Stepmom's Sex Shocker Ch. 06

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Ann sexually humiliates cross-dressing stepson.
3.1k words
4.35
95.4k
34

Part 6 of the 6 part series

Updated 10/29/2022
Created 08/21/2005
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My step-mother, Ann, jolted me out of my dreams by slapping me across the face.

"Rise 'n' shine, bitch," she said. "I need some entertainment."

My eyes strained against the sunlight streamining into my bedroom window. Ann stood next to my bed with her hands on her hips. She wore a purple, push-up bra and a matching thong. Her ample bush pushed against the sheer fabric. She dropped a tangle of lace and silk on my chest.

"Put it on," she said.

I picked up one of the lacy garments by my fingertips. It was a bra identical to the one Ann was wearing. The panties on my chest were also the same.

I was still in a dreamy haze

"You want me to wear this?" I asked.

Ann's answer couldn't have been clearer. She wound up and back-handed me across the face like a pimp.

Without a word, I sat up and threw back the covers. I slipped off my boxers and put on the thong. As the string slid up my backside, my balls and cock settled neatly into the triangle up front. I hooked the bra behind my back and then slid my arms through the straps. The cups held my tits like a pair of hands.

Ann frowned and shook her head.

"You dirty, little whore," she said.

Ann kneeled on the bed next to me. She pinched my nipples and leaned in close. Her breath smelled like mint.

"You're mine, faggot," she said, while rolling my nipples between her fingers.

Her deep, brown eyes swallowed me whole. Her cruel gaze made me yearn for her abuse.

"I want you to go into the bathroom," she said. "Put on your dress, shave and do your make-up. Everything you need will be in there."

Ann followed me down the hall and into the bathroom. I found a black cocktail dress hanging on the door. She watched me pull it over my head. The fabric squeezed me in all the right places from my thighs to my shoulders.

After I shaved, Ann watched me lay on the make-up extra thick. Black eyeliner. Mascara. Red lipstick. I looked and felt like a whore.

"Not bad," she said. "For a faggot bitch."

Ann opened a closet and pulled out a pair of black high heels. My feet slipped comfortably into them. Ann slid on a pair of her own heels and grabbed me by the hand. She led me down the stairs to the foyer where she opened another closet. Ann put on an overcoat that covered everything above her knees. She reached up to a shelf and pulled out a red duffle bag. She handed it to me.

"A t-shirt and jeans are inside," Ann said. "You can put them on when we're done."

I quietly wondered, "Done with what?" But Ann didn't explain further.

She grabbed me by the hand and led me to the Mercedes parked in the garage. Ann opened the passenger door for me. I looked at her.

"Get in," she said.

"I'm going out in public like this?" I asked.

Ann hit me with another pimp-style backhand.

"Yes," she said. "Any other questions?"

I got in the Mercedes without another word.

We drove in silence for about 45 minutes to a Holiday Inn about three towns over. Ann parked in front and turned off the car.

"Follow me," she said.

We went into the front lobby. Carrying the duffle bag, I made my walk as feminine as possible, but I knew I wasn't passable as a woman. I could feel strangers' mocking eyes on me. I tried to ignore them. A group of men in business suits sitting in a lounge area chuckled as I passed.

"Hey, baby," one of them said.

The rest howled with laughter.

I followed Ann to an open elevator door. She hit the button for 12, the top floor. When the doors shut, we were alone. Ann slid behind me and grabbed my tits. She pulled me in to her body. Her tits pressed against my back, as her minty breath caressed my neck.

"You like being humiliated, don't you, bitch?" she whispered.

Ann pinched my nipples and started rolling them between her thumbs and forefingers.

"Yes," I said breathlessly.

When the elevator stopped at the fourth floor, the door opened with a ding. A guy in a golf shirt stepped inside and hit 12. Ann refused to let go of my tits. The guy tried to pretend to not notice, even though my cock was pitching a tent with my dress.

"I'm gonna fuck the shit out of you," Ann whispered in my ear.

