Strangest Requests When Hooking Up

[SpectreAgent]

4 hours ago, ErosWired said:

She wanted to watch…the schoolboy spanking?

One wonders what goes on in that flat on nights when they don’t have a guest…

I think there were definite weird vibes in that relationship. A couple - one English, one Spanish - once picked me up at a sex party and took me to their rather expensive pad in Greenwich. The English guy drew up a chair and wanted to watch his Spanish partner fucking me, which I found....interesting. But this was on a whole differnt level of weirdness.

 

 

[BritishCumdump]

5 hours ago, rawsatyr said:

Oh I forgot to mention, I'm kinda vers and actually really turned on by tops whose cunt looks well-fucked. Most likely he took a few poz loads that day himself and that INCREASED danger thrill turns me on!

As to sexy bottoms: I'm more turned on by verbal powerbottoms with a pretty, cut dick getting hard from being penetrated or even NUTTING without touching the dick, than with "I'm justa hole!" vanilla bottoms going ass-up and doing nothing more. Same though goes for boring tops who just screw from behind and are done with it... 

As 'they say': "It takes all kinds!" But just sharing my personal angle for entertainment purposes.... 

 

 

You're right, I totally agreed about it being weird for a top to want to see a bottom's dick but I guess if you enjoy playing with it ot seeing it there as you fuck it makes sense. I just don't like the request because a) I don't like being sucked off so need to put it out to the guy that I'd prefer that doesn't happen, b) I'm usually locked in chastity so even if I sent a pic of my dick, that's not gonna be an option on the night. 

It's nice to see it from the top's perspective tho 😘

[BritishCumdump]

4 hours ago, T-Girl-Cumdumpster said:

I had a guy who took me to a really cruisy park to strip me naked and specifically watch a bunch of homeless men fuck me and blow loads in me out in the open where anyone could see. he legit hate fucked me semi regularly and legit thought I was a disgusting fem whore and would often tell me I’m a “worthless piece of $hit" and that if I was his son he would have sold me as a sex slave. he was always trying to find new degrading stuff to do to me. so he prearranged for a few dirty homeless men to meet me there with him and several other homeless and regular cruisers ended up using me while he watched and told them to rape me and piss on me and ended up ramming his entire forearm up my as while I laid naked on a picnic table getting strangled and pissed on.

there is another guy who liked to dress me up as his daughters and fuck me in their actual beds. I actually look exactly like his older daughter.he also has me call him daddy and dad and he calls me by their names while he brutally sodomizes me.

This is crazy hot, I'd fucking love that to happen to me. I gotta get some homeless dick now ❤️❤️❤️

[BritishCumdump]

1 hour ago, RawPlug said:

I think there were definite weird vibes in that relationship. A couple - one English, one Spanish - once picked me up at a sex party and took me to their rather expensive pad in Greenwich. The English guy drew up a chair and wanted to watch his Spanish partner fucking me, which I found....interesting. But this was on a whole differnt level of weirdness.

 

 

Yeah see that's far more standard than having your female housemate watch, especially if she's giving Linda vibes. I'm still laughing at the mental image of them having a relationship where he dresses as a schoolboy and she's totally into it.

[jeff238]

This didn't happen to me, but I saw it on a Craigslist ad one night.

The guy wanted you to come to his house, door unlocked, come in and go to the kitchen and find a little wooden toy airplane sitting on the counter, then jack off and cum on the airplane, while he remained upstairs and not seen, then let yourself out. To sweeten the deal, he offered 3 hard boiled eggs in the fridge, as compensation. He also had a picture of the cute little airplane in the ad. I laughed so hard, I was useless for the rest of the night.

Another one. My friend, a top, had a guy that wanted to come over, get naked, lay face down on my friend's dining room table, while my friend made a tossed salad with specifically Italian dressing on the small of his back, and eat it. No sex, just salad.

[ErosWired]

1 hour ago, jeff238 said:

Another one. My friend, a top, had a guy that wanted to come over, get naked, lay face down on my friend's dining room table, while my friend made a tossed salad with specifically Italian dressing on the small of his back, and eat it. No sex, just salad.

He clearly misunderstood what is meant by ‘getting your salad tossed’.

Edited July 27, 2023 by ErosWired

[PissPigBrooklyn]

9 hours ago, HoneyBuns1980 said:

it just seems so incredibly strange to me why a top would want to give 3 shits about a bottom’s dong. You certainly don’t see any bottoms pining to see a top’s ass. 

Well, frankly I am an assman but a total bottom. I love to rim a top before he fucks me !

[SpectreAgent]

50 minutes ago, PissPigBrooklyn said:

Well, frankly I am an assman but a total bottom. I love to rim a top before he fucks me !

 

50 minutes ago, PissPigBrooklyn said:

Well, frankly I am an assman but a total bottom. I love to rim a top before he fucks me !

We're two of a kind.

[SpectreAgent]

3 hours ago, jeff238 said:

This didn't happen to me, but I saw it on a Craigslist ad one night.

