Story: A Simple Act of Delegation. Chapter 4.

by Jackie J

The drive to the shopping area was a quiet affair hardly a word spoken. Debbie tugged her coat around her sat in the back of Mrs. Ross’s limousine Mrs. Ross sat facing her with the driver making good progress through the light traffic.

What was happening? Why was Mrs. Ross so calm about the situation? Had she really agreed to be her secretary’s secretary not in some contrived game, some fantasy but for real? Mrs. Ross speaking of Miss Jackson in the third person, Miss Jackson’s reputation had to be saved, Miss Simpson will be taking over from Miss Jackson, Miss Simpson will be Debbie’s boss but she was Debbie, was she? What of Miss Jackson, she was Miss Jackson, no she was Debbie? 

Mrs. Ross chuckled watching the expressions change on Debbie’s face she could almost hear the cogs of Debbie’s confused mind churning. An exposed submissive in conflict and denial, straining to mask her delusions, delusions that had at first seeped then cascaded from her in a torrent fueled by her desires, weakness and the contrivance of her secretary, to become her reality.

Disturbing Debbie’s mental turmoil the Limo came to an abrupt halt at the side of the avenue, the door opened and in slithered a smiling Miss Simpson hutching onto the soft leather upholstery next to Mrs. Ross.

Debbie just stared her mind still in conflict at her situation.

Mrs. Ross welcomed Miss Simpson.

“Debbie dear I thought it best that your manager Miss Simpson accompanies you on your shopping trip to ensure that your purchases are in line with company policy. Now you wait outside the car I need a few words with Miss Simpson in private.”

The driver was out of the car and held the door open for Debbie to exit the swiftly closed it.

Mrs. Ross turned to Jane.

“You were right, she is a submissive, full blown and you are to fuel the flames of those hidden desires until every ounce of its self confidence is sucked from it until Miss Jackson is so distant a character in its mind it will forget it could every have been such a person. I will keep my side of our agreement now you make sure you keep yours if you want its car, apartment and its job on a permanent basis. Remember until it is totally subjugated it is a threat to the company. If any of what it knows leaks out, I will be ruined.

Jane chuckled.

“Don’t worry Mrs. Ross this will be my pleasure I have suffered that stuck up bitch long enough and to think all the times it was being so high and mighty in the office it was jealous of me, wanting to be in my skirts and heels. Well now it is in them and its pretty little body will be trapped in them for good. You can rely on me to deliver a simpering sweet thing for your needs whatever they are.”

Mrs. Ross Smiled.

“Good that is what I want to hear Miss Simpson I will leave matters in your capable hands.”

Jane left the limousine and it sped off into the distance. Debbie was stood on the pavement looking lost and Jane smiled.

“Well it seems we got out of that situation better than I thought, come Debbie let’s get a coffee and talk about what Mrs. Ross said to me and of course to you?”

Debbie was cautious of Jane, Miss Simpson and followed behind her to the local Costa.

Inside Debbie sat and Jane went to order, what had Mrs. Ross said to Miss Simpson, Debbie just couldn’t stop herself from thinking of Jane her secretary by her preferred title Miss Simpson? What was wrong with her?

Miss Simpson sat opposite Debbie and stirred in her sugar.

“Well Debbie every cloud hey, who would have thought Mrs. Ross would be so understanding of, well you know what we were doing. I thought we may have been out on our ears but she seemed to understand when she spoke with me. She said we were to carry on me your boss and you my secretary it would be fine given it was what we both wanted. What about you what did she say to you?”

Debbie for the first time for some hours showed a weak smile in part from embarrassment. What Jane was saying seemed to marry up with what Mrs. Ross had told her. That she would continue in a subordinate role to Miss Simpson much like their charade had been. Mrs. Ross however was a little more forceful in that there was no other option mentioned. 

Jane knew exactly what Mrs. Ross had told Debbie but could understand Debbie’s reluctance to confide that just now. The poor thing needed a nudge back into her pathetic submissiveness.

“Debbie take your coat off dear come on we have a month of this it will be fun won’t it, it’s what you wanted isn’t it wearing my tiny skirts and heels serving your boss’s needs, you looked great in that jumper and those earrings, you will make a great girl Friday, I will make sure you are. Mrs. Ross told me just then she wanted to make it real for you, to help you with these desires you have. She told me that Miss Jackson’s good record and name at Sapphire and Ross could not be tainted with what we were doing and especially Miss Jackson’s breach of confidentiality with the Tax file program so allowing you to be Debbie makes sense doesn’t it, protects Miss Jackson. I also get to be your boss wearing nice business suits. 

Mrs. Ross hinted to me that she had something special in mind for you given you are a good little girly for me in your cute outfits and you let your true submissive feelings flourish. It’s what you wanted and don’t worry I will be there to help you every step of the way. No more pretending, enjoy being Debbie for real.

