Your first escort experience

[JB85]

Okay, everyone. I'd like to hear your first experiences hiring an escort. What was he like and what did you do?

 

Please start with where and the year...

 

example: OMAHA, 1983.

 

and don't leave out any delicious details!

[Epigonos]

San Francisco, 2002

 

I retired from teaching in June of 2002. I spent the summer researching escorts on the internet. During that research I luckily happened upon HooBoy’s old site. At that time he has an adjacent site where escorts advertised. I thought I had died and gone to heaven. After much drooling and beating off I settled on a San Francisco escort by the name of Steven Kesslar. We set up an appointment and I made arrangements to fly from L.A. to San Francisco and booked a room in the Stanford Court Hotel atop Nob Hill. I was so nervous waiting for him to arrive that I damn near wet my pants. Until he walked into my room I had never touched another man erotically. Just the trill of kissing him and stoking and playing with his body damn near sent me over the top. Sucking his cock while he sucked mine did send me over the top. I had always believed that the term cock sucker was an insult but from that moment on I knew I was most definitely a cock sucker and proud of it. I have been with dozens if not hundreds of escorts since that faithful day with Steven Kesslar but he is still my go to guy.

[+ purplekow]

Picture it, Siciiy 1914...I mean, NYC 2002

 

After my wife died, I tried dating several women and found the experience trying and boring and it felt like a hollow attempt to regain the great relationship my wife and I had. Still, I found that i was sexually excited and at times downright horny. Sexual interactions with women had previously been terrific and my sexual relationship with my wife was active and exciting until she became ill. About two years after her death, on my fiftieth birthday, I decided to go outside the "box". As a teen, I had one brief interaction with a driver who picked me up while i was hitchhiking for which I was paid and another interaction in drunken lust seduced by my closest friend in college, age 17. I always considered those as fun but out of my comfort zone. My attraction to men was a vague sense of longing for the Superman type as a youngster and an interest muscular men which was more an "I wish I had that body rather than I wish that body had me". So for my birthday, I rented a Hotel Room at the Marriott Marquis and hired and escort Tony Pitt. Tony had, and still has, a great body. He is essentially a straight guy. I arranged for him come to my room by phone. He called me several times while I was in the room to delay the start time, turns out he was dancing at the Gaiety which was a few blocks away. By the time he showed up, I was ready to forget the whole deal, but when I opened the door, he had a great infectious smile and was wearing tight jeans and a sleeveless shirt, so I invited him to enter. He said he needed to shower and stripped down and walked into the shower. I was awe struck by the body and the physical confidence. I started speaking to him from outside the open bathroom door. He then invited me to open the shower curtain so he could hear me better. He started lathering up his cock and balls and then rinsed them, he cock getting harder as he washed. He then asked if I had ever sucked a cock and when I told him I had not, he changed that in about 15 seconds. Needless to say, I have hired him and many others since. I still occasionally have sex with women and I find that to be a much better experience than I did, but I have really enjoyed exploring the world of man on man sex.

[maninsoma]

San Francisco, late 1980s.

 

I'm not even sure exactly when my first hire occurred, but it was sometime around 1989 or 1990 which would have made me in my late twenties at the time. I was in an open relationship and not really happy about it. I decided to hire someone when he was out of town and chose a guy whose description and photo I liked in the Bay Area Reporter. I was quite pleased with the guy who showed up since he was muscular and handsome and also seemed like a nice guy, and I was basically a still relatively thin, average guy. We basically just kissed a lot and did mutual oral. The only real disappointment I remember is that the guy couldn't cum; he had had testicular cancer and had had both of his balls removed and replaced with, I assume, something similar to what women get when they have boob jobs.

[+ azdr0710]

Phoenix, late 2001....

