I waited down the block at 72nd Street and Columbus Avenue and watched as the boys came out and down the steps of the high school prep school. He was there, as he was every Friday afternoon. For some reason he could stay out until late in the evening on Fridays.
As he had done before, he took the straight shot southeast on 72nd Street, across Central Park West, into New York’s Central Park, headed over to the lake, and grabbed the bench that he’d claimed as his own on previous Friday afternoons. As he sat down, he unbuttoned his school shirt to show his torso. He was in good shape, slim, smooth-chested, hard, some muscular development already. Beginnings of a six pack. But still boyish, not overbuilt for his age. His sunny blond coloring and ready smile for prospects made him a standout.
As I’d done before, I followed him into the park and took another bench across the path and down a bit. This was my fourth time checking out his routine and he hadn’t varied it. The first and third times he’d picked up a john—both times a man older than I was, but he liked them in shape. I was in shape. Those times he walked out of the park with the man and didn’t come back. The second time, no one took him away. A couple of men had stopped and talked with him briefly, clearly interested, but he must have had a bad day, because he didn’t spend time with them. He’d sat there for a couple of hours and then left alone.
Each time I’d sat at the same bench as always—I wasn’t hiding from him—and worked with my sketch book. I’m sure that by the third time he knew I was as regular on Fridays as he was. He also knew I was sketching him. I couldn’t be positive what he was involved in until this Friday—today. Another boy who worked the park, one who had given me the name Tim, was walking the path and stopped at the bench and did leg stretches with his feet, alternately, pressed into the front edge of the bench beside where the boy was sitting. The two chatted like they knew each other—like they came to the park for the same reason.
Then I was sure. So today I looked at him more openly. I made it more obvious that I was looking at him and sketching. It caught his attention and he got off his bench and came over to me and stood there in front of my bench, hands on hips, a bit challengingly.
“Hi,” he said. He was a bit hesitant, but he’d done this before—struck up a conversation with an older man in the park. “I couldn’t help seeing you over here, looking at me and sketching something. The last couple of Fridays too. Is there something you are interested in discussing with me?”
I gave him a warm smile. “Yes. I was sketching you. I’m in men’s wear. I design clothes for them—mostly young me. You look like a male model. I couldn’t resist drawing you in some clothes I’ve been designing in my mind. Here. You want to see some of my sketches?” I gestured for him to sit down beside me and he did so. I flipped a couple of pages on my sketch pad and turned it to where the boy could see it.
“Hey. That’s really good. It looks like me. I like what you’ve clothed me in in that sketch. I think you should make that cut of T-shirt. I’d wear it. I think mid-drift belly shirts are ass kicking. You showed my six pack off really good in this picture.”
“That’s because you have a really nice six pack.” I didn’t go on to say that he had nice abdominals for a boy his tender age, but I was trying to make him, not be technically correct. “What do you think of mine?” I looked around to make sure no one was watching us and unbuttoned my white shirt and spread it open across my flat belly.
“Ass kicking,” he said.
“I could design one of these for you,” I continued as I buttoned up my shirt again. “I’ve been wondering what you might do to get one,” I said. “Do you do anything else other than come to the park on Friday after school? I know you go to that prep school over on Columbus. I don’t know how old you are, though.”
“Yeah, I know you have followed me over here from my school. I’m a senior there. I’m eighteen.”
“The school is only ninth and tenth grade. You don’t seem to be dumb, so I don’t think you’re eighteen. I don’t want you to be eighteen. I want you to be fourteen.”
“OK then, I’m fourteen,” he said amiably.
I knew then that he’d go with me and that we were just dancing around the issue.
“And I asked what else you might do for me,” I said. I’d turned the sketch pad to another page but only now, as I gestured to it, did he take a look. It was a sketch of me and him naked. I was fucking him in a doggie in the sketch, and he was liking it. I indeed drew for fashion designing and he could clearly see that the figures were him and me, me dominating him in a fuck. To his credit, he didn’t lose his teeth in surprise or disgust.
