Fun with my assistant part I [MF] [bdsm] [rape] [anal] [impact play]

Eliza gripped the white leather armrest as the Gulfstream lurches, the wheels screeching as they meet the cold tarmac. Eight trips in as many weeks and she still isn’t accustomed to flying. She leans forward, her auburn locks falling over her face, as she tries to control her breathing. The plane is a modified G650 owned by Jones & Hastings L.L.C., the large law firm where she was employed as personal assistant to Brian Jones. The cabin had been stripped down to only allow seating for eight in order to make room for the large conference table in the rear of the plane.

Mr. Jones looked up from the papers spread on the table, “For Christ’s sake Elli, I thought you took some fucking dramamine before we left Chicago.”

“I did,” she replies. God she hated it when he called her Elli. Of all the iterations of her name, Elli was the one that made her hair stand on end. It was what her bastard of an ex-boyfriend used to call her.

“Well go to the bathroom and get yourself together. This is a huge case and I need you to be on point.”

In response, Eliza stood, her legs shaking, and stumbled down the aisle. This bathroom is nicer than my entire apartment, she thought, and probably cost more too. Collapsing on the padded leather cushion that doubled as a toilet lid, she reached out and turned on one of the silver taps on the sink. Grabbing a soft, white towel from the hook, she moistened a corner and placed it on her neck. “Damn,” she muttered as the icy fingers of water ran down the inside of her dress and pooled in her bra under her breasts. Tossing the wet towel in the sink, she grabbed the remaining dry towel and began rubbing at the darkening material.

“You almost done up there?” Came Brian’s voice from across the plane. “What time are the reservations?”

“Just a minute, sir.” Eliza said exasperatedly as she returned to the cabin. “I reserved a private room at Per Se for six o’clock.”

“And you confirmed this?” He asked, staring at her.

“Yes sir, right before we left.”

“Alright.” He nodded. He was turning back to his papers when he whipped his head around to look at her once more. “What the hell is on your shirt?”
“It’s just water. I put too much on the towel.”

“I thought you were cleaning up?” He said with disdain. “Go change, we’re leaving in five minutes.”

Sure enough, Eliza looked out the window to see the black Navigator driving up the tarmac to collect them. She sprinted to the front of the plane and pulled her garment bag from the closet. She had only packed one extra outfit, and it was a size too small. Glancing back she saw her boss absorbed in collecting his papers. Quickly, she unzipped her dress and dropped it to the ground. She didn’t notice Brian’s lingering stare as she pulled the new dress up, struggling with the zipper. By the time she turned around her boss was looking down, closing the clasp on his briefcase. Tossing her wet dress unceremoniously in the garment bag, she hurried up the aisle just as the door to the plane opened.

The meetings that day were grueling. Physically and mentally exhausting. They’d met with three separate, demanding clients, back to back. Arriving back to the hotel at 8 pm, Eliza wanted to change into loungewear and turn on a movie to fall asleep to. These trips took it out of her, and they were happening often lately, but hopefully they would settle down soon. She worked hard, rising to all the demands, balancing them like plates of dinner on a tray. She did it for her kids, she worked hard so they could have a decent life.

Turning down the bed and ready to dive in, her phone rang. She let out an exasperated sigh before picking it up, for it could only be one person.

“Meet me in the lobby in five minutes,” Brian said on the other end. He wasn’t asking, it wasn’t a suggestion. He didn’t even want her company, he just didn’t want to be hanging around the bar alone.

“Yes, sir,” she said with false energy. She stomped her foot and gave the bed one last longing glance before changing again and heading out the door. At least he would pay for the drinks.

