Boss

BossRoss looked at the torn-out magazine page tacked onto the wall of his cubicle. In the picture, a man lounged in a reclining with a drink in his hand. A bikini-clad woman, who looked a little like Carmen Electra, leaned against a palm tree and gazed blissfully at the man. The headline across the top said, "Palm Resort and Spa -- The Sexiest Singles' Scene on the Beach"Ross sighed."One more day," he whispered to himself.He had the next morning all planned out. His alarm would ring at 5:30 a.m. He'd drive himself to the airport, board the plane and try to live a life that didn't so closely resemble hell. If it all worked out, he'd be sipping a daiquiri on the beach before noon. All that lay ahead was one week's vacation -- his first since taking a job analyzing computer code three years ago. Maybe he'd even get laid by a real woman, not his usual, which was a hooker or some transsexual weirdo he'd meet in an Internet chat room.Ross heard his boss' voice down the hall. He couldn't make out the muffled words but could tell she was closing in on him fast. Breaking himself from his daydream, he shook the mouse on his computer to remove the screen saver. A spread sheet popped up just as the boss rounded the corner with her assistant. Ross hunched over to make it look like he'd been closely studying the screen."Hello, Ross," the boss said.Ross spun on his swivel chair and rubbed his eyes, as if they were strained from hours of analyzing numbers. When he looked up, the boss was standing uncomfortably close to him, as she usually did."Hello, Mrs. Michaels," he said.The first thing he noticed was her scent, which never failed to knock Ross off guard. Mrs. Michaels wore an expensive French perfume that he recognized from a peel-and-sniff ad in Vanity Fair.Lisa Michaels was a beautiful woman who knew how to use her sex appeal to get what she wanted. It was simple with Ross. All she had to do was talk to him. He became a stammering mess. Authority figures and sexy women always made him nervous. Merge the two into one and it was more than he could take.Ross had to work hard not to stare at his boss' tits. Even under her gray jacket, they looked huge --- a D cup at least, he though. She left the top three buttons undone, exposing the top of a lacy, pink corset. Ross forced himself to look higher. His eyes slowly moved up to the pearl necklace hanging elegantly around her neck. He made himself keep going until he reached Mrs. Michaels' deep, brown eyes. Her gaze always left him wondering if she wanted to fire him or fuck him."Ross," she said, "I'm leaving for Portland tomorrow and will need you house-sit for me. I'll be gone about a week. You can stay in the guest bedroom and eat whatever is in the fridge.""But Mrs. Michaels," Ross said, "I'm supposed to leave for vacation tomorrow. It's my first in three years."Her face turned to stone."I see," she said. "That's disappointing. I was really counting on you to be a team player."Ross gulped. Any employee deemed to not be a team player was instantly fired. And it didn't take much. One analyst got canned for leaving work two hours early to take his grandmother to the doctor.Ross forced a smile onto his face."Oh, you can count on me, Mrs. Michaels!" he said. "I don't know what came over me. In fact, I eagerly look forward to the opportunity to help."The edges of Mrs. Michaels' mouth curled up, which wrinkled the corners of her eyes. The wrinkles reminded Ross that Mrs. Michaels was about 15 years older than him. It was easy to forget with that body of hers."Good," she said. "Well, see my assistant before you leave today. She'll give you the key and directions.""Yes, ma'am," Ross said.Mrs. Michaels stomped away. Ross watched her hips sway. Even after she shit-canned his vacation, he couldn't help but appreciate her sexy switch.. Her tight, little ass and slender legs were almost too perfect. Ross guessed that she worked out everyday.When Mrs. Michaels' rounded the corner down the hall, Ross snatched the magazine ad off the bulletin board. He took one last look at it before crumpling it up and tossing it in the trash can next to his desk.By the time 5 p.m. arrived, Ross was absolutely stewing. He'd spent half his afternoon on his cell phone in the parking lot. The airline and the resort had refused to refund his money or allow him to reschedule. He was out about a month's pay, thanks to Mrs. Michaels' last-minute trip to Portland.When he left work, he swung by his apartment to pick up a change of clothes and his laptop before heading to Mrs. Michaels' house. She lived in Ravenwood, a ritzy subdivision about 10 minutes from the office.He turned on her road just before dusk and saw just how rich his boss had become since founding the company. Every house had at least an acre of green, manicured lawn surrounding it. Parked in each driveway was either a BMW, Lexus or Mercedes.Ross had trouble finding the house and ended up driving through the