What's the nastiest thing you've ever done sexually that you still tingke over today?

Your story is bullshit OP, but hot nonetheless.

Once when a little drunk and posting on Craigslist I accidentally invited 2 separate guys over at the same time. But it worked out well with me fisting both of em, and all of us cumming multiple times. I even hooked up with both of them again but unfortunately not at the same time.

I hear lots of maximum security prisons let the teenage volunteers mingle with the guests.

0/10

Was Bernie Madoff a good top?

R3

This was 1960 in a Memphis prison. I was pretending to be 22. The storage room was in the courtyard. I wasn't a guest, I was staff.

I believe OP truly was a teen slut.

Dear Lord in heaven!

during senior year of high school, my best friend was fucking his girlfriend in his bed while i laid half asleep on the floor. this was not uncommon. after he finished he dared me to swallow his cum out of the condom, so i let him squeeze it out into my mouth. i know... prudence petunia.

R7, was it yummy? Was he hot?

I had a huge guy on a poz guy. Once Injnew U=U, he fucked me bareback and came in me.

Hottest fuck in my life.

That was three years ago. I’m still neg and we’ve been going strong as a couple

R5 and has the prolapse to prove it.

ass-to-mouth with butt plugs

Al Capone says thanks!

Fucked a homeless guy while he was drunk as shit. Disgusting dirty hole if I remember.

R13, yes, I'd say that you were.

R13: so you were touched by a hobo?

A fragrant vagrant in flagante

Flagrant fragrant vagrant

I was living in Texas and via online forums at the time had hooked up with this gorgeous, tall, model-fit guy. He was exceptionally hot and definitely out of my league (while I have plenty of self confidence and I am plenty handsome, I am not deluded enough to think that I am some sort of a "10"......he was). The power of being a masculine top does come in handy - alone it can get you ass that you would never get otherwise). We fucked around on and off for years, but he was pretty closeted and I just enjoyed his hole when he was itchy for dick. One day I needed some construction done at my house and who shows up but this tall, gorgeous, fit, stud that was basically the spitting image of my fuck buddy - just a few years older. One was not really hotter than the other - they were just genetically blessed siblings. Said contractor was hot as fuck and married with young kids (he was on his cell many times during the day with his wife and even the kid's school). My guess was that he was maybe 28 or so at the time. I would never "out" my fuck buddy or even draw attention to the fact that I knew this stud's younger brother, but I was pitching a tent just thinking about it. I did the smile/googly eye/staring/guy flirting with my married stud and even complimented his ass after an hour or two passed (none of this is like me at all - but I was horned beyond belief and somehow the brother-connection just had me on cloud nine). Being forward is always a risk. You have to assess the situation, but years of hitting on straight guys has taught me that most WANT to be complimented - whether they take the bait or not. He was timid at first (yet coyly eating up the attention) but enjoyed the flirtation more and more as the day wore on. As gorgeous as my closeted bottom fuck buddy was (and he WAS - model face and all), his older brother had an even bigger, plumper ass on him (fuck buddy probably had a slightly better face, brother was a little more muscular with a bigger butt).

The construction required getting into the attic and lucky me - my attic ladder/stairs were never terribly stable. He actually asked me to hold the stairs behind him as he stepped half way up and used his flashlight to take a look. That ass was on full display in those painted-on-jeans and I was literally feverish. I grabbed his calves to "stabilize" him and he had no reaction whatsoever. I was really sweating the decision to move my hands up to his thighs but went for it (taking my time - let a few seconds go by first). Finally I told him yet again that he had a great butt. He seemed put off this time and went both silent and very stiff. I took the hint and removed my hands from his legs. Talk about sweating bullets, I'm 6'1" myself but this stud was taller and more muscular. At the time I wasn't thinking about fighting him but rather the embarrassment of interacting with him for the next few hours. He broke silence after what felt like hours (likely only 60 seconds of so) and asked me in a very low/quite voice to place my hands back on the back of his thighs for "support". He then timidly asked why I complimented his butt and not his crotch. Both dizzy and relieved, I told him. We proceeded to have a very bizzare and ridiculously hot conversation about gay sex - which included rimming. The entire thing was a very awkward and very delicate dance - but he was ready to tango - kinda...maybe.....no....yes... I finally just asked him if he had ever been "kissed on his butt". The terminology sounds stupid, but it was hard to describe to this guy and I didn't want to scare him off any more than necessary. Whether or not he had seen any straight porn that involved rimming, I have no clue - but he seemed both ignorant and quite interested. We never verbally agreed to anything, but he unbuckled his belt and unbuttoned his jeans. By now I was grabbing a handful of clothed ass cheek and took his lead. I tugged the tight fabric down (his ass was huge and the jeans were tight). He was wearing Hanes briefs that were warm, moist and sweaty in the crack area. I quickly tugged them down and over those very plump, sweaty, pale and almost hairless ham hocks - exposing his sweaty and musky man parts - crack, taint and a glimpse of the big balls swinging up front. When he pushed his big butt right into my face, he didn't arch his back like an experienced bottom normally would, but just stuck it straight out and almost lost his balance. The scent was intoxicating - like he had showered thoroughly that morning and then had been working and sweating in those tight, confining jeans most of the afternoon. I grabbed both giant buns and spread them apart roughly (they big and meaty and hard to open) - revealing a tiny salmon-tinted hole surrounded by a sprinkling of brown pubes. The scent was like a drug - man sweat and musk with nothing dirty so I dove right in and started eating him like he was my last meal. He wiggled a lot and let out a few audible gasps/moans.

