Strangest sexual encounter

[pace_purr]

I remember at one swingers party I was fucking the hostess and the bedroom door opened and this girl walked in came up to the bed and tapped me on the shoulder before asking her mother where her school blouse was and if it had been ironed talk about passion killer.

 

[BInowGay]

I remember at one swingers party I was fucking the hostess and the bedroom door opened and this girl walked in came up to the bed and tapped me on the shoulder before asking her mother where her school blouse was and if it had been ironed talk about passion killer.

Wow, sounds kind of hot to me.

 

[Mrman69]

1. Fucked in a club by some guy I didn't know.
2. Gave a handjob to someone while hiking, simply because he said he liked my nails.
3. While masturbating in the dilapidated toilet of a bus station, someone climbed the wall and saw me.
4. I asked my first boyfriend to cum into a cooking pan. I put it on the stove, and tried frying it like an egg.

OMG I would never eat that…without ketchup

 

[Mike130]

1. Fucked in a club by some guy I didn't know.
2. Gave a handjob to someone while hiking, simply because he said he liked my nails.
3. While masturbating in the dilapidated toilet of a bus station, someone climbed the wall and saw me.
4. I asked my first boyfriend to cum into a cooking pan. I put it on the stove, and tried frying it like an egg.

Can’t top that last one. And the dilapidated toilet at the bus station sounds intriguing and begs some additional clarification. Like what happened next? Did you stop masturbating? Did you put on a show? If it was a guy, did you at least give him a blowie? Inquiring minds here….

 

[KindredFlame]

Watched two young guys mutual masturbating in the public park.

Nothing wrong with that. As I saw them I walked over to them and asked if I could join in. Only dreaming

 

[SirSparky]

Nothing wrong with that. As I saw them I walked over to them and asked if I could join in. Only dreaming

So rude hehe

 

[LoveAllKink1972]

I had a gentleman pleasure me with his tongue right after he orgasmed in me.

Nothing wrong with that

 

[Japansurfer]

Tied to the bed by mistress. She steps out for water and her daughter walks in. Takes a look - smiles and leaves

 

[Mike130]

I had a gentleman pleasure me with his tongue right after he orgasmed in me.

Do that all the time for my wife, she loves it.

 

[aquam34]

It was a boring day and I was lazing at the edge of a football field with a drink watching some guys play football. One of players looked at me as he ran past me. He was well built and lean muscular and sweating. I had always fantasized about sucking cock. But until then, it was only a fantasy. It was as if he saw it in my eyes. An hour later he took me to his place, let me suck his pornstar cock and then fucked me. I enjoyed the time with him, but it all happened so unexpectedly that I still sometimes wonder how it happened.

 

[neighbourly]

I had a gentleman pleasure me with his tongue right after he orgasmed in me.

It's the done thing, or at least it should be

 

[BillyWalrus]

While we were on vacation in Bangkok. Me and my wife visited a nightclub in the basement of the hotel we were staying. The club was pretty crowded since its the weekend. It is customary there to share the table if it's crowded. A group of 6 woman join our table which is just us 2. We talked to them and kinda hit it off, we danced, drink with them. I even ordered another 2 bottles of vodka and share with them. One of them really grinded her ass into me and got me hard on.

Nightclub in Thailand closes about 2AM. So, I invited them to join us in our room for after party. I bought another bottle for the after party. We and the group got into our room. After awhile the one that grinded her ass with me started kissing me and another was with my wife. Turned out all of them are well hung shemales.

It was a strange feeling fucking a shemale in her ass while seeing her fucks my wife in her ass and another shemale's dick in her pussy and another in her mouth. Interesting experience indeed.

Sounds like everyone had a good time. Waiter, cocks all around!

 

[kreemi_pi]

They're ALLLLL fucking strange in some way.

One time i went out with a guy, first date but i waa feelin him, so we went back to his place. THERE WAS A GIRL IN HIS BED. I was weirded out, she was apologizing, he said let's chiil abd get high and everybody relax.

