A Safe Space - Chapter 1

Printer-friendly version
Safe Space Edited.jpg

Chapter One – A Sister’s Love

Author’s Note: This story begins with a loving sister helping her twin brother with his transition to womanhood. It begins at a leisurely pace and gains momentum as the protagonist struggles with her gender dysphoria and her sexuality. I have set the story in Sydney Australia where I lived and worked for many years of my life. Also be warned that this chapter contains incest.

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.

Monika found them both tight fitting nurse’s uniforms and she shortened the hems and than tastefully ripped and stained the pristine starched white dresses. She dressed 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 the year before, 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 Alex's 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.

Monika came back with vodka tonics and helped Alex with the more difficult part of the makeup process: eyeliner, lipliner and eyeshadow. She made sure he got it right and after a few attempts she told he was doing ok and that with practice he would soon become adept.

She sprayed him liberally with perfume and saw the excitement in his eyes as they gazed at Alex’s purchases. Something had happened and they both felt it. Neither of them thought of Alex as he any longer. Alex was she. Well Alex was Alexis… except for one thing and that thing was going to be a problem. In her excitement and anticipation of dressing in her new clothes Alex had sprung an erection or at least what Monika’s boyfriends called a ‘semi’.

For now Monika ignored it and they unwrapped and laid out pantyhose, bra and panties, skirt and blouse on the bed and selected a pair of high heels to go with the outfit.

Alex was no stranger to putting on pantyhose and Monika looked away while she stepped into them and smoothed them along her freshly shaven legs. The feeling of the expensive, sheer nylons on her freshly shaven legs caused Alexis’ erection to become fully tumescent. Out of frustration she positioned the erection along her lower belly and pulled her orange satin and lace boy-leg panties up over it.

Ignoring the lump in Alexis’ knickers Monika helped her adjust the matching bra and showed her how to put it on.

“Put these in the cups like so and get them to sit right. The silicone will adhere itself to your skin so they shouldn’t move,” Monika explained as positioned the ‘chicken fillet’ breasts enhancers just right.

Alex had a little trouble buttoning the red satin blouse because the buttons were on the opposite side to what she was used to but she got it done and stepped into the black leather Carla Zampatti skirt. She sat on the bed while Monika helped her put on her high heels. She made Alex walk in them and gave her pointers on how to walk with a feminine gait: take smaller steps, swing one foot directly in front of the other, toe pointing down. Alex cautiously made her way around the room a few times and then she settled at the vanity and put on her jewellery.

“Look at the beautiful young girl in the mirror,” Monika pointed to the full-length mirror and there was indeed a beautiful young woman looking back at Alex.

This was no boy in clown makeup wearing mismatched clothing stolen from his sister’s wardrobe. This was a gorgeous, sophisticated and yes… sexy young woman standing beside her almost identical twin.

They both ignored the elephant in the room which was the bulge in the front of Alexis’ skirt. Seeing herself like this for the first time was both emotional and arousing and try as she might she couldn’t will her erection away.

“Thank you so much Mon. From now on I'm going to call myself Alexis but I will still abbreviate it to Alex so that I don't feel weird when people call me that, ” Alex hugged her sister and began to cry.

“Don’t you cry, you’ll ruin your makeup,” Monika held her new sister tight, trying to ignore the bulge pressing into her belly.

“There are tutorials online on how to tuck. You’ve seen Drag Race, those girls have a perfect pussy in their leotards but I think you will need to get rid of this before you attempt it,” Monika squeezed Alexis’ erect penis through her skirt.

Alex shuddered as she felt her sister’s fingers grip her cock through the layers of panty and pantyhose.

“Best not do that again Mon otherwise the problem will solve itself,” Alex whispered.

“Girls at school do it for boys all the time. We don’t even consider it sex. We’re just doing them a favour,” Monika softly gripped her brother’s penis through her skirt.

They were still embracing, Monika’s chin resting on her brother’s shoulder but it wasn’t her brother anymore, it was this pretty young girl who had a package in her panties and Monika found it quite erotic.

Monika had been with a plenty of boys and regularly satisfied Brad orally and vaginally and was not averse to giving him a handjob if the situation warranted it such as when they were at the movies and he pestered her for sex in the dark public place. It was a slight annoyance but it was worth it just so she could watch the movie in peace. She’d also experimented with a couple of her girlfriends when they’d had a little ecstasy and she found girl on girl sex quite pleasant and less gruelling than hetero sex but this was different.

