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 drive over to your buddy's place.

"Finally, what took you so long? C'mon, go get dressed," He points upstairs.

You rush off to obey. There's just something about losing your virginity dressed like a girl that has you tingling with excitement. You put on the bra and panties, the wig and dress, and finally the makeup and nail polish. Twenty minutes later, you can proudly say you're all done.

"What's taking so long? We're not going to the fucking opera!" Bob angrily barges in.

"I'm sorry, Bob! I just wanted to make sure I looked good!"

"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. "So, uhm, where..."

"Downstairs," He orders.

Awkwardly, you walk downstairs as fast as your heels will allow you. As you wait for the inevitable, 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 'tits' are shaking with worry, but Bob grabs your shoulders, holding you steady.

"Calm down, missy. Everything's going to be fine. 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 as you ignore his toast. You're drunk within a minute, skinny as you are, and so you move to deposit the glasses into the sink, unconsciously sticking your ass up as you bend over to 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 glasses into the sink.

"Shit! They 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!"

"No! Please! I'm sorry!" You laugh, unable to keep acting serious.

"Oh, you think this is funny?" He tries to keep up his dominant persona but he too breaks down laughing.

"Come on then, tough guy. Take my beta ass." You beg when you've both recovered.

"Damn, if I new you was so slutty, I'd have done it long ago!" He pulls your pants down. You try to peek over your shoulder when you feel the absence of his touch, but you can't see anything. If you had to guess, he's probably slipping his condom on. Horny, you try humping back into him, hoping for at least some stimulation.

But when you feel his monster cock pressing against your rear you freeze, shivering in anticipation.

"And in we go," 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 ****.

"How's it feel?" He teases.

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

Bob's response is to laugh. "I though you knew me better than that? You wanna find out what all the way in feels like?"

"Don't you fucking dare!" You whole body tenses up, bracing itself for the coming pain.

Thankfully, it doesn't come. Slowly, Bob continues his advance, taking at least another minute before he's balls deep in your tight back. He gives you another pause and you try your best to relax, though of course you can't.

"What's the matter, girl? You look like you have a stick up your ass!"

"Can we please just get this over with?"

"What a fucking mood killer, man! I think you're going to have to get me horny before we continue."

"Find a fucking porno!"

"Now now, what kind of language is that for a nice and proper sissy like yourself to use?"

"Please take me, mister!"

"Tell me how much you want it, little girl."

"Oh mister, you're so strong!" You grit your teeth and start grinding back into him. "Your pole is just so big, it's longer than anything I could have imagined!"

"You like imagining naked men, do you?"

"Oh yes," You giggle as Bob starts pumping into you, "every night I dream about being together with a big strong man, pleasing him with my body."

Your dirty talk seems to have an effect as you notice your friend picking up the pace. He pulls your blond hair hard, driving you wild with lust. As if at odds with your brain, your muscles desperately squeeze, futilely trying to **** him out and deny you your bliss. Soon you can't help but moan as every rub on your prostrate sends shockwaves of pleasure through your body.

By the time Bob orgasms, you're not even sure that you wanted it to end.

"God, your ass is so tight, girl!" His voice cracks with pleasure. "I'm gonna cum! I'm gonna cum in your virgin ass!"

"Oh fuck yeah! Give me my breakfast daddy!" You scream as your buddy's dick spasms, the rubber collecting all his seed.

Exhausted, he collapses back into a chair, while you finally push yourself off of the sink, allowing your aching arms some rest. But you're still horny.

"Oh fuck, they don't tell you how much it hurts in the pornos!" You finally drop your girly pretense and use your manly voice, "...Aw, what's the matter? Is the big strong alpha male out of energy after just five minutes?" You tease, running a finger along his chest.

"That's it. Next time I'm not taking any pity on you..." He grumbles, weakly trying to shake you off.

"That's right, next time you better give me an orgasm." You seductively reach down to his crotch and pull the condom off, appreciatively swishing it back and forth. Then, seeing that he's still not moving, you stick a finger inside, getting it all nice and wet before presenting it to Bob's mouth. "Have you ever tasted yourself?"

"Fuck you," He grumbles again, pushing you away.

"Ha! I wasn't going to waste it on you anyway." You try to make yourself look as sexy as possible as you sit down on the sink before him and spread your legs wide, giving him an excellent view up your skirt. "Oh fuck yeah," You moan as you stick the finger inside, finding your prostrate for the first time. With your other hand you pour the remainder of the condom into your fist and start jacking off, doubling your ecstasy.

Bob just lies there with a smile on his face watching you get off, too tired to do anything else. You find yourself determined to put on the best show you can, moaning loudly and stretching wide, giving him the perfect view. The perfect view of the beta cock he's sucked. The perfect view of the sissy butt he's just fucked. The memories are too much - you blow your load right on Bob's face.

"Dude!" He jumps up in shock.

"Ha ha! Looks like someone finally got their energy back!" You point to Bob's bouncing boner.

Lustfully, cum running down his face, he approaches you and hikes your legs up in the air, lining his dick up with your quivering pucker.

"Uh uh uh." You whisper huskily, his face inches away from yours. "What's the next challenge?"

You smile as you catch a drop of cum from his nose, then deviously lick it up. The way you're teasing, he can't think straight. Hopefully he chooses something advantageous too you.