Chapter 4: Initiation

Mary Pilson had been working at the Chez Ami for six months when Millicent Varity asked her to come in early one day. Mary finished at the shop and went straight home, washed, fixed her makeup, put on her cigarette girl uniform and got the first bus she could to the Chez Ami.

“Come in Mary; close the door behind you,” Millicent called out from her office.

Millicent was dressed in her daytime attire; an expensive cotton and silk suit that clung to her curves, her hair was coiffured and her makeup perfect. It was too early for her to have changed into her evening gown. Mary sat on the uncomfortable wooden chair when bidden to do so; she squirmed as the hard wooden seat dug into her thighs.

A distinguished looking gentleman in an immaculate suit sat on chair in the corner. Millicent did not introduce him.

“I told you that I only employ virgins but you have been here long enough to know that that is not quite true,” Millicent lit a cigarette and slid the pack across the desk to Mary.

“I know all about the so called extras that the girls earn,” Millicent blew smoke at the ceiling.

“Silly sluts selling their future for a pittance. At least the ones who marry the rich punters have some sort of a future,” she continued.

Mary blushed; there was no need for her to answer.

“To the best of my knowledge you have kept your virginity; am I right?” Millicent looked Mary in the eyes looking for any tell that she may be lying.

“Yes ma’am; I’m still a virgin,” Mary whispered.

“I’m going to make you an offer on behalf of a very special friend of mine. His name is Lord Edward Tilsbury and he owns Chelmsford Hall. He has a position open for a Novice such as yourself; young, virginal, pretty, intelligent and astute.”

Mary opened her mouth to reply and Millicent raised a finger to silence her.

“The life I’m offering you is not for everyone, it is difficult at first and requires devotion and dedication. You will be required to devote yourself to the Masters of the Circle and to be disciplined and discreet. You start as a Novice much like a nun in nunnery, but the dedication required is not to a deity, it is to a flesh and blood human being, a man, your Master.”

“Once you complete your training you become an Acolyte; a devotee to our way of life, even after you leave Chelmsford Hall you have a lifelong commitment to the Circle. But you will never be poor, never be alone, and never suffer any indignity from those outside the Circle. By learning to serve you will set yourself free,” Millicent crushed out her cigarette.

“Those of our order care for each other and for as long as we remain Acolytes to our Masters; we want for nothing. Once you reach the age of twenty-five you will be released from servitude at The Hall and be given a stipend that will set you up for the rest of your life; you will live like an entitled Lady. Of course there are conditions imposed but that is to be expected; you are an Acolyte for life.”

Mary didn’t hesitate.

“Yes I want to do that Millicent,” Mary whispered.

“Are you sure? You will get only one chance to leave once you begin training and that is prior to graduating to become Acolyte, which for you is likely to be about two months away,” Millicent lit another cigarette.

“Yes,” Mary said a little more forcefully.

“Yes mistress!” Millicent barked.

“Yes mistress,” Mary replied in a loud clear voice.

“I would like to introduce you to Sargent William Pitt,” Millicent indicated the gentleman sitting silently in the corner.

He nodded at Mary but did not speak.

“He is Lord Tilsbury’s chauffeur and gentleman; what the lower classes sometimes incorrectly refer to as a butler if you will,” Millicent explained.

“He is here on behalf of Lord Tilsbury to conduct a final inspection before you are accepted as a Novice. Lord Edward has seen you on numerous occasions here at my Club unbeknownst to you. I recommended you to him and he likes what he sees. But Mister Pitt will need to confirm to him your chastity,” Millicent tapped ash into the ashtray.

Mary blushed a dark crimson.

“Oh my! Milli ... er mistress?” she squirmed on her seat.

“Yes I understand I suppose, but couldn’t ... er couldn’t you do it?” Mary’s acute embarrassment made it hard for her to talk.

“You will learn not to question your Masters. No; I cannot do it; it is Sargent Pitt’s duty to do so and report back to Lord Tilsbury. I will remain here as your chaperone throughout,” Millicent replied.

William Pitt arose and his chair scraped ominously on the polished wooden floor.

Millicent arose too and butted out her cigarette.

“Come Mary. Stand over here and bend over; hold onto the desk. It won’t take long,” Millicent’s voice had changed to a soft soothing tone.

Mary nervously did as she was told. She approached the desk, bent over and placed her palms on the desk.

Sargent Pitt opened a small valise and extracted a surgeon’s glove and jar of Vaseline. Mary began to shake as William Pitt snapped the glove and then pulled it onto his right hand.

“There, there. This won’t take long and it won’t hurt; it will just be a little uncomfortable,” Millicent stroked Mary’s shoulder.

“Let me help you,” Millicent pulled down Mary’s satin frilly knickers to mid-thigh and then the tight nylon panties she wore underneath with the stockings sewn to leg openings, exposing her sex.

“Mm; you will need to shave that thatch Miss Pilson,” Millicent commented.

“Open your legs slightly and allow Sargent Pitt to perform his duty. Squeeze my hand if you need to,” Millicent moved aside to allow William Pitt access to Mary.

