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Ms. Sandstrom’s Assistant, Part 2: The Interview

Cheryl asks Mike some unusual interview questions

I held my hands in front of me as I walked, trying to conceal the erection that was rather obviously tenting the front of my slacks. My heart was still pounding as I tried to slow my breathing and stop thinking about the interrupted blowjob from the secretary — Liz, I reminded myself. Don’t forget her name! Despite my arousal, I needed to get my head straight and nail this interview.

I followed Liz into the most attractive office I’d ever seen in my life. Whatever I had imagined a sex toy company CEO’s office would look like, Cheryl Sandstrom’s defied expectations. The wall behind her desk was floor-to-ceiling glass with a fantastic view of downtown. She’d had the left-hand wall entirely covered with shelves. Nestled among the books were some of the company’s most popular products, displayed like works of art. The carpet on the floor was so soft-looking that I wanted to take my shoes off and scrunch my toes into it.

Mrs. Sandstrom sat behind a beautiful antique desk made out of some sort of dark wood. It was neat, with no clutter to distract from her laptop other than her mobile phone and a mug of coffee. She did not look up as Liz gestured for me to take one of the seats in front of the desk. I sat carefully, adjusting my pants in a way to hopefully make it less noticeable that I was still rock-hard.

As she sat there, typing, I had a moment to regard her. She was an attractive woman in her late forties. Her dark hair ended at her shoulders, and she wore a simple cardigan over a floral-print top with a v-neck that teased her large breasts.

I shook my head to clear it. What was I doing? It’s a terrible idea to objectify the woman you’re asking for a job. I took a deep breath and tried once again to move past the fog of arousal clouding my thoughts. My erection twitched disappointedly, but with relief, I felt it begin to diminish.

As if sensing my interest, Mrs. Sandstrom leaned back in her chair and regarded me critically. Her dark eyes were piercingly intelligent and seemed to see right through me. They drifted down to my lap for a moment, and my heart skipped a beat, terrified that she’d see my hard-on and kick me out. Thankfully she didn’t seem to notice and made eye contact once again.

“Thanks for coming in, Mike.”

“Thanks for the opportunity, Mrs. Sandstrom.” I swallowed nervously.

“It’s Ms, actually, but please call me Cheryl. If you get this job, we’ll be working …closely together.”

“Of course. Cheryl, it is.”

She paused for a moment after I said her name and then nodded to herself. She held out her hand, and Liz gave her the clipboard with my forms.

“Thanks, Liz. Will you wait over there?” She gestured at a couch against the frosted glass wall separating her office from the waiting room.

I watched Liz saunter over to the couch and settle comfortably on it. She didn’t seem to be having any difficulty with lingering arousal. Of course, she wasn’t the one who had been about to cum. Shit. I was thinking about it again. I crossed my legs and tried to clear my head.

“Mike,” said Cheryl, sensing my distraction. “You’ve done well so far, and I think it’s safe to say we’re interested in you. Before we can extend an offer, however, I’ve got some questions for you.”

“I’d be happy to answer them,” I replied as she pulled up a document on her laptop.

“How do you feel about working under a woman?”

“No problem, I love women.” She looked up from her questions and raised an eyebrow at me. I stammered and tried to fix my answer. “I mean, I think women can be smart and great leaders, and I’m in favor of women running things. I voted for Hillary!”

She blinked and looked back to her laptop. Oh Shit. I was fucking this up already. How did I not expect a question about feminism from Cheryl Sandstrom? I licked my lips and resolved to do better.

“Do you take orders well?”

“Yes, I think so,” I answered, relieved to have a straightforward question. “The most effective executive assistants work as force multipliers. I make you more efficient by taking problems that don’t warrant your full attention off your plate so you can focus on more important matters.”

“That’s great, Mike, but it doesn’t really answer the question.” She looked me in the eye again and clarified: “If I ask you to do something, will you do it, no questions asked?”

“Um,” I hesitated, concerned this was a trick question. I didn’t see any way around it, though. “Yes, within reason?”

She nodded and moved on. “Would you say you have an adventurous personality?”

“Uh, yeah. I mean, I enjoy kayaking and stuff. I like to stay fit.”

