Missy Carries on for Me

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Training her supervisor meant all kinds of service.
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[This story arose from close collaboration with SplendidSpunk, to whom I am deeply indebted for his major contributions. The initial idea was mine, but after that, we shared equally in its development. Those offended by enemas and excrement or humiliation generally should stop right here.]

I've had what some might regard as a peculiar life story. Raised as the middle child in what we increasingly would call a normally dysfunctional family, I couldn't wait to get away from home and find my own way in the world. Home was a place I learned to avoid by the time I was in high school.

First, our parents believed in imposing strict discipline in an age when hardly anyone else did. My older brother, younger sister, and I were spanked from when we were little until well into our teens. I'm not at all surprised that the rather weird practice Mom and Dad had of punishing us at the same time helped lead my siblings into an incestuous relationship. But that's only one reason that I hardly ever see any of them and haven't for some time.

Every Friday before supper, Mom took out her little book and had the three of us standing before her as she read out our demerits for the week. If one of us had behaved reasonably well and had acquired a very few marks, Mom would go easy and it would be a light spanking on the bare bottom. Greater amounts of offense marks meant that you had to strip in front of everyone and Mom or Dad might have you over the chair or the bench for the strap, switch, crop, or cane.

Embarrassment was the norm, although we soon became accustomed to seeing each other in the nude. Susie was two years younger but she matured more quickly and became very self-conscious as her bust expanded to a nice 34B. Harold invariably had a hard-on, which he had no ability to hide or, apparently, control. I remember crying my eyes out because everyone would see that I had a tampon string hanging out of my vagina.

Once I got to university, everything changed. I met a whole group of marvelous people, some of them boys who were very attractive and attentive. I had been much more academically focused, so I went to a first-class college, unlike my sibs. I became enamored of smart people, even if they were duplicitous. I even joined a sorority, although I never found it worthy of much of my attention once I was initiated.

When I graduated, I was offered a generous fellowship program to pursue my studies at the graduate level. My supervisor in the department was named Diane and she was an attractive auburn-haired woman in her 30s who was an associate professor. She found my work more than acceptable and we quickly became close friends. I always had dated and had several regular guys after me, and yes, I slept with some of them sometimes.

But one day Diane returned to the spacious apartment we now shared—as she was single—and told me she was having serious problems with her research. As she described these to me, it did not take me long to analyze her subject and suggest several approaches, all of which would be difficult but rewarding, but which would help her toward overcoming her obstacles. Privately, I wondered how someone brilliant enough to have attained her position, could lack the basic puritan work ethic so essential in research. My suggestions were not earth shattering and should have been obvious to her.

A few weeks passed and one day she returned home to tell me that my ideas had produced totally fine results for her, and she would soon be finishing the project that had caused her so much concern.

Smiling, she looked into my eyes and managed to inquire, "Leslie, you do have to tell me how I can repay you for your help. I feel as if I should be the grad student and you the professor."

While I appreciated the compliment, something inside me made me feel that she was looking for me to assert myself, even though I was still officially under her academic supervision. I looked her straight in the eye and hoped my perceptions were on target.

"Diane, I'm so happy for you," I began, but then my tone grew more firm, "but I think you would benefit from more discipline in your life than you have had. Had you been more grounded in this assignment, you would never have found yourself in need of assistance. Discipline and structure will enable you to easily meet the challenges of your position. If you agree with my assessment, I am going to make some changes around here."

Diane seemed torn. "I think I see what you mean, Leslie," she said haltingly, "although when you use that word 'discipline,' do you mean in a physical kind of way?"

I felt she was moving right down the track. "Yes, Diane, I mean it both ways, mental and physical," I responded quite brightly.

"Basically, I will set out your duties and responsibilities—both here and at work, and I will, at least initially, make sure you are actively carrying them out," I started, "and yes, there will be rules for your behavior here, especially. You will be responsible for cleaning up and not leaving your dirty clothing lying around."

"And if I cannot perform to your exacting standards?" she asked, knowing what was coming.

