Kinkiest real life experiences

[WhiteTrashDaddy]

Well one night I was at a bar with my husband and sister wives, well I went up to the bar to get another round of drinks for us. During the long wait, a old guy beside me that looked to be in his late 70's, started flirting with me. After a few minutes of him flirting, I decided I hadn't done anything naughty in a while. So I whispered to him, "Want go out in the parking lot, I'll give you a blowjob by the dumpster where it's dark."

He said, "Sure give me a few minutes, I got to take a leak."

Well I got our drinks and took them back to the table I whispered in my sister Toni's ear, "I'll be back in a few minutes, cover for me, I'm going to go be naughty. " Well I looked around for the old guy and didn't see him, so I figured, he must have gone outside already.

Well I went outside and looked over towards the dumpsters in the back of the parking lot, I could see a man's shadow standing there in the dark. I said to myself, "There he is," so I headed over. It was dark I said to him," I'm going to suck your old dick off real good," as I got down on my knees in front of him.

In the dark, I unzipped his Dickies and reached in and pulled his dick out of his boxers. Then slid my lips over head of his dick and started on sucking on it real good, massaging the shaft of his dick with my soft lips while swirling my tongue around the head of it. He was Breathing heavily, I think he could barely stand.

Then he grunted out loud and semen started oozing out in to my mouth, then I thought he was done. So I pulled my mouth off of his dick, I got squirted in the face with this enormously very thick rope of warm semen. It squirted on the left lens of my glasses, It was a enormous thick rope of semen, that strung down the lens of my glasses and all the way to my chin. Then hanging down off the side my chin a good four inches, Like a big thick gooey string of raw egg white.

Well I got up off my knees and was trying to clean my glasses off, by using my tongue licking the lenses, to put saliva on them to get the semen off. Then, Just as I was cleaning my glasses off with my tongue, the headlights of a car that was parking shined over to where we were. Well I looked up to ask the old guy, if he enjoyed it.

That's when I thought I was going to die, I was frozen in shock. In the light of the car headlights and seen that I had just given the local neighborhood smelly dirty old homeless guy a blowjob. The one that everyone sees in town asking for money in front of the supermarket and sleeps in the local Brentwood park, in the baseball dugout.

I just looked and didn't see anything and walked quickly back the bar, I ran into the old guy that I was supposed to do it, on the way in. I was in such shock, I didn't say anything to him, as I went back into the bar. I went over to our table, where my husband and sister wives were sitting, the entire time I sat there, I was thinking to myself, "Oh my god, I see him all the time when I go to the supermarket, I've even given him money, shit shit shit, I hope he doesn't tell anyone." Well I didn't say a word of what had just happened, my sister Toni noticed something was wrong, I whisper to her, "I'm okay, I'll tell you later sis."....

I love this story. probably made his year!!

 

[VampirTARA]

I love this story. probably made his year!!

it's one of my most embarrassing moments, I didn't know what to do, when I realized who's dick I just sucked it off. If that wasn't bad enough, I was in one of those moods and I was really sucking that dick real good... when I got home that night, I told my sister wife/ sister what happened and she freaking rolled,

 

[prop69]

Well one night I was at a bar with my husband and sister wives, well I went up to the bar to get another round of drinks for us. During the long wait, a old guy beside me that looked to be in his late 70's, started flirting with me. After a few minutes of him flirting, I decided I hadn't done anything naughty in a while. So I whispered to him, "Want go out in the parking lot, I'll give you a blowjob by the dumpster where it's dark."

He said, "Sure give me a few minutes, I got to take a leak."

Well I got our drinks and took them back to the table I whispered in my sister Toni's ear, "I'll be back in a few minutes, cover for me, I'm going to go be naughty. " Well I looked around for the old guy and didn't see him, so I figured, he must have gone outside already.

Well I went outside and looked over towards the dumpsters in the back of the parking lot, I could see a man's shadow standing there in the dark. I said to myself, "There he is," so I headed over. It was dark I said to him," I'm going to suck your old dick off real good," as I got down on my knees in front of him.

