The New Executive Assistant

Malena had never had a cock that large in her mouth. Mr. Hegworth's was much larger than her dad's, or that boy from school, and she was afraid she would choke on it. He wasn't pressuring her, not grabbing the back of her head like she was used to, but she wanted to do a good job; her employment depended on it.

In retrospect, she should have been more cautious when she was asked to sign the NDA to never talk about her employer, or the contract waiver that said she would "cheerfully" perform any other job-related duties as assigned. The HR woman, Maggie, assured her it was all standard, and that the other girls had all signed the agreements, and they all seemed happy.

So, she found herself in the executive suite of her new company, just fresh out of her ninety-day probationary period, wearing her assigned uniform consisting of white, thigh-high stockings, a garter belt, and white lace bra. She remembered visiting the assigned tailor who got her measurements, murmuring appreciatively as he poked and prodded her body to determine the best fit. At the time she had no idea what kind of uniform she was being measured for, as no one really knew what happened in the executive area, just that the tailor seemed to think that white would suit her complexion best.

Malena had darker, toffee colored skin like most Mexicans of indigenous extraction, and long, jet black straight hair she typically wore in a bun for work. Her rounded face and full, generous lips topped a body with wide hips, slim waist, and full, firm breasts. Her eyebrows were thick, requiring constant attention, and her areolas and nipples were a chestnut brown, matching her eyes. Mr. Hegworth's eyes nearly popped out when he saw her dressed for her new assignment the first time, the white lace contrasting with her dark features.

All she knew was she'd be working with top executives and clients, her background in marketing a desirable asset. She spent the first morning getting oriented by Maggie who showed her the dressing area with her collection of specially selected lingerie and meeting the three other young women who appeared to be happy enough with their current assignments.

There was Libby, with a full curvaceous figure, milky skin and coffee colored hair wearing dark red lingerie, Jamie, who was tall, skinny, and blond with creamy rose skin and light blue eyes wearing light blue lingerie, and Linda, a petite Asian woman with honey skin, short, bobbed hair, small breasts, slim hips and black lingerie. She had seen them before in normal street attire, entering the suite or exiting, and all three seemed friendly enough but the presence of Maggie put a damper on their meeting. Malena had a growing list of questions.

She remembered being instructed to change into her new uniform, and Maggie reminding her of the NDA and special contract. Offering her a chance to back out without knowing precisely what she was in for, only saying it might "stretch her limits from time to time," like now, with that huge cock in her mouth.

She shuddered when she thought of what that monster would feel like if it ever found its way into her pussy, and Mr. Hegworth chided her in his deep, gravelly voice, "Don't be playing with yourself, we'll get to that, and I get to watch."

"Yes sir, er, no sir," she gasped, thankful for a moment to suck in some fresh air.

After changing and introductions, she had been immediately set to some task, writing copy for an internal HR project for a manufacturing company in Indiana. It wasn't particularly challenging, and she really had no idea why she or the other young women were dressed that way except as some kind of twisted office fantasy (which paid too well and came with many perks), until Mr. Hegworth summoned her to his office.

"Do whatever he asks of you cheerfully," Libby whispered to her, looking almost relieved. Maggie shot her a stern glance and smiled at Malena, flicking her head to indicate she should follow Mr. Hegworth.

"You'll be his assistant for now, make sure he gets whatever he wants," Maggie instructed, and Mr. Hegworth beamed at her appreciatively. He was a portly man, with a wide girth and slightly disheveled, ill-fitting clothes. His thinning hair failed to conceal a balding spot on his head, and his ruddy jowls crinkled when he introduced himself and shook her hand. He had to look up slightly to meet her eyes, but it was only a glance, as he seemed more interested in sizing her up and admiring her body in the white lingerie. She was not accustomed to being so brazenly gawked at but realized the lingerie perfectly accentuated her figure.

"Let's see how good you are," he said, as he motioned for her to walk in front of him out of the Assistants Lounge and down the hallway. "Third door on the left." Once inside, he shut the door behind him, and she heard the latch click loudly. "I don't suppose anyone has told you what the other duties as assigned are," he stated more than asked, "Let's see if you'll keep your job." The way he said it made her nervous.

