Madison Avenue Advertising Men: Peggy

AMC recently launched a new series, Mad Men focusing on a Madison Avenue advertising agency, beginning in April 1960.  The series demonstrates that things that seem to be, seldom are.  The satirical stories herein are set in an alternate universe where Dick Nixon eventually wins the election of 1960.  They reveal that which I would like to see occurring in Mad Men.  But I doubt that AMCTV will follow up on these suggestions.

A Bridge and Tunnel Girl Does A Cross-Town Commute  As Peggy boarded the downward bound elevator from the Cooper-Sterling Agency offices she held her two hand tightly together gripping her purse so that their shaking would not be apparent to the other occupants of the elevator.  But that didn’t entirely work because her right leg started to shake as she clenched her buttocks tightly together.  Now she became conscious that clenching her butt was thrusting her pelvis forward, she blushed.  She was the only woman in the elevator and she felt that all the men in their grey suits were looking at her as if she was naked, examining directly her breasts beneath their concealing layers of blouse, slip and sturdy bra.  However the only thing that the men took note of was her rhythmically moving leg and one, a seemingly nice man from another firm remarked, “Oh, I see that you’re into the latest hit”.  Peggy’s mind raced at the suggestion of “hit” and she blushed before realizing that he wasn’t referring to a beating but to the popular Top 40 tunes.  She nodded to him but remained silent as her heart raced in panic.  Would this elevator ride never end.  But then, on the other hand, every second that ticked on brought her another second closer to her Friday evening appointment with Joan Halloway, her office manager.  One week at her new job, her first job after secretarial school, and she was quaking.  And not with joy but with dread anticipation.

At last the doors of the elevator opened and Peggy walked out into the lobby of the Meisian glass tower box housing the ad agency where she worked, or hoped to continue working, and prayed to continue working.  Although it was a bright early summer’s day in midtown Manhattan, she was shivering as she walked up Madison Ave. toward the street where she would catch the cross-town bus that would take her to the West Side address that Joan had given her.  “Be there by 6:00 and we will take things the next step” were the instructions given her.  “If you’re not there I will take it as an indication that you are no longer interested in this job” was the verbally stated conclusion.  Each click of her heels as they struck the sidewalk seemed to match a thump of her terrorized heart and she mulled things over.  She had cut her ties with home quite thoroughly.  All of her money had gone to secretarial school.  If she left her first job it would be without references.  This was early in the summer of 1960.  Although the economy was picking up after the recession of 1957-8, it was a hard time for secretaries.   All too many post-war brides, their children now well into elementary school, were seeking to return to the work force.  This was not the time for a penniless girl to be looking for another job.  She knew what she had to do.

A cross-town bus arrived, she dropped her token into the fare box and grabbed the first available seat as the bus lurched west.  As Peggy smoothed her somewhat voluminous skirt she remembered Joan’s caustic comment on its mid-calf length.  “1958 is long gone”.  Joan had made a similar comment when observing Peggy’s light brown bangs and ponytail.  Yes, Joan was a vixen but that was the way with this world.  But Peggy loved her boss, Don Draper with his well cut suits, gentlemanly manners, rugged Korean war-hero handsomeness and, of course, his petite beautiful wife Betty.  It was worth an extra five bucks a week to be secretary to Mr. Draper and she could certainly use it.  Even living on a rather crummy block of the Lower East Side, and with sharing her tiny apartment with a roommate, it was tight to make ends meet.  As the bus pulled up to the appropriate avenue, Peggy got off and looked around to see what building corresponded to the address Joan had given her at the end of their evaluation interview.  At times nothing seemed right, everything always seemed to be shifting around.  Like watching a horror movie where in one scene Igor’s hump was on the right and in the next scene the hunchback’s hump was in his left shoulder.  Her shiver just got worse. 

Peggy was impressed. Joan had directed her to a 12 story apartment on a nice part of Eleventh Ave but then there was a rumor that Joan got just over a hundred dollars a week, well over five thousand a year.  You could bet that she didn’t have to share a one bedroom apartment with a roommate.  As the wind blew in from the Hudson River Peggy felt a spring chill coming out of New Jersey.  She hoped that this wouldn’t take too long.  She hadn’t brought a sweater and after dark her nervous shaking would only make a chill shiver all the worse.  She dreaded what was to come, not entirely sure what would happen.  Mr. Draper had indicated that her first week’s performance, although not discouraging, needed significant improvement but that “Miss Halloway will of course show you the ropes and whip you into shape”.  Peggy entered the lobby of the building, constructed well before the war, but none-the-less impeccably maintained.  She noted a doorman, not bad for the West Side, although being born and raised in the outer boroughs, Manhattan still remained, by and large, a mystery to her.  Peggy noted the location of Miss Hallowoy’s apartment, the 11th floor, and approached the elevator.  An elderly Negro operated the elevator and Peggy ignored him during the slow ride up.  Her thoughts centered again around the strange conversation she had had with Joan earlier that day, “A need for discipline, have you ever had discipline in your life?, you need to be motivated to focus on your appearance and what it is you should really be doing”.  What the hell was that all about? 

