Jay peered up nervously as the manager’s new assistant swiftly approached him, a small but impertinent smirk on her face. In a small amount of time, she quickly learned that she was his superior in every way and reveled in the knowledge.
“Miss Lord would like a word, in private.” She swished her shoulder-length jet-black hair as she spun away.
His eyes followed her helplessly as she sashayed back to her desk, transfixed by her perfect form. Jay had been delighted when the previous incumbent in the role, Miss Powell had been promoted, finally breathing some sense of ease into the workplace. She had used her sexual allure to tease and torment him since his appointment and had publicly humiliated him on more than one occasion.
His serenity evaporated when the new recipient started, Miss Jessica Chen made his mouth drop and his cock hardened immediately. The most perfect petite oriental girl had walked into his life and was soon taught that the men of the office were nothing but playthings and she toyed relentlessly with him.
She snapped him out of his gawping as she fixed his attention with a stern glare, angrily mouthing “now.”
Jay leaped up and rapidly made his way to the main office, tentatively knocking under the continued watch of Miss Chen. “Come,” the loud demanding answer made him hurry inside.
“Sit boy,” Miss Lord clicked her fingers towards the seat facing her.
Taking the seat Jay waited nervously as his manager ignored him and continued to read her report. The room was silent except for a low hum of a fan, keeping the room at a cool, almost cold temperature.
Finally, she broke the quiet with a hard slap of the files on the desktop and scrutinized him with her icy blue eyes. “As you may have heard I will be away next week for a conference.” Miss Lord leaned back in her leather chair and crossed her achingly long legs, dangling one red high heel in front of him. “Normally I would require my assistant to accompany me but in this instance, I will be taking you along.”
The last sentence brought his jaw to slacken open, “Me Miss Lord.” The words made his body stiffen and flicked some electricity into him. “I have no experience with that work.”
She waved his question away with a flippant disregard, “you’ll have nothing to do but look pretty.”
Jay flushed with embarrassment at being called pretty, although he had grown accustomed to being treated in this manner.
“Most conferences are dominated by men so I take my prettiest assistant to disarm and confuse them.” Miss Lord brushed her long blond hair from her face, “but this one is mainly women so I think you will be perfect.”
By now Jay had learned the correct response to Miss Lord was always to nod in agreement, “yes Miss Lord.”
“Good boy, we will be chauffeured down on Tuesday at six so be ready and waiting at the front door.” Miss Lord’s implacable features finally broke into a smile, “and I don’t think I need to tell you to be on your best behavior.”
“No Miss Lord,” Jay shook his head energetically.
“Good because I’m more than happy to put you over my knee anytime or anywhere if the need applies.” She playfully tapped her knee to confirm her intention.
“Oh yes Miss Lord I fully understand,” the memory of every painful spank flashed through his head. Jay nodded his thanks and retreated to the safety of his desk. Amid disappointed groans from the rest of the office staff who had grown accustomed to hearing his painful humiliations emitting from her room.
~~~~~~~~~~~~~~~~~~
His quiet lunch respite was broken by the looming figure of Miss Lord whose looming shadow made him gape up at her. She leaned over him and locked her blue eyes on him, her perfume filled his nostrils as she edged closer.
“Come with me on a little trip,” Miss Lord held out her ivory white hand and tightly gripped his like a child. She led him out and strode powerfully towards the exit forcing Jay to scamper after her.
Outside a sharp-suited woman held open the door to the long black car waiting for them, Jay slid into the deep leather interior next to Miss Lord. “Grayson’s please Angelica.”
“Yes Miss Lord,” the driver nodded and the car smoothly proceeded on its journey.
Jay sat stunned and silent, confused but fearful to question his superior. Miss Lord sat quietly beside him and stretched her long smooth legs before her. To escape staring at them Jay gazed ahead and caught a glimpse of the driver in the mirror, her steely grey eyes fixed on the job. Her blonde hair was cut short and it emphasized her perfect bone structure.
His examination of the driver ended as they arrived at their destination, catching him looking she smiled back at him with her full thick lips. Miss Lord gripped his thigh, “we’re here.”
The driver slipped from her seat and opened the door for Miss Lord and Jay, she was even prettier up close. “Come, boy, don’t stare at Arabella.”
Arabella grinned back at him and Jay flushed caught red-handed, running marmaris escort after Miss Lord to escape. Miss Lord strode into the elegant shop and stridently rang the bell for service, as Jay caught up behind.
