Tight Butt

You spend half the night thrashing in bed, unable to fall asleep. All you can think about is Bob. His eyes, his face, his ass, his cock. Fuck, have I really fallen in love with my best friend?

Even as you eat breakfast all you can think about is how much Bob enjoyed your cooking, and you find yourself having to awkwardly hide a boner when your sister comes into the room.

But you have a nice surprise for your friend today - you ordered that whip he was joking about a few days ago. His eyes go wide as he lets you in.

"So who needs the shrink now?" He asks.

"Mmmm, I think I'm going to have to test out a new kind of therapy on you," You carefully rub the leather over his body.

"I only approve of peer-reviewed methods."

"Funny, I didn't think you were the sharing type.... Now pull down your pants."

"What?"

You crack the whip in the air and he immediately obeys, stripping completely naked. He flinches as you glide the whip along his erection, the leather irritating his soft skin.

"Just don't hit me," He asks.

"Upstairs!" You crack the whip again.

He runs into his bedroom, and you're not far behind.

"Bend over!"

"Wait, you're not going to - " CRACK!

"I said bend over!"

He meekly obeys, sticking his ass up and bracing himself for the pain. He screams as it comes, shivering under the blow, but when he hears you break down laughing he realizes that you only smacked him with your hand.

"Very funny," he flips over onto his back, giving you a nice view of his body.

"I know! Damn, I should have recorded you - the neighbors must have heard that scream!"

All this foreplay seems to have gotten Bob worked up, and the naughty boy reaches down with a hand to jerk himself. Little does he know you have other plans.

"Bad boy!" You slaps his hand away, "No touching yourself today."

"What?"

"Those are the new rules."

"Make me!" He glares in mock defiance.

You just grin and picks up the whip again.

"No, sorry! I'm a bad boy," He lifts his hands in surrender.

"That's right," You grab the offerings and place them on your ass. Then you climb on top of his chest and present your hard-on to his lips, "But I'm all for second chances."

And he eagerly takes it. Sensually he begins to kiss the tip, closing his eyes in obvious pleasure. His tongue gently flicks at your meatus as he slowly savours the make-out session. Gazing at his beautiful face, you feel like you're lost in a dream, the eroticism of it all driving you wild.

He squeezes your buttocks in a sign for you to get aggressive, and you start to move in and out of his mouth. For his part, Bob makes sure to use plenty of spit on your tool, getting you lubed up for the main course.

"Oh fuck yeah, suck my cock. Ah fuck, you're so good I don't even want to fuck your ass anymore."

"Grehhamhn," He tries to speak with a full mouth.

"I know, I know, don't worry. A deal's a deal. Here, let's get you started," You spit on a finger and reach around to your buddy's tight sphincter, lubing it up.

Then you spit again and stick it inside. He tenses up as his muscles involuntarily clench, but when you find his sweet spot he begins to relax. You make sure to take it slow, rubbing his prostate gently, looking at his blissful face for signs when what you're doing works.

But it seems its working too well - he's having so much fun that he's forgotten about you.

"Don't forget about my prick."

Soon you're both ready, and you pull your finger out of his anus.

"Just go slow," He pleads.

"Just shut up," You retort.

You line up your wet tool and gently push in. You groan in pleasure as you expose yourself to sensations you've never felt before. Getting a blowjob is one thing, but this is on a whole other level!

Farther and farther you push, making sure to take it slow. You already know how much it can hurt. One minute passes, then two, then three, and then finally you bottom out.

"So, how's it feel?" You smile, squeezing his thighs.

He doesn't answer, but the look on his face lets you know everything.

Grinning, you begins to pull out, dragging your cockflesh along Bob's inner walls, the tight vice-grip feeling better than anything you could have imagined. Then, after about two inches, you starts to thrust back in. You repeat this over and over until you've got a steady rhythm with which to pound his ass. He grunts on every thrust, but you can see in his eyes the joy he's experiencing. You swat away his hand when he tries to touch himself again, and as punishment you pick up your pace.

You slam into his hips faster and faster, and you don't stop as your orgasm overtakes you, your cock spasming inside of your best friend, painting his tight pucker white with your cum. You utter a low, primitive growl, squeezing his legs so hard that you worry there'll be bruises left over.

When you finally come down from your high you give him a last few sloppy thrusts before pulling out and collapsing on the bed, in a similar state as he was the last time.

But denied and horny, now Bob's in a similar state as you were. He gets up and sticks his ass in your face, letting you see the result of your hard work.

"That's the sexiest ass I've ever seen," You mumble.

Unsatisfied, he reaches down with a finger and grab some of the cum and rubs it on your lips.

"Fuck off," You wave your arm around and flip over, too tired to fight.

"No way, bro, you promised me an orgasm yesterday. And since I'm not allowed to touch myself..."

Before you can remember what he's talking about his eight inch dick is pressed against your lips, asking for permission of entry. You know this wasn't part of the bet, but you don't care - you want him to have fun too.

So you open your mouth. Eager to take control, Bob grabs your head as he pumps in and out of your mouth, using your face like his own personal fleshlight. As sexually frustrated as he is, he does it rough, but he's careful not to overdo it and go into your throat. That's really caring of him.

When he feels the end approaching, he pulls out and climaxes into a towel. Utterly spent, he collapses onto the bed beside you and you both fall asleep for a nice, long nap.