Friday Nights with Lenny

I stepped back from the sidewalk, hugging my arms close to my sides, and leaned back on the wall at the corner into the alley, raising one leg, knee bent, and my cowboy booted foot flat against the wall. The hole in the sole of that boot was worn clean through and the cold of the wall wasn't as cold as that of the sidewalk pavement. Besides, it was a good pose for the purpose.

While still watching up the conveniently one-way street for slowing cars, I cupped my hands over my mouth and blew. The breath came out in steam and, I'm sure, made it look like I was smoking a cigarette. I decided that was rather cool for the pose I was taking.

I needed a heavier jacket than this leather vest. It was almost Christmas and once again I had failed to migrate to Florida for the winter. I must remember to berate my social secretary for failing to schedule that. A bulky jacket wouldn't work as well, but if I froze to death, it wouldn't matter what I was wearing. The worst of winter was coming on. I definitely needed a warmer jacket than this.

I heard the slamming of a door back in the alley, and in a few moments I heard his lumbering steps. Just like clockwork at this time. I'd decided a long time ago that the guy must work someplace back there that stayed open late. Wherever he worked, it fronted on the street behind me and I hadn't had the curiosity yet to check it out.

"Hi," he said, as he hit the head of the alley. A big-boned guy somewhere in his thirties. Always looking hangdog when he came out of the alley. But it was after 1:00 a.m., so that was understandable. A big lug. Clumping feet, big hands, a head with hair that had a mind of its own. Cauliflower ears and a bent nose. He looked like he'd been in a lot of fights—but not fights of his choosing because he had sort of a teddy bear demeanor. But not fights that he'd lost either.

I said "Hi" back as he passed and huddled my arms into my chest again, looking up the street, not at him.

I'd been staked out here since late summer and we'd only gotten to the "hi" stage. Of course, I only saw him here once a day, if even that. Sometimes, if I was lucky, I was someplace else when he came out of the alley. I did look forward to the "hi," though. It's about the only thing anyone said to me that wasn't just demanding something they wanted.

I watched him lumber up the street, and I had turned my head, looking for slowing cars coming from the other direction, before realizing that he had turned and come back at me.

"You look cold," he said.

I turned my head, surprised. "My fur coat's in a storage vault in Boca Raton," I said. "I'd meant to be down there for Christmas, but you know how it is when business gets crazy."

"Mine is too," he answered with a little laugh. "In a storage vault somewhere. Just can't remember where the storage vault is. But seriously, you look cold and like you need to warm up someplace. You got a place?"

"Yeah, my mansion's back there in the alley. The second cardboard box on the right."

I wasn't being snotty on purpose. I couldn't be seen standing and talking with someone who liked like he might be a john but wasn't while a real one might be just about to cruise by.

"You hungry?"

"I'm always hungry."

He stood there for a moment, in silence, like he was thinking something over. I desperately wanted him to move on, but he was the only guy who said "hi" to me, so I reined myself in. There weren't any cars moving on the street anyway.

"What the hell," he said. "I had a good night. Thursdays are always light. And I'm not feeling like eating alone. My place isn't far from here. It's warm and I don't feel like eating alone. Come on up and I'll fix you something to eat and you can warm up before coming out on the street again."

"Well . . ." I couldn't think of a way to say no without hurting his feelings and I'd gotten used to hearing that "hi." He looked like such a teddy bear. And there weren't any cars cruising down the street.

"You look like you could use a shower too. When was the last time you had a shower? You got any clean clothes back there in that cardboard box mansion? And I could throw these in the washer and dryer while you have a meal. Come on. Winter's coming on is a lonely time, especially in this season if you don't have someone special to spend it with, and there's nothing on the television late Thursday nights I like to watch."

"Well . . . . OK, thanks. Give me a minute." Still looking frantically down the street for the hint of a john promising a better opportunity, I backed into the alley and headed for my stash. Someone special to spend Christmas with, I thought. Yeah, I wish. I'll bet this guy wishes too.

We were walking the couple of blocks to where he said his apartment was and he was slowing down while we walked and not saying anything when he abruptly stopped by the door of an all-night bodega.

