By Mickey S.
When I got home I found that Steve had chicken breasts marinating in the refrigerator but left them there as I took out the rest of the dinner fixings. Steve loved to cook and was much better at it than I but on days like this when he had a late class it was my job to do the basic preparation. As I chopped veggies to steam and prepared a salad my mind went back to Richie.
* * * * *
Once Richie had left the hospital and was out of my world I had no intention of ever seeing him again. His dick really excited me but everything else about him scared me. He was rude and aggressive, almost forcing me to suck him. It wasn't really force because every time I saw that dick I was drawn to it as if it were a magnet, but he sure wasn't gentle. And then there was Karen's story about him being in the Mafia. Besides, he was old.
But all day Thursday I couldn't stop thinking about him. As I took temperatures that morning I stared at every patient's crotch. With every back rub I imagined Richie's muscular back. While straightening the linen closet after lunch I kept glancing across the hall to room 5210, imagining Richie just inside the doorway, stroking that massive tool of his.
So at five to seven I found myself behind the supermarket, half-hoping he wouldn't show up. I'd been waiting nearly fifteen minutes and was beginning to think he'd probably forgotten all about me when the white Cadillac appeared around the corner of the building. It rolled to a stop alongside me and I opened the door.
"Get in kid, I haven't got all night."
I hopped in and he was tearing off before I'd even closed the door. We drove in silence for a few minutes to the East Orange Water Reserve, a large wooded expanse covering the whole southern end of town. He turned around at the end of a deserted dead end road and parked facing back in the direction we'd come.
"Okay kid, get to it." He half-turned in the seat, unbuckled his belt, opened his pants, lifted his butt off the seat and pushed his pants and his boxers down to his thighs. His thick cock was swollen but not yet fully hard. I leaned over and took it in my hand, moaning as I felt that hot flesh. I immediately bent over and sucked it into my mouth. Since he wasn't totally hard all of it fit. It immediately began to swell and I was about to pull back but he put his hands on my head and held me in place.
"Just relax, breathe deep through your nose and suck. Don't move."
The last time I'd sucked him in the hospital I'd finally overcome my gag reflex but still hadn't been able to deep throat him due to his size. It just wouldn't fit in my throat. But since it wasn't completely hard it was already in my throat, so as it grew it stretched me from within. I loved the feel of that flesh hardening inside me, stretching my throat, but all of a sudden it reached a point where it was blocking my air passage and I couldn't breathe. I pulled back a bit and took a deep breath through my nose and then went down on it again.
Richie moaned as I went up and down on him. I sucked hard each time I pulled off and he seemed to really like that. In no time he was bucking his hips up into me, fucking my mouth. I wrapped my hand around the base of his dick and squeezed. He groaned and began to shoot his hot seed into me, pulsing over and over again. It was all I could do to swallow fast enough to take it all. As it was a little bit leaked out and ran down his shaft. When I sat up I knew there was some running down my chin as well. I used a finger to scrape it off and then licked it. Richie smiled when he saw that.
"Can't get enough of my cum, kid? Then clean up my dick. I think there's a little more for ya." I bent over and took his softening cock in my mouth and sucked off the rest of his juice. He was probably sensitive after coming and pushed me off after a second. He quickly pulled his pants up and fastened them.
"That was good kid but I've gotta get going."
He drove me back to the supermarket in silence. As I started to get out of the car he spoke.
"Same time Tuesday."
Before I could even say anything he started off. I barely had time to swing the door shut and let go as the car pulled out. I stood there, watching it disappear, wondering if I should show up again. I'd enjoyed sucking him, to some extent anyway, but it was all so one-sided. I wanted more. More of that huge cock, but more than just a quick blowjob, too.
So I went back Tuesday, and the next Thursday as well. Both times it went the same, a drive to the deserted dead end road, a quick blowjob and then a return in silence. The next Tuesday when Richie picked me up he surprised me by heading west.
"I've got a little more time today so I thought we'd do something a little different."
He pulled into a motel a few miles out of town and parked around back, then led me to a room. He already had a key and let us in.