 

had been following the old Hooboy site (precursor to this site) for a while, intrigued that I might be able to hire a stud in person to do whatever I want....my coming to terms with my sexuality was much, much delayed...looked thru the local reviews and ads and finally contacted a dude with appealing pictures and text...good communication and we agreed to meet at a hotel a discreet distance from my 'hood....nervous as all holy hell, I feared it would all be a setup with the PPD busting down the door....we met at the hotel's front door and he was very cautious, too...I suggested a short walk and chat around the parking lot to loosen up and he nervously looked over his shoulder for LE to bust him....I'm sure my nervousness didn't help things in the beginning....seeing he was nervous about being outside, I quickly moved us to the room....he was a tiny bit older than I'd hoped for, but was in decent shape and not a moron or addict....mostly well-known for being well-endowed, he quickly got completely undressed and we started a little body rub/massage thing....me being very nervous about disease (and it being a first time with an escort), we only went as far as rolling around and then each getting off on our own while hugging a bit....we chatted a bit, which I always like at these encounters, and he had some smart things to say....paid him at the end and he counted it in front of me, thanking me for the tip....

 

will say my second meeting was with Haus Weston a year or so later.....oh, man, the best.....my nervousness almost sabotaged the meeting at the last minute as he didn't want to do it if it wasn't going to be fun....again, I held back on doing much and wish I'd been more confident with him before he died a few years later....

[TruHart1]

Okay, everyone. I'd like to hear your first experiences hiring an escort. What was he like and what did you do?

 

Please start with where and the year...

 

example: OMAHA, 1983.

 

and don't leave out any delicious details!

 

New York 2011.

 

I went to NYC with a close friend for a 1½ week Broadway junket: a total of 13 shows including matinées! I had been looking at Rentboy ads for about a year before that trip, fantasizing about hiring, reading Daddy’s reviews, and building up enough courage to decide to take the plunge! About two weeks before the trip, I called the man I had decided on and found a very nice voice that was happy to set up a date and time. He asked that I give him a call when I got to the city and confirm our appointment. I called him after I got to NYC about 3 days before our appointment and confirmed.

 

When I arrived at his place at the appointed time, he came down, welcomed me and we climbed up the three floors to his apartment. He offered me a drink, and he led me to his bedroom, where we talked chit-chat for about 10 minutes while he slowly began touching and caressing my arms and legs and back. I have to admit I was so very unsure of what might be about to happen that I was literally shaking. This man is gorgeous with an almost movie star face and I was this older, overweight newbie, completely ill at ease.

 

There was a lull in the conversation and he moved in to kiss me. He told me to relax and we began to make out in earnest. He started to undress and also to remove my clothes. When he got down to his bikini underwear and I could see his hard-on trying to push out, I could not believe it. He turned around and took off the bikinis and gave me a view of his perfect ass before turning back around and taking my breath away at the sight of his thick, super-hard cock.

 

He invited me to take his cock in my mouth and I began to struggle with that unbelievably impressive tool. My sucking technique needed a lot of work at that time (I like to think that since then a number of generous men have been kind enough to help me improve it with tips and mini-lessons!) but he appeared to be so into that blowjob from me! I moved on down to suck his balls lightly and found his hot hole was so close to his taint that I just had to move my tongue on into that hole! No non-escort I had ever hooked up with had ever been so clean before so this was actually the first time ever that I was turned on by eating out another man!

 

He then started blowing me and we 69’ed for a short time but I knew I could not last that way and pulled his mouth back to my mouth for more kissing. Then he began playing with my butt and using his fingers to gently open me up. I told him I was afraid I would not be able to take his dick inside me but asked if he could maybe just rub the full length of his thick cock between my ass cheeks. He was happy to comply and I was in frottage heaven for a bit. The hour was almost over so he lubed up my dick and started jacking me while at the same time licking and lightly sucking my nipples until I couldn’t hold back any longer and shot a huge load which splashed on both of us.

 

We just lay together there for a minute or so and this may sound strange, but at the time it seemed to be such an intimate action: my face was covered in sweat and he took his hand, wiping away some of that sweat while at the same time blowing gently on my face to help dry the excess sweat there. That struck me as such a unique act of kindness and intimacy. Then he got me a towel so I could clean up.

