Chapter 1: A Sister’s Love

Monika Dupree always knew that her twin brother Alexander was different. Many twins, whether due to nature or nurture, have the same instincts, tendencies, and preferences, explaining why they may do eerily similar things simultaneously. Ultimately, regardless of whether it’s described as telepathy, twins often share a special sibling bond that makes them especially close.

Monika and Alex shared that special bond. As well as being identical they often felt the same emotions, they sensed when the other was feeling discomfort, they got sick together and got well together and they liked the same things.

But they had their differences too. Monika was outgoing and inquisitive and as they grew up Monika became popular and gregarious. She had an abundance of friends, was a school prefect, attended study groups, was captain of her netball and soccer teams and when she entered her teens she was popular with the boys.

The more extroverted and outgoing Monika became, the more introverted and solitary Alex became. They both attended Saint Barnabas coeducational school in Sydney’s trendy Rose Bay, the exorbitant fees paid for by a guilty father who had made his fortune in mining and when he finally became filthy rich he ditched his family and ran away with his personal assistant who was fifteen years his junior.

Alex participated in mandatory extra-curricular and sporting activities. He was a member of the chess club, a contributor to the school newspaper and had middling track and field abilities; all activities that required minimal interaction with others.

Although not exactly identical, you could put Monika and Alex side by side and except for the way they were dressed and Monika’s budding breasts it would be difficult to tell them apart. They stood only 170cm tall and were lithe of body, long-legged and were incredibly good looking. Their faces were narrow with high cheekbones, slightly upturned soft and angelic noses, full lips, dark narrow eyebrows, long dark eyelashes and wide-set green eyes; their faces framed by ash-blonde hair.

At sixteen Monika became fashion forward and as her family were wealthy she could afford to be. ‘Saint Barbs’, as they called their school, had a uniform code but wasn’t overly strict in its application. Monika’s grey pleated skirt was worn a little shorter than mandated, her white blouse a little too tight to accentuate her small breasts, her tie fashionably loose, the school blazer tailored to her every curve and her black shoes were platformed with gold buckled ankle straps.

The mandate for black tights in winter and white ankle socks or beige tights in summer was interpreted as glossy black fifteen denier pantyhose in winter and sheer flesh-toned pantyhose in summer. Girls sixteen years and over were allowed to wear makeup, but sparsely, and could wear sleepers or small studs in their ears. Liberties were taken here too as the teenage girls pushed the boundaries.

Saint Barnabas catered for the wealthy, famous and elite and the faculty and staff were smart enough to know that parents wanted their children educated not overly disciplined so they allowed their students to push the boundaries a little. While Monika’s mom was paying forty thousand dollars a year school fees for each of her children and another ten or fifteen grand on top for extra-curricular activities there was little incentive to piss off Monika’s mother by complaining that her daughter wore a little too much eyeliner.

Not that Monika and Alex’s mother really cared about what her children did or did not do at school so long as they made their grades and didn’t bring the family name into disrepute. Susan Dupree saw it as her duty to spend as much of her ex-husband’s money as possible and to make sure that he knew she was doing so. Susan wore couture, travelled first class, drank only the best booze and used the best designer drugs. She dated male models and minor celebrities and lived a lifestyle that would have made The Real Housewives of Sydney look tame.

Susan was seldom home and was usually found at some gala or event in Sydney, Melbourne or Perth or more likely overseas. The family had a beach house in Nusa Dua Bali and apartments in London and LA and Susan saw no reason not to use them at every available opportunity. Her children had nannies and governesses to look after them and she had made a deal with them both that when they turned eighteen and provided they made their grades and enrolled in a suitable university, they could be emancipated and live in the Rose Bay mansion unsupervised but with a housekeeper and groundsman provided of course.

When Susan Dupree was home she liked to entertain, which to her meant inviting everybody on Sydney’s A-list to party at her mansion. She would insist that Monika and Alex dress in their best clothes and she would parade them around and show them off. Her perfect little twins who were topping their grades and went to the right school, knew all the right people and were enrolled in university. The twins hated it but tolerated their Mother’s attempts to show the world that despite her absences she was ‘Mother of the Year’.

