*DING DING*
The bell situated above the entrance to Miss Scarlett rang as Markus nervously walked in and closed the door behind him. It was a Sunday afternoon, two weeks since his first visit to Club Ishtar. This was the appointment he’d been dreading. Unless Shireen had set this up as an elaborate joke, the store was going to doll him up for a second trip into the Femdom underworld.
Markus was decked out in a button-down shirt, slacks and a classic flat cap. The knowledge that he wouldn’t be wearing them for long hung over him like a dark cloud. That was the reason for the backpack slung over his shoulder. He needed somewhere to store his normal clothes once the ordeal was over.
He proceeded into the store and scanned it from the entrance. It was clearly a women’s boutique, yet it seemed not all their customers were female. Shireen had been specific about their willingness to outfit both women and men. The rows of the shop were fairly close together and the store was filled with dresses, gowns, costumes, lingerie and other feminine apparel.
In no time at all, a curvy Latina with shoulder-length black hair strolled into view. She wore a sparkling, clingy red dress and matching red rimmed glasses. Markus wondered if she was the owner and eponymous ‘Miss Scarlet’ or if everyone who worked there was encouraged to wear red in accordance with the theme.
“Hello! I’m Rita. Can I help you find something today?”
“Hi Rita. I’m Markus. I believe I have an appointment?”
“Ahhh, yes. You’re my two o’clock! I was told you’re looking for a costume, but wasn’t given any specifics. What is it you need?”
“Ummm, I know I shouldn’t be bashful about this, because I’ve been told you provide such services, but it still feels a little odd to me…”
“Something intimate I take it?”
“Yeah, let’s go with that.”
“For your significant other, or…?”
Markus’ cheeks burned with awkwardness as he removed his cap. His gaze fell to the floor. “No. I’ll be needing something in my size.”
Rita’s professional demeanor faded into a sly smile and she placed a hand on her hip. “Out with it, then! How is it you’d like to dress up?”
“It’s not what I’d like, Ma’am. You see, I’m in this theater group and right now we don’t have enough women to play all the roles.”
“Uh huh.” Rita’s smirk was growing more amused by the second. “It definitely sounds like you’re into role playing.”
“It may sound silly, but it wasn’t an uncommon practice in the days of Shakespeare. Men dressing as women.”
“It’s never been uncommon. And you are being silly right now.”
Markus laughed nervously. His eyes darted away as Rita’s gaze remained locked on him. There was a few moments of painful silence before the haughty woman spoke again. “How will I be dressing you today, Markus?”
“Like a maid.”
“A French maid?”
“Yeah, I suppose…”
Rita snickered and lifted one hand gracefully. Her index finger pointed to the back of the shop, behind her. “This way. Follow me.”
She turned and they headed further into the store, her high heels pumping like a runway model as Markus followed the hostess in. They passed many aisles of dresses, formal wear, undergarments, shoes and boots before taking a turn into a large room in the back. As they emerged, it became clear that they were in the kink section of the store. Leather, latex, fur, silk and kinky costumes of all kinds were bountiful.
Rita opened her mouth to speak, but was immediately silenced by the sound of a phone ringing in the distance. She pointed to the rows of fetish-wear around her. “Have a look around. I’ll be right back.”
The lady in red strutted back to the front counter and picked up the receiver. “Miss Scarlet. Rita speaking. How can I help you?”
“Hi Rita. My name’s Shireen and I’m just calling with a heads up. If he’s not already there, a man named Markus should be stopping by shortly.”
“Oh, yes, he’s here. We were just getting started with his appointment.”
“Perfect! Now, just so you know, this man is here to dress up like a slutty maid, but he’s probably going to try and get away with the bare minimum. I would ask that you not let him do that. Make sure he gets the works. Dress, lingerie, wig, makeup, nails, heels, etc. You have a couple hours before I arrive to pick him up. If he gives you any fuss, tell him Shireen said to obey Ms. Rita or the date is off.”
Rita’s laughter echoed through the store. It was loud enough for Markus to hear all the way in the back room. It sent a chill down his spine as he examined the ‘French maid’ section of the costume department.
“Thank you so much, Shireen. It seems I’ll have no trouble hitting my sales target today.”
“My pleasure. Oh, and one more thing…”
“Yes?”
“He loves purple.”
Rita laughed again before saying goodbye and hanging up. She darted to the back of the store where one of the other women on duty was stocking shelves.
“Hey Katy, can you watch the front for a while?”
“Sure thing” the young blonde answered with a smile.
“Thanks. I got a special client in the back room and I might be a while.”
Rita returned to the back room hastily and found Markus where she’d left him. She pointed to a short hallway just behind him. “We have special dressing rooms for our adult section right back there. Head into room one and remove your clothes.”
“You mean down to my boxers?”
“No. Everything comes off.”
“What?!?”
“I know we’ve just met, but I was a nurse in another life. You’ve got nothing I haven’t seen before.”
Markus stared at her in disbelief, frozen for a few moments before acquiescing. “Alright, but don’t I need to pick out some clothes first?”
“I’ll handle that. I’ve just spoken to Ms. Shireen and she filled me in on everything. Give me your waist and shoe size. I can eyeball the rest.”
