Boss Lady

Boss Lady

Status: Finished

Genre: Erotica


Status: Finished

Genre: Erotica


Reggie learns that working late comes with some sexy perks.


Reggie learns that working late comes with some sexy perks.


Submitted: March 05, 2016

A A A | A A A


Submitted: March 05, 2016




A Short Erotic Story


Sharae Lyles



It was after ten on a Monday night. Reggie should have been gone hours ago, but he’d had a lot of research to finish up for his boss. His job as a paralegal was a stepping stone to starting his own high powered career as an attorney and he needed this to look good on his resume. He’d been working for Josslyn Roberts for three months. She was a successful, no nonsense personal injury attorney with a reputation for winning at all costs. Reggie thought she was also one of the most beautiful women he’d ever had the pleasure of meeting. She was of average height for a woman, skin the color of nutmeg, and sharp whiskey brown eyes. Even though she had twenty years on him, she could give any woman closer to his age a run for their money. She was wealthy, educated, and very well respected in the community. She’d never been married and had no children. Reggie suspected her career was what was most important to her. He was on his way out for the night, but he had to drop off some papers to her before he left. When he arrived at her office door, he found it open just enough that he could peek inside. Long brown legs were propped up and crossed on top of her glass top desk, naturally wavy dark brown hair was piled up in a messy bun, and a pen was between her teeth. She was thumbing through a Today’s Law magazine while jazz music played softly in the background. Reggie felt like a peeping Tom while he took in his boss, but he couldn’t help it. She was just that gorgeous. Finally, he cleared his throat and tapped on the door to announce his arrival. She looked up at him, offered a small smile and waved him inside.

“I didn’t realize anyone was still here,” she told him. Her honeyed voice still had signs of a Brooklyn accent even though she was now a Floridian.

“I wanted to finish the research on the Milsap case.”

He handed her a manila folder and watched as she opened it and briefly scanned his work.

“I’m impressed, Mr. Price. Thanks to your great work it looks like I’ll have another win under my belt. You’re going to make a great lawyer.”

Reggie blushed a little at her comments, nodded his head in thanks. He was trying to keep his gaze from landing on her cleavage. Josslyn was wearing a white blouse and two of the pearl buttons were undone. He could just see the tops of her smooth brown breasts and it made his mouth water just thinking about how soft they must be. His eyes locked with hers and she was watching him with a knowing grin on her heart shaped lips. He cleared his throat. He was embarrassed that she had caught him looking and even more embarrassed that she knew exactly what was on his mind.

“Have you eaten, Mr. Price?”

“Uh, no. Not since lunch. And you can call me Reggie.”

“OK, Reggie. I’m starving. There’s a Chinese restaurant a few blocks away that stays open late and has delivery. Care to join me for a late dinner at the office? My treat.”

Josslyn didn’t wait for him to reply. She was already reaching for the phone on her desk and dialing the number to the restaurant. Reggie removed his black tote from his shoulder and took a seat in the comfortable black chair on the other side of Josslyn’s desk. After she placed the order and hung up, Reggie thanked her and they spent a few moments conversing about law and his personal life. Josslyn didn’t seem eager to offer up much about herself, and Reggie didn’t push. The food arrived fifteen minutes later.

“Thanks for dinner, Ms. Roberts. I don’t think I realized how hungry I was.”

“Call me, Josslyn. We’re off the clock. And you are very welcome, Reggie.”

She licked a bit of duck sauce from the corner of her mouth and he was instantly turned on by the pink of her tongue. Reggie discreetly shook his head...he had to get a grip.

Josslyn took a generous sip from her water bottle, watching Reggie the entire time as she did.

“Something on your mind, Reggie?”


“You’ve been giving me some interesting looks. Not only tonight, but pretty much every time we see each other.”

Reggie lowered his head as a blush crept upon his ebony skin. He’d never found a woman so intimidating yet fascinating at the same time.

“Don’t be shy now. Why don’t you tell me what you’re thinking? Or would it make you feel better if I told you I might be thinking the same thing?”

“I highly doubt that.”

“Oh, you’d be very surprised.”

Josslyn rose from her desk and walked around to the front of her desk. The fitted black pencil length skirt perfectly hugged her generous curves.

“I think you are a very good looking young man with one sexy pair of lips. I hope that isn’t too forward.”

Reggie let out a nervous laugh. He hated that he was acting this way...losing his normal cool.

“It’s not. I...uh...I think you’re pretty good looking yourself. That’s why you find me staring sometimes. It’s hard to take my eyes off of you. But, I’m just a guy in my twenties trying to work and make it through law school. Not what you’re used to.”

“How would you know what I’m used to?”

He shrugged. “I guess I wouldn’t.

“Stand up, Reggie.”

When he was on his feet, Josslyn reached for his hands and pulled him closer, placed his hands on her hips. The scent of the floral perfume that radiated from her body was hypnotic and intoxicating.

“Have you ever been with an older woman?”

“No. My age or younger. I don’t think I’ve met an older woman I was really interested in until recently.”

