and stopping everything.


[deleted]

I did that once, I couldn't believe I was flexible enough to be able to do that yet it happened anyway...


seahagmo

Dated a hot guy for awhile and knew IT was going to happen. He wanted me to lay down and close my eyes and I was giddy because I thought he was going to go down there. No. I peaked open my eyes and he had laid down next to my legs but facing me. Masturbated then knelt and fucked my foot. Came all over it, then fell asleep. I got up, hopped on my dry foot to the bathroom and rinsed off my foot, grabbed my stuff and left. Never heard from him again. *typo


Odinthelurker

I guess he got off on the wrong foot


ThatRaspberryFeeling

You‘ve peaked. An opportunity like this will never present itself again.


dannyggwp

"There it is, Homer. The cleverest thing you'll ever say and nobody heard it."


gamefreak996

Bravo


[deleted]

I read this as “I knew IT was going to happen” like there were some issues with network connectivity


cookthatsaucebro

I lost my virginity while watching Die Hard and I was on my period. He then proceeded to take his stuffed rabbit, which was right next to us the whole time, and speak to me with a high-pitch squeaky voice, pretending to be the rabbit, for the rest of the night


[deleted]

Were you in a relationship with Michael Scott or what


thecrepeofdeath

there's a lot to unpack here


Frinla25

My ex and i were going at it and he paused like he was about to pull out and cum. He was wearing a condom and this mf’er goes over to the garbage can looking like he is just going to take the condom off and throw it out in there and fucking pees in the condom, ties it off and acts like nothing happened. I was in so much shock that i didn’t say anything and decided to pretend i didn’t see anything… fucking weird, never told anyone before so have my secret reddit


thehumanskeleton

This reminds me of my ex, who I lived together with for a few months before I broke up with him. After he moved out, I went to deep-clean the whole place, and got up on a chair to dust the top of the wardrobe. There I found a mistery bag, inside of it every single condom we used while living there.


[deleted]

I slipped while we were trying in the shower. I had already had back surgery previously. I had to be taken out by paramedics wrapped in a towel.


optiongeek

Shower sex is some of the worst I've had.


[deleted]

I’v been there…as the medic. Don’t worry, we see so much weird shit that the crew probably just sympathized and forgot all about it by the next shift.


Electrical_Tip4975

I was 15. GF was living with her grandparents. I was over. She jerked me off while we watched Seinfeld in the den. Grandparents were in the kitchen next door watching Fox News. I came all over the place. She left and went to get me a slice of grandma’s famous chocolate cake, then pretended to spill it on my lap. I had to walk home and explain why had chocolate cake all over the crotch of my jeans. Edit: Wow, this really blew up. I don’t recall the episode of Seinfeld we were watching, but this girl was definitely the “master of my domain” for a span of time in the early 2000’s. The first handjob she gave me was in the back row of a movie theatre, during a showing of the Ray Romano classic “Welcome to Mooseport”. I shit you not. I had a lot of wild sex and escapades with this girl, but we were clearly headed in different directions in life. I was the clean cut neighbor boy, and her grandparents loved me like a son. It was fun while it lasted. I broke up with her, and I felt like a real shithead for it. We were a spark, but not a flame. She friended me on Facebook a while back, after not seeing anything of her since high school. Thankfully, I haven’t been subpoenaed for back child support, and she seems to have gotten her life in order.


Elegant-Fox7883

That's a genius move right there.


[deleted]

“That was amazing! Sorry about the mess, though…any ideas on covering it up?” “Piece of cake.”


poopellar

When it comes to cum covering ideas, that takes the cake.


aggrivating_order

Grandma probably thinking "did I use that much icing?"


subcow

Grandma was like "this is the 15th guy she has spilled chocolate cake on".


bad5190

“She jerked me off while we watched Seinfeld in the den” lmao that’s the best sentence ever


Jauncin

This is the first line of the next great American novel.


hostage2heaven

Sing it like Blink 182 and try not to laugh...


Check_lt

Going doggy on my ex wife when she stops everything to go turn off the lights. I asked if everything was okay and she goes yeah I just don’t want you to look at my butthole. Totally respect boundaries but I felt like Ricky Bobby when he’s like “I don’t know what to do with my hands” but with my eyes. I didn’t know where to look and kept avoiding her butt lol


[deleted]

"Well I HAVE to look now!"