I'm not sure if the guy heard, but he looked up. When the elevator opened, the guy scurried out and down the hall to the right. Ann released my tits, grabbed my hand and led me to the left. At room 1217, she drew a card out of her purse and inserted it into the electronic lock.

The room was a suite with a king-size bed and a view of the suburbs. It was all traffic-clogged roads, strip malls and office buildings for as far as the eye could see. We were in the tallest building for miles, so we had total privacy, even with the curtains open.

Ann didn't waste any time. As soon as the door shut, she said, "Hands up!"

I dropped the bag on the floor and raised my hands. Ann pulled the dress over my head. Then she yanked my panties to my ankles. I stepped out of them.

"Get on the bed now," she said. "Doggy-style."

I obeyed, while Ann shrugged off her coat and then dug through the duffle bag. Her hand emerged with a chrome dildo and a tube of lube. She kneeled on the bed behind me.

"Spread your ass cheeks," she said.

I did as I was told. Ann put a dollop of lube on her index finger and then touched it to my asshole. Goosebumps formed on my arms. She massaged the entryway for a minute and then slowly pushed her finger inside me. My butthole loosened up. I was ready for anything.

Ann pulled out her finger. I braced for the dildo, clenching the bedspread and squeezing shut my eyes. I took a deep breath and held it. And then...

Nothing.

Releasing my breath, I began to turn my head to see what was the matter.

That's when she hit me.

Ann pumped the plastic cock inside of me.

"Uh!" I said.

Ann pulled the dildo about halfway back.

"I love abusing you," she said.

My spine tingled.

"Do you like being abused?" Ann asked.

I grunted.

Ann pushed the dildo forward. I arched my back.

"Answer me, bitch!" she yelled.

"Yes, mommy!" I screeched. "Abuse me some more! I'm your little cunt!"

Ann slammed the dildo all the way up my ass. It felt as if she'd pushed a button deep inside me for the first time. I felt humiliation, pleasure and pain all at once. My cock swelled.

Ann slowly pulled back until the dildo was a half cunt hair from leaving my ass entirely. Breathing heavily, she paused. I knew something violent was coming. My fingers balled into tense fists. And then...

Nothing.

Ann just sat there with the tip of the dildo barely inside my bunghole. I relaxed my hands. It seemed that Ann had decided to show mercy. I started to turn my head to look back at her.

"Thank you, mommy, for sparing my ass--," I started to say.

Ann hit me again, her toy prick blasting inside of me like a nuclear bomb.

"Whore!" she yelled.

My body shuddered. Ann withdrew slowly. She paused and pounded me again.

"Cunt!"

And again.

"Twat!"

And again.

"I fucking hate you!"

Ann yanked the dildo out of my ass. With astounding strength, she grabbed me by the hips and rolled me onto my back. The bed shook. I thought the head board was going to fall off. I looked up at Ann. Her brow was furrowed. She drew back her arm and smacked me across the cheek.

"You are a piece of shit," she said.

My cock was ready to explode. Ann dropped down and took my entire schlong into her mouth. Her head bobbed three times. I couldn't hold on. Our eyes met as I shot my load. I'd never cum so hard in my life. I must've sprayed a gallon of goo. Ann took every drop and held it in her mouth.

After sucking the last drop from my pecker, Ann pulled herself up until her face was even with mine. Her deep, brown eyes blazed with hatred. Like a dam ready to burst, her sealed lips held back my jizz.

I knew what was coming.

"Do it," I whispered.

Ann drew a deep breath through her nose. As her chest rose, I opened my mouth and closed my eyes.

The dam burst. Cum splattered all over my face. I felt it running down my cheeks and trickling down my neck. Some of the salty mess landed on my tongue. I closed my mouth and swallowed. The jizz effortlessly slid down my throat.

When I opened my eyes, Ann's face was still there, glaring at me. She rubbed the goo into my face and then made me lick the palm of her hand.

"You fucking disgust me," she said.

I felt humiliated-- and loved it. I didn't want it to end. Ann wasn't about to let it.