An improbably coiffured immaculately suited gentleman arrived from the back and extravagantly welcomed Miss Lord, “my dear it’s been too long.”
Miss Lord squeezed back the embrace, “much too long Nigel.”
“So what can I do to help you today?” Nigel leaned on the counter putting a finger to his lips.
“I need a suit for this young boy, make him more presentable.” She waved a hand in Jay’s direction.
“Mmmm I’m sure I could do something with him,” Nigel smirked with a lascivious gleam in his eye.
“I’m sure you could which is why I will observe,” Miss Lord winked back at the tailor.
“Spoilsport,” with a giggle he clapped his hands. “Follow me.”
They entered a dark oak-paneled room with a thick red carpet to sink into, amid racks of clothing. Miss Lord relaxed in a studded leather armchair as she sat back to watch the show. “Strip to your underwear for the nice gentleman, boy.”
Coyly Jay removed his coat and slipped off his tie, undoing his shirt buttons under their watchful gaze. As he slipped down his trousers he remembered to his horror that he had put on his Christmas present from an auntie, SpongeBob boxer shorts.
Miss Lord and Nigel exchanged raised eyebrows at the sight of the childish underpants, “how old are you, boy?”
Crestfallen Jay looked to the ground as Nigel got to work with his measuring tape, before disappearing into the stock room. As he stepped out of his shoes Nigel returned with a variety of white shirts for him to try. The first shirt fitted great for Jay, with plenty of room to move but Miss Lord shook her head.
The second shirt was tighter but still comfortable enough to wear, again she shook her head. The third shirt he struggled to button, clung skin tight to his slim body, with just enough room to button it up.
“Perfect,” Miss Lord clapped her hands in delight. “That size in white, pink, and lavender.” “Let’s try that color,” she pointed to the pale blue trousers on the bench.
Jay stepped into the legs and wriggled them slowly up his legs, they clung so tightly he had to inch them past his thighs and took a deep breath to zip and button the waist. They looked like they’d been painted onto him as he winced at his discomfort in the mirror.
“Oh Nigel, you always know what I want.” Miss Lord applauded the fitting of the boy. “Look how perfect his little bottom is in them.”
Nigel grinned back at her, “Oh I am dear.” With a short slap on Jay’s rear, he returned to the stock room for the matching jacket. “I think I have the perfect fit for him.”
Slipping into the pale blue jacket Jay was happier with this fit, finally having some room to move. Checking the mirror he was surprised by the length, just past his waist covering none of his posterior. “Is it not a little short?”
“Silly boy, it’s perfect.” Miss Lord arose to hug Nigel for his services. “Be a shame to hide such a wonderful pert bottom.” Quickly paying for the clothes Jay carried the bags back to the car and the awaiting Arabella.
She easily took the weight of the bags and located them in the boot before opening the door for Miss Lord. She slipped back into the driver’s seat and awaited her instructions.
“One more trip I’m afraid, off to ‘Forbidden Pleasures.” Miss Lord relaxed back in her seat as she exchanged a glance with the driver.
After a short while they stopped outside a small shop with darkened windows, under a bright pink sign. Jay stared wide-eyed as they maneuvered their way through the aisles of sex toys and lingerie stopping only at the men’s clothing area.
“What size waist are you?” Miss Lord asked as she perused the underwear section.
“I’m usually a 30 waist,” Jay replied hoping this ongoing embarrassment would quickly end.
“We’ll take these two then,” she carefully pulled two pairs of jockstraps from the rack. Miss Lord strode to the desk and confidently pushed them to the girl at the counter, “we’ll take these please.”
The young blonde assistant smirked towards Jay who tried to hide behind his manager, “I’m sure they’ll look great on him.”
“Well if you have a changing room I’m sure he wouldn’t mind showing us,” Miss Lord pulled Jay back into the full sight of the girl.
“Why of course we do, just through there.” Her grin grew as the color flushed on his face, “if your sure he’s ok with it.”
“Oh, he’ll be delighted to model for us,” with a heavy shove Miss Lord propelled him towards the small curtained changing area.
Jay closed the heavy black curtain and shuddered as he watched himself strip in the full-length mirror, goosebumps raised on his pale skin. Carefully unwrapping the package he slipped on the white skimpy jock, once again Miss Lord seemed to have picked a size smaller.