William dipped his gloved fingers in the Vaseline and moved behind Mary and leaned down to inspect her. Millicent pulled Mary’s skirt up and out of the way; Mary shivered.

There is a common misnomer that a girl’s hymen is located inside her vagina; it is in fact a band of tissue located at the entrance. Sargent Pitt spread Mary’s labia majora and carefully inserted a finger inside her labia minor, the inner lips of her mons. He felt the constricting ring of her hymen at the entrance to her vagina. Mary winced.

William removed his fingers from her vulva and without warning inserted a finger into her anus. Her sphincter was tight despite the lubrication.

“Oh my!” Mary hissed and pushed herself up on her tippy toes.

William retracted his hand from her sex, stepped away and began taking off the glove.

“Pull up your knickers girl and wait outside please,” Millicent patted Mary on the shoulder.

Mary pulled up her underwear and went outside; closing the door behind her.

“All indications are that she is celibate and she has a tight anus indicating that it is likely she hasn’t been taking it up there to keep herself intact. I will report that this young lady meets our requirements,” William Pitt returned his tools of the trade back into the valise.

“No reports of her Frenching the punters to make money on the side?” he closed his bag with a snap.

“None; she is perfectly behaved,” Millicent replied reaching for her cigarettes.

“Leave those. I invoke my right as a member of the Circle; I have needs of you service,” William ordered; his tone suddenly authoritative.

Millicent’s demeanour changed immediately. She bowed her head awaiting the command of her Master. She saw the bulge in his trousers and smiled to herself.

“You have a need sir? I see Mary has caused you some excitement,” Millicent whispered.

“Bend over the desk,” was William’s response.

Millicent bent over the desk.

William stroked her buttocks as he unbuttoned his flies. Millicent became wet in anticipation; years of conditioning created an instinctive response.

“Lift your skirt,” he commanded as he began to unbutton his trousers.

Millicent took the hem of her tight skirt and pulled it up her thighs. William gasped as the dark welts of her stockings came into view and then her milky white thighs. Millicent was wearing tight white silk knickers that stretched over her voluptuous buttocks.

William growled deep down as he caressed her silken-clad globes. Despite her advancing years Millicent as still a magnificent specimen. Her affect on him was evident by the large appendage protruding from his trousers.

He positioned himself behind Millicent and eased the gusset of her knickers aside; the aroma of her sex assaulted his nostrils further inflaming his desire. He gripped her hips and thrust forward, impaling himself deep inside the splendid example of mature womanhood.

“Oh my Master; you were indeed ready,” Millicent gasped.

William said nothing; he gripped her tightly and began to thrust himself in and out of her sodden minge. Millicent pushed back against him; his thick shaft was stimulating her clitoris and she concentrated on keeping the rhythm. William kept a steady pace; enjoying the feel of Millicent’s vagina gripping his hard phallus, he was close to extremis.

He needed to be necessarily brisk; he had his duties to attend to.

He pulled Millicent’s ample derriere hard against his groin and ejaculated deep inside her; Millicent dutifully ground her buttocks against him and used her vaginal muscles to milk him of his spend. Her own orgasm rocked her and she bit her lip and whimpered.

“There, there,” Sargent Pitt patted Millicent on the bottom and extracted himself.

He took a handkerchief from his pocket and wiped his appendage dry while Millicent remained bent over the table; William’s issue dribbled from her vagina and ran down her thigh. William dabbed at it before it soaked into her stockings. He lifted the gusset of knickers back into place and pulled down her skirt.

“Thank you Millicent; you are relieved of your duties,” he said matter-of-factly as he buttoned his flies.

“Thank you Master,” Millicent replied and her demeanour changed again.

She was once again his equal.

Millicent smoothed out her skirt and reached for her cigarettes offering one to William who declined.

“I must away on my duties. Have the girl pack up her things tonight and tell her I will pick her up outside her flat at eleven o’clock. She knows what to expect?” he picked up his valise, ready to leave.

“She knows enough,” Millicent inspected the filter on her cigarette.

“Make sure she’s ready,” Sargent Pitt demanded as walked out the door.

“Come in Mary,” Millicent called after him.

The scent of sex assailed Mary’s olfactory senses as she entered the room.

One year and three months later

Mary was combing Charlotte’s hair. Charlotte’s blonde hair had thickened and become longer. Her curls had been tamed and her tresses fell to her shoulders, she wore her fringe straight; above her shaped and pencilled eyebrows.

Charlotte’s body had softened; becoming more feminine after three months of massive doses of female hormones. The doctor had completed her silicon injection regime and she proudly displayed a pair of small but pert breasts. It wasn’t to be until ten years later that the silicone granulomas caused by the treatment would be discovered during breast implant surgery.

Mary had requested that Sargent Pitt conduct some research amongst transvestite prostitutes and female impersonators to solve the problem of Charlotte’s unsightly bulge. He described a method of tucking involving pulling the penis backwards in between the legs while simultaneously pushing the testicles up into the inguinal canal which Charlotte eventually perfected. She held her ‘tuck’ in place with tight panties under her directoire knickers at night and surgical tape during the day.

