Fantasy: What’s the Weirdest Sexual Request Ever Asked of You?

(Photo Credits: Next Door Raw)

Hey, guys! What’s the strangest, most bizarre sexual request a hookup or a partner has ever asked of you? And, well, how did that go for you guys? Did you end up enjoying it or did you, er, walk out of the bedroom door and was never heard from by the other party again?

Anyway, we are asking because we stumbled upon a thread on Reddit regarding this topic. Some of the guys said their boyfriend asked them to spit on their face while they were having sex. Some of the tops said they experienced an instance where a hookup asked them to pee on him—in his mouth, or inside him. Others said their hookup asked them to lick their armpits or feet or suck their toe while some were asked to cum on their partner’s face. Also, I’ve read about two or three guys who said their hookup wanted to rim them but that they were asked not to “wipe after pooping.”

On the other hand, quite a few guys confessed to having a cock or ball abuse fetish, some of them discovered they enjoyed it after being asked by their hookups or when their partner accidentally did it to them.

Anyway, if there’s something I learned in this life it’s that what’s weird for me might not be weird for others. That being said, what about you guys? Has a hookup ever asked you to do anything sexual which you found strange or bizarre? Did you grant their request? If you did, how did that go for you? Did you like it? Share with us your thoughts and your bizarre sexual request stories in the comments section below.

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  1. jackhammer_69

    I hooked up with a hot young muscular guy a couple years ago. He was a total bottom and wanted to rim me from his rim chair. While rimming me, he asked if I needed to shit and if so, would I do it while he was rimming me. It was the most unusual request I ever had, but I decided to remain open minded and granted his request. I can’t say that I would seek out that sort of thing again, but I am glad that I at least tried it, because he enjoyed it.

  2. PostGayGrandDad

    Once, years ago, a woman asked me to have sex with her. She knew I was gay, but she was insistent. She was the friend of a straight roommate. I made sure I was not around for the remainder of her visit. I was not about to be treated like a sex object. It was totally creepy and revolting.

  3. Charles

    Once I hooked up with a married dude who asked if He could call his wife and let her listen as he sucked me off. Of course I let him and I did over exaggerate his oral skills(he was a horrible cock sucker). Obviously she was masturbating during my blow job and after she got off she hung up.

  4. Takingpoundings

    The weirdest sex I’ve had was a threesome with a father and son. The son was my FWB and when I was at his house, his father came home and my fwb asked if his father could join. I said fine, and I sucked the son and ate his ass while the dad fucked me.

  5. tom

    Have had a guy who wanted to rim me right after I took a dump. But the all time weird one was when a guy wanted to come over and have me jack in a peanut butter jar so he could have my cum later. Different strokes for different folks I guess.

  6. Marko

    Being in my early 60’s I’m able to look back and recall so many wonderful moments, not that any were ever bad, but it often seemed as if the next was always better then the last.
    In my early 30’s I met a young sub bottom 20 year old kid who had a playroom set up in his rented house.
    I fucked him unmercifully in every manor at every opportunity. How we didn’t rip out the bolts and collapse his ceiling rafters from constantly abusing his sling still escapes me.
    As the dildos got bigger and longer the day came when I used tubes of lube and started working his hole with my fingers followed by my hand eventually inserting past my wrist.
    Once inside him, I’d make a fist and forcefully rocked rhythmically against his anus. Protruding and raising my thumb I’d work his hole as my thumb massaged his prostate.
    His young rock hard cock would leak precum out of the excitement, but once my thumb worked his prostate he’d jet nonstop wads of cum in waves of pleasure as his own convulsions now worked my fist.
    I never got up to the elbow with him, but it wasn’t from a lack of effort. One day he met another kid his same age and that was that, not even a goodbye fuck.
    Never again was I able to find a sub bottom boi that so eagerly wanted to be abused to such levels.
    At my current age I’m often routinely overlooked by the 18 to 35 crowd with extreme prejudice, but it’s thier loss.
    I often see a hot young man who I know with two hours of time and a tube or two of lube, I could fist into convulsing bliss, ensuring he’d be back day after day for more time with his “special” daddy.

