I started seeing this girl. One night we were making out and it got pretty hot and heavy. She even sucked me for a bit, and she wanted to go all the way but I got in my head, because I was a virgin - I’d gotten head before, but I’d never fucked.
It ended awkwardly, so the next day at work I told Benny about it. He’s a cook at the restaurant where I do dishes, and he’s a couple years older than me and pretty sexually experienced.
“Aw, don’t get stressed about it, little man,” he said, holding my shoulder as he puffed on a cigarette. “Tell you what: come over to my place after work and I can give you some tips.”
So I did. I liked hanging out with Benny anyway - he was a nice and patient guy. And by all accounts he was a stud - broad-shouldered with a muscled, hairy chest, big legs and a solid butt. The waitresses were always flirting with him.
He invited me in wearing a pair of shorts and a t-shirt and smelling like he’d just showered. “My man,” he said, and we slapped palms. He had a beer and gave me a pop and we sat on his couch.
“So what’s the anxiety about? I’ve seen your girl, she’s hot!” he said.
“It’s just never having done it before, I’m afraid I’ll hurt her I guess. Or that I’ll cum too quick, or won’t be able to cum at all.”
“Yeah I hear all that,” Benny said. He took a big swig of beer. “I got an idea, though…” he said, swirling the dregs of his beer in his bottle. “But the thing is, it’s gotta stay between us.”
“Okay,” I said, and for some reason instantly started getting hard. Benny leaned into me.
“Okay, so…I’ve put stuff up my ass before when I’m jacking off. It gets me off. Hard! You ever do that?”
“No,” I said.
“Try it sometime. But all I’m saying is: I think I could take a dick. So maybe you could use my ass, like to practice? You could close your eyes and pretend I’m your girlfriend. Then you would at least have some experience for when it’s time to actually lose your virginity.”
“For real?” I said, but my cock was so hard. “You wouldn’t mind?”
“Nah, man,” Benny said, tweaking his cock through his shorts. “To be honest, it would be good practice for me, too. I’ve been talking to Angel about her taking it out on me with a strap-on,” he said, with a raised eyebrow. Angel was one the waitresses and she was really hot.
“Wow,” I said.
“So, you know. But listen, nobody can know about this, okay?”
“Okay,” I said. We were both tweaking our cocks right now and smiling so big. It seemed insane that I was about to fuck Benny in the ass but here we were, and it was Benny so I didn’t feel any anxiety at all.
“Decent,” he said. “Let’s go to my bedroom and give it a shot.” I followed him to his room where he started stripping off his clothes. I did the same. Our cocks were both fully stiff and bobbing around.
“Alright,” he said, slapping his palms together. He really did have a killer body, all thick muscle with hair in the right places. “We can just take it step by step. So you make out with her, right?”
“Yeah…” I said.
“Well, you’re probably good on that, then. And she’s sucked your cock?”
“Some,” I said.
“Have you eaten her pussy?”
“No,” I said.
“We can practice that if you want. I’m clean as a whistle so no worries there,” he said as he got on his bed, lowering his torso and perching his butt out over the edge of the mattress. He spread his furry cheeks and I could see his pink asshole. “Just pretend it’s pussy.”
I got down in front of his butt and ran my hands up his thighs. “So just put my tongue in it?”
“Work up to it,” Benny said. “You want to get her pussy nice and wet before you slide your cock inside, and the more the anticipation builds the wetter she’ll get.”
“So like this?” I said, and ran my tongue up the back of his thigh and then to the space under his balls, stopping just before I got to his hole.
“Fuck yes,” Benny said as he gave his hard cock a stroke. “Keep doing that. Go from the other angle too - lick down my back and into my crack.” I followed his instructions. Benny really did have a great butt. I kissed and licked all over his muscled cheeks and delved into his crack but avoided actually tonguing his hole. My cock was raging and dripping.
“Now go for the hole but be gentle at first…oh, fuck,” he said, his voice getting low as I touched my tongue to it. It made my cock throb and I pressed my tongue deeper as his moans got more resonant.
“Jesus, little man, that’s fucking it, keep tonguing it like that…oh fuck yeah, flick it, fuckin good,” he said, keeping up a steady stream of encouragement as I ate him out. I’d thought about eating pussy a lot, I’d just never got the opportunity, and this was even better than I’d imagined.
“You’re doing great, bud. She’ll be super horny and ready for you to fuck her if you lick her like that.”
“Yeah?” I said, and stood up. I slid my cock against his crack and he held his breath.
“Oh damn, that’s a good move,” he said. “Ride your cock against me…Jesus, dude, you’re a natural,” he said as I wrapped my arms around his thick chest, bringing him up and pressing my body to his back. My cock started to catch on his hole - it wanted to go in him so bad.
“Alright let’s lube up before we go any further - I mean, she’ll be wet as hell but for practice we need this. Are you gonna use a condom with her?”
“I don’t know. Probably,” I said.