Her previous position was good enough, but she needed the money for her family, especially since her dad was now in prison, much to the relief of her and her sister. But this new position was too good to be true. She could provide for her mother, sister, and brother, and have extra left over. Her college debt was not onerous, and she could easily pay it off now. So, when Mr. Hegworth casually remarked about keeping her job, her heart sank. She resolved to do whatever was required to show she was up to it.

Most of the office spaces in the rest of the building were modern, all chrome and white. Here, things had an older, more classical look. This office was clean, but slightly shabby, with an air of neglect. Mr. Hegworth went to stand behind his massive desk and motioned her over. "Undo my belt and lower my zipper." It was a command, not a question. Malena looked confused. "Duties as assigned, you signed a contract," he flatly stated, waiting impatiently as Malena processed the full import of what she was realizing. "Well?" He looked at her, scanning her face. "Are you cut out for this job or not?"

Malena swallowed hard, fighting back shame and fear, and reached out her hands, as if she were watching someone else's hands, and fumbled at his belt, getting the buckle to unclasp. He didn't have a button or snap at the top of his trousers, apparently it had popped off at some point, so she grasped the small plastic zipper pull and slid it down.

"Now, remove my shoes," and he lifted one foot. She kneeled to pull the loafer off his foot, and he shifted feet. She did the same for the other and he pushed his pants down and stepped out of them, as she knelt staring at his chubby, hairy legs. "Now my underwear while you're down there."

Her heart was racing in fear and shock as she started to pull his white jockeys down, and once the waistband had fallen enough, she saw his shriveled penis peeking at her from within a tangled mass of hair. She fought revulsion and shame as she continued pulling his white underwear down to his feet and he stepped out of them. He took off his suit jacket and was left wearing only his patterned button-down shirt and tie.

He sat down in his leather chair and rolled it back, indicating that she should go... under his desk? She looked confused again. "Your job is to get me hard and keep me hard while I work on a spreadsheet. Do you think you can do that?" Again, while phrased as a question, it really was not.

"Yes sir," she quickly replied, and in a dreamlike state she squeezed herself under the desk as he patted and squeezed her ass while she crawled on all fours. It became very cramped when he rolled the chair back in, and she was sharing the space with his knees and thighs, but she was able to reach her hands out and her slim fingers set to work tugging on his flaccid penis. She tried massaging it, and stroking the head, but that did not seem to be working.

"Use your mouth," came the terse command, and she leaned forward with a hollow ache in her stomach, fighting the smell of sweat and... something, as her mouth opened and tugged on his slightly hardened penis to get it past her lips. Once in her mouth it seemed to respond better, and after some sucking and attention with her tongue, it swelled massively, slowly filling her.

She wondered if her duties would involve him shoving that thing in her pussy, and she shuddered. Mr. Hegworth chided her in his deep, gravelly voice, "Don't be playing with yourself, we'll get to that, and I get to watch." Her heart sank again at his brazen treatment of her as an object, a plaything for his amusement to be ordered about, but she did sign an agreement and could not afford to lose the job. So, she continued to suck and lick at his thick cock, and soon she could hear him starting to wheeze.

"OK, slow down, use your fingers again, slowly," he commanded. And she obliged, grateful for a chance to reset her mouth. She felt that surely, he should have cum by now, it had never taken this long with her father or boyfriend.

The phone chimed, and she heard a young woman's voice: "Mr. Hegworth? Your wife is on line two", there was a pause, "Shall I tell her you're busy?"

"No, I'll take it," she heard him say, followed by "Antonia." He said it flatly, and she could feel him leaning back in the chair. Fortunately, her head was clear of his now shrinking cock, or she might have gotten it crushed by the underside of his desk when he shifted. She couldn't make out what Antonia was saying, but Mr. Hegworth was being agreeable and saying "Uh huh" a lot. Malena had stopped stroking him, but a hand shot down, feeling for her, and she felt it grab the side of her head and pull it forward as he sat back up straight, inviting her to start sucking him again.

