What's your craziest sexual experience thread?

MusicForFish · Jun 9, 2020

Once gave a German Knuckleduster to a very nasty thing back in my late teens.
That's where you fist thier ass open, then pour sand in, then fist until bleeding.
Was traumatic to me back then but rather tame compared to the joys of the internet these days.

Come on guys, up your game.

DrFukasaka · Jun 9, 2020

I once dated a redhead who was bat shit crazy and while the sex was great the crazy scale got to much for me so I dumped her. Crazy woman had a teen age daughter who I spent entirely too much time looking at and thinking about. The daughter was half Mexican and sexy as hell she was about 90lbs with dark skin and a bubble butt. Out of the blue the daughter found me on face book and we got to chatting, she was out of school and wanted to know if I was hiring we also talked about her crazy mom and how I make the best grilled steaks so I invited her over for dinner and drinks and to talk about what position at my company she would be good at.

As we talked and grilled I made her mojitos it was pretty hot and I noticed she was sucking them down really fast so by the time dinner was done she was pretty buzzed and hanging all over me. After dinner I have her the tour of my new home and once we got to my bedroom she just sorta stood in front of the bed so I came up behind her and kissed her neck and after a few minutes she turned around and kissed me back.

As soon as she paused to take a breath I pushed her onto the bed jerked off her shorts and panties and buried my face in her pussy I also shoved a finger up her ass and in less than a minute she proceeded to have the biggest and longest orgasm I have ever seen a woman have and as soon as she caught her breath I shoved my dick inside of her, I didn't even take the time to get my shorts all the way off she immediately gasped at the size of my cock and we came together in under 30 seconds.

After that we both had a good laugh at how fast things went and we proceeded to have sex for the next 8 hours with very few breaks. She told me how she had only been with 2 other guys and my penis was by far larger than both the others she also told me that she thought she had had orgasms before but after what I did to her she was unsure.

We were hot and heavy for that whole summer but shortly into her first year in college the allure of guys her age pulled her away but she would still come pay me a visit from time to time and still does really only now its mostly pay to play.

Zhavric · Jun 9, 2020

Being 22 and having grown up in the "WEAR CONDOM OR AIDS" generation finally blowing my load into my girlfriend's 19 year old vag bareback.

Aside from how good it felt... afterwards it was like, "Wait... she's on the pill so she's not pregnant. And neither of us have AIDS or any disease. THE FUCK ELSE HAVE YOU ASSHOLES LIED ABOUT?" Had a lot of fun that summer.

j00t · Jun 9, 2020

DrFukasaka said:
I once dated a redhead who was bat shit crazy and while the sex was great the crazy scale got to much for me so I dumped her. Crazy woman had a teen age daughter who I spent entirely too much time looking at and thinking about. The daughter was half Mexican and sexy as hell she was about 90lbs with dark skin and a bubble butt. Out of the blue the daughter found me on face book and we got to chatting, she was out of school and wanted to know if I was hiring we also talked about her crazy mom and how I make the best grilled steaks so I invited her over for dinner and drinks and to talk about what position at my company she would be good at.

As we talked and grilled I made her mojitos it was pretty hot and I noticed she was sucking them down really fast so by the time dinner was done she was pretty buzzed and hanging all over me. After dinner I have her the tour of my new home and once we got to my bedroom she just sorta stood in front of the bed so I came up behind her and kissed her neck and after a few minutes she turned around and kissed me back.

As soon as she paused to take a breath I pushed her onto the bed jerked off her shorts and panties and buried my face in her pussy I also shoved a finger up her ass and in less than a minute she proceeded to have the biggest and longest orgasm I have ever seen a woman have and as soon as she caught her breath I shoved my dick inside of her, I didn't even take the time to get my shorts all the way off she immediately gasped at the size of my cock and we came together in under 30 seconds.

After that we both had a good laugh at how fast things went and we proceeded to have sex for the next 8 hours with very few breaks. She told me how she had only been with 2 other guys and my penis was by far larger than both the others she also told me that she thought she had had orgasms before but after what I did to her she was unsure.

We were hot and heavy for that whole summer but shortly into her first year in college the allure of guys her age pulled her away but she would still come pay me a visit from time to time and still does really only now its mostly pay to play.

This reads like one of those Playboy letters.

Cutlery · Jun 9, 2020

After my divorce, I met this gal who was pretty open and upfront about her sexuality. She asked me if I minded toys, told her I was married for 18 years, I don't give a shit about toys. She said some dudes get real weird about them. I dunno why, do whatever works for you.

