Cross Dresser Enslaved
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Step-Mother's Sex Slave-Cross-dresser Blackma free porn video
My heart pounds as I tip-toe across the soft, pink carpet in my parents' room. I'm home alone. My stepmother's lingerie collection awaits.
A floorboard creaks as I make my way to the dresser. I'm facing my worst nightmare--getting caught playing with Ann's lacy undies. But I'm totally hooked on wrapping myself in her silk and lace. I decide to move forward. The risk adds to the adrenaline rush.
I stretch out my fingers to grab the drawer's brass knobs. The sensual pleasures of cross-dressing are tantalizingly close when I hear a car door slam outside. The breath leaps from my chest, and I think about scampering out of the room. I hear women's voices outside. Then I realize the sound is too far away to be in our driveway. It has to be the neighbors. I exhale.
I slowly open the drawer and let the scent of cinnamon rise into my face. Ann keeps her lingerie drawer smelling fresh with a lacy bag of potpourri tied at the top with a pink ribbon. I close my eyes and inhale deeply.
When I open my eyes, a treasure chest of neatly folded lingerie is spread out in front of me. Silky camisoles. Lacy teddies. Satin gowns. I have my pick, but I know exactly what I want. A lacy, black bra with matching panties, thigh-high stockings and garter belt. The outfit has been on my mind since I saw it in a Victoria's Secret catalog two days ago.
I begin searching through the stacks of underwear. Just touching all that lace and satin is enough to put goosebumps on my arms. As I peel back the top layers, I do my best not to ruffle the lingerie. I want everything to be in order the next time Ann opens the drawer.
Finding the bra is easy. All I have to do is feel for the stiff wire that pushes up your tits when it's wrapped around your body. It's almost as easy to find the stockings and garter belt because Ann keeps those in one section of the drawer. But the panties are tougher to find. She has so many pairs, and they're divided among all the little stacks of lingerie, mixed with the camisoles and everything else.
I dig. I begin to make a mess but hope it's not so bad that Ann will notice. My hand suddenly comes upon something strange-- something not silk, lace or satin. It's a folded piece of paper.
I pull it out and open it. There's a note-- and it's addressed to me.
"Dear Will,
I know what you're up to. If you don't want your father to find out, call me the moment you discover this note.
Ann"
The note wallops me like a Louisville Slugger upside the head. I stagger backwards and fall to the floor, slumping against my parents' bed. My whole life flashes before my eyes. I see everything being taken from me. The Lexus SUV. The trust fund. Everything. My father hates fags. No way he'd tolerate one in the family.
I dig into my pocket for my phone and dial Ann's number. She answers on the second ring.
"Hello," she says in her gravely voice-- a dead ringer for Demi Moore.
"It's me," I say. "I found your note."
"Surprised?"
"Very."
"I thought you would be. Since you called, may I assume that you would like to keep our little secret from your father's ears?"
"You may."
"Then do exactly what I say."
"Fine."
"Dress up in some of my clothes and make up. Get as slutty as you can. I want to see you in lingerie and a dress. I've left a wig and size 12 high heels in the closet for you. Wear those, too.
"Then drive to the Westin hotel in Longwood. It's just off the interstate at exit 21. Check into a suite and call me back with the room number. Can you do that?"
"I think so."
"You better know so-- unless you want your father finding out about your little fetish."
"I'll do it."
"Good. And one other thing. I want you dressed like a woman when you check into that suite. This isn't my first stay at that hotel. I have friends there. If you're wearing a T-shirt and jeans when you check in, I'll find out-- and you will suffer the consequences."
"This is fucking crazy. You want me to go in public dressed like a fag?"
"Yes."
"And if I don't?"
"You may as well pack your bags right now because your father will have you out of the house before dinner tonight. So, do we have a deal?"
I sigh.
"Yes."
"Good. I'll expect to hear from you soon."
She hangs up, and the line goes dead.
I can hardly believe what's just happened. My whole life has changed in one phone call. I feel used and abused, like a cheap prostitute. It begins to sink in that I'm going to have to go out in public in women's clothes for the first time. I'm horrified but also strangely aroused. My heart is pumping like I've just drunk three pots of coffee.
I don't think I've ever been so confused in my life.
As I strip off my T-shirt and jeans, I begin to absorb the depth of my step mother's sickness. Never before has she shown any signs of being a pervert. She's always been a typical rich-bitch step mom. She leaves the cleaning and cooking to the maid and spends her days at the spa, gym or mall. Ann has always been a little bit of a flirt, but I never would have dreamed that she fucked around on my father or that she would be into anything harder than going doggy style.
It takes a special kind of weirdo to give the kind of orders she did. Almost as surprising was that line she gave me about having friends at the hotel. It's as if she's done this sort of thing before.
I stretch the bra across my chest and fasten it behind my back. My tits get a lift as I lace my arms through the straps. I put on the panties, arranging my cock so the underside presses against the lacy fabric. The panties are "boy shorts" that fully cover my ass and leave plenty of room for my balls.
I unroll the stockings up my legs. I love how the tight fabric feels against my skin. With my cock hardening, I fasten the garter belt around my waist. Hooking the straps to the stockings takes some effort. Every time I think I've got a hook secured it slips out of my masculine fingers. I wonder if women are born knowing how to do this.
I finally get the stockings hooked up and go into Ann's closet to choose a dress. I quickly find a little, black cocktail dress that I pull over my head. The stretchy material forms to my my body. I check myself in the mirror on the closet door. The scoop neck top leaves lots of chest exposed without showing the bra straps. I see that the tops of my thigh-high stockings are just barely exposed. I pull at the hem of the dress. The stockings are covered, but the moment I move the fabric slips and the stocking tops are exposed again. I say, "fuck it" and head to the bathroom to do my make up.
I paint my face as slutty as can be in cherry-red lipstick, black eyeliner, gray eyeshadow and mascara. Checking myself in the mirror, I see that I'm not quite passable as a woman, but I'm getting closer. My prick stiffens.
I go back in the bedroom and search the closet for the rest of the outfit Ann had directed me to wear. A box on the shelf above her blouses is labeled "wig/shoes." I take it down and set it on the bed to open it.
The wig fits snugly on my head. I suddenly have straight, black hair that falls just below my ears. The bottom edge is crisp and sharp like a broom. The bangs are just as dramatic, going straight across my forehead just above my eyebrows.
