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Chapter 20
by GuerrillaShark
The Next Day
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 groggilly 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!"
"Apologize!? For what!?" He spits out the last words as if they're toxic. 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!"
"Yeah? For what?"
"How the fuck should I know!?" SLAP! SLAP! SLAP!
By now, even your hand stings from the effort. You can only imagine the pain Bob is going through.
"I've been a bad boy! I'm sorry! I've been such a bad boy!" He's half screaming, half whimpering the words, though not quite crying. Taking pity, you decide you don't want him to.
"Alright, maybe I forgive you...."
"Maybe!?" He says it so incredulously you're heavily tempted to give him another one.
"It depends on how well you take my cock," you say, pulling 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 stops moving 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 to avoid a fight. 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. A loud, obnoxious, demeaning laugh. "Almost," you lie and then thrust all the way in. He screams. He screams so hard, the neighbors must have heard, but it only makes you laugh harder. "See, wasn't that bad, was it?"
Bob's trying his best to fight it, but tears start running down his red face as he comes to terms with the shock of pain coming from his virgin ass. You, on the other hand, revel in the pleasure. And it's not just the pleasure of the vice-grip around your tool, but pleasure from the way you emasculated Bob - the way you once again turned him into a squealing bitch. You reach over and wipe a tear from Bob's face.
"Mmm I love the taste of tears in the morning. Maybe I can get you a nice glass of water with your milk?"
And now you're really surprised. Instead of crying more, he actually pushes back into you with his ass!
"Oh, you dirty slut. Are you actually enjoying this?" Damn, it doesn't feel like my smile will ever go away! "You want your best friend to fuck you?" You don't move, waiting for him to respond, but he's still to shy, just gyrating his hips. SLAP! "Good boys answer questions!"
"Yes, fuck me! I need you to fuck my ass!"
And you oblige. You start to bang him hard, pulling all the way out before thrusting back in. His muscles desperately squeeze, trying to **** you out, but it only makes every thrust feel like the first. You pull out, he goes back to normal, you push in. All the way, over and over again. Bob's moaning with pain and pleasure as you pound the life out of him. 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 ass!" You dick spasms inside your friend, 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. When the moment has passed, you pull yourself up and out, holding the full condom before Bob's ashamed face.
"Shall I get a bowl, or will you have it straight?"
He manages to smile, but is too weak for anything else. Who wouldn't be, after a pounding like that? You take pity on him and bring down a pillow and blanket from his bedroom, allowing his naked form to relax comfortably. You go to the kitchen and make him some porridge (so he doesn't spill the cereal). He eats only half from his prone position, too tired to have any more. Not wanting to get up at all, he just lies there for the rest of the day, watching TV. When he starts snoring, you ask yourself why you're still here, but you find some odd sense of responsibility to take care of him after the way he pleased you. Besides, he looks real cute curled up like that. Soon, still with a smile, you fall asleep as well.
What's the next challenge?
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From Friend to Girlfriend
Sexual game changes your sexual preference
Updated on Feb 28, 2025
by knight26
Created on Feb 14, 2006
by boywearspanties
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