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Kinkiest real life experiences

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swmichcuck said:
My exwife was always a huge flirt and very kinky. She always said she wanted to be gang banged.
I wanted to help her realize her fantasy but it kind of worked against me. I told her that during poker night I would bet "her" on a losing hand and she would have to have sex with who ever won her in the hand.
She agreed and dressed extra slutty for poker night. The guys showed up (five of them) and we proceeded to get drunk and play cards.
My ex was serving drinks and had a plunging top on along with a short skirt that left nothing to the imagination. Comments were flying back and forth and the flirting was hot and heavy. She was all but giving lap dances to my friends. They had heard all of my stories about how kinky the wife was and there was something in the air that seemed that this may be a special night.
About three hours in, a ton of money was on the table and I saw my opportunity. I had shit for a hand and got into a bidding war with my buddy Steve. He raised me two hundred which I couldn't cover. Instead of folding I told him I'd offer up an hour with my wife to call. He couldn't call me quick enough and turned over his full house. I quickly mucked so that the gang couldn't see that I didn't even have a pair.
"She's all yours Steve." I said. The wife said it would be a minute and left for the bedroom, came back in a minute with two sets of handcuffs and proceeded to cuff my arms to the captains chair I was sitting in.
She then pulled out a roll of duct tape and taped my legs to the chair legs. My dick was getting hard at the though of having to watch my buddy fuck my wife while I watched helpless to stop it.
Seems I must have missed a memo or something because before I knew it the wife was naked and on her knees sucking off Steve. This I expected but then the other guys were all stripping as well. I guess we're going to watch her get gang banged after all.
Little did I know that after Steve finished in her mouth that she stood up and came over to me, grabbed me by the chin and proceeded to force me to swallow Steve's load as she spit it into my forced open mouth. She then announced that I would be her "fluffer" and suck each man til they were nice and hard to save her jaw some wear and tear. This is how I became a cuckold. Each of my "buddies" lined up and I was forced to suck them to full on erection, then the wife took over, finishing them off and then snowballing their loads down my throat.
Over the next hour I can't tell you how many more times I was forced to suck and watch as my poker buddies gang banged my wife or how much cum I had to swallow. My life would forever change. Good thing I've developed a taste and a desire for cum because I've become a cum dumpster. Even after the break up I still get my fill at the local ABS sucking anonymous cocks through the glory holes.
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SO FUCKING JEALOUS!!!!
 
This past New Year's Eve, I was involved in a mmmf. A couple I have played with many times and a stranger. Hubby jacked off while I played a cuckold type role with the other guy (his cock was a lot bigger than mine). I licked and sucked her and him while he fucked her hard for hours with me fucking her occasionally. Finally we moved to the bedroom and he finished inside her doggy style. I had already been told what to do and I didn't hesitate. I got under her just in time as his HUGE load spilled out of her gaping cunt. It was indescribably delicious. After the first gush, I proceeded to suck as much of his sweet cum as I could out of her. Then I took my turn behind her and flooded her loose hole with my own big load. Again I was ordered to take my place underneath her and I finally ate my own cream pie from her sweet pink hole. Once I finished cleaning her pussy a second time, I was told to clean the stranger's cock. I did so happily while she and hubby watched. I've fucked her many times since then but they haven't invited another cock since. I've told them I'd like to go to an adult bookstore with them and clean her up after each stranger uses her but so far it hasn't happened.
 
hey...

shelbakk said:
Damn that’s hot. I love the ending.
Click to expand...

so far you and me are the only ones who loved the way it turned out...
My friend at a later date told me he almost had to fight to get out of the apartment, because I never came back with those cigarettes.
 
This thread is super hot! My wife and I have had a few pretty kinky real life experiences but nothing compared to some here.

Once my wife and I helped whip/spank a female friend as her husband recorded us on video and my wife ended up using a dildo on her as I spanked her.

We have had sex on a boat on a public lake while people passed by and I’m sure they could get glimpses of what we were doing.

I have rimmed a female friend of ours in front of a group during a game of truth of dare.

I have also jacked off into a shot glass and had to drink it with rum as a dare one night.