neighborhood twice before realizing he'd been missing a narrow driveway wedged between two bushes. It led into what looked like an empty lot filled with trees. But then Ross noticed Mrs. Michaels' address painted on the curb.The driveway wound up a hill for a quarter mile before a house appeared through the dense, green forest. From the outside, it looked like a small, single-level home that blended in with its leafy surroundings. But the inside was jaw-dropping. Mrs. Michaels' favored a modern design with leather furniture, abstract art and a giant flat-screen television that hung on the living room wall.Ross heard his stomach growl. He dropped his duffle bag in the living room and went into the kitchen. He checked the fridge. There wasn't much. He helped himself to some salmon spread and crackers and washed it down with soy milk. It was enough to quiet the rumbling.Ross set his laptop on the kitchen table and flipped it open after dinner. He searched for a Wi-Fi connection and, upon finding one, went to his favorite Web site, www.freeones.com. Ross began his nightly porn ritual. He started with softcore-- just chicks stripping off lingerie-- and moved to cum shots. Within an hour, he was rolling his nipples between his fingers while watching transsexuals jizz on each other's faces.The same thing happened every time he started on the porn: An irresistible urge to dress in lingerie sunk into his groin and refused to budge until he shot a load. Most of the time, he'd jerk off and be done with it. But on special occasions, he'd give in. Ross would buy or find a slutty outfit somewhere and play dress up. When the urge was strong enough, he'd find another cross-dresser who wanted a blow job.His mind flashed on the corset Mrs. Michaels had worn under her business jacket. He realized that she probably had a whole drawer full of sexy unmentionables. What a thrill, he thought, it would be to dress up in his boss' lingerie. Stupid? Yes. But fuck it.Ross half-ran down the hallway and found the master bedroom. He switched on the light. Almost everything in the room -- from the bedspread to the plush carpeting -- was white and immaculate. He tip-toed to a chest of drawers, as if Mrs. Michaels might be able to hear him. Then he realized how ridiculous this was and started checking drawers, starting at the top and working his way down. He hit the jackpot on the third one from the bottom.Just as he'd expected, Mrs. Michaels had a drawer full of expensive lingerie. Bras, panties and stockings sat in neatly folded stacks. A lace bag of potpourri, tied shutwith a pink bow, kept it smelling fresh. Ross carefully lifted a stack of bras to see what was underneath. He found exactly what he wanted -- a lacy, black corset with matching panties and stockings. Ross pulled the outfit out of the drawer, taking note of its position so he could put it back in the exact same spot.He stripped off his khakis, boxers and blue shirt and threw them onto the floor.Squeezing into Mrs. Michaels' corset wasn't easy, but he made it work. The garment had about a dozen hooks in back. Ross found it impossible to fasten them all behind his back, so he put on the corset backwards and then twisted it around his torso. Ross finished by slipping his arms through the shoulder straps. To his surprise, his tits almost filled out the cups.Sitting on the edge of the bed, Ross slowly unrolled the thigh-high stockings up his legs, careful to not put a run in them. He knew that the four straps hanging off of the corset were supposed to fasten to the stockings tops, but he didn't know how. Ross figured it out after about a dozen false starts. But even then, he had to redo each strap a couple of times to make sure it was straight.The last part of the outfit was the easiest to put on. He slid on a pair of thong panties and did his best to tuck his cock and balls into the little triangle of fabric up front. The string settled nicely in his ass crack. Ross knew from watching porno videos to put on the panties last. That way, he'd be able to take them off quickly to get access to the genitals when he needed them most.He looked at his reflection in a mirror hanging on the closet door. Ross knew he had too many bulges in unusual places to pass for a woman. But he felt sexy as hell. The corset, stockings and panties squeezed him in all the right places. It was as if the garment had a mind of its own and was passionately feeling him up.Ross walked with a feminine lilt into the living room. He opened the glass door on the entertainment center and scanned Mrs. Michaels' CDs. It didn't take him long to find something totally appropriate: Madonna's greatest hits. He put the disc in and hit play. Sound poured from speakers hidden in the walls, filling the house with Madonna's voice: "Come on girls! Do you believe in love? 