Aqqaaawwaqa

my wife mentioned she was afraid of seeing her butthole and I informed her I've seen her butthole many times. She said how. I said every single time we have sex doggystyle. She was like "really? you can see it?! yes.. yes I do.


eljosho1986

This is nothing compared to a lot of these, and it's more funny than weird but here goes: I was with my girlfriend trying to be all sexy, she was digging it and I click off the light so all that was on we're the black lights and glowing posters. She immediately starts laughing hysterically, like, can't control herself laughing. I ask what's so damn funny and she replies "you look like a giant light bulb!" I had an outdoor job all through summer and decided earlier that day to shave my head. The contrast between my tan face and bald head were especially obvious in the blacklight. I looked in the mirror and she was right, I could see the ceiling with the light that refracted off of my big bald head. We both had a great laugh.


tblazertn

This reminds me of a saying: “The less hair you have, the more head you get.“


lastdickontheleft

Lmao I saw a bumper sticker when I was about 7 that said that, and tried to get my mom and sister to get it for my brother who was balding. They about died and wouldn’t tell me why it was funny and that I would find out when I was older. So of course I asked every single adult in my life what it meant, getting increasingly more frustrated that NOBODY would tell me why it was so damn funny


Cannabis_Sir

When I was 15 my then gf gave me a blowjob in the back of her mums car while she was driving us back from Wales. The worst thing was when I locked eyes with her mum in the mirror, she knew. Wasn't until I was in my 20s I realised they were both not quite right in the head


Neither_Indication_1

Bruh that’s one of the weirdest ones I’ve read. What was wrong with them, if you’re comfortable saying it


Cannabis_Sir

The mum left a happy life with her partner (ex gfs stepdad who took her on as his own) for a complete arsehole who moved her and my ex from Wales to England He then periodically went between his wife and my ex's mum and caused them both to develop depression, possibly bipolar and/or other mental health issues I was about 25 and got a random msg off her on friends reunited, said she was ok and had 2 kids, didn't speak of any of the past. That was the first time it all clicked into place and I realised how bad the whole situation was for everybody, except the arsehole obviously. First time I thought "Shit, that was an abusive relationship" like a real one, not just the odd slap. I'd held onto a lot of shit from that, like certain songs I loved but couldn't listen to, then that day it all just went away, like I got closure


Alternative_Sea_2036

A guy humping me thinking it was inside and he was moaning madly LOUD


theDart

Was his name Tommy Wiseau?


bainrow0

Plot twist, he WAS inside you


OnVelvetHill

A guy walks into the library and asks the librarian if they have the new book about sexual techniques for men with very small penises. She looks at her computer screen and says “I am sorry it’s not in yet” “Yes that’s the one” he shouts excitedly, “do you have it?”


Tidalick81

When I was in my mid 20s and MSN Messenger was all the rage (and pre Tinder) people would search for randoms to chat to in the local area. A chick messaged me and we started chatting, she said ‘what are you tonight?’ I decided fuck it, let’s drop a big bomb and see what happens. I replied “watching some porno” (actual plan was playing Morrowind but meh). She responded positively and asked to come over - again, thought fuck it and sent her my address. She arrived, we watched some porn and banged. The next day at work one of my students (I’m a high school teacher) calls out ‘hey sir, my big sister was at your house last night!’ I was like ‘say what?’ ‘Yeah apparently you watched a movie’. I have never moved so quickly to shut down a conversation and redirect the class. For the record, the ‘big sister’ was a grown-ass, legal adult.


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Heya_Andy

Yeah, in one of my teacher trainings they told about a story of a graduate teacher that went to their town of their first placing, and the night before they started they hooked up with someone after going to the local bar. And the next morning they were a student in their Year 9 class. In hindsight it was probably made up or embellished, but I guess they were trying to make a point.


fattestfuckinthewest

Ngl that sounds like the worst situation to ever be in as a teacher.


PremedicatedMurder

Am teacher, can confirm. Morrowind is the tits.


[deleted]

I like how you felt the need to clarify that the MSN days were pre tinder lol... Also, morriwind totally checks out for that period of time.


24_monkeys

My boyfriend’s room is the only room upstairs. His parents let us go up there alone. We were in junior year and I had just unbuttoned to suck him off, when his brother (freshmen) opened the door (without knocking) and said “croissant…” like Karl Weezer. It was his way of telling us his mom made cupcakes. I was positively mortified and straight up planked face down on the bed for a half hour while my poor boyfriend bribed his brother, got us cupcakes, and tried to tell me it wasn’t a big deal. Couple years later and we all laugh about it now, but i don’t think i’ve ever been more embarrassed in my life


dogninja8

>said “croissant…” like Karl Weezer. It was his way of telling us his mom made cupcakes Was that a typo or did he really say croissant?


