Interview With Miss Dubin

Story Info
Pain and pleasure for a young job applicant.
6.9k words
4.39
15.6k
5
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Parts of this are based on stories I published a while ago. But while those depicted role plays, the characters here really are a manager and a job applicant.

One Saturday afternoon I got a call at the apartment where I was living with my family. My dad happened to answer it and said it was for me.

I said, "Hello, this is Paul."

I heard a woman's voice, "Paul A'mato? This is Janice Dubin, you know, from Trylon Typesetting. We met this week."

This was in the late spring of 1976. I had applied for a job as a part-time paste-up artist and proofreader at a Manhattan typesetting company. It seemed to dovetail nicely with what I had learned at my campus newspaper at the City College of New York. I already had gone through an interview with Janice, an assistant manager at the firm.

Janice said, "I was wondering if you could come down tomorrow evening for part of your job interview process? Say about seven-thirty. And bring another copy of your résumé."

I had never heard of interviews being done on Sunday evenings, but I figured that it was their company and they must have their reasons.

I said, "Sure Janice, I can do that."

"It's Miss Dubin, if you please."

That seemed a bit much; this was an era when the use of first names was becoming more common in the business world, even with superiors. But it seemed like a small thing and I would go along with what she wanted.

In fact, she had seemed quite nice to me during our initial meeting on Wednesday. I had the impression she was flirting with me a bit but maybe I had imagined that. I had broken up with my girlfriend over the winter and I was feeling lonely and, beyond that, I missed having regular sex.

She had casually asked me if I had a girlfriend. That was a rather personal question, and if a male had asked me that I might have been taken aback. But Miss Dubin was cute and personable, so I answered with the truth and didn't give it much thought.

On Sunday evening I was on the elevator of a Manhattan loft building going to the tenth floor. This was on West 24th Street. Nowadays realtors refer to the neighborhood as the Flatiron District, but back then it was merely a nondescript border area between Chelsea and the Garment District.

I was wearing the only jacket I owned then, a blue sport coat that dated back to 1972. I had a tie, nondescript pants and my usual unruly hair to make an impression. My résumé was in a manila envelope and that was the extent of my professional gear.

Just before I rang the bell at the company entrance I tried to clear my mind and prepare myself for whatever would happen next. I had a slight case of job interview jitters. Janice opened the door and smiled at me.

She was a fairly tall woman with dark-brown hair that she tied back into a tight bun. Even though it was a weekend she was dressed as if it were a workday. She had a blue jacket and skirt suit combination; the skirt was tight enough to give a good indication of what her body was like underneath it.

The rest of outfit was basic but neat: a white blouse, stockings, and black high-heel shoes. She was wearing the same black-rimmed glasses I had seen her wearing during the week. I noticed that her bright red lipstick matched the red of her fingernails,. Overall, she had a "hot librarian" look going, which I liked. I took a guess that she was about ten years older than I was; I had just turned twenty-one the month before.

"Hello Paul, I'm so glad you were able to come down here this evening."

I thought, she really is cute, even more so the second time around. I don't remember exactly what I said; it was something along the lines of, "It was no trouble at all. I'm glad I could meet with you." I realized that if some guy had asked me to arrive at his odd time, I would have found it strange. Being here with Janice, however, seemed just fine.

She put her right arm out with her hand drooping down. It didn't seem like I was supposed to kiss it; I guessed she was just avoiding a manly handshake. I lightly gripped her fingers. This slight contact sent a buzz into my skin.

"Well, let's go to my office and discuss things, shall we?"

With that she turned and walked away from me. Her high heels gave a nice shimmy to her ass which I couldn't help but notice. Later on I surmised that she knew I was looking at her.

The company filled the entire tenth floor and it seemed deserted. Miss Dubin confirmed that for me; she looked back and said, "As you can see, we're the only ones here tonight."

I was again struck by the unusual circumstances for this interview. I guess she trusts being alone with me here; maybe she's got a panic button somewhere under her desk. Then I focused again on whatever I'd have to do to get the job.