"You will be subjected to discipline," I answered. "You may lose some privileges, such as going out to dinner or the movies...or if I feel it necessary, yes, you may be spanked."

"Spanked?" she repeated, "like a child?"

"Yes," I agreed, "for I have found that childish punishments are very effective with grown women like you as they are with little ones."

"This may end up being very embarrassing for me," Diane stated.

"Think of how embarrassed you would have been if you had failed to complete your project," I said, bluntly.

Diane turned to me and without any further inquiry, kissed me deeply on my lips.

"I am ever so grateful to you, Leslie," she said, "and if this does embarrass me, I suppose I deserve it and it will help me in the end."

While the kiss surprised me it did not stop me from returning it with as much passion as Diane. Yet, I knew this was the time to begin drawing the line, asserting my authority and control. I gently pushed Diane away and suggested that she should begin by cleaning her room and that I'd be by later to inspect it.

I then left the apartment more to give myself time to cool down, that kiss had me very distracted. I also wanted to allow Diane some time to accomplish her initial assignment. I felt a few hours would be sufficient and pulled my cell phone out and made a call.

"So glad I caught up with you, do you have time to meet me for some dinner? Great! Yes I know the place. I'll meet you there in fifteen minutes or so."

Well that worked out nicely, I get to have dinner with Kevin while Diane cleans and wonders what it will take to please me. Smiling I met Kevin outside the Bistro and gave him a light peck on the cheek then grabbed his hand and we went inside.

"You seem so happy Les, and while I'm not complaining, a middle of the week date is not your usual style."

"Kevin, I am happy at some recent developments and I want your help in them, if you will."

"I've never been keen on saying no to you, in fact I don't recall denying you ever, so yes, what is it you want from me?"

I explained what had happened with Diane ending with the kiss. Kevin was not stupid, heavens I've no time for men who can't think. He realized that Diane wanted nothing so much as my approval and was obviously willing to do almost anything for it. Kevin knows my history of the childhood spankings and humiliation I'd experienced. He's the first lover who feels it's not his job nor is it necessary to apologize for my parents. In fact he has said on more then one occasion that if more parents took half the time my parents had with their kids the world might be a better place.

He felt my siblings and their incestuous couplings would have happened anyway, that the communal nudity of our disciplinary sessions may have put the ball in play sooner but that the two of then had been born with the team uniforms and would have played that game regardless.

"So what is it you want from me? You've the capability of handling Diane."

"Yes, I know and while I do enjoy the prospect of sex with her, I want to make sure she understands her position with me will be one of subservience and obedience, not as a lover."

"Agreed, I don't see you limiting yourself in that way."

"So once I've begun to actually exert myself, I will need you to be her initial embarrassment, if you will. Someone she knows, seeing her naked and her ass striped."

"Well you have a lot of choices there, some would even present a better option, so why me?"

"Quite simply dear Kevin, I enjoy fucking you and who better then my lover to assist me with my new sub?"

We both smiled and discussed the plans for Diane. While I had a basic program in mind and Kevin was on board, a lot of details needed to be worked out. We adjourned to Kevin's apartment after dinner and planned to work out some of those details; however, once inside his door, I let the passion ignited by Diane's kiss earlier in the evening mature in Kevin's arms. Given his reciprocating gestures, I assumed correctly that our plans for Diane had not only taken root in Kevin's mind but that his cock was up for the idea as well.

"My god woman, you are one sexy treat. I often feel as if you have some mystical hold on me, it so rare for me to not feel like a brainless male bimbo when I'm with you."

"Well, Kevin, I do so like that male bimbo and what he and his cock can do for me."

Like teenagers finding a moment when no one was looking, we ravished each other's mouths as our hands groped and opened the bits and pieces of our clothing. By the time we'd reached the arena of our desires, the bed, we were naked and panting. One of the reasons I continued to see Kevin was that each time we met up we had eventually ended up having sex and each time the passion was equal to that usually experienced by lovers on their first fuck, but with Kevin, it was every time. I've tossed too many ripped blouses and broken clasped bras, not to mention retuning to my own place half exposed from a blouse with no buttons and a bra that could not be worn.