An Interview with Joan  Exiting the elevator Peggy found Joan’s apartment just across the hallway.  She had hardly had a chance to turn the door chime when the door opened.  “Come in Miss Olson” stated the red headed Joan.  Peggy’s hostess was wearing a long dark blue housedress with buttons down the front and a peter pan collar buttoned all the way to the top.  This was about the last thing that Peggy anticipated given Miss Hollowoy’s usual attire in the office – low cut sack dresses with hemlines at the knee, and her constant upbraiding of Peggy for her dowdy skirt and blouse combinations.  And Joan’s bustline was radically different from the hard cones that jutted out at the world of the office.  Her breasts still pressed against the fabric of the dress but were more rounded and gave an impression of softness.  And Peggy swore that she could almost see nipple marks though the thin fabric.  Joan’s hair was undone and cascaded down to her shoulders in a soft wave and for the first time Peggy noticed that her eyes were actually blue-green.  “Well Miss Olson, I presume that you are here to discuss your chastisement” continued Joan as she closed the door behind her.  Peggy could only gape and make a quiet “Ah, Ah, Ah” noise.  Joan continued “We will discuss these matters over supper.  I see you have no wrap.  You are likely to be quite cold going home later this evening.  We will have to see to this.  Ordinarily, you would get only a hour of my time on a Friday night or Saturday morning, there being so may girls in the office for me to manage, but since this is your first time you will have my whole evening.  You new girls need careful breaking in.  And there is so much turn over what with the Sterling Cooper’s policy of employing women only prior to their marriage.” 

Most of this went right past Peggy and she looked around the beautiful apartment.  White walls had real art work hanging on them.  The chairs and the sofa matched and the end tables and lamps went beautifully with the major furniture.  She thought to herself, “I’ll bet that the sofa is a real sofa and not just a Castro convertible bed”.  As she followed Joan she noticed that there was a separate dinning room with a view of the river and New Jersey beyond.  And then they walked into the biggest kitchen that she had ever seen in an apartment, it was even bigger than the kitchens in some homes she had been in.

Cooking on the stove was a pot roast with an aroma that made Peggy’s stomach rumble.  The fashions of the day (or, at least of 1958, when Joan considered Peggy’s tastes to have been arrested) called for a girl’s waist to be narrow.  Peggy managed to attain that ideal only by usually forgoing lunch and using a girdle with tight “tummy control”.  Besides, going without lunch saved money and that was plenty tight enough.  The savory dish cooking tormented Peggy and distracted her from what Joan was saying.  Therefore Joan removed a bottle of white burgundy from the refrigerator and motioned Peggy to follow her into the living room where a pair of glasses awaited them on the coffee table.  Joan removed the cork with a large wooden handled corkscrew, poured the wine, cleared her throat and began.  “Peggy, your presence here right now indicated that you are willing, at least initially, to follow our rules at the Cooper-Sterling Advertising Agency, is this true?”  Peggy nodded her head.  Joan looked deep into Peggy’s eyes and continued.  “Mr. Draper, the executive who you serve, has concluded that you are naïve and careless but he sees hope for your continued service with proper training.  I, of course agree with him and he has instructed me as to the broad outlines of your training.  Before we proceed any further I need to ask you a few background questions.”  At this point Joan took a sip of her white wine and sat back on the sofa, looking up at an abstract painting on the catty-corner wall.  “I need to evaluate your disciplinary background and your willingness to undergo chastisement as part of your service training.”  Upon hearing this, Peggy almost audibly gulped.  She had certain fears and suspicions that had caused her anxiety on her way over.  They were now confirmed.  About the maximal response that Peggy could muster was a barely perceptible “OK”.  Joan slightly raised her voice, “What did you say?” “OK” more clearly said Peggy.  Joan replied, “Would not ‘Yes Madam’ be more appropriate”.  Peggy now clearly said “Yes Madam”, she knew she was sliding down a path she was not sure she wanted to take.

“Well, before we begin supper let us clarify and seal these matters” said Joan.  She fired a series of questions, rapid-fire at Peggy.

“As a child were you ever spanked”. 

On the one hand, the question was wildly inappropriate.  Peggy suspected where this was going, she knew that she was trapped and that she had no choice.  She mumbled out, “Yes, my mother would. My father died when I was a year old”.

Joan questioned further, “Were you ever spanked on the bare behind?”  Peggy was now sure she knew where these questions were likely to go and to what they would inevitably lead. 

“Yes”

“At school was corporal punishment ever administered”

Peggy’s heart was racing and her hands were shaking.

“Yes”

“Have you ever received chastisement on a place other than your bottom?”

“Yes”

“Are you willing to receive corporal punishment as part of your training and management”

Peggy stared off into space for a long time before replying with a lump in her throat.

“Yes”

“Alright” said Joan, “that part is over and the border is crossed”.  Drink your wine and we can continue.”  The office manager looked at the new secretary in a manner that expected a reply.

“Yes Madam”

After Peggy downed her glass of chilled white Burgundy, Joan motioned to the closest in the apartment’s foyer and told her “Remove your blouse and skirt and hang them in the closest.  Take off your girdle and panties and place them on the shelf.  You will find a pair of garters there.  You can use them to hold your stockings up”.

Peggy Reacts  She should have been outraged but instead felt singularly powerless.  Ordinarily, she would have responded by spitting in Joan’s face, calling her a pervert, storming out of the apartment, and maybe even calling the police.  But it was all too slickly done.  The planning probably began when she was still in secretarial school and Joan had talked with her instructors, evaluating who were the candidates for such a plum job.  She knew that they had interviewed three or four candidates, before settling on her.  Everything in this first week was set up to lead to this moment.  And now her will was eroded, she had no choice but to submit.  God knew where this was going to lead but Peggy couldn’t figure out any alternative.