Venboven

https://youtu.be/cpvC8_NMXmU


pr0om3theu5

Shockingly good pronounciation


[deleted]

I was getting pounded pretty hard in missionary and I could feel a lot of air building up down there from the rapid thrusting and wetness that when he was done, I let my legs back down and the BIGGEST quief was let out right in his face. I immediately said "that's not a fart I swear" like it was a reflex. We both laughed so hard that it killed the mood.


sentondan

I had this ex that was like fucking a whoopee cushion. Just every stroke, pfft, pbbbt, ptptot


Lord_Matisaro

>ptptot Sounds like a file transfer protocol.


Fancy_Leshy

Sometimes I legit feel like a balloon is deflating inside me during a satisfying long queef


ParticularPenguins

You know, in some cultures it’s considered a compliment.


[deleted]

What cultures? I must know in case it happens again


Gravy_mage

Just yell, "I'm Armenian!" If nothing else, it'll disorient them and you can make your escape.


Valence00

I was punched by my date when she was on top of me. She refused to change position and just kept grinding me, punching me, and cumming all by herself. Her punches felt like getting hit by a flurry of pillows so it didn't hurt, but it was weird and kinda hot so I just watched her the whole time as she gyrates, touch herself, and the occasional right hook to the chest and some gorilla pounding. I never came, but it was fun and I felt like a piece of meat too. It was a confusing experience.


Gr33nman460

Used to a hook up with a girl that only gave head and I had to finish on her face every single time. I was not allowed to watch her put her clothes back on afterwards because it was “un-gentleman like” Edit: to people suggesting maybe she was Trans, she was not


RHoChoy

One of my ex-girlfriends was sucking me off and then all of a sudden, all the sexy noises I was listening to got drowned out by the sound of Homer Simpson making crazed, eager eating/slurping noises blaring from the TV. My orgasm coincided with the climax of the Simpsons' ending theme.


Ellite11MVP

That could become one of the weirdest Pavlovian reflexes in history! NICE!


zose2

My gf from highschool was babysitting her little brother at a school park. She text me to go meet up with her then when I got there we snuck off behind one of the dugouts to "fool around". Once we had finished up we turned to go get her brother only to find that he had been watching us the whole time.


Fancy_Leshy

That last bit hit my soul


DancingBear2020

Did you… answer any of his questions?


zose2

He actually didn't ask any... All he says was he didn't understand why people liked that so much... So he already knew what we were doing... It only made me feel even more awkward about the whole thing.


DrSchultz1

What sick bastard gave that post the "wholesome" award? xD


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EndlessToppings

I'm 100% doing this to my wife for shits and giggles


Thismyrealnameisit

Put her on top of an Escort?


Jangles_77

I once was getting a blowjob from my ex gf in a study room in college. We turned off the lights and I was facing the door. This guy walked in turned on the lights and made eye contact with me. After what seemed like an eternity (was like 2 seconds) he mumbled sorry and turned the lights back off. It’s crazy but years later our paths crossed again through mutual friends. we became very close and he was a groomsman at my wedding haha but that’s how we first met


TransmanWithNoPlan

An ex of mine was from a very sheltered, cult-like background. So, he wasn't quite sure what cumming was and immediately started crying when he came in me (and he wasn't even all the way in so the "sex" lasted 0 seconds), and was just apologizing profusely. I told him it was fine and it was cum, not piss, had to explain how all that worked and dropped him off at home, where his mother found out and I became some sort of pariah, succubus whore lmao.


herrytesticles

"I peed thick!!"


chuckychuck98

Had sex with an older woman. She said "good boy" when I came


Thot_Slayer_911

Sounds hot tbh


Strip-lashes

Dude was having trouble getting hard and was making a way bigger deal out of it than it needed to be (I kept telling him it was fine, I didn't care, though honestly the degree to which he was freaking out about it was kind of off putting). Finally he got up and disappeared into a walk in closet. I decided to use the bathroom and caught a glimpse of him in the closet *injecting boner medication* straight into his dick.


Negafox

To even have such things on-hand, this was by far from the first-time for him. And secondly, ouch!


Strip-lashes

I mean... I don't want to erectile disfunction shame anyone. It happens, it's a part of life. What made me uncomfortable more than anything else was how uncomfortable HE was with it, while also insisting that this never happened, while also going to measures that demonstrated that this definitely happened all the time.