She was an ex who still had a key. She was sexy and we dug eachother. Yes we had a 3some.

 

[CuriousDavid38]

I had a gentleman pleasure me with his tongue right after he orgasmed in me.

My go-to move! Lol

 

[Sir_Timo_Volodok]

Does it count if the sex was normal/boring but the aftermath was strange?

I hooked up with this older married woman early in my 20s, last call, we were both drunk kind of thing. Next morning, she offers me breakfast, and wouldn't you know her husband (who was "out of town on business") walked in the door about five seconds after she put it in front of me.

This dude is RIPPED, like 6'5", all muscle, probably has 100 pounds on me. He's instantly pissed -- go figure -- and locks eyes with me. He walks over to the breakfast bar as I steel myself for the mother of all ass kickings...

... except he doesn't throw a punch. Instead, he takes the plate, and without breaking eye contact starts screaming "YOU CAN FUCK MY WIFE, YOU CAN PET MY DOG, YOU CAN SLEEP IN MY BED, BUT YOU CAN'T HAVE MY MOTHERFUCKING EGGS!!!"

He then takes the plate out to his truck and proceeds to calmly back out of the driveway like nothing had happened.

I excused myself and had a long drive home to think about my life choices.

Side note: The breakfast I picked up at McDonalds didn't smell nearly as good as what his wife had prepared. No wonder he was so possessive about it.

 

[Sexysally1234]

I know this thread is super old, but I think my strangest was with my dad on one of our "date nights" in Dallas a couple of years ago.

Ok, so first off this is family stuff so lease don't bash me if it's not your thing. Anyway, my dad and I have been sexing together for a good while and we always have a "fantasy date" about once a month where I dress up a certain way, etc for a night of fun in a bigger city than the little town we live in. He usually gives me his credit card number and I order anything I want. Sometimes he picks something out, or at least a style. Usually aways see thru or strappy, anything that has that baby girl look, or a trashy slut, or innocent but naughty look. He loves me wearing sheer or semi sheer body stockings with nothing underneath and just a micro skirt or scarf around my waist and some hooker heels when we go out sometimes. Always crotchless. I've been fucked in an ally, bathroom, or theatre countless times wearing something like that. So the strangest time had to be in a park in Dallas right around dark with a old drunk watching us. LOL

This night I had a turquoise semi sheer lace body stocking on with a gold metallic wrap around my waist, and gold sequined spike heels. I had my hair curled but hanging free, and I had slutted up my makeup just to add to the naughtiness of it. We had just left this cool sushi steak house place and were headed back to the motel. We had been teasing each other under the table and showing my tits in the body stocking discreetly to some guys and we were both horny as hell. We cut through a little park with playground equipment and had stopped and were kissing and groping against the playground stuff. It was late, probably 11:30 or midnight, and chilly. I think it was in November. Anyway, this old drunk guy just stumbles past and plops down on a bench and starts watching us. We didn't stop, but dad kept a close eye on him. I even turned towards the guy as dad was groping my tits from behind and next thing I new dad was fingering me with one hand and pulled off the scarf and dropped it on the ground, so this guy's watching him finger me. I had never done anything like that before. Not that blatant in front of a stranger. I was so damn turned on, and scared too. My nipples were like rocks. i knew he could see my tits and everything under the soft sidewalk light close by and that made me even wetter. Then, dad had his cock out and was sliding it against my pussy and i almost came right then. Haha. He shoved it in me and we fucked, me facing this guy, I was playing with my tits and squeezing my nipples and dad just thrusting into me from behind. I even pulled down one shoulder strap and pull out my right tit for him. dad came in me and never got soft. just kept fucking me. the guy never said a word. just watching and rubbing his cock thru his pants the whole time. Dad was tearing my pussy up and was fingering my clit and I knew I was about to explode. My legs were shaking and I spread them even wider and leaned back against dad and wrapped my arm around his neck and the guy was watching my pussy and dad's cock fucking me. I groaned "I'm gonna cum daddy" and and he started ramming me harder. He pulled my other tit out and is squeezing my tits and playing with them and taking dirty to me and this drunk is still watching. i just groaned "watch me fucking cum mister" and fuck! That was it. I exploded. I was cumming and almost screaming it was so intense . dad was holding me up cause my legs were about to give out and I came in waves. Dad came again while I was cumming and I could feel it all just pushing out of me as he slammed into me. As soon as we gathered our senses we got dressed and hauled ass out of there. LMAO. God it was great but we've never let ourselves get carried away again like that. I can remember walking to the hotel he had to help support me to keep me from falling. And I remember his and my cum had run down the inside of my thighs and was soaking the bodystocking. It was fabulous

