A Sissy Surprise

I got home early from my night out with the girls. Jeff wasn't in the living room watching tv so I figured he was in the bedroom jerking off so he wouldn't have to bother me with a request for sex when I was toasted. I decided to surprise him and slowly made my way up the stairs.

I walked into the bedroom and stopped dead in my tracks. My boyfriend was on his knees facing away from the door and sucking on the cock of some guy I'd never seen before.

"Jeff? What the fuck is going on?" I demanded as I walked towards them, wondering why he was wearing my dress and where he got the black fishnet stockings and red spike heels.

He pulled away and tried to stand up as he stammered, "Oh god, I ... I'm so sorry Nan! I thought you were ... oh damn."

When he finally stood and turned around I saw the smudged bright red lipstick, blush and blue eye shadow. I thought to myself, "When did he learn to apply make-up?" That's when I noticed he was also wearing a short curly blonde hair wig.

The dress he'd chosen was one of my favorites--a black figure-hugging skimpy dress that was extremely low cut. We were about the same weight so he easily fit into it, though it was a bit more snug across his shoulders and only went to about mid-thigh on him because he was so much taller than me. I could see the outline of a bra and wondered if it, too, was mine and if he'd stuffed it or if it was his moobs filling it out.

"Who's your boyfriend?" I demanded as I crossed the room to where they stood. Jeff was shaking as I stared at him.

"Franco, a guy I know from the bar."

"Hello, Franco," I greeted and shook his hand. Franco was about the same height as Jeff but slim and muscular. He looked European and had dark tanned skin with brown eyes and shoulder-length wavy brown hair. "Have you two been lovers for very long?"

"No," Jeff answered. "This was ... is the first time."

"I see," I replied as I trailed my finger down Jeff's back and felt panties. I wondered if they were mine or if he had the decency to buy his own. "So, then, do you wear my clothes often?"