Job Interview, Anal Intentions

She felt pressure, a bit of pain and then an erotic sensation that radiated up to her now swollen and hypersensitive clit. It never left her mind that the small team must have been having a good time with this. It was so damn humiliating and so delicious.

The fingers pulled out, leaving a feeling of loss in her asshole, which was now coated with lube.

She heard the package being opened. It was time.

"I'm an anal virgin," she reminded them.

"Not for long."

A smooth material was pressed against her anus. The curved head of the anal toy was unlike anything she had ever felt before. Just when it felt like entry was impossible, the hands of the associates came to the rescue, spreading her asshole even wider, allowing the toy to 'plop' its way inside her hole. Her sphincter put up a fight but it finally gave way and she felt the penetration.

Hannah wasn't sure which feeling was more surreal; that a foreign object was now in her butt, or that the people she'd soon work with every day had seen and helped with the backdoor entry. And if she were honest, she liked both feelings very much. God this was obscene, filthy, and... wonderful?

With her face pressed onto the table, eyes squinting, jaw clenched, all she could focus on was the insertion. The sex toy was smooth, and with the lubrication, it slowly slid deeper inside of her. She could feel her anus and rectal cavity stretching and expanding.

The hands of the associates kept her small asshole open and she could hear the chatter and small comments:

'She's a tight one.'

'I can only imagine what she's going through,' the female colleague added.

They couldn't see Hannah's face, nor the crooked smile. If the colleagues thought she was humiliated and degraded, they were right. However, if they thought she wasn't enjoying this at all, they were wrong. The experience and anal play were scratching an itch Hannah never knew could possibly exist.

Her eyes nearly crossed when the vibration was turned on a low setting. There was a moment when she was fearful she might literally lose control of her facilities. That was a second, and then Hannah relaxed and learned to enjoy. And it was very much a learned experience.

She felt the light buzz and her body instinctively wanted more, wiggling her small, tight ass, and pressing her sex harder into the desktop. There was this almost unworldly sense of being filled. She felt her ass spasm, twitch, and then she was giggling. Fuck it felt good. Her little hands and feet started to curl and she was digging her toes into her flats, moving her ass in rhythm, and then she didn't even recognize the growl that came out of her mouth.

And there was the oh-so-sweet buzzing. It was the most intense thing she had ever felt. Her clit was on fire and she was practically dry humping the table, pressing in, pressing hard, and needing more. Her entire lower body was spasming and she knew she was cumming hard.

Wave after wave washed over her. She felt she might explode from what was happening in her asshole. Puddles rolled down her thighs and still she kept cumming, whether it was one incredibly long one, or a series of short spasms. All she knew was someone turned off the vibrator in her ass and her body kept jerking like she had been shocked, collapsing onto the table. Her legs turned to jelly when it was over and she whimpered like a kitten.

"Excellent so far," Mr. Brennan approved, in what had to be the understatement of all time. "You have a delicate frame, yet your rectal area is quite strong and adaptable."

Was that even a compliment? Hannah wanted to ask, 'So did I get the job?' but that seemed a bit tacky given her sexual state of being with her asshole still buzzing.

The boss continued, "Keep holding her cheeks open. I'll need to give the final inspection with my penis."

And there it was, the inevitable ending that she needed to get her body ready to go one more time. Gasping in shock, Hannah was in a state of panic. She was going to be fucked now? Her orgasmic daze was the only thing that kept her from putting up an argument.

And frankly, deep down, that orgasmic state also left her wanting more. She was curious. Maybe the sex toy that had just ravished her asshole was exactly as advertised?

Turning her head, she used one eye to take a peek at the boss. The employees were still holding her asshole open and she could see Mr. Brennan working to undo his pants.

When the pants dropped, Hannah could see that the boss wasn't entirely hard yet, as if her young body being used by the sex toy did nothing for him. He stroked himself to get hard, looking at her asshole. It was apparent that Mr. Brennan lived up to his reputation-- he was a machine. This wasn't solely about sexual pleasure.

This was business.

