tagTranssexuals & CrossdressersStepmom's Sex Shocker

Stepmom's Sex Shocker


My stepmother is the hottest, wildest piece of ass in town, and I've wanted to bury my nose into her musty pussy since we first met. She's literally twice my age. I'm 20. She's 40. But I know she's a freak. When my dad fucks her, she screams, "Owie! Owie! Owie!" You can hear it across the hall in my bedroom. It's better than a porno movie. I picture my stepmother taking it hard and fast in the ass. Then I jerk off while fucking my own ass with a lubricated dildo. My favorite way to finish is to cum in a cup and drizzle the contents on my face.

Her name is Ann. She's not the type of woman you'd expect to be a Level Five butt slut. I mean, it's not like she's an ex-stripper or anything. Ann runs corporate accounts for a Fortune 500 company. You can tell she's a powerful woman by the way she dresses for work. Business suits. White collared blouses. Short skirts. She keeps her fingers sparkling with diamonds and gold, her neck draped in pearls. And, oh, how she smells! Ann wears this French perfume that leaves a wisp of dick-rising wind wherever she goes. Her attire is sexy, probably too sexy for middle management. The top brass might send her home to change some days, if she didn't rake in so much cash.

I had to have her, but any move on her would be highly risky. She and my dad have an "open marriage," meaning they fuck other people. But it would be more than my dad could take if he found out I tried to bone his wife. I could kiss the family fortune good-bye. No more Ferrari, beach house on St. Bart's or high-class hookers. I would even have to do the unthinkable. Get a job.

I eventually decided it wasn't worth the risk. I'd have to be content with my fantasies. But it turns out, I wasn't the only one with an unholy tryst on my mind.

Ann made her move when my dad went to Europe with one of his mistresses. We were the only ones in the house on a Friday night. I was downloading cum shot movies when Ann opened my door without knocking.

"What ya doin'?" she asked.

I tried to play off my rock-hard boner and the hardcore porn playing on my computer screen. Moans oozed out of the speakers.

"Uh, nothing," I said.

Ann snickered. She looked hot as ever. A half-unbuttoned blouse revealed a Grand Canyon of cleavage. She was wearing a lacy, black bra.

"Yeah, I'd probably say the same thing," Ann said. "It's OK. I'm glad you've been getting yourself in the mood."

"What do you mean?" I asked.

"Well," she said while twirling a few strands of blonde hair around her finger. "Want to play?"

With her flowery breeze drifting into my nostrils, Ann led me by the hand to her bedroom. She went directly to the walk-in closet. When she came out, a lacy, blue teddy dangled from her fingertips by a pair of thin straps. Ann held the teddy in front of her body, so I could imagine what she would like in it.

"You like?" she asked with raised eyebrows.

"Yes, very much," I said.

"Good, put it on," Ann said.

She flung the teddy at me. I caught it at my chest. My heart started to pound like a series of bombs exploding beneath my breast. Every fantasy I'd ever had was melding together and coming true at once.

Ann's bedroom screams left no doubt she was sexually adventurous. But this was a surprise -- a beautiful, bi-sexual surprise. With a huge grin, Ann put her hands on her hips and watched me slip into her underwear.

The teddy was the kind of slutty lingerie you find in Fredrick's of Hollywood but was definitely too racy for Victoria's Secret. It fit perfectly, like a dozen hands squeezing and caressing all of my most sensual body parts. The straps gently touched my shoulders. The bra cupped my tits. The thong backside slipped up my rear end. My balls and cock barely fit into the front, but I made it work.

"Very hot," Ann said, dipping back into the closet. "Now put these on."

She handed me a pair of white six-inch heels. They were size 13. I don't know why she had shoes that big, but I didn't care. My feet slipped into the shoes with ease.

Then Ann swooped back into the closet and emerged with a black wig. I put it on and looked at myself in the closet door mirror. The wig looked natural. It was the style the flappers wore in the 1920s and Goth chicks have co-opted for the 2000s. The bangs barely touched the eyebrows, while hair on the sides fell straight to the neck, framing my face.

"Are you having fun?" Ann asked.

I gulped and nodded.

"Good," she said. "You look beautiful. Now come with me."

She led me to the bathroom. A tray filled with makeup sat next to the sink.

"Time to put on your face," she said.

I chose candy-apple red lipstick, charcoal eyeliner and sea mist gray eye shadow. As I painted my face, Ann pressed her body against my back. She put her hands on my waist and slid them upwards until she found my tits. Her thumb and forefinger pinched my nipples. We gazed lustily into the reflection of each other's eyes.

