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Remembering Ricky
Okay, here is the story of my first attempt at anal intercourse, actually my first four attempts; it did not go well.
I was fifteen. Ricky was a year older. He lived in the neighborhood. I really didn't know him that well. One reason I didn't is because he went to a private school, a religious school; his mom was really religious and wanted her son to be as well. If she only knew! Well, maybe she did, but didn't want to see. I don't think it was in their religion's tenets for her son to use most of the younger boys in the neighborhood to provide sexual services.
I had known Ricky since I was about twelve and he was thirteen. He was bigger physically and more athletic than most of the boys in the neighborhood. He was really good at baseball; and football and basketball for that matter. All the boys looked up to him when it came to sports.
There was another reason guys looked up to Ricky - the size of his package. It was very noticeable. I know Ricky had shown his cock to some of the boys in the neighborhood, I had heard about it. I imagine more than that had occurred, but I didn't know that for sure. I just knew Ricky had a pretty big cock from seeing him in his jeans.
Once Ricky had gone off to high school he really didn't play with the kids in the neighborhood anymore. I would still see him around and say hello, but that was about it until one summer between my sophomore and junior year in high school. I saw a Ricky around the neighborhood at the beginning of summer vacation and he came up to me and said that we really ought to get together and hang out. It seemed a little strange, but I said okay.
It was a hot Tuesday afternoon the next time I saw a Ricky around the neighborhood. He said there was something he really wanted to talk to me about at my place and asked if he could come over. He also asked if anybody were home besides me. I told him no because both of my parents were at work. I wondered what he wanted to talk about. I really wasn't thinking that he had an ulterior motive because we really hadn't been close friends before.
Ricky came into the apartment and I offered him a cool drink because it was about 85° outside. After little bit of small talk standing in the kitchen, Ricky came to the point.
"Hey, Brian," Ricky said in serious, lower tone of voice, "I heard that you and Jared had been fooling around."
I was taken aback. One, I was surprised that Ricky would bring up the nearly unspoken subject of guy sex, a real high school no-no unless you were berating someone's masculinity in jest or having a contest of macho dominance. Two, I was surprised that Ricky knew about the activity between Jared and me; not that Jared wouldn't have let something slip indirectly to someone, but I knew Jared and Ricky never talked to one another, Jared was too immature to associate with someone with the elite social status of Ricky.
I didn't say anything to Ricky's leading statement, just a hesitant "umm" hoping that the subject would pass. I was very conscious of being alone in my apartment with Ricky.
"Hey, you don't have to be embarrassed, it's cool with me."
Ricky played it off. Where was he going with this?
"Actually, I was kind of hoping that maybe you might be interested doing some stuff with me."
Wow! I was definitely interested in sex, but I wasn't too sure about doing it with Ricky. I didn't really know what he had in mind. I didn't know what he knew about what I had done before with others. Adding even more to my uncertainty was that this wasn't kid fooling around, I was fifteen and Ricky looked eighteen. And what if Ricky told others? I didn't know if I could trust him.
"I don't know."
I tried to delay so I could think.
"C'mon, I won't tell anyone."
I didn't know what to say or what to do.
"I heard about you and Tommy," Ricky bluntly stated.
I was mortified, but I couldn't deny to myself what had happened. How did Ricky find out? Ricky continued before I could deny it out loud.
"You don't have to pretend. I know you sucked his cock," Ricky continued.
"That was a couple of years ago," was all I could think of saying.
"C'mon, let me at least show you mine and you can decide if you want to," Ricky reasoned.
Ricky opened his legs slightly and I looked down and could see his cock bulging down one leg of his jeans. When I looked back up I knew that by looking at Ricky's crotch that Ricky knew I was interested. He didn't hesitate.
"C'mon, no one will find out."
"I ... uhh ..."
"C'mon, let's go to your room."
"O-k-kay," I agreed with a stutter.
I was flustered, but, leaving our drinks on the kitchen counter, I turned to lead Ricky down the hall towards my bedroom. I went in first, but I didn't know what to do when we got in there. Ricky took charge. He started unbuttoning his jeans.
"Why don't you kneel down on the floor?" he suggested, indicating a spot in the middle of the room on the rug.