The shoes Ann has chosen for me are totally slutty. Shiny, black, six-inch heels. I slip my feet into them and take a few tentative steps across the room. I feel the shoes forcing me to perk up my chest and ass. The line from that Shania Twain song flashes through my brain, "Man, I feel like a woman."
I borrow a cute, black purse from Ann and throw my wallet inside.
It's time to leave.
My Lexus SUV is parked in the garage. I climb in and crank it up, thankful that I spent extra to have the windows tinted. At least I won't have to humiliate myself in front of my neighbors.
Longwood is usually about 45 minutes away. I'm careful to obey the speed limit. The last thing I need is a brush with a cop. Once on the interstate, I find myself searching my iPod for Britney Spears, Madonna and Lady Gaga. The drive flies by. When I hit the exit, I'm tapping my foot to "Poker Face."
Not until I pull into a parking spot does the full weight of what I'm about to do hit me. A chill is in the air as I open the SUV door and swing my heels onto the pavement. I'm shaking as I click-clack on the concrete toward the entrance.
I'm noticed for the first time by the bellhop, who can't help but grin as he tips his hat. I return the gesture with a nervous smile of my own. The automatic doors slide open. The lobby's heat envelops me as I walk inside.
I'm hoping to get to the front desk with as little attention as possible. But the floor is ceramic tile, and my heels must be made of some uniquely hard plastic because the clicking reverberates around the cavernous lobby. I feel like the whole world is watching as I approach the clerk behind the front desk. He's got his head down, and he's typing on a computer keyboard. He senses my presence and greets me without immediately looking up.
"Hello, ma'am, welcome to the Westin," he says.
The clerk looks up. His eyes pop.
"Er, I mean, sir," he says. "Terribly sorry-- which do you prefer."
I think about this for a second.
"You can call me Stephanie," I say in my best female voice.
"Very good, Stephanie," the clerk says. "How may I help you?"
"I'd like a suite, please," I say.
"Yes, of course," he says.
I hand him my credit card.
As the clerk taps on his keyboard, I notice that he's handsome, even in the lame red uniform the hotel makes him wear. He couldn't be more than 30, and he's got blonde, surfer-boy looks. His name tag says "Phil."
He hands me back my credit card.
"Thank you very much, Stephanie," he says.
He banged a couple more keys on the computer and then ran a plastic card through a machine next to his computer.
"Here's your room key. You'll be in suite 2204. And I'll be up to see you soon."
"Up to see me? For what?"
Phil smiles.
"Your stepmother invited me to the party."
I'm stunned.
"Party? What party?"
Phil's smile widens.
"We're gonna have fun," he says. "The elevator is around the corner to the left."
I step onto the elevator with a guy in a crisp suit and a briefcase. His eyes linger on me just long enough to register that something isn't right and then divert to the floor. They stay there until he steps off the elevator on the ninth floor. I ride up to 22 and find my room.
The suite opens into a living room with white tile floors and black leather furniture. A big picture window looks out over the interstate, the suburbs and the city skyline off in the distance.
I daintily lower myself onto one of the black leather chairs, careful not to tear my dress. I open my phone and call Ann. She answers on the second ring.
"I'm here," I say. "Room 2204."
"Good," she says. "Order up some porn on the TV, and I'll be there in 20 minutes."
I close my phone and pick up the remote control. The hotel offers an extensive list of pay-per-view sex flixks. One called "Cum Suckers No. 18" looks promising. I order it for $21.95. The movie has no plot, just an endless series of guys cumming on chicks' faces. My cock stiffens. I've picked a good movie.
The 20 minutes flies by. A knock comes at the door. I open it. Ann struts by me without saying a word. She's looking sexy as ever in her tight, gray business suit and black high heels. She reminds me of Sara Palin, except with bigger tits and red hair.
When I close the door behind me, Ann looks me over from head to toe. A massive boner pokes into my dress, making it stand up like a circus tent.
"I see you're ready for our party," she says.
"I don't get it," I say. "What party?"
Ann sits on the leather couch.
"Come over here," she says, while patting the cushion next to her.
I go over and sit. Ann takes me by the hand and looks into my eyes.
"You know your father is cheating on me, don't you?" she asks.
I shake my head.
"It's true." She sighs. "Unfortunately, there isn't much I can do."
"Why not divorce him?" I ask.
"I thought about that. I could divorce him and take half of everything he owns. But you know what? It's not enough. Your father has so much money he wouldn't even notice. He could keep right on with his women and cars and trips to Europe without even pausing to catch his breath."
"OK, then. What do you want?"
She comes in close, boring into me with her brown eyes.
"His son's soul."
I jump back.
"What the fuck are you talking about, Ann?"
A truly evil grin spreads across her face as one eyebrow arcs.
"You are going to be me bitch."
"What's that supposed to mean?"
"It means that I'm making you into my sex slave. Your main purpose in life will be to satisfy my twisted appetites. See, I'm a member of a secret little sex club. There are about 20 of us. I think you've already met one of the other members-- Phil, down at the front desk.
"Anyway, we get into all kinds of weird group sex. And when I put the word out that I could blackmail you into being our bitch, I got a very enthusiastic response."
"This is too fucked up to even think about."
"Maybe you can think about this--what would your father do if he knew you liked to dress up in girl's underwear? Think he might kick you out of the house? Think he might write you out of his will?"
"You are one sick bitch."
"You don't know how sick-- not yet."
Another knock comes at the door before I can even begin to digest what Ann is telling me.
"But you're about to find out," Ann says.
She goes over to the door and opens it. Phil, the front-desk clerk, walks in. As Ann lets go of the door, Phil leaps on her. He wraps her in a bear hug and grabs the hair at the back of her head. He jerks back Ann's head and plants a sloppy kiss on her lips. I can see their tongues darting into each others' mouths.
When Phil has enough, he pushes Ann away and fixes his gaze on me.
"Is that her?" he asks.
"Yeah," Ann says.
Phil licks his lips. I squirm and pull at the hem of my dress.
"She'll do nicely," Phil says.
"She's a virgin," Ann says.
"Even better," Phil says. "Can we start now?"
"No," Ann says. "We have to wait for the others."
"Others?" I ask. "What others."
Phil looks at Ann with a smirk.
