Strangest sexual encounter

[Rayyj97]

5. Getting fucked in the woods, leaning on a railing, with a path just below us, and people walking on it.
6. Rubbing guys' dicks under restaurant or cafe tables using the sole of my high heel shoes, and occasionally planting my sharp heel into it. But nothing too strange here.

2, 5 and 6 sounds like a lot of fun… sign me up

 

[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.

 

[Roleplay_Hugo_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