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Just His Luck Ch. 01

Copyright 2015 Lara Longstaff
All Rights Reserved



Chapter One

Joseph had just finished ticking off the last item on his inspection report when he heard the truck pull up to the loading dock. He grinned as he tucked his clipboard under one arm and walked over to the big rolling door. He slammed the green button on the wall and the corrugated steel rose slowly, revealing the small blue and white delivery truck.

"Want me to check that in, Boss?" one of the men from the receiving area asked. Joseph waved him away without a word. He'd been waiting all day for this delivery. The truck came to a halt as it just nudged the heavy rubber bumpers at the edge of the dock. Its big diesel growled to a halt as it opened up and a cute little brunette hopped out.

"Good Morning!" Joseph waved cheerfully. As one of the plant's engineers, it was far beneath his duties to check in one of the venders. Particularly the vender who filled up water tanks in the break rooms and managers' offices. Ever since he'd seen the company's new driver, however, he'd made a point to be around on Thursdays to check her in personally.

"It's one o'clock, you big goof!" the pretty woman grinned impishly as she hopped up the steps beside the dock. Her olive jumpsuit wasn't exactly flattering, but even so he could tell that she had a tight little body under there. Little being the operative word, as the slender woman barely topped five feet. Still, she had curves in all the right places.

"Time flies, Rachel," Joseph stammered as he pulled open the door for her. She looked up at him and rolled her big brown eyes. Even without make up, she was gorgeous. She had plump lips, a cute button nose, and tan skin with just a bit of freckles across her high cheekbones.

"Gonna let me in or just stand there blocking the door?" she asked as she handed him the invoice. She craned her neck to look up at him and tried her best to look annoyed. The twinkle in her eyes gave her away.

"Only if your papers check out, Miss," he said. He scanned over the invoice. Everything was clearly in order but he took his time any way. He was a tall, slender guy, just over thirty but already one of the lead engineers at the plant. He'd had his share of girlfriends in the past, despite being what he considered to be completely average, save for his height. He had brown hair, brown eyes, a slender body and everyday looks. Rachel the water delivery girl seemed to like flirting with him, though. Checking her in, and checking her out, was the highlight of his week.

"I'd love to stand here all day, but I really should head in and start filling up your tanks," she said at last.

"We'll need extra today," Joseph said as he signed off on the paperwork. He stepped aside so the petite woman could move around him. She pulled open the doors on the back of her truck and hauled out a collapsible metal cart.

"Oh, I think I've got more than enough to satisfy all you thirsty boys," she winked. She was surprisingly strong, and loaded several huge jugs of water onto her cart with only the cutest little grunt to betray her effort.

"Six should do it," Joseph said, impressed as always, and by more than her strength. When she bent over, the dark green canvas of her jumpsuit stretched across her firm little bottom quite nicely indeed.

"Are you sure six is enough? Seems like an awfully small number to me. Down right tiny," she said over her shoulder. A strand of soft brown hair and come loose from under her hat, falling over her eyes. She pursed her lips and blew it out of her face. She glanced down at the modest bulge in his khaki pants, then back up to his face again.

"Oh I don't know," Joseph gulped. He almost had six inches down there, almost. He really was quite average in every way. His face felt hot and he looked down at his shoes.

"You're cute when you blush," Rachel said as she wheeled the cart past him. She reached up, coming up on her tip toes as she patted his cheek.

"Uh, thanks," he mumbled, and met her gaze. She was grinning like a she-devil.

"But you're pretty cute all the time, Joseph. I won't be long. I just have to deliver my big load to all your thisty men and I'll be out of your hair!" she said before wheeling her cart further into the plant.

"I'll be waiting!" Joseph managed to say as she departed. Even in tennis shoes and pushing all those heavy water bottles, the small woman managed to swish her round ass quite seductively. Joseph smiled and starting humming to himself. He loved Thursdays.



***

How quickly things changed, Joseph mused. He'd screwed up the courage to ask Rachel out, only to be rebuffed. She hadn't rejected him outright. She'd merely blushed and looked really uncomfortable as she beat a hasty retreat. The pretty delivery girl had claimed to be busy all weekend, then had retreated so fast her truck left skid marks on the concrete.

