He would be thinking the gal had sex with him because she liked him and he would then expect it to continue.

If she tells him the truth he'd be crushed and if she just ignores him he'll be hurt by that too.

If you tell the guy you are setting him up with a provider, he'll feel hurt that you think that is the only way he could ever have sex, and won't see you as much of a friend (and for good reason.)

The best way to help out a friend who isn't finding a gal is to coach him (Or get him some professional help to do it.  Such people do exist - I saw one, for example.) and then bring him to places to meet women for RL experiences.

The hobby is not the place to find satisfying real life romance.  It is a sexual amusement park.  You don't send a person who needs help with finding a career to Disneyland to live his life.

I am painfully shy as well, if anyone wants to set me up with a hooker without telling me, please feel free to do so, but make sure you spring for an overnight, i will get suspicious if she doesn't want to cuddle, and by all means make sure she is a hottie.

and do you really think that Tardwell is going to coach anyone on how to scored with women? Come on fisher, what were you thinking??

but to actually answer the OP, i have never set a friend up that way, but I have done it for clients visiting town, Usually what I have done is paid a stripper to pretend to like the guy and leave the club to fuck him without charging him, and without telling him that I paid for it. It gives the guy a great story to tell when he gets home, it's a huge boost to his ego, and people tend to spend more money when they are feeling all "macho" about themselves.

I actually AGREE with you, with a couple of caveats of course.

One thing you will need to do is create a viable reason that he will never be able to contact her again, Make sure she is either from out of town, or is in the CIA  or "something" so he won't wonder why this new "love of his life" has disappeared without a trace.

Guys like you describe are prone to fall in love with any woman they sleep with, as others have said, you don't want to do more harm than good, but other than that, it could give him a boost of confidence that he seems to desperately need, I mean after all if YOU are calling him bashful, he really must be a wallflower.

Now don't get any delusions of us all of a sudden becoming buddies or anything, but I did say that if you stopped posting like a moron, i would stop treating you like one, and this was a legitimate 'non idiotic" OP IMO. Hopefully your first of many.

The slightest clue the ladies  are providers.  I keep my lips sealed tight,  very tight like my favorite girls poon.  Never told any of them cuz that's private matters for the girls especially when they trusted me enough to transition to civvy friendship.  

as there will no money exchanged, that he knows about at least, and he will never know she is a hooker.

now a "nut bar" is a different story, but despite all the ladies claims that they would have to screen the guy, I guarantee you it would not be that big an issue, and could easily be overcome.

Explains why he doesn't have too many friends here,  if he's the type to deceive his friend and play a very cruel prank like this.  
It would give his friend false hopes of a real civvy date.  That's just very cruel and I'd give the biggest wedgie to any friend who does that to me.  

but you need to tell him what you did right after the experience. He got the experience of a lifetime and then finds out immediately what the deal is so there is no illusion of an extended romance, unless, of course, he starts to pony up the dough. BTW, you can be my friend anytime, but it will have to start with a free hooker!

...great line. Sorry but I'm going to steal it.

Just because you pass her screening..
What would make her think your friend is okay too?
He could be a nut bar, or a cop!

Can you imagine anyone being a bigger doofus than Roddy?  My suggestion is he should just take his friend out and shoot him.
[Earth to Roddy.  I am not actually suggesting you kill your friend, any more than I ever suggested you were like a rapist.  Kind of sad I need to say this, but....]

Would want him screened too, directly and not through you. You might think he is a nice guy but you are not the one spending alone time with him BCD.

"Your body isn't a temple, it's an amusement park.  Enjoy the ride."
From his book, "Kitchen Confidential."

-- Modified on 3/14/2014 9:55:21 AM

I did NOT want to lose it from seeing escort.  Yeah some people have these little wishes and I'm sure your friend might too.  

Just let Roddy know the donation is for my time and companionship only.
Anything else that takes place is between two consenting adults.
You get a pass because you are a Bond girl. :

Getting ready to start the day...  At 11:30.  Damn I'm so lazy.

That's what Jim Carry did to Mathew Broderick in The Cable Guy

I'd be uncomfortable...very awkward situation, not only during the 'date' but afterward.  

Ummm, nice name for game. Let me see, if can create an app for that!

Many years ago. Only it was never made clear if his friend knew I was paid for my companionship. It wasn't a pleasant experience for me at all. The guy had fun, but I was underwhelmed and a little turned off. Even during dinner I was thinking how challenging it would be. It reminded me of why I'm indie.

Please do not tell someone else they will have a good time, especially in the bedroom department. You have no idea what he is like with women in that setting. Unless of course you have fucked him or been fucked by him. And even that is not an indicator that his fucking style is what a lady would enjoy.  

I was getting worried because I hadn't heard any chatter about girl friends (he's 23 and on his own for a couple years).  We talked, and he's been getting laid, just thought I'd be prudish about it.  I told him to get his sexual experience now while he can and figure out the difference between lust and love.  He's got a really crappy job, so cash is very tight for him.  Now he hits me up for date night money.

I'll help out dear ole dad on that mission!!
She seems like a kinky porn star older lady who is super hot, and experienced.
Just keep your whale dick away from me, and we are all good

My very first thought when I read the OP question was "I haven't, but I think that would be a really bad, idea". And for all of the points Mrfisher described, plus one.  

...is to "double date" with two escorts at a hotel nightclub. Assuming you and your friend have separate rooms, and assuming that the escorts understand that nothing beyond being good company over drinks is EXPECTED, you could pair off and let the night be what it turns out to be. Could be an interesting experiment if handled correctly, but could also fail on all fours. But that's the nature of anything experimental, isn't it? Beauty demands risk.

I can get to Vegas.
That's it!

Since I am already spending your inheritance anyway, I'll spring for Robbin.  Besides, she's heard so many tales about my Manly Shaft I think she'll do us both for free as long as we give her a great review.
I can guarantee her that because I'm as big a whore as anyone.
Book it, Hound-O!

Unless he asks you for help, let him be a man, and take care of this himself.        

-- Modified on 3/15/2014 2:32:01 AM

...the proverbial dirty old man.  Had a stack of Playboy/Penthouse, and occasionally rougher stuff like the old "Screw" magazine, and my personal favorites, Penthouse Forum and Penthouse Variations.

If you feel like such a loser for being here, i can think of a great solution, and don't let the door hit you on the ass on your way out.

Is that the woman he is with is the one that will be teaching him how to please her, not any other woman. I employ one thing, be very gentle to start and let her guide. As for anything else, IMHO  is very woman specific and not to be used gender wide.

That puts a lot of pressure on a lady. You hear the guys testing the waters before overnights, well some of the ladies would not touch that scenario with your pole, so maybe you might want to rethink this surprise and let your friend deal with his libido and sex life.

But some things are nearly universal.  Among them, take your time, more foreplay is better, don't rub too hard right there, very light caresses are always good, and you're right, learn how to read body language.

Interesting thought... Doubt the guy will just give up his work info. before he understands what this is about. Also, the provider would want to protect herself from any possible exposure.  

Ive had several regulars try and hook up these situations... one guy caught on and when i took him to the room he said we should just pretend to "do the deed" and not tell his friend we didnt do anything.... cause he felt his friend (the one who set it up) liked me a lot and he didnt feel right about it! I knew this man well and saw him often... met most of his friends and hooked up with a few (at his expense)  
But an unsuspecting friend is probably not the best one to set up in this situation... may make him pretty uncomfortable if he isnt into "hooking up" on a random thing!