Saturday, August 11, 2012

The Perfect Client

It started out as a working dinner date at Busboys & Poets. I sometimes think the perfect scam for a straight guy would be to pose as an escort that insists on dinner only first dates. Many clients are happy to do dinner - and only dinner - as a first meeting. He was rather well dressed and fresh from the Kennedy Center piano recital. Tall, handsome, confident, imposing looking man with slicked back silver hair and angular features of considerable intensity. In his sixties at a guess.

Rather easy conversationalist, I must admit, I felt at ease with him very quickly. After some brief pleasantries and exchange of compliments he tells me that he's fascinated by my age limit. I will not accept clients under 45 years of age. I tell him the honest answer, that it wouldn't feel right, that I am, and always have been, attracted to mature men. He has a concentration to his gaze and as I sip on my smooth tasting Merlot I realize that I'm attracted to him. He takes what I say at face value, he's not shocked that I'm an ambitious graduate student and also pleasantly interested in my field without seeking out details of my affiliation. He's a retired IMF man, adult children and recently out of his first gay relationship. He's already talking about weekends in his West Virgina holiday home and his Fort Lauderdale time share. My interest is more than peaked. This is what the industry refers to as "The Boyfriend Experience" and I'm all about that, especially when I'm paid by the hour.

He offers to drive me home which I accept. I want a chance to talk business. He's a top which makes me a little uneasy. I can bottom, but I'm not naturally passive. I don't like to promise it to clients as I have to be in the mood, I can't always relax. I tell him that I have to get comfortable with someone in order to be the passive partner and of course protected only. He doesn't object. As we enter my neighborhood I tell him to pull over a few blocks before my building. He takes the hint and avoids the light of the streetlamps. He leans across and kisses me. He's quite sensual, not at all awkward. I reach down and he's hard, I ask if I can see it and he unbuckles and unzips to reveal his manhood with a mischievous grin. It's quite beautiful, the head mushrooms from the shaft. I unzip myself to show him I'm hard. He spits onto his fingers and begins massaging the head of my erection. I'm in ecstasy as he whispers to me "You're beautiful". I go down on him and he's very responsive, he reclines the drivers seat in deep moans of joy. I have to admit I'm thoroughly enjoying myself. He warns that he's nearly there and I intensify my efforts. He shoots three short spurts of creamy semen into my mouth which I eagerly swallow as a toke of my desire to please him. The two of us lay there out of breath for a moment.

"We need to do this properly next time" he says as he fishes out an envelope from his jacket pocket. I think I made the right move, he's a plumb client. I'm looking forward to more with this one.

Thursday, August 9, 2012

Rentboy Express

I have been convinced for some time that clients pay rentboys not because they could not feasibly date one but because it's quicker and more convenient. If any of you have frequented the popular gay dating sites you will notice how jaded gay men have become. Spoiled for choice maybe, but nobody seems to hook up quick these days and if you don't have several pictures to exchange you can forget it.

Rentboys offer a hassle-free alternative. They save time and energy and therein lies their value. I am objectively quite attractive. Certainly above average but not - realistically - to the level of a fashion model. I have done some modeling work but nothing major. Of course, you have to be in good shape, rentboys can't be fat but I do firmly believe it's mostly about convenience. Generally my clients like my clean-cut image and ivy-league education too. However, as much as I would like to flatter myself, being willing and able to do what they want, when they want and where they want it is the key to success in this town.

Upscale hotel, discrete male early 50's with large cock seeks college kid with deepthroating skills. Must be orally talented. Upscale hotel across town asap. I make the unfortunate decision to drive, traffic sucks and parking sucks and by the time I arrive at the hotel room I'm running a full 20 mins late. As I knock on the ornately decorated door I see a flurry of emails coming through. My bad.

Client is not happy. He has to be at a meeting in 20 minutes. He's already dressed for it with an immaculate shirt and tie. He's giving me a bit of a chewing out as I notice just how handsome he is. Perfectly combed silver hair frames his nicely tanned face. Chiseled features, neat moustache, perfect teeth. The kind of silverdaddy I would date in a heartbeat really. I'm regretting my choice to drive as he talks of calling it off. I step closer and touch the soft fabric of his suit trouser. Based on his body language I don't think he wants to kiss. It's relatively common that, it helps some people to feel like they're not cheating, that a certain kind of intimacy is reserved for their wives or partners. It's not macho to kiss, at least not in some people's minds.

I unzip and fish out his cock, he's not wearing underwear. It is rather large, he wasn't lying and I'm not complaining. It's swelling quickly into a beautiful erection. His glans is a beautiful shade of pink even when erect, and it has a lovely texture against the tongue, smooth and hard. I'm rock hard inside my own chinos as I slowly stroke his muscular thighs and calves. "Get naked quick", he's in need of release I can tell. I strip frantically throwing my clothes, haphazard on the floor. This is the truly glorious part of my career. Getting paid to do this is like a drug, totally intoxicating.

I carefully untie his shoes and remove them slowly, left first then the right, safe for the socks. He drops his pants and grabs the hair on my head in his fist as he face fucks me. I notice he's manscaped, trimmed pubes, shaved balls. He knows he's handsome. His skin smells faintly like perfumed soap. He tells me to lie across the bed on my back. I know what he wants. I hang my head over the edge of the bed, the deep throat position. He cups my chin with his hand as he inserts his erection deep into my throat. He stops and revels at the feeling of the soft palate against his glans. He slowly pushes deep into my throat as I swallow, the head almost pops as it goes down. He's in ecstasy with this. He's gentle enough too. He removes to let me catch my breath and inserts again. This time he can't hold hit, he spurts as he withdraws, shooting some on my tongue, the rest across my chest. "Fuck yeah" he chuckles and throws me a towel.