So one night, I'm about to leave work, and she's gonna meet me at my place. She comes over prepped - she's got a vibrating plug already in her ass when she shows up. I hop in the shower, she heads to the bed to get warmed up. She's got this in.

We-Vibe+Ditto+Butt+Plug+Anal+Sex+Toys+Vibrators+Blue+in+Hand.jpg

We get to getting to it, doggy style. At some point I feel it stop vibrating, and she mentions that the battery only lasts about an hour. So yeah, that's right on queue. I don't know exactly what happened, but I looked away from her ass for a few seconds, and when I looked back, the plug was gone. I assumed that she palmed it in the pause.

We finished, and are laying on the bed and after about 5 minutes she goes "Alright, that was great...now, where'd the plug go?"

"Uhh, i thought you took it out."

"No, it must have fell out."

We strip the bed. Nothing.

We check under the bed. Nothing. I told her "Look, I've got a dog and the kids come back here tomorrow, so we need to find this thing right the fuck now before my dog does." So we go back over everything. We literally tear my bedroom apart. We're emptying pillowcases, looking under the mattress, in the laundry basket, EVERYTHING.

I sit down on the bed and tell her "Well, I think there's only one place that thing could possibly be. And when you find it, I'm gonna need you to never speak of it again." She said "uhh, yeah...." and left without saying another word.

Her ass swallowed that whole thing up whole. Now, I get it - her theory is the small end basically got dragged in while we were fucking, and then assholes do what asshole do ---which is close up behind things. All that makes perfect sense to me. What I will never understand is how you can have an asshole that's so fucking cavernous that you could not notice AN ENTIRE SEX TOY IN THERE SIDEWAYS.

She texted me the next day with "Round 2?" A woman who literally should have died of fucking embarrassment went home, fished that thing out, and then said "Alright, what else you got?"

Nope.

Rajaah · Jun 9, 2020

TheNozz said:
Once met this random BBW in a bar that gave head so good, when I came, I felt like I was being pulled inside out through my dick.

That's how it was with the older 39 year old I dated. She was incredible at it and if she had a few drinks first she'd be even more incredible at it for some reason. The first time we hooked up I had no idea how good she would be. She went straight for the BJ and went all the way with it. I was like "cool I guess she's getting me ready WHOA HOLY SHIT."

lurkingdirk · Jun 9, 2020

DrFukasaka said:
I once dated a redhead who was bat shit crazy and while the sex was great the crazy scale got to much for me so I dumped her. Crazy woman had a teen age daughter who I spent entirely too much time looking at and thinking about. The daughter was half Mexican and sexy as hell she was about 90lbs with dark skin and a bubble butt. Out of the blue the daughter found me on face book and we got to chatting, she was out of school and wanted to know if I was hiring we also talked about her crazy mom and how I make the best grilled steaks so I invited her over for dinner and drinks and to talk about what position at my company she would be good at.

As we talked and grilled I made her mojitos it was pretty hot and I noticed she was sucking them down really fast so by the time dinner was done she was pretty buzzed and hanging all over me. After dinner I have her the tour of my new home and once we got to my bedroom she just sorta stood in front of the bed so I came up behind her and kissed her neck and after a few minutes she turned around and kissed me back.

As soon as she paused to take a breath I pushed her onto the bed jerked off her shorts and panties and buried my face in her pussy I also shoved a finger up her ass and in less than a minute she proceeded to have the biggest and longest orgasm I have ever seen a woman have and as soon as she caught her breath I shoved my dick inside of her, I didn't even take the time to get my shorts all the way off she immediately gasped at the size of my cock and we came together in under 30 seconds.

After that we both had a good laugh at how fast things went and we proceeded to have sex for the next 8 hours with very few breaks. She told me how she had only been with 2 other guys and my penis was by far larger than both the others she also told me that she thought she had had orgasms before but after what I did to her she was unsure.

We were hot and heavy for that whole summer but shortly into her first year in college the allure of guys her age pulled her away but she would still come pay me a visit from time to time and still does really only now its mostly pay to play.

TheNozz · Jun 10, 2020

Rajaah said:
That's how it was with the older 39 year old I dated. She was incredible at it and if she had a few drinks first she'd be even more incredible at it for some reason. The first time we hooked up I had no idea how good she would be. She went straight for the BJ and went all the way with it. I was like "cool I guess she's getting me ready WHOA HOLY SHIT."

Speaking of older women

I was in a relationship with this cougar back when I was 24. She had just got out of a 7 year, mostly sexless relationship so I'm guessing she was making up for lost time...

