Mistress Cruel Love Ch. 03

"Lay down, Pookie. Face up!" she commanded over her shoulder.

Darius smiled and moved to comply as Heather retrieved the TV remote. By the time she returned, he was relaxing comfortably with his hands behind his head.

"Move down farther! I want your face in the middle of that first cushion."

Darius' cock twitched in its metal housing. He knew where this was going and the blood had already begun flowing to his member. He pushed himself down the sofa as Heather stripped off her sweatpants and underwear. Soon her bulbous, peach-toned ass was hovering just above him.

As he stared up at his girlfriend's giant, fleshy cheeks, covered in lovely creases and patches of cottage cheese cellulite, she looked over her shoulder and spoke to him sternly.

"I did my aerobics about twenty minutes before you got home. Haven't showered yet. Why should I when I have you to clean my ass? I'm going to enjoy my show now. Get to work, slut!"

Darius was cast into complete darkness as she lowered her massive, sweaty shelf-ass onto his head. Her full weight fell onto his face smoothly. His nose and mouth were sealed in the deepest part of Heather's crack as she shimmied on him, making sure he was jammed as far into her rear as he possibly could be.

He inhaled deeply of her sweaty musk before extending his tongue and lapping away at her taint. The feeling of compressed ass flesh pushing down on every square inch of his face felt heavenly. It was difficult to breathe, but Darius didn't care. What little air he could suck through flattened nostrils was one hundred percent pure Heather.

She rocked her ass back and forth over Darius' face for the next fifteen minutes, guiding where his tongue should go. She lifted her full weight from his nose and mouth only occasionally to give him a few scant breaths before dropping her gelatinous mass back on his eager nose and mouth.

Darius moaned in her depths, swabbing his tongue up and down wherever Heather demanded he do so. His neck, sandwiched between the sofa and her crushing flab had no room to move. He could only lick and probe where his demanding Domina let him. His nose ring dragged across her flesh, stinging his healing septum with every lick and brush, but it was worth it. So worth it to an ass fiend like him.

Heather rose from the sofa and turned, her pussy visibly dripping as she stared lustfully at her drooling, sweaty, mess of a boyfriend. She leaned down, grabbed him by the chin and shook his face a few times before releasing it and scorching his cheek with her palm.

*SMACK*

"Thank me for rescuing you from your old life."

"Thank you for the wonderful new life, Mistress!"

*SMACK*

"Use my new name!"

"Thank you Duchess Daphne!"

*SMACK*

"Do you know what this is practice for?"

"...Mistress?"

*SMACK*

"The rest of your life, bitch! Now get your tongue in my asshole!"

She turned and lowered her mountainous ass onto his face once again. Darius' left cheek, scorched from several slaps, was granted the soothing balm of doughy, white flesh. His face was thrust into her saliva and sweat drenched crack as Heather positioned her pucker directly over his mouth.

Darius' wet tongue speared into her silky cavern as Heather settled in to watch the rest of her show. Forty five minutes of wondrous ass worship proceeded as he sucked, slurped and tongued at his Goddess' silky portal.

* * * * *

It was Thursday afternoon and Darius moved around the condo, swishing his feather duster over every surface that needed his attention. His black high heels clicked on the hard wood floor as he moved from room to room. Almost every square inch of his body was covered in shiny satin and clingy silk.

Heather dressed him every day now, and each time he was dressed as a maid she found another garment or accessory to add to his ensemble. Black arm-gloves extended all the way past his elbows and white stockings crept up to mid-thigh. Light, wispy petticoats traveled from his waist down to his knees and under them, silky ruffle panties encircled his locked manhood snugly.

He couldn't deny these garments felt amazing on his bare skin. Darius couldn't think of another time when the simple act of wearing clothes put him in such constant communication with his body. Every turn, every bending motion, every flourish made his entire form tingle with the thrill of forced femininity.

Darius wished his chastity cage was off, if only so he could feel that wonderful velvet texture against his cock. He knew better than to ask for luxuries, though. He was beginning to wonder if Heather would ever unlock him again.

No sooner did he think about his big, beautiful woman than she walked out of the bedroom. She was wearing a tight, mint green top and light purple shorts; one hand clasped to her forehead. Her body was almost Easter egg-like in the combination of pastel colors. She eyed Darius with a look of pure irritation.

"You're still not finished dusting? Get moving! You got other chores."