I followed her into her office and she closed the door. "Have a seat, please." Her room was quite plain, but the entire floor had an industrial feel that was common at such firms. All the walls were painted green except for the lower three feet which were a glossy gray. Harsh fluorescent tubes lit everything.

Janice sat behind the desk and immediately started some business chatter. I remember her saying, among other things, "Now I wear several hats here; I fill in as receptionist sometimes and I'm both assistant office manager and also assistant personnel manager." I thought of a junior high school-level quip like, you're not wearing a hat right now, but I stifled it.

After a couple of minutes of this tiresome talk she said, "May I see your résumé?" I had already given her a copy during the week, but I removed the one from the envelope and gave it to her. The amount of time and attention she spent reviewing and marking this skimpy document would have suited the Magna Carta.

Just as I was sinking into job interview boredom and irritation Janice pulled a big surprise on me. She rustled through some papers on the desk, "I know you have yet to fill out a full employment application."

That was true, but I hoped that I wouldn't have to work on it tonight. I hoped to be able to mail it in by the next day. Anyway, within a few minutes I would know all this had nothing to do with a job interview.

She said, "Excuse me for a moment while I get a form."

Janice got up and went to a filing cabinet, bent over and opened a drawer at the lowest level; then she peered into it. She was upright but bending over as far as possible to look inside. I heard her say, "It's really a mess in here."

Then she got down on her knees and wiggled her behind in the air as she made another pass through the drawer. Then with a not so subtle move, she reached behind herself and yanked her skirt up.

There was no way I could avoid looking at her. Now I was sure this lady was wearing pantyhose - but she didn't seem to have any panties underneath. I tried to confirm that. The stockings were a nude/tan color or whatever they called the standard version. I could look right through them,

I searched for a thong perhaps but that wasn't there either. The pantyhose had a seam in the back, but I could clearly see her anus and her dark pubic hair.

It was quite a shock to my system. My God, this chick is cock-teasing me like crazy. I felt both anxiety and a strong arousal. I didn't want one, but I got an instant erection. What does she think I'm going to do about this?

What she did was let have me have a good, long look, finally saying, "Ah hah, I got one." I assumed she meant an application form. As she pulled back she looked over her shoulder at me and put a hand to her lips, "Oops, sorry, I forgot." A highly unlikely explanation, I thought. I knew after this display of female ass I would have to spend much of the interview hiding a boner.

Janice looked somewhat flustered when she stood up. I know I was too; I could feel warmth in my face. She patted down her clothes and regained her composure as best she could before sitting down.

My impressions of her coming together; she was officious but sexy. Maybe her sexiness was just an affectation; maybe she simply enjoys discomforting men, including young job applicants like me. My concentration was certainly blown by her exhibitionism. I almost wished I could cancel the interview and get out of there. I wasn't sure I wanted to work at a place with the likes of her around.

I was glad to hear, "Why don't we save some time and you fill that out at home and mail it to me?"

Then she continued the interview with the usual vapid questions common to these proceedings. However, more subtle yet sexy bits of business kept occurring. She got rather intimate with a ballpoint pen; she kept putting this pen to her mouth. She got to licking the little clicker at the top and then pushing it up and down with her tongue. Click, click; the point at the other end went in and out. Then she moved the pen across her lips and managed to leave lipstick on it.

"What would you say is your greatest weakness?"

I wanted to say, that would be that I like to have attractive personnel assistants get their lipstick on my cock. Now she had the pen in one hand while using the other to stroke the shaft. This didn't seem like fun as I squirmed in my seat.

Janice said, "It seems a little warm in here." The HVAC system was off but it didn't seem that bad. Nevertheless she took some tissues out of a box. I noticed that her blouse was unbuttoned down to her bra. She used the tissue to wipe nonexistent sweat off the top of her chest.

Then she said, "Excuse me." She took off her jacket and let it droop over the seat back. Then she found some reason to put her hands on her hips and push her breasts forward.

"Where do you see yourself in five years?"

I could see myself in five minutes banging her right on her desk. However, I didn't like being toyed with like this. She put the pen on the desktop as she run a red fingernail along its length. This was distracting me from my already incoherent answers. Janice didn't seem to be listening to me anyway until she suddenly blinked herself into focus. She leaned forward and folded her hands.