 

I have to admit that I was apologetic to him at various times during the session about my looks, my age, my lack of technique, etc., so before we began getting dressed, he sat me down next to him on the bed and lectured me in a very kind way about my apologies during our time. He said that I had some wonderful physical qualities and named them to me. He called me handsome and told me he couldn’t understand why I felt in any way unattractive as he found me very attractive. He also said that if I ever hired another escort I should never apologize for anything about myself. Ever!

 

We got dressed, he walked me down to his street door, put his arms around me and kissed me three times. He asked me to keep in touch and call him when I got back after my trip to tell him I had arrived home safely. He also invited me to call anytime I wanted just to catch up on our lives a bit. As I walked out that door and headed uptown, I felt as if my feet were floating above the sidewalk. All in all, this true boyfriend experience became the measure with which to compare all my future escort hires. It also made me decide that hiring escorts was definitely a hobby I wanted and needed to pursue.

 

Oh, and every time since then I have travelled to New York, I have hired him again and each time just gets better and better!

 

TruHart1:cool:

[Traveler North]

Buffalo NY 2001

 

Had gone to a gay film house. Was really aroused after movie. Called local agency and a guy was sent over. Meeting was a bust. A real arrogant guy who did next to nothing but took my money in advance. Later when at my place in Florida, found number of agency in phone book and called. Guy came over who taught me ins and outs of man2man sex. A young college student who worked with other guys to make tuition money. When he came, it was like a waterfall. Had one other guy who was a student but soon stumbled on a website and noticed reference to Steven Kesslar. Called him and set date and flew to San Francisco. Called several times to tell him I had arrived but no answer. Was really worried until he called and said he had been riding his bike and forgot his cell phone. Meeting was great and have been seeing him ever since. A great guy in all ways.

[+ Charlie]

This question has been asked before, and I have answered it a few times over the years, so you can find the my story (and others) in the archives. This is a brief recap.

 

New York, 1978

 

I have just returned to my apartment after three weeks at home in Virginia with my family following my father's funeral. I am very horny, but in no mood to go out to search for sex in the usual places. I pull out the The Advocate's "pink pages" (the PC and the Internet haven't been invented yet) and find an ad for an agency. I call, make an appointment, and am directed to an old office building in Chelsea. I emerge from the elevator on the 4th floor and enter an office, bare except for a receptionist sitting at a desk and a broken down sofa with three or four nelly youths lounging on it. I have already specified that I want something more butch, and the receptionist--whom I recognize as a face from the bars--says that my guy is on his way, and tells me to go into the neighboring room to wait. It is a large office with a double bed and not much else. I lie down on the bed and wait about twenty minutes. The door opens and a very tall, slim, dark-haired man, probably around 30, in tight-fitting leather, saunters in. His face is so ugly it's surprisingly sexy. He walks over to me, unzips, and pulls out one of the most enormous cocks I have ever encountered. He invites me to suck it. I do for several minutes, and he cums. He smiles, zips up, and leaves. After a few minutes to figure out how I feel about all this, I decide that it probably was not the exciting experience I had hoped for. Nevertheless, I go out, pay the receptionist, and go home. I don't hire again for months, and when I do, I look through the individual ads in the pink pages, and choose someone who I think will be more compatible; he is.

[UconnFlyer]

Washington, DC...early 2013

 

This may sound dumb/naive, but up until late in 2012, I never really knew male escorts existed. My only image of escorts was more along the line of random back alley hookups in seedy areas. Or of call girls working a street corner. My eyes were finally opened when I came across RB, M4RN and this site.

 

Anyway, it was a Friday night and I was horny and tired of getting no action. I came across a very cute escort on RB who I had seen before in porn. He wasn't in as good of shape as his porn days, but still really cute and had a great butt. He had no reviews, but I decided to take a chance. He was busy on Friday, but available for an appointment on Sunday. I was super nervous from then until Sunday. I had all kinds of thoughts...would I be bad at this, would he get aroused with me, would I go to jail?? Needless to say I was very nervous. When he arrived, we chatted a little bit and I felt a little less nervous. Then, it was off to the bedroom.