"Okay kid, strip," he ordered as soon as the door was shut. I was kind of surprised at that. Why would he want me to be naked? He'd never shown any interest in any part of my body except for my mouth and that didn't require undressing. I would have thought a man like him wouldn't want to even see another guy's dick. But I did as he said, slowly and self-consciously stripping as he watched. When I was completely naked he smiled although it looked more like a sneer. He pointed to the floor in front of him.
"Get on your knees and take my dick out."
I quickly did as he said, feeling very weird kneeling naked in front of a fully clothed man. I unbuckled his belt, unbuttoned his pants and pulled down his zipper. His pants fell to the floor and I grabbed the waistband of his boxers, pulling them down, stretching them out and over his thickening rod. Without a second thought I took it in my mouth as soon as it appeared.
"Oh yeah, suck me, kid. Nothing as hot as having a naked fag-boy on his knees sucking my dick." He moaned as I swallowed his organ, taking it nearly to the base, which was easier this way than it had been in the car. I sucked for a minute and he pulled me off. He kicked off his shoes and stepped out of his pants and shorts. "Let's try it a little different."
He had me lay down on my back on the bed with my head almost over the edge, then stood over me and presented his tool at my mouth. I opened up and he slid it in. He gently began to pump into me, each time going in just a little further. With my head back he was able to go straight down my throat until his balls were banging against my nose. He fucked my mouth and throat for a few minutes, groaning in pleasure, then surprised me by pulling out.
"Damn, that's a great warm-up. I could almost be happy doing that all night."
Warm-up? This was already more than anything we'd done before. What else could he have in mind? I soon found out.
"Get up on your knees on the edge of the bed and bend over, kid. I wanna fuck your other end tonight."
No way! I mean, I'd had anal fantasies as long as I'd had any sexual ideas at all, but I was sure that something that size would kill me. Almost as soon as I'd learned how to masturbate I'd discovered that I loved to play with my asshole while I did it. At first I just ran my fingertips over it, pressing against it. Then I found that it was even better when I inserted a finger. I loved the stretching feel itself, but then discovered there was a spot inside me that sent shock waves through my body when I touched it. And when I came while pressing it I shot what seemed to be a gallon of cum. I was soon cramming two and three fingers up my ass and by high school was using things I found around the house to fuck myself - candles, carrots, a banana. Once I tried a cucumber but it was just too big to fit. That didn't stop me from eying up the occasional zucchini Mom brought home from the market, though.
But Richie's dick was easily as thick as the cucumber that I hadn't been able to handle, and even longer. As much as the thought turned me on and made my dick jump, I knew it was physically impossible.
"I can't. I've never done that and you're huge. You'd tear me apart."
"I'm sure you can take it. Assholes stretch quite a bit. A coupla whores I've been with loved it. And I know I'm gonna love takin' your cherry."
I looked at that thick dripping tool and was so tempted. I thought about how good my fingers felt inside me and wanted it, but was really scared.
"I don't think so. You're just too big."
"I'll go easy on ya since it's your first time. I'll even let you loosen yourself up." He took a small tube of Vaseline from his pocket and tossed it on the bed next to me. "Go ahead, work your fingers in your hole, get it ready for my big dick."
So in spite of my fears I lay back on the bed, bent my knees up and spread my legs. I greased up my fingers and reached down under my balls to begin playing with my hole. I easily slid one finger in and then a second. As I worked three fingers in and tried stretching myself even more Richie stood by the bed stroking himself.
"Damn, that is so hot, watching you finger fuck yourself. You're a pussy boy, a real slut. I just know you're gonna love this tool of mine inside you."
I managed to get a fourth finger partway into me and then Richie stopped me and got me into position. I knelt on the edge of the bed and bent forward, my shoulders and head on the mattress, my ass in the air. He stood behind me and pressed the mushroom head of his massive cock against my stretched hole. Even with all of the fingering, it hurt like hell as he tried to push his way in.
"Push out as I push in. A hooker once told me it's easier that way."
