Second Anal

You spend half the night thrashing in bed, unable to fall asleep. All you can think about is that damned dress. You won, so its going to be Bob's turn to wear it, but you can't help but feel that it would be much better if it was you again. Winning is supposed to be fun - why does the loser get the reward?

Then you get an idea - who says we can't both be girls?

You silently raid your sister's wardrobe while she's breaking her fast, taking whatever you think will fit.

Bob is dressed and ready when he opens the door, but his eyes go wide when he sees you likewise.

"So you liked my cock so much you came back for seconds? " He asks.

"No, I liked the dress so much I decided we can be lesbians for today."

"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!" You slap him 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!" He meekly obeys, bending over and pulling down the pink panties.

You frown as his erect penis flops free. "Looks like we're going to have to take care of that problem."

Bob blushes and reaches down to his eight inch behemoth.

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

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

"Has missy never played with her pussy before?"

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

"And good girls obey orders don't they?" You let the suggestion hang in the air before continuing. "Cum for me, sissy!"

Immediately, he starts squealing as he 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 she's going to get hard again, but thankfully she just quietly sits there while you place his best friend in prison.

"I think you need a new name now," You muse.

"What?"

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

"OK, Veronica," Brittany cuddles up into your bussom, resting her exhausted body in your domineering embrace.

You're so hard you worry that you'll rip your sister's lingerie, but you **** yourself to stay calm for the time being. Brittany is so tired from her session, you can't possibly bring yourself to upset the cute girl. Instead, you pull her closer into your chest, idly stroking her blonde hair as she recovers from her sissygasm.

After a few minutes she starts to stroke your clitty, and at that point you can't take it anymore. You climb atop of her and pull down your panties.

"Just go slow," She pleads.

"Of course, dear."

You line up your wet tool and gently push in. You groan in pleasure as you expose yourself to sensations you've never felt before. Getting a blowjob is one thing, but this is on a whole other level!

Farther and farther you push, making sure to take it slow. You already know how much it can hurt. One minute passes, then two, then three, and then finally you bottom out.

"So, how's it feel?" You smile, squeezing her thighs.

"Oh, it really hurts!"

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

True to your word you pull out at a snail's pace, dragging your cockflesh along Brittany's inner walls, the tight vice-grip feeling better than anything you could have imagined. Then, after about two inches, you start to thrust back in. You repeat this over and over until you've got a steady rhythm with which to pound her tushy. She moans on every thrust, but you can see in her eyes the joy she's experiencing. Brittany even tries to touch her clitty, only to remember that it's been locked away for good.

You slam into her hips faster and faster, and you don't stop as your orgasm overtakes you, your penis spasming inside of your best friend, painting her tight pucker white with your cum. You utter a low, primitive growl, squeezing her legs with all of your strength.

When you finally come down from your high you give her a last few sloppy thrusts before pulling out and collapsing on the bed, in a similar state as she was the last time.

Similarly tired, having had sex twice in a day, Brittany cuddles up with you and slowly falls asleep.