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Did you ever escort ... ?


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I was approached to become an escort in a large expat community in Southern Spain by the owner of the small apartment where I was living in 1973. Not interested because his motivation was partly my staying there much longer than I wanted. I had more than enough of the twice weekly bull fights.

 

And I didn't need the money.

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I was hitchhiking home from class when an older man picked me up and started chatting me up. Eventually he asked if I had a girlfriend and if she cleaned my pipes. I lied and said I did. He told me he could do a better job and told me he had fifty dollars to prove it. That was a month's worth of spending money. He pulled over and told me to drive. He then felt me up and undid my zipper and pulled my cock out and began to suck in earnest, After a short bit, he said his back was hurting and he wanted to go to a hotel. I told him know and grabbed the back of his bald head and pushed it back down onto my cock, He resume sucking and I held him there, As I got closer to coming, my foot got heavier on the gas pedal and we were speeding along pretty quickly when I came in his mouth. He then told me he did not have the fifty and when I began to make a fuss he gave me 20. I got out of the car and went right into my house to shower, I would up jerking off in the shower thinking about it. So a one time escort.

He did offer to bring me to a hotel to meet some friends of his if I wanted to do this again, but as this was my first blow job and my first time with a man, I had a lot to process. Heavy set, totally bald said he was new in town from Cincinnati.

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I have NEVER even considered it. Primarily because I have a little dick, but I am basically shy when it comes to meeting people. Oddly, a few people have asked me this question in the past two months.

Congrats on becoming a “staff member”

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I never had the social skills for escorting but I was not bad looking in my late 20s and early 30s and I did take advantage of that financially. I would sell used clothing items on eBay and other sites. I always took lots of photos for the listings, including face and full body, and I received so many sales and compliments that it turned into selling custom photo sets to some guys who became regular buyers. Not kidding, I once sold a dirty pair of cheap white ankle socks on eBay for $100.

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Strangely enough, I thought about this string earlier today when I got a text from someone I met on Seeking Arrangements. It was from this 25 year-old dude that I'd gone out with for the last 2.5 weeks. Unlike most men I've met from that site, he really seemed to dig me for myself, and had no interest whatsoever in my money. Maybe he digged me too much. I've never had someone so crazy about me. The 2nd time we got together and first overnight, we had sweaty sex, then went on a hike in the hills, then came back and had more sex, then had dinner, saw a movie (during which he was pawing me the whole time), then had sex again before going to sleep. I told him that his sexual appetite was a bit much for me, and he said "You know, you can get an operation so that you can get an erection any time!". He wanted sex again in the morning, but I told him I wasn't a morning person.

Then last week-end, sex before the hike, at bedtime, and he got me to do him again in the morning. Good loads each time. He says he finds me "really sweet," but that our interests are too different for a LTR. Indeed, I told him my greatest passion is travel, and he hates to travel. I told him that when I move to LA, I wanted to get dogs, and he doesn't like that idea either. Also no interest in the performing arts (plays, operas), and even our tastes in movies and TV are totally different. The only TV show I could find that he liked, Space Force, I found really dull. He didn't like any movies I liked, not even comedy (I like slapstick-type comedy, he likes deadpan), which was the only type of show or movie he seemed to like.

I got another text from him today wanting to get together, and it crossed my mind to jokingly text back "How much would it be worth it to you?" Looking back, I think the main thing I appreciated about him was that I felt an ego-boost from his insatiable attention to me. If anything, it was too much attention. Sigh, I suspect I may never find someone that age who's so crazy about me. He's decent looking, just not my type, so I guess I'll let it die out. And I will not have that surgery!

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I have NEVER even considered it. Primarily because I have a little dick, but I am basically shy when it comes to meeting people. Oddly, a few people have asked me this question in the past two months.

Please don't think that all gay men like big dicks. For me, the smaller the better. The last time I went to LA, I sought out the escort who had the smallest dick, because I wanted to suck some cock, a pleasure I developed in my relationship with the Lyin' Paraguayan (he had a somewhat smallish cock). I cancelled the appointment because he wanted to charge me extra for licking his armpits, which I felt was ridiculous. He keeps texting me every couple of weeks, though. I'm going back to LA in a couple of weeks. I may just ask him if he's changed his mind, and would be willing to let me get my mouth around both his cock and armpit for the same fee. I really wish more men with smaller endowments would escort. It's challenging finding less-endowed escorts. Maybe you would have had good business due to a unique offering.