"You didn't tell her?" he asks.
"Not yet," Ann says.
Phil shakes his head.
"You evil bitch," he says.
Ann smirks back.
"Got that right," she says.
I've had enough. I stand up.
"What the fuck is going on?" I ask.
"You're going to get gang-fucked," Ann says.
"Gang-fucked?" I ask. "How many we talkin'?"
"Depends on how many can make it," she says.
"I never agreed to that," I say.
"It was never up to you," she says. "Now sit down and shut up before I decide to call your father."
She was right, but I didn't have to like it. I dropped down onto the couch and folded my arms defiantly. Before I could think of anything else to say, someone else knocked at the door. Ann opened it and in walked one of the hugest men I've ever seen. He was like a side of beef on legs. The guy was over six feet and at least 250 pounds of pure muscle. He had short, black hair and wore a black shirt that barely contained his bulk.
"So I hear you got a whore that needs some abuse," he says.
"You heard right," Ann says. "That piece of shit on the couch is what you're looking for."
Muscles zeroes in and lunges toward me. I flinch. Ann catches him by the collar, and Muscles stops dead in his tracks. Although he's twice Ann's weight, she has total control over him.
"Not yet, Luke, " she says. "More are on the way."
Phil laughs and claps Luke on the shoulder.
"That's why I like you, Luke," he says.
Luke grunts and relaxes his shoulders. But he never takes his eyes off me. He's like an a****l, working on pure instinct. I stare back at him, wondering where I've seen him. Then it hits me: he's been at the house. He is Ann's personal trainer.
Ann and Phil come sit on the couch with me, while Luke settles into a love seat. We all sit around the TV, silently watching porn for about 15 minutes. The room is totally quiet, except for the moaning and grunting coming from the movie. I sneak peeks at Luke and Phil. They have big bulges in their pants. Pressure in the room is building. It feels like it could blow at any moment.
I'm totally shocked at who knocks at the door next. It's our next door neighbors, Tom Lundgren, and his trophy wife, Lisa. He has good looks like George Clooney and probably as much money. She's about half his age with blond hair and legs that go on forever. Both are in business suits, looking like they'd just come from the office. Ann greets them both with outstretched arms and kisses on the cheek.
"So glad you could make it," she says. "Hope you brought your appetite-- your sexual appetite, that is."
Tom grabs his crotch.
"My fuckin' cock is hard as a rock," he says in that thick New York accent. "Just like always."
Lisa snickers girlishly. Ann winks at her.
"And we all know you're ready-- right, Lisa?" Ann asks.
"Always," Lisa says.
"Good," Ann says. "I don't think anyone else is coming, so let's start."
Luke scoots forward and perches himself on the edge of his seat. He's ready to attack but holds back. It's clear that Ann is running the show-- that she gets first crack at me.
Ann struts over to me and stands in front of me, looking down her nose into my eyes. The rage builds. She winds up and backhands me across the cheek.
"Fucking slut!" she shrieks.
My face stings as Ann pulls up her skirt and straddles my lap. She begins dry-humping my stiff cock and pulling the hair at the back of my head. Her hands find their way to my tits. Ann pinches my nipples and rolls them between her thumbs and forefingers.
I begin breathing hard. I'm beginning to like this.
Just when I'm about to cum in my panties, Ann pushes herself back to her feet.
"OK," she says to the crowd. "Go get her."
Luke lunges. Ann stretches out her hand to block him.
"Uh-uh," she says. "Ladies first."
Lisa comes over to me with a twisted smile on her face. She reaches behind her back and unzips her gray skirt, letting it fall to the floor. Her panties are purple satin with lace trim. With her blue eyes fixed on me, Lisa unbuttons her jacket and slips it off her shoulders. Her purple bra barely contains her voluptuous tits. She reaches into the pile of hair piled on her head and removes a bobby pin. She shakes her head, and wavy hair falls to her shoulders.
Lisa smiles seductively and slides her hand between her legs. She grabs her crotch.
"You want some of this?" she asks.
I swallow hard, thinking that maybe this gang-fuck thing won't be so bad. The words won't come, so I just nod.
Lisa reaches slowly into her panties. I'm thinking she'll go as far as her clit and start fingering herself. But her hand goes deeper-- far deeper-- almost to her ass. I can't figure out what the hell she's doing. Is she going to finger her asshole?
Lisa doesn't leave me wondering for long. Her hand suddenly emerges from her panties with a cock that hangs halfway down her thigh. My eyes bulge. Everyone in the room laughs, except for me. I'm stunned that Lisa-- our sweet next door neighbor-- could have kept that monster hidden so well. In all the years the Lundgrens had lived next door, I never for a second thought that Tom's bride was actually a man.
"Now it's time to play," Lisa says. "Get over here and get on your knees."
Lisa pulls down her panties and steps out of them.
Her cock begins to stiffen as I slide off the couch and drop my knees onto the hard, white ceramic tile. I'm not exactly sure what I'm supposed to do so I just stare at Lisa's manhood for a second. It's sticking straight out of a patch of neatly trimmed pubic hair and pulsating with her heartbeat.
"Go on, bitch!" Ann says. "Suck it!'
I make an "o" with my mouth and slip Lisa's cock inside. The guys whoop as I push my head down her shaft. I think of the blow jobs I've seen on porn movies and try to imitate them. The best cock-sucking queens maintain eye contact, so I turn my eyes up toward Lisa's face. She looks back with her lips slightly parted and a building fire in her eyes. My head bobs. On the down strokes, I'm taking about half of her schlong into my gullet. It doesn't seem like it can go any further.
I'm settling into a nice rhythm when Lisa suddenly jerks her prick out of my mouth.
"Turn around and bend over," she says.
"Why?" I ask.
"It's hammer time," she says.
As I get into the doggy-style position, I see that Phil, Luke and Tom have stripped naked and they're watching Lisa and I, as if we're the floor show in some Vegas club. Phil and Tom are leaning back on the couch and stroking themselves. Luke is laid out on the love seat with Ann between his legs. She's blowing him.
The wig is hanging in my eyes and tickling my cheeks as I wonder what Lisa will do next. My panties are still on, so she doesn't have access to my bunghole. But she solves that problem quickly. Lisa grabs the panties by the waistline and yanks hard. They tear but don't come all the way off. Lisa yanks again, and this time I feel the panties disappear.
