The Assistant

By Tiffany Reisz
Mar 7, 2019 · 3,954 words · 15 minutes



From the author: Ivy's been in love with her boss Lennon from day one. She's even his work wife. Will sneaking into a party he's attending help her convince him she wants to serve him by day and by night?

“What would you say to a three-day weekend?” Lennon asked, and Ivy could have rung his beautiful neck for even suggesting such a thing.

“Why?” she asked, turning from the filing cabinet in his private office to face him. She’d been digging for something she hadn’t actually needed, which she did about five times a day simply to have an excuse to go into Lennon’s office.

“Why? You don’t say ‘Why?’ when your boss offers you a three-day weekend. You say ‘Hell yes, boss. Best idea I’ve ever heard.’”

Ivy pursed her lips at him. “Why?” she asked again.

“You and I both worked all weekend last weekend,” Lennon said, leaning back in his vintage leather swivel chair. He put his hands behind his head and raised his eyebrows, waiting for her to contradict him. Ivy envied the hands on his hair. Lennon was a young silver fox, and didn’t seem to mind at all that he was mid-thirties and already mostly gray.

“No big deal.” She waved her hand and sat in the club chair across from his desk. When she crossed her legs, she watched him, hoping he’d look at her legs. He did for a split second before meeting her eyes again. “It’s not like you didn’t pay me overtime.” And it’s not like she hadn’t loved every second of it. Weekend work meant Lennon out of a suit and in jeans and his favorite ratty concert T-shirts. Saturday had been Pink Floyd. Sunday belonged to Eminem.

Lennon leaned forward, rested his elbows on his desk and looked her in the eyes. Blue eyes, bright but tired.

“Katie broke up with me,” he said.

“What? Why?” Breaking up with Lennon seemed as insane as setting a Rembrandt on fire. Who did that?

“This is awkward.” Lennon wrinkled his face up, and it was as handsome wincing as it was smiling.

“Me?” Ivy asked.

“She said I spent more time with my assistant than I do with her.”

“You do.”

“If you weren’t, you know, you, it wouldn’t be a problem. But you are you and that’s a problem. For her, not me.”

“Did you just tell me I’m pretty?”

Lennon glared at her. “You know you are. Katie wouldn’t care about that if I didn’t spend my weeks with you and my weekends with you. She says you’re my work wife.”  

Then make me your real wife, you beautiful idiot.

“So why the three-day weekend? You trying to get rid of me?” Ivy asked.

“Never,” he said vehemently, and she cherished that vehemence. “Jack’s taking me out tomorrow for a recovery day of hiking and drinking. Then he’s forcing me entirely against my will to go to a party at a friend’s house Saturday night. And if I’m not here, there’s no reason for you to be here.”

“Three-day weekend it is then.” Ivy stood up and smoothed her skirt down. “And thank you. I got invited to a party too this weekend,” she said, a lie. It wasn’t a party so much as brunch with her sister. “Maybe it’s the same party as yours.”

Lennon stood up and walked around his desk. Gently he lifted the little gold Star of David pendant she wore on a necklace. His fingers were so light on her skin she felt goosebumps all over her arms. And Lennon stood so close she could smell his light cologne.

“No offense, but I don’t think you go to the same parties Jack and I go to. Although if you want to come with us, you can. Beautiful women are always welcome at that house.” He said it like a dare, like a challenge.

“Is it one of those parties?” Ivy asked as Lennon played with the six-corners of the star. They were as comfortable with each other as people who worked in close quarters had to be. She’d smack his hand when he reached for her food. He’d let her sleep on his shoulder when they took red-eye flights to London. But this little moment felt different, felt personal.