Markus gave her the numbers before slinking off to the dressing room. He passed a pair of women carrying bags of their purchases. They eyed him suspiciously as they passed in the hall. Once they’d walked by, he could hear them comment behind him.
“Ugh… There’s always a pervert or two in here.”
“I know, right?”
Markus sighed and entered the changing station. He began removing his clothes and placing them in a neat pile on the table. When he was finished, he turned and kept his back to the door. He wasn’t about to put on a show for Ms. Rita unless he had to.
After a couple lonely minutes of standing in the quiet, cool room, the door opened and Rita entered. “Still shy I see?” She tossed a couple garments on the table, both contained in neat plastic packaging. “Put those on. I’ll be back with more, shortly.”
She walked out, leaving the door wide open. Markus turned to find what she’d left. His eye bulged as he discovered a premium set of satin, crotchless panties and some white pantyhose with garters.
“Oh, god…” he muttered as he took them up and started dressing. He slid the panties on first and his cock poked right through the hole in the lacy, stretchy garment. Markus couldn’t deny that they felt nice on his skin. Nicer than any pair of boxers or briefs ever had.
“HAHAHAHA!” a voice boomed from the hallway and Markus practically jumped out of his own skin. He never even saw the woman who’d spotted him sporting his new, silky undergarment. “Close the door next time, sissy!” her voice chided him as she continued down the hallway.
Markus’ hand flew to his chest as his heart pounded. He crossed to the door and shut it firmly. Had Rita done that on purpose or was she just so casual about people being naked that she didn’t think twice about it? Both seemed plausible.
Next came the pantyhose sliding up his dark skin. Soon his legs were covered in a frilly, white tint and his cock was trapped against his body. Markus had to admit, the silkiness outlining his unit felt oddly pleasurable. It made his cheeks go red. Markus’ every instinct told him to put his old clothes back on, run out of the store and never look back.
*CLICK-CLACK*
The door opened and Rita entered once again. She was carrying a shiny purple and white dress, a long pair of purple leather boots and some item he didn’t recognize. This time she had a full view of Markus in his panties and silky leggings.
“Hmmmm! That’s more like it!”
“The pantyhose are are little tight, Ma’am.”
“They’re supposed to be, but if you think they’re too tight we can go up a size.”
“I’m amazed you have this stuff in my size at all.”
“Miss Scarlett caters to everyone. Women. Men. Big Women. Even big men! You are all sexy little tarts in waiting.”
“That’s very egalitarian of you.”
Rita chuckled before setting down the dress and boots. The other garment she was carrying unfolded in her hands and Markus finally got an idea of what they were. They looked like… fake breasts?!?
She held the bra-like apparatus up for Markus to see. The weighty breast forms dangled and stretched up and down in between her outstretched hands. “This is next.”
Markus folded his arms over his chest. “Is that really necessary?”
“They’re just little B-cups to help complete the look. Surely they’re not too heavy for a big, strong man like you?”
“I don’t know…”
She raised an eyebrow and pointed at him sternly. “Ms. Shireen said you would dress the part completely or the date is off!”
Markus sighed. “Fine.” He let his hands drop to his sides and turned around at her direction.
Rita guided him to one of the long mirrors on the wall and started wrapping the breast forms around his chest. She pulled the stretchy bindings around his back and hooked them together, then followed suit with the top straps that went over his shoulders.
Markus cringed as he watched his feminization begin. He stared at his own sad visage as a woman’s hands reached around and maneuvered his new milkers until they were in perfect position.
“There we are! Now for your dress.”
He turned and watched Rita stalk back to the pile of clothing. She pulled the slick, protective plastic film from the dress and displayed it on the hanger for him to see. A second, internal cringe hit Markus as he studied the shiny garment. It was purple PVC surrounded in snow white maid adornments.
It featured ruffled shoulders and elbows, a large white apron on the front and long stripes of silky white along the bottom of the dress and at the wrists. She spun it around and Markus got a look at the finishing touch, a thick white ribbon tied in a bow at the back. Wherever the dress wasn’t covered in plumage, it shined glossy purple.
“Well, I can’t argue with the color” Markus quipped, trying to find some humor in the horror.
“I’ve been saving this piece for just the right customer. I knew it was you as soon as you walked in! You’re going to turn heads wearing this” she announced with a sinister grin.
“Yeah, that’s what I’m afraid of.”
Rita motioned for him to turn around again and Markus obeyed. Another short sigh escaped his lips. At this point he just wanted to get the whole thing over with. She closed the distance to him and Markus could hear the back of the dress being unzipped.
“Stand up straight and arms forward!”
She circled to his front as he reached out with both hands. Within moments the cool, slick feeling of PVC began creeping up his right arm. It stretched and clung to his skin as Rita worked the first arm of the dress up his limb carefully. Markus shivered as the shiny, lacy ensemble began to surround him.
* * * * *
After ten minutes of careful direction by Rita and another five minutes of violently yanking the thigh-high boots over his feet and up his calves, Markus stood in awe of himself. He stared in the mirror, inspecting his form as he waited for the haughty clerk to return. The purple dress shined in the overhead lights. The glossy gown flowed down to his knees where white, PVC boots took over. Billowy fabric, the color of snow, accented his dress everywhere, covering half of his front and giving him the classic maid look.