She walked over to the closet by the entry door, unbuttoning and then unzipping her full, long skirt as she did.  Joan was obviously some sort of a pervert, in league with all the executives at Sterling-Cooper, who were also undoubtedly some sorts of perverts, and she was stuck.  Trying to stall for time and being coy and modest was probably not going to work.  Peggy suspected that Joan had been through this sort of thing before, probably many times and would enjoy watching the novice secretary try and disrobe as slowly as possible.  Well she would go about it in as business-like a fashion as possible as though this sort of thing went on all the time.  She stepped out of her skirt and passed it through a coat hanger folding it as neatly as possible.  Then she untied the bow she had around her neck and hung it around the crook of the hanger.  She unbuttoned the cuffs of her blouse before she started unbuttoning the front, starting at the bottom and continuing until the collar button was undone.  Then with a professional shrug she took off the blouse, hung it on the hanger and hung the hanger in the closet.  She wondered how many girls had undergone the same ritual.  Joan’s earlier comment about others getting only an hour on a Friday night or Saturday morning now began to make more sense.  Clad in her long nylon slip that reached to just below her knees, Peggy contemplated how to remove her girdle with a minimum of fuss and commotion.  There is no way I am going to give Joan any more of a show than I have to, she thought.  Facing the open closet Peggy raised the hem of her skirt to mid thigh and folded the lower hem of her girdle up, exposing the metal and rubber slip fasteners holding up her nylons.  She deftly unfastened the snaps from the tops of her nylons, grasped the hem of the girdle, exhaled and with a mighty tug pulled the girdle down to the level of her ankles.  She then stepped out of the steel-boned rubber and fabric appliance as daintily as could be done.  “Bravo, well done my dear girl” commented Joan.  Peggy loathed her, frustrated at giving her the pleasure of the least bit of show.  Peggy placed the girdle up on the shelve, her fingers searching for the circular garters that she could not see.  Eventually finding them, she once again raised up the hem of her slip, pulled up and straightened the stockings somewhat disordered by the lowering of the girdle, and drew the garters up first one leg and then the other.  She rolled the ends of her nylons down over the garters to an inch or two above her knees and then with her slip still hiked up, grasped the elastics at the leg holes of the lower portions of her white cotton panties and pulled them down.  After she folded her panties and placed them on top of her girdle, she closed the door of the closet and turned to face Joan to see what the manager now had in store.  It was only at this point that looking across the room and beyond Joan that she noticed hanging on the opposite wall from a hook is a leather strop.  Somehow the very public display of a strap for beating people did not surprise her.  Standing there in a full slip and bra, nylon stockings and shoes with nothing covering her bottom but thin clinging fabric, Peggy had a pretty good idea of where this Friday evening was headed.  At the same time one part of her really couldn’t believe the reality of what was going on.  That part of her mind was reeling with the surreal scene she was playing out.

Fine Wines and Sophisticated Explanations 

Joan motioned to the sofa, indicating that Peggy should sit down, and sat down herself. 

“Well, Miss Olson, you have passed the next part of the test.  Much to my surprise, I have not had, in the last five years, a trainee fail the test.  The pot roast is on the stove and the salad is in the fridge.  Therefore let us sit and enjoy this bottle of wine for a while and I will tell you some things about the realities of the business world.  Everything they taught you about business in secretarial school is bullshit.  Yes, the typing and shorthand is technically useful but that is not really what you are employed for.”

Not entirely surprised at what her office manager was saying, Peggy queried her, “Well what are we supposed to do?”

“Serve their needs, my girl, serve their needs.  Secretaries are the modern equivalent of domestic servants, that says it all, pretty much.  Think of yourself as Susanne in Mozart’s “Le Nozze di Figaro”.  Yes, a sophisticated role.  Just observe the wine we are drinking, a white burgundy from the town of Macon.  Light, a tiny bit dry, and above all refreshing, just like Susanne.  Not too expensive.  Just the sort of thing to have before supper.  A good secretary can be sent off by her boss in a pinch and should be able to pick up a bottle or two of wine, or flowers, or a box of candy so that he can be prepared for what ever comes up.  You should know his tastes and what is good taste.  That is one of the reasons why your dress and appearance are so important.  Clients will judge him based on how you look.  Likewise with deportment.  How you talk, how you walk, your vocabulary, all are important.  And you are assigned, not to some whelp of a junior executive but to one of the most successful chiefs we have – Don Draper.  And someday this firm could be known as Cooper, Draper and Sterling.”

“So what else are we expected to put out?” queried Peggy.

“Plenty much what ever is asked of us.  However, being a slut really doesn’t get you anywhere very quickly.  Which is one of the reasons you are here tonight.  Jumping in bed with Pete Campbell within a day or so of coming on board, just before he is married, is not good form.  I am the arbiter of mores in this office.  Coupling with a junior executive who is not your boss is a quick way to earn a sound chastisement.  We have to maintain standards.  A long clever seduction of the prettiest virgin in the office by a senior executive is a work of art that will fuel gossip for months if not years.  But sluts are out.”

A visibly upset Peggy retorted “But I thought we were supposed to take care of whoever needs being taken care of.  Why else would you have sent me to your own gynecologist to get these novel contraceptive pills.  Peter had such a cute, hurting-puppy look when he showed up at my door late that night.  I felt so sorry for him that I couldn’t put him out in the rain.  Besides, how did you hear about it. Only he and I knew.  I didn’t tell anyone and he would be a fool to tell anyone.  He didn’t blab, did he, the little rat?”