When he had absorbed the sketch and instinctively had looked around to see if anyone else nearby could see them, I turned to another sketch—me fucking him in a missionary. The man—me—in the sketch had a beautiful, hirsute body. I’d just shown him my fine six pack and hairy chest. He knew I wasn’t exaggerating the sketch.
In the sketch, I was holding the boy’s hips between my hands and I was inside him deep. I had drawn a sketch of my cock and balls over at the side to show him I was hung. If he went with me, he would find I wasn’t exaggerating with the sketch in that regard either. The boy of the sketch—the boy I was showing the sketch to—had his legs raised and spread and his head was arched back looking at the viewer. The expression on his face was one of ecstasy.
Before the boy could think of anything to say, I continued. “I saw you talking with Tim just now.”
“You know Tim?” he asked, still not sure what to say about anything.
“Yes.” I turned to a sketch I’d done when I’d taken Tim home and fucked him. Tim was belly down on a bed—my bed, as this boy would find out, if this transaction worked out. The sketch was made from the other side of the bed, Tim turning his face up to the viewer, and me, naked, behind him, standing on the floor on the other side of the bed, my hands grasping his hips, my dick up his ass. I’d drawn Tim with a look of pain-pleasure ecstasy on his face. “Do you do what else Tim does other than go to school?” I asked.
His eyes riveted to the sketch, the boy said, “Go with men for money, do you mean?”
“Yes. Tim has gone with me. I’ve paid him to let me fuck him. I’ve paid him well.”
“That’s what he said,” the boy said with a shaky voice. “I asked him just now if he knew you, because I’ve noticed you following me and sketching me. He said he’d gone with you.”
“Is this how Tim said it would be with me?” I whispered, showing him the “he and me” missionary position sketch again—the one with the side sketch of my erection.
“Yes,” the boy said, with a low moan.
“Did he say he was disappointed with going with me?”
“No, not at all. He told me I’d have a ball with you balling me. That’s why I came over here. You want me to go with you?”
“You suck cock?”
“You take cock, with a rubber?”
“Would you go with me for a few hours today ... now? Suck me and take my cock a couple of times? My place is a couple of subway stops away.”
I named a fee that was quite generous. He accepted the deal readily. I gave him half up front, the rest promised when I was finished with him.
We hopped a subway at the 72nd Street station midway at the park on Central Park West and rode it down to the port authority stop at 42nd Street. The boy introduced himself as Kyle and I identified myself as John, which made both of us chuckle a bit, he more nervously than I. I held his eyes with mine during the journey, but I didn’t otherwise touch him or show evidence of possession or dominance. We chatted a bit, which put the boy more at ease. I revealed I ran an exclusive men’s shop, designing and showing my own clothes designs to an invitation-only list of well-heeled patrons.
“I design clothes for young guys too. You could be a model for them. You have a great body.”
I could tell that pleased him for me to say. “You look good too,” he said. He touched me on the forearm with the fingers of one hand and let them play in the black curls there. “I like men with hair,” he said.
“I like beautiful blond boys,” I responded.
Kyle said he was living with his grandmother, who pretty much let him do what he wanted, and who played bingo at her church on Friday afternoons and evenings. That’s why he worked the park then. He did it because he liked having nice things she couldn’t give him, and though he had a trust for his living expenses and school, he was on a tight allowance. She never asked where the nice things came from, though. He had indulgent uncles.
“So, I’m going to be one of your indulgent uncles today?” I asked.
He laughed, but didn’t answer.
“You think being picked up by men in the park is a good way to augment your income?”
“I like going with men ... men like you appeal to me. I don’t have any trouble going with you.”
“So, you could stay out all night and your grandmother wouldn’t care?” I asked.
“Not tonight. But I have a friend who covers for me. He says I’m staying with him sometimes when I’m not. She never asks. I tell her in advance.”