“Is everything marmaris escort bayan all right in there?” the assistant giggled as she shouted the question.
Jay peeked his head around the curtain towards Miss Lord, “they fit fine.”
Miss Lord scowled back at him, “get out here and show me, I want to see what I’ve purchased.”
Nervously pushing through the curtains Jay’s heart thumped through his chest as the check-out girl loudly wolf whistled him. Hesitantly he crept forward towards the women who applauded his appearance.
A brunette shopgirl had joined the audience and loudly cheered, “isn’t he just delicious.” Her blonde friend squealed, “give us a twirl.”
Miss Lord motioned to the boy to turn and give the ladies a full view, “show the girls that sexy little butt.”
His small round firm bottom pushed out through the tight jock, the underwear perfectly presenting his prize procession. The roar of enjoyment grew as he turned his back on the girls, giving him a tingle in his cock.
Miss Lord laughed to the girls, “well did I lie, lovely bottom.” The girls high-fived her as they visually groped the boy. “Boy, get dressed. We do have some work to do today.”
His naked bottom flew wiggling into the shelter of the changing room and threw his clothes back on to flee to the sanctuary of the car. Grabbing the package he returned to Miss Lord’s side as she paid for the purchase. “Say thank you to the ladies.”
“Thank you,” he meekly replied to the girls. Both of whom appeared to be no older than himself and snickered at his subservience to the older lady.
A sharp slap to his bottom brought his escape from the shop and he gladly fled to the car. Angelica held the door open and could barely conceal her smile. Miss Lord slid her long smooth legs into the leather seat and passed the package to Jay. “Back to work, Arabella.”
Arriving back to work, Arabella opened the door for her passengers and proceeded to the boot of the car. She passed the bags back to Jay and nodded her goodbye to Miss Lord.
“Right, I want you ready and waiting back here tomorrow.” Her high heels clicked away before she turned, “be dressed and shave your body, no one wants to see that little fluff on your chest.”
~~~~~~~~~~~~~~~~~~
At six sharp the car approached and Miss Lord’s distinctive voice called from the darkened window, “come boy we don’t have all day.” Jay scampered to the vehicle and the impressive figure of the driver took his bag to the boot.
They drove in silence, Miss Lord’s head lost in her laptop and the driver’s eyes locked on the road. Jay’s mind wandered towards the passing landscape to keep from remembering his usual altercations with his supervisor.
At the hotel, Miss Lord took control and marched confidently to the reception desk. Arabella followed swiftly behind carrying the luggage without breaking a sweat, leaving Jay to scurry after them like a lost child.
“Two rooms in the name of Lord,” she stared down the male receptionist as he checked. Confirming the rooms she passed a key to the boy hiding in her shadow, “your key boy, don’t lose it.”
Jay took the key from her in the smirking presence of the receptionist and sullenly followed the two women to the lifts. Both of them towered over him in the cramped lift, “don’t pout boy.” Miss Lord scolded him in front of the impressive driver who held the luggage without flinching.
Miss Lord entered the room and nodded to Arabella to place the bags in her bedroom and handed his key to Jay. “Your room is next door and be ready when I call for you.”
“Yes Miss Lord,” Jay removed himself from her presence and slipped into his noticeably smaller room. Finally able to remove his constricting suit and relax on the bed in his jockstrap.
~~~~~~~~~~~~~~
Jay dutifully accompanied Miss Lord to each conference and presentation, blissfully unaware of the information expressed. With each, he would be introduced to an ongoing collection of impressively imposing women. Each seemed to compete to crush his hand when they shook, grinning as he winced.
In each room, he felt noticeably the only male in attendance although on closer inspection he found similar slim young boys dotted around the seats. They have all dressed in equivalent tight-fitting suits with matching confused looks on their faces.
After the final talk on female representation, Jay was introduced to Miss Brianna Brown, a hugely imposing woman in her forties. Her gym body bulged through her tight-fitting business suit, it was only the slight wrinkles at the edge of her mouth that gave any appearance of her age.
Her white blonde hair was worn tightly in a bun, contrasting with her deeply tanned skin. Her cool grey eyes conspicuously scanned his body, slowly taking in every inch of him. When she shook his hand she gripped it hard and squeezed long and hard, her eyes locking on his mockingly.
Jay rubbed his hand as Miss Brown left with marmaris eskort her team, “wait in your room until I call you.” Miss Lord patted his bottom, “I have a very important meeting with Brianna and I hope we can finalize some business before the days through.”
