The Assistant: Owned by the Boss

Bob Anderson grinned like the cat that was about to eat the canary, as he stood up, holding his slick rectum wrecking flesh torpedo by the base.

"Certainly, Becca! Now, this is going to hurt me a lot more than it's going to hurt you!" He said with all the honesty of a used car salesman promising the 20 year old car only had 30,000 miles and the engine was good.

Becca had been to paradise, via hell's own highway tonight. She had felt pain that turned pleasurable repeatedly. She thought she was ready. She hoped she was.

She wasn't, and her soul be damned, she was glad for it.

Bob slowed only enough to fit the enormous head of his cock through her virgin anal ring, giving her just the barest amount of time to register the feeling of pain that could become pleasure.

Then he grabbed Becca by the hips and shoved.

She worried her squeal could be heard from the ground floor.

+++++++++++++++++

Becca was expecting searing pain and to be split in two by Bob's battering ram-slash-cock, but instead, all she felt was a sense of euphoria so overwhelming she had a fleeting thought that she must have simply passed away, and was now in heaven, despite being more deserving of the other place.

His cock in her asshole was the only thing that existed, and if it wasn't, then it was certainly the only thing that mattered. He wasn't gentle, but for whatever reason her hole simply took whatever he gave it and turned it into pure pleasure that spread from the place where he stretched her so impossibly wide it was cartoonish.

She could vaguely register Amanda's singsong voice coming from somewhere above her -- "God, Daddy, she's doing so good, maybe I'll get a sister!" -- *whatever that means,* Becca thought, her brain a fuzzy, hazy mass of confused goo. She opened her eyes and realized that Amanda was standing behind her, leaned over her body, holding her legs apart for Bob. Her perky tits were swinging inches away from Becca's face as she giggled and cooed and encouraged her "Daddy". *He's never getting me to call him that,* the sane part of Becca's brain piped up, but was soon quieted when Bob's thrusts became harder and faster than before.

"That means he's gonna cum," Amanda said matter-of-factly, looking down into Becca's face, which was contorted and pained-looking. "Your ass must be really good, Becca!" She was so enthusiastic, it was almost contagious, and Becca found herself feeling... proud? *I'm so fucked,* she thought wildly, realizing an orgasm was fast approaching with no way for her to stop it.

Bob was pumping into Becca's tight pucker at a pace that she was sure would break records, his heavy balls slamming forward and impacting her gaping pussy and slapping her clit.

Becca felt the whole world spinning down into a vortex of orgasmic bliss as she inadvertently screamed out in glorious release.

"FFFFUUUUUUUUUUUCCCCCK! Fuck my ass! Fuck it! Fucking fuck it, you dirty bastard!", she screamed out, as she clenched around his meaty maypole so hard he had difficulty moving, and she blasted out who knew how many blasts in a series of squirts that sprayed Bob's balls and lower legs and the chair behind him.

Bob continued to slam into her even though the clenched walls of her ass made it difficult to move, causing Becca to start shaking and moaning, and then she was pushing back, trying to bury him into her intestines.

"Fucking rearrange my guts with that fucking huge cock! Fuck my ass like you mean it!" She begged, unable to hold herself up as her screaming, squirting orgasm seemed like it would never end.

"Ooh, Daddy! She's a natural butt slut! Look at her squirt! She's like a fucking lawn sprinkler!" Amanda clapped with glee, before leaning down and pulling Becca's face to hers.

She kissed Becca, jamming her tongue into her mouth, and Becca eagerly responded, screaming into Amanda's mouth as the feeling just never stopped.

Bob gave a mighty bellow, ramming into Becca as deep as he could and unleashing what must have been his biggest load of the evening. His thrusts caused his cum to come out around his shaft as he pumped more and more into her, with Becca howling like a banshee into Amanda's mouth.

After he had finished spurting, he pulled out of Becca's gaping, open asshole with a wet squelch, rivers of cum leaking out after him.

He looked up at the two women still making out on his desk, proud of the day's accomplishments.

"I think it's a good thing most of the workers have gone home already, otherwise, they would have heard you, Becca," Bob said with an evil grin.

Becca was beginning to come back to her senses, and wanted to be notified, but she just couldn't work up to it. That had felt fucking amazing.

"Thank you, sir!" She said, and felt guilty towards Alex as she realized she really meant it.

Becca had cum more times tonight than she ever had in a single night, let alone a single week, with Alex. And damn her soul, she was glad she had.

She stood up with a sultry smile, walked over to Bob on her wobbly legs, hair plastered to her forehead with the sweat of the day's activities, and knelt down in front of him.

"Please, sir, allow me to clean you up," she said, before taking his dirty cock into her throat, sloppily sucking him clean of her, and letting him finally go soft inside her mouth, before taking him out and standing back up.

Fuck, even soft, he was as big as Alex.

"Thank you, sir. Will that be all for the evening?" Becca asked, not sure if she hoped he would answer yes or no.

Bob looked her up and down, happy with how she had turned out this evening, and walked over to the desktop monitor on his computer, shaking his mouse to wake it up.

There, on the screen, was the bald, wizened face of Harold Greenstein, the representative from SureTek who Becca had the unfortunate luck of dealing with. The man whose call she had missed.

He smiled lecherously from the monitor, greedy eyes having clearly seen something that excited him.

"Now, then, Harold," Bob said, "has this made up for the unfortunate mishap this morning?"

"You know, Bob, I think it's a great start. Just make sure to send her round to my office sometime this week, and we can call the issue fixed!" He said, running his dry tongue over his shriveled lips.

"Sure, thing, Harold. Give your wife my best!" Bob said with a wave, disconnecting from the call.

"Actually, Becca," Bob said, looking back at her and waving Amanda to his side as she brought him his pants, "I'd like you to accompany Amanda as she helps you expand your wardrobe this evening. The company's treat for your new promotion to my Junior Assistant. Amanda will be your new supervisor, and will help you accordingly."

Bob pulled his wallet out of his pants, and extracted an AmEx Black card from it and handed it to Amanda.

"Make sure she gets the La Perla I like, as well as...the other outfits she'll need. And don't forget her new collar." He told Amanda, groping her ass almost affectionately.

"Now, then! We'll expect you to actually be on time tomorrow, Ms. Ambrose! I'm quite looking forward to working in you!" He said with a smile that quickly turned dark before adding, "be aware. If you try to renege or back out of our arrangement, your young beau will receive a copy of today's activities."

Then back to a smile and a "Have a good evening! You are dismissed!"

With that, Amanda helped Becca get dressed and the two women headed down to the company gym to use the showers before heading out to the night's adventures.

Amanda couldn't wait for her turn with Becca tonight. She had so many festivities planned!