"I'm an idiot," the young engineer growled and stomped on the gas pedal. His sensible little sedan lurched forward on the highway. He passed one car after another, his knuckles white as he held the steering wheel in a death grip. How could he have misread the signs so badly? For weeks she'd flirted with him, or so it had seemed to him. But when he'd finally gotten up the nerve, it was like he'd caught the brunette completely off guard. For a moment, she'd even looked frightened!

His engine whined as he rapidly approached the back of a heavily-laden pick up truck. He was driving like an asshole, and if he kept it up, he was going to have an accident. With a sigh he eased off the gas, and just in time. A loud bang from the truck nearly made him jump out if his pants. The rusty blue truck swerved on the highway as bits of black rubber flew from its left rear tire. The cardboard boxes stacked high in the bed wobbled and nearly spilled out onto the highway before righting themselves.

"Shit!" Joseph cried as he hit the brakes. He nearly slammed into the back of the vehicle before it lurched off onto the shoulder. Panting, he passed it and pulled over in front of the truck, his heart thudding in his chest. He threw his car into park and took a moment to collect himself. He glanced into the side mirror to see a woman slip from the truck. He peered closer at the mirror to get a better look at her. She was tall, with long, light brown hair and a curvy body tucked into a white blouse and short denim cut-offs.

"Damn," he muttered and shut off his car. After Rachel's abrupt rejection earlier, maybe a damsel in distress what just what he needed. He got out and hurried up the side of highway with cars and trucks barrelling down the road beside him.

"Hey," the woman smiled tentatively as he approached. She was flushed and her nostrils flared. She still looked a bit stunned by the blow out. Her big round breasts heaved against the flimsy white fabric of her top.

"Nice bit of driving, Miss," he said with a friendly smile. "You nearly scared me to death but you kept control of your truck there."

"You think?" she turned to face him, and Joseph tried not to gasp. She was quite pretty, with big hazel eyes, a wide mouth and legs that went for miles. She looked like a swimsuit model.

"For sure," he held up his hand. It trembled slightly, but whether it was from almost getting into a wreck on the highway or from being face to face with a beautiful woman, he wasn't sure. "Look, I'm still shaking!" he laughed.

"Tell me about it!" she laughed, and it seemed to release the tension from her body. Her smile was like the sun breaking through the clouds on a rainy day.

"Are you all right?" he asked.

"Nothing broken," she nodded. "You?"

"Nope. But I may need a new pair of underwear," Joseph smiled, and the woman laughed, her voice surprisingly rich and deep for a woman.

"Is he going to help?" another woman asked. Joseph looked up to see another brunette crawl out of the truck's cab, followed by another. Both were tall and busty like the first, and just as pretty. They were dressed like the first woman: sneakers, jean shorts and short little tops. He'd never seen so much tan shapely leg in his life.

"I don't know," the tall woman shrugged. "Are you?" she arched a thick eyebrow at him.

"Sure," Joseph gulped. "Got a spare tire?"

"God, thank you!" the first woman said. She held out a hand. Her fingers were long and manicured, but she had a strong handshake. "I'm Rosie, by the way. These are my roommates, Cindy," she nodded to the bustiest of the three, a girl with black hair and pink shorts. "And Lotta," he turned to the young brunette with a huge smile and cute dimpled chin.

"I'm Joseph," he gulped as she shook Rosie's hand. There was something about her. Her grip was better than a lot of guys. Her hands were large, her voice husky. She was easily six feet tall in sneakers. If it wasn't for her rather impressive bust and the prettiness of her smile, he'd have said that she was almost mannish. All three of them were, in fact. Still hot, though. And they still needed his help. He put on his most charming smile. "Happy to help."

"You're a prince!" Rosie said. She finally let his hand go and guided him to the back of the truck. All three woman gathered around him on the shoulder as cars whizzed by. If he hadn't been so tall himself, they would have towered over him.

"I don't know about that," he chuckled as he crouched under their old pick up. He grunted as he freed their spare from under the chasis.

"It's pretty cliche, having a man help us change a flat," the cute one, Lotta, giggled, an odd sound with her deep voice.

"Yeah, but look at him go! He's got such strong hands!" the black-haired beauty, Cindy, purred like a cougar.

"You two are terrible!" Rosie laughed. "And I saw him first!"

"Don't fight over me, now," Joseph laughed as he pulled himself up from under the truck. Being an engineer had it's advantages. He worked quickly to jack up the truck and replace the blow out with the full-sized spare. It wasn't easy to concentrate with those three tall beauties laughing over his shoulder, but he got the job done in record time.