She was caressing a very attractive and sexy girl but the girl had a penis; it was both intriguing and provocative. Alex felt like a girl, she smelled like girl, she looked like a girl but she had this protuberance under her skirt which was beguiling. She had stopped thinking of Alex as her brother as soon as she had put on her makeup. He had simply disappeared and this wonderful girl had taken her place.

Monika felt that stirring deep in her pussy that she got when she knew she was going to have sex and was really in the mood for it.

Was it wrong?

As far as she guessed Alex was a gay boy although she had never seen him with another boy. But she had never seen him with a girl either for that matter either. They shared everything but the one thing they never spoke about was sex. This was quite a dilemma.

“Alex… are you gay?” Monika whispered in her ear.

Alex didn’t answer for a while. Alex was enjoying being cuddled by her sister while she was dressed so provocatively. It wasn't the first time they had cuddled. Growing up without their parents around meant they had often found solace in each other’s embrace but this was different. Alex was dressed as a girl and sporting an erection that refused to go away and her sister had touched it through her skirt.

“I don’t know what I am Mon. I’ve never had sex. I look at the women in the magazines and online and look at your girlfriends. But I’m actually more envious of how they are dressed rather than being aroused by them. I look at boys too but I wouldn’t know what to do with one,” Alex whispered her reply.

“I’ve seen your browsing history Alex. I know that there are some porn sites you visit but I didn’t have the nerve to open them,” Monika stroked Alexis' back, holding her close.

They found comfort in each other’s arms; two sisters cuddling and nuzzling but there was an undercurrent of desire there. They were both acutely aware of Alex’s penis pressing on Monika’s belly. Monika was becoming a little wet inside her tights and her breasts were tingling. This was how Brad made her feel when she teased him before they made love, making him beg for her to lie down with him even though she had every intention of doing so.

For Alex the feelings were both baffling and delightful. Being dressed properly like a girl and taking on her latent female persona for the first time was incredibly empowering but also arousing. The breeching of the ultimate taboo, being sexually aroused by her sister was both terrifying and gratifying.

Alex kissed Monika gently on the lips. Her sister tasted sweet, her lips soft. Alex had kissed her sister plenty of times but nothing like this and they kissed again, this time crushing their lips together and Monika slipped her tongue into Alex’s mouth. Alex had never had this done to her before and it was delightful, her cock throbbed inside her pantyhose and panties and Monika felt it pulsing on her belly.

“The porn sites are all videos of crossdressed women making love,” Alex whispered.

“I don’t think I’m gay Monika but my fantasies involve me being dressed like this and making love to someone dressed the same,” Alex admitted.

“So not your sister dressed in Lorna Jane spandex tights and a crop-top?” Monika teased Alex a little.

“You feel wonderful Mon. I know what we are doing is wrong but it feels so nice,” Alex admitted.

“I think we crossed a boundary when I helped you dress like this but doing what we’re doing now is really wrong and we both know it,” Monika sighed.

“But…” Alex was about to object but Monika put a finger to her lips to silence her.

“But it feels so nice. I’ve been with boys Alex and I’ve also been with girls. Boys are usually demanding and a little rough and sometimes I like that. Girls are more sensuous and gentle and I like that too. You seem to be a combination of both and I find your virginity intriguing. If we go any further Alex we must swear to keep this secret or it will ruin us,” Monika said suddenly very serious.

Alex just nodded.

“This house is a safe space Alex; no one knows what we do here,” Monika continued.

“Yes I get it but I’m sure what we are doing is wrong,” Alex sighed.

Monika kissed Alex softly and slid her hand along Alex’s thigh, circling her fingers on the silky pantyhose. She continued upwards to the crevice where Alex’s thighs joined her torso and stroked the delicate flesh there. This drove Monika wild when Brad did it to her and she was sure that Alex would like it.

Alex did. The featherlight touch of her sister’s fingers on her upper thighs caressing her flesh through her gossamer nylons was delightful. She mimicked Monika’s actions and tentatively put her tongue into her sister’s mouth and reached down and stroked Monika’s thigh clad in the slinky lycra tights.

The ‘sisters’ gasped into each other’s mouths.

Alex had never thought of his sister carnally despite their closeness but now that she was Alexis ‘the girl’ she was a completely different person and the gorgeous creature she held in her arms was invoking feelings she had never felt before.

Monika’s fingers crept across the front of Alex’s panties and Alex shivered as she felt the soft caress of her sister’s finger’s on her panty-clad penis.

“Your knickers are wet,” Monika whispered.

“You’re making them wetter,” Alex sighed and shivered as Monika gently grasped her penis through her panties and pantyhose.

