Most memorable escort encounter ever?

[Boston Guy]

I was talking to a friend about escorts we had hired. He asked me what I would consider to be my most memorable escort encounter ever. I found it to be a difficult question to answer.

 

I've met a ton of nice guys, interesting guys, sexy guys and some who were not so nice or not so interesting or not so sexy upon close examination. I've met guys with lots of attitude and guys so charming they'd melt the coldest hearts. But the single most memorable single encounter???

 

There have been lots of guys I've hired multiple times, guys I've had great times with. My first inclination was to pick one of my favorites. But I'm not sure that would necessarily lead to my most memorable encounter. I thought about guys I met in other countries, when I was traveling alone and not completely certain about culture, safety, etc. I tried to think of memorably bad experiences, but I've had few bad experiences and none of them have been particularly memorable.

 

I thought of one young guy in LA for whom I was the very first client and, it turned out, the very first guy he'd ever fooled around with. That was fun. But it's just one memory among many.

 

Ultimately, I guess, it would be with an 23 year old escort in LA who came to my hotel one night. I didn't know him and had arranged for an hour and he ended up staying for most of the weekend, at no charge. Half a dozen years later, we're still friends, even though he hasn't escorted in several years. I look back at meeting him with great fondness.

 

So while I thought I'd end up with some odd or funny encounter or one that scared me or involved particularly memorable sex or multiple partners or something, it comes down to remembering first meeting a person I've grown fond of.

 

How about the rest of you? What's your single most memorable encounter with an escort? And why is it your most memorable?

 

BG

[jackhammer91406]

BG,

Like you, it takes some sorting out for me.

 

If I go by just the thrill of the sex, it would be the guy I hired on a trip to NYC who retired the day my review of him was posted here. He was so hot and something electric went through me when he took me inside himself and squeezed the very essence out of me. A Canadian dancer from the Gaiety would run a close second. (looking back, that was a great trip to NYC.)

 

BUT if I go by who has had the most lasting effect on me, it would be the escort (also in NYC) who has become a good friend over time. Because his nature and good humor are so enjoyable, and because we click so well together, this is the guy that I most remember.

[+ Lucky]

When I came out of the closet, 31 years ago this month, I was propelled by my feelings for one certain individual, a straight guy. I knew I could never experience that kind of thing for a woman, so I came out and went looking for what I really wanted.

 

One night, cruising Santa Monica Boulevard, I saw a guy who was the exact twin of the guy I had wanted so badly. So close in fact that I actually could imagine that it was in fact him...thus able to give in to all that lust I had locked in so tightly.

 

So he wins the "most memorable" award for me. I remember that his shoes were so stinky that I had to put them outside! But a total sweetheart in every way. I never saw him again.

[Luv2play]

I have hired at least 500 escorts in my life and only a handful remain truly memorable. These days I use the services mostly of one escort, one masseur and one ex-dancer altho I dabble on the side (be still my promiscous heart!).

 

Anyway, the most memorable escort I ever experienced was in the days before Internet and when one consulted the escort columns of small community gay newspapers. It was a small ad with no pic and little to go by except a hint of class. Well, he turned out to be a lot of class! And one of the hottest men I had ever encountered!

 

He was expensive for the market I was living in at that time. But the sex was so good (he was gay, totally masculine looking big blond guy with a mischeivous twinkle in his eye, with a great big 9 inch cock). And totally in command in bed, verbal, physically demanding, the works!

 

Did I say he was expensive? He was "working" his way through university and was totally discreet in his business activities as he came from a well-connected family in the community. His clients were people like me, professionals who demanded discretion in return. Being a small city we lived in, we met frequently in the few gay bars there were and we would acknowledge each other without ever betraying our other "relationship".

 

One day he said to me that he would reduce his rates significantly for me as I was a repeat client (althought I had been moderating myself in view of his steep prices). Well, it was as if the price of drugs had just been slashed for a drug addict, I went to town! I started seeing him a lot more, sometimes in mid-day when business was slow, and we had sex in virtually every room of the house. I even had a floor to ceiling mirror installed in my basement with a large bed beside it.

