I love raiding my younger stepsister's panty drawer. Lisa has some of the sexiest lingerie I've ever seen. When she leaves the house, I sneak into her bedroom and pick out a few pieces to try on. She keeps everything folded in neat piles of silk and lace. A small bag of potpourri keeps the drawer smelling fresh.
I know things about my stepsister even her best friends probably don't. She wears a 36c bra and medium panties. Most of her lingerie comes from Victoria's Secret but she also has a corset from Fredrick's of Hollywood. It's quite a collection for a girl who's barely 18.
When she went away to college, a few neon stripper outfits appeared in her drawer. At first, I thought she was working at a strip club, maybe just for kicks. But then I found her diary and learned that her boyfriend, Rick, was into the slutty look.
Whatever sensual treats she had in the drawer, I was happy to borrow. It was my way of playing along with her sex life. When I put on her intimate wear, I was becoming her. The same bra that pushed up her tits would press into my chest. The same silk that rubbed against her young, wet pussy would caress my cock.
I once found a thin, silver vibrator at the bottom of her drawer. I fucked myself with it on her bed, wishing that she and I could one day share the same cock.
Never in my life did I ever dream it could happen.
Until I found the note.
It was on a Friday afternoon when my stepsister was home from college for winter break. I went into her room to borrow a bikini for a jack-off session while she was shopping with some friends. When I opened the lingerie drawer, I was shocked to find it empty, except for a pink piece of paper with a message printed in neat, cursive writing:
Rick,
I know what you're doing. If you don't want your dad to find out, be home at 8 tonight.
-- Lisa
My heart skipped. If dad found out, I'd be kicked out of the house forever. I could say goodbye to my Porsche, allowance and inheritance. I'd have to go back to college or -- even worse -- get a job. I decided right then to do whatever Lisa wanted.
My dad left about 7:30 to have dinner at the country club and I assumed my stepmother was with him, although she'd later prove me wrong. Lisa came home 20 minutes later. I was sitting on my bed and pretending to read the new issue of Rolling Stone. But I couldn't concentrate on anything. Instead, I listened closely to the muffled voices echoing up from the kitchen. It sounded like Lisa had brought home two or three friends.
My heart raced as the footsteps moved up the stairs and then down the hall to Lisa's room. Her bedroom door closed. Relieved, I took a deep breath. Maybe she'd decided not to blackmail me after all.
I went back to reading my Rolling Stone. Just as I was beginning to absorb a cover story about Slipknot, I heard Lisa's door open again. She and the others giggled. Then Lisa said, "OK, just wait here. I'll see if he's home."
My door opened two seconds later. Nothing could've prepared me for what I saw next.
Lisa was standing in the doorway with a crooked smile on her face. She wore nothing but my favorite corset, panties and fishnet stockings. Her wavy, blonde hair was draped over one shoulder. A diamond pendant hanging from her gold necklace twinkled in the light. She had a pink Victoria's Secret bag in her hand.
"OK, you sick, little bitch -- you know why we're here," she said. "You've been stretching out my bras and panties for years and I haven't said a word. It's payback time."
"No shit?" I asked. "I thought you wanted to play checkers."
Her face twisted into a scowl.
"Are you getting smart with me?" she asked.
Lisa lunged at me and smacked me across the face before I could defend myself. The sting lingered.
"Listen, you piece of shit," she said with her finger wagging an inch from my nose. "You're going to do exactly what I tell you or your dad is going to find out his son likes to dress up like a little girl."
I folded my arms and looked sullenly into my lap.
"Fine," I said. "Whatever."
Lisa dropped the pink bag onto my bed.
"Put that on," she said.
Lisa stepped back and plopped into the chair next to my computer desk. She crossed one long, smooth leg over the other and bobbed her foot. For the first time, I notice she had on black six-inch heels.
"Go on," she said. "Look in the bag."
I emptied the contents into my lap. It was everything I'd need for a night of cross-dressing: make-up, perfume and a corset identical to Lisa's, except that mine was purple. I pressed the fabric to my nose.
"New?" I asked.
Lisa nodded. The crooked smile was back on her face.
"Put it on. Now. People are waiting," she said. "And don't ask another question."
As I stripped naked, I threw my guy clothes toward the bookcase in corner of my room. My transformation started with the corset. It had a dozen hooks in the back, so I put it on backwards and then slid it around. Then I slipped my arms through the straps and pulled as much flesh into the cups as possible. The corset squeezed me in all the right places. My cock sprung to life.
"Looks like somebody is enjoying this," Lisa said. "Keep going."