In the dark, I unzipped his Dickies and reached in and pulled his dick out of his boxers. Then slid my lips over head of his dick and started on sucking on it real good, massaging the shaft of his dick with my soft lips while swirling my tongue around the head of it. He was Breathing heavily, I think he could barely stand.

Then he grunted out loud and semen started oozing out in to my mouth, then I thought he was done. So I pulled my mouth off of his dick, I got squirted in the face with this enormously very thick rope of warm semen. It squirted on the left lens of my glasses, It was a enormous thick rope of semen, that strung down the lens of my glasses and all the way to my chin. Then hanging down off the side my chin a good four inches, Like a big thick gooey string of raw egg white.

Well I got up off my knees and was trying to clean my glasses off, by using my tongue licking the lenses, to put saliva on them to get the semen off. Then, Just as I was cleaning my glasses off with my tongue, the headlights of a car that was parking shined over to where we were. Well I looked up to ask the old guy, if he enjoyed it.

That's when I thought I was going to die, I was frozen in shock. In the light of the car headlights and seen that I had just given the local neighborhood smelly dirty old homeless guy a blowjob. The one that everyone sees in town asking for money in front of the supermarket and sleeps in the local Brentwood park, in the baseball dugout.

I just looked and didn't see anything and walked quickly back the bar, I ran into the old guy that I was supposed to do it, on the way in. I was in such shock, I didn't say anything to him, as I went back into the bar. I went over to our table, where my husband and sister wives were sitting, the entire time I sat there, I was thinking to myself, "Oh my god, I see him all the time when I go to the supermarket, I've even given him money, shit shit shit, I hope he doesn't tell anyone." Well I didn't say a word of what had just happened, my sister Toni noticed something was wrong, I whisper to her, "I'm okay, I'll tell you later sis."....

Awesome story...made my cock hard

 

[Lustyem6969]

Enable your PM's

I did.

 

[HighPlainsDrifter]

it's one of my most embarrassing moments, I didn't know what to do, when I realized who's dick I just sucked it off. If that wasn't bad enough, I was in one of those moods and I was really sucking that dick real good... when I got home that night, I told my sister wife/ sister what happened and she freaking rolled,

But, you enjoyed it. I'm sure he enjoyed. Would you do it again?

 

[Ralf913]

This is a great thread,read them all.Wish I had something to add.

 

[Dreamer110]

I'd have to say eating the wife out after her dates. Mmm.

 

[VampirTARA]

But, you enjoyed it. I'm sure he enjoyed. Would you do it again?

I don't get where you see anywhere in my story that says I enjoyed it and no I would not do it again...

 

[Hedonboii22]

First story would have to be when after a long time of searching I had finally met a transexual, male to female from Craigslist. She had just moved to town and was looking for casual friends. I went to her apartment later that night, she answered in a tank top and sexy black lace thong..After a few minutes of small talk we were on the couch kissing and ripping off each others clothes. Then I kissed my way down to her cock, licked it once..Then deepthroating her, loving every second of it..It was one of the first cocks I had sucked and the first tranny..Soon we were on her bed, 69ing until I told her to fuck me..I had my first prostate orgasm from her. It was unfuckingbelieveable, I had never came that hard before..She finished and then licked me clean..We hooked up for a few weeks until I got a gf and ended it..

 

[zotique]

Not that kinky, but here goes:

Wife's lesbian high school friend was visiting from Europe.

She'd been trying to get my wife in the sack since they were 15, so after a couple of bottles of wine she finally did. With me included in the package.

She's the only woman my wife approved of me fucking in our relationship.

Even though Iva was lesbian, I think she liked me too and we'd usually fuck after my wife participated a trois for a while then went to bed, leaving us to it.

 

[bone251]

I had a FWB that ...insert long story..... has several like minded girlfriends. They has an initiation party for her on a boat in the Great Lakes. In the front of the boat was a center bench that had large dildo mounted. They tied her up on this dildo with a whole bottle of lube and rode around the lake bouncing in the waves. She said she came more then she thought she could. It was a good party I guess. She was boat fucked.

She told me about this after I tied her up and made her cum over and over. She told me about the boat story after our fun time and said I was the only one who made her cum more then the boat ride.

A boat ride on the Great lakes in a small boat might be more intense then a Sybian.

