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Did you ever escort ... ?


orville
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... or sugar-babied in your life?

 

This is a question for clients. Those who think it's too private please ignore this thread. :)

 

I don't think I had the materials to ever escort in my life, but I "sugar-babied" few times during my 20s.

I think I did it as an average-looking guy, with daddy issues, who all of a sudden started receiving attention from "absent father figures".

I think the main factor for repetition was the thrilling sense of novelty and being looked-after by guys older than me.

But they were always short-lived love-stories because the mature guys were always looking for another baby to sugar.

Over time, I also became less tolerant to the possessiveness of those men and their rants when things weren't done their way.

I think if I had the body and the "gifts" of an escort I could have considered doing it at least for a season to know what it's like.

 

My story did not directly involve e$corting as it does not necessarily have to do yours, but feel free to share any exciting stories : )

Edited by orville
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I had a co-worker who was a sugar daddy. What made it horribly awkward was when a nice looking young man came in to say hi, I said "So is this your son?" Oops. I got the look of death, and he said, "no, this is my 'room mate'". Even weirder, he left this nice 20-something kid for the kid's dad, and told me he doesn't no how much longer he could go on secretly seeing both of them - I'm sure they knew, but my co-worker really had it gong on downstairs, so they probably just didn't care. His heart cared, however, as he died of a heart attack just a couple of months after quitting his job with me.

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Back in the days of gay.com, I got hit up on my profile by a couple of doctors in NYC who were basically looking for a houseboy. I was 29 and gainfully employed at the time, and I declined but was bemused.

Once in the Gaiety I was standing along the wall in the audience wearing cargo shorts and a Tshirt and an older guy leaving said 'you should be up on stage there" and I wondered if he was making an opening offer but I just laughed and said I wasn't sufficiently endowed to pull that gig off.

 

Temperamentally I don't think I could have ever done it. I certainly couldn't have done it for someone I wasn't attracted to. But hey, if, say, Pierce Brosnan had made me an offer...

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...

 

I don't think I had the materials to ever escort in my life, but I "sugar-babied" few times during my 20s.

...

Maybe I'm confused about the terminology, but I've always expected that "sugar babies" have intimacy with their "sugar daddies." The difference between the escort and the "sugar child" is that the former does it with multiple men over short periods, whereas the latter only does it with one person, and has more expenses taken care of. I must admit that when I've been with men I've been taking care of, I often have to shrug off comments such as when I'm looking for him in the drugstore and the employee says "You're son's on aisle 12."

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I was "approached" by an older businessman when I was in college. At the time, I was too clueless to figure out what the hell he was asking. If I'd known then......what I know now...... ;) :cool::p

Were you a jocktek instead of a jawjateck in those days?

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When I was in my early 20s and an impecunious grad student, I decided to try hustling one day. (There were no escorts in those days, because there was no gay media in which to advertise as one.) I knew where to go downtown to try to get picked up by someone who would pay, and I did it for several hours (I was young enough to be able to cum multiple times in one day), but I realized it was not something I was very good at, because I had a hard time performing with men I wasn't attracted to, so I didn't continue.

 

Around the same age, I was introduced to a man who was looking for a kept boy, and I had a few dates with him. He was a doctor who was in his early 50s, and I found him quite attractive, which was the main problem: I could have enjoyed having an affair with him as equal partners, but I couldn't have been comfortable being used as a boytoy. When I explained that to him, he made it clear that he was looking for someone who would simply fulfill a utilitarian role, not complicate his emotional life, so we became merely casual social friends.

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When I was 17 (few decades ago...) and living in Milan, Italy, very cute and shy (and a gay virgin), being a young opera lover I once saw a small music store basically dedicated to classical music and opera. I went in to buy an opera in LPs (LPs...!!) and there was the owner, a man in his late 40s/early 50s. He was very friendly and taken by my unusual passion for my age. Married with kids. I spent a good hour there, he started to tell me stories about past famous singers, all the famous old productions at La Scala which he saw, he would put records on for me to listen to. At the end he actually gave me a record for free (...) and told me to go back anytime to chat. (...).

I knew I was gay and I never told anybody, but I wasn't at all attracted to him. I felt something wasn't exactly "friendly behavior", but I was genuinely interested in his opera knowledge.

After 2/3 times I visited him, he told me I was very cute, he asked me if I ever had sex with a man, I said no, he smiled and he closed the door of his store. He took me to the back room and I lost my virginity there. I really didn't enjoy it particularly, but hey, what did I know? Before I left he gave me 10,000 liras (about 12$ of that time) because he wanted me to "enjoy some fun with friends".

I left a bit in shock for the loss of my virginity and for my extra 10,000 Liras I had in my wallet (I think my parents gave me around that amount for a month as a "salary" for my pocket money).

I went back I would say once a week during a couple of months to listen to records, to fuck in the back room and to get my 10,000 liras (once he gave 20,000 actually!), until I realized I really didn't like to have sex with him and I also felt it wasn't a "kosher" thing to do (also because I was totally in the closet, we are talking about the late 70s in Italy...), so after the last fuck I told him I didn't want to do it anymore, I proudly told him I didn't want money that time, and that it was better for me not to see him anymore.

So yes, I "escorted" in my teens! ?

 

6/7 years later (I already had totally come out of the closet, started to really enjoy sex and I even had a boyfriend) one day I was passing by his store and I decided to go inside. He greeted me, looked happy to see me, he told me I had become very handsome but he understood there was no chance anymore with me, so we chatted about music and life for a bit and I left.

