Charlie

Tylenol hadn't yet been invented when my mother was pregnant with me, so I can't use that as an excuse.

Typically when I know someone well enough to share personal details about my life, I know them well enough to ask their thoughts on what I shared. Especially if it's my BF, or if I get a response from anyone else that I didn't expect or  understand. 

I'm not sure how much they would really care. And if I were a provider, and my client seemed fairly knowledgeable about how sessions go, wasn't very nervous, etc., I'd probably assume they had hired before. 
 
I don't really see the point of telling most people unless you know they have a similar 'hobby.'  I especially don't see the point of telling someone on a first date.
 
lf I consider a slightly different but related scenario-if I were straight and met a woman on a casual date for the first time, I can in no way picture myself telling her about all my previous sexual experiences whether those were 'free' or bought and paid for.

The tone was somewhere between judgmental and curious with a significant dollop of insecurity.  He mentioned several times that he did not know how he would measure up to a professional.  Again, I used the car analogy of a racing car getting you where you are going fast and in an exciting yet expensive manner but is impractical for real life use. and a roadster that can get you their in style with a much less intense ride in comfort and it is practical for every day activity.    Both are fine rides, different for different purposes and clearly not in competition with one another.  
Not a perfect analogy for sure, so if anyone has a better one please feel free to include it here.  
When I was in school, I used to consider classmates as either racehorses or plow horses.  The race horses got there quick and easy but they did not get all the work done.  Plow horses were much more reliable and could be counted on the get all the rows straight and done professionally.  I always considered myself a plow horse.  Unfortunately, no matter which kind of horse I may have been, I was never hung like one.  

To answer the question. We are pretty circumspect about who we tell. Mostly, it's very close friends who are extremely sexually liberal. They don't care. There's another level - also very small who know that we're "monogamish" (as we only see others together). We sometimes share our adventures (both hiring and not) without mentioning when we've hired. 

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