The very first time I got my mother in law to orgasm orally, she could not believe I could make her orgasm with my tongue and to her delight that day, I got her to orgasm over 18 times. We started at 8:12 a.m. and ended up that afternoon at 4:29 p.m. She was 57 at the time and had never experience oral sex in her 38 years of marriage. She had never had an orgasm on top of my father in law either, she went nuts when she climaxed on top of me. She is religious, but she used every profanity in the book that morning. I was only the second man to ever see her nude and the only one to ever get her to orgasm so many times in one day.
Kinkiest real life experiences
- Thread starter preacher72
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These are great stories, so I felt I needed to share.
I had gone to a bar/wing joint to meet up with some coworkers. Keep in mind this was almost 20 years ago, so texting and cells were not all that common. I didn't know it, but the party spot had shifted to another locale. I ended up at the bar having a few and talking to a woman a bit older than me (early 30's). After an hour or two, she invited me to join her for a party with some of her friends.
I followed her to the apartment we went to and walked in. I immediately saw three woman hanging out and music playing. The lady I followed there motioned me to sit on the couch. Once I did, she was on top of me, rubbing her hands on my chest and pants, telling me how great the night the night would be. As this was going on, one of the other girls came over and pulled my pants down and started sucking on my dick. Now, I like to think I'm all cool and stuff, but this was too much, and I lasted about a minute, blowing my load down her throat.
After I recovered, the original girl and my blowjob babe invited me back to another room. In there, the original girl continued with her rubbing and nasty talk, as my blowjob girl worked on me. As I rubbed my finger along the asshole of the first girl, my blowjob girl worked on my prick. Unfortunately after many beers that night, once was enough and we left the room. I walked out to see another guy sitting in the same spot, but with a naked girl dancing in front of him.
Long story short, I soon realized that blowjob girl was actually a guy...I know...hard to believe, but it never actually came up. Just some signs (lack of actually touching female parts, "her" actually doing the active part, etc). I wasn't mad about it. It was actually fun, and I wish at the time I would have known. I think it would have been fun to explore. While that part of the situation ended, I developed a friendship with the real woman. She was a total freak sexually and we talked freely about our interests. She was way out of my league I'm that category with interests in choking/hard core BDSM.
One of my big fetishes has always been used panties of a woman. Once she learned that, she was a steady supply of worn panties for me to enjoy. With mixed emotions, my situation changed and I lost contact with both of the ladies. But, at the end of the day, I am thankful for the experience.
I had gone to a bar/wing joint to meet up with some coworkers. Keep in mind this was almost 20 years ago, so texting and cells were not all that common. I didn't know it, but the party spot had shifted to another locale. I ended up at the bar having a few and talking to a woman a bit older than me (early 30's). After an hour or two, she invited me to join her for a party with some of her friends.
I followed her to the apartment we went to and walked in. I immediately saw three woman hanging out and music playing. The lady I followed there motioned me to sit on the couch. Once I did, she was on top of me, rubbing her hands on my chest and pants, telling me how great the night the night would be. As this was going on, one of the other girls came over and pulled my pants down and started sucking on my dick. Now, I like to think I'm all cool and stuff, but this was too much, and I lasted about a minute, blowing my load down her throat.
After I recovered, the original girl and my blowjob babe invited me back to another room. In there, the original girl continued with her rubbing and nasty talk, as my blowjob girl worked on me. As I rubbed my finger along the asshole of the first girl, my blowjob girl worked on my prick. Unfortunately after many beers that night, once was enough and we left the room. I walked out to see another guy sitting in the same spot, but with a naked girl dancing in front of him.
Long story short, I soon realized that blowjob girl was actually a guy...I know...hard to believe, but it never actually came up. Just some signs (lack of actually touching female parts, "her" actually doing the active part, etc). I wasn't mad about it. It was actually fun, and I wish at the time I would have known. I think it would have been fun to explore. While that part of the situation ended, I developed a friendship with the real woman. She was a total freak sexually and we talked freely about our interests. She was way out of my league I'm that category with interests in choking/hard core BDSM.