"Gosh, you're quite the handy man, aren't you?" Rosie said as she lay a long hand on his chest. "I like a man who can handle big tools."

"It was nothing, really," he coughed and shuffled his feet. With three pairs of dark, glittering eyes staring at him, he suddenly felt like a deer surrounded by a wolf pack.

"Nonsense, Joseph!" Cindy laughed. She bent over and kissed his cheek, her lips hot against his skin. Lotta did the same on the other side, and before he could offer a spluttered response, Rosie leaned forward and gave him a quick, hot kiss on the lips.

"Heroes are always modest," she said as she pulled back.

"We should reward him," Cindy said, brushing her long fingers through his hair just above his ear.

"Really, I'm no hero," Joseph blushed. "I just couldn't leave three pretty girls stranded on the side of the highway, could I?"

"I want to bake him a pie!" Lotta announced. She pushed her curvy body up against his side. She was the shortest of the three, but easily five-nine or ten even so. Her huge breasts pressed against his arm.

"I do like pie," he chuckled. His day had gone from good to crappy to amazing in just a few short hours.

"Hopefully not too much!" Rosie winked. She opened the truck's door and pulled out a slip of paper and a pen from her purse. "Here's our address, Joseph. Our boyfriends are helping us unpack tonight, but tomorrow?"

"I'll make that pie!" Lotta nodded eagerly.

"I'll throw some sausages on the grill," Cindy added. "I hope you like a big juicy sasuage."

"Sure," Joseph meeped as he took the paper.

"Six o'clock, don't be late!" Rosie patted his cheek.

"Wouldn't dream of it," he muttered. His cock throbbed in his grimy khakis as he watched all three leggy women climb back into their truck. They waved, and Rosie blew him a kiss as they pulled back onto the highway. He glanced down at the paper and wondered if the address written on it in Rosie's big, looping hand was for real. They'd mentioned they had boyfriends, but they'd fawned all over him even so.

"We'll just see," he said to himself as he stuffed the paper into his pocket and walked back to his car. Even if all they wanted to do was feed him dinner, he could do a heck of a lot worse than a free meal with three tall, exotic women!



***



"You've got a really nice place," Joseph said through his last bite of fresh apple pie. He sat at the head of a big pressed-wood table and smiled at the three women watching him eat. They were model hostesses. They laughed at his jokes and told more than a few of their own. They had a dirty sense of humor, and he found himself relaxing more than he'd ever managed to do when around beautiful women. They'd fed him and entertained him in their spacious new home all evening long before they'd decided, around ten that evening, to finally dig into that pie Lotta had made for him.

"Yeah, Fox Wood is a pretty exclusive community," Rosie said slyly.

"I noticed that," Joseph nodded. The trio lived in a gated community with big houses clustered around a clover-leaf of cul de sacs. They even had an armed guard at the gate. The big man had waved him on through after asking his name. "You girls must do pretty well for yourselves. Are you models?"

"How'd you guess?" Lotta laughed, which made her massive bosom jiggle in her tight pink tee shirt.

"Well, you're all so tall and pretty!"

"Thank you! You're pretty handsome yourself!" Cindy chimed in.

"I'm just a regular guy," he shrugged off the compliment. "I'm sure your boyfriends are better looking than me!"

"So cute," Rosie shook her head.

"Have I seen you on any magazine covers or anything?" Joseph asked. They were all staring at him again, and he squirmed on his chair.

"I kind of doubt that," Rosie shook her head.

"You never know, Rosie," Cindy shook her head. "Do you read magazine about T-girls?"

"Uh, what's a T-girl?" Joseph asked. He had an idea, but he wasn't quite certain. He set his fork down onto the plate with trembling fingers.

"We're transwomen, Joseph," Rosie explained. "If you watch porn, they call us shemales," she made a disapproving face.

"You know, chicks with dicks!" the light-hearted Lotta laughed.

"Oh, I see!" Joseph coughed. That certainly explained a few things. "Well, the three of you are very pretty women," he said nervously. He'd heard of shemales before, heck, he'd even watched some porn along those lines once or twice. He never thought he'd meet a girl like that in real life, let alone three!

"And you were worried he'd freak out, Rosie!" Cindy said. She patted Joseph's arm. "You're not freaking out are you?"

