Secretary gets trained for her new (anal) position

It was the third and final interview for Vanessa Flores. If everything went well, and she had a great feeling it would, she would land a high-paying job as the personal secretary for the boss of Satisfaction. Sure, it was an adult club located on the top floor of a downtown commercial building, but with the sexual appetites that corporate men had, long-term employment seemed assured.

So far, she had met with a few employees of the club, but never the actual boss himself. She found it strange, that the man who’d she’d potentially be working for hadn’t taken the time to meet her until the very last interview, but she figured this line of business was strange enough already.

On that morning, she had almost become used to showing up at the swanky club. It was like a sassy office floor, except instead of traditional office work, it was built for sex. Corporate sex, to be more precise. Even the employees of the club dressed the part, with the men wearing suits and the women wearing office skirts and blazers.

This was a newly opened branch of the Satisfaction franchise. Things were still getting settled in and hires were still being made. There were butterflies in Vanessa’s stomach as she proceeded down the hall to the main office to meet her potential boss for the first time.

Caleb wore a nice suit and was on the phone with his lawyer when she entered. They shook hands, even as he finished his conversation, which was purely professional. They both sat down; Caleb behind his desk and Vanessa in front.

When the call ended, introductions were skipped and it was straight to business.

“Firstly, I have to apologize,” he said, finally giving her the proper attention she deserved for a job interview. “I promise we’re a tightly run organization. It’s my fault for dropping the ball with your interviews. Since we’re such a unique business, I should have been here to properly explain everything to you.”

She flashed a polite smile. “It’s not a problem. I know what I’m getting into.”

“Is that really the case?”

Caleb sifted through a stack of papers on his desk until he found what he was looking for. He leaned back and his eyes scanning the page.

“32 years old,” he said, reading off the resume. “Nice employment history. You were previously an executive assistant at a big bank. Very nice. However, that’s nothing related to this industry, so to speak. Are you sure you’re up for it?”

Vanessa fiercely nodded her acceptance. “Definitely. To be honest, sex has never bothered me. I applied here because I had heard about the stellar reputation of Satisfaction through an old colleague. If it’s elegant enough for wealthy men to come visit, then it should be a safe environment for me.”

“Has it ever occurred to you that maybe people come here because it’s sleazy?”

Caleb raised an eyebrow in a questioning way, and Vanessa remained undeterred by this form of interrogation.

“There’s nothing sleazy about this place,” Vanessa firmly stated. “And I know for a fact that successful women come to these sorts of places as well.”

“You know you’re stuff, Ms. Flores. I like a woman who’s well researched.”

“As you can see from my resume, I’ve worked for men who are non-stop in their careers. Being prepared is essential for my duties.”

Caleb purposely showed an unimpressed look. “You’re smart, talented, and hard working.”


Vanessa had read his clear signs of wanting to reject her. Or maybe it was all a ploy of some kind. Whatever it was, she knew this man was tricky and was purposefully playing games with her.

For a sex club franchise like Satisfaction, she was certainly prepared for whatever would come her way. In her experience, the social elites don’t just let anyone into their circles. There’s always a cost.

“Like I said a moment ago,” Caleb reminded, “I was busy traveling this past week and I should have been the one to conduct the initial interviews. I take full responsibility for this error.”

“Error? Is something wrong?”

“Well, I spoke with my assistant before you arrived. It seems she hadn’t mentioned certain aspects of the position you’re seeking. Again, my fault entirely. My assistant acted in good faith and wasn’t aware of particular details.”

A slight sense of panic set in with Vanessa, but she refused to show it. She wanted this job. The pay was fantastic, the hours were reasonable, and an added perk was that it was walking distance from her tiny apartment.

No. She refused to give up. She gathered her courage and decided to fight back. Nothing in life comes easy. There are certain things which need to be worked for. And now, she was a determined woman, ready to close the deal.

“Tell me what the issue is,” she said. “Be straight with me. I’ve spent hours applying for this job and coming here to do interviews. And don’t even get me started on the time it took for my hair and makeup. Secretaries need to look the part; we both know that. Now tell me.”

Caleb showed a genuine smile. “Feisty, I like that. Though I’m not sure you’ll like what I have to say.”

“Either you tell me, or your incompetent assistant will.”

He leaned forward. “This is a sex club, Ms. Flores. As my personal secretary, you’re expected to wear… well… less than that.”