One of my big fetishes has always been used panties of a woman. Once she learned that, she was a steady supply of worn panties for me to enjoy. With mixed emotions, my situation changed and I lost contact with both of the ladies. But, at the end of the day, I am thankful for the experience.
preacher72
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My husband and I were at a party and we were giving a friend a ride home as he had too much to drive. I was feeling pretty good myself. When my husband stopped for gas, he went inside to pay, I slipped into that backseat with our friend. When my husband returned he never noticed and filled up the car. When he finished he got in, saw I was not there and turned around. By that time, our friend had my top down and wad sucking my breast. My husband, never said a word. He just smiled, adjusted the mirror and startef driving. He took every detour he could think of for the next hour as we playef in the back seat.
very hot
bryanbreeze
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WebTraveller
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Mine would probably be when I was single and dating a woman who was very open minded to say the least. We were in the party stages of our life and were always having big parties at her house and having a great time, usually ending up with us fucking like rabbits after everyone left.
When my birthday came around she had a big party planned and had been giving me presents all day, but no sex so I wondered what was up since we usually were all over each other all the time. Finally later in the evening she came in and said... "I bet you wonder why we haven't had sex today?" I laughed and played it off, trying to be cool. We were standing in the kitchen with a couple of her friends and she told me she had another present for me. She nudged her best friend who promptly got on her knees and gave me a long slow blowjob right in front of her. I made it clear I wanted to take the two of them to the bedroom, but she said my birthday gift was not going any further than the blowjob... which I didn't complain about.
When my birthday came around she had a big party planned and had been giving me presents all day, but no sex so I wondered what was up since we usually were all over each other all the time. Finally later in the evening she came in and said... "I bet you wonder why we haven't had sex today?" I laughed and played it off, trying to be cool. We were standing in the kitchen with a couple of her friends and she told me she had another present for me. She nudged her best friend who promptly got on her knees and gave me a long slow blowjob right in front of her. I made it clear I wanted to take the two of them to the bedroom, but she said my birthday gift was not going any further than the blowjob... which I didn't complain about.
leather_spitfire
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my kinkiest real life experience was probably a long weekend visit with a friend. we had talked at length (on messenger) about our respective sexual desires and fantasies. she was intrigued at my inclination to cross dress and wanted me to bring some clothes along for my visit.
she got me to dress up in a corset, ladies fitted shirt and high heel boots, along with my tight black jeans. she put a dog collar on me, which she had purchased previously with the intention of having me wear it all weekend. we then went to the supermarket and got all the food and booze we'd need for the weekend. she stopped short of using a lead because that would have raised a few too many eyebrows for her.
over the course of the weekend she waxed my legs, made me model more clothes for her, took me for dog walks in the twilight with a lead attached to my collar, cuffed me to her bed and used toys in my arse and took photos. I wish I still had copies of the photos!! it was a great weekend!
she got me to dress up in a corset, ladies fitted shirt and high heel boots, along with my tight black jeans. she put a dog collar on me, which she had purchased previously with the intention of having me wear it all weekend. we then went to the supermarket and got all the food and booze we'd need for the weekend. she stopped short of using a lead because that would have raised a few too many eyebrows for her.
over the course of the weekend she waxed my legs, made me model more clothes for her, took me for dog walks in the twilight with a lead attached to my collar, cuffed me to her bed and used toys in my arse and took photos. I wish I still had copies of the photos!! it was a great weekend!
swmichcuck
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poker night
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.
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.
E
ExiledWelshman
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Thought of another one from way way back in my uni days.
fucking one of my housemates during a party...and then fucking her sister about an hour later before going back to my housemate for more.
fucking one of my housemates during a party...and then fucking her sister about an hour later before going back to my housemate for more.
lgustosmio
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kinkiest experience ever was attending a doggie show in Amsterdam long time ago. Best part was watching some of the female attendees.
magicalmoments
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Now that needs a little more detail please.
What were the circumstances?
Like... did you walk in on her in the middle of a session at home? or did you both happen to turn up at the same B&D party?
AstorPlace
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Probably the time I slept with my friend's girlfriend while he watched. I don't really remember it, but I'm assuming it was kinky.
And then there was the time I had sex with the woman who was having an affair with me in an open bathroom at a party. People walked in and out. We just didn't care--too much wine, probably.