Joan laughed.  “No one else knew? How about your roommate? Don’t you remember what company she works for, NBC?  And how much time do our clients buy on NBC.  Lack of thinking ahead will cost you dearly in this case.  Come Monday you will tell no one of what happened tonight.  But when the other girls notice that you are moving gingerly and sitting very lightly, and they know that I had to rearrange my usual Friday night schedule.  Well they will put one and one together and come up with two very bruised buttocks.  Don’t be surprised if they ask you to go to the powder room and show them you bare behind.  If they ask, do it.  It will help to restore your reputation.  In fact, come to think of it, there is an idea.  Monday you are not to wear either panties or a girdle.  Just a garter belt and stockings.  With the type of skirts you wear no one will know the difference.  And show up for work prior to 7:00 AM.  I will take you to the powder room and freshen up you up a bit.  Then I will float the suggestion to the girls that they can inspect my handiwork and determine if I have lost my touch.  Well, in any case, it is time for pot roast.  Come along.  Let us change our white wine glasses for some more suited for red.  We will be having one of these new California wines.  Not quite up to the French but at a fraction of the cost.  And bring the strap with you.  You have been staring at it all this while.  Yes, that is what you are going to be punished with.  When you sit down to dine, you will hoist up the hem of your slip above your waist and sit on your bare behind.  That way, as you eat you will be reminded of why we are here.  Quite a charming way to enjoy dinner, don’t you think.?

The First Course – A Spanking 

“Ah but I am getting ahead of myself” Joan exclaimed.  “It seems that we have totally forgotten why you are here tonight.  Before we attack the pot roast, I think we should have a spanking, don’t you.”  Peggy looked at her, not knowing entirely what to think, but she knew that it wasn’t going to work out well for her.  But she had no choice but to go along with it. 

The secretary complied as Joan indicated.  She was to stand in back of the chair of the living room set, then raise up her slip until it was gathered just below her brassier, and bend over the back of the chair.  It was a familiar enough drill from Peggy’s childhood.  But she had to admit that there was a certain erotic charge that she had never noticed before, to exposing herself to someone who was not a family member or a teacher.  Also familiar was the charge to count each stroke out loud and clear or face further punishment.  With this Peggy had never had a problem.  And it came as no surprise when the first blow landed, “One, thank you Mamam”.  It was a substantial strap wielded by an experienced hand and Peggy knew that there would be pain and damage.  There was a reflex flinch and forward lunge when the blow landed.  Peggy recovered quickly and resumed the subservient position before Joan ever had a chance to comment.  Peggy was not going to give Joan the pleasure of seeing her cringe and squirm and hearing her cry.  She too was an old hand at this game.  She was going to show Joan that she could take what ever Joan could dish out. 

By the twelfth stroke, the office manager knew that the pony-tailed ingénue from Brooklyn had been disciplined before.  She was taking her beating with a stolidity that implied a considerable experience with corporal punishment before.  Joan shifted over to the other side and began a series of blows that would treat Peggy’s left side to the fast whipping tail of the strop.  “Twenty-four” recited Peggy with scarcely a deep breath drawn.  At this point Joan had to reconsider her entire strategy.  She had assumed that Peggy would quickly break down after half a dozen blows, but Peggy was hardly panting after two dozen hard swats.  In fact, Joan was breathing harder from her effort.  However, Peggy’s behind was now covered with what amounted to a single large welt mottled with bright red and purple splotches.  At occasional spots, minute drops of blood were even beginning to bead up.  Joan thought “OK, this girl has won the first round.  She was obviously telling the truth when she said that she has been spanked before.  She has not only taken a spanking or two, she has probably been thoroughly beaten on a dozen occasions.  I’m pretty sure that Peggy had the living shit whipped out of her prior to graduation from high school.”  It was going to take a bit more effort to break this puppy.  But Joan was up to the challenge.

 

     

Pot Roast and Punishment 

Joan, reconsidering her strategy, was thankful that she had refrained from scheduling anything else for this Friday night and was further grateful that Don Draper would be stopping by later to give a hand.  On their way to the dining room Joan popped into the bathroom and grabbed a towel to cover the seat of the chair that Peggy would be sitting in.  Although the blood drops on the secretary’s fanny were tiny and looked very pretty, there was no sense staining the beautiful brocade fabric of the chair’s seats.

The pot roast was quickly demolished together with the remainder of the California Gamay Beaujolais that had not been used in the making of the pot roast.  Joan reflected that although chuck was despised by all too many cooks, it had flavor that held up to the prolonged cooking that a pot roast required.  Let the Philistines have their grilled steaks.  A real cook would always grab the chuck and slowly simmer it with salt and peppercorns in red wine.  About two thirds of the way along, you add the onion and celery.  By the end the onion will almost entirely cook down but the celery slices will remain intact.  Only toward the end do you throw in the potatoes, carrots, Italian parsley and mushrooms.  Such is it with chastisement of a new secretary.  Only a fool would go with a hot fire and quick punishment.  Better to take one’s time and slowly break their will with unexpected twists and turns.  Peggy, despite her naïve appearance, had depths that were unexpected and facets that were unexplored.  It would be worth the time and investment of patience to bring her to the edge.  Just like a pot roast.

