Kinkiest real life experiences

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About 15 years ago I was on a boat party with my girlfriend and some other couples drinking rather heavily. When we were done we decide to go out so my girlfriend and another couple went back to my girlfriends house to get cleaned up and change. My girlfriend and her female friend went into her bedroom to shower and myself and the friends boyfriend were in the other room. My clothes were in her room so I went in to get my bag when they both appeared from the shower together wet and naked. They got on the bed and started making out. Her friends boyfriend came around the corner and saw what was going on so we both joined them on the bed. I started eating out my girlfriend from behind while she was between her friends legs. The other guy was trying to get his girlfriend to give him a blowjob but he couldn’t really get it up. My girlfriend finally rolled over and I climbed between her legs and I started missionary with her. Her girlfriend was doing everything she could to get her boy friend hard and he couldn’t get it up. Finally her girlfriend crawled across the bed and got on top of my girlfriend. I pulled out of my girlfriend and started doing her friend from behind. The whole time the other guy was in the corner trying to get it up. I guess he was a little intimidated, HAHA!

I broke up with that girl and every 6 months or so afterwards her girlfriend and I would hook up again just for fun.
 
Banged a chick on the train between France and England ( the Chunnel) without saying a word, learning her name or talking afterward.

My brother, who I was traveling with watched it all unfold.
 
About 15 years ago I was on a boat party with my girlfriend and some other couples drinking rather heavily. When we were done we decide to go out so my girlfriend and another couple went back to my girlfriends house to get cleaned up and change. My girlfriend and her female friend went into her bedroom to shower and myself and the friends boyfriend were in the other room. My clothes were in her room so I went in to get my bag when they both appeared from the shower together wet and naked. They got on the bed and started making out. Her friends boyfriend came around the corner and saw what was going on so we both joined them on the bed. I started eating out my girlfriend from behind while she was between her friends legs. The other guy was trying to get his girlfriend to give him a blowjob but he couldn’t really get it up. My girlfriend finally rolled over and I climbed between her legs and I started missionary with her. Her girlfriend was doing everything she could to get her boy friend hard and he couldn’t get it up. Finally her girlfriend crawled across the bed and got on top of my girlfriend. I pulled out of my girlfriend and started doing her friend from behind. The whole time the other guy was in the corner trying to get it up. I guess he was a little intimidated, HAHA!

I broke up with that girl and every 6 months or so afterwards her girlfriend and I would hook up again just for fun.

That would make a great story! ;)
 
There was another couple that we swapped with when we lived in Germany. Our first swapping with them happened after we biked down the Bavarian Alps. In the hotel that night we were playing dare or dare. (no truth.) My wife and I had already had several couples we had swapped with and she had already done other things when I was not around. (I am in the process of writing those stories with her help.) We were not going to go too far unless they did a dare first. For the most part it was dare to show something or touch something; my wife dared the other wife to take her panties off and sit with her legs spread so we could see her open pussy. Of corse she did then her husband dared me to stick my dick balls deep in her. I of corse gladly did. Once I was balls deep she told her husband, "I want him to fuck me." He picked up his German beer and said: "Go for it." I said only if you start fucking my wife." I fucked her several different positions until I shot my full load of cum in her beautiful trimmed red haired pussy. He was having a little trouble cumming. This was the first time he was screwing someone in front of others and someone other than his wife since they were married. His wife whispered to me that he would cum if he did her anally. By then my wife was bent over the bed and he was doing her from behind. I sat up, pulled her ass cheeks apart and said: "I dare you to let him do you in the ass." We had only done anal 5 times in 10 years to that point. His cock was about an inch longer than mine and a little girthier. My wife could not back down from a challenge and grunted "OK" He slowly worked his cock into her ass as she groaned in the pillow. At that point it did not take him long before he pulled out and shot his load all over her back.

I am looking forward to reading the full story! ;)
 
It was New Years, a few years ago. My wife and I had a small party at our home with a couple friends. We all had quite a bit to drink and about an hour after midnight our male friend had gone home and the only people left were my wife, her friend (female), and myself. Then my wife told us that she was going to bed and walked out of room we had been hanging out and into the bedroom. I didn't think much of it as I knew she was quite drunk. But then all of a sudden our female friend told me she was going to fuck my wife and before I could respond she got up and went into the bedroom!