"No," Joseph said. Nothing to freak out about, really. All they'd done was make him a very nice dinner and stroked his bruised ego a bit.

"Do you have a girlfriend, Joseph? Anyone special?" Rosie asked. She sat across from him, and she leaned over the table on her elbows. Her breasts nearly spilled out of her low cut dress as her deep cleavage called to him seductively.

"No one special," he shook his head. He felt a stirring in his pants as he tore his eyes away from the transwoman's chest. "I actually asked a girl out yesterday right before I helped you guys on the highway. She said no."

"You poor thing!" Cindy cooed. Her big hand slid up his arm, under the sleeve of his short-sleeved button-down shirt.

"That's awful!" Lotta echoed. She took his other hand, giving him a squeeze. He nearly jumped out of his seat when he felt her bare foot touch his leg under the table.

"She doesn't know a good thing when she sees one," Rosie snorted dismissively. "I like you, Joseph. You're a good guy and a lot of fun to be around. I do have a boyfriend, we all do. But still, she's a fool to turn you down."

"You're different than our boyfriends," Lotta added.

"In what way?" Joseph asked nervously. Cindy's wandering hand caressed over his shoulder and down his back, while Lotta squeezed his hand affectionately.

"Tom, my boyfriend," Rosie licked her plump lips. "Is a big hunk who spends half his time at the gym. When I have him over, he," she stopped and blushed ever so delicately. "He makes me feel like a woman. Like I'm all woman."

"So does my Damien," Cindy piped in.

"Roger is a bit more versitile," Lotta said.

"That's nice," Joseph said, not quite sure what the tall shemale was getting at.

"Well sometimes, I don't like to feel like being all woman. Sometimes I like to use what I had as a man," she said softly.

"Oh?" Joseph scratched his head before it dawned on him. "Oh!"

"We all three talked about it," Lotta said cheerfully. "We all want to take turns filling up your hot little butt!"

"You're going to scare him away!" Cindy admonished.

"You're joking!" Joseph protested. His cock throbbed to life in his pants.

"Sorry, but no," Rosie laughed. "When you bent over yesterday to get under the truck it was all I could do not to fill you from behind right then and there! I haven't felt that way about a man in a long time!"

"I'm flattered I guess?" he looked around, licking his lips. It was only a short walk to the door. He could be up and out of there in seconds.

"More than flattered, I'd say," Cindy said breathily as she reached under the table to fondle the stiff pole in his pants.

"Is he hard?" Lotta wondered with a look of playful delight in her soft brown eyes.

"Like a rock!" Cindy confirmed.

"I don't know if you've ever had a bisexual experience, Joseph," Rosie said. "But if you haven't tried being a bottom, you really should experience it at least once in your life."

"I haven't!" he yelped. Cindy's strong hand squeezed his cock tighter.

"I'll let you fuck me after," Lotta offered. "That is, if you aren't too big. I hate it when guys are bigger than I am!"

"No worry there, Lotta!" Cindy gave his cock a pat.

"Hey!" he yelped.

"How fun!" Rosie laughed. "I've got a full inch on Tom and it always makes him so mad!"

"Just one?" Cindy arched her black eyebrows. "I'm more like three inches bigger than Damien!"

"You girls can't be serious!" Joseph managed to gasp at last.

"Only because he's hung like a mouse, Cindy!" Rosie laughed.

"So is Roger, but I think it's cute!" Lotta laughed. She leaned back and clutched at her massive bust with both hands. "He really likes my double D's and my eight inches both!"

"Great, so you're all well endowed?" Jospeh shook his head. He pushed back, about to stand, when Cindy latched onto his bulge yet again.

"Aww, come on! You shouldn't go without at least seeing what top-notch breast implants can do for a girl!" the raven-haired shemale laughed. "And how nice a cock can feel inside you!"

"Don't be pushy now, Cin," Rosie said a she stood. She walked around the table, her hazel eyes locked on the tall young man. When she reached his side, Lotta scooted over to make room. She pulled her short dress over her head. "I like a more natural form of persuasion!"