 

When we entered the bedroom, he immediately took all his clothes off and hopped into bed. This caught me a bit off guard, but I just kind of went with it and got naked myself. We started making out and then I gave him a blowjob. He got hard which made me feel a bit better since it gave me some hope that my skills were ok. However, he was very large and I struggled to get even half of him in my mouth. He tried to blow me, but I was just too nervous and couldn't get aroused. I had kind of wanted to top his beautiful butt, but again too nervous. So I decided to bottom for him. This also proved challenging due to his size and my inexperience. However, he was gentle and patient and eventually we got a nice rhythm going. I eventually came while he was fucking me and then he pulled out and came all over me. Success!!

 

We laid there for a few minutes and chatted. Then he cleaned up to leave. He gave me a nice kiss good bye and away he went.

 

Overall, it wasn't too bad for a first time. My skills weren't great and my performance probably subpar due to nerves, but still I consider the visit a success (compared to some of the horror stories I've read here). I probably should have picked someone less endowed, but that's actually a bit tough in the escort world, where most escorts are above average. I was sore for about 3 days after him and a little worried he might have done permanent damage. Thankfully, I was ok.

 

I'll never forget that first experience.

[JB85]

What were the shows? lol

[leigh.bess.toad]

October 25, 2010. Herndon, Virginia (the location played a key part in making it so memorable). Escort name: Sean Knight.

 

Some of this is covered in my review of Sean. But a lot of the background isn't. I had joined the forum about 2 months earlier. When I joined the forum I was convinced that I was the only married gay man in America. Boy was that quickly disabused. So I made friends with quite a few of the men here who graciously took a nervous as hell newbie under their wing. I had played around with men when I was a young man but hadn't been with a man in decades, and hadn't had sex with anyone in 15 years. There were a few escorts I was interested in seeing. I had already arranged to see Romann when he came to DC on October 29. I thought he would be my first experience. But another escort I was interested in was Sean Knight. Sean ended up coming to DC first. But my schedule didn't allow me to get away until that Monday, the 25th. His announced return home date was the 25th. But a friend here was one of his anchor clients and contacted him. He actually was going to stay in DC for another day or two and visit friends anyway and agreed to see me on the morning of the 25th. At noon. Unfortunately, as sometimes happens in DC, hotel room rates for the weekend were inexpensive, but starting that day went through the roof. For example, a room that on Sunday night was $100, on Monday night would be $350. So Sean asked if I would mind switching to a hotel out near Dulles airport since the rooms were much less expensive and that was near his friends. Since I was coming up from Richmond, it worked for me. So I waited and waited and waited for Sean to let me know what hotel it was. Finally, about midnight Sunday he told me -- the Hyatt. No problem.

 

So the next morning, the morning of our appointment, my first time with an escort, the first time with a man in decades, I was nervous as hell, and wanted to make sure that DC traffic didn't cause me to be late. So I left Richmond early. Like 7 AM. So I got to the hotel at 9 AM. For a noon appointment. I figured I had time for breakfast. So I went for breakfast and then came back and started to wait. And ran through in my mind why this was a bad idea. He didn't choose the hotel because he didn't want to see me. He wasn't going to show up. I was going to be lousy. On and on. All while staring at the hotel. After about 90 minutes though, something else starting bothering me. The hotel looked familiar. Why? Why would a hotel at Dulles airport be familiar to me? I had only stayed at a hotel at Dulles airport one night. And it hit me. Like a ton of bricks. The ultimate sign this was a bad idea. The hotel Sean had chosen, of all the hotels around Dulles, was the hotel I had spent my honeymoon night with my wife 33 years earlier. Now that really freaked me out. The gods were trying to tell me something. So I really spent the next 30 minutes debating: do I stay or go? And Sean was running late. He wasn't coming. He didn't want to see me. Why I didn't leave I will never know.