sooo horny

 

[strokinnoff1]

I know this thread is super old, but I think my strangest was with my dad on one of our "date nights" in Dallas a couple of years ago.

Ok, so first off this is family stuff so lease don't bash me if it's not your thing. Anyway, my dad and I have been sexing together for a good while and we always have a "fantasy date" about once a month where I dress up a certain way, etc for a night of fun in a bigger city than the little town we live in. He usually gives me his credit card number and I order anything I want. Sometimes he picks something out, or at least a style. Usually aways see thru or strappy, anything that has that baby girl look, or a trashy slut, or innocent but naughty look. He loves me wearing sheer or semi sheer body stockings with nothing underneath and just a micro skirt or scarf around my waist and some hooker heels when we go out sometimes. Always crotchless. I've been fucked in an ally, bathroom, or theatre countless times wearing something like that. So the strangest time had to be in a park in Dallas right around dark with a old drunk watching us. LOL

This night I had a turquoise semi sheer lace body stocking on with a gold metallic wrap around my waist, and gold sequined spike heels. I had my hair curled but hanging free, and I had slutted up my makeup just to add to the naughtiness of it. We had just left this cool sushi steak house place and were headed back to the motel. We had been teasing each other under the table and showing my tits in the body stocking discreetly to some guys and we were both horny as hell. We cut through a little park with playground equipment and had stopped and were kissing and groping against the playground stuff. It was late, probably 11:30 or midnight, and chilly. I think it was in November. Anyway, this old drunk guy just stumbles past and plops down on a bench and starts watching us. We didn't stop, but dad kept a close eye on him. I even turned towards the guy as dad was groping my tits from behind and next thing I new dad was fingering me with one hand and pulled off the scarf and dropped it on the ground, so this guy's watching him finger me. I had never done anything like that before. Not that blatant in front of a stranger. I was so damn turned on, and scared too. My nipples were like rocks. i knew he could see my tits and everything under the soft sidewalk light close by and that made me even wetter. Then, dad had his cock out and was sliding it against my pussy and i almost came right then. Haha. He shoved it in me and we fucked, me facing this guy, I was playing with my tits and squeezing my nipples and dad just thrusting into me from behind. I even pulled down one shoulder strap and pull out my right tit for him. dad came in me and never got soft. just kept fucking me. the guy never said a word. just watching and rubbing his cock thru his pants the whole time. Dad was tearing my pussy up and was fingering my clit and I knew I was about to explode. My legs were shaking and I spread them even wider and leaned back against dad and wrapped my arm around his neck and the guy was watching my pussy and dad's cock fucking me. I groaned "I'm gonna cum daddy" and and he started ramming me harder. He pulled my other tit out and is squeezing my tits and playing with them and taking dirty to me and this drunk is still watching. i just groaned "watch me fucking cum mister" and fuck! That was it. I exploded. I was cumming and almost screaming it was so intense . dad was holding me up cause my legs were about to give out and I came in waves. Dad came again while I was cumming and I could feel it all just pushing out of me as he slammed into me. As soon as we gathered our senses we got dressed and hauled ass out of there. LMAO. God it was great but we've never let ourselves get carried away again like that. I can remember walking to the hotel he had to help support me to keep me from falling. And I remember his and my cum had run down the inside of my thighs and was soaking the bodystocking. It was fabulous

That's gotta be one of the sexiest fucking stories I've read in years. What a good girl you are.