"Just a minute," he said, his voice a little nervous. "I remembered I needed something in here. I'll be just a sec. You can wait out here."

I watched him out of the corner of my eye as he entered the mom and pop store. He was acting nervous enough that I half thought he was going to hold up the place. But he went down an aisle and stopped right where I sometimes stopped in this store. With a knowing little sigh, I turned and propped my back on the support column next to the bodega window, lifted my cowboy boot with the biggest hole to the wall behind me, hooked my thumbs in my jean pockets, and looked up the street while he picked out what brand of condom and lube he wanted.

I knew how I was going to pay for the shower and dinner. I had gone naturally into "the pose," because there always was a chance that something more promising would be cruising by in a flashy car.

At the street door to his apartment building, not much more than a tenement, he stopped and turned to me and, in an earnest voice, said, "My name's Art."

That put us past the "hi" stage. "I'm Jimmy," I answered. I'm not Jimmy, of course, but it's a good enough name for johns—more often than not more than enough—and a lot easier for them to remember than my own name.

His place was small, but clean, and actually had a separate bedroom, with a brass head-boarded double bed, and bath, in addition to the room that served as living room, dining room, and kitchen. The poor excuse for a Christmas tree he had propped up in a corner was pathetic looking, and made me feel sorry for him—which may have been the tone he had been going for when he leaned it into that corner. The apartment was toasty warm, though, which made all of the difference. And he had a compact washer-dryer unit and was washing the clothes I had been wearing and fixing some dinner as I showered.

He'd shyly looked away as I'd taken my clothes off, and I had to clear my throat for him to reach out a hand to take them. I made no effort to cover myself. I knew he intended to fuck me—that he was just slow in working up to it.

After the time I'd spent out on the street, the apartment was actually a bit more than toasty warm, and when I came out of the bedroom after my shower, I was just wearing low-rise jeans and a flannel shirt over my shoulders that I didn't bother to button. I hadn't put on any briefs or socks and shoes, either. I knew the score here.

His eyes went big when he saw me pad out into the living room, and the skillet he held in his hand wavered for a moment. But then he smiled and said, "Spaghetti OK? From a can? I'm not much of a cook. Got some store-bought Christmas cookies we can have for dessert, though."

"Spaghetti's fine," I said.

"I do have some Chianti to go with it," he continued. "If you . . ."

"Yeah, that would be good. I'm old enough."

He smiled a little smile and I saw him relax noticeably. I knew what he'd actually been asking. The way he was playing this he couldn't very well come right out and ask for ID. The johns rarely did, although with me they probably should. One of my "come ons" was that I looked so young.

We didn't talk much over dinner. We both sat at the table with the chairs reversed and our arms reaching over the backs like we were in some sort of macho man mode—denying what we both knew we were going to do afterward. I wasn't much for chit chat, and I could tell that he was nervous. Probably had never picked a rent boy up off the street before. Half way through his meal, he looked up and saw that I had wolfed my food down and, without asking, got up and opened another can of spaghetti. He was walking on eggs and doing everything he could to be nice to me. Very much the teddy bear. Big and lumbering and looking like a bouncer in a club, but a shyness and gentleness in him as well.

Time to put him out of his misery.

"So, are you going to fuck me now?" I asked after my plate was clean and my Chianti glass empty, doing my best to keep anything out of the tone of my voice that would be hurtful to him.

"I . . . I . . ." He looked almost frightened. "The dessert . . . Christmas cookies."

"It's OK. I saw what you bought in that bodega. I expected it. Unless, of course, you don't like men."

"Uh . . . I don't know what . . . what you get for . . ."

"You're giving me more than enough," I answered. "You're being very nice to me. I'm good with a fuck . . . if you're interested. So, are you going to fuck me now?"

"Yes," he said in a small voice as if it was a revelation to himself, "I'm going to fuck you now. Shall we . . . should we . . .?"

"On the bed's fine with me. Or the floor if you don't want to use your bed that way."

