What is the strangest sexual encounter you ever had?

I was lying in bed, dead asleep. And, the SO rolls over and says, "You awake? I'm horny as hell!"
I was lying in bed, dead asleep. And, the SO rolls over and says, "You awake? I'm horny as hell!" Originally Posted by Billogoods
I think this one is the hardest to believe. LOL!
rexdutchman's Avatar
^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^Now that's fucking funny right there ^^^^^^^^^^^^^^^^^^^^^^^^^
mikehammer002001's Avatar
I was lying in bed, dead asleep. And, the SO rolls over and says, "You awake? I'm horny as hell!" Originally Posted by Billogoods
calling bs!!! sounds more like a dream, LOL
I was lying in bed, dead asleep. And, the SO rolls over and says, "You awake? I'm horny as hell!" Originally Posted by Billogoods
Now there is a fantasy I won't get to experience
Randall Creed's Avatar
Excellent stories so far, especially the first one. If it were any juicer, I'd be jacking off right now.

Mine's probably a bit boring, but I'll take a swing here.

We've all grown up knowing hot chicks that were either a bit too old for us or, unless you're the high school QB, wouldn't give you the time of day. There's this one, who fit the 'a bit older than me' category...not creepy old, but 'old enough to be your mom's youngest friend' old. She was fine as all fucking get up. Big booty, thick thighs, made a habit of wearing hooker style miniskirts, the look that made guys say 'DAMN!!' all day long. She looked like she could've been in rap videos.

For YEARS I drooled over her every time I saw her. I actually tried to make a move on her years before, at the club. But I was such a nobody that she probably didn't remember (cold, hard rejection, fwiw).

Fast forward a few years later. A little older now, low 20's, some definable muscle structure. On a rare night, I didn't feel like going out to a club. Had a cousin of similar age who wanted to go out. I wasn't feeling it, but he was soooo insistent. Oh, fuck it. I'll go if shut you the hell up.

We go. We're at the club. He's doing his thang, dancing, drinking, flirting with chicks, the whole nine. Meanwhile, I'm in the corner, babysitting a drink, watching the clock to when this is all over. Lo and behold, guess who comes walking up. Yes, it's the big booty, high school queen, rap video body chick that would've give me the time of day years ago. She's wearing one of her little signature, way too short, hooker skirts.

Truth be told I wasn't expecting much out of situation, but she's hell bent on carrying a conversation with me (actually pulling up a seat next to me, even violating that personal space area). I feign juuuust enough interest to maintain said conversation. It drags on. So finally, club is approaching closing time. She's still talking to me, and start throwing hints that she may be too drunk to drive home (she wasn't TORE UP slobbering drunk or anything...but a bit tipsy). Then she suggests that I follow her home, to make sure she gets there safely.

Mind you, when it comes to women, I'm the no hint gettingest mf'ker walking the entire Earth!!! Women can't be subtle with me. They have to pull my dick out and start sucking it for me to get a hint that they want to do something

[Woman: after many failed attempts to flirt, pulls me out and starts sucking.

Me: Ohhhh, you wanna mess around huh......ok, I see where you're going with this!]


Oh, but on THIS NIGHT, I was a complete 180 of myself. I KNEW EXACTLY WHERE SHE WAS GOING WITH THIS!!!

I found my cousin, dragged him to the car, and was like, COME ON, MAN!!! WE GOTTA GO!!! BOY, COME ON!!!! I'MA LEAVE YO ASS IF YOU DON'T HURRY UP!!

(The things we do for pussy, I tell ya)

[I didn't want to lose track of her, and have some other fucker end up with her]

We follow her home, I drop him off, and head over to her place.

I end up TEARING THAT PUSSY UP for for the next 2-3 hours (wee hours in the morning, after club closing time). Mish, doggy, cowgirl, over and over (she's one of those moaner/screamer types, too, as it turns out). We started off using a rubber, but not long after we ended up going raw, completed with me cumming deep inside of her by the end of it.

Talk about a night to remember, one that started with me not even wanting to go out at all.

This was the first a few encounters between us, before drifting apart and moving on in life.

