Dear Diary,

Well, I did it! Joe took the bait and I actually bullied him into Dare. So once he chose that, I got him to dress up in my heels, blouse, and miniskirt “for the evening”. We are the same size! You should have seen his face five minutes later when the doorbell rang!!  He ran for his room, but I said, “Oh no you don’t!! That’s Master Brent, and if you try to hide, I will tell him where you are and he’ll see you all dolled up like that. I’ll tell him who you are!” He looked petrified. “But …. if you just pretend to be a girl tonight – you’ll pass with a wig, from my bedroom. I won’t tell him as long as you say you are my room mate named Jill!”  He thought it over quickly, then ran to my bedroom for the wig. I let Brent in, and told him if he would wait on the couch for a few minutes, I had a surprise for him. He waited – he likes my surprises. Joe won’t like them so much though.

I went to the bedroom and fixed Joe … Jill! … up with the wig and some make-up. Then I dragged him – or her – out of the bedroom. I could almost feel him shaking.  “Brent, I want you to meet my room mate – this is Jill,” I said with a cheeky grin. “Jill … huh? Ok. Nice to meet you…” Brent said. He knew my room mate was actually named Joe. He also knew what a pain Joe was. But he could see I wanted him to play along.  “Jill bought a present for you Brent,” I said, giving him the wrapped hairbrush. “That’s why she’s so nervous …. this is her first time.”

“My first time what??” Joe said, forgetting to be nervous about his voice. Then he went silent as Brent held up the hairbrush.  “Does this mean what I think?” he asked. “Oh yes, I told Jill all about how you spank me, and you asked me to find another girl so you could spank the two of us together. Jill was so curious, she volunteered! I think she should go first though, since if I go first she’ll get too scared and bail!”  I pushed Sissy boy Joe toward Brent, who caught him by the arm and pulled him over his knee. Joe’s skirt flew up as he landed – perfect! A few warmup spanks with the hand over the panties. Joe thought he could get out of it – so cute. “Wait! No! I’m not … ow! I’m a … OUCH! No…… nooooooooo………” Soon the panties came down. Since Brent already knew it was Joe, there was no surprise there for him. The barebottom hairbrush spanking was just GLORIOUS! He was yelping and sniveling and wiggling all over Brent’s lap – so much so that he actually had an orgasm! I found I enjoyed watching that spanking almost as much as I like getting them myself. But… after Brent finished with Jill, he reminded me how much I like getting them too.  So – now I am in my bed, bottom red and stinging, laying on my tummy to write this entry. I peeked in Jill’s room a little while ago – she is still in my make-up and wig, wearing only a pink shirt. What do you suppose that might mean? And, it looks like there are two girls sleeping on their tummies here tonight! Call me for some spanking Fetish Phone Sex

888-430-2010

#crossdressingsissy #notaboo #spankingfetish