I've done this before a couple of times and have always found it to be pretty fucking exciting and invigorating. But it’s been quite a few years ago now. Still, I have a few buddies that I know who do some pretty high profile "escort" work and for some major agencies around the city. Two have actually been young guys out of my same firm (who just loved the sex) but most from the very expensive fitness club I've gone to almost from my first year in the city.
The current "ask" for me to assist has come from my buddy Xander since as expected he becomes way too over-booked (or I should say "over requested") around Valentines Day. He has only a limited number of hours and just one cock (sizeable as it is) to service all the requests. And let’s face it, a lot of guys can only cum just so many times in a span of say 48 hours. Of course, he's hardly a low-level rent boy and his rates are pretty impressive. He won't even see a client for less than 4 hours, and most are over-nighters. Which obviously puts him in quite a bind around any holiday (particularly one where the whole rest of the world will likely be fucking).
I wouldn't be able to "sub" with any new client, but he can hook me up with one of his many repeaters if they are agreeable. Fortunately, we have a lot of similarities, height 6'3", hair and eye color, he says he's 230 in weight but I'm the same and am quite a bit more muscular. The added weight he's packing somewhere couldn't come all in cock since even though he's well known for possessing a womb busting near 11 inches -it's relatively thin (according to him). I'm just over 10 (on a bad night) but still a jaw breaker and much thicker.
I really don't want to say too much in advance only that he has scheduled me for a full evening with one of his regular clients. All the arrangements still go through his agency so money never even gets mentioned during the "date". I never accept anything anyway. But the client still thinks she's paying for my "services" and that's the fucking thrill. At first, she was evidently quite unhappy about Xander not being available, but when presented with some other possible options she obviously changed her mind. She's already reserved a room for the night at the Knickerbocker, one of the corner suites I believe. Which considering the night and the location on Times Square was no mean feat. I'm supposed to try and arrange dinner reservations!! THANKS. Good fucking luck in Manhattan on Valentines night. Fortunately, I have a lot of good connections, and friends with even better connections. I'm going to need it.
I haven't yet seen a pic or talked to the lady. She's actually supposed to call me at this point. Guys in the agency are never to photograph their clients. What I do know from Xander is that she's in her late 40's, maybe 5' 7 with large natural breasts (FUCK YEAH) and just about the meatiest, thickest set of beef curtains he's ever had to work his cock through. It's not the tightest pussy, but I'm also thicker than he is - so we'll see. He's purposely not going to tell me anything more about her, yet refuses to say why? Which is curious, but only makes me hornier.
As if me being horny was going to be any real problem at this point. Valentine's Day is also Ash Wednesday and therefore the first day of Lent! Who the fuck was in charge of the calendar this year? Sorry bitches, when I cum on Wednesday night I'll be cumming like a motherfucker. Because I also know I won't be cumming again for a long time. The only question is if this lady is going to let me go raw and blow deep inside her pussy. She'll be past child bearing age, but if there's any way, I can still manage to flood her womb I'll sure as fuck try to find it. I'll have some of the specialty condoms I get in London that ARE large enough, but even though I keep them in the frig. they're still nearly 2 years old. My cock is just too fucking thick for any other condom to work god damn it. I've had this conversation too many times already. I'm actually excited as hell about this. My body is really in pretty spectacular shape, and my balls have been churning out precum for days now. Lets hope she's not too disappointed.
Ok, Snorre (my golden retriever) needs to go out for a run and a pee. Actually, I also need to go out for a run and a pee.
UPDATE:
I finally got a call from my lady yesterday afternoon while still at my office and must say I very nearly creamed my suit during the conversation. She certainly sounds like a pretty demanding mature sex goddess to say the least. The fact that she admitted to likely having hired over 60 different male escorts in her life probably says something. I'm just not entirely sure what yet. She did allude to really hating guys being "wrapped" as well, which I took as a very good sign.
She was indeed a little anxious about dinner reservations, dreaming about landing a place like "Per Se" -which would indeed have been impossible and besides I fucking hate the ambience of that place (even though I haven't been in years now). The fact that I was able to score a much harder reservation I'm going to keep from her until we arrive. I just thought that dining in a very elegant dark wood paneled place with paintings of horses and assorted stallions adorning the walls would help set the right mood for whats to come after. I'm just worried that I may now have to seriously let a guy attempt to blow me for the favor. Lets just not dwell on that too much at the moment. The other caveat to getting this score is that we'll need to dine there late. Our reservation is around 10:30. Fortunately that doesn't bother either one of us too much. It just means we likely won't even leave the place until after midnight. This is going to be a fuck that brings in the morning light most likely.
