Crossdresser is punished for raiding panty drawer

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:


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."

I sat on the edge of the bed to roll the fishnet thigh-highs up my legs. I was careful to not leave a run in them. Lisa smiled.

"You're good," she said. "A real natural."

I made quick work of fastening the corset's garter straps to the stocking tops and then slid on the thong. The thin string settled into my ass crack, but I struggled to tuck my cock and ball into the little triangle of fabric up front.

"It's OK," Lisa said. "You won't be wearing that for long anyway. Do your make-up."

I gathered all the tubes and bottles on my bed and took them to the mirror above my dresser. Lisa had brought me the sluttiest shades of black and red. I laid them on thick and then sprayed perfume on my wrists.

I examined myself in the mirror. I wouldn't pass for a woman, but I did well for a novice. In the reflection, I saw Lisa slide in behind me. She pressed her tits against my back and wrapped her arms around me, as she licked my ear.

"I'm gonna have fun abusing the shit out of you," she whispered.

Her hands slid up to my tits. She pinched my nipples between her forefingers and thumbs. They rolled back and forth. My knees wobbled. I could've cum in panties right there. Lisa sensed it and stopped. Her hands left my tits to grab my shoulders. She spun me around, pointing me toward the door.

"Walk," Lisa said. "To my room."

I did exactly as I was told with Lisa following close behind me.

When I opened her bedroom door, I was stunned yet again.

My stepmother, Ann, was on her knees in front of a young, black-haired muscle man, who sat on the edge of Lisa's bed with his legs spread. Ann was sucking him off, her head bobbing with her lips around his cock. She wore a pink corset and stockings. The guy was naked. As if all this weren't weird enough, another naked muscle guy was filming Ann's performance with a video camera.

Everything stopped and their heads turned toward me when I entered the room. My stepmother looked sexy as hell. She was 40 but had the body of a woman half her age.

"Well, well," Ann said. "It looks like someone's ready to play."

She cast her eyes at the raging hard-on sticking into my panties. I shrugged.

Lisa shoved me toward the action.

With the camera guy focusing on me, Ann stood up and then moved in close to me -- so close I could smell the spearmint on her breath. She and her daughter had the same deep, brown eyes.

"My lips have been on that man's cock," she said. "His pre-cum dribbled onto my tongue. Want a taste?"

Before I could answer, Ann smashed her lips onto mine. She forced her tongue into my mouth. If any jizz lingered in her mouth, I couldn't taste it. Ann must've swallowed it. As Ann and I kissed, Lisa pressed herself into my back and rolled my nipples again. I almost collapsed.

Ann broke off the kiss. She looked over my shoulder at Lisa and said, "Let's peg this bitch."

"Fuck yeah," Lisa said.

Ann slapped me across the face, even harder than the smack her daughter had given me earlier.

"Get on your hands and knees, you he-cunt," Ann said.

Lisa disappeared into her walk-in closet. Silence fell over the room. The black-haired muscle guy was leaning back on the bed and stroking his prick. He stared at me vacantly, as if I were a picture in a porno magazine.

"You're in for it now, bitch," Ann said.

Lisa returned quickly. She had a strap-on dildo attached to her pelvis that she was lubing with KY Jelly. The fuckstick must've been at least six inches and looked just like a real cock. Lisa knelt behind me. She tugged at the panties so hard they tore off my flesh.

"Spread your cheeks, whore," she said.

I buried my head into the pink carpet while reaching behind me.

Lisa didn't shove the dildo inside me right away. She teased me first, barely touching the tip of the rubber cock to my bung hole. The cool lube gave me the shivers.

Lisa rocked back and forth, taking the dildo away from ass and then pressing it against the flesh without going inside me. It was as if she were knocking but refusing to come in. Each time she thrust forward, I wondered if it were my time for deep anal love. My cock swelled with anticipation.

And then she did it.

The thrust that broke the surface was deep and hard. An involuntary, "uh," popped out of my mouth. The two guys in the room whooped as Lisa started working my ass. She took long, aggressive strokes but never hurt me. I had to fight to hold the cum in my balls.

While Lisa ass-fucked me, I felt a hand on the back of my head. It grabbed a handful of hair and yanked. My head snapped up. A stiff dick pointed at my face, barely two centimeters from my nose. Out of the corner of my eye, I could see the camera man moving in for a close up on me and the dick.