“You have a cellphone?” I asked. “And does she?”
“Yes to both,” he said.
“Call and tell her you’re staying out all night tonight. I’ll double the fee.”
He called and told her.
Our destination was a narrow, five-story brownstone on a quiet block of 39th Street, smack dab in the middle of the garment district, the ground floor of which had a garage door at one side that led back to several parking spaces across the back of building to accommodate my personal car and a couple of shop vans. A shop was on the other side of the ground floor, with large windows toward the street with mannequins, in men’s clothes, on display. Between them was a door and a hallway with an elevator and a stairwell beyond. The second and third floors were devoted to clothing production and stock storage. The fourth and fifth floors were my living space. I lived well. I’d inherited a comfortable fortune, much of which went into what I was in the process of doing now.
As we waited for the elevator, I pulled Kyle gently to me and we engaged in our first, tender kiss. While we kissed, I copped a feel of him and put one of his hands on my basket, so he could feel me. He sucked in his breath when he did. I was still only half hard.
“You sure you can handle that?” I asked.
“Sure,” he said. His voice didn’t show any doubt.
“That was a nice kiss,” I whispered as the elevator arrived and we pulled away from each other. “Tell me again that you’re fourteen.”
“I’m fourteen,” Kyles answered in a murmur.
“Last chance. You go upstairs with me, you’re going to be fucked silly with a big cock.”
“I’m OK with it,” he answered.
“I’ll expect you to be a lot better than OK at it.” He was being a bit cocky.
I had a moment of indecision on how I wanted to do it this time—upstairs and slow and easy or straight on back in this corridor to the garage and do him, at least first, in the back of one of the shop vans. One of them was equipped with restraints and had quilts I could lay him on. Sometimes, when the boy was cocky or otherwise needed to be broken quickly, I just took him from here into the garage and into the back of a van, bound him, rode him, and broke him. When he had surrendered completely there, I would throw him over my shoulder, take him upstairs, and use him totally. They always behaved after being broken in the van.
The elevator was here, though. The kiss had been sweet and so was he. I had him for the night. Upstairs it would be then. I’d work him slow. I liked how he hadn’t flinched when I showed him the fuck sketches and that he’d said he liked hairy men.
He gave me a nervous smile as we went up in the elevator, past the workroom floors that weren’t occupied now nor would they be tomorrow. I drew him close in to my side again—he was a whole head shorter than I was and half my size—and kissed him on the mouth. I cupped his basket and he put his hand over mine there. He was trembling. I was too, a bit, in anticipation.
My chosen technique was to work slowly but deliberately and always with the climax to come anticipated, and it usually worked a charm with rent-boys like Kyle, who were used to the fumbled fondle, a fast lay, and a faster good-bye.
The bottom floor of my living quarters was essentially all one room, with one area flowing into the other and the back wall, overlooking a floor-light swathed lush garden, being entirely glass. The seduction sofa faced the wall of glass, so that when I’d gone went to the kitchen area marked off with a breakfast bar island to fetch our drinks, Kyle couldn’t see me unless he turned completely around in the sofa, which he didn’t do. He was looking into the garden.
“A beer OK?” I called out from the kitchen.
“Not old enough. What else do you have?” he called back.
“You’re not old enough to be here, and yet you are. You can have a beer if you want. I won’t make a citizen’s arrest.”
“Fine. That sounds good.”
When I came back with drinks—one beer for me, two for Kyle—I had stripped down to a pair of filmy white cotton nearly knee-length boxer shorts. The shorts were from a line of sexy men’s clothes I designed myself, constructed to give dueling impressions that I found was successful in heightening the other guy’s arousal. On the surface they were very modest, covering a lot and looking like dowdy puritanical undergarments. But as Kyle could see when I was standing before him, holding the two beer bottles out to him, they were so gauzy that they were functionally transparent.
