The day began with a pleasant exchange of emails from a new client. Sometimes you can tell from a person's way of communicating that they're inexperienced. It comes across in subtle yet unmistakable ways. I have never before been asked if I have "done this before". Nor have I been asked if I would be comfortable stripping, if I wasn't willing to strip I think I'd have to find another past-time. This rookie John seemed to think he was pushing the limits by wanting to see me naked. I had to giggle, although I wasn't quite sure if it was role play; your standard corrupting an innocent young man routine. He did comment on how my ad was new, however, I would have thought it was obvious from the basic information and the pictures on there that I'm willing to do more than strip. A ping-pong of emails revealed his fears that I would be uncomfortable, I assured him that I would be more than willing. The reality is I drifted towards being paid for sex, being attracted to older men money is always floating on the horizon. I was offered it all the time, usually in the form of vacations, travel, etc. Then the "generous" phenomenon started and the first time I walked into a hotel room to see hundreds of dollars in a neat little pile on the dresser I was hooked. I have to be honest, it's a huge ego trip to be paid for sex. For those of you who don't know, the "generous" phenomenon is still prostitution but both parties just choose to ignore it. It's generally an arrangement between an older man and a younger man, usually on a regular dating site rather than an escort site. Amateur prostitution if you'll pardon the oxymoron. It's a hook, a kind of coaxing on the part of the older man to get his younger man at a time and place that is convenient for him. That's how I entered the game. I was amazed at how much busy professionals are willing to pay for a few minutes of lustful indulgence. It's far less intimidating than the real thing, you usually get to see your suitor and since everyone is pretending that it's a regular date, there is less pressure to be "on".
So I met him outside the hotel lobby as he smoked a cigar, visibly nervous, shaking hands, shifty eyes. He seemed like the married New England type. We clocked each other right away, conversation was awkward but he was eager to get back the room. The bellhop sensed his anxiety, looked at the John somewhat puzzled and then looked at me, back at the John and then he knew. He restrained a smirk as the elevator came to a smooth pause. I suppose I didn't fit the business colleague age range and given my John's casual chinos and polo shirt versus my shirt and tie, I wasn't the client. Hotels don't really care, at least not in my experience they don't. They just want discretion, as do I, and of course, the client too. A church-going old lady would never clock me like the bellhop.
The questions continue in the bedroom. By this point I'm fully convinced that I have found a newbie John. The shaking hands are not an act. This man is genuinely terrified. I'm fascinated by this, I must admit. I've never really been with a first-timer. I don't mean a virgin, of course, his wedding ring is visible. I mean he's never paid for sex. He looks like the kind of man that plays golf and owns a yacht, country club-esque. The kind of suburban executive with the silver edges and the spoiled blond daughter that gave me so many raging hard-ons in middle school. I'm already drunk on the rush of my first newbie John. My own private fantasy. I step closer, he doesn't seem to want to kiss.
I'm rock hard and he sees though my trousers. I begin to unbutton his shirt and he unbuttons mine. I remove each article of clothing slowly and carefully, as if they were items of great value. He seems to be getting excited. He caresses my erection with an unsteady hand, gazing at it in awe. His trembling had caresses my torso circling my nipple slowly. He nods towards the bed and I lay down. He finishes undressing and joins me. He spits in his palm and massages it around the head of my erection. "Beautiful" he whispers. He's exploring my young body with his hands and his eyes. I lean across and kiss his chest and nipples imbued with the sweet and pleasant scent of cologne and his cigar. I work my way down his navel with slow and soft kisses, he's hard and standing to attention by the time I reach his pubic hair. He has a small but nicely shaped penis with full plump balls, neatly trimmed hair. "It won't take much" he warns. I masturbate him slowly as I kiss around his erection. I lick up and down the shaft and then take the plunge and suck his erection. I can take it to base and tighten my lips around the base, his hips are lifting off the bed to thrust deep into my mouth. Five or six thrusts and he withdraws to cum. Generous spurts one after the other of white creamy textured liquid. I have always found something terribly endearing about bring a man to the point of ejaculation. An orgasm is almost enfantalising. It's a return to the real, pure bodily pleasure unmediated by language.
As his stomach stops contracting from the ejaculation, there is a rather impressive little white puddle of cum on his belly. It's almost a pity, I thought to myself, that he didn't let it pop in my mouth. Of course, he was being a gentleman. It looked so pretty though, I would have enjoyed swallowing the first few spurts maybe let the rest drip out as I eased off. I kissed around the little white puddle admiring the fruits of my labor. He laid there catching his breath and then toweled it away.
He asked if he could touch my face as I masturbated, I said he could. He's was very gentle, the scent of cigar on his fingers was pleasant. He dipped his fingers in my mouth as I shot cum all the way the headboard. He giggled, thrilled by the sight of it. I've always shot far, five or six feet at times.
This is to be a repeat arrangement, he travels to DC at least once a month. So I made my merry way home with a thick bundle of twenties pressing against my thigh. The inexperienced executive is my fantasy, you could spend months looking for that in the dating world and not find it. I do love this gig sometimes.