 

But finally, I got the call from Sean saying he had checked in. And he would meet me by the elevators since you needed a room key to go up to his room. Scared to death, I walked into the hotel, and waited by the elevators. Soon one of the elevators open and a greek god walked out -- Sean. For those of you new here, Sean had one of the most remarkable bodies ever to work as an escort. Completely flawless, head to toe. He was wearing a polo shirt that barely contained his muscles. And the biggest smile imaginable. Somehow I managed to walk up to his room. We talked for a bit, which helped calm me down. A bit. I know he could tell I was scared shitless. And he came over and started to hug and kiss me. And the nerves and fear melted. And I realized as we started to make out how much I missed this. The simple things. The hugs, the kisses, the cuddling, the caresses. Yes, the sex was incredible. I spent a couple of hours eating that incredible ass of his over every square inch of that room. But it had been so long since I had any intimate contact with anyone, the simple things are what I missed most of all. And to share it with someone of the strength and yet tenderness of Sean was remarkable.

 

After we came, we just lay in bed for a bit talking, about me, my life. Sean was the first man I had been with. I had been on the forum less than 2 months. And yet I knew I needed to come out of the closet. Desperately. It wasn't an option. So we talked a bit about it. I had been talking with my therapist about it before then. And about 3 weeks later, I came out to my wife.

 

The funny thing about the Hyatt in Herndon though. After the trauma initially of seeing Sean there, it sort of came to mean the place where I started new phases of my life. My married life. My life as a gay man. So one year after I saw Sean there, I took the man I was dating on an overnight trip to DC for his birthday. He'd never been to the Air and Space museum near Dulles. So we went. So the man who is now my partner and the man I plan on spending the rest of my life with spent our first night out of town together as a couple at the Hyatt Herndon.

 

My review of Sean is the last one up for him. Daddy quoted from it when Sean was named 1st runner up as EOY in 2010. But it wasn't too long after that Sean disappeared, seemingly from the face of the earth. No one I know has heard from him in several years. He had numerous fans and he is missed greatly. I hope he is doing well. But wherever he is, I hope he knows how much that memory he helped create for me means. And the path he helped start me on.

[whipped guy]

October 25, 2010. Herndon, Virginia (the location played a key part in making it so memorable). Escort name Sean Knight... Sean was named 1st runner up as EOY in 2010. But it wasn't too long after that Sean disappeared, seemingly from the face of the earth. No one I know has heard from him in several years. He had numerous fans and he is missed greatly. I hope he is doing well. But wherever he is, I hope he knows how much that memory he helped create for me means. And the path he helped start me on.

Lee... When I saw that you posted in this thread even before I read it I had two tears in my eyes. You had told me the story a while back so I knew the basics. So that first tear was one of happiness for all that you have accomplished since. However, that second tear was for Sean. Yes, Sean with the body of a God, and yes the Sean of that infectious smile. But mostly for the Sean who is one of the most honest and forthright individuals I have ever met. I penned two reviews for him and the day the first one was to be published Daddy called him. Sean suspected a possible bad review... but actually it was to let him know that he had just gotten his most stellar review to date.

 

The last time I saw him he was in NYC as he always attended the Macy's Thanksgiving Day parade. After our session we talked until about three in the morning as I recall. He was a prince of a guy and I likewise sincerely hope that he is well. He also opened up a doorway for me that brought me down a different path and for that I will forever be grateful to him. Damn! I pray that he is okay! I hate to seem as though I am hijacking this thread. That is not my intention, but I am sure that there are countless others who feel the same way as do I. If he still monitors this site I genuinely hope he realizes now many lives he has touched in a such positive manner... I think about him often.

[leigh.bess.toad]

WG -- the curious thing is that although Daddy shows him as inactive under the reviews, his website still is functioning. Someone is paying that web hosting bill.

[whipped guy]

WG -- the curious thing is that although Daddy shows him as inactive under the reviews, his website still is functioning. Someone is paying that web hosting bill.

Yes.., I have been checking his site periodically as well and that gives me hope that he is well and will return. Also, when I get the chance I promise to post regarding my first escort experience to make amends for this slight detour. No time now...

