Second Anal

You spend half the night thrashing in bed, unable to fall asleep. All you can think about is Bob. His eyes, his face, his ass, his cock. Fuck, have I really fallen in love with my best friend?

Even as you eat breakfast all you can think about is how much better Bob's cooking tastes, and you find yourself having to awkwardly hide a boner when your sister comes into the room.

Even still when you finally make it over to Bob's place, you have to sit in the car for ten minutes playing Angry Birds until you're decent enough to present yourself.

"C'mon, man, what took you so long? Go get dressed 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.

But when you make your way downstairs you're greeted with a sight you definitely did not expect - there is Bob all dressed up as well!

"What?" You stupidly say.

"Today I decided we can be lesbians," Bob says as he seductively places a hand on your chest.

"Well, so long as you're not sticking anything in my -"

"Don't get your hopes up, baby girl. In fact, I brought you another surprise - your very own chastity cage!"

"Wow, for me? I can't wait to fit it around your cock."

"Bad girl!" He slaps you hard. "What kind of way is that to talk? Now pull down your panties so we can lock up your little clit."

"Hey, this wasn't part of the bet." SLAP! "OK, alright!" You meekly obey, bending over and pulling down the pink panties.

He frowns as your erect penis flops free. "Looks like we're going to have to take care of that problem."

You blush as you reach down to jerk your little penis.

"Here, let me help you out," He says, bending you over and shoving a lubed up finger into his anus.

You tense up as your muscles involuntarily clench, but when Bob finds your prostate you begin to relax. Opening yourself up to this forbidden pleasure, you find yourself content to just let Bob do his thing.

"Oh fuck, why does that feel so good?" You moan, getting more aggressive with his fist.

"Has missy never played with her pussy before?"

"No, ma'am! Sissy's a good girl!" You're barley able to form words, so lost are you in this new pleasure.

"And good girls obey orders don't they...?" An awkward silence follows. "Cum for me, sissy!"

You don't know how, but you immediately start squealing as you lets out what pitiful amount of sperm his testes managed to produce onto the floor.

"Good girl! Now that you're soft, we can fit your little clitty in its new home." You worry that you're going to get hard again, but thankfully you're able to control yourself while your best friend places your other best friend in prison.

"I think you need a new name now," Bob suggests.

"What?"

"Yeah, so do I. Hmm.... Let's call you Veronica, and I'll be Brittany!"

"OK, Brittany," You cuddles up into her bussom, resting your exhausted body in the dominatrix's embrace.

You close your eyes as Brittany strokes your blonde hair, thankful that you have such a loving friend. You would be content to just lie like this all day, but you know that a bet is a bet, and Brittany deserves your cunt. You snake your hand into her panties and star to stroke her clitty. It's already so big you wonder how it hasn't ripped through her panties yet.

Ready to go, Brittany climbs atop of you and hikes up your dress.

"Just go slow," You plead.

"Of course, dear."

She lines up her wet tool and gently pushes in. You grit your teeth in pain as your virgin pussy is stretched like never before. Farther and farther Brittany pushes, soon one minute passes, then two, and then you once again find yourself wishing that her clit wasn't as big. Finally after another minute, she bottoms out.

"So, how's it feel?" She smiles, squeezing your thighs.

"Oh, it really hurts!"

"Don't worry missy, I'll take it nice and slow."

She begins to pull out, dragging her cockflesh along your inner walls, pleasing your sensitive innards. Then, after about two inches, she starts to thrust back in. She repeats this over and over until she's got a steady rhythm with which to pound your ass. You wince on every thrust, but you can't deny the joy you're experiencing. Lost in a haze, you absentmindedly reach down to your own clit, only to be reminded that its been locked away forever. Being unable to touch yourself hurts almost as much as losing your virginity, but fortunately for you, it's soon over.

Your friend slams her hips hard into your legs as her cock spasms inside you, painting your tight pucker white with her cum. She utters a low, primitive growl, squeezing with all her strength.

When she comes down from her orgasm she gives you a last few sloppy thrusts before pulling out and collapsing on the bed, in a similar state as you were the last time.

Similarly tired, having had sex twice in a day, you cuddle up with her and slowly fall asleep.