Sister’s Surprise_(0)

This is my first story, and I apprieciate any constructive critism.


A closet cross-dresser is caught and exposed, but gets an even bigger surprise from his sister.

Sister’s Surprise

My parents would never understand. How could they? They raised my to be a good little boy, and that was all they knew. They had no idea about my cross-dressing fantasies. It was a life I kept secret from everybody. And until three days ago, it was secret I kept even from my girlfriend April. A business meeting that ended early also ended our relationship.
I was always small growing up, but that didn’t stop me from being active. In Junior High, I had wrestled and was on the track team. In high school, I joined the swim team, but it was my track career that excelled, breaking a few school records in the high jump (and only a fraction of an inch from a state record). It was during my athletics career, that I met April, a cheerleader, who I thought was the love of my life. We moved in together right after graduation, but soon life together began falling apart. It wasn’t the romantic ideal that we had both envisioned, and soon our life together became unbearable. In a way, I am thankful for her meeting ending early.

That was why I was standing at the door of my sister’s apartment, knocking softly, with boxes of my stuff sitting next to me, containing a total of the life I had left. “April kicked me out”, I said trying hard not to start crying, as the door opened with my sister Jessica standing at the threshold.
“I know”, she replied evenly, a worried look on her face. “She plastered the breakup, along with what you were doing, all over Facebook. You might want to save yourself the trouble and just delete your account”. She smiled weakly at me, as she grabbed a box and hauled it inside. “Jen’s at Tyler’s for the next few weeks for summer vacation, so you can have her room”, she took the box into her daughter’s room.
“You aren’t mad?” I asked, still standing outside the door.
“Of course not”, she replied with some mirth. “We’re family. And besides, growing up, I always thought it was odd that some of my clothes would go missing, and return a few days later. I kinda knew you were closet cross-dresser. But if it made you happy, I wasn’t going to stand in your way, or rat you out”. She seemed to smile at some secret memory, and then she smiled knowingly at me. “Look, there are no judgments here. I love you no matter what. If you want to parade around as Michelle here”, she used the feminine of my name, “then that’s fine by me”.
She help load the rest of my things into her daughter’s pink room without much more conversation, then excused herself to make dinner, and so I could put away some of my things. After she had gone, I stared at the simple brown box April labeled ‘fag’, and that I had crossed out. Inside were a collection of clothes that would take me from Michael to Michelle. I had thought about what Jessica had said about this being a place without judgments.


“I hope you like spaghetti”, Jessica said from the kitchen when she heard my door open. Her back was turned to me, as she scooped the noodles from the pot to a nearby plate. “Oh, and I already hacked into mom and dad’s Facebook and deleted April from their friends, so hopefully, they won’t know about it until you decided to tell them”, she said, adding the red tomato sauce to a pile of noodles on a plate. All strength must have left her hands as she turned to see me, dropping the freshly prepared plate on the floor.
I stood for a while under her shocked gaze. My heart was beating uncontrollably out of my chest. I had decided that for the night at least, I was Michelle. I wore a wrinkled white blouse with nearly exposed shoulders. The straps of my white bra visible as they arched over my shoulders, secretly stuffed with breast forms to give myself some cleavage. I had on a faded pair of hip-hugger levi’s, and some cute yellow socks, no shoes. I also donned a wig, turning my usual short dark hair into long, wavy platinum blonde tresses. Red lipstick coated my pouty lips, my mouth open so I could breathe.
We both stood in silence, the sound of a nearby clock starting to drive me insane as my heart beat at least twenty times per tick-tock. The eons ticked by on that annoying clock, as both of us just stood there. My fears creeping into my mind, suddenly thinking this was a horrible idea. I turned, ready to run back to the room, and return as Michael.
“Wait”, Jessica called after me. “Aren’t you even going to help me clean this up… Michelle”, she said, the name sounding foreign to me, but also so right.
I was unable to form words, my voice fleeing as my heart wanted to. I slowly nodded, as I took a step closer to the kitchen. My knees trembled trying to hold up my own weight.
“When I had read the mean things April has posted about you, I just couldn’t believe them”, Jessica said as I took another shaky step forward. “But now I can see that she was just jealous. Jealous that she will never look half as good as you do right now”.
It was all I could do to smile at her. Growing up, my sister and I were always close. Even though she was three years older, and made some different life choices that had her with a six year old daughter, and a ex-husband at the age of twenty-two.