First Anal

Your first thought when you wake up is that there is something you need to do, but you can't remember what it is. It consumes your mind as you get dressed to go over to Bob's, feeling as though you've forgotten something as important as brushing your teeth.

It's just as you close the door that you remember - you need to shave your ass! There's no way you can let Bob fuck you in a sissy dress with hairy pubes covering your boy pussy! Undressing, you hurry into the shower and get to work. You're not sure if you get every spot, but you just have to hope Bob will be too horny to notice.

All done, you rush into the car, hoping you can make your way over to your friend's house in time to cook him a meal.

"Oh, there you are! I was just thinking I would be making breakfast myself today!" He jokes.

You awkwardly blush, trying to pretend that you're not happy about it, even though you're sure he can see through your facade.

"But get dressed this time," He demands.

You rush off to obey. You **** yourself to calm down enough to put on the clothes just as carefully as last time. You take especially extra care with the makeup, using all the new tricks you learned from those YouTube videos you've been watching. Twenty minutes later, you can proudly say you're all done.

"We're not going to the fucking opera!" Bob angrily barges in, "And if we were, I'd have starved to **** before the intermission."

"I'm sorry, Bob! I just wanted to look so good that I forgot you were hungry!"

"Always thinking about yourself," He condescends.

"No! I wanted to look good for you!" You start to protest, but you see that he was just joking with you.

Ashamedly, you walk downstairs as fast as your heels will allow you. As you start to cook, the realization of what is about to happen dawns on you. I'm about to let a man fuck my ass! Am I really going to do this? There's no coming back from this! Your hands are shaking as you bring the plates over to the table, so Bob rushes up to grab the silverware before it shatters on the floor.

"Calm down, missy. Here, I know what you need," He reaches into a cabinet and pulls out a bottle of whiskey. Pouring two shots, he proposes a toast: "So you can have a smooth transition into your new life - cheers!"

You down your shot without hearing his toast. You're drunk within a minute, skinny as you are, and so you have a hard time forcing yourself to finish the food. You smile into Bob's expecting gaze when you're done, enjoying his attention. It isn't until a few seconds later that your intoxicated brain processes that you're expected to wash the dishes. You get up with a giggle and make your way over to the sink, careful not to drop anything. Proud of yourself, you bend over and turn on the tap.

Unfortunately for you, bent over in that position you give Bob a great view up your skirt, and he's unable to control himself.

SPANK! You let out a yelp of shock and drop the plate into the sink.

"Shit! It nearly broke!" You exclaim.

SPANK! He hits harder this time, and you can feel your ass jiggling from the blow.

"Now what kind of language is that?" He scolds.

"I'm sorry."

SPANK! Your whole ass is burning by now.

"You didn't mean it!"

"Oh, I'm so sorry, Bob! I'll be willing to make it up to you in any way!"

"Is that a fact?" He hikes up your dress and grinds his pelvis into your back. "I said is that a fact!?"

"Yes!"

"Then beg for it!"

"Please fuck me," You whisper, not yet at terms with what's happening.

"I can't hear you over the sink!"

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

"Oh yeah, I'm the best."

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. You're the most sober you've ever been in your life, all the **** seemingly chased from your system as your rectum burns, 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 no, look at you. All that hard work in the bedroom all gone," He holds up a black finger to your eyes, showing you your ruined makeup.

"Oh no...."

"You want to at least do something for me, don't you?"

"Of course."

"Then get back to work!" He shouts, pushing your head into the sink. Again you pick up the plate, mopping it with the sponge while the stud abuses your ass. On every thrust your blonde hair keeps flapping into the sink, getting all wet under the tap. Although part of you wants to focus on doing what you've been told, the stronger part of you wants to ignore everything and focus on the pleasure. Soon, 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. "You know your alpha's pleasure comes first."

"That's right, Bob, I'm your beta bitch. 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.

It's not long before his orgasm arrives, but thankfully you've finished cleaning the dishes.

"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.

You feel yourself collapse into the sink, without any more energy to hold yourself up.

"Damn, is that ass shaved?" He marvels as you feel something wet on it.

You turn around to see Bob smearing the contents of the condom onto your ass. You don't have the energy to complain, at least not until you see him pull out his phone.

"Smile!" He snaps multiple pics, "Man, wait until Tony sees this!"