A Crossdresser Gets Fitted

He nervously returned my smile as I approached him and asked, “Are you going to try those on?”

“I wasn’t,” he said, blushing a little and looking down at his selection.

“You should definitely try them on,” I said with a wink, taking the clothes from him, “you don’t want to get home and find out they don’t fit properly.”

I tugged on his t-shirt sleeve and said, “Come on,” as I lead him to the fitting rooms.

“I’m Vennessa,” I told him as we weaved through the racks in the nearly deserted store heading to the fitting rooms.

“I’m Mike,” he said shyly.

“Nice to meet you Mike,” I said turning and smiling a him as we arrived.

“I could use some help getting into these things,” Mike said winking at me, seeming to overcome his initial shyness at being caught buying girl’s clothes.

“Ok,” I said with a sultry grin and led him into the fitting rooms.

I found a large room at the back, and we went inside and closed the door. The fitting rooms in this store offer better privacy than most because they are large, heavy wooden doors that go all the way to the floor and can be locked from the inside. Not like the usual saloon doors that most places have. They also have large full-length mirrors inside.

I closed and locked the door behind us then told mike to strip. I was pleased to see that he was wearing taupe pantyhose under his jeans and was completely smooth and hairless all over. His toenails were painted a dark red and his stiffening cock was nice and thick, about 7 inches long. I rubbed it with my hand through the sheer nylon and it got even harder, beginning to throb. Mike let a little gasp as I squeezed and stroked it.

“Here,” I told him, holding out the little plaid miniskirt and the white silk blouse, “put these on.”

Mike did as he was told, putting the silk blouse on first then stepping into the miniskirt and pulling it up to his narrow little waist. I turned him around and zipped up the back of the skirt, giving his firm little ass a squeeze. Then, I handed him the 5 inch strap sandal heels he had picked out and watched as he slid his femme little, nylon-clad feet into them and buckled the straps around his ankles.