Monika and Alex were closer than other kids growing up and spent most of their time together. It was that special bond they had as twins but also the chaos and turmoil as their parents fought and eventually separated then divorced that brought them closer together. They played with each other’s toys and Monika would sometimes dress Alex up in her clothes and he didn’t seem to mind in fact he seemed to enjoy it.

They grew out of it but it did manifest itself later in their teenage years. Halloween is not traditionally celebrated in Australia but because of global consumerism and the influence of American television and the media it had suddenly found traction. Monika and Alex decided to dress up and go trick or treating. Alex insisted that Monika dress him as a zombie nurse, showing his sister a picture he had found online.

She found them both tight fitting nurse’s uniforms that she shortened the hems and tastefully ripped and stained the pristine starched white dresses. She put them both in white bra and panties, stuffing the cups of Alex’s with balled up pantyhose, put them in white pantyhose which she laddered and put black fishnet stockings over which she also laddered. She found white high heels online and flaming red wigs which she distressed before she put them on. Their makeup was heavy and smeared, very zombie but very sexy.

Under the full moon they both looked like highly sexualised ghoul nurses and when Alex struggled to walk in the high heels it gave him the perfect zombie stumble and stagger.

Alex insisted they do it again the following year but Monika wanted to go out with her girlfriends so they compromised and Monika and her girlfriends dressed as the heroes of The Walking Dead and dragged Alex along behind them on a chain dressed as the sexy zombie nurse.

Alex’s everyday dress became very androgynous as he grew older. His school uniform was tight fitting and he wore his ash-blonde hair shoulder-length with a fringe. He experimented with eyeliner a little but the Brothers at Saint Barnabas told him he had overstepped the mark. He did have his ears pierced and wore gold studs in his earlobes to school.

Outside of school he favoured skinny jeans or tight leather pants teamed with cropped midriff t-shirts or flowing open blouses, with a vest, tailored jacket and in winter long coats. He replaced his ear studs with long dangly earrings and wore stacked chokers and bangles and a little eyeliner. His footwear was either ankle boots or loafers.

At home in winter he often lounged around wearing expensive men’s sports tights or leggings with long-sleeved t-shirts and in summer he wore tight lycra sports shorts and singlets. Sometimes the housekeeper would mistake Alex for Monika when he entered a room.

Alex had few friends and liked to hang around with Monika and her friends and they tolerated him to some extent. Some of Monika’s girlfriends had a crush on Alex but their secret consensus was that he was gay.

Monika also thought that her brother was gay although she had never seen him be intimate with a boy or anyone for that matter. He was very standoffish and was liable to blush if he was even kissed on the cheek.

After an initial period of experimentation where Monika sampled the delights of both sexes, Monika had entered in an exclusive relationship with a boy named Brad Brody who was attending Sydney University. His father owned shipyards with lucrative government contracts and expected Brad to follow him into the business but Brad was only interested in cars, booze, recreational drugs and what Monika Dupree kept under her skirt. He was very jealous and clingy and although her girlfriends were jealous because she had Brad, Monika planned to dump him before she went travelling around the world during her gap year.

So it was that when they finished year twelve, having both turned eighteen, that Monika became concerned about her brother.

At first she thought she was just imagining things when items of her underwear went missing and she sensed that someone had been messing with her things. At first it was easy to blame Gloria their housekeeper and she and Monika had a falling out resulting in Monika banning Gloria from her room. But Monika still sensed that someone was stealing her lingerie, using her makeup and wearing her clothes.

If it wasn’t the housekeeper the only other suspect was Alex.

Alex had gone to see a revival of The Rocky Horror Picture Show at The Dendy Cinema in Newtown and Monika decided to search Alexis room. What she found both surprised and didn’t surprise her. Her intuition was such that she was almost certain that Alex was to blame for stealing her underwear and meddling with her clothes and makeup.

He’d made no real attempt to hide his cache because there was no one to really hide it from. In a large drawer in his walk-in wardrobe she found her missing bras and panties and a collection of pantyhose that she had thrown out. There were also a couple of satin full-slips. The mystery of the missing lingerie had been solved but what else was her brother hiding?