Shrugging her dress back on Eliza looked herself over in the mirror. The too-small dress clung to her chest and hips. She frowned as she tugged at the hem, her brows tightening as she turned slowly. “This is ridiculous, why do I even still have this stupid dress?”. She asked herself as she noticed the fabric bunching around the strap of her bra. She wondered if it had been like that the entire day. They were in such a rush when she got dressed on the plane that she didn’t take the time to look. She reached in and unclasped the strap and slid her bra out. The sudden chill caused her nippled to constrict, pressing against her dress. She fruitlessly tried to adjust the dress to make them less prominent to no avail. Sighing, she gave her hem one last tug and walked out the door.

Brian was sitting is one of two large, brown leather chairs situated in the corner of the swanky bar. A gas fireplace was crackling between the chairs, and as she approached she saw him cross his leg while looking over some papers. He had a glass of amber liquid in his left hand and a cigar was smoldering in an ashtray on his right. When she was feet away he looked up and his face softened slightly.

“Didn’t bother changing?” He asked with a raised eyebrow. It was only then that Eliza noticed that he had donned a black polo and dark denims instead of the crisp blue suit that he wore earlier that day.

“I didn’t know I needed to,” she mumbled under her breath. Truth be told, she didn’t have many decent clothes. Almost every dime that she earned was spent on her children who, having entered middle school, seemed to go through clothing and food with equal speed. She had bought the dress she soiled earlier for her interview nine weeks earlier. This one was a gift from her ex-husband who couldn’t be counted on to remember her birthday, let alone her dress size.

Brian’s eyes raked over her curves as she delicately sat in the opposing chair and crossed her legs. “Where are the expense reports for the Jennings file?” he asked brusquely.

“I – what?” she stammered. “I put them in the portfolio yesterday so they should be in there.”

“I know they should be in there,” he said, putting extra emphasis on ‘should.’ “But the fact is they’re not.” He closed the manilla folder and tossed it onto the zebrawood table between them. Eliza reached out and opened the folder and began leafing through the pages within.

“This doesn’t make sense, are you sure you didn’t leave it on the plane?” she asked incredulously.

“Yes, I’m sure. I didn’t even look at the Jennings file until this evening since that appointment isn’t until tomorrow.” He seethed, his mouth becoming a thin line. “I hope to hell you didn’t leave them back in Chicago.” He swallowed the remainder of his drink and raised the empty glass into the air. A nimble girl of barely 20 came over immediately and reached for the glass. As she turned Brian closed his fingers around her wrist, “Another Blue please and why don’t you bring one for my Elli here.” The girl nodded curtly and hustled off in the direction of the bar.

“I’m so sorry sir, I don’t know what could have happened to it.” Eliza whispered. “I can call someone and have them fax over a copy, or-”

“That’s going to look like shit.” Brian interrupted, looking around for the waitress.

“I could see if they could locate the original and have them overnight it…?”

“Elli,” he started, grabbing her elbow, “I’m going to look like a world-class fuckup if I set foot in that meeting tomorrow without having looked over the expense reports. We need them now!”

The chink of glasses signaled the return of the waitress with two glasses overfull with the blended scotch. She bent over and placed them on the table and hurried away. I’ll tell you what,” Brian said, reaching his hand into his right front pocket and withdrawing a hotel keycard, “run up to my room and grab my tablet. It’s in the front pocket of my briefcase on the dresser. Room 187.”

As she grabbed the card from his outstretched hand he drained one of the two glasses in a single gulp. She stood and walked as quickly as her dress would allow out of the bar and toward the elevator. As the doors were closing she could see him pick up the other glass and finish it too.

“Yeah, it’s 20 pages. You can charge them to the room if I need to pay for them?” Eliza had found the expense report on Brian’s tablet and asked the front desk in her sweetest “help me” tone if they could possibly print it for her. She was a smooth talker and really good about getting people to do things they wouldn’t normally do. She wasn’t drop-dead gorgeous but she had a soft, gentle air about her that put people at ease. She was upstairs and back to Brian with the full report printed in less than ten minutes.

“Jesus, Elli, how did you pull that off?” Brian asked her when she returned. He looked impressed and pleased.