I'll try to keep you updated as best I can if anyone is interested.
Happy Valentines Day, Happy Ash Wednesday, Happy Hump Day everyone one!!!
The current "ask" for me to assist has come from my buddy Xander since as expected he becomes way too over-booked (or I should say "over requested") around Valentines Day. He has only a limited number of hours and just one cock (sizeable as it is) to service all the requests. And let’s face it, a lot of guys can only cum just so many times in a span of say 48 hours. Of course, he's hardly a low-level rent boy and his rates are pretty impressive. He won't even see a client for less than 4 hours, and most are over-nighters. Which obviously puts him in quite a bind around any holiday (particularly one where the whole rest of the world will likely be fucking).
I wouldn't be able to "sub" with any new client, but he can hook me up with one of his many repeaters if they are agreeable. Fortunately, we have a lot of similarities, height 6'3", hair and eye color, he says he's 230 in weight but I'm the same and am quite a bit more muscular. The added weight he's packing somewhere couldn't come all in cock since even though he's well known for possessing a womb busting near 11 inches -it's relatively thin (according to him). I'm just over 10 (on a bad night) but still a jaw breaker and much thicker.
I really don't want to say too much in advance only that he has scheduled me for a full evening with one of his regular clients. All the arrangements still go through his agency so money never even gets mentioned during the "date". I never accept anything anyway. But the client still thinks she's paying for my "services" and that's the fucking thrill. At first, she was evidently quite unhappy about Xander not being available, but when presented with some other possible options she obviously changed her mind. She's already reserved a room for the night at the Knickerbocker, one of the corner suites I believe. Which considering the night and the location on Times Square was no mean feat. I'm supposed to try and arrange dinner reservations!! THANKS. Good fucking luck in Manhattan on Valentines night. Fortunately, I have a lot of good connections, and friends with even better connections. I'm going to need it.
I haven't yet seen a pic or talked to the lady. She's actually supposed to call me at this point. Guys in the agency are never to photograph their clients. What I do know from Xander is that she's in her late 40's, maybe 5' 7 with large natural breasts (FUCK YEAH) and just about the meatiest, thickest set of beef curtains he's ever had to work his cock through. It's not the tightest pussy, but I'm also thicker than he is - so we'll see. He's purposely not going to tell me anything more about her, yet refuses to say why? Which is curious, but only makes me hornier.
As if me being horny was going to be any real problem at this point. Valentine's Day is also Ash Wednesday and therefore the first day of Lent! Who the fuck was in charge of the calendar this year? Sorry bitches, when I cum on Wednesday night I'll be cumming like a motherfucker. Because I also know I won't be cumming again for a long time. The only question is if this lady is going to let me go raw and blow deep inside her pussy. She'll be past child bearing age, but if there's any way, I can still manage to flood her womb I'll sure as fuck try to find it. I'll have some of the specialty condoms I get in London that ARE large enough, but even though I keep them in the frig. they're still nearly 2 years old. My cock is just too fucking thick for any other condom to work god damn it. I've had this conversation too many times already. I'm actually excited as hell about this. My body is really in pretty spectacular shape, and my balls have been churning out precum for days now. Lets hope she's not too disappointed.
Ok, Snorre (my golden retriever) needs to go out for a run and a pee. Actually, I also need to go out for a run and a pee.
UPDATE:
I finally got a call from my lady yesterday afternoon while still at my office and must say I very nearly creamed my suit during the conversation. She certainly sounds like a pretty demanding mature sex goddess to say the least. The fact that she admitted to likely having hired over 60 different male escorts in her life probably says something. I'm just not entirely sure what yet. She did allude to really hating guys being "wrapped" as well, which I took as a very good sign.
She was indeed a little anxious about dinner reservations, dreaming about landing a place like "Per Se" -which would indeed have been impossible and besides I fucking hate the ambience of that place (even though I haven't been in years now). The fact that I was able to score a much harder reservation I'm going to keep from her until we arrive. I just thought that dining in a very elegant dark wood paneled place with paintings of horses and assorted stallions adorning the walls would help set the right mood for whats to come after. I'm just worried that I may now have to seriously let a guy attempt to blow me for the favor. Lets just not dwell on that too much at the moment. The other caveat to getting this score is that we'll need to dine there late. Our reservation is around 10:30. Fortunately that doesn't bother either one of us too much. It just means we likely won't even leave the place until after midnight. This is going to be a fuck that brings in the morning light most likely.
I'll try to keep you updated as best I can if anyone is interested.
Happy Valentines Day, Happy Ash Wednesday, Happy Hump Day everyone one!!!