She looked at his laptop sitting on his cluttered desk and was not surprised to find it was not password protected. Once again there was no one in the house to hide things from.

Monika started with Alex’s browsing history. He was a member of website named TVChix frequented by crossdressers, transvestites and those who admired them. His profile under the name Alexis Sydney T-Girl was quite vanilla with a few thumbnails of what was obviously a young man dressed in women’s lingerie and the accompanying text was very nondescript basically saying that he was an eighteen year old with an interest in wearing women’s clothes. She noticed that Alex had also posted some pictures of himself as the zombie nurse taken at Halloween.

He frequented women’s fashion sites. A lot of retro eighties glam shots were saved to his favourites and of course the obligatory porn site links which she decided not to open.

She opened his picture files and couldn’t help giggling at the plethora of selfies that Alex had taken of himself in full drag wearing her clothes and very crudely applied makeup.

The mystery of who was messing with her wardrobe and makeup had been solved.

But it didn’t make sense. Alex and Monika had a very generous allowance and Alex could easily order female clothing online and purchase lingerie almost anywhere saying it was for a girlfriend. Same with the makeup, he could order it online and follow the numerous tutorials on YouTube.

Monika decided she would confront her brother about his crossdressing but do it with compassion and love. She could sense that he was in turmoil and was experiencing supressed anxiety over something and this was likely it.

They were both taking a gap year before beginning university and Monika intended to travel extensively and she wanted to ensure her brother was in a safe space before she left.

“How was the movie?” Monika walked into Alex’s bedroom unannounced carrying two icy stubbies of Iron Jack beer.

Alex was propped up on his huge bed wearing his daytime livery of black leggings and loose-fitting white silk shirt. She noticed he’d worn a little eyeliner out to the movie and it had smudged a little. As usual she couldn’t help noticing how handsome his facial features were and with his elfin form and long blonde hair he looked almost delicate. He could easily model, which for a fleeting period of time Alex had considered.

“It was fine,” Alex was engrossed in something on his tablet.

Monika fell on the bed and handed Alex a beer. She fluffed some pillows and snuggled up next to him. She kissed his cheek and he blushed.

As Alex had matured he became very aware of how pretty his sister was and also of the sensuality she exuded. They were so close and so intimate that Monika was not aware of the effect that her sensuality and sexuality had on her brother; she thought it was platonic sibling love. He inhaled her perfume and sighed. It wasn’t that Alex wanted his sister ... he wanted to BE his sister.

“Were there the usual devotees dressed as the characters in the film quoting the lines?” Monika asked.

At The Dendy Cinema during each showing of ‘Rocky’ a group of loyal fans would do a shadowcast. They dressed up in the costumes and acted out the film as it was being shown while the rest of the audience engaged in pre-planned shenanigans and hurled hilariously insulting lines.

“Yeah, the usual crowd was there,” Alex dropped his tablet on the bed and took a pull on his beer.

“You should go dressed up. You looked really good when I dressed you as the nurse,” Monika smiled at her brother.

Alex flicked a wayward lock of hair out of his eyes and looked at his sister and blushed but said nothing.

“Would you go as Frank N. Furter or Magenta?” Monika asked coyly.

Alex turned to look at his sister.

“Why would you assume I would go as a sweet transvestite or a castle maid, why wouldn’t I go as Riff Raff?” Alex stiffened.

“I don’t know. Don’t most of the guys who go to see the movie take the opportunity to dress up in drag?” Monika offered.

Alex just sniffed and took a sip of his beer.

“Alex ... are you ok? Is something bothering you?” Monika asked.

“I’m fine. Why would you ask?” Alex stared out into space.

Monika took a deep breath.

“Because I know that you’ve been wearing my clothes,” she whispered.

Alex froze and said nothing.

“I don’t mind or anything. You can wear my clothes anytime you want,” Monika murmured.

The silence in the bedroom seemed to suspend time.

“And my makeup. You can use it but I’d prefer you get your own and you definitely need to get your own underwear,” Monika reached out and stroked Alex’s arm.

