Shy first-timer in NYC wondering if anybody's ever hired someone with a friend

[whatsthefuss]

I've been window shopping for a while but just a bit shy to pull the trigger. I hired an escort a couple years ago but that was in a different location and sort of fell into my lap coincidentally. I'm worried I might just get so anxious that I end up not being able to perform or enjoying it fully. Part of it is just feeling a little awkward or self-conscious b/c I don't fit the prototypical older businessman daddy image.

I'm wondering if anyone has ever had experience hiring an escort with a friend? For some reason it just occurred to me that it might really take the pressure off some of my concerns. I also really like voyeurism too so I wouldn't mind sharing anyway. 

Thoughts?

Edited June 15, 2021 by whatsthefuss

[+ poolboy48220]

Nothing from me.  I only have one friend who knows I hire, and we have very different types.  I have hired two providers at the same time, there are plenty of threads discussing doing that.. 

[RyanDean]

I don't think "fitting" the "prototypical older businessman daddy image" matters much to providers.

That said, making sure YOU are feeling comfortable SHOULD be a priority for a skilled/responsible provider.

I suspect hiring a duo might be less complicated than hiring with a friend but I might also suggest that you seek feedback here on a few providers of interest to you. It might help to identify the right gent to ease you through your anxiety about taking the plunge.

 

[TruthBTold]

I have never hired with a friend however I think the situation might not help you create the perfect situation.  When I think about it, the feeling that are making you uncomfortable in the first place will still be there.  The addition of a friend won't really erase those feelings and although it may layer on a certain voyeuristic element at the same time it may add other feelings you are not aware of now.  For instance, are you and your friend planning on having sex or are you just planning on watching him have sex with the escort?  Depending, have you had sex with your friend before?  I just think you will be adding so much to the situation that it won't make you feel any less nervous.  As someone already wisely mentioned "making sure YOU are feeling comfortable SHOULD be a priority for a skilled/responsible provider." 

[jjkrkwood]

35 minutes ago, TruthBTold said:

I have never hired with a friend however I think the situation might not help you create the perfect situation.  When I think about it, the feeling that are making you uncomfortable in the first place will still be there.  The addition of a friend won't really erase those feelings and although it may layer on a certain voyeuristic element at the same time it may add other feelings you are not aware of now.  For instance, are you and your friend planning on having sex or are you just planning on watching him have sex with the escort?  Depending, have you had sex with your friend before?  I just think you will be adding so much to the situation that it won't make you feel any less nervous.  As someone already wisely mentioned "making sure YOU are feeling comfortable SHOULD be a priority for a skilled/responsible provider." 

 

It would have to be a friend whose dick is SMALLER than mine  !  😉

[kingsley88]

I'm curious if the provider will charge you more if you choose to bring a friend along.

If the provider offers an erotic massage, perhaps go for that option first. You get to meet the provider in person and see if he really makes you feel relaxed.  After the massage session, if  you had a great time, then talk to the provider about hiring him as an escort sometime in the future.

[+ WilliamM]

Suggest meeting him a few days before for coffee.

[MscleLovr]

To answer the OP’s question, I hired together with a good friend several times. It worked very well. 

The reasons it worked well are various. Our personalities mesh and we both enjoy handsome muscleboys. I arranged the hiring. He’s shy, I’m not; he loves to rim, I don’t rim; I love to top, he doesn’t; I don’t bottom, he does; and we both enjoy getting our cocks sucked. 
 

I guess @whatsthefuss it will depend on your relationship with your friend and what in particular you and he enjoy doing and having done to you. I suggest you have a good long talk with your friend about the details before you arrange the hiring. 

[+ Snbrd]

My first hire was with a friend. I naively knew little about the business beyond seeing ads in the personal section of the local DC gay rag. A FB invited me to join him for a birthday celebration. He had arranged a hire from an agency and we had a ball. That was so many years ago!

A few years later a couple I was friends with hired a guy to liven up a small group party. I got his number and called him later. That was my first "official" hire.

I think doing so with friend is a comfortable way to try it out. 

[CuriousByNature]

4 hours ago, WilliamM said:

Suggest meeting him a few days before for coffee.

This sounds like a great suggestion.  Have you found that providers are generally open to this sort of thing, and would the regular donation amount for their time be expected/offered?

[+ WilliamM]

9 minutes ago, CuriousByNature said:

This sounds like a great suggestion.  Have you found that providers are generally open to this sort of thing, and would the regular donation amount for their time be expected/offered?

Depends on the provider. But, it worked for me.

[+ JEC]

Lots here to unpack. 

Re: "with a friend", that could be awkward too depending on the friend.  Not all friendships will thrive or survive that kind of experience.