My excitement level couldn't be higher. Finally I would be living out my fantasy of having a threesome and my wife was likely drunk enough to go along with it. Wanting to make the most of the occasion, I quickly went to the bathroom and gave my cock a nice washing to make it ready for the 2 ladies in my bed. I then made my way into the dark bedroom and slipped into the bed. It was only then that I realized both girls were already asleep / passed out!

I tried as much as humanly possibly but at 2am, after a night of drinking, these girls were down for the count and there was seemingly nothing I could do to wake them, let alone convince them to engage in the fantasy that seemed like foregone conclusion just minutes before. But my excitement was just too high, I couldn't give up. Finally, after a long time of trying, I finally woke my wife and convinced her that I wasn't going to be able to sleep until I came. So there in out bed, in between my wife and our sleeping friend, she gave me and job and let my cum on her tits. All the while the friend asleep and totally oblvious as to the level of pleasure going through my body just inches from hers. After I came I finally managed to fall asleep.

We have all since laughed and talked about the situation but never again gotten close to pulling it off despite our friend's attempts to make out with my wife and play with her tits when partying together. Unfortunately the friend moved away so that opportunity has now slipped away.

Anyhow, not necessarily the kinkiest thing I've done, but definitly the closest I've come to the kinkiest thing I'd like to have done!
 
Wow,
Where do I begin? I have a lot of real life experiences. I've been trying to "find" myself for a good 30+ years, I'm 41 yrs old, and I'm also disabled, paraplegic, I can't walk/stand and I use a wheelchair. I also can't feel my penis. I can't feel it so I don't bother with it. I was taught to adapt what I can't do, so I have, I find where I can feel and find pleasure in those ways. One of those ways in anally. I can feel my butthole. I treated like a vagina, which is how I masterbate. Because of my disability I wasnt able to be naked, except in the bathtub. I had a few surgeries in "97" and have slept, been naked as much as I can since then. I apologize for the continued explanations.

Because of the way that I choose to pleasure myself, its made me wonder about my gender, I've been experiementing with cross-dressing since I was a child as well. And have been "designing"/refurbishing my male clothes since I was 11. I was a bit of an exhibitionist when I young, but not in front of others. I was hidden, but risked getting caught multiple times. Our second house had a wrap around porch amd our ouse was set back from the street. Many times, I would go out onto the porch, take my clothes off and sit on the wicker sofa, just lay there, and I wasnt caught.

It wasn't until 2015 that I considered transitioning. (male to female) I'm not ready to do it. I'm too afraid of public perception. That I'm going to run into that one person or persons who would get into an argument with me, or worse if I did transition or during my transition.

Ive had several experiences that I won't soon forget.
 
real life

im not sure if its the kinkiest of all ....but it is something i like to think about