 

[american_beauty]

my most intense lover was much older and related

 

[mortis]

I had a FWB that ...insert long story..... has several like minded girlfriends. They has an initiation party for her on a boat in the Great Lakes. In the front of the boat was a center bench that had large dildo mounted. They tied her up on this dildo with a whole bottle of lube and rode around the lake bouncing in the waves. She said she came more then she thought she could. It was a good party I guess. She was boat fucked.

She told me about this after I tied her up and made her cum over and over. She told me about the boat story after our fun time and said I was the only one who made her cum more then the boat ride.

A boat ride on the Great lakes in a small boat might be more intense then a Sybian.

This sounds like a great idea

 

[sexymanlick69]

Helping a lesbian couple get pregnant

 

[yesandfun]

Somewhat of a long story but by it was by far the kinkiest experience of my life so far so here goes.

I've always been into bukkake. When I first started watching porn some of the earlier videos I watched were bukkake videos. Watching a woman submit to multiple men coating her face in their cum turns me on a lot. I already find the female figure very beautiful but have her on her knees with cum all over her face and it's just sensory overload for me.

Naturally I always wanted to be one of the guys in a bukkake gang bang because of my cum fetish. When I was in my teens and early twenties I was an extremely heavy cummer. On average I would shoot about 10 powerful ropes of cum and knew I would fit in with a bukkake. Unfortunately I've yet to be in a one so a few months ago I figured I would try my luck on craigslist and make a post asking to join an established bukkake group. I knew my chances were slim but also knew I had to ask if I wanted to find out.

Coming with the territory I got a few responses from guys that seemed to be a few cards short of a deck. I didn't get any legit responses either of course. However, the next day I got a response from a guy saying that he would donate his wife for my group. Being the honest person I am I told him that I'm not in a group and was looking to join one but would love to set one up for his wife. Not expecting a response from that I was very surprised to get an email back from him saying they were cool with that. He sent a few pics of her and I was pleasantly surprised with how attractive she was. Short brunette hair, early 30's or so, petite and fit. Exactly how I like them. I was getting excited for this.

Originally they would only write me on Saturday nights. This went on for easily three weeks of our emails only taking place on Saturday's due to them only emailing me on that day. So he and I established what type of guy she was looking for in this event and with that info I made a detailed craigslist post asking for guys to join and what the qualifications were. As the responses rolled in I forwarded them to their email. After that first few forwarded emails to their craigslist address, she took over the emails to me and sent me another picture of herself holding a piece of paper noting the date and saying that she was a real person. I gave her my phone number too just in case the craigslist email expired as I wasn't sure if that was a possibility.

Keep in mind this correspondence between us was going on for over weeks now. It wasn't moving fast but that was okay with me because I wanted to make sure I was meeting normal people (other than the fact that we were setting up a bukkake party through craigslist lol). Since this was all taking place over a few weeks everyone's horniness was slowly creeping up over time as the emails went back and forth. The emails were pretty lurid too and lets just say not very bland. She would tell me how she has an insatiable craving for cock and cum, calling herself a cumslut, and I in return would tell her I love getting head and seeing a woman take my cock and cum down her throat.

After another week or so of emails or so I finally get a text from her one weekday night. Their Saturday plans fell through and she wanted to know if I wanted to meet them on Saturday, plan the event for the following Saturday, as well as have some fun with each other to see how we feel about each other. I was assuming me and her husband would double team her. Obviously I jumped at the offer and we set it up to meet to meet at a local bar that upcoming Saturday night.

So Saturday arrives and I'm on my way to the bar. I get a text from her switching locations because the bar was insanely crowded. Instead we decided to meet at a local all night restaurant. I pull up, walk in and see her and her husband sitting at a table. Fortunately she looked just like her pics. We all met and started talking and the conversation, while a bit awkward, went well enough and got more fluid as time went on. They told me about past experiences and how they don't do this type of stuff that often. They were also happy I was who I said I was as in the past they've had people turn out to be a bit loony. So much so that one of them supposedly borderline stalked her after she turned him down. Anyways, after maybe 30 minutes of conversation her husband suggests we get a hotel room so we can go over the candidates and email them. We picked a nearby hotel and drove separately there.

