Chapter 1: Catamites and Rent Boys

The big dark car cruised slowly along the street; the windows were dark, the grille and bumper bars were all chrome; the large headlights sitting atop of the gleaming front wheel panels glowed an ominous dull yellow.

Charlotte leaned against the rough brickwork in the dark railway underpass hoping the car would pass by without incident. A small suitcase on the filthy pavement beside her contained all of her worldly possessions; she hadn’t eaten for four days nor bathed for two. She wanted no truck with whoever was in the car.

As the black behemoth entered the tunnel, the high beams lit up, dazzling her. She raised her hand to her eyes to shade them.

“There. That one,” the man in the backseat of the limousine pointed to the dishevelled young girl shielding her eyes.

“She looks pretty shabby Guvnor,” the chauffeur commented.

“They always do when I first get my hands on them. She’s the Eliza Doolittle to my Henry Higgins,” the man in the backseat replied.

“You might be Rex Harrison but she is definitely no Audrey Hepburn,” the driver sniffed.

Charlotte picked up her suitcase and began walking but there was nowhere to go. She was effectively trapped in the tunnel; she shuffled along the pavement, leaning heavily to one side to compensate for the weight of her suitcase. She struggled to walk in her high heels, which were two sizes to big for her.

The car pulled up beside her and the back window wound down.

Charlotte glanced over and saw a handsome, middle-aged man beckoning to her; he seemed refined and was very well dressed. His black mane was shot through with distinguished streaks of grey. She felt even shabbier but more importantly if the man got too close to her, her secret would be revealed.

“Come on over I won’t bite,” the man said in a clipped British accent.

Charlotte kept walking; deliberately looking away. She stumbled and fell; skinning her knee and tearing a hole in her already laddered nylons.

She kneeled on her hands and knees and began to sob. She didn’t care what the men in the car wanted with her; Charlotte was despondent, dejected and rejected. She felt worthless and fatally depressed.

Charlotte felt the presence of the man beside her. She could see his immaculately shined shoes and pressed trouser cuffs. Feeling shame wash over her, she looked up at him.

He was offering her a leather-gloved hand, which she reluctantly took.

The man helped Charlotte to her feet; he was smiling, not in a wolfish sort of way, which is what she has continually experienced since she had been thrown out on the street. He seemed genuinely concerned for her.

She stood shaking, leaning one hand on the cold damp brick wall for support. The man pulled a pristine white handkerchief from his pocket and dabbed it on her face. Grime and caked-on makeup soiled the cloth, now moist with Charlotte’s tears. This made Charlotte feel even more abject.

The man took her shoulder to steady her and started to lead Charlotte to the car, which idled at the curb, a plume of blue smoke snaking from the exhaust. The chauffer had got out of the car and picked up her shabby suitcase.

“Where are we going?” Charlotte whimpered.

“Does it matter?” the man replied.

He helped her into the car and Charlotte offered no resistance. The car was clean and warm; two circumstances she had not experienced for some time.

The man climbed in the backseat after her and Charlotte clambered across and hunched in the corner, as far away from the man as possible.

“Are you scared?” the man asked.

Charlotte nodded.

The chauffer slammed the boot and came around to the front of the car; he got in and started driving.

The man reached inside his coat and produced a small bar of chocolate. He offered it to Charlotte who snatched it from his grasp and began to wolf it down.

The chauffer watched in the rear-view mirror and tutted his disapproval. The man flicked a switch and the dark glass window separating the rear passenger compartment from driver’s seat slid into place.

The man lit a cheroot and contemplated the waif. He reached across and turned her face to his, holding her by her pointed chin.

“I bet you’re pretty under that grime,” he groused.

“I’m not a girl; at least not a real one,” Charlotte whispered her confession.

“Oh I know. But I’m going to help you become the next best thing,” the man smiled at her and ruffled her hair.

One year earlier...

Charles Beason was on school holidays, home alone.