 

Then the day came when he walked out of my sex life forever! I was at a gay pride event in another city when I spied him with another man (gasp), my family doctor! He saw me and gave me a wicked wink! He later informed me he was moving in with my doctor and giving up his "business". That was the end of my most memorable escort experience! ;(

[jawjateck]

Because of Hooville, thankfully, I have no horror stories to tell. Never been mistreated. Never been ripped off. Never been stood up. My most memorable, was my first escort about six years ago. Not only my first escort, my first experience with another guy; late bloomer here. I was traveling in Denver on business and arranged to have a masseur drop by my hotel for a 2 hour appointment. I knew he provided erotic massage, but didn't know the other escort services that he offerred. Well, he came over, sexy, hot, handsome, 30 something latino stud, nice, friendly; he not only gave an awesome massage, but stayed around for an extra hour of play, during which all my years of dammed up passions broke loose. :9

 

He was such a great guy, professional, yet cool and awesome fun in the sack that I invited him back over two nights later. The reason it was most memorable to me is because he, being friendly, helpful, and understanding of my situation, allowed me to enjoy myself, and I realized it was OK for me to meet with other guys. If he had been a jerk or a con, I would have completely written off the man2man thing, paid or not. Since meeting him, I have met dozens of great guys, and had sooooooo much pleasure. [Editorial note: after re-reading that last sentence, do I qualify to be labeled a 'ho'?] }(

 

I intend to make this, my 40th year, the best ever. ;-)

[Lankypeters]

I've had good luck and so many great sessions that I couldn't single out one as the best ever.

 

But a composite of highlights from most of my encounters includes:

 

-- Patrick/Mason formerly of Chelsea Guys. The second time I booked him I was rebounding from an affair with a shitty married man. Five minutes after Patrick arrived he buried his head in my ass, his teeth lightly pressing against the tender skin of my butt cheeks, his toungue swirling around my butt hole;

 

-- the first time I stripped and faced off with Derek Ross, he clad only in a jock strap. We traced each other's nipples with the tips of our fingers. His cock slowly pushed out above his jock strap;

 

-- stripping down and standing between Derek Ross and Rick Munroe. I stroke their cocks and, like Romulus and Remus, they start sucking my tits.

 

-- capping a great session, I looked up at Luke of Chelsea guys drove his gorgeous blond cock into my butt, squeezed a tit with one hand and jacked off my cock with the other.

 

Two minutes before I come I always decide the fuck is the best I've ever had.

 

Lankypeters

[JT Brooklyn]

JT's Best.....A Gorgeous Tall Green eyed... Brazilian, Novella Star..Who now is a Lawyer in where else..Miami!

Luv'd contributing to Higher Education. The Guy was great at doing MY Home-work! LOL :+

[Epigonos]

My background in the world of hiring escorts mirrors that of jawjateck. I hired my first escort in the fall of 2002 at age 61. God how I agonized over the right guy to hire. I consulted one escort site after another until I finally, by accident, ran onto this site. I'm a research freak and damn did this site fill the bill. After reading all the reviews from both Southern (where I live) and Northern California I settled on STEVEN KESSLAR in San Francisco. Contacting STEVEN was easy and his emails were informative, fun, and sexy as hell. I booked a flight to San Francisco and a room at the Stanford Court Hotel. After checking-in I waited for his arrival with both anticipation and a hugh case of nerves. Now not only was STEVEN the first escort I ever hired he was also the first guy with whom I ever had sex. STEVEN put my nerves to rest immediately and during dinner I came to realize just exactly what an outstanding human being this man is. Later back in the hotel room he opened up a whole new world for me. Since that awsome day I have hired numerous different escorts. The honest truth is that I have never had a really BAD experience. Many of the guys I have hired I have reviewed here and many I have not. The interesting thing, at least to me, is that I keep returning to STEVEN KESSLAR. We take two trips together each year and meet for overnights. Over time a friendship has developed and that friendship makes the sexual relationship we have even more enjoyable and memorable

[+ Charlie]

There are many different kinds of memorable escort experiences: exciting, funny, frightening, etc. The first ones often stand out because the whole thing is so new--when I look at the list of the escorts I hired in my first year, I can remember each of them clearly, yet many of the names from later years summon no image at all. I tend not to re-hire, for various reasons, so the few whom I hired several times tend to be more vivid (especially the one I kept accidently re-hiring, because he kept advertising under different names in different cities, with no picture). But the single hires could also be striking, like the superbutch porn star who shocked me by inviting me to come back for breakfast the next morning, or the scary hunk who I later learned ended up in a prison for the criminally insane after murdering a client, or his straight brother who was actually better sex, or the former lover of an old friend (a real surprise when he opened the door!), or the guy I realized I had had for free several years earlier. Sometimes it was memorable because there were two together, like the strange little (5'4") twins, or the gorgeous Israeli lovers who gave me a great birthday gift, one of the only times in my life I have been simultaneously penetrated from both ends.

