This is a story based on a true experience. Copyright 2017 by Chastebob

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.

"Let's deal with this matter of your dishonesty regarding your appearance first," I said and tapped the switch on her up turned ass lightly, finding my best position and angle.

"I'm sorry! I didn't do it to deceive, only to feel like a normal woman," she blurted out rapidly, her shame and humiliation were palpable.

I struck her in the middle of her cheeks, though the blow was clearly not hard the surprise of it made her gasp and she tried to raise up, which moved her ass and that lovely hairy pussy down and under from their beautifully exposed position.

"Silence! I didn't ask for an answer from you. You will know it when I do. And keep that ass up and your head and shoulders down!" I punctuated this last with another stroke of the switch.

"Yes, sir. Sorry, sir."

"I'm inclined to believe that your primary motive wasn't deception. If it were I think you might have gone for a larger cup size, or more revealing blouses." I continued applying the switch, with increasing force and spreading the strikes out all over her lean rump.

"Still, you are a married Christian woman. What should it matter to you what others think? Are you trying to be attractive to other men?" She tried to bear the strokes stoically while I continued to lecture her, but a flinch or a gasp now and then bore witness to their effect, even though probably more psychological at this point than physical. "Or is it a matter of ego? A little pride? An A cup pride, hidden behind high collar blouses?" She was weeping now, and clearly not from the pain of the switching. I decided to press on as this looked like it could be a cathartic moment.

"Isn't that right? Answer me!" A slightly more emphatic strike with the switch.

"Oh! Yes, yes, that's right. I'm sorry. I'm so ashamed." There were actual sobs and catches in her voice as she continued. "I want to be attractive to men, I want them to think I'm pretty. I want you to think I'm pretty. I went with the A cup only because more would have been too obvious if ... anyone ever saw me naked."

I was surprised by the depth of her revelation and realized that this was beyond our role play, but I couldn't stop now. I lightly rubbed the switch up and down her rear, being sure to tickle the pubic hair that stood out from between her legs and cheeks.

"You are pretty, inside and out." This obviously had an effect on her, her whole posture relaxed a little and she turned a little as if she would break position and reach for a hug.

"And you have confessed to harboring lewd and lascivious thoughts about other men." At this she stiffened a little and made sure her position was as prescribed. "You masquerade as a good Christian woman and wife, but in your heart, you are a slut!"

I punctuated this last with the strongest blow yet. It crossed her butt cheeks lower down and hit her protruding pussy lips. She shrieked and her hand flew back to cover her stinging privates. A faint red line was visible across her mildly rosy red butt.

"Don't you dare hide yourself from me!" I almost shouted and brought the switch up between her legs to strike the protecting hand a few times, more to show my insistence than to cause her hand pain. She quickly removed it.

"Yes. Yes you are right, sir."

I continued to bring the switch up between her legs to punish her pussy, but with much less force. She gasped and cried out but her movements were positively sensuous, as if her sex was reaching out to meet the switch. I had the most amazing hard on I could remember getting without any touching since adolescence. I dropped the switch to the floor and ran my hand over her cheeks, and between her legs, feeling the soft mat of her bush, and the moist, full lips guarding the entrance to her vagina.

As soon as I released the Velcro ankle restraints she spun around and hugged me so tight that I thought I might not be able to breathe. Then in an instant she was tearing my clothes off, almost literally. When my erection popped out of my underwear she barely let me kick them off my feet before she had her mouth on my cock. She was doing her best to deep throat it, but quickly settled for really working the head. Through my movements I indicated that I wanted to lie down in the 69 position. We got into that position without my cock ever leaving her mouth.

The ass and pussy lips I had just switched were now just inches above my face. I could see the red mark from hardest stroke, but it wasn't swollen, it would fade in hours. Still it gave me some satisfaction to have evidence of her punishment still visible. I took in the sexy sight and scent of her and then parted her thick dark bush to get at her secret charms. She was so wet that my tongue didn't need to provide any lubrication to separate the petals of her flower.

Her actions on my cock could only be described as frantic. On pure technique it wasn't going to rank in the top half of my experiences, but her eagerness and enthusiasm, together with the heavenly sight on my face, made it memorable in the extreme. I got one of her long lips between mine and gently pulled it out as far as it would go, sucking and licking it. Then my tongue found her little button.

Mimicking her pace I alternately sucked it into my lips and tormented it with rapid flicks of my tongue. She made little squeals in her throat while her tongue was furiously polishing my knob. Just then her legs stiffened and her mouth came off my dick for just a moment. During that moment she called out “AAAHHHHHH”, but it sounded like a single note. Then she was back on my cock and I could take no more and felt my nuts draw up. The ejaculatory spasms actually hurt. I could feel the hot semen shooting out of my penis and into her mouth. Her lips made a seal on my dick and not a drop of at least 5 spurts slipped out. She swallowed every bit, and then kept suckling on my cock as if it were a teat and she a hungry baby. I slowed my attentions to let her recover, while thinking to myself, ‘so that’s what a good Christian cunt tastes like.’ I couldn’t resist planting a ‘seed’ in her head.

“Tomorrow, in church, when you are singing, remember that note, and the moment that brought it out of you.”

Her embarrassed giggle confirmed for me that she wouldn’t be able to stop herself from thinking about it. So I pushed just a little further.

“While you’re at it, imagine I’m under that big, billowy robe, helping you hit it again.”

“You know I won’t be able to think of anything else!” she said blushing profusely.

“I’m counting on it,” I said enjoying my own mental picture of her face turning red in the middle of a song, wondering if the Choir Director would notice and wonder what she was thinking.

Our intimate discussions continued at work and I told her that I was thinking that my submissive side might actually be the stronger of the two. I confessed to her one of the more puzzling fascinations I had. While the thought of actual castration terrified and repulsed me, in an erotic story setting it had a strange appeal. Women were the ones taught to be ashamed of sex and sexual desire, not men. So a woman’s interest in her own mutilation might be like casting it out. In theory the same could be true of a man, but it seemed rare and didn’t fit with me at all. She could easily understand a woman’s interest in male castration.

The next time we were together was supposed to be a turnabout of sorts, with her helping me experience submission. However, her dialog was minimal and sounded forced while the switching was not forced enough. The encounter was not the torrid affair of our first tryst, but I did get to fuck that married choir girl pussy. I also got a demonstration of just how powerful the castration fetish was. I was deep in her and holding out fine until she reached around and cupped by balls, and whispered firmly in my ear.

“If you cum before I do these are coming off.”

I was immediately over the line spurting my cum in her till my balls ached.

We never hooked up again. I believe she was truly feeling guilty about cheating on her husband. My girlfriend and I moved in together, eliminating the ease of a place to go. Another reorganization and promotion sent me to the headquarters office, again with a staff in place.

It’s just as well that we didn’t have the opportunity to continue. These things never end well, and the longer they go on, the worse they end. Still I wouldn’t trade the experience for anything