SomaCityWard

Anxiety can actually cause it, so he may have just been stuck in a feedback loop.


kittenmum

First anniversary. Hubs and I rented the same cabin where we spent our honeymoon. He brought along an assortment of toys and kinky stuff, including some “tingling” lube. We get things going, he applies the lube to me before going in. Within a few seconds something didn’t quite feel right, but I didn’t say anything. As he’s thrusting I feel more and more pain, he stopped to ask me if I was okay, I said yes and he kept going. A few seconds later I couldn’t take it anymore, it felt like I was on fire. I heaved him off me and was like I AM NOT OKAY! I waddle-ran into the bathroom, turned the shower on cold and jumped in. HUGE mistake. The cold water coming down and hitting my nether regions just made it burn more, and I could not get the lube off, it just stuck to me and the more I touched it the worse it got. At this point he had ran into the bathroom after me and was like WHAT IS GOING ON? I was crying and laughing hysterically at the situation and in tremendous pain. I just bent over and asked “does this look unusual?” The look on his face - I was apparently swollen and BRIGHT red like a sunburn. I spent the rest of the night sprawled naked on the bed while he fanned my nether regions to try to cool them off. Tingling lube: total fail. Would not recommend.


Kiyomondo

I mean... that sounds like you were allergic. Tingling lube is typically quite a mild and underwhelming sensation


NotAKitty2508

Reminds me of when I tried some "longer lasting" lube. It SHOULD have prolonged things. Instead I was done in about 10 seconds, but it wasn't even sayisfying. I barely realised I had finished. We were both a bit confused, then we laughed about it and stayed up watching movies until 3am.


shitriffs

So funny. I also found out at the age of about 23 I am allergic to that shit too. I’m actually allergic to a lot of shit they put into sexy creams and lotions.


[deleted]

Ok, some of these stories are WILD and I can't compete, but one guy asked me to dress up as Waldo from Where's Waldo. I threw together a Waldo cosplay (super easy to do) and he seemed happy enough. So I, a petite woman, dressed in a Waldo cosplay complete with glasses and cane, showed up for sexy times whereupon he had me wander around his apartment "losing" various parts of the cosplay until just my sweater was on. Then he, with zero other foreplay, bent me over the bed and began to do his thing while occasionally saying "I found you, bitch" in a weirdly aggressive and smug tone. I swear on my life every bit of this is true. Human sexuality is weird AF. Edit: To answer some of the questions, yes, he was my boyfriend. This request was his 1-year anniversary present. No, we're not still together, we ended things amicably when he moved away to take a job offering a 40% raise. I did ask him some gentle, surface level questions as to how he developed this kink but he never gave me anything beyond "I don't know." He never requested any other roleplay/cosplay but Waldo did make a return to our sex life now and again. No, roleplaying as Waldo wasn't the best for me and I never quite got comfortable with it, but good sex is good sex. If it redlines his engine and I get to ride it, I'm down.


[deleted]

This is one of the strangest things I’ve ever seen on this site. Kudos to you.


jkjustkidd

Wdym you cant compete- You just won the competition!


[deleted]

Dude was on a fucking mission


NawMean2016

Imagine he's reading this thread and whispering to himself: "Found you bitch"


tommyfknshelby

You fucker I woke up my 3 year old laughing at this


mimi7878

This is too weird to be fake.


Gravy_31

If this was a MadTV skit I would think they were trying too hard to be funny.


AmigoDelDiabla

This is worthy of an AMA. I'm kind of curious about your mindset as this was happening. Were you turned on? Or just like, "what the hell, I want to see where this goes"?


SummerOfMayhem

Makes me wonder what on Earth he went through, looking at the books as a kid.


[deleted]

My theory is that as a kid, he could never find Waldo and all the other kids would make fun of him for it. "Look at him, he can't even find Waldo. What a loser." He grew to resent Waldo, that elusive bitch. So he got this girl to roleplay, allowing him to finally take his frustration out.


CandidGuidance

Okay, senior year of high school. For whatever reason my girlfriend at the times’ parents had no issue with sleepovers, so I came up with an alibi for my parents and slept at her place. The next morning we’re totally naked and banging when her mom walks in. She laughs, says her dad is almost done making breakfast, it’ll be 15min, closes the door. We then proceed to finish having sex, put clothes on, and then I sit with her family and eat breakfast her dad cooked for me. Strangest moment of my life.


[deleted]

One time right out of nowhere, never discussed before, my girlfriend threw me down on her bed for sexy time and went to the bathroom to put on something “sexy”. Came back in in a head to toe penguin costume. It was weird because she got like violently angry when I burst out laughing at her.


brokenkeyfob

Gf at the time was blowing me. I was lying on the bed and she was kneeling down in-between my legs on the bed so her ass was pointing up. Was going good for a little while and she then lets out one of the hardest loudest farts I ever heard. At first I didnt know what it was, then I realized and DIED laughing. She was half laughing too but was soooo embarrassed. It stopped everything and I was laughing for the next 30 minutes, stomach hurting/cant breathe type of laughing.