"Now Paul . . ."

"Yes, Miss Dubin?" Women liked hearing their own names, right?

"There is a very important issue I want to discuss with you. It's right here in our employee handbook." The publication she picked up was obviously not the handbook; it was some magazine from a printing company. She flipped through the pages and then stabbed a spot with a red fingernail.

"Here's the section, Employee Discipline." The second word of that caught my attention. Something interesting seemed imminent.

Quoting some obviously made-up material, Janice said, "The basic information here is that in the case of certain infractions like excessive tardiness, absenteeism, insubordination, having an overly messy work area, et cetera, one warning will be issued and for the second offense, the assistant personnel manager"- she pointed to herself -- "that would be me, Janice Dubin, shall administer the punishment regardless of the gender of the miscreant."

I was impressed at how she seemed to make up this babble on the fly. Then maybe she hadn't; probably she had planned this game some time in advance of my arrival. In any case, she looked up and did some exaggerated blinking. Obviously this was my cue.

"What exactly are these punishments, Miss Dubin?" At that moment I enjoyed saying her name.

She went into the desk drawer and pulled out a big wooden ruler; then she put it on the desk and gave it a little pat. I struck again by the idea that all of these gestures had been rehearsed.

Janice looked straight at me and said, "Well Paul, these are always corporal punishments."

That immediately clued me into the game she was playing. I thought, some guys have to pay for a dominatrix, but I may get a job out of this. Actually, I was no stranger to spanking games with a few girls I had known, both as a top and a bottom. However, I didn't mention that. I was curious how she'd work out the next steps in her scenario. I wanted to know the exact path to fruition here.

My next line would move it along, I hoped, "Could you explain that in more detail, Miss Dubin?"

Her next gestures went as follows: she put her elbows on the desk. Her hands were palms down, fingertip to fingertip, forming a little platform on which to rest her chin.

"I'd be glad to; in fact I insist on it. It's quite simple, actually; I spank or paddle, or both usually, the buttocks of the offending employee. On the seat of the trousers or skirt first; then on the bare behind."

She likes spanking other women too? I didn't need to know that right away, so I stayed silent. She had her follow-up ready. Her hands went down on the desk and she leaned forward. There was a school teacher or guidance counselor feeling to her look. She wanted my complete attention and she was getting it.

"I'm going to demonstrate this on you, right now."

"But I haven't done anything."

"Not yet, you haven't. In any case, this will get you to concentrate your mind. You won't be as tempted into misbehavior if you know the consequences. Keep in mind, this will be only a fraction of what could actually be administered by me."

"Whatever you say, Miss Dubin."

"You really want this job, don't you?"

"Indeed I do." I rarely used the word "indeed" but with her it seemed appropriate.

Without further comment Janice got up and went to another chair, taking her ruler with her. It was a very utilitarian chair without arms, ideal for the purpose she was going to use it for. She said, "Come over here, please."

I had the problem of the bulge in the front of my pants which had been there for a while. There was nothing I could do about it now. It was up to Miss Dubin to decide to either comment on it or ignore it.

I stood at Janice's left but she was right handed so she told me to go to that side. Then she touched me for the first time that evening. With one hand on my back and the other tugging on my shirt she gently guided me over her lap. A little tap on my side indicated that that I should move closer to her.

She said, "First I'm going to give you some whacks of the ruler on the seat of your pants. It's sort of an introduction to our company discipline, I would say."

She pushed my coattails back and gave me a couple of pats on the butt with her implement.

"Ok, hon, are you ready?" Did she just call me hon, as in honey?

"Yes, Miss Dubin, I'm ready."

I wondered how much protection I would get from my cotton pants. She started with long swings from the very beginning, steady but not too rapid. I grunted each time, more from the impact than actual pain. I didn't keep count but she seemed to keep at for a while. Maybe there were fifteen but it certainly was bearable. At least my erection went down.

