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Speak Out: What’s Your Hottest, Most Scandalous Hookup Ever?

(Photo Credits: Raging Stallion)

It’s as the title says: what’s your hottest, most scandalous hookup ever? Steamiest, dirtiest, sluttiest, kinkiest, and sleaziest—I’m running out of adjectives but you get the drift so ‘fess up, guys!

I’ve been reading online confessions and some guys admitted to sleeping with their ex-boyfriend’s best friend, their best friend’s boyfriend, while there’s one who slept with their ex’s younger brother. Others had sex with their boyfriends with their sleeping roommate was only a few feet away although there was a guy who did sleep with his roommate per se. Others confessed to sleeping with a priest (though he didn’t know until they were done), psychologist, footballer, a cop, their doctors, colleague, lawyers, professors, and frat brothers complete with lurid details. Some men admitted to fondling, brushing their seatmate’s arm, or touching their thigh to see how they would react during a plane or train ride. The men talked about doing it in a toilet, getting a blowjob in a car, of threesomes, of making out and jacking off in the lounge area of a hotel, or at the sofa in his parents’ living room. You can read their confessions here.

What about you? What’s your hottest, most scandalous hookup ever? Have you ever experienced anything similar to the ones mentioned above? One of the guys who commented pointed out that since it’s an online confession, then it must be a lie. Maybe, maybe not though I think people will most likely tell the truth on online confessions; you see, people tend to be bolder because they enjoy the veneer of anonymity online.

Thoughts? Share it with us as well as your very own scandalous hookup confessions in the comments section below.


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  1. Steph

    One time I had sex with my brothers wife’s brother , downstairs , in a wine cellar during a family reunion it was hot as hell. We always had eyes for one another and it had always been awkward around each other at family functions because we were so hot for one another. We are both masculine guys but he is more rugged and I am more refined. He wanted to fuck my butt so bad that when we finally made our way to the cellar he ripped my shorts and underwear ! It was one of those spontaneous moments and it will never happen again. Makes for a really good memory to think about from time to time.

  2. Scott

    I don’t know about hottest, but this one was definitely scandalous.

    In my 20s, I had a relationship with a married man that was strictly physical. He had an attraction to me the day we met, and after carrying on a business relationship for a few years, he decided to admit his desires to me. I was surprised, but enticed by the offer to play. One day I paid him a visit at home. I figured that if the missus was there, he wouldn’t do anything untoward. Well, I was wrong about that! While she’s upstairs shoveling snow, he and I are in the basement and he’s pounding my hole like a jackrabbit. It was exciting. I felt amazing the rest of the day.

  3. Clausen

    I was a super horny, married bisexual man at the time. I would play with men in the dark evening at a local hot springs. One night my wife asked me to meet her at the big pool at the hot springs, once I got off work.
    I arrived seperately, got undressed, ( clothing optional), and walked out into the super dark night to find her somewhere in the pool area. I could easily hear her talking with a female friend with both knew amongst the guests scattered throughout the soaking area. I snuck into the pool, unnoticed, and swam over to a hot water inlet area, across the pool from where I was hearing my wife. It was at this point that I bumped into, and could barely make out in the darkness, a familiar man whom I have played with before at this hot spring. We both acknowledged each other by furtively reaching for and fondling each other beneath the water. I was thoroughly enjoying how he stroked me into a raging hard on. I layed back into the warm water, gently wrapped my legs around his body, as he stood in the 5 feet of water, and I pulled my open thighs up to his warm belly, and secured myself against him, my legs spread around him. My 7.5″ cock were grasped gently in his hands, and he sensuously stroked my throbbing cock. We were enjoying our lustful sex, amid the other patrons in the pool, but we were sexually pleasing ourselves in the pitch black darkness, as I lay floating on my back. The stars bright in the Sky, and the cackling of my wife’s voice only 5 feet away. She had no idea I was being jerked off by a MAN, only a few feet away.
    My friend’s sensual hand job brought me to a wondrous orgasm, while I took a breath, held my nose, and leaned back under the surface to stifle my moans of hot man to man sexual pleasure! I was only 5 feet from my wife and her friend, and it was so erotic to have this man, gently massage the cum from my swollen cock. He is so gentle, so hot, so Fucking wonderful to enjoy.
    After my body stopped shuddering from my orgasm, I leaned back up to the surface, disentangle my legs for him,wrapped my arms around him, once we sunk lower into the water. It was then that I leaned my pjs up to his face while I hugged him, kissed him on the side odd his face, nibbled on his ear, and then whispered into his ear, informing him that my wife was only 5 feet from us the entire time. He whispered back, ” that is so fucking hot ! “

