Strangest sexual encounter

[xdresssissytoes]

Getting groped by hiking strangers camping alone on the App. Trail, ending up naked on my knees, sucking every cock . .. my face glazed with cum......some ending in my belly......a trail cock slut is born!

 

[69Explorer]

Possibly getting back after a night out with my housemate and her boyfriend at university. They started making out in the living room and then it turned into oral sex and then sex. They asked me to stay and watch. She had always been a little wild but nothing like that had ever been discussed. I watched until they invited me to join at which point I politely declined and left them to it

So if you could go back with what you know now.. would you have joined in ???

 

[LittleGreene]

So if you could go back with what you know now.. would you have joined in ???

I’ve asked myself that many times. Probably not. I didn’t really like him that much. He was annoying as hell. Decent cock though from what I saw.
I still see her occasionally and we’ve talked about it a couple of times. Shes so respectful nowadays though. Kids, husband, upstanding community member - ha ha.

 

[Dearelliot]

Visiting an older woman who lived next door, and yes I wanted to fuck her..I was 18, and had zero experience with any women, never really been kissed other than a peck on the cheek thing. It started with playing scrabble on occasion while her husband was fishing sort of thing, and then one night, we were talking about a lady next door who had breast cancer, and the older woman still talking about the womans breast cancer opened her blouse and took out her breast...saying "You 've seen a woman's breast before," and she pointed to the nipple area and said, "Her cancer was a lump, here, just below the nipple." It was a dream come true...within 2 or 3 weeks I was licking her between her legs.

 

[WhO2]

Hmmmm... not many I'd consider really strange, but my first-ever blow job was in my GF'S living room while her parents watched TV in the den. The couches in each room backed up to the same wall, so her parents were just a foot or 2 away as she's sucking my dick.

They knew we went to the formal living to make out, and i was more than shocked they allowed it. I was a little less shocked the first time I went in the parent's bedroom (she was also the first girl I went down on, but she would only let me do it in her parent's BR closet when they were both at work). On on a shelf in their BR was a pic of mom fully nude.

 

[EllaB_17]

May I know more about how number 1 went?

I wrote a long description of it some months ago but I won't post it here.
In sum, I was with some random guy on the dance floor, and we started kissing and the usual, he was touching my ass, and putting his hand inside my ultra-short ultra-tight mini dress.
He took my hand and we walked away, entered a toilet inside the club.
We locked the door.
I put my palms onto the wall, facing it, pushed my tiny ass out, arched my skinny back, adjusted my position, keeping in consideration the ridiculous height of my high heel shoes (19 cm, my favourite black patent pair), and he lifted my mini dress, pulled down my thong, ruined my pink lace thong, slid his dick inside my wet cunt, and fucked me from behind.
I had to make a makeshift ribbon on the side of my thong, the elastic was broken. I couldn't continue my clubbing without panties, it would have been too much even for me.
---
Actually I was smoking a cigarette while being fucked, but I omitted this detail because that's only of interest to people who are into smoking fetish like me.

 

[Hugo_Agogo_UK]

I wrote a long description of it some months ago but I won't post it here.
In sum, I was with some random guy on the dance floor, and we started kissing and the usual, he was touching my ass, and putting his hand inside my ultra-short ultra-tight mini dress.
He took my hand and we walked away, entered a toilet inside the club.
We locked the door.
I put my palms onto the wall, facing it, pushed my tiny ass out, arched my skinny back, adjusted my position, keeping in consideration the ridiculous height of my high heel shoes (19 cm, my favourite black patent pair), and he lifted my mini dress, pulled down my thong, ruined my pink lace thong, slid his dick inside my wet cunt, and fucked me from behind.
I had to make a makeshift ribbon on the side of my thong, the elastic was broken. I couldn't continue my clubbing without panties, it would have been too much even for me.
---
Actually I was smoking a cigarette while being fucked, but I omitted this detail because that's only of interest to people who are into smoking fetish like me.

Thank you. It’s wonderful

 

[EllaB_17]

Thank you. It’s wonderful

Welcome, thank you too.