“I asked. Nicely.” She smiled her sweet smile at him. It’s why he needed an assistant; he didn’t know how to ask nicely nor did he have any desire to do so.

“Sit down,” Brian demanded. He’d ordered another round of drinks and she emptied hers in one fell swoop. “I’ve been thinking, Elli. And I’ve decided that I’m giving you a raise. I was originally prepared to pay your position a lot more but I wanted to give you a trial before paying you that much. And you have proven yourself. I’m giving you two grand more a month. And I’m giving you a three grand bonus. A wardrobe bonus. Go get some clothes that fit, something a little more professional and less….frumpy than what you usually wear to the office. Maybe a skirt suit? Some pant suits?”

Eliza sat shocked for a moment. She clasped her hand over her mouth and fought tears. “Oh, thank you!!” she said, standing up and hugging him. She pressed her ample chest against him then remembered she wasn’t wearing a bra and broke away. She didn’t care. She was so excited. She would be able to get a new apartment now, a much nicer one. She could enroll Elaina in gymnastics and get Justin that new skateboard he’d been wanting. Their basement apartment was drab, dark and small, not to mention right next to the very loud L-train. Eliza was crafty and had gone to great lengths to spruce it up on almost no budget at all, always refinishing or refurbishing something or making a wreath or curtains or a pillow in a bright pattern. A new life flashed before her eyes.

And a wardrobe budget! As with most things Brian said, she didn’t really know whether to be excited or offended. Had he called her frumpy? She had lost a fair amount of weight during the divorce and after. It was a nasty divorce. She knew most of her clothes were a little too big for her. But frumpy?

Her divorce had been nasty. It was no wonder she’d lost weight. She’d lost her appetite not only for food but for living. Her children were the only reason she even pushed through. Keith, her ex, had gotten her pregnant at seventeen. He was twenty six and already very successful, owning and operating his own business. Eliza lived a comfortable life in the suburbs without working. She raised the children, made the home. Loved the roles. But Keith cheated on her relentlessly. He wanted his women young, and continued to even as he matured. When she couldn’t take it anymore, Eliza filed for divorce. Keith’s wealthy parents hired the best lawyers and fought her tooth and nail and since his business was there before she was, she got hardly any of it. They fought for joint custody, too, so she didn’t receive child support. He may have messed up over and over, but he was an amazing father to their children and she didn’t have the heart to take that away from them.

“No calm down and bring me up to speed on the Jennings account,” Brian says, smiling in spite of himself. They sit there for another hour going over the papers and talking shop. The stress of the day melts away as they throw back one after another drink. They are cozy and laughing at something a client did last week during a meeting. His eyes are twinkling as he chuckles, and she loves it when gets like this. She has seen it a few times since starting work; it’s his fun, gentle, caring side.

They pack up the papers and head up to their rooms, right next to each other. “Hey, I need your opinion on which tie to wear tomorrow,” he says, just as she’s reaching for her doorknob. He’s colorblind and vain and she rolls her eyes and smiles, walking into his room as he holds the door open.

Eliza’s head wasn’t exactly spinning as she walked into his room, but she was far from sober. She decided it would be prudent to sit down before she fell, and the bed was as good a place as any. The mattress sagged slightly under her weight and she swayed a little, but by leaning back on her elbows she was able to maintain a somewhat normal appearance. She heard Brian close the door and the subtle click of the lock. “Wait, did he just lock the door?” she thought to herself, but before the thought was completed it was gone.

Brian walked slowly into the room, gazing sidelong at Eliza as she leaned back on the bed. Turning left, he passed by the bed and over to the closet where his garment bag was hanging. He removed four ties and walked back over in front of her. He carefully draped them, one at a time, over his left arm. “Okay Elli, what’ll it be.” He asked, a slight slur noticeable in his speech.

