Story about your first hire.

[Tom C. Sinclair]

In retrospect, a poor experience. I didn’t realize it at the time. I flew him in from Vegas. He slept a lot of the time. He also never engaged in anything sexual. I have since learned a lot. 

[+ Vegas_Millennial]

The first time I hired an erotic masseur was in the late 00's. I hired him from his advert in the yellow pages. I received my first message at Massage Envy a few months prior and was seeking another legitimate massuer at a more convenient time. The massage ended with him blowing me.

The first time I hired an escort was when I was going back to school for my Master's Degree in the mid 10's. We met for a 2 hour session after an evening class. The escort and I shared the same birth year. I remember needing the session as a way to cope sitting through class... It gave me something to look forward to at the end of the class

[dutchal]

First guy I remember hiring was a beautifully built black guy, imagine a sculpted college football linebacker or running back.  Closely resembled DeAngelo Jackson in his early years.  Met him at one of the Times Square area peep shows. I couldn't believe a guy that gorgeous was cruising there, and I couldn't resist.  Our first encounter was in one of the booths.  I was naive enough not to realize he was looking for customers.  In any event, he was so hot I couldn't say no, and I paid whatever he asked to give me oral and finish me with a hand job, so long ago I don't remember how much.  We met that way a couple more times, and then I summoned up the courage to hire him to come home with me to bottom for me.  Again, I don't remember the rate he asked/I offered.  We had a few of those sessions.  (This was before cell phones, and he didn't have a phone number I could use for these purposes, so we only met by serendipity when we were both at the particular peep show.)  One time we even had sort of a date--I took him to see "Purple Rain" before we went back to my place.  That came out in 1984, so we probably met in 1983.  He was not only gorgeous but a genuinely nice guy with a very hard-luck life story, the details of which I don't remember.  As best I remember, not long after the movie "date" he told me he was moving out of town.  I still remember him fondly.    

[NJF]

4 hours ago, dutchal said:

First guy I remember hiring was a beautifully built black guy, imagine a sculpted college football linebacker or running back.  Closely resembled DeAngelo Jackson in his early years.  Met him at one of the Times Square area peep shows. I couldn't believe a guy that gorgeous was cruising there, and I couldn't resist.  Our first encounter was in one of the booths.  I was naive enough not to realize he was looking for customers.  In any event, he was so hot I couldn't say no, and I paid whatever he asked to give me oral and finish me with a hand job, so long ago I don't remember how much.  We met that way a couple more times, and then I summoned up the courage to hire him to come home with me to bottom for me.  Again, I don't remember the rate he asked/I offered.  We had a few of those sessions.  (This was before cell phones, and he didn't have a phone number I could use for these purposes, so we only met by serendipity when we were both at the particular peep show.)  One time we even had sort of a date--I took him to see "Purple Rain" before we went back to my place.  That came out in 1984, so we probably met in 1983.  He was not only gorgeous but a genuinely nice guy with a very hard-luck life story, the details of which I don't remember.  As best I remember, not long after the movie "date" he told me he was moving out of town.  I still remember him fondly.    

@deangelojackson | Linktree

TR.EE

---

Multi Award Winning Adult Film Actor || Producer || Activist ||

Deangelo is muscular but I wouldn’t consider he is built like a linebacker 😂 

[+ José Soplanucas]

I do not remember who my first hire was. Back in the 80s, I used to cruise Avda Santa Fe and calle Lavalle in Buenos Aires, and sometimes hire street hustlers to take to my place. I cannot recall who the first one was.

I do remember my first hire from an agency. When I turned 30 (1992), I called one of the agencies that advertised in Clarín, the main local newspaper. In their Classifieds section they had a chapter for "personal services", the back then famous "Rubro 59". There, gay and straight agencies and individuals would advertise escorting services.

I called (remember, 1993 is before Internet and smart phones) one of the agencies, and provided them with a detailed description of what I was looking for.

First, they sent me a guy I did not find attractive. I paid him for his transportation, and called back the agency with adjustments to my description. This process repeated three times, until the fourth escort turned me on and provided me with an outstanding experience. 