He sat on the side of the bed, his thighs spread, and I was standing, facing him, between his legs. Before he had collapsed on the bed, we'd both been standing there, plastered against each other and rocking back and forth while he kissed all over my face and neck and brushed my shirt off my back. I pulled his T over his head and took the measure of his bulging, hairy pecs, and then ran my hands down his torso and unzipped him and fished his cock out. He was horse hung. God, maybe more than horse hung. What's bigger than a horse's dick? An elephants? The bigger-than-life proportions of the rest of him held true with his equipment. I held him, needing two hands to make the effort worthwhile, as he engorged and went into a frenzy of kissing down my neck and mouthing and sucking on my nipples as his butt slowly descended to the mattress and his lips went down to my belly.

I had let loose of his dick on his way down, and just placed my hands on his head and ran my fingers into his hair.

He tongued and sucked on my belly, making little guttural sounds deep inside him, with one hairy arm encircling my waist and the hand of the other one working hard on the buttons of my jeans fly. That open and spread, his mouth went lower and swallowed my cock and started to give me slow head, while I worked my fingers in his coarse, mussy hair and arched my back.

I wasn't used to a john taking this much time with me. Of course a lot of this was him working himself up to doing something he'd probably rarely done before.

I let him suck me for a good ten minutes until I felt I couldn't take any more without coming—he seemed content to continue working the cock in his mouth and he seemed to be gaining expertise there with each passing minute—and then, slipping out of his mouth, I went down on my knees on the floor between his thighs, took his cock in my mouth, and started showing him what an expert blow job was like.

I was more interested now. The guy's cock was huge. I'd become jaded with the homeless rent boy stuff to the point that it took a really thick and long cock to impress me, and this was one that I knew would stretch me to the limit and let me know I'd been fucked.

I placed a palm on his belly and gently encouraged him to lay back on the bed, wanting to convey that we were going to be doing this for a while, and then I gripped both of his wrists in my hands, to give him the symbolic sensation that he was mine and under my control now, and I sucked on. He lay docilely back on the bed and shuddered and moaned.

When I stood up, deciding he was engorged and throbbing enough, I held our cocks together for a few minutes, stroking them lightly and looking down into his face. His expression was one of lust and wonder and more than a touch of fear. I knew that, at that moment, he wasn't sure what was going to happen next. Was I going to push my cock into his hole? It was right there. He was in position. I could tell that he wasn't sure who was going to get fucked—and that he was so far gone that he would have taken it if I'd nailed him.

But then I reached over for the plastic bag on top of his night stand and took out the box of condoms and opened it. He had gotten Magnums. At least he knew what he needed. I wondered, though, for a second or two whether there was a size larger than that.

When I was rolling the condom down on his cock and spraying it with lube, I could see any fear in his eyes was being pushed out by the look of arousal and anticipation.

He groaned and grunted and reached for my waist with his big hands as I straddled his torso with my knees right there next to his thighs and with his legs over the side of the bed, and, holding the root of his cock in a hand, working my channel down on the staff.

Once he was bottomed—which was one hell of a job for me to accomplish—he seemed to begin thinking in terms of him being the big man and me being not much more than a boy. He also showed that he had stamina. I started the rise and fall rhythm, but increasingly he was using his hands to lift and lower me on the cock. Slow at first, and he murmured, almost apologetically, "Am I hurting you? Should I—?"

"Do it. Fuck me harder, fucker," I hissed through clinched teeth. "Make me feel it. Give me a Christmas present."

He answered by jerking me up and slamming me down on the cock, harder and harder, faster and faster. With me flopping around on top of him, letting him control the frenzy of the fuck.

It was a monster cock, filling and stretching me, and I came quickly, spouting up his belly.

Taking that as a signal to take full control, he turned and moved both of our bodies up onto the bed, placing me on all fours, crouching over my hips, and fucking me hard, deep, and fast in a doggy fuck, until spasming and jerking his cock out of me and ripping the condom off, he ejaculated up my back.

He collapsed to the side on the bed, turning me as well and pulling me into his belly. We lay there, both panting, him nuzzling his scratchy chin into the hollow of my neck.

"I'm sorry. I lost control. I'm—"

"Do it again," I growled. And I meant it. I hadn't been touched like this for some time. It really was a good Christmas present. I liked being fucked, but I'd done it so often, so routinely, that it took a fuck like this to remind me that I wanted it. He'd been a pleasant surprise.