“One of those parties, yeah…” He looked a little embarrassed and she adored him for it. He’d been careful to keep his personal life separate from his professional life, even with her. But one Sunday afternoon she’d had to run to his apartment for reasons entirely work-related, and while he’d been on the phone in the other room, she’d glanced through a half-open door and seen Lennon’s bedroom. A leather flogger sat on the pillow and handcuffs dangled from the headboard. When Lennon had caught her looking he’d blushed and stammered an apology. She’d told him she didn’t care as long as what he was doing in his free time was consensual. It had been the first thing she’d thought of to say and only later had she realized it made her sound boring, virginal and utterly vanilla. What she’d wanted to say was, “The handcuffs? The flogger? Lennon, that’s nothing to apologize for. It’s sexy as hell, and I volunteer as your next victim.” There hadn’t been a night since she hadn’t fallen asleep dreaming of his body, that bed, and those handcuffs on her wrists while she made herself come.

Ivy wrapped her hand around his fingers holding her pendant.


Lennon let the pendant go like it had burned him.

“You work for me,” he said.

“I know. I know.” She raised her hands in surrender.

She knew. She knew. They’d had this discussion once before on a night flight when neither of them could sleep but seemingly the rest of the plane could. He’d admitted his attraction to her, and she to him, and the only thing that had stopped them from joining the mile-high club had been Lennon’s innate sense of decency that kept him from sleeping with an employee ten years his junior. She knew if she made the first move it would happen. But she just couldn’t bring herself to do it.

Lennon took a step back. She stopped herself from taking a step forward. “Have a good three-day weekend. I’ll see you on Monday.”

Ivy smiled. “Monday.”

Then she took her file, walked out of his office, and sat at her desk. She didn’t trust herself to walk back into Lennon’s office without declaring her love and/or lust for him, so instead she opened their messenger app and typed, “Need car service for the party? Where? When?”

Lennon wrote back thirty seconds later. “Yes, please. Saturday, nine. 152 Riverside Drive. Warn the driver we’ll be dressed weird.”

“How weird?” she typed back.

Eyes Wide Shut weird.”

“I’ll make a note the comment field.”

And that’s when it hit Ivy…she knew where the party was. She knew when it was. She knew she could go to it if she wanted to go to it.

She wanted to go to it.

Lennon had said “Eyes Wide Shut weird” and implied he’d be dressed in some sort of costume. That would make it much easier to slip in and out. She didn’t want to do anything but see him, and be part of his world for a little while. She wouldn’t even talk to him. But to pass unobserved she’d have to dress the part herself. Saturday morning she made an appointment with her stylist who did her hair in a complicated and very un-Ivy updo. She bought a slinky white dress and a white masquerade mask. Lennon had never seen her wear her hair like this. He’d never seen her wear white. And with the mask covering half her face, he’d have no idea it was her. Since it was one of “those” parties, Ivy also invested in a pair of white seamed stockings and a garter belt and white high heels with white ribbons that tied at the ankle. Once dressed she looked the opposite of her usual work self. Her own mother wouldn’t recognize her.

When nine o’clock rolled around, she grabbed a cab. On her way there she told herself that if the party wasn’t her scene, all she had to do was turn around and leave. She could do this. Get in, get out, don’t cause trouble. Don’t reveal herself and whatever she did, no contact with Lennon. None.

The cab dropped her off, and she paid her driver. It took her a couple seconds to work up the courage to step out and climb the stairs of the black-and-white three-story townhouse. Through the door she could hear the sounds of music and laughter and the usual party revelry going on inside. Before she knocked she tried the knob and found the door unlocked. As quickly and quietly as she could, Ivy stepped inside.



Oh, no.

Lennon hadn’t been exaggerating. It really was one of those kinds of parties.

Everywhere she looked she saw couples coupling. Kissing in doorways, draped over each other on sofas and in the room to the left, some sort of sitting room, she saw a woman kneeling on her hands and knees on a coffee table while a man in a dark three-piece suit and devil horns fucked her from behind. They weren’t alone in the room, not at all. People stood around watching, cheering. Someone even held a stopwatch in his hand. Cash was scattered on the table around the woman’s hands and knees. From what Ivy could tell it was a contest and The Devil was contestant number two. The previous contestant had fucked the woman twelve minutes and sixteen seconds before coming. The current contestant just fucked his way past the ten minute mark. Someone in the crowd said they were neck in neck. Someone else said they were cock in cock.

