This is a fiction story that features explicit behaviour between men. Consider donating to Nifty to encourage stories like these.
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I knock on the door to room 504 and a tall, I would even go so far as to say strapping, man answers it. He looks like the guy with the mustache from Gone with the Wind, but more cowboy-like. About forty-five, thick mustache, well-built. I was semi-hard at the idea of meeting a complete stranger that would be fucking me but having no idea what he'd look like, and now I was fully hard because, wow, Henry was a handsome man.
He was wearing a white cotton t-shirt and a pair of underwear and that was it, like he'd just gotten out of bed. "You must be Nate," he said. He stuck his hand out for me to shake. I shook it. He had a firm grip and his hands were massive. I imagined one of those giant fingers in my ass.
"And you're Henry," I said.
"Hank," he replied.
"Hank, then. Hello, Hank."
He gave me a little wave and then stepped aside. I walked past him into the room.
He followed me and then walked to the table next to the floor-to-ceiling window that overlooked the harbour. He picked up a wine bottle and said, "Do you like red wine?" he asked. "I thought if you're feeling nervous, it could help..." He trails off, seeming to wonder how to finish the sentence."Make you not-nervous, I guess." He laughs slightly.
"I've never had red wine," I say. "I've never had wine, period." This is true.
"Want to try it?"
"Sure."
I sit down at one of the table's chairs and Hank sits at the other. He pours us both a glass and I sip red wine for the first time in my life. It tastes like juice that's gone bad and I hate it, but I'll keep drinking it if it makes Hank happy.
We drink each of our glasses as he asks me about school and life and it's pretty boring small talk. He pours me another glass of wine and we continue our conversation, but at this point I start feeling the wine and the idea of seeing Hank without the shirt and underwear is becoming more and more urgent in my mind.
He looks at one of the double beds behind us. "I lost my virginity the exact same way, did Cale tell you that?"
I nodded.
"One of the best experiences of my life," Hank said. "He was forty-one, though, I'm forty-six."
If I stood up, my erection would be completely visible.
He puts his glass down on the table and stands up. "Alright, get up," he says.
I stand up. He motions for me to come to him, which I do. I'm standing in front of him and he puts his - very sturdy - arms around my waist. "Have you kissed a guy before?"
I shake my head, trying to appear as nervous as possible, even though in my brain I'm like: fuck yeah! I can't believe this is about to happen.
He leans in and puts his lips on mine and we kiss for about thirty seconds, just lips. I like it.
He pulls away. "How was that?"
"Good," I say. He leans back in and we kiss some more, until he tilts his head and suddenly his tongue is in my mouth. It tastes like wine and the promise of sexual intercourse. I try to act like I don't know what I'm doing but that I'm a quick learner.
He pulls away from me after a minute and says, "You're pretty good at that!"
"Thanks," I say.
He grabs the waist of my shirt and pulls it over my head, then does the same to his own. He has an extremely well-built and hairy chest and my excitement could not be higher. He wraps his hands around my waist again and sticks his tongue in my mouth. I can feel his erection through his underwear and I have no doubt he can feel mine through my pants.
I make little mm-mm noises as we kiss, because I want him to know I'm enjoying it.
As we make out, he unbuckles my belt and unzips my jeans, then pulls them down as much as he can. I grab his underwear and do the same. I pull away from Hank for a moment to look down at his dick, which is, I would say, about average size but above-average in thickness.
"You like what you see?" he asks, then starts kissing my neck.
"Yeah," I say.
"Put your hands on it," he says.
I put one hand around his balls and the other around his shaft. I start jerking him, but he puts his mouth next to my ear and says, "Kiss it."
I give it a moment, pretending to be thinking about it, pretending to be a little scared, and then get on my knees. I look at his dick as though I've never seen another guy's dick before and that I'm having doubts about this whole becoming-a-cocksucker thing. Then I pretend to muster up the courage and lick the tip of it, sit back and look at it again, then move forward and wrap my lips around the head. Then I start sucking Hank's forty-six-year-old dick. It is absolutely marvelous.
Hank puts his hands on the back of my head as I suck and says, "Good news, Nate, you're a natural."
He enjoys the fellatio for what feels like a very short amount of time before he gently removes my head from his cock and lies down on the bed. "Climb on top of me, Nate."
I do as I'm told and get on top of him. We kiss for a moment and he says, "the other direction."