The Second Bedroom

Well the time had come for the main event of the evening to begin.  Joan intended to break Peggy once and for all.  She would punish the girl until she had no control left and collapsed in a quivering, weeping mass of jelly with no will of her own.  Her punishment would have to be taken to an extreme.  That after all was why Roger Sterling had given Joan this apartment.  Not simply to get rid of her roommate so that Roger could fuck her when ever he pleased without have a second bothersome female around.  Roger wanted a place where the women of Sterling Cooper could periodically be sent for proper chastisement.  That was the reason for the second bedroom.  There was a need for a soundproofed room in a well built building where even the loudest of un-muffled screams would not be heard beyond the confines of the apartment.  Only prewar construction was that solid and had rooms large enough to swing whatever implement of punishment was necessary.  And closets spacious enough to store furniture not meant for comfortable reclining, but designed for the bondage of women in need of a sound beating.  For punishment at Cooper Sterling was not simply a crude pummeling, but a combination of the humiliation of being forced to strip and expose oneself combined with the feeling of helplessness and hopelessness that came from being strapped into the most uncomfortable and embarrassing positions devised by truly sick minds.

So it was into the second bedroom, the guest bedroom, that Joan led Peggy.  The secretary recoiled a bit when the door was opened and the light switched on.  In the center of the room, what was virtually the only piece of furniture stood revealed.  It was a wooden frame, with feet long enough for stability despite the most extreme struggles.  From the base a post extended upward into a crosspiece with three holes.  The central hole was obviously just the right size for a neck.  There was a hole to either side of the main hole of about the right size for a feminine wrist.  And yes, the upper part of the cross-piece was split and hinged so that it could swing up for placement of the penitent’s neck and wrists in the holes.  And lowered, securing the victim firmly.  “Oh lord” exclaimed Peggy, “the stocks”.  ”Actually,” corrected Joan, closing the heavy door behind them, “a pillory.  Stocks were the device used in bygone times to secure the feet, and occasionally the hands as well, of a sitting misencreate.  The purpose of stocks was to expose you to public humiliation.  This is a pillory and it has a darker purpose.  You are held helpless while punishment is applied to your body.”  Peggy gazed with dread anticipation at the apparatus constructed of thick wood.  As she looked around the room at the heavy drapes covering the far wall where the window undoubtedly was, she realized the room was probably heavily soundproofed.  Although she refused to make any outward expression of her feear that would please her office manager, it required all of her effort to contain that terror which now she felt.  “Take off your slip and give it to me” Joan commanded.  With an effort Peggy kept her hands steady as she lifted the tricot nylon slip above her head, pulling it off.  She folded it in half at the waist, and then folded it again, neatly enclosing and wrapping the lacy bodice in the lower portion.  As she handed it to Joan she stood there, naked except for bra, stockings and low heels.

Peggy was relieved when Joan pointed to a bedpan sitting over against a wall.  She not only had a full bladder from the two bottles of wine they had drunk, but her bowels were beginning to roil from the pot roast they had for supper but even more from terror.  She squatted down and after a few seconds of tinkling came what seemed to her like a roar of flatulence and endless volumes of loose stool being expelled.  Peggy began to blush but soon she was consumed by wracking cramps as her colonic contents continued to spew forth.  After what seemed to be an eternity, the diarrhea finally ceased and Peggy began to clean herself with the toilet paper sitting on the floor next to the bedpan.  Joan made a motion toward a nearby cupboard and Peggy realized that there was where the bedpan was to be stored.  With her bowels finally quiescent, she began to appreciate the humiliation of her nakedness.

Now Joan undid the upper part of the crosspiece of the pillory and motioned to Peggy to come over.   The girl willing placed her neck and wrists onto the semicircular openings realizing that at this point she had little other alternative.  Joan brought the heavy upper arm of the crosspiece down, securing it to the frame with a pin and Peggy realized the true degree of her entrapment.  She was bent over with her ass thrust into the air with her arms secured.  She didn’t even have the option of turning around and seeing what Joan was in the process of doing.

What’s a Bit of Skin Anyway

What Joan was in the process of doing was opening a door in the side of the room.  On the inner face of the door were hooks from which were suspended a variety of rather nasty implements to be applied to the body of the woman being disciplined for the purpose of inflicting pain.  A few were straps but they were very few.  Most were far nastier - whips of various sorts, switches and above all, canes.  Such was the three foot long piece of rattan fitted into a leather wrapped hand that Joan selected.  She flexed it a few times and took a practice cut or two, swishing it through the air. 

“Well Peggy, I guess it is time that we finally get down to business, the two of us.  This is after all, what it is really about, isn’t it.  You have really fucked up, you know, with your silly affair with Pete Campbell.  As the word around the office puts it, you were a nice fresh fruit that went bad in a remarkably short time.  Now there is nothing wrong with sleeping around.  All of us do it.  Some of us do it even more than others.  But Don Draper is your boss, not that little pipsqueak of a junior executive.  And you don’t sleep around without the approval of your boss.  I am going to teach you a lesson that you will remember the rest of your life.  You think that you are pretty tough and you aren’t going to admit to me your fear and your pain and your vulnerability.  Well I have news for you.  You may have been spanked a few times and somebody may have put a switch to you butt.  So you think you are tough?   But you have never taken a licking from a real pro, and I am a real pro.  Your ass is grass and I am the lawnmower.  By the time I am finished, I will have stripped the skin off your backside and you will be sobbing for mercy.  By the time I am done, you will do whatever I tell you.  If I say, ‘lick my toes’ you will lick my toes.  If I say ‘suck my clit’ you will do a job on my genitals that would put a Hoover to shame.  You will weep and whine and I will have no mercy.”  And with that the office manager drew the cane back over her shoulder and brought it down on the buttocks of the secretary with the full force of an experienced chastiser.