'Cause I got something to say about it. And it goes something like this."Ross bounded back into the bedroom and then into the adjoining bathroom. He took a moment to admire the layout. A four-person Jacuzzi sat in the corner. He could see through a glass door that the shower was big enough for two and had two gold shower heads on opposite ends of the enclosure. The bathroom had two sinks. When he looked under the first one, he found shaving supplies, apparently for Mr. Michaels. But Ross hit the jackpot again when he looked under the second sink -- Mrs. Michaels' perfume and makeup.Ross pulled out the makeup kit and set it on the counter. He found the sluttiest shades possible and laid them on thick: black eyeliner, red lipstick and gray eye shadow. When finished, Ross sprayed his wrists with perfume and checked his work in the mirror. Not bad, he thought. He wouldn't pass for a woman, but he had plenty of Internet buddies who would accept a blow job from him.The thought of a man's cock in his mouth energized him. "Vogue" was pumping through the speakers. He started striking poses like a fashion model. A voice in his head directed: "Give me pouty. OK, now sexy, Now flirty. Yes! Work it, baby, work it!"He'd totally lost himself in the music when he noticed one pair of hands clapping out of tune with the music. Ross' first thought was that he didn't remember "Vogue" having a hand-clap section. But then it registered that the sound wasn't coming from the speakers. It was in the room with him. When Ross turned his head, his stomach leaped into his throat.Mrs. Michaels was leaning against the bathroom door with a look of disgust on her face. She was wearing the same business suit and corset as she did at the office."Bravo," she said mockingly. "You want to tell me what the fuck you're doing?""I-I-I thought you were in Portland," Ross stammered."Flight was cancelled," Mrs. Michaels said.Ross scanned the room for something to cover himself. There was nothing, not even a towel. He'd have to go through Mrs. Michaels to get to his clothes."This isn't what it looks like," he said."Oh, really," she said. "Then tell me what it is.""Well," Ross said, "I guess I just got to thinking, and I just wasn't sure if you'd mind, and...""Save it!" Mrs. Michaels snapped. "It looks to me like you're a little, fairy. What I want to know is if you're a fairy who likes the cock only, or if you like the cock and the pussy.""Oh, Mrs. Michaels," Ross said, "I love the pussy. You don't know how much I --""Save it!" she snapped. "Get on your knees."Ross hardly believed his ears."What?" he asked."You heard me, bitch," Mrs. Michaels said. "Get on your fucking knees."Ross kneeled on the cool tile floor.Mrs. Michaels locked her gaze on him and slowly unbuttoned her jacket. She held her arms out to the side and shrugged it off. Without averting her hawkish eyes, she unzipped her skirt and let it fall to the floor. She had an even more spectacular body than Ross imagined. A corset-and-stockings get-up, much like the one Ross was wearing, squeezed her body into a sexy hourglass figure. The heels made it all the better by emphasizing her two best assets: her tits and ass. She let him take a look before stepping forward, stopping a half inch from his nose. Through the sheer, white panties, Ross could see that Mrs. Michaels had recently trimmed her pussy hair into a neat Mohawk.Without uttering a word, Mrs. Michaels put her hand on the back of Ross' head and forced his nose into the thin fabric. She grinded her pussy against his face, rubbing her clit on the bridge of his nose. Her panties were already wet. Ross inhaled deeply, enjoying the musty scent.Mrs. Michaels suddenly took a step back and looked at the boner poking into Ross' panties. The corners of her mouth curled up, wrinkling her eyes."So, you DO like the pussy," she said. "I'm glad. You can be useful to me."Ross wanted to ask what she meant, but before he could, Mrs. Michaels' cell phone rang."You stay right there," she said.From his spot on the cold tile, Ross watched Mrs. Michaels go into the bedroom and dig the phone out of her purse. He could hear only her end of the conversation, but he gathered from the context that her husband was on the other end. It didn't take long for it to turn nasty."...Well, fuck you too," Mrs. Michaels said into the phone. "...None of your business what I'm doing... Yeah, so what? I'm listening to Madonna. I can listen to my own CDs whenever I want...No one... Well, which one of your whores do you have with you in Aspen?... Yeah, I bet...Fuck you, too."Mrs. Michaels snapped the phone shut and hurled it across the room."I fucking hate men!" she screamed. "One is stealing my lingerie! The other is fucking some whore in Aspen!"She pointed at Ross."You," she said, "Get in here."Ross got to his feet and walked into the bedroom."Closer," Mrs. Michaels said.Ross inched forward."Closer," she said again.Their noses were an inch apart. Mrs. Michaels slapped Ross on the cheek. It shocked him more than anything, but the sting lingered."You want to know what it feels