Then she did something unexpected. She stuck the ruler under my shirt where she could easily retrieve it. Then she started rubbing my behind.

"My, your backside certainly has heated up under there."

All I could think of saying was, "Yes, Miss Dubin." I was getting stiff again.

"It's such a nice, taut ass; it's a pity to have to punish it so harshly. But business requires strict protocols, I'm afraid. Now for the next phase. Lower your trousers, please."

I had to get up for a moment to do that. When I got back in position, she yanked my underpants down below my knees without comment. Now my erection was pressed against her skirt. It was her call, and she didn't seem to notice or care.

"Hm, I see a few minor marks. What I'm going to give you is a good hand spanking to warm up your tush a bit more before the finale."

I almost chuckled at her phrasing. Anyway, hand spankings were interesting. They sting but they can have a pleasant sensation on sensitive areas, erotically charged places directly connected to the genitals.

Janice had a strong arm, and she hit me hard each time. A few times she moved to my thighs for variety. She had some stamina for it; I knew her own hand was getting warm too. As she spanked me both my pain and pleasure seemed to go up at the same rate.

She stopped for a moment and said, "Your backside is reddening up nicely now." I thought about the connection between the physical and emotional side of these events. It couldn't be hurting too much if I was having these musings.

Then she rubbed each cheek again, on the bare this time.

"Does that feel good?"

Man, did it ever. "Yes, Miss Dubin, it really does."

"Now it's time for the ruler again." She got it from under my shirt. "Brace yourself please."

It knew this was going to have some bite to it, and she seemed to be uninhibited in her swings. After a few of those she said, "I know it hurts, but try not to move around so much." I looked back at her. She seemed focused on her task.

I didn't keep track of the number; somewhere beyond twenty she stopped. She poked me with the end of her implement. "These darker spots, I certainly made an impact in those places." Yes, Janice, you certainly did.

Then she said, "Time for my hand again." I was a bit worse for wear now and this time it was less pleasant.

"I hope you know now not to misbehave. Believe me, Miss Dubin can do this all night if she has to." Referring to herself in the third person was a notable touch. Anyway, I was beginning to wish that she was a bit more dainty But I knew that smaller women could accomplish a lot regarding discipline if they were motivated.

When she stopped again she said, "I've considered that a guy should take off his belt to get a punishment with that. It would be humiliating to be beaten with your own belt."

Why not humor her? "If you say so, ma'am."

"Please, I'm still young. Call me miss."

"Yes, miss."

She finished with six more of the ruler; I kept track of those. She said simply, "That's enough." It had been a successful session I suppose, although I didn't have the endurance that some other people had for hard spankings. Anyway I wondered what would come next.

She said, "I know that was a bit harsh; I see the marks the ruler made. But it's effective that way." She began rubbing my sore ass. "You're really burning now. However, you took that very well; I'm quite pleased with that. I hope you're always such a good employee." Baby, I'll be the best employee you ever had if you give me a chance.

Janice moved her right hand over and held my far hip. I'm not sure what the point of that was but it definitely make me even more turned on. Maybe that was the point. She said, "The ruler definitely goes deeper - deeper than the hand, I mean. There's the whole horizontal versus vertical dimension aspect to this."

Despite the odd phrasing I think I knew what she was getting at. Then she moved to the anticipated next phase. She said, "Lift yourself up a bit, get up on your toes I mean." Then, "I thought so." Her left hand went under me and she ran one finger along my cock. It didn't seem I needed to comment so I didn't.

She said, "I've seen this before; men often get erections when disciplined but I can take care of that." I hoped that didn't require more of the ruler.

Fortunately it wasn't to be that. She reached up for a bottle of hand lotion on the shelf behind her. Oh, it's like the ruler; another prop she had in place before hand. Her right hand was resting on my back while her left one was underneath wanking me. She was effective too; Janice seemed to have some experience with giving handjobs.

I looked up at her and caught her eye. I saw some glint in her expression I couldn't interpret. I then thought, when I come some of it may get on her skirt. She must have realized that so there was no point in worrying about it.

I had an inspiration. "Miss Dubin, may I give you a hand with this?"

12