[+ poolboy48220]

17 hours ago, dutchal said:

I was naive enough not to realize he was looking for customers. 

I've been there 😊 Like you, by the time he said "You do realize I'm an escort, don't you?", I was hooked. 

[marylander1940]

taking this off subject:

Damn dyslexia.... I keep reading SORRY about your first hire!

 

[eric thome]

My first time was around 2003, downtown Manhattan.   Craigslist was great and found a nice young and athletic asian guy to give me an amazing massage on his bed in his own apartment.  60 minutes of sensual bliss and ended it with a slow and satisfying hand job.  Went back many times over the years until he moved away. Ahhh the memories.  😃

[Nightowl]

My first hire was a masseur I found on Masseurfinder.  I had no idea what a “gay” massage was but I took the chance and set up an appointment with the hope of finding out.  When the day arrived I nervously drove 40 minutes to his home, where he greeted me warmly at the door and led me back to his massage room.  I’d had many massages at spas and hotels in the past but I knew this was going to be different when he instructed me to undress but didn’t leave the room, just watched me strip down.  There was no draping offered so I lay on the table, fully exposed, and he proceeded to give me one of the best massages I have ever had.  I wasn’t sure what to expect but was hopeful that it wouldn’t be strictly therapeutic. It wasn’t.  His hands explored areas that are usually off-limits and when I turned over, obviously aroused, he gave me the first happy ending I’d ever had from a man.  I remember that, as things progressed, his shorts disappeared and I felt his erection near my hand.  At that point, I just fondled what I could reach and explored areas within reach.  Over the course of several years, oral and MT became the norm.  I probably visited him a dozen times and each time was incredible.  Unfortunately, he is no longer working but I’ll always remember him as the one who got me hooked on erotic massage and gay sexual exploration.

[TruHart1]

My very first hire was all I could have wished for and more of a fulfillment of so many sexual fantasies I’d had for years, an NYC escort who acted in film and on stage, but whose career turned out to be a true expertise at making men happy.

Now retired (though we still keep in touch!) his escort name was Ares, and later, AresApollo. Needless to say, he set me on a path to pleasure that has made my life and sexual fulfillment extraordinary, with very few bad or mundane sessions since that first amazing and revelatory experience!

TruHart1 😎

[Nue2thegame]

On 1/12/2026 at 8:44 PM, NJF said:

@deangelojackson | Linktree

TR.EE

---

Multi Award Winning Adult Film Actor || Producer || Activist ||

Deangelo is muscular but I wouldn’t consider he is built like a linebacker 😂 

Linebackers aren’t built like they used to be. 

[Whippoorwill]

In the 1960s, I was in my early '20s and living and working in a small town in provincial Iran (this was pre-Islamic Republic days). There was a lot of gay activity in town, and there was a bathhouse where I heard guys went for sex, but I was too nervous to be seen at the bathhouse. One time I was in Teheran with a group of  American coworkers, one of whom went to the neighborhood bathhouse for a massage. (In those days all Iranians went to the bathhouse weekly for a bath, massage, and depilatory treatment). Iranians wore a tight fitting bathhouse towel, that was almost like a diaper...keeping the family jewels off limits. Fathers, knowing what masseurs were known for, always accompanied their sons. My friend (who was straight, well hung, and had the biggest balls I had ever seen up to then), not knowing about the bathhouse towel routine, laid down on the massage table, nude, ass-up. The masseur, not knowing Americans were casual about nudity, took this as the sign the customer wanted sex. A few minutes into the massage, the masseur wrapped my friend's hand around the masseur's hot erection. The friend jumped up, threw the masseur out of the room, left and rejoined our group, and relayed this awful experience he just had. As soon as I could inconspicuously leave the group, I made a beeline for the bathhouse, paid my 25¢ for a massage, laid down naked and ass up on the massage table. A few minutes into the massage, the masseur went for the jewels and I let him know I wanted to get fucked. He said that would be another 25¢ to which I readily agreed. After that, whenever I was in Teheran, I would go to different bathhouses to have sex with a variety of masseurs. It was cheap, convenient, professional, and anonymous. Here today it's convenient, professional, and anonymous, just not cheap. But it's worth it. 