 

However, the most memorable was probably the strangest experience of them all. He was a somewhat exotic looking redhead with a soft, insinuating manner, and after I had been sucking his cock for about ten minutes, he suddenly slipped into a kind of trance state, and began to tell me all sorts of things about my family and friends. Since we had barely spoken beforehand and he didn't even know my name or where I lived, I was dumbfounded as he described my late father with incredible accuracy, and then transmitted messages from him to me about matters that virtually no one outside my immediate family could have known. This sort of thing went on for more than an hour, as he talked about unusual things, such as a mental breakdown suffered by my best friend's mother. By the time he came out of the trance, I had forgot all about sex, and I left so shaken that I headed straight for the nearest bar and a couple of stiff drinks. I finally got up the courage several months later to hire him again, and nothing at all unusual happened--he couldn't even remember that first episode.

[Guest zipperzone]

>Then the day came when he walked out of my sex life forever! I

>was at a gay pride event in another city when I spied him with

>another man (gasp), my family doctor! He saw me and gave me a

>wicked wink! He later informed me he was moving in with my

>doctor and giving up his "business". That was the end of my

>most memorable escort experience! ;(

 

Was your doctor a proctologist by any chance?

[Lookin]

Charlie, you need to do a series on Logo or Here! "The Israeli Lovers" could own Sweeps Week!

 

While I can't top your stories, I do have fond memories of my first escort experience about twenty-five years ago. I was getting plenty for free, and hadn't even thought of paying for sex. Then I ran across an ad in the Bay Area Reporter for Rick Donovan. I had fantasized about that guy for years and here he was, ready to be all mine, for a mere $125! It took me a couple of days to scrape up the cash, get over to the little trick-studio he had near the Panhandle, and ring the bell.

 

Although I had looked at his pictures many times, I wasn't prepared for how beautiful his eyes were. They were blue-green, with flecks of hazel, and deep set under long lashes. He could have had one of the world's smallest dicks, and I would have been happy. As it turned out, he had one of the world's largest dicks, and I was ecstatic. It wasn't long at all before our clothes were off, and I was in a position to let him know how glad I was to see him.

 

After awhile I stood up, and got to see the rest of him. His skin was clear and tan all over, and his buns were like two smooth bronze melons. I think he liked my buns too, since he grabbed them and tried to spin me around. I had to politely inform him, "Sorry, I don't get fucked." Even today, those words come back to haunt me. What in the world was I thinking?

 

Well, we found lots of other things to do, and we both ended up shooting healthy loads, and finished with a nice relaxing shower. We didn't talk much during our time together, but I do remember him telling me about his investments in the Cayman Islands. That was the first time I realized that business and pleasure do mix quite nicely.

 

I didn't hire another escort for more than twenty years, and the memory of that first time has kept me going strong. I am now, however, actively pursuing new memories, and hope to be able to top this one in the near future. Maybe you can tell me how to get in touch with those twins.

[buttnovice]

one word. . . "SHAMUS"

 

My three encounters with him in NYC set the standard. Each was unique and memorable.

 

All others. . . . well, let's just say there are no others!

 

BN

[KY_TOP]

I'm sorry I can't really post one. For everytime I think back to a certain one to comment about here, I then remember another. Thanks for the walk down memeory lane, even if it is only in my head or a few reviews. :+

[+ cougar]

My most memorable single encounter was with an escort named Paulo in DC a couple of years ago. We had communicated via phone and e-mail several times and had all our "simple" plans made out.

Our session was planned for my second night there, and he had asked that I call him when I got into DC just to let him know I got there and was settled in. After I got all settled into my hotel room, I called him and through our conversation, he realized that I had no specific plans for that night and offered to come to the hotel and drive me around DC, so I could see the sights in the night time. That night we drove around for about 90 minutes and he showed me some sights I would have otherwise missed. and since he had told me our date for the next night was still on and this little tour was off the clock, the least I could do was to offer him to join me for dinner.

We went to Annie's Steakhouse, had a couple of drinks and a steak. Needless to say, his kindness and interest in me made our date the following night very comfortable for both and I left town with an impression of him that has yet to be topped.

I will alwys remember meeting him and our time together!

I understand that he retired shortly thereafter.

[Guest msclonly]

A once in a lifetime experience of Crossing Over!

