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, Bob." 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 soft 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 disgusting, you creep! I want 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 spank.

"Ow! What was that for?" SPANK!

"The first one was for being a bad girl and not dressing up, and the second was for speaking without permission."

"Get of off me you bully!" SPANK! His ass is nice and red now, and more importantly you're nice and hard. He tries to get up, but he's way too weak - you can easily hold him down with one hand while you punish him with the other.

"I'd have worn a belt if I had known you'd be such a naughty girl today. Do you know how much we paid for your dress? And you don't even bother to wear it? I don't think we can continue until you apologize!"

"But it's not my fault!" He complains. But he knows what that means. SPANK!

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

"No! Please! I'm sorry!" He starts to cry again, sobbing from your rough treatment. But you're not going to go any easier on him.

"Yeah? For what?"

"I've been such a bad girl! I deserved all of it!"

"Alright, maybe I forgive you...." He seems like he's faking it. "How are you going to apologize?"

"Uh... I'll go upstairs and get dressed for you!" SPANK!

"Daddy isn't pleased with that apology. You see, you got daddy so horny that he needs to fuck your sissy ass right now. What do you say to that?"

"Yes. Fuck my sissy ass." Bob's so enthusiastic about it that he might as well have been a robot querying a response from the internet. But it doesn't matter to you - what matters is the humiliation of making him say those words.

You're in for a surprise when you pull down his underwear - everything is shaved! The pathetic kid did it so you wouldn't get mad, but he got a spanking anyway. The irony is too much for you to resist laughing and you spank him once more.

"Owie! Stop it, pretty please?"

"I can't resist it with how slutty your ass looks, Bob. Did you shave this all just for me, or do you keep it like that all the time? Does it make you feel more girly? Does it help you fit with your true gender identity?"

His starts crying again, but he does his best to remain composed. "I'm a boy! I mean a man! Why are you always so mean? Just screw my ass and get it over with!"

"Well, if that's what you want...." You tear open the condom and pull it over your erect dick. You smile as you rub all seven inches above Bob's back. You were going to break this bitch today. 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. Not that you'd mind seeing him cry again, but if he tells his mother you definetley won't be playing again. 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.

"You like my cock?" You gruffly ask.

"Yes," he lies. "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 sissy tears in the morning. Would you like to try?"

He looks like he wants to respond, but he's in way too much pain to do so.

"Oh, what's that? Are you enjoying this? Do you want daddy to fuck you?" You don't move, waiting for him to respond, but he's still clinging on to his last fragment of masculinity. SPANK!

"Good girls answer questions!"

"Yes, fuck me daddy! I need you to fuck my boy pussy!" It might be your imagination, but you think you even notice a hint of sincerity in his voice.

Since he's asking so nicely, 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 in pain as you pound the life out of him. You feel a surge of pride at your prowess, and it's not long before your orgasm arrives.

"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.

"I'm ripped, baby boy! You feel that? That's what cucks like you can never have!" Silence. You pull yourself out and spank him hard again. "I asked you a question, bitch!"

"Ow! Yes I feel it." He's too weak to say anything else. Who wouldn't be, after a pounding like that?

You go to the kitchen and grab yourself a beer. When you come back to the living room Bob still hasn't moved. You fish out your phone and snap a few more pictures of his shaved red ass in the air. Then you walk around where you're sure he can see you and take some more from another angle. He doesn't move.

"You gonna lie like that all day, slut?"

He just gives a weak nod. You scoff.

"Kay, I'm sure I was too big for you to handle. But I like your ass nice and tight, now, don't you be sticking anything in there while I'm not around." Pleased with yourself, you head out the door.