Here is my dilemma!

Years ago, I did pop the cherry of a virgin boy.

He was 19 and adorable, never been with a woman and I did make sure his experience was the best ever and I really wanted to be one in a lifetime experience for him.

Now, years later, he found my site and contacted me:

"""Hello ***,

I don't know if you remember me.  We met about 8 years ago when I was a virgin.
We met across from *** in the parking lot of the Marriot and you took me to your room.
I will never forget the experience I had with you, the things you did to me.
I want to remind myself again how it feels.
After all these years, you are always in my mind.  
Would you consider meeting me again?

Please!

S.T."""

Now, should I meet with him again?

Do you think if I do I will ruin his memory of his first sexual experience?

I still remember, fondly, of my first. At the time, he was the best to me but I think if I meet with him again I will be disappointed and think "I lost my virginity to THIS guy?"

lol, I don't want to spoil this young man memories. He might have the same feeling I have for my first, thinking I was the best he ever had and  might get disappointed if we fuck again.

We all remember our first, right? What should I do?

Thanks for your help!

BDG

Somehow I suspect that any repeat with you would set new records and create new memories just as sweet and unforgettable as the previous encounter. Just a hunch

I didn't lose my virginity to a lady in the hobby but I have a similar tale.  There's a lady--I won't say where--whom I saw after I started hobbying and the time with her was better than anything before or since.  I've had the opportunity to see her again but I haven't taken advantage of that opportunity because I don't think anything could top the first time I had with her.  Maybe I'm being short-sighted.

Rinse, Lather, Repeat - when does the madness stop!?

I see this as a case of things only getting better with experience - you rocked his world, and I'm betting you have only gotten better since then.  And likely so has he.  And the fact that both of you are thinking so much about it - well that bodes explosively for the both of you!  

So I say - have at it, and hopefully the evening will be even better still for the both of you.

 -- D 'would bang ya again' H

I feel the same. BDG is exciting in her posts, so her appts must be outstanding as well. He will never lose the great memories of his first time with her. This would be a new chapter, and I'm pretty sure he'd hold her in even higher regard should she see him again. Guys always remember the good times!

with some chat before you meet.

The worst that can happen is, if he's disappointed, then he grows up a little, and you've given him another valuable lesson.

Voice of experience here.....

I think it would be fun.  If he was worried about his memories being ruined, he wouldn't have contacted you.  Still, I raised an eyebrow when I got to the "after all these years, you are always in my mind."  Not sure if that's sweet or creepy.

Good luck!

show you what he's learned in 8 years!  lol.  He'll always have memories of his first time.  This is an opportunity to make new memories.

I think it would be good for you to see him again.  Maybe in these 8 years he hasn't had anywhere near as good of an experience with other women and remembers that tremendous first time with you. Plus, maybe he has a few new ideas of his own he wants to try with you!

I remember my first time, and if I had the opportunity to see her again, I would.
Just imagine the disappointment this guy will go through if you decline.

Do him.  The rest of us can wait.

Fuck him again and write back with the details.

If he is willing to pay your current rate and you have time in your schedule, why not?

BDG -

A thought struck me as I was reading your post. He wrote "After all these years, you are always in my mind." He comes across as sounding just a tad bit obsessed to me. But maybe I’m reading too much into that. For your safety you might want to consider screening him just like you would any hobbyist who is new or who you have not seen recently.

Have fun, but be careful

C_K

I would say enthusiatically, YES.  Just the fact that you hesitated shows a degree of caring & concern, because of that you'll make it special once again.  The only problem I see is that you may set the bar too high to continue.  

You know how guys like the GFE...  reunion of long lost loves...  this is it.  It's his fantasy...   it could be a grand time for both of you...  enjoy it.
S

and that (based upon my past weekend) alters how I view this.... If this was a civie encounter... I would say - do not see him... why?  because what passed between you is totally innocent... keep it that way - but obviously if he found your web site... he was looking.  and what you may ask was he lookin for!   hee hee.... and there is the issue... someone who is professional - would you now charge someone who you shared a great time with?  or would you say - just for you...   well - you get the drift...

NOW - if he paid you!?  I am with all the rest - by all means see him.  He sounds mature enough to see you!  I am considerably older than he is - and there is one woman who I will not see again... as I am afraid of not being able to live up to the memory of the one time I saw her.... it was magical - no other encounter (not my first time ever... not my honeymoon... not any sex ever compares with that night with her - and I just would not want to tarnish that evening...) so for him to contact you!?  well he seems to have a grip on the reality of it all...

I think you will have a great time - for as some have hinted... he may wish to try some "new" things with you!  

What a problem to have!   and here I thought it was someting (along the lines of Eliot Spitzer) to do with Hillary Clinton... and dodging bullets.... hee hee

i don't see this as a problem...see him don't see him it's up to you.

I suspect that he is older and more experienced he will be a better lover as well.....

From what I have read about you, you didn't get any worse in the sack and he is probably even better now then he was 8 years ago.


Fate has again brought you two together. Heck he may even give you a fond memory.

You might want to find out what he became, job wise, after he grew up.

Hope he is not a _________.

SexyMaddy

No doubt, do it!
It will add another chapter to the nice memory

The guy is asking you, so he has thought about it before.

I'm not sure this is for real? Someone who's been in sex work for at least 8 years -- you'd think this situation would have come up already? And she'd be better off asking other providers for input no? But maybe it is for real so:

The tone of his email sounds rather immature for a guy who's almost 30, and therefore trips my creepy meter. I'd probly ask him about his experiences since seeing you, whether he's had experience with other escorts, or at least strippers, etc. If the answer is no, I'd personally stay away.

The best clients shower, show up on time, tip well, and don't say stuff like "after all these years you are always on my mind". ya know?