I remember being aware that light was coming in the bedroom window. It was daylight already. We had been fucking for how long? But not that long if you took into account that it had been after one thirty when he picked me up and we'd messed around a lot before getting to the bed. I didn't normally overnight with johns. We usually fucked where that wasn't possible, and it was usually wham bang good-bye. This wasn't really overnight, though. The guy worked someplace where it was practically the night shift. It probably almost always was getting light before he went to bed.

This wasn't anything like overnight. Nothing special at all, I thought, wanting to denigrate it so that I wouldn't miss not having it when it was over, as I drifted off to sleep. Nothing special here at all. Warmth for a few hours, a nice big cock, and a nice guy really, but nothing . . .

When I woke we were both still stretched out on the bed, on our backs. But not touching. Art was sitting up against the headboard, a couple of pillows propping up his back. He was smoking a cigarette and looking at me. His cock was in full erection.

"What time is it?" I asked, rubbing my eyes.

"Ten in the morning—but still early for me . . . for us. Go back to sleep."

"What is this?" I asked, reaching for and enclosing his erect cock. "This isn't sleeping."

"I was thinking of you. How sweet you are and what a great fuck. But I brought you up here . . . not thinking to . . . at first . . . well, when I first asked you if you wanted to come up. What are you doing?"

What I was doing was turning over on top of his thighs, my face next to the erect cock, my arms running up his torso, palms laying on his hairy pecs, the pad of my index fingers on his nipples.

"I'm going to give Willy what he wants and then I'm going to put him—and you back to sleep. You need your sleep."

His voice was thick and low. "I can't let you . . . you're not just giving it away, I know. I can't expect . . ."

"You're going to let me shower again and you're going to feed me breakfast, aren't you? Even if it's in the afternoon. You aren't going to throw me out on the street again right away, are you?"

"No, I'd never throw you out," he murmured, and then, in a guttural voice, "Oh, shit. Oh, fuck."

I had swallowed his cock and was giving him slow head. He writhed a bit under me and told me it was time for me to pull off him so he could fuck me, but I held him there and sucked on him until he'd ejaculated in my throat. Then I laid my cheek on his stomach, with his cock under my chin, and we both found sleep.

The next time I woke, the clock on the nightstand showed 1:15 in the afternoon. He'd said his shift started at 4:00 p.m. He worked in a music club called the House of Blues as the bartender and the manager most of the time. He'd be the bouncer too, he said, but it wasn't usually that sort of club. He'd worked those clubs—which I could tell from his battered face—but, he said, had gotten tired of that sort of stuff.

He wasn't in the bed. The shower was going. I leaned over to the nightstand and fished for the box of Magnums. There were fewer left than I would have thought.

He had his back to me, standing in the shower, when I entered the bathroom. I wrapped my arms around him. He gave a jerk and a low, guttural sound when he realized I was rolling a condom on his cock. I'd encased his staff in both hands—it took both of them—and had started slow stroking. He'd gone hard immediately. While, still standing behind him, helping the cock fill out inside the condom with one hand, I soaped up every surface of his skin with the other one.

After that he took charge, turning me in the small shower and lifting me and settling my channel on his cock. With my shoulder blades against one wall and my knees bent and my feet flat on the opposite wall, he palmed and squeezed and separated my buttocks cheeks with those big hands of his, crouched between my thighs, and fucked me under the stream of hot water, to a mutual ejaculation.

At breakfast, after a silence during which I put away three fried eggs and a mess of bacon, he said, "I want you to stay here, with me, not out in that alley. At least until you can find something better. It's getting too cold for you to be out there."

"You'd let me turn tricks during the day and stay here at night?" I asked, looking up at him and raising my eyebrows.

"If that's what you want. But it would be OK if you stayed here—just with me. I know I'm not—"

"You're just fine. And your cock and your fucking are more than fine. Your eggs could stand a bit longer on the grill and more salt, though."

We both laughed; he nervously.

"What do you say? You stay with me, and I'll take good care of you."

"You wouldn't ever say anything if I just didn't show up for a while?"

"No, I wouldn't. Whatever it took to get you warm and dry and well fed."

"And riding your cock?"