Hannah watched the boss tug himself, then with the right stimulation, that cock turned into the biggest thing she had ever seen. It looked like something out of a porn movie, by her standards at least. She hadn't been with a lot of guys as she was more of a long-term-relationship kind of girl. And most of the guys she had gravitated towards tended to be smaller in stature, which was her taste and what her body was built to accommodate.

Now she was expected to handle this? How on earth was it going to fit inside of her backdoor? The thought didn't seem possible, even after the sex toy.

But she wanted this job and she knew better than to question the boss. She was so close she could almost feel herself sitting behind a desk here, even with a sore bottom. She no longer questioned everything. Her body was on fire from the orgasm and these feelings were all so new. Everything was still exciting, the humiliation, the vulnerability, even the anal pleasure, which she could hardly believe was a source of orgasms now.

She faced forward, not wanting to see this happen. It was like being in the doctor's office and looking away when it was time to get injected by a needle. Sometimes it's better not to see it happen. She heard the tube open again, followed by the sound of the boss slathering his cock with lube. She knew she'd soon be mounted for the sake of 'research.'

The associates worked together on this, making a team collaboration to fit the cock into her asshole. The cock slid surprisingly easy into her as the toy had already left her gaped and ready. Inch after inch, he went in, steady, never slowing, deeper and deeper into her rectum until she felt the hair on his balls tickle her ass. Once mounted, she found out how relentless and focused the boss was, fucking her hard after taking a short moment for her rectal muscles and sphincter to get settled. Rhythmic slapping noises filled the room.

Her chest rubbed back and forth across the desktop as the boss took her. She didn't even know how loud she was moaning. All she knew was how desperately she wanted to reach back and play with her own clit.

While her asshole was stretching and being used for a man's sexual pleasure, all she could this was; so this was anal? This is what it feels like to have a man pound your little asshole. The mystique of porn was gone. Now she understood.

The pressure was intense, painful, but such sweet pain. She was ashamed while her body was rocking back and forth. For years she had thought of this as a horrendous sin, yet now, at this moment, a cock buried deep in her asshole, she was loving it.

This was also her job. She savored and contemplated every second of the carnal ecstasy and agony she was getting from the stretching and fucking. Finally, she couldn't help herself.

"Oh, fuck me a little harder," she let out, then regretting it.

The boss obliged and she heard the female colleague giggle the words, 'Well I guess the sex toy really does work.'

She had been raised conservatively, but she had read voraciously, and always hoped that one day she might find the right situation to test her sexual desires. However, she had never dreamt of this. She had solely been thinking about mutual exploration with the right lover, an Asian lover of course, as her parents had instilled into her.

"Mr. Brennan, a reminder for your 10:30 meeting," a familiar voice said sheepishly, yet professionally from the hallway.

The voice was almost too familiar and Hannah, with an asshole that was being pillered, was terrified of looking. But she had to. Turning her head to the door, she saw her sister Gina with a well-composed look on her face.

Being sisters, Hannah could sense how painfully awkward, yet slightly hilarious this was for Gina to be in the presence of this anal violation. She wondered if Gina felt sorry for her, or knew that she was living out the greatest sexual adventure of her life.

"Are they in the room?" Mr. Brennan grunted with slowed down thrusts.

"Yes, sir. I've escorted them to the conference room where they're getting set up."

The boss didn't miss a beat. "Thank you. They can wait an extra 10 minutes. I need your help with something. Grab some wet paper towels and come back."

Come back!? Hannah was aghast that her receptionist sister was going to return after seeing this. When the receptionist said, 'Yes, sir,' and stepped away, Hannah felt a burning shame which somehow managed to top everything that was going on up to this point.

It felt like a strange loss when her sister left, but at least she was still in good hands, literally. The associates massaged her butt and it felt like Mr. Brennan was fucking her like something out of a hardcore porn; the man truly had skills. From the smooth penetration, to working at just the right intensity and depth, Hannah's ass was taking quite the ride.

Her asshole was pushed to the brink as the boss squeezed her hips and went to town on her. Her teeth were gritted.

"I'm going to fill your asshole," Mr. Brennan said with his gathered strength. "These little details will help with your story. It will assist in selling the device as a great present for couples."

