Friday Story 24 Jan 2025

Leanne sat primly at her desk, wondering what today would bring. A week into her new job and she was getting a weird vibe from her boss, a good looking black man with high cheek bones and broad shoulders. She knew that from his desk he could see the back of her through the soundproof glass wall, and she constantly had the feeling his eyes were burning into her. Her office chair left her lower back exposed, and the crop top she wore today rode up, baring her midriff above her short skirt.

When she had taken the job she had been desperate, and when her boss had said he was looking for someone good at taking orders and willing to go the distance, she had gulped but agreed that she was that girl. But yesterday, as she stood next to him at his desk, looking at a spreadsheet open on his laptop, he had casually placed one large, dark hand on the smooth, pale skin of her thigh and slowly slid it up under her skirt as he spoke to her about work. She had pretended it wasn't happening and didn't react. When he had slid one finger along the crotch of her panties, tracing the crease of her pussy slowly back and forth, she had frozen and gripped the edge of the desk, holding in a breath as he talked about the excel document. The finger had slid under the elastic of her panties and dipped into the opening of her pussy, sliding slowly in and out as he droned on in his deep voice. She was sure he felt that she was wet, as she had felt her pussy grow hot as soon as she felt his hand on her thigh.

Her boss had slowly removed his hand, wrapped up whatever he had to say, and sent her stumbling out of his office. She had gone to the bathroom and masturbated furiously until she came.

Now she sat, feeling his dark eyes watching her. She shifted, crossing her legs and trying to relax until the buzzer on her desk sounded, his signal to her to come into his office. She rose as it buzzed, already trained to jump at the sounds of it. She walked into his office, reminding herself to breathe.

"Leanne," her boss said, in his sexy deep voice, "You know this company sells sex toys. Well today, I have a few products I'd like to test. Come here please."

Leanne walked nervously over, and her boss instructed her to lean over his empty desk. She bent over, leaning her front against the wide wooden surface. He rose from his seat, walked around to the front of the desk, and grabbed her arms. She realized then that he was carrying padded handcuffs, and he swiftly cuffed one arm to the front leg of the desk and then reached for the other arm. She struggled but it was too late, he easily overpowered her, and soon she was spread eagle on the desk top. She tugged at the cuffs but she was held fast. "Hey!" She said, "Wait!"

But he was already back behind her, lifting her skirt and pulling down her panties. He tugged them off her feet, then reached around and stuffed them in her mouth. He pulled off his tie and wrapped it around the front of her face and tied it behind her head so she couldn't spit out the panties, effectively gagging her. "She moaned through the gag, shaking her head but the tie stayed in place. She strained to look back, her eyes pleading as she made short huffing noises through her panties, but her gaze was met with cold dark eyes that started into hers with no remorse. She was now his to do with as he pleased, and he did look pleased about it. A mischievous smirk played on his full lips.

"First up is this new vibrating anal plug set." From a drawer he pulled out a bottle of lube, and held up a massive anal plug, far larger than anything she had ever taken before. "Mmmmmmfffff!" She said through the panties, and squirmed as he applied lube to her puckered anus. He started with a finger, slowly easing one large finger tip into her ass hole, while using his thumb to caress her pussy. Soon he had a whole finger up her ass, then two, slowly fucking them in and out as she became accustomed to the stretching. Her pussy ached as he rubbed her clit with his thumb, slowly getting her worked up and relaxed. Then she felt cold pressure as he pressed the lubed up tip of the anal plug against her loosened hole. He slowly began working it in, twisting it back and forth and continuing to push it into her as Leanne felt her ass hole stretch wide. It burned, and tears streamed down her face, but she tried to take deep breaths and relax. A moan escaped her though, as the plug reached it's widest point and then settled in. Suddenly she felt it begin to vibrate within her, and beads moved around inside where her sphincter pinched it, and an orgasm began to rise in her.

