I was just past 30 when I got my first supervisory position with a staff, including a secretary. My secretary wasn't hired by me, but assigned from somewhere else in the company following the massive reorganization that got me my supervisor's job. Sherry was tall and very thin, with small A cup breasts tastefully concealed behind high collar blouses. She wasn't unattractive, but she also wasn't the kind of woman to turn heads and elicit lustful thoughts. She was smart and competent and my career needed that much more than eye candy I shouldn't be involved with in any event. Although not married, I had a steady girlfriend. As I got to know Sherry she looked exactly like what she was, a married Christian woman who sang in the choir every Sunday.
The reorganization of the company was one of those things that executives do when they think they are being "visionary" or at least want others to think so. Where the work of the business actually gets done the result was less efficient procedures and processes. There was a lot of stress trying to make things work as well as they used to; while fighting ridiculously higher objectives that sought to validate the reorganization as an improvement in productivity. As a first time supervisor this was quite a bit more than I was ready and able to deal with.
Sherry could tell the stress was eating me alive and we began to talk in bits and pieces about our lives. I was pleased that she didn't try to convert me or tell me how Jesus was the answer to all my problems; frankly I respected her more for that. Through the course of conversations stolen in moments when, despite our heavy workload, we could go no further while waiting on decisions from above, I learned she wondered about a life outside the fairly rigid and predictable roles she found herself in, it was after all the 70s, the age of the sexual revolution. It wasn't that she truly wanted to leave her life, it was just idle fascination about what would a freer life look and feel like. It was much the same as a guy might wonder what it would be like to be some international spy or action hero. Somewhere in all of this the book The Story of O came up.
We both knew only a little about it, mostly just its subject matter of domination of a female known only as "O". As a piece of pure escape, and to have someone to discuss it with, we read it at the same time. My girlfriend had already made it clear that she was completely uninterested in the subject, no matter who dominated whom. I was not surprised that it turned me on. I had read similar literature since college and recently explored my own submissive desires with a professional domme.
Discussing the book at lunch I learned a great deal about female submissive fantasies. While Sherry's were rooted in her specific childhood experiences, she assured me that many women seem to have at least a little of this. Whether due to our culture, upbringing, socialization or whatever or some tendency from biology, she assured me that it was far from uncommon. Confessing that while dominating a woman as the character did in the book was a turn on, I was also aroused by the reverse. We talked about that some and I suppose apart from our personal paths, we concluded that a degree of submissive fantasy might be common for both sexes as a way to avoid the responsibilities of adulthood, and return to what from this perspective seemed a simpler and happier time when we had no decisions to make and we only had to be concerned about pleasing one person, our principal parent. So you see our conversations were personal and in a way intimate, but also intellectual and philosophical. At the time I didn't even see it as leading where it did.
A turning point of sorts came when the movie The Story of O was going to be playing in town. After all of our discussion of the book we simply had to see the movie and assess how well it was made into film. To avoid uneasy discussions we told no one else of our plans. She told her husband that she was meeting some friends after work, and I had no one to answer to, but would use a similar excuse if needed. We left the office in separate cars as always, but rendezvoused at the art theatre where the film was showing.
After, discussing the film I said how much I liked that the actress had a full bush, as that turned me on. Sherry squeezed my hand with a little smile. It wouldn't be long before I validated what I thought that meant. It must be 20/20 hindsight that makes our arrival in bed at my house on a Saturday seem inevitable, because it did not seem so certain at the time. I honestly cannot even remember who or how it was first suggested. Ostensibly we were to try some of the scenes from the movie on her, to let her live out the fantasy experience. I had acquired a few whips and crops and thought I could do a good job of giving her a painful feel, while tied down.
When the prim and proper clothes came off I discovered that her bush was thick and dark with wild and untamed hair; an interesting counterpoint. I also discovered her "A" cups were actually a padded bra and she was flatter than me. Her eyes had a slightly fearful look, wondering if I would be disappointed in her appearance. I was about to have a unique in my life experience, I would not let that spoil it. I put my hand on her pussy, luxuriating in her thick hair, feeling for her lips.
"I positively LOVE this!" I said while gently rubbing her. I leaned over and kissed her left nipple. She responded as if she were close to orgasm. I didn't know which action had excited her so much, or if it was the combination, but the uncertainty and worry left her face and was replaced by a small confident smile.
Seeing her confidence that I was pleased with her, I immediately dropped into "character" to get her ready for her whipping.
"So in addition to being punished for being a slut, and a cheating wife, I see we have one more issue to deal with." I nodded to her breasts. "Just because I don't have a problem with them is no reason to let you off for deceiving everyone about them." At this last she actually looked guilty, since technically she wasn't (yet) guilty of being a cheating slut.
"Kneel down and beg me to punish you like you deserve," I ordered and she was on her knees in an instant.
"Please, sir, whip me for being a bad girl."
It wasn't very creative but it was our first time. I ordered her onto her knees on the bed. I used Velcro cuffs on each ankle which were already attached to ropes that were secured to the feet of the bed. Making sure her knees were far apart I put two pillows in front of her legs so that her ass would be up high and splayed open and her chest could lean forward and down on the pillows. The position presented her ass beautifully and also spread that hairy pussy wide. I could see those long pussy lips in her thick bush. Her butt cheeks had very little padding due to how skinny she was. I silently wondered if this would interfere with our activities. Then she broke character to remind me that she couldn't have any marks left on her. That disappointed me and made me slightly mad, even though we had discussed it before. I was just thinking that to give her the proper experience would be difficult without leaving marks. Plus I had no experience with this, I didn't know how hard a blow to give that wouldn't leave marks. So that suggested I go very light and build up.
I decided that the intensity of the scolding might augment the reality of the scene and make up for the lack of welts on her backside. It came to me that the padded bra was a good place to start because it was undeniably true.
