Legally 'F' Pt. 01

Deportment not so much, hour after hour of sitting in a variety of chairs, hand sweep behind you to brush your skirt so it didn't crumple when you sat, stand up, sit down, stand up, "don't flash your panties unless you really mean to Josephine, and I know you don't fancy me," sit down, stand up, repeat.

How to walk to a door, how to open it, how to take a mans coat and hang it while looking elegant and seductive. How to enter a car, how to enter a bed, how to bend over to pick something up, seductively, and non-seductively.

The choice was always binary, seductive, come on, non-seductive, back off.

Sitting with your legs bent to the right, right leg over left, I'm not interested in sex. Sitting with your legs bent to the left, left leg over right, I'm happy to consider sex, if you ask nicely. Sitting with your legs open, fuck me, with your legs open flashing your panties, fuck me now or I will find someone else who will.

As I lay in bed after another exhausting day I realized it wasn't the lessons I objected too most, but the endless repetition of an invitation to sex, with no possibility of sex on the horizon.

Shorthand, Transcription from tape, Typing, Stenography. Each week one more of these old fashioned classes were added to my workload, I hated them, but I worked hard to excel at them as I wanted to get them out of the way as quickly as I could.

I thought they were useless until Mrs. Brown explained to me that executives of a certain generation may not expect you to take shorthand any longer during the normal course of business, but will judge you poorly on your competence if you do not have the complete set of skills a senior PA should have.

She invited me to her rooms that night, poured us each a Brandy and told me her life story. She had been the PA to the CEO of a fortune one hundred company, she knew more secrets about American business than the CIA.

She was independently wealthy, very wealthy in fact, her net worth was well into eight figures, her pay and bonuses had been large and her CEO sponsor has invested her wealth wisely.

"Why this then?" I asked motioning my arms around.

"Long ago, another teacher took time to lead me on the journey which brought me my success, I would serve her memory poorly if I was to l to just disappear to a Caribbean beach into a life of hedonism.

"Youth may be wasted on the young, but we elders can at least help them avoid the mistakes we made, and appreciate the successes we had."

She stood and let her skirt fall to the floor, underneath her legs looked as young and slim as mine, as she pulled her panties down her erect cock sprang out, standing large, hard, and proud.

"You're not the first to suffer the pain of this course, Josephine, been there, done that, you won't be the last either. If I have a true legacy, it will be that one of my students will occupy this room one day."

I laughed.

"What?" She asked as she redressed herself.

"Sorry ma'am, but I'm just hearing the Disney song, 'Circle of life' in my head."

"It's not entirely inappropriate," she replied, "now stand up dear, skirt up, panties down."

I left her room with permission to masturbate myself silly until first light, I was to count how many times I came, and let her know as she refastened my chastity device in the morning.

'Six, Ma'am."

Phase 7 -- Deportment School Thirteenth Week.

I was a 3.8 average student, no one ever received a 4.0, but those who averaged 3.75 or above were allowed a weekend visitor on the middle weekend of their course.

It was Friday evening, and I stood at the front door of the castle waiting on Steph, Mrs. Brown had given me a lovely yellow summer dress, with matching lingerie and pumps as a gift so that I wouldn't greet Steph in the blandness of my school uniform, and I hopped from foot to foot with great impatience, she was late.

Finally, the Uber broke through the trees and sped up the path, the doors of the car opened and I sped into Stephs waiting arms, she laughed, "it's not been that long Josie, and I've been through this, it's not that horrible either."

"Oh yes it has been Steph, horrible, horrible, horrible, when I leave here I'm burning that flannel nighty right over there," my arms pointed to the flag pole which was the centerpiece of the front lawn, "and I will dance around it as the flames consume it and my hatred of it."

She laughed, "do you really think you will be the first to think of that honey?" She held up an Agent Provocateureur bag, "anyway, no flannel nighty this weekend."

"Agent Provocateur?" I asked.

"Very expensive, very sexy underwear, I have a little something for both of us," she was grinning, "I was no fonder of that flannel nighty that you are."

The Uber driver had already unpacked her bags, and was heading to one of the guest bedrooms, "shall we follow?" I asked.