"Shit," Joseph gulped. Her body was long and lean, with just a whisper of a curve around her hips. Her belly was flat and toned, and every square inch of her was nicely tanned. She wore no bra or panties. Her huge breasts, easily a full D cup or larger, sat high, round and firm on her chest, topped by long brown nipples. Between her slender thighs hung the biggest piece of meat the young man had ever seen. Framed by a tiny patch of dark hair above and smoothly shaved, egg-sized balls below, her cock dangled before him. Even soft the light brown tube was nearly as long and thick as the hard on throbbing in his pants.

"I haven't used this in over a year, Joseph. You should feel honored," Rosie smirked as she watched him stare. She wrapped her long fingers around herself and gave a long slow pump.
"My turn!" Lotta said eagerly. She shoved the table across the hardwood floor as she stood. The tall, husky-voiced girl had an oddly girlish manner, and she giggled as she too stripped. Not to be outdone, Cindy joined in. Clothes went flying, and Joseph sat there stunned. In moments three enormous pairs of naked breasts and three big soft shemale cocks surrounded him.

"I think the cat's got his tongue," Lotta laughed. She leaned her hips forward and slapped his left cheek with her heavy, half-hard cock.

"What do you say, Joseph?" Rosie asked, staring down at him. Her cock was inches from his lips and as she stroked it grew longer and thicker. The pink head flared with her excitement, dripping clear fluid from the tip. His heart thudded in his chest. This was so strange. So fucking gay, even. Yet he was hard.

"This really isn't fair, all three of you are bigger than I am," he croaked, running his tongue over his lips. His mouth was starting to water. His experienced eyes took in the sight of her cock. She had a full nine inches, easily!

"If your'e going to be the best of both worlds," she shrugged. "Might as well be the very best. I know another t-girl with eleven inches, but she's a freak of nature! Strict top too. She'd really tear you a new one!"

"Jesus," he groaned. It was like he was in a trance. His hands rose, almost of their own accord. He glanced to his side. Cindy's bust was every bit as impressive as the other two shemales, and her cock a solid eight inches. His fist wrapped neatly around it as he took both her and Lotta's equally huge member in hand. He shuddered. They felt truly massive, filling his hands and throbbing against his skin. He'd never held another cock besides his own, and the feel of it shocked him. He stroked them up and down, moving the silky skin back and forth over their steely shafts.

"Good boy! Now open that mouth," Rosie urged him, her deep throaty voice soft as velvet. Joseph met her eyes. She put her hands on her hips and pushed her huge cock closer to his face. It was incredibly thick, and covered with fine veins. His own cock throbbed urgently in his pants. His not-quite-six inches would have looked like a baby's dick next to hers.

"You're so big," he whispered before pushing his soft lips against her. The sticky drop of precum smeared over his lips, and his tongue flicked out to taste it. It was salty and tangy, and the musky smell of it set his brain on fire. He lapped up more, dragging his tongue over her rubbery flesh. He closed his eyes and moaned. She tasted delicious.

"Too fucking easy!" Lotta giggled. She wrapped her fist around his, guiding his hand up to squeeze at her cock just below her bulbous purple head.

"Big tits are like big dicks. They can make anyone bi!" Cindy winked at her roommate.

"I said open your mouth," Rosie said sternly, ignoring her friends. "Licking is nice, but you really need to suck it!"

"Sorry, I've never done that before," Joseph blushed as he looked up at the gorgeous model's face over her huge breasts. Cindy's and Lotta's cocks began to leak precum too, and he smeared his thumbs in the sticky fluid, massaging their shafts just below their heads.

"First time for everything, sweetie!" Rosie said. She pushed forward, and her cock barged into his lips hard enough to push his head back few inches. He steeled himself, then obligingly opened his mouth. She pushed right inside. Her girth stretched his lips into a wide O as his jaw was forced open as wide as it could go.

Joseph sat there for a moment, thinking about what an odd turn his life had taken. One minute he was being pampered by three gorgeous ladies, the next he had a cock in his mouth. A cock longer and thicker than his own. It helped that that cock sprouted from a gorgeous woman. He closed his eyes and began to suck. She smelled of perfume with just a whiff of masculine musk. Her rubber skin was hot against his tongue. He bobbed his head, feeling her slip further past his lips.

"Don't forget me!" Cindy slapped her meaty tool against his cheek. Joseph pulled off of Rosie just long enough to wolf down the black-haired woman's fat cock. She was a little smaller than Rosie, but just as hard. She smelled a bit different, but it was just as intoxicating. He wondered, between slurps, if Lotta was just as good.

