The Boss

"I want you to think about this," Jane told him. "Do you like me as your boss or do you want to be my boss?"

"I like you as my boss."

"Good. You didn't even have to think about that, did you? I like being your boss, too. So why are you telling people you want to show me who's boss?"

"Because..." he trailed off. "I'm... I dunno. I brag to my guy friends about it."

"I know. But who cares what they think? Why do you care?"

"Because you're intimidating. You're... strong. Smart. Beautiful. Funny. In control. It... makes me feel... jealous, I guess."

"There it is," she sang to him.

"I'm sorry. I know it's unfair and shitty. I don't mean to--"

"Do you know why I like being your boss? You're a really good worker. You do what you're told. You never really complain. You ask how I'm doing almost every day. You ask if I need help when you have time to spare."

Ty's eyes moved across her face and he started to think.

"I'm not doing this to punish you," she said. "I mean, that is half the fun of it in a way. But I gave you those two options earlier for a reason. I want you to be here. Not just for the job... but for me. I'm not expecting or wanting you to be the boss. I'm hoping you'll like the boss and maybe like her enough to bend over and take it for her every now and then."

"You're something else," he laughed. His smile instilled her with new confidence.

"Then what's keeping you from letting me show you who the boss is?"

A peaceful quiet hung over the room for a moment. "Nothing important, I guess."

"In that case... let me show you something." She brought a new toy out of the bag. Something long. At the end of the black harness was a thick flesh-colored dildo. Ty's eyes widened and he felt his pulse quicken.

"That's... fucking huge."

"It better be," Jane replied. "I have to make damn sure you remember I'm the fucking boss."

"Oh boy," Ty gasped.

She slid on the harness and fastened it around her body. Looking to the side, he could see her monster cock hanging starkly in the air, almost taunting him. As she moved behind him, he could hear her squirt lube before she applied it to his asshole and her dildo. His thoughts wandered as she went to work preparing the both of them, and it occurred to him that this didn't seem like her first time doing something like this.

"Deep breaths," she instructed.

He felt pressure on his asshole. Something big was trying to get in and would not be kept out. Distantly, he heard her telling him to relax. A hand soothed him by caressing his right butt cheek gently. Then he started to give. It did hurt at first. She talked him through it and slowly pushed in further. She's really good at this, he thought.

Before he expected it, she thrust her cock all the way into him. He let out a loud moan. Another thrust. He felt her stretching him from the inside. Her strong hips began to collide against his ass. After the first push, he realized she was too big for him to do anything but relax and take. So he did.

"That's it," she complimented. "You want every inch of my cock. Good boy."

Just then a knock on her door startled and alarmed him. On the verge of panic, he felt her put a hand on his back and press down slightly, as if to say he should trust her.

"Come in," she said out loud. She didn't pause or even look up.

Ty mumbled something incoherent at this and moved. She drove her strap-on deep into him to regain control.

"Shhh," she whispered. "Behave."

A key rattled in the lock and the door opened. A tall, good looking security officer entered the room. He approached Jane without appearing to bat an eye at any of what was going on.

"Package came for you, Ma'am," he said, handing her the item.

"Thank you, Marcus." She put it away out of sight and continued on.

Without anything further, the guard left, closing the door behind him. The keys rattled again from outside.

Ty took a moment to collect himself. When he had, he spoke: "What. What was that? He saw us. We're caught!"

"Shhh," she said softly. "Marcus won't tell a soul. He's a friend."

"A friend?" Ty asked in confusion.

"Handsome boy," Jane teased. "I'm the boss. I'm in charge around here."

She pushed in a little harder and deeper, to give an added incentive for him to relax. He instinctively let go and moaned for her happily.

"You'll learn soon enough. It's nothing to be afraid of. I'm even in charge at home. People trust me to lead for a reason. I know what I'm doing. I take very good care of those that trust me. And especially those that serve me."

Her rhythm had relaxed him to the point of a quiet bliss. In. And out. In. And out. Slow and steady.

"Now," she said. "I wanna hear you tell me who the fuckin' boss is."

She jerked him back, grabbing a fistful of his hair. Slow and steady turned into something like the feeling of a python forcefully invading his helpless asshole. With her other hand, she smacked his ass hard. And again. And again. Jane rocked him back and forth on her cock while he let out a series of gasps, moans, and yips.

"Y-y-you..." he mumbled.

"I can't hear you. Speak up, butt slut."

"You are."

"Louder, boy. Who's fucking who's ass?"

"I-I... I'm..."

"Are you the boss now?"

"N-no," he groaned.

"No? Your little cock isn't fucking my ass?"

"No, Ma'am."

"Go on," she scolded, smacking his ass and pumping it repeatedly with her strap-on.

"You're the boss, Ma'am."

"Terrible. Make it come from the heart."

"Ahhh," he grunted in frustration, wriggling his hair free of her hand.

"Oh, have it your way," she said in a mean tone of voice.

Before he could realize what was going on, he found that she had lifted his legs up and caught them under her arms. Her strong hands clasped around his waist, making him feel vulnerable in a new way. Somehow, some way, she did this without breaking a stride, even when it caused him to lose his balance and his face hit the desk lightly. He followed her lead and raised up his upper body with the use of his arms. She commenced pounding him so hard he worried something might break, occasionally lifting a hand in between to strike his trembling bottom.

"Oh my god," he said quietly.

Slap. Slap. Slap. She took him like it was sport.

Smack. Smack. Smack. Her hand beat on his ass.

"Say it," she commanded. He exploded in a flurry of confessions.

"You. You're the boss. My ass is yours. You fuck my ass. I'm. You're. Uhhh... You're the fucking boss, Ma'am. You're my boss."

As he said this, she reached between his legs and grabbed his balls in her hand. Possessively and firmly, like saying this boy is mine. After a minute, he felt her start to slow down. She continued using his ass until the pace dropped to a crawl. His cock had long since been unable to keep up with her and retreated into its flaccid form. When she finally pulled out, he gave a little yelp and shuddered.

"Get up," she ordered, handing him wipes. "Clean yourself off."

She began cleaning her own things and putting them away in her bag under the desk. When he had wiped himself down, she told him to get dressed while she did the same. Still reeling from their time together, he started to feel the cold professionalism slipping back in. This was how it had to be, though, he knew. Nonetheless, he was grateful.

Before he started for the door, she called his name and pulled him to her, tangling her arms in his body and kissing him passionately. Her eyes met his and both smiled at each other.

"Don't forget this," she said. "I expect you to be on your best behavior now, as I will be. Until I have use for you again."

"Yes, Ma'am," he answered.

"Don't worry, handsome boy. It won't be long."