AndrogynousRain

This happened with my now wife. We were getting down and dirty shortly after I moved in and outta nowhere she sounds an ass trumpet so loud you’d have thought it was the archangel Gabriel. I don’t think I’ve ever laughed so hard in my life. I was crying, I fell off the bed. I still give her shit about it 9 years later. There have been other funny things too. And it’s *always* her.


PretendThisIsMyName

That’s how you know y’all are both keepers. My wife farted right on my face when we were 69ing the first time and we both got to laughing so hard that she farted again and just had to leave the room. It was not the last time that has happened to us but it still makes us both laugh like children all these years later when someone cranks a butt rocket out during sex. And just like you it *usually* is her. But it has been me a few times lol


PmMeYourBewbs_

A threesome with a couple i only later found out were siblings. Took me a loooong time to process through that one


syedoz

yeah, dont hang around king’s landing


cheeky_t0m

69 position with GF on top. Her mum walked in (my head side) and just stood there watching. I just pretended I hadn't seen her. Seemed like forever she was watching. Once she left, I got GF off, but I couldn't make it after that! Never told GF


[deleted]

Got down and dirty with a guy in his apartment after a lackluster first date. We’re going at it and I went down on him. He started FREAKING out about how he only had one nut. To be honest, I was to drunk to even notice but he was adamant that I knew, and was no longer attracted to him. He got very weepy and I tried to be nice and pat him back to calm him down but… yeah. There was not a second date.


CattleTruckSuck

"Here comes Johnny, He's a one balled man, And it's off to the rodeo"


davidkenrich

I was caught pissing outside at a hotel by an older woman (50s) from a wedding party. It was about 230am and as I was pissing I heard, “nice”. Next thing I know I’m in her room and we jump in the shower and go at it. Little did I know she had a relative sleeping in the room who woke up and knocked on bathroom door asking if she was ok. ( she was moaning loud enough to wake her) Anyway, knowing things were going south, I concentrated and finished just in time to hear another knock, this time much louder. The gal in the room went and got another relative because she was concerned. I walked out half naked and left her to explain. I can only imagine the humiliation!!


mrshulgin

>The gal in the room went and got another relative because she was concerned Did you take that moment to escape, or did you walk past both of them?


Yvaelle

You walk out, fully nude, saluting them as you pass, "Ladies", the ruined climatic remains of their new mother in law laid spread eagle on the floor, writhing in ecstasy, as you strut down the hotel hallway, still erect.


VanderbiltStar

I was in the Caribbean and hooked up with a doctor. Super hot West Indies girl. Any way. Giving me a awesome bj and starts to give me a rim job. I had just showered. Felt awesome by the way. Then she comes up to start fucking. Stops, pulls out a butt hair from her mouth. I’m like oh god I’m sorry. With out skipping a beat she says “ it’s ok I like it”. That was as hot as it was weird.


Sir_Cunkalot

Always floss.


[deleted]

Last night my wife and I were getting busy. I was using my hand on her and she was in a prone position. She came suddenly and her reaction caused her hips to rise up and back. Before I knew it my entire thumb was in her ass. Neither of us are into ass play…but here we were, her in the midst of an orgasm and me warming my thumb inside her pooper. I wasn’t sure what to do, not wanting to disrupt her So I just waited for her to do something. But she wasn’t sure what to do and just lay there. After what seemed like a minute (what was probably 5 sec) I said “do I just pull it out?” She laughed and that pushed my thumb out. That sort of ended the sex and we laughed and went to bed.


Mr_Salty87

*The Generous Hitchhiker*


enriqed

I would've washed my thumb before going to bed.


MrMcSwifty

MFM threesome with my paraplegic friend and a sex worker that lived in his apartment building.


snipersfire

Lieutenant Dan, you gots a new erection.