My entire face was covered with his smell and my tongue wrestled his tight little hole until it gave entry. I couldn't get deep enough inside him (although, it was hard to do). At some point, I pulled out of his hole and started tonguing the bottom of his huge balls which sent him through the roof..literally. He squealed and then sat back on my face even harder and mumbled "more". The entire oral scene only lasted 5 minutes or so. When he started jerking while still ass out and balancing on the ladder - he came..well...quickly. His cum splashed all over the carpet and onto his tool box. "Damn" was his one word response. He froze and kept the same pose for an awkward 45 seconds or so. I started jerking myself while sniffing his exposed butt and was able to blow relatively quickly also. I gave his crack an extra kiss or two and pulled up his briefs for him. We didn't say anything after that. He just got back to work. When he left, he shook my hand, grabbed my arm, gave me a wink and shot me a huge Texan grin and that was that. I never heard from him again, never called him and never pestered him in any way. This 5 minute rim job goes down in my sex history as ranking up with the hottest anal fucks that I have ever thrown. I asked my fuck buddy if he had a brother (he said yes) and left it at that. Neither knows a thing about the other - at least not in relation to me and something about that makes it even more exciting. Dirty little secrets - and sex with two of the hottest brothers that I have ever encountered. Great memories..

After R2 fisted both of them at the same time while calling them “my gloves”, he stuck one foot up each ass and then walked around wearing them like slippers. Motorists and other pedestrians were rather startled to behold such a sight.

Only in Texas is my mantra. About 2 years after my encounter with brother2, I was having a beer at Hoppin' John's, my local, and sitting at the other end of the bar is a hot silver fox, tall, model-fit. Just my type. At first I thought it was my fb, but then I realized this guy was definitely older. Long story short, we hooked up.

This guy had the moves 7 ways to Sunday. I'm pretty experienced, but he knew stuff that had me screaming with apleasure, like the Golden Spike (think about it). Afterward, as we lay soaked in sweat and cum, we got to,talking and he started to tell me about his kids. You guessed-- he was the father of my two hot brothers! I had the whole family! The asses of Texas were upon me, sure as shootin.

0/10

Not surprised, R22. But from here on in, no getting pissed off when the rest of us refer to Southerners as cousin-fuckers.

As a teen I once volunteered on a handyman crew. I would go out driving with the hairy mature handymen in their rough, beat-up old Ford trucks. They would drive to remote stretches of road or to the back of quiet city lots, unbuckle their belts and unzip their jeans and make me blow them.

That's awful. And no matter how many times they drove you to remote spots, they always made you blow them. Something similar happened to me, so I know how a guy keeps figuring that the next time it won't go down (heh) that way. So you keep giving the guys another chance not to force you to blow them.

I used to accept money from older guys for sex

My FWB buddy, who was a police officer, suggested we get on both ends of his night stick. We used lots of lube. It was a bit difficult to get the motion down, but once we did.... I ended up topping him to finish the experience.

The only other experience was when I gave a hand job to my boyfriend while we were swimming in Hanauma Bay. We laughed that he was feeding the fishes with his cum. We wondered if anyone could tell what we were doing. It wasn't like we found some remote part of the park.

Hmmm...No.

[QUOTE] This was 1960 in a Memphis prison.

We now have verification that OP is older than dirt.

r8 i don’t remember how it tasted, but he was a tall, athletic skater and to me was quite attractive. light reddish-brown hair everywhere and always smelled like bar soap, even “down there” as the anti-redhead troll would say.

i blew him for the rest of the year, then left for college. he showed up at my house a time or two when i was home the next summer. now i only see him on social media under an assumed name... hiding from baby mama.