"Give your cock too, Lotta," he whispered at the curvy young shemale, and she smiled sweetly as she shoved her big cock into his mouth. She was the sweetest of all three of them, and he moaned around her cock as he did his best to stimulate her stiff girly-dick. He gave her a solid two minutes of licking and sucking before moving back to Rosie's jaw-breaking monster of a cock.

"Pretty fun, isn't it? The tall woman smirked down at him. He nodded with his mouth full of her dick. He made the rounds, sucking and slurping and stroking the two other cocks as he took turns pleasuring them with his mouth. Drool spilled down his chin, staining his shirt as he devoured them in turn. It was such a submissive, faggy thing to do, but he was beginning to love it.

"Enough, I call first dibs on his ass!" Lotta squeaked.

"I'll get the lube!" Cindy said cheerfully. Rosie and Lotta pulled him to his feet. With four pairs of hands, they had him stripped in no time.

"Gosh, he's even smaller than Roger!" Lotta laughed.

"Does it matter? He's our little bottom boy tonight." Rosie laughed.

"Hey, I didn't exactly agree to all of that!" Joseph yelped. It didn't matter though. The two of them lead him to a clear space on the carpeted living room and had him on his hands and knees by the time Cindy returned with what looked like a gallon jug of clear sex lube and a giant box of condoms. Tall as they were, he could have easily put a stop to it. They were aggressive, but he was pretty sure that they wouldn't try to force the issue. He shivered on the floor. He wasn't going anywhere.

"Gear up girls!" Rosie barked as she rolled a condom down her titanic shaft. Lotta practically jumped to get in line behind him.

"You've got the tiniest butt!" the cute brunette giggled. She squirted lube all over herself before sliding her huge shaft between his cheeks. The fluid was cold and sticky, and Joseph braced himself, gritting his teeth.

"Relax, or she's gonna hurt like hell," Cindy said as she crouched beside him. She stroked his face and kissed his cheek. "I promise you, you'll love it, though!"

"All right," the nervous young man whispered. Lotta's big cock felt like an arm sliding back and forth between his buns. He took a long, ragged breath and forced himself to stay calm.

"Here goes nothing!" Lotta said excitedly. It was clear she was done waiting. The fat head of her latex-clad cock punched against his tiny brown ass.

"Christ that hurts!" Joseph grunted as a stab of pain shot up his spine.

"Relax!" Rosie slapped his cheek gently. She feel to a knee in front of him. Her pretty face was stern. Her hazel eyes bore into his. "Just accept it and the pain will go quick."

"Okay," he muttered. Lotta tried again. Then again. Each over-eager thrust brought another twinge of pain as his stubborn, virgin ass refused to give. He lowered his head to the floor, pushing his ass up higher and panting. Just accept it, she'd said. He closed his eyes and tried to think of something pleasant. Rachel's face filled his mind, cute and smiling as she blew that strand of hair from her face.

"Gee whiz he's tight!" Lotta gasped as her big cock finally crammed into his ass. The pain was hot, liquid, and thankfully, short-lived. She held herself still while he squirmed and moaned and got used to a wrist-thick slab of flesh spearing his tiny sphincter. His muscles relaxed bit by bit, and the pain evaporated.

"Wow," was all he could manage to croak.

"Feels good, doesn't it, Tiger?" Cindy asked, her low voice breathy in his ear.

"Yeah," he nodded.

"Remember, you can take a crack at my butt when we're done with yours!" Lotta reminded him gleefully. She began to rock and back and forth, sawing her cock in and out of his overstuffed back door.

Joseph moaned and grunted and from time to time even screamed as he held still and took it like a good little bitch. Rosie and Cindy cheered their roomate on as she fucked him faster and faster. Her big balls slammed into his as he rode a tidal wave of sensations. Burning pain and sparks of pleasure joined an incredible feeling of fullness.

"Fuck me!" he cried at last. He'd never felt anything like it. It was rough. It was raw. It was oh so gay. He fucking loved it.

"That's the spirit!" Lotta laughed. She began to pant as she worked on his ass like a heavy-weight boxer, breaking down his resistance bit by bit. She pummeled faster and faster, and the hot friction thrilled him with unknown pleasures.