  4. Hotass196648

    When I was 18 I was given to a 60 year old man as a birthday present. I went to the party with the man who i met when I was 16 he was 49 ,he was the first man I had sex with. I had never met the birthday Daddy, there were 10 men there, some I have met and played with before. I am a very submissive exhabitonest bottom, so I loved the idea of being a birthday present for the 60 year old Daddy. I the party was under way when I arrived, I was wearing some very short shorts, at 18 I was slim tall and very tanned. A big bowe was put on me , I went out into the room just weariny very short shorts, the Daddy was blindfolded, I stood in front of him ,the blindfolde was removed and I was smiling at him as he got a big smile on his face. He stood up and remove the bowe, and my friend told him I was his birthday present and was his for the weekend. He removed my bowe and I kissed him,a very hot passionate kiss, he say back down and I stripped for him , nude now I have h a lap dance, removed his clothes, got on my knees and started sucking his cock as the others watched. He had a very nice 7″ thick cock. He took me to his room and fucked me , bareback, I was so horny. He was a great fuck. When he was done he took me back out to the party. I was then gang banged by the 10 men there, that weekend I was introduced to BDSM, WS, and that was my first gang bang, and I loved it .

  5. Matt

    Here goes. I would say when my wife and I went to Baltimore md on vacation. It was raining one day and her hair got wet. She looked in the yellow pages and found a beauty salon about 15 mins from our hotel. I took her to the salon and told her I was going back to the hotel to watch tv and told her to call me when she was ready. I went back to the room and called a buddy in the area that I had chatted with before on a sex site and he came right over. We had a great time!!!!!

  6. rivahdude65@gmail.com

    I was dating a guy , he was in the hospital for Chemo , huge sex drive he had , so i visited , next thing i know he and I are in the bathroom to his hospital room , going at it like dogs in heat , nurse walks in , opens the door , says OMG – long story short it was hot !

  7. Avery

    Outdoors behind a senior home, around midnight, with one of the orderlies. He was 50 or so, and fucked like a champ. We were in a small mostly secluded grove of trees. We were fucking missionary style, and he pick up my ass and fucked me pile driver style with his big cock. Delicious!

  8. parshoot

    It has been a few years ago. One of FWB buddies desired to have a birthday surprise for me at a local hotel. we arrived, after a few drinks he said “it’s tome”. I removed my clothes then he put a mask tight over my eyes. Immediately he rammed his big cock into my throat deep. After he finished fucking me me I could hear others in he room. When he snickered saying let the fu begin I felt a dick slide into my cum lubed ass. I knew it wasn’t my friend because this dick was larger. It felt so good but I felt this guy cum in my ass. Quickly another dick entered me longer but not as fat. Then another dick, another. After what seemed hours I only hears my FWB in room. He removed he blinfild hen fucked me again nice and slow. When we went to his house. Here is your surprise. My buddy gad filmed the entirety of the sexcapades. Upon watching it there had been 22 guys fucking my ass some my throat. No wonder my ass hurt for several days.

  9. Mm

    Hottest = Met a guy who was traveling past me at a hotel and had the best sex ever, like slow motion movie sex.
    Most Scandalous = Did portraits for an extended family; mom, dad, kids and their families. The son came back a few times for cock.

  10. Eric

    I Had had sex with a chaplain in a hospital. He took me down to his private room and worked me good. It was great and having to subdue my moans while he banged me so nobody heard was such a turn on!

  11. Hunter0500

    “What’s Your Hottest, Most Scandalous Hookup Ever?”

    It begs the question, “how unsatisfied are you in your own life that you need to drool over what other guys do?”

    Really, if you have your own life going on, you don’t need to know what other guys are up to.

    And really, what other guys are up to is not rocket science. It doesn’t take too much imagination.

