First Time Experiences

[ad rian]

A post this morning made me wonder what other people's first time escort experience was like. This question is addressed to both escorts and clients. For clients, was it awkward? Did you cum? If so, how fast, or how slow? For escorts, did you grow close to your first client? In either case, if it was bad, why did you persevere?

 

For me, my first experience was in Amsterdam. I did not fuck, but had an earth-shattering blow job. I have been No. 1 for a few escorts, and it seems like I occupy a special place in their affections!

[chrismac]

Overwhelming, frightening, painful, sometimes embarassing.

 

I never got hard, certainly didn't cum. The guy had a beautiful body and matched my fantasy in the looks/dick department - and was clean and nice, but I was glad to see him go after the two hours were up. He was WAY too rough and intense.

 

He didn't believe me when I told him upfront that it was my first time.

 

I stayed away from gay sex for 8 months after that - thinking, "if this is what it's like, I think I'll have another go at the hetero lifestyle"

[langster]

ad rin, I remember my first one like it was yesterday, 1999. Me, my boss, and another coworker were in Philly on business. Got on M4M and choose a very handsome, masculin, muscular, and hung guy(eyes were bigger than my stomach). I was a total wreck making sure I wasn't going to get caught by my boss and meeting my first escort. He arrived WOOF, I was in a handicap room and I am not, and he almost left because he thought I hadn't told him about this. I never notice it until he told me. We talk and started. Well when I pulled that big cock out out of his Calvin's, must have been 10x8, I knew I was in trouble. I had only had one other top before and he was small but I was going to be a trooper and go for it. So nervous couldn't get a hard on, he offered me a Viagra, but declined. When it came time for the dance he put on a condom and lubed me up and worked and worked to get it in. After quite some time he succeeded and started to pump and I thought he was going to split me wide open. Then there was a little mess, I was so embarrassed, and finally told him to please get that big cock out of me and he did. He told me previously he was not into oral before but he felt so sorry for me he played with me until I got a hard on and gave me a blow job and had me promise that I would not tell anyone. What an Escort!!! Then he let me play with him till he shoot a huge load on me. He is out of the business now so I don't think I'm breaking the promise but will not give you his name. Do you think I could EVER forget that? I still email him every now and then and he and I still get a good laugh out of it. So thats my first experiance and I am sure I'm not the only one to have something like this happen to them on their first appointment. But I put that behind me and am still using HooBoy and have meet some great escorts out there and will keep doing so until I can't anymore. Anyone out there have a simular story?:+

[Prime Muscle]

Starting off was simple and my first experience was very easy and hot as hell. I started when a friend asked me to partner with him for one of his clients. In addition to escorting, my friend was in porn and had an incredible body. O loved having sex with him and never passed up an opportunity and I didn't care who was there. My very first appointment was more a show because my friend and I went at it and the client just wanted to watch. We partnered a few more appointments which were traditional 3ways. Then my friend broke his leg and could not make his appointment so he called and asked me to take it for him. The client was a regular and I had been with him before but never solo. The client was very open to this and we had a great time.

[Guest lipstick]

Folks,

 

This may not quite fit in with the subject, but here goes...

 

My first experience with a guy in which I paid for the sex was with this street hustler on San Francisco's Polk street back in 1990. His rate was 40 bucks (if you can believe that). I couldn't bring him home, so we went to the nearest hot-tub place.

 

He was probably of Italian or Mediterranean background and he was definitely good-looking in a masculine way. But as with most street hustlers, I suppose, he made excuses to not deliver what he had promised, and I was too naive at the time to make a stink about it.

 

That said, though, I look back on the whole situation as being a bit sad. It was probably HIS first time (or he was very new at it), and though he was a big guy (about 6 feet tall) and with a good body, he had the SMALLEST cock I had ever seen on a person. It could not have been any bigger than my index finger. Of course he did not get hard in any way that I could tell. The only good part about it was that I think he was aware of his penis size, and given that he didn't do what he said who would do (mutual sucking), he was as accomodating as he could have been under the circumstances. I'm the type that likes cuddling, and he did engage in that with me, and he did let me touch his body, including his pucker hole.

 

When I look back on it, I'm a bit sorry that I never thanked him for his time.

