The dead guy, Marten Santos, had been notoriously rich and depraved while he was alive. He had never tried to pass as righteous, though, never pretended to be perfect. We all knew about his peculiar tastes and erratic passions, and loved him for that. Nevertheless, he’d been raised a strict Roman Catholic and so the funeral was a stuffy, conservative affair, held at Our Lady of Divine Sorrows. After the funeral, as the teary-eyed pallbearers removed the casket from the church and solemnly loaded it into the back of the hearse, Our Lady’s bell tolled mournfully, sounding all the more poignant in the gray drizzle of rain. He was a man who was going to be missed by a lot of good people.
In life, Mr Santos had been one of my favorite tricks. When he died suddenly of a heart attack three days ago, the newspaper said that he was pushing seventy. During the year when he’d been one of my regulars, he claimed to be fifty-five. It says a lot that after all these years I was moved enough by a sense of loss to attend his funeral. But then, he hadn’t always been a trick. With Mr Santos, I’d done the unthinkable and allowed a favorite John to become a lover, or nearly so. The shame of that slip-up on my part, and a difficult scene he put me through in a cheap hotel room, had caused us to part on uncomfortable terms. Still, it made me no less fond of him.
I don’t turn tricks anymore, I haven’t for years. I’m almost forty now. I work in a respectable office and I earn a respectable living. I present a very hard-assed, successful-bitch version of myself to the world and it’s helped me to succeed and keep my past where it should be, in the past. The frantic, frenetic survival skills acquired by all New Yorkers makes the town a forgiving place. As long as you don’t wind up at the heart of a sordid public scandal in a court of law, where New Yorkers show their ugly sides and revel in seeing your past mistakes slung at you like so much mud, you can do just about anything to get ahead in this town and not have to worry too much that it’ll come back to haunt you.
Mr Santos and I first met in an upscale espresso shop on the Upper East Side. This was back in the 80s, when a whole lot of people had money to burn. Mr Santos was friends with the owner, Hajid, who was one of my regulars, too. Hajid liked getting blow jobs behind the desk in his office. His office was in the basement of the coffee house. It was decidedly downscale in that dark, damp, vermin-infested cellar. However, a simple blow job, as long as I was willing to have my pants around my knees and keep my naked ass out for his viewing pleasure, lasted only about ten minutes and garnered me two hundred tax-free dollars, so I found ways to make even that
The evening I met Mr Santos, I was actually just having coffee. I wasn’t engaged in business. Hajid and I were on friendly terms. He introduced me to Mr Santos, with a nod and a wink, and Mr Santos pulled up a chair. He got right down to the business of getting to know me better. He ended the meeting by paying my modest tab and then asking me for my phone number, which of course I gave him since it was obvious he was loaded – even more so than Hajid.
Our trysts started out simple and straightforward. Mr Santos would always arrange for me to meet him in other rich people’s high-class apartments. The people he knew went on extended vacations, traveled on business to faraway places, or had primary homes in other countries. Mr Santos was married back then, and apparently he and his other married male friends formed a cozy circle of infidels, each leaving the rest of the crew a key to his empty apartment for extramarital liaisons in his absence. I don’t think the wives ever had a clue what was taking place in the sanctity of their homes while they were off on holiday.
I was never to touch anything, never allowed to get too comfortable in the jaw-dropping luxury of our trysting places. Mr Santos liked anal and that was pretty much the sole basis of our get-togethers, at first. Without fanfare, he would unzip his trousers; let them fall unceremoniously to his ankles, along with his boxers. He’d slip on a rubber; slather it with the lube that he carried in his pocket in handy individual foil packets. Then I’d bend over anything steady and he’d slide his cock up my ass.
He fucked me like a man who had important meetings to get to, so he usually came pretty quickly. I didn’t have to say anything weird, or dress in anything unusual. I simply had to show up with an absolutely clean asshole, bend over and let him ream me; that was all he required. For that, I got five hundred dollars cash; five crisp, one-hundred-dollar bills, folded in the middle, which he’d place under my nose while I was still bending over – before he’d even pulled his cock out of me, I’d get paid.
There was something about the way he paid me that tended to make me feel a little humiliated, but he didn’t seem to think twice about it. By the time I’d turn around, he’d have the used condom off, his trousers pulled up, and would be heading to the toilet to flush the condom down. He never said anything like. “Here’s your money you whore,” or “Take that, bitch.” He just had a funny habit of leaving it parked under my nose while my ass was still stuffed with him.
I remember when we had our first real conversation. It was a day when he seemed to be at leisure. He wasn’t pressed for time, wasn’t hurrying. It was a day when he wandered around the spacious apartment we were using, looking for the perfect place to bend me over, making small talk, making jokes. “Bend over that chair there, let me see the view. Pull up your skirt. No, we can find something better.”
When he finally decided on the perfect spot – an economically correct artist’s stool – he lifted my skirt himself, pulled my panties down (an intimate gesture he’d never once done before) and then said, “You know what this reminds me of?”
My naked ass in the air, my thighs spread in anticipation, my head hanging down, I said, “No, what?”
“Church. This reminds me of church.”
He didn’t elaborate and I had no idea what he was talking about. But the thought of church seemed to make him feel even more jovial. He sank to his knees and rimmed me, his hot, wet tongue expertly stroking my puckered hole. It felt sensational. I actually moaned and felt like touching myself.
Having his nose in my ass seemed to arouse his passion, for that day he fucked my ass especially vigorously, nearly knocking me off the stool several times. The mounting pressure of his thickening hard-on sucking in and out of my ass made me cry out. When he came, he pulled his cock out a little aggressively, gave me a resounding smack on my upturned ass, and said, “Here you go. Thanks, kiddo.” And the money was once again placed in front of my face – on this occasion, I’d been staring at a parquet floor.
His breezy pre-sex conversing, combined with his sudden rugged manner with me during sex, made me see Mr Santos in a different light. He was a handsome man, I decided, as I watched him zip up his trousers and go off in search of the toilet. I still had my panties around my knees when he came back into the room. I was lingering in my little swoon.
“What’s with you?” he asked.
Snapping out of it and feeling embarrassed, I moved to pull up my panties.
“No, wait.” He stopped me. “Not yet. You feel like making a little extra money today?”
I was caught off guard. He fished out his wallet and surveyed its contents. “Well, I have ten whole dollars.” He found this amusing. “What do you feel like doing for ten dollars?”
“What did you have in mind?”
“I want to try something and see if I can make you come.”
I never, under any circumstances, came with a trick. But Mr Santos intrigued me. “You think you can make me come for ten dollars?”
“Ten bucks, and a nice dinner. What do you say to that? My wife’s out of town and I’ve got all the time in the world. I’ll make it up to you next time about the money. You know I’m good for it.”
I was feeling game. I liked Mr Santos. I wasn’t worried about the money.
He told me to step out of my panties completely, then to squat down on the parquet floor. He told me that under no circumstances should I touch myself; he wanted to do all the work. He lubed two of his fingers, squatted down next to me, held me around my shoulders to sort of brace me, and then he stuck the two lubed fingers up my ass. He wiggled them vigorously in there, pushing hard against my perineum, rubbing the wall of muscle with all his strength.
“
“Go for it, baby. Let everything go. We can clean this up later. Bear down on me.”
I did as he suggested, pushing my asshole down around his hardworking fingers, never dreaming that I could be launched into orgasm like a rocket without direct pressure applied to my clit. But it happened. My thighs shook as I squatted and bore down, more fluids gushing out of my open pisshole. My body was overwhelmed by waves of pleasure as his fingers rubbed more vigorously against the pressure of my now frantically contracting sphincter.