She blinked her eyes several times to get them to focus on four of the twelve ties in front of her. She tried leaning forward but the alcohol was in full effect and, she had to spread her legs to stabilized herself. Brian’s eyes flitted momentarily downward as she wobbled on the bed. “Can you bring them a little closer?” she slurred. Her words feeling like molasses on her tongue with the effort she had to put into enunciating each one.

Brian leaned over her, hanging the ties over her head like a child playing with a kitten. “Is this better Elli? Can you see them now?” He taunted.

Eliza groped blindly for the nearest tie and accidentally pulled it from his arm. The tie dropped onto the bed landing so that the tail was draped over her neck. Brian leaned further over to collect it and, losing his balance, landed with a squeak of the bedsprings directly on top of her. Without thinking, Eliza tilted her head and kissed his lips. Shocked at her forwardness, she began to withdraw but she felt Brian’s strong hand grip the back of her head, pulling her closer.

They laid on the bed, three of the ties still wrapped around Brian’s left arm as his right cradled the back of her head. She breathed deeply through her nose and the scent of his cologne invaded her nostrils. She embraced him with both arms feeling the taut muscles on his back rippling under his shirt. She could feel his manhood pressing against her through their clothes and the thought of it made her moisten. The next thing she knew his left arm was hiking her skirt higher and higher up her thigh.

“Wait, wait,” she stammered. “We can’t do this.”

“Elli, come on. We both want this.” He replied, the scent of the sixty dollar a glass scotch heavy on his breath.

“Brian, I can’t-” she protested, but his hand continued creeping up her thigh.

“Elli, I just gave you an extra twenty-seven grand. I think you can.” He said matter of factly as his fingers hooked under the elastic of her panties.

She gave an involuntary moan as the warmth of his hand mingled with the heat radiating from her loins. Before she could protest further his finger had slipped inside her. “Ahhh” she breathed aloud as his digit penetrated her silky depths. She tried to clamp her thighs together but his own more powerful leg was wedged between them.

“Don’t fight this.” he whispered in her ear as he nibbled on her lobe. ”You know you’ve been asking for it all evening.” When she tried to protest he said, “Changing clothes in front of me on the plane, coming downstairs without a bra on, kissing me. I’m just giving you what you asked for, and, believe me, you’ll enjoy it.”

Eliza was shocked. On one hand she had done all those things, but it wasn’t done to sleep with her boss. These thoughts kept getting pushed further and further away the more he pumped his finger in and out of her now-drenched vagina.

She made one more attempt to dislodge him by pushing on his chest, but he caught her wrists in one hand and pushed them over her head. With the other hand he deftly picked up one of the discarded ties and bound her hands together. Panicking, she began to struggle in earnest, writhing and bucking on the bed.

“We’ve got a live one here.” he laughed aloud. He withdrew his finger, but instead of climbing off of her he lifted he moved onto the bed, pinning her hips to the mattress. As she opened her mouth to shout or scream, even she didn’t know what she intended to do, he roughly stuffed another tie into her mouth. “Tsk tsk tsk, that’s not any way to repay your boss for such a generous gift,” he said as he waggled his forefinger in her face like he was scolding a toddler. Bending down, he picked up yet another tie and, turning around, bound her ankles together as well.

She lay on the bed, completely vulnerable as he stood and began methodically removing his clothes. When she tried to plead to him with her eyes he simply reached out and turned her over onto her stomach. Brian continued to disrobe until he stood in front of the bed completely naked; his semi-erect phallus protruding in front of him. She felt him grab her legs and pull her toward the foot of the bed until her hips were pushed out over the edge. He stepped up behind her and she could feel him pulling her panties to the side, exposing her most intimate parts.

Eliza suppressed a shudder as she felt the head of his penis at the opening of her folds. She knew there was no way to resist and so she relaxed her body in preparation for the assault. Without warning, he thrust forward, burying his entire length inside of her. She gave a muffled cry that went completely unnoticed as he withdrew and plunged in again. The smacking sounds of flesh on flesh echoed through the room as he relentlessly fucked her swollen cunt. Her head was suddenly jerked back as one of his powerful hands intertwined in her hair.