[Rick Munroe]

I'd placed an ad on the phone line (550-1000) and got hired literally within minutes. My rate was really cheap because I had no idea what I was doing. He lived on the upper west side in a tiny studio that smelled like moldy lilac and he was old (somewhere between cataracts and Depends). He pulled down a Murphy bed and his "scene" was to have me stand over him on the bed and jerk off onto his chest. It was taking me a while to shoot because I had a million things going through my head (Am I gonna get arrested? Is he gonna go into cardiac arrest?) and I think he kind of started to doze off because my cum hitting his chest startled him.

 

Ironically, a month later, he was Derek's first client, too. Isn't that romantic?

[Guest curious2000]

My first experience came out of reading a sex column in Details magazine in the early 90's by a female writer called "Anka". Every month she wrote about different subjects dealing with sexuality, and one month was about the world of both escorts and clients who hire them. I was fascinated by this article and also the hot pictures of escort ads I had seen for years in the back of gay magazines and local gay community newspapers. The article was very favorable and interviewed both gay and straight escorts, mostly in NYC. What convinced me to actually try hiring an escort myself was how enthusiastic the escorts seemed in the article in pleasing their clients and how mush they loved what they do, and love sex, and getting other people off. I was single and out of a two year relationship and about 30 years old. I was fit and attractive and didn't have any trouble picking up other guys in bars, but I was just not into the b/s and games and stopped enjoying the bar scene...so, I got up the nerve to finally call an agency that sent over a very handsome, blond, built young hunk.

 

I couldn't believe I was doing this and was very nervous at first, but he was really cool, and nice and then I started stroking his thighs through his jeans and he leaned in and kissed me. It was great! we then went to the bedroom and were all over each other, sucking,kissing,rubbing,rolling all over the bed. We didn't fuck, because I was so excited and ended up cumming too soon. He was also turned on and his face was bright red and then he shot a huge load all over me.

 

I almost forgot to pay him when he left, but he was so nice about it. We chatted a while more and then he left. He was a student and had a roomate in college and gave me his personal phone # which I found to be very flattering. I called him a few times and he even called me back. I was naive at the time, and got a crush on him and invited him over for dinner...thinking he would learn to like me as a possible future boyfriend. He accepted the dinner date, but then the day of the date, he called and left a messege saying that he could not make it, and cancelled. I called and talked one more time, but nothing more came of it. I was a little hurt, but quickly got over it, and reality set in that hiring an escort was just a transaction of "pay for play" and not to expect anything more ( although through reading about other's experiences on this site, there are rare exceptions for others).

 

I would still date other guys from time to time, and also "sneak" in an escort when I wasn't dating anyone at the time, just for fun. One escort experience turned out to be a regular thing, we really clicked and he was new to escorting and I was the first guy he ever kissed. It was cool because he was so shy and relunctant to kiss another man in the beginning and would just let me kiss his neck ( he is a really butch,masculine acting /looking guy), but months later when we got together he would meet me at the door and shove his tongue down my throat and take me to bed kissing me wildly! When I made a comment on how he sure gets into kissing guys now , he said " yeah, I really like it now!" I havn't seen him in years, but remember him and all the hot sex we had fondly.

 

Now, I see escorts maybe 4 or 5 times a year, or when I travel to a new city, and enjoy hiring new guys ( many times from the great reviews I find here at this website).

 

Brett Silvers was one of my all time favorites, but unfortunatly he retired from the biz. I would love to meet Michael Vincenzo and Haus Weston. And of course the delightful and sexy Rick Monroe and Derek Ross!

 

:9 :9

[ted]

My first escort experience was pre-Hooboy. I searched the web for weeks and weeks and finally settled on Jon Ramsey. I emailed and emailed and finally on the third try got an answer. I was very nervous to start but Jon was great and got me off twice. That's very unusual for me, particularly since I was also feeling slightly under the weather, at least until we got together. 5 years, and a lot of meetings later, we still see each other regularly, in fact I'll be seeing him in a few days. We know each other pretty well at this point. After Hooboy started up, I reviewed my first meeting with Jon even though it had been a while before. I've hired a lot of other escorts over the years, but Jon has obviously been my most regular.

[Guest Thunderbuns]

Curious2000

 

Thanks for sharing your experiences with us. You sound like a really nice guy and your comments were very well put.