So she books us the room and we split the cost. All they had was a suite but since it was so late (around midnight or so) they gave us a good rate. She was sitting at the desk in the room on her phone going through the emails picking the ones she liked and deleting the ones that weren't what she was looking for or the ones that in no way responded to her email questions.

After roughly an hour of that and small talk between us three her husband asks if she and I were going to get down to some fun. She and I locked eyes, grinned and she came over to the couch I was on as he dimmed the lights. She sat next to me and I asked her husband if there were any rules. There weren't many. No watersports, anal or pain basically. So she and I started to make out really heavily, my hands exploring her hips, chest and crotch. After a little of this she gets on her knees in front of me and started to undo my belt buckle after she took her shirt and bra off while I sat on the couch. Her tits were proportional to her size. Petite but enough to get a handful of. She pulled my pants down and started to almost literally inhale my cock. When we first started making out, her husband was on the bed watching us. Sometime or another he moved over to the other side of the couch while she was blowing me. I've gotten lots of great blowjobs before but this one was quite possibly the best I'd ever had. She definitely walked the talk and what she said in her emails about her love for giving head were absolutely true. She was going to town and barely coming up for air. Exploring every inch of my cock and taking her into her throat, working the balls and shaft. At one point about ten minutes into the blowjob her husband commented on how impressive it was that I was lasting that long and that he would have cummed already by then. My stamina was high that night and it made me happy because I would have let her blow me for an hour if she wanted to. The blowjob was that amazing. I was both talking dirty to her ("You love being a cumslut don't you?") and complimenting her ("Fuck you are so god damned hot. You look incredible with my cock in your mouth.") and she would just purr a "thank you" to me, like a cat in heat almost. The lust was off the fucking charts and we were out of our minds.

Maybe 15 minutes into the blowjob I tell her how badly I wanted to fuck her brains out. She looked at her husband, he looked and her and then asked her if she was cool with that (as if they were only planning on her blowing me). She grinned and said yes to him. So I pulled her panties off her and put her on her back on the hotel room floor. As I entered her while she was on her back, her hands were on my shoulders and she started to grip them even harder. Her eyes glassed over and she just sighed. As I was pounding her I would reach down and suck on her nipples. Her body was so fucking hot and making me stay rock hard. I lasted for another ten minutes before I stood up and had her blow me some more because I was ready to cum on her. Another few minutes went by and I told her I was gonna cum all over her face. My cock started to twitch and tingle and I let loose around 6 or 7 strong shots of cum to her face. It was definitely a very impressive load and one of my biggest in a long time. So there I am at around 2 in the morning or so standing above this random woman on her knees covered in my cum in some random hotel room while her husband sat on the couch watching lol. The places that unchecked lust will take me!

She asked me if she could wipe the cum off her face as her husband went to grab a towel. After taking mental inventory for a few more seconds I of course said sure. After she wiped her face off she laid on top of her husbands and my lap while we sat on the couch, the two of us in a post amazing sex high. We spoke for maybe thirty minutes talking about how crazy fun that was as well as both of them complimenting me on how big of a load I shot on her face before I had to go because I had to work the next day. I thought it was going to be a MFM and didn't think it would be hot wife play but honestly that was more than cool with me ha! I was surprised he didn't join in though.

Around five in the morning she texted me thanking me for a great fuck and great load and that they were both happy that I was who I said I was. She also said that she couldn't wait to meet again. Our texts went on for another day or so before communication slowed down. I actually didn't hear from her for another month or so and when I did it was basically a text saying sorry for no communication and that she wanted to meet again. Unfortunately we never did meet again so as of now it was just a one off, crazy night. The bukkake obviously never happened but honestly the night we shared was better than any bukkake because it was much more intimate.

 

[zotique]

I was in LA when I was 19 visiting a platonic girlfriend in Topanga Canyon.

Friday afternoon her boyfriend came over and said a gal from work was heading out to the disco (1973) pick a guy up and fuck.

My friend's bf said "I know a good looking young guy from Vancouver who might do that for you."

