First Anal

Today is the day. Today you were going to have sex for the first time. It might be with a man, but hey, an ass is an ass.

"Open up, dude." You knock on the door.

"Morning," he groggily opens the door with half-opened eyes, still in his boxers.

"Sweet, you already undressed!" You press yourself forwards against him as you squeeze his tight ass with both hands.

"Whoah, whoah, whoah!" He tries pushing you off as you kick the door closed behind you. "I haven't even ate breakfast yet!"

You flash a devious grin as you let go and fish out a condom. "Half an hour, and your breakfast will be all ready."

"Ewwwwwww! That's fucking gross, man! I'm getting some cereal." He turns around in an attempt to leave, but you take the opportunity to bend him over the couch.

"For cereal you need milk," You pull his boxers down and give him a hard slap.

"Ow! What the fuck?" SLAP!

"The first one was for being a bad boy, and the second for speaking without permission."

"Get the fuck off me!" SLAP! His ass is nice and red now, and more importantly you're nice and hard. He could easily get up, of course - not only is he bigger than you, but you're also only holding him down with the one hand. But he doesn't want to, you think, noticing his stiff dick humping the couch.

"I'd have worn a belt if I had known you'd be such a naughty boy today. I don't think we can continue until you apologize!"

"Oh yeah? Make me!" He's getting into the spirit. But he knows what that means. SLAP!

"You know, I think I'll actually go take a belt from your dad's closet."

"No! Please! I'm sorry!" He laughs, unable to keep acting serious.

"Oh, you think this is funny?" You try to keep up your dominant persona but you too break down laughing.

"Come on then, tough guy. Take my virgin ass." Your friend begs when you've both recovered.

"Damn, if I new you was so slutty, I'd have done it long ago!" You pull your pants down. You're as hard as Bob, and have no trouble slipping the condom on. Your buddy is trying to peek over his shoulder, but due to the angle he's **** to use his imagination.

He freezes still when he feels you pressing against his entrance, shivering in anticipation.

"And in we go," You push in. Slowly, you stretch Bob with your girthy tool, giving his virgin pucker time to adjust. As much as you want to just slam your hips into his, you know you have to go easy if you want him to give you the same courtesy next time. Deeper and deeper you go, spoiling yourself with sensations you've never felt before. It's so fucking tight, you have to really fight your mating instincts and take it slow. About half-way in, his butt clenches tight around your cock, and you take it as a sign to stop.

"How's it feel?" You tease.

"It's a mix," he admits. "You're all the way in, right?"

You can't help but laugh. "I though you knew me better than that? You wanna find out what all the way in feels like?"

"Don't you fucking dare!" He clenches down hard on your tool, trying his best to stop your advance.

But again, you take pity on him and go in slow. It takes at least another minute before you're balls deep in his tight back. You laugh to yourself at the glory of it all, feeling like a kid opening his Christmas present. Poor Bob, on the other hand, is trying his best to relax but failing miserably.

"What's the matter, Bob? You look like you have a stick up your ass!"

"C'mon, let's just get it over with."

"What a fucking mood killer, man! I think you're going to have to get me horny before we continue."

"Find a fucking porno!"

"Oh damn, Bob, I'm getting soft!" You lie, "looks like we're going to have to start over later."

"Fucking limp dick," He mutters to himself.

"What's that? I can't hear you."

"I said, oh yeah, that's a fucking machine you have on you!" He starts grinding back into you. You appreciatively watch his ass gyrate into your hips as he goads you on. "Your cock is so fucking sexy, man, it's better than anything I've seen online!"

"You like checking out cocks online, do you?"

"Oh yeah," He giggles as you start pumping into him, "why do you think I watch so much blowjob porn? Fuck those dumb dykes, I only care about those beautiful cocks!"

You know he's just fucking with you, but still he turns you on so much that you start to get rough. Picking up the pace, you grab his tight ass hard, providing some leverage for your forceful ****. His muscles desperately squeeze, trying to **** you out, but it only turns you on further. Appreciating your technique, Bob starts to moan in pleasure as every rub on his prostrate sends shockwaves of pleasure through his body. Of course he's enjoying it. The way I fuck, anyone would enjoy it.

It's not long before you feel an orgasm arriving.

"God, your ass is so tight, Bob!" Your voice cracks with pleasure. "I'm gonna cum! I'm gonna cum in your virgin ass!"

"Oh Hell yeah! Give me my breakfast daddy!" He screams as your dick spasms, the rubber collecting all your seed.

Exhausted, you collapse on Bob, tipping him over the arm, face first into the couch. You love the feel of your chest on his back, the feel of your individual muscles working as you recover.

Pushing you off, Bob gets off and grabs his ass in pain.

"Oh fuck, they don't tell you how much it hurts in the pornos! ...Aw, what's the matter? Is big daddy out of energy after just five minutes?" He teases, running a finger along your spine.

"That's it. Next time I'm not taking any pity on you..." You grumble, trying to shake him off.

"Oh yeah, next time you better give me an orgasm." He seductively pulls your condom off, and appreciatively swishes it back and forth. Then seeing that you're still not moving, he sticks his finger inside, getting it all nice and wet before presenting it to your mouth. "Have you ever tasted yourself?"

"Fuck you," You grumble again, pushing him away.

"Ha, I wasn't going to waste it on you anyway." True to his word, Bob sits down on the table before you and spreads his legs wide before sticking the lubed up finger in his ass. "Oh fuck yeah," He moans as he finds his prostrate. Then with the other hand he pours the remainder of the condom into his fist and starts to jack off.

You just lie there with a smile on your face watching your friend get off, too tired to do anything else. A few weeks ago, you realize, seeing your friend with a finger up his ass would have freaked you out, but now here you are, unable to look away. You watch how his biceps curl as his fist gets rough, how his pecs jump with every pump. You watch his hairy ass and the finger inside it. You watch his heavy balls, swinging back and forth. Then you look up at his cute face, and marvel at the expression of pure bliss. It's at that moment that he blows his load... right on your face.

"Dude!" You jump up in shock.

"Ha ha! Looks like someone finally got their energy back!"

You think he's talking about you, but then you notice he's pointing at your boner. Did I just get hard watching my friend jerk off in my face?

Too horny to care about that, you hike Bob's legs up in the air and line up your dick with his quivering pucker.

"Uh uh uh." Bob whispers huskily, his face inches away from yours. "What's the next challenge?"

He smiles as he catches a drop of cum from your nose, then sexily licks it up. Your cock pulses with anger, begging you to fuck this teasing boy, but you know you can't - the rules are the rules.