Serving up this steaming pile of
Celebrity Gossip
Gay Politics
Gay News
and Pointless Bitchery
Since 1995

Strangest sexual requests

A few weeks ago someone mentioned a guy that liked to ride piggyback on men as a fetish and this got me wondering - what is the strangest or just most "random" request anyone's asked you as something that gets them off?

I had some dude ask me to wear a stained T-shirt and then rip it off for him. Super specific and random, right?

What weird shit have you been asked to do to get the mood going or to get your hookup/partner off?

by Dr. Ruthlessreply 9201/27/2013

Feet, just lots of stupid things with my feet

by Dr. Ruthlessreply 101/25/2013

I've had alot of guys tell me about their foot fetishes.

by Dr. Ruthlessreply 201/25/2013

I have a foreskin fetish, i love when guys who are uncut play with it and show me things they can do with it, as i am cut. I guess some guys would think that is weird.

by Dr. Ruthlessreply 301/25/2013

A guy asked me to pee on him. This was during my experimental phase. I was glad to oblige, and equally glad to know that it did absolutely nothing for me. If nothing else, it taught me to leave the fetishists for other fetishishts.

by Dr. Ruthlessreply 401/25/2013

Years ago, a guy asked me to demolish his piano with a hammer. The guy was hot so I obliged.

Of course, I learned the next morning that he taught at a Catholic school.

by Dr. Ruthlessreply 501/25/2013

I had a guy who once gave me large eyeglasses and a hair piece - and asked me to say "Gobble, Gobble Gobble", before going down on him, in my best Charles Nelson Reilly voice.

by Dr. Ruthlessreply 601/25/2013

Some guy wanted to role play, where we were both Roman gladiators. At some point, he gave me a clam shucking knife (I swear), and had me hold it against his nipple, saying I was going to cut it off. He masturbated while doing this, after which I fled.

He lived in an apartment furnished entirely by a Soloflex-type exercise machine, which is where we carried out this little charade. Worst hookup ever.

by Dr. Ruthlessreply 701/25/2013

Yogurt Guy.

Back in the late 90s there was this hookup who ate a LOT of yogurt (plain/unflavored, the funky-tasting kind) out of my ass, one sloppy dollop at a time. It got him insanely turned on. It helped that I was doing tons of power yoga at the time and had an amazing ass - round yet lean, muscular.

The yogurt aspect did nothing for me, though a crazily enthusiastic rim job by a goatee'd person is always a sensation that turns my crank. So, win-win.

by Dr. Ruthlessreply 801/25/2013

OP, the stained tee shirt fetish might be simpler than it appears:

He might just have liked the thought of your ripping off a tee shirt, and was thoughtful enough to suggest one that you'd certainly discard anyway. It's not as if he'd asked you to take a cold shower, put coins on your eyes and lie very still.

by Dr. Ruthlessreply 901/25/2013

R8, low fat, or no fat?

by Dr. Ruthlessreply 1001/25/2013

Somebody wanted to place the penis in their mouth and just keep it there for several minutes, like their mouth was a bathtub. No fellating. Just.... yeah.

by Dr. Ruthlessreply 1101/25/2013

I knew a guy who liked to have me wear nothing but jeans, then he'd slather them, and me, in lotion. I wasn't crazy about the smell, so I made him buy me a new pair of jeans every time he wanted to slather, and he did. Hey, free 501s.

Then there was the guy who liked me to drink lots and lots and lots of water, then process it into his mouth when the time came. Strangely, I never wanted to kiss him.

And there was a guy who liked for me to beat him with my belt. It had to be *my* belt. That was significant. I liked this request better than the other two.

That's about as strange as it's ever gotten.

by Dr. Ruthlessreply 1201/25/2013

R10: I think it was regular (full fat)

by Dr. Ruthlessreply 1301/25/2013

A girl asked if he could massage my feet, but she seemed to enjoy it much more than I could understand. I noticed a self published magazine about foot fetishes thumbtacked to her wall. I was creeped out.

by Dr. Ruthlessreply 1401/25/2013

The one other very odd request I've had was from a very hot farmer.

He confessed to me that he had a fantasy that a guy would "squeal like a pig" and eat from a trough for him.