i have a sister 2 years older than me. i was always the dorky nerd kid and she was always the beautiful super hot most popular girl around kid. around 13 or so, i became acutely aware that she was literally the hottest girl around. she was one of those rare girls who had amazing big titties AND a beautiful bubble butt. we lived in a pretty big 2 story house and she and i had the upstairs and our parents the downstairs. they rarely ever came up and we rarely ever went down except to eat. most of the time, my sister ran around in panties and a tank top. we played alot of games back then and i cant even count the times she sat indian style across from me where i could plainly see her bush and sometimes the shape or her lips etc. i looked and she didn't care. i usually had on nothing but those ridiculous little gym shorts we wore back in the 70s. sometimes id get rock hard looking at her and id see her looking as well. we grew up very close and spent alot of time laying side by side listening to music or just talking or just staring at the ceiling fan. i guess i was about 14 when i began to really fantasize about her. there was no internet and there was certainly no porn around our house. my sole sexual inspiration came from her. on a rainy saturday night, she was supposed to have a date but her bf canceled on her and our parents were gone out. it was just me and her at home. i knew she was disappointed about her date so i went to her room just to check on her. she was laying on her stomach on the bed. we started listening to albums (yes - you know....100 years ago).....and when it was my turn i put on santana moonflower (which to this day i reckon is one of the best albums ever)....as we laid there listening she was grimacing a little and complaining about her back hurting. i asked her if she wanted me to rub on it - which i had done before - and she said yes. now it should be noted that i loved my sister very much.....and although i did fantasize about her ....i truly had no intention of really ever doing anything at all with her or to her. i got up and got some lotion she had on her dresser and straddled her and pushed her shirt up and started really rubbing on her back. she purred like a kitten and in a few minutes she leaned up enough to pull her tank top off. i clearly saw her bare breasts in a dressing mirror across her room as she lowered herself back down. as i kept massaging her back i was more or less rocking back and forth. my cock just naturally nestled into her butt crack and the movement made me get hard as a rock pretty quickly. i knew she had to feel it and i didnt want to be some creepy perv so i asked her if she wanted me to stop. i could see her face in that same mirror and her eyes were closed and her mouth partway open when she just barely whispered "no...its helping my back alot"......even at that point, it was not like i had a plan.....other than to try to make my sister feel better.....she reached and pulled her panties down maybe 2 or 3 inchs.....and said it was her lower back that was really hurting....i had to shift backwards some in order to be able to really rub on her butt......i was so hard.....and trying hard not to be too? obvious....but my precum had already made a big wet spot on my shorts....the way i had shifted had positioned my head right against her promised land. i could feel her heat.....and when i looked down, i realized that my head, although through my shorts and her panties, was pressed into her a good inch or more......i was just about to stop.....figuring she surely realized my situation....when she rearranged.....i almost got off her.....but she cocked her left leg out some....and somewhat cocked her beautiful butt up into the air .....the effect was that my head went deeper inside her.....i could see some of her pussy along the leg of her panties....it was all hotter than i could have made up in my best fantasy......all the while her eyes remained closed.....and her mouth remained partly open.....i kept rubbing on her butt but i realized i wanted to be leaning much more forward and so i shifted to her neck and shoulders.....occasionally sliding my hands along her sides and the sides of her boobs too....the effect of leaning forward and working up and down essentially had my cock sliding somewhat in and out of her.....i realized that my head was actually almost coming out of the waist of my shorts .....i finally reached down and pulled them down until my cock was free.....instantly i was completely aware that her panties were soaking wet.....being out of my shorts allowed me to slide deeper into her.....which enhanced the action of our movements....i knew that i was moments away from cumming....i had only recently learned to masturbate......i knew the sensations of the impending orgasm.....i was going to get up and go to my room where i could just stroke it on out.....when she reached back and pulled her panties to the side.....it all happened so fast......she pulled them aside....and my next stroke literally just buried me to the balls inside her......she gasped in one of the most gutteral animalistic moans i have heard to this day.....i didn't know girls had the ability to grip onto one's cock so tightly.....but she did....she gripped me....and all of the movements began to come from her....she fucked back .....i had no idea.....as i was almost to the point of not return....our eyes met in the mirror.....i more read her lips than heard her say "its ok....i love you".........those young orgasms......they were like finally peeing after having had to wait for hours and hours.....i could feel the streams .....one after another spraying into her.....i just kept cumming and cumming.....i had never seen or heard her cum before and i thought something was wrong and she was crying.....as she suddenly started gasping and moaning......i could feel the intense pressure on my cock as she squeezed against me.....a flood of liquid gushed from her......together we had made a huge puddle on her bed.....i watched her face through it all....finally, embarrassed, confused, somewhat scared.....i pulled out, pulled my shorts up and more or less ran back to my room......in a few minutes she came to my door...."come here".....she took my hand and led me into the bathroom that we shared.....and we showered together....she washed me....like she had done when i was little.....she washed me and she washed herself.....the whole time she just quietly talked....."its ok.....lets dont tell anyone.....but....dont feel bad about it....we did it for each other....its ok"

i loved her for that....for making it be ok. it never happened again. i did feel terribly guilty about it. i did masturbate 1000 times thinking about.....probably more.....it did make us different.....sweeter i think......more in love with each other than we always had been....which was alot.....we never talked about it......there were a few times when i know she offered more.....and a time or two where she did things to "teach me"......but we never had intercourse again.....