Caleb’s eyes looked over her outfit in a rather suggestive manner.

Vanessa looked down at her own professional clothing. “What’s wrong with this?”

“For starters, you’re covered.”

She nearly gasped. “You expect me to be naked?”

“I told you, you wouldn’t like it.”

“This must be a joke.”

“That’s only half of it.”

She clenched her jaw briefly. “What’s the other half?”

“As you already know, we deal with a lot of rich clients. Men and women. Mostly with kinky tastes. Obviously, these clients expect confidentiality of the highest order.”

“Beyond me being naked?”

“Yes. The secretary, whoever it is, will be entrusted with all the clients’ identities and billing information. It’s a highly sensitive position. I must be cautious with whom I chose. Surely you can understand that.”

“Of course I do,” she said.

Instead of replying, Caleb gestured to the wall. There was a black and white photograph of a woman in a prone position from behind. It was an artistic picture of a woman’s spread butt. Even more striking, there was a silver butt plug nestled inside her anus.

“A plug?” she questioned. “There?”

“I need full obedience. And what shows obedience more than anal discipline? In my world, anal control speaks volumes.”

Vanessa’s butt clenched onto the seat. She was an anal virgin. Like most women her age, she had been flooded with requests from past sexual partners to try anal sex. It especially seemed like a common interest for city men, though she never understood why. Especially with, her ex-fiance…

Caleb looked closer, “Did I lose you?”

“Oh,” she said, snapping out of it. “I’m here. You just caught me off guard. That’s all.”

“Based on your reaction, you seem uninterested. My apologies once again for the confusion. I’ll have my assistant compensate for your time. You look ravishing. I’m sure you’ve put a lot of effort into that.”

Before Caleb could gesture for her to leave the room, Vanessa instantly thought of her ex-fiance. A man she deeply loved. They were set to get married two years ago when he inexplicably dumped her for the flimsiest of reasons.

She remembered his words. ‘Vanessa, I love you. But we’re both still young. There’s still a lot to explore.’

Vanessa knew exactly what her ex-fiance meant. On several occasions, he had called her a prude because she refused his requests for anal sex and threesomes with other women.

In her world, she was far from being a prude. She had deepthroated him in the car on a regular basis to show her adventurous side, and as a sexy Latina, being called a ‘prude’ in bed was a massive insult. Apparently her willingness for sexual adventures wasn’t enough for him.

That horrible memory of being dumped brought something out of her.

“I’ll do it,” she told Caleb. “I’ll fucking do it. After it’s done, you’re going to hire me, and I’m going to work here as your secretary. And if I do a good job over time, then I also expect a pay raise too. Got it?”

He smiled his approval. “There’s a special quality within you. I like what I’m seeing. My assistant, Ms. Chen, will handle this. She’s an expert on the matter.”

“What? You mean…”

He mildly looked confused. “You understand that if you get the job, plenty of people will be seeing you, if you catch my drift.”

“I understand,” she said with a forced smile, then taking a deep breath. “I’m ready now.”

“Good. Let me call her in.”

Caleb called in his assistant, and he even informed her to bring the ‘training supplies’ as well. The sound of that made Vanessa shudder.

“Will she be naked too?” Vanessa asked.

He laughed. “No, she’s my personal assistant. She doesn’t directly work for this club. Speaking of which, start by removing your top. It’s a beautiful blouse and blazer and I’d hate to see it wrinkled.”

“Now?” she gulped.

“Ms. Flores, you’ll be bent over my lap. Your clothes would get wrinkled. And I need to see if you have the fortitude for a job like this. Speaking of which, I don’t mean to be rude but an investor is calling. Please, excuse me.”

Caleb’s phone had been beeping and he answered it. He spoke on the phone the way most businessmen would; loud, confidently, and having a bit of laughter before going straight to numbers.

His attention was on the call, but his eyes remained on her. Waiting. Wanting to see how far this would go.

As he spoke finances on the phone, Vanessa focused on business of her own. Nudity was never something she was uptight about. In fact, as an avid fitness enthusiast, she was extremely proud of her figure and shapely rear end.

She stood up and removed her blazer. That was the easy part since her silk blouse was still on. Caleb’s eyes looked her over and Vanessa unbuttoned her blouse. She removed it and placed it neatly on the couch.

Maybe it was the atmosphere of the place, but she felt strangely comfortable standing in her bra, in front of her soon-to-be new boss. Normally, she’d have guys fawning all over her at this state; not Caleb though. He’s probably seen countless gorgeous women like this, so he was used to it.