We also use to do a lot of amateur porn and would have guys buy our used underwear, condoms , sex toys and videos of us using them. It was always kinky to be making a video for a specific person knowing they wanted our stuff. Then many would send us pics/ videos of them using our underwear or sex toys to masturbate which was sooo hot!
 
Where to begin, I guess it really started as a teen at a concert, in the middle of a huge crowd and my bf eases my skirt up and panties down while dancing, I was pretty intoxicated so I went wth it, I figured no one could tell because of crowd and loud music, I had cum a few times and he whispered he need a break so I slid my skirt down and left my panties to the side when a few minutes later I thought he wanted more when I felt a tug at my skirt and then a cock finding its way home, I didn’t know it was my bf I just figured it was but something felt different every time I tried to look back he’d dodge out of site , until I felt it run down my thighs and he went soft , I turned around and my bf was no where around and a strange guy stood there grinning, he could have been my bf brother but a longer cock
 
When my then GF sucked my cock dry while my mom watched us from the back window. (We were out on the patio at night)
 
MarciMay said:
Where to begin, I guess it really started as a teen at a concert, in the middle of a huge crowd and my bf eases my skirt up and panties down while dancing, I was pretty intoxicated so I went wth it, I figured no one could tell because of crowd and loud music, I had cum a few times and he whispered he need a break so I slid my skirt down and left my panties to the side when a few minutes later I thought he wanted more when I felt a tug at my skirt and then a cock finding its way home, I didn’t know it was my bf I just figured it was but something felt different every time I tried to look back he’d dodge out of site , until I felt it run down my thighs and he went soft , I turned around and my bf was no where around and a strange guy stood there grinning, he could have been my bf brother but a longer cock
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Very hot sexy story!
 
Not sure if this qualifies as “kinky” but it was hot!

Another first date with an older woman I met online on an adults dating site. She was in her late 50s but Had a body the looked 10 years younger. Her hair was greying but she had a tan smooth body and great fake tits she was proud about. We made it past the online flirting stage and graduated to a meet up over drinks.

Drinks and conversation went well though it was pretty tame compared to our online conversations. I remember she showed up in a lovely sun dress that gave me a clear view of her breasts and I’m sure she caught me looking as I saw no need to hide my approval. It wasn’t until the end of drinks the conversation became charged when she asked what it was I wanted. I laid out my case as I always do, that being a single father made anything regarding a social life next to impossible but I still liked to have fun when the right person comes along. All the dirty conversations we had prior came rushing back into memory and I could tell she was thinking the same as she got a bit flustered while being ready to leave.

I walked her back to her car, and we kissed in the parking lot. The kind of kiss that takes the wind from you as we both were turning the other on by now. We agreed on no expectations beyond drinks but she invited me to her place for a swim. I had no boardshorts on me so told her I’d like that, but I’d have to swim nude. But I could tell that wouldn’t be a problem. ;)

So I follow her back to her home for a good 30 min which only ramped up anticipation to even higher levels along the way. When we arrived she walked me to the backyard and offered me a beer while she went to go change. Things were going fast as we just met for the first time only two hours ago, but I took a swig and began to strip butt naked in the evening sun before wading into her pool. (She later admitted to watching me through the window). Here I was now, nude, in an older woman’s pool, blood pumping but still nervous about where the night would head. I was alone for a good 15 min before she finally came back out and in with me. She had a bikini on but I protested that since I was nude it was only fair she stripped too. She agreed and removed her top and bottoms. We kept up the conversation from drinks earlier as we built upon the comfort level. She was easy to talk to, open, funny, and flirtatious and the conversation flowed.

It was all stalling for what we both wanted to do however and so I remember making the first move as my arousal got the best of me and I kissed her in the middle of a story she was telling. My hands explored her body underwater and she did the same as she stroked off my erect cock. We went back and forth between making out, touching, laughing and masturbating the other off. I’d suck in her wet tits then she’d pull me off to sit me on the steps and suck me down. We were both so comfortable and confident that the sex flowed. I remember guiding her off my cock to bend her over the steps. She happily obeyed and raised her ass just above the water so I could penetrate her straight. I mounted her from behind and began to fuck that wonderfully mature pussy like the younger stud I was and she was loving it. The whole time she kept encouraging me to take all the pleasure I wanted from her to which I greedily did. I have good control so was able to throttle up and down accordingly to keep her full of cock and coming hard. I’m not sure if any neighbors saw us bit I have no doubt they heard. I pulled out to enjoy her sweet ass with my tongue until she told me to switch.