ive never told it to anyone in person.....or in "real life"......but it is the gospel truth.....of my first time ever.
 
im not sure if its the kinkiest of all ....but it is something i like to think about

i have a sister 2 years older than me. i was always the dorky nerd kid and she was always the beautiful super hot most popular girl around kid. around 13 or so, i became acutely aware that she was literally the hottest girl around. she was one of those rare girls who had amazing big titties AND a beautiful bubble butt. we lived in a pretty big 2 story house and she and i had the upstairs and our parents the downstairs. they rarely ever came up and we rarely ever went down except to eat. most of the time, my sister ran around in panties and a tank top. we played alot of games back then and i cant even count the times she sat indian style across from me where i could plainly see her bush and sometimes the shape or her lips etc. i looked and she didn't care. i usually had on nothing but those ridiculous little gym shorts we wore back in the 70s. sometimes id get rock hard looking at her and id see her looking as well. we grew up very close and spent alot of time laying side by side listening to music or just talking or just staring at the ceiling fan. i guess i was about 14 when i began to really fantasize about her. there was no internet and there was certainly no porn around our house. my sole sexual inspiration came from her. on a rainy saturday night, she was supposed to have a date but her bf canceled on her and our parents were gone out. it was just me and her at home. i knew she was disappointed about her date so i went to her room just to check on her. she was laying on her stomach on the bed. we started listening to albums (yes - you know....100 years ago).....and when it was my turn i put on santana moonflower (which to this day i reckon is one of the best albums ever)....as we laid there listening she was grimacing a little and complaining about her back hurting. i asked her if she wanted me to rub on it - which i had done before - and she said yes. now it should be noted that i loved my sister very much.....and although i did fantasize about her ....i truly had no intention of really ever doing anything at all with her or to her. i got up and got some lotion she had on her dresser and straddled her and pushed her shirt up and started really rubbing on her back. she purred like a kitten and in a few minutes she leaned up enough to pull her tank top off. i clearly saw her bare breasts in a dressing mirror across her room as she lowered herself back down. as i kept massaging her back i was more or less rocking back and forth. my cock just naturally nestled into her butt crack and the movement made me get hard as a rock pretty quickly. i knew she had to feel it and i didnt want to be some creepy perv so i asked her if she wanted me to stop. i could see her face in that same mirror and her eyes were closed and her mouth partway open when she just barely whispered "no...its helping my back alot"......even at that point, it was not like i had a plan.....other than to try to make my sister feel better.....she reached and pulled her panties down maybe 2 or 3 inchs.....and said it was her lower back that was really hurting....i had to shift backwards some in order to be able to really rub on her butt......i was so hard.....and trying hard not to be too? obvious....but my precum had already made a big wet spot on my shorts....the way i had shifted had positioned my head right against her promised land. i could feel her heat.....and when i looked down, i realized that my head, although through my shorts and her panties, was pressed into her a good inch or more......i was just about to stop.....figuring she surely realized my situation....when she rearranged.....i almost got off her.....but she cocked her left leg out some....and somewhat cocked her beautiful butt up into the air .....the effect was that my head went deeper inside her.....i could see some of her pussy along the leg of her panties....it was all hotter than i could have made up in my best fantasy......all the while her eyes remained closed.....and her mouth remained partly open.....i kept rubbing on her butt but i realized i wanted to be leaning much more forward and so i shifted to her neck and shoulders.....occasionally sliding my hands along her sides and the sides of her boobs too....the effect of leaning forward and working up and down essentially had my cock sliding somewhat in and out of her.....i realized that my head was actually almost coming out of the waist of my shorts .....i finally reached down and pulled them down until my cock was free.....instantly i was completely aware that her panties were soaking wet.....being out of my shorts allowed me to slide deeper into her.....which enhanced the action of our movements....i knew that i was moments away from cumming....i had only recently learned to masturbate......i knew the sensations of the impending orgasm.....i was going to get up and go to my room where i could just stroke it on out.....when she reached back and pulled her panties to the side.....it all happened so fast......she pulled them aside....and my next stroke literally just buried me to the balls inside her......she gasped in one of the most gutteral animalistic moans i have heard to this day.....i didn't know girls had the ability to grip onto one's cock so tightly.....but she did....she gripped me....and all of the movements began to come from her....she fucked back .....i had no idea.....as i was almost to the point of not return....our eyes met in the mirror.....i more read her lips than heard her say "its ok....i love you".........those young orgasms......they were like finally peeing after having had to wait for hours and hours.....i could feel the streams .....one after another spraying into her.....i just kept cumming and cumming.....i had never seen or heard her cum before and i thought something was wrong and she was crying.....as she suddenly started gasping and moaning......i could feel the intense pressure on my cock as she squeezed against me.....a flood of liquid gushed from her......together we had made a huge puddle on her bed.....i watched her face through it all....finally, embarrassed, confused, somewhat scared.....i pulled out, pulled my shorts up and more or less ran back to my room......in a few minutes she came to my door...."come here".....she took my hand and led me into the bathroom that we shared.....and we showered together....she washed me....like she had done when i was little.....she washed me and she washed herself.....the whole time she just quietly talked....."its ok.....lets dont tell anyone.....but....dont feel bad about it....we did it for each other....its ok"