Tonight was no different, our clothing ripped from our bodies and strewn in a path from the front door to the bed. Diane would have to wait: I had a nice hard cock here and a man who knew what I liked and was currently feasting on my tits. I could only lay back and enjoy as his lips, his tongue and by god his teeth pulled my sleeping nipples from their cozy retreat and set them aflame with passion.

"Damn it, man! Why do you make me so damn horny? I'm already wet and ready."

"Les, it's always been this way and with any luck it will stay this way. It's all I can do to not cum now, you've got me so hard and ready I doubt I'd get halfway in your puss, before exploding."

Yes, Kevin never failed in that way no matter how ravenous we were. He let me take him in my mouth and while I am no pro, I do know what a man loves a woman to do orally; he can hold back if he wishes. He has amazing control and so I ignored his plea and managed to put my head between his legs, and his head between mine. It was time for a bit of dessert before the brandy. I eagerly took Kevin's shaft into my mouth as his lips worked magic on my labia and clit.

It was so basic and yet so fucking good: mutual oral stimulation. I had to stop sucking his rod for a bit as his tongue and lips were being particularly efficient with my pussy and his fingers were probing both openings. I had to pull my mouth from his cock so I could let go:

"You bastard, I love it, Oh shit, lover, that feels so damn good."

Then I slammed my mouth back down on his cock, feeling his stiff pubes on my lips as I took all of him. Oh god, this was so good but still only a fraction of what was to come that night.

It's not a stretch to realize that we both were about to cum in each other's mouths when I managed to see my watch and remember that I needed to return to check on Diane. Kevin and I both would remain horny enough to resume this later.

Men react badly to what some now called "ruined orgasms"—you know, when they're all hot and bothered and about to spurt when you call a halt, for whatever reason. But this time he and I were on the same wave length, so he grunted and then smiled at me.

"I'll make it up to you, darling," I said with sincerity, "and I also think that coming with me to check on Diane will stimulate that not so little thing of yours."

This time my clothing had not been so mangled that getting dressed would prove a challenge, so I quickly put my panties back on and retrieved bra, blouse, and skirt, as I watched Kevin become respectable as well. I knew that just from what we had been doing my slit would keep flowing and thus I would have a wet panty crotch, but some things just can't be avoided.

We returned to the apartment where Diane was still making piles of her material and had not progressed very far in her assigned clean-up task. She did seem mildly surprised to see me accompanied by Kevin, although she knew he was my boyfriend.

"Diane," I began, "you have not made very much progress toward completing your assignment."

"I know, Leslie," she responded, realizing that she was going to be in trouble, "but this is all a bit new for me. You have made me realize how much I need the kind of direction you are providing."

"That's all well and good," I said, "but I expect better effort on your part. I'm afraid we shall have to begin your discipline regimen now."

At that, her eyes flashed and she asked, almost plaintively yet with a challenge, "And I suppose he will be here to witness...my punishment?"

"Having Kevin witness you being disciplined, Diane, is apt to make you all the more likely to try harder from now on so this occasion is not repeated very soon," I answered calmly.

I knew that in terms of setting a pattern for making this discipline effective, I would have to employ a good deal of ritual and that someone as intelligent as Diane would probably get off on it, anyway.

Diane was wearing a short tan skirt and beige blouse, her auburn hair worn up as she had clearly intended on becoming engaged in her cleaning assignment. She was wearing flats and had no hose on.

"Let's start by having you stand right here in front of me and lift your skirt, Diane," I said most calmly.

She slowly walked round the bed and came to stand where I had instructed and then, already assuming a subservient role, took her skirt hem with both hands and lifted it above her waist, disclosing a pair of red-and-white striped hi-cut panties.

I looked over at Kevin long enough to see that there was a true tent in the front of his trousers rising about as speedily as Diane's skirt had.

As I reached for the waistbands of her panties, I kept on with the ritual tone, "I'm now going to lower your panties, Diane, for your spanking."