Markus walked back and forth awkwardly, testing his footing. Thankfully, the boots only had short heels and they were fairly thick. His face still gave him away as a man, but he had to admit, Rita had done a bang-up job. He looked pretty hot from the neck down.
As if thinking the devil’s name made her appear, the door opened and she walked back in. Markus turned and found her holding two more products with a wicked smile on her face. He didn’t like the look of either.
“What are those?”
“A cock cage and a butt plug. You want to go all the way for your lady friend, don’t you?”
“Ohhhhhhhhh NO!” Markus shouted, holding a hand up defiantly. “I told Shireen I’d dress up. I didn’t agree to no freaky toys!”
“Cmon Markus. You can trust my gentle touch” she implored with a wink.
“That’s a hard no, lady. I know you think I’m secretly into this, but I’m just doin it to humor Shireen.”
She lowered the toys, a glum expression registering her disappointment. “If you say so… Alright, follow me. We still need to find you a wig and do your makeup and nails.”
“How much longer is this gonna take?”
Rita put her hands on her hips. “It will take as long as it takes. You can’t rush beauty. Besides, do you really want to wait outside until Ms. Shireen gets here? You still have an hour before she arrives.”
Markus’ face drooped and his eyes went wide with fear. “You know what? That’s an excellent point. Please do take your time, Ma’am.”
Rita chuckled as she turned and exited the dressing room. “Good sissy” she taunted as he followed her out.
* * * * *
Markus’ heart beat a hundred miles an hour as he stumbled into Club Ishtar at the end of Shireen’s leash. He struggled to walk in his new heeled boots. The bag at his side contained feminine products and extra cosmetics supplied by Ms. Rita in case he needed to freshen up. He’d never felt more out of place in his life, dressed as a maid and being led into a sex club wearing a collar, wig and a pound of makeup. He couldn’t deny the silky lingerie and smooth costume made him feel tingly, but that was the last thing on his mind as he entered the den of lustful, empowered women and dutiful male submissives.
‘Why did I agree to this? Jesus Christ! There are other fish in the sea!!!’
As if to answer his question, Shireen turned to check on him. Her gaze lingered and, for once, the look wasn’t dismissive or annoyed. It was genuine delight. Markus’ mouth hung open as he stared back. Her smile was worth all the treasures in the world. That’s why he’d returned to this insane place.
They came to a stop about fifty feet from the dance floor. Shireen unclipped the leash from his collar and took a step back. “Okay. I’m gonna go do some shopping of my own. I’ll be back to get you in a few hours.”
“What?!?”
“It’s time for you to go on a journey of self-discovery, Markus.”
“What about the rules?!? I’m not supposed to be here by myself!”
“Relax. You stuck out like a sore thumb last time in that purple suit.” Shireen eyed him up and down, studying his satin, lace and PVC clad form. “You blend in much better now.”
“But what if some of these ladies realize I’m on my own?”
“Then, I guess you’ll have to do what they say” she answered with an amused smile.
Markus had no reply; just a look of growing anxiety. His brain was melting at the prospect of what he was about to do.
Shireen rolled her eyes. “Don’t be so dramatic. It’s innocent fun and it’s just for a few hours. When it’s over, you can take me out wherever you like.” She pointed to the phone in the pocket of his dress. “I want pictures of you from all around the club! No shenanigans, like hiding in the bathroom!”
Markus sighed and nodded.
The domineering diva flashed him a fresh smile and waved as she walked back to the lobby. “Bye! See ya in a bit!”
* * * * *
Markus put on the biggest smile he could and tapped his phone to take the selfie. The flash went off and there he was, a black man in drag steeped in a purple and white French maid costume. He studied the picture for a few seconds and nodded thoughtfully. Now that his ensemble was complete, he had to admit, he was pulling it off.
He’d seen advertisements for drag queen shows that were popular in recent years. As far as he could tell, he passed for a woman at least as good as their contestants did. It was a weird thing to note and even more odd that he would have any sort of pride in it, and yet, that’s what he was feeling.
It’d been a half hour since Shireen left him. Markus had wandered up to the second floor of the club and taken pictures of himself in front of several different venues. It was a miracle he hadn’t been accosted yet. He knew the longer he stayed by himself, the more likely someone would notice he wasn’t being escorted. He walked along the corridor above the swirling mass of dancing and lights below. Markus tried his best to look interested and happy to be there.
He stopped in front of the next showroom and took another picture of himself. In the background was the entrance to the venue. The marquee over it said ‘Mistress Hannah – Shibari Queen.’ There were depictions of ropes, knots and people hanging in suspension bondage on either side.
Markus stepped away from the attraction as soon as he confirmed it was a good picture. He crossed the hallway and took another look at the party below. He found a solid looking pillar to rest against and leaned his back on it. He needed to find somewhere to sit down and give his poor feet a rest from the stifling heels. A remix of RuPaul’s ‘Supermodel’ blasted through the club. The tune’s echoes cascaded upward through the escalating floors of debauchery.
You better work! Cover girl!
Work it, girl! Give a twirl!
Do your thing! On the runway!
Work! Supermodel!
You better work it, girls! Of the world!
Wet your lips! And make love to the camera!