Jay watched the two ladies hug and laugh together before the lift doors closed and he could escape back to the relative normality of his room. At six he made his way down to the restaurant and ate, confidently expecting his work to be over for the day.
By eight he was sprawled on his bed watching a film, he’d kept his laptop on the floor to keep from the temptation of porn. At the rap of the door, he knew instinctively it was Miss Lord by the sharpness of the knock. Wrapping himself in a towel he answered and Miss Lord brusquely passed into his small room.
Locating herself on the edge of his untidy bed, she tapped the place next to her for him to sit. “Come, boy, sit next to me.”
Feeling underdressed and self-conscious Jay nervously sat alongside her as she confidently leaned over him. “I’ve had a very productive meeting with Brianna which could be very lucrative for the company.” She playfully stroked his hair as she spoke, “but we just need one more little incentive for her to sign on the dotted line.”
Jay peeked up through his fringe as she toyed with the strands, knowing that his real part in this charade was about to come to fruition.
“Brianna finds you very attractive and she requests the pleasure of your company tonight,” she tapped the end of his nose. “Do you understand?”
To be honest Jay had found Brianna pretty fearsome looking and certainly not his type but he understood what was being asked of him. “Do i really have to?”
Miss Lord teased his lips, “most men would jump at the chance to bed a voluptuous older woman in her prime.” “I mean if you think you could satisfy her.”
Her teasing rose some ire in the boy and although he wasn’t the most experienced sexually he’d never had any complaints. “I can and I will.”
Her hands engulfed his face as she drew a deep red lipstick kiss down on his forehead, “good boy, I knew I could rely on you.”
The boy blushed under her embrace, enjoying the delight that had risen to her sometimes haughty features.
“Now I can see that you shaved as I asked but I want you to take this and shower ready for your appointment at ten,” she pushed a small sachet into his hand.
Pulling the towel over his smooth chest he pondered the gift, “what’s this?”
“This is an enema, it’s to clean out your insides.” She stood tall over him, “take it, clean yourself out, then shower.”
“Is it really necessary,” his small grey eyes gazed up at his superior.
“Yes, I have no idea what sexual shenanigans you will get up to but it’s always better to be ready for any surprises.” Miss Lord playfully tapped his head, “now be a good boy and truly make me proud tonight.”
With one last look at her delicious beaming smile, Miss Lord left him alone with nothing but the remains of her intoxicating perfume and a growing erection. Finally, a chance to restore some masculinity and to gain a sexual conquest to boast to his friends about.
~~~~~~~~
Jay arrived at her door, promptly at ten. The uncomfortable experience of the enema was now behind him, clean, primed, and ready to show Miss Lord she was right to trust in him.
Nervously he tapped on the door and gulped as the imposing Brianna Brown opened it with a smile. She still wore the tight suit but the buttons had been loosened and an impressive cleavage pushed upward. Her long white hair flowed around her shoulders, released from the cage of the bun. It made her disposition less formidable and more arousing.
“Come in, boy.” She kicked off her high heels and walked towards her bedroom, “take a seat, I’ll be out in a minute.”
Jay sat uncomfortably on the edge of the chaise lounge, his hands shaking in anticipation. His cock bounced at every noise from the outer room and his eyes stared at the doorknob awaiting some movement.
When she stepped back into the room the boy’s eyes popped out of his head like a cartoon, she stood in the doorway basking in the reaction. “Do you like it?”
His eyes scanned her from foot to face and his mouth dropped dopily open, “y-y-yes.”
She wore a black and red lace basque with sheer black stockings which clung to her muscular body. Her powerful thighs swung as she strode purposely towards him, seeing the poor boy quiver before her.
His only previous sexual experiences had been with girls of his own age and the sexiest lingerie he’d seen in the flesh had been sheer panties. The sight of this immensely impressive older woman prowling towards him was akin to a fantasy coming to life.
“I’m so glad you like it,” she turned to let him get the full glory of the outfit.
The stockings attached to the basque over her firm curvaceous derriere, and her thong disappeared between the tanned round buttocks. At the sight of her bare ass, he was sure he let out an audible intake of breath.
She pulled Jay up with ease and replaced him on the seat, “let’s see what you have under there.” Relaxing back she spayed her hands out behind her and watched with relish his discomfort. “Strip boy, don’t keep a lady waiting.”