I self-consciously got down on both knees. Ricky undid his belt, opened the front of his jeans and dug around for his cock, pulling it out of the fly of his underwear. He let it hang there in a fattening arc. Ricky was uncut, but the tip of his triangular head pointed out of a brownish ring that had retracted a bit. It was narrower than the plump shaft a couple of inches back. Ricky was much bigger than Tommy had been. It was a magnificent sight to behold.
There was a tightness in my chest and my heart pounded; desire coupled with sheer nervousness. I wasn't hard yet, but I could already feel a seeping dampness at the tip of my own cockhead.
"Go on," Ricky gently tempted.
I wanted to. I took his swelling cock in hand and eyed the pouting lips, the curves of the half-revealed cockhead, the ready to unfold wrinkled edge of the dark ring of skin. I put it in my mouth.
I heard a sigh. It could've been me, but it wasn't.
The taste of the arrowhead-shaped glans was that of salty sweat and an unwashed tang of a lusty cock. I licked around the pulsing knob whilst unrolling Ricky's slippery foreskin; his flavor intensified on my tongue and I began to lose myself in the moment as I rapidly hardened in my jeans.
"That's it, suck it good."
Ricky's voice had less menace and more of a husky excitement. I had to stretch my jaw as his cock quickly expanded. Ricky's cock jutted forward, a teenage-hardened six inches. I took as much as I could down my throat, loving having a cock as fully as possible. I would soon have Ricky's cock more fully than I ever had a cock before.
I was now painfully hard in my jeans. Not just the thickness, not just the savor of Ricky's cock in my mouth, but the smell of Ricky's crotch, seemed to excite me at some sort of primal sensory level beyond my control.
That was why I was taken aback by Ricky's voice commanding me from above.
"Stop."
What? Didn't he want to shoot his load in my mouth as much as I wanted to taste it?
Ricky slid his thick erection from my wet lips.
"Take your pants off."
I sat dumbfounded.
"Take `em off," Ricky demanded, insistent.
I undid my jeans; my boner stuck up in the white cotton of my underwear. I could see Ricky's erection a foot or so from me. I was distracted from thinking about how I was going to take off my pants while still on my knees when Ricky changed his demand.
"Take off all your clothes."
"What?" I managed to question.
"Take off all of your clothes," Ricky repeated, adding an adamant directive, "now!"
I stripped in a haphazard manner trying to comply. My t-shirt came off over my head, I sat back to kick off my sneakers, quickly pulled off my socks, scooted my jeans and underwear down and off. My clothing was strewn across the floor of my bedroom; I was naked and self-consciously aroused before the older boy.
"Get on your hands and knees."
Did Ricky want me on all fours? I gulped nervously.
"Move!"
I complied. My hands touched the still warm fabric of my crumpled t-shirt as I got into position and presented my backside to Ricky.
Ricky kicked off his Chucks and used his toes on the cuffs, first one foot, and then the other, to slide his Levis off. He kicked them to the side, losing a sock in the process.
"I'm going to fuck your ass."
It was a statement, simply put; what was going to happen and that was that.
I felt all sorts of things. I was excited. I wanted to be fucked. But, I was apprehensive, I needed time to think. I wouldn't get the time. I didn't think I would be able to take Ricky's cock. I had tried putting other things in my ass, like candles and douche nozzles. Even at less than an inch in diameter, they hurt. A lot.
Ricky pulled his second sock off and down came his underwear. He knelt between me and my bed, then spit on his fingers and slid them into the crack of my ass. I shivered at the slick feeling. I spread my legs without being told and Ricky roughly fingered my asshole.
Ricky was impatient. He forced his fingertips into my tight ring.
"Uh-n-nh," I moaned with discomfort.
Ricky withdrew and spit on his fingers again. He shoved two of them partially in, indelicately.
"Uhnn ... Oww."
I tried to stifle my groans, but it hurt.
That was it as far as Ricky's preparations were concerned. He moved his cock into range.
"I'm going to stick in."
The tip touched my opening. I was so keyed up, I felt every millimeter of Ricky's glans as it tickled my moist pout. Ricky pressed forward. There was a slight give and the barest penetration before my ring tried to clamp down at the intrusion. Ricky eased up for a moment.
"C'mon, relax and give it up."
I tried, but Ricky wasn't waiting. With a few moans on my part and grunt or two on Ricky's, the repeated pressing of the older teen forced his pointy glans into my anus.