Wanting that extra bit of attention, she looked him straight in the eyes and unclasped her bra, letting it fall to the floor. Her pert breasts and dark nipples were exposed. It made Caleb smile ever so slightly.


Caleb sat forward on his chair and patted his own lap. He signaled for her to bend over his knee. She complied and approached him near the desk. All while Caleb was still talking to the investor.

As she stood by him, with her long dark nipples so close to his face, the office door opened and Ms. Chen entered. She was a petite little Asian woman who had a no-nonsense, yet sexual aura about her.

In the assistant’s hands was a clear container which was thoroughly prepared. It included oils, lubricants, and a small silver butt plug. All the items were then placed on the desk.

Vanessa suddenly felt awkward being topless in front of the female assistant, but the assistant didn’t mind. This all seemed routine for everyone except Vanessa.

Caleb briefly covered the phone and whispered, “Vanessa, bend over on my lap. I love seeing this part. Don’t worry, my assistant used to be a nurse, she’s good at this.”

In a split second, he returned to his phone call and spoke of numbers and financial figures. Vanessa’s butt involuntary clenched, and when she turned to look at Ms. Chen, the assistant was ready for action and gestured for her to lay across the boss’s lap.

Without saying a word to interrupt the call, Vanessa took the demeaning position by bending over and laying across Caleb’s lap. She was light and he was strong, so weight wasn’t a big deal.

Once in position, Ms. Chen went straight to work and lifted Vanessa’s office skirt. Vanessa was proud of her shape. She had the stereotypical attributes many people loved about Latinas; wide hips, round butt. As she looked down at the floor, she wondered what they must have thought of her posterior.

Vanessa felt her panties sliding off. She made the process easier by lifting her legs so that Ms. Chen could pull the panties away easily. Her thighs were strong and she could have easily clenched her butt tightly in an impenetrable manner. Instead, she relaxed and let Ms. Chen spread her luscious cheeks.

It felt strange. As an anal virgin, Vanessa now had two professionals, who were not doctors, staring directly at her anus. When Ms. Chen spread the cheeks further apart, they had a clear view of her rectal passage. The thin, feminine fingers spread the alluring butt cheeks even further, and Vanessa could feel air flowing into her tight, virgin hole.

This was a different sort of shame. All her life, only doctors had seen this area. Now here it was, for her next boss and the assistant to admire, or whatever the hell they were doing to her behind.

As Caleb continued a conversation about money, Vanessa could hear the sound of Ms. Chen opening a bottle.

“It’s a silicone based lubricant,” Ms. Chen whispered softly, careful not to disturb the boss’s important call. “It’s perfect for anal play.”

Anal play. What an obnoxious phrase, Vanessa thought. Her body suddenly jerked when she felt the substance being poured to her anal region, as two fingers held her asshole open. It felt cold and it tickled her anus.

What came next seemed even more intrusive. Vanessa felt a bare index finger touch the outer ring of her anus. The assistant didn’t even bother to use a glove. The hand rested on Vanessa’s plump butt and the finger gently massaged the anal ring in firm circles.

“I can’t believe this is happening to my asshole,” Vanessa sighed.

The assistant reached below and pinched Vanessa’s labia as punishment.

“Shhh…” Ms. Chen hissed. “The Boss is speaking. We mustn’t be rude.”

As feisty and strong as Vanessa could be, she didn’t want her labia pinched again, so she kept quiet. The gentle finger returned to her anus and the massage continued. In all honesty, it felt nice. The more Vanessa relaxed her posterior, the more she enjoyed Ms. Chen’s finger circling her hole. It felt so tender and vulnerable. There was nothing to compare this too.

Suddenly, the lubed finger plunged into her asshole and Vanessa’s eyes widened. Although the finger was thin, it made an impact in Vanessa’s virgin hole. The finger probed inside her rectum in a circular motion, coating her tight passage.

When the finger quickly pulled out, Vanessa was left with a false sense of relief, because immediately after, she felt the butt plug pressing against her anus.

“Relax,” Ms. Chen whispered. “I’ll need your cooperation on this.”

The assistant used one hand to hold Vanessa’s anus open, and with her other hand, she pushed the plug in. Vanessa resisted every urge in her body and fought to remain calm. She could only imagine what her rear end looked like, with her anus being stretched in the most unnatural way possible.

