The Male Escort

To my readers. I know, it's been a very long time since I've published anything, and I'm sorry. I had a vicious case of writer's block, getting stuck on some of my previous stories and I lacked any good ideas for something new. I started a few things, but after a few thousand words, they didn't work out. I still hope to return to some of my old 'friends', but it's uncertain whether that will come to pass.

So here is something different, something new. The story of a male escort/gigolo who is asked to do something unusual by one of his best clients. That will happen later in the story, but first, we're going to see how Paul, the protagonist, gets to that point. I'll probably make a number of mistakes in the set up for this story regarding how a man could end up as a high-end sex worker, and I apologize in advance for them. I've never been a gigolo or an escort (the thought that I could have been is just not credible) so a lot of what I write here is a mix of things read about, seen in movies and pure guesswork. I also touch on some Dom/sub themes and I have little personal experience with that, so again, I hope those who know that world better will also forgive my errors. I hope it won't keep you from enjoying this and just letting yourselves enjoy it for the erotic adventure that it is. Thanks, and thanks for your patience with me. Rabbitman55

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My name is Paul Miller, or that's the name my clients know me by. My real name is unimportant; I use the pseudonym to protect my personal privacy. I'm 28, with a master's degree in Psychology and an undergrad minor in Philosophy from an Ivy League university. I'm well versed in all sorts of subjects, from art to politics (which I try to avoid in my work) to finance to music of all kinds. The most important thing about me is I'm an excellent listener. My clients can talk to me about anything they like, and they know I will be as silent as a tomb. I'll talk to them, but I'll never betray their trust in me to anyone else. It's an essential part of my job, but I'm not a practicing psychologist. For the last three years I've been working as an escort to wealthy ladies in New York City.

Let me give you some details about me besides what I've already told you. I'm 6'2, a very solid 200 lbs. I'm muscular from spending four or five mornings in the gym, doing a mix of swimming and weight training. I've got wavy dark hair and deep brown eyes and perfect white teeth with a strong jawline. I did a little modeling back in college to pay the bills, modeling clothes for magazines. I had the looks (still do) but it was barely enough to pay the bills.

One day, one of my fellow male models was in the changing area with me, and we got to talking and he mentioned how he was working for this woman as an escort. The money was amazing, and the job comprised taking wealthy ladies, mostly older, mostly divorced or widowed, to dinners, opera and symphony performances, as well as parties for very upper crust society events. He knew I had my undergraduate degree by then, and I was going for my master's, so he knew I was well educated, and he could tell I could hold my own in conversation. I was just the type his boss was looking for.

I was not exactly comfortable with this suggestion. "Hal." I asked with an unsure voice, "is this strictly socializing? Or is it a sexual thing as well?"

He smiled, his own winning grin. "Well, officially, if Mrs. Royce (his employer) hires you, she'll tell you sex is not permitted, especially for money. If she finds out that it happened, she'll fire you. But that's just her story in case you should get arrested for prostitution. In fact, most of her clients expect or desire sex with a handsome young man and they pay extra...a LOT extra... for the service, as it were. And Royce will expect her cut, 30%. She even sets up your appointments and knows which clients are expecting sex." I never saw myself doing such a thing, and the word "prostitution" really took me aback. "Look Paul, if you're in any sort of situation with a woman, engaged or a serious relationship, it wouldn't be for you, probably. She does have a few other clients who just want the companionship, but that doesn't pay as well, and besides, I would think any sort of girlfriend would be pissed off if you even took the 'straight' path. But if you're single, willing and up to the tasks, the money is incredible."

"How incredible is it? Just so I have an idea." In fact, I couldn't see myself doing this. Maybe the escort part. But sex for money? With strangers? I wasn't exactly raised that way.

"At least ten grand a week, if you can put in 3-4 nights a week. Possibly more." My eyes must have popped open and Hal half laughed at my expression. "You should really talk to Mrs. Royce. She needs to interview you, of course. And", he said conspiratorially, "she needs to make sure you're built for, and able to do the job." He chuckled and that was the last he said about it, aside from telling me he would tell her about me, and I should call her in two days if I was interested. He gave me her card, just a name and a phone number, and Hal left as I sat dumbfounded on the chair, half dressed.