"Not yet, he knows where he's going."

She stepped back to look at me, "you're looking great honey, yellow really suits you, that's a very pretty dress."

"A present from Mrs. Brown. She didn't want me looking all dowdy when one of the school's former star pupils returned to visit."

"Talking of Mrs. Brown," Steph said, "the first thing we need to do is visit your form mistress."

"Really, Mrs. Brown, why?"

"I wouldn't want to spoil the surprise, shall we?" Her arm waved me towards the door and out of the summer sun.

I looked over Steph's shoulder as she handed a form to Mrs. Brown 'Waiver, consent for mutual masturbation'.

Mrs. Brown took out my permanent record and inserted the waiver inside it. She removed my chastity device, whispered "enjoy yourself, Josephine," then waved us off.

Once we had left the office I whispered, "how did you get that Steph, I'm not meant to have any sexual contact with others until graduate school, it's in the rules."

She laughed, "you'll find out in time Josie, there are rules, and there are rules, let's just say that I was owed a favor by someone for whom few rules apply."

She took my hand and we ran up the oak railed central staircase towards the guest quarters. As her bedroom door closed behind us I fell into her arms and her kiss. I was so happy, her light fingers undid the zipper of my dress and I stepped out of it and back to be admired.

I was wearing yellow stocking and suspenders, with a yellow teddy top, the matching panties had been left on my bed, and my erect cock was highly visible.

I winked at her, "do you like what you see Steph?"

She kissed me as she slowly pushed me back towards the bed, her hand rested lightly on my cock, then gathered around it and softly began to move.

"If I remember my lessons properly, the 'fuck me now' signal is to sit with your legs open flashing your panties, a little hard to do if you're not wearing any panties dear."

She pushed me on to the bed, pausing only to drop her own dress to the floor, underneath she wore black hold up stockings, and nothing else, her own cock was erect as mine and she joined me on the bed.

I reached for it and she swatted my hand away, "we've three nights, and two days to enjoy let's try to take it at least a little slowly at first."

Her arm went around my neck and she pulled me in for a kiss, she was establishing her role as the dominant member of our duo, which was fine by me, my arms went around her neck as her hands slipped down to feel my ass, and I opened my mouth to receive her tongue.

We made out for a long time, lying on top of the bedspread, while the sun streamed through the large bay windows of the room, to give us light and warmth.

Steph got up, went to her bag, and came back to the bed with a tube of KY lotion, Hers and Hers. I was lying back with my head propped on the pillows, just a little nervous.

"Let me go first Josie, then you can do me before we try to do it simultaneously, agreed?"

I nodded my head and watch as she squeezed a large drop of lube into the palm of her hand, she lay down beside me and kissed me as her hand found my cock, very softly she spread the lube along its length, not forgetting to make sure a little covered my balls.

The lube went on cold, but quickly warmed and tingled, still in her embrace, I felt her hand slowly move, it started at the head and moved down until it touched my balls, then returned to cover the head once again.

I broke from her kiss, this was the first human being to genuinely sexually touch me, and I wanted to watch, at least I wanted to watch the start of the thing. My eyes were fixated on her hand as it softly moved up and down my shaft, I had to concentrate on not cuming instantly, I couldn't watch any longer, satisfied I lay back to receive her tongue in my mouth once again.

She stepped up her pace gradually until finally, she was moving so fast, that my balls hurt a little as her hand slapped into them, I could take it no longer.

"Oh god Steph," I cried, "I'm cumming."

A vast stream of spunk flew from my cocks eye and covered me from chest to belly button. Steph removed her hand from my cock, let her fingers lap up the steaming spunk and lasciviously licked them.

"Would you like a taste, Josie? Would you like to taste yourself?"

I nodded and accepted her fingers into my mouth, my tongue lapped off the salty warmth, and she pulled into her arms to spoon.

I was facing the bedside table, I could see the lube taunting, tempting me, it was time, my turn. My hand reached for it, and I turned back to her. She was ready, she lay back on her pillows her hands behind her head, a figure of naked confidence, and smiled at me.

