Chapter 2

Cabin 121 Park Motor Lodge, Engadine NSW, Australia

Sarah lay under Loyd feeling his semen seeping from her sphincter and dribbling between her buttocks. She was still feeling the aftereffects of her orgasm and oblivious to her surroundings but then the handcuffs rattled as Loyd moved on top of her and she suddenly became aware of the three other men standing next to the bed waiting their turn.

Once again she pondered the happenstances that had led to her current predicament. Of course she was well aware of the circumstances as to how she had been lured to the cabin but her thoughts drifted further back in time to when she had first become aware that she was different to most of the other boys and how her compulsion to crossdress and her inclination towards promiscuity had begun.

Kurrajong Street, Sutherland NSW, Australia – 1979

Stefan Lang had been a crossdresser for as long as he could remember.

He’d started out like most of his ilk, fascinated with ladies lingerie, hosiery and shoes and enchanted by frocks, crinolines, skirts and blouses. Like most serious crossdressers, he had graduated from nicking his mother’s and sisters ‘unmentionables’ from the washing basket and rummaging through their wardrobes to try on their clothes when he had the place to himself. Stefan made choices that separated him from the ‘hairy-panty-wearers’, determined to learn how to present himself as realistically feminine as possible.

He saved his pocket money and his earnings from his paper route and the odd jobs he performed for cash and purchased himself a proper wardrobe. A small selection of clothes that fitted his svelte frame, a pair of high heels that fit, a decent wig and his own cosmetics. Most of the clothes came from the Op Shop as did the heels but the lingerie and hosiery and underwear came from Myer. Stefan had made the train journey from Sutherland to Sydney to acquire his necessities, the journey taking around an hour each way.

Stefan did this for two reasons. One: there was every chance he would run into someone he knew in the local Op Shop and nearby department store and it might prove embarrassing explaining why he why he was purchasing ladies clothing. Two: There were more stores to choose from and a better selection of goods in the city.

The women at the Op Shop on Oxford Street were used to men coming in and purchasing women’s clothing and more than willing to help them find attire that suited them and fitted properly. Oxford Street was at the centre of Sydney’s burgeoning LGBTI community, although in the 70s the queer community had not begun their appropriation of half the alphabet and were known disparagingly as: poofters, homos, and ponces. Those who had a predilection to dress up as women were: fairies, nancies and nellies. Another reason that Stefan needed to shop in secrecy.

Myer was one of the largest department stores in the city at the time and Stefan stuck out like a sore thumb as he roamed the aisles of the lingerie department selecting lingerie and hosiery. The hoity matron behind the counter had given him a withering look when he took his purchases to the sales registry and Stepfan had blushed and stammered his way through the exchange of cash for goods. There was no ‘tap-and-go’ in those days.

The wig he had purchased in a costumers on Oxford Street. The shop was little more than a front for crossdressers and transgender women (another term that had yet to be coined) to purchase their necessities in a safe space.

He’d seen the Bettie Page wig sitting on a wig stand in the storefront window and immediately fell in love with it. The combination of thick, straight bangs and flowing curls that spanned just past her collarbones was Bettie’s trademark. The wig had nearly cleaned out the remainder of his savings, but on the train ride back to Sutherland Stefan was so excited that he counted down the stations until his train arrived at Sutherland station and then he ran all the way home.

Stefan had to wait for what seemed like an eternity for Saturday when his mother took his sister Julie to her weekly netball carnival, this time being held at Miranda. They would be gone all day and afterwards his mother was treating Julie to a shopping spree at Miranda Fair where they would also have dinner, meaning Stefan had the house all to himself all day.

As soon as they left Stefan showered and plucked the few hairs that grew on his chin and in the hollow of his chest. At school Stefan was sometimes teased in the changeroom because unlike most of the other boys who had suddenly become hairy yetis when they hit puberty, Stefan’s body and legs remained smooth except for the patch of pubic hair between his legs.

Stefan pretended that he was jealous of the other boys hirsuteness and muscled frames but secretly he was pleased that his body had become muliebral, svelte and curvy rather than rugged and masculine like his peers. It was easier to fit into his mother’s and sister’s clothes but now he had his own wardrobe which he was keen to put to the test in the privacy of his bedroom.

