Tell me about your wildest hookup experience

[cfsdbf5010]

Was in California at a famous Tiki Bar, Trader Sam's, near Disneyland. I was seated aside of a gay couple, the two were, probably 15 years apart in age. I sat next to the younger dude, who was probably in his late 40's, I was 55, this was two years ago. Super cool guy, dude with him, maybe a sugar daddy, IDK. The younger dude and I were chatting, he has a few drinks in him, we somehow got started on talking sex. I wax my cock and balls, have an incredible woman do this for me, (sometimes a little extra when she's done. She's usually hornier than hell and either sucks me off when done while she takes care of her self, was telling him this and he was beyond hard in his jean shorts, he wanted to see this.

I was reluctant due to his dude, however he seemed to care less, so I went to the BR, and he closely followed, came in, locked the door! We had the room to ourselves. I dropped my shorts and jock strap, it was a NP jock, super hot, he came over, and yanked my jock off, my cock flopped out, before you know it, his shorts are off, BR was spotless, he was a bit taller than me, he had an awesome cock, 3/4's hard, well I just got down and took that big cock in my mouth, shoved him in balls deep before he was completely hard... He got hard as a rock, precum spewing, I really worked him over, no hands, and I felt him throbbing hard, he was ready to cum soon, then there is a pretty firm knock on the damn door, so he zipped up, I zipped up, this guy kept knocking, so we washed our hands like we were in there for the right reasons, casually walked out pretty discreetly.

Went back to our seats both had not unloaded, talked more sex, what we liked which was pretty similar, I'm bi, and just got out of a pretty toxic relationship with this psycho, who though was nuts in bed, regular pegging, occasional other chick, her pegging me, the other sucking me off, a bunch of other stuff, anyway this is too long already.

The core of the apple is that the dude that was knocking on the door, who was pretty hot as well, and super hung in his board shorts comes over to us, told the two of us, he kind of knew what was going on and he was their to join it!

This guy had a room in the hotel, we went up to his room, the guy I was with left his guy at the bar, and in his room we took turns sucking each other off, two on one until the three of us came, the other guy was huge, my hookup and I worked on him for 15 minutes until he popped, and gave each of us our fair share of his load.

When my time came around I was never sucked off by two guys, it was incredible, both sets of lips and tongues up and down my shaft, I was ready to cum in 5 minutes and the dude I was with grabbed my hips and kept me in his mouth until my load was long gone and started to get soft...

Got dressed and went back down to the bar. Long story, but never expected!

 

[snakeeater1]

I was traveling down an interstate one time just about dark, playing with my cock and listening to music, when I came onto a rest area advertising Rest Rooms. I had to take a pee do I pulled in and parked. Just as I was starting to pull up my pants and put my cock back in, a big rough looking guy walked past my car and glanced in the window. He kept on walking, but I knew he saw me!

As I came out of the john he was standing there and as I turned to leave he walk along beside me. After a few steps he said “you know I saw you back there in your car, what were you doing jackin off?” I must have looked kind of embarrassed and said “yes, I sometimes play with myself out of boredom and to stay awake.” Then he says, “did you ever get a blow job from someone seeing you?” I said no and kept on walking, then he says did you ever give a blow job to a guy at at rest area? I stoped and I said no, why are you aaaking?asking

 

[snakeeater1]

The rest of the story above (look up)

 

[txboyalone]

Contacted a guy via CL one time. Listed mutual oral and maybe more. Sounded like what I was looking for. He gave me the address of his apartment. Told me to park in the front and walk around to 402b. I left the office at 2:30. Figured would be a quickie and be home by 5:00pm.
Arrived around three Nice garden apartment complex. Knocked on his door and he opened it, wearing a kilt and nothing else. He was an older gray haired guy but in great shape. Tanned and nice crop of grey hair on his chest. I was 32 in good shape with a wife and baby who didn’t know I was bi and in the closet. So I was alway careful and some what shy.

He dropped the kilt and I started in on a very nice uncut 7 cock with good girth. Wow he was fun to suck. Will I am sucking him he manages to get my cloths off and is playing with my low hanging balls and my dripping 7”
cock.
He gets close and says. Wait let me do you. Sits me in a leather barrel chair and starts sucking me while his finger goes exploring my rose bud. He then starts licking and sucking my nuts and then pushes my legs up and is tongue fucking my hole. He is good at this and it feels fantastic.

He ask me to lay on the floor with my ass in the air and he goes back to tonguing my ass hole. I am drooling precum everywhere and he is jacking my dick with it. I am thinking I am ready for him to fuck me when there is a gentle knock on the door.

He says oh that’s a friend I ask him to join us.
What the fuck I said. He is rubbing my ass with one hand and stroking my hard on and assures me they are discrete and fun guys. Guys? Plural.?

George comes back with two guys about his same age 60+ to 70 and in good shape.
They skin off their cloths and are pretty hot looking with their bouncing hard ons.

