Strangest or unique request you've received or given

[Boaxxx]

I'm curious as to some of the strange or unique request/roleplay scenarios that clients have made when setting up an appointment. Whether it be a request for certain attire (superhero costume, cowboy athletic gear, etc), a specific roleplay scenario or even a request regarding the atmosphere/environment (romantic candle light, outdoors adventure, sex club vibe, etc). We all have certain preferences so I'm sure requests run the spectrum. Do tell. 😁

 

[jeezifonly]

One provider I knew had a great space for his work, the right kind of passion and knowledge of the body, and as I had a few combo sessions (always including massage), I was comfortable asking him to use on me adventurous toys of mine I had brought. Hardly strange, not unique, but maybe rare?

[Boaxxx]

1 hour ago, jeezifonly said:

One provider I knew had a great space for his work, the right kind of passion and knowledge of the body, and as I had a few combo sessions (always including massage), I was comfortable asking him to use on me adventurous toys of mine I had brought. Hardly strange, not unique, but maybe rare?

And I'm sure he was open to the idea.

[jeezifonly]

16 minutes ago, Boaxxx said:

And I'm sure he was open to the idea.

Almost as much as I was.

[Wolfer]

Apparently asking for real, good, full body cuddles has been overwhelmingly strange to most providers when I ask for them. Almost all were not very good nor comfortable at cuddling and could only do it for about 5 minutes before getting bored or uncomfortable. 

And yes, I do explicitly make it very clear that cuddling is really important to me when enquiring about a provider's services. 

[BigK]

Just seems like a simple request that I feel most escorts would be able to accommodate.  Luckily a number of guys I meet are world class cuddlers.

[soloyo215]

I fisted Jesus.

Jesus is a masseur provider I see in Mexico, and since I met him back a few years ago, I always look for him and fist him.

I know the practice of fisting is not rare nor is it weird, but it's weird how it happened in my case. When I met him the first time, I went to get a massage, not even an erotic one. I'm not into fisting at all, and to this day I have no clue how my fist found its way into his butt in that first session. The thing is that I loved it as much as he did, and now I look for him when I go to Mexico.

I don't even think about fisting outside of those 4 walls of his studio.

[Wolfer]

3 hours ago, BigK said:

Just seems like a simple request that I feel most escorts would be able to accommodate.  Luckily a number of guys I meet are world class cuddlers.

I haven't been so fortunate. Where I live the overwhelming majority are focused on providing the "no strings attched, treat you like dirt" dominant top fantasy. And I love (and long for) intimate, sappy, gazing in each other's eyes, cuddle sessions with cute, insatiable bottoms. 

[+ Jamie21]

Quite a few lol. One of the more unusual ones is a boxing role play. I’m the coach, client is my boxer who I am massaging before his fight. He has ambient boxing sound playing in the background, wears boxing gloves, shorts and a box to protect his cock. I start to massage him, giving him tips on the fight and as the massage progresses we both get naked and I end up fucking him. 

[dutchal]

To turn this around, to strange requests from a provider, I once had an escort, after sex, ask me to shave his (hairy) back.

[CuriousByNature]

5 hours ago, soloyo215 said:

to this day I have no clue how my fist found its way into his butt

[la_connor]

3 hours ago, dutchal said:

I once had an escort, after sex, ask me to shave his (hairy) back.

Me too! Incredible. I would have done it for $350...

[la_connor]

Once a provider asked me how he should dress when he came to my hotel. I said he should dress like Allen Iverson. I was joking but he knocked on my door kitted out in a Pistons jersey, sweatband, long baggy basketball shorts and a very stinky pair of sneakers. 

[Boaxxx]

5 hours ago, Jamie21 said:

Quite a few lol. One of the more unusual ones is a boxing role play. I’m the coach, client is my boxer who I am massaging before his fight. He has ambient boxing sound playing in the background, wears boxing gloves, shorts and a box to protect his cock. I start to massage him, giving him tips on the fight and as the massage progresses we both get naked and I end up fucking him. 

That's definitely a unique scenario that I would have never thought of but a hot one too.

If you've had quite a few do tell.

Edited yesterday at 01:20 AM by Boaxxx

[+ glutes]

Fairly vanilla here, but I was staying at a very nice hotel and asked the provider  not to show up slovenly dressed. When I met him in the lobby he was in  a (almost) Brooks Brothers suit!

Edited yesterday at 01:47 AM by glutes

[big-n-tall]

Not really strange, but one now retired provider, I asked him to treat me like the guy on the team who needed to be whipped into shape. We got so into this, that even now when we text each other, I still reference him as coach. 😁

[+ Jamie21]

7 hours ago, Boaxxx said:

That's definitely a unique scenario that I would have never thought of but a hot one too.