Her thick body brushed past him, her pudgy curves pressing against his frilly uniform as she headed for the bathroom with her palm clutching the top of her head.

"I'm almost finished. You ok, baby?"

He heard Heather open the cabinet and rattle around the shelves, looking for something. Moments later she reappeared.

"No, I'm not ok! I have a splitting fuckin headache and we're out of Tylenol!"

"Oh, I'm sorry."

"Don't be sorry, just go get me some!"

"Get some... where?"

"The convenience store on the corner. It's not far."

"I... I better get changed."

Heather's expression turned furious, her eyes glaring in disbelief. "You're going to make me wait when I'm in pain?!?"

Darius opened his mouth to speak, but no words came. He had nothing to say that wouldn't make things worse. He was mortified. Darius knew this day was coming, but he'd hoped it wouldn't be so soon. He was going to reveal his new self to the world.

"GO! NOW!" she shouted, no doubt exacerbating her condition.

He dropped his duster and snapped into action; stopping only at the entrance of their room to grab his wallet. Lacking any pockets, he stuffed it down the front of his dress and headed for the door, the silky petticoats swishing all around him.

As he stepped into the hallway, Darius hoped the store was as close as he remembered. The pavement wouldn't be kind to his high heels and his feet were already killing him.

* * * * *

Darius was visibly sweating. He prayed that his makeup wasn't running too bad. The cross-dressing maid looked up and down the medicine shelf at the convenience store's meager offerings. It was no pharmacy, but it had most of the things you might need in a pinch. He scanned the rack of pain relievers until he found what he needed: Top Care Acetaminophen. 500 mg Extra Strength. 100 capsules. It wasn't name brand, but it would do.

He grabbed the small bottle and hurriedly moved to the front counter to pay for it. Darius wanted to get this errand over with as quickly as possible. The looks of disgust, gazes of intrigue and colorful comments he'd received on the way here had already put him on edge.

Darius got in line and a woman walked up behind him. He retrieved his wallet from the front of his dress as they waited for the man at the front of the line to pay for his booze and lottery tickets.

"Nice dress, honey. I like the shoes too!" the woman behind him said with a chuckle.

Darius froze. He wasn't sure what to do. He pretended he hadn't heard her over the low hum of filler pop music playing in the store.

Finally, the man in front of him collected his brown paper bag of vices and moved to exit. Darius walked forward and found himself face-to-face with an amused looking middle-aged woman. She had curly red hair and wore a white apron over her clothes. She eyed him up and down, her eyebrows arching as he drew near.

"Oh my god! Another sissy in a dress? Is it just me or has there been a five-fold increase in bitch-made sissies lately?!?"

The woman behind Darius laughed, cutting off her guffaws with a hand over her mouth. His nerves spiked and his heartbeat shot through the roof. His palm was sweaty around the bottle of meds as he set it on the counter and nodded at it.

"That'll be all."

The clerk ignored him. "So, is this something you enjoy? Or is it a 'Mistress made me do it' kind of thing?"

"Mam, that's really none of your business."

"Oh, lighten up! I'm just making conversation" she said with a wave of her hand. "That means you like it, right?"

"Please just ring me out. I don't want to file a complaint with the owner, but-"

"I AM the owner" she cut him off with a sneer.

There was a few seconds of silence that felt like an eternity before Darius spoke again.

"Ma'am, please, my girlfriend is waiting."

"I bet she is! With a BIG, FAT STRAP-ON!"

The women behind Darius burst into a fit of laughter. More women must have gotten in the queue while the haughty ginger took him to task. He didn't know if she was really the owner, but it didn't matter. He could hear multiple female voices behind him, chortling at his expense. The cruel clerk grinned as his shame took hold. The worst part was his rapidly stiffening penis. Blood flowed to his trapped unit, engorging it until it pressed painfully against the sides of his cock cage.

The woman finally tired of her games and picked up the bottle to scan his purchase. "Seven fifty nine" she stated flatly.

Darius heard the other women making comments under their breath as he paid for the meds. They exchanged lewd remarks about his dress, body and heels. His face burned with embarrassment as he waited to complete the transaction. The redhead took her time counting out his change and handing him the little bag with his item and receipt.

"Run along now sissy!"

He didn't need any encouragement. Darius was already headed for the door. His heels clacked on the tile and his maid costume ruffled around his tense, sweaty body as she called after him.