I got the fuck out of there as soon as I could. I wasn't even worried about myself, but I sooooo didn't want to think about what that said about him and the pigs he owned.

by Dr. Ruthlessreply 1501/25/2013

I had a trick demand I take money from him. I was 43 at the time! A hell of a time to take up prostitution!

He was about 30ish and we connected on Manhunt. I went to his place (close to mine) and gave him a good fucking. When I was getting ready to leave, he tried to hand me three $100 bills. I didn't make any motion to take it.

"This is for you."

"Huh? Um, no. Not sure what you mean. No."

"You have GOT to take this. It's for you. I want to pay you."

"I don't want any money from you. What are you talking about?"

"Just take it. You've GOT to take it. Please, just... it's for you and I want you to have it." He then shoved the bills in my jacket pocket. I walked out.

Very strange. I still have no idea what it was all about. This was three years ago.

by Dr. Ruthlessreply 1601/25/2013

R16, still got his #?

by Dr. Ruthlessreply 1701/25/2013

Oh yeah... my other strange one was about 20 years ago (time flies, by the way... still feels like yesterday), a guy on the street who was around my age (mid 20s) approached me out of the blue and asked to smell my socks! It was about 7pm on a warm night, at 83rd and Lex.

I actually looked around wondering if this was some kind of hidden camera prank.

He asked a few more times "come on, I just want a sniff." Shocked, confused, suspicious... but intrigued, I said he could. He said he knew where we could go, and he took me to the back entrance of a building that seemed reasonably deserted.

He took off my shoes and sniffed and licked them all over. Then he started sniffing my socks as requested, taking long deep breaths and some licking. After maybe 5 minutes of that, he unzipped his pants and started jerking off.

After he came, and we started to get ready to leave, I stopped and asked him if he wanted my socks. Geezus, he was SO happy I offered them, like if I'd given him a lung he needed or something. "thank you thank you thank you."

So I gave them to him. It was really uncomfortable walking in my shoes sockless, but I was able to buy socks nearby.

I always wondered whatever happened to that guy. Approaching random men on the street and asking if you can sniff their socks has to eventually lead to some suboptimal outcomes.

I think that and my story at r16 are the two strangest sex requests I've ever had.

by Dr. Ruthlessreply 1801/25/2013

I'd sniff you R18. LOL

by Dr. Ruthlessreply 1901/25/2013

I once made a weird request of a guy I met at a bar around Christmas one year.

He was wearing one of those stupid Santa hats. Got him back to my place and naked, except for the hat. I asked him to leave it on when I fucked him.

It was insanely hot for some odd reason.

by Dr. Ruthlessreply 2001/25/2013

Nothing really, except I'm always amazed when mtf transsexuals and cross-dressers contact me online. They're usually very presumptuous or agressive, assuming I'm going to go wild with excitement in response to one message. I identify as openly gay and list the various types of men that I like, which doesn't even include ef-feminates who identify as male, let alone transsexuals or females of any stripe. Just so bizarre. I guess I attract them.

by Dr. Ruthlessreply 2101/25/2013

A guy who wanted to beat me with his belt. It was Hermes, so I told him "sure, but I'm keeping the belt."

by Dr. Ruthlessreply 2201/25/2013

Silly is how I felt beating the guy with the belt, R23, but he liked it, and I liked him, so we did it R12. We saw each other for months, only breaking up because I moved. I wonder what ever happened to him.

by Dr. Ruthlessreply 2401/25/2013

This was strange to me at least. I met this cute guy out at the bar. Cute as a button, pre-med student a few years younger than me. We hit it off and had a few beers. Ended up inviting him back to my place. This was in early fall. He asked if I had a down North Face jacket, which I did, but he asked me to put it on with nothing else so we could service my cock on his knees while I wore it then he wanted to be bent over and plowed while wearing it. I did it, but mid-coitus I thought it was a bit strange. I guess I still do. I see him once and a while and wonder if he still asks guys to put on thier North Face jackets? Stranger sexual requests exist I suppose.

by Dr. Ruthlessreply 2601/25/2013

I once had a guy that wanted to watch me smoke fully clothed while he jerked off. (I don't smoke, but I did it because he was cute)

I have size 11 feet, so quite a few foot fetishists have gone gaga over my bare feet.