Anyways, on the second night we hooked up, after we finish having sex, she pulls off my condom and throws it away. When she comes back, I'm still hard so she starts giving me this slow handjob. I pop after several minutes but still stay hard. She just keeps on going and I'm telling her "it feels pretty good, but I don't thWHOAH!" and pop a 3rd time for a total of 3 shots in roughly 10 mins of each other. Had chest pain later on while we were at store and by the next day, when she would finish me off with her hand, literally nothing was left to come out.

She said something like "oh dear, looks like you've been pumped dry." Greatest weekend of sex I've ever had.

Aychamo BanBan · Jun 10, 2020

DrFukasaka said:
As soon as she paused to take a breath I pushed her onto the bed jerked off her shorts and panties and buried my face in her pussy

This is the best move. I don't just pull their pants off, but like if we are kissing, making out, I'll always start kissing the neck, then the chest, and then kind of work my way down and kind of start eating their pussy on top of their clothes. This way they don't feel like a slut like we are just already fucking or something. They're still clothed, but now their pussy area is getting licked, and I'll kiss their inner thighs, etc. Makes them so fucking insanely horny that they don't resist when you just want to pull their shorts down a little to actually eat them out, then you can just slide the dick on in after a few more minutes of that.

Caeden · Jun 10, 2020

I realize now that my quantity (and quality) has added up to nothing wild.

One girl I would tie up and whip/spank some. Used actual rope on a four poster. She liked the anal to hurt so I’d go as hard as possible. Still that’s not really wild today.

I always thought the sneaking and screwing in public places was fun.

I dated this nurse briefly and had her bent over on the side of the road on the Blue Ridge Parkway. I’d just finished blowing into her mouth when an Indian family came around the corner. We just got our pants up.

slippery · Jun 10, 2020

Hoss said:
I honestly was not planning to fuck her any of those times.

You dirty fucking liar

Foler · Jun 10, 2020

DrFukasaka said:
I once dated a redhead who was bat shit crazy and while the sex was great the crazy scale got to much for me so I dumped her. Crazy woman had a teen age daughter who I spent entirely too much time looking at and thinking about. The daughter was half Mexican and sexy as hell she was about 90lbs with dark skin and a bubble butt. Out of the blue the daughter found me on face book and we got to chatting, she was out of school and wanted to know if I was hiring we also talked about her crazy mom and how I make the best grilled steaks so I invited her over for dinner and drinks and to talk about what position at my company she would be good at.

As we talked and grilled I made her mojitos it was pretty hot and I noticed she was sucking them down really fast so by the time dinner was done she was pretty buzzed and hanging all over me. After dinner I have her the tour of my new home and once we got to my bedroom she just sorta stood in front of the bed so I came up behind her and kissed her neck and after a few minutes she turned around and kissed me back.

As soon as she paused to take a breath I pushed her onto the bed jerked off her shorts and panties and buried my face in her pussy I also shoved a finger up her ass and in less than a minute she proceeded to have the biggest and longest orgasm I have ever seen a woman have and as soon as she caught her breath I shoved my dick inside of her, I didn't even take the time to get my shorts all the way off she immediately gasped at the size of my cock and we came together in under 30 seconds.

After that we both had a good laugh at how fast things went and we proceeded to have sex for the next 8 hours with very few breaks. She told me how she had only been with 2 other guys and my penis was by far larger than both the others she also told me that she thought she had had orgasms before but after what I did to her she was unsure.

We were hot and heavy for that whole summer but shortly into her first year in college the allure of guys her age pulled her away but she would still come pay me a visit from time to time and still does really only now its mostly pay to play.

Wait are you a pedo?

Foler · Jun 10, 2020

Cutlery said:
After my divorce, I met this gal who was pretty open and upfront about her sexuality. She asked me if I minded toys, told her I was married for 18 years, I don't give a shit about toys. She said some dudes get real weird about them. I dunno why, do whatever works for you.

So one night, I'm about to leave work, and she's gonna meet me at my place. She comes over prepped - she's got a vibrating plug already in her ass when she shows up. I hop in the shower, she heads to the bed to get warmed up. She's got this in.

View attachment 276760

We get to getting to it, doggy style. At some point I feel it stop vibrating, and she mentions that the battery only lasts about an hour. So yeah, that's right on queue. I don't know exactly what happened, but I looked away from her ass for a few seconds, and when I looked back, the plug was gone. I assumed that she palmed it in the pause.

We finished, and are laying on the bed and after about 5 minutes she goes "Alright, that was great...now, where'd the plug go?"

