A Safe Space - Chapter 3

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Chapter Three – Lady of the House

Carlos was well aware that Alex had watched him masturbate in his workshop. When Alex had moved the bougainvillea out of the way, the light from the window became brighter. He had considered stopping what he doing but then decided to see how it would play out, besides he was close to coming and he needed release.

It was Alexis’ fault that he was masturbating anyway. Carlos’ wife was a strict Catholic who believed that sexuality is a gift, but sex acts are only allowable between heterosexually married partners and each act must be both loving and open to procreation. Carlos had no interest in bringing any more than the three kids they already had into the world and his wife rationed sex like it was priceless.

Carlos’ sexual gratification came from his encounters with Gloria. Her husband had just about given up on sex but she still had a very active sexual appetite and fucking Carlos at work while the house was empty, which was most of the time during the day, was convenient, discreet and satisfying. Now that Alex was home all the time Gloria was reticent about having sex on the Dupree property.

They had managed a couple of quickies when Alex made her very infrequent ventures outside the residence but Carlos was frustrated

That, plus Alexis’ coquettish behaviour was the reason Carlos was constantly sneaking away to the toolshed to masturbate. Knowing that Alex was watching him piqued Carlos’ fervour. The girl in the cheesecake magazine he was looking at resembled Alexis’ which was why he had taken it from the rack in the newsagent. When he spattered his issue all over the centrefold he imagined that it was Alexis’ face he was spattering his spunk over. Knowing that she was watching him made his orgasm even more satisfying.

When he left the toolshed he noticed little puddles of semen on the sandstone path and another gobbet dribbling down a leaf in the garden. The dirty little tranny bitch had whacked off while she was watching him.

Carlos wasn’t sure at first if he found that exciting or repulsive. He found Alex very attractive in a Lolita kind of way but of course he knew that she was eighteen and legally an adult, but knowing that she had male genitalia hidden inside her swimsuit and under the little pleated skirts that she liked to tease him with was disturbing. What he knew right now was that despite having just masturbated, knowing that Alex had watched him and had masturbated herself whilst doing so aroused him intensely.

He strode to the house, walking around the edge of the flagged patio. Alex was lying on the sun lounge fresh out of the pool, her white swimming suit clinging to her body. Her little titties, long tanned legs, ash blonde hair and pretty face behind her sunglasses were a distraction and made Carlos more resolute. Gloria was putting out Alexis’ lunch when he called to her in Spanish and told her that he needed her to come with him.

They had a short heated conversation in Spanish so that Alex wouldn’t eavesdrop and Gloria relented and told Alex she was going shopping briefly with Carlos. Alex just sipped tea and seemed disinterested in what the hired help were up to.

“Where are we going? You are acting crazy!” Gloria said a little excitedly as they drove through the gates.

“I am crazy. There is the little travestida lying around in her swimsuit all day or strutting around in little skirts and heels, then there is you with your big sexy ass, long legs and big tetas wrapped up in that sexy uniform and I’m getting nothing!” Carlos slammed his hand on the steering wheel.

“You fancy the little travestida?” Gloria said with some amusement.

“I fancy you Gloria but we can’t fuck at work and we can’t meet outside of work,” Carlos was taking New South Head Road heading towards South Head away from any of the businesses they usually frequented.

“Where are we going Carlos?” Gloria asked.

“We’re going to fuck,” Carlos growled.

“There are no motels around here,” Gloria sniped when Carlos turned onto Hopetoun Avenue.

“We’re not going to a motel or a hotel. It would be obvious what we are doing arriving in a motel in the middle of the day without luggage and besides I can’t afford a hotel around here,” Carlos followed the bends of Hopetoun Avenue past more mansions and luxury apartments.

He turned onto Military Road and finally Cliff Street where he turned into the car park adjacent to Camp Cove. He reversed into a space in the furthest corner of the car park where the car was shielded by gum trees and coastal scrub on three sides.

“What are we doing here Carlos?” Gloria sounded very perturbed.

Carlos ignored her and put the sunshade up to cover the windscreen. He left the engine running and set the air conditioning on high and jumped out of the F-150 and slammed the door. He walked around to the front passenger door and half dragged Gloria out of the car.

“Carlos! What are we doing here? This is crazy!” she whined when Carlos opened the door to the rear cabin of the twin-cab utility.

“I told you what we are doing here,” Carlos growled as he pushed Gloria onto the back seat and climbed in after her, locking the doors.

“This is madness!” Gloria cried but her cries were stifled when Carlos pressed his lips to hers.

His hands went to her breasts and kneaded them through her pink polyester–cotton box dress uniform. He slipped his tongue into her mouth and Gloria stopped struggling. She too was sexually frustrated and although the circumstances were not ideal she was prepared to let Carlos have his way with her. It was exciting being in the back of the cab, canoodling in broad daylight in a public car park. It reminded her of her youth.