She asked if I enjoyed receiving as much as I did giving and I had to honestly answer I didn’t know as no woman had ever rimmed me before. She got excited and told me to relax as she slipped a finger up my anus. I wasn’t expecting this so I’m sure I squeezed up at first, but her instance on giving me pleasure along with some pleasant stroking on my cock got me to relax and let her in. It did actually feel good. Soon she warned me she was ready to pull out and I then felt her hungry tongue exploring my hole and spreading me wider. Fuck it did feel good as I stroked myself and she teased.

By now it was dark and we literally spent the entire night in that pool fucking each other freely in-between breaks of cuddling and talking. We shared a sexual connection to just be our horny selves and had no problems sharing our bodies, naughty thoughts and experiences with one another. We took turns watching the other. She let me suckle her tits in the shallow water. I tried floating on my back as she stroked me in the moonlight. If we had to pee we got out did so in the rocks in plain view. I didn’t leave until 3 or 4 in the morning it was all so intense.

The next day we were both recovering and still feeling euphoric and in shock at what took place. It was just pure raw sustained sex. And it was amazing.
 
AZsurfer35 said:
Not sure if this qualifies as “kinky” but it was hot!

Another first date with an older woman I met online on an adults dating site. She was in her late 50s but Had a body the looked 10 years younger. Her hair was greying but she had a tan smooth body and great fake tits she was proud about. We made it past the online flirting stage and graduated to a meet up over drinks.

Drinks and conversation went well though it was pretty tame compared to our online conversations. I remember she showed up in a lovely sun dress that gave me a clear view of her breasts and I’m sure she caught me looking as I saw no need to hide my approval. It wasn’t until the end of drinks the conversation became charged when she asked what it was I wanted. I laid out my case as I always do, that being a single father made anything regarding a social life next to impossible but I still liked to have fun when the right person comes along. All the dirty conversations we had prior came rushing back into memory and I could tell she was thinking the same as she got a bit flustered while being ready to leave.

I walked her back to her car, and we kissed in the parking lot. The kind of kiss that takes the wind from you as we both were turning the other on by now. We agreed on no expectations beyond drinks but she invited me to her place for a swim. I had no boardshorts on me so told her I’d like that, but I’d have to swim nude. But I could tell that wouldn’t be a problem. ;)

So I follow her back to her home for a good 30 min which only ramped up anticipation to even higher levels along the way. When we arrived she walked me to the backyard and offered me a beer while she went to go change. Things were going fast as we just met for the first time only two hours ago, but I took a swig and began to strip butt naked in the evening sun before wading into her pool. (She later admitted to watching me through the window). Here I was now, nude, in an older woman’s pool, blood pumping but still nervous about where the night would head. I was alone for a good 15 min before she finally came back out and in with me. She had a bikini on but I protested that since I was nude it was only fair she stripped too. She agreed and removed her top and bottoms. We kept up the conversation from drinks earlier as we built upon the comfort level. She was easy to talk to, open, funny, and flirtatious and the conversation flowed.

It was all stalling for what we both wanted to do however and so I remember making the first move as my arousal got the best of me and I kissed her in the middle of a story she was telling. My hands explored her body underwater and she did the same as she stroked off my erect cock. We went back and forth between making out, touching, laughing and masturbating the other off. I’d suck in her wet tits then she’d pull me off to sit me on the steps and suck me down. We were both so comfortable and confident that the sex flowed. I remember guiding her off my cock to bend her over the steps. She happily obeyed and raised her ass just above the water so I could penetrate her straight. I mounted her from behind and began to fuck that wonderfully mature pussy like the younger stud I was and she was loving it. The whole time she kept encouraging me to take all the pleasure I wanted from her to which I greedily did. I have good control so was able to throttle up and down accordingly to keep her full of cock and coming hard. I’m not sure if any neighbors saw us bit I have no doubt they heard. I pulled out to enjoy her sweet ass with my tongue until she told me to switch.