  7. Smeg4me

    I’m usually the one to ask for wierd stuff. I have a foreskin and smegma fetish and can’t get enough of a dirty, smelly, cheesy foreskin. Also love to sniff and lick rank pits and balls. WS is fun and love to be showered or drink it straight from the tap. Really into having my cock and balls tortured and have a ball crusher I like to bring out if the guy is into it. Lastly, I love felching, especially if it’s a group atmosphere and the guy has multiple loads in his anus. Once it starts dribbling cum, I’m there to suck it out of him and lick his hole clean before they start giving him more.

  8. Johnny

    An older chap once asked me if I would put him in a diaper, give him a pacifier and rattle, and then literally bend him over my knee and spank him. Saying things like “who’s been a bad baby?!” I gave it my best shot, but it wasn’t until I heard him pooping in the diaper and then whimpering that he needed to be changed, that I couldn’t escape fast enough. A friend always told me that we don’t get to pick our fetishes which was consoling that night.

  9. bill

    I was having intercourse with a guy just as I came and then he wanted me to piss in him Thank God my dick got limp and fell out and that was the end of that. Well I did tell him the next time I would and glad there wasn’t a next time Don’t get me wrong he had one of the nicest asses I ever tapped Just not into water sports much

    • Justweird

      Wanted or did you do it? I once shit for another guy into his mouth, and he swallowed my whole load straight out of my ass.

  10. Dennis

    I had a guy I had been with before ask ahead of time that he come in, undress, bottom for me and leave without either of us saying a single word. It was fun and an experience I would do again.

  11. DM

    I don’t think having a guy cum on your face and lick it off is weird. Or licking armpits and feet. Rimming a dirty ass, though, is weird to me. I only rim clean asses and like being rimmed. I guess something that was strange for me was fucking a guy in the mouth while he was wearing a rubber hood. I did it, but it didn’t do much to excite me. I had a friend who had a guy who asked him to bark like a dog during sex.

  12. parker

    I was young and traveling on a bus to Chicago when waiting at a station in Cincinnati this guy csme over and ask me to the bathroom and wanted me zo shit in his mouth!

    • funsexguy

      Thanks no so weird, I’ve done it with a guy. Was in an arcade booth, and he wanted to rim me. Sure no problem, but I said I might be kind of dirty back there as I told him I needed to take a shit. Well, he started rimming me and said, you can give me a taste if you like. So I pushed out a little poop. He swallowed it, then he said you have any more, sure I said. So I shit a nice big load of poop into his mouth and he swallowed it all. We both jerked ourselves off and I never seen him there again.

  13. guy4oral

    I have been having some hot sex with a friend for a long time. He has recently become interested in scat play. He wants me to use one of his and put iit on his mouth like it was a cock. Sliding it in and out of his mouth. Don’t know if I want to do that, but I do like him and the sex has always been great with him.

  14. Centralflbttm

    Had a guy who wanted me to sit in his rim chair and literally shit in his mouth. He said he swallowed his wife’s shit all the time and she wanted to watch him swallow some guy’s shit. Didn’t want a blow job, didn’t want to fuck or get fucked in the ass, didn’t want to suck my dick…all he wanted was for me to squeeze a turd into his mouth while his wife watched, then I could go and he and his wife I guess would get so turned on they’d fuck each other. WEIRD.

  15. Daniel

    Weirdest sexual request?


    Young asian twink (I’m 52, he’s 26) I was having a fling with was so turned on by the amount cum I can ejaculate that he requested a pair of my underwear soaked in my loads.

    He’s currently working in Japan and often sends me emails saying he wears the undies around his apartment with every free moment he gets.

    Says it reminds him of the “wonderful moments” of our fling.

    Funny part is… He’s coming back to NYC in December for the holidays and wants to spend a weekend milking me for more to add to the garment!

    Gotta think that thing smells like a bag of assholes by now.

  16. asslover

    This is a really hot topic for me. After doing some cock sucking, I asked a guy if he would like to rim me. He said sure, so I turned around and spread my cheeks. I did say “I might be real clean back there” as I told him I needed to take shit. He said “that ok”. He started to rim me and he said “you can give me a taste if you like”. So I pushed out a little bit of my poo, and he swallowed a little piece. I said “you want some more”? Sure, and he ended up swallowing my whole load straight from my ass.


