Sleeping on the Job

NOTE: Henry's a binary trans man who has had top surgery but not bottom surgery. I refer to his anatomy with masculine/male terms. Later on, he will be penetrating with his dick. Some transmen can do this in real life if they have a certain amount of bottom growth, but this is also meant to be fantasy on some level, so cut me a break. I am a transman myself. Any transphobic hate or comments will be deleted. First chapter is pure smut, but I'm hoping to have this be a romance-focused story with bdsm smut. idk man just enjoy it or not, if specific kinks end up happening I'll add them. There will be no effort towards security tech accuracy

Full Summary: Abby has been sleeping with her boss, the millionaire security company owner Henry Knight, for a while now. So far it's been a strictly BDSM-flavored friends with benefits style of relationship. But when a week long work trip leads them to spending more time together outside of the office and the bedroom, they discover an unexpected and intense spark. Can they really stay just FWB?

Now the Actual Story:

The door opened, and Abby saw him, his fresh cologne hitting her. Henry. His dark hair was still slightly damp from his shower that morning, small strands hanging in his face.

"Hello Ms. Lawson," Henry Knight greeted her neutrally, but had a soft, confident smile.

"...Good afternoon Mr. Knight," she said, instantly feeling a bit shy.

"Please, come in." He moved out of the way for her, and she stepped inside. He closed the door behind her.

His office was well lit and decorated, items from the young business owner's travels adorning the walls. It felt cozy, two scented candles lit on a nearby bookshelf. It was small and cozy, enough room for his large desk and technology, but with just enough space for two comfortable armchairs to sit for employee or client meetings.

"How was your day so far?" Mr. Knight asked. The door lock clicked.

"Long. Lots of phone calls," she confessed. She felt his hand grab the back of her neck, fingers immediately massaging. Some of her anxiety melted away, her shoulders drooping some. "It's been insanity. Lots of peer reviewing code and troubleshooting."

"It's been a busy day," he agreed. "I've been dealing with a lot of meetings and calls myself. Especially with all those issues in Colorado."

"Is there anything I can do to help?" she asked.

"Oh man, that's an odd way of offering to do all my meetings for me," he teased. Abby snorted.

"You wanna trade? I'll take business meetings with professionals over 'let me correct all of your mistakes' meetings with the newbies," she said. Henry sighed, pretending to be deep in thought.

"Nah, not worth it," he chuckled. "I have another way we can fix some stuff."

"Oh?"

His grip tightened on her, and Abby's heart thumped excitedly.

"Stress relief," he replied simply. "Are you still wearing it?" Abby was suddenly too shy to reply. She simply nodded. "Show me."

She bunched up her loose flowy skirt in her hands, pulling it up to expose her lacy pink underwear. It was a contrast against her otherwise all-black attire. It barely covered the black remote vibrator that was connected to said underwear.

Henry's free hand reached down to brush his fingers against the toy. She bit her lip to stifle any noise, shifting to allow him. A small yelp escaped as he slapped her ass. Another slap, and she was able to keep silent. Four more slaps, each one harder than the last.

"Good girl."

Those words were enough to make her melt. Any praise from her boss meant the world to her. The "good job" when she finished her tasks on time and well. The "excellent addition, Ms. Lawson" during meetings. The "what's your opinion on the matter?" as their team tried to come up with a solution to the problem. She had quickly become one of his best employees. Her desperate desire to please him, for his mentor-ship, to earn his praise and get his attention is how they ended up in their perfect situation.

"On your knees," Henry ordered, and he firmly pushed her to the ground. She went down willingly, and he let go of her.

He took a step towards one of the armchairs, taking his seat. She needed no further instruction. Abby eagerly crawled to him. She slipped between his open legs, and she reached to undo his belt. He reached into his pocket, pulling the remote out.

She pulled his pants and boxers down, Henry shifting his hips up to help her. Henry's erection was exposed. It was a perfect three full inches. Abby gave an excited sigh as she immediately wrapped her lips around him.

She heard him give a soft groan, his hand wrapping in her hair to push her down until her nose was pressed against his lower stomach. Her tongue lapped against his dick, flipping between soft and hard.