I did as he said but still let out a yell when he popped through my ring. He didn't ram into me but he did keep pushing, steadily sliding that huge piece of meat into me. It felt like he was ripping me open. I stuffed the bedspread into my mouth to keep from crying out in pain. When I felt his pubic hair on my ass I knew he was all the way in but the pain hadn't subsided. I had no idea how I was going to get through another minute, much less an extended fucking. He usually came pretty quickly when I blew him and I hoped it would be even faster this way.
He wiggled his hips a bit and it was more like he was getting comfortable in me than allowing me to get used to the feel. Then he slowly began to pump in and out of me. Each time he pulled back it felt like he was pulling my insides out. Tears were running down my face as he picked up speed. In no time he was forcefully fucking me, pounding into my hole. The intense pain had faded but I was still sore and uncomfortable. Fortunately it was only a few minutes before I felt him stiffen up behind me as he plunged into me with one last powerful thrust. His huge rod throbbed in my hole as he shot his load. Almost immediately he withdrew, leaving my hole feeling like it was gaping open. He got off the bed and went into the bathroom where I heard him cleaning up. I curled up in a fetal position and cried. That's the way he found me when he came back into the room a minute later.
"What the fuck's wrong with you? Didn't you like that?"
"It hurt," I sobbed. "It hurt real bad."
"Ah, c'mon. It couldn't have been that bad. Fags love to take it up the ass. Happens all the time."
"Not to me. I hoped it would feel good but it just hurt." I couldn't stop sobbing. Richie then surprised me by sitting on the bed next to me. He lifted my head onto his thigh and gently stroked my hair.
"I'm sorry, I didn't mean to hurt you. I just assumed that it would feel as good for you as for me. I don't understand why it didn't."
I had calmed down quite a bit and while my ass was still very sore it wasn't hurting anymore.
"I've always fantasized about doing that but maybe you're just too big."
"Maybe you just weren't ready for it. We'll have to work on getting you better prepared the next time."
I wasn't happy hearing him talk about another time but then he surprised me by rolling me over, carefully spreading my cheeks and gently touching me.
"Doesn't look like any major damage. Real red and puffy but that's to be expected. No bleeding, anyhow. I think you'll be okay."
He gave me a light slap on the ass. "C'mon, let's get moving. There's someplace I gotta be."
I had trouble sitting in the car on the way back to town and went right to my room when I got home. I didn't want my parents seeing me moving around gingerly and asking questions. I wasn't sure I was going to go back to meet Richie Thursday but when the time rolled around I went. My ass wasn't hurting but my hole was still sore. He surprised me by driving back to the dead end road in the woods for a blowjob. When we got back to the supermarket he handed me a small envelope. I opened it and there were half a dozen pills inside.
"We're going back to the motel Tuesday. I figured you wouldn't be ready to try that again today. Take one of these pills an hour before you meet me."
"What are they?"
"Valium, a tranquilizer and muscle relaxant. That should help."
I wasn't sure I wanted to take any kind of drug but I knew that half of my mother's friends took Valium so it couldn't be too bad. I decided to give it a shot. I took the pill a little while before walking over to the supermarket to meet him. As usual he was a few minutes late and when he picked me up we headed to the motel. This time when we got to the motel room he was in less of a rush. I took off my clothes without him having to ask and got on the bed. He surprised me by taking all of his clothes off, too. I'd seen his upper body many times in the hospital. Whenever I'd gone down on him, whether there or in the car, he'd lowered his pants just enough to give me access to his dick. The week before he'd taken his pants off but left his shirt on and I hadn't been in a position to get a good look anyhow.
This time I lay on the bed and watched as he undressed. He wasn't slim but he was all muscle with almost no fat on him at all. His body was smooth with only a dusting of black hair on his arms and legs and a thick bush around his huge dick. As he took off his pants and draped them over a chair I was able to get a good look at his round, firm muscular ass. I'd spent a lot of time secretly ogling other boys in the locker room in high school but this was the first time I had a chance to openly stare, and he was certainly no boy. He was a man, a totally hunky stud, even if he was twenty years older than me.
The Valium must have been working because I was feeling very relaxed, almost drowsy, as I lay on the bed. He took a tube from his jacket pocket and handed it to me.
"Better get yourself ready, kid. Lube yourself up and do some stretching."