The satin panties and diaphanous pantyhose encasing her hard cock felt delightfully silky as her sister gently stroked Alex’s cock.

Monika took Alex’s hand and guided it between her legs and Alex imagined that she could feel the heat of her sister’s sex through her lycra tights. She could certainly feel the outline of Monika’s shaven mons and she could feel that her leggings were damp.

“My tights are wet too,” Monika sighed and kissed Alex deeply.

Alex clumsily explored the folds and crevices of her sister’s vulva through the sleek fabric moulded to her sex. Alex had seen vaginas before but she had never touched one and now she was touching her sister’s while Monika stroked Alex’s hard cock through her knickers and pantyhose. It was bizarre but it was delightful.

Feelings of carnal delight radiated from Monika's pudenda; she had butterflies in her stomach and her head was spinning as Alex held her tight and kissed her passionately while she fumbled with her sex. Monika felt something uniquely incredible being kissed and caressed by this pretty girl who possessed such a potent and virile appendage in her panties.

The softness of Alex’s body, the feel of her small breasts, her sleek satin blouse, the hem of her skirt tickling Monika’s wrist as she reached under it to grasp the throbbing appendage encased in satin, nylon and lycra, the scent of Alex’s perfume and the taste of her makeup was a beguiling combination. A beautiful young woman who possessed a large penis… how could Monika resist such temptation.

The fact the gorgeous young woman was her brother dressed as a girl only inflamed her desire for forbidden fruit. Alex had no idea what she was doing down there but she had somehow instinctively opened the folds of Monika’s snatch and was pressing two fingers into her cleft and rubbing Monika’s slinky tights on her labia and occasionally brushing her clitoris.

Monika softly squeezed Alex’s cock, feeling the heft of it, impressed by its girth, and she began to slowly stroke it causing Alex to moan as the silky fabric of her panties and hose grazed her sensitive organ causing another release of pre-ejaculate that soaked Alex’s already wet panties. Alex’s tongue writhed in Monika’s sweet mouth, and she held her sister tight, encouraging her to keep stroking her quivering organ. Feelings of blissful sensuality were building and Alex could feel her orgasm simmering deep inside her, waiting to erupt as she pressed her fingers deeper into Monika’s cleft.

“Oh god!” Monika gasped as Alex’s fingers grazed her clitoris through the spandex tights.

It was delightful but it was frustrating.

Monika let go of Alex’s cock and hooked her thumbs in the waistband of her Lorna Jane tights which were moulded to her buttocks and legs and forced them down her thighs and kicked them off exposing her freshly shaven pubis and long tanned legs. She took Alex’s hand and put it between her legs and wrapped her body in Alex’s warm soft embrace and kissed her deeply as she reached for her sister’s cock.

Alex explored her sister’s sex with her fingers. It was moist, warm and intriguingly fleshy, the outer folds opening to reveal smaller delicate inner folds that guarded the entrance to her vagina. She experimentally pushed a finger into the tight, sultry hole and was rewarded with a gasp from Monika and then a purring sound from deep within Monika’s chest as Alex’s thumb found Monika’s clitoris and pressed on it.

Monika pushed down on the front Alex’s underwear, bunching her pantyhose and panties down so that Alex’s erect penis sprang free. She grasped the hard sleek appendage and squeezed it and was rewarded with a mewling groan and a pulsing throb from Alex’s penis. She could feel the string of slippery pre-ejaculate dangling from the tip of her sister’s cock.

Then Monika committed the ultimate taboo.

She guided Alex’s penis to her succulent furrow and steered to the entrance of vagina.

Alex froze. The feeling of her cock pressing on her sister’s forbidden vulva was unimaginably gratifying and carnal but it was also unquestionably wrong. The warm fleshy folds of Monika’s labia seemed to lure in Alex’s phallus as they clung to her shaft. The glans of Alex’s penis was inside Monika’s vagina and her soft spongy flesh clutched at the sensitive corona. Such feelings of wonton delight and forbidden pleasure were compelling as much as they were venal.

“This is wrong Monika,” Alex whispered.

“I know Alex,” Monika replied and thrust her crotch into Alex’s and jumped up and wrapped her legs around Alex’s waist.

She clung to Alex. Her arms wrapped around her sister’s neck and her legs locked around her waist as Monika impaled herself on Alex’s long thick cock, kissing her passionately, her tongue wriggling in Alex’s mouth.

Alex felt her sister’s cunt envelop her throbbing organ, clasping at her engorged flesh. The steamy maw quivered as the concentric rings of Monika's slippery, spongy clunge seemed to milk her penis. Monika’s orgasm was shattering. She clung to her sister, pressing her body against Alex’s, wanting to feel her heart beating wildly though her blouse as Alex also orgasmed, filling Monika with a flood of hot musky seed that dribbled from her vulva and ran down her thighs.