“I have my own underwear!” Alex said in a huff.

“You know what I mean. Not boy’s underwear, I mean panties, bras, pantyhose,” Monika’s voice trailed off.

Alex lay dead still, his beer forgotten. A single tear ran down his face.

“You know then?” he whispered.

“I know Alex and there is nothing wrong with it,” Monika stroked her brother’s arm.

“Mom will find out and she’ll throw a fit. Dad will disown me. Everyone will laugh at me,” Alex turned his back to his sister and cuddled a pillow.

“No one needs to know Alex. But look, we’re not living the dark ages. People are coming out all the time,” Monika snuggled up to her brother and kissed the back of his neck.

“But I don’t want to come out. I’m not sure if I’m trans; I just like to wear girl’s clothes. I feel comfortable in them. When I’m dressed like that I feel like I’m the real me,” Alex said in hushed tone.

“Besides I look stupid,” Alex continued.

Monika thought of the selfies on Alex’s laptop and his vain attempt at drag.

“What if someone helped you?” Monika snuggled closer to Alex.

Alex said nothing and Monika waited a beat.

“But why didn’t you buy your own clothes? You could have bought them online or at one of the big stores in town,” Monika was inquisitive.

“Honestly ... because I was shit scared. Mom and Dad’s accountants see my credit card bills. The housekeeper gets the mail. People know who we are. How do I explain buying panties and lingerie if someone sees me?” Alex said; his tone peeved.

“You silly boy. Credit card purchases aren’t itemised on the statement. It would just show up as five hundred dollars at David Jones, Castlereagh Street Sydney, not as knickers, bras, skirts and blouses,” Monika dug her brother in the ribs and he turned to face her.

“But the risk Mon ... don’t you see if I got caught I would just die,” Monika could see the fear in her brother’s emerald green eyes.

“What else do you know?” Alex frowned.

“I know that you follow ladies fashion from the eighties. I know about your little collection in the drawer in your walk-in, I know you have a profile on a transvestite website and that you watch tranny porn on XHamster but I didn’t click on any of it,” Monika gave her brother a mischievous grin.

“You searched my room and looked at my computer!” Alex said indignantly.

“You’re stealing my knickers, putting on my makeup and wearing my clothes Alex! I knew someone was doing it and I knew it wasn’t Gloria,” Monika countered.

“I’m sorry. I’m an idiot and a freak,” Alex whispered.

Monika leaned in and kissed her brother softly on the lips.

“You’re not a freak. I’m clearing my weekend and tomorrow we’re going shopping and I’m going to teach you,” Monika said in her authoritative voice that Alex knew meant that she was not to be argued with.

“Going to teach me what?” Alex asked.

“How to be a girl silly,” Monika kissed the tip of Alex’s nose and leapt off the bed.

“See you tomorrow,” Monika smiled at her brother and left the room, her little pleated skirt flicking up behind her.

Alex so wished that it was he in that little skirt and that he knew how to prance like his sister. He picked up his beer and took a long swallow.

Maybe Monika was right? Maybe he just needed some tuition.

Once Alex got over his trepidation the next day turned out to be wonderful. Alex came to appreciate the anonymity that crowds provided. The twins drove to Westfield Shopping Centre at Bondi Junction in Monika’s little red BMW 4 Series Coupé and used the valet service to park.

At first Alex was nervous because of the crowds; he hated being around people and the shopping centre was packed.

“Don’t be silly! The crowds are your friends. Nobody is paying you any attention whatsoever. Anyone under thirty is too busy phone-walking and anybody over thirty just sees two spoiled brats amongst the other million spoiled brats they ignore on a daily basis,” Monika looped her arm through her brother’s and they walked arm in arm.

Other than brief appreciative glances from both sexes Alex and Monika were invisible among the masses of shoppers.

Brother and sister had sketched out a plan before they left home. As Monika was the same build as Alex, he would select the clothes he liked and she would try them on and model them for him. They had established that Alex had a particular style that he liked and had done some online research.