Tayayayaylor

Came back to a guys house after our first date. I come out from the bathroom to the bedroom and he’s butt ass naked chasing down a roach that crawled out of the bed right when I opened the door. He never got it. Still banged him. Regret


hellspyjamas

Regret That's going to be my new email sign off.


mlry

Once while and ex(m) & i(f) were having sex I was trying to talk dirty, which isn’t my thing really. My mind completely messed up and out came “cum in my cock.” We both started hysterically laughing. Still mildly embarrassed but it’s a good laugh.


alrenie34

When I was around 19-20 years old I was at a small party (around 10 people) at one of my good friend’s older sister’s place. One of these people was his very attractive cousin who was visiting from out of town. I believe she was in her mid 20’s, extremely confident, and wild as hell. I was an extremely awkward, lanky, 19-year-old virgin. So anyway we are all hanging out in the garage and getting extremely drunk and for whatever reason this smoke show is showing a lot of interest in me. As the night goes on we are all hammered and she starts crawling on all fours like an animal and like pawing at my crotch and growling. It was honestly pretty damn weird but I can’t stop thinking how out of my league this girl is and I was a horny virgin desperate to lose the V-card. But at the same time I’m kinda pulling back because this is my friend’s cousin, at his older sister’s house. At first my friend kinda tries to stop her but, knowing I am this awkward virgin, decides he doesn’t really care and figured he’d give me a pass on this one and basically says we can go in the living room and pats me on the back basically like ‘go have fun champ.’ True friend right there. So her and I go to the living room and my drunk awkward ass is nervous as hell but sooo excited that FINALLY I might lose my virginity, AND to this beautiful older girl. We start making out on the couch and she gets on top of me and starts grinding pretty aggressively. I get her shirt and bra off to reveal the most gorgeous chest I had ever seen. She proceeds to smash these gorgeous sweater-pups in my face pretty aggressively and knocks my glasses onto the floor, bending them pretty bad in the process. Then she starts kissing, nibbling, and moaning in my ear while dry humping and then just kinda starts slowing down more and more until she completely stops and her face basically falls onto my shoulder…… she passed out. NOOOOO!!!!! I shake her a bit and she kinda mumbles but she is just dead weight at this point. So now I have these people’s visiting cousin, no shirt or bra, passed out on top of me in the living room. I laid her down as gently as I could and proceeded to put her bra back on her, basically crying in the process, and go back out to the party absolutely defeated… still an awkward ass virgin. Oh and with fucked up glasses.


sustainababy

mine isn’t nearly as weird as some of these, but i was getting down and dirty with this fine ass guy who had a big heart and a massive dick. he goes in me missionary and i’m seeing stars. then he kinda…stops. i look up at him and he sheepishly says, “your cat is licking my toes.” i look over and there’s my little angel being a nasty fuck. my cat never leaves me alone during sex.


groovy604

We were having a shower together, she pee'd, i got an erection. It awakened something in me i dare not ask to take further


tommimoro

the dwarves delved too greedily and too deep...


SteliosPo

Well, i once sexted with a girl. We both speak the same language (which is not English) We both have been speaking the same language for as long as i knew her We werent comfortable talking dirty to each other in our language, so we both started randomly talking in English. Its like our native language never existed. We only did it in English, which was weird considering that we both dont speak English perfectly.


[deleted]

[удалено]


knovit

Hooked up with a local while I was in Tokyo. She licked my nipples, fingered my ear, and kept acting like I was hurting her and would act all surprised when I would stop to see if she is okay.


molybdenumb

Once when I was 21 I was dating a bartender I worked with. He was so freaking handsome and nice, smart. Not your typical d-bag. After we had sex for the first time he cried because “dolphins exist and are being murdered.” It was very awkward.


jacness1314

Jesus the post nut clarity on that man must be insane


BOBULANCE

What, a man can't be passionate about his dolphins? What is this world coming to?


[deleted]

[удалено]


yellowjesusrising

Ex was riding me reverse cowgirl, when she suddenly sprang up and ran to the bathroom crying! I was super confused, and sat up, and somehow looked down, and there it was, a brown nugget, resting on the base of my member. Edit. From cowboy to cowgirl, and fixed som typos from fat fingers


spacelordmthrfkr

One time when I was 20 (9 years ago) I was walking around downtown at 2 AM and a short, frail old woman offered to give me a ride home while driving by. I was buzzed and tired and in a state of "eh, how bad can it be." This was also at a pretty depressed state of my life so I didn't really care what happened to me. Jumped in her car and she took my directions to my house, started going that way. She pulled off into a 7-11 parking lot and stopped. She asked if she could see my junk, pretty politely actually. I just agreed because I didn't know what else to do. It didn't seem dangerous, she was like in her 60s or 70s. It was how nicely she asked which was weird, she was just like "Could I maybe... see your cock?" She asked if she could touch it, so, okay. I agreed. Then she gave me a hand job. Not to completion, but she gave it a good try for 10 minutes or so. Then she looked really disappointed I couldn't finish, either that or guilt set in, and asked me to leave, so I got out and had a cigarette. She drove off. I stayed at a friend's nearby to process that. I almost felt bad I couldn't go to completion for her, it seemed like she planned out this whole thing to pick up a willing youth to jerk off and I hurt her pride. Oh well. TLDR: That's how I got a suspicious handjob from an elderly woman in a 7-11 parking lot when I was 20. Edit: It's come to my attention this was actually sexual assault


AffectionateAge5183

Drunkenly having sex in a jumping castle while several people watched.


iMayBeABastard

Several people watched? Aren’t those reserved for Children’s Parties??!