He claimed he was concerned about her safety picking up strangers but I think he just wanted me away from his gf.who was described in a Joni Mitchell song:

Estrella circus girl
Comes wrapped in songs and gypsy shawls
Songs like tiny hammers hurled
At beveled mirrors in empty halls
Empty halls and beveled mirrors
Sailing seas and climbing banyans
Come out for a visit here
To be a lady of the canyon


Anyway, they introduced me to this woman and she took me home and sucked and fucked me good on her black silk sheets on the water bed, bought me a carton of smokes and dropped me off on the freeway on ramp for Arizona.
Wouldn't let me eat her out though, sadly.

 

[Grey Shadow]

That's an awesome story. All the better because it didn't work out exactly as planned. In the real world sex never does but the unpredictability of it is part of the fun.

Somewhat of a long story but by it was by far the kinkiest experience of my life so far so here goes.

...After roughly an hour of that and small talk between us three her husband asks if she and I were going to get down to some fun. She and I locked eyes, grinned and she came over to the couch I was on as he dimmed the lights. She sat next to me and I asked her husband if there were any rules. There weren't many. No watersports, anal or pain basically. So she and I started to make out really heavily, my hands exploring her hips, chest and crotch. After a little of this she gets on her knees in front of me and started to undo my belt buckle after she took her shirt and bra off while I sat on the couch. Her tits were proportional to her size. Petite but enough to get a handful of. She pulled my pants down and started to almost literally inhale my cock. When we first started making out, her husband was on the bed watching us. Sometime or another he moved over to the other side of the couch while she was blowing me. I've gotten lots of great blowjobs before but this one was quite possibly the best I'd ever had. She definitely walked the talk and what she said in her emails about her love for giving head were absolutely true. She was going to town and barely coming up for air. Exploring every inch of my cock and taking her into her throat, working the balls and shaft. At one point about ten minutes into the blowjob her husband commented on how impressive it was that I was lasting that long and that he would have cummed already by then. My stamina was high that night and it made me happy because I would have let her blow me for an hour if she wanted to. The blowjob was that amazing. I was both talking dirty to her ("You love being a cumslut don't you?") and complimenting her ("Fuck you are so god damned hot. You look incredible with my cock in your mouth.") and she would just purr a "thank you" to me, like a cat in heat almost. The lust was off the fucking charts and we were out of our minds.

Maybe 15 minutes into the blowjob I tell her how badly I wanted to fuck her brains out. She looked at her husband, he looked and her and then asked her if she was cool with that (as if they were only planning on her blowing me). She grinned and said yes to him. So I pulled her panties off her and put her on her back on the hotel room floor. As I entered her while she was on her back, her hands were on my shoulders and she started to grip them even harder. Her eyes glassed over and she just sighed. As I was pounding her I would reach down and suck on her nipples. Her body was so fucking hot and making me stay rock hard. I lasted for another ten minutes before I stood up and had her blow me some more because I was ready to cum on her. Another few minutes went by and I told her I was gonna cum all over her face. My cock started to twitch and tingle and I let loose around 6 or 7 strong shots of cum to her face. It was definitely a very impressive load and one of my biggest in a long time. So there I am at around 2 in the morning or so standing above this random woman on her knees covered in my cum in some random hotel room while her husband sat on the couch watching lol. The places that unchecked lust will take me!

She asked me if she could wipe the cum off her face as her husband went to grab a towel. After taking mental inventory for a few more seconds I of course said sure. After she wiped her face off she laid on top of her husbands and my lap while we sat on the couch, the two of us in a post amazing sex high. We spoke for maybe thirty minutes talking about how crazy fun that was as well as both of them complimenting me on how big of a load I shot on her face before I had to go because I had to work the next day. I thought it was going to be a MFM and didn't think it would be hot wife play but honestly that was more than cool with me ha! I was surprised he didn't join in though.

Around five in the morning she texted me thanking me for a great fuck and great load and that they were both happy that I was who I said I was. She also said that she couldn't wait to meet again. Our texts went on for another day or so before communication slowed down. I actually didn't hear from her for another month or so and when I did it was basically a text saying sorry for no communication and that she wanted to meet again. Unfortunately we never did meet again so as of now it was just a one off, crazy night. The bukkake obviously never happened but honestly the night we shared was better than any bukkake because it was much more intimate.

