First Anal

Today is the day. Today you were going to have sex for the first time. And it'll be with a man. If it were anyone else, like your other friends Mike and Tony, you would have turned them down in an instant. But not Bob.

With how often the two of you are hanging out this summer, he doesn't even bother locking the door anymore, and you make your way to the kitchen for a beer to loosen your nerves.

"Bob! I'm here!"

"Morning," he grogs downstairs with half-opened eyes, still in his boxers. Normally, you wouldn't have given it a second look, but after last week, after yesterday, you can't tear your eyes off his well-sculpted form as he splashes some water onto his face. "Want some cereal?"

You can't help but feel that he's doing it on purpose - the way he flexes his perfect muscles as he eats, and then the way he angles his hips when he washes the dishes. Eventually, you can't take anymore.

"I want you now!" You aggressively bend him over the couch's armrest as he gives you a knowing smile.

Pulling down his underwear, you give his muscular ass a light slap for the way he's been teasing you. "Naughty boy! You've been doing this all on purpose, haven't you?"

"I was just trying to make sure you'd be able to get it up." SLAP!

"The fuck did you say? I think I'm having some hearing difficulty, you'd better repeat that again," You grind roughly against his back, your stiffy distending your jeans enough to slip between his crack.

"I said I'm sorry!"He moans as he humps back, his own dick fucking the couch.

"Yeah, and how are you gonna apologize?"

"With this," he hands you a condom. Dirty boy really did have this all planned.

You tear it off as your friend keep humping, and then start to unbutton your jeans. When your clothes are gone, you slip the rubber over your erect dick and slowly line up with Bob's hole.

He stops moving when he feels you pressing against his entrance, completely changing behavior, just shivering in anticipation. You too stop your rough teasing and gingerly lean over him.

"Are you ready?" you whisper.

"Mhm," he breathes, and then you push in. Slowly, gently, you stretch Bob with your girthy tool, giving his virgin pucker time to adjust. Deeper and deeper you go, spoiling yourself with sensations you've never felt before. 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 ask, leaning over his tense back to whisper again.

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

Ordinarily you would have burst out laughing, but instead you playfully bite his ear as you whisper "half-way." That triggers another butt clench of surprise, and you have to struggle not to cum then and there. Instead, you massage his cheeks with your hands, helping him loosen up while you slowly push yourself further in. Bob groans in pain when you're three quarters inside, and though you slow down a bit, you do not stop. You're 100% determined to fully burry yourself in his virgin ass.

After what feels like an eternity, your hips collide. You reach over and wipe a tear from Bob's face.

"There, there. It's over."

He nods, but it seems to take all his effort. "Just go slow," he pleads.

Although a part of you wants to pound the life out of him, a greater part of you wants to make sure he enjoys this. You pull your hips back - not the whole way, maybe just one or two inches - and then push forward again. This way he gets the pleasure of his prostate without the pain of being banged. And you get to enjoy the warm confines of his ass, muscles still furiously squeezing, trying to **** you out. 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.

As much as you would like to stay like this, you know silent Bob needs to recover as well. Gently now, you pull out as his ass quickly tightens up. Kneeling down in front of your friend, you lift his face in your hands.

"You alright? You haven't said a word." When you speak, gone is the rough tough guy 'bro' voice you always use. Instead, your sound is now one of genuine concern.

"I'll live."

"That bad, huh?"

"I'm just glad you're happy." He manages a smile. That's so nice of him to think of my pleasure first. You leave him be as you dispose of the condom and clean up.

Bob says he's too sore to do anything besides watch TV, so that's what you do for the rest of the day. When you head home, together you decide on the next challenge.