She went to the phone on the nightstand and picked up the receiver. She dialed a few numbers, paused and then said, "Yeah, we're ready. Send the first one in."

The knock at the door came almost instantly.

"I hope you're ready for some punishment because you're about to get it," Ann said. "There are five perverts next door. Each one gave me $500. Know what that buys them?"

I shook my head.

"Ten minutes with you," Ann said. "Anything they want."

She opened the door. A dark-haired beefcake of a man stepped inside. His biceps strained the sleeves of his black T-shirt. The lump in his jeans extended most of the way down his thigh.

He looked at my face and nodded.

"Mmmm," he said. "I like it."

Ann went to the overnight bag on the desk and pulled out a video camera. She flipped open the side viewer.

"And don't forget," she said, "with your purchase today, I'll send you a souvenir video for free."

Beefcake smirked.

"Cute," he said.

The guy grimaced at me. He looked like a lion three hours before feeding time. And I was his prey. I shuddered.

"On your knees, bitch," Beefcake said.

I slid off the bed, took two sexy steps and dropped to my knees in front of him. Beefcake unzipped his jeans and hunched over to push them to his ankles. He wasn't wearing underwear. His cock almost smacked my chin when he stood up.

As a former football player, I've been in a lot of locker rooms. But I've never seen a thick-a-saurus quite like this. The guy had at least nine inches.

I wrapped my lips around the head and slowly slid my head down the shaft. I made it about a third of the way down before my mouth was full. I pulled back and inhaled deeply through my nose, preparing for another dip.

"Don't tease me, cunt!" Beefcake yelled.

He grabbed the sides of my head and thrust his whole salami into my mouth. I gagged. But the guy showed no mercy. He pulled back and rammed me again.

"Take it, bitch," he said.

I loosened my throat and decided to let him do whatever he wanted. I had no choice anyway. The guy relentlessly and repeatedly forced his cock into my mouth. I made sure to keep my teeth out of the way. Every time he thrust himself forward, my nose dipped into his curly, black pubic hairs. He smelled like Polo cologne.

Beefcake didn't last long. After about 30 strokes, he pulled out of my mouth and aimed his prick at my face. I threw back my head and opened my mouth. The guy either had terrific aim or was incredibly lucky. Almost every drop splattered across my tongue. When he finished, I sealed my lips and swallowed.

The guy pulled up his pants, pivoted and walked out of the room, slamming the door behind him. Beefcake didn't even say thanks or good-bye.

"Another satisfied customer," Ann said.

The phone on the desk rang. Ann picked it up.

"Hello," she said.

After a pause, Ann nodded and said, "OK, consider it done."

She hung up.

"The next guy doesn't even want to see your face," Ann said. "He wants you on the bed with your asscheeks spread."

I climbed onto the bed and got in the doggy-style position. Burying my head in a pillow, I used both hands to spread open my buttcheeks. Ann got the tube of lube and put a dab on her index finger. She worked the lube around the entry to my bunghole.

Three hard knocks at the door shook the room, as she put the cap back on the tube. Ann rushed to answer. I heard the door swing open and bang against the wall. Short, quick footsteps came toward me. The door closed. I heard a swift swishing as the client's pants fell to the floor. The headboard banged against the wall as the guy pounced on the bed. An iron grip fell upon my hips. He pumped himself inside me all at nice.

I never saw his meat rod, but it had to be at least as long as Ann's dildo. The guy fucked like he was mad at something. He took long, punishing strokes. Each one was harder than the last. The best part was that he never made a sound. Not a single grunt or moan. It was like getting fucked by a serial killer. Some people might find that creepy. Not me. My prick felt like bursting. But I held back.

I knew the guy was about to cum when I felt him shake. He pulled out and blasted a load on my back. It was a big one. The jizz ran down my spine and dripped down my buttcheeks. There was a silent pause. Then the guy snapped his fingers twice.

"Oh," Ann said. "You want me to clean him up? OK."