Ivy stared, mesmerized by the scene. It was porn—beautiful, erotic, playful live porn—and she couldn’t look away. Her nipples tightened under her low-cut dress and her pussy swelled at the sight of the woman taking the cock so casually in a room of a dozen people. Ivy flushed and felt herself growing wet, and her vagina clenched at nothing, wanting something inside it.

“Want to play?” came an accented voice from behind her. She turned and saw the man who’d spoken. He wore a military-style long coat, white shirt open at the collar, plus breeches and Hessian boots polished to a high shine. He was impossibly handsome, with shoulder-length, dark, wavy hair and a wolfish gleam in his dark eyes.

“I…no. Just watching,” she said.

“I shouldn’t play anyway,” he said with a dramatic sigh. “I always win. Hardly fair, is it?” He lifted her hand to his lips at if to kiss the back of it. Instead he flipped her hand over and pressed his lips to the center of her palm. With a wink he walked away, no doubt seeking out more amenable prey.

Ivy turned to leave and came face to bare chest with a man wearing nothing but leather pants. Nothing. Not even shoes. He had shaggy hair, brown skin and a wicked smile. She felt a sudden pang of attraction to him.

“Oh, sorry,” she said. “I—”

“You must be new,” he said, narrowing his eyes at her.

“I’m very new. Very, very new.”

“We like newbies around here.” He cupped her chin. “Tell me what you want, and I’ll make sure you get it.”

Ivy opened her mouth, closed it, then saw Lennon striding down the hallway toward the front door. He wasn’t dressed nearly as oddly as everyone else at the party. He had on black trousers, a black vest, and a white shirt with the cuffs rolled to his elbows. His only nod to the party atmosphere was the black mask he wore over his eyes. Impossible not to know it was him, however. Not with that smile and that salt-and-pepper hair.

“Him,” Ivy whispered. “I want him.”

“You sure about that?” the man in the leather pants asked. She couldn’t believe she’d spoken her wish aloud.

“I am.”

“Then kiss me.”

Ivy kissed the stranger and found his mouth warm and his lips skillful. She’d been so busy with work for Lennon she hadn’t gone on a date in six months. Whoever this man was, she didn’t know, but she also didn’t care. He had big hands that felt good on her waist, and a girl needed kissing sometimes. Even by a stranger.  

And then Ivy was off her feet. Entirely, completely and totally off her feet, being carried over the man’s shoulder.

“Oh my God,” she said, and the man heard her.

“I’m a firefighter in real life,” he said, slapping her on the ass. “Trust me, I know what I’m doing.”

“Glad one of us does.”

“Come on, man,” he said as he carried her into a room. “I caught something for you.”

“Aw, you shouldn’t have, Jack.” Ivy recognized Lennon’s voice.

“You’ve had a hard week. You’ve earned some fun.”

So this was Jack, Lennon’s kinky friend who dragged him to parties? Is this something they did together? Share women? Ivy wanted to be jealous if it was, but instead she found the prospect arousing, the thought of being passed back and forth between them.

Ivy gripped the sofa cushion hard and tried to get her bearings. She was in a room, a very nice but small room with antique furniture like out of Pride & Prejudice or something. Door closed. No lights on but for the fire burning in the fireplace. No bed. Fireplace with an ornate, dark-wood mantel and a low fire burning. Other than the couch she and Jack sat on, there was one armchair across from them and a huge steamer trunk that acted as a coffee table. Lennon sat in the chair and held his wine glass lightly between his fingertips. He was watching her.