"Uhh, i thought you took it out."

"No, it must have fell out."

We strip the bed. Nothing.

We check under the bed. Nothing. I told her "Look, I've got a dog and the kids come back here tomorrow, so we need to find this thing right the fuck now before my dog does." So we go back over everything. We literally tear my bedroom apart. We're emptying pillowcases, looking under the mattress, in the laundry basket, EVERYTHING.

I sit down on the bed and tell her "Well, I think there's only one place that thing could possibly be. And when you find it, I'm gonna need you to never speak of it again." She said "uhh, yeah...." and left without saying another word.

Her ass swallowed that whole thing up whole. Now, I get it - her theory is the small end basically got dragged in while we were fucking, and then assholes do what asshole do ---which is close up behind things. All that makes perfect sense to me. What I will never understand is how you can have an asshole that's so fucking cavernous that you could not notice AN ENTIRE SEX TOY IN THERE SIDEWAYS.

She texted me the next day with "Round 2?" A woman who literally should have died of fucking embarrassment went home, fished that thing out, and then said "Alright, what else you got?"

Nope.

A++. Maybe best so far

a c i d.f l y · Jun 11, 2020

This is not my craziest story. I'm not sharing that one, other than that it likely dealt with Russians and the sex trade.

This one girl and I both were still living with our folks due to college, so we had to find locations away from home mostly. Our first time was in my tiny ass Civic. She pulled the parking brake on a very steep hill while climbing on top of me, fortunately, I was still in gear.

Another time, we spent like 6 hours at an apartment hot tub finishing a case of beer. It was dark, likely midnight, who knows, I can't remember. Pull her bottoms off, start. I carried her all over the seating area. Lawnchair. Doggy up against the big sign with the pool rules. Finish. "Phew. No one saw us." As we're putting on our clothes, some dude carrying a laptop walks down from the top part of the seating area that we couldn't see. "Oh. Shit." He doesn't say anything, and just hurriedly leaves the area. We go back the next day and the hot tub had been drained. For some reason, she knew all the apartments with hot tubs. Pretty sure we defiled all of them within a 20-mile radius.

She was a pretty intense lay. One night after clubbing, she hiked her skirt up and bent over my car's hood in the parking garage. People would look out of their windows and stare awkwardly as they drove by.

Guurn · Jun 11, 2020

I've only had two things happen i thought were crazy/weird. I mean, we all have sex stories and toys...sure whatever but crazy stuff? My first sexual encounter was when i was in high school. It was normal fingering stuff and i had no clue it was unusual till many years later. I put my hands down her pants (yes she was great looking) and literally everything in her pants was soaked. Not pee and it didn't stop me. As i put my fingers on and in her there was no resistance, like none. I could have shoved my whole hand in easily. On top of it there was a crazy amount of extra goo. If you saw what my hand looked like after i took it out you would have thought it was a bad movie. I wiped it off on my cords and the soaking wet patch on them was football sized. She contacted me a couple years back. Married and still amazing looking. Oh well, should have shoved the fist in i guess.

Number two. Late in my college years and with a good amount of experience under my belt, to be fair i still had little clue what i was doing, i contacted a friend for some casual sex after i had just broke up with a girlfriend. I knew she had been around and she dated a buddy of mine earlier on. Grrr naked sick my duck in and Wtf. Her vaginal walls were the stuff of dreams. Honestly to this day i have no clue how she did it but she could make them vibrate/wave. The walls of her vagina had a suction thing as well. It's really impossible to describe. Afterwards all i could think is why would she get so good at that, guys cum fast enough as it is. Later on during a bender i asked her who was better my buddy or me. College kids ask stupid stuff. Her reply? She was. She was correct.

Caeden · Jun 11, 2020

Weirdest was hooking up with a slightly older woman when I was about 31. She was probably closer to 40 (which means she’d be younger for me now...sigh). Had had kids but aside from some stretch marks was in good shape. Going down on her and decide to toss a few fingers in to give her the ol’ one two. There’s like this hard plastic support in there. Kinda weird. My dumbass thought it might have been a nuvaring. I now know it was a vaginal mesh. She’d gotten her lady bits totally messed up in last baby.

I soldiered on and didn’t feel it during the actual sex. Was decently tight too. Never saw her again. Hopefully I didnt give her number 3!