Carlos managed to get three of the large white buttons on the front of Gloria’s tunic open and he lifted her heavy breasts free of her bra cups. He put his face to them and suckled her big fat nipples which hardened to his touch. Gloria gasped as rings of pleasure emanated from her breasts.

It was uncomfortable in the back of the twin-cab but Carlos did the best he could. In between kissing her passionately and sucking on her big breasts Carlos managed to ease Gloria down on the bench seat while he straddled her. He kissed her passionately and Gloria fumbled at his flies until she freed his huge cock which was already distended and dripping pre-ejaculate. She hefted the girth of it in her hand and enjoyed the feel of his masculine appendage that was so much bigger than her husband’s useless little acorn. She missed feeling its ponderousness, the very magnitude of its latent power.

Time and childbirth had not been kind to Gloria’s vagina but when Carlos put his ‘polla’ inside her it filled her and made her feel like a girl again. She was getting wet and impatient as Carlos kissed her and mauled her teats. She wanted him inside her.

She pushed him away and began to unbutton her dress.

“What are you doing my love? We don’t have the time and this isn’t the place to get undressed,” Carlos said as he pushed his shorts down to his knees and ripped open his work shirt.

“What then?” Gloria looked up at him impatiently, her red lipstick smeared around her mouth.

“This,” Carlos grinned at her and spread her legs and lifted them up.

He pushed her dress out of the way and quickly admired her white nylon granny-panties that for some reason turned him on. He pulled the gusset of her panties aside and revealed the dark coffee coloured crotch of her control-top pantyhose and snagged a fingernail next to the seam and ripped them open.

“Oh Dios mío!” Gloria yelped as Carlos probed at her fleshy labia.

“Here let me,” she slapped his hand out of the way and took his rampant member in her fingers and guided it to her steaming cooch.

The head of Carlos cock slipped inside her warm wet opening and then he thrust it all the way in.

“Good boy!” Gloria sighed as Carlos’ steely phallus filled her steaming maw.

There was no time for gentle leisurely lovemaking. Carlos jackhammered his cock in and out of Gloria’s vagina and she mewed and moaned as he fucked her. She had missed this so much and she kissed him passionately and rubbed her pantyhosed legs on his flanks because she knew he loved the feel of her nylons on his skin.

Her cunt felt distended by Carlos’ huge cock and his pubis was pressing on her clitoris bringing her close to climax. Her vagina clung to Carlos’ meaty appendage as he drove it in and out of her; he loved the feel of her fleshy ‘coño’. His wife’s cunt was so much tighter but he seldom got to use it and whenever he did she complained. This mature woman with her earthy beauty was far more desirable to him although for a fleeting glimpse he thought of Alexis Dupree as his orgasm approached.

“Yes! Yes! Yes!” Gloria moaned like a slattern as her orgasm exploded, rings of pleasure expanding outwardly from her clitoris and her g-spot as Carlos pounded her into the seat.

She scissored her legs, rubbing her nyloned thighs on Carlos’ sensitive skin as her cunt clutched at his throbbing manhood. Carlos grunted and roared as his cock suddenly quivered and erupted, filling Gloria with his seed. Despite having masturbated not that long ago his spend was prodigious and Gloria felt him fill her with his seed.

She could feel him ejaculating inside her as he clung to her, kissing her almost violently. She wrapped her arms and legs around him and held him tight as his orgasm peaked.

They couldn’t lie together in post-coital bliss. It was too dangerous and as soon as they had both descended from their orgasmic highs they began the awkward task of dressing in the confines of the back of the utility. Gloria’s crotch was sodden and Carlos’ semen dribbled from her snatch. Some of it soaked into her pantyhose and the rest was absorbed by the crotch of her high waisted, full brief nylon panties. She would change them back at the house along with her pantyhose. She kept spare underwear in her handbag which she had left at the house.

She put away her breasts and adjusted her bra and buttoned her dress while Carlos buttoned his shirt and pulled up his khaki King Gee work shorts. He opened the door and looked around. A young couple dressed in wetsuits were attaching their surf skis to the roof rack of their SUV down the other end of the car park but otherwise the car park was void of people.

Carlos hopped out and helped Gloria step down. He pulled her into his arms and kissed quickly.

“Thank you mi amour,” he whispered in her ear.

“No thank you. I needed that,” Gloria grinned up at him as she adjusted her uniform.

She fixed her makeup using the sunvisor mirror during the ride back to the Dupree house. Her knickers felt squidgy but it felt kind of nice; kind of naughty and reckless.

When they parked in the motor court in front of the four car garage they grinned at each other and Carlos let Gloria go ahead into the house where she heard music coming from Alexis’ room. She grabbed her large handbag and scurried away to the staff toilet where she took off her knickers and pantyhose, washed her privates and replaced them with fresh underwear.

Later that day she snuck down to the toolshed and left her soiled pantyhose and panties on the workbench as a present for Carlos. She frowned when she saw the magazine opened at the centrefold where a cute teenage girl posed in a swimsuit with her legs spread. The young girl looked disconcertingly like Monika or Alexis Dupree and the page seemed to be marred by some sort of liquid stain. She decided it was best to say nothing and after taking one last sniff of the pungent aroma of Carlos’ semen on her panties she left the toolshed and closed the door.


Time passed slowly at the Dupree household. Twice a week Carlos and Gloria would make an excuse to drive to a secluded spot usually in parkland or a quiet car park and fuck in the back of Carlos’ utility. When Gloria couldn’t get away and Carlos was horny he would lock himself in the toolshed and whack off, usually thinking about Alex Dupree, looking at pictures of young women he found in magazines that looked like her because she continued to tease him in her tight white bathing costume or little skirts, nylons and heels, her makeup always alluring.

Monika was up on her socials. The online war with Brad Brody was over and they ignored each other. Monika was having too much fun in London to worry about Brad. She kept in touch regularly with Alex and asked how her transition was going and Alex sent her pictures which Monika dutifully commented on stating that Alex looked beautiful and promised to keep them secret. They did not talk about their incestual encounter.

Susan Dupree was ensconced in her Nusa Dua beach house in Bali with a German she had picked up in a nightclub in Kuta. He was a penniless backpacker but he was brutally handsome, had a big cock and knew and how to use it and was young enough to be her son but she didn’t care. She checked in with Monika and Alex once a week by phone but Alex had not yet come out to her as trans. She decided that it was something that needed to be done face to face.

Brad Brody was bitter about the breakup with Monika but was more concerned about his growing infatuation with Alexis Dupree. Initially he’d been disgusted with what he had done with her and wondered if he was some sort of faggot. He knew that he wasn’t and he was busy warring with Monika trying to pity fuck those girlfriends of hers that he hadn't fucked already but there weren't many. When the war was over he wondered if his fascination with Alex was because she looked identical to Monika but deep down he knew that wasn’t the case. Alex was uniquely beautiful in her own right.

He was also terrified that Alex was going to out him for having sex with her, especially if she chose to come to the defence of her sister, but Alex remained detached from Brad and Monika’s breakup. Brad was also aware that Alex would have to out herself as a trans femme to do so and she had confessed to Brad that she was too early in her transition to be confident enough to come out.

Having worked his way through all of Monika’s girlfriends who would fuck him Brad tried fucking his way around town to get Alex Dupree out of his mind but it wasn’t working. Every time he kissed a girl he imagined Alexis’ soft lips. Every time he held a girl against his body he remembered holding Alex in her satin evening gown. The part about her having a penis he somehow rationalised away, he just remembered coming inside her panties, rubbing his cock on her pantyhosed pubis with her silken limbs wrapped around him.

He became addicted to watching tranny and crossdresser porn online whilst masturbating into silky pantyhose and it brought him relief for a little while but it also fuelled his desire for Alex.

As for Alex, she too had been watching a lot of crossdresser porn online and was getting adventurous with her vibrator until one day she actually inserted the tip of it into her anus which produced an amazing orgasm. The next time she tried it she put it in all the way and found her prostate gland and the effect was amazing. Extracting the plastic vibrating penis from her anus afterwards she realised that she needed to learn how to douche and she bought herself a douche kit at the same adult store where she had purchased the vibrator.

On the rare occasions that she ventured out Alex was presenting more and more femme. She wasn’t quite up to going out in skirts and heels but she wore lycra leggings, crop tops and sandals. She wore eyeliner and pink lipstick, perfume and a little too much jewellery. She was very androgynous and was aware that some people were staring at her and that some boys and older men were giving her appreciative glances. She liked being appreciated but it made her extremely nervous and reinforced to her that she was not yet ready to be openly out as a transgender woman.

‘Have you told anyone?’ Alex received a DM from Brad on her Twitter.

She had wondered if he would ever contact her again and was amused.

‘Told anyone what?’ Alex replied.

‘Don’t be coy – you know what I mean!’ Brad’s well known temper was already beginning to flare.

He knew inwardly that his self-justification for contacting Alex was really just an excuse to engage with her again. Yes he was terrified that she would come out openly as trans and tell someone what she and he had done. But… he remained besotted by her.

‘I think it’s a conversation we should have face to face.’ Brad’s fingers were sweating as he typed the text into his iPhone.

Alex tapped a manicured fingernail against her brilliant white teeth and considered Brad’s proposal. She suspected that Brad was using it as an excuse to see her again and possibly to engage in sexual congress. Had she liked what they did last time? There was no doubt that she did but was it appropriate to do it again?

There was no doubt that Brad was a shit. He’d vilified her sister online although Monika had won that battle. He’d pretty much forced himself on Alex but she’d submitted to his advances pretty easily and then he’d regretted doing so and threatened her not to tell anyone.

That said he was incredibly handsome and she had enjoyed their tryst. She was also safe and secure in the knowledge that there was no way Brad was going to tell anyone who she was and what they had done. This was her safe space and she was in control.

‘I agree. Come here tonight at 9pm.’ Alex texted back.

‘Ok but don’t tell anyone I’m coming.’ Brad replied nervously.

‘AS IF!’ Alex typed her response and logged out of twitter.

She dropped her phone on the bedspread and considered what she had just done. Was it foolish? Probably yes. Was it dangerous? Definitely yes. Was it exciting? The bulge in her panties answered that question.

That evening she showered, did her makeup and then decided what to wear. She wanted to wear something dramatic and sexy; something that was fashion forward and sophisticated. She wanted to demonstrate that she was a smart young woman, not some ditzy teenager. Teasing Carlos was quite pleasurable and she liked the dynamic of it. Teasing Brad would probably be even more pleasurable because there was always the possibility that she might give in to her desires if he was insistent and she was in the mood.

She’d popped an eccy had been drinking wine steadily all evening and had a nice buzz going. Alex stepped into a bustier which was overlaid with red satin and trimmed with black lace. She put on a pair of red satin panties and slid her legs into the black fifteen denier fully-fashioned stockings, marvelling at the feel of the diaphanous nylons as she pulled them up her legs and fastened them to the suspender straps.

There. The sexy part of was done; now for the sophisticated. Alex took the black V-neck ribbed-knit long-sleeved dress with embossed gold-tone buttons, shoulder pads and two front welt pockets from her wardrobe and admired it.


She put it on and immediately felt more adult and refined. The dress was cut short and displayed her long legs sheathed in the gauzy black nylons to their full effect. The hint of red satin bustier visible between the lapels complemented the black dress perfectly.

She accessorised with costume jewellery, doused herself in perfume and slipped her feet into her highest heels. The headlights of Brad’s car flashed across the curtains as he drove down the driveway and parked in the motor court. She heard the car door slam as she made her way carefully down the staircase.

Alex watched the security system monitor and saw Brad trying to use his remote to open the garage door to let himself inside as he done the last time he had come to the house. Alex had had Carlos change the code on the garage doors so Brad’s clicker was useless. She smiled to herself and when he tossed the remote away and made his way to the front door and pressed the door chime.

Alex opened the door and Brad was met with miasma of perfume. He took in how Alex as dressed and swallowed hard; it was amazing how much Alex looked like Monika but that dress, those nylons and those heels! Monika would never dress that way. Brad looked at Alex appreciatively and Alex stood in the doorway and let him; unconsciously posing like a model.

“Yes sir; may I help you?” Alex smiled cheekily at him and Brad returned her smile.

“You know why I’m here Alexis,” Brad said.

Alex appreciated that Brad used her full name but she was not letting him off that easily.

“The last time you were here you said that quote: you and your fucking sister are fucking dead to me! I never want to see either of you again, unquote. Then you bullied Monika online,” Alex tapped her toe.

Her arm remained extended across the door preventing Bradley from entering.

“She gave as good as she got!” Brad bristled.

“Oh I’d say she did better than that Brad. I’d say that she outed you for the philandering little shit that you are,” Alex grinned at him.

“You should talk! She’s your sister and you let me… you let me…” Brad trailed off, his face red with embracement.

“I let you what Brad?” Alex gave him a coquettish smile.

“You let me kiss you and stuff,” his embarrassment escalated.

“And stuff? I think you were the one who forced me to do the ‘and stuff’” Alex was having fun teasing Brad.

“Are you going to let me in?” Brad whined.

“Are you going to behave yourself?” Alex teased.

“Yes of course!” Brad’s temper flared.

“Well in that case I’m not letting you in. Where’s the fun in that,” Alex made to close the door, enjoying the shocked look on Brad’s face.

She started to laugh and opened the door wide.

“Of course you can come in Brad. I was just fucking with you,” Alex beckoned him inside.

She could see the emotions churning on Brad’s face. He was not used to being messed around with by women. It was he who monkeyed about with them! But she could also see that Brad was besotted with her. He hadn't stopped looking her up and down since he had arrived. She stepped aside to let him in.

Brad followed Alex into the open-plan lounge, all the time staring at her legs, sheathed in those gorgeous black stockings with the seam running up the back of them. He knew that they were stockings not pantyhose because he could see the gauzy welts every now and then because Alexis’ dress was so short. He also checked out her ass. It wasn’t as plump and rounded as Monika’s but it was still magnificent and that dress clung to her buns.

“Drink?” Alex pointed to a white leather four-seater and indicted Brad should sit.

He sat down and nodded and contemplated what his next move should be. Brad was nervous and that was unlike him. He was usually confident and commanded the conversation but there were so many questions and so many thoughts churning in his brain.

Alex was making drinks at the bar. He found her beguiling and so different to her male alter ego. She was confident, sophisticated and articulate; all the things that Alexander was not.

“So this is you now? I mean this how you’re going to live now? I mean… shit… I’m sorry… I mean you have transformed into this other person,” Brad stumbled and fumbled as he tried to make conversation.

Alex smiled at him and walked over to the settee carrying the drinks. Brad noticed that she had long acrylic nails painted blood-red to match her lipstick. She handed him a drink and sat down beside him, smoothing her skirt under her in a very ladylike way. Brad noticed that she seemed even more naturally feminine than the first time he had met her. She seemed very comfortable in her new skin.

“I told you Brad that I have yet to make up my mind as to how far I intend take my transformation. I don’t know if I’ll alter my body or not but as I said to you before I feel like who I'm destined to be when I’m presenting as Alexis. There is no part of Alexander left inside me except his intellect,” Alex explained.

“And besides me, only Monika knows about this? What about your gardener and housemaid; they are here all the time?” Brad sounded anxious.

“Gloria and Carlos know but no one else does. And what are they going to say and who are they going to say it to? They are well paid loyal servants and know that the Dupree family has the power to see that they never work again if they cross us but we’d never use that threat openly of course,” Alex explained.

“You know you look so much like Monika but you're so different too. You really are beautiful,” Brad grinned at her bashfully.

“Well thank you for the complement,” Alex extended her drink and they clinked glasses.

“And you haven’t told Monika about what we did?” Brad’s cheeks burned deep red.

Alex sighed; she’d rather not have this conversation. Besides if Brad knew what she and Monika had done, her little dalliance with Brad would pale into insignificance.

“Brad I stayed out of your online war with Monika. You know that. I want anonymity so why would I tell anyone about our… encounter. Your secret is safe and you can regret that it ever happened knowing that nobody knows that it did,” Alex took a sip of her gin and tonic.

“I didn’t say that I regret that it ever happened,” Brad’s cheeks were burning again.

“You regretted it instantly. You called me a faggot and threatened me,” Alex said dryly.

“I know and I’m sorry. I was confused. I was stupid. I was homophobic and transphobic,” Brad sighed.

“Yet you are still terrified that I will tell someone what we did,” Alex smiled at him a little snarkily.

“It’s because you're Monika’s sister,” Brad protested.

“Brad. You’ve been fucking Monika’s girlfriends. Even when you two were together you were fucking her girlfriends so why would it make any difference if it got out that you had also fucked her sister? Isn’t that what you and your friends do at the footy? Swap stories about who has committed the most heinous act on a girl? Fucking your girlfriend’s sister would be right up there I reckon,” Alex took another sip of her drink and drilled Brad with her stare.

He put his head in his hands and studied his feet.

“Monika told me about your ‘dirtiest deed’ contest. Admit it. You couldn’t tell anyone because I’m trans and you're worried they'd call you a homo,” Alex said, a little triumph in her tone.

“But you want anonymity anyway,” Brad countered.

“Yes that’s right. But you didn’t hold back to protect me, your held back to protect yourself,” Alex whispered.

“Brad raised his head and gazed into Monika’s emerald green eyes and felt himself drowning in them.

“You really are beautiful. I can’t stop thinking about you. I can’t stop thinking about what we did. It turns me on so much,” Brad admitted.

“Yes I was churlish and said those horrible things last time I was here but that was because this is all new to me. I’ve never been with a trans girl before and I panicked. I thought I was somehow punishing you. Using you to get back at Monika but now I realise that I fucked up the opportunity to be your friend,” Brad sighed.

Alex couldn’t help but laugh.

“You popped my panties Brad. We didn’t fuck. You’re not gay. Yes I liked what we did but I’m not besotted with you. You are simply the first boy I have ever been with,” Alex said coolly.

“And you don’t want to be my friend Brad. You’re back here for more of the same, admit it,” Alex patted his knee.

“Well I guess both things are true,” Brad couldn’t help but smile.

That smile had broken many a girl’s heart and Alex was no exception.

She leaned in and kissed him.

“You’re secret is safe with me Brad because we both have secrets to keep. Now what do you think of these stockings?” Alex extended a leg so that Brad could appreciate it.

He ran his fingers along her leg and leaned in and kissed her. Alex was comfortable with Brad’s mouth, they had kissed passionately before and it was just how she remembered it. He was a good kisser and he used his tongue expertly while his hand softly stroked her legs, his fingers tracing the backseam on her stockings.

This time his hand didn’t stop at the welt when it disappeared under her dress, it continued on to her silky panties searching for something that wasn’t there. Alex was a little surprised at Brad’s bold move but her cock was uncomfortably hard, pressed along her perineum and she wriggled a little and let is spring free, all the time kissing Brad passionately.

Brad touched Alexis’ penis through the gauzy material of her panties and cautiously felt the outline of the appendage. Alex could sense his hesitancy and she understood why. She reciprocated and pulled at Brad’s trousers and there was an awkward moment while they broke apart and Brad stripped down to his jockey shorts and Alex took off her dress.

After ruining her expensive satin evening gown during their previous encounter there was no way she was going to ruin this dress!

Brad gasped when he saw Alex dressed in the red satin bustier with the garters attached to those magnificent stockings. This was his fantasy. Alex looked gorgeous and sexy with her blonde hair, heavy makeup and fuck-me heels; he wasn’t even repulsed by the bulge in her panties, in fact it fascinated him.

He pulled her down into his embrace and they rolled around on the couch, kissing, fondling and canoodling. Alex’s tongue invaded her mouth and his hands were everywhere: stroking her legs, squeezing her buttocks and sometimes stroking her cock through her panties. Alex responded accordingly and she stroked Brad’s cock, feeling the precum leaking from the eye in a continual dribble. She used the viscous fluid to lubricate his shaft and slowly stroked him as he gasped into her mouth.

She was glad that she had taken her dress off because Brad’s pre-ejaculate was getting everywhere. He moved her hand out of the way and rubbed his cock on her stockings and rings of intense pleasure radiated from his cock. He had wanted to do this for so long with Monika but she was far from his thoughts. His only thoughts were of Alex and how beautiful and desirable she was and how desperately he wanted her.

Their kisses were becoming frantic and Brad guided his cock to Alex’s panties and he rubbed it there, pressing it against Alex’s cock through her panties. Her panties soon became soaked in precum and Alex had a wicked thought. She wondered what Brad’s precum would taste like?

He grumbled when she broke their embrace but when she dropped to her knees on the floor and put her head in his lap his whining soon stopped.

Alex looked up at Brad and grinned at him wickedly and he looked down at the beautiful young woman on her knees holding his cock inches away from her ruby-red lips and his heart skipped a beat. Alex licked her lips seductively and gazed at Brad’s cock, the shaft was girded by blue veins, the skin translucent, the head bulbous and pink, a clear droplet of pre-ejaculate formed at the eye.

Alex tentatively extended her tongue and licked the bubble of precum off the tip of Brad’s penis and he nearly came. It tasted clean and salty and then Alex put Brad’s cock in her mouth. It was first time she had ever sucked a cock but she’d watched plenty of crossdressers do it online and it instantly became an instinctive skill.

She closed her mouth on the shaft and worked her tongue on the flange of Brad’s cock and lapped at his fraenulum and felt his cock judder in her mouth and heard him groan. His hands went to her head and he entwined his fingers in her hair but he wasn't rough. He gently guided her mouth up and down on his cock and Alex enjoyed him doing so.

She freed her cock from her panties and began to stroke it in time with her fellation. As her head bobbed up and down on Brad’s hard rod, she moved her hand accordingly along her own cock. Brad was mewling and moaning as Alex used her soft lips to suckle his shaft and her wet silky tongue to slather at his glans. He was going to come soon and he was tempted to push her away but it was just too sublime.

Alex felt Brad’s cock begin to throb and pulse in her mouth and she sensed that he was about to ejaculate so she sucked it harder and faster and lashed his glans with her tongue.

Brad held her head still and fucked her face as he unloaded stream after stream of hot, viscous semen into her pretty mouth and Alex savoured the salty, musky issue and swallowed most of it but saved some to relish, as her own orgasm exploded and she spewed her spend onto the black Italian tiles that her mother cared so much about.

Alex sucked very drop from Brad’s cock and held some of it in her mouth until his penis began to become flaccid. She jumped up on the couch and pressed herself to Brad and kissed him, spitting his remaining semen into his mouth.

She expected him to be repulsed. It was a test. But he relished the taste of his own issue then spat it back into Alex’s mouth. They kissed passionately and Brad’s hands went to her legs and played with them and Alex delighted in the feel of his hands rubbing her diaphanous stockings on her soft skin. His hand drifted upwards and was surprised to find that Alex was once again engorged. Rather than pulling his hand away he stroked her cock until it was rock hard. Alex took Brad’s semi-hard cock in her fingers and improved his erection.

They kissed and fondled and stroked each other until they were both close to coming again and then Brad surprised Alex even further when he wrestled her into a 69 position with her underneath him and he sucked her cock while she sucked his. He stroked her legs while he sucked her penis and Alex really enjoyed it and of course so did Brad. In fact he enjoyed it so much that he ejaculated a second helping of semen into Alex’s mouth at exactly the same time that she exploded into his.

They spent the evening on the couch, kissing, caressing and canoodling. Both too spent to orgasm a third time but it was a very pleasant evening.

Brad and Alex drank more vodka and he kept apologising for being a prick until Alex got sick of hearing it and told him so shut up. Then he started to become sentimental as the alcohol took effect. He told Alex how much he desired her and how much he respected and admired her. Alex knew that many a girl had heard these same supplications from Bradley Brody and she treated them accordingly.

She showed him to the door just after midnight and promised him that she would see him again but she was actually unsure if she ever would.

If she wanted a toy boy she had one; that was for sure.

She slept soundly that night, her dreams pleasant and undisturbed.


Besides practicing her makeup skills and putting on fashion shows for herself in the evenings, lazing around the pool listening to music and compulsively masturbating during the day, Alex had a daily exercise routine to keep in shape. She started doing yoga and bought herself some Lorna Jayne tights and tops to do it in. Of course she would do the yoga on the lawn beside the pool patio so she could tease Carlos. She knew that he was fascinated by how she created a smooth pubis in her tights and Alex spent a lot of time in yoga positions that showed off her buttocks and crotch.

Then she would change into her swimsuit and do laps of the pool until she was exhausted. She’d lay down beside the pool until her energy returned and then she’d do another set of laps and finish off with a series of pushups and sit-ups.

Afternoons were reserved for sipping wine; by the pool if it was sunny, inside watching Netflix if the weather was inclement. Alex was going through a bottle of wine a day and also drinking vodka in the evening. She decided to make two days a week alcohol-free to prove to herself that she was not dependent. Many of the kids at school started to binge when they turned eighteen and Alex didn’t want to become like them.

During one of her weekly phone calls with her mother, Susan told Alex that she was extending her stay in Bali for two weeks and then flying onto LA to tend to some business. She did not tell Alex that she was taking her German toy-boy with her. Alex became upset because she desperately wanted to come out to her mother. She told her mother that it was important that they meet up face to face and Susan told Alex to get on a plane to Denpasar or it would have to wait until she returned to Sydney.

The thought of travelling overseas presenting enfemme terrified Alex and alternatively the thought of becoming Alexander again once again just to travel was repugnant and she wouldn’t do it. She begrudgingly told her mother that her news could wait until her mother returned from her travels.

The next day was one of Alexis’ alcohol-free days but she broke her promise and after doing her yoga she began drinking. She had changed into her brilliant-white swimsuit and put on her makeup hoping that looking pretty would distract her from her angst and frustration.

As usual Carlos found a reason to trim the hedges near the pool patio even though he had only trimmed them two days earlier. He spied on Alex while she was doing her yoga and stretched and preened before she dove into the pool and then he watched her when she climbed out; her tight white spandex swimsuit clinging to her body. Gloria had the day off so his sexual release would have to come in the form of masturbation. Watching Alex parade around in her swimsuit put some images in his wank-bank for later.

Carlos didn’t mind that Alex only had small breasts. He knew they were some sort of prosthesis. Gloria had huge tits and he got his fill of them when they engaged in their trysts, he thought that being flat-chested actually enhanced Alex’s unique sex appeal. As usual he was drawn to her pubis. How did she hide her genitals in such a way that her crotch looked just like a woman's? He would like to find out.

Carlos noticed that Alex was drinking early and drinking heavy, she stumbled on her high heeled sandals when she went inside to get her cigarettes. She seldom smoked and almost never smoked in front of the help. She lay on the sun lounge smoking and drinking listening to Adele on the sound system and eventually Carlos had to move on; he’d spent too much time snipping at the same hedge.

He decided to get the hand mower and clip the grass at the back of the patio. It was an ornamental lawn where Alex liked to put her yoga mat to do her yoga routine and it was lush and green and Susan insisted that it be hand mown. Carlos didn’t mind; pushing the hand mower was therapeutic and he didn’t want to start a noisy motor-mower and ruin Alexis’ serenity. Also it was an excuse to perv on her.

He heard the scream and the splashing and at first thought that it was Alex messing about until he realised that she had fallen into the pool. Usually a strong swimmer, Alex was flailing around in the deep end and was obviously in trouble. The wine had got the better of her and she had tripped and stumbled into the pool and caught unaware she had taken a mouthful of chlorinated water.

Carlos kicked off his boots, ripped off his shirt and dove in the pool.

Alex struggled against him as drowning people were want to do but she was no match for his strength. He managed to hold her against him and swam sidestroke into the shallows where he held Alex close to him until she stopped struggling.

“It’s ok Miss Alex; you’re safe, you’re safe,” he cradled her and patted her back.

She was crying; more embarrassed than anything else now that she was safe.

Carlos couldn’t help but take advantage of the situation. This was the closest he had ever got to Alex and her tiny body clad in the spandex skin-tight swimsuit felt delicate and delightful against his bare chest. Her skin was soft and tanned and he could smell the remnants of her perfume. Her face was framed by her straggly wet blonde hair and even though she wore waterproof makeup her eyeliner and mascara had run a little. Far from making her look ugly the effect made her look very pretty and vulnerable. Her full red lips, painted with ruby-red lipstick, were trembling.

She looked up into Carlos eyes, her gaze full of gratitude, and smiled at him demurely. She made no effort to disengage and she clung to him as he held her tight.

“Thank you,” she whispered and batted her eyelashes.

Carlos was becoming tumescent. Holding this pretty young thing, almost naked, against his body was very arousing. He interpreted her demeanour to mean that she felt the same way and lowered his face to hers and kissed her.

It was delightful to be kissing this beautiful young woman whilst they were both nearly naked in the warm water with the sun beating down on them. Her body was supple and her lips were soft and yielding. She tasted like Rosé wine and menthol cigarettes but it was not unpleasant. She did not exactly return the kiss but she made no effort to push him away.