“Well this is just practice so we don’t have to,” he said, grabbing a jar of Vaseline from under the bed and globbing some on my dick. “Damn you’re really huge. Okay I’m gonna talk you through it but it’s gonna take some time so be patient, I’ve never had something this big up my ass before,” he said, putting some Vaseline on his hole then flipping on his back.
He lifted his legs. “Hm, maybe a pillow…” he said, and put one under his lower back, which propped up his spread ass perfectly. “Awesome. So we’ll try missionary first.” His pink hole was winking at me. I got on top and positioned my cock at his hole. “Alright I’m gonna guide you in,” he said, grabbing my cock from me and inching toward it. “Go ahead and push in some…little lower…there you go…oh fuck, there it is,” he said as the head of my cock pushed inside of him.
“Oh man,” I said, feeling his hole swallow my cock head.
“Feels good right?” he said, a little out of breath but smiling up at me. “Just rest it there for a sec. Let me get used to it. She’ll need that too, especially if she’s a virgin.”
“She is,” I said.
“This is great practice for both of you then. Okay, push some more in. There you go. Goddamn,” he said as another couple inches sank into him.
I was in heaven. It was this warmth that went from my cock up into my whole body. I found myself having to hold back from sliding the rest of myself into him and I guess I got carried away without realizing it.
“Slow down, oh fuck…” he said and I stopped myself just before my balls were pressed against him.
“Sorry,” I said.
“It’s okay,” he said, all out of breath. “Just a big dick. Gimme a sec…feels okay…feel okay for you?”
“Yeah,” I said.
“Get that last inch in,” he said, and I did. “Damn, little man! That’s a thick cock. Is it all in me?” he said and went to feel the root of my cock stretching him out. “Alright, you can start to fuck but go slow, okay?”
I slowly inched out then back in. It felt so good. Then I started to pump. Every time I’d go deep his eyes would get really wide.
“That’s good, little man. So when you’re fucking you want to like, feel up her tits. Maybe even play with her clit,” he said. I was happy to do it, he had such a hot chest. I grabbed his hairy pecs as I pumped a little faster. Then I went for his dick and stroked it some.
“Good, good. Not getting close are you?”
“Not yet.”
“Let’s try another position since you’ve got this one down,” he said, and helped me pull out of him. “Go ahead and get on your back - she might want to ride you.”
I did and he straddled me and held my cock in place as he sat down on it. “There we go,” he said. “This gives her more control.” He started to ride me. Something about looking up at him - his big masculine body and handsome face as he took my cock again and again - it got me close almost instantly.
“Slow down,” I said.
“Yeah?” he said with a big smile. “Nice. I’ll go slow. Damn honestly it’s got me close too,” he said, stroking his rod as he ground on me slowly.
“You’re doing great, bud,” he would say from time to time. “You’re gonna fuck her so good. Ready for doggystyle?”
We switched positions. “I know this always gets me off fastest when doing a chick so be careful,” he said as he arched his back and spread out his butt. “Go for it.”
I slid into him. It was getting easier each time, I guess cause he’d loosened up. I got caught up in the sight of it, my rod going in and out of his hole.
“You got a good rhythm going,” he said after a minute.
“I feel like I could cum from this.”
“Perfect. But first I want you to go a little wild. Fuck a little harder,” he said. I did as he said. “Yeah, really slam into me. There you go. Holy fuck. Pound me, pound my ass. Slap it.”
I did as he said, whacking my palm against his meaty cheek then grabbing that butt with both hands and really thrusting into it. He arched his back and came up toward me, I wrapped my hands around his tits and tweaked his nipples as I pounded him.
“I’m gonna cum,” I said into his ear.
“Okay, you gonna pull out?” he said.
“Should I?”
“Fuck it just blast into me. Don’t do this with her, though. Fuckin cum in me, little man,” he said, and I noticed he was cumming all over the bed. With each shot his hole contracted around my cock and it was like his asshole was milking my load out of my balls. I felt the first shot go into him.
“I’m cumming in you,” I said.
“Pump it deep, little guy. There you go, holy fuck…” he said as we shot together. I sucked on his neck - it just came naturally.
And then he was shaking the last drops of cum off his dick.
“All done? he said, turning his head to me. I had this urge to kiss him.
“Yeah,” I said.
“Okay, go ahead and pull out. Take it slow…ah!” My dick flopped out. His asshole was gaping and leaking cum. He reached back to feel it.
“Damn you really filled me up!” he said. “Well, shit. Great first lesson,” he said, standing up. He held out his hand and we slapped palms. “You did great, little buddy.”
“Thanks,” I said. We were smiling at each other.
“You’re gonna fuck her so good,” he said, all proud. It just felt natural when we came together and kissed, even better when he slipped me the tongue. I gave it right back.
“Well shit, let’s not get carried away,” he said, looking down at our cocks which were both rising again. “Gotta save some for her, you know?” he said, and punched my shoulder before he headed to the bathroom the clean up.