"Somebody get me the lube," she says.
Out of the corner of my eye, I see Tom scramble to his feet. He darts to the bathroom and comes back with a mini bottle of lotion. He unscrews the top and hands it to Lisa. She dumps a liberal dollop onto her fingers.
I feel a finger slide into my ass. I immediately tense up. Lisa gently works my hole, never going more than a knuckle or two deep. I'm surprised to find I kind of like it. As I loosen up, Lisa starts shoving her finger further inside me. The deeper and harder she goes, the better I like it. My cock is stiff. Pre-cum starts to leak from the blowhole.
The finger suddenly disappears from my bunghole.
"Spread your cheeks," Lisa says.
I reach back with both hands and do as I'm told. The side of my face is planted on the cool tile.
Lisa grabs my hips and eases the tip of her cock against my hole. My first instinct is to squeeze shut. But then I remember Lisa's gentle finger. I relax. Lisa senses the exact moment I'm ready for her, and she pushes herself inside me.
No feeling compares to having a cock thrust inside you. It's pleasure, pain and humiliation all rolled into one inexplicable emotion. I wouldn't say it's for everyone, but I sure like it.
Lisa pumps me with gentle, shallow strokes. I'm breathing heavily. So is she. My cock feels ready to pop, even though no one has touched it. Lisa picks up the tempo and depth.
"You want it harder, bitch?" she asks.
"Yeah, fuck me harder," I say.
Lisa jams her cock all the way inside me. I grunt as a shiver runs up my spine. Goosebumps form on my arms.
"Like that?" she asks.
"Yeah," I say.
Lisa hammers me again, only this time she keeps going. She pounds my hole with everything she's got. Then she suddenly takes one last thrust and blows her wad inside me.
"Oh fuck yeah!" she says.
Lisa pushes back and flops onto the love sat next to Luke. My ass is throbbing as I raise my head. The first thing I notice when I brush the wig out of my eyes is that Ann has gone from blowing Luke next to the love seat to jerking off Tom on the couch. She's naked. Everyone is, except for me. I'm still in my dress and lingerie. Phil has put on Ann's bra. He's standing next to her and Tom, watching them while stroking his meat.
"OK, everybody," Lisa says. "She's all yours."
Luke doesn't hesitate for even a second. He bursts from the couch and rushes toward me. This time, Ann doesn't try to stop him. His cock is hard as he grabs the back of my head and pokes the head into my lips.
"Open up, bitch," he says.
"If I were you," Ann says, "I'd do it."
Luke is merciless. He shoves himself all the way inside me. I gag as my nose digs into a thick patch of pubic hair.
Luke slowly pulls back. A second before the head exits my mouth, he rams himself back into my gullet. He repeats twice more before yanking his prick out of my mouth and jizzing all over my face. I try to keep my eyes open, but it's impossible with all that spunk flying at me.
When I open them, Luke is staggering back to the love seat. Cum is streaming down my forehead and into my eyes. I can taste it on my lips. I reflexively reach up to wipe my face, but Ann yells, "No!"
"Leave it," she says.
This must turn on Tom because he rolls over onto her. Ann lets him do it. She lays back on the couch and spreads her legs with one on the floor and one up in the air. Tom thrusts himself inside her. He grunts as he pumps. Their union lasts for about 20 strokes. Tom shuts his eyes and shudders, then rolls off Ann.
She looks over at me.
"Come get sloppy seconds, bitch," she says.
Tom gets off the couch to make room for me. I ease myself between my stepmother's legs. Her eyes burn with lust, revenge and hatred. My cock is harder than it's ever been.
"Go ahead," Ann says. "Fuck my pussy."
I ease myself inside her. Her cunt is slippery with Tom's cum and her own natural juices. I begin thrusting slowly and gently. She pinches my nipples and rolls them between her fingers. As I hover over Ann, Luke's jizz streams off of my face and drips onto hers. She opens her mouth and tries to catch the droplets on her tongue.
Phil comes over and aims the head of his prick at Ann's face. He gives himself two strokes before blasting his wad. The first spurt lands on Ann's tongue. The rest splatters all over her face. When Phil backs away, it looks like someone has unloaded a bottle of Elmer's glue. Ann closes her mouth and swallows the cum that landed in her mouth.
I can no longer hold back. Watching Ann drink goop pushes me over the edge. My prick unloads what seems to be a gallon of jizz. Ann arches her back. Her pussy seems to be sucking the spunk out of my body. I never knew it was possible to cum so hard.
I'm empty. I begin to pull my prick out of Ann's cunt, but she grabs my ass cheeks.
"No," she says. "Not yet. Clean my face."
Phil's jizz glistens on her face. With my cock still in her pussy, I lower my head. I start by dragging my tongue across her cheek. Phil's salty cum fills my mouth.
"Just like that, you dirty bitch," Ann says.
I lick Ann's skin from neck to forehead. When she's clean, I pull my cock out of her pussy and flop back on the couch.
"You aren't done yet," Ann says.
"What do you mean?" I ask.
"Clean my cunt," she says.
Ann spreads her legs a little wider. I kneel on the tile floor and put my head between her thighs. Cum is dripping from her pussy, leaving a wet mark on the couch cushion. Ann doesn't give me long to look. She forces my head into her twat. I thrust my tongue as deep inside her as I can. Ann squirms with delight. Jizz drips down my chin.
When I can't possibly suck another drop out of Ann's pussy, I pull myself onto the couch and take a deep breath. Everyone but Ann and I have dressed and look ready to go.
"We'll have to do this again sometime," Lisa says.
She click-clacks toward the door with Tom trailing her, followed by everyone else. They leave with a chorus of "byes" and "see ya laters." When the door slams shut on its own weight, Ann and I are the only ones left in the room.
"I liked that," I say.
"Good," Ann says, "You're going to be doing a lot more of it."
"Really?" I ask. "Everyone left so quickly. I thought they were unhappy."
"Not at all," she says. "That's just how we do things. We don't get to know each other, like neighbors or bridge partners. We use each other for sex. Nothing more, nothing less."
"I can live with that," I say.
"I knew you would," she says. "Now go get cleaned up. I've got plans for you."
"Like what?" I ask.
"Well," Ann says. "We've got the room all day. No sense in letting it go to waste."
"What did you have in mind?" I ask.