      There’s more! I have tasted poo, shared my poo, drank piss, and shared mine. I love taking a crap while being given a blow job, and have also given blow jobs as my friend took a crap, followed by a piss in my mouth. I also love lying in bed naked with a guy, as I dig in his ass pulling out a nugget. I have also said many times while in a bathroom to someone, “wanna watch”. One time I was jerking off in an open stall, and a guy approached me and said when you cum can I have it in my hand? Sure, no problem. I ejaculated a bunch right in to his hand and he licked it up.

  17. Brk_bad09

    1 guy asked me to shit on him.
    1 asked me to bite his balls
    A couple asked me to not wash my uc cock to build up cheese they could eat it
    A couple asked to roleplay as children and I daddy. I find role play corny and that particular kind creepy.
    I had one guy a town over hint at bestiality. I reported him.

  18. Jbobblj

    I was asked by a hookup to tie him up and literally beat the hell out of him. I did whip him but i didnt get off on that

  19. Michael

    The only weird thing I had was a married guy wanted me to take him out into the woods after dark after his wife went to sleep, tie him up naked and fuck him . That was a little bizarre to me.

  20. John Edwards

    I live in Palm Springs, where there are lots of clothing optional resorts. Last spring, around the time of the Coachella Music Festival, a very muscular and very handsome 35-ish guy chatted me up in the jacuzzi at one of the more infamous of those resorts. Bear in mind that I am 60 years old and *not* muscular or even “in shape.” The guy eventually got around to “confessing” that he was “straight” (as if!) and in town for his stag party before getting married … to a woman … that coming weekend. He claimed that he was on a mission assigned to him by his fiancee: to get fucked, so that he would know what it is like to get fucked. “Ok,” I thought, “I will play along with this rather bizarre fantasy, just to see how far it goes.” But upon arriving in his room, he announced that not only had the fiancee given him the assignment, she also wanted proof that he had carried it out. To my shock, that “proof” had to be provided in the way of a live Skype feed of the entire event! And I was asked to agree to be “coached” by the fiancee over Skype. Now, I have been exclusively gay my entire life. I have never once had sex with a woman, nor have I ever wanted to do so. And I am NOT into the whole “bi” thing. So I bolted. Too bizarre for me.

  21. Jason K.

    Once had a man (very hot older daddy) cum in a clear coffee cup and ask me to drink it. He was so turned on that he instantly came again.

    Another guy I used to hook up with would pull out and stare into my hole with a flashlight.

    Had a straight buddy of mine Ask me to lay back and he put his phone under my balls and watched straight porn while he licked my cock very very very slowly. I didn’t enjoy it at all, and after about 45 minutes I had to ask him to stop.

  22. Jeff

    I was asked o cater a gay couples anniversary dinner at heir house. But was to cook the dinner nude wearing only an apron.

  23. Miguel

    A guy who was a widower at an early age was definitely lonesome. It was to have been a simple 69 session. Turns out he wanted to be degraded, in a specific way. He wanted me to dump sweet and sour sauce from his fridge on top of his head and rub it into him while he sucked me. The smell was terrible and I had difficulty keeping from retching as the smell became more intense, which it did as the sauce hated up. And yeah, he wanted me to film him while doing it. I wasn’t able to stay hard with that nasty smell, so went to wash up before leaving. The stuff was all over my dick and the front of me and the smoky, sour smell was gross. When I got back out of the washroom, he was watching he video and jerking off to it. No harm done, but it was not my, um, cup of tea.

  24. Tim

    Weirdest request? There were a lot asked from me but the weirdest and down right disturbing to me is thus. One guy asked me to stick a thermometer up his butt and take his temp. Asking me to be his “daddy” mind you this guy was about 35.

  25. BryBry

    Had a guy, who was a hook up, ask to allow him to make a mold of my cock, so he could duplicate it.
    I said “nope”.

  26. Thad

    One guy online wanted to buy my socks — the ones I was wearing — as he had a socks fetish. I gave him my socks. Getting money for them felt too much like “socks”stitution, so he got them gratis.

