Would it be rude to ask escort to wear sexy outfits/jockstrap for me

[Nvr2Thick]

walk in my hotel room wearing nothing but a jockstrap with a long coat covering his body (legal). He would only take of the jacket once inside the room.

 

JJkr that's a hot outfit

 

It's worth asking as long as you realize that you're just asking and not demanding. I can imagine that this might not be the easiest request to execute, and that some escorts might not be cool with it.

 

I used to often ask escorts to be shirtless when we meet. Some refused to pull of their shirts before knocking on the door to my hotel room, while others were happy to do it. I tried to ask in a way that was flattering and played to my fantasy. The guys that refused sometimes gave pretty good reasons, but I understood regardless. There was one guy who went apeshit on me for asking; suggesting that I'd be auditioning him through the peephole.

[cany10011]

I have a nice selection of undies and jockstraps that I find sexy and purchased them for my regular guys to wear after showering before playtime. I love Modus Vivendi underwear with their snap closures and openings for easy access and sexy Pikante underwear. Of course, Andrew Christian is a staple too.

[+ Keith30309]

Sort of an inverse scenario: there was a companion who I had seen several times and with whom I had become very comfortable. We had settled into a bit of a rut... different day, same thing.

One day he asked me if wanted a surprise... "sure". He disappeared for a minute and came back wearing a pair of ladies panties - black, lacy and with mesh in the front.

I had never imagined he had a fetish for that and was astounded. After an ahha moment of brief explanation we had an interesting time playing with them... he immensely enjoyed my rubbing them over his skin, drawing them tight, etc., and couldn't contain his 'happiness'.

It's not my thing but watching him enjoy himself so much was a turn-on.

[Frequentflier]

Im thinking about asking the guys that Im going to book in NY to wear some sexy outfit/underwear for me. Ranging from walking in my hotel room in nothing but a jockstrap to wearing army uniform etc... Would it be rude to ask the ask to wear specific outfits and wear jockstrap before our first meeting.

 

Heck its a compliment to them. Your request says you find them attractive and sexy. That they have a body that would look good in a jockstrap! I could see a guy being upset if you asked them to wear a tarp over their bodies

[Becket]

I require all my guys to wear a burka

[ACoupeur]

Couldn't agree more, Keith, it's great to see @ACoupeur commenting [i already said welcome to Slimtwink].

Well thanks guys!!

[Frequentflier]

I require all my guys to wear a burka

 

Some men do have beautiful eyes and a Burka is good way to highlight them. And then there is the whole mystery before you unwrap him

 

I'm off to write another romance novel.

[BaronArtz]

I have asked escorts to model several pieces of underwear that I bought for them. It was fun. They didn't seem to mind.

[seaboy4hire]

Im thinking about asking the guys that Im going to book in NY to wear some sexy outfit/underwear for me. Ranging from walking in my hotel room in nothing but a jockstrap to wearing army uniform etc... Would it be rude to ask the ask to wear specific outfits and wear jockstrap before our first meeting.

 

I would avoid asking a hooker who hasnt served to go out in public in military uniform. I'm too lazy to confirm but I'm pretty sure that doing so could land you in some trouble. And not to mention someone who has served might stop the hooker and ask about his service and what he did to earn the stripes and ribbons.

 

Hugs,

Greg

[mattr]

I would avoid asking a hooker who hasnt served to go out in public in military uniform. I'm too lazy to confirm but I'm pretty sure that doing so could land you in some trouble. And not to mention someone who has served might stop the hooker and ask about his service and what he did to earn the stripes and ribbons.

 

Hugs,

Greg

 

I don't think there are any laws preventing someone from wearing a uniform as long as they are not representing themselves as military, police, etc. (e.g. trying to arrest someone) Otherwise thousands of people would be in jail on halloween.

[Boomer]

It would be rude if you ask rudely.

 

But otherwise, you can pretty much ask if he is open to pretty much anything. If you do it in a polite and respectful manner, every escort who knows what he is doing will be receptive and will answer honestly and openly.

 

I vote against him entering into your room wearing nothing but a jockstrap, unless he is also into getting arrested.

 

Aside from that, if he owns a jockstrap, I am sure he would be thrilled to wear it for you. There is nothing sexier than getting ready in a way that we know our partner likes.

[Boomer]

I did this with Juan when I was in Vancouver for work, which at the time was frequently. Juan has this request mastered. What's the worst case scenario, he says no? Politely excuse yourself and move on.

[Juan Vancouver]

I did this with Juan when I was in Vancouver for work, which at the time was frequently.

 

Ah, the good old times!