 

[Erosfan]

A very long time ago, I was at a friends party, in the country. I was with my wife and her best friend. We left to go home around 2:00 AM. My wife drove because I had way too much to drink. As we pulled out onto the highway, I took all my clothes off. I was in the back seat. I tapped my wife's friend on her shoulder and she turned and saw that I was naked. She looked at my wife and said, "your husband is naked." My wife turned the interior light on and looked back at me. She didn't say anything, she just turned the light off. Her friend asked her, "what should we do with him?" My wife stopped the car and said, "let's get him in the headlights and jack him off." Being so late at night, on a backwoods county road, there was no traffic. They drug me out, walked me into the headlights and took turns jerking me, in an effort to make me cum. I guess I had had too much to drink because there was nothing they did that even got me close to cumming. We got back in the car and went home. I dressed before we got home because we had a baby sitter.
I missed a dream cum true because I drank too much.

 

[bobb_sledd]

One of the strangest; I was in town for work and decided to arrange an erotic massage off of Craigslist. I sent feelers out to both men and women posters. Two responses stood out, one from a guy and another from a woman. I realized they had come from the same email account. Turns out it was a young married couple, very new to pay4play, that were offering services to "make ends meet" financially. When I expressed a desire to meet with her, they indicated they would offer a discount if he could be in the room. I asked if it was a kink thing or a safety thing. They said it was for her safety. I countered by offering to pay them more than I would have for an erotic massage to let me watch and direct them having sex. They agreed and came to my hotel room a few hours later. The session started as agreed with my directing them having sex. After many compliments, comments, and crosstalk I was invited to participate as long as I didn’t try to fuck her. A very oral threesome ensued. My mouth and their mouths were every were.

I tried to repeat with them the next time I was in town, but we were never able to align our schedules.

 

[AverageJoe44]

I’m not sure if this qualifies as super strange but looking back on it…but was awkward and super dangerous. I’ve wrote before about how when i had turned 21 a local cougar in her late 40’s poached me out of a local tavern and rocked my world. Well I hadn’t a lot of sexual experience at that point, especially not a cougar in the middle of her sexual prime who just had an insatiable appetite. So needless to say this went on for awhile. Usually she’d go for runs in town, I’d pick her up on a side street and we’d park and fuck.
One particular time she completely floors me as she’s sucking my cock while I’m driving and says I want it buried in my ass. At this point I don’t think I’ve really even considered what anal sex may look like or feel like but there was no telling her no. So she gets on top of me and just uses her saliva from blowing me and slides down on me and goes to town. Looking back there was no gentle or ease in like you’d think. She obviously was experienced anally. I’m like trying to hold on for dear life and not bust too quick. She’s riding me, telling me to suck on her tits and cumming loudly while pressed on top of me. Needless to say it was all overwhelming and I probably came after about 3 or 4 mins - lol maybe it was less?!
Here’s where it gets weird. She’s like, “ did you just cum in me? “ I was like yeahhh, sorry, is it like too messy to do it there?”
She just starts laughing and says “I hit that first orgasm and just slipped you inside my pussy, I thought maybe you realized…”
I kinda froze as she had given me strict instructions the first time we hooked up a a few times after to not cum inside her because she was still extremely fertile.
So I had just planted my 21 year old seed inside a 46 year old. I asked her why she was laughing and she said probably because I’ll have to find somewhere that I can discreetly get a morning after pill. Then she’s like damn you really couldn’t tell the difference?! I think I stammered around that answer but I remember thinking to myself I was probably trying to concentrate on anything but the concept of what was happening so I could hold off for a few minutes!!

 

[Mu5tang]