 

Charlie,

I don't know how you think of the 'trance' experience now, but that is a very rare invent, and I actually looked forward to just such a happening. It is a natural phenomenon and I believe really is out of the control of the person able to see into another world. It really is a gift to have this ability! And it is best received as a gift, as opposed paying someong for this kind of information. Do you remember anything, that proved to be helpful after the experience inspite of your fear of the unknown.

 

I was talking to a women on the phone, because her boy friend wanted me to talk to her about some of the problems she was having. I had never met her. I met her BG in a printer repair shop and recognized the origin of his last name, and we had a nice conversation.

 

She started to tell me about my Father, my life, and other members of family. Dead on! Then she related messages from my Father concerning current events in my life, that I wanted to know. In the process, many things I discussed with my Father as a youngster, a life time ago, that NO one else ever knew was brought up without my prompting. Now, a year or two later, that information has proved to be very valuable in making me far more assured and confident with more focus on current life decisions. Especially investments.

 

It was a very uplifting and profound experience, that I had been looking for and waiting to happen. It gave a natural high, that I think still lasts till today. Would have loved to had further contact with the gal. Even though, I gave her encouragement and support unlike her Mother, when she was a child with this gift of having angels around her and giving her information, since they were Italian Catholics. She has been asked to solve Criminal cases, but just does not feel comfortable, since her Mother tried to bury the extra sensory ability. Incidently, I don't believe this gift worked for her in her life struggles.

[+ deej]

I've been hesitant to post this.

 

My most memorable experience isn't the most pleasant memory. It will, however, be with me forever.

 

I was walking home from a bar in Chicago's boystown and a guy working the street "approached" me. He was cute .... tall, lanky, good looking, and had a butt to write stories about. And did I mention I was on the way home from a bar? My judgement wasn't running full throttle.

 

We went to my place and had a good time. He got paid. I thought it was over.

 

Beginning that night and over the next week, he showed up again -- at 4am. He'd knock on the door of my apartment loudly, shout my name, and generally be a nuisance looking for cash. I generally fended him off and refused to open the door. (He left permanent dents in that metal door he was so insistent.)

 

The Chicago police were sympathetic (to a point) but couldn't get there in time to nab him.

 

One morning, relieved that I hadn't had the nightly disruption, I did my morning routine and headed out for the office. When I opened my door, there he was, and he forced his way in. With a friend. Who was armed.

 

They tried to rob me but I'd been prescient enough to empty my wallet of everything except the day's spending money. And that was in a cheap dime store wallet. They did, however, crack a rib. That gave the police enough to move.

 

I spotted him again about a year later. He was again walking the Haltead strip. He looked rougher, sort of jail-hardened, and had a new tattoo that looked very prison-ish. I don't think he saw me. But by then I'd moved to a different place so at least I knew he wouldn't be trying to break down my door.

 

This isn't the best memory, but it's the most lasting. And it makes every great escort encounter seem all the more better, and me all the more thankful!

[Boston Guy]

You're lucky it didn't end worse than it did. And smart to call the police.

 

And we're all lucky that this kind of story isn't much more prevalent today. I have a feeling it might have been once, falling into the category of under-reported crimes because guys were just too embarrassed or frightened to report it. Do any of you remember the story of the Canadian guy who was being blackmailed by an escort -- and had been for something like the previous 10 years?

 

This site has contributed a deal of transparency to escorting. I think the shared wisdom here has helped in many ways, including reducing the risk of violent crime.

 

BG

[+ Lucky]

Deej, someone should have warned you about those Chicago boys!! Every once in a while one of them can get pretty wacky!

[+ Lucky]

Deej, someone should have warned you about those Chicago boys!! Every once in a while one of them can get pretty wacky!

[+ deej]

Oh, I'm well aware how lucky I was.

 

I'd like to think this site played a role in raising awareness, if nothing else. And that's why I posted this story.

[+ deej]

Oh, I'm well aware how lucky I was.

 

I'd like to think this site played a role in raising awareness, if nothing else. And that's why I posted this story.

[+ deej]

And once in a while, one of them gets Lucky. }(

[+ deej]

And once in a while, one of them gets Lucky. }(

[uwsman2]

I started hiring almost thirty years ago when I first moved to NYC and was myself only in my 20s... It was an interesting alternative to bars and the baths, and it was before we had so many community organizations where one could meet people. And every now and then I wanted to have fun with the physical kind of man I fantasized about.