 

[athelticguy04]

I know this thread is super old, but I think my strangest was with my dad on one of our "date nights" in Dallas a couple of years ago.

Ok, so first off this is family stuff so lease don't bash me if it's not your thing. Anyway, my dad and I have been sexing together for a good while and we always have a "fantasy date" about once a month where I dress up a certain way, etc for a night of fun in a bigger city than the little town we live in. He usually gives me his credit card number and I order anything I want. Sometimes he picks something out, or at least a style. Usually aways see thru or strappy, anything that has that baby girl look, or a trashy slut, or innocent but naughty look. He loves me wearing sheer or semi sheer body stockings with nothing underneath and just a micro skirt or scarf around my waist and some hooker heels when we go out sometimes. Always crotchless. I've been fucked in an ally, bathroom, or theatre countless times wearing something like that. So the strangest time had to be in a park in Dallas right around dark with a old drunk watching us. LOL

This night I had a turquoise semi sheer lace body stocking on with a gold metallic wrap around my waist, and gold sequined spike heels. I had my hair curled but hanging free, and I had slutted up my makeup just to add to the naughtiness of it. We had just left this cool sushi steak house place and were headed back to the motel. We had been teasing each other under the table and showing my tits in the body stocking discreetly to some guys and we were both horny as hell. We cut through a little park with playground equipment and had stopped and were kissing and groping against the playground stuff. It was late, probably 11:30 or midnight, and chilly. I think it was in November. Anyway, this old drunk guy just stumbles past and plops down on a bench and starts watching us. We didn't stop, but dad kept a close eye on him. I even turned towards the guy as dad was groping my tits from behind and next thing I new dad was fingering me with one hand and pulled off the scarf and dropped it on the ground, so this guy's watching him finger me. I had never done anything like that before. Not that blatant in front of a stranger. I was so damn turned on, and scared too. My nipples were like rocks. i knew he could see my tits and everything under the soft sidewalk light close by and that made me even wetter. Then, dad had his cock out and was sliding it against my pussy and i almost came right then. Haha. He shoved it in me and we fucked, me facing this guy, I was playing with my tits and squeezing my nipples and dad just thrusting into me from behind. I even pulled down one shoulder strap and pull out my right tit for him. dad came in me and never got soft. just kept fucking me. the guy never said a word. just watching and rubbing his cock thru his pants the whole time. Dad was tearing my pussy up and was fingering my clit and I knew I was about to explode. My legs were shaking and I spread them even wider and leaned back against dad and wrapped my arm around his neck and the guy was watching my pussy and dad's cock fucking me. I groaned "I'm gonna cum daddy" and and he started ramming me harder. He pulled my other tit out and is squeezing my tits and playing with them and taking dirty to me and this drunk is still watching. i just groaned "watch me fucking cum mister" and fuck! That was it. I exploded. I was cumming and almost screaming it was so intense . dad was holding me up cause my legs were about to give out and I came in waves. Dad came again while I was cumming and I could feel it all just pushing out of me as he slammed into me. As soon as we gathered our senses we got dressed and hauled ass out of there. LMAO. God it was great but we've never let ourselves get carried away again like that. I can remember walking to the hotel he had to help support me to keep me from falling. And I remember his and my cum had run down the inside of my thighs and was soaking the bodystocking. It was fabulous

You are amazing.so sexy

 

[AZsurfer45]

Pretty tame, but at the time it was a thrill.

In college went out downtown to the local bars with some friends bar hopping. While at one of the bars I was squeezing up to the counter to order a drink with a buddy of mine and we were shoulder to shoulder next to an older birthday girl and her friends doing the same. Bday girl was celebrating hard and was pretty tipsy even though the night was still fairly young. Probably late 40s, average slim body from what little I remember, dark hair, Italian I think. What I DO remember is we started talking while waiting for drinks and she slips her hand down the front of my jeans to feel up and grab my cock! Just as normal and plain as day as if she was looking for car keys. 100% this was sexual assault but of course I 100% didn’t mind, lol. We made small talk for maybe 30 seconds with her hand on my dick but it felt longer.