I took a deep breath pooled the lube in my hand and reached for her wonderful cock, as I grasped it I was almost overcome by emotions, I didn't know whether to cum or cry, but after a few deep breaths, I steadied and let my hand do the work.

I had masturbated myself often enough, thousands of time, tens of thousands of time maybe, but doing so for someone else wasn't as easy as it seemed, each of us has a personal preference on the mechanics, tightness of the grip, the length of stroke, the speed of the stroke, and you had to adjust from your own preferences, communicate with your partner to ensure you were pleasing her.

Steph was a great instructor, she told me exactly how she wanted me to do things and gave me a constant stream of encouragement as I touched my first human cock other than my own. I gazed into her eyes and saw love and lust and I hoped mine returned the compliment, she didn't come for a long time, my arm was a little tired by the time she arched her back, groaned and sent a river of spunk running down her chest.

It was a totally spontaneous thought on my part, she hadn't done it to me, but I just put my head to her chest and my tongue began to lap her clean, her fingers grasped my hair, "oh Josie, you are so fucking good."

We had a quick shower, redressed, and hurried off to the master's private dining room for a meal with Mrs. Brown. Steak au jus, mashed potatoes, a deep dark red wine, after weeks of my nutritionist's regime of terror, this was heaven.

Mrs. Brown wanted Steph to tell her all the things happening in the city, and the two monopolized the conversation, Steph played footsie with me under the table, occasionally her toes would pop under the hem of my dress and feel their way along the inside of my thighs. I was hard the entire meal.

We finished the bottle of wine, Mrs. Brown looked at us and said, "well I suppose I have kept you girls long enough, thank you for your company."

We stood and waited until she had left through the door into the master corridor, and the rushed back to our bedroom, I was in a rush to get naked again, but Steph stopped me. She went to the table and held up the Agent Provocateur bag, "why don't you try this on, Josie," she smiled.

Phase 8 -- Deportment School Back to work.

Steph had left me, facing another thirteen weeks of lonely misery, now languages were added to my burden, French and Spanish, Accountancy, Librarianship, the academic classes piled on, and I still had the advanced classes for transitioning my life from geek to womanhood to get through as well.

To be honest, the school's work was subtle but effective, I never thought of myself as male now, I was she, her, herself, and very comfortable in that.

My rooms were spotless tidy and clean a miracle my deceased mother would have fainted at if she had lived to see it. They also had a little more color to them, as I was now allowed some modest decoration. I had picked a few window treatments and prints to make my room look less like a prison cell.

While the workload was crushing, there was some relaxation of the rules, the chastity device was removed for longer and longer periods of time, until I began to miss its feel, just a little.

The hated school uniform was still forced upon us during the week, but at the weekend we were allowed to wear casual clothes. My wardrobe was expanding, Steph had sent me my first classical little black dress with matching lingerie which according to her accompanying note was a necessary weapon in any ladies armory.

Via Skype I was introduced to the Maitre Ds of the best restaurants, the concierges of the best apartments and hotels, the managers of Broadway theaters, client relationship managers in Vegas, my Rolodex had a few cards added to it each night as Mrs. Brown introduced me to the people I would need to build relationships with to keep Mr. Devonports life on schedule.

A large part of that life I now understood was lived outside the office entertaining clients, It was all part of a world I had never understood existed, but it was very real, and soon I would be throwing myself into the depths of it.

There were contacts to a few less than savory characters too, business was business, and from coke to hookers, a good PA had to know how to procure anything one of her bosses clients may require. There were also contacts on the right side of the law, cops and ADAs, discreet bail and the disappearance of minor charges was another skill I had to learn, along with knowing how much each service should cost.

"You can use one of those apps on your phone to keep your contacts in order dear, it's not a bad thing, but trust me, a bulging Rolodex will always be looked on appreciatively by your boss, and you're unlikely to ever drop it accidentally down your toilet, and yes trust me, that happens, more often than you would think."

I learned how to judge everything, from steak to wine, from bed linen to suits, flowers, chocolates, fragrances, everything material, and also the more subtle skills of judging were on the social matrix a client was positioned, and the exact grade of gift, entertainment or favor their position had earned them.