I didn't call her two days later. In fact, it took almost a week before I decided to make the call. I wasn't seeing anyone seriously at that time, so that didn't hold me back. Money was the deciding factor. My parents were very middle-class people, and I was lucky to have most of my college expenses paid by a scholarship. But grad school was going to cost serious money and I dreaded the thought of borrowing as much as 100K. So, shaking like a leaf, a week later I made the call.

A woman answered, and she sounded like she was in her 40s or 50s, very cultured, if a little 'cool'. Mrs. Royce (she didn't use her first name then and I didn't know if Royce was her actual last name) asked me some questions about my background, my health and my personal habits. Did I eat well, did I practice good hygiene, those kinds of things. Passing that initial test, she had me come to her office in a small building in the East 60s.

I dressed in my best suit, went to my barber to get a fresh cut and shave, and I admit, I did look damn good. I always was a good looking male, even since I was a boy and then teen. Starting when I was about 13, I always had girls interested in me and I'd been involved with girls/women since I was about 15, losing my virginity when I was 16, and since then, I rarely was without female companionship when I wanted it. I know that sounds incredibly arrogant. But I never mistreated a woman, some turned into monogamous longer-term relationships, and some were casual. Sometimes they got hurt and sometimes I got hurt. God knows I'm not perfect. I know it as well. But I did have certain things going for me, a sharp mind, an easy-going nature, and very good looks.

When I got to the office, a 30-something, very pretty blond let me in and called into the inner office to let Mrs. Royce know I was there. While I waited to be called in, I made small talk with the receptionist, Alicia, flirty but polite. I reminded myself I was on a job interview. After ten minutes, I was summoned, and I went into the inner office.

Mrs. Royce was pretty much what I expected. A very well-maintained redhead somewhere in her late 40s to early 50s. Extremely attractive, with an elegant bearing, and at the same time, a very businesslike way about her. She wore a power green jacket with a black shell and black business-length skirt and black hose and heels. She looked every bit the upscale professional woman.

We shook hands and I could easily sense her giving me a sharp look, taking mental notes about my own bearing, appearance and social and intellectual skills. When she offered coffee, I said 'please' and 'thank you', always aware that manners are important.

"Mr. Miller, may I ask, why would you want to do this kind of work? You're obviously intelligent and you could almost certainly get a good job in the business community with your education. Besides the money, why this?"

"Honestly, Mrs. Royce, I hadn't thought about it until Hal spoke to me last week. I admit, the money is a very strong motivator. I'll be going to graduate school and I don't love the idea of starting off my professional life with six figures of debt. When I was young, I had a close relationship with my grandmother and she took me to museums and concerts, art galleries, and I really enjoyed it. I also enjoyed being with her, a real old-country woman (she was born in Austria) with a strong cultural background. While my parents were working, and when they weren't working, they were fighting, my grandmother took great care of me and opened the world to me. So I enjoy those cultural activities, but I don't have the money to go more than occasionally."

She took that in, making some mental calculations. "You know," she said, lowering her voice as if others were nearby, "just so we understand each other, officially I'll tell you that you shouldn't have sex with any clients, especially if they offer you money. That would be illegal. Unofficially, most of my clients are seeking sex and they'll let me know, even what they want, so I can tell them what your time will cost them. Most of them even have an account with me and I bill them accordingly. Many haven't had sex in a long time, or, if they have, it's been a while since it was satisfying. Are you willing to have sex with these woman, mostly older, some not your idea of attractive? Please be honest. I can still use you; some women just want a companion to escort them to functions. And you really shouldn't worry about being arrested. This is all very discreet, I know these women and they're from prominent families, so they're not looking for any legal problems. They're not going to call the police."

"Well, I tend to think almost all women are attractive in their way. Unless they are unpleasant in their personalities, I can find something in just about any woman to motivate me."

"Some of them want to fulfill fantasies they've long had that never were explored. They may want you to play certain roles. You can refuse anything you find truly uncomfortable, but I hope you are very open minded when it comes to playing along. The only thing I would recommend you refuse is any situation where a woman would want to bind you, with ropes or scarves or cuffs. You couldn't protect yourself if she got out of hand, and, rarely, some women do have their dark sides like some men do. Otherwise, you can do as you please and we'll discuss whatever fees you should charge if it's not arranged in advance. Beyond the basic fee for your time, which I determine and usually get paid for before your date. I'm very fair, I think. I keep 30% and you get the rest. For another 5% I can generate tax documents and such so you can keep the IRS off your back. That's your choice, but I suggest if strongly.