Now that I think about it, it was kinda like winning the lottery.
KitchenAid's Avatar
I debated about whether or not to share this event, because I figured to some it would seem too good to be true, but since it did happen, I don’t care is some people don’t believe it. It still ranks at the top of my “highlight reel”. As such it’s still crystal clear in my mind; trust me, my imagination isn’t good enough to make this up! Many, many years ago I was in the military, stationed in California. I was a member of my division’s MWR (Moral, Welfare & Recreation) committee. There was a woman on the committee that somehow always drew my attention. She was very light, almost pale skinned with red hair. She was average I guess, in my opinion there was a better looking woman on are committee, I had fantasized about. Nonetheless this one woman, we’ll call her Nadine; there was just something about her. I couldn’t identify it, but I could feel something when she was around. She always seemed to almost flirt with me often.

One year, our committee had the day off to set up for the Divisional Spring Picnic/Party. We rented a keg trailer with taps and had cases upon cases of soda donated that we had to ice down in coolers. Being California, everyone on the committee and other volunteers were dressed in light casual wear, shorts, T-shirts, etc. We ended up not having enough coolers. Nadine offered the use of two extra large chest coolers her husband had in the shed. Great! She asked me if I could drive her home so we could load them up in my pickup. I said sure, let’s go get them. We made casual chit chat about the event, volleyball and softball tournaments, etc. She lived in base housing about 5 minutes away.

We arrived at her house and she told me to park under the carport to make loading easier. I turned the key off and she invited me in while she got the key to the shed. Initially I thanked her, but told her I’d wait for her outside. She told me that she wasn’t sure where her husband kept them so it may take her a few minutes and offered again. This time I accepted. We went in and she showed me to the living room. I sat on the couch while she went to the back of the house, presumable to search for the key. After a minute or two she came back out, barefoot and in only her T-shirt. Before I could think of anything to say she straddled me on the couch and shoved her tongue in my mouth. I could feel her unrestricted breasts pressed against me. I reacted I think the way most men would have. We began making out with deep passionate kisses. My hands went to her ass where I soon felt that she wasn’t wearing any panties either. The bulge in my shorts began to grow. I began to reach around and play with her surprisingly moist and shaven pussy. After a few minutes she began to moan, while gyrating on my lap. I started fingering her making sure to tease her erect clit. She switched from French kissing me to sucking my tongue before sitting up abruptly, staring deep into my eyes and saying “take your shorts off!” She hopped off me, and I kicked off my shoes and in one swoop pulled off my shorts and underwear. Nadine got on her knees between my legs and engulfed my now swollen cock.

Now, in one respect, I’m only slightly above average but my thickness makes up for that. For that reason, throughout life, I’ve only had a handful of really good blowjobs with some great deepthroating. To this day, Nadine’s work ranks among the best I’ve ever had. She worked my cock with just the right speed and suction. Her eye contact was amazing, almost as if to say “feed me!” She worked my cock for about 10 minutes before switching to stroking me while she took my balls in her mouth. I remember sitting there with my head thrown back thinking “What the hell am I doing”? Suddenly she stopped. I looked at her and thought “Oh shit, what? Was that a car door?” She stood up and straddled me again guiding my rock hard cock into her wet pussy. She started thrusting and bucking. I could see her erect nipples pointing through the shirt. I wanted to suck on her tits so bad! I worked my hardest to pull her shirt up and over her head. I sucked on her tits while she grinded on my cock. She began breathing heavy, then moaning. She arched her back further shoving her pale but plump tits in my face. Her eyes were closed, and she began to shudder a bit. Her face started getting flush with color and she rode me harder. Then she said “Make me your bitch!” Oddly enough (I thought at the time) my reaction was to reach up and wrap my hand around her neck. “That’s it, ride that cock baby” I told her. “Yes, yes,” she moaned. I began to pressure the sides of her neck just a little. Her face was getting very flush. She began screaming “Yes, yes, yes!” and gushed all over my cock. “That’s it baby” I said as she began to slow her gyrations. I released her neck. Her eyes looked almost glossed over. She looked at me and said, “Pound me from behind, make me your bitch!”

