Stepmom's Sex Shocker Ch. 02

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Son goes shopping for dress with stepmom.
2.5k words
4.49
184.6k
44

Part 2 of the 6 part series

Updated 10/29/2022
Created 08/21/2005
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My stepmother, Ann, was straddling me and leaning forward when I woke up. Her tits dangled in my face.

"Remember these?" she asked.

How could I forget? I was staring directly at the freckles in her cleavage where I'd shot my cum and licked it up just two days earlier. Ann had seduced me by dressing me in her sexiest lingerie.

"You did so well the other day, we're going to have another nasty, little adventure," Ann said. "Are you ready?"

I gulped and nodded. My parents kept an "open marriage," but acting out perverse fantasies with your step mom was taboo, even in my family. If Dad ever found out, I'd lose everything - my inheritance, my Ferrari and probably even my weekly allowance. But it was impossible to resist. Ann's soft, Texas drawl put a lasso around me.

She dropped a handful of black lace and straps on my chest.

"Put these on," she said.

Ann sat in my favorite chair, the one shaped like an oversized catcher's mitt, and crossed her legs seductively. At 40, she was twice my age but still built like a college cheerleader. Her tight, blue sundress showed off every curve.

With her watching, I rose out of bed and stripped off my boxer shorts. Ann had picked out a sexy ensemble for me. The package included a push-up bra, thong panties, fishnet stockings and a garter belt. All of it came from her lingerie drawer. I could tell because it smelled like her sweet perfume.

The clothes made me feel like a slut the moment I touched them. The bra was my favorite. The cups squeezed my tits like a horny set of hands. Lingerie is way more complicated than men's clothes, but I managed to hook and strap everything myself. Years of studying lingerie shots while jacking off to Victoria's Secret had finally paid off. But it didn't teach me everything. The girls in lingerie catalogs wear panties under the garter. But I know from strip clubs that the garter's straps can get in the way when you're trying to tear off the panties to access the genitals. So, I slipped the thong over the garter. Ann seemed pleased.

"Very nice," she said. "Now, put on a white T-shirt and jeans and meet me in the garage."

Ten minutes later, Ann was behind the wheel of her white Mercedes. I got in the passenger side. A Burberry overnight bag sat in the backseat.

"Where are we going?" I asked.

"I'm going to teach you about something all girls love," she said. "Shopping!"

I had a feeling she had something more in mind.

Ann slipped on a pair of cat-eye sunglasses and shifted the car into reverse. We headed out along Van Buren Drive, then hopped on the interstate, heading north. Madonna's greatest hits blasted out of the speakers. Ann sang along in her best girlish voice, "We are living in a material world, and I am a material girl."

We pulled the into a mall parking lot about 45 minutes later. We were in an upscale suburb on the other side of the city where no one would know us. Ann slid the car into a spot near the food court.

"We're here," Ann said.

"What are we shopping for?" I asked.

"I'm glad you asked," Ann said. "We're going to get you a new dress."

My cock rose at the idea. But there was just one problem.

"Look at my shirt," I said. "The bra shows right through this white fabric. People might see and know I'm cross-dressing."

Ann frowned thoughtfully, tilting her head to the right. Then her eyes suddenly lit up.

"You're right," she said. "I've got an idea."

Ann pulled a black eyeliner pencil out of her purse. I looked at the ceiling while she traced the bottom of my eyes and shut them when she penciled over the lids. Ann did nice work. The reflection in the vanity mirror reflected flirty but not slutty eyes. It was still too early to be slutty.

"I'm wearing make-up!" I said. "Now people really are going to know something's up."

Ann giggled.

"I know," she said. "The bra was way too subtle."

A teen clerk at Gadzooks was the first to notice my feminine fashion. It was the kind of store Britney Spears wannabes go back-to-school shopping. The clerk, a blond with big tits, whispered in a manager's ear. They both giggled. The clerk could still barely keep from bursting with laughter in our faces when she came over to ask if we needed help.

"Yes," Ann said. "My stepson needs a new dress."

The techno music thumping in the background came to an abrupt halt. Every eye in the store turned on me. At least a dozen shoppers - all women -- watched my cheeks turn pink. But what they didn't see was my dick stiffening even more under my panties. I was so humiliated - and I loved it.

The clerk's attitude changed sharply. You could tell she was shocked. She must've thought she was being Punk'd when we first walked in.

"Um, did you have anything in mind?" she asked.

Ann pulled a black and white tube dress off the rack.

"Do you have this in a large?" Ann asked.