"I thought we'd fuck a while," she says. "And maybe later, we'll call Phil and order some room service."
A floorboard creaks as I make my way to the dresser. I'm facing my worst nightmare--getting caught playing with Ann's lacy undies. But I'm totally hooked on wrapping myself in her silk and lace. I decide to move forward. The risk adds to the adrenaline rush.
I stretch out my fingers to grab the drawer's brass knobs. The sensual pleasures of cross-dressing are tantalizingly close when I hear a car door slam outside. The breath leaps from my chest, and I think about scampering out of the room. I hear women's voices outside. Then I realize the sound is too far away to be in our driveway. It has to be the neighbors. I exhale.
I slowly open the drawer and let the scent of cinnamon rise into my face. Ann keeps her lingerie drawer smelling fresh with a lacy bag of potpourri tied at the top with a pink ribbon. I close my eyes and inhale deeply.
When I open my eyes, a treasure chest of neatly folded lingerie is spread out in front of me. Silky camisoles. Lacy teddies. Satin gowns. I have my pick, but I know exactly what I want. A lacy, black bra with matching panties, thigh-high stockings and garter belt. The outfit has been on my mind since I saw it in a Victoria's Secret catalog two days ago.
I begin searching through the stacks of underwear. Just touching all that lace and satin is enough to put goosebumps on my arms. As I peel back the top layers, I do my best not to ruffle the lingerie. I want everything to be in order the next time Ann opens the drawer.
Finding the bra is easy. All I have to do is feel for the stiff wire that pushes up your tits when it's wrapped around your body. It's almost as easy to find the stockings and garter belt because Ann keeps those in one section of the drawer. But the panties are tougher to find. She has so many pairs, and they're divided among all the little stacks of lingerie, mixed with the camisoles and everything else.
I dig. I begin to make a mess but hope it's not so bad that Ann will notice. My hand suddenly comes upon something strange-- something not silk, lace or satin. It's a folded piece of paper.
I pull it out and open it. There's a note-- and it's addressed to me.
"Dear Will,
I know what you're up to. If you don't want your father to find out, call me the moment you discover this note.
Ann"
The note wallops me like a Louisville Slugger upside the head. I stagger backwards and fall to the floor, slumping against my parents' bed. My whole life flashes before my eyes. I see everything being taken from me. The Lexus SUV. The trust fund. Everything. My father hates fags. No way he'd tolerate one in the family.
I dig into my pocket for my phone and dial Ann's number. She answers on the second ring.
"Hello," she says in her gravely voice-- a dead ringer for Demi Moore.
"It's me," I say. "I found your note."
"Surprised?"
"Very."
"I thought you would be. Since you called, may I assume that you would like to keep our little secret from your father's ears?"
"You may."
"Then do exactly what I say."
"Fine."
"Dress up in some of my clothes and make up. Get as slutty as you can. I want to see you in lingerie and a dress. I've left a wig and size 12 high heels in the closet for you. Wear those, too.
"Then drive to the Westin hotel in Longwood. It's just off the interstate at exit 21. Check into a suite and call me back with the room number. Can you do that?"
"I think so."
"You better know so-- unless you want your father finding out about your little fetish."
"I'll do it."
"Good. And one other thing. I want you dressed like a woman when you check into that suite. This isn't my first stay at that hotel. I have friends there. If you're wearing a T-shirt and jeans when you check in, I'll find out-- and you will suffer the consequences."
"This is fucking crazy. You want me to go in public dressed like a fag?"
"Yes."
"And if I don't?"
"You may as well pack your bags right now because your father will have you out of the house before dinner tonight. So, do we have a deal?"
I sigh.
"Yes."
"Good. I'll expect to hear from you soon."
She hangs up, and the line goes dead.
I can hardly believe what's just happened. My whole life has changed in one phone call. I feel used and abused, like a cheap prostitute. It begins to sink in that I'm going to have to go out in public in women's clothes for the first time. I'm horrified but also strangely aroused. My heart is pumping like I've just drunk three pots of coffee.
I don't think I've ever been so confused in my life.
As I strip off my T-shirt and jeans, I begin to absorb the depth of my step mother's sickness. Never before has she shown any signs of being a pervert. She's always been a typical rich-bitch step mom. She leaves the cleaning and cooking to the maid and spends her days at the spa, gym or mall. Ann has always been a little bit of a flirt, but I never would have dreamed that she fucked around on my father or that she would be into anything harder than going doggy style.
It takes a special kind of weirdo to give the kind of orders she did. Almost as surprising was that line she gave me about having friends at the hotel. It's as if she's done this sort of thing before.
I stretch the bra across my chest and fasten it behind my back. My tits get a lift as I lace my arms through the straps. I put on the panties, arranging my cock so the underside presses against the lacy fabric. The panties are "boy shorts" that fully cover my ass and leave plenty of room for my balls.
I unroll the stockings up my legs. I love how the tight fabric feels against my skin. With my cock hardening, I fasten the garter belt around my waist. Hooking the straps to the stockings takes some effort. Every time I think I've got a hook secured it slips out of my masculine fingers. I wonder if women are born knowing how to do this.
I finally get the stockings hooked up and go into Ann's closet to choose a dress. I quickly find a little, black cocktail dress that I pull over my head. The stretchy material forms to my my body. I check myself in the mirror on the closet door. The scoop neck top leaves lots of chest exposed without showing the bra straps. I see that the tops of my thigh-high stockings are just barely exposed. I pull at the hem of the dress. The stockings are covered, but the moment I move the fabric slips and the stocking tops are exposed again. I say, "fuck it" and head to the bathroom to do my make up.
I paint my face as slutty as can be in cherry-red lipstick, black eyeliner, gray eyeshadow and mascara. Checking myself in the mirror, I see that I'm not quite passable as a woman, but I'm getting closer. My prick stiffens.
I go back in the bedroom and search the closet for the rest of the outfit Ann had directed me to wear. A box on the shelf above her blouses is labeled "wig/shoes." I take it down and set it on the bed to open it.
The wig fits snugly on my head. I suddenly have straight, black hair that falls just below my ears. The bottom edge is crisp and sharp like a broom. The bangs are just as dramatic, going straight across my forehead just above my eyebrows.