As the plug kept on being pushed, and Vanessa’s asshole opened, the plug was able to enter. Penetrating the anal ring was the most difficult part and Vanessa felt her lubed rectal passage being overwhelmed as the plug made its way in.

“Fantastic!” Caleb exclaimed as the phone call finally ended. “Vanessa, you’re a trooper. And you already know this, but you have a movie star’s ass.”

He gave her butt a soft rub, then a spank, which only made her ass clench around the plug.

“What now?” Vanessa asked, slightly annoyed. “Do I have the job?”

“Would you buy a car without a test drive?”

“What does that mean?” she asked, turning her head to them.

“Stand up. Lose the skirt. Then walk back and forth. Like I said, we’ll need a test drive of your anus.”

When Vanessa stood, she felt an incredible uncomfortable feeling as her butt clamped around the plug. Her anus had never felt this uncomfortable since… ever.

She removed her skirt and stood naked in front of both of them. All she had on were her heels and some jewelry. She walked back and forth across the office like a fashion model, trying to be as bold as possible with her own nudity. She refused to look them in the eyes; that would only make her more nervous and self-conscious that she was the only one naked.

“Excellent,” he said with a pleased look. “Now, if I hire you, you’d be at the desk outside of my office. Shall we?”

Vanessa gazed through the office window and saw a few employees and clients down the hall. She gulped. Hard. But at the same time, she felt a rush of excitement in shedding her sexual skin. ‘Prude’ no more. She was game. And nothing would stop her from landing this job.

“We shall,” she replied with a confident smile. “Can I lead?”

“Please do, Ms. Flores.”

“I’m about to become your new secretary. Call me Vanessa from now on.”

She strutted to the door. With each step, especially with her heels on, her rectum would clench against the plug. It became easier when she learned to relax her steps. The next hard part was opening the door and stepping into the hallway.

They followed her to the secretary’s desk. Eyes from the hallway turned to see naked Vanessa. Between the other employees doing their jobs and clients heading to different rooms, Vanessa was the only one naked. It gave her a perverse sense of confidence and power as she was being admired as a sex object.

“Ms. Chen,” Caleb said with calmness. “Show Vanessa her new workspace.”

The assistant gave a brief tutorial on the public workspace, while Vanessa made note of everything. When the assistant pulled open the drawer, there was an assortment of lubes, paper towels, and other items used for anal entertainment.

“What are those for?” Vanessa asked. “Why are they at my desk?”

Caleb seemed puzzled for a moment. “Did I forget to mention?”


“It must have slipped my mind,” he said. “Every once and a while, I’ll need something for relief.”

Vanessa raised an eyebrow. “And that relief would be… my asshole?”

“Smart girl. Is that a deal breaker? Or are you interested in expanding the scope of your duties?”

She sighed. “I’m naked in a fucking commercial building. Your uptight assistant has stuck a butt plug up my ass, which I’m still wearing. I’ve already come this far. I want the job.”

“This part is easy to learn. I like women bent over the desk.”

She nodded. “Yes, Boss.”

Vanessa assumed the position and bent over the desk, which as it just so happened, meant that she’d be facing the open hallway along with anyone in the area. Her breasts and hard nipples felt cold against the desk when she laid on it. This was never a position she thought she’d be in professionally. It seemed like something only found in porn.

She spread her legs, wondering what would happen next. Sure enough, Ms. Chen pulled the butt plug out of her ass, leaving Vanessa with a gaping feeling. Then the assistant reached for more lubrication in the drawer, opened it, and poured directly into her asshole. The assistant used her magical finger once again to massage the anus into relaxation.

Ms. Chen held Vanessa’s asshole open. “It’s ready.”

Each of Vanessa’s butt cheeks were squeezed tightly and held apart. She pressed her face onto the desk and waited for her first anal fuck session. She heard the boss unzipping his pants and positioning himself behind her.

The tip of the hard cock touched her ass and she felt Ms. Chen doing all the work to ensure that the cock would have a smooth entry passing her anal ring and into her rectum.

“You’re very tight,” he said after a light thrust of his cock head.

“I take pride in that,” was all she needed to say on the matter.

She clenched her teeth as her rectum was being stretched. To make matters easier, Ms. Chen caressed her hair and whispered in her ear to relax and enjoy it, and that it would make things so much more pleasurable.

By :HeyAll

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