Sissy Gets Ready to go Out

Two months ago, my little sister had caught me dressed up in mom's clothes and make-up when she came home early one afternoon.  She said that she would tell mom and dad -- unless I did exactly what she said from now on.  I guess I had always been a bully to my little sister and now was payback time.

Since then, we've been playing "dress up" almost every night.  After dinner, we run up to her room where she makes me practice doing my make-up and styling the wig she made me buy.  She makes practice walking in high heels and sounding like a girl when I talk.

She told all her friends about what a sissy I was -- and how I was really cute when dressed up like a girl.  Tonight, my sister told me, was going to be my "coming out" party.  She was going to take me, along with three of her friends, to a fancy club downtown where they never check IDs of cute girls who want to go in.  I'm the only one old enough to have a license, so I have to drive.

Mom and dad went out early to go to a party so we spent most of the afternoon getting ready.  My sister picked out my outfit for the evening from mom's closet -- a fancy gold and white Lily Pulitzer dress and a pair of strappy high heels.  She helped me get my wig and make-up just right.

"Hmmm," she said with a smile while looking me over when we were done.  "You know, Michael, you really do look like a pretty girl.  I don't think any of the guys at the club would ever guess that you're really a boy when they start flirting with you.  Just be careful when they start feeling you up."

When she said that, I broke down into tears, panic suddenly overcoming me.  "Please don't make me do this!  PLEASE!"

"Oh for God sake STOP CRYING!," my sister yelled.  "You're ruining your make-up!  You are such a big sissy!  Get it together and fix your make-up before the girls get here!  NOW HURRY!"  She slammed the door and went downstairs.

I stared at my reflection in the mirror.  My sister was right -- I did look like a pretty girl.  And she was also right about me being a big sissy. I knew I had to obey my sister or she would tell mom and dad.  As I started redoing my make-up, I tried to imagine what it was going to be like, being in a fancy nightclub in a pretty backless dress, sexy stilettos and glamorous make-up, knowing that men would be trying to talk to me and buy me drinks and...other things.

"Michael!  I mean Michelle!" my sister yelled from downstairs.  "Hurry up!  The girls are here!"

I dried my tears and fought to calm myself down.  I fixed my mascara and finished putting on my bright red lipstick.  I grabbed my little clutch purse and headed down the stairs.

When my sister's friends saw me, they screamed with delight.  They all told me how pretty and sexy I looked.  They said that all the guys would be drooling all over me tonight.  I enjoyed hearing the girls say that I was pretty -- but talking about the men at the club made me feel  sort of sick to my stomach.

One of the girls said, "And when you're giving some guy a blow job tonight, be sure to swallow every drop.  You don't want to get any stains on  your mother's pretty dress."

The girls howled with laughter at that.  I almost started to cry again.

"Time to go, Michelle," my sister said.