"I'm going to treat you like a little cunt," Ann whispered. Her breath smelled like spearmint. She rolled my nipples between her fingers.

My cock felt like a shaken can of Coke. It could've popped at any moment. But I held back. I wanted to save myself for whatever Ann had in store next.

She brushed some rouge on my cheeks, then stepped back. We both took stock in her handiwork. I wasn't going to win the Miss America pageant, but I felt sexy. And that's what mattered.

"Very nice," Ann said. "Now, go to the bed and pose like a lingerie model for me. I'll be right there."

I slid onto the white satin sheets feeling like a beautiful woman. Pictures of my favorite lingerie models turned over in my head. How did I want to present myself? On all fours and ready for back door action? Or on my back with a feminine arm over the head? I decided to compromise and go with a pose I'd seen in Victoria's Secret. Lying on my side, I propped myself up with my left elbow and leaned forward to accentuate my breasts.

Ann loved it. She strutted into the bedroom moments later wearing a lacy white ensemble that showed off her best curves with a bra, thong panties, thigh-high stockings and heels. Ann gripped a chrome dildo about six inches long in her right hand and a "Larry's Lube" tube in her left.

"You look like you're ready for a fucking," she said. "Get on all fours."

I obeyed. Ann stood in front of me as she unscrewed the tube of lube. She squirted a glob in her hand and rubbed it on the dildo like she was stroking it off. The rod looked like a model of a next-generation ICBM. It was about as wide as two fingers pressed together and had a blunt top.

"Move that thong out of the way and spread your cheeks, bitch," Ann said. "It's time for the silver bullet."

She twisted the bottom of the dildo. It hummed like a set of clippers. But this was no haircut.

Ann set the humming dildo on the outside of my asshole. It was a little tight because I was nervous. But the gentle vibrations put me at ease. Ann knew exactly when I was ready. She slowly started slipping it in. First, just the tip. Then, deeper. Finally, the entire width of the dildo was stretching my ass. I watched in the mirror as she started pumping my ass. Ann was entirely focused on my rear. She took shallow strokes at first. But she went deeper as I began to moan. My cock felt like a boiler under pressure. But there was no chance of slowly letting the steam whistle off. I was working toward an explosion, but I forced myself to hold back. Ann got on her knees behind me and held the dildo to her pelvis. She drove the rod all the way into me as if it were her own cock.

Ann finally couldn't stand it anymore.

"On your back, slut!" she yelled.

Ann took off her panties so fast, she tore them. She flung them to the floor where they laid in tatters. The last thing I saw before squeezing shut my eyes was her leaping at me. When I opened them, her knees were by my ears and her dripping pussy was an inch from my nose.

The musty smell mixed with her sweet perfume as it drifted into my nostrils. She had a thin Mohawk of a bush. Everything else was completely hairless.

I licked all around the pussy, starting with the thighs and working inward. She groaned with ecstasy. When I went for the outer folds of pussy flesh, she moaned. Her legs gave way when I thrust my tongue inside her. Ann began grinding fanatically as I moved to the clit.

"Owie! Owie! Owie!" she yelped.

But she wasn't hurt. Quite the contrary.

I didn't have to lick long. She juiced all over my face with a shudder that seemed to last forever. When she composed herself, Ann flopped onto her back.

"OK baby," Ann said. "Your turn. Cum on me me."

I kneeled beside her and whipped my cock out the teddy. All it took was three strokes. I must've shot ten gallons of cum. The first spurt landed in her cleavage. The second splattered across her cheeks. The third hit her mouth and chin. She looked like a "Got Milk" commercials gone mad by the time I was done.

Ann laughed. I was nearly out of breath.

"Come on, baby," she said. "Clean up your mess."

I licked every drop of jizz off of her, starting with the puddle in her cleavage. My own warm, salty cum slid down my throat. I loved it.

When I was done, I laid on my back next to her. But she wasn't in the mood for cuddling. Ann jumped up and slid on a fresh pair of panties.

"Thanks, hon," she said. "I've got a dinner meeting. Let's do this again sometime. I'll save the outfit just for you."

Ann winked and disappeared into the bathroom.

And that's how our relationship has gone since then. We get into all kinds of nasty, little adventures. One time we even brought the gardener, Juan, into bed with us. The best part is my dad hasn't figured it out.

As far as I know.

Report Story

byStephanieSeymour© 1 comments/ 303558 views/ 74 favorites
1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartCaques, Ultimak and 72 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

There are no recent comments (1 older comments) - Click here to add a comment to this story or Show more comments or Read All User Comments (1)

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: