Chapter 2: A Boyfriend Scorned

Brad Brody was tall, muscular, handsome and rich. These were all attributes that some girls found very appealing but along with these much desired qualities there also came a sense of entitlement, arrogance, conceit and narcissism. Brad was also intelligent, athletic and eloquent and additionally: conniving, jealous and spiteful.

He spent Sunday morning trying to contact Monika Dupree. He’d sent texts, left voicemails, trawled her socials and in desperation called her friends. No one had heard from her since Friday and she had told her close friends that she wanted to spend the weekend without interruption but she had told Brad nothing.

Brad was pissed because he sensed that Monika was about to break up with him and no chick broke up with Brad Brody; he broke girls hearts not the other way around. His plan was simple. He was going to find her, fuck her one last time, hopefully up the ass, then ditch her and then hit the socials and advertise exactly what he had done and if he could get some pictures or video of him doing so, even better.

But first he was going to join his mates at the Sydney Cricket Ground and watch his beloved Sydney Swans crush the Melbourne Demons, or so he hoped. He arrived at the ground at 1pm and joined his friends, taking it easy on the beer because of his plans for later in the day. Between quarters the handsome young studs exchanged stories of conquests made and conquests forthcoming. Every dirty detail was dissected and two bon vivants who had taken a girl high on ketamine into the toilets at a swank Sydney nightclub and spit roasted her won the competition for dirtiest deed.

Brad didn’t talk about Monika that way, nor was it expected because she was his girlfriend. The young libertines had a partisan code of conduct that they never dissed their girlfriends or female relatives but any other female was open sport. Brad did share a story about how earlier in the week one of Monika’s best friends was performing fellatio on him while he was on the phone talking to Monika.

Brad declined the offer to go across the road to the pub and celebrate the Swan’s victory saying he had a prearranged date with Monika which in a way was true. It’s just that she didn’t know about it. He went home, showered changed and took a hit of MDMA to take the edge off and jumped into his MG Roadster and hit the streets heading to Rose Bay and a date with destiny.

Alexis Dupree had spent the day practicing her makeup skills and trying on the rest of the wardrobe she had purchased with her twin sister. She tried out bold exotic makeup, subdued makeup for around the garden and pool and dramatic makeup to complement her evening wear. She mixed and matched her clothes, pairing skirts with blouses and shoes with accessories until she got bored.

She’d had only coffee for breakfast, her stomach still queasy from too much vodka the previous evening and the thought of eating anything riled her stomach. It was a beautiful day outside and she suddenly had the urge to take a swim. She stripped naked and tucked then put on a silk robe and made her way down to Monika’s bedroom. Monika had packed in a hurry, taking little but leaving a mess regardless. Clothing was hanging out of drawers and her walk-in robe was a shambles.

Alex found the drawer with Monika’s bathing suits inside it: three bikinis and two bathing suits, all designer. She selected a one-piece, shocking-pink, cotton-lycra swimsuit cut high in the legs and low in the back but with a modest neckline. It was the bathing suit Monika wore when her mother was home or when friends and family visited, the most modest suit among a collection of thongs and string bikinis.

Alex didn’t have the exact body shape of her sister but it was close. Her hips weren’t quite as wide and even though Monika had small breasts, Alex of course had none; she remedied the problem with the use of her ‘chicken-fillet’ breast enhancers.

Alex checked herself out in Monika’s mirror and was pleased with what she saw. She wished her ass was a little plumper and her tits were real but other than that she was quite stunning. The bodysuit clung to her curves, her belly was flat and her chest unpretentious, the cut accentuating her long tanned legs, her makeup was perfect for a poolside party but it would be a party of one.

Alex took a bottle of crisp New Zealand Sauvignon Blanc, icy cold from the wine chiller, a pre-chilled crystal glass and padded barefoot through the glass sliding doors, across the warm Sydney sandstone patio to the daybed beside the pool where she set up her little nest. She selected her favourite playlist, drank a glass of cold wine and dived into the warm, crystal clear pool and swam ten laps. She spent the day in and out of the pool, dozing on the daybed between dips.

In the late afternoon, having drunk all the wine and wrinkled her fingers and toes she retired to her bedroom where she took a long nap, waking in the early evening with nothing to do.

She’d dreamed of her sexual encounter with Monika. The day had started out full of promise when Monika took her on a shopping spree and feminized her brother Alexander, finally releasing Alexis from her cocoon. Then they had spoiled it by giving in to their carnal desires. Alex had enjoyed her first sexual encounter there was no doubt about it but the guilt they had both felt afterwards was crushing.

All that said, Alex was content having the house to herself. It was indeed her safe space. She was a princess alone in a palace, free to live her life as she pleased without interference. Eventually that would have to change. Her mother would finally come home or Monika would return from her travels but for this moment in time and for the near future Alex had the run of the house.

She showered and blow-dried her ash blonde hair admiring the versatility of the shag-cut as she combed out the fringe. She did her makeup, heavy on the eye makeup for the evening and used plum-red lipstick on her full lips. She desperately wanted to try on the red satin evening gown, generously strewn with sequins around the bodice. It was spilt to the hip on one side, sleeveless and low-cut with spaghetti straps. She laid it on the bed and selected the red Christian Louboutin high heels and went searching for underwear.

Alex selected a pair of nearly transparent, silky, sheer-to-the-waist pantyhose and a pair of red microfiber seamless panties which would help keep her tucked and not ruin the lines of the gown. She sat on the bed and slipped on the pantyhose, marvelling at the feel of the cool nylons on her recently shaved sunkissed legs. The pink tinge from her poolside sunburn actually looked quite lovely under the gossamer pantyhose.

She stood up and stepped into the panties and pulled them up to just above her knees and then rolled down the gusset of her pantyhose and put her hand between her legs and pushed her testes into her inguinal canals, and pushed her scrotum and penis along her perineum, carefully holding it all in place as she hitched up her pantyhose and pulled them up tight and then pulled up her panties and smoothed them out.

Alexis admired the effect briefly in the mirror before she mooched through her costume jewellery and selected an emerald choker, matching drop earrings and a bracelet. These she placed beside the shoes and checked her makeup one last time before she slipped into the evening gown. She was tempted to try to attach the silicon prosthetics to fill the bodice of the gown but she actually liked her miniscule décolletage, her own meagre breasts worked fine with the tight-fitting gown. She slipped on her heels and jewellery and doused herself with Dior Poison perfume.

Alex looked at herself in the mirror and saw a beautiful teenage princess staring back at her. Sure she was a little flat-chested but that actually complemented her aesthetic. She smiled at herself and for a fleeting moment she was a little bitter that no one else would see how beautiful she was. She carefully walked down the winding staircase to the open-plan lounge and entertainment area replete with glass walls offering magnificent views of the gardens and the pool with the vista of Sydney Harbour in the background. The pool and garden lighting had switched on automatically at sunset and Alex used the smart app to lower the house lighting, set the air conditioning down a notch and selected Monika’s playlist on the surround-sound system because her sister’s music seemed more appropriate for the way Alex felt.

She opened a bottle of Deep Eddy lemon vodka, filled an ice bucket and took a crystal glass into the lounge area, treading carefully in her high heels. She downed her first drink, a double, in one hit and then poured another double to sip. She cranked up the music and danced by herself on the Italian marble floor, content with her own company.

Brad had the security code for the gate and parked his Roadster on the sweeping driveway motor court adjacent to the four car garage. He’d tried Monika’s phone again using both text and voice but she was till ghosting him. He noticed that the house lights were dim but still burning and the pounding beat of Rihanna’s Shut Up and Drive, one of Monika’s all time faves, reverberated around the grounds.

“I hope that it’s her at home and not her homo brother,” Brad hissed as he leapt from his car.

As well as the gate access code Monika had given Brad a remote for one of the four garage doors because he had whinged when his car got rained on in the driveway once while he was visiting her. Alex used the remote to open one of the garage doors.

Monika’s red BMW 4 Series Coupé was parked in her spot as was Alexander’s black Lexus SUV and their mother’s racing green Jaguar XF. Brad smiled. Although he and Monika usually took hire cars when they went out on the town, the fact that Monika’s car was in the garage was encouraging. The connecting door to the main house was unlocked and Brad brazenly stepped inside, his ears immediately assaulted by the loud music.

He was wearing black designer skinny jeans, a flowing white muslin shirt and black Gucci’s Jordaan loafers and hardly made a sound as he entered the house.

Had Alex not been dancing to the music and a little high on the wine she had drunk earlier and the vodka she was drinking now she might have registered the alerts on the home security system when the garage door and the connecting door opened. The alarm system was not armed but was still active and the screen on the wall flashed the information whenever a door or window was breeched.

Brad followed the music along the short corridor and opened the door to the kitchen and peeked through it. The music became marginally quieter as it shifted to a ballad; more chick music that Brad hated but pretended to like because Monika did.

The bitch was home!

But not for long it looked like. She was wearing a very provocative evening gown and heels and she’d had her hair styled differently. He liked the new hairstyle and he liked the way she was dressed. His eyes immediately went to her long legs sheathed in the gossamer pantyhose. He loved legs clad in nylons and Monika sometimes humoured him and put on hold-up stockings when they fucked but despite his repeated requests she refused to wear pantyhose or stockings when she wore skirts or dresses claiming it was ‘so eighties’.

But there was something else about Monika that he couldn’t quite put his finger on. The lighting was muted and he couldn’t see her properly but her ass and tits seemed a little smaller, not much, but he noticed these things. Also her makeup was a lot heavier than how she usually wore it but he liked it.

What riled him was not knowing who this new makeover was for. She obviously had a new boyfriend or was wrangling for one because her style had changed completely and dressed as she was, she was obviously going out somewhere chic.

His anger returned and he seethed.

She didn’t know he was in the house that was for sure and he wondered if her creepy twin brother was around; he knew that her mother was overseas on one of her jaunts. Brad kept low and made the staircase without being seen and crept upstairs.

Monika’s room was a mess which was unlike her but there was no maid service on weekends so the bitch would have had to clean up after herself and that was unlikely. The door to Alexander’s room was open but the lights were out. He stuck his head inside to make sure Alex wasn’t in his ensuite taking a shit or a shower but the light to the bathroom was out too. He couldn’t make out much in the gloom but the scent of Poison perfume assaulted his nose.

“Fucking fag!” Brad hissed under his breath assuming that Alex was using some faggy aftershave or cologne.

Assuming that Alex was out, Brad made his way downstairs determined to confront Monika and hopefully wrangle one last pity-fuck out of the bitch before he dumped her, even though it was obvious that she had for all intents and purposes dumped him.

Alex was dancing in a circle, her arms across her chest, imagining that she was dancing with a partner who was holding her close and whispering endearments into her ear. She had no idea who this partner was or what gender; they were simply an amorphous being who filled the void of Alexis’ solitude.

Brad stood at the bottom of the stairs and watched his girlfriend dance by herself. She was beautiful. This demure eighteen year old girl who looked stunning in the red satin dress that clung to her lithe body, the split opening wide to expose her legs from ankle to thigh. Her legs were long, shapely and sheathed in gossamer. Her face was strikingly attractive. Her eyes were closed and Brad could see the full effect of her heavy mascara, eyeliner and eyeshadow; her exquisite cheekbones highlighted with rouge, her full lips coated with glossy red lipstick.

What irked Brad was that this was how he wanted Monika to dress but she refused to do so. At school she plied on the makeup and wore her skirts short and nylons sheer in an effort to push the boundaries in an act of teenage defiance and rebellion but outside of school her style was more subdued.

Brad was becoming concupiscent as he jealously watched Monika dance with herself. She stopped briefly to take a gulp of vodka, barely opening her eyes, and then she continued to dance. If he knew that Monika had this particular aesthete inside her all this time, Brad may have considered keeping their relationship intact; indeed it would have rekindled his passion and his devotion for her.

But this was all for someone else. He wondered how long it would be before her suitor called by or the chauffeur of her hire car pinged her mobile. It was time to act.

Brad stepped into the spacious open plan room with its black Italian tiled floor, white leather recliners and blonde on blonde Scandinavian design furniture. The room was as soulless as Susan Dupree who had overseen every aspect of decorating the huge waterside mansion but seldom lived there. The stark monochrome was a perfect background on which to capture the vibrant tones and pigments of Alexis’ red dress and the intense tinctures of her makeup and hair.

“What the fuck Monika!” Brad screamed out over the music.

Alex came out of her reverie, startled and confused. The lights were dimmed but she recognised Brad Brody as soon as she saw him. She was stunned.

“I’ll say it again ... What the fuck Monika!” Brad’s voice was not quite as loud now that he had her attention.

He snatched up the remote for the home automation system and turned off the music.

Alex stood in the middle of the room clutching her crystal glass to her chest. She was in a total panic but unable to move. A thousand thoughts ran through her head the primary one being that Brad thought that she was Monika. She knew the misconception would not last long and that she would be outed by a man she loathed.

It was a fight or flight situation and Alex chose flight.

She dropped her glass and bolted for the stairs and likely would have made it except for her high heels skittering on the marble floor and the fact that Brad played on the wing for the Sydney University Football Club and his speed was legendary.

He caught Alex around the waist and drove her onto a plush white leather divan and lay on top of her. She looked up at him, her green eyes filled with fear. Brad felt her body trembling beneath him. Monika didn’t quite feel the same but she felt nice. Her breath was sweet with the scent of lemon vodka and her perfume was exotic; something he had not known Monika to wear but something he had recently smelled.

She was like a fawn that had been taken down by a lion: small, quivering and frightened with big beautiful eyes and a pretty face. He could feel her heart racing and her heavy breathing.

Brad lowered his face to Alexis’ and put his lips on hers.

He kissed her and Alex let him. She didn’t know what else to do. She was stymied, dazed and confused.

Her lips were soft and her breath was sweet and Brad slipped his tongue into her mouth and she made no move to stop him.

It was then he realised that something was wrong.

Monika was not at all embarrassed about being small chested. All of the latest supermodels had small breasts and Monika slipped into the latest couture as easy as they did. But ... she did have breasts and she was proud of her petite 30B’s. Brad had stroked and suckled them often enough to know that they were pert, round and bell shaped, being fuller at the bottom.

This girl had nothing more than chest bumps with nipples.

Brad was a conceited narcissist but he certainly wasn’t stupid. He realised who was lying beneath him as soon as he realised that she had no breasts. His rational mind told him that he should stop kissing this faggot immediately and give him the beating he deserved for masquerading as Monika but the primitive part of his brain kicked in.

The girl lying beneath him felt wonderful, her satin-sheathed body was moulded to his. He knew that her legs were long and shapely and just to confirm it he slipped a hand inside the split in her dress and stroked her silky gossamer-clad thigh. She was as pretty if not prettier than Monika and there was something about her when he had watched her dance that awoke a yearning he hadn’t felt for some time: a sense of renewed excitement.

Brad kept kissing Alex as much to see how she would respond as anything else. She had tensed up when he put his hand inside her dress so he removed it. He stroked her hair as he continued to kiss her softly, the tip of his tongue gently exploring her mouth.

Alex was bewildered. She guessed that by now Brad had figured out that she was not her twin sister Monika and yet he continued to lie on top of her and kiss her. She had expected him to beat her because he was embarrassed by being misled into thinking she was Monika and also she knew that Brad disliked Alexander intensely. It was one of the many reasons that Monika intended to dump him.

And Alex hated Brad in return. Yes Brad was handsome, articulate and moneyed but he wasn’t good enough for her sister; she found his narcissism repellent. Alex felt totally vulnerable, expecting to be beaten or at least outed and mocked by Brad Brody.

But...

She had to admit that having this ruggedly handsome young man lying on top of her, menacing her, kissing her without her permission, was somewhat exciting. She had felt nothing but feminine since she had transitioned from Alexander to Alexis but now she also felt effete.

Alex had little experience of kissing and being kissed and most of that had come from the incestuous encounter with Monika which was something they were both still trying to come to terms with but Brad’s soft kisses were beguilingly sweet and yet at the same time masculine and dominant. She felt vulnerable but she also felt something else; she also felt avidity for what he was doing to her, how he was treating her. He was treating her like a woman.

As abruptly as Brad had started to kiss her, he stopped.

“Where is Monika?” Brad hissed; his face inches from hers.

“I don’t know,” Alex whispered.

She had been practicing her femme voice all weekend but she didn’t need to force the inflection. She was so scared that her answer came out as a squeak.

“Don’t lie to me Alex,” Brad slipped his hand inside her dress and squeezed her thigh.

Alex gasped and wriggled like a hooked fish but Brad pressed his body into hers and she could feel that he was becoming concupiscent, his package pressed against her stomach.

“She’s in Singapore by now, on the first leg of her holiday,” Alex stopped struggling and couldn’t help but feel a little schadenfreude at the look of disappointment on Bradley Brody’s face.

“I was supposed to go with her,” Brad sighed, his anger temporarily forgotten.

“I know. She’s ghosting everyone. She has issues that she wants to deal with alone,” Alex replied telling a half-truth and wondering why she was even bothering to explain anything to this dolt.

Brad suppressed his rage as it began to roil again. There was nothing he could do to Monika now that she had escaped his clutches but he had Alex to play with.

“So what’s your story Alex? Why are you dressed like this? I always took you for a faggot but I would never have guessed that you were a crossdresser,” Brad made no effort to climb off her.

“Let me up and I’ll tell you,” Alex smiled up at Brad, hoping to charm him a little.

“I don’t think so. I quite like it here. You don’t have all of Monika’s bumps and humps but you feel kinda nice and you’re prettier than she is,” Brad grinned down at Alex; the compliment clothed in menace.

“I’m trying to find the real me if you must know. I don’t know if I’ll transition; it’s too early to say, but I feel more comfortable presenting as a woman; presenting myself as Alexis Dupree and leaving Alexander Dupree behind. This is all new to me,” Alex blurted out and immediately regretted it.

Why tell a man she hated her most intimate secrets?

“Well you certainly look the part. I thought you were Monika right up until I was kissing you,” Brad chuckled but there was no mirth in it.

Alex blushed.

“Can I get up now please?” Alex whispered.

Brad lowered his face and placed his lips against Alexis’ and softly kissed her. Alex froze, not knowing how to respond.

“Kiss me back and I’ll think about letting you up,” Brad broke the kiss and smiled at her, his deep brown eyes actually showing some affection.

“I’m not sure if I’m ready for that yet,” Alex demurred.

“Come on. One little kiss and I won’t tell everyone that you are a homo, skirt-wearing faggot who takes it up the arse,” Brad smirked.

Alex was appalled. She didn’t really have any friends but she had acquaintances and Brad had met some of the Dupree family including their parents Susan and Francis Dupree at one of their rare family get-togethers. There was the family name to consider. Alex had thought about coming out openly eventually but only after she had come out to her mother and father first. Brad was vindictive and was likely to embellish the story, making Alexis out to be some sort of sexual deviant.

“Why Brad? You know who I am and you have always hated me,” Alex relied defiantly.

“I don’t like Alexander Dupree but I kinda think Alexis Dupree is hot,” Brad winked at her salaciously.

He lowered his mouth to hers again and this time Alex responded; tentatively at first. Brad kissed her sensuously and when his tongue began to explore her mouth she slid her tongue into his. This was so different to kissing Monika. Monika’s kisses were soft and feminine even when they were engaged in full-blown lust. Brad’s kisses were manly and a little insistent but not overly so. She could smell his aftershave and his muscled body pressing on hers. She could feel the bulge of his cock through her gown.

It both terrified and excited her. She wanted him stop but she also wanted him to continue.

Brad was also feeling perplexed. He’d fucked plenty of young women and even a few matrons; he had an eclectic taste when it came to women and he had once won the dirtiest deed competition by fucking one of Monika’s girlfriends and then the very next evening fucking the same girlfriend’s mother. He’d been tempted once by a transgender woman he met at the Stonewall Hotel on Oxford Street but had chickened out.