Alex felt the most delicious raw sexually gratifying feeling well up from her engorged phallus as it throbbed deep in her sister’s tight plush vagina. Alex returned her sister’s frenetic kisses and began to thrust her cock in and out of Monika’s steamy hole.

Monika was steadily climaxing. Circlets of delight had radiated from deep in her vagina as soon as Alex’s cock slipped into her buttery cunt but when Alex actually began to fuck her, her glans pounded Monika’s G-spot and her pubis pressed on Monika’s clitoris.

Alex staggered over to the big bed with her sister clutching her, hanging on for dear life as multiple orgasms wracked her body. She lowered Monika onto the bed and began to fuck her, Alex’s cock still engorged despite having just ejaculated. The feel of the slinky pantyhose on her legs, her satin panties caressing her buttocks, the hem of her skirt tickling her thighs, the taste of her lipstick and the scent of her perfume was overpowering. Alex wondered why she had denied herself this pleasure for so long.

Monika was sobbing, her legs wrapped around Alex, her crotch rising up off the bed to meet Alex’s thrusts as yet another orgasm struck her, causing her to mew and moan and her body to shake as she felt Alex ejaculate a second time deep in her bruised, sensitive cunt. This woman lying on top her, her body so feminine and her face so pretty, while she ravished Monika with her long hard thick cock invoked a devastatingly sublime sexual sensation that she didn’t think was possible. The fact that it was her sibling only intensified the pleasure.

Alex was spent. Her first sexual encounter had been overwhelmingly resplendent. Being dressed as she was, her feminine persona appropriating Alex’s body and replacing his psyche with her own. The only vestige of masculinity being the organ between her legs with which she had ravished her sister. Alex had never felt so gratified but also so guilty.

Alex had fucked her sister. Alex still thought of herself in feminine pronouns and she felt entirely womanly but what did Monika think? Had she just fucked her brother dressed in drag or did Monika think of Alex as a woman?

It was too difficult a conversation to have and with little encouragement, Alex slipped off her heels, her skirt, blouse and bra, leaving on her pantyhose and panties and Monika shimmied out of her spandex crop-top so that she was naked.

Alex used the bedside remote to dim the lights and close the curtains and Monika went to fetch a bottle of vodka, ice and two glasses. Monika giggled as she snuggled under the covers and pulled Alex into a warm embrace. Her sister was erect again. Was she insatiable? Monika intended to find out.

Monika spent most of night educating Alex in the art of lovemaking until they finally fell asleep in the early hours.

Just before she fell asleep Monika realised the enormity of the sins they had committed and she prayed silently to a god she didn’t believe in to forgive her.


Monika Dupree sat in the cocoon of seat 1A as Qantas flight 81 thundered down the runway at Kingsford Smith Airport. She’d drunk two glasses of champagne prior to take-off and had drunk four gin and tonics in the Qantas Executive Lounge before she boarded but she couldn’t drink away her shame.

She had used the first class around the world ticket pre-purchased by her father as a graduation present and had obtained seats on the first leg of her planned journey that morning whilst Alex was still in a deep sleep. The crushing guilt of the incest they had committed weighed heavily on her. After the unbridled lust she had felt fucking her brother/sister had dissipated, the enormity of what she had done crushed her like a giant stone.

Monika had packed lightly; she would buy clothes as she travelled. She was still ghosting her friends and her boyfriend Bradley who had sent a series of phone texts and DMs on her socials alternately begging her then threatening her to let him come see her. She couldn’t face him and intended to break up with him anyway so running away without sending him any messages suited her even though she knew it was cowardly and cruel.

She would DM her girlfriends once she was in a better frame of mind. Her real concern was what to say to Alex. She had left Alex a DM telling her that she was taking a well-deserved around the world holiday and not to worry; she would send socials from each place she visited. She made no mention of their incestuous melee or of the crushing guilt she felt.

As the flight levelled out the flight attendant brought Monika a gin and tonic as requested and she only managed to finish half of the drink before she was in a deep sleep as QF 81 soared over the Simpson Desert.

Alex woke up late and lay in bed thinking about the previous day. She could feel that she was still dressed in her pantyhose and her orange satin and lace panties and a satin negligee. She could taste the lipstick on her bruised lips and smell her perfume. She could feel the stickiness on her semi-engorged phallus and smell a scintilla of Monika’s vaginal secretions.