“Hey! You gonna stand there all night?”
Markus looked up to see a short, blonde woman in red leather and latex standing in the doorway with her arms crossed. She was staring at him intently. He pointed at himself and gazed back at her with a quizzical expression.
“Yeah, you! The slut in purple! I don’t see anyone else loitering outside my door. C’mere!”
He pushed himself off the column and started toward her. Markus knew he had to play it cool, or he’d be in real trouble. This was one of the club Dommes.
“Hello… Mistress Hannah?”
“That’s right. I’m the Mistress of Ropes. Queen of Shibari!” She studied Markus up and down. “Wanna get tied up? You look like the kinda tart who enjoys some bondage!”
“Love to, but I’m following orders right now.” He responded in the most foppish, feminine voice he could emulate. “Mistress told me to take pictures all over the club before returning to her.”
“Mistress who?” she asked suspiciously.
“Mistress Shireen” he answered. “And my name’s Markus. You can check the guest list if you like. We arrived not long ago.”
Hannah relaxed. “I see. Still using a male name, huh?”
Markus waved at her with his painted nails and offered a weak chuckle. “Oh, you know, there’s just so many lovely names to choose from. I haven’t decided yet.”
The woman in red seemed less amused. “Generous of your Mistress to let you choose” she replied, stone faced. “When you find her, tell Mistress Shireen that the Queen of Shibari would love to show you the ropes. My knots and ties would look wonderful digging into that purple dress of yours!”
“I will. Thank you Mistress!” Markus said before hefting the front of his dress and strolling off. “Maybe I’ll see you later!”
“I look forward to it” Hannah spoke before turning and re-entering her domain.
Markus scurried down the gallery, sweating bullets as he fled.
‘Holy shit, that was close! New rule: no loitering!’
He made his way to the next set of staircases and marched his way up. As soon as he emerged on the third floor he instantly regretted his decision. There was a medium build woman in neck-to-toe black latex waiting outside her door. Markus couldn’t escape the feeling that Club Ishtar was built like the classic Bruce Lee film Game of Death. More difficult opponents waited on each ascending floor until you reached the final boss.
She leaned against the doorway running a nail file over the fingers of her left hand. Her hair was jet black with a streak of pink dyed into it. The marquee above her establishment said ‘Mistress Cindy – Exquisite Torturess.’ The signs to either side of the room displayed a fist colliding with the outline of a scrotum and a woman kicking a man in the balls.
“Hey there Miss Purple! You’re not one of the club maids. What are you doing up here by yourself? Do you still have your balls? I’d be happy to punch them, if you do.”
Markus bubbled over with nervous laughter as he slowed to a stop. He lifted one flattened palm up to his brow and made a show of looking across the way, inspecting the horizon. “No, thank you, I’m just looking for my Mistress!”
“Oh, come now! I know a pain slut when I see one” the haughty woman persisted. She stepped forward and closed in on Markus, smiling wickedly. “A lot of women in this club like to bust balls, but I promise you, I’m the best. I know how to do it slow and sweet. I can soothe you in between each delicious wave of pain. Doesn’t that sound nice? Let me be your Mistress for the next little while…” Her eyebrows raised and she curled her index finger in the come hither motion.
“Uhhh, my Mistress isn’t here! Thanks, but I gotta go or I’ll be in trouble!”
Markus turned and hurried off, heading back down the staircase he’d just climbed.
Cindy snickered. She returned to her customary waiting position, leaning against the doorway. “You’ll be back!” she called out before she resumed filing her nails. It was important to keep them short and smooth in her profession.
* * * * *
As he reached the ground floor, Markus breathed a sigh of relief. Going upstairs to take pictures among the severe club Dommes of Ishtar would be the hardest part of the evening, he hoped. That was behind him now. All he had to do was get some more snaps of himself at the various attractions around the dance hall and he would be set. Then he could find somewhere to chill. Maybe if he went to the bar and ordered a drink, he could take it easy for the last hour or so.
*SMACK SMACK*
“MUSH! MOVE, YOU WORMS!!!”
Markus turned and beheld what had to be the most bizarre sight he’d witnessed in his entire life. A woman dressed in Amazonian warrior garb was following behind a team of men, saddled in full leather horse tack. Each male slave was decked out in a full gimp suit, overlaid with a leather harness around their torso, legs and head and a gag fixed in their mouths. All of them were collared and leashed. The buckles and chains of their getup clinked and jangled as they pranced forward.
The tall brunette towered over them, grasping the reigns that led to an O-ring where all their separate leashes connected together. Her other hand lashed out with a braided cat-o’-nine-tails as she barked orders at her bound sluts. When he realized they were approaching swiftly, Markus got out of the way and gazed in fascination as the fiery woman whipped and cursed her leather team right through the concourse where he’d been standing.
As they headed into the distance, Markus watched them turn into a hallway with a bright, flashing neon sign above it. It read ‘PONY GAMES’ and had an arrow pointing toward the entrance. He’d noticed the sign before and wondered what the hell it meant. Now he had some idea. Markus shook his head, at once frightened and confident he didn’t want to learn more.
“OH. MY. GOD! Mr. Purple?!?”