"Now, one more thing, and it's important. I need you to undress down to your underwear. From the outside, you are a very attractive man. But I need to see the rest." I figured this would be a part of the interview, so I got up and disrobed, folding my clothes carefully as they came off, down to my boxers. Mrs. Royce got up and walked around me, slowly, taking in my physique and my definition. She suggested a few weight exercises to bring out certain muscles, but overall, she was very pleased.

"Now, you need to take off your shorts. I need to see everything. Some women want a man of a certain...size, shall we say. And I have to ask, not to embarrass you, but I need to see if you can get erect here. Again, I need to know."

"Sure, I figured this would be a part of it." I dropped my draws, so to speak and she checked out my package, soft, and she gave an appreciative nod. Then I needed to get hard for her. "Ummm, you don't mind if I touch myself, do you? It will help. Don't worry, I won't masturbate. Just enough."

Mrs. Royce nodded; I'm sure she had to deal with that before. So I stroked myself, thinking of Alicia in the front office, even thinking about Mrs. Royce. I'd been with a couple of older women in my life. Sure enough, my 8-inch cock didn't let me down. Within a minute or so, I was at full staff. I stood with my legs about a foot apart so she could inspect me thoroughly. She even asked if she could touch me, and I said yes, so she put on a rubber glove, professionally, and held my cock, then held my balls, and I couldn't help from twitching in her hand and letting out a soft moan. She smiled approvingly before she snapped off the glove and told me to get dressed.

"I like what I see, Paul. Your body is in excellent shape, very fit. You could tighten a little bit, but it's not necessary. Your penis is a nice size, large but not too large. Some women will ask me for someone very large, but more prefer a more...comfortable fit. And you can get hard without embarrassment in front of a relative stranger. I think you'll do well."

"Thank you. I'm looking forward to this chance, to make some serious money, and I promise, I have proper manners and I'll always treat your clients right."

"I expect nothing less. Let me ask you about your wardrobe. Is this your best suit?" I answered yes, because it was. "Well, it's nice but you need a better wardrobe. Do you own a tuxedo?" I didn't and I told her so. "You'll need at least one to start, and ideally, three in your closet. You also need fine underwear. I am going to send you to an old-fashioned haberdasher, a man who will custom fit you for five suits, a tux, a couple of pairs of shoes, socks, ties, underwear. It's Spring now, so you don't need outerwear yet, but you will need a good raincoat and umbrella."

"Mrs. Royce, I can't afford all that. That's got to be ten thousand dollars in clothing."

"Try double or triple that. Don't worry, you'll pay me back. I'll take half of your share of your earnings until it's settled. If you do well, it won't take long at all. Do you have plans for tonight?"

"No, but I don't have anything to wear for your clients yet."

"No, it's not business. Well, it is. You're going to join me for dinner. I'm going to see how you are when you're out with a lady. Just wear your suit and meet me at ______ at 8:30 sharp. Don't be late. Never be late to meet one of our clients. I have a good feeling about you, Paul. If we get along well tonight, I think we'll both make a lot of money and you'll have a good time." For the first time, she gave me a very warm smile, friendly, inviting, even. She stood up and extended her hand and we shook, gently. I didn't shake like I would with a man, but with a lady. And I do mean a LADY. She was a sharp businesswoman, but she was also classy with an elegant bearing.

It was 4:30, four hours before we were to meet for dinner, so I went to my apartment (almost a closet) on West 103rd Street. I wasn't exactly living in squalor, the neighborhood wasn't a bad one, but rents in Manhattan being what they are, it was what I could afford while going to school (ok, I guess I can say I went to Columbia, not far from there). I carefully took off my suit and rested on my bed while I thought carefully about what I was about to get into. I could still change my mind; no money had been exchanged or spent. Once I went to get the wardrobe, I would kind of be committed. I asked myself if I could do this physically, sleep with older women, not all of whom would be attractive to me. I convinced myself I could; if I had to, I would divert enough of my mind to think of more attractive women. I know that sounds kind of shallow, but a man still has to get an erection to 'perform'. It requires a certain amount of attraction. I was sure I could do it.