She asked if I enjoyed receiving as much as I did giving and I had to honestly answer I didn’t know as no woman had ever rimmed me before. She got excited and told me to relax as she slipped a finger up my anus. I wasn’t expecting this so I’m sure I squeezed up at first, but her instance on giving me pleasure along with some pleasant stroking on my cock got me to relax and let her in. It did actually feel good. Soon she warned me she was ready to pull out and I then felt her hungry tongue exploring my hole and spreading me wider. Fuck it did feel good as I stroked myself and she teased.

By now it was dark and we literally spent the entire night in that pool fucking each other freely in-between breaks of cuddling and talking. We shared a sexual connection to just be our horny selves and had no problems sharing our bodies, naughty thoughts and experiences with one another. We took turns watching the other. She let me suckle her tits in the shallow water. I tried floating on my back as she stroked me in the moonlight. If we had to pee we got out did so in the rocks in plain view. I didn’t leave until 3 or 4 in the morning it was all so intense.

The next day we were both recovering and still feeling euphoric and in shock at what took place. It was just pure raw sustained sex. And it was amazing.
Click to expand...

Did you continue fucking her?
 
peterthelicker said:
Did you continue fucking her?
Click to expand...

We did keep in touch online and there was no doubt we both wanted were looking forward to round 2.

It did happen maybe a month later. We both had schedules that made meeting up difficult. However this time in order to squeeze in play, she had just gotten off a long shift and was tired. It was late and I may have been too so sadly it ended up being a pretty normal encounter instead of the passionate fuckfest from earlier. But, that was such a high peak nothing we could have done would have topped it.

After that I lost track of her. Like I said, I have little free time for a social life or relationship and we not had gotten what we wanted from the other already. ;)
 
I like this thread because of the short stories of what people have done. I know some people just say, "FFM" or "Public Handjob" but I prefer at bit more elaboration.

I met a very sexy Black Woman in LA many years ago. She was tall for a woman, almost my height which is 5' 11". She had a great body, well toned, like your typical Women's Volleyball player.

She liked strapons so one day she came over to my hotel with a strapon. She went into the bathroom and came out wearing nothing but the strapon. It looked great on her. She had it secured so tight that it looked like it was part of her. I thought she was going to fuck me with it but she just wanted me to get on my knees and suck it.

So I kneeled down before her and started to suck it. I did not know what to do since I had never sucked before so she instructed me. I took part of it into my mouth, then a bit more, and so on. She seemed to get turned on by it and started to push the dildo further into my mouth while talking dirty to me. Soon she was fucking my mouth with the dildo while I was trying to hold onto her hips to prevent it going too far. She grabbed the back of my head as she lost control in an intense orgasm, screaming out and freezing in place.

She had pushed the dildo past my gag reflex and down my throat. I was really sacred at first but surprised I could take all of it. My lips were at the base of the dildo! She could not thrust because her body was going through a major spasm. I could feel all of her vibrations through the dildo inside me and on my lips as she came and came. Instead of fluid going down my throat, her energy and vibrations were. It was amazing. I could not breathe, but knew she would be done soon. Sure enough a few seconds later, her body relaxed she pushed me away and we both took in deep breaths then collapsed on the bed.

ES
 
Having a scantily clad, drop dead gorgeous girl impale me with a fairly large (9" x 1.75") plastic appendage.

She had told me to take initiative and work up to it; at the start, she had me buy plugs to stretch my rectum. I would add that this is good advice for any novices interested in anal play. You will be very tight the first time you try to insert anything in there, and even a much smaller one will damage you. So we worked up to this, a few sessions earlier she did me with a six and a half inch plug, and I proudly took it,. But she said, that's nothing, a true slut ought to be happy to take a much bigger one. So one day she broke out her purple buddy. When I first saw it, I was scared at the size of her appendage, but in the end, I was proud of myself for being able to take it- especially for her. In those days, I wanted to put myself through a lot of things for her, because she was, in many ways, my dream goddess.