Edited February 26 by Whippoorwill

[dutchal]

On 2/26/2026 at 2:56 PM, Whippoorwill said:

In the 1960s, I was in my early '20s and living and working in a small town in provincial Iran (this was pre-Islamic Republic days). There was a lot of gay activity in town, and there was a bathhouse where I heard guys went for sex, but I was too nervous to be seen at the bathhouse. One time I was in Teheran with a group of  American coworkers, one of whom went to the neighborhood bathhouse for a massage. (In those days all Iranians went to the bathhouse weekly for a bath, massage, and depilatory treatment). Iranians wore a tight fitting bathhouse towel, that was almost like a diaper...keeping the family jewels off limits. Fathers, knowing what masseurs were known for, always accompanied their sons. My friend (who was straight, well hung, and had the biggest balls I had ever seen up to then), not knowing about the bathhouse towel routine, laid down on the massage table, nude, ass-up. The masseur, not knowing Americans were casual about nudity, took this as the sign the customer wanted sex. A few minutes into the massage, the masseur wrapped my friend's hand around the masseur's hot erection. The friend jumped up, threw the masseur out of the room, left and rejoined our group, and relayed this awful experience he just had. As soon as I could inconspicuously leave the group, I made a beeline for the bathhouse, paid my 25¢ for a massage, laid down naked and ass up on the massage table. A few minutes into the massage, the masseur went for the jewels and I let him know I wanted to get fucked. He said that would be another 25¢ to which I readily agreed. After that, whenever I was in Teheran, I would go to different bathhouses to have sex with a variety of masseurs. It was cheap, convenient, professional, and anonymous. Here today it's convenient, professional, and anonymous, just not cheap. But it's worth it. 

I asked Google what 50 cents in 1960 is worth today:  $5.66.  Imagine massage plus full service for six bucks!    

[Chibttm]

I’m pretty new to this and my first time was a couple years ago. All in all it was fun. I’m a total size queen and size is my primary criteria when looking (always open to some recommendations from some other size queen’s ). The first guy claimed he had a 10 inch dick and really got my hopes up. He was really hot and a really nice guy but he had about 8.5 inches. He kinda apologized and said that guys couldn’t take it, usually just wanted to admire it and those that did liked the thought of double digit inches. 
 

I still had a great time and I’d have been ok with the 8.5 inches if it had been advertised but he did get my hopes up. It did teach me to do a better job of laying out my expectations.  I don’t hire one very often but every experience I’ve had has ranged from pretty good to amazing. I’ve been disappointed so many times with Grindr and Scruff hookups with guys claiming to be a top with a rock hard 9” and instead have a spongy 7 and want me to top them. I like the (relative) certainty of knowing I can find a dick big enough to send me to my happy place. 

[mtaabq]

My first hire had to have been in the 1st decade of this millennium; I couldn’t say exactly when. I do remember that it was at the Doubletree Hotel near Phoenix Sky Harbor. It did not go well; I had no idea how to go about it or what I was doing, really.  I recall I paid $150 just for him to show up; once he got there the upsell began. Cute guy; I found him in Echo magazine’s porn/personal services supplement - was it called X-Factor? (Echo was the Phoenix-area gay magazine.) Anyway, again, it wasn’t a good 1st hire. The 2nd, 3rd and subsequent hires went much, much better. In the past 20 years I’ve had some great hires and some not-so-great hires. I recall a long weekend in Phoenix in 2011 that was an embarrassment of riches and a plethora of naked man flesh all fueled by Benjamins with all providers plucked from CL. 2012 was another bountiful year in Phoenix. Since then most of my hires are found in Dallas, Phoenix, Las Vegas and Los Angeles/Long Beach. Getting a waiter or bartender to allow me to hire him for dessert is a fantasy still unfulfilled. 

[Muscle_Admirer]

@Muscleking thanks for creating this thread.  Such a wonderful trip down memory lane!