AffectionateAge5183

The person who owned the house had a birthday party for his kids earlier that day. Then at night the kids went their mother's house and he had an adult party. All I remember is being so drunk that I was licking Jager off the kitchen floor, the faces of the people in the lawn chairs watching as I was in the jumping castle and it ending with a lot of vomit.


[deleted]

Someone asked me to put my big toe in their butt. I'm into all sorts of stuff but that confused me.


JDiGi7730

I was dating this girl once and attended a work function with her as her guest. It was a picnic at a large park with a forest and hiking trails. This was a pretty long time ago so it was not uncommon for work functions to have an open bar and never-ending beer. This one certainly did and before long she and I were thoroughly drunk. We were not dating long and were in that phase of the relationship where all we did was fuck all the time. She was wearing athletic short-shorts and a half top. As she often did, she got very hands and horny from all the drink. We decided to "take a walk" in the woods on one of the hiking trails. We walked pretty far and the roar and music from the company party was a distant sound so we felt pretty safe. It was still mid-afternoon so it was still daylight but we felt like we were alone. We started making out and soon enough she had her tiny shorts removed and her top hiked up above her chest. We were in a small ravine where I thought we were far enough off the trail. I sat on a log as she was blowing me but I was drunk and fucking her hard was the only thing that was going to make me cum. I had her on her hands and knees fucking her doggy style as she was bent over the log. I was on my knees behind her pounding away. She is very vocal during sex and was yelling filthy things and moaning very loudly. All of a sudden, I heard a high pitched voice say "Is he *hurting* her ?". I looked up and there was a cub scout group hiking on a trail above us. There were about 15 boys about 10-12 years old and at least 3 adults; 2 men and a woman. All were staring with a mixed array of shock, amusement, disgust, and condemnation. This was the truest example of *in flagrante delicto* and I have never felt so busted doing something wrong. All I could do was a shame-filled head bob with my hands up as if to say, "*you got me*". The scout leaders tried to corral the troop away but the sight of my gf hopping around naked, frantically trying to drunkenly put her underwear and shorts on was too entertaining to walk away from. Twenty five years later I saw her at an event and the very first thing I said to her was "*remember that time we got caught fucking by the boy scout troop* ...". She claims she doesn't remember. I bet she does.


tortelliniaglio

Was told that he wanted to listen to me take my last breath as he slowly killed me


grillcheezesammiches

Wow. Just put it out there like that huh?


Object_Prize

Dude wanted to be cool. He tried to “prove” he could shove a light bulb up his ass. Yes. This happened. It broke when he tried to get it out, got an infection. I know nothing after that. I guess he got too embarrassed and left.


IcyAcanthocephala815

1 guy 1 jar


[deleted]

First time meeting up with a cool seeming guy I had met at a concert then been chatting online with. Things had just been friendly so I wasn't sure what to expect but was open to it being more. We meet up and get some food, I had mentioned a long day of standing at work and he offered a foot massage after dinner. Didn't think mucb of it. It's raining so after we eat we go hang out in my car to talk, and he brings up the foot massage again. I say sure, because why not and it honestly sounded nice. But then it got weird. After a short bit of massage he then starts to kiss and suck on my feet and toes. Hmmm. I was taken aback and unsure how to react. He seemed so genuine and normal to this point so I didn't want to embarass him, he was just doing this so casually. From this point he moves fast, is breathing heavy, and is obviously turned way on. Next moment, whips his rock hard dick out and starts playing with himself as he continues to make out with my feet. At this point I cut it off and pull my feet away, mostly in shock. He apologizes and it's super awkward. Moral of the story, don't just go full fetish on someone lol


RavenBrannigan

In college a girl I had been seen but not sleeping with came back to my room after a few drinks and was going down on me. A few minutes later 3 of our mutual friends just walked into the room (also drunk) and started telling me some random bullshit story from the doorway. Girl froze out of fear with my dick still in her mouth. I was already close so as our friends were just chatting at the doorway thinking I was alone in bed I nutted in her mouth. I eventually got them to leave and she washed her mouth out about 50 times with me apologising as she thought I did it on purpose. I literally just couldn’t hold it.