So, I was on my knees, face buried in the pillow, and I could feel her gradually, slowly, and excruciatingly working it into me. The feelings during were indescribable- pain, discomfort, followed by a weird and sudden, powerful urge to pee, then a feeling of total violation. I remember burying my head in the pillow and moaning as she slid it in deeper. At one point, I must have moaned too loudly for her, because she slapped me hard in the buttocks as she moved it gently in and out. That did it; at this, the feeling of utter submission and surrender to this gorgeous goddess became indescribably powerful.

I remember afterwards, this indescribably feeling of wanting to just curl up at her feet and worship and caress them, just worship her power over me, because it was so intense. I have never experienced a sub space high that was that intense before- or since. That was easily the most intense sexual experience ever, and I only wish things with this wonderful woman would have continued to be so wonderful (while pegging was my main kink, her main kink was financial domination, and she turned out to be wayyy too much of a gold digger for my tastes.)

This is a true story- not just personal wank fodder- and it almost makes me regret the fact that I had to end the relationship with her. Because when it was awesome... it was awesome!!! Until I remember how I would spend more than my entire monthly paycheck on her and fritter away at my savings...
 
About a year ago, my boyfriend's brother graduated from high school (yes, he was 18). My bf had promised that if he kept a 4.0 GPA, that he would make sure he got laid so that he didn't go off to college a virgin. Well, the summer was going by quick and he had to follow through on his promise. Eventually, he asked if I would be willing to help him fulfill that promise. And of course, me and my depraved mind loved how kinky the whole thing was and didn't hesitate to say yes. My bf got a hotel room for us and didn't tell his brother who the girl was going to be. He just told him he had to be blindfolded. I showed up and his brother was sitting on the bed and I pushed him back so he would lay down. I started by going down on him and then got on top of him. It wasn't until I was already riding him that I took his blindfold off and he realized who I was. He freaked out a bit at first but my bf told him to just relax and enjoy. My bf just watched at first but couldn't help himself and ended up joining for a bit. He left us for the night though and his brother made use of every last second with me. I made sure he was ruined and I'm sure it's going to be a while until he finds a girl who will rock his world the way I did that night LOL. Unless he gets very, very lucky.
 
My sister-in-law was curious about what it would be like to be with another woman, and my wife volunteered me, I started with me just kissing her, but we'd all been drinking and we were both turned on by the whole thing and it escalated to having sex with her pretty quickly. My SiL either forgot her sister was in the room watching us, or drunk enough that she didn't care, and while I was going down on her I looked up and saw my wife vigorously making out with her sister and I nearly came on the spot! My sister-in-law lives on the opposite coast, but she's in the process of moving to our area as her divorce gets finalized and she's told my wife she'd like to spend another night with us
 
peruvianchica said:
About a year ago, my boyfriend's brother graduated from high school (yes, he was 18). My bf had promised that if he kept a 4.0 GPA, that he would make sure he got laid so that he didn't go off to college a virgin. Well, the summer was going by quick and he had to follow through on his promise. Eventually, he asked if I would be willing to help him fulfill that promise. And of course, me and my depraved mind loved how kinky the whole thing was and didn't hesitate to say yes. My bf got a hotel room for us and didn't tell his brother who the girl was going to be. He just told him he had to be blindfolded. I showed up and his brother was sitting on the bed and I pushed him back so he would lay down. I started by going down on him and then got on top of him. It wasn't until I was already riding him that I took his blindfold off and he realized who I was. He freaked out a bit at first but my bf told him to just relax and enjoy. My bf just watched at first but couldn't help himself and ended up joining for a bit. He left us for the night though and his brother made use of every last second with me. I made sure he was ruined and I'm sure it's going to be a while until he finds a girl who will rock his world the way I did that night LOL. Unless he gets very, very lucky.
Click to expand...

Very hot! Lucky brother, think he needs a semesterly reward to keep him focused and motivated in college :devil:
 
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