    Do you stay at home all day surfing the Internet about what others are doing while not investing time in your own happiness or satisfaction while contacting live, real men?

    If your own life isn’t happening for you sexually (or frankly for any aspect), take a look at what you’re doing:
    – are you demanding about what you want? Not good.
    – what are you offering others? Or is it only about what you want? Not good.

    Spend time getting to know quality men, where their superficial traits are inconsequential. That’s a good investment.

    And be ready to offer other guys something of quality.

    Why do you need to know about other guys “Hottest, Most Scandalous Hookup Ever?”
    Answer: Because you need to get out into life and be a quality guy who finds quality guys.

    • WhyYOUhereThen?

      You never cease to amaze me. No matter what, you always put your long two cents in, usually to say that what others think, do, or say is wrong. Question is, why are you always responding if you don’t like the question or aren’t interested in participating? You know, YOU ARE ON THIS SITE also, so tell me you don’t have interests and that it isn’t your RIGHT to think, feel, read, or do whatever you want … if THIS isn’t your cup of tea feel free to move along, NO need to tell us your thoughts, and as for offering quality, you are so negative towards many of the fine gay men here, you really should take your own advice and offer QUALITY over all that quantity you spew.

  12. Cumpup39

    Getting fucked in the hot tub by my then girlfriends brother! Her, her sisters and mom were just a few feet away as I slid my ass down his hard dick and took an intense fucking! He filled me with his load and I was slipping off of his big dick as the door around the corner opened and I was sitting across from him as the girls got back in the tub.

  13. Steve

    I saw a cute guy at the tire store. …made eye contact and went to the mens room. He came in a few minutes later…showed his nice hard dick..i sucked him as soon as i saw it but knew we didnt have any time…so we exchanged numbers and left. He called later that day and we met at his apartment…the first of several meetings. We dated for several months.

  14. Nick D

    Most guys in here will call Bullshit, but many years ago I was a bartender in country bar in a medium size city. After closing a bunch of us would get together to have a drink. One night nearly everyone had left and as I went to leave I ran into a scruffy hot guy in the parking lot. He was a little drunk, and when I asked him if I could help he asked me to take him to his hotel, so I did. He asked me in and as soon as we went in, he started stripping. I didn’t think much about it till he grabbed my cock and started deep kissing me. I fucked him twice and he fucked me once, risky and RAW. Heat of the moment. It was a hot night. I drove home as the sun was coming up. Next night at work one of the gals said Ty Herendon left his rental car in the parking lot. He was new and I’m a metal head at heart, so she showed me his pic. All I said was Oh. Never let on what happened as I wasn’t out. That’s my true story in 1994!

    • Dick N

      You spelled his name wrong (Herndon) … but he is now divorced from his second wife, living with a man, and has come out as gay … so there is probably some truth to your story mate

  15. bob

    quite a lot. most recent was a guy i met in his shed at 2am and we did oral while inside his house was his lover, his mother and his sister. another time met a guy in a parking lot to be inspected as hot enough, i was and when we got to his house he made me take out my dick in my leather pants while i walked in his yard that way and then on to a 3way with his lover. another time a guy i used to meet in a park late at night. once we did it and came on the bleachers and picnic tables. another with the same guy we played in a gazebo while about 30 feet about 30 guys were playing basketball. about a year ago with a guy in his truck in the middle of a field. another with a guy in his back yard in his pool while his lover was inside. those are just the ones i recall at the moment.

  16. bob

    oh and my naughtiest was with a married guy who had only ever been with his wife, no other women, never a man. he was curious. i blew him, he blew me but once i came in his mouth that seemed to overwhelm him and we ended. but it was hot.

  17. Charles

    My most,was when I was at the bookstore one nite an meet this middle Eastern man that work at corner store,I stop at alot,we talk,we connected,he liked his meat suck(no fucking).I suck him off probably 10 times!