That answer seemed to please Josslyn. She pulled him a little closer and now their lips were just inches apart. She looked up at him and the lust in her eyes matched his own. She closed the small gap and pressed her lips against his...they were softer than rose petals. As their kiss deepened and became more passionate, her hands explored his body...his hard chest, strong back, rubbed his low cut black hair. Reggie was feeling bolder now. He gripped her firm ass and grinded against her. He wanted Josslyn to feel just how hard she was making him. He couldn’t wait to be inside of her and there were just way too many clothes standing in his way. She broke their kiss and gently pushed him backwards until he flopped down on the black leather couch close to the door of her office. Mesmerized, he watched as she slowly unbuttoned her blouse and exposed her chocolate brown breasts clad in a skimpy light pink lacy bra. Her stomach was flat and toned and gazing down lower he caught the small diamond navel piercing, exposing a wild side. The clasp to her bra was in front. Once unhooked, the beautiful mounds sprung free. Reggie was ready to get up from the couch and go to her, ready to take them into his mouth but Josslyn stopped him by wagging a finger at him.

“Don’t move. I want you to watch me undress and then I’ll come to you.”

Josslyn did a slow, seductive dance to the jazz music that had continued to play in the background. She stripped down to her thin pink thong and black heels. Her body was absolutely perfect...curvy in all the right places. Reggie sat in awe, still not quite able to believe this was happening. He was about to have sex with his boss. He didn’t want to think about what would happen tomorrow or any other day after. He just wanted remember this moment. She slid her thong off and stood before him in her heels. It was clear she was very proud of her physique and she should be. She was obviously a woman who took care of herself...and she was completely shaved. That was a major turn on for him.

“What do you think?”

“I think you’re fucking perfect.”

She granted him with a mega watt smile and walked forward, straddling herself on his lap...she was already hot and wet between her legs.

Josslyn gripped the back of Reggie’s neck and lowered his head, allowing him to finally take an erect nipple between his lips and then his teeth. On and on he lavished her going from one sweet breast to the next...licking, nibbling, sucking. Her hands gripped his shoulders tightly as soft moans escaped her. After a few more minutes, she pushed him away and practically tore his blue pullover sweater and white undershirt from his body.

“Don’t want those getting messy. Lay back on the couch.”

He didn’t hesitate, he was eager to do anything she wanted him to do...eager to please her.

With one foot on the floor and the other leg resting on the couch, she straddled his face. She was so wet, so sweet and wet. He greedily lapped at her swollen clit with his tongue, took it between his thick lips and tugged. His hands reached up to rub her breasts and pull at her nipples as she rode his tongue up and down. Josslyn gripped the couch and tossed her head back. She muttered almost every curse word she knew as Reggie continued to devour her pussy. He was really getting into it when Josslyn stopped him and stood up on shaky legs motioning for Reggie to stand up. She sat as he stood in front of her and began to unzip his pants. He was so hard and for a moment she marveled at the length of it.

“Damn,” was all she could manage to say as she took the tip of his dick in her mouth, her eyes on his in order to watch his reaction.

His eyes rolled back and mouth dropped open. He let out a sound so loud it almost sounded like a lion's roar. That encouraged her to take the full length of him into her mouth. The tip of it touched the back of her throat.


Reggie could feel it when she smiled around his dick, took it all the way out and put it in again keeping her mouth wet. She started out stroking slowly and he could do nothing but give her the power and fall under her spell. She picked up the pace. He moved his hips and fucked her mouth, freed her hair from the messy bun and held on tight as he pumped with primal intensity. He was ready to cum, but no...she had something else in mind, not to mention there was no way he was going to do that before he had the opportunity to feel that wetness on his shaft. Josslyn pushed him away and got up from the couch. Her purse was in the top drawer of her desk and she dug around inside until she found what she was looking for...a condom. She pulled down Reggie’s pants and let them fall to his ankles then placed the condom on his waiting erection. Josslyn once again pushed him down onto the couch before straddling him. His hands went to her waist and guided her as she rode him up and down, her breasts bouncing from the effort.

“Shit, this dick is so good,” she purred.

Reggie’s head was resting against the back of the couch and his eyes were closed, small ragged breaths escaped his slightly agape lips. Josslyn leaned forward and closed her mouth over his, swallowed his groan of satisfaction as she began to ride faster and faster. When he felt her body writhing under his touch, he knew she was getting there and so was he. With a strength he didn’t know he possessed, he rose from the couch still holding Josslyn. A look of surprise and curiosity crossed her features, but she quickly got the hint when Reggie rested his back against the cool wall of her office and rammed into her with powerful intensity. She wrapped her legs around him. Josslyn may have controlled a majority of this night together, but Reggie wanted to be the one to end it his way. Finally, Josslyn cried out her pleasure as her orgasm hit. She held on to him tightly and whispered in his ear how good he had made her feel, nibbled his earlobe and begged him to cum for her...which seconds later he did. A low growl came from deep within and it took his breath away. His legs were too weak to make it back over to the couch, so they just kind of slid and tumbled to the floor, letting out exhausted little laughs. Together they sat in silence for a while. They were both thinking about what had happened and where things would go from there...probably not very far. Josslyn wasn’t looking for anything serious with a younger man and Reggie had law school and work to think about, but a few more hookups like this wouldn’t hurt. Maybe at his place or hers next time. For now, they just leaned on each other and enjoyed the afterglow until Reggie checked his watch and noticed the time.

“It’s after midnight. I’d better go. I have to work in the morning and my boss doesn’t like it when I’m late.”

There was more tired laughter.

Josslyn gave him a sweet kiss on his forehead.

“See you tomorrow, Mr. Price?”

“Yes, Ms. Roberts. Tomorrow.” 

© Copyright 2020 Dee Derico. All rights reserved.

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