She was happy that she finally had the nice curved V at the front of her knickers that she longed for.

Charlotte was without a doubt the most beautiful woman at Chelmsford Hall with Mary a close second. They had formed a bond with Mary mentoring and tutoring Charlotte but the effort to fully feminise and educate Charlotte had taken time and it was now three months since she had first arrived.

“Are you excited?” Mary asked as she fussed around Charlotte.

“Of course! Weren’t you when you lost your virginity?” Charlotte replied.

Charlotte was no longer the meek, passive, young girl that she had been when she arrived. She had developed self-confidence as well as femininity; but she knew how to be demure and accommodating to her Masters and mistresses when necessary.

“Yes; but it was different for me. I lost it twice. Once in the front and again behind,” Mary joked playfully tugging at Charlotte’s hair.

“It will be painful enough losing it for me. When Sargent Pitt examined me back there when I first arrived it was excruciating,” Charlotte recalled her ‘virginity inspection’ on the morning of her second day.

“Well you have no hymen to break put you obviously convinced William that you were chaste,” Mary preened at Charlotte, making adjustments here and there.

“Well I was chased once through that bloody railway underpass; but he never caught me,” Charlotte could joke about her past now that she was safe and secure at Chelmsford Hall.

“There; done!” Mary helped Charlotte to her feet so that she could see herself in the full-length mirror.

Her hair was perfectly coiffed and her makeup was heavy, sexy. A leather choker around her neck had a silver ring to which would be attached a leash, she also wore a silver necklace with an emerald stone, matching earrings and bracelets; a graduation present from the other girls.

Charlotte wore the eveningwear of an Acolyte for the first time. The heavy, green, cut-velvet evening gown under which she wore a black and red basque, the bodice of which pushed up and supported her breasts and cinched her waist. The waist-cinching bustier was trimmed with lace and had attached to it four suspender straps which were clipped to the gauzy welts of her black fully-fashioned nylon stockings. Mary had helped her straighten her seams; her feet were shod in four-inch heels, which made walking difficult but lifted her buttocks and thrust our her breasts invitingly.

She was tucked but not taped; a pair of full-cut tight satin knickers held her penis in place between her legs.

“You look stunning,” Mary grinned, equally proud of her achievements as Charlotte’s mentor and teacher.

“I know,” Charlotte said and pirouetted before the mirror.

Mary clipped a black leather leash to the ring on Charlotte’s choker.

“Ready Charlotte?” she brushed Charlotte’s fringe lovingly.

“Yes. And thank you,” Charlotte leaned forward and pecked Mary’s cheek.

Mary led Charlotte out of her room and they were greeted by the current class of Novices standing either side of the passageway like an honour guard, each holding a candle. The Acolytes did not participate in graduations; Charlotte would soon be an Acolyte herself and they would greet her then as a peer.

Mary led Charlotte through the dark lamp-lit corridors until they came to the imposing door of Lord Edward Tilsbury’s bedroom. Mary solemnly knocked on it three times with the heel of her palm. It creaked open and Edward Tilsbury stood there barefoot, wearing only a black silk robe tied at the waist.

Mary silently offered him the leash and he took it, pulling Charlotte into his lair and closing the door behind them. Mary smiled and returned to her room remembering what her first night with Lord Tilsbury had been like. A smile crossed her lips and she felt herself become moist.

Charlotte kept her head bowed as she had been instructed; she should have nothing to fear, she had been trained in the arts of femininity and knew all there was to know to please a man theoretically. All she needed to do now was to put it into practice.

This was of course not a new experience for Edward Tilsbury; he had deflowered many a virgin right here in this room. But this would be the first time he deflowered a transvestite. Edward had wide and varied tastes when it came to sex; he had sampled just about every perversion and fetish that a virile predominant sexual man possibly could. When he had succumbed to an invitation to sample a lovely young effeminate transvestite who was the favourite of a friend of his, it gave him the idea to recruit such a girl as a novel way to entertain the other Masters of the Circle. Edward and his fellow Masters enjoyed variety.

The Circle, as they called themselves, were not sadists as such, although some of them liked to spank and occasionally lightly whip the Acolytes. But they were all predominant and the Acolytes were very submissive and totally accommodating to their Masters needs.

Edward reached out and lifted Charlotte’s chin so that he could gaze upon her face. The magnificent creature before him was a vast improvement on the pretty but pathetic orphan that he had rescued from beneath the railway underpass.

He tugged on the leash and pulled her to him; he lowered his face and kissed her. She tasted sweet; her mouth was succulent and yielding. He slid his tongue into her mouth and wrapped his arms around her and pulled her to him; enclosing her in his arms.

Charlotte’s head was spinning; she felt so womanly and cherished. Edward whispered pleasantries in her ear, telling her that she was adorable and beautiful, he unclipped the leash and stroked her face and nibbled her ears. She felt his erection pressing against her body; her own penis was uncomfortably tucked under her groin as it distended. She responded to Edward’s kisses and slid her arms around him; they embraced, kissing whilst enfolded in each other’s arms.