f***ed to cross dress on Halloween - Sex Stories

f***ed to cross dress on Halloween

... down the rest of his body. With the help of gravity, the long dress fit like a glove around my corseted victim. “Let me zip you up.” I said as I grabbed the zipper which started at his lower back. Slowly, suspensefully, I zipped him up while whispering into his ear, “Once you are zipped, there is no way out.” He almost lost his balance right there, standing in his high heels. He was so scared and horny at the same time. It was making me wet seeing him like this. Once the zipper was all the way up, I used a padlock to clasp the two metal rings at the back of the neck together. *Click* Another padlock to make sure he would behave. I folded the collar of the dress over the padlock so it would be our little secret. The thought of having him locked in this sea of satin made me even hornier. The white satin garment on the bed was next. I grabbed it and tied it tightly onto my new maid. It was a long white pinafore apron which matched the dress. “Turn around for me.” Mark's new uniform transformed him into a Victorian maid. Mark’s new uniform transformed him into a Victorian maid. Slowly, my new perfectly-shaped maid turned towards me, his head bowed downwards in shame. He must have realized he was in some sort of uniform, though he probably did not want to believe it. “Very good, just a few minor details.” I said while grabbing my lipstick. Getting the lipstick on neatly was no work at all, but the blonde wig was a whole different matter. Since my maid was still blindfolded, I had ...

... to work a bit to keep him from seeing while I put the wig on his head. He must have felt the hair tickle his face because I could sense he was getting more and more anxious. I was soon ready to unveil his new identity for the day. *** I stood behind him as I asked, “Are you ready to see your Halloween costume?” “I… I… don’t know.” He meekly answered, clearly confused by the complicated mix of arousal and fear. Honestly, him being so scared only made it more fun for me. It got me really excited to see what the night would bring. “Well, here goes!” I said joyfully as I undid his blindfold. “Oh my…” his mouth fell open. He was almost in shock, looking at himself in the full length mirror on the back of our bedroom door. Well, not really himself since it was a Victorian maid who was staring back at him in the mirror. I went all out, making sure his costume included heels, bright red lipstick and a blonde wig. “Why?” he managed to squeak out the question. “Well, you weren’t very helpful with selecting a Halloween costume this year, so I figured I would help you a little.” “But, I can’t…” He tried. I did not let him finish. With my right hand I pushed him forward abruptly, him swaying on his heels, and lifted the long skirt of his uniform from behind. I found his panties and through the soft satin material I immediately grabbed his balls and squeezed them. He stopped talking right away and just made pleading sounds instead. “You were saying something?” “No… ahh… I…” “What is it?” ...