Quality time with sis

"Okay slut, when Daddy's gone the rules are a little different. You don't always need to be on your hands and knees but you do still need to when I tell you too. You don't have to ask permission to speak, but never interrupt me and don't **** that privilege. Otherwise, just do what I say. Any questions?"

You thought for a moment then asked, "What did Daddy mean by 'make me pretty?'"

Lena's devilish smirk reappeared, "That's the perfect segue into what I was about to do next! Stand up and follow me."

You did as she said while she led you to a room in the back you had never been in. This room was similar to the room with the bare mattress that Jacob fingered you in. A mattress and box-springs on the floor with pink satin sheets and pillows, a few girly stuffed animals, and some dildos and vibrators on it. The walls a similar shade of light pink, there was a white desk with a Mac computer on it and an-expensive looking webcam. Against another wall was a white vanity with lights on it and a makeup box and brush set. The walls were decorated with posters of interracial porn and Christmas lights.

"This is my room sissy, we'll be sharing it when Daddy wants you to stay the night."

"You live here?"

Lena slapped you hard across the face, "What are you supposed to call me?"

"I'm sorry Big Sis. Do you live here Big Sis?"

"When Daddy's not loaning me out to one of his friends, yes. That's why you haven't seen me before, Daddy lost a bet in a game of basketball and I had to stay with one of his friends for a week. Now then, go sit on the stool in front of the vanity."

You did as she said, nervous about what would come next. Lena sat down next to you and grabbed a tube off of gel. "This is primer, it will make sure that your makeup stays on."

"Makeup?"

"Of course sissy! What did you think Daddy meant by 'make you pretty?' Now then, I'll just dab a little bit of this on over your face..." she dabbed a little on your face and spread it around, "Now for foundation... let's see, this matches your shade." She applied the foundation using a sponge, "Now highlighter to hide your stubble... some pink eyeshadow... eyeliner, mascera. Finally some nice plumping pink lip gloss. Don't look in the mirror yet though sissy! One minute." She stood up and walked behind you to the closet. When she came back you felt something being placed on your head. "All done!"

You turned and looked in the mirror and could not believe your eyes. You not only looked like a girl but you actually looked pretty hot, the brunette wig Lena gave you framing your now femme face perfectly.

"We can't really call you John anymore though... how about, Cierra?"

"Okay. Thank you for making me pretty Big Sis."

Lena leaned down and kissed your cheek, "I'm glad you like it! You need to start learning how to do it yourself though, I'll give you some stuff to get you started and send you some youtube videos you can use for practice." Lena looked down towards your crotch, "Oh now that won't do! We can't have you getting distracted by your little clitty while we're cleaning. Pull your panties down sissy."

You did as she said and she reached down, grabbing your dick and balls and squeezing hard, eliciting a moan of pain from you.

"I know it hurts sissy, but we need to get you soft without releasing you." Once you had soften up, she opened a drawer and pulled out something pink and plastic that looked somewhat like a cock with a ring. "This is a chastity cage, it'll make sure that your little clitty can't get hard and that you can't touch it anymore." She slipped the ring around your balls and placed the cage on, sliding a small padlock through it and clicking it shut. "I have the key, and I'll give it back to you if Daddy thinks you've earned it."

You stared down at your encased cock, the image of Alexis from your training video flashing in your mind. Unconsciously a small pout formed on your lips as you resigned yourself to this newest low: wearing women's underwear, face covered in makeup, wearing a girly wig, a buttplug up your ass, and now a cage on your cock. Lena must have sensed your displeasure because she grabbed your hand and guided it into her panties.