I left Italy 32 years ago, but I went back to see my family at least once every year since.

 

About 10 years ago one evening I went to La Scala in Milan to see an opera, and in between acts while I was making time in the foyer I saw this older gentleman together with a guy in his early 20s. Of course I recognized the older man, so I approached him and told him my name, that I used to be an old client (...) of his store and that I really enjoyed our chats about music back then. He told me he wasn't really sure he remembered me, but anyway he introduced me to his "grandson", and after 3 minutes of chit chat I said bye and left.

 

I am curious to know how many Euros was he giving to his "grandson". ?

Edited by Italiano
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The bigger question is have you ever escorted and be a client on the same day? I admit to having done it when I first started as a hustler but a couple of years ago I saved up my earnings to spend some time with my favorite escort.

 

Give it a try again!

 

Spend your hard earn money in an hour of pleasure with an escort. It's a win win situation!

 

 

When I was in my early 20s and an impecunious grad student, I decided to try hustling one day. (There were no escorts in those days, because there was no gay media in which to advertise as one.) I knew where to go downtown to try to get picked up by someone who would pay, and I did it for several hours (I was young enough to be able to cum multiple times in one day), but I realized it was not something I was very good at, because I had a hard time performing with men I wasn't attracted to, so I didn't continue.

 

Around the same age, I was introduced to a man who was looking for a kept boy, and I had a few dates with him. He was a doctor who was in his early 50s, and I found him quite attractive, which was the main problem: I could have enjoyed having an affair with him as equal partners, but I couldn't have been comfortable being used as a boytoy. When I explained that to him, he made it clear that he was looking for someone who would simply fulfill a utilitarian role, not complicate his emotional life, so we became merely casual social friends.

 

Thanks for your honest post!

 

Even with looks and stamina like you had at the time, a special mindset is required to do it to make a living and to last in the business.

 

Don't be so humble, I'm sure everybody who hired you wanted more!

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When I was in my early 20s and an impecunious grad student, I decided to try hustling one day. (There were no escorts in those days, because there was no gay media in which to advertise as one.) I knew where to go downtown to try to get picked up by someone who would pay, and I did it for several hours (I was young enough to be able to cum multiple times in one day), but I realized it was not something I was very good at, because I had a hard time performing with men I wasn't attracted to, so I didn't continue.

 

Around the same age, I was introduced to a man who was looking for a kept boy, and I had a few dates with him. He was a doctor who was in his early 50s, and I found him quite attractive, which was the main problem: I could have enjoyed having an affair with him as equal partners, but I couldn't have been comfortable being used as a boytoy. When I explained that to him, he made it clear that he was looking for someone who would simply fulfill a utilitarian role, not complicate his emotional life, so we became merely casual social friends.

@Charlie that sounds quite like the movie script!

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Give it a try again!

 

Spend your hard earn money in an hour of pleasure with an escort. It's a win win situation!

 

 

 

 

Thanks for your honest post!

 

Even with looks and stamina like you had at the time, a special mindset is required to do it to make a living and to last in the business.

 

Don't be so humble, I'm sure everybody who hired you wanted more!

?

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During the summer before my senior year in college, I worked at a large hotel in downtown Cincinnati as a night auditor at the front desk. The resident manager was in his 50s and was as handsome as he was gregarious. Right after I started working, one evening the office manager asked me to stick around because the boss wanted to have breakfast with me when my shift ended at 7. Cutting to the chase, he made it abundantly clear that he saw “special” qualities in me and hoped I realized just how helpful he could be with my future career. I was a swimmer, and so was he, which made our frequent dips in the hotel indoor pool a lot of fun. Terribly naive, I fell for his offer and we started meeting in his apartment a couple of mornings a week. Within a few days, after some arm stroking and a few lingering shoulder pats, I knew something was up. One morning, when I knocked, he invited me to come on in, as he was just stepping out of the shower, and needed a towel. (Cue the cameras, action!) I’ll spare you the sordid details, but for the remainder of the summer, let’s just say that his tutelage and mentoring opened up a whole new world. Alas, summer ended and I was back off to campus. Of course, we had a few holiday visits, but by spring, he had moved on to another city and I never heard from him again. Thank you, Leonard, wherever you are - I’ll never forget your classic Dunhill cologne and cigarettes. So did this romp qualify as escorting? Let’s just say that I had no financial issues for quite some time.

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Um, sordid details are what we're all here for. Spill!

 

 

 

Okay, if you insist. At this point, I was still a little unsure of my sexuality. I had dated women (yes, screwed) however, my “bi” line was ever growing. I’d done a bit of oral with dudes, but not much else. My mentor traveled a lot and had quite a collection of fragrances, etc. and was particularly fond of La Mer face cream. One day we were about to get down to business when he asked me to massage his phallus with the cream. But of course, with pleasure, monsieur. Next, he flipped over and had me rub some of the luxurious stuff between his cheeks and on the inside. By this time I was at full mast and in return, he spread a nice little dab of it on my dick. It didn’t take a split second to figure out what was coming next (pun fully intended) as I gladly slid into him. Like dipping into a warm, velvet sleeve, he sucked me in and I never wanted to leave. But when you’re 20, and full of juice, it’s not always easy to slow down a moving train. Let’s just say it was a top-notch explosive experience that got repeated many times. Can you still buy La Mer?

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