She made some comment about liking what she found and then her drinks came and she wandered off. I didn’t think much of it, but my buddy saw it all and was stoked and the bartender might have as well as he had a scowl on his face I remember. Maybe the woman was just being an ass and he was glad she was gone? I dunno, but it seems more people saw than I realized.

Of course I found her in the crowd and tried talking to her some more. She was thrashed but frisky and we were scheming some way to go back to her place later to fuck. But she drove with her friends and they were having none of that. They soon whisked her away and that was that.

She totally would have passed out if we tried to hook up, but at the time, I’d never been with an older woman and I would totally be down to fuck and roll the dice as a horny college guy.

 

[KindredFlame]

Pretty tame, but at the time it was a thrill.

In college went out downtown to the local bars with some friends bar hopping. While at one of the bars I was squeezing up to the counter to order a drink with a buddy of mine and we were shoulder to shoulder next to an older birthday girl and her friends doing the same. Bday girl was celebrating hard and was pretty tipsy even though the night was still fairly young. Probably late 40s, average slim body from what little I remember, dark hair, Italian I think. What I DO remember is we started talking while waiting for drinks and she slips her hand down the front of my jeans to feel up and grab my cock! Just as normal and plain as day as if she was looking for car keys. 100% this was sexual assault but of course I 100% didn’t mind, lol. We made small talk for maybe 30 seconds with her hand on my dick but it felt longer.

She made some comment about liking what she found and then her drinks came and she wandered off. I didn’t think much of it, but my buddy saw it all and was stoked and the bartender might have as well as he had a scowl on his face I remember. Maybe the woman was just being an ass and he was glad she was gone? I dunno, but it seems more people saw than I realized.

Of course I found her in the crowd and tried talking to her some more. She was thrashed but frisky and we were scheming some way to go back to her place later to fuck. But she drove with her friends and they were having none of that. They soon whisked her away and that was that.

She totally would have passed out if we tried to hook up, but at the time, I’d never been with an older woman and I would totally be down to fuck and roll the dice as a horny college guy.

Can I use this to try to turn into a story. 750 words probably. Please.

 

[AZsurfer45]

Sure lol. Just share it with me once done.

 

[KindredFlame]

Sure lol. Just share it with me once done.

I have already started hoping you would say yes. Just playing with your words at the moment. But sleep is filling my eyes at the moment so a task for tomorrow.

 

[gonzo1025]

I know this thread is super old, but I think my strangest was with my dad on one of our "date nights" in Dallas a couple of years ago.

Ok, so first off this is family stuff so lease don't bash me if it's not your thing. Anyway, my dad and I have been sexing together for a good while and we always have a "fantasy date" about once a month where I dress up a certain way, etc for a night of fun in a bigger city than the little town we live in. He usually gives me his credit card number and I order anything I want. Sometimes he picks something out, or at least a style. Usually aways see thru or strappy, anything that has that baby girl look, or a trashy slut, or innocent but naughty look. He loves me wearing sheer or semi sheer body stockings with nothing underneath and just a micro skirt or scarf around my waist and some hooker heels when we go out sometimes. Always crotchless. I've been fucked in an ally, bathroom, or theatre countless times wearing something like that. So the strangest time had to be in a park in Dallas right around dark with a old drunk watching us. LOL