More important though was SHOULD I do this? What would it say about my moral compass? How would I feel about myself? I guess no one's parents raises them to want to sell themselves sexually, including my own. But I had to admit, the money as described was very tempting and it could make life much easier. It would just be something I would keep to myself, never telling family nor even my closest friends.

At 6 I took a shower and a fresh shave, applied a little cologne, and dressed again, same suit but with a fresh shirt and underwear and socks. I wanted to be sure I was on time so I splurged and took a taxi to the West 60s, where the restaurant was, and I was ten minutes early. Mrs. Royce walked in a couple of minutes later and was pleased to find me there already.

We sat and shared a bottle of wine and after we ordered, we discussed the job in more detail. "One thing you'll like about this job is that you never pay, Paul. Not for anything. The client pays always, whether you're escorting her to dinner or a gala or a show or concert. They understand this is part of the deal. And the women I deal with are always kind and never abusive to my men. If they are, I never deal with them again. So you need to tell me if they mistreat you in some way. By the way, you don't smoke, right?"

"No, never. I really hate smoking."

"Well, some of these women do smoke. You need to get a cigarette lighter. Not a Bic. A real lighter. Those that smoke usually expect the gentleman to light their cigarettes for them. So go to a smoke shop and invest a few dollars in a nice lighter and make sure it's full."

I was taking mental notes as we ate, a very fine French meal, and I also could detect Mrs. Royce was flirting with me. I had a feeling that night was going to be my first test.

Sure enough, after she took care of the bill, we stepped outside (I held the doors and her chair for her each time) and she said :"Paul, I'd like you to come with me to a hotel. I do need to know about your 'abilities', but I don't want to take you to my home. I never bring the young men I hire home with me. My private life is my own, and I never cross work with personal. And to be honest" she said as she lightly touched my arm, "I am in need tonight. Are you ready for this?" Her eyes told me not only was she hot, but my employment depended on what I did next. It was expected as part of the job, after all.

"Mrs. Royce, I'd really enjoy being with you tonight. I don't have to 'work'. I find you very attractive."

She smiled appreciatively and said "Call me Diana. It's not my name, but I feel ridiculous if you keep calling me Mrs. Royce." We caught a cab and she told the driver to take us to the Pierre Hotel, one of the finest in New York. "I have an account there" she kind of explained, even though I didn't need an explanation.

We were mostly silent on the short ride, though she kept touching my arm and I touched her knee. I admit, I was aroused. Diana was a very attractive woman; I didn't lie when I told her so. A few blocks away, she turned to me and leaned in to kiss me, and I returned it, willingly. It was tentative at first, but quickly our arms were around each other and the kisses became much more passionate. I didn't know if this kind of thing was expected with a client, but Diana wasn't a client and she wanted this. So did I.

We stopped at the desk, and they immediately gave her a room card, and we made our way to the 8th floor to the room. When we got inside, we took turns using the bathroom, then we were together. And I was nervous. I didn't have any idea how to start, if I was to lead as I would with a woman I was dating. It was a different situation for me.

"Diana, I'm not sure how to start this..."

"Don't worry. The client will always let you know whether she wants to be in charge or if she wants you to take the role. I make a lot of decisions all day long. But now, I want you to lead. And I like men to be dominant with me." Her eyes were brilliant with lust. I could feel her heat glowing off her.

I stepped forward a little towards her, butterflies in my gut, but with the definite stirrings of an erection in my pants. I took her in my arms and kissed her again, darting my tongue in and out of her mouth, and she audibly moaned, letting me know she was genuinely hot for me, which in turn raised my own heat. I helped her out of her jacket, then I took off my own, and carefully draped them over one of the chairs in the room. Diana untied my tie as we kept kissing, then she unbuttoned my shirt and was kissing my chest as I became exposed. I shivered a little from my arousal, and I reached behind her to unzip her skirt, which fell to the floor. She was very sexy in her shell with a pair of black panties and thigh high stockings and her heels. It was like she knew how her day was going to end up when she dressed that morning.