Sissy to Military School Pt. 03

"Kay's my new girlfriend, and we're just having a slumber party. Girl talk and a makeover. She's my sissy mentor", I replied.

"You're mentor? A makeover? Let me see, send a pick." Jack replied.

I was about to take the selfie when Kay blurted out," Stop, just one finishing touch!"

Kay pulled a lipstick from his makeup bag and said," Lip gloss, purse your lips like your kissing!"

Kay applied the lip gloss, I snapped the selfie and hit send.

Jack's reply was immediate. "OMG, you're totally gorgeous! You're the most beautiful girl I've ever seen!"

Kay looking up from the phone said, "My masterpiece! Quick put your thong back on!" I was just slipping my leg into the thong when Kay approached with the butt plug in his hand and said, "Forgetting something? Bend over the chair I'll put it in for you, sissy sister!" I did as Kay asked. Kay slipped the mentholated butt plug back into my ass. I pulled the thong elastic into place over my hips.

Kay retrieved my phone and told me to resume my position bent over the desk. I did as Kay asked, and the flash went off.

"Pull your thong to the side," Kay instructed.

I did, and Kay took another photo with my phone.

"Now for the grand finale, pull your ass cheeks apart!", Kay directed.

I did as Kay requested, spreading my ass cheeks, and Kay took the final shot.

I looked at each of the shots. The first photo was almost artistic. I looked like an amateur model. The second photo was erotic. I was pulling my thong to the side, but only the cheek showed. "I would give it an R rating," I said. I fully expected the third and final photo to be vulgar, but as I viewed the photo, I saw an azure jeweled circle in place of my anus!

I looked at Kay and he said, "OK, I neglected to say it was jeweled, but it does suit you!" Kay hit the send button three times. "Oh my god, you did that didn't you?" I said with surprise and amusement.

Kay typed, "Remember, no masturbating, no cumming unless you're with me!"

Jack replied after a few minutes, "Too late, with a smiley emoji. Thank your girlfriend Kay for me." Kay and I shared a giggle.

Kay typed, "I will, Kay wants to see what Cedric looks like."

A photo of Cedric on his bed, back against the wall, very much as I had met him initially, came across the screen." Kay let out a sigh, fanning his face with his hand and said, "Oh my, that's just my type. like a challenge! My 'she monster's hungry for masculine man ass!"

Jack texted, "Night baby it's late. We have to be up early tomorrow for orientation and classes. See you at breakfast, cantina side."

I took the phone from Kay and typed, "See you tomorrow at breakfast. Who's my boyfriend?"

"I'm your boyfriend!" Jack replied.

I said goodbye to Kay kissing him on the lips. I gathered my shorts, some makeup remover, foundation, and the mentholated butt cream. I walked down the hall and to my room wearing only my belly shirt, and thong, reveling at my bare ass on display. Once I was in my room with the door shut behind me, I declared, "I'm in the sissy sisterhood and I'm proud!"