"Fill him up!" Rosie reached over and slapped her friend's plump ass as she fucked. That was all it took to drive her over the edge. The cute young brunette squealed girlishly as she stabbed his ass one last time. He could feel her cock pulse inside him, filling her condom with her cum.

"My turn!" Cindy leapt to her feet. Lotta had no sooner pulled out of his poor, tender ass when the black-haired beauty took her place. Her cock felt strangely cool as she sank into his well-fucked ass. She slid to the hilt with ease.

"God, give me a second to catch my breath!" Joseph protested. It fell on deaf ears. Cindy took a tight grip on him around his waist and hunched her round ass back and forth like a jack rabbit. Her thick shaft almost seemed to vibrate deep inside him, and he found himself thrashing under her in ecstasy.

"Take it, take it!" Cindy panted as she worked herself into a frenzy. Even at her frantic pace, she held out for surprisingly long. Joseph whimpered pathetically as she took him. Every part of his body felt numb and cold. Every part but his burning, blazing ass.

"Come on. Fuck me harder!" he surprised himself by begging. He rocked on his hands and knees, pushing his tight little ass hard against the shemale's curvy body.

"What a little slut!" Rosie cackled in glee. Joseph looked up to see the statuesque transwoman smirking down at him as she stroked her gigantic cock.

"Yes, oh God yes!" Cindy shuddered, her hips spasming against him as she came. Joseph squeezed his ass around her, surprised by how pleasurable it was to feel her throbbing erection inside his rectum.

"Finally!" Rosie pushed her roommate out of the way and took her her turn. She slapped his reddened butt with both hands before pushing her condom-covered cock up to his gaping, wet hole. Joseph hissed loudly as she slowly pushed her way inside. She was considerably thicker than either Lotta or Cindy, and his ass clenched painfully around her big pink head.

"Easy!" he yelped.

"I'll give you thirty seconds," Rosie said smugly. She pushed herself slowly into him, sighing in pleasure as his hot, sucking ass took in inch after inch. A little twitch of her hips drove the last inch into him.

"Ouch!" the tall man grunted as her huge cockhead forced itself deep into his guts. His belly rumbled, and he could feel his insides shifting to accommodate her over-sized invader.

"You'll get used to it," Rosie said, rather matter-of-fact. She pulled back and thrust in, harder and faster. Joseph screamed and bucked, but she didn't stop. Again and again she forced herself to the hilt. He growled and took it, surprised at how eager he was to feel her. Her huge cock hurt, but it hurt so damn good!

"He got it all on the first try?" Lotta gasped. "He's an even bigger slut than Roger!"

"I'm jealous!" Cindy pouted. "Damien won't even blow me!"

"Neither will Tom," Rosie grunted. Her huge tits wobbled as she steadily filled Joseph's tender bottom. "That's why I'm going to really enjoy this!"

"You're not the only one," Joseph admitted.

"Yay!" Lotta almost bounced in excitement. She and Cindy sat back on the couch, idly stroking their hardening cocks as Rosie slowly, steadily, built to a climax.

"Such a hot little ass! I need to find guys like you more often!" Rosie growled. Her body slammed into his faster and faster. Joseph moaned in pleasure, for the pain was all but completely gone, leaving only pure, incredible bliss in its wake. He had no idea how long that tall shemale drilled his ass, he only knew that he loved every dirty, sweaty second of it.

"Cum in me, Rosie! Take my slutty ass!" he screamed.

"Yeah, you like it?" she replied through gritted teeth. She reached over his heaving back lean against his shoulders. Arched over him on the tips of her toes she pumped like a demon. Joseph could only scream as her wildly thrusting cock finally erupted into its condom.

"Good God," he groaned as he flopped onto his belly. His hard cock jabbed painfully into the carpet.

"You're telling me!" Rosie sighed as she rolled off of him and peeled her bloated condom from her shrinking cock.

"Now its your turn, handsome!" Lotta said sweetly. Joseph smiled as the cute young shemale urged him onto his back. His cock thrust up into the air, hard enough to cut glass. She wasted no time rolling a condom down his length and squirting lube all over him.

"I need to cum so bad," he croaked at the pretty shemale. Her huge tits wobbled as she settled over him. His cock slipped into her ass easily. Even through the condom he could feel how hot and tight her back door was.

"Mmmm, that hits the spot!" Lotta giggled and wiggled her plump bottom against his lap. Her ass squeezed and milked him as she moved.