Leanne heard her boss walk around the desk and a massive black cock appeared in her vision. "Next up," her boss said, "is this strawberry flavored lube. Let me know what you think." He pulled the tie off her head and the panties out of her aching mouth and replaced them with the head of his dick. He grabbed a handful of her hair as he thrust into her mouth, and stared down into her terrified eyes with is cold dark ones as he skull fucked his little white assistant. "Bitch" he said, "cock-loving slut, I knew as soon as I saw you that I would wind up fucking your ass. Today is just the beginning, whore, and who knows, maybe I'll invite my friends soon."

Leanne came, her eyes rolling back in her head as her boss' cock slid down her throat and the anal plug vibrated inside her. Now she knew what he had in store for her and she was gripped with apprehension. The plug was one thing, but this cock currently fucking her face was something else completely. Insanely long and girthy, even with it sliding into her throat she couldn't even get half of it in her mouth.

Her boss pulled his dick out of her mouth and replaced it with the panties and tie set up again. He went back around behind her and fingered her pussy as the anal plug continued to vibrate inside her. "mmmmm," he said, leaning over and speaking quietly into her ear while he fingered her pussy, "so warm and wet, you dirty little slut, next I'm going to make you cum on my cock while I fuck your brains out, and then I'm going to fuck your ass and you're going to like it."

Leanne leaned her cheek against the cool wood of her desk and closed her eyes. The vibrating anal probe was keeping her in a state of wild arousal, and she didn't want to let him know that he was right.

She held in a breath as she felt the tip of his cock against her pussy. He hadn't turned off the anal plug, and the beads moving inside it around her anus were driving her wild. She squeezed her eyes shut and moaned as she felt him slowly work his dick inside her hot cunt, double penetrating her. He grabbed her hips and bucked against her, and she moaned through her gag as he penetrated her with his long black dick. Finally his balls were slapping against her clit, and she felt her knees go weak. He was deeper inside her than anything had ever gone before. He used his feet to push hers further apart as he fucked her, this little white female who had wandered so willingly into his clutches.

His dick slid in and out in long thrusts, each one pushing her up against the desk. As her boss humped her from behind, his body hunched over hers, he pushed against the anal plug still lodged deep within her ass, wiggling it around inside her and making it hit every nerve as it vibrated. At the same time, his massive cock seemed to stroke against every part of her insides, and soon she was coming on his cock just as he had predicted. She screamed through her gag, arching her back as he plowed into her. When she was done she went limp, sagging against the padded hand cuffs.

Leanne felt her boss finally turn off the anal vibrator and slowly pull it out. She winced a little as she passed the fattest point again, but she was well stretched out by now. Leanne felt her feet being pushed further apart, and she was sure her ass hole was gaping. She felt the tip of her boss' lubed up cock press against her anus, and let out a long, low moan as he slowly began to force his big black cock into her little white ass hole. He pushed first just the head of his cock into her, stretching her as wide as the toy had done. He gazed down at his cock, slowly disappearing into Leanne's bowels. He pulled back and then pushed forward again, back and forth, slowly working his cock further and further up her anal passage. She moaned and shook her head back and forth as he began fucking her ass a little faster, pounding a little deeper each time. He pulled out and then slammed back inside, grabbing her shoulders to use as leverage. He was all the way in now, and Leanne had her eyes squeezed shut and was gasping through her panty gag. Slowly he pulled out again and then slammed back down, sheathing himself completely within her bowels. She moaned through her gag, from pleasure and pain, and he looked down at her, her ass stuffed with his cock, arms pulled tight against the desk, eyes squeezed shut and completely as his mercy. His cock throbbed with need and he began to fuck her ass hard, pounding into her over and over again. He grabbed her hips and plunged into her, riding her like an animal as he fucked her ass. She came again as he plowed into her guts, howling like a wild beast as she was fucked mercilessly. He came next, filling her ass with his semen as he loomed over her. He stilled for a moment inside her, then pulled out of her ass and left her there, dangling off his desk, while he went into the bathroom and cleaned himself up.

He released Leanne from her bonds and then scooped her up and carried her to the bathroom, her body limp from being used so intensely, He helped her clean up, then slipped her damp panties back on her body and instructed her to wear them the rest of the day.

Leanne spent the rest of the work day at her desk, knowing her boss' eyes were boring into her. She wondered if she would come back the next day, but knew deep in her soul that she would.