 

A nice change of pace......

 

Thunderbuns

[Guest curious2000]

Thanks for the kind works Thunderbuns. I haven't posted anything in a while. I go through phases when I will. I posted a question once a year or two ago and sort of got scolded that my topic had already been discussed before and to do a research in the archives. It can be pretty intimidating in here sometimes

 

But things seem to have lightend up some lately with posts such as your's and Rick Monroe's refreshing posts, so I decided to post and not be such a lurker like I have been most of this year.

[Rick Munroe]

>I posted a question once a year or two ago and sort of got

>scolded that my topic had already been discussed before and

>to do a research in the archives. It can be pretty

>intimidating in here sometimes

 

That's terrible. Between that elitist mentality, the personal attacks and the grammar police, it did become a bit dismal around here for a while. I'm so glad things have changed, and hope you (and the other lurkers!) continue to enter (or re-enter) and contribute. Your first-time experience story was very sweet. I especially like the part where you referred to Derek and me as "delightful and sexy." :*

[Will]

It seems incredible to me now, but only four years have passed since my first time with an escort. I won't say that I've made up for lost time, as neither my energy level nor my bank account would make that possible. But I can say that, thanks to escorts and to this site, now in late middle-age I have finally figured out how to conduct an erotic life that is satisfying, healthy, guilt-free, and -- most important -- lots of fun.

 

Like some other men who frequent M4M, I was born at a time and place, and into a social milieu, that all but guaranteed my reaching puberty and young adulthood with an ego so fully indoctrinated in the self-destructive mechanisms of internalized homophobia that -- frankly -- I never did learn how to behave the way responsible, self-respecting adults behave when they go looking for a mate or even a sex partner. After all, I felt guilty about my desires for men (never little boys, not even when I myself was a little boy!) long before I ever reached puberty. Once at puberty, all of my fears materialized, to say nothing of the unpredicatably powerful urges that forced me to choose between a sexual life that was quite literally dangerous and no sexual life at all.

 

I chose the latter and entered young adulthood, to be brutally honest about it, as a psychosexual cripple. Ironically, I was wildly successful in the profession I had chosen; and in my profession a certain degree of what I call my "sexual anorexia" can actually further one's career. In other words, I got rewarded, outwardly, for being a disaster area inside. Compulsion, alcohol, depression, and a remorseless capacity for sublimation did the rest. By the time I had reached middle age, my outer life was a spectacular success, and my inner life was a desolated ruin, a sexual and emotional wasteland.

 

Despite all that, I finally managed to work out a long-term and very loving relationship with a man who is still, regardless of my feelings about him now, one of the most irresistably attractive people I have ever met. He looked like a cross between Cary Grant and Tom Sellek; he was a brilliant sculptor whose star was very much in the ascendant in the international firmament of contemporary art (he was in the Whitney Biennial, for instance); he was warm, sweet, funny, tremendously affectionate, deeply spiritual, and hard-working. He was also -- I must add -- bisexual with (I later learned) a textbook case of narcissistic personality disorder.

 

It took four years after we broke up before I could pull myself together enough to seek some kind of sexual experience. I was too burned to look for a volunteer, and that's how I came to the world of escorts. I called an agency in New York, ("WOW" I think it was called), who sent over a goodlooking, sweet, graduate student whose looks made him a cover boy for some Chelsea Clone magazine: steroid-pumped, shaved-bodied, topiary pubic hair. The experience was OK, but not my idea of the Real Thing. I tried a well-known local escort. Ditto.

 

Then, a year later, in the autumn of 1999, I found M4M. I was spending the year in Italy, but planning a trip to New York in February of 2000. I made inquiries through the Message Center, followed suggestions, read reviews, and struck up a correspondence with Rick Munroe. Remember that I was a perfect stranger, writing from Europe. Rick couldn't have known whether he was wasting his time. Even so, he couldn't have been more generous with his time and wit. We threw e-mails back and forth at each other for weeks before my trip. And by the time we met -- at Cafe Luxembourg, if you'd like to know -- I felt that we were already friends. Over the dinner table, we laughed and laughed and laughed. We then went back to my apartment and did other things.

