Sydney's Play Toy, part 1

I first met her working at the restaurant. I was waiting tables and Sydney was a manager. I had always been attracted to women in power and she was certainly no exception - long blond hair, deep green eyes, perfect breasts, long toned legs and a smile that had just a hint of raw sex. And I knew she could tell I was interested.

One night Sydney invited me to stay after work for a glass of wine while she finished with the books. I knew she was way out of my league but I was hoping to find myself writing a letter the next day that started out "Dear Penthouse...” We began putting back glass after glass of wine, and I wasn't about to let her drink me under the table. I was wrong. I started to get very light-headed and drunk and began flirting with her - poorly. The next thing I knew - I was out.

I woke up the next morning in my bed with a splitting headache. I knew better than to get wine drunk but I had at least made it home safely. That's when I saw Sydney. She was grinning from ear to ear. "DAMMIT!" I screamed inside my head as I realized I had bagged this total hottie and didn't remember a second of it.

"I found your stash, Chris...,” she said, nodding towards the plastic storage bin in the corner of my room that held my deepest, darkest secret. It was my collection of lingerie, panties, stockings and other girlie things I would dress up in and prance around in when no one was around. I had left it out before going to work.

My face flushed and I thought quickly to keep my secret safe. "Oh, that stuff," I shrugged it off like it was no big deal. "That's some stuff my ex left here when she moved out."

"Really?" she asked, her grin growing larger. "I remember your ex - she was petite. And there's nothing in that box in a petite size. In fact, it all looks like it would fit someone your size. Interesting. By the way, you really should password protect your laptop. Otherwise anyone could find all of the sissy sites you have book marked on the Internet."

I felt my stomach sink, as I knew I was busted. My mind raced as I realized someone knew my secret and it wouldn't be long before everyone knew. I was terrified.

"I'll do anything you want, Sydney. Please don't tell anyone. I'll give you anything," I stammered.

"You? You have nothing I want, Chris. Or should I say, Chrissy?" Just the sound of it struck fear in my heart. "You want to keep this our little secret, you're going to have to earn it. Put these on," she said, throwing my hot pink pair of my panties. I had worn them hundreds of times before but this time I couldn't, not with this gorgeous woman watching me. "Go on, sissy. Hurry up."

"I can't, Sydney. You don't understand," I finally blurted out.

"Oh, no, sweetie, I do understand. You're a lil sissy who likes to dress up all girlie and pretend to be a hot woman like me. Well, if you want to be a woman like me you're going to have to do everything I tell you. Starting with putting on those panties. You want me to keep your nasty lil secret? Then you're going to be my new play toy."

To be continued...

Story by Chrissy