Charles was a slender lad who was clumsy and ill-suited to play cricket, squash or rugby, which was almost a religion at the public school where he boarded. He was bright and performed well academically; but not being sporty and considered rather delicate meant that Charles was ostracised by his Housemates. Life at Harrow School was hell on earth for him and he longed to be home where his mother doted on him.

Charles’ father was an Old Harrovain and expected Charles to follow in his footsteps and become a prefect or even a House Captain. The rather exorbitant expenses that his parents paid for the privilege bestowed on Charles was a frequent conversation piece whenever Charles’ poor performance at Harrow arose.

“Leave him alone Reginald; Charles is doing his best. His grades are good and he’s excelling in arts and music,” his mother defended him.

“They should bring back fagging and corporal punishment; toughen him up a bit,” his father made no effort to hide his disappointment.

His mother would usually take Charles in her arms and smother him at this stage of the altercation and Reginald would sniff disapprovingly, flick his broadsheet and mumble something about pansies.

Charles delighted in his mother’s soft embrace, the smell of her perfume, the gentle caress of her Angora sweater.

“The boy will end up a fucking homo if you keep mothering him like you do!” Major Reginald Beason (Rtd) growled, pouring scotch and lighting a cigar.

“Reginald!” Wendy Beason said disapprovingly and put her hands over Charles’ ears.

Charles liked it when he had the house to himself. His father was thankfully often away on business and his mother had endless rounds of social engagements that demanded her attention.

She would cuddle her beloved son before she went out for the day or the evening, kissing him all over his face. Quite often when she came home ‘in her cups’ she would slink out of her gown, kick off her heels and climb under the covers to snuggle and cosset her beloved teenaged boy.

There was nothing sexual between them, but Charles adored the feel of his mother’s soft body sheathed in satin and lace pressed against his; her legs encased in sheer slippery nylon wrapped around his as she held him tight until she fell asleep. Then he would breathe in her smells: lipstick, powder, and perfume with an undertone of champagne, gin or whisky.

From an early age Charles had been fascinated with the look and feel of ladies intimate apparel. Sheer stockings and nylon and satin knickers and underpants, full-slips and half-slips, bustiers and brassieres, suspenders and garter belts; all these things were sacred to him. He loved how they looked, he loved how the felt, and he loved how they smelled after his mother had worn them.

Another passion was shoes. Specifically women’s high heeled shoes. Pumps, stilettos, ankle strap heels, wedge heels, sling-back heels, high-heeled sandals, peep-toes, mules; they fascinated him equally. And his mother had plenty of them all.

Charles could not remember exactly when he first tried on ladies clothing. He remembers encountering his mother’s stockings drying on the towel-rail and her knickers and brassieres and slips hanging from the clotheshorse near the fireplace. He remembers taking soiled undergarments from the laundry basket. He remembers rubbing the items against his bare skin and revelling in the wonderment of their feel.

Charles does remember however numerous occasions when he did wear the garments; late at night in his room, under the bed covers. The stockings were baggy on his legs but they felt luxurious, the same with the knickers, slips and bras.

He would slide into a pair of stockings, pull on a pair of satin panties and then a nylon or satin full-slip and roll around under the covers delighting in the delectation of the garments against his soft, unblemished, sensitive skin.

Charles became brazen. He stole lingerie from the neighbour’s clothesline; they had a daughter who was close to him in size. He spent the day dressed in her lingerie and stockings, clunking around in a pair of his mother’s pumps. He had the house to himself so often that it became routine and he had to admit the chance that he might get caught only added spice.

He wore his hair long; well longish, as did most Harrovians, just below his collar. It was whispy, blonde and curly and his father hated it; said he looked like a London rent-boy. Charles would brush it out and centre part it with a fringe while he was dressed enfemme and brush it back severely at other times.