“Do you have any allergies? Such as latex or silicone?”

“No allergies,” I answered. Those were weird examples, I thought.

“Would you be willing to shave for this job?”

“I’m already clean-shaven,” I answered, confused.

“I’m not talking about your face.”

“Um, sure?” What the fuck?

“Have you ever been tied up during sex?”

“Hold on a second, what’s going…”

Cheryl held up one hand as I started protesting and looked me in the eye as she explained.

“You wouldn’t have made it through the door if you didn’t have the requisite qualifications. This is a prestigious position. You will learn a great deal. After working in this office for a year, you’ll be able to command a higher salary than you’ve ever dreamed of. If you’re uncomfortable with the direction this interview is proceeding, you’re welcome to leave. But if you stay, I insist you take this seriously and answer my questions.”

My hesitation drained away. I needed this job. I nodded, and she returned to her questions.

“Have you ever been tied up during sex?” No.

“Have you used a cock ring to delay orgasm?” No.

“What’s the longest you’ve gone without an orgasm?” A few days?

“How many times per day can you cum?” Maybe 4, with enough rest.

“On a scale of 1 to 10, rate your enjoyment of the following activities: Solo masturbation.” 7.

“Mutual masturbation?” 8.

“Group masturbation?” 6.

“Public masturbation?” 1.

“Phone sex.” 7.

“Talking dirty.” 6.

“Hearing dirty talk.” 9.

“Receiving oral?” 9.

“Giving oral?” 8.

“69?” 5.

“What about spanking?”

“5 for giving, 1 for receiving,” I replied, getting into the spirit of things.

“Anal sex?”

“10 for giving, 1 for receiving”

“Pegging?”

“What’s that?”

“That’s when Liz over there wears a strap-on and fucks you with it.”

“Oh,” I turned around and looked at Liz, who grinned devilishly. “Oh, uh, still a 1, I think. Sorry, Liz.” She looked disappointed.

“Do you have any STDs?” No.

“Would you be willing to be tested?” Sure.

“Very well.” Cheryl looked up from her laptop and met my eye for the first time since starting the questions. She spent a long moment looking at me, and I had the sense she was making up her mind. My heart was pounding. Did I get the questions wrong? Was I not into enough of the things they were looking for? I should have said I’d be willing to try being pegged.

“Here’s the deal, Mike.” She leaned forward, resting her elbows on her desk and steepling her fingers. “I won’t lie to you, this is a high-stress position. Liz and I work long hours. I’ve learned that mental determination will only take you so far. At some point, the body has physical needs. The sooner and more thoroughly they are addressed, the better we can stay focused on the job at hand. Do you understand?”

“I think so. You’re looking for an assistant who can help you blow off some steam so you can get back to business.”

“That’s right,” Cheryl nodded, looking pleased.

“I do have one question.” She nodded for me to proceed. “Why do you need an executive assistant if you already have a secretary?”

“Secretary?” She looked confused. “What do you mean?”

“Liz,” I said, glancing back towards her on the couch. She winked at me. “Is she not?” I looked back at Cheryl and felt the heat rising in my face as I realized my assumption was wrong.

“Elizabeth — who might be better known to you as Ms. Holman — is my Executive Vice President. She’s not my secretary.”

Elizabeth Holman! I knew that name. She’d been on the 40 under 40 lists before the company she founded failed dramatically. She’d dropped out of the public eye after that. Apparently, she’d convinced Cheryl Sandstrom to give her another chance. How had I not recognized her?

“I’m so sorry,” I stammered. “I just assumed.” I shot an apologetic look at Liz, who seemed amused by my confusion. “She was sitting at the desk and gave me the paperwork…”

“It’s alright, Mike,” Cheryl reassured me. “I asked Liz to greet you and …warm you up for your interview.”

I’m pretty sure my jaw hit the floor at this point. Cheryl smiled and moved on:

“Not just anyone will be capable of integrating into this team. In terms of prior experience, you seem to be a solid candidate. Now I need to see if you can perform. Your final task will be to make Liz cum. You have 10 minutes. You may start immediately.”

I didn’t move for a long moment. Cheryl looked at her watch. “Tick-tock, Mike.”

TO BE CONTINUED

 

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