Peggy heard the swish of the rattan and felt the thud of it impacting her well padded bottom.  What caught her totally by surprise was the explosion of pain that occurred about a second after the impact.  It was pain of a magnitude that Peggy had never experienced before.  Although she managed to suppress, by the greatest exercise of a quite considerable will, any exclamation, she was unable to suppress the reflex jump that her entire body made.  Rather it was the pillory that absorbed the spasm of her body and this shook the heavy frame significantly.  Joan chortled having finally connected with her stolid victim.  “Well my dear, being stoic goes only so far.  Just wait, after a few of these you will be singing for me.”  She waited almost a full two minutes before putting the cane into play again.  Peggy was better prepared this time and the searing pain of the impact elicited no more than a minor flinch.  Joan delivered another four blows in quick succession and then backed off to admire her handiwork while demons wailed and ran about Peggy’s consciousness.  When the caning started, the skin of Peggy’s buttocks and upper thighs was swollen a bit and colored a mottled red with an occasional blue bruise beginning to form from the belting she had endured over an hour before.  But the application of the cane quickly made it’s mark.  Wheals, almost an inch across were swelling up within a couple of minutes of the blow.  Peggy had never experienced anything like this.  Since she couldn’t actually see the welts forming, her imagination ran riot.  But once again, unwilling to allow her tormenter the pleasure of seeing her reaction, Peggy focused all of her attention on suppressing any verbal response.  But physiology will have its way and Joan was gratified to see the almost obscene way in which her cane marked Peggy’s buttocks. 

After about a five minute wait Joan started going at it again with a vengeance.  But since she was a well practiced disciplinarian, she had the self control to allow almost a full minute in between strokes.  This allowed the full extent of the pain to sink in before another blow was delivered.  Enough time for the victim to spend a while anticipating the next cycle of swish, thud and agony.  Yes, Joan had been caned herself – caned by experts – and she knew the nuances.  Joan maintained a running commentary as she unmercifully beat Peggy’s behind.  “You know girl, I am quite expert at this…” pause followed by the swish of the cane and the sound of its impact.  “You should see the piece of art work that I am creating of you…”  pause, swish, thud.  “All of the welts that I am placing on your buttocks are exactly parallel…”  more of the same.  “There is a wheal and then a strip of relatively normal skin, no more than the width of a pencil, and then another wheal.”  The long pauses between strokes were taking their effect.  Peggy knew that Joan was toying with her and she resisted mightily.  But she could not hold back the tears that were pouring down her face.  “Ah, yes.  Let us step back and admire the pretty picture…”  pause, swish, thud.  “You know Peggy, you really have a quite pretty ass…”  “which you artfully conceal beneath those dowdy skirts that you wear…”  “It is a fulsome ass, not boyish at all…”  “Not at all like the skinny asses of some of the secretaries that I punish…”  “It is in fact what I would call an eminently beatable ass…”  “And that is what I am doing with it…”

After twenty or so strokes of the cane, Joan stopped for a prolonged rest.  Peggy’s behind was covered with parallel welts from just below the narrowest part of her waist down to where her stockings were gartered just above her knees.  And particularly well worked over was the lower part of the globe of her ass, just where the thighs joined.  This was the sweet spot where the vibrations from the blow of the cane rippled through the vagina.  It had a peculiar effect on particular women.  Joan loved it.  And beneath each of the welts a bruise was beginning to form, a dark purple blotch that warned of lasting pain to come which would make sitting an agony for a week.  Although Peggy had managed to suppress a vocal response to the punishment she was receiving, sweat had not only broken out on her forehead, but fine beads of sweat were erupting all over her body.  Her legs were visibly shaking. Tears ran from her eyes and out her nose although not a sob or a whine escaped her lips. Her face was beet red from keeping it all in.  All of Peggy’s mental faculties were focused on maintaining control but Joan’s voice still penetrated through the fog of pain.  “Well girl.  We have raised welts all up and down your ass…  Do you know what happens next, girl?  We alter the angle at which the cane is aimed and cross the strokes a little.  As we go back over where we just caned you the new strokes will overlap the previous strokes…  Take a guess what happens when the cane hits swollen, welted skin… We tear the skin right off those welts…  What do you have to say about that girl?”  Although Peggy remained silent she could not suppress the shudder that wracked her body as she contemplated what was to come.

Then the blows started again and with them the terrifying agony.  Peggy couldn’t actually feel the skin abrading because the intense pain she was in caused almost every sensation other than pain to dim.  But she soon became aware of wetness as drops of blood began to trickle down the backs of her thighs.  She also noticed that Joan had a dish towel in her left hand and that during each pause between strokes, the office manager was wiping the cane.  Peggy could occasionally catch a glimpse of the towel out of the corner of her eye.  There were red lines on it – lines of her blood.  Joan, fastidious as usual, did want spatters of blood to dirty her walls.  Peggy was no longer distinctly sensing the pain from each blow even though Joan was allowing plenty of time in between strokes.  It was just a continuous roar of pain that almost approximated a noise.  It was like being run over by a train time after time again.  Peggy marveled that at one point the only thing she was really sensible of was that her tears were causing her nose to run and that her hard breathing was causing the runny mucous to shoot out of her nose.   Aware that the secretary was on the border of loosing consciousness, Joan stopped at fifty strokes of the cane.  Any more punishment of this sort would be futile.  You would just be ripping the skin of a numb lump of flesh.  And yet the girl still hadn’t broken.  She was red faced, shaking, gasping for air and blowing snot all over the place but nary a cry or sob or plea for mercy was coming from lips that were bitten bloody in agony.