The shoes Ann has chosen for me are totally slutty. Shiny, black, six-inch heels. I slip my feet into them and take a few tentative steps across the room. I feel the shoes forcing me to perk up my chest and ass. The line from that Shania Twain song flashes through my brain, "Man, I feel like a woman."
I borrow a cute, black purse from Ann and throw my wallet inside.
It's time to leave.
My Lexus SUV is parked in the garage. I climb in and crank it up, thankful that I spent extra to have the windows tinted. At least I won't have to humiliate myself in front of my neighbors.
Longwood is usually about 45 minutes away. I'm careful to obey the speed limit. The last thing I need is a brush with a cop. Once on the interstate, I find myself searching my iPod for Britney Spears, Madonna and Lady Gaga. The drive flies by. When I hit the exit, I'm tapping my foot to "Poker Face."
Not until I pull into a parking spot does the full weight of what I'm about to do hit me. A chill is in the air as I open the SUV door and swing my heels onto the pavement. I'm shaking as I click-clack on the concrete toward the entrance.
I'm noticed for the first time by the bellhop, who can't help but grin as he tips his hat. I return the gesture with a nervous smile of my own. The automatic doors slide open. The lobby's heat envelops me as I walk inside.
I'm hoping to get to the front desk with as little attention as possible. But the floor is ceramic tile, and my heels must be made of some uniquely hard plastic because the clicking reverberates around the cavernous lobby. I feel like the whole world is watching as I approach the clerk behind the front desk. He's got his head down, and he's typing on a computer keyboard. He senses my presence and greets me without immediately looking up.
"Hello, ma'am, welcome to the Westin," he says.
The clerk looks up. His eyes pop.
"Er, I mean, sir," he says. "Terribly sorry-- which do you prefer."
I think about this for a second.
"You can call me Stephanie," I say in my best female voice.
"Very good, Stephanie," the clerk says. "How may I help you?"
"I'd like a suite, please," I say.
"Yes, of course," he says.
I hand him my credit card.
As the clerk taps on his keyboard, I notice that he's handsome, even in the lame red uniform the hotel makes him wear. He couldn't be more than 30, and he's got blonde, surfer-boy looks. His name tag says "Phil."
He hands me back my credit card.
"Thank you very much, Stephanie," he says.
He banged a couple more keys on the computer and then ran a plastic card through a machine next to his computer.
"Here's your room key. You'll be in suite 2204. And I'll be up to see you soon."
"Up to see me? For what?"
Phil smiles.
"Your stepmother invited me to the party."
I'm stunned.
"Party? What party?"
Phil's smile widens.
"We're gonna have fun," he says. "The elevator is around the corner to the left."
I step onto the elevator with a guy in a crisp suit and a briefcase. His eyes linger on me just long enough to register that something isn't right and then divert to the floor. They stay there until he steps off the elevator on the ninth floor. I ride up to 22 and find my room.
The suite opens into a living room with white tile floors and black leather furniture. A big picture window looks out over the interstate, the suburbs and the city skyline off in the distance.
I daintily lower myself onto one of the black leather chairs, careful not to tear my dress. I open my phone and call Ann. She answers on the second ring.
"I'm here," I say. "Room 2204."
"Good," she says. "Order up some porn on the TV, and I'll be there in 20 minutes."
I close my phone and pick up the remote control. The hotel offers an extensive list of pay-per-view sex flixks. One called "Cum Suckers No. 18" looks promising. I order it for $21.95. The movie has no plot, just an endless series of guys cumming on chicks' faces. My cock stiffens. I've picked a good movie.
The 20 minutes flies by. A knock comes at the door. I open it. Ann struts by me without saying a word. She's looking sexy as ever in her tight, gray business suit and black high heels. She reminds me of Sara Palin, except with bigger tits and red hair.
When I close the door behind me, Ann looks me over from head to toe. A massive boner pokes into my dress, making it stand up like a circus tent.
"I see you're ready for our party," she says.
"I don't get it," I say. "What party?"
Ann sits on the leather couch.
"Come over here," she says, while patting the cushion next to her.
I go over and sit. Ann takes me by the hand and looks into my eyes.
"You know your father is cheating on me, don't you?" she asks.
I shake my head.
"It's true." She sighs. "Unfortunately, there isn't much I can do."
"Why not divorce him?" I ask.
"I thought about that. I could divorce him and take half of everything he owns. But you know what? It's not enough. Your father has so much money he wouldn't even notice. He could keep right on with his women and cars and trips to Europe without even pausing to catch his breath."
"OK, then. What do you want?"
She comes in close, boring into me with her brown eyes.
"His son's soul."
I jump back.
"What the fuck are you talking about, Ann?"
A truly evil grin spreads across her face as one eyebrow arcs.
"You are going to be me bitch."
"What's that supposed to mean?"
"It means that I'm making you into my sex slave. Your main purpose in life will be to satisfy my twisted appetites. See, I'm a member of a secret little sex club. There are about 20 of us. I think you've already met one of the other members-- Phil, down at the front desk.
"Anyway, we get into all kinds of weird group sex. And when I put the word out that I could blackmail you into being our bitch, I got a very enthusiastic response."
"This is too fucked up to even think about."
"Maybe you can think about this--what would your father do if he knew you liked to dress up in girl's underwear? Think he might kick you out of the house? Think he might write you out of his will?"
"You are one sick bitch."
"You don't know how sick-- not yet."
Another knock comes at the door before I can even begin to digest what Ann is telling me.
"But you're about to find out," Ann says.
She goes over to the door and opens it. Phil, the front-desk clerk, walks in. As Ann lets go of the door, Phil leaps on her. He wraps her in a bear hug and grabs the hair at the back of her head. He jerks back Ann's head and plants a sloppy kiss on her lips. I can see their tongues darting into each others' mouths.
When Phil has enough, he pushes Ann away and fixes his gaze on me.
"Is that her?" he asks.
"Yeah," Ann says.
Phil licks his lips. I squirm and pull at the hem of my dress.
"She'll do nicely," Phil says.
"She's a virgin," Ann says.
"Even better," Phil says. "Can we start now?"
"No," Ann says. "We have to wait for the others."
"Others?" I ask. "What others."
Phil looks at Ann with a smirk.
"You didn't tell her?" he asks.
"Not yet," Ann says.
Phil shakes his head.
"You evil bitch," he says.
Ann smirks back.
"Got that right," she says.