The somewhat familiar voice sent chills down his spine. Markus looked to his side and, sure enough, there they were. The three enormous white girls who’d attempted to lure him into their booth of servitude the first time he was there. One wore thick leather, another flowing satin and lace, and the last donned shiny latex around her humongous curves. They were like some bizarre team of hellish female super villains existing purely to torment him. Markus cursed his rotten luck.
“Is that really him?” the blubbery blonde inquired.
“Yup, that’s him” the raven-haired behemoth confirmed. She placed her hands on her bulbous hips. “That scrawny woman who owns him must’ve got em a makeover!”
“A definite improvement” the pudgy woman with dark brown hair chimed in.
“He’s collared this time, but still no leash! We can fix that, right ladies?” the blonde chuckled. She opened her leather bag and pulled out a thick leash with a metal fastener on the end. All three women closed in on him. Blondie approached from the front, holding forth the snap clip of the leash while the other two boxed him in from the sides. Markus backed up as far as he could before running into the wall. He held his hands up in surrender.
“Please! I’m just looking for my Mistress!”
“If she keeps leaving you alone in the club, that means she wants you to have some fun with us” the black haired Giantess replied. She pushed her satin-clad bulk up against him until her ample curves were pressing into his sides.
“That’s right. So we’re gonna oblige” the brunette added, pushing her bulging latex body into him from the other side. “Unless you’d rather we take you to Lost and Found?”
Markus grimaced. If they reported him to the club and they found out Shireen wasn’t here, that could get them both in trouble.
“No, please! That won’t be necessary! I’d be happy to, uh… entertain you, for a while.”
The busty blonde pressed in from the front, completing their fleshy barricade. With three ample guts pressing on him from all sides in various fetish attire, she reached up and clicked the fastener around the O-ring of his collar.
“That’s more like it. Now, follow us, Miss Purple.”
* * * * *
“HAHAHAHAHA!!!”
The women hooted and laughed at Markus, trapped below their booth and licking away at the blonde’s leather boots. Blondie was decked out in full leather attire and an officer’s cap to complete the look. He remembered her from the first visit to Ishtar. Some poor maid had lavished her boots with a long, thankless tongue bath. Now, that maid was him. After just a few minutes of anxious lapping, his tongue had grown painfully raw.
He slurped his wet, warm pink appendage up and down her glossy leather. Markus considered himself lucky the boots had been shined recently and didn’t seem too dirty. That didn’t make the taste of leather polish any more welcome, but it was better than tasting dirt and mud. His tongue slobbered up and down loudly in between grunts from his PVC clad form. The other two ladies reached out with their feet and gave his ass and side gentle nudges as they commented on his performance.
“Sounds like he’s new at this.”
“Yeah, I’ve gotten much better service from the club maids. That’s for sure.”
“Maybe his skinny owner isn’t big on foot worship?”
“All the better for him to get some training from me!”
Markus continued lavishing blondie’s boots and listening to their lewd comments until the leash was handed to the next woman. The brunette in black latex pulled him to her side of the table until Markus’ face was right in front of her thick, rubbery calves. She ducked her head down briefly to give him instructions.
“Take my shoes off, gently, and get to work. I expect a nice, long massage and kisses all over my glorious feet!”
“Yes, Ma’am” Markus answered in his girliest voice, eager to please the demanding Dommes so he could be on his way.
He slipped her shoes off to reveal bloated, pudgy white feet. The smell of them hit like a punch to the face. It was the thick odor of sweaty feet that had been crammed into heels all day. He began massaging them as he reached down to place his first kiss on the top of her left foot. Markus cringed as he got his first taste of her flesh. A powerful whiff of her toes followed as he began making his way up and down her bridge with gentle kisses.
Markus couldn’t believe he was doing this. Every vestige of his will that remained screamed at him to get up and leave, but the fear of being found out and disappointing Shireen kept him in line. He’d done crazy things for pussy before, but even he was shocked by how far he was going this time. The power women wielded over men was fearsome and growing by the day. Even men who weren’t into Femdom.
“So, how does he rate as a masseuse?”
“Amateur at best” the brunette scoffed. She pushed him away with her left foot and stuck her right one in front of his face. Markus went back to work, hoping to get it over with as fast as possible so he could move on to whatever his final task was. Her caressed her fat, fleshy foot up and down; littering it with dutiful kisses.
“No surprise. Any slave who can’t lick boots properly isn’t going to give a good foot massage!”
“Yeah, he’s pretty worthless as far as I can tell.”
When she’d had enough, the brunette mashed the bottom of her right foot into his face and pushed him away. “He’s all yours” she said to the black-haired matron before handing her the end of the leash.
The enormous woman in satin shifted her bulk to the side, yanked on his leash and pointed her finger down at the dent in the leather cushioning where she’d just been sitting. “Your head, right there slut!”
Markus gritted his teeth and stifled a whimper as he crawled to the end of the booth. He knew what she wanted after witnessing the arduous affair during the previous visit. He turned around, put his back up against the bottom of the seat and poked his head out. He got a brief view of the ceiling of the club’s first floor before the gigantic woman shifted her flab across the leather. She lifted up the bottom of her silky dress and her bulbous mound of giggling flesh slowly blotted out his vision like the dark moon of a solar eclipse.