Joan decided that at this point a bit of first aid was in order.  She went to the bathroom and retrieved a bottle of brine vinegar and an alum stick used to staunch shaving nicks.  She moistened the towel with the brine and began to daub at the place where the skin had torn and was oozing blood.  Then she applied the alum stick.  This caused Peggy to flinch at the unexpected astringency but again the girl remained silent.  Just as Joan finished staunching the last major laceration, the door to the bedroom opened and Don Draper sauntered in.     

What Weapon is Mightiest of Them All 

“Whew Wee” Don whistled through his lips as he surveyed the buttocks and thighs of his secretary, bent over at the waist restrained in the pillory before him.  “Now that is quite a sight.”  Peggy’s entire backside was essentially a single red-purple bruise with tags of torn skin hanging in scattered strips.  The whole mass looked more like hamburger than skin.  “Well Joan, thank you for cleaning things up,” he said ”I always appreciate it.”  Peggy was startled by the entrance of her boss.  Nut honestly she was too befuddled by her pain to either think the implications out further or even to be embarrassed by her nakedness, disheveled appearance or bizarre position bound in the pillory.  Draper asked her, “Well Peggy have you learned your lesson, not to screw around like a cheap slut?”  The pony-tailed head bobbed up and down in concurrence. Joan interjected, “she really has not yet expressed sorrow or begged for mercy.”  Don said, “I can fix that” and unzipped his fly.  He took his right index finger and inserted it into Peggy’s vagina.  “Hmm” he observed as it readily entered all the way, “remarkably moist.  Peggy you must have been enjoying yourself.”  Only then did Peggy’s fogged brain begin to realize that he was right.  She was now aware that her pussy was oozing wetness.  She could not remember ever being this moist before.  Peggy was startled by being fingered by her boss, who had never expressed any sexual interest in her.  Of course considering the range of sexual demands being placed upon him he must be superman. First, he had that beautiful wife Betty to service.  Then there was his mistress Midge to keep him busy. Lastly, he was inundating the exotic Rachel Menkin with sufficient charm to melt even that Jewish iceberg.  Peggy couldn’t imagine that he would waste his time and energy on a lowly secretary.

Don now inserted two fingers into Peggy’s vagina and began to harvest the juice to lubricate her perineum.  She responded by wiggling her ass around and thrusting herself onto his fingers whenever they were inserted.  Then he did something that really startled her.  He took his index finger and stuck it suddenly and forcefully into her rectum.  “Ouch! No! Don’t you do that.” she said as she suddenly broke her silence.  Although she had been fingered before my many men, she had never been fingered in that way.  She was an anal virgin.  Don smiled and began to vigorously lubricate her anal ring with her vaginal secretions while at the same time stroking his penis with his left hand to bring it to full erection.  “Oh no, you aren’t going to take me like a boy, you’re not.  Oh please no, don’t do that to me, please.” the pony-tailed girl pleaded.  Joan also began to smile.  She had never thought about it that way.   She realized that Don had an insight that she had missed.  The slut had a virgin asshole.  He was trying to accomplish with his cock what she had failed to do with her whip.  And looking back at it, Joan realized that she never had any hang-ups about taking it up the ass.  Well different strokes for different folks.

As Don’s fingering of Peggy’s asshole continued, the girl’s protests became louder and more vociferous.  “No, No, NNOOOOOH!” she exclaimed as he forced the head of his penis into her anal ring.  When he thrust his shaft into her rectum she rent the air with a scream.  And as he began moving his penis in and out, she struggled against the bondage of the oaken pillory, albeit to no avail.  Peggy became livid from trying so hard to contract her pelvic muscles and keep him out.  But Don only smiled at the stimulation that the tight grip on his cock provided.  He reached up and unclipped the back of her bra unleashing her surprisingly large tits.  He gripped the dangling globes firmly, one in each hand and squeezed as hard as he could when ever he thrust in.  When ever the mood struck him he shifted his grip to grasp her nipples between his thumb and forefinger and twisted as hard as he could.  Peggy became hysterical and bucked like a wild animal, but to no avail.  Don was an experienced rider and she was firmly restrained by the pillory.  Finally, he gave one last, deep thrust and shot his woad.  Peggy went rather limp and just sobbed quietly.  Joan stood by amazed. Don had indeed conquered with his prick wherein she had failed with her strap and cane.