[bigvalboy]

Los Angeles....The year is unimportant, but I was 17. At seventeen, gay, hormones raging, and living over an hour outside of Hollywood out in 'burbs' with my parents, there was precious little for a kid to do. No one in my school or neighborhood was gay that I knew about, too young for bars or bathhouses, I didn't even know anyone that was gay. So I said to myself, self you need sex, period. With the parents on an extended summer vacation, I looked in the Advocate. In those days there wasn't any pictures, just ad copy. I think the ad said something to the effect: 28 yr old White 6 ft 250 blond muscle boy. Model looks. He gave his arms, chest, and waist measurements. Very friendly, avail to travel. 75 per hr. What the Hell, I called, he seemed nice, and he said the distance wasn't a problem.

 

We made arrangements for a meet in two hours. He called back and said that he had just looked up my address and it was really further than he realized, and could I give him an extra 5 dollars for gas....seems funny now. A couple of hours later, he drove up in a 1963 red corvette convertible. I was watching from the window and praying that he matched his description. When he stood up....he was stunning, built like a brick shit house. Just as promised. My parents lived in a rather large house, so he was kinda looking around a little on his guard, wondering if all of this was legit, and not someone who sent him on a 'wild goose chase'...

 

When I answered the door, ( I was cute in those days) he said, "I'm looking for Jon" I said, "I'm Jon" he said, "are your parents home?" I told him that they were on vacation, and that I was staying by myself. I invited him in. I was so nervous, he was gorgeous, and this was going to be the second time that I had been with a man. We had lunch and chatted, played pool, and then he suggested that we go to my room. In those days I knew nothing about top or bottom...lol...well we were both tops. We played around and still managed to have some fun, and when it was over, and I was handing him the money, he said, "Ya know Jon I should be paying you"....I didn't really understand the comment, until years later. Now I always chuckle when I think of him saying that. From that day on, I was off an running. I love hiring escorts. There were a few duds along the way, but for the most part, I found it exciting, and met tons of really nice guys.

[whipped guy]

As promised... and I was not 17...

 

It was a hot and humid Wednesday at 1 PM in early August at the turn of the century... I needed to experience BDSM on a professional level and experience it I did... I was in NYC for a series of meetings and also to catch a few ball games at Yankee Stadium.

 

Only shortly before I had stumbled upon the old Hooboy site and I was astounded to find that there were escorts who specialized in BDSM. I would never have believed it, but I could hire a guy who would show me the ropes on a professional level. In retrospect that was a golden age in NYC with such names as Gino Mancuso, Cole Davis, and Rex Brandt to just name those that quickly come to mind. In any event, I did my research by reading reviews and also by lurking here at the message center to see what the general buzz was about the guys about whom I was considering. After much thought I made a decision and after exchanging a friendly number of emails I subsequently scheduled a two hour session as that is what the escort had suggested would be best as it would allow enough time to get acquainted and not be rushed. I then got cold feet. So a few days prior to our scheduled meeting I emailed to cancel saying that there was a conflict with my schedule.

 

I subsequently arrived in town but with a feeling if emptiness and desolation deep in my gut. I knew that I had made a mistake. I also knew that it was imperative for me to have the S&M experience on a professional level that I so craved. Consequently on the morning of the originally scheduled appointment I called the escort's cell. I got his voice mail and explained that I would be able to keep our original appointment after all if it were still available. There was no response.

 

Totally frustrated I went down to the gym at the hotel and began a vigorous workout. I bench pressed I curled. I pumped. The phone never rang. I then pumped harder and even harder. Again the phone was totally silent. I then began doing crunches and then feeling totally unfulfilled began the routine from the top. I was exhausted and the phone was still mute. By this time it was well after 12 PM so I headed back to my room for a shower. I jumped in, was totally soaped up, and the phone rang. I could not get out of the shower fast enough and almost fell head over heals doing so as the soap dripped into my eyes. It was the escort. The time was still available. I guess he could hear the fear in my voice as his final words to me were, "Don't worry. You're in good hands..." Buy this time it was about twenty of one. I threw on a pair of shorts and a tee shirt and jumped on the E train downtown to Chelsea.