One day he sat beside his mother who was at her vanity table putting on her makeup dressed in stockings, knickers, bra and slip; her beautiful silk evening gown hanging on a satin-padded hanger ready to slip into before she left for her engagement. Her satin dressing gown was cinched at the waist but Charles could see quite plainly what she was wearing underneath. Wendy ruffled his hair and moved over so her beloved boy could sit beside her while she preened. She was drinking a gin and tonic and gave him a sip.

“Don’t you tell daddy,” Wendy kissed him quickly and then rubbed her lipstick off his rosy cheek.

“Is that hard what you are doing mom? You seem to have to have to really concentrate when you put on your makeup?” Charles asked, innocently enough.

“It’s something all girls learn to do as soon as they can; I could do my makeup by the time I was thirteen,” Wendy grinned at him.

“Did your mother teach you?” Charles was interested.

Wendy turned to him and looked at her son very seriously for a beat.

“I know you like to wear my clothes sometimes Charles,” she said to him.

Charles sat stunned; his mouth agape. Tears formed at the corners of his eyes.

“There, there,” Wendy pulled him into her embrace and patted his back.

“Look Charles; it’s not unusual for men and boys to be fascinated with ladies clothes, especially their underclothes. Why do you think women wear them?”

“We wear them because we like to but also because men like us to wear silky undergarments; they like to see us dressed in them and feel us wearing them. For instance daddy especially likes me to wear stockings and sometimes I wear them to bed for him. You understand what I’m saying? Your father has had THAT conversation with you surely?” she held him at arm length by the shoulders and looked him in the eyes.

Charles lied to his mother and nodded. Reginald had not had THAT conversation with his son because he fully expected that his son would find out all about the birds and the bees from the upper-classmen at Harrow, just as Reginald had and his father before him. Charles knew enough about THAT to know that his fascination with women’s apparel was not sexual.

“I do too. That is I like the feel and I like the smell,” Charles admitted.

“You mean this smell,” Wendy pointed her ornate perfume bottle at him and pressed the bulb.

“Mom!” Charles whined; but they both laughed.

“Now you smell like a girl,” his mother teased.

“Mom!” Charles whined again.

Wendy had been drinking gin and tonics all afternoon. She and Reginald had had a huge fight the evening before when he was packing for another of his business trips. Wendy suspected that he had been having affairs while he was away and Reginald had scoffed at her when she had shown him receipts for flowers, chocolates and lingerie that she had never received.

“You’re being silly, woman!” Reginald had simply declared; closed the lid on his trunk and stormed out the house to his car.

This seemed like a good time to pay him back somewhat; knowing how much Reginald hated that their son was not the rough and tumble larrikin that Reginald wanted him to be.

Wendy puffed the little bottle again and giggled.

“Now you definitely smell like a girl,” Wendy laughed, finishing her drink.

“I do mother. I smell like you,” Charles blushed.

“Well I’ll tell you what. You go and pour your mother another drink and we’ll play dressup together ok? It will be our secret. Just this once and we never tell daddy. That way, when you get married, you will know how much trouble your wife goes to make herself beautiful and enticing for you. You won’t want women other than your wife, because you will appreciate her,” Wendy’s voice caught.

Charles was too excited to notice his mother’s distress and he skipped away to pour his mother a generous gin and tonic just like he’d been taught.

When Charles returned he handed the drink to his mother who downed half of it in a single gulp.

“Go and get your little collection of ladies wear,” she smiled knowingly at him.

Charles blushed. His mother had told him that she knew that he liked to dress in ladies underwear; it should not be a surprise that she knew where he kept it.

His heart thumped in his chest as he went to his room and pulled out the pathetic collection of ‘unmentionables’ from their hiding place at the back of his wardrobe.

When her returned his mother was applying the finishing touches to her makeup.

“There’s my lovely boy. Let’s see what you have,” she smiled at him.

Charles felt embarrassed and ashamed as he held up each piece of his piteous little ensemble. His mother mooched around and selected a pair of full-cut nylon underpants, a suspender belt and a satin full-slip.