Also briefly dated a physical therapist that had a kid and severe self esteem issues. This girl had no business with me but her estranged husband had mentally destroyed her to where she felt worthless. Hottest girl I’ve ever snagged, even with a kid. Anyway she was so worried her kid would think she was a ho that I’d sneak over after bedtime and leave before he woke up. One morning she asked me to stick around for more sex. We finish up and I hear kid feet in the hall and a knock. I’m upstairs with her in her room. She freaks. And proceeds for the next several hours to essentially keep me prisoner in her bedroom until she can figure out how to get the kid out. There’s no way out due to the open floor plan where the kid won’t see me. I play along since I respect what she’s trying to do there. But at hour four I get ready to leave. She freaks out and starts crying. Finally she calls a friend and the kid goes to play and I leave. Last time I went there. Also during the in total 5-6 hours she sneaks up there and we fuck two more times while the kid is playing. He was probably 7 or 8. Which Is kinda fucked up looking back, but meh. Wasn’t my kid. Sorry I came in your mom while you watched Disney little buddy.

Caeden · Jun 11, 2020

Oh. One other single mom story. This ended up a one night stand. Social worker. Tons of social worker single moms. You’d think given their profession they’d be better at marriage.

Anyway, I met this one online. Maybe eharmony or match? Can’t remember. We go out. Get pizza. She’s a little thick. Fatter than my preference but wears it well. Cute face and those lips that scream “I give great head”. Go back to her place and it’s all going great. Fingering her. She starts blowing me and is amazing. Too good. So I stop her and strip her down. Rawdog her and then cum on her big ass tits. She does a little freaking that pulling out is how she got pregnant before. But my game is good. Round two a couple hours later. Leave the next morning planning to go out next weekend.

we text up until like Wednesday. Then radio silence. I call. No answer. I call one more time on Thursday and get an answer but it is more like I can hear background noise then hang up. I don’t know what’s up. Texting had been super positive.

few weeks later, a coworker gets arrested. No biggie and charges dropped. But his mugshot goes online in the local gossip rag. I’m scrolling through and who do I see - Social Worker!!!! Arrested for fucking prostitution! I show my buddy and tell him I was just out a pizza! She even paid for the PPV movie we fucked during. Hooker with a heart of gold and financial fairness?

I, of course, go get some testing done that I can and keep watch. All clean.

Bruuce · Jun 11, 2020

anytime they say yes

Hoss · Jun 11, 2020

Caeden said:
Going down on her and decide to toss a few fingers in to give her the ol’ one two. There’s like this hard plastic support in there. Kinda weird. My dumbass thought it might have been a nuvaring. I now know it was a vaginal mesh. She’d gotten her lady bits totally messed up in last baby.

I went down on a girl with a nuva ring once. No idea what it was, I'd never even heard of them before. But when I figured out it was possibly latex it got in my head and I was afraid it was a condom. I soldiered on and dug it out. Took a look at it and was like "GOD DAMN WAS SHE FUCKING A HORSE". Threw it to the side and finished up because I could tell it was just a ring of some sort. Kinda figured it might be a toy. Showed it to her afterwards and she explained what it was. She had not noticed me digging it out. I'm glad it wasn't the mesh that you're talking about because I might have hurt her digging it out.

Caeden · Jun 11, 2020

Hoss said:
I went down on a girl with a nuva ring once. No idea what it was, I'd never even heard of them before. But when I figured out it was possibly latex it got in my head and I was afraid it was a condom. I soldiered on and dug it out. Took a look at it and was like "GOD DAMN WAS SHE FUCKING A HORSE". Threw it to the side and finished up because I could tell it was just a ring of some sort. Kinda figured it might be a toy. Showed it to her afterwards and she explained what it was. She had not noticed me digging it out. I'm glad it wasn't the mesh that you're talking about because I might have hurt her digging it out.

Hahaha. My wife used the Nuvaring. We sometimes have to remove it. Can feel bad on the ol’ pecker at times.

Search

What's your craziest sexual experience thread?

MusicForFish

Ultra Maga Instinct

DrFukasaka

Lord Nagafen Raider

Zhavric

Molten Core Raider

j00t

Silver Baronet of the Realm

Cutlery

Kill All the White People

Rajaah

Honorable Member

lurkingdirk

AssHat Taint

TheNozz

Ssraeszha Raider

Aychamo BanBan

Caeden

Silver Baronet of the Realm

slippery

The_Black_Log Foler

Stock Pals Senior Vice President

The_Black_Log Foler

Stock Pals Senior Vice President

a c i d.f l y

ಠ_ಠ

Guurn

Caeden

Silver Baronet of the Realm

Caeden

Silver Baronet of the Realm

Bruuce

Blackwing Lair Raider

Hoss

Make America's Team Great Again

Caeden

Silver Baronet of the Realm