  18. Jeremy

    When my boyfriend is at work, I like to have guys over and put his pillow between our cocks and hump it it. That way my man is sleeping where some dude rubbed his junk and he has no idea hehe

  19. Kenneth Bublitz

    Took my jeep to have oil change just recently. Had late afternoon appointment. Asked the tech if he had any special for a retired dude. He moved back from the counter and grabbed his crotch and said “I can offer you this” He was much younger and definitely Hot. When I came back to pick up my jeep, the place just closed. He unlocked the front door and marked my bill Paid. Told me to follow him leading to the employee break room. The next hour or so was awesome. After we fucked he said this was a fantasy of his to fuck a customer. Can’t wait for my next oil change.

  20. Mel

    My partner and I were on a flight home from Rome and the flight was sold out. I got up to go to the WC and the guy on the aisle right across from me looked up and winked. Came back, sat down and after a couple of minutes I looked over at him and he had a blanket across his lap and opened it up to show off a really big cock. He was slowly rubbing it and I knew I had to have that cock. Really bold since the person next to him was a woman., Went back to where the WC’s were and stood there a minute. He got up and came back and we went into one. No need for me to speak Italian, I was down on that cock so fast and he only took a minute to explode down my throat. Stood up and he yanked my pants down and fucked me like a stallion. When we left the WC there were 2 flight attendants outside. The woman attendant looked shocked while the guy laughed and said good for you guys. You just joined the mile high club. We did in a big way. Never told my partner about it.

  21. vaguy495

    During noontime while sitting on one of the National Mall park benches catching some sun rays shirtless (mid-30s at the time). This hot looking early 40s guy walking along the sandy trail unexpectedly approaches me. He begins the conversation by complimenting me on my tanned body and my left nipple ring. Before I was able to respond, he immediately asked if I’d like to accompany him to one of the restroom facilities to have sex. I was somewhat hesitant at first, explaining to him about my concerns of it being a potential privacy issue. He said he knew of a particular downstairs men’s restroom which is seldom known & used; so I told him I’m definitely interested. So I put on my shirt and off we go.

    We enter inside as I follow him down this set of stairs, continuing along a short hallway to this remote restroom. He directs me into a particular stall, as he closes the door. Immediately, we peer into one another’s eyes as we begin embracing our bodies together, start to kiss by feeling one another, then move our hands downward to press firmly against one another’s “hard erect” penises. Next we each remove our shirts placing them over the garment hook. As we’re touching & feeling one another’s nipples, he leans his head downward to tongue lick mine, gently nibbling each nipple. He immed. unbuttons & unzips my shorts, pulling them off to hang over the garment hook. Myself following in direct pursuit, I do likewise with his pants. Nearly unclothed, we each remove our briefs, eyeing one another’s hard cocks. Grabbing ahold of mine, he firmly presses the palm of his hand around my shaft, masturbating it. I too grabbed ahold of his hard piece in mutual joy. We each take turns giving one another BJs. As he continues to suck me, I tell him I’m getting extremely close whereas, I’m about to climax. He continues sucking me even faster without pause, my dick climaxing by shooting my cum inside his mouth, watching as he swallowed it all, then tongue licked my piss slit (afterwards) to lick up whatever residual morsel that oozed out. Returning the favor, he moaned in pure delight just as someone unexpectedly entered the restroom, LOL. We briefly paused to wait until that person used the urinal, washed up, & left before continuing. As his moaning signals began to pickup speed, he asked whether I had any preference, of which I responded back; “unload your manhood anywhere you’d like to.” He instructs me to standup & turn around facing the opposite direction, then very slowly & gradually penetrates my anus, pounding me just briefly until he releases his full climatic pleasure.

    We each redress & exit outside, both of us walking back with one another to the sandy trail where we’d originally met. He then opened up by explaining he was stuck in a bad marriage whereas (at the time), his wife was adamantly against a divorce. I most definitely wanted to ask for his contact information, assuming he’d even be interested in connecting up again. But I decided that may not necessarily be a good idea, after he confided about his bad marriage situation. I deeply regret by not asking for his contact; because the little sexual time we each spent together, was most definitely “so” doggone phenomenal!

