Billy Is Billie on Halloween

"Loose the robe. Let me see what I've got to work with" Jenny said as if she was an artist beginning a new piece of work.

As I let the robe fall from my hairless body I could feel the air brush past me like soft breath from a warm mouth. This new feeling was invigorating and I felt incredibly sexy at that moment. Then I realized what was about to happen, Jenny was going to make me wear women's clothes. Not just any clothes though, an outfit suitable for a sexy schoolgirl. My thoughts turned to panic again, knowing that dressing this way could not lead to anything good, but I couldn't shake the thought of what Jenny might let me do to her later on.

"Start by putting these on" Jenny said as she handed me a red laced thong and bra. I did as I was told, sliding the soft fabric up my legs and then letting it strap against my thigh. My stomach started to turn as I could feel my cock harden. Feeling the thong start to ride up my ass and the way the fabric moved against my cock was amazing. After the thong came the red bra, with more room in the cups than I needed. Little did I know that Jenny had two C-cup breast forms for me to place inside, giving me a nice and soft rack that any girl would be proud of.

"Now we can slip on your blouse and gorgeous checkered skirt" Jenny smiled, I could tell she was enjoying this immensely.

I no longer hesitated, quickly trying to get the skirt on to cover my small erect penis. Everything felt so soft and sexy on my body. While keeping my ass nice and warm, the skirt let any small breeze violate my entire genital region.

"Ok, now lets get these stockings on those long legs!" Jenny seemed to grow more excited with every piece of clothing we added. Although I was getting just as excited, I kept my mouth shut and just enjoyed the experience of pleasing Jenny. She helped me as I put the lace stalkings on one by one, making sure the get an even stretch and covering everything just above my knees. After we finished I felt like a real woman and wanted to see just what I looked like. But before I could get to a mirror I was stopped by Jenny saying, "Not yet hun, first we need to get some makeup on that pretty face of yours."