“This is how it works,” Jack was saying as he slowly eased her panties down her legs. “Since you’re new…I do whatever I want to do to you and you say ‘Red’ when and if you want me to stop. And what I want to do to you is fuck you while my friend watches. Then he will do whatever he wants to do you. He won’t be nearly as gentle with you as I will. Yes? No? Red?”

Ivy glanced at Lennon, who grinned at Jack’s warning.

She was scared, her heart pounding, her blood pumping so hard in her ears it sounded like the roar of an ocean.


She whispered the word so Lennon couldn’t recognize her voice. But Jack heard.

“Good answer,” he said, and casually unzipped his pants to pull out his cock.

He reached for a condom from the bowl of them on the steamer trunk. She couldn’t believe this was happening as he stroked himself to his full hardness and rolled on the condom so matter-of-factly he could have been tying his shoes if he’d been wearing any.

“You can say ‘Red’ anytime,” Lennon said from his armchair. “We’re big boys. We have self-control.”

Ivy nodded her understanding, taking comfort in his words. It made it easier when Jack pushed her legs wide open. Out of the corner of her eye she could see Lennon leaning forward, lifting his chin to see her better. Since she’d gotten a full wax yesterday, she knew he could see everything—her open labia, her clitoris, her wetness—and it aroused her even more to know Lennon was seeing her body without even knowing it was hers. Jack inserted his index finger into her and rubbed along the walls of her vagina.

“New and eager,” Jack said with a dirty grin, clearly impressed by how wet she was. She realized quickly he wasn’t talking to her, but Lennon. “I’ll open her up for you. You finish her off. Sound like a plan?”

Lennon answered, “A perfect plan.”

Jack gripped her by the back of the knees and knelt between her thighs. This was happening…it was actually happening…Ivy breathed quick, shallow breaths to calm herself. It didn’t work. Jack had his cock in his hand, and the tip pushed against her clitoris. A spasm of pleasure shot through her, and Ivy instinctively lifted her hips to offer herself to him. With one smooth stroke he was inside her. He pushed her dress up to her stomach, gripped her waist and rode her with firm steady thrusts. She couldn’t believe she was doing this, letting a strange man fuck her while her boss watched. She lifted her head and watched Jack’s cock pumping in and out of her. No denying it—she was doing this. Her head fell back on the sofa and she turned toward Lennon. She didn’t mean to meet his eyes but as soon as she did, she couldn’t look away. See me…she wanted to say to him. Look at me. I’m not who you think I am. I’m not just your assistant. I’m a woman, and I need you like this…He saw her. Those blue eyes of his never left hers as Jack fucked her. If only he knew her, knew it was her. It’s me…she told him with her eyes. It’s Ivy, and I want you enough I did this for you, to be with you…

Jack was fucking her hard now, and Ivy opened her legs wider for him. Lennon moved from the chair and sat on the steamer trunk next to them. She wasn’t ready for him to touch her, but touch her he did, pressing his hand onto her lower stomach and pushing down as if trying to feel Jack’s cock moving inside her. Then Lennon dipped his fingertips into his white wine and touched her clitoris with them. She inhaled sharply, nearly flinching at the sudden coolness on her burning body. He grinned as he rubbed the swollen knot of flesh, toying with it at first before giving it the serious attention it needed. Her hips moved in tight circles as Lennon touched her and Jack fucked her. All sensation was concentrated in her pelvis, in her sex. Lennon worked her clitoris with two fingers and it more than she could take. This man she adored and lusted after touching her so intimately while she was being fucked…she came with a cry and a shudder, her hole gripping and grabbing at Jack’s cock still pounding her. He slammed his orgasm into her as Ivy lay back, closed her eyes and took it.

She was empty inside again and her body felt warm and drowsy. Somewhere she heard a door open and close. Ivy was being lifted into strong arms. Limp and spent, she let the strong arms pull her upright and press her into the back of the couch. Thighs nudged her legs open and someone penetrated her again. Ivy opened her eyes and found herself in Lennon’s arms, her chin on his shoulder, her legs wound around his waist, as he pinned her to the back of the couch with his cock inside her.