These guys wanted me to wear my high school cheerleader uniform while they wore singlets and jockstraps. (I had it in town with me because I wore it for Halloween one year)

I also had a guy want me to pee on him. It did absolutely NOTHING for me, but he really enjoyed it, so I thought, "What the hell!"

by Dr. Ruthlessreply 2701/25/2013

I was once intimate with a guy who had a major fart fetish and he wanted me to rip bare ass farts on his face.

When I said no he even offered to pay me

by Dr. Ruthlessreply 2801/25/2013

A guy wanted to come on my ass hole then lick it out. Didn't want me to touch him. Said he was married with five kids.

by Dr. Ruthlessreply 2901/25/2013

A guy who wanted to be hit, hard - during sex, including during foreplay. He also wanted to hit me. I didn't know this until we were making out and he slapped me across the face.

I gave him a huge shove, which just got him more excited. Thankfully, this wasn't at my house. Forest Gump didn't run as fast as I did!

by Dr. Ruthlessreply 3001/25/2013

I was one the submissive in a domination scene. I was terrible at it. I can't be dominated. Apparently I talk too much.

by Dr. Ruthlessreply 3101/25/2013

[quote] A guy who wanted to be hit, hard - during sex, including during foreplay. He also wanted to hit me. I didn't know this until we were making out and he slapped me across the face

You....love to make me hit YOU!

by Dr. Ruthlessreply 3201/25/2013

I had a brief fling with a guy who wanted me to squeeze his nuts HARD. I mean between both hands with fingers clasped, squeezing with all my might.

He was a nice guy and had an enormous cock but the nut squeezing thing was just too weird.

by Dr. Ruthlessreply 3301/25/2013

I don't know if this is true - but I met a guy 25 years ago who said he tricked with a guy who would bend over at the end of a hallway while the other guy threw oranges at his butt.

Made a messy hallway. Still don't know if it's true as I think I heard a similar story later by someone else.

Thankfully I haven't had any really weird requests.

by Dr. Ruthlessreply 3401/25/2013

r16, it was his need to justify what he did. If he paid for it, it wouldn't mean anything remotely emotional.

by Dr. Ruthlessreply 3501/25/2013

Weirdest one was a guy who would sit naked at the end of a table and I would have to roll hard-boiled eggs at him while yelling, "Bombs Away"!

by Dr. Ruthlessreply 3601/25/2013

In college a fuck buddy of mine introduced me to a professor who was into roleplay. I got paid $50 twice a month to let "daddy" spank me with a hairbrush.

The profesor was loaded because of patents from his research. Famous in his field, and a nice guy with a kinky side. I made $100 a month getting punished for being "a bad, bad boy."

Mid 70's, and it paid the rent. Also was paid to shit in front of a business ex who LOVED to watch guys drop a log.

by Dr. Ruthlessreply 3701/26/2013

A guy wanted me to wear a bra and panties. He showed me a catalogue with hot guys wearing women's lingerie to coax me into it. I met two different guys who liked to drive naked - at night but in heavy freeway traffic.

by Dr. Ruthlessreply 3801/26/2013

There is a guy on Craigslist in New Orleans that wants to have sex with men who "blow up their stomachs". When I asked him about it, he said he wanted someone to Puff out their stomach for him while having sex.

The was the strangest I've ever seen.

by Dr. Ruthlessreply 3901/26/2013

Once, many years ago, I tricked with a necrophiliac who wanted me to breathe as little as possible so he could pretend I was dead.

TRUE STORY!

by Dr. Ruthlessreply 4001/26/2013

Years ago when I was 21, I briefly had relations with a slightly older guy who asked if he could give me an Enema.....with his dick. Same guy on another occasion excused himself while we were in bed and left the room for several minutes.Than came running into the room yelling while dressed as a nun and holding a large kitchen knife jumped on top of me while straddling my chest. I was too naieve to be afraid. But when i performed it for my lesbian roomate from time to time. Sans nuns habit she would scream with delight. And ask me to do it for friends who visited. She forbade me to see him again.

by Dr. Ruthlessreply 4101/26/2013

I also had a guy who wanted me to step on his cock when it was hard. I felt weird doing it, but he begged me. He had a big one and I thought he could support my weight, so I did it.

by Dr. Ruthlessreply 4201/26/2013

A guy who wanted me to punch him in the balls.