This night I had a turquoise semi sheer lace body stocking on with a gold metallic wrap around my waist, and gold sequined spike heels. I had my hair curled but hanging free, and I had slutted up my makeup just to add to the naughtiness of it. We had just left this cool sushi steak house place and were headed back to the motel. We had been teasing each other under the table and showing my tits in the body stocking discreetly to some guys and we were both horny as hell. We cut through a little park with playground equipment and had stopped and were kissing and groping against the playground stuff. It was late, probably 11:30 or midnight, and chilly. I think it was in November. Anyway, this old drunk guy just stumbles past and plops down on a bench and starts watching us. We didn't stop, but dad kept a close eye on him. I even turned towards the guy as dad was groping my tits from behind and next thing I new dad was fingering me with one hand and pulled off the scarf and dropped it on the ground, so this guy's watching him finger me. I had never done anything like that before. Not that blatant in front of a stranger. I was so damn turned on, and scared too. My nipples were like rocks. i knew he could see my tits and everything under the soft sidewalk light close by and that made me even wetter. Then, dad had his cock out and was sliding it against my pussy and i almost came right then. Haha. He shoved it in me and we fucked, me facing this guy, I was playing with my tits and squeezing my nipples and dad just thrusting into me from behind. I even pulled down one shoulder strap and pull out my right tit for him. dad came in me and never got soft. just kept fucking me. the guy never said a word. just watching and rubbing his cock thru his pants the whole time. Dad was tearing my pussy up and was fingering my clit and I knew I was about to explode. My legs were shaking and I spread them even wider and leaned back against dad and wrapped my arm around his neck and the guy was watching my pussy and dad's cock fucking me. I groaned "I'm gonna cum daddy" and and he started ramming me harder. He pulled my other tit out and is squeezing my tits and playing with them and taking dirty to me and this drunk is still watching. i just groaned "watch me fucking cum mister" and fuck! That was it. I exploded. I was cumming and almost screaming it was so intense . dad was holding me up cause my legs were about to give out and I came in waves. Dad came again while I was cumming and I could feel it all just pushing out of me as he slammed into me. As soon as we gathered our senses we got dressed and hauled ass out of there. LMAO. God it was great but we've never let ourselves get carried away again like that. I can remember walking to the hotel he had to help support me to keep me from falling. And I remember his and my cum had run down the inside of my thighs and was soaking the bodystocking. It was fabulous

super sexy story ...

 

[WendyTrilby]

Strangest sexual experience. I was in college, participating in a theater production of A Midsummer Night's Dream. I played Titania, the fairy queen, who is tricked by her husband, Oberon into falling in love with a guy who's been turned into a donkey.

Peter Webber played Oberon, and he and I did not get along. The show involved elaborate costumes, but the guys, wore ballet leggings as pants.

Before the show, I would go onto the stage and peek through the legs (the curtains on the side of the stage) to see the audience. I know this was a theater faux pas, but it was exciting. Peter showed up and we snuck a look at the crowd. I placed my hand on his butt to keep myself from falling behind the curtains and commented on how nice his ass was.

Well, all that tension we had built up during rehearsals came crashing down as our hands began to wander. Five minutes to curtain, and my hand was down his leggings, gently stroking him.

He, on the other hand, was unable to get to my intimate areas as I was wearing leggings under a leotard covered in a costume. Access denied.

But we had created a bigger problem. The curtain was about to go up in three minutes, and he was hard as a rock, and there was no hiding that from the stage lights.

Well, the show must go on. I contemplated finishing him off with my hand, but the mess—what would we do about the mess? So, I dropped to my knees and finished him orally, making sure to leave him clean and flaccid… well, semi-flaccid. No mess, other than a stray drip on my chin, that he wiped off.

I’m not sure if any other actors saw us, but they were probably obeying stage protocol and not creeping behind the curtains.

After that outstanding performance, we completed an almost three-hour play, and the commentary from those watching was that our chemistry was amazing. We went back to my place and rehearsed our chemistry so we could be ready for the next show.

 

[Baron50]

Watched two young guys mutual masturbating in the public park.

Mmm…. I met a young guy in the park wandering around looking lost … our eyes met as we passed each other first time and then 10 minutes later I was sitting on a bench in a secluded glade when he appeared at the end of a narrow path walking towards me… blond, effeminate and shy..I asked him if he was lost and he said no, he was following me.
He blushed and said he thought I was handsome and I was smitten by his smooth face and slim arms a very pretty boy… I couldn’t keeep my fingers to myself and stroked his thighs and shoulders as we talked and sat close to each other on the bench… until he leaned over suddenly and kissed me on the mouth, quickly and shyly then pulled away embarrassed.