Within seconds his face was enveloped in gelatinous ass and her weight shifted down on him until it felt like his head was going to burst. She wiggled her hips from side to side, pressing him down with her bulk firmly into the warm leather that had previously cradled her incredible girth.
“Start licking, bitch!” she yelled as she swatted at his sides. Markus could barely hear her words below the mountain of blubber. He obeyed instantly, lest one of her stinging palms find a more tender spot to encourage him.
He worked his tongue up and down her crack, his hot breath blowing across her flesh as he bathed her ass in warm saliva. Markus had eaten booty before, but never one this massive. Never one that was so giant and all-consuming that he was bathed in darkness as his tongue wormed its way through her cheeks. Never one so fat that his tongue could barely touch the vinyl thong wedged deeply in her crack.
His lipstick had already worn off while pouring affection onto the first two women’s feet. Now his mascara, blush, and the rest of his cosmetics were running as he labored away under her shelf of an ass.
He inhaled what precious air he could get through the tiny split in her enormous, clamped cheeks. He continued slurping away, hoping she’d dismiss him before he passed out. Markus bolstered himself and began to kiss and lick with vigor. He hadn’t come this far to have it end in failure.
After a few more minutes of servicing her crushing folds, the giant woman’s ass cheeks slurched off his face as she shuffled to the side of the booth. Markus gulped at the air like a goldfish out of water and gasped in relief. The three women all glared down at him with looks of disgust as they began to exit the booth.
“You SUCK, purple!”
“Seriously, get some skills.”
“C’mon, girls! Let’s go find some club maids.”
The leash was unclipped from his collar and the three haughty, super sized Dommes squeezed out of the circular booth. Their latex, leather and silk garments squelched, meshed and rippled against the leather seating until they’d extracted their hefty curves from its luscious grip.
The trio waddled off, chatting among themselves and leaving Markus in an exhausted daze. His body was drained and his makeup was ruined, but at least he’d survived the encounter. Once he recovered his strength, he’d head to the bathroom and fix his face before getting himself a stiff drink.
* * * * *
Darius hummed to himself as he emptied the dryer. It had been a peaceful weekend and the apartment was full of music as he went about his chores. He was on schedule, so far. Just a few more tasks and he could get started on dinner.
When the dryer was empty, he lifted the basket and exited the washroom into the hallway. He proceeded into the living room, his heels clicking on the hardwood floor. His satin and lace maid outfit tightened around his body. He’d come to love the feeling of the silky fabric on his skin.
Heather was seated on the sofa, her head bopping to the free-form jazz that streamed through the house. She wore a white tank top and leopard print yoga pants around her thick thighs and ample ass. Since finishing her workout, she’d been on the internet posting on her fan site. Darius smiled as he approached her.
“How’s it goin, baby?”
She looked up cheerfully. “Awesome! Seven new paying subscribers so far this weekend! And a lot of likes and comments on the first video I uploaded. They loved seeing you get pegged in your maid outfit, so we’ll be doing a lot more of that! A lot of them want you to take off the mask.”
Darius blushed. Doing that in front of the camera had made him nervous at first, but after a while, it felt like any other time she fucked his ass. He liked having the eye mask on, though. It allowed him to retain a level of anonymity. Not that he was really worried about being discovered, since the likelihood that anyone watching the video knew him personally was minuscule, but still, he preferred to play it safe, for now. “I dunno honey… I-”
“Don’t worry” she interrupted. “You can wear it until you feel comfortable without it. I’m not gonna jump through every hoop these horny sluts ask me to. If I start, it’ll never end.”
“Thank you, baby” he replied earnestly.
“Hey, before you put that stuff away, get me a drink. I’m in the mood for an orange Crush.”
“My pleasure, Mistress.”
Markus set the basket down on the sofa beside her. He walked to the kitchen to fetch her drink. Heather finished typing and set her laptop aside with a sigh of contentment. She looked over at the laundry basket and her eyebrows began to scrunch. The plump Goddess reached in and felt the clothes, her expression growing more annoyed by the second.
“Dammit Dana!” she yelled as he walked back with her beverage. “Did you forget to use fabric softener again?!?”
Darius flinched, realizing instantly that she was right. “I’m sorry, baby. I know I keep forgetting. It’s just, before I met you, I never used to…”
“I know you didn’t” she responded, shoving the basket aside. “That’s why your clothes were all faded, dried out and crinkly! Is that how you want our clothes to be?!?”
“No Ma’am” he answered while setting her drink on the coffee table. “I’m sorry.”
“This has happened too many times! Come here and get over my knee! Right now!”
Darius grimaced, but obeyed without hesitation. He lowered his form gently onto her enormous thighs. Heather reached over, pulled up his skirt and yanked down his panties. His butt-plugged hole and caged cock were exposed to the cool air as she grabbed his sides and molded him into the position she wanted. Darius’ ass was thrust up and his face buried in the couch cushions.
“After these fifty spankings, you’ll remember to use fabric softener. Isn’t that right?”
“Yes, dear.”
Heather grabbed his buttplug, pulled it free and tossed it on the floor unceremoniously. Darius’ stretched pucker slowly contracted to its normal diameter. His fleshy walls already missed the invader he’d grown so accustomed to. Darius was addicted to the sensation of fullness and the gentle pressure it placed on his prostate as he went about his daily chores.