They hit the stores in a preplanned attack that any general would have been proud of. First off it was David Jones to buy dresses, skirts and blouses. In their shopping cart they threw in an A-line mini and a longer pencil-skirt with a matching notched collar single buttoned blazer, both navy blue and three longsleeved blouses in red, white and silver-grey but in different styles.

Alex saw a black V-neck ribbed knit long sleeved knit dress cut short with embossed gold-tone buttons, shoulder pads and two front welt pockets on a store display dummy. It was Italian and a steal at $3000.

When Monika asked if they had one in her size that she could try on the snooty shopgirl looked the brother and sister up and down. They were both dressed casually in black leggings and loose tops, Monika in gold sandals and Alex in black loafers. While the shopgirl tried to assess if the twins were moneyed elite or suburban pretenders Monika dug her American Express Centurion Black Card out of her purse and tapped it on her lipsticked lips.

The shopgirl nearly wet her knickers and invited Alex and Monika to sit on two velour upholstered chairs while she found said item. She took the trolley containing the other items of clothing and put them aside.

What followed next was a small fashion parade, with Monika modelling the clothing and Alex critiquing and the shopgirl running away to find garments that fit Monika perfectly. The shopgirl talked Monika into trying on a red satin evening gown and Alex nodded his head appreciatively. He wanted that dress!

Having racked up a nice bill and giving the shopgirl a generous cash tip they instructed her to have the clothing delivered to the valet parking for pickup.

Shopping for lingerie was fun for Alex once he got over his nerves. Of course Monika couldn’t try anything on but she knew her sizes. The brassiere would be a problem. Alex told Monika that he wore her brassieres stuffed with old pantyhose to fill the cups like she had done to him when he dressed as the nurse for Halloween.

“We can do better than that,” Monika grinned and led Alex down an aisle in the middle of the brassiere section.

“These are called breast boosters, boob enhancers or chicken fillets. They are basically silicone inserts that women use to up their breast size. They aren’t prosthesis like breastforms but you are slim like me so you would look silly with big tits. The larger size enhancer will give you a B-cup which is all you need,” Monika explained.

Alex looked puzzled and she smiled at her brother.

“I’ll show you when we get home,” she grinned at him and threw two different brands and sizes into their cart.

Alex took forever looking at the pantyhose and hold-up stocking display examining the packaging and looking carefully at the colours. Any trepidation he had seemed to have had disappeared.

“You know that girls today hardly ever wear pantyhose. They’re for secretaries, office workers and businesswomen,” Monika turned down her mouth.

“We have to wear them for school but outside of school we might wear opaque tights sometimes but not the sheer type you’re looking at,” Monika said.

Alex turned to his sister and frowned.

“If I was a girl I would wear pantyhose all the time. They feel so lovely and make my legs look great. Also I would like to try those ones I see women wearing in some of the movies I watch. You know the ones with the seam down the back and the dark top,” Alex sounded excited.

A ‘yummy-mummy’ with a toddler in a stroller was standing nearby and heard Alex’s excited vociferation and gave him a filthy look and wheeled her brat away in huff.

Monika looked at Alex with alarm and then they both burst out laughing.

“You mean fully-fashioned stockings you perv. Worn by prossies and loose women but they are making a comeback. I think drag is influencing fashion. We’ll need to go to a specialty lingerie shop for those and we will need to get you a suspender belt,” Monika said and Alex grinned in anticipation.

They threw a pile of pantyhose and holdup stockings into the cart on top of the lingerie they had selected and proceeded to the checkout, stopping briefly to select some costume jewellery and perfume. A stop at a specialty lingerie shop added a garter belt a bustier with suspender straps and five pairs of fully fashioned stockings to the cart.

Alex and Monika knew that shoes would be a problem because Alex had tried on Monika’s shoes and they just didn’t fit. Monika guessed Alex needed a shoe two sizes lager than hers; probably a ladies size 10.

They made their way to Payless Shoes and browsed the aisles after dropping off their other purchases at the valet parking station. They found a pair of cheap plain black pumps in a size 10 with three inch heels and Alex simply slipped off his loafers and tried them on.