And then there was the time I had sex with the woman who was having an affair with me in an open bathroom at a party. People walked in and out. We just didn't care--too much wine, probably.
My wife called me at work one afternoon and said "when you get home, I want you to get naked, jack off and cum on my tits".
Well, my day was shot at that point. All I could think about was getting home and doing just that.
We have a large deck in the back yard and a privacy fence. When I got home, she wanted me to do this on the deck. No problem for me, I love being naked outside.
I got naked and she removed her top and bra.
I jacked for a short while and came on her tits as she had asked.
Afterward she told me our neighbor had watched us through a small opening in the fence. We were just sitting and having a drink now, me still naked and her topless with my cum on her tits.
I told her she should have stopped me.
She said she it turned her on knowing he could see me jacking and he could see her tits.
After the fact, it turned us both on and we enjoyed ourselves even more.
Well, my day was shot at that point. All I could think about was getting home and doing just that.
We have a large deck in the back yard and a privacy fence. When I got home, she wanted me to do this on the deck. No problem for me, I love being naked outside.
I got naked and she removed her top and bra.
I jacked for a short while and came on her tits as she had asked.
Afterward she told me our neighbor had watched us through a small opening in the fence. We were just sitting and having a drink now, me still naked and her topless with my cum on her tits.
I told her she should have stopped me.
She said she it turned her on knowing he could see me jacking and he could see her tits.
After the fact, it turned us both on and we enjoyed ourselves even more.
Frindsinitaly
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Tuff to choose just one, but this is a memory I have used many times since.
While at school to become a Military Police officer I shared a barracks room with a buddy I was stationed with for a few years prior. He and I were both fleet returnees so had more freedoms than the people coming right out of boot . He started dating a beautiful 18 year old. 5'4" 110 lbs blonde hair, stunning green eyes , about 32 C cup firm breast, and a high and tight ass. One night we were all in the room getting ready for bed. They were on his bed and I was on mine only about an arms length away. She started to touch him but he would always push her away. Then I started telling him "it's okay man , I don't mind go ahead" that seemed to relax him and he got more in to it. He stripped her down and started fingering her pussy, very timidly though. She kept staring at me and smiling as I showed her I was touching myself. I then suggested he handcuff her and make it a bit more interesting. I wasn't sure if he'd do it but she wasn't going to give him a chance to say no. So with her hands behind her back she started to suck his tiny dick. After about 5 mins he said he need to use the bathroom. That was all the break she needed. As soon as the bathroom door closed she mouthed for me to please fuck her. I couldn't deny a girl in need, so I picked her up and slammed her on his bed. I wasn't sure how long id have but I had to taste that gorgeous pink pussy. She was moaning and biting the pillow in no time. After about a minute she couldn't wait any longer and begged me again to please fuck her. I took my hard cock out and slammed it hard to the hilt. The look of pain and ecstasy on her face still burns in my mind. I gave her about 25-30 hard long strokes before we heard the toilet flush. I was able to pull out and jump back in bed just as he was turning the corner. I had her cream all over me and there was still some around her tight pink rosebud. I'm not quite sure how he didn't notice but as son as he got back he dove face first in to her pussy and started lapping the juices all up. That may have been the best part. He probably thought he was really turning her on. Little did he know it wasn't him.
While at school to become a Military Police officer I shared a barracks room with a buddy I was stationed with for a few years prior. He and I were both fleet returnees so had more freedoms than the people coming right out of boot . He started dating a beautiful 18 year old. 5'4" 110 lbs blonde hair, stunning green eyes , about 32 C cup firm breast, and a high and tight ass. One night we were all in the room getting ready for bed. They were on his bed and I was on mine only about an arms length away. She started to touch him but he would always push her away. Then I started telling him "it's okay man , I don't mind go ahead" that seemed to relax him and he got more in to it. He stripped her down and started fingering her pussy, very timidly though. She kept staring at me and smiling as I showed her I was touching myself. I then suggested he handcuff her and make it a bit more interesting. I wasn't sure if he'd do it but she wasn't going to give him a chance to say no. So with her hands behind her back she started to suck his tiny dick. After about 5 mins he said he need to use the bathroom. That was all the break she needed. As soon as the bathroom door closed she mouthed for me to please fuck her. I couldn't deny a girl in need, so I picked her up and slammed her on his bed. I wasn't sure how long id have but I had to taste that gorgeous pink pussy. She was moaning and biting the pillow in no time. After about a minute she couldn't wait any longer and begged me again to please fuck her. I took my hard cock out and slammed it hard to the hilt. The look of pain and ecstasy on her face still burns in my mind. I gave her about 25-30 hard long strokes before we heard the toilet flush. I was able to pull out and jump back in bed just as he was turning the corner. I had her cream all over me and there was still some around her tight pink rosebud. I'm not quite sure how he didn't notice but as son as he got back he dove face first in to her pussy and started lapping the juices all up. That may have been the best part. He probably thought he was really turning her on. Little did he know it wasn't him.