“You can clean that up when I’m done. Then, get back to your duties.”
“Yes, Goddess.”
She chuckled and rubbed his ass in gentle, circular motions; preparing his buttocks for an open palm beating. “You know Mistress does this because she loves you, right?”
“I do, baby.”
*SMACK*
Her first blow snapped off his bare, black ass. The loud, familiar sound of harsh skin-on-skin contact pierced the air.
“Don’t call me baby when you’re being punished!”
“Yes, Mistress! Sorry, Mistress!”
“Good. Now start counting.”
*SMACK*
“One.”
*SMACK*
“Two.”
*SMACK*
“Three!”
* * * * *
Markus relaxed at the bar, his feet mercifully getting relief as they rested on the metal rung at the bottom of his stool. He’d been wearing heels for three hours or so and gained a new level of respect for women who wore them regularly. He took a sip of his rum and coke and thumbed through his phone, inspecting the pictures he’d taken thus far. Markus had gotten a few more on his way to the bar.
‘This should be plenty for Shireen. Now all I gotta do is find a way to kill an hour without getting into more trouble.’
He pocketed his phone and took a quick look up and down the bar. Markus scanned the faces of several patrons until the sight of one, in particular, made him freeze in place.
‘OH MY GOD?!? MARY???’
Seated just nine stools down from him was the administrative assistant of the firm he worked for. Markus almost didn’t recognize her in the skimpy outfit. He’d never seen Mary show that much skin before. Regardless, it was definitely her.
Mary sat at the bar with no one around her. She almost looked bored. The racing event on the big screen, which featured the same kind of leather pony slaves Markus ran into earlier, was the one thing holding her interest.
She was a big woman, although not nearly as bulky as the women who’d accosted him twice now at the club. Mary could definitely be described as thicc with massive, white milkers that her pink, spaghetti-strap dress barely contained. Her substantially plump caboose bulged outward from the confines of the silky dress that ended just above her knees. Mary was a shoulder-length brunette with matching brown eyes that shimmered with warmth.
Markus wasn’t sure exactly how old she was, but by his estimation she had about twenty years on him. She looked good for her age. Her finer physical features were highlighted, for a change. She was dressed for fun instead of her typical, conservative work attire.
He cautiously backed out of her field of vision. Markus thought about sneaking away to some other part of the club, but quickly realized that would be foolish. If he played his cards right, Mary might be his ticket to safety! There were disadvantages to approaching her like this, but Mary was an older, more experienced woman. She would understand! She had to.
Summoning up his courage, Markus slid off the stool, strode down to where Mary was sitting and took a seat beside her. He looked straight ahead, saying nothing at first, until Mary broke the silence.
“Hi there! Having a good time tonight?”
He peeked over at her with a sheepish expression on his face. “…Hey Mary.”
The hand not holding her drink flew directly to her chest as she hopped up in her seat. “Oh my god! Markus?!?”
“Shhhhhh…” he said, holding a finger to his painted lips.
“I… I had no idea!” she exclaimed. Her eyes were wide as she scanned him up and down.
“Mary, I swear to you, this is not something I normally do!”
She let her hand slide from her upper chest. Her eyes returned to normal as she adjusted to the surprise. “What do you mean? Is this your first time? Did you lose a bet? Help me out here.”
“Something like that. Look, what I need you to know is this… The woman who brought me here ditched me and I’ve been very nervous ever since.”
“Oh” she giggled. “Sounds like someone’s having fun with you.”
“You could say that.”
“Why don’t you just leave?”
“It’s complicated.”
Mary’s giggles broke into outright laughs. “Okay, now I think I know why you’re here!”
Markus couldn’t tell if it was the alcohol talking or if she really thought it was funny. Either way, Mary hadn’t reacted to the revelation poorly, so he didn’t care.
“Listen, could you do me a huge favor? Let me hang with you for the next hour or so? Assuming you’re planning to stay that long. I don’t want to ruin your fun, but it would mean a lot to me.”
Mary leaned back in her seat and took another sip of her cocktail. She looked at Markus dreamily, leaving him in suspense for a few moments before answering.
“Of course I will. Don’t be silly.”
“Thank you! Needless to say, no one at work ever hears about this. Right?”
“Naturally.”
Markus breathed a sigh of relief.
Mary stirred her drink before returning her gaze to his sissified form. “I’d like to know the rest of the story, though.”
He nodded. “Sure. I owe you that much, at least.”
The voluptuous secretary chuckled while scanning him up and down a second time. “Hope you don’t mind me saying… You make one hell of a sexy maid!”
* * * * *
8:44 PM
SHIREEN
Hey beautiful, where you at? You can’t keep dodging
my texts! I did what you asked and now we got a date
to plan!
Hi Markus. I promise I’m not avoiding you!
It’s just been a crazy week. Beyond crazy, really.
I’m having a glass of wine to unwind. And to celebrate!
Celebrate? What’s the occasion?
Some very good news. Although, I’m sorry to say,
it may seem like bad news to you.
Oh?
I just got a big promotion. One I’ve been working
for a long time. Higher salary, bigger office, the
whole nine yards.
What? That’s great! Congrats!