A pale, goth looking guy who wanted to be beaten with a large leather belt with the equally large buckle on his side of the exchange.

Guy who wanted me to pull on his weave. Seriously.

Construction worker type who was wearing pink lacy panties and bra underneath his clothes and wanted me to tell him what a pretty girl he was while fucking him.

Guy who wanted to verbally abused while he was blowing me. Another guy who wanted the same while I was fucking me.

When I was young I had a "why not?" approach to these requests. As I got older, I just said no thanks.

by Dr. Ruthlessreply 4301/26/2013

"Another guy who wanted the same while I was fucking me."

O.K. That was an interesting Freudian slip.

by Dr. Ruthlessreply 4401/26/2013

I wonder if that isn't a bit of an urban myth R34, as I remember a guy at a party talking about doing the same thing to a trick. Unless that guy who liked having oranges heaved at him really got around?

A guy called for my roommate (who wasn't home) started flirting with me. I ended up at his place jacking him off with melted butter. Is this a common thought? Hmmmm, melted butter, I wonder what that feels like to jack off with?

He was cute but I kind of got skeeved out and got out soon after he shot his load.

And, no, I doubt if my roommate gave a shit I tricked with one of his buds. He slept with lots (and I mean [italic]lots[/italic]) of guys.

by Dr. Ruthlessreply 4501/26/2013

[quote]He was wearing one of those stupid Santa hats. Got him back to my place and naked, except for the hat. I asked him to leave it on when I fucked him.

Fuck me, Santa! Fuck me, Santa! Fuck me, Santa!

by Dr. Ruthlessreply 4601/26/2013

would love to hear from an escort on this topic. you know they must get it all

fetishes are so weird to me. the way everything HAS to be sooo specific. what does psychology say about fettishes? are they the result of abuse?

I like touching and kissing, a lot, almost like a fettishes in the sense that climax and actual sex are secondary to me. I am more satisfied with foreplay.

by Dr. Ruthlessreply 4701/26/2013

"Guy who wanted to be verbally abused while he was blowing me. Another guy who wanted the same while he was fucking me."

This is actually fairly common... It's just an outgrowth of traditional 'dirty talk'.

by Dr. Ruthlessreply 4801/26/2013

[quote] the way everything HAS to be sooo specific

Yeah, I always figure that either the shit these guys asked for happened the first time they had sex and they think they can't get off otherwise, or it happened once and it was hot for them, so they want to repeat it every time.

by Dr. Ruthlessreply 4901/26/2013

A guy I was dating wanted to be sealed in garbage bags...and fucked. He was so gorgeous, it was a bit of a turn off, but I fulfilled his fantasy ... Many times...

I think it was a latex fetish at a bargain price.

by Dr. Ruthlessreply 5001/26/2013

A guy wanted me to watch him fuck his wife then right before he came to fuck him. It seems She had trouble getting pregnant and that is how she got pregnant the first time. He was cute and so was she so I did. He was prelubed, and I wore a condom. He later told me she got pregnant.

To this day I wonder if they really had used the load I had left in the condom to impregnate her.

by Dr. Ruthlessreply 5101/26/2013

You should have taken the condom with you, r51

by Dr. Ruthlessreply 5201/26/2013

R52 is right. That's probably your kid.

by Dr. Ruthlessreply 5301/26/2013

Another vote that R51 is a daddy.

by Dr. Ruthlessreply 5401/26/2013

And another.

Time for Maury to get involved, gurl!

by Dr. Ruthlessreply 5501/26/2013

Once hooked up with a guy who wanted me to hold a knife to his scrotum and threaten to cut off his balls and cock while he jacked off. I didn't have to touch him or do anything sexual, just press the knife against him and threaten to castrate him. (It was a one-time thing and he did offer money after I persisted)

by Dr. Ruthlessreply 5601/26/2013

I was asked to make a doody on someone, but not by accident...

by Dr. Ruthlessreply 5701/26/2013

Cemetery sex.

More than one guy.