Mr. Davenport would handle all the face to face interactions obviously, but I would handle everything behind the scenes to support him, Mrs. Brown was at pains to reinforce just how great a level of trust was being shown in me, and the pressure was becoming overwhelming.

I had missed a scheduled appointment with Mrs. Brown, she had a passkey to my room and found me lying in bed sobbing into my pillows. She sat on the bed beside me, and her hands softly brushed my long hair.

"Josephine, whatever is the matter dear," I looked up at her, my face must be a ruin, and she handed me a glass of water from off my bedside table to sip.

Once I had settled down a little I responded, "It's too much ma'am, no one can learn all of this in such a short period of time."

"Of course not dear, no one expects you too, these are the foundations, no one becomes fluent in French in just thirteen weeks, even if they are immersed in the language.

"These are foundation courses, you will expand your knowledge at graduate school, and you will refine it much more during your apprenticeship as Junior PA. This is a life long exercise, I may be mostly retired these days, but I am still learning.

"It was nearly thirty years ago I found myself in your position," she sighed, "This room was mine once Josephine, so many young ladies have slept in it since, but I think you may have the most potential of any of them.

"Every girl has a breakdown at some point during this course, you made it to ten weeks into the second term, I would need to check, but that might be something of a record."

She stood, "no more work today, rest, and we will pick things up in the morning, but I told you once before, this course is designed to put an unbearable strain on its students, trust me, Josie, you are doing very well."

The room door closed behind her. Josie, she never called me Josie, it was always Josephine, that single simple act went a great deal towards restoring my equilibrium, and I slept the sleep of the just.

The final two days were a nightmare, there were no written exams this term, no, it was a murder board, panels of three teachers, most of whom I had never seemed before would fire off question after question, two two hour sessions on each day.

It was discombobulating, they never stuck to one subject, I'd get asked an accountancy question, then need to translate a phrase into French, or translate from Spanish, then take shorthand notes, sometimes they would fool you by asking you five or six questions on one subject in a row, before suddenly switching the subject again.

Eight hours of constant questioning, with no sign from the questioner if you were doing well, poorly, just a stern face asking, "is that your complete answer," before the next would jump in with a question.

It was the hardest thing I had ever done, and thankfully I passed. I think I would have rather had expulsion and financial ruin, rather than have to sit through that nightmare once more.

I was called into Mrs. Brown's room, Steph was already sitting in a comfortable chair talking to her.

"Josephine, your final results have been tabulated, you have passed, and your place at graduate school has been confirmed, I will be sending your records on from here, but let me just say your record of achievement here was excellent.

"You have the weekend girls, and I have a few presents you, the first is I have reserved you a suite at the Sagamore Hotel on Lake George, and the second is a little addition to your permanent record, Josephine."

She turned over a piece of paper on her desk, opened the large manila folder on her desk, signed it at the bottom, and inserted it in place.

Steph was closer than I, she read it and gasped, her hand went behind her back to beckon me over.

"Mrs. Brown," Steph exclaimed, "how did you manage this?"

Her hand tightened on mine as I approached her, and I read the top sheet, 'waiver for oral sex.'

I stopped to stare at Mrs. Brown.

"You Steph," she said, "are not the only person owed a favor by people of certain importance. The Sagamore is about an hour and halfs drive in a fast car, if you girls hurry, you may have time to explore a little before the restaurants close."

My suitcase was already packed, I was going to leave every item of the school uniform behind on my bed, Steph looked at the pile and said, "Take the tie, Josie, you've earned those shields."

"I so wanted to burn that flannel night down to embers Steph, but..."

She joined my laughter, "let's get the hell out of here."

It was dark by the time we ordered room service, although when we checked in it was broad daylight.

We took our time, laid out the clothes we were going to wear, had a bubble bath, did each others hair and makeup, then hand and hand, wearing our matching Agent Provocateur Lingerie we settled on the massive bed in our suite.

Even though it was early summer, a fire roared in the corner, we had opened the windows, patio door and blinds and the fresh air and sun streamed on top of us.

We didn't speak, our panties were crotchless, and we each sported an erection, Steph arms brought me into her arms and we kissed, softly, my hand was wrapped around her cock but I wasn't making any serious efforts yet.