“Come on Debbie take that coat off for your boss, that’s a good girl.”

“Yes Miss Simpson of course whatever you say.”

Jane smiled seeing the same glint in Miss Jacksons eyes that she saw the first time their office role reversal and their cross dressing arose. Jane hid her amusement watching the smart sophisticated women who was her boss, now exposed to be a closet submissive, open up her coat and slide it from her shoulders.

Shedding her coat was like a butterfly emerging from its chrysalis the harsh reality of what Mrs. Ross had laid out for Debbie’s future evaporated like mists on a spring day. She was Debbie the secretary taking coffee with her boss her pert breasts straining in her tight jumper a soft waft of cool air, from the café’s door opening, fluttering the hem of her short skirt teasing her intimacy through her cotton panties and Debbie let out a soft submissive sigh.

“O Miss Simpson what is to become of me?”

Jane’s eyes tightened at her ex boss’s overt words of capitulation to her situation.

“Don’t worry Debbie Miss Simpson is going to take good care of her secretary now clear these cups and bring me another coffee that’s a good girl.”

Debbie stood her eyes weak overcome with emotion and her uncontrollable urge to serve the smartly dressed women sat opposite not Jane her secretary, her boss Miss Simpson and collected the crockery.

“Thank you Miss Simpson I will be a good secretary.”

When Debbie’s tight ass wiggled to the counter Jane chuckled under her breath.

“O yes you will girl I will make sure of that you will soon regret the day you ever even thought of being in my skirts and heels.”

Miss Simpson finished her coffee and with Debbie’s coat buttoned they left the Costa and headed toward the shops.

“Now Debbie my appointment at Jaggers and Brown, the exclusive tailors Mrs. Ross arranged for my business suits is not until six so we have some time to get your things. Come with me I know just the place and we need to get you a proper coat, that one is just too, well too expensive looking.”

Debbie followed Miss Simpson into a large department store that Miss Jackson would never consider buying clothes from but Debbie?

On entering the ladies wear section Debbie was heading towards the lingerie department having seen a delightful camisole.

Miss Simpson tugged Debbie’s arm.

“Not their silly that’s the expensive section we need to be through here.”

Loud music was playing and a girl chewing gum leaning on a high desk by a till smiled.

“Can I help you guys, new stuff is on the back rail?”

Miss Simpson drew a bewildered Debbie through the closely arranged rails of cheap clothing and within half an hour Debbie was loaded with underwear, outfits and accessories that met Mrs. Ross’s dress code. Miss Simpson made one concession to an increasingly eager Debbie, two short dresses that in truth were a little too slutty for work.

Whilst reluctant at first, for Debbie, it was an Aladdin’s cave of forbidden attire. Miss Jackson would never contemplate being here let alone try on and then purchase this stuff. All low end, cheap cotton knickers not silk, push up bra’s, short skirts tiny jackets and tight jumpers. Jazz leggings, knee socks, heels, including a ridiculous pink pair to match a pleated pink skirt she had tried on for Miss Simpson who nodded her approval suppressing her giggles. There would be no more diamond studs, gold necklaces and bracelets Miss Simpson had selected all the cheap tacky jewellery her secretary would need.

With branded bags swinging Debbie was trooped out of the store by a chuckling Miss Simpson.

Debbie with her fingers aching from the bags she was carrying followed Miss Simpson to Jaggers and Brown a store Miss Jackson had visited many times for her clothing but it was her boss Miss Simpson how was attending her fitting appointment Debbie would not be calling here again.

Debbie ignored by the shops staff sat in the waiting area with her cheap branded bags whilst Miss Simpson was greeted by smiling faces and a warm welcome.

“Miss Simpson, we have been expecting you please follow me Madame we have a selection prepared for you on the advice of Mrs. Ross she likes her executives to look their best.”

Measured fitted and conservative business suits selected a selection of modest pumps and court shoes, silk blouses, sheer stockings and underwear to die for added to the growing ensemble gathered by Miss Simpson.

At the doorway of the shop the manager stood and having sneered at the impatient girl in the trench coat surrounded by cheap store bags smiled at the advancing Miss Simpson.

“Thank you for your custom Miss Simpson may I, on behalf of all the staff here at Jaggers and Brown, wish you all the very best with your new appointment at Sapphire and Ross and we look forward to seeing you again.  We will delivery your purchases tomorrow so you will be properly attired for your first day on Monday.”

The Manager pointed to Debbie beginning to stand fussing with her bags getting ready to leave and spoke in a low voice but loud enough for Debbie to hear.

 “Is she with you Miss Simpson, she looks familiar but I was about to ask her to leave all those cheap bags of rubbish around her from Pollock’s, a ghastly place, all imported you know from sweat shops.”

Miss Simpson smiled and looked towards a forlorn looking Debbie; Miss Jackson would have been greeted and treated like Miss Simpson but Debbie?