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Dickstroker81
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I can identify. I have fucked my mother-in-law's ass while my wife got her ass fucked by her father right beside us.
soflabbwlvr
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Bravo! A good smaritan fuck. Well played.
Dickstroker81
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I can identify. I have fucked my mother-in-law's ass while my my wife got her ass fucked by her father right beside us.
haurni
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I fucked my ex from behind in a public park while lying on the grass with our lower halves covered by a blanket. A guy walking his dog about 15 m away was looking at us a bit suspiciously but kept going, then we finished.
Another time I met a guy here on Lit and sucked his cock in my car in a deserted parking lot. I hadn't had a cock in my mouth in decades, but when he told me he was about to cum I kept going and swallowed it all.
I also post nude pics & videos of myself (or parts thereof) online.
Apart from a few group strip poker sessions, that's unfortunately about all I have to add to this thread
Another time I met a guy here on Lit and sucked his cock in my car in a deserted parking lot. I hadn't had a cock in my mouth in decades, but when he told me he was about to cum I kept going and swallowed it all.
I also post nude pics & videos of myself (or parts thereof) online.
Apart from a few group strip poker sessions, that's unfortunately about all I have to add to this thread
Let's see.. Kinkiest experience for me was my first time swinging with my hubby.. We met up with a couple, who was"in the lifestyle".. Not my cup of tea, but it was my first time tasting a woman, and I loved watching the other woman's man order her to suck my husband's cock. He really liked watching the girl girl action, and I loved him mounting me from behind while I ate her out.
Drunk sex with a roomie who told me it was time that We weren't ass virgins anymore. He lubed me up with massage oil and talked dirty to me while he let me back into him slowly. Was an amazing experience (we had such good sex), and I remember falling asleep on the couch with an ass full of his seed. He couldn't believe how much of an ass whore I was..neither could I! Don't have it that often now, but I sure have some good memories of kinky times.
Drunk sex with a roomie who told me it was time that We weren't ass virgins anymore. He lubed me up with massage oil and talked dirty to me while he let me back into him slowly. Was an amazing experience (we had such good sex), and I remember falling asleep on the couch with an ass full of his seed. He couldn't believe how much of an ass whore I was..neither could I! Don't have it that often now, but I sure have some good memories of kinky times.
mikeRotch69
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Hmm
I'd have to say... I was Very young and she was well into her 40's. We were sort of hanging out and watching a movie at night and I had my legs in her lap and my head on the sofa and her hands started to wander and play.
I got very hard, came all over her hand, she licked it up. We did it a couple of times after
I'd have to say... I was Very young and she was well into her 40's. We were sort of hanging out and watching a movie at night and I had my legs in her lap and my head on the sofa and her hands started to wander and play.
I got very hard, came all over her hand, she licked it up. We did it a couple of times after
TomBoner
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Gave a guy his first blow job from another dude while we were in a steam room of a cruise ship. Another guy was in the steam room watching and stroking himself as I sucked the guy all the way off into my mouth. He told me afterwards it was his first time getting sucked on by another guy but he'd been curious and wanted to do it for a long time. Glad I could be his first. It was a bit more kinky in that other guys were coming in and out of the locker room next to the steam room. In fact when I got done swallowing his nice big load he got down on his knees and started sucking me ... but about 15 seconds into it we heard someone coming towards the steam room and we just barely got covered back up with towels by the time the new person entered the room.
Dickstroker81
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My Mom would have help me rather than just watching.
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