As I found was usually the case, Kyle immediately took a huge gulp from his beer bottle, didn’t remark on me trying to get him drunk by giving him two beers, and stared at my crotch.
I was dark haired and hirsute—a modern orthodox Jew in New York’s garment district, where my family had fit right in and turned a good profit for four generations. I made no apologies for being Jewish. I wore my yarmulke—my black velvet skull cap—to the park, and the sketches I showed the boys made no attempt to hide my hairiness. If either of those put them off, I wanted it to do that in the park, not after I’d gotten them home. I did gravitate to Nordic blonds in my boys, getting an extra thrill of a dark Jew fucking them, and I counted on them getting the same extra arousal in reverse. I usually kept my yarmulke on while I was fucking them. It featured in my sketches.
I was built solid and muscular without being overbuilt. I kept trim. I spent considerable time trimming the patterns of curls on my forearms and thighs and swirling around my pecs and down my sternum and belly and into my pubes—the grooming was designed to make a boy follow the line of hair down to discover that I was a bull. The curls of my pubes were also tight but manly. Most significant, they could clearly be seen through the material of the underwear.
My half-hard cock was mammoth, the exposed bulb huge and pressed against the material of the cotton shorts, hiding nothing while declaring the garb as seemingly pure innocence. I fought hard at this stage to not be fully erect. I wanted to arouse, not scare the boy. He could be scared later when I put it in him—when it was too late to withdraw. Although not fully erect, I did nothing to prevent a wet spot of precum to spread on the material where the bulb pressed the material out. I wanted him to see that. I wanted him to know I was hot for him.
I also didn’t want to hide from him that I was hirsute. I had found that that was an advantage with boys. Men were more iffy about it, and women, of course, but with boys, their much older partner being hirsute became part of the mystique of being taken by a man. Having hair on my chest meant I was a man.
I looked down into Kyle’s eyes. “Satisfactory?”
He hesitated. “I mean the beer,” I said, giving him a little laugh. We both knew I wasn’t really talking about the beer.
“Very,” He whispered in a breathy voice. I knew that, in his mind, he was already riding my juicy cock.
But I made him wait. I’d discovered that a long buildup softened them up to be able to take it longer, deeper. I always played them to the point where they begged me for it. They couldn’t very well say I forced them after that. Then there was just the issue of maybe them getting far more than they thought they were asking for. But there was a bit of thrill for me in that.
We sat close to each other on the sofa, looking out into the garden as the natural light floated away to be replaced by the spotlights highlighting new and different aspects of the foliage. I’d put in exotic plantings to distract those I was stripping down on the sofa. I sipped my beer and Kyle took gulps from his third one. I sat with him in my embrace, his zipper down, my hand inside his fly, playing with his hardening cock. The more beer he drank the more I could feel him relax, with moments of jerking tension as I pressed my pinky into his piss slit, smearing his precum around on his cock head, and then released the cock for a moment, feeling him relaxing again when he thought I was backing off. Of course I wasn’t going to be backing off until I’d had him—repeatedly.
I murmured in his ear a mild, romantic version of what I was going to do with him and praising him for his beauty and luscious body, and he was moaning softly. He was already giving himself to men, but he hadn’t been doing so long enough to build up defenses against a man who took his time, as I was doing, and cajoled him into giving more, to go soft at his core, than he would for a casual john. I could feel him loosening up, his control slipping away from him. I wanted to take him back to his earliest experiences with men, to regain in him a sense of vulnerability and virginity—to make him soft and yielding—and then to fuck him to the quick at his core.
We kissed and fondled each other. My hands going everywhere, slowly disrobing Kyle until the boy was naked and hard and throbbing. I brushed the boy’s hand away each time he tried to lower or remove my gauzy underwear shorts, but I didn’t stop the boy I’d bought for the night from slipping his hand under the garment’s waistband and fondling my balls and stroking my cock bigger and bigger and bigger yet.