I took the tube and squeezed some gel onto my fingers. It was slipperier than the Vaseline he'd used the other time. I lay on my back with my knees bent and reached between my legs, rubbing some of the lubricant around my hole and then carefully inserted a finger. It slid right in with no problem at all. I worked it around a bit and then put in a second, then a third. I'd fingered myself a lot and was used to the feeling but the Valium made it so much easier. After watching me finger fuck myself for a few minutes, Richie picked up the tube and slathered some of the gel over his hardon. He grabbed me by the knees and pulled me to the edge of the bed. I pulled my legs back toward my chest, feeling excited and scared at the same time. I really wanted him to fuck me but after the last time I was afraid it would hurt again. He slipped a pillow under my ass and lined his huge tool up with my loosened pucker.
He placed the head against me and pressed, just lightly at first. I was looser than before so he started to slide in. Even so, there was a bit of a roadblock when he hit my ring. He increased the pressure and I felt a sharp stab of pain as he popped through and I gasped. He looked into my eyes as the pain quickly faded and I nodded, letting him know to keep going. His thick rod continued to slide into me, feeling like it was a foot long. When he was in all the way he stopped.
"Feel better this time?" he asked.
"Lots. It's still a very full feeling but it doesn't hurt."
He slowly withdrew almost entirely and then pushed back in. He repeated that motion several times, picking up speed each time, thrusting more forcefully. Soon he was fucking my butt pretty hard. After a few minutes my legs were getting tired and kept slipping from my hands. He surprised me by stopping and wrapping my legs around his waist. I had thought he wouldn't want any part of my naked body that wasn't completely necessary for fucking to touch him. He then bent over, putting a hand on the bed either side of my shoulders for support, and began to plow my ass even harder. I looked up into his face which was now only about a foot from mine and had the urge to kiss his thick lips. It was a good thing he was too far away for that to happen because I knew he would never go for anything as queer as that. He had his eyes closed, probably because he didn't want to look down into my male face, so I knew there was no way he'd ever kiss me.
His big dick was hitting my prostate with every thrust and in no time I was on the verge of coming without even touching myself. I grabbed my dick and squeezed the head, hoping to prevent my orgasm but it had the opposite effect. I exploded immediately, shooting a huge load all over my chest and stomach, clamping my ring on his dick with each shot. He grunted and plunged all the way into me and froze. I felt his cock pulse in my hole as he shot his load into me. As he came down from his high he removed my legs from his waist and slowly withdrew from me, leaving my hole feeling empty and gaping.
"Damn, that was good. Much better than last week. Make sure you take one of those pills every time from now on. And let me know when you run low and need more."
I stared at his muscular butt as he walked to the bathroom to clean up. I lay on the bed feeling a bit sore, somewhat tired but also very satisfied. After years of fantasizing about being fucked, my first time had been a huge disappointment. But now I knew that reality could be every bit as good as my fantasies, if not better. Of course it would be nice if I were with someone who was into me as much as my ass, but for what it was, it was good.
* * * * *
When Steve got home from school he found me sitting at the counter between the kitchen and dining room, sipping a glass of wine, lost in my memories. As we finished preparing the meal together and then ate, I told him about meeting Richie and that summer of sex. It was late evening and we were cuddling in the den with snifters of brandy by the time I finished.
"We kept up a regular schedule the rest of the summer. He must have had more free time on Tuesdays because that's when we always went to the motel. On Thursdays it was just blowjobs in the car."
"As much as you love sex I can imagine your getting into that, especially as a horny teenager. But weren't you scared? I mean, you're such a sweet, shy guy, even now. I can't imagine you being comfortable with a gangster."
"Sure, I was a little scared, having heard rumors about his background, but he was always pretty nice to me. I mean, he was gruff, crude and assertive, but aside from that first fuck he never hurt me. He didn't force me to do anything I didn't want to. And I really didn't know much about him for sure. We barely talked about anything. By the end of the summer I didn't know any more about his life than when I met him in the hospital. And he knew nothing about me. He didn't even know I was going off to college until a few days before I was leaving."
"So you never got more involved with him then? That was the end of it when you left for school?"
I smiled. "Not by a long shot, babe."
To be continued.