I'm not sure what he means, until he grabs both my shoulders and starts turning me, and I quickly get his meaning and turn around so I'm on all fours, my ass in his face, and his cock in my face. Are we about to sixty-nine?
"Get to it, Nate," he says, and I immediately grab his dick and start going down on it.
But instead of sucking my dick in response, I suddenly feel a tongue on my asshole and I feel like I could pass out. This is amazing. I make a million little moans and grunts around his cock as he rims me. This is heaven.
After a few minutes, we stop and he sits up, his back against the headboard. He instructs me to sit with my back against his chest, which I do. He moves my legs so that my knees are up and my ass is exposed, then he wraps an arm around my chest and kisses my ear and, to my unending delight, licks the massive pointer finger of his other hand and sticks it in my asshole.
"Oh my God," I say. It feels incredible.
"Just need to loosen you up a bit," he says. "Does it hurt?"
"A little," I say, remembering that I'm a virgin as far as Hank knows.
"That'll go away," he says.
As he fingers me, he turns my head toward his as much as it can go and sticks his tongue in my mouth. After a minute he sticks his middle finger in my ass along with his pointer finger and there is nowhere on earth I'd rather be. His dick is pressed against the small of my back and I desperately want it inside me.
After a few minutes he says, "What do you think, Nate? You want to ride me?"
"Yes," I say.
He pulls his fingers out of me and moves me to a sitting position next to him on the bed. He leans over to the nightstand, pulls out a bottle of lube, and starts greasing up his dick. He reclines on the bed so that he's fully horizontal and says, "Alright, then, get on."
He holds his dick straight up in the air and I crouch over it. I lower myself until the head is pressed against my asshole and then Hank says, "Remember to breathe, Nate."
I take a deep breath and give a deep exhale and then lower myself onto this dick. "Ouch," I say, frowning and pretending I've never done this before.
He puts his hands on my hips. "Go as slow as you want, my boy," he says.
I bravely soldier on, or at least pretend to, as I eventually sit all the way down on his dick, his dick all the way up inside me. "Holy shit," I say, acting surprised.
He smiles. "It's in there."
I nod. "It's in there."
"No turning back now."
"I suppose not."
I lift my ass up a few inches, then back down a few inches. Going slowly at first, trying to maintain the virgin lie. Then pretty soon I'm bouncing up and down on it and moaning like it was my first time getting fucked, which, as far as Hank knew, it was.
"How's it feel, boy?" he asks.
"Amazing," I say.
"Any other position you want to get fucked in?"
I think about it for a moment. "Uh, yeah, actually."
I climb off Hank and the bed itself, and walk over to the TV stand, atop of which, next to the TV, rests a giant mirror. I put my hands on the TV stand and bend over, my ass in the air.
Hank rises from the bed and stands behind me, sliding his thick cock into my now-widened ass with ease. He grabs my hips again and starts fucking me. He smiles down at my reflection as he fucks me and the sight of him behind me, fucking my ass, sends me into overdrive. I have to fight the urge to close my eyes so that I don't miss the visual of him behind me.
As he's fucking me, I look over to the floor-to-ceiling window and realize this hotel neighbours another hotel and that if you were to look from one of those rooms into Hank's window you would very easily be able to see a middle-aged man plowing a high schooler against a TV stand. That got me kind of hot too.
I start jerking my own cock as Hank fucks me and after what feels like a very long time he says, "Any other requests, Nate? Because I'm about to shoot."
"Please do," I say.
Hank grunts loudly and though I can't feel it happening, I know he's unloading his cum in my ass. After a moment, he sort of collapses against me, his hairy chest against my hairless back, and then he reaches around to my cock and starts jerking me off. I cum about five seconds later and my jizz is all over the side of this TV stand.
Hank kisses my neck one last time and then backs away, putting his clothes back on.
"Did you want to shower?" he asks.
"Nah," I say, also putting my clothes back on.
He takes a seat at the table and pours me another glass of wine. I sit at the table with him and we both drink.
"Everything you thought it would be?" he asks.
"Mmm," I say, giving him a tired, satisfied smile.
"I'm in town about once a month if you ever want to do this again," he says.
"I definitely would," I say.
He smiles. "Of course, if you need to be somewhere, feel free to take off, but if you stick around for twenty minutes or so, I can fuck you again if you want."
I decide to stick around.