Dressing enfemme for Stefan quickly became more than just something sexual or fantasy fulfilling. He’d adopted the femme name Sarah because it was close to ‘Stefan’ but not too close. Sarah wanted a name that reflected a complete change of gender and praised herself for not adopting the name Stephanie which would have continually reminded her that her ‘boy name’ was Stefan.

When she dressed, Sarah did not just dress like a girl, she became a girl both physically and mentally. It was a total transformation. She was another person, unencumbered by her male identity. She adored her small collection of feminine essentials, especially her Bettie Page wig. She practiced her makeup skills and became adept at presenting her own unique, feminine persona. She learned to walk and talk like a girl and instinctively adopted feminine mannerisms.

It was the little things about being a girl that Sarah adored: the faint hiss of her nylons as they rubbed together, the gentle flutter of the hem of her skirt on the back of her legs when she walked, the taste of her lipstick, the smell of her perfume, the gentle caress of her hair on her neck and shoulders.

She looked forward to Saturdays when she had the place to herself and she could roam around the house freely. Simple things brought enjoyment such as reading Julie’s Dolly magazines or her mother’s Women’s Weekly, washing and ironing her clothes, trying on different outfits. She’d try to imitate Bettie Page, wearing a tight basque, fully-fashioned stockings and severe makeup or maybe dress as a sexy secretary dressed in a tight pencil skirt, satin blouse and fleshtone sheer-to-the-waist pantyhose.

Sarah was limited by her wardrobe. She had only one wig and one pair of black high heels and her collection of op-shop clothing but she made do with what she had and perfected her looks.

Of course there was a sexual component to Sarah’s compulsion to present femme. When she had finished ‘playing house’ she would retire to her bedroom and drag out the small collection of soft porn that Stefan kept hidden under his bed. Of course there was a Bettie Page magazine but also some editions of Fiesta, Club International and Escort, where women posed provocatively in sexy lingerie and titillating stories were published, usually claiming to be real-life adventures. The threads to these stories were the usual schlock that titillated the male readers: naughty nurse, licentious secretary, horny next-door neighbour or busty librarian. Most of the women characters were at first reluctant to unleash their secret desires but the male protagonists always got into their knickers.

About an hour before her mother and sister were due home from their weekly sojourn Sarah would look at the pictures in the magazines or read the stories while she draped a nylon stocking over her erect member and slowly bring herself to climax. In the fantasies she wove while she masturbated she was one of the women in the pictures or a female character in one of the stories and some faceless but surely handsome man would seduce her. When Sarah climaxed she recalled how wonderful it had felt when Rita Blackwell had stroked Stefan to climax in the bushland behind the scout hall. Rita had lifted her skirt while she did it so that Stefan could stroke her pantyhose-sheathed thighs and panty-clad pubis.

At sixteen years of age Stefan was still a virgin when he’d had the handjob from Rita Blackwell. Rita had left school at fourteen and was still working at the same grocery store. She had become promiscuous very early and she was the type of girl who would show you her knickers for a couple of bob and she would give you a handjob for a dollar if she liked you.

The stories in the magazines that Sarah read were not exactly explicative when it came to the sex acts themselves but even though Stefan had no father to give him ‘The Talk’, Stefan knew enough about the mechanics of sex and exactly what words like coitus and fellatio entailed. In Sarah’s imagination she was the one performing fellatio or lying on her back with her legs open, while the faceless but handsome man lay on top of her rutting.

Everything changed one fateful Saturday afternoon. Sarah was dressed in a rather demure navy-blue A-line skirt, a crisp white blouse, and her black high heels. Underneath she wore black satin full-cut panties and a matching bra stuffed with balled up pantyhose because she had no breastforms and at this stage of her life didn’t even know they existed. Of course she was also wearing hosiery, in this case cheap tan pantyhose she’d purchased at the Coles.

She was sitting in the loungeroom flicking through Julie’s latest edition of Dolly, envious of the young women pictured in the fashion section when she suddenly became aware that she was not alone.

Billy Barton stood directly in front of her, staring lustfully at her, and by the bulge in his jeans his intentions were obvious.