When I tingke over it, I tingke over when I let Huffenpuff violate me with that flute. That was some nasty shit we did.

Like I'd ever post it on DL. LOL.

I love how almost all of DL's past sexual experiences featured tall, lean and/or muscular model types.

r34 are you joking? the one i referenced above absolutely was. then once i got to college i discovered stocky gays. “nasty” veut dire bien des chôses...

Sordid.

Fucked a FWB,then stuffed a Heineken bottle up his ass and drank the beer straight from his hole

Did it have a frothy head?

I cleaned the toilet with my roomates toothbrush.

When I was a 22 year old twink, I worked at a theme park and would flirt with a hot, muscular, black Park Attendant (swept up the side walks) who was probably late 30s. There was an upstairs storage room above on of the food concessions that I was assigned to organize one week. I let him know I was up there and he came up and we were all over each other. He was over six feet, the most muscular body I'd ever been with and a huge curved dick. I let him fuck me on an old wooden table in the unair conditioned attic like room in sweltering summer heat. He carried around condoms in his park uniform which made me think he got a lot of action. He made me cum, came himself and then left me as a sweaty mess, lying on that table. I tried to get his attention again but he must have lost interest after he turned me into a horny slut and got what he wanted.

Ahem.

I fucked this young guy once in the backseat of his car in the parking lot of my apartment - broad daylight. We barebacked. Without showering, I went over and met a fuck buddy an hour or so later, fucked him bareback as well. I'm not proud of the risky bareback side of it, but it was still very hot at the time.

We know. We got the alert.

Let a guy lay down a line of coke on his condom covered cock and the shove it up my ass.

After a few drinks, I went home with a guy. Before we got deeply into anything much, (thank God!,) I finger fucked him for about a minute... and he shit the bed.

I left.

Well, shit the bed!

Those nursing home patients can have unpredictable sphincter control, eh, R45?

I prefer being a top but I learned how to bottom 14 yrs my guy and I take turns. Nasty dirty? I went through a fucked up break up and I was popping xanax and ritalin and getting horny. I was on some hookup site...manhunt I think. I got a bunch of offers and dudes came and went for about a month. I'm blond and my cock is a grower and shower. about 7in thick and a dark blond bush. Anyway, this really fucking hot guy kept messaging me begging to fuck me. I was like....man, NO! A shot of tequila and a crushed up snorted ritalin had me saying...safe only and if I don't like it you gotta stop. So he comes to my house I met him in comfy underwear with holes in them. we complimented each other. I told him I don't really kiss. He didn't either so it was cool. So, he had a hefty cock like me and offered his ass next time. First time I heard the term "you have an amazing perfect bubble" so, first time I got eaten out. man, his whisker stubble raking accross my pink was so fucking cool. He started slow with a special numbing lube. About 40 minutes later he blew his load on my dick...and he swallowed mine. (I think I actually screeched) It was the hottest 2 night stand I ever had. He was an amazing teacher, tall manly and no shaved bush or nothing like that...he was showered and he was a lot like me when I'd hook up with a sexy as fuck bottom. I fuck like a rockstar. I can't do mercy or pity fucks or blowjobs. I just can't. I gotta be really into a guy. So it was sweaty, he taught me how to recieve (ie push your bum muscle out a little as you feel my mushroom popping in and start contracting your bum as I go deeper.

I got pounded by a Bangladeshi sewer employee, inside a port-o-potty.

Bangladeshi is hot. Working class is hot.

The port-a-potty is a deal breaker. Mos def.

[quote]When I was sixteen I volunteered at a prison.

Wait. What??

You expect us to even believe that? People do not “volunteer” at prisons, let alone minors. Never mind that no visitor would ever be allowed to be alone with prisoners without supervision.

This is incredibly stupid trolling.

R51 meet R4.

Thanks.

I met this "famous" person on Grindr, we hooked up at a motel and things were cool until he packed out disco lights, a portable massage table, a s/m mask and overdosed right in front of me while I was still fisting him.

I was really into random sex with strangers.I grew out of it ....the thrill was gone as they started revealing things about themselves that i disliked. Druguse,random violence/crime,deadbeat parenthood,alcoholism....folks really do have alot of baggage once they hit 35

I once judged a guy so hard he cried...It was electrifying!

Better shape up, R55.