Ann dragged her tongue across the small of my back, smacking her lips dramatically as she lapped up the guy's jizz. She worked her way to my ass crack. Ann didn't shy away from it. To the contrary. Her licking intensified as she buried her face into my upper crack and then made her way down. Pausing at my bunghole, Ann spread open my cheeks with her fingertips and dug her tongue inside me. My cock felt like bursting again. But she pulled out before I came.

"Time's up," she said to the customer.

I heard him pull up his pants and walk to the door. When it shut, I flipped over on my back. Ann looked at my boner and shook her head with a smile peeking out the corner of her mouth.

"Fuckin' weirdo bitch," she said under her breath.

The phone on the desk rang. Ann picked it up.

She nodded a couple times and said, "Yeah. It's your money. You can do whatever you want."

Ann hung up and went to the door.

"Get ready," she said. "Because here comes the grand finale."

Ann didn't even wait for the knock. When she swung open the door, three guys stepped in. They lined up along the edge of the bed. A guy in a Brooks Brothers suit glared at me. A blonde surfer dude smiled eagerly. A dark-haired Latino in tight jeans licked his lips.

Ann aimed the video camera at them.

"Go to it, boys," she said. "The clock is running."

No one needed to be told twice. The three of them had a coordinated attack that they'd clearly planned before coming in the room. They flung clothes into the corner and leapt on the bed. Brooks Brothers hoisted my legs above his shoulders and pressed his cock into my asshole. I grunted involuntarily as his meat filled my pipe.

The Latin guy kneeled next to my head to my left. Surfer boy did the same to my right. They pointed their cocks at my face and started stroking themselves.

Brooks Brothers was working hard. He furrowed his brow as he plowed my ass. A trickle of sweat dripped down his temple. It was my first time taking cock in the missionary position. I liked it. I knew my legs would be sore the next day, but the guy's dick was hitting a special place inside me. A cum volcano bubbled inside me.

There must've been one inside the Latin guy, too. He came first, erupting on my face in powerful spurts. The sight of cum dripping down my face triggered a chain reaction. The surfer guy popped next, adding to the mess on my face. As I licked the salty jizz off my lips, Brooks Brothers pulled out and dropped his load on my stomach.

Cum dripped down my cheeks and pooled in my bellybutton. Brooks Brothers fell back on the bed.

"Fuck," he said breathlessly.

Ann handed the camera to him and flopped onto her back next to me with her legs open.

"Fuck me," she said.

Brooks Brothers aimed the camera at me as I rolled onto my stepmother. She guided my prick into her hot, wet pussy and squeezed my titties as I began slowly pumping her. Cum dripped off of my face and splattered onto her cheeks and nose. Ann opened her mouth to catch the drops on her tongue. I lowered my head to give her a long, slow kiss. As soon as our tongues met, I shot my gook. Her pussy accepted it like a hungry mouth. Time no longer had any meaning. Our tongues wrestled, as cum flowed out of me.

After I squeezed the last drop out of my prick, Ann pushed me off of her. She sat up and pointed at the three clients.

"You three got the bonus plan," she said. "But time's up."

They put on their clothes and scampered out of the room.

When the door closed, Ann went into the bathroom to clean up. I did the same when she finished. I threw my bra in the garbage and put on my t-shirt and jeans.

"Let's go," Ann said.

We drove all the way home without saying a word to each other.

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8 Comments
AnonymousAnonymousalmost 8 years ago
went flaccid the moment she said i hate you

I just dont get it. He likes it I get that but why does she hate him so much as long as its consensual and there's some form of love I like the story but that was just fucked up i only read this fhapter not the others.

AnonymousAnonymousabout 10 years ago

Just keeps getting better

AnonymousAnonymousover 12 years ago
Woah

Pretty sure the quiet guy was his dad.. Hot. Creepy, but hot.. I'm not usually into crossdressers though

AnonymousAnonymousover 13 years ago
Great story!

I think this silent guy was his father :)

AnonymousAnonymousover 13 years ago
wish it was me

I loved every minute of this story. I pictured myself being the one sucking and fucking and cleaning cocks mmmmm yummy. I love them all big or small long or fat they all feel good.

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