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Strangely enough, I thought about this string earlier today when I got a text from someone I met on Seeking Arrangements. It was from this 25 year-old dude that I'd gone out with for the last 2.5 weeks. Unlike most men I've met from that site, he really seemed to dig me for myself, and had no interest whatsoever in my money. Maybe he digged me too much. I've never had someone so crazy about me. The 2nd time we got together and first overnight, we had sweaty sex, then went on a hike in the hills, then came back and had more sex, then had dinner, saw a movie (during which he was pawing me the whole time), then had sex again before going to sleep. I told him that his sexual appetite was a bit much for me, and he said "You know, you can get an operation so that you can get an erection any time!". He wanted sex again in the morning, but I told him I wasn't a morning person.

Then last week-end, sex before the hike, at bedtime, and he got me to do him again in the morning. Good loads each time. He says he finds me "really sweet," but that our interests are too different for a LTR. Indeed, I told him my greatest passion is travel, and he hates to travel. I told him that when I move to LA, I wanted to get dogs, and he doesn't like that idea either. Also no interest in the performing arts (plays, operas), and even our tastes in movies and TV are totally different. The only TV show I could find that he liked, Space Force, I found really dull. He didn't like any movies I liked, not even comedy (I like slapstick-type comedy, he likes deadpan), which was the only type of show or movie he seemed to like.

I got another text from him today wanting to get together, and it crossed my mind to jokingly text back "How much would it be worth it to you?" Looking back, I think the main thing I appreciated about him was that I felt an ego-boost from his insatiable attention to me. If anything, it was too much attention. Sigh, I suspect I may never find someone that age who's so crazy about me. He's decent looking, just not my type, so I guess I'll let it die out. And I will not have that surgery!

Well ... Now I know that there is a subset of hot daddy escorts in their 50s in RM, and I would suspect that they have their fair amount of fans who dig the assets and experience of a mature man, so it wouldn't be so strange to think that a young guy would pay an older one for service.

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Please don't think that all gay men like big dicks. For me, the smaller the better. The last time I went to LA, I sought out the escort who had the smallest dick, because I wanted to suck some cock, a pleasure I developed in my relationship with the Lyin' Paraguayan (he had a somewhat smallish cock). I cancelled the appointment because he wanted to charge me extra for licking his armpits, which I felt was ridiculous. He keeps texting me every couple of weeks, though. I'm going back to LA in a couple of weeks. I may just ask him if he's changed his mind, and would be willing to let me get my mouth around both his cock and armpit for the same fee. I really wish more men with smaller endowments would escort. It's challenging finding less-endowed escorts. Maybe you would have had good business due to a unique offering.

Now I'm curious. Link?

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Please don't think that all gay men like big dicks. For me, the smaller the better. The last time I went to LA, I sought out the escort who had the smallest dick, because I wanted to suck some cock, a pleasure I developed in my relationship with the Lyin' Paraguayan (he had a somewhat smallish cock). I cancelled the appointment because he wanted to charge me extra for licking his armpits, which I felt was ridiculous. He keeps texting me every couple of weeks, though. I'm going back to LA in a couple of weeks. I may just ask him if he's changed his mind, and would be willing to let me get my mouth around both his cock and armpit for the same fee. I really wish more men with smaller endowments would escort. It's challenging finding less-endowed escorts. Maybe you would have had good business due to a unique offering.

I'm curious, what is considered 'smallish'? As much as some people overestimate their size, others tend to underestimate. I find relative terms to be potentially depressing I guess.

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I'm curious, what is considered 'smallish'? As much as some people overestimate their size, others tend to underestimate. I find relative terms to be potentially depressing I guess.

I personally prefer a penis that I can fit completely in my mouth without any gagging or choking, so less than 6 inches. Try to find an escort with that. Not easy.

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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.

 

When you first told this story years ago I pasted it into my journal because I loved it and didn't want to forget it. I need not have bothered, in the interim I've thought of it many times.

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