  27. BJ

    I met an Asian bodybuilder who wanted to be muscle worshiped. But also wanted to be in control. He wouldn’t let me touch him while he flexed and posed until my mouth was watering and my eyes were begging to service him. Then he took out a container of chocolate pudding and ordered me to lick only where he spread the pudding. Yes, it was weird. But also hot as hell! :)~

  28. Markus

    I’ve been asked to pee in a dude’s mouth. I did and found it pretty arousing. I’ve been asked to shoot my load on a guy’s face, and on his dick so he could use my load as lube. I’m pretty open to most requests.

  29. Antonio

    I’m always being asked to fuck someone’s wife or girlfriend with them, to be some old white guy’s Mandingo/BBC, but the craziest was some Hispanic guy asked me if I could fart and take a shit before he came over because he liked the smell of it

    • bikiniguy

      been there, done that more than once….. That’s a fun thing to do when you’re both into the hot undies swap…. or just asked if you could have his as a momento

  30. Charles English

    Some would consider this a “TABOO”subject…but whatever two consenting adults agree to do in private is their business. I have a friend whom I play with on a semi-regular basis….he is much more adventurous then I am. We set up a time to play one time and he had a special request…he wanted me to wear the same pair of briefs for a week or more….pissing in them and letting it dry…cumming in them and letting it dry…. I thought it strange but I obliged…I would piss and cum in those briefs for almost 10 days before we met….when he saw that I was wearing those briefs,,,he immediately feel to his knees and buried his face in my raunchy and crusty crotch….taking the cotton fabric in his teeth…pulling my briefs down and then stuffing them into his mouth…..HE WAS IN HEAVEN….I jacked off watching him and gave him a facial.

  31. Jbobblj

    Ive bee asked to tie a guy up and veat the hell outta him. I did but didnt like it. Ive sniffed dirty piss stained jocks. Hot

  32. arthur

    SCAT. well I just couldn’t rap my head around it. I now understand what it is and still cant. I beleave to each there own. after all. I love smelling mens arm pits and balls. but cant bring myself to shit in someones mouth. which is funny cause I could do the golden shower. enjoy your day guys….hug and kisses to you all….art

  33. lee

    met a guy that took me to a supermarket and bought lots of sweet runny stuff. we went home and opened all the cans and covered each other with it and then had the most amazing sex ! his roomie came in later and started sniffing , said ” do you smell chocolate?” we died laughing

  34. Nastydogboy

    Nastiest request, I was asked by a buddy if I would eat out a homeless guy’s ass and suck his dick, and swallow as he watched. Wasn’t bad at all.

  35. subfaggot Chris

    I didn’t used to be kinky but now I’m open to everything because I always tried to be open minded. Only exception is anything where the person can not give consent or it could be dangerous. Cbt was my gate way and I found myself smiling during, so I became a very good sub lol.

  36. Lamar

    Wow, lol, at 19-20yrs old, I had pretty much just come-out. One night I met this dude in this one park in my hometown well known for cruising back in the very early 80’s, he lived literally across the street from. We when to his place and to the bedroom, undressed started to kiss, he gets up and goes to the drawer and pulls out a straight-razor!

    I asked what the fuck are you doin’ man? He said, “I’m going to shave you.” I said, “uh-ah, oh no you don’t”, as he started towards me, I picked up a chair a clobbered his ass- getting my buck-naked ass out into the hallway, dressing as I went down the stairs. I ran into another dude asking me, “You must of come from #6, my roommate-he should tell people before hand what he’s into.”

    The only thing I could think of was the movie, “Looking for Mr. Good bar” when he grabbed that goddamn razor, lol.

  37. tightass4cocks69

    I had a guy at the bath house one time come in with a raging hard on. He wanted to suck my toes. It was pleasant at first but he wouldn’t suck my cock or let me suck his. I had to end it when he started trimming my toenails with his teeth!

  38. Mike

    Back in days that I kept smooth I had a smooth guy as well that I flip fucked with. We smeared white glue all over each other and had sex in it until it was dry. Sexy feel and smell to white glue. We then peeled it off each other while making out after we got done cumming in each other’s asses.

  39. Terry

    Had a guy who wanted me to tie him up and fuck him.
    Had a guy who wanted me to put my fist in his ass.
    Had a guy who wanted me to piss on him and in his mouth.
    Had a guy who wanted to wear a mask so that I did not know what he looked like.
    Had a guy who wanted me to rip his panty hose and fuck him.
    Had a guy who wanted me to fuck him in his garage so that his wife would not find out.
    Had a guy who wanted to watch me fuck his boyfriend.