 

The rest is history. Although I know this post is "supposed" to be amusing, fun, and even sexy, I couldn't tell my story without telling the truth. Not all of it is amusing, fun, and sexy. But Rick Munroe is all of those things, and more. And by using him as my standard, I have been with other escorts in New York and elsewhere who have enriched my life more than I can possibly say. When posters on this site hurl ugly and disrespectful remarks at escorts, it not only makes me feel protective of the escorts, but it makes me sad that others haven't had the same kinds of experiences with them that I have.

[Guest curious2000]

Rick, thanks for your thougthful response! What a great way to start the day! You are definitely a "bright spot" on the messege boards.

 

:*

back atcha!

[Houston Bonfires]

Dear Will:

 

Your thoughtful, sentiment-filled note brought a lump to my throat as it paralleled my life in many ways. We brushed by each other in posts on other rooms and I felt a closeness and a comraderie and now your sweet words here have made the feelings all the more real. You rate highly in the echelon of potential good friend. Thanks for making 19 Jul 02 better than it would have otherwise been.

 

Your fan,

 

Houston Bonfires

[+ Charlie]

My first experience paying for sex came after I had been actively gay for twenty years. My father had died and I had just returned from a draining, cloistered month with my family. I decided I really needed good sex, but I wasn't in the mood to go out cruising, and potentially dump an emotional load on an unsuspecting partner. So I looked in the Advocate pink pages (this was 1978) and found a listing for an agency, that had an in-service.

 

I went to a small office building, and on an upper floor were the facilities: a lounge area with a manager sitting at a desk, and a couple of bedrooms in back. I had not given them much direction except that I wanted a "hot top". I was sent into a bedroom and told to undress, and then I waited until the door opened and the "escort" entered. He was very tall and skinny, dressed in leather, and had a face so ugly it was perversely erotic. He pulled out an enormous cock, told me to suck it till it got hard, and then flipped me over and, despite my feeble efforts to resist, fucked the shit out of me.

As soon as he came, he left.

 

I jerked myself off quickly, went out to the desk, where a couple of fey young men lounging on the sofa gave me a bored glance, and paid the manager the fee ($65). I never went back, and it was months before I decided to try sex for pay again, this time with a free-lance advertiser, who was so much better that I got hooked on it.

[Rick Munroe]

I'm with you re: Will, Houston. His combination of honest self-analysis, humor, and a common sense approach to escorting, sex, and LIFE in general (not to mention the nice stuff he says about me ) make me his #1 fan as well.

[Will]

See? That's why I come here. Where else can gay men say such things to each other without fear of embarrassment or of being misunderstood? Where else can I find people who know what I'm talking about and will respond from their own experience? When is the last time you got a lot of heart-felt support and encouragement in a gay club?

 

Thanks Bonfire and Wildfire (aka Rick). My heart feels like a Parker-House roll, risen in a warm room and ready for the oven.

[Guest 7Zach]

Ironically, a month later, he was Derek's first client, too. Isn't that romantic?

 

 

And u knew it was true love at that point.

[Guest miketx]

Well it's been about 14 hours since my first experience (private at the Nob Hill). While the surroundings were not the most condusive to a romantic encounter, the gentleman more than made up for it! He was wonderful, passionate, patient & safe. I could not be happier.

[jack]

Though I had turned down my buddy at prep school when he came in my room one night to put his hand beneath my blanket onto my hard cock, though I learned from the showers at prep school and college that the slightly built guys really have the nicest package of cock and balls, though the slightly built medic at the army physical gave me a hard on (afterward, becoming an Officer) and remember seeing guys sleeping with hardons in the barracks and the solf spoken small guy in the shower from Utah with those sincere blue eyes and thin lips with the fat soft cock, though I became a high ranking principle in a major corporation with a wonderful family and elite social and international travel life, though . . . all that . . . I knew. . . I knew that there was one thing . . . to be at peace with myself, honest with myself, that to be a complete person. . .

I was surprised to see the Gaiety, which I had heard about for years, was across from the Marriott in NY where I was staying. Milo, the Brazilain/Japanesse, 5'8", plus, performed. Just my type physically and spiritually, soft, low keyed, gentle, sincere.