On 2/22/2026 at 6:22 PM, Nightowl said:

My first hire was a masseur I found on Masseurfinder.  I had no idea what a “gay” massage was but I took the chance and set up an appointment with the hope of finding out.  When the day arrived I nervously drove 40 minutes to his home, where he greeted me warmly at the door and led me back to his massage room.  I’d had many massages at spas and hotels in the past but I knew this was going to be different when he instructed me to undress but didn’t leave the room, just watched me strip down.  There was no draping offered so I lay on the table, fully exposed, and he proceeded to give me one of the best massages I have ever had.  I wasn’t sure what to expect but was hopeful that it wouldn’t be strictly therapeutic. It wasn’t.  His hands explored areas that are usually off-limits and when I turned over, obviously aroused, he gave me the first happy ending I’d ever had from a man.  I remember that, as things progressed, his shorts disappeared and I felt his erection near my hand.  At that point, I just fondled what I could reach and explored areas within reach.  Over the course of several years, oral and MT became the norm.  I probably visited him a dozen times and each time was incredible.  Unfortunately, he is no longer working but I’ll always remember him as the one who got me hooked on erotic massage and gay sexual exploration.

My first hire was interestingly similar in San Francisco back in the early 2000s.  On massageM4M as well, I was in my early 20’s and first time even having a massage, let alone going to a stranger’s apartment to receive one.  My masseur was a muscular Asian guy probably in his mid 30s who only did incalls.  He was quite attractive to me at the time.  In retrospect it appears he was running a factory assembly line of an operation because the encounter as I remember it now was so mechanical and formulaic.  At the time, I thought I was getting a legit massage from a gay man so it wouldn’t be embarrassing if I inevitably became aroused during the session.  I was mortified of having such a physical reaction at a hotel spa among straight people, so I searched for this alternative in need of a massage sans embarrassment.  Obviously, this was no hotel spa massage because midway through the massage, my masseur left the room for 5 minutes with the spa music playing.  You can imagine I’m lying face down on the cushion wondering why the massage stopped and why my masseur had disappeared into the other room. First thing I wondered was if I did something wrong, then whether he was going to harm me in some way while I lay practically naked and vulnerable… the usual mental spiraling of a baby-gay not knowing what to expect in an uncomfortable situation in a stranger’s home.  Once the 5 minutes were up, he reemerged into the room sporting a massive, thick, purple boner - cinched with rubber bands at the base.  He continued the massage, but now rubbing what looked like an uncomfortably swollen eggplant all over me.  I didn’t know better and thought the poor man needed to get off soon otherwise he’d be in priapism territory… I learned through the grapevine at the time the horrors of that affliction.  I offered to stop the session so he can take care of himself… he politely declined then suddenly took firm control and gave me the best damn handjob I ever had.  It’s almost as if he found the secret cheat codes to sudden, crippling orgasm and just mashed all the buttons.  I nearly passed out.  After I collected my wits, I was offered aromatherapy, fresh linens and a shower in a well appointed bathroom.  The whole session from start to finish including shower took a little under 90 minutes IIRC.  I paid the man, he gave me a quick warm hug then I’m out of the apartment and down the stairs encountering what appeared to be his next client.  I figured as much since he was ringing the same call button I had pressed earlier.  After that, I cringed wondering whether my masseur would have to go to the ER later that day being aroused as long as he had.  It’s hilarious thinking now how naive I was.

[WoolCave]

This was my first hire 16-18 years ago. He’s still using the same photos today, and they were old then. I wanted the guy in the pics. I started disappointed by what showed up and it was a bad session. 
 

https://rentmen.eu/BrettNYLA

 

I’ve since had many great hires all over the world. 

[+ StLouisOct]

I remember it so well because it was also my first time with a guy. Luciano was a RentMen escort about 25 with a lean, but well sculpted body and lovely brown eyes. As I recall, he was from Venezuela. He was the first guy I ever kissed and it was a long passionate one. I thought, “God, this feels REALLY good!” It didn’t take long to get naked and hugging him made me quiver. I was only a top back then and I vividly remember him looking up at me saying, “I want you in me.” It felt so natural. Later on he excused himself to go to the bathroom and when he walked out I felt like I was witnessing a modeling photo shoot. My only regret is that he retired before I became versatile. He’s one of many that I have topped who I would have loved to have top me.

Edited yesterday at 05:27 PM by StLouisOct