I had an epitaph from a flat grave cover impressed backwards on my ass.

by Dr. Ruthlessreply 5801/26/2013

Knew a hot, younger guy (younger than me, anyway) who was into frottage, but only while he was wearing his underwear. He'd pull my boxer briefs down and rub his cotton-encased bulge in my naked ass crack until he came. He and I went to the same gym (it's where we met) so I saw him naked all the time. But I never saw his dick when we were having sex. Odd.

by Dr. Ruthlessreply 5901/26/2013

When I was in college I met a high school dude who wanted me to fuck him in the locker room at a wrestling tournament while you could hear the noise from everybody in the gym outside. But he wanted it set up so that I came in from outside (like I had been wrestling) all upset and pissed off that I had lost. He was sitting on the bench wearing white socks and briefs. Also, he wanted me to piss on his dick while he jacked off to finish. Thankfully, nobody interrupted. He supplied the singlet and it worked out pretty well.

by Dr. Ruthlessreply 6001/26/2013

Too many spanking guys to mention, but one:

Hot blond guy, 6'2" with a nice big eight inch cock.

Wanted to be spanked but would not let me touch his enormous, rock hard cock.

Too frustrating for me. I sent him away.

One afternoon, he showed up at my condo, unannounced, hoping to be spanked. Men!

by Dr. Ruthlessreply 6101/26/2013

One older guy used to like for me to kick him in his balls repeatedly. He also liked me to give him heavy whacks on his nutsack with a ping pong paddle.

It was an easy hundred bucks whenever I was low on cash.

by Dr. Ruthlessreply 6201/26/2013

What is it with the spanking and pain stuff?

I always feel so bad when a dude asks me to do that. I don't want it done to me!

by Dr. Ruthlessreply 6301/26/2013

The only pain I want is Zak's eight inch blonde dick whipping me with that sizemeat.

by Dr. Ruthlessreply 6401/26/2013

What does a blond dick look like?

by Dr. Ruthlessreply 6501/26/2013

[quote] The only pain I want is Zak's eight inch blonde dick whipping me with that sizemeat.

Uh, that should have had an apostrophe. I meant the blond dude he mentioned.

Derp.

by Dr. Ruthlessreply 6601/26/2013

R47, the psychology behind fetishes is based on what fetishists have self-reported, so who knows if their reasons apply to everyone with a fetish.

But the theory is that people with fetishes have an experience before puberty and during that experience, they become sexually aroused. Maybe it happens many times over a period of weeks or months and every time, the prepubescent child gets turned on. For instance, the babysitter touches a boy with her bare feet. Maybe she tickles him with her feet every time she babysits. That boy then grows up associating bare feet with sexual arousal and, voila, a fetish is created.

It's a theory. Perhaps some of DL's fetishists will share their earliest memories of getting turned on by their particular fetish.

I always had a problem with this being a blanket explanation. How do crushing fetishes start? Some are so specific. Are there a lot of people who, when they were kids, saw fruit/mice/dirt/etc. squished between toes and got turned on by it?

by Dr. Ruthlessreply 6701/26/2013

I would like to tinkle on someone at some point

by Dr. Ruthlessreply 6801/27/2013

Come on over, r68!!!

by Dr. Ruthlessreply 6901/27/2013

Once, this guy in a bar begged to lick my sneakers. I was willing, so off to the Men's room we went. When I got the big idea of stuffing one of my socks in his mouth, he shot a load all over one of the sneakers, so I made him lick it again.

Later, he told me that he had driven all the way from Toronto (4 hours!) to engage in this activity, as he didn't want his friends to find out he liked it.

That's about it for me....pretty tame. On the other hand, there's a whole bunch of stuff mentioned upthread that I wish some guy would do to me!

by Dr. Ruthlessreply 7001/27/2013

I wouldn't call this a request since the guy did this spontaneously, but it was the weirdest thing I've experienced. I was making out with a somewhat mature Middle Eastern man (think younger Omar Sharif type) and he started probing my ear with his tongue. No problem with that. Then he put his tongue up my nostrils and started cleaning them out! How bizarre?? I let him, because as another poster said, I was naive. But I think a nostril cleaning is a pretty gross fetish. I was more aroused at the fact he was such a freak as opposed to how it felt, this was years ago and when I think of it now I get a little nauseated.

by Dr. Ruthlessreply 7101/27/2013

I hate it when guys try to lick inside my ears, R71. That's definitely the weirdest, freakiest thing I've encountered... I accepted it when I was younger, but I told the last guy who tried it to please stop (he did).

by Dr. Ruthlessreply 7201/27/2013

I had a guy that like to pour heinekin down my ass crack and slurp it out.

by Dr. Ruthlessreply 7301/27/2013

[quote] tinkle

I think if you said "tinkle" like a 5 year old you'd kill all chances of anyone wanting that done to them.