“I’ll turn around while you get dressed. I’ve seen you naked many times of course but now that you are of the age of consent I do not think it prudent for me to do so now,” she turned back to her mirror and fussed with the cosmetics.

Charles was quivering with embarrassment, trepidation, excitement, and expectation all at once as he shucked out of his clothes and slipped into the proffered lingerie. He had to sit on his mother’s bed to slip on the knickers and suspender belt and it felt surreal to be doing so.

He nervously padded back to where his mother sat at her vanity table. She turned and smiled at him.

“Well not too bad I suppose; they don’t fit you very well but that’s as expected. Here. A little present for you, you can’t wear those pathetic laddered hose,” she extracted a package of stockings from one of the drawers and handed it to him.

Charles took the package with trembling fingers. His very own brand new stockings! In the past he taken his mother’s discards from the bin or stolen them from the drying horse or from next door’s clothesline.

Dorothy smiled as her son sat on her bed and excitedly opened the package with trembling fingers.

“Be careful not to snag them darling,” she called across the room, sipping on the remains of her drink.

She giggled as she watched Charles struggle to roll the nylons up his legs and clip the welts to the garters. She became a little frustrated and, ensuring her gown remained closed, she strode across the room and sat beside her son.

“Here; watch how I do it,” Wendy entreated.

She smoothed the diaphanous nylon sheath along his leg; took one of the suspenders and adeptly slipped the little rubber disk under the gauzy welt at the stocking top and clipped it to the silver snap.

She smiled at Charles and ruffled his hair.

“Easy, see. Now you do the rest,” Wendy left him to snap the rest of his suspenders in place while she went and refilled her glass.

When she returned, Charles was dressed in knickers, stockings, suspenders and slip. He looked very embarrassed and his face was glowing.

“Don’t be scared darling we are doing this just once to get back at daddy for being mean to both of us,” Wendy hiccupped and spilled a little of her drink.

“Ok you sit at the vanity and bush out your hair and then mommy will do your makeup. I’ll do it as best as I can and we’ll see what you would look like if you’d been born a girl instead of boy,” she beamed.

First Wendy patiently painted his fingernails with two coats of glossy plum red nailpolish. She told him not to smudge the nailpolish before it hardened and explained how women often tried to match their nailpolish with their lipstick.

Wendy applied a coat of foundation to Charles’ face and neck and then set it with a liberal dusting of matching face powder and then went to work on his eyes. She brushed mauve eyeshadow onto Charles’s eyelids working from the inner corner of each eye to the centre above his pupils. She worked the powder upwards up to his eyebrows and then applied a coat of blue eyeshadow out to the far corners of his eyes, lightening the makeup as she worked it up to his brows and blended the two shades where they merged.

Wendy tut-tutted a little and reached for some pink eyeshadow and applied it liberally around the edges; blending the eyeshadow with a small brush and making final adjustments with her fingertip.

Charles was fascinated with the changes that his mother was making to his appearance. He was transforming into a girl right there in the mirror.

“Ok Charles; turn to me and keep very still now and just half-close your for me; here comes the hard bit; the eyeliner.” Wendy’s breath smelled heavily of gin and tobacco.

Wendy applied black eyeliner to his upper and lower eyelids, working outwards so that Charles’ eyes were framed by the black makeup.

“Open your eyes; lift your head up but look down at my tummy and keep still for me darling ok; I’m going to do your mascara,” Wendy explained.

She applied plenty of thick black mascara to his upper and lower eyelashes; fiddling a little as she worked. She explained that as his eyelashes were very fine she had to apply lots of the product to get a good effect,

“Ok nearly there,” she sighed and took a sip of her drink.

Wendy applied blusher to his cheeks, then she dusted his whole face and neck with a coating of finishing powder, being careful not to smudge the mascara and eyeliner.

Finally Wendy coloured his lips with a coat of plum-red lipstick, applying a second coat after the first had set. She had him bite down on tissue to take up any excess.