The feeling of being totally feminine had not left her; she was still Alexis the girl not Alexander the boy in her head. She surveyed the purchases still scattered around the huge bedroom. She and Monika had not had time to put them away in their haste to feminise Alex. What followed was both surprising and amazing. Did Alex feel guilty about it? Yes; undoubtedly. Did Alex enjoy it and want to do it again? Yes; undoubtedly.

The house was eerily quiet but it was Sunday so there were no staff in attendance but Alex expected to hear Monika rattling around the house and the sound of her music. Maybe she was wearing headphones? But the place felt empty. Maybe she had gone to meet her girlfriends or Brad. How would they react if they knew what Alex and Monika had been up to? Brad would throw a fit because he was insanely jealous of Monika. But they would never know. The ‘sisters’ had sworn each other to secrecy. Both their lives would be ruined if the scandal ever came to light. Alex wondered if Monika would be up for doing it again. She definitely wanted to but she was also terrified of the consequences were they to get caught.

As teenagers are want to do, the first thing Alex did was to reach for her phone. She smiled when she saw the red acrylics glued to her fingernails; she and Monika had gone all out. Her phone vibrated when she picked it up indicating that she had messages waiting which was unusual for Alex because she was such a loner.

It was a DM from Monika and Alex was at first confused and then she had an inkling of what had really happened. Monika had always intended to go traveling during her gap year and had told Alex that the only reason she had delayed her trip was because of her concern for her brother and the need to summon up the courage to ditch Brad.

Her sister was experiencing post-coital regret which was understandable. It must be incredibly confusing for her. Monika had basically diagnosed her brother’s gender dysphoria, helped her to transform from Alexander into Alexis and then had succumbed to forbidden carnal desires. It was probably good that Monika was away from the house while she came to terms with what had transpired.

Alex however was in a completely different frame of mind. Transforming from Alexander to Alexis had freed her and given her newfound confidence and purpose. She intended to use the safe space of the Rose Bay mansion to live her life as she now believed she should. She would perfect her femininity and live full time as a young woman in the confines of the house until she was ready to announce her transformation to the world.

She shucked out of her soiled panties and ruined pantyhose and took a long leisurely shower then put some fresh pantyhose and panties and sat at the vanity and did her makeup and fussed with her hair. The expert hairdressers at Alana Kristian had given her a shag-cut that was easy to maintain but looked great. She slipped into some lycra leggings and a loose silk blouse and slipped on some cherry-red pumps and carefully walked downstairs to the kitchen to make coffee.

This was now Alexis’ house. She had it to herself and it was her domain. Of course Gloria the housekeeper would still need to keep the place spotless and Carlos the groundsman would tend to the gardens and the pool but Alex was mistress of the house.


To say that Brad Brody was pissed at Monika Dupree was an understatement. How dare she ignore him! Monika had seemed distant and distracted recently and although she had not withheld sexual congress he could tell that her heart wasn’t in it. He sensed that she was about to dump him. He knew about the around the world airline ticket that she intended to use during her gap year and he had even proposed that he accompany her on the first couple of legs of the trip but she seemed reluctant.

Brad had to spend part of the break between semesters at university working with his father at the company’s headquarters in Newcastle where one of their main shipyards was located. Brad didn’t think much of Newcastle but the small city was only a two and half hour drive from Sydney so Brad could go home for the weekends.

What really pissed him off was that he suspected that Monika was going to dump him. Not that he would be heartbroken. He had already shagged two of Monika’s close girlfriends and had his eyes on another but he wanted to be the one who dumped Monika. But before he did he wanted one last shag. Monika was pretty, had a great body and knew how to fuck. She whined when he asked her to pamper his fetish and asked her to wear sexy lingerie and high heels while they shagged but she sometimes agreed to do it to shut him up. She was a great girl but he was done with her but it needed to he who broke up with her… but not before he had fucked her in the ass which was something she hadn’t allowed him to do so far.

None of Monika’s friends knew where she was and she was not active on her socials. Brad guessed that she was holed up in her house, probably with that creepy fag twin brother of hers. Maybe he would make an unannounced booty call and then he would dump Monika before she dumped him.

Yes… that was a good idea. That’s exactly what he would do!

To be continued

101 users have voted.
If you liked this post, you can leave a comment and/or a kudos! Click the "Thumbs Up!" button above to leave a Kudos


Maybe Not So Safe

joannebarbarella's picture

Alexis may be in for a surprise and so might Brad.

In a Michele Nylons story sex always plays a huge part. I won't guess any more for fear of spoiling. Don't dawdle with the next part Michele.