For Eliza, the sensations were overwhelming. Here she was, being taken by her boss, but at the same time she was enjoying it. Prior to this exact moment, the only person to have ever even seen her naked was her ex-husband. They had met while she was in high school, and he had been her one and only lover. Now, as she lay here being ravaged by her employer, she couldn’t stop herself from thinking what pencil-dick her ex must have been. Never before had she felt so completely filled as she did right now.

A stinging slap to her ass brought her back to reality and, even though it hurt, she realized that it heightened her pleasure. Again and again the slaps came until it felt like her ass was on fire, but now she realized that she was pushing back with each of Brian’s strokes. His pace quickened and she felt something warm and wet drip onto her ass. There was a moment of confusion until she felt his thumb rubbing around her tight, puckered anus. “Oh no, surely not!” she thought and his thumb pressed lightly against the opening with every other circle. Suddenly, his thumb was inside her and she could feel a wave of sensations that she’d never before experienced.

Brian began alternating thrusting his thumb and cock like some sort of perverse synchronized maneuver. Eliza felt the tremors building and, before she could even think about it, she exploded in an orgasm unlike any other. She bucked as wave after wave of pleasure washed over her. Taking advantage of her relaxed state, Brian withdrew his cock from her, still glistening with her juices, and pressed his head to her anus. Eliza realized what was happening too late as her asshole expanded to accommodate his girth. He eased it in, her body shaking, until he was completely enclosed by her tight asshole. A few minutes later she felt his body tighten as he shot his seed deep into her ass.

When he climbed off her, he pulled the tie from her mouth and unbound her. His penis still hanging in front of him, wet with the combination of his and her cum. He walked her to his door and unceremoniously pushed her into the hallway. Looking her in the face he said, “Get to bed Elli, we’ve got an important meeting tomorrow.” As she turned to walk to her room he grabbed her by the elbow, “Oh and Elli, this should stay between us. Understand?”

As Eliza slinked slowly back to her room she could feel Brian’s cum draining from her ravaged ass, pooling in her underwear. She keyed the lock and pushed the hotel door open. The lights were still on from earlier and, as she closed it behind her, she leaned against the door and slid to the ground. Tears stung at her eyes as she replayed the scene over and over. A wave of fresh emotions washed over her. She was outraged that she had allowed Brian to use her like that, but at the same time she felt conflicted over the absolute pleasure caused by his actions. The way he was so forceful and domineering; just the thought of it sent a jolt down her spine.

“What the fuck is wrong with me,” she said aloud as she pulled her knees into her chest and rested her head against them. Her hair draped down like curtains, shielding her from the harsh light of the room. Her head was spinning and she choked back the nausea. Suddenly aware of the wetness spreading in her panties she frantically began stripping off her clothes. Her dress caught on her shoulders as she tugged with increasing desperation. Her chest heaved as she gulped down shallow breaths of air. Finally, with a jerk, the dress wrenched free and she tossed it on the ground. She peeled the now soaked panties off in disgust and carried them to the bathroom. Eliza dropped the soiled panties into the trash can and turned the shower on full hot. As the steam began billowing over the curtain she slid it to the side and stepped into the shower.

The water stung like the pricks of a thousand needles as it beat against her back. It flowed down her spine and washed away the evidence of the evening. She turned around and watched the water turn her breasts red. Leaning her forearm against the wall, she pressed her head against the cool tile. How did I even end up here, she wondered to herself. Her fucking ex-husband, she thought, answering herself. If he hadn’t left her in this state she wouldn’t have had to go get a job and she certainly wouldn’t have just gone through all of that.

Source: reddit.com/r/sexystories/comments/6l1806/fun_with_my_assistant_part_i_mf_bdsm_rape_anal