Why would I think that’s bad news?
Because it comes with certain conditions. I’ll be
moving away. Very soon. They want me halfway
across the country by next week.
Oh. I see.
Yeah, my life is kind of being upended. I’m not even
gonna have time for a proper move. I’ll be relying on
Heather and Darius to pack up and send most of
my stuff. I’m going to be living out of a suitcase for
a while.
Yeah, I get it. Your career comes first.
No time for a date before you go.
I understand.
I’ll be flying back whenever I can to see my friends.
I promise, you’ll still get that date! You earned it.
It’s all good, girl. I’m happy for you.
Thank you for understanding, Markus. 🙂
I’m having a “goodbye” get-together Saturday
night if you want to join in. We’ll be getting drinks
and having fun at Dango’s.
Yeah, maybe. Let me see how my weekend
is shaping up.
Of course. You take care, slutty maid. 😉
I’ll be in touch.
You too, Queen of Kink.
* * * * *
“Ooof, that’s rough” Mary imparted as she looked at him with genuine sympathy. “Some pretty terrible luck on your part. I’m sorry it turned out that way.”
“I don’t know” Markus replied with a shake of his head. He took a swig of his drink before continuing. “I feel like I was kidding myself about Shireen all along. Like it wasn’t meant to be, you know? It might be for the best.”
The duo sat at the table of a local diner, waiting for their lunch orders. It was Friday afternoon, the time they’d agreed to meet and debrief after their encounter at the club. Markus found Mary surprisingly easy to talk to, even after the conversation shifted to his recent woes.
She’d always been kind to him and helpful at the office, but Markus was gaining a whole new appreciation for the busty brunette. Not only had she shielded him at the club, but she’d been very understanding about his predicament. Aside from a few booze-fueled chuckles, she’d been nothing but considerate. Mary was the shoulder he needed to cry on right now. He certainly wasn’t going to tell Darius about his cross-dressing adventures any time soon.
“Markus, you showed incredible courage and an open mind by getting out of your comfort zone like that. Maybe it would’ve blossomed into a relationship with her and maybe not, but the important thing is, you know how to treat a woman. And you’re not afraid to let her take the lead. Any woman would be lucky to land a guy like you.”
He sighed and smiled weakly. “Thanks, Mary. Yeah, I gave it a shot. At least I won’t regret not trying.”
“And you got a hell of a story out of it!” she said with a sly grin and a wink. “Even if it’s only me you’re telling at the moment.”
Mary was dressed in one of her typical office outfits; a thick, gray one-piece that glided over her pudgy curves. Her ample sweater puppies jutted out from the stretchy fabric and her perfume wafted across the table. A series of white and silver necklaces dangled down from her neck, contrasting nicely with her dress and drawing attention to her most prominent assets.
Hairstyle aside, her glasses, outfit and full figure reminded Markus of Velma from Scooby Doo. The nerdy cartoon girl had been one of his first crushes as a boy.
“So, is that why you go to the club? You like it when women take the lead?”
“I think it’s a nice change of pace” she replied confidently. Mary lifted her coffee cup and took another sip. “I’m no Dominatrix or hardcore deviant, but I’ll admit, I get a little thrill out of it. When you’re my age, you get your thrills where you can. It’s either that or subsist on those cheap romance novels they write for bored house wives.”
“Your age? What’s so bad about being thirty five?” Markus asked with a grin.
Mary laughed giddily and waved him off. “Oh, stop! See, I knew you were a smoothie! I’ve seen you hit on women at the office.”
“You have? Damn, I hope I wasn’t being too obvious…”
“You weren’t. Or your ass would’ve been reported to HR and booted, by now.”
“Good point” Markus noted, his eyebrows lifting as he nodded his head.
The waiter arrived with their food and they both dug into their lunches. Markus had a delicious burger platter while Mary enjoyed a bowl of tomato soup and a pesto grilled cheese. They chatted about work as they ate. As the meal wound down, they shared a few tales about the crazy things they’d witnessed inside Club Ishtar. Many laughs were shared before it was time to head back to the office.
“I got this” Markus announced, signaling for the check.
“Oh, thank you so much” Mary responded with a smile.
“No problem. Let’s do it again some time.”
“Or, instead of lunch” she perked up. “Why don’t you come over to my place for dinner? I make a hell of a lasagna.”
Markus’ eyes opened wide at her sudden and very forward proposition. He knew she was single, so there was a good chance she was asking for more than just a dinner guest.
“The problem” she continued “is that I always have too much leftover. So I don’t make it often, because I hate throwing out food.”
The waiter came and took Markus’ card. Markus waited for him to shuffle off before responding.
“Throwing away good food is certainly a shame” he answered, smiling back. “And I gotta be honest, you hit my weak spot there. I love a good lasagna.”
– – – – – – – – – –
Only half of my content is published on this website. The other half is available to my subscribers. (Chapters 6 – 10 of Mistress Cruel Love are available now!)
If you enjoy my work, wish to support it and want to read the latest chapters in all my series, check out my Patreon and SubscribeStar! (Do an internet search for “Patreon James Bondage” or go to SubscribeStar.adult and search for “James Bondage”.)
Thanks for reading! Your votes and feedback are always appreciated!