Billy Barton lived across the street from the Lang’s and was in twelfth form, the same form as Stefan but Billy was one year older. He was tall and lanky and a better than average cricketer and footballer but disliked by his peers. He was a bully both on and off the playing fields and had been appointed as a school prefect and he thought nothing of twisting the ear or cuffing the back of the head of any student he found breaching the school rules. Male students either feared or avoided him and the girls were not attracted to his plain looks and scruffy appearance. His clothes were far from fashionable hand-me-downs or purchased at discount stores and his hair was lank and always looked unwashed. Billy was also afflicted with teenage acne which at the age of nineteen was a curse.

Billy converted the frustration and misery caused by his family’s financial status and lack of acceptance into anger and was inclined to lash out without warning. Fear of reprisals kept those who were the victims of his anger from reporting him. In some ways he and Stefan were similar in that they both came from fatherless homes, were far from affluent, and both solitary. But in other ways they were opposites. Stefan was meek and studious whilst Billy was brash and athletic.

“How long did you think you could get away with this?” Billy asked as if he was just confronting Stefan in the school quad rather than having broke into his house.

“How did you get in?” Sarah’s voice was a terrified whisper.

“You left the door unlocked you dickhead. I kicked my football over your fence a few Saturday’s ago and when I came over to retrieve it I saw you through the window. At first I thought you were a girl, one of Julie’s friends, but I knew that Julie had netball all day Saturday and your mom’s car was gone,” Billy answered Sarah’s question and extrapolated further.

“What are you doing here?” Sarah was still terrified.

If Billy were to blab to the students and teachers at school, or even worse, tell Stefan’s mother or sister that Stefan liked to dress in ladies clothing, Stefan’s life would be ruined.

“I’ve been watching you putting on your little fashion shows, parading around the house like a girl and of course I’ve seen you wanking while you look at those dirty magazines,” Billy hadn’t answered Sarah’s question and the sneer on his face did not bode well.

“You still haven’t told me what you are doing here,” Sarah tried to sound defiant but she just sounded meek.

“You even talk like a girl when you’re dressed like that, do you know that? You’re very pretty. I doubt anyone would know who you were under that wig and makeup and your legs are stunning,” Billy still didn’t answer the question but while he was talking he took a step closer to Sarah and began to unzip his fly.

“If you give me a headjob, I won’t tell anyone I promise,” Billy’s sneer became a leer.

He was looking at her legs and up her skirt at her panties and Sarah realised that she was sitting with her legs wide open, the discarded magazine beside her. She demurely closed her legs and straightened her skirt.

“You even act and move like a girl Stefan,” Billy chuckled.

“It’s Sarah!” this time Sarah did sound defiant.

“Ok Sarah, you suck my dick and I won’t tell everyone that you are a crossdressing sissy,” Billy took another step forward and his cock was inches from Sarah’s face.

Sarah had to think quickly. At the moment Billy Barton held all the cards. If he blabbed, the consequences were unthinkable but if Sarah did what he asked, Billy became complicit. She could blackmail him in return. Sure he could out her as a Nancy but it would be her word against his regarding her giving him a blowjob. Deep down inside, where Sarah kept her secret thoughts and yearnings, hadn’t she always wanted to know what it was like to be woman in that way? Her masturbatory fantasies involved a faceless handsome man doing things to her. Billy Barton was far from handsome and in many ways despicable but Sarah was trapped. It might have been her subconscious justifying her actions but she made the decision then and there to cross the Rubicon.

“You can’t tell anyone,” Sarah whispered.

“Don’t tell me what I can and can’t do,” Billy waggled his hard cock in Sarah’s face.

“Ok, here’s the deal. You call me Sarah. You treat me like I’m a girl. You never mention Stefan’s name or refer to me in the male vernacular while I’m dressed like this,” Sarah was becoming confident.

This might be her way out of being publicly disgraced whilst at the same time discovering if her sexual fantasies were anything like she imagined them to be.

“Fine with me. I don’t want anything to do with Stefan, just with you ... Sarah,” Billy said impatiently.

Sarah actually smiled as she reached out and put her hand on Billy’s rampant organ. It was long and smooth with blue veins running down the girth of it and instinctively she traced one with her red-painted fingernail. Billy shuddered and his cock juddered. He unbuckled his jeans and they fell around his ankles.