We quickly re-positioned, her on all fours on the couch, me with one bent knee on the couch and one leg standing on the floor. I didn’t hesitate to slip right into her. I started thrusting into her while slapping her pale skinned ass. I swear the smell of sex was in the air making it all so…..primal. Her breathing pattern changed again to deeper more deliberate breaths. That drove me to grab her by her pony tail. I leaned back just a bit to thrust deep and upward while fully extending her neck as I pulled her hair. She squealed with every thrust. I fucked away at her for a few couple more minutes before releasing her hair. I was in full primal mode now. I thrust her head down to the cushions face first and grabbed her wrists, pulling them back like reigns on a horse. I shoved myself as deep as I physically could into her. I started pounding her hard and fast, my balls slapping against her clit every time I buried my shaft. She began moaning loudly saying “pound your pussy Daddy!, pound your pussy!” That was like adding fuel to the fire. I don’t know if it was possible to pound her any harder, but hearing her say that sure made me want to. Once again she worked up to a trembling orgasm, her pussy contracting on my cock as she came. That feeling pushed me over the edge, “I’m going to cum!” I blurted out. She leached forward uncoupling and spun around. Once again she took me deep in her mouth. My nipples were tingling as I held the back of her head and exploded down her throat. She made sounds that were part gagging and part gulping but never stopped sucking. After she emptied me she left slouch back into the couch. I felt light headed. She leaned against me for a couple of minutes before gathering her shirt and heading down the hallway. She brought me a hand cloth and went to get dressed. I wiped down and got dressed.

We did end up bringing the coolers back, we were gone about 40 minutes, but nobody seemed to really notice. The picnic was a great success. Late in the afternoon Nadine came up to me and said “I’d like you to meet my husband Jim.” She introduced us. I thanked him. I said “Thanks Jim for the use of…… (my mind said “your wife” but my mouth said) your coolers.” All the while knowing that her scent was on my cock and my cum was in her stomach.
Don't know about strange but fun and funny.
Was in New Orleans Monday night, picked up a hot thin ho with pure ghetto attitude. After drinking a few headed back to my room with couple bottles. She said she wasen't a pro but for a hundy she was game cause she "had been needing sum dick". Started out great she was a really good fuck hair pulling, ass slapping, moaning etc.
Between the blue pill and a couple bottles, we fucked on and off for bout 3 hours.
Tuesday night lying in the room I call her up:
me - waz up you busy wanna come on over?
her - naw my shit broke
me - oh you on the rag
her - no dawg it sow
me - naw...for real?
her - I can come suck your dick for fifty
me - how bout that booty for another hundy?
her - on my way!
I popped another blue pill, we drink when she got there.
I rolled on that ass until she tapped out.
I called her today at lunch time:
me - what up?
her - i ain't coming back. lose my number...my pussy and my azz hurt. shit now i can't make no money
me - i thought you said you wasen't a pro
her - i lie
me - ight den catch you next time... she hung up.
I just got a text from her "my cousin says she needen sum dick. I told her she best go somewhere else but she don't listen where yat?"
Hurricane Harbor in the bathroom stall
Slam bam thank you ma'am. Wish it had been be Tara. I've had some great wet bathing suit encounters too ��
  • greko
  • 11-09-2018, 03:38 PM
Family restroom in Central market
Slam bam thank you ma'am. Wish it had been be Tara. I've had some great wet bathing suit encounters too �� Originally Posted by Tsmokies
Jules Jaguar's Avatar
Idk about the strangest but I know what the funniest was. Years ago I did a duo with daaaaaman and a girl that’s no longer around. She was one of those dumb “don’t get cum on or near me” type of hookers. It was super annoying to both of us and she was clearly bsc so I was ready to get the hell away from her.

She was sitting on his face and I was doing a bj when he got ready to cum i shot it all over her on purpose and acted like it was an accident.

Him and I both got a kick of seeing her squirm.
billdwyer18's Avatar
Idk about the strangest but I know what the funniest was. Years ago I did a duo with daaaaaman and a girl that’s no longer around. She was one of those dumb “don’t get cum on or near me” type of hookers. It was super annoying to both of us and she was clearly bsc so I was ready to get the hell away from her.

She was sitting on his face and I was doing a bj when he got ready to cum i shot it all over her on purpose and acted like it was an accident.

Him and I both got a kick of seeing her squirm. Originally Posted by Jules Jaguar
Now that's a great story! Did the two of you high-five while she was cleaning herself off?
Hurricane Harbor in the bathroom stall Originally Posted by Tara Evans
What I would not give to see you in a bikini walling around there.