When I was a senior in High School, I worked at a pizza shop.
A new girl, Julie was hired and started work on a Friday night. We instantly began flirting. She had wrecked her car the week prior and now depended on her mom for transportation. She got off at 9pm and I worked til 11pm. She was still there when I got off work so I offered her a ride home.
Her house was dark, and she remembered the neighbors having a party down the street. I took her there and she asked me to come in.
We eventually sat in a dim, empty livingroom on the couch talking and began kissing. Soon, she covered my lap with a pillow, pulled my cock out and began stroking it. A couple times, when it got a little dry, she pulled the pillow back for a few seconds to suck it, then quickly covered it back up.
After a few mintues, her mom came in with another woman and sat beside me. She apologized about forgetting to pick up her daughter and thanked me. The other woman sat across from us. Her and Julie's mom began talking to each other. All the while Julie was still secretly playing. The other woman got up and walked out and Julie's mom turned facing me. She began talking to me again. I could tell her mom was definitely feeling a bit of alcohol. I kept trying to get Julie to stop, and I was desperately trying to figure how to put my junk back without telling on myself. Im sure she was seeing that pillow moving slightly. And, why was it in my lap to begin with.
After a minute or 2, Julie's mom just stopped talking mid sentence. I looked over at her and she was just smiling at me. She jerked the pillow away and seen my exposed hard cock. "I knew it..... Julie" with a grin.
Her mom hurried and put the pillow back. Julie continued playing. Her mom quickly moved to get up and walk away, but stopped, giggled, and quickly sat back down. She reached under the pillow and pushed her daughter's hand away. She lightly squeezed my cock and slowly stroked it 4 or 5 times, raising the pillow to peek at it. Julie said, "Mom?!" Her mom said, "Oh my God" realizing what her intrusive thoughts made her do, and quickly got up. As she walked away, she said "Dammit, you guys go to the house". Julie laughed, said her mom is drunk. AND... that her dad was outside on the back deck.
We left, and Julie finished me off in her driveway. We did not fuck.
She never came back to work at the pizza shop after that.

 

[Samantha47]

It was with fat old guy here

561.973.1450

Older men turn me on so much

 

[Deadygirl]

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

 

[CuriousJInLA]

Maybe not the strangest but certainly stranger than usual and memorable:

I stayed out at the bar as a work function died down. I was chatting with a cute girl and obviously we were getting along. I was in a long distance relationship and her boyfriend was deployed. I had no intention of being a home wrecker but it was clear we were both lonely and looking for the same thing for just one night.

She invited me to her apartment and as I was going down on her she was incredibly wet. We fucked for an hour or so and she apologized that she was a gusher (which I loved and assured her was a good thing). But that was an understatement. When we were done her sheets and our bodies were completely soaked to a point I’ve never seen before or since. At one point i sat her on her bathroom counter and she left a puddle on the counter and floor. She insisted we shower, where I fucked her again. As she came again she said her boyfriend was a Navy SEAL and she hoped he wouldn’t find out. To which I replied I sincerely hoped not as well because I didn’t want to be killed for a simple night of mutual passion. She repeated that a few times and I decided it was time to go and we agreed not to exchange numbers.

I didn’t go back to that bar for years

 

[UncleJunior]

Backyard handjob from my bully of a cousin while the family watched fireworks in front of the house.

It was the way she kept threatening me to stay quiet while pinning me against the wall and kissing my neck that made it strange. When it was over, she licked her hand clean and made me kiss her.

 

[VDrago_1369]

A few years while driving for Uber I answered an add on Doublelist for a guy that wanted to jerk off with another man. There wouldn't be any contact on the respective parts, and he had a major cum fetish and wanted to cum into his girls panties and film it, just the lower regions. So I went over to his apartment, and his girl was there. I quickly picked up that this was a dom/sub type relationship, but both were super nice. So he and I are chilling in the living room, and this guy had a python down below, and while I'm no slouch this guy was hung. So we strip down, and he puts on some porn as we start stroking. His girl soon comes out to watch us, and he motions for her to come over. She sits between us as we're stroking, and he starts to play with her pussy. She reaches over and starts to stroke him, and she gives me permission to start playing with her tits. Soon she's stroking both of us at the same time, then she gets on her knees and starts stroking and sucking us both. She ultimatly lays down on the coffee table and spit roast her until it's time to blow our loads and he lays her panties out and we cum all over them as she films it. It was certainly a strange encounter, but one that was a lot of fun.

 

[desire30]

I visited my Aunt in Miami , I had no idea she was having company for the week. She gave me her study which has a large sofa . It was about 11pm and I had changed into a night shirt when my cell phone rang. It was my Aunt saying she and her husband just watch me strip on cc camera, Told me to come to their room and watch the video with them. There was a knock on the door and it was Jim her husband, "COME ON LYNN " the other couple was in the bedroom also and I was fuck and eaten all night

 

[Vitriolhack]

I visited my Aunt in Miami , I had no idea she was having company for the week. She gave me her study which has a large sofa . It was about 11pm and I had changed into a night shirt when my cell phone rang. It was my Aunt saying she and her husband just watch me strip on cc camera, Told me to come to their room and watch the video with them. There was a knock on the door and it was Jim her husband, "COME ON LYNN " the other couple was in the bedroom also and I was fuck and eaten all night

wow, quite a story!

