The Choice You Make

This actually happened to me when I was younger. The names and details have been changed to protect a not-very-innocent supervisor.

She called herself Brimstone Bree because she was hell on the employees. I don't know why human resources put up with her, because any man who behaved like her would have been fired on the first day. She supervised the technology group and managed it like her own personal harem of college boys, a group of IT nerds who all lived in fear of her whips, which decorated the walls of her office. Many was the time, I heard her tearing a new hole into some over-confident computer nerd, "I don't care if you can't reprogram the mainframe! This new virus can access the whole company's password system! I want a fix in half an hour!"

Tom's voice argued plaintively, "But Bree..."

As usual, Brimstone wasn't listening, "Don't you 'But' me, Tom! I will whip that lily white butt of yours til it bleeds if you don't get me a solution." Tom's face was ashen white as he fled her office and ran to his cubicle to solve a problem that he had not even heard of an hour before.

"John, Get in here!" Bree ordered sharply at me across the office.

I glanced at Tom and shrugged my shoulders in sympathy as I steeled myself to take my turn at being dressed down for some problem that I have never heard of. Like the whole of the department, I thought I was hot stuff behind a computer screen, but like most young men who loved coding more than athletics, I was young, scrawny and more prone to spending time playing video games than football. I walked into her office reluctantly slow.

Brimstone was a nightmare in the office, but her office was decorated for a young man's fantasies. I think she did it to put men ill at ease. Behind her desk was a large poster of Michelangelo's David beside a Chippendale calendar that was probably the largest calendar that they published. The young exotic dancer was pictured in glossy 18 inch by 18 inch muscular splendor. Everywhere you looked in the room was paraphernalia that could only be purchased from adult bookstores. Dildos and vibrators rested on every surface. A metal frame was above a black futon that mounted various whips and black leather paddles. Not least of all was Brimstone herself. The rubenesque lady wore a tight leather corset that squeezed her generous cleavage up so that looking at her behind her desk made you wonder when her breasts would come bursting out. I tried hard to find a place in the room that I could look without getting a hard-on or blush in my innocence.

In spite of the harsh demeanor that I heard her strip the hide off of my colleague a minute before, she was sweet with me. "John, I need you to type up some correspondence for me." and handed me a notebook full of letters. I did not ask why somebody who worked with computers all day did not type her own mail or email them. You just did not ask her stupid questions. I was the one that all my friends turned to help type their papers in the dormitory, because I would correct their grammar and probably more than a few of my friends passed their courses due to my help, so I assumed that she wanted me to clean up her language and phrase her correspondence more diplomatically.

But this time she admonished me, "I want you to type that top letter exactly as I wrote it." I glanced at the letter, "Dear Burlesque Lingerie Customer Relations, I recently purchased..." It went on to describe in explicit language the poor quality of their underwear and how their one-size-fit-all stretchable material was not designed to withstand the forces of her voluptuous figure and just exactly what she thought of them, their mothers and their mothers' mothers.

I gulped, swallowed, and nodded my head. "Yes, Ma'am."

She continued, "And I want to mail it all today, so get it to me as soon as possible. I will be leaving in an hour."

I looked up at her in shock, not even stopping to consider why her nipples did not show from the top of her outfit. "But this will take me hours to type and find the addresses!"

"Then you will have to bring them to my house, won't you? I want to sign them and put them in the mail this afternoon."

I looked dejected, but acquiesced, "Yes, Ma'am." My hopes of making it back to the dorm in time to go to a kegger at the lake with my friends just dashed.

I finished typing the letters, finding appropriate addresses, envelopes, and stamps in record time. It only took me about two and a half hours, but my supervisor had already left, so I put the correspondence in my courier bag and biked it three miles to her house. I had never been there before, so I was surprised; It was much larger than a single woman needed. I knocked on the door. Nobody home. It was a boiling hot summer day, so I found a spot under a shade tree and sat down to read material for one of my classes. In about half an hour, she pulled in the drive in her mercedes. "Were you waiting long, John?"

"No, ma'am. I just got here."

The voluptuous woman steered me into her house, "Good. Come on in. I will fix us some lunch."

I was more than a bit nervous to be dragged into the abode of the succubus who called herself, my supervisor. "I am fine, Ma'am."

"Nonsense. You came out here on a hot day. At least have something to drink." We went into her kitchen. In contrast to her office, the house was surprisingly tasteful. There was a nude painting on the wall, but no whips or sexual implements lying around. I curiously glanced down the hallway, half expecting to see a St. Andrew's cross at the end, but I was disappointed. It could have been the domicile of any industry executive.

She said brooking no argument, "I will sign these and run them to the post office. You will stay for supper. I have an old swimsuit of my ex that you can take a dip in the pool while you are waiting."

I politely deferred as I stood at attention, "I don't need supper, Ma'am."

"It's a hot day, John. I am sure you will enjoy a dip. Just relax." She went back into the bedroom and came back with a thong bikini that would hardly cover any of me and dropped it on the table. "I will be back in a little bit. Enjoy yourself." Her shapely ass swayed as she headed out the door to run her errand.

I picked up the bit of cloth that she had left for me as a covering and wondered if she realized how big my cock was. The strip of pale blue bikini would barely cover my genitals when soft and slip up the crack of my ass. Was she testing me? If I got a hard-on in that skimpy swimwear, I would be completely exposed, but it was obvious that Brimstone was not shy about seeing men naked and I might as well be naked in that bit of swimwear. I knew that my supervisor liked dating younger men and this all seemed like a pretense to get me in a casual situation outside the office. This could be my chance to get a permanent job with the company, perhaps even a raise if I put on the swimwear and demonstrated my willingness to do what I was told.

I picked up the strip of fabric and felt its silky smooth texture and considered what might happen if I put it on. All of those whips in her office... I had no doubt somewhere in this house, there would be ropes and handcuffs designed to suspend a young man and hold him in her thrall. But if I accepted this role, would I be undermining the professionalism that they taught us in college? Would the good recommendation that I was counting on from her perhaps be thwarted by some failure in a romantic relationship? On the other hand, if a romantic relationship developed, I might find that her connections would lead to a position similar to her own, supervising a major company's IT in a developing field. I might even end up owning a house as large and ostentatious as hers some day.

Better yet to my lustful young mind was the possibility that I might become Mr. Brimstone, her permanent consort fulfilling her and my desire for a cougar/cub relationship. I started getting hard thinking about the role that I might play, being smothered in her plump curves, laid across her thighs and spanked, used as a boy toy. I would be under her as she trained me to greater and more pleasurable service. She was clearly experienced and demanding with men. My future fate was right there in that piece of cloth that I was holding in my hand and I wondered what harm would there be, if I just enjoyed a quick swim in her pool.

Postscript. In real life, I put the bikini bottom down and ended up working a different career path, but thinking back to this liminal moment I might have been better off putting on the bikini. I certainly would have had more fun.