The guy wanted you to come to his house, door unlocked, come in and go to the kitchen and find a little wooden toy airplane sitting on the counter, then jack off and cum on the airplane, while he remained upstairs and not seen, then let yourself out. To sweeten the deal, he offered 3 hard boiled eggs in the fridge, as compensation. He also had a picture of the cute little airplane in the ad. I laughed so hard, I was useless for the rest of the night.

Another one. My friend, a top, had a guy that wanted to come over, get naked, lay face down on my friend's dining room table, while my friend made a tossed salad with specifically Italian dressing on the small of his back, and eat it. No sex, just salad.

A therapist could make a career out of those two alone.

[damsonffpig]

10 hours ago, rawsatyr said:

Oh I forgot to mention, I'm kinda vers and actually really turned on by tops whose cunt looks well-fucked. Most likely he took a few poz loads that day himself and that INCREASED danger thrill turns me on!

As to sexy bottoms: I'm more turned on by verbal powerbottoms with a pretty, cut dick getting hard from being penetrated or even NUTTING without touching the dick, than with "I'm justa hole!" vanilla bottoms going ass-up and doing nothing more. Same though goes for boring tops who just screw from behind and are done with it... 

As 'they say': "It takes all kinds!" But just sharing my personal angle for entertainment purposes.... 

 

 

Hey totally agree 🐷😈

 

[NWUSHorny]

5 hours ago, jeff238 said:

This didn't happen to me, but I saw it on a Craigslist ad one night.

The guy wanted you to come to his house, door unlocked, come in and go to the kitchen and find a little wooden toy airplane sitting on the counter, then jack off and cum on the airplane, while he remained upstairs and not seen, then let yourself out. To sweeten the deal, he offered 3 hard boiled eggs in the fridge, as compensation. He also had a picture of the cute little airplane in the ad. I laughed so hard, I was useless for the rest of the night.

Another one. My friend, a top, had a guy that wanted to come over, get naked, lay face down on my friend's dining room table, while my friend made a tossed salad with specifically Italian dressing on the small of his back, and eat it. No sex, just salad.

Neither of those scenarios sound that strange to me after living in the PNW for 16 years. I've learned that not mentioning fucking in their profile or in the initial communication usually means they don't. The salad scenario not only doesn't involve penetration, it doesn't even require a dick, which is another problem I run into frequently.

[T-Girl-Cumdumpster]

8 hours ago, BritishCumdump said:

This is crazy hot, I'd fucking love that to happen to me. I gotta get some homeless dick now ❤️❤️❤️

yeah it was pretty hot. he said he read about something like that on breeding zone and wanted to find a t-girl that was both sexy and willing to have it done to her and he heard my boyfriend liked getting me fucked by homeless men in the parks and porntheatres

[PozTalkAuthor]

Former fuckbud who was close friend of my ex's: he wanted me to eat his hairy armpits like I would have been eating grass from the ground. Rejected, I'm not into those "animal roleplay" things. 

My current bf, when we first became sexually confident, wanted me to fuck him doggy style on my piano bench, and when he felt me close he called me FREDDIE (I let you guess the name's origin) and begged me to... Censorship on myself because I'm out of the backroom. 

Gladly, but I don't deserve to be compared to Freddie! 

This play has gone now, we have fun anyway. 

And, from my part, I ask him to hold objects with his ass and push them out. Of course this is not the only one but he does not want me to share. 

 

My ex (the abuser) wanted me to wear female underwear and call me "Sandra" I had indulged him only because I feared to lose him -what always happens between abuser and abused-. Water under the bridge.

[BootmanLA]

23 hours ago, HoneyBuns1980 said:

See, that’s the issue: it’s nice that you identify as versatile, but, they’re the ones who have the most trouble understanding that not everyone else does. Someone who is a self-identified bottom doesn’t want to be fooled by a “top” before sex, who turns out to be versatile, or even a bottom during it. That has been my experience far too long. 

I'm a "self-identified bottom" and I always appreciate a nice ass on a top man. It's great for grabbing hold of if we're fucking face to face, pulling him in deeper, for one thing. Deciding what all "self-identified bottoms" want is pretty presumptuous. I understand some bottoms - not pointing any fingers - want nothing more than a dildo on a vaguely human-shaped body, because they literally don't care about anything but the dick, but that's not everyone.

To answer the OP's question, the weirdest thing I've ever had someone request is to be force-fed an entire loaf of Wonder Bread (the basic sliced white bread version) before sex. 

[Ieatcumholes]

Having read through this thread, all I can say, is 🤯🤯🤯!

My fantasies/kinks are just that - mine! If the vibe is right, I'll mention them as a possibility to the bottom I'm going to hook up with. If they're not into them, I drop the conversation as I don't need to have my fantasies/kinks happen every time I have sex.

Some of the listed requests are so weirdly specific, that I have to wonder what happened in those people's lives to get them to that point...