"Suck that cock, you cunt," Ann said.

I realized then that Ann was the one pulling my hair and that it was the black-haired-muscle guy waiting for a blow job.

I was completely in their hands as I opened wide. They could give me as little or as much cock as they wanted.

On the first thrust, the muscle guy slowly shoved about his prick halfway into my mouth. He still had three or four inches of meat before my nose hit pubic hair, but the tip of his Johnson was already tickling my tonsils. I did my best to relax my throat as he pulled out, but the second thrust was so deep I couldn't help but gag. Showing no mercy, Ann held my head in place.

The face-fucking began. The muscle guy shoved his entire cock into my mouth each time he pressed himself forward. I adapted quickly, gulping air through my nostrils each time he pulled back.

"Look at this whore," Ann said. "I think she likes it. Fuck her harder, Lisa."

Lisa gave me a big thrust from behind.

I moaned appreciatively. The smallest dribble of pre-cum splashed across my tongue. The muscle guy's thrusts quickened. I squeezed my eyes shut and got ready for his load.

But then he pulled out.

And Ann let go of my hair.

And Lisa pulled the rubber cock out of my hole.

At first, I was disappointed. But then I saw what was happening.

The grand finale.

Ann flopped onto her back, while the black-haired muscle guy inched over to her face on his knees. She opened her mouth. He blasted his gak all over her face. About half of his load pooled in her mouth. The rest dripped down her cheeks, chin and neck. Ann kept her mouth open, flipping her tongue back and forth in the cum, while the cameraman zoomed in for a close-up.

Lisa shoved me toward her mother.

"Put your cock inside her and take a drink," she said.

I looked at Ann and nodded solemnly. She couldn't speak, but her eyes did all the talking. Ann wanted this badly.

Lisa stripped off her mother's panties. Ann's pussy hair was trimmed into a neat Mohawk.

I laid on top of my stepmother and pumped my pecker inside her. Her pussy was smooth as a silk purse. I didn't start thrusting. If I had, I would've cum almost immediately. I wanted to save my load.

With my cock in Ann's pussy, I leaned forward and lapped the salty jizz out of her mouth. It slid down my throat with almost no effort on my part. I finished her off by licking the cum off of her face and neck.

A split second after I took the last drop off Ann's cheek, a pair of hands grabbed me from behind and yanked me to my back. When I looked up, Lisa was on her knees, towering over me.

"Watch this," she said.

The cameraman positioned himself in front of Lisa. He pointed the camera straight down at his hard cock. Lisa absolutely threw herself into blowing him. She did it with such grace, she could run a school on cock sucking. The cameraman had nearly a foot of beef, but she never gagged once.

The guy didn't last long. He threw back his head and grunted while cumming in her mouth. Lisa took it all and held it.

I knew what to do when she started inching toward me on her knees. I opened wide.

With her bulging lips a foot above my exposed tongue, Lisa let a slow stream of jizz leak into my mouth. I let it pool until she finished. And then I swallowed.

When Lisa pulled away, I saw that Ann was lying on her back. She made eye contact with me.

"Cum on my face," Ann said.

My cock was at the breaking point. I couldn't hold back anymore. I had to let the dam break.

I lunged at Ann and aimed my cock at her open mouth. All it took was two pumps for the jizz to flow. I've never cum so hard -- or so much-- in my life. Almost all my gak hit the target. By the time I finished, Ann had a mouth so full, my gunk was spilling out the sides and dribbling down her cheeks.

Ann closed her mouth and got up on her knees. She looked longingly into my eyes, as if she were about to tell me that she loved me.

And then she spit. A torrent of my own jizz sprayed right back into my face. Ann used her open palm to rub it into my skin.

"Fuckin' cunt," she said.

Lisa and the two muscle guys laughed. The one with the camera was filming.

"Get the fuck out of here, you piece of shit," Lisa said.

"Maybe next time you'll ask before raiding someone's lingerie drawer," Ann said.

I went to the bathroom to clean up. The laughter penetrated the walls as I wiped the cum and make-up off my face.

I deserved every bit of their humiliation -- and hoped they would give it to me again.
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