First Anal

Today is the day. Today you were going to have sex for the first time. Yet worryingly, you find yourself wondering whether you would prefer to be on the bottom.

"Why aren't you dressed yet?" You cockily ask as you open the door.

"You're enjoying this too much," Bob grumbles as he begrudgingly goes upstairs to obey.

You nervously wait five minutes, then ten, then twenty, and then you decide you've had enough.

"What's taking so long? We're not going to the fucking opera!" You angrily barge into his room.

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

"Always thinking about yourself," You mock.

"No! I wanted to look good for you!" God, he looks so cute when he's upset. "So, uhm, where..."

"Downstairs," You order.

You try not to laugh as you watch Bob awkwardly make his way down the stairs. When you see him shaking with worry you realize he's even more nervous than you are.

"Calm down, missy. Everything's going to be fine. Here, I know what you need," You reach into a cabinet and pull out a bottle of whiskey. Pouring two shots, you propose a toast: "So you can have a smooth transition into your new life - cheers!"

You down your shots with a smile, the **** helping you work up your courage. Bob looks like he's feeling better too, embracing his feminine side and deciding to wash the glasses.

Unfortunately for him, bent over in that position he gives you a great view up his skirt. You can see the pink panties stretching around his crack without a single hair in sight. It's too much - you need him now.

You spank him as hard as you can, causing him to let out a scream and drop the glasses into the sink.

"Shit! They nearly broke!" He exclaims.

SPANK! You hit harder this time, and you can feel your hand sting from the blow.

"Now what kind of language is that?" You scold.

"I'm sorry."

SPANK! His ass is red by now.

"You didn't mean it!"

"No! Please! I'm sorry!" He laughs, unable to keep acting serious.

"Oh, you think this is funny?" You try to keep up your dominant persona but you too break down laughing.

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

"Damn, if I new you was so slutty, I'd have done it long ago!" You pull his pants down as you pull on your condom. The horny slut tries to peek over his shoulder, but in his position he's not able to see anything and is **** to use his imagination. He starts humping back, but when he feels you pressing against his entrance, he freezes, shivering in anticipation.

"And in we go," 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 him to give you the same courtesy. 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.

"How's it feel?" You tease.

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

Your 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!" He clenches down hard on your tool, trying his best to stop your advance.

But again, you take pity on him and go in slow. It takes at least another minute before you're balls deep in his tight back. You laugh to yourself at the glory of it all, feeling like a kid opening his Christmas present. Poor Bob, on the other hand, is trying his best to relax but failing miserably.

"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!" He starts grinding back into you. You appreciatively watch his ass gyrate into your hips as he goads you on. "Your pole is just so big, it's longer than anything I could have imagined!"

"You like imagining naked men, do you?"

"Oh yes," He giggles as you start pumping into him, "every night I dream about being together with a big strong man, pleasing him with my body."

You know he's just fucking with you, but still he turns you on so much that you start to get rough. Picking up the pace, you reach under his skirt to grab his tight ass hard, providing some leverage for your forceful ****. His muscles desperately squeeze, trying to **** you out, but it only turns you on further. Appreciating your technique, Bob starts to moan in pleasure as every rub on his prostrate sends shockwaves of pleasure through his body. Of course he's enjoying it. The way I fuck, anyone would enjoy it.

It's not long before you feel an orgasm arriving.

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

"Oh fuck yeah! Give me my breakfast daddy!" He screams as your dick spasms, the rubber collecting all your seed.

Exhausted, you collapse back into a chair, only looking on with one eye as Bob stretches from discomfort.

"Oh fuck, they don't tell you how much it hurts in the pornos!" Bob unfortunately decides to use his manly voice now, but you're so tired you don't do anything about it. "...Aw, what's the matter? Is the big strong alpha male out of energy after just five minutes?" He teases, running a finger along your chest.

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

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

"Fuck you," You grumble again, pushing him away.

"Ha! I wasn't going to waste it on you anyway." True to his word, Bob sits down on the table before you and spreads his legs wide before sticking the lubed up finger in his ass. "Oh fuck yeah," He moans as he finds his prostrate. Then with the other hand he pours the remainder of the condom into his fist and starts to jack off.

You just lie there with a smile on your face watching your friend get off, too tired to do anything else. A few weeks ago, you realize, seeing your friend dressed up like a girl with a finger up his ass would have freaked you out, but now here you are, unable to look away. You watch how his blond hair shakes as his fist gets rough, how his boobs bounce with every pump. You watch his shaved ass and the finger inside it. You watch his cute balls, perched beneath his prick. Then you look up at his pretty face, and marvel at the expression of pure bliss. It's at that moment that he blows his load... right on your face.

"Dude!" You jump up in shock.

"Ha ha! Looks like someone finally got their energy back!"

You think he's talking about you, but then you notice he's pointing at your boner. Did I just get hard watching my friend jerk off in my face?

Too horny to care about that, you hike Bob's legs up in the air and line up your dick with his quivering pucker.

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

He smiles as he catches a drop of cum from your nose, then sexily licks it up. Your cock pulses with anger, begging you to fuck this teasing girl, but you know you can't - the rules are the rules.