“Yes, she insists on buying that smutty stuff.”

Miss Simpson chuckled.

“You know how Mrs. Ross likes her young things to dress around the offices.”

The manager looked over again at Debbie and smirked.

“Yes, indeed I do she likes a clear demarcation between executives and staff.”

Outside Jaggers and Brown only a half mile from the offices of Sapphire and Brown cutting through the ally ways all though perhaps almost two miles by the main roads Miss Simpson smiled at the weighed down Debbie.

“Right Debbie go and get Miss Jackson’s company car that you drive and you can take your boss home, I will be in Fitches wine bar meet me there.”

With that Miss Simpson turned on her heels and headed down the Avenue towards Fitches.

Debbie sighed at the daunting prospect of hobbling all the way back to the office car park in her heels, especially loaded down like she was?

Debbie hailed a taxi and was soon pulling out of the company garage grateful that she still had her company car.

Pulling up outside Fitches wine bar Debbie could see Miss Simpson stood at the bar and entered to join her and they both sat in a booth to share a bottle of red.

Jane chuckled and smiled across the table at Debbie.

“You loved that didn’t you? You were like a little girl in a sweet shop in Pollock’s weren’t you; I bet you can’t wait to get into those cute outfits you bought?”

Debbie could not help but giggle Miss Simpson was right.

Jane topped up Debbie’s glass drawing her ex boss deeper into her fantasy.

“This is going to be so good for you Debbie, such a release of all your submissive desires, I saw you squirming away when the manager in MY shop looked at you. How did that make you feel, me being pampered and you being treated like that in Jaggers and Brown a store Miss Jackson used to frequent? Did you want the manager to recognise you; would that have been better for you, that stern looking lady manager knowing who you were and what you are now? I should have told her shouldn’t I, what do you think she would have done with you? Should I have taken you to see me being fitted for my expensive business suits like my ex boss Miss Jackson used to wear. Let you touch the expensive lingerie Miss Jackson used to wear to the office, Lingerie I will be wearing under those expensive suits?”

Listening to her new boss Debbie began to feel weak looking wide eyed at Miss Simpson. 

Jane chuckled seeing the tell-tale signs of Debbie becoming submissively stimulated and aroused whilst she spoke.

The bottle drained Debbie pulled on her coat and having left the wine bar Miss Simpson and her secretary headed for the car parked across the road.

The traffic was heavy driving to Jane’s out of town apartment and having dropped Miss Simpson off and been told to pick her up on Monday morning in time to be back at the offices by eight thirty, the journey back was no less time consuming.

Debbie scampered into her apartment laden with her shopping and giggled closing the door. Over the remainder of the weekend Debbie tried on all her outfits and when Monday morning came, having selected what to wear for her “introduction” stared at her reflection in the large bedroom mirror twisting the beads on the plastic bracelet and matching necklace. Turning her head, the baubles on her earrings tugged on her lobes and glinted. This was really happening wasn’t it? Debbie stepped into her heels and pulling on the short fake fur Jacket Miss Simpson had selected for her waggled herself through the reception of the apartment block. Never in the two years she had lived in the block had such a thing happened but the wolf whistle from the concierge behind his desk was clear and loud. Of course, he would never have dared to whistle after Miss Jackson but Debbie?

Debbie blushed and giggled to herself at the attention and shuffling out into the parking lot the unfamiliar feel of the cold breeze, offered no resistance from her flapping short pleated skirt, made her sigh. Yes, this was all real and there could be no turning back now, this is what she wanted wasn’t it?  It was what Mrs. Ross wanted; Mrs. Ross wanted her to get through this, help her, didn’t she? Mrs. Ross had something special waiting for Miss Jackson a transfer leaving all this behind her and all would be well, wouldn’t it? All she had to do for a month, with Mrs. Ross’s blessing and encouragement, was to become the submissive girly secretary of Miss Simpson’s like she had secretly desired and she was ready.

Jane ran her hands over her fine designer business suit feeling the slide of her silk lingerie beneath before stepping her stocking feet into her Italian courts and chuckled after ending the call she had received from Mrs. Ross. All was ready for the introduction of the new manager of compliance and her secretary at the company briefing later that morning. This was real wasn’t it, she was replacing her smug and superior boss Miss Jackson who she had helped to expose to be a weak submissive. Mrs. Ross had promised her all of Miss Jackson’s privileges, her apartment her car her salary and a long-term contract at Sapphire and Ross.  All she had to do, by the end of the month, longer if necessary, was to ensure Miss Jackson became totally absorbed into the persona of Debbie the simpering submissive girly secretary she always wished to be.   Twisting the diamond stud earrings, she had already taken from her ex boss she was ready.

Jane smiled seeing Debbie pulling up outside her apartment block in the car that would soon be her own.

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