"It's spandex," the clerk said. "One size fits all…well, most."

"Good," Ann said.

She shoved the garment at my chest. "Go try it on," she said.

The dressing room didn't have a door. All it had was a curtain that covered me from the knee to the neck. Anyone watching would be able to tell I was wearing fishnet stockings.

More humiliation.

This shopping trip was getting better by the minute.

I stripped to my lingerie and slid the dress over my head. The fabric hugged my body like a warm, silky pussy around a stiff dick. I was so excited, I popped out of the dressing room and struck my best supermodel pose.

"Wow!" Ann said. "Very sexy! Very slutty!"

By then, most of the decent people had sensed the perversity of our show and had decided to leave. But a pair of teen girls looking like Jessica Simpson and Christina Aguilera kept the humiliation going. They pointed and laughed at me without even trying to hide it.

Ann ignored them.

"I like this outfit," Ann said. "But it's not quite what I had in mind. Let's check Victoria's Secret. But, first, come here and give mommy a kiss."

She pulled my body against hers and French kissed me for the world to see.

Our shopping trip lasted another two hours. We put on a show every time we went into a store. Teen-agers thought it was funny. Some adults found us repulsive, while others seemed entertained. Ann dropped a few hundred dollars on me. She bought me a string of pearls, a black wig, six-inch heels and a black cocktail dress.

"Every girl's got to have one," she said.

Whenever she bought me something, I'd add it to my ensemble. I was fully dressed in female clothing and make-up by 2 p.m. To get back to the car, I had to walk from one end of the mall to the other in drag. We might have fooled a few people, but almost everyone could tell I was no woman. One guy sporting a Confederate flag cap and walking the other direction, bumped into my shoulder and said, "Take the freak show back to Atlanta, faggot."

"Maybe you'd like to come," I said.

He just kept walking. Ann and I cackled like crazy.

We got back into the car and drove to a hotel on the other side of the suburb. Ann parked by the front door, went to the front desk and returned a minute later with a key to an executive suite.

"Boy, have I got a surprise for you," she said.

My cock was pulsing by now. The slightest breeze could've made it squirt. I had to hold back with everything I had, especially in the elevator on the way up to the room. A group of six businessmen looking very serious in their Brooks Brothers suits slid in just before the doors closed. They were so focused they didn't notice the transsexual and beautiful woman standing in their midst. But Ann wouldn't let them get away that easy.

"You sure are looking pretty today, girlfriend," she said.

"You are, too," I said.

Ann dropped the Burberry bag, leaned into me and sucked on my neck. I moaned like a foghorn. That got their attention. They crowded to the front of the elevator as if we had a catchy disease. Maybe we did. But I never had so much fun being sick in my life. When the door opened on the 11th floor, they sprinted out.

We went all the way to the top. The penthouse. Ann was bouncing with excitement as she slipped the key in the lock.

"You aren't going to believe this," she said.

Ann swung open the door. She was right. I never would've guessed.

Rico, our pool guy, was lying naked on the couch, almost in a statuesque pose. Sun pouring through the window bathed his rippling stomach muscles in light.

"You, me and Rico," Ann said, "we're going to have some fun."

Rico smiled devilishly and leapt off the couch. He and Ann dove into each other's arms. They kissed madly as Rico pulled up her dress and squeezed her ass. She started grinding her pussy against his cock before he could take off her panties. They didn't stop until Rico literally ripped Ann's silky underwear right off her hips. Ann chomped playfully at him and shot him a "grrrr." Rico flipped his tongue suggestively.

"Rico," Ann said, "after five years you've still got it. I knew there was a reason we hired you, 'cause you sure can't clean a pool worth a shit."

Rico either didn't understand or pretended he didn't. Ann brushed back her tussled hair and lugged the suitcase to the bed. She unzipped it.

"Take off your panties and come here," Ann said.

I daintily slipped the panties off my hips and let them fall to floor. Ann had a pink dildo in one hand and a jar of Vaseline in the other. Rico was grinning like he'd seen all this before. His six-inch pecker stuck straight out.

"Good girl," Ann said. "Now, hike up your dress and get on the bed, doggy style. Rico, you go sit on the couch and keep your dick hard. We'll need you later."

I could feel my tits hanging down in the bra as Ann twisted the bottom of the dildo to turn it on. A gentle hum filled the room. My cock stiffened. I stared directly into the headboard and waited, but nothing happened. I began to wonder if something was wrong.