  40. Texan09

    I had a guy ask me to put on boots and stand on him while his boyfriend watched. He had a spot below and to the left of his navel he wanted me to put my full weight on while he jerked-off. I did give him some pressure but when he wanted me to jump up and down I wasn’t sure I wouldn’t do serious damage even with his boyfriend monitoring the situation. It was apparently enough though because when he came he gave his boyfriend the most complete facial I’ve seen from a single orgasm.

  41. Seaguy

    I was a little drunk walking home alone from the club when a truck pulled up along side me and the driver asked me if I wanted a blow job. I said no, and kept walking thinking “I am not some cheap whore” But then he pulled up along side me again on the next block and said something like are you sure? He got me to change my mind and hop in his truck. Come to find out he lives a couple blocks away from me. So we get to his apartment strip down and he is blowing me. Then he asks me to try fisting him. I thought sure why not, had to piss so I asked where the bathroom was he asked if he could drink it. I was like sure, figuring I would see what it felt like. So I started to piss and he was taking it all down his throat and I did like how it felt but when I finished I got weirded out by it all the sudden and told him I needed to use the bathroom. Once in there I climbed out the window and ran home.

  42. Chris

    Love BBC , one black guy I hook up with likes me to call him nigger and beg for nigger dick. At first I was not into it but the more you said it, the harder he fucked.

    • Lamar

      “Race-Play,” he, is into that, they’re out there. I think that’s what the whole “thug-thing” is about to a lesser degree, I’m guessing.

    • bjjj

      Hey race play, huh? Yes, it really turns some guys on. I know it’s a turn on for white guys to want the challenge of having sex with a black guy and vice versa. However my BF is black and I am white, and I don’t feel we became lovers because of our racial differences. Knowing each other for almost 2 years now, our racial differences really doesn’t play a part in our wonderful relationship. There is a lot more to being lovers, being gay, etc than just having sex. We just have so much in common, like the same things, and care so much about each other, who cares about our skin colors. He isn’t my “black friend” he’s just the wonderful man I really love.

      • bjjj

        I think it would be very demeaning if I were to call my BF a “nigger” We have no reason to call each other names. If I did, It would be just in fun, something to laugh about. I can say anything to him, and he can say anything to me, and he and I don’t keep secrets. I think we know more about each other than our own families do. (like stuff you never share with your closest relatives). Oh yea, almost forgot to mention, I am white and my BF is black, not that it matters to either of us.

  43. Bi_Marriedtravel

    When I was younger there was an older guy that loved to edge me until he was ready for me to cum. He got off on me begging for him to let me and saying kinky shit while he was doing it. If I made it until he was ready he would pay me. He got off on the control (paying me was his idea) and never even took off his clothes. The orgasms were great and I made some extra cash so it was cool.

    Had one guy who wanted to drink my piss while he was sucking me. It actually felt great and after I came I gave him some more piss as I had been drinking pretty heavily that night 🙂

    One guy had a rim chair that he asked me to sit on. He sat on the floor in front of me and slid his legs and crotch underneath. He asked me to shit on his dick while he sucked me. That was too much for me and I had to say no.

  44. TxBoy008

    This is going to top all of y’all. I was asked to pretend to impregnate a man and he would put a pillow under his shirt. He would walk around the house and act like he was 9 month pregnant. Then we would have to deliver the baby(pillow) and he would scream and cry and slap me for getting him preggo. He got so turned on by this lol.

  45. Dylan

    You will think I made this up. No one I tell believes it. It’s is NOT BS!