She felt her hips being grabbed and the boss going balls deep, with his crotch slapping against her flat butt cheeks. The cock was stuffed all the way and she could sense that Mr. Brennan's muscles were tensing and flexed.

The truth was, Hannah had never gone bareback with a guy. Now she felt rope after rope of hot cum shooting inside her lubed anus. There was now more of the hot cum than there was lubrication. It tickled almost as everything was jettisoned inside of her rectum.

When the boss pulled his softening cock out, Hannah felt a gaping sensation in her once virgin hole, and she could also feel cum flowing out. She could no longer claim to be a virgin there, not after the toy and that large cock. The other employees released their grip on her butt, making her asshole close.

Her small hole clenched around the cum filling and she rested her head on the table, feeling a mixture of shame and sexual indulgence. When she heard a light set of footsteps returning, her shame only grew worse.

"Clean me first, Gina," the boss said. "Then clean our new staff writer."

"Yes, Mr. Brennan," the dutiful receptionist said.

In a state of horror, Hannah turned around and peeked with one eye, to see the sight of her sister on her knees, using a wet paper towel to clean the boss's flaccid penis, which had just been pulled out of her asshole less than a minute ago.

She laid her face on the table once again, listening to the sounds of the other associates getting up and making themselves presentable once again.

When she heard the sound of Mr. Brennan pulling up his pants and zipping himself, Hannah knew it was her turn for a cleaning. The water was cold as it pressed against her outer anus and she wondered if her sister had gotten cold water on purpose.

The wet paper towel cleaned the ring of her anus in smooth circles, before digging inside with the push of a finger. After all the anal trauma her opening had endured that morning, entry was easy. A delicate finger was nothing in comparison to the sex toy and big dick.

"Give a little push for me," the receptionist said.

Miffed, Hannah did as she was told, giving a short push so that cum would seep from her asshole, onto the paper towel. It was working so she gave another push for good measure, not wanting cum to drip out of her ass later. The finger twirled around in her butt to clean as much of her anal cavity as possible. Then the finger finally pulled out after what felt like the longest minute of her life.

"All clean," the receptionist noted, giving a gentle pat on the butt.

Hannah stood upright and pulled her skirt down so that no one could see her exposed pussy or butt. She was positive her face was beet red. The boss looked casual after fixing his pants and the other associates looked ready for work.

And then there was the receptionist, blushing with a cute smile on her face, holding a wet paper towel that was drenched in cum. Hannah avoided direct eye contact with her sister at all costs instead focusing her attention on the boss.

"You mentioned a moment ago that I'm the new staff writer," Hannah said with her brave face, feeling that she's more than earned this.

Mr. Brennan picked up her panties. "You are. Mind if I keep this?"

"Go ahead," she replied, knowing it would be her first time walking around with no panties underneath.

He twirled the panties and put them in his pocket. "Get to work. There's a big sale coming and your support is needed. Gina, please show Hannah to her new desk."

"Right away," the receptionist replied.

Mr. Brennan headed towards his meeting, giving Hannah a quick congratulatory handshake. The other associates had the same welcoming attitude.

When they left the office, it was just Hannah and her receptionist sister, who said 'Follow me,' before guiding her to the workspace.

Fixing her outfit and smoothing her skirt, Hannah followed, doing her best to walk straight down the hallway with a sore asshole.

"Not a word of this to anyone," Hannah said discreetly, barely moving her lips. "Not to our parents, our friends, or even me. Don't mention this ever again."

Gina kept looking ahead as they walked. "Never, ever."

Ever since she was young, Hannah had dreamed of being a reporter or a journalist. Sure, she had role models. At first it was Lois Lane, with the quiet strength and smarts to support Superman. Later it was Diane Sawyer on 60 minutes. She liked women who stood for something, as opposed to being eye candy.

With cum seeping from her well-used asshole, she was on her way to settling into her dream job. The political topics would come later. She had to earn her status, and with a sore rectum that was still buzzing with pain and pleasure, she had certainly done that.

The End

Co-written by the great and talented Homerun2611.

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