First Anal

You make sure to clean yourself thoroughly and then drive over to Bob's.

Like yesterday, the door's open and the first thing you do is grab a beer. Whereas last night you were excited, today you're nervous. Am I really going to do this? There's no coming back from this! Your hands are shaking as you try and open the can, so you set it down on the table and **** yourself to take deep breaths to calm down.

Trying to help you in his own way, Bob gives your rump a hard slap when he walks in, causing you to jump up in shock.

"What the fuck was that for?"

"For you. Here, I know what you need," He grabs a bottle of whiskey and proposes a toast. "So you can remember this for the rest of your life - cheers!"

You knock back the drink, but, just like an alcoholic, your hands are still shaking. You grab the bottle to pour two more. SLAP!

''SHIT! I nearly dropped it!" You exclaim. SLAP!

"Oh no, you wouldn't do that, would you? You want to be a good boy tonight," Bob squeezes your burning ass as he aggressively bends you over the table.

"Wait! I'm not ready!"

He pulls down your underwear and gives you another hard slap.

"Ow!" Your tight butt is all red by now, but you're more turned on than angry.

"Don't lie to me boy, tell me the truth. Tell me how much you want me," Bob teases as he grinds his pelvis on your naked back.

"You're hurting me!"

"Turns you on, doesn't it?"

You start, but realize there's no point in denying it. He can see your hard-on as well as you can feel the pain. "Yes, Bob. You turn me on so much," you whisper.

"What was that? I can't hear you over all your moaning!"

"You're right, Bob. You turn me on so much. Your cock is the sexiest! Your cum is the best thing I've ever tasted! And now I need you in my ass, Bob! Please fuck me! Fuck my ass!"

With an XL rubber and a huge grin, he pushes in. Slowly, he stretches you with his girthy tool, giving your virgin pucker time to adjust. It's a bit painful, but nothing crazy. Actually, on some level it feels pretty good. Deeper and deeper he goes, exploiting you with sensations you've never felt before. You're so tight it starts to feel more and more uncomfortable until your muscles clench down on his member as hard as they can, desperately trying to **** him out. Recognizing your pain, he ceases his ****.

"You like that?" He teases.

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

Bob's response is to laugh. "I thought your throat knew me better than that? That was only half - here's all the way in," He slams his hips into yours as you scream at the top of your lungs. Your rectum is on fire, feeling as though it's being split in two. Although you try your best to fight it, tears start streaming from your eyes as you come to terms with the shock of pain coming from your virgin ass. Your friend reaches around to wipe the tears off your face.

"Oh yeah, I can tell you love it. Not even the whores online can scream like that."

You don't know what it is, but something inside you snaps, and to your surprise, you fell yourself pushing back into him.

"That's the spirit," Bob chuckles. "I'm gonna make you feel nice and good."

"No, Bob. I'm going to make you feel even better. Come on and fuck my ass like you really mean it!"

And he obliges. He starts to bang you hard, pulling all the way out before thrusting back in. Your muscles, at odds with your mind, desperately squeeze, trying to **** him out, but they can't stop his fierce prowess. They actually make things worse, making every single thrust feel like the first. You moan and groan in pleasure and pain, goading Bob on to claim you for himself. Time from time he responds with a light slap or a squeeze to your rump. At one point he reaches to grab your balls, giving them a hard pull.

It's not long before his orgasm arrives.

"God, your ass is so tight!" His voice cracks with pleasure. "I'm gonna cum! I'm gonna cum in your virgin ass" Your friend's dick spasms inside you, the rubber collecting all his seed.

If you still had the energy, you would feel disappointment that you didn't get any of it. But you don't, and all you can do is lie there, bent over the table like a cheap whore as Bob basks in his release.

"So, does the little man need some help over here?" He grabs your penis after a while, feeling some remorse at having had all the pleasure.

But you reassure him that's not the case. Your pleasure was his orgasm. You try to get up, but it's way too painful.

Anxiously, Bob helps you over to the couch, awkwardly muttering an apology about how he shouldn't have been so rough. You don't care about any of it, though, happy that the first time was so memorable for the both of you. Not a minute later, you've fallen asleep.