I then sat down on the armless desk chair that was to my left and tapped on my lap, making the age-old sign that meant she should drape herself across my skirt for her spanking.

Diane said nothing but arranged herself as comfortably as she could across my skirted lap. Now was when she would begin to learn the true meaning of embarrassment as I looked at her panties around her ankles and noticed a small skid mark.

"I notice that you have stained your panties, Missy," I stated, using a favorite name when punishing a woman. "You will receive extra strokes for that, I'm afraid, and I shall also have to examine your bottom to see if you are clean in there."

Diane let out a large sigh and turned her head to me, "I hope you realize, Leslie, that this is horribly shaming for me, especially for Kevin to observe me now." I could see that as tough a facade as she normally could maintain, she was now close to tears. Indeed, her emotions were welling up enough to emit droplets that began to make her mascara run.

"That is one of the purposes of this discipline, Diane," I commented in reply, and I poked my finger between her cute bottom cheeks, realizing that the alabaster hue would soon turn pink and then crimson.

I ran my finger deep into her rear crack, from high on her rear down through her furrow, stopping before the vaginal opening, however. When I removed it and brought it to my nose, it clearly smelled of her last movement and I held the finger in front of her face, with the slight smudge on the tip visible to her.

"In future, Diane," I said, "it appears that you will need to see me twice each day for a panty and bottom inspection until you learn to keep yourself clean back there." I could see that Diane's face had already reddened with embarrassment. There was even, to my experienced eye, a glimpse of possible rebellion as my shaming effort proceeded apace.

"Leslie," she managed to gasp in a very small voice, "I don't think I realized how difficult this experience would be." She paused and I awaited her next words.

"But you have no idea how I also appreciate how much I need this and how grateful I am to you," she somehow got out.

Even though the expected rebellion never occurred, this did not diminish my effort to make her realize her new reduced status around here. Then I had an even better idea.

"As I will be away from here at times, going to work, etc," I added with a grin at Kevin she could not see, "I will use Kevin for your inspections should I not be about for a scheduled or surprise check-in. I want you to understand that I am giving him complete authority to discipline you in any manner he feels appropriate based on your conduct."

Then I proceeded to the business at hand. I started spanking Diane, increasing the velocity of the slaps as I alternated giving her first five strokes on one cheek and then the same on the other, repeating this until her bottom attained the desired degree of redness. I should note that she began by letting out small moans that turned to exclamations and almost screams as her bottom grew ever more tender.

I was not altogether satisfied with the spanking and when wisdom had me check between Diane's legs I found that her puss had gone soggy and her clit swollen with desire. I looked at Kevin and said.

"I believe Diane is actually a bit of a pain slut. Kevin, come feel her pussy. See how wet and ready she is!"

"Oh no, no please Leslie, please no. Please don't allow Kevin to touch me there."

"Leslie, I believe that it's time to explain a few of your rules to Missy!"

I watched Diane squirm on my lap. I believe she had hoped that her outburst would give her an additional spanking, something I came to learn she both needed and wanted. Instead I pulled her to her feet and commanded:

"Missy, clothes are for good girls and you are not a good girl tonight. You've embarrassed me in front of Kevin, you've insulted him with this silly tirade of yours, now take everything off, and do not think to challenge me on this."

"But...."

"NOW, MISSY!"

She slowly started the process of removing her blouse, then skirt and finally her bra. Standing naked but facing me, hiding her body from Kevin I made her turn about.

"Missy from now on, you will refer to me as Ma'am or Mistress. Until you have proven yourself a capable adult, you will not address adults by their first names, not in this house. Kevin will be Sir. Now I see I have some work to do with you."

I had decided that in her new role as a child she looked ridiculous with pubic hair and I was about to march her into the bath and have her take care of it when Kevin said:

"I'm going to step out and pick up a few things I believe we will need tonight Les. I should be gone no more then twenty minutes, perhaps you can organize Missy a bit while I'm away."

Kevin left and I took Missy to the bath. I handed her the soap and razor and said as I pointed to her pussy,