 

The escort had an apartment on the fifth floor... The number was E3... an alphanumeric combination I will never forget. There was no elevator, but I never climbed stairs so fast. My heart was racing when I knocked on the door. When the door opened and I saw the godlike figure that was standing in front of me my heart raced ever faster. That was the first time that I met Reece Rothmeier and it was a meeting that would change my life forever. I still shudder at the thought when I think of that moment to this very day.

 

We sat down and had a nice chat. I was nervous as all hell and after he got into my headspace Reece placed his hand on my thigh, gave my a slight wink, and nodded his head in the direction of his fully equipped fifth floor "dungeon" space saying with a sly evil grin, "Let's go..."

 

Well, I stripped down. He had me wear black leather parachute boots and he gave me a jock to wear. I have it to this day. He placed a old tee shirt on me and in the process of our play he ripped it off my body. I had never really been tied up before and then flogged. Damn did I have a smile on my face. He told me to count ten blows as they landed on my butt and back. However, I was only to count off the "good ones". I remained silent to his astonishment and he ripped into me harder and harder until finally I got to nine... then nine and a half... then nine and three quarters... and ultimately an even ten. WOW! I was in S&M heaven... "More Sir... Please Sir!"... and thus it continued. As the session wound down he untied me and I got on my knees and put my face in his crotch. We were both dripping in sweat. He smelled so freaking good, but I had experienced enough pleasure for one day. For some strange reason I did no go for a taste of Reece that day. I needed to save something for the future... And a future there certainly was as there would be many more visits over the next three years. Three years and three reviews. He was ultimate master and teacher.

 

Reece changed my life forever. There was no return. That Pandora's box had indeed been opened. I often wonder if he monitors this board as he has been retired for many years. If he does he needs to know that I and a few others that post and lurk here still consider him to be the absolute best... a gold standard if there ever was one!

 

I thank the OP for allowing me to relive what was a life-changing moment... but most of all I thank Reece.

[+ purplekow]

It was a hot and humid Wednesday at 1 PM in early August at the turn of the century... I needed to experience BDSM on a professional level and experience it I did... I was in NYC for a series of meetings and also to catch a few ball games at Yankee Stadium. QUOTE]

 

A 'Yankee fan, you deserved a good whipping but not the good kind.

[whipped guy]

A 'Yankee fan, you deserved a good whipping but not the good kind.

Now now!!! Be nice PK!!!

 

Well... as a matter of fact Reece and I did talk some baseball prior to our session getting underway and he was in the Yankee camp as well...

 

Interestingly, the last escort that I hired was a Red Sox fan... and being versatile when it comes to S&M... I turned the tables on him by playing the part of the dom to his sub and had him begging for more... And yes! Balls were definitely part of the fun-filled equation... but not baseballs... ;)

 

So big smile on my face... Actually smiles on both of our faces!!! :)

[Decatur Guy]

Gosh -- everyone remembers their first escort in such vivid detail! I'm not even sure. I know I hired "hustlers" a couple of times in my 20s at bars when I was drunk. Completely unmemorable except it seemed like a rip-off.

 

My first two hires in the Internet age of hiring true professionals were Rob/Alex in Orlando and Renn Callahan in NYC. This was circa 2005, 2006. I can't remember which was first. I think it was Renn.

 

Renn is an aggressive top, and I was quite nervous and tired after a long day of sightseeing in NYC. I hired him only for an hour, and I was pretty unprepared to so quickly have a dick in me after I got there. I more endured the fuck than anything. Still, I was attracted to him. After it was over, I decided not to hire again. It was too much money and literally a pain in the ass.

 

About a year later, I think, I was in Orlando, horned up as hell and striking out in bars and online. I decided to give Alex/Rob a try. This time went a little better, but I still didn't like it too much. They both had HUGE cocks (too big for me) and I was nervous. On top of that, I actually came pretty early in the session. After that, I once again vowed not to hire again. I didn't see it as financially justifiable for what I was getting out of it.