  22. Steve

    I was about 22 just got my forst apartment. One of the guys in the building used to get the paper delivered
    And as it turned out i knew the paperboy one thursday he came to collect the momey for his paper delivery. I was getting out of the shower when he knocked, answered the door wrapped in a towel. He is wearing a pair of basket ball shorts and a tank top, when i went to get my wallet my towel came undone and it fell to the floor.
    With out a pause he grabbed my ass spun me around dropped to his knees and started sucking my cock, he had me close to cumming in no time. I stood him up and pulled his shorts down and started sucking his cock, rock hard and about 8 inches and thick.. he blew his load fast loud and lots. he turns around grabs my cock lines it up with his hole shouts fuck me !!!!! He bemds over the the table just backs up forcefully onto my cock .. groaning and growling fuck me good and hard as im poundinghis ass the table is in the corner against the wall,and every time i slam his ass the table slams into the wall.. after 15 20 minutes i blast a load in him and am cleaning us up.. i catch movement in the window of my apartment.. the really old guy next apartment over was watching us.. I just smiled waved he hurried away.. i only hooked up with him one time after that as i found out he was only 16 and i fucked him on his 17th birthday
    He came to collect the rest of his money

  23. PostGayGrandDad

    I fucked Donald tRump back in the 70s. Such a needy little bottom. Please be sure to give Mr. Cohen my address.

  24. Steve

    Once when I was at Myrtle Beach, South Carolina, I was cruising in a public restroom, and to my surprise was able to pickup a young and incredibly good looking man in the next stall. We walked around the pavilion a bit and made small talk, and confirmed that we were interested in hooking up. His motel was several blocks away, but the walk seemed short as I looked at him as much and as often as I could, not believing my good fortune at picking up such a hot man. When we got to his motel it turned out that his little brother was with him. He told little brother to leave us alone so we could talk, and locked the door behind him as he left. I think he knew we weren’t just going to talk. We got busy getting naked and crawled on the bed. He was awesome and we had some mind-blowing sex together. After we both had came and were recuperating, the small talk began. What do you do for a living, I asked. I almost crapped on myself when he said “I’m a policeman.” I have never been so flabbergasted. He could tell and quickly said, “don’t worry. I’m not from here and I’m not on duty, and you’re not in trouble.” It took a bit for me to calm down, and I will never, ever forget him, how awesome and handsome he was, and how scared I was when he revealed his profession. Even some cops like to get laid by another man.

  25. Steve

    On my last trip to the beach with my family, I got a friend who was working there for the summer to give me a ride to a gay bar. Hours later, after a great time of drinking and mingling, it was closing time. So dressed in only buttock-bottoms exposing shorts and a mesh tank top, I made my way outside wondering who I could get a ride back to the motel with. A nice looking guy, we will call him Dave, came up beside me and asked where I was going. When I said I didn’t have a ride he offered one. I had no clue how this night would unfold from there. He had a nice sleek convertible with the top down. Soon I was sucking Dave’s dick while he drove. It was maybe 80 degrees that night and felt awesome. Soon we both had shucked all clothing and were totally naked. After a bit we started trading places every now and then, and the driver was always being sucked by the passenger. He would even drive into car washes or other well lit places and we would suck each other there in full view of any who mite look. We did this all night until dawn. He asked me to come to his room so we could finish our lovemaking. I told him I could not because my family would freak out if they woke up and I wasn’t there. I really wish I could have finished our loving in his bed. I will never know how good it might have been, but I also will never forget that romantic night with a stranger at the beach, riding up and down the highway sucking dick naked in a convertible.

  26. B.W.

    I was at work one day and a guy I had messed with came in,I walked up acting like I was helping him.I asked if he would like a BJ, he looked at me and ask when?. I said right now, he was a little on sure but I told him to follow me. We slipped into the back and into the men’s restroom. He asked again, are you sure,I told him it’s cool I am the only guy working right now and these are not public restrooms. I dropped down to my knees and reached to undo his jeans. His cock busted out of his dropping pants already 1/2 hard. I took him into my mouth and worked him over. He loved having his nuts sucked and pulled on and told me to get on them. I switched to sucking on his nut sack some. He was ready to blow so I got back on his stiff cock and sucked him deep as he blew his load into my mouth. He zipped up and we exited the restroom and I went one way and he went another.

  27. bjjj

    I appreciate the photo at the top of the 2 gay men, one white, the other black. With the shhhh!! finger saying don’t tell anyone. I am white and my BF is black, and many times we need to keep our relationship quiet.


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