"Hey, Ann," I said. "What's the ma---"

Then she did it. Ann softly, but quickly, shoved the dildo up my ass. She took long, deep thrusts. Ann touched parts of me I didn't know existed. I always knew that someone could fuck you with a dildo. But I never imagined someone could make love to you with one. Ann did.

I was almost ready to cum when Ann pulled out.

"My turn," she said. "Don't move."

Ann put the Vaseline in front of me.

"First, eat my ass," she said. "Then lube it up for Rico."

Ann slipped her dress over her head, got on all fours and spread open her cheeks in front of me. She had the cutest little button for a hole - and it smelled like a rose. No, really. I know the only people who will believe me are the ones who've eaten my stepmom's ass, but it's true.

Ann groaned as I worked on her. I licked her crack from her pussy to the small of her back. Then I stuck my tongue as far up the hole as I could. It might sound sick, but I wanted to crawl up inside her.

"Now, the lube," Ann said.

She was so out of breath, she could barely get it out. I scooped out a blob of Vaseline and fingered Ann's ass. Once she was lubed up, Ann crawled next to me, so our asses and faces were right next to each other.

Rico knew exactly what to do. He popped off the couch without Ann saying a single word and kneeled behind her.

"Ladies first," he said in that beautiful Costa Rican accent.

Ann winced. I looked back. Rico was pumping her ass. He was doing her good and hard but not in a mean way. Ann's face unfolded into a slight smile. Her eyes were half-lidded and rolling back.

"Uhh!" she said. "Rico, you're the best!"

"I like you, too, baby," Rico said.

He pulled out his cock and kissed the small of her back.

"But I like the girly men, too," he said.

Ann stayed next to me as Rico playfully slapped my left ass cheek and positioned himself behind me. His hands fell firmly on my hips. I gripped the sheets in my fists. This was it. My first cock up the ass. There was no turning back after this. I would be officially part homo.

I thought about running. Rico must've sensed it because that's when he used his thumbs to spread me open and shoved his cock inside me. A painful shock ripped through my virgin hole. But it quickly faded and gave way to an indescribable ecstasy. I felt like Rico and Ann - and maybe even the whole world-truly loved me. My body pulsed with energy. Rico must've felt the energy, too. He trembled and tightened his grip on my hips. He was going to cum! Yes, I wanted him to do it inside me so bad.

But then he yanked out. I opened my eyes and turned around in time to see Rico cumming on Ann's arched back. The goo shot for a very long time. When he was done, he and I watched it run into a puddle in the small of Ann's back.

She didn't have to tell me what to do. As Rico slid back, I slid forward and leaned over. My nose hovered over the jizz lake for a few seconds so I could take in the aroma. Then I dove in, lapping the gooey mess into my mouth and swallowing it down like a cat does a bowl of milk.

Rico was putting on his Speedo-style underwear when Ann flipped me onto my back. She deep-throated my entire stiff cock without saying a word. Her head bobbed. On every down stroke, she dug her nose into my pubic hair. Her lips puckered at the very tip each time she pulled her head back. Ann had to take only about a dozen strokes before I came. I could tell be the way she looked at me that she knew it was on the way. But Ann didn't pull back and let me squirt in the air. She took every last drop into her mouth, held it and positioned her mouth a couple inches above mine. I opened and let the cum slowly drip into my mouth like Ann was a coffee maker and I was the cup.

Rico clapped.

"Good show," he said, "good show."

So, that's how my stepmom got me into my first homosexual experience. My dad hasn't found out.

As far as I know.

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5 Comments
AnonymousAnonymousalmost 12 years ago
I love shopping

This story got me so hard because it reminds me of what I do almost every month -- go shopping with my sister for women's clothes for me. We don't make it a secret and the salesladies all know the clothes are for me. Just like in your story, trying on clothes at Victoria Secret with everyone watching me makes me so horny. I love it that everyone knows and can see that I'm a sissy faggot bitch who enjoys getting fucked by my sister and her boyfriend, while I'm dressed in sexy women's clothes.

I love your stories -- please tell more !!!

AnonymousAnonymousalmost 17 years ago
Double Fantasy Fullfilled!

Wow! What a great fantasy! Being Bi-sexual, into panties, turned on by my step mom while a kid, all sexual fantasies fullfilled. Very awesome story, a dream come true.

AnonymousAnonymousabout 18 years ago
more please

very good.please write more

AnonymousAnonymousover 18 years ago
Why??

Why isn't pussy boy allowed to fuck Ann, everyone else in town does????

AnonymousAnonymousover 18 years ago
Good story

My Cock is hard and I wish that was my ass being pumped with Rico's Latin cock

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