i loved her for that....for making it be ok. it never happened again. i did feel terribly guilty about it. i did masturbate 1000 times thinking about.....probably more.....it did make us different.....sweeter i think......more in love with each other than we always had been....which was alot.....we never talked about it......there were a few times when i know she offered more.....and a time or two where she did things to "teach me"......but we never had intercourse again.....

ive never told it to anyone in person.....or in "real life"......but it is the gospel truth.....of my first time ever.


I am not into the incest scene but that was a hot experience
 
I have a young lover (23, 40 yrs younger). In order to be invited to a swingers party last New Years Eve with hubby and I, he had to have his own female partner. It was his mother. I do not know who they had sex with at the party.

They traveled with us so we took them home and were invited in for a night cap. We ended up having a wild foursome and spent the night in one bed. I sucked and fucked my lover while the mother did the same to my husband and eventually her son. I was spitroasted by the two men; the mother was too. Both men and the mother performed cunnilingus on me. Can it get kinkier than that?

This!! This is awesome!
 
ive never told it to anyone in person.....or in "real life"......but it is the gospel truth.....of my first time ever.

Quite a story that I'm sure happened while you were at least a senior in HS I'm guessing and over 18. Maybe you should do a colab with one of the writers here. Come out with a polished version for the stories part of the site.

the closest I ever came to anything kinky: When we were both college aged I had a cousin start playing footsy with me while I we were in my parents hot tub one drunk Christmas Eve.

It really took me by surprise. Not only was this my cousin, but we'd never really had a playfully flirty connection or anything like that which would hint that she might be interested. But I'm a bit of an autistic (diagnosed by a professional) outcast and struggle reading people and situations, especially when it comes to women and sex and all that, which can get pretty subtle. Anyway, I ended up giving her leg a little squeeze and she didn't like that. Stopped rubbing her foot against me and moved away from me. That still puzzles me, that it bothered her so much, considering what she was doing.

She seemed kind of mad at me the rest of the night. The next time I saw her though everything was back to normal between us. We were friendly with each other but not close at all. I'll never know what was going on in her head.

That's my boring little story. It's not much, but thought I'd share anyway.
 
IsitBad ... just wanted to say that was very exciting that you shared that experience with us. It was very erotic. Big hugs for you. :heart:
 
I love this thread. I am able to post all my past stories.

Years ago after my divorce, I met a woman on Alt.com that was into pegging. We agreed to meet on a Saturday afternoon. We hit it off right away and went to her bedroom. When I started fucking her doggy bare back (as always) she reminded me that when I finished it was her turn. It took me about 3o minutes to cum then I laid next to her on the bed. I watched her get up out of bed with my cum dripping out of her pussy, grab her strap on off the dresser, slide her legs through the harness, tighten the buckle, lub it up with petroleum jelly, climb back into bed, slide a pillow under my ass, ask me if I was ready (I nodded yes) she lined the head of her cock up to my ass hole and slid it in. She leaned forward into the missionary position, she rolled me on my side, doggy style, rolled me on my other side, and bent me over her desk. I jacked myself off in every position we were in. We took a break to get a small snack and a drink. I put my boxers back on and she just wore her strap-on. Her roommates were all watching tv in the living room while we got our refreshments. When we finished, she said: why don't you drop your boxers and I will do you over the sofa for my friends to watch." I said "OK" I dropped my boxers, bent over the arm of the sofa and she pegged me until I shot another load. (On her girlfriend sitting there.) They all cheered and I went to clean up. One of the roommates kept my boxers (I don't know which one but I always hoped it was the one I shot my wad on.) I came several times that afternoon over the course of 4 to 5 hours. We made plans to meet up again but it never happened.
 