The conversation seemed so ordinary and casual, and there she was sucking on her new boss's swollen cock while he was talking to his wife. Her head bobbed and her lips gripped him as she tried to listen and learn what she could of the conversation, but all she got was that she might stop by around lunchtime, and he mentioned "Breaking in the new girl". Malena hoped it was soon so she could collect her thoughts and try to get a grasp on what was happening to her, it all still seemed so unreal.

After the phone call was over, he had swelled up to his full length and girth again, and after a while of sucking and bobbing her head on it, he began to wheeze, and stopped her, rolling the chair back and motioning her out. "That was a good first try," he said, almost approvingly, "next time you'll know what is expected from you." He pointed to the couch at the side of the room. "Go sit over there and pleasure yourself, toys are in the end table. Make sure I can watch you."

Malena opened a drawer in the end table and selected a rabbit style vibrator from the sizable collection. Dildos of varying sizes, eggs, a couple butt plugs and some things she could only guess at. "When you're done, leave them in the basket by the door." He watched as she picked up a lotion dispenser, the sole object on the table. "Lube," Mr. Hegworth said. "Water based. In case you're not wet enough after this," he added as he waved his semi erect penis in front of her.

She wasn't, so she smeared a couple pumps of lube on the rabbit, and then sat on the couch. She spread her crotchless panties wide, affording the older, fat man a clear view of her pussy with its neatly trimmed black bush and sank into the cushions. The vibrator hummed to life, and she teased her clit and her opening with it, spreading her lips open, revealing a surprisingly pink pussy. She felt like she was expected to put on a show, but the now flaccid again Mr. Hegworth had other plans. He pushed a button on the desk phone, "Maggie? Send in Linda."

"Right away Mr. Hegworth."

Mr. Hegworth idly stroked his cock up to some semblance of erectness while he waited. He watched Malena as she inserted the lubed toy into her pussy, positioning the little rabbit head against her clit and started slowly stroking it in and out. His cock stiffened a little further. "Take off your bra," he said idly, and when she did not do it instantly, he added "Now."

She immediately ceased with the rabbit and unclasped the front hook on the white lace bra, the vibrator rumbling on the couch next to her. She slipped the shoulder straps off as the bra slid to the couch. Her boss wheezed his delight at seeing her dark breasts, with even darker nipples and licked his lips. "Watch and learn," he said, "This is what is expected."

Linda, the petite Asian woman opened the door and came in, shutting it behind her. She was nearly Malena's opposite, with short black hair, small breasts, slim, boyish hips and black lingerie. She immediately went to the gross caricature of a man, who seemed entranced by her, and asked if she could remove his shirt. He took his hand off his cock long enough for her to unbutton and remove his shirt. Linda looked past him to Malena, and rolled her eyes, giving Malena a wink before dropping to her knees unasked for and started stroking and licking his cock.

Malena became excited at this, and picked the rabbit back up, inserting it back into her still moist pussy. Watching the slim Asian girl swallow the larger man's full erection caused her cunt to tingle, and she started thrusting the vibrating dildo in and out with a smooth regularity.

Mr. Hegworth reached down to stroke Linda's hair, in the first gesture resembling affection or tenderness she had seen so far. But just as suddenly he yanked her up by her hair, wheezing and sputtering. Linda immediately spun around, pulling the crotch of her panties wide and jutting her hips backward, exposing her hairless and glistening pussy. She planted her hands on his desk, spreading her legs and slightly bending her knees, waiting for him to enter her. It all happened so fast, the suddenness and surety of her motions sent a thrill through Malena, who now pushed the rabbit tight inside her snatch, rabbit head whirring against her clit.

The rotund man wasted no time positioning his fat cock against the petite Asians waiting hole, and without fanfare, shoved it in quickly. Linda yelped at the abruptness of this, despite being clearly prepared for it. Malena was struck by the casual normalcy of all this, as women were simply regarded as things for men to use, and willingly obliged them their whims. The thought of this, plus the sight of the engorged thick member plunging in and out of the tiny Asian, as she braced herself for his violent thrusts, made Malena dizzy. She pressed the rabbit tighter against her clit as her head swam and her legs spread further, and heard a moan escape her lips.