 

A few years later, I found Daddy's and the other websites and actually did some reading before my next hire -- which I believe was Renn Callahan again. This time, I was ready for him and much more at ease. It was an epic fuck.

 

I'm glad my first two times weren't disasters, because I probably wouldn't have tried again. But I've definitely had some great hiring experiences once I got the lay of the land better and got over my nerves and self-esteem issues about hiring.

 

I'd like to hire Rob/Alex again, because I think this time around, I'd be such a better client and enjoy it so much more.

[jojo307]

West Hollywood Ramada Inn----hired Jon Vincent---1998 as I remember. Actually meet him at a bar on Santa Monica---I do not remember the name. He was a bit high---I later learned he was falling deeper into drugs---he asked me to hire him----was $75---I had it so I did---I assumed it would be quick---it was long---as things went on he asked me to top him---I did and he said I hope this last a long time---he stayed for hours---he was completely different than his persona. I later learned about all his demons---I always hope he is at peace,

[+ poolboy48220]

1987 or 1988, in Detroit suburbs. I'd recently had my first ever experience with a guy, a quick blowjob at a glory hole. There was an agency that advertised in the local alternative newspaper, and I'd talked to them and gotten descriptions of some of their guys. I went with Jake, a guy he described as having "truly gorgeous body hair". Jake showed up and I was clearly nervous, Brown curly hair and kind of a baby face. He was very sweet and understanding, I think he got a kick out of being my first. We made out for a bit and undressed each other. The guy was right about his body hair, We went on to mutual oral, the first time I'd ever had my cock sucked, and then I topped him. When I finished he jumped out & ran into the bathroom to clean up, I thought it was a bit abrupt but he came back in and laid down on top of me, looking down into my eyes, and we chatted for a while. He said he danced on a local dance show and let his real name slip, he didn't seem too bothered by it though. I didn't hire again for a couple of years and I never met up with Jake again, I think he must have retired.

[gallahadesquire]

From the old Hooboy site-annex, MEET LOCAL MEN, was a tall football-player-ish guy who was self-proclaimed " you're own personal Hoover". And he was! Thereafter was my life of depravity. There was Number 3, though … I'd im'd him on AIM ( remember AIM) for about five years before I ever actually saw him. We meta couple of times a year and then he retired.

[unsub2O17]

Sacramento--late 2011

 

Was certain I was gay from age 17 on. Didn't really do much about it except fantasize and jerk off until I turned 65. Realized I could die without ever experiencing this deep fundamental of my life. Went at it with determination and logic. Found my first escort on M4RN (was the first site listed on Google). He was a local guy (btw, he told me about Daddy's). I picked him because not only was he gorgeous, but his ad specifically said that he enjoyed older guys and newbies. I've never done anything harder than climb those stairs to his apartment. But I did it. We did it all. I loved it, and I haven't looked back since. I still see him at least twice a month for sex and another time socially. We've become great friends. The word is over used, but he's become very very "special" to me. After all, he set me on this great road, taught me how to navigate, and, then, pushed me to seek ever more.

[leigh.bess.toad]

I just wanted to thank the OP for this thread. It has brought some wonderful stories, some great PMs and emails off the thread, and has been a lot of fun to read the experience of others. Thanks.

[DeNeufaille]

Las Vegas in October 2010

 

I was in Vegas for a concert with a group of old college friends and decided to get a massage instead of going out for brunch with the guys. Funny thing is that I had ZERO clue what an "erotic" massage entailed. So, my first ever m4m experience at 35yrs was with the AMAZING Shaun Ross. He gave a full nude massage and then moved onward to "breaking" me into the succulent pleasures of man play. Damn, I miss that guy... totally, at hot time and he lies about his cock size to a fault as he is MUCH larger than the 7inches he advertised at the time. Thanks for cultivating the memories via this thread.