Happycpl69 ... you had a pair of hot kinky stories here. Very exciting. Loved them both.
 
Crazily enough this happened yesterday afternoon. I was trolling a guy-guy hook up site, hoping to find a quick hook up. I was chatting with a hot guy and we agreed to meet along the route I take to exercise. I was hoping to giet my hands (or mouth) on a hot cock, and maybe taste some cum.

We IM'd while we converged, and I forgot to confirm what kind of car he drove. We were going to meet in a relatively quiet corner of a parking lot, and I was going to get there first so I figured it'd work out.

After a few minutes of waiting a nice little sports car pulls up and a hot, dark, bearded gent nods to me. I go over and he rolls down his window. We greet each other and he asks if I want to get in. Of course!! So I hop into the passenger seat, say hi and grab the bulge in his jeans, while unzipping and freeing my smooth, hardening cock.

We are touching each other, gushing compliments about our new found partner's goodies. I've got a respectable 6", cut cock, medium girth, pretty straight, nice head with a smooth playland, a patch of bush, and closely kept fuzz on it creamy balls. I play with guys periodically and get complimented often. He is stroking me, rubbing precum on my head and cupping my balls then plants a passionate kiss on me nearly sending me over the edge.

He then leans back, unbuckles his jeans and pulls out a gorgeous thuck, veiny uncut cock (his profile said cut?) with smooth bslls and a thick raven haired bush. I lavish attention on his cock and balls, stroking, rolling his foreskin, massaging his balls. I'm thinking 'if he knew he was going to whip out his cock, why didn't he wear something easier?'. Oh well, I don't get to play with guys much? so no biggie.

He asks if I suck too, and I dropped down and engulfed this veined treasure. I'm sucking him,sucking his balls while he moans and urges me on. In a few minutes, he erupts and feeds me a hearty, sweet salty load. Once he's cleaned up I kiss him and give him some of his seed and he responds hungrily kissing back almost licking the inside of my mouth.

We straighten up and he asks if I come by here a lot, but I just say we can IM and arrange things, do we part ways.

When we part, I check my phone and I have a final IM from my date, "going to be late. Let me know if you still want to hookup. "

WTF? So if my date, with the cut cock is late and unsure if we should postpone, then who's uncut cock did I just suck and swallow?
 
Mine was a bi experience. I was his first. He was nervous of course we all are. He said he would cum 3 or 4 times with his wife. He came 6 times with me.
 
That's funny!

WTF? So if my date, with the cut cock is late and unsure if we should postpone, then who's uncut cock did I just suck and swallow?[/QUOTE]

That's funny!
 
If you jump back one page there is a 3rd experience.

I found it. That was a hot swap story. And just about it finding out how promiscuous she was. A very unique way to handle it which no doubt led to all the other stories. Bug hugs for you. :kiss:
 
I have posted a few here and there at this forum I think my kinkiest were:

1. My wife her sister & husband and me having a few sex nights
2. Masturbating with my brother in law watching his homemade porn videos
3. Getting naked on a friend's pontoon boat at 1 am and watch my wife get kissed and rubbed and kissed by my fiend's wife
4. my wife telling me to help her strip one of her drunken girlfriends and put her to bed only to have my wife start to kiss and suck her nipples and stripping down herself telling me to get naked and she starts licking and sucking her girlfriend only to have her friend lean over the side of the bed to puke in the bucket!

There are a few others but I need to go jerk off now!
 
Back during my army days, fucking my friend's wife, while he watched. I was to pretend he was not there, while she just stared at him. She wanted to be fucked hard, and we did a lot of force play where I just had my way with her. After I finished, she would suck him off.
 
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