It's PISS play. You PISS on someone else.

by Dr. Ruthlessreply 7401/27/2013

Does it make me a bad person to LMAO at some of these kinks?

People are weird.

by Dr. Ruthlessreply 7501/27/2013

I once spoke to a guy over one of those phone-based dating services (LavaLife), who wanted me to "force" him to clean my house.

It was very specific: he'd be naked except for an apron, and would have to clean the kitchen and then the washroom, while I mocked and insulted him the whole time.

Then, when he was done cleaning, he would act as my footstool for a few hours while I watched tv, and hopefully I'd put my bare feet in his face.

That was all he wanted, there was nothing sexual involved, AND he was willing to pay me $100 for it.

I was realllly tempted to take him up on the offer (free money AND a maid service?) but was too skeeved out.

by Dr. Ruthlessreply 7601/27/2013

I think I might know that guy, r76! His name Pete by any chance?

by Dr. Ruthlessreply 7701/27/2013

This confirms what I have always known,... men are PSYCOS.

by Dr. Ruthlessreply 7801/27/2013

[quote] men are PSYCOS.

Oh, dear.

by Dr. Ruthlessreply 7901/27/2013

Meh, typos happen.

by Dr. Ruthlessreply 8001/27/2013

R76 ripped that one straight out of the movie "Going Down in La La Land"

by Dr. Ruthlessreply 8101/27/2013

Wow, R71. In high school, I briefly dated a Punjabi guy who wanted us to lick out each other's noses. He did it to mine and I thought it was weird, but I couldn't do it back to him. I think I timidly licked the outer edge of his nostril. He was upset about it.

Another guy wanted to piss in my mouth while he was hard because he said it felt better than an orgasm; have us both wear diapers and just hang out watching a movie; pee in diapers and then masturbate, because the pee turns into gel and feels good; cut holes in our diapers and fuck through the diapers. I couldn't get into it.

by Dr. Ruthlessreply 8201/27/2013

I guy wanted me to ribbet (sp?) like a frog. I kid you not. And I was the one on drugs, not him.

by Dr. Ruthlessreply 8401/27/2013

I get that R26, I find those jackets a turn on.

by Dr. Ruthlessreply 8501/27/2013

[quote]fetishes are so weird to me. the way everything HAS to be sooo specific.

There is a wonderful scene in "Belle de Jour" where this John kicks Denueve out of his room because she can't do things just right and his regular girl comes in to do the job instead.

by Dr. Ruthlessreply 8601/27/2013

I see those puffy jackets everywhere.

It makes skinny and or chubbo types all look muscular.

by Dr. Ruthlessreply 8701/27/2013

I'll just say that it involved frozen turkey meatballs and leave it at that.

by Dr. Ruthlessreply 8801/27/2013

I'm 6' 4", size 14 feet, black hair and blue eyes. You can imagine the weird ones I attract. Unfortunately for them I'm about as vanilla as one can get. I'm probably one of the most boring lovers anyone could have.

by Dr. Ruthlessreply 8901/27/2013

I know there are a lot of posts here about spanking, rough-housing, etc., but this one man I got down with wanted me to haul off and hit him with a closed fist while I was fucking him. I had already begun fucking him when he made the request, so I did it on the side of his head where it wouldn't leave a visible mark. Later, he brought a 2x4 into the bedroom, at which point I said I needed to go.

It turned out that he had unsuccessfully run for Congress. He kept calling me asking me to go camping with him after this incident. Well, he kept calling my voicemail, because I was not at home for any more of that shit.

by Dr. Ruthlessreply 9001/27/2013

Damn. I love it rough, but I 2x4?

by Dr. Ruthlessreply 9101/27/2013

Indeed R91. I didn't know what to make of it.

by Dr. Ruthlessreply 9201/27/2013
Loading
Need more help? Click Here.