But Don was not done yet.  He walked around to the front of the pillory and grasped Peggy by the pony tail.  As her head came up, the secretary finally understood an aspect of the pillory’s geometry that had early eluded her.  When she looked up from her bent over position, her face was almost exactly in the middle of the tall man’s crotch.  “Oh no.  I don’t do that either.” she exclaimed, anticipating his next move before he even made it.  Don once again smiled as he rubbed his now flaccid penis against her nostrils.  “Come on Peggy, don’t you like the smell of cum and shit.  You’re going to give me a nice cleaning.  I need my pecker Hoovered.  Open up.”  Peggy’s eyes widened as she watched the penis being waved in front of her face.  But she kept her lips tightly sealed.  Don remarked, “Don’t want to open up, we can fix that.”  And taking his left hand he squeezed her nostrils shut cruelly.  She wouldn’t open her mouth and now she couldn’t breathe through her nose.  Her face started turning redder and redder.  Finally the need for oxygen overcame her pride and she opened her mouth just enough to draw a gulp of air.  “OOUUCCH – ak” she went as her protest was cut short by the insertion of his cock.  Don looked her in the eyes and said softly, “Now Peggy, be a good girl.  Because if you bite, that nasty lady Joan over there has a pair of pliers and she will pull out your teeth.  Then you will have to suck me off with your bloody gums.   And you will have to wear dentures all the rest of your life.”  Peggy didn’t know whether or not he was kidding.  However she was sure that once Don gave the order to Joan, there was no action, no matter how cruel or outrageous, that the office manager would not do.  And Peggy suspected that Joan would enjoy it.  So she was stuck with it – a very large cock in her mouth.  And so it went, as Don’s cock engorged, he thrust it deeper and deeper into first her mouth and then progressively her throat.  There wasn’t much she could do.  The smell and taste of shit was overwhelming her and making her nauseous.  Don’s fully erect cock was intermittently obstructing her airway.  Her nose was full of snot.  And the battering of the back of her throat was making her gag.  She was gasping for air as he ejaculated into her throat.  And just as he pulled out she blew her supper.  Don was an old enough hand at this game to have foreseen what was about to happen.  He dodged off to the side just missing the spewing forth of a mix of wine and half digested chunks of chuck and potatoes and carrots.  “Oh Shit” exclaimed Joan as the mix spewed out over the white rug covering the floor under the pillory.  Peggy continued to gag and retch.  At one point she willfully pursed her lips together in an attempt to halt the stream but this only forced vomit up into her nose. 

At this point Don motioned Joan over to him.  “Kneel and make me hard” he commanded, wiggling his limp dick in front of her.  Joan knew better than to argue.  She knelt and went to work to revive a penis that had already had quite a workout.  However, Joan was a master at limp-dickology.  The road to office manager had been paved by resurrecting many an elderly executive organ.  Soon Don’s tired and weary warrior was ready for battle again.  There was one hole in Peggy that he hadn’t properly plugged yet and he went at it doggy style.  Totally exhausted, beaten and degraded Peggy just moaned as he fucked her pussy from behind.  She didn’t even try and struggle but merely meekly moaned and occasionally retched as he thrust in and out of her vagina.  He did what he could to arouse her by squeezing repeatedly her pendulous breasts.  This seemed to work.  It never ceased to amaze him how really mashing a woman’s jugs got the muscles of their pelvic floor to function.  She would have some nasty bruises tomorrow morning but compared to the slaughter inflicted on her backside, his ministrations were gentle.  Beside, he was sure that Joan would minister to her later.  His third ejaculation in forty five minutes was a relatively weak affair but he was satisfied with his evening’s work.  He did make sure, however, that Joan licked him clear before he slipped his pecker back into his pants.  “Well folks, see you bright and early Monday morning” he quipped knowing that the women would be in the office at 7 AM sharp while he would saunter in about 9:30.  He had given Joan some very specific instructions about that.  As he walked out the door he wondered where and how and why was he going to get it up with Betty when he got home -and whether he really cared.

After Joan released Peggy from the pillory she showered herself and the young secretary.  She loved toweling off the inflamed body of a secretary made totally submissive by a very thorough beating.  She laid Peggy prone on her bed and rubbed a healing ointment into her backside.  Joan knew from experience the wonders that Aloe vera worked on the badly beaten backsides of the ladies of Cooper Sterling.  Despite the shower, Peggy’s vagina and rectum still held a surprising amount of semen.  Joan thought it was delicious.   That night the naked girl cried herself to sleep nestled in the arms of the equally nude office manager.  Joan appreciated that life was wonderful.

Epilogue

Monday morning there was a spring in Peggy’s step as she entered the lobby of the Sterling Cooper building at 6:45 AM.  She was wearing a brand new suit cut to the latest fashion, the skirt of which revealed a great deal more leg than she had ever dared to reveal before.  In fact, it might be said to almost be daring even for the summer of 1960.  “But what the hell” she thought “I am twenty, single and all of Manhattan is my oyster”.  Even more daring than her skirt was the fact that beneath her half slip she was without a girdle.  In fact underneath that half slip was nothing more than a garter belt.  She had been instructed, No Panties and No Girdle.  And Peggy always followed instructions.  To be sure, it would have been torture to be wearing a girdle this morning, especially the panty-leg type that she often wore.  Anything compressing her tattered and torn backside would be agony.  On the subway this morning she was fantasizing that everybody could see up her skirt her naked pussy and battered buttocks and thighs.  The thought excited her so much that her vagina started pumping out slime again.  Oh but wasn’t it a great day to be alive! 

When she got to the 23rd floor Peggy immediately went as instructed to the ladies room.  Joan was already there.  “Take off your jacket, blouse and bra” the office manager instructed as she pulled a segment of chopped down fiberglass fishing rod out of the cabinet.  “Hands clasped behind your back and kneel down” Joan commanded.  She continued, “You know the really nice thing about a breast beating is that you can watch the wheals and bruises form right before your eyes.  And it is really cute when the blood oozes out of the nipples just like milk.  Except it is red.”