"She probably won't cum from this." Malena suddenly realized he was addressing her. "I'll need you to hurry up so I can hear you." He turned his attention to Linda's back again, and holding her slim hips, continued to thrust in a rocking motion while wheezing faster now.

Malena was entranced by the sight, and she pinched one of her nipples as she felt herself nearing climax. Realizing their boss only needed to hear it, she started exaggerating her moans and writhing with slow undulations as she felt herself growing closer. Her moans became louder, and she started breathing heavily and exhaling quickly in sharp, high-pitched grunts. Hearing herself out loud with an audience excited her further, and soon her body caught up to her voice as she felt a spasm build. Her tension released, along with her inhibitions as she cursed, and let out a sequence of high-pitched breaths, her body shuddering in a toe-curling orgasm.

This was all Mr. Hegworth needed to hear as Malena saw him, through half closed eyes, bury himself in Linda's cunt and grunt a few times. He gave a few shallow thrusts, and then pulled out suddenly. Finished. Drops of cum dribbled out of Linda's pussy and she quickly closed the crotch of her panties, before kneeling in front of the wheezing man, and giving his cock one last suck to clean it of his cum and her juices. She arose, and dressed him again with sure, practiced motions, gathering each pant leg so he could step into before she raised them to his hips. He looked over at Malena while this was occurring and told her, "You might even be able to cum while I'm in you, now won't that be delicious," and he licked his lips and leered at her in anticipation. Linda finished tightening his belt and gave his belly a little pat.

Malena lay there enthralled by the display, and not as disgusted by Mr. Hegworth's attention as she thought she should be. The rabbit still vibrated in her cunt, and she felt herself approaching another climax when she realized they were both being dismissed. Reluctantly, but quickly she pulled it out, her legs still shaking from her previous climax, and turned it off, retrieving her bra and rising from the couch. "I hope you are as tight as Linda, but I doubt it," he said in a challenging tone, as he pointed to the basket by the door, where Malena was expected to deposit her toy. Linda pulled the door shut behind them.

"Welcome to the executive suite," Linda said wryly. "Hegworth's not always like that, he's just showing off for you." They started walking back to the assistant's lounge. "If you're lucky, it will be days until he summons you again. Hopefully you are tighter than me, but I doubt it." She laughed and winked at Malena. "God, I need a shower after that."

Each assistant had their own changing area, with a stall shower and vanity and their own toilet. Linda explained it was the one area where no one would intrude, and while an extended absence would be frowned upon, at least for a while you could have some peace and privacy. She had invited Malena into hers and quickly stripped out her black lingerie to quickly shower, explaining to her how there were sometimes days where no one would summon them and they were free to do light work on projects or relax, as long as when someone needed them, they were ready.

"Occasionally, you'll be asked to stay late, but that's rare. You might even be taken to a party or a client meeting," she said as she was changing into another fresh set of black lingerie, "They spare no expense in getting you dressed up for those, and it's all part of the contract. They even pay you overtime!"

Meals were provided in suite, and they had a menu of items to choose from. Malena was too excited and still in shock to be very hungry but ordered something light just to keep her energy up. She was still reeling from the morning and the vast sea of implications this all had on her life. She learned that Mr. Hegworth was sterile due to a vasectomy he received at the urging of his wife. The others were not but would wear condoms unless the assistant was on birth control, which could be prescribed by a private Gyno. Linda had done that, just to make it easier, it also increased her value to a couple of the men, which was why she was the eldest assistant there.

Jamie was the newest, jokingly referred to as the diversity hire due to her blue eyes and blond hair, and Libby had been there as long as Linda, nearly a year. They were able to chat almost freely under the watchful gaze of Maggie from HR, if they didn't discuss personal matters between themselves and the executives, again, all covered by the NDA they had signed. Libby was the more serious of the three, and she freely offered general advice, most importantly, that their pleasure was a bonus, not an entitlement.

Malena went back to work on her project but kept replaying the events of the morning in her head. The oversized cock stuffed in her mouth and the casually indifferent attitude towards her. Seeing her coworker getting freely fucked by her boss and the shuddering orgasm she had just to enhance his pleasure, was something she could not have conceived of just the day before. She wondered if anyone else in the company knew about this. She certainly had no idea.