You could make a literatica story about it, I would love to read the details of that story.

 

[UtilityCurve]

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

We're out there, waiting to do what other men won't for you.

 

[Italianstud59]

Got a BJ while her son was in the room playing his XBox. Posted about this many times.

funny. i was seeing s coworker who's boyfrienf had

Got a BJ while her son was in the room playing his XBox. Posted about this many times.

so funny you should say that. i was fucking a much younger coworker way back when. her bf couldnt stay hard anymore and she was always horny! one day i brought my son over so he could hang out with hers to play video games(teens). she needed help putting her new nipple rings on, so we snuck in bedroom. she got too horny so knowing teenage boys are clueless,we fucked for an hour lol

 

[lokiboy]

I know this doesn't totally fit what the OP was asking for. But I find it humorous and it does in volve as sex organ.

While I was in the military, my appendix ruptured. I was lucky enough to be one of the people that, while I knew something was wrong, I didn't notice a difference in how I felt when it ruptured (my body tried to encapsulate the bad stuff). It wasn't until I got a CT scan that they found out what happened. I didn't have to have emergency surgery, but they wanted to keep me in the hospital for a few days and firebomb my system with antibiotics (which had to work, otherwise I'd need surgery). So they started giving me IV drips of the stuff and monitoring me pretty closely. I had someone come in every few hours around the clock to check my vitals and listen to my gut sounds.

Well, I wasn't that sounds a sleeper to begin with, plus having to sleep propped up on my back made things more difficult, so I was kind of groggy one morning (around 4am) when a cute young nurse came in to those checks. She gave the usual quick greeting to someone that you don't want to bother but have to 'hi, just need to check how you're doing'. So I just kind of said OK, and tried to keep my eyes shut so I didn't see a bunch of light from the hallway and could get some more sleep after she was done. I had one of those gowns on, so she just pulled it off my shoulders and down so she could listen to various areas of my torso. As sleepy as I was, I recall thinking I was happy is such good shape for a cute girl to see me like that (even if she was doing her job). Anyhow, she listened to my heart and lungs, and then both sides of my abdomen (lower quadrants). Due to her height, and the bed's, she didn't pick the stethoscope up after listening to the near side. It must have been a more ergonomically comfortable motion for her to just slide it across the far side of my lower abdomen. Well, being a fit young man (aside from the appendix), and it being 4am, her forearm slide up against and was very obviously resting against my morning wood when she got the stethescope to the spot she needed to listen to. I'm sure it wasn't intentional, but I'm also sure she noticed it.

I wish I could say something else happened after that, but she just stayed professional and said 'ok, everything looks good' after she was done listening to that side as well. I didn't think too much about it at the time (too tired), but I thought about it later and was like - 'wait, don't they make pornos that start like that' lol

 

[live4thebj]

funny. i was seeing s coworker who's boyfrienf had

so funny you should say that. i was fucking a much younger coworker way back when. her bf couldnt stay hard anymore and she was always horny! one day i brought my son over so he could hang out with hers to play video games(teens). she needed help putting her new nipple rings on, so we snuck in bedroom. she got too horny so knowing teenage boys are clueless,we fucked for an hour lol

One time my daughter was at my and fiancés house. I was upstairs in the bedroom getting ready to leave with my daughter and then my fiancé pulls out my cock and sucks it then has me fuck her hard and quick on the bed. Didn’t realize at the time but the bed was hitting the wall. I know this because after I got downstairs my daughter asked if I was working out because she heard a lot of banging. I just said yeah.

 

[Imperfect_Guy]

One time my daughter was at my and fiancés house. I was upstairs in the bedroom getting ready to leave with my daughter and then my fiancé pulls out my cock and sucks it then has me fuck her hard and quick on the bed. Didn’t realize at the time but the bed was hitting the wall. I know this because after I got downstairs my daughter asked if I was working out because she heard a lot of banging. I just said yeah.

Well you weren't lying. You did get a workout!

 

[jd_sw]

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.