February 14, 2019
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 […]