"ENJOY THAT RUBBER DICK!"

The women broke into raucous laughter yet again. He only had to listen to it for a few seconds before stepping onto the street.

* * * * *

Darius hurried back into the condo and headed straight for their bedroom. He didn't want Heather to suffer another minute. As he moved down the hallway and turned into their room, a surprise awaited him. There was Heather, waiting for him with her hands on her hips and a smile on her face. The fat, peach-toned monster length of Moby Dick hung from her thick, leather strap-on harness.

"Hey Pookie."

"Baby! I got the Tylenol" he said, holding up the bag.

"Oh, I found some in my purse. Remembered I had a backup right after you left." Her smile curled into a much more sinister grin.

Darius set the bag and his wallet on the end table. He couldn't believe he'd gone through that for nothing. But it wasn't for nothing, was it? This was the next step that his dominant girlfriend had planned. This was part of his evolution. This was what he'd signed up for. What he kept putting up with. What he seemed to enjoy, whether he wanted to admit it or not.

"Kneel on the bed. Face down, ass up! Back up right to the edge! Do it NOW, Dana!"

Something was different this time. It wasn't just her commands or the use of his female name. Perhaps his public humiliation had put him in a different mental state. He eagerly moved to comply.

His asshole twitched in the frilly lingerie. He felt a throb of lust start there and pass through his entire body; a ripple of electric anticipation. For the first time ever, Darius realized with crystal clarity that he enjoyed submitting. Even more while dressed as a woman. He wanted that big white cock in his hungry black pucker.

Sure, he'd said the words before, in the throes of passion when Heather demanded it, but he'd never really believed it about himself until now. She had tapped into something deep within him and stripped away the silly pride and fragile ego his true nature had hidden beneath. He could no longer deny his desires. He belonged under his girlfriend's heel and he'd do anything to earn the privilege of being deep-dicked as her slutty maid.

As he got into position, Heather grabbed a bottle of lube and sauntered toward the bed. The massive cock bobbed in front of her, looking more fit to plug a fire hydrant than a human asshole. She leaned over, flipped Darius' dress up and ripped his panties down with no ceremony. His ass now bare and exposed, Heather opened the snap cap and squirted lubricant all over Darius' crack. She repeated the feat on her giant strap-on before closing the bottle and tossing it aside.

Heather stroked the massive dong up and down, smearing the viscous lube all over the head and shaft. The power-drunk Domina pressed the massive head of her white weapon to his small, shriveled black sphincter and traced small circles around his vulnerable opening. She was going to make him beg.

"Did you enjoy your little errand, Dana?"

"Yes, Ma'am."

"Uh huh. The truth comes out... It's about fucking time!"

*SMACK*

Her open palm blistered his ass and made it jiggle. Darius whimpered as the lube-slick glans circled around his entrance. He wanted it so bad. He bit his lip and grabbed the blanket in tight fistfuls.

"Mmmm... fucking time! Double entendre!" Heather laughed. "Tell me what you want, Pookie."

"Please fuck me, baby."

*SMACK*

"Be more descriptive, bitch!"

"Please, ma'am, I need your big white cock in my filthy black ass!"

Heather stopped circling his pucker with the tip. "Ma'am? What am I? Your fucking Aunt? A complete stranger? I don't think you want this cock at all..."

"Please, Mistress! Duchess Daphne! Whatever title my Goddess wants! PLEASE--"

Heather shoved the fat tip of the bulbous monster into his fleshy ring. His walls parted eagerly, inviting the slick, weighty glans and thick shaft into his sensitive walls. Six inches of Moby Dick glided in with no resistance, the bulging phallus expanding his pucker to accommodate its massive girth. Darius moaned into the bedding like the cock hound and size queen he was. His cheeks went flush and his body turned to jello as his prostate lit up like a Polish church.

"You love this cock, don't you?"

"Yes, Goddess!"

"Almost as much as you love being dressed up like a sissy whore!"

"Yes, Goddess! I love it all!"

"That's good, because you're never wearing regular clothes in our home again, you fucking slut! We'll see how much longer I allow you to keep any male clothes at all!"

Heather seized his hips and began thrusting into him fiercely as her libido surged. She shoved more of the milky white tree-trunk of a dick into his yielding black starfish. She grunted and flared her nostrils as more cock was packed in his asshole, sinking it deeper and forcing his pucker wide with each forceful fuck. Her fat ass bounced around the tight leather of her harness as she settled into Domme space and channeled all her energy into spearing her slave bitch.