His hands were on her back, lowering the zipper on her dress. She stiffened, suddenly wide awake.

“We’re alone,” Lennon said, kissing her bare shoulder as he slid the straps of her dress down her arms. Down, down it went until he’d pushed her dress to her waist, baring her breasts for him. “Don’t be shy.”

Shy? She was finally having sex with the man she’d adored for two years. Ivy leaned back, arching for him, offering her breasts to him. He ran his hands over them, squeezing them lightly, holding them in his palms as he licked and sucked her nipples. Lennon was sucking her nipples and it felt better than anything had ever felt in her life. Fucking her softly at first, deeply, and then harder and harder. Jack had warned her Lennon would be rougher with her than he was. But Jack hadn’t warned her it would feel this good. He was fucking her so hard now she could feel it in her stomach. She loved it, needed it, had needed it ever since she went to work for Lennon. He pulled out of her but only to turn her, bending her over the sofa arm. He entered her from behind and fucked her deep, his hands holding her breasts and squeezing them, tugging the nipples until she moaned.

“You like this?” he asked, and his voice sounded so unlike him. So forceful and dominant.


“When I’m done fucking you I’m going to flog you. Then fuck you again. You want that?”

“Yes.” She was so wet from his thrusts she felt it dripping down her thighs.

“I knew you would.”

But how did he know? He didn’t even know it was her.

He didn’t know…

“Red,” Ivy said.
Lennon pulled out of her immediately as Ivy yanked her dress back up.

“What’s wrong?” he asked, looking scared, concerned. He touched her arm. “I didn’t hurt you, did I?”

“No,” she said, scrambling off the sofa. “I’m sorry.”

He reached for her again as she headed for the door, but she kept walking away from him and out of the house.

What was she thinking, having sex with her own boss without telling him it was her? Jack knew he was having anonymous sex with a girl he’d never met before. But Lennon didn’t, and that wasn’t right. No matter how much she wanted him, how good it felt, it wasn’t right.

By Monday morning, Ivy had pulled herself together as best as she could. She dressed in her normal clothes, did her hair the normal way, prepared to act as normally as she could. She wouldn’t blow her cover. She wouldn’t confess. She wouldn’t put Lennon in a horribly awkward position because she’d followed him to his party like some lovesick puppy. She would be a grown-up and carry the secret.  In the break room she poured two cups of coffee and marched into his office like it was any other day.

“Morning,” she said, handing him his coffee.

“How was your weekend?”

“Good. Yours?” Ivy asked, keeping her face empty of expression.

“Good. Too short.”

“Typical, right?”

“Right. But back to work. Can you bring me the Close Brothers file?”

She walked to the filing cabinet and opened the top drawer. When she pulled out the file, something fell out onto the floor.

Ivy bent to pick it up and found a black mask in her hand.

She looked at it, then looked at Lennon who was smiling smugly at her with his hands clasped behind his head.

“You tan easily, you know,” he said. “But your Star of David pendant blocks the sun. You have a six-pointed pale spot on your chest.”

“You knew it was me?”

“The whole time…”

“I didn’t mean to. Jack was there and he asked me what I wanted and I said you. What’s going to happen?” Ivy’s heart pounded outside her chest, the mask clutched in her hand, memories of his mouth on her breasts and his fingers on her clitoris setting her to blushing and flushing and burning inside and out.

Lennon stood up and walked over to her. As he passed the door, he closed it and locked it.

“What would you say to a four-day weekend?” he asked. Before she could answer he dipped his head and kissed her slow and deep and long, his tongue touching hers, his hands on her lower back and roaming lower, and his hips pushing into hers. She pulled back from the kiss and stared up at him. He knew. And she knew. And they’d done it anyway. And now they were going to do it again.

“I would say…Hell yes, boss. Best idea I’ve ever heard.”

This story originally appeared in Best Women's Erotica of the Year.