His hand guided her, forcing her to suck up and down. A small click, and her vibrator turned on. She moaned around his cock, sucking hard and moving faster of her own will.

"Tell me when you're close," he said, and she gave a moan to acknowledge him. She jumped as he increased the vibrator's speed.

She could feel her cheeks flushing, and she let go of his cock to gasp in pleasure. Her tongue still slid up and down his cock, her hot breath as she continued to groan. Her hands gripped his thighs to help her stay steady.

"I'm close," she panted. She wrapped around his dick again, only for his grip in her hair to tighten before yanking her off. He slapped her across the face before turning the vibrator off. Abby gave a desperate whine.

"Not until I say so," he said. His thumb lovingly brushed against her reddening cheek. "Good girl." She pressed her thighs together maddeningly.

He pushed her back onto him, and she immediately got back to work. The vibrator turned on again, causing her to move in a near frenzy. She buried herself to the hilt, sucking hard and fast. After a few moments, Abby replaced her lips with her hand, stroking him.

"Am I doing good, Sir?" she croaked out.

"Less talk, more suck," he replied. He pushed her back down again, and she eagerly swallowed his cock. The hand in her hair forced her up to the very tip and down to the hilt. "But yes, baby girl, you're doing great."

The praise flooded her with pride. Any good word from Henry drove her crazy. Just those few sweet words drove her crazy. It wasn't long before she was rewarded with the best words.

"Keep at it, just like that," his voice, gruff and breathy, groaned. "I'm close."

Abby obeyed, so desperate for his approval. Soon, she felt him shudder and buck his hips, and she knew he had cum. She slowed her tongue before stopping entirely, staring up at her boss with wide, eager eyes.

"May I cum, Sir?" Abby asked, slowly moving her hips side to size as the vibrator brought her to the edge. She nearly cried as it turned off.

"Stand up," he ordered, tugging her hair up some. As she stood, he pulled her towards him and over his lap. He gave her a hard slap! on her ass. She yelped.

Another spank. And another, and another. He kept on until her rear end felt raw and sore. She had tears welling up until it finally stopped. An involuntary gasp caught in her throat when her underwear was roughly pulled down and two of his thick fingers slipped into her soaking wet cunt. Henry chuckled.

"Slut." He could call her whatever he wanted. She bit her lip as he pumped them into her, quickly adding a third. He knew exactly where and how to use those perfect fingers. "Man you're just a needy little cunt. What are you gonna do when I leave for my business trip next week? A whole week without my fingers in you."

"I'm gonna go crazy!" she cried out. He slipped a fourth finger into her, and all he was doing now was thrusting into that sweet spot. She was a melting mess, squirming in his lap. "Oh god, Sir, I'm gonna cum!"

His fingers disappeared, and several harsh slaps on her ass. Abby cried out.

"Please!" she begged.

"What are you doing next week?" he questioned. Abby tried to think through the brain fog.

"Um..."

He thrust his fingers into her hard, and her mind melted. He kept them far inside her, wiggling them and brushing that special spot.

"Wrong answer," Henry said, even though she had never given him an answer to begin with. "You're coming with me. I need both my top engineer and my special slut."

His top engineer! His special slut!

"Of course! Whatever you want!"

"Good girl. Cum."

He aimed right for the sweet spot, wrapping his other hand around her mouth to stifle her. Abby nearly screamed as she came, rocking her hips against him. Henry pumped into her as she rode it out, her breathing hard and raggety.

"You good?" Henry questioned. He let go of her mouth, his hand cupping her cheek. Abby gave a breathless nod before resting her head on his hand. "I mean it though, I was going to ask you regardless. The whole literal reason I called you in here."

"Oh, that wasn't just a cover for wanting some action?" Abby replied sarcastically. She jumped as he slapped her ass. His eyes stared at her, pretending to be serious, but his amused smile gave everything away.

"That's just a bonus," he said. "Do you wanna come with me next week to Colorado? I really could use you, you're my best code troubleshooter."

"Yes," she said. "I'd love to go. It'll be easier for me to see the problem in person rather than over the phone."

"Sounds good, I'll make sure I book us both a flight then," Henry said. He pulled her face to his, giving her a soft peck. "Make sure you pack some toys. I'll be keeping you busy all day and all night."

Abby grinned.