When the shop assistant approached Monika and Alex they told her they didn’t need any help and would prefer privacy. Monika guarded the aisle while Alex clomped up and down wearing the pumps while Monika tried her hardest not to laugh at him. The shoes fit, even though Alex was hopeless at walking in them so they purchased them and dropped them in the nearest bin and went back to David Jones where they bought the only three pairs of Christian Louboutin high heels available in size 10 and a pair of silver high heeled sandals keeping the shopgirl happy with a hundred dollar tip on top of the three grand dropped for the shoes.

They were taken to a VIP booth and Alex tried the shoes on in privacy. On their way out they picked up a professional makeup kit and their shopping was done.

When they got home with their purchases it was difficult to tell who was more excited Alex or Monica. Whilst they were shopping Monika had received the usual melee of texts, tweets and DMs from her girlfriends telling her things that were of no real importance but that they thought she definitely needed to know about right now. She had told her friends that she wanted to be left alone for the weekend but her friends didn’t believe that extended social media. Also Brad began to bombard her with texts as he fuelled up on booze and the afternoon dragged on. He demanded that she meet him. He was horny and he loved her.

Monika did the unthinkable and turned off her phone.

“Alright young man or should I say young lady, time to get you dressed,” Monika rubbed her hands together as she surveyed the mountain of packages strewn on her brother’s huge bed.

“I can’t wait!” Alex was excited.

“Well first we have to do some prep work. Go and shower and shave any bum-fluff you might have on your body,” Monika ordered.

Monika had seen Alex’s body often enough in their pool to know that he had hardly any hair on his body and his face was as smooth as a baby’s bottom. Alex sauntered off to his ensuite and Monika busied herself clearing all the junk off Alex’s vanity and replacing it with cosmetics, makeup brushes, a jar of sponges, hair brushes, tweezers, nail clippers and emery boards and other paraphernalia that women needed to maintain their grooming.

Alex came out of the bathroom freshly showered and beaming with only a towel wrapped around his slim waist. He was keen to begin.

Alex and Monika were not offended by nudity; they saw each other naked occasionally and thought nothing of it. Monika whipped off Alexi’s towel and helped him put on a silk dressing gown. Alex shivered as the slippery fabric slid along his sensitive freshly-shaved skin.

“This might become a problem later,” Monika put her hands between her brother’s legs and yanked on his well-endowed penis.

Even flaccid it was quite large and the accompanying scrotum was also quite the bundle.

Alex blushed and slapped Monika’s hand away and she giggled.

“Ok sit down here at your vanity. I’ve got rid of all your crap and laid out your makeup and accessories in a logical order. Take a picture because I presume you will be hiding all this from Gloria,” Monika said and Alex complied.

“Ok let’s start. I need to shape your brows,” Monika reached for the tweezers.

Alex always kept his brows neat but Monika showed him how to shape them in a feminine high-arch to complement the shape of his face. Next she began a makeup tutorial and made up Alex’s face.

“I know you favour the eighties look and this style of makeup will complement most of the clothes we’ve bought,” Monika explained as she applied cosmetics to Alex’s face.

She walked him through every step and explained what she was doing.

Alex was amazed at the results. His face, framed by his shoulder-length ash-blonde hair that had been coiffed at the Alana Kristian hair salon in Rose Bay, their last stop on the way home, looked absolutely feminine and gorgeous and even though it was unspoken between them, they both knew that Alex looked almost exactly like Monika but with a different hairstyle.

“Now you’re going to remove all that makeup and you do it yourself while I get us both some drinks,” Monika fussed with Alex’s hair to get it just right.

“But what about the clothes Mon? I wanna try on the clothes,” Alex whined.

When he whined like that he sounded just like a girl and she told him so.

“Maybe you should practice that voice while you practice your makeup. You won’t become a makeup artist overnight Alex but you’re going to practice until you can do reasonable job. You look like Coco the clown in those selfies you took and I won’t have it!” Monika stamped her foot but she was laughing which caused Alex to blush.

She went to him and cuddled him and kissed the top of his head.

“Do you want to do this or not?” she whispered in his ear and Alex nodded.

“Then practice makes perfect,” she squeezed him gently and went away to get drinks.