 

So, after all those years, there are many memorable experiences to recall, especially from when I started experimenting with an occasional bondage/SM fling. (My first time with Master Victor in New York was extremely memorable...)

 

But the most memorable escort experience took place on the upper East Side in about 1979 or 1980 or thereabouts. In those days, if you were not into street trade or the few hustler bars, the main source was escort classifieds in The Advocate. Most of them did not have pictures, so you were relying on interpreting text. I was living on the upper East Side at the time, and spotted an ad from a 20-something "foreign student" in my neighborhood. His name was George. I went to his apartment, a studio far east near the river. He was Greek, with lustrous curly hair. He actually looked a bit more mature than 20-something, more like early 30s. He was dressed in a loose sweatshirt and lo0se sweatpants, not particularly tall, but with a classically handsome face and friendly smile. The loose clothing concealed his body, but his arms were thick and muscular. There was a big drafting board taking up lots of the room in the studio (he was an architecture student) and a very high bed. He asked if I felt comfortable with him, and I said yes, so he said why don't you get more comfortable? After we removed our shirts I was immediately thrilled at his beautifully developed muscles, really gorgeous. He immediately put his arms around me and swiftly lifted me up to sitting position on his bed. I reached down and felt through the sweatpants the biggest, hardest cock I could possibly have imagined. It turned out he was a totally passionate lover, a great kisser, and a magnificent top. After we had both experienced explosive orgasms while he fucked me on my back, we lolled next to each other, casually stroking each other's cocks and kissing until we were both hard again, and he stared at me mischievously and asked, "good for another"? And so we repeated. And we had a wonderful conversation, and he was urbane and witty and sophisticated. I saw him again once or twice before he finished his studies and returned to Greece.

 

So my very memorable experience was not with a "professional" escort, as such, but with a graduate student who was doing this on the side to help pay for his education. He was clearly a serious, intellectual person who was meticulous about his body. The muscular development was astounding without being overdone. I still remember the smooth hardness of his pecs, and his big chewable nipples....

 

Since then I have had many extraordinary escort experiences, but so far none has "topped" this early one.

[uwsman2]

I started hiring almost thirty years ago when I first moved to NYC and was myself only in my 20s... It was an interesting alternative to bars and the baths, and it was before we had so many community organizations where one could meet people. And every now and then I wanted to have fun with the physical kind of man I fantasized about.

 

So, after all those years, there are many memorable experiences to recall, especially from when I started experimenting with an occasional bondage/SM fling. (My first time with Master Victor in New York was extremely memorable...)

 

But the most memorable escort experience took place on the upper East Side in about 1979 or 1980 or thereabouts. In those days, if you were not into street trade or the few hustler bars, the main source was escort classifieds in The Advocate. Most of them did not have pictures, so you were relying on interpreting text. I was living on the upper East Side at the time, and spotted an ad from a 20-something "foreign student" in my neighborhood. His name was George. I went to his apartment, a studio far east near the river. He was Greek, with lustrous curly hair. He actually looked a bit more mature than 20-something, more like early 30s. He was dressed in a loose sweatshirt and lo0se sweatpants, not particularly tall, but with a classically handsome face and friendly smile. The loose clothing concealed his body, but his arms were thick and muscular. There was a big drafting board taking up lots of the room in the studio (he was an architecture student) and a very high bed. He asked if I felt comfortable with him, and I said yes, so he said why don't you get more comfortable? After we removed our shirts I was immediately thrilled at his beautifully developed muscles, really gorgeous. He immediately put his arms around me and swiftly lifted me up to sitting position on his bed. I reached down and felt through the sweatpants the biggest, hardest cock I could possibly have imagined. It turned out he was a totally passionate lover, a great kisser, and a magnificent top. After we had both experienced explosive orgasms while he fucked me on my back, we lolled next to each other, casually stroking each other's cocks and kissing until we were both hard again, and he stared at me mischievously and asked, "good for another"? And so we repeated. And we had a wonderful conversation, and he was urbane and witty and sophisticated. I saw him again once or twice before he finished his studies and returned to Greece.

 

So my very memorable experience was not with a "professional" escort, as such, but with a graduate student who was doing this on the side to help pay for his education. He was clearly a serious, intellectual person who was meticulous about his body. The muscular development was astounding without being overdone. I still remember the smooth hardness of his pecs, and his big chewable nipples....

 

Since then I have had many extraordinary escort experiences, but so far none has "topped" this early one.