 

[darlasmaster01]

Getting a blow job from my sub on a city bus. No one was in the back so we sat down her the window seat. I tapped Darla on the shoulder and took my cock out of my pants. She knew what to do and started to suck me off till I came in her mouth. Every time someone headed for the back of the bus Darla hoped they would watch her enjoy blowing me.

 

[Hedonboii22]

Can't give out all the details but....

Accepting "donations" from men I met online for "massages"

Going out in public in women's leggings, wig, makeup, and of course heels and lingerie underneath...

Fucking my girlfriend in a dressing room.

Taking my step siblings virginities..

 

[PurpleSatin]

wildest thing I've done so far is meet a ladyboy that I had been chatting with for a while. She was so hot, like hotter than most real women. Anyway that was one hot experience, I don't want to get too explicit

 

[Jules2372]

Dogging in a local lay-by resulting in my shagging a stranger whilst being watched by my boyfriend and five strangers - mind blowing. Some years back now but wow!

 

[applc]

Alot of great topics on here where people share really kinky and/or taboo fantasies. Some share things they have done in real life. Thought it would be a good idea to start a thread where people can share some of their best real life memories or secrets. I can start:

I was out with a cousin one night and we met a couple we ended up all going to their hotel for more drinks when the bar closed and we all ended up doing the woman together. I remember how hot it was getting a bj from her while my cousin went down on her and hubby watched. Than we were watching and stroking while she rode her hubby, than hubby invited me to take her ass and she blew my cousin. It was sooo hot for each of us to cream in each of her holes.

Anyone else care to share?

For over 4.5 years I made a living stepping into G-strings of just about every style and variety. I was an ex ballet dancer who began doing striptease adagios in 1979. Back in that era just about everything and anything went and some exclusive Clubs actually had guys come in and perform with the girls. This is almost unheard of today. My very last gig I did was a really good, well-choreographed number with a really good dancer. Towards the end of it we had to unlatch each other's G-strings and perform a short adagio segment in the nude. They had me put on a really thin waistband that was attached to a no shit sequined cock ring. The whole number ended with us simulating sex on an elevated bed. That's how we did things in the 70s and 80s. Back then, there was an entirely different mindset on what constituted beautiful eroticism.

 

[annainnj]

Went to my (former) lovers second home as he invited m, saying his wife was fast asleep & we could fuck endlessness & she wouldn't wake (apparently she drank a bit, that part is sad, I know), anyway, got to the house & the door was open.. walked in & didnt see him, crept tot he bed & ran my hand over what I thought was his leg under the covers Ran my hand up to his face to kiss him & VERY quickly realized it was his wife. In the pitch dark turned around to leave & call his cell from the porch when walking out thru the living room I see him on the sofa. I woke him with my mouth on his & my hand around his cock. Of course we got right into it (and trust this man KNEW how to fuck). After about 45 minutes of both of us cumming hard, he wants to go again but this time leads me down to the bedroom so he can fuck me bent over the bed one arm on my hips the other holding me in place by my hair in a fist in his hand me REALLY was fucking me hard first pussy, then moved his wet cock to my ass.... making me whimper. Iva's so concerned I'd wake her but he took my hand in his & with is cock deep inside me thrusting made me touch his wife's leg under the covers while he whispered how much more he loved me. Saying things like he was "cock deep fucking" me rights in front of her. Led me down the bed so we were nearly over her.....actually fucked me towards her. Was one of the hottest experiences of my life. He remains one of my best lovers ever. And his cock (actually entire body & face) was fucking perfect. We still talk, years later, and just saying "my other house"turns us both on.

 

[Sweetsweatymango]

The kinkiest was when I witnessed a woman taking a shit on a man, it got me hooked on scat play. She shat a perfect, beautiful sausage coiler shit. The guy casually rub it on himself, got dressed and left. Fucking incredible.

 

[JackOffer]

The kinkiest was when I witnessed a woman taking a shit on a man, it got me hooked on scat play. She shat a perfect, beautiful sausage coiler shit. The guy casually rub it on himself, got dressed and left. Fucking incredible.

If I was him I would have eaten it while I fucked her ass!