"Thanks, Lotta," he reached up took a fat titty in each hand. He'd never been with a girl with breasts as big or as firm as hers. "Your ass feels great! I've never tried anal before!"

"Hold on tight, then!" she winked. She rose up on her knees and started bouncing on his lap like a girl riding a wild mustang.

"Fuck!" the slender man gasped. Her ass squeezed at him, hotter and tighter than anything he'd ever felt. If it wasn't for the condom, he'd have cum then and there. Even then, he couldn't hold out long. Those three shemales and their huge cocks and tormented his ass and had him on the brink of orgasm for over an hour!

"Your little cock feels so nice!" Lotta cooed, licking her luscious lips as she rode.

"Fuck!" Jospeh cried a few minutes later. It was all too much. He came long and hard, filling the condom to the breaking point as his fuzzy balls emptied again and again. He jerked his hips under the bouncing shemale, sending her half-hard cock flopping against his stomach.

"I'm so glad you liked my pie," Lotta giggled as he finally finished cumming. She bent down and kissed his cheek. "You're welcome over any time!"

"Thanks," he grinned up at her shyly. His luck could be odd sometimes, that was for sure.



***



Joseph shivered as he stepped into the cold gray morning. His body ached from the night's abuse, but it was a good ache. He grinned to himself as he walked down the sidewalk to his car. He'd never really thought of himself as a stud, but he'd left three beautiful, very satisfied women behind him. Granted, they were shemales and he'd mainly satisfied them but letting them take turns fucking his virgin ass. Still, it felt good to know that he'd gotten them off so well.

"Good morning!" he cried to the jogger coming up the sidewalk next to his car. He did a double take. She was short, with her long brown hair trailing in a ponytail behind her. Her compact little body was encased tight gray spandex. Her breasts seemed pretty small after Rosie and her friends, but perky nonetheless.

"Joseph?" she stopped dead, her mouth agape.

"Rachel?" he dropped his keys as he stared at her. Of all the places in the world to run into his crush. He silently cursed his luck. He'd just have to meet her as he was doing the walk of shame after getting gangbanged by transsexuals!

"What are you doing here?" she demanded. "In Fox Wood, I mean?"

"Uh, I just met a couple of girls..." he stammered. That's when he saw it. The water company's driver didn't just have cute little breasts, but she had the biggest, fattest bulge between her shapely thighs.

"God damn it!" she stamped her little foot, and turned to face him. "You're not stalking me or something creepy like that are you?"

"Hell no!" he backed away defensively. "The girls that live here had a break down on the highway and they made me dinner!"

"And breakfast too?" she asked, arching an eyebrow. Her lips twitched, as if she were about to smile. She turned a knee to one side and cocked her hip out. Her staggering bulge was on full display.

"No, they're too busy sleeping," he said sheepishly.

"You big goofy fucker!" she laughed. "If I had known you were into T-girls I wouldn't have run off so fast yesterday!"

"Ah, I see," he said, a bit at a loss for words.

"I would have said yes," she added.

"Really?"

"Sure! I'm not dating anyone right now and you're a cute guy. I think you'd be fun," she shrugged. "Unless you really were stalking me?" she asked sharply.

"Nope, talk to the girls here if you want. Rosie, Cindy, and Lotta. They're t-girl models, they said. I've never met a t-girl before them. They, uh, introduced me," he blushed.

"Great, now you're probably dating one of them and I missed my chance!" she frowned. "I was just being cautious. You never know how guys are gonna react. I wasn't prepared to tell you my secret just yet."

"They all have boyfriends," he said quickly. "It was just a one-time thing."

"You're not some sort of man-whore are you?" she asked, barely stifling a giggle.

"I swear, I've never done anything like that before. Not even with regular girls!"

"Okay. I believe you. You don't look like the player type," she frowned, thinking.

"Well, I'd better get going," he said awkwardly. "I'll see you on Thursday, I guess?"

"Yes," she nodded. "And Joseph?"

"Yes?"

"Ask me again when you see me next. You may get a different answer this time," with that she was off, resuming her jog down the sidewalk with nary a backward glance.

"Huh," the engineer sighed as he slipped into his car. She was a strange one, that was for sure. Did he still want to go out with her, now that he knew her secret? He started the car and quickly drove home, lost in thought.

just   his   luck  

Apr 19, 2018 in anal

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