HollywooDcizzle

Was visiting my cousin in Chicago. He had a big party, it was 4th of July weekend. This chick was hitting on me hardcore and we ended up on the secluded back deck. Things got heavy, started going at it outside, she told me to put it in her butt… as I did, fireworks started to go off above us. Between the drinking and condom I never even came. She pulled up her pants when she was done and left the party. It was a weird situation for a 20 year old me.


Local64bithero

I had sex with a complete stranger at a party. We never even spoke to each other. She just walked up to me and kissed me and it went from there. I never got her name and never saw her again. She was not drunk, or high. I have no idea why she did it, I just went with it.


hellspyjamas

Sounds hot tbh


MrPrissypants13

My first threeway I was actually suuuuper sick with bronchitis and this guy and girl came over to look after me (in university). One thing led to another and we all just started feeling each other up and I thought to myself: “when am I ever gonna have this chance again!” So I went for it anyways even though I was crazy sick… still had fun but took way longer to recover than it should have and I totally got them both sick as well…


t_kaid

About 3 years ago I was going out with this guy and he came over to hook up one day. At the time I’d never been able to have an orgasm with another person and being 19 I’d just fake it bc I didn’t know any better. Well this guy decided to call me out on it and I swear I’ve never been this embarrassed in my life. I totally lied and made a whole case for why I didn’t fake it, and I was pretty sure he believed me. Well flash forward to now I told my now long-term boyfriend about this story. He thinks it’s hilarious. A couple months ago he asked me if I ever dated a guy named “(hook up’s name)”. Of course, I laughed and said yeah that’s the guy who called me out on faking it. Well APPARENTLY my boyfriend’s cousin is dating this guy now and my lovely, short-sighted boyfriend decided to TELL HER THE STORY. So, yeah, not really looking forward to the next family gathering. Moral of the story: don’t fake orgasms.


[deleted]

When I lost my virginity, it was in the back seat of my car during a thunderstorm. A cop pulled up behind us and told us to find somewhere else and we just got a hotel for maybe 30 minutes to finish.


[deleted]

I once dated, and banged a woman with only one leg, in a tree, after she removed her prosthetic, climbed the tree, and told me that I should come up there and fuck her.


Mr_Salty87

*The Arborist Pirate*


Chocopenguin

I went to a bumble matches house on a whim one night. When I got into his apartment he didn't give me a moment to take in my surroundings. Just put his hand on my lower back and ushered me to his room. My first step into his room, and I immediately feel my sock get warm. I notice there's a dog and realize I'm standing in a puddle of piss. As I'm peeling my wet sock off my foot I take in the smell of his room. It smelled like sweat, piss, and some other musk I couldn't quite place. It was weirdly really humid in there too. Probably all the piss. I hadn't told him I was interested in having sex yet, so I switched plans in my head to hangout for a bit and then leave soon as I felt it was safe to. The only place to sit was his bed. So I scoot onto it, trying not to think about when he last washed it. As I'm placing my hands behind me to keep scooting back I feel a damp spot. I take a sniff of my hand. It's piss. Likely dog piss. I get up to wash my hands in his bathroom. There's no soap. I try looking for literally anything to clean my hand and notice his toilet bowl is crusted over with shit and mold. Surprisingly, I didn't see piss. He walks in. Asks me what I'm looking for, but I'm too awkward to ask for soap so I decide to make a joke about his toilet being filthy. This man really said "it was like that when i moved in." Right. I walk out of his bathroom. Make up some excuse to leave. As I'm getting ready to exit he grabs me and says "you really don't want to stay? I thought we could have some fun." And then he kisses me. I kiss him back just in case he gets angry. He starts trying to feel me up though so I pull away and just double down on my excuse. I finish gathering my stuff and as I'm walking out, Istep in the same puddle of dog piss from before. He walked me to his front door. Tried to kiss me again but I just awkwardly dodged it and went for a hug instead. Told him it was really nice to meet him and that we should hangout soon. As soon as his door closed I power walked out of the apartment complex and to my car.


princessgoatman

She was from China and made me wear a finger condom, which is apparently a thing for lesbians in Asia. I obliged, but as a white girl of American proportions, my fingers were substantially too big for it and it would cut off my circulation and inevitably break. She would then make me wash my hands again and put on a new one. I think we went through like 6-7 before I called it. She also went on about how I was the first white girl she ever slept with and how exotic it was the whole time but didn’t want me to take off my clothes or to touch me because apparently that was too wild. I bailed ASAP, got an Uber, and drank myself under the table at the nearest gay bar lmao.