We talked. He said yes and knocked on my door in half an hour. I had had noooooo male sex ever. Didn't even know what it sounded like. I didn't know what to do, except when he came in and I shut the door, I took him in my arms and we kissed, kissed, kissed deeply, . . . his tongue rubbed against by ankles . Then he asked if he could take a shower. I stood outside the bathroom in a nifty T-shirt and dark blue running shorts. Milo came out with a towel around his waste. I stood there looking at him, not knowing what to do. He looked at me. In another second he had dropped his towel and plopped himself on the bed on his back with his legs spread out. His fat uncut cock lay toward his navel. I did what was natural (for me at least). I dropped down between his legs and with an sudden instinctive gutteral sound from the base of my being and throat, put my mouth over his cock. Home at last.

Milo taught me how to deep throat him. Milo taught me how a fucking could be, each time, a life experience. Milo enriched my life. I work with Mike at Campus and appreciate the wonderful service that escorts perform for people like me. I am a whole person.

[Will]

That is a beautiful story. That's the only word for it: beautiful. Thank you.

[+ Axiom2001]

If I had not been determined and curious as well as perpetually horny, I would never had engaged the services of an escort.

 

I found his enticing ad in San Francisco's BAY AREA REPORTER-- "...hot Russian, hung, muscular...etc." I telephoned him and made arrangements to meet him at the Travelodge which is not very far from SF's Castro District. The wait began. The anticipation magnified. At nine p.m., he knocked on the door. As soon as I opened the door, he looked slightly perplexed and entered the room with my urging him to do so. This comely, built man sat in the chair that I offered him, and we began our chat (in an attempt to get to know one another). We talked and continue to talk. Suddenly, he began to motion in that area rather furiously, as if to tell me that he was ready for some action. I looked at him and smiled, for I interpreted his actions as his being quite itchy.

 

We continued our in-depth conversation on a variety of subjects until he and I stood to begin why he was there in the first place. He stripped to his boxers (white) revealing his six pack and wonderfully well-shaped, slightly hairy legs. I attempted to kiss him only to be told that "he didn't kiss". I then proceeded to tell him that I needed that, or we should bring everything to a halt right there.

 

This man became somewhat irrational and slightly furious and told me that men hire him in order to suck his eight inch cock; I told him that I didn't, and that I would pay him some of the fee but not the fee to which he and I had agreed. I gave him eighty dollars (much, much, much, much too much). If I had not blurted this amount out beforehand, he would have gotten his supposed twenty dollars for the taxi ride to the motel.

 

Cutie dressed; and while he proceeded to do this, he stated a lot of stuff which indicated that he was not comfortable escorting. He said something about being treated like a piece of meat, etc... (My memory of other particulars has since lapsed.)

 

Once dressed-- he left. I sat there in the room being very, very, very disappointed and invariably "ripped off"! This experience caused me to be shy with the three other escorts I hired since the time I had engaged the services of this "HOT RUSSIAN"!

 

Today I have recuperated from my first experience-- a bad one! And since then, I have concluded that my sexual tastes are eclectic as well as the men that I seek. I am NOT having any qualms about any of my experiences. (I do know that although I've enjoyed most of the men I've seen, I would like to have the $$$'s that have been expended; guys, as you know, it can really escalate and very quickly at that!):9 :9

[Traveler North]

First time I hired an escort, it was a total bust. Was married and wife died. After two years, decided to experiment with my gay side. After seeing a hot gay movie, returned home and called a local service to send a guy over. The guy that arrived at my door was a handsome dreamboat.

 

I was hot with anticipation. Made the mistake of telling him our meeting was my first time. He asked for the money up front which I gave him. When I tried to kiss him and hug him, he drew back and said this was not allowed. He did take off all his clothes as did I. All I could get from him was permission to play with his cock a while. He jerked me off and did not come himself. He dressed and then left. All in all he was with me for 20 minutes. What a letdown!

 

When in Florida several months later, I felt very horny one night and called a local gay owned service. The guy who showed up was really hot. Great voice, beautiful eyes and massive cock which I had to myself as long as I wished. He did not originally kiss but did when I saw him later. Gave a a great massage with his magic fingers. He gave me a heavenly BJ. He then JOed bursting with a huge load all over the place. What an experience. It restored my desire to hire escorts but taught me to do a lot of research before doing so. Have since then had great luck with well-reviewed guys in Florida, Toronto, Atlanta, Las Vegas, etc.