DOX TRYORY

OP just wants to use your story against you in an unrelated thread.

Bump

tingke? Injnew U=U?

i let 3 guys who were practicing hitting a softball shove a baseball bat up my asshole one hot july night in 2011.

I picked up 3 Honduran guys from a bathhouse and brought them home. We fucked and did blow all night.

So this is just going to be creepers’ chance to foist their purple, amateur erotica on all of us?

I don’t need r20’s 3,000-word essay.

R62 forgot to put the husbear in

[quote]I once judged a guy so hard he cried...It was electrifying!

YOU ARE DEPRAVED, LINDA

I slept with someone who admitted voting for Dubya. I took a Silkwood shower afterwards.

[quote]tingke

Past tense "tungke"?

Injnew U=U?

to tingke, to have tingked, to have been tungked

I let a guy piss in me after he was done fucking me.

Can we get this going again?

I let a guy fuck me raw in Griffith Park while about 5 other guys gathered around and watched, jacking off, one them fucking me after guy #1 was done.

R71, are you Shawn Mendes?

When I came to the big city for college I was a horny gay virgin. I started going to these fascinating things called adult bookstores, putting tokens into the machines and watching real naked people having sex (we didn't have cable where I was from).

I blew a couple guys through glory holes whom I chatted-up in there.

Whenever I've told someone that, they look at me like I'm some kind of sleeze, so I stopped confessing it.

It was very innocent. I guess you had to be there.

O M G you are all a bunch of whores.

Mary! You all are vial. Hand me my fainting couch.

I was visiting New York for a long weekend and met a guy online for what was supposed to be just a hookup.

Got to his place. His picture did not match his current physical appearance. Also, he was wearing a diaper and started immediately saying things like "you're not going to rape me, are you?"

So I went back to my hotel ASAP. That was the first day of my trip. It really killed any mood to fool around.

[quote]You all are vial.

Oh, dear!

3-way Injnew U=U in Timbuktu with 2 horse hung librarians.

I heard horse hung and ran right back to the thread.

4-way ajubba in Kenosha, post-prandium, marsupial-style

I once viciously mocked a tedious A-gay to his face until he cried, the sight of his tears washing away his foundation got me so hot!

I’ve done so many nasty things that nothing gets me tingly any more... except that handsome muscular hunk in a bathhouse years ago made me cum three times during a visit.

First he sucked me off and I came in his mouth . Then I hooked up around the bathhouse and then went back to him and barebacked him. By the third time, also in his ass, I doubt I had much cum left. Even years later, I think he was the sexiest man I ever fucked.

Laid in bed from fri night until monday morning fucking over and over again. We didnt bathe,we barely ate,we just fucked.Come monday morning I was a fucked out,wrung out 6 ft tall gaping asshole. It hurt to shit for days afterwards. The gentleman in question was a deranged psychopathic hustler who made my life a nightmare for 1 1/2 years,but I just couldnt give up that dick. He had salt and pepper hair and cobalt blue eyes . 9 inches and a southern accent you could cut with a knife. I was completely addicted.

Being a bottom sounds painful and also kind of sad and scary.

Got fucked by a hairy, smelly Italian hunk in a toilet stall, thick, veiny cock it hurt like hell and took a while to stretch my hole to accommodate all of it. I was so turned on I licked the toilet bowl seat while he raped my hole.

I tingke.

R85 forgot: rock-hard, uncut, 10 inches, geyser-spurting

I hope I haven't done it yet.

blew a random European at heathrow airport in one of the family bathroom's while i jerked off and came on the floor.

I used to vote republican. Dirty guilt

I kissed a boy once! Don’t tell Mother!

Back in the 80's I was a renowned sex fiend, albeit one with a limited repertoire, I guess the nastiest thing I ever did was at a huge private glory hole club in New York City. It was actually called "The Glory Hole". An old multi-story warehouse type building, I think it was on 11th Ave. They had each floor packed with all sorts of booths & rooms. The action didn't get hopping usually until after midnight. One night I was there and was on a particular tear. as the libido was raging. Got there around 12:15am and by 4am I had finished off 12 guys. Yes, it was nasty, but I still remember it as great fun.

Are you the real guy that stomach pumping full of cum story is about R92?

Did you need poppers or other drugs to keep up the stamina through a dozen blow jobs?

Sorry, no R93. Not me. And besides I learned how to spit long before that night.

No R94, no drugs or any other substances involved. Just raw lust.

I sucked off a hot homeless methhead in a dirty bookstore in Portland. Not very bright. Yes it was hot.