There was a pause after the breach.
My ring was tingling like it was conducting an electric current. I was almost breathless at having a cock in me for the first time. This state of exhilaration was short-lived.
Ricky tried to force himself in full length all at once; he had fucked girls before, it was known around that he had. Ricky was just trying to do the same to me, but I couldn't take his substantial cock in my virgin ass. His cockhead slipped out as Ricky's ardor almost pushed me off my hands and knees.
"C'mon, Brian" Ricky complained, urgent and raring to go.
He grabbed my hips and replaced the pointed end of his rod. It popped in quicker this time. Ricky forced himself against me.
"Uh ... Nnnh ... Ihhnnn!"
I gasped in pain from the penetrating phallus.
"C'mon!" I was admonished by the frustrated older teen.
Even though Ricky's cockhead was relatively narrow, once past the head his shaft thickened and was like a rod of steel compared to the softer glans. I could take the first couple of inches of Ricky's rod in my unfucked hole, but beyond that was just a searing pain of penetration.
"I can't," I pleaded.
My anus was quivering in agony.
"Yeah, you can. Once I get it in you'll get used to it, I promise."
Ricky wasn't going to be denied.
He forced his cock in again. It was slick enough to slide, but my muscle involuntarily clamped down at the intruding ramrod.
"Ihhnn! S-ss-t-t-top!"
Ricky only paused before giving a full length push. The intrusion was overwhelming; the tremendous pressure! My rammed anus burned fiercely, stretched beyond any previous measure.
"Owww! Owww! Take it out! Take it out!" I begged.
Ricky did. He knew I was in real agony.
"Give it a minute, Brian, it'll hurt less."
I wasn't really listening. My asshole was on fire; I had lost my erection from the pain. I whined a little.
"C'mon, Brian, you're loosened up now."
Ricky got in position again. I let him. He got it in an inch or two. My asshole just gave up at this point. Ricky pressed in again, all the way.
"Ihhnn ... Ihhnn! ..." I snorted, desperate as my body rebelled.
I tried to hold on as Ricky started shoving his cock, but it was too much.
"Stop! Stop, Ricky!"
Ricky pulled back and I eased off his cock. I could feel my opening was all puffy and swollen. My penis hung limp, dripping and sticky as all the precum of my recent arousal drained out.
"Just let me finish, Brian."
"I don't know ..."
I wanted to be fucked, but it hurt so much. I waited a bit for the throbbing to subside.
"I'll go real easy ... C'mon, the hard part is over."
I was torn. I was scared and didn't want Ricky to be angry with me. Ricky was the neighborhood stud and I always wanted his cock even if I wasn't aware until that day that I did. But, I didn't want the neighborhood to know that I wanted to have sex with guys, let alone that I wanted to be fucked in the ass.
"C'mon, just let me finish."
I could hear the need in his voice.
"Okay," I agreed meekly.
Ricky spit on his hand a few times and lubed up his shaft. He put it back at my ravaged opening.
What can I say? It hurt going in. I moaned, in pain, not lust. Ricky didn't hammer me hard like some sort of porn story; he just tried to get his nut. I tried to push back, to take his cock. I reached for mine, jerked it a little, but couldn't get it up.
He came soon enough, cursing with satisfaction, and pulled out. He wiped his dick off on some of my dirty laundry; I think I saw a little bit of brown near the end of his cock. I wiped my burning ass to keep from dripping.
He got dressed and I did too. We headed for the front door in an uncomfortable silence. Perfunctory goodbyes were said.
"See ya."
"Yeah, see ya."
I went back upstairs to the bathroom, took off my pants, and looked in the mirror. My anus was all puffy, like a fat lip. It was red and purple, bruised from being stretched so far. It took three or four days to stop hurting.
I did it with Ricky three other times over the next three or four weeks. It hurt every time, but it got easier knowing what was coming. I never got off when Ricky fucked me as it hurt so much that I lost my erection every time. I jerked off after he left the last three times we did it, but my ass hurt too much for it to be a real pleasure.
Remembering ... remembering being fucked ... and Ricky's cock ... and the summer's heat ... and us being alone in the air conditioned apartment when my parents were away at work ... that was the real pleasure.
It is to this day.
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This was another story destined for the trash, half finished. But, here it is anyway. Maybe too realistic and not fantastic enough for porn?