I've had enough. I stand up.
"What the fuck is going on?" I ask.
"You're going to get gang-fucked," Ann says.
"Gang-fucked?" I ask. "How many we talkin'?"
"Depends on how many can make it," she says.
"I never agreed to that," I say.
"It was never up to you," she says. "Now sit down and shut up before I decide to call your father."
She was right, but I didn't have to like it. I dropped down onto the couch and folded my arms defiantly. Before I could think of anything else to say, someone else knocked at the door. Ann opened it and in walked one of the hugest men I've ever seen. He was like a side of beef on legs. The guy was over six feet and at least 250 pounds of pure muscle. He had short, black hair and wore a black shirt that barely contained his bulk.
"So I hear you got a whore that needs some abuse," he says.
"You heard right," Ann says. "That piece of shit on the couch is what you're looking for."
Muscles zeroes in and lunges toward me. I flinch. Ann catches him by the collar, and Muscles stops dead in his tracks. Although he's twice Ann's weight, she has total control over him.
"Not yet, Luke, " she says. "More are on the way."
Phil laughs and claps Luke on the shoulder.
"That's why I like you, Luke," he says.
Luke grunts and relaxes his shoulders. But he never takes his eyes off me. He's like an a****l, working on pure instinct. I stare back at him, wondering where I've seen him. Then it hits me: he's been at the house. He is Ann's personal trainer.
Ann and Phil come sit on the couch with me, while Luke settles into a love seat. We all sit around the TV, silently watching porn for about 15 minutes. The room is totally quiet, except for the moaning and grunting coming from the movie. I sneak peeks at Luke and Phil. They have big bulges in their pants. Pressure in the room is building. It feels like it could blow at any moment.
I'm totally shocked at who knocks at the door next. It's our next door neighbors, Tom Lundgren, and his trophy wife, Lisa. He has good looks like George Clooney and probably as much money. She's about half his age with blond hair and legs that go on forever. Both are in business suits, looking like they'd just come from the office. Ann greets them both with outstretched arms and kisses on the cheek.
"So glad you could make it," she says. "Hope you brought your appetite-- your sexual appetite, that is."
Tom grabs his crotch.
"My fuckin' cock is hard as a rock," he says in that thick New York accent. "Just like always."
Lisa snickers girlishly. Ann winks at her.
"And we all know you're ready-- right, Lisa?" Ann asks.
"Always," Lisa says.
"Good," Ann says. "I don't think anyone else is coming, so let's start."
Luke scoots forward and perches himself on the edge of his seat. He's ready to attack but holds back. It's clear that Ann is running the show-- that she gets first crack at me.
Ann struts over to me and stands in front of me, looking down her nose into my eyes. The rage builds. She winds up and backhands me across the cheek.
"Fucking slut!" she shrieks.
My face stings as Ann pulls up her skirt and straddles my lap. She begins dry-humping my stiff cock and pulling the hair at the back of my head. Her hands find their way to my tits. Ann pinches my nipples and rolls them between her thumbs and forefingers.
I begin breathing hard. I'm beginning to like this.
Just when I'm about to cum in my panties, Ann pushes herself back to her feet.
"OK," she says to the crowd. "Go get her."
Luke lunges. Ann stretches out her hand to block him.
"Uh-uh," she says. "Ladies first."
Lisa comes over to me with a twisted smile on her face. She reaches behind her back and unzips her gray skirt, letting it fall to the floor. Her panties are purple satin with lace trim. With her blue eyes fixed on me, Lisa unbuttons her jacket and slips it off her shoulders. Her purple bra barely contains her voluptuous tits. She reaches into the pile of hair piled on her head and removes a bobby pin. She shakes her head, and wavy hair falls to her shoulders.
Lisa smiles seductively and slides her hand between her legs. She grabs her crotch.
"You want some of this?" she asks.
I swallow hard, thinking that maybe this gang-fuck thing won't be so bad. The words won't come, so I just nod.
Lisa reaches slowly into her panties. I'm thinking she'll go as far as her clit and start fingering herself. But her hand goes deeper-- far deeper-- almost to her ass. I can't figure out what the hell she's doing. Is she going to finger her asshole?
Lisa doesn't leave me wondering for long. Her hand suddenly emerges from her panties with a cock that hangs halfway down her thigh. My eyes bulge. Everyone in the room laughs, except for me. I'm stunned that Lisa-- our sweet next door neighbor-- could have kept that monster hidden so well. In all the years the Lundgrens had lived next door, I never for a second thought that Tom's bride was actually a man.
"Now it's time to play," Lisa says. "Get over here and get on your knees."
Lisa pulls down her panties and steps out of them.
Her cock begins to stiffen as I slide off the couch and drop my knees onto the hard, white ceramic tile. I'm not exactly sure what I'm supposed to do so I just stare at Lisa's manhood for a second. It's sticking straight out of a patch of neatly trimmed pubic hair and pulsating with her heartbeat.
"Go on, bitch!" Ann says. "Suck it!'
I make an "o" with my mouth and slip Lisa's cock inside. The guys whoop as I push my head down her shaft. I think of the blow jobs I've seen on porn movies and try to imitate them. The best cock-sucking queens maintain eye contact, so I turn my eyes up toward Lisa's face. She looks back with her lips slightly parted and a building fire in her eyes. My head bobs. On the down strokes, I'm taking about half of her schlong into my gullet. It doesn't seem like it can go any further.
I'm settling into a nice rhythm when Lisa suddenly jerks her prick out of my mouth.
"Turn around and bend over," she says.
"Why?" I ask.
"It's hammer time," she says.
As I get into the doggy-style position, I see that Phil, Luke and Tom have stripped naked and they're watching Lisa and I, as if we're the floor show in some Vegas club. Phil and Tom are leaning back on the couch and stroking themselves. Luke is laid out on the love seat with Ann between his legs. She's blowing him.
The wig is hanging in my eyes and tickling my cheeks as I wonder what Lisa will do next. My panties are still on, so she doesn't have access to my bunghole. But she solves that problem quickly. Lisa grabs the panties by the waistline and yanks hard. They tear but don't come all the way off. Lisa yanks again, and this time I feel the panties disappear.
"Somebody get me the lube," she says.