If you've had quite a few do tell.

One interesting one was being hired to go to a sauna. The client had used a sauna (bath house) a few times and was annoyed that no one would play with him. He wanted to get into some group action there and get DP’d. So he hired me to hit him up at the sauna and make this fantasy happen. Basically I had to turn up after he’d been in there for an hour, find him, act as if we’d never met before, and have sex with him so that it would attract guys to watch and join in and he’d get DP’d and have multiple loads. I did warn him it might not happen and he should hire two of us to be certain of it but he didn’t want to spend that much and he was convinced he’d get loads of guys if they saw him with me. 
It wasn’t entirely successful…The place was busy enough and I found him in the jacuzzi. I sat next to him and after an appropriate period of time we started kissing and playing. Another guy in there joined in for a bit but then the attendant saw us and told us off for sucking cock in there so we went to the steam room. I sucked the client in there but no one seemed interested in joining, plus it was too steamy and hot. We tried a few other places; cinema room, sauna, corridor but guys seemed only interested in me not my client which started to annoy him.

I suggested we find a cabin and leave the door open while we fucked to see if anyone would join us. He was up for this so we found a nice cabin where lots of people walked by and it didn’t take long for a guy to come in. Unfortunately the guy who joined us just wanted to get fucked so I did him and then he left. Next guy was also a bottom so he didn’t stick around.. All we seemed to get was guys who wanted to get fucked so I left the client in there and went out to find another top for him. Eventually I found someone, took him back and we fucked the client but the guy wasn’t really into it and it didn’t last long before he made an excuse and left. I had to say to my client that trying to force these fantasies isn’t the way to realise them. His anxiety and demands were the barrier to him just relaxing and enjoying himself. I don’t think he really understood that. 

[Dicastri]

A provider really wanted to grind his dick on my couch/bed to finish. I just wanted to see him cum somehow, so that’s what he did to ejaculate. 
 

Apparently he has an idiosyncratic masturbation style

[jackcali]

10 hours ago, glutes said:

Fairly vanilla here, but I was staying at a very nice hotel and asked the provider  not to show up slovenly dressed. When I met him in the lobby he was in  a (almost) Brooks Brothers suit!

Similar story here.  I asked a provider I'd seen a couple of times before to dress like an applicant for a professional job for a roleplay with me being the hostile interviewer.  He came to my hotel room in a suit and tie and white shirt (I specified that detail).  We started the "interview" but within 60 seconds I was so revved up I said "forget the roleplay, let's just get to it."  It was a great session.  

[+ DrownedBoy]

This year I've been hiring almost exclusively non-English speaking Latinos, and I insist they speak only Spanish and correct mine.

It's a great addition to Rosetta Stone, real (but very simple and basic) conversation. And I file the Zelle payments as "Spanish instruction".

They seemed more flattered to end up as a language tutor than finding it weird. And glad this hobby can lead to personal improvement.

Edited yesterday at 01:48 PM by DrownedBoy
clarify

[Peter Eater]

18 hours ago, soloyo215 said:

I fisted Jesus.

Ding-ding-ding! We have a winner!

[+ KensingtonHomo]

18 hours ago, soloyo215 said:

I fisted Jesus.

Please make this a T-shirt. 

[+ PhileasFogg]

On 3/19/2026 at 10:30 PM, Boaxxx said:

I'm curious as to some of the strange or unique request/roleplay scenarios that clients have made when setting up an appointment. Whether it be a request for certain attire (superhero costume, cowboy athletic gear, etc), a specific roleplay scenario or even a request regarding the atmosphere/environment (romantic candle light, outdoors adventure, sex club vibe, etc). We all have certain preferences so I'm sure requests run the spectrum. Do tell. 😁

 

The providers usually request that I remove my superhero costume 🤣

then I tell them - “it’s not a costume” 😉

Edited yesterday at 08:46 PM by PhileasFogg

[Braziliancutee]

Some clients love some outfits and my style (kind of European) from my pics on RM and sometimes they ask me to wear those clothes when we are going out for dinner or whatever. Also a few clients already asked me to wear suit with them. And I love to be always well dressed 

[Braziliancutee]

19 hours ago, dutchal said:

To turn this around, to strange requests from a provider, I once had an escort, after sex, ask me to shave his (hairy) back.

What??????? That’s disgusting a provider can’t ask this. He need go ready and perfect for the client. I care a lot with this things that why I spend a lot money on laser hair removal.

Edited yesterday at 04:16 PM by Braziliancutee