George goes back to eating my ass, while one guy offers his dick for me to suck And the other gets on his back and slides under me and starts sucking my cock. About this time George replaced his tongue with his well lubed cock. I had only done anal with one friend but was not very expereiced.
His dick slide right in with no discomfort at all. Afterwards I though probably because with sucking one guy and get sucked by another it was kind of sensory overload.

George was going after my ass and it felts really good but you could tell he was having problems physically on his knees.
He stopped and said, “Mark I have a sling I the other room would you be willing to get
In it so I can stand up.” What the hell sounded like a good idea. I have never been in a sling but knew what they were

George led me down the hall with the other two and we went into a room that looked
Out on the garden. The sling was in the middle of the room and had receded lights accenting it. A little strange. The three guys helped me in. George raised one leg
Up and put my foot in the strap. Then he buckled a lambs wool covered strap around my ankle. He winked and said that’s so you foot doesn’t fall out during intercourse. Then they did the other ankle. They laid me back and made some adjustments so my head laid back and one guy I think his name was
Tim held his cock out for me to suck and the pulled out and said that looks right.

The only thing that keep me from throwing
a fit and bolting was George was still sucking my cock and finger fucking my ass.

Then the guys said here this will be more comfortable for you and they bound my wrist to the webbing.

I looked over and one wall waa covered in mirrors, i was a little shocked because i looked like the Christmas Turkey all trust up.
Then the boys got series. George started fucking me. Tim had his cock down my throat and the started swinging me with George driving me down on Tim’s hard cock.
It actually felt pretty good and I was tingling all over. The other guy comes over and puts clamps on my nipples. Ouch they hurt but I was kind of in sensory overload by now.

Then he started messing with my cock and balls. I couldn't see what he was doing it felt like he was attacking a cock ring around my balls.

George was getting close and after a couple of deep thrust came hard in my ass. Wow that flats great. As he pulled out the other guy put his cock in and started fucking me hard.
With out a cock down my throat I looked down and there was some kind of cock ring around my cock and balls. Goerge was rubbing my chest and started attach wires to the nipple clamps and the cock ring. I then noticed he had a Tims unite and I ask what’s that far. He smiled and said oh it will be a better experience for you Mark.

Then the other guy pulled my head back and put his cock in my mouth.
I though I heard the door bell but really between the guys using my bottom and the
Guy shoving his cock down my throat and the electric tingle between my nipples and my cock. I wasn’t sure what was going on.
After my friends came in me In looked over and there were three more naked old men.
I never was sure how many loads I took that
Afternoon. I am sure everyone got off twice at
Least. Aroud 7 pm. They got me out of the sling and helped me into the shower. They washed me off and dryied me off. They insisted a put on disposable underwear before I got dressed. One guy winked and said you’ll be leaking for a while.

George walked me to my car and said,I hoped you had fun.
I felt abused but at the same time oddly satisfied and sated.
Later in life I have longed for an afternoon like that, but not to often.

Mark.

 

[Hornypossum]

My wildest hookup was more than a decade ago.

I was browsing on some hookup site or another and came across a profile for someone rocking a big, thick 8.5" (22 cm) cock. Beyond the drop-field stats like age, sizes, and the indication they wanted to top, all their profile said was "I'm trans". Their skin was a dark ebony, and the only thing thicker than her natural curves (no breast implants, and hormones hadn't yet established very pronounced breasts) was her beautiful cock with its blunt head, uniformly thick shaft (not much difference between the shaft and head either) and slight curve to her left.

For whatever reason, this represents a body type that SERIOUSLY gets me hot. We agreed to meet, talked ground rules and boundaries, and then she rocks my world with a question: "Would you mind if my boyfriend joins us?"

I asked if she had pictures and she directed me to a profile. No face pictures, just a reasonably fit black man about it age with a dick as big as hers, only straight as an arrow who made no bones about exclusively being a top.

Nowadays, I'd assume I was being scammed. Fortunately, younger me was incredibly turned on and went directly over to their place, an old trailer in a park on the edge of town. I was incredibly nervous when I arrived, and the guy sitting outside the back door eyeing me with suspicion and a bit of anxiety didn't calm me down. After verifying the address, I got out and greeted the guy quietly; he was the boyfriend and seemed only a little less nervous than me.

Inside, we were all standing awkwardly for a moment as they looked at each other and at me. She reached over to him and felt him up, and then fondled her already burgeoning erection through her thin pajama bottoms. It was all I needed to break the ice. I knelt down in from of her, she pulled out her gorgeous boner and I took it with both hands, briefly amazed by the hot, thick mass of cock now in my hands. I started licking the smooth, warm head of her member, then worked my tongue down her hard length until I could lick her clean-shaven balls a few times.