like to be a woman?" Mrs. Michaels said. "Then I'm going to show you. Get on your fucking hands and knees on the bed."Ross did as he was told without question. Mrs. Michaels disappeared into a walk-in closet, leaving Ross to wonder what she had in store for him. He was sure he'd be fired. It was now only a question of how much pain and humiliation he'd have to suffer before she let him go.Mrs. Michaels emerged from the closet with a strap-on dildo protruding from her pelvis. She stood in front of Ross and let him watch her squeeze a dab of lube in the palm of her hand. She stroked the long, white, slender shaft, as if it were her own cock and then climbed onto the bed, positioning herself behind Ross.He noticed that the closet had shut most of the way on its own. Ross could see their reflection in the mirror hanging on the door. Mrs. Michaels kneeled behind him and gazed contemptuously at his ass. She suddenly grabbed one of the panty strings on his hip and tugged. She was trying to tear the panties off of his ass, but they wouldn't give. Mrs. Michaels pulled harder. The string burned as it pressed deeper into his flesh, but Ross didn't take complain. The panties broke before Mrs. Michaels' will did. She threw the frayed mess into the corner with his khakis."Spread your fuckin' ass cheeks," she said.Ross reached back to do as he was told. Without his arms to support himself anymore, he buried his head in the comforter and waited in darkness for Mrs. Michaels to make the next move. She touched the tip of the dildo to Ross' asshole without sticking it in, left it there for a beat and then pulled back. She began rocking her hips back and forth, teasing him with the plastic cock."You know," she said, while pushing the dildo against his bunghole, "I love abusing the shit out of you."He felt her take the dildo away."You're just a faggot bitch, you know that?" she asked.Ross grunted."Shut up!" she snapped.Mrs. Michaels pressed the dildo against his hole again, this time harder than before. It was close-- so damn close-- to breaking the surface and slipping inside him. Ross surprised himself by wanting it badly.But Mrs. Michaels pulled away."I'm gonna bang your shit so fuckin' hard," she said.When Mrs. Michaels rocked forward again, the fuckstick slipped inside Ross. He gasped."Like that, huh?" Mrs. Michaels asked.Without waiting for an answer, she slowly slid the dildo deeper into Ross' ass pipe. He grunted with joy as it filled him. But Mrs. Michaels didn't give him a full taste of the rod on the first stroke. When it was halfway in, she stopped and pulled back just as slowly as she entered.Ross felt his tits sway as Mrs. Michaels began to fuck him. With each stroke, she picked up speed and thrust the rod deeper into him. She knew exactly how to pound him without causing pain. The fuckstick caressed something deep inside Ross that he never knew existed. Whatever it was, it caused his prick to swell. No one had touched his cock. Yet, he felt like he could've burst right there. But he didn't. Ross held back. He sensed that Mrs. Michaels had more in store for him. He didn't want to ruin it by shooting his load early.Mrs. Michaels' thrusts started slowly and lovingly but quickly became angry and punishing. Her fingertips dug into Ross' hips. The rod went all the way inside him each time she pushed her hips forward."You fucking like that, you faggot weirdo?" she asked breathlessly. "You like getting fucked like a bitch?"Mrs. Michaels gave Ross' bunghole one last thrust before pulling out. She unsnapped the strap-on dildo and threw it in the corner in one fluid motion."Get on your back," Mrs. Michaels said, while kicking off her heels. "You're going to eat my pussy."Ross flopped onto his back as Mrs. Michaels detached the corset's straps from her white, thigh-high stockings. She propped one leg onto the bed and hooked her thumbs under the stocking top. She pushed the sheer fabric down her leg, revealing a milky thigh. After easing around the bend at her knee, she slid the stocking past her sleek calf. Then she did the same thing with the other leg.Ross watched with helpless yearning as Mrs. Michaels struck a Marilyn Monroe-style pose and reached down to her knees. She slowly righted herself, gently caressing her own flesh. She drew her hands over her thighs, stomach and tits before twirling her finger around her string of pearls and throwing a flirty smile at Ross. With a sexy tilt of the head, Mrs. Michaels pivoted on one foot and reached behind her back with one hand. She unbuttoned the corset one clasp at a time with a speed and grace that amazed Ross.He admired her ass -- two perfect bubbles split by a white string without a pimple, hair or bruise in sight. Mrs. Michaels slid her thumbs under the panty strings at her hips and swayed back and forth as she pushed them down her lovely legs. Ross realized he was seeing his boss naked for the first time. It made him want to cum in his panties.