He would easily win the bet for dirtiest deed of the week if he fucked Alexis Dupree but it could backfire on him. Alexis was not out as a transgender woman and his friends might accuse Brad of being a fag for fucking ‘a boy in a dress’. There was also his plan to finally fuck Monika in the ass and slut-shame her on their socials after they broke up but that opportunity had been taken from him. Was Alexis a suitable substitute?

He pondered all these things but what he couldn’t suppress was that he actually found Alexis attractive and alluring. There was something about her. Not just her beauty and femininity. She was demure and reticent, unsure of herself and vulnerable.

When Alex began to return Brad’s kisses he did not think of Monika’s brother whatsoever; he thought only of the lovely creature beneath him who had a striking resemblance to his ex-girlfriend but who was uniquely beautiful and feminine in her own way.

Her mouth was sweet and her satin gown slithered on her lithe frame whenever he moved above her. He would like to feel the cool silkiness of that gown against his naked flesh. His hand strayed to the split in her dress and rested just above Alexis’ knee. He gently caressed her nylon-sheathed limb, the slinky diaphanousness of her pantyhose felt delicious and inviting. His cock began to uncoil like a snake awakened from its slumber.

Brad’s kisses were exciting and instinctively Alex draped her arms around him. She stroked the hard muscles of his biceps through his muslin shirt with her fingertips. This too was an instinctive reaction; a response to her bourgeoning femininity and her ingrained need to feel wanted.

When Brad’s fingers began to caress her leg at first she froze but his kisses were becoming fervent and his fingers circled her thighs just above her knee where they illicited wonderful little sparks of delight which she relished.

Was this as wrong as fucking her sister? Not anywhere near it but Alex still couldn’t shake off the fear that she was committing a sin. Brad was technically still Monika’s boyfriend as neither of them had formally broken off the relationship and there was also the fact that Alexis was still wrangling with her gender issues. There was no doubt that at this moment in time that she wanted to be a young woman but what if that sentiment changed? There was also the issue of being sexually active with a man. Did she really want to do this so early in her transformation?

Brad answered that question for her when his fingers began their journey up her thighs, exploring her pantyhosed limbs and stirring feelings of delight as he softly caressed her slinky nylons. She felt herself becoming tumescent; uncomfortably so. She gasped into Brad’s mouth when he reached the top of her thigh and his fingers caressed the crease where her legs joined her torso.

Brad decided to throw caution to the wind. He was sexually charged, having intended to fuck Monika and the MDMA had increased his libido. He was alone with this lovely young trans woman who was presenting exactly the way he wanted his girlfriend to do but wouldn’t. Why not take advantage? There would be no witnesses and Alexis was such a novice that she would hardly know what to do or what to say to whom if he pressed his needs on her.

Stroking her pantyhosed legs and feeling her satin gowned body against his was charging Brad’s sex drive and he kicked off his loafers and broke their kiss momentarily to take off his shirt. Alex was disappointed when he stopped kissing her and she had to admit that she was probably more disappointed that he had stopped playing with her legs.

The removal of shirt and shoes did not take long however and the two timid lovers, if that’s what they were, took up where they had left off. Alexis opened her arms and invited Brad to kiss her and when he did she wrapped her arms around him. While Brad was taking off his shirt Alex had surreptitiously snaked her hand inside her pantyhose and untucked her penis and allowed her testes to descend back into her scrotum. She was no longer uncomfortable with her penis flat against her stomach held there by her pantyhose and panties.

Brad was so hard that it hurt; his penis was confined by his trousers and he needed to release it but once he did that he was committed. He was no longer just teasing this pretty tranny; he was fully culpable of engaging sexually with her.

“You better not tell Monika! You better not tell anyone!” Brad hissed as he struggled with his trousers.

“Tell anyone about what? We haven’t done anything wrong,” Alex bleated; annoyed that Brad would think her a gossipmonger.

“Don’t tell anyone about this,” Brad smiled down at her salaciously and placed his penis on her thigh.

“Oh my!” Alex was just able to exclaim before Brad closed his mouth over hers.