I then worked back up, sucking little spots in tongue-heavy kisses until I got back up to that splendid head. I ran my tongue around it in orbits, licking every inch before choosing my lips over her and sucking that whole head, alternating suction with rapid flicks of the tip of my tongue before putting her back in my mouth to close down around her while I slid my tongue back and forth under her girth, trying to get as much surface area if my tongue both on her and simultaneously moving as possible. Just as I was wondering if my efforts meet with her approval, I felt get manicured hand rest on top of my head as she released a soft, approving moan.

Now encouraged, I decided to find out exactly how much of her beautiful length I could get into my mouth and throat. Remembering an old porn video where the star was coaching her friend in how to properly deepthroat the star's husband's above average dick, I pushed my head down, stuck my tongue out and swallowed. I got most of her in me, then pulled back because I didn't want to stop working that beautiful cock while I figured things out. A few more strokes in and I was getting her nearly balls-deep. I have once or twice, but either kept that truck hard dick in my mouth or pounded right back on it.

I went in again, and this time I felt that pretty hand wrap around my head just before she shoved my face all the way into her hips. I gagged, but fought through. She started throat-fucking me fairly slowly, and eventually I grabbed her ass while I was all the way down and stuck my tongue out as far as I could, trying to lick down towards her balls with her meat shoved all the way down my throat. I didn't make it, but she held me there while I moved my tongue as much as her girth allowed, and repeatedly tried swallowing in hope of at least letting her feel the movement in my throat if but holding off the gagging. As I started to gag she yanked my head off her rigid dick, plunging in deep a few more times before yanking my head off her one last time, letting me briefly glimpse her raging hard-on, glistening and slick with the sit and mucus from my throat before turning my head towards the very erect meat of her man.

He was waving his dick at me, inches from my face, so I jumped right on it and started sucking him for everything I was worth. After a couple minutes of this (I think, I wasn't exactly keeping time) they told me to get up and he laid on the bed, head on the pillow and legs spread while he waved his big big and smiled wryly at me. She was opening a condom. "Come and get it", he said.

I got in all fours on their bed and started trying to suck her man's soul out of his cock. Behind me, I heard her deftly unrolling the Magnum onto her hardened rod, which she'd just opened, all in long nails. I didn't think too much on that feat, as I was also enjoying the Moana I was getting out of her man by continuing to test the limits of my throat. I was incredibly turned on already, and hit the roof when I felt the thick head of her magnificent cock, covered in lube, rubbing it up and down between my cheeks. It stopped, pushing its throbbing stiffness maddeningly gently against the ass that so wanted to swallow it whole. I felt one hand pull my ass cheek aside while the other guided her against me. I stopped blowing her man so I could focus, relax and let her into my ass.

It was incredible! Two huge, thick cocks using me at once had been a fantasy, and now I had a hung trans woman pushing my ass lower so she could get a better angle to pound me, all while having a perfect view of her man's face while he fucked the life out of my throat. She eventually got on top of me so she could pound me with long, hard strokes. I was damned near getting off without even touching myself when she pulled out and yanked the condom off, switching places with her guy.

I went to town on her cock; lips, tongue and throat working at a frenzied pace hoping I could get her off in me. Once her man got the condom on he went to work on my ass, starting with a few slow thrusts, then eventually grabbing my hips and fucking fast and hard when he was sure he wasn't going to hurt me, slapping his hips against my ass. After several minutes of this, through communication I was too full of cock to hear, the birth stood up, side by side, jerking off to finish. I got on my knees in front of them again, grabbing his cock first and sucking absolutely as hard as I could while still moving back and forth, his soft, fleshy bell-end cushioning the back of my thrust just enough against his steel-hard, aching erection. As he stated to moan she breathe heavy, I plunged him all the way down my throat to get his cum all the way inside, swallowing until his orgasm passed. Then I pressed the tip of my tongue as hard as I could against the underside of his cock, squeezing every last drop of semen into my mouth as I slowly pulled my head off him, using the withdrawing volume of his manhood to suck harder and harder, squeezing the cum from his urethra with my tongue until he emerged from my lips with a satisfying "pop".

After watching her guy react, it was no surprise that the lady of the house was eager for her turn. I trusted the procedure with her, relishing every wonderful inch of her until her moans reached a peak and announced she was going to cum; once again, I plunged down on her as deep as I could. This time though, I started pulling back as she started to blow, squeezing and sucking a surprisingly large load all over the inside of my very, very happy mouth.

We said our goodbyes afterwards, as we all had things to do. I met her once afterward, but this was, by far, the hottest fuck of my life. I've had several great encounters before and since, but this one reads (and felt) like porn or erotic fiction. I get off thinking about it semi regularly, and hope that maybe some of you can now, as well!

 

[Sniffademskidz]

He stood in a secluded corner of the park and had graciously eased his trousers down exposing his tighty whities undies!

I dropped to my knees and buried my face in those heavenly orbs!

The smell was intoxicating and i breathed in the life giving scent from between the cheeks of his arse!

I was already transported into another world before i yanked down his panties and began to navigate his muddy brown river with my hungry cock!