Sometimes I think it might be fun to surprise a client and tell them I want a date. Of course, I would never cross that line but it's fun to think about. I wonder would he be flattered if he knew I would do it all over for free. Or would he feel cheated?

I'm right for this job.

Wednesday, August 8, 2012

First Problem Client

So we had a lot of back and forth emails. Client seemed a little anxious. I was about to give up on him for asking my availability one too many times then not following through but then he emails me at just the right time looking for "now". It does involve a drive out to a beautiful Maryland country home. Nice winding tree-lined driveway. Must be pleasant to arrive home to such bucolic affluence after the day's work.

He's definitely edgy and he's been drinking but nothing threatening. Besides, he's a small chubby man, I would say late 50's, no taller than 5'6" or so. Bald, round face and features, not without a smidgen of cuteness to his short rounded stature. He does offer me a glass of wine but I politely decline. A few awkward questions are posed and I'm worried that he's got a touch of cold feet. He does eventually concede that "You're a goodlooking kid" so I express my desire to be shown to the bedroom and we're off. I move in for the kiss and it's well received, I can tell, however, that he's intimidated by me. I do enjoy that edge.

I unbuckle his belt and undo his fly but he's not hard. He proceeds to strip me too kissing and licking the newly exposed skin as he goes. So far so good but he's not getting hard. He sheepishly removes my sock and pressed to sole of my foot against his cheek before sucking my toes. He then switches to my ass and finger it gently before tonguing it vigorously. He's not holding back but he's still soft. Then he lays back panting, "do me" he says. I have to admit as I rub his feet, they're not manicured enough in appearance for my taste and I do not want to rim him either. So I drop his foot and lift his arms and begin to kiss and lick his sweaty underarms. He groans approval, a look of bliss on his face and I move down to his still worryingly flaccid penis. It's smaller than average and showing no signs of becoming erect. After what seems like a long time trying I tell him he's getting fucked instead which he reluctantly agrees to. I lube him up and put the condom on. He has nice round white buttocks, he's tight at at entry and soft and sweet upon penetration. I thrust into him hard making a smacking sound with my hips against his buttocks on each thrust. He's breathing heavily eager for my orgasm which I give him loudly as I spurt  out mutual satisfaction deep inside him.

As far as I'm concerned we're done at this point but my my client wants more and becomes indignant when I mention time. He's quite visibly drunk too. He eventually concedes, not without seriously irritating me. When it comes to the cash I can tell he's short. He admits it before I even say anything. I used to be terribly shy about the money part, but I realized that was stupid. I'm a whore and I know it. My clients are not shy about sex so why should I be bashful about my cash reward. I tell him it's not acceptable and offer to drive him to an ATM but as I suspected the nearest is several miles away and he's clearly too drunk to drive. He start with a litany of mutually exclusive excuses: he can't afford that much, (he clearly can), other guys charge far less. I'm furious at this point and questioning my policy of never asking for cash until afterwards. It reassures both parties that neither is law enforcement when sex is initiated before money is sought. Now, I'm learning why it's not always such a good idea.

I have never had an issue with payment before and I'm surprised at how furious I am. I drove for forty minutes late at night on this clients whim to be offered whatever notes were left in his leather wallet. I get the impression that he had no idea what cash was on him in the first place. He has certainly rubbed me up the wrong way.What pisses me off is that he's not apologetic in the slightest. He's screwing me over and he thinks it's amusing. I'm quite a bit taller and stronger than he is. I'm not a violent person and although I'm confident I could could take this white collar drunk in a single swipe I'm not looking to escalate this into something nasty. He could have a gun or something else, he might call the police. I'm trying to think how to play this situation so as to intimidate him a little without resorting to the kind of threat that could escalate an argument with a drunken executive in what has become the early hours of the morning. He's standing there chuckling to himself and I'm having a hard time keeping my cool. I don't think I can leave this situation as is. The idea of him waking up in the morning in his multimillion dollar home and laughing at how he got me to drive from DC for whatever chomp change was in his wallet is just not something I can tolerate. It's like being robbed, that money became mine as soon as his lips touched mine. That's the way it works. There are no negotiations after the fact. He's laughing at me because I'm standing there clueless like a deer in headlights and he knows I wont hit him. This is a total affront and I have to do something.

I walk to the beside table and and pick up his wristwatch. It's a Rolex, I slide it onto my wrist. There's an instant reaction.

"That's not funny! The worst thing you can do is steal from someone, is that what you are...a thief?"

His expression is a little more sober now. I have to admit as hypocritical as it is, it stings to be called a thief. For a split second, it bothered me to be though of as a thief. That surprised me, I thought he might call me a whore. That wouldn't have bothered me in the slightest. I would have even enjoyed that maybe. But he didn't and the calm and polite tone he took had quenched my rage entirely. It seemed unwarranted now and I was about to take it off under the shaming glance of this portly little republican when he left the room. He came back with more bills, fives, tens and twenties. He was still more than eighty dollars short. He said he took them from his sons room. I handed him the Rolex suddenly very ashamed of myself. For reasons I'm not quite sure of, I suddenly wanted to regain his favor. I thought maybe if I knelt down in front of him and unzipped his fly that it might remedy the situation. I have never known a man that was not softened and appeased by the sincere desire to fellate him, but it didn't seem right. The mutual satisfaction of consideration was destroyed.

I like to think of what I do as a form of unorthodox therapy. I'm unusual in my taste and I'm often attracted to my clients, even when I'm not, I can still enjoy bringing a man to orgasm. It's something you have to have respect for. The last time I felt like this is when I was a waiter in my teenage years and had clients skip out on their check. Maybe I'm not in a position to moralize, but it's hard to tolerate someone who relishes the prospect of taking without paying when payment is so obviously not beyond their reach.