There is just something about dressing up a sissy boy that delights me. I guess all girls loved to play dress up, but dressing up as sissies is so much more fun. Surely I could play in my closet, trying on all the sexy dresses and heels I’ve acquired, but I’d rather dress up my sissy boy. He gets so excited when I call him over because he already knows what to expect. Today was slightly different, but I’ve decided to surprise him once I’ve dressed him all up.

He arrived hours later, full of excitement and ready to be my personal mannequin. I’d already picked out a few looks to put on him and had them laid out on the bed. His face lit up when he noticed the sex sequined, backless red dress. I noticed him eyeing it in my closet a few times, and since today was a bit different from other days, I’d decided to add it to the selection. My pretty sissy boy was tall and thin with an almost modelesque frame, which made it so easy to dress him.

I would have him try on three or four dresses before we got to the one he really liked. I already knew it would be my final choice. Once we got him dressed and painted his face to match his sexy red dress, we found the perfect shoes. He loved sexy, high-heeled shoes and nice, sexy nylons. After the look was complete, he stood smiling at himself in the body-length mirror. I played with his hair as he admired the final look. “Perfect! Now you are all ready.” He wore a look of confusion. “Ready for what, miss?” I could only release a wide smile as my surprise entered the room. There stood a tall, dark, muscular black man wearing only a sly grin. I turned to him and spoke, “My pretty sissy boy is ready for you now.”