Out of the corner of my eye, I see Tom scramble to his feet. He darts to the bathroom and comes back with a mini bottle of lotion. He unscrews the top and hands it to Lisa. She dumps a liberal dollop onto her fingers.
I feel a finger slide into my ass. I immediately tense up. Lisa gently works my hole, never going more than a knuckle or two deep. I'm surprised to find I kind of like it. As I loosen up, Lisa starts shoving her finger further inside me. The deeper and harder she goes, the better I like it. My cock is stiff. Pre-cum starts to leak from the blowhole.
The finger suddenly disappears from my bunghole.
"Spread your cheeks," Lisa says.
I reach back with both hands and do as I'm told. The side of my face is planted on the cool tile.
Lisa grabs my hips and eases the tip of her cock against my hole. My first instinct is to squeeze shut. But then I remember Lisa's gentle finger. I relax. Lisa senses the exact moment I'm ready for her, and she pushes herself inside me.
No feeling compares to having a cock thrust inside you. It's pleasure, pain and humiliation all rolled into one inexplicable emotion. I wouldn't say it's for everyone, but I sure like it.
Lisa pumps me with gentle, shallow strokes. I'm breathing heavily. So is she. My cock feels ready to pop, even though no one has touched it. Lisa picks up the tempo and depth.
"You want it harder, bitch?" she asks.
"Yeah, fuck me harder," I say.
Lisa jams her cock all the way inside me. I grunt as a shiver runs up my spine. Goosebumps form on my arms.
"Like that?" she asks.
"Yeah," I say.
Lisa hammers me again, only this time she keeps going. She pounds my hole with everything she's got. Then she suddenly takes one last thrust and blows her wad inside me.
"Oh fuck yeah!" she says.
Lisa pushes back and flops onto the love sat next to Luke. My ass is throbbing as I raise my head. The first thing I notice when I brush the wig out of my eyes is that Ann has gone from blowing Luke next to the love seat to jerking off Tom on the couch. She's naked. Everyone is, except for me. I'm still in my dress and lingerie. Phil has put on Ann's bra. He's standing next to her and Tom, watching them while stroking his meat.
"OK, everybody," Lisa says. "She's all yours."
Luke doesn't hesitate for even a second. He bursts from the couch and rushes toward me. This time, Ann doesn't try to stop him. His cock is hard as he grabs the back of my head and pokes the head into my lips.
"Open up, bitch," he says.
"If I were you," Ann says, "I'd do it."
Luke is merciless. He shoves himself all the way inside me. I gag as my nose digs into a thick patch of pubic hair.
Luke slowly pulls back. A second before the head exits my mouth, he rams himself back into my gullet. He repeats twice more before yanking his prick out of my mouth and jizzing all over my face. I try to keep my eyes open, but it's impossible with all that spunk flying at me.
When I open them, Luke is staggering back to the love seat. Cum is streaming down my forehead and into my eyes. I can taste it on my lips. I reflexively reach up to wipe my face, but Ann yells, "No!"
"Leave it," she says.
This must turn on Tom because he rolls over onto her. Ann lets him do it. She lays back on the couch and spreads her legs with one on the floor and one up in the air. Tom thrusts himself inside her. He grunts as he pumps. Their union lasts for about 20 strokes. Tom shuts his eyes and shudders, then rolls off Ann.
She looks over at me.
"Come get sloppy seconds, bitch," she says.
Tom gets off the couch to make room for me. I ease myself between my stepmother's legs. Her eyes burn with lust, revenge and hatred. My cock is harder than it's ever been.
"Go ahead," Ann says. "Fuck my pussy."
I ease myself inside her. Her cunt is slippery with Tom's cum and her own natural juices. I begin thrusting slowly and gently. She pinches my nipples and rolls them between her fingers. As I hover over Ann, Luke's jizz streams off of my face and drips onto hers. She opens her mouth and tries to catch the droplets on her tongue.
Phil comes over and aims the head of his prick at Ann's face. He gives himself two strokes before blasting his wad. The first spurt lands on Ann's tongue. The rest splatters all over her face. When Phil backs away, it looks like someone has unloaded a bottle of Elmer's glue. Ann closes her mouth and swallows the cum that landed in her mouth.
I can no longer hold back. Watching Ann drink goop pushes me over the edge. My prick unloads what seems to be a gallon of jizz. Ann arches her back. Her pussy seems to be sucking the spunk out of my body. I never knew it was possible to cum so hard.
I'm empty. I begin to pull my prick out of Ann's cunt, but she grabs my ass cheeks.
"No," she says. "Not yet. Clean my face."
Phil's jizz glistens on her face. With my cock still in her pussy, I lower my head. I start by dragging my tongue across her cheek. Phil's salty cum fills my mouth.
"Just like that, you dirty bitch," Ann says.
I lick Ann's skin from neck to forehead. When she's clean, I pull my cock out of her pussy and flop back on the couch.
"You aren't done yet," Ann says.
"What do you mean?" I ask.
"Clean my cunt," she says.
Ann spreads her legs a little wider. I kneel on the tile floor and put my head between her thighs. Cum is dripping from her pussy, leaving a wet mark on the couch cushion. Ann doesn't give me long to look. She forces my head into her twat. I thrust my tongue as deep inside her as I can. Ann squirms with delight. Jizz drips down my chin.
When I can't possibly suck another drop out of Ann's pussy, I pull myself onto the couch and take a deep breath. Everyone but Ann and I have dressed and look ready to go.
"We'll have to do this again sometime," Lisa says.
She click-clacks toward the door with Tom trailing her, followed by everyone else. They leave with a chorus of "byes" and "see ya laters." When the door slams shut on its own weight, Ann and I are the only ones left in the room.
"I liked that," I say.
"Good," Ann says, "You're going to be doing a lot more of it."
"Really?" I ask. "Everyone left so quickly. I thought they were unhappy."
"Not at all," she says. "That's just how we do things. We don't get to know each other, like neighbors or bridge partners. We use each other for sex. Nothing more, nothing less."
"I can live with that," I say.
"I knew you would," she says. "Now go get cleaned up. I've got plans for you."
"Like what?" I ask.
"Well," Ann says. "We've got the room all day. No sense in letting it go to waste."
"What did you have in mind?" I ask.
"I thought we'd fuck a while," she says. "And maybe later, we'll call Phil and order some room service."
Marisol
- 21.01.2021
- 36
- 0