Darius groaned and howled in brain broken pleasure. His heels slipped off his feet and tumbled to the floor as Heather thrashed him with her hips. He pressed his ass back on her cock in time with her thrusts, willing more of the fleshy length into his ass. His cock grew hard for the third time that day, stiffening and expanding until it reached the painful limits of what his chastity allowed.

"Hands behind your back, Dana!"

He complied and Heather seized them at once. She wrapped her thick digits around his silk-encased wrists and pulled his arms back. Darius' chest lifted off the bed as she shafted him relentlessly. His frilly dress bunched up and his body shuddered as she assaulted his exposed bottom with endless rubber schlong. His head bobbed and his tongue hung out between low, slutty moans.

Pre-cum dripped from the tip of his sad, imprisoned penis. Darius knew his only chance of reaching climax was the mega-cock pummeling his man-cunt. As it thrummed over his prostate continuously the pleasure built at an agonizingly slow pace. His orgasm was always just out of reach... Until suddenly it was on the verge! Then, the fat horse-cock would sink even deeper in his anatomy, delivering a fresh dose of light pain to go with the overwhelming pleasure.

It was everything. It was his whole existence. In that moment Darius earnestly hoped that he never came again. He wanted nothing more than to be railed forever, his sissy body suspended on the edge of climax.

* * * * *

Darius' body buzzed with nervous energy as he was led down the sidewalk by Heather's leash. She walked just ahead of him, tugging it gently in between smug backward glances at her collared property. She'd allowed him to wear regular clothes tonight, but donning the symbol of her ownership had been the compromise.

He'd begged her not to put him in a dress for their Friday night date with Shireen and Markus. Darius had come a long way, but wearing women's clothing in front of his best friend was the one thing he still couldn't abide. It was the last barrier Heather hadn't crushed, though he knew in his heart she would eventually. This time, she'd shown loving mercy.

In place of a maid outfit or something else feminine, Darius was dressed in conventional formal wear. A smart looking yellow, button-down shirt covered his top and was tucked neatly into a pair of brown dress pants. His burgundy dress shoes, which he hadn't worn in years, tapped along the pavement as they made their way down the street.

For her part, Heather wore a satin, one-piece red number that hugged her plump curves and showed off her enormous ass. A small opening between her breasts gave a peek at her underwhelming cleavage while see-through floral patterns around the sleeves allowed one to glimpse her chubby arms. Below that was nothing but thick legs and heels that looked way too thin to carry her.

Beside her was Shireen. The diva's tight, hour-glass figure was traced by an amazing blue dress. Her dark hair fell in long, curly waves and the sides of her outfit featured thick webbing that allowed anyone to behold her sultry, dark flesh pressed against its silky straps.

Markus plodded along next to Darius. Shireen wasn't leading him by a leash, but she might as well have been. He couldn't take his eyes off her generous figure, strutting ass or the knee-high black leather boots that contained her well toned calves.

Darius' dapper friend was classing it up with a purple fedora, purple suit jacket, a white dress shirt and matching purple slacks. He may have looked the part, but he was no pimp and everyone knew it. Following on Shireen's heels, Markus looked more like a lovesick schoolboy the teacher kept smacking with a ruler.

They were dressed in their best because they were all going somewhere new. Somewhere special. Darius hadn't learned what 'somewhere special' meant until just hours ago when Heather let it slip. When he heard the name, he wasn't surprised at all. The prophecy of the cruel convenience store clerk had come true, so why wouldn't another one? After his odd encounter in the gym shower, Darius suspected that destiny would eventually bring him to this place.

He looked up as they drew closer and beheld another extravagant sign. It was even more flashy and suggestive than Queen Shit's welcoming display. The dark outline of a woman with glowing devil horns and a red succubus tail could be seen stepping on the dark outline of a prone male. Her heel was planted in the center of his back and her right hand flashed a glowing whip up and down in the background. Below the figures, the words CLUB ISHTAR were lit up in bright white.

Darius swallowed as they approached the long cement steps leading to the massive club. Shireen had a mile-wide smile and Heather tittered with glee. She yanked on Darius' leash and to hurry his pace. Markus took a long look up at the flashing, animated sign and the building's six story height. He seemed to be in shock that an establishment of this type was seated so prominently in the city.