    I was in Ogunquit, Maine (maine’s Gay town) met this guy in a booth and we fucked several times there. He eventually trusted me and invited me to his apt. He was so fucking HOT! Way out of my league. He belonged on the cover of men’s health. He was 26 5’10” 170lbs ripped, 8″uncut Latino/Asian. The sex went on for hours. Anything you could think of we did. He d open the window and I’d fuck him as we looked down into ppl in the street. He loved when they looked up. This became a regular thing. I come over one morning during pride. The town was packed. When I got there he was in the kitchen wearing a jock and an apron, making eggs. I walked up behind him and kissed the back of his neck. He turned around and we started making out. I immediately dropped to my knees and began blowing him under his apron. He turned off the eggs. We went to the bed room. Just like always kissing, rimming, sucking (30min at least). We are getting ready to fuck I motioned towards the window and he got weirded out. He said,”ughhh not my thing!” I thought that was odd as we’d done it there many times. So I fucked him on his bed. It was awesome. He blew his load all over me as he rode me. He got up and went to the bathroom. Came back and started kissing me and blowing me, licked cum off my chest. I was so turned on. He got up on top of me again. He begins to ride me. We start making out. He points to the window. I oblige. I’m fucking him where everyone can see (and doing my best to put on a show with a bunch of ppl watching). I can’t hold back any longer. I bust inside him. I drop to my knees and blow him until he shot down my throat. He goes to the bathroom as he is all sweaty and was going to run a shower. I was picking up my clothes. Joined him in the shower. All of a sudden the bathroom door opens (I thought roomate), the shower curtain opens and there is a naked identical twin standing there who jumps into the shower with us. I was speechless. My mouth hung open wide, I could have sucked off john Holmes. They were laughing. So the guy I first met told me we do this a lot. Even in grade school we’d switch classes Their mom couldn’t tell them apart until they spoke. he reveles to me I’ve been fucking both of them for almost a month. We never had sex together as a thressome other then in the shower, but I continued to fuck them that whole summer. They had the exact same moves. The only difference was the window sex. I so wanted a threesome. Then they moved to South Carolina. I was so upset when they left. Never heard from them again.

  46. dirtyfun

    A weird thing that I did once was in an adult arcade. Found a pair of small, skimpy, dirty panties. Way too small for me, but never the less I couldn’t help but to stretch them on over my cock and ass. They were cum, poo, and pee stained, and just the idea made me super hard, knowing I was wearing someone else’s dirty panties, having no idea who left them there. I ended up shooting my load in them and left them there for someone else to enjoy.

  47. Mark

    After the gym, I hooked up and the guy who just wanted to eat my sweaty ass raw … to my surprise, while being rimmed, he was tonguing cherries up my hole & deep tongue fuck my ass.
    After some time, he asked to cum in his mouth, which I obliged. He then went back to rimming me and tonguing my cum up my hole. He then continued to rim me slurping/eating all the cum laced cherries from my ass … I came again which he slurped up and filled my ass along with cherries … I shot another load which again, we went full circle … that was an awesome hookup!

  48. Art

    I had an older top dress me in his wife’s lingerie and heals and do me bent over their bed while he showed their home made porn on a big screen TV on the wall.

  49. Jockn2cbt

    Wow, if I can remember them all;

    Fucking on top of a children’s platform at a strip mall photographers.
    Gut punching this super hot blond guy, felt bad to a degree but that’s what got him off.
    Jacking off on this bodybuilder’s chest was the only way to get him to cum.
    Hot sub blindfolded and tied to a chair by this gruesome hetero couple, asked him to suck my nuts hard, he did….nearly castrated me….loved every wince. Untied him and escaped while our hosts were preoccupied by their young kids downstairs….weird night.
    Tied to the rafters of a Silverlake bungalo basement, sounded and kept in place with a condom and a tight rubber cockring as this muscle couple fucks on a mattress at my feet, not really a request. Turned into a real memorable night.
    Lots of weird location requests for sex, I’m an exhibitionist but not into offending innocent bypassers which leads to the number of homes/apartments I’ve been in that are essentially oversized fishbowls, no curtains, no blinds and the place will be lit up like a stadium. And lastly, I have had this run of good looking masculine athletic guys (think minor league baseball team) 20-somethings sucking me off completely emotionaless and having me videoing me cumming on their faces with their smart phones… this a “thing” now? Their demeanor has been like gay-for-pay straight guys hired to do a distastefully boring job or points for an extreme scavanger hunt. I don’t get it, but who am I to argue with a pretty face wanting me to paint it? Anybody else experiencing this? Any thoughts?

  50. dave

    weirdest was the first time a guy asked me if I was a real red head
    before that question he had aroused me fully
    when to the parking lot to his car and said check for your self

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