Re: "not the typical businessman daddy type", there are many types I wouldn't sweat this one

I'd try to focus on someone who will make you feel comfortable.  At the risk of stereotyping, maybe someone who's a little older (not early 20s), a little less perfect (not a chiseled god), and has been doing this work a few years with good reviews.  They should be mature and experienced enough to make you comfortable (while draining your balls 😃).   I'm sure there are lots of folks on here who would give you a recommendation.....

 

[Islesguy]

5 hours ago, JEC said:

Lots here to unpack. 

Re: "with a friend", that could be awkward too depending on the friend.  Not all friendships will thrive or survive that kind of experience.

Re: "not the typical businessman daddy type", there are many types I wouldn't sweat this one

I'd try to focus on someone who will make you feel comfortable.  At the risk of stereotyping, maybe someone who's a little older (not early 20s), a little less perfect (not a chiseled god), and has been doing this work a few years with good reviews.  They should be mature and experienced enough to make you comfortable (while draining your balls 😃).   I'm sure there are lots of folks on here who would give you a recommendation.....

 

I have written about my first hire here. While it was with someone most people here would consider a chiseled muscle god, he was also well known and we'll reviewed and his ad specifically stated he good with first timers and like guys of all sizes and shapes. I felt pretty good about my choice and he became a regular of mine.

 

[whatsthefuss]

Thanks for all the kind, thoughtful replies. I like the idea of hiring with a friend and of course making it all transparent and consensual and comfortable. I just like having a third party to defuse any awkwardness. It'll be my goal 

[dbar123]

If you choose the solo route I would suggest getting your feet wet with a 1 hr session. IMHO the older guys (over 35) are better to start off with. Usually they are better communicators and more relaxed. For a first experience have a few clear objectives to accomplish and just get comfortable….and enjoy. 

[rvwnsd]

On 6/14/2021 at 11:22 PM, whatsthefuss said:

I've been window shopping for a while but just a bit shy to pull the trigger. I hired an escort a couple years ago but that was in a different location and sort of fell into my lap coincidentally. I'm worried I might just get so anxious that I end up not being able to perform or enjoying it fully.

Let me start by saying I am not trying to be a smart-ass with what I am about to say. There's no reason to worry about worry. Stop worrying and find someone to hire!

 

On 6/14/2021 at 11:22 PM, whatsthefuss said:

Part of it is just feeling a little awkward or self-conscious b/c I don't fit the prototypical older businessman daddy image.

I think you mean "stereotypical." There is absolutely no "prototypical" client type. I started hiring when I was in my thirties because I had no time or patience for the bullshit associated with finding hookups. Ask some of the escorts who post here. They will tell you they see men of all ages, shapes, and sizes. 

 

On 6/14/2021 at 11:22 PM, whatsthefuss said:

I'm wondering if anyone has ever had experience hiring an escort with a friend? For some reason it just occurred to me that it might really take the pressure off some of my concerns. I also really like voyeurism too so I wouldn't mind sharing anyway. 

Thoughts?

I've never hired an escort with a friend and I don't think I would do so. I am not sure why having a friend along would take some of the pressure off. If your thought is the escort could be disappointed by you alone and having the friend along would satisfy the escort, just remember who is hiring whom and why. The escort is there for the client (you), not the other way around. That's not to say the client should behave poorly, treat the escort rudely, or do things that the escort does not want to do.

BTW: there can be bullshit to be had when hiring. If/when that starts, move on. My advice to you is the following:

• Get a clear picture of what you want out of the playdate and find an escort who can help you get it.
• Get to the root of your concerns.
• Look at the escort listings and make a top three or four list. Ask members about the escorts you find attractive.
• Talk/text/email the escorts and explain what you are looking for, your experience level, and your concerns.
• MOST IMPORTANT: relax and let yourself have fun.

[jeezifonly]

This friend would have to be a friend with whom you’ve already had …benefits… and would be someone you’d gladly share in a three way that he put together with an unknown third. Because that’s what you’d be asking of him. If you don’t have that friend, you might try a couple things in your search. 

Look for the mature, experienced guys, and guys who welcome newbies/inexperienced/married

Providers sometimes say in profile if they have a buddy they like to work with, and I imagine any guy you like will answer the question by the 2nd or 3rd text you if he thinks you are serious.

Do as much review reading as you can, because those will be where “my husband and I both had fun with him” will show up.

Im older and am sorta self conscious about my body. I would be more so with a trick or date than I am with providers. They’ll already have suffered through worse than what I bring to the party. 
Someone long ago said “you’re not paying the hooker for the sex, you’re paying her to leave”

A variation, you’re paying them to pretend they’re having as good a time as you are. Take the compliment, and have fun!