This was the first time that Alex had been kissed by a real man and it was amazing. She could feel Carlos’ muscled body, so much bigger and mature than Brad’s. Carlos’ face was bristly with five o’clock shadow even though it was still morning. His arms were big and strong, his tongue was insistent and she could feel that monster penis pressing against her flat tummy.

Alex had seen that penis and knew how big it was and the power of it. She had watched Carlos stroke it to climax and seen it throb and spew forth a geyser of semen, spattering on a picture of a young woman who had similar features to her. She was aware that Carlos was holding her close, squeezing her tight and her own penis was beginning to engorge; it was uncomfortable between her legs.

Alex panicked.

She began to push against Carlos, drumming her fists on his chest.

“Let go of me! What do you think you are doing you oaf!” she wriggled in his grasp which Carlos briefly enjoyed but he released her.

“Sorry Miss Alex; I thought you were drowning,” Carlos said.

He suddenly realised the stupidity of his actions. This teenage travestida held his destiny in her hands. His job as groundsman for the Dupree family paid exceptionally well and had many benefits including his affair with Gloria. Alexis Dupree could ruin him with a single phone call to his employment agency. She could fire him, refuse to give him a reference and tell prospective employers he was a pervert. Not to mention what the Dupree lawyers would do if they came after him.

Not for the first time Carlos’ little head has a one-track mind and when aroused it overruled the logic of his big head. He had allowed himself to become infatuated with this travestida Lolita.

“And what? You thought I needed mouth to mouth?” Alex chided him.

“I’m so sorry. I overstepped. It will never happen again,” Carlos hung his head, unable to look Alex in the eye.

“You bet it will never happen again!” Alex snipped and turned and reached for the ladder and climbed out of the pool.

Despite having just being admonished Carlos couldn’t help taking a final long lustful look at her ass.

The truth was that Alex was embarrassed about falling into the pool and nearly drowning in her drunken stupor but also scared of the masculinity and maturity of Carlos. Brad was strong and handsome, he was a sportsman but he was immature and surly whereas Carlos was ruggedly handsome and confident; weathered and powerful with his big broad shoulders, thick muscled arms and legs; his leonine head topped by an unruly mane of jet black hair sprinkled with grey and he had deep piercing blue eyes.

Brad and Carlos were opposites but she was attracted to them both ephemerally but it was a fantasy. With Brad she had actually morphed into two brief sexual encounters and with Carlos she had teased and taunted him and watched him masturbate.

But the danger of doing so had manifested itself when Carlos took advantage of her in the pool.

Alex sulked off to the kitchen to get more wine and Carlos hid in his workshop sharpening tools that didn’t need to be sharpened.

Alex lay on the sunbed sipping wine and smoking, staying well away from the pool and eventually she fell asleep. She had weird dreams in which Brad and Carlos competed for her favours. She awoke hungover and fuzzy-headed. She called out for Gloria and then realised that Gloria had the day off. The house was silent, her playlist long played out.

Alex stood up and peered into the elongated shadows. There was no sign of Carlos. She knew his hours were from eight in the morning to five in the evening but she knew that he often left early, sometimes giving Gloria a lift. Gloria would sometimes ask to leave early but Carlos just took off. Maybe she should fire him!

Her resentment grew as she made her way upstairs and took a long hot shower, shampooing and conditioning her hair. She sat at her mirror blow-drying her bangs then she did her makeup. All the time her resentment for Carlos was growing. He came to work late and left early, he leered and ogled her, he masturbated in his toolshed. She giggled at the irony of the name toolshed. He was arrogant and worse of all he had taken advantage of her whilst she was most vulnerable.

As she slipped into pantyhose and panties and stuffed her prosthetics into her bra cups she began to realise that she was behaving like Brad. She was pouting and whining to herself like a brat. She thought more about it as stepped into a little black miniskirt and pink satin blouse. She had teased and taunted Carlos and when he made advances she had reacted badly.

All she had to do was say no. She didn’t have berate and threaten him. He had probably saved her life and she had rewarded him by threatening to sack him. Sure he shouldn’t have tried to take advantage of her but she had been teasing him for weeks. As she slipped on her high heels she decided that she would apologise the next time she saw him and she would stop taunting him.

Alex eyed the kitchen when she got to the bottom of the staircase knowing that the Deep Eddy lemon vodka was lurking in the freezer, calling to her. No! She would wait until later; at least until the sun had gone down.

Alex took a trip around the ground floor of luxurious house to keep her mind off the booze in the freezer. She opened the connecting door to the garage and saw her black Lexus SUV and wondered if a drive might clear her head. Should she venture out dressed enfemme for the first time? She thought probably not. She would likely blow over the legal BAC if she was stopped for a Random Breath Test. The cops liked to hide in the layups on the curves of New South Head Road and pull over unsuspecting drivers, especially those driving luxury vehicles.

It was then that she noticed that Carlos’ utility was still parked in the motor court. She wouldn’t be able to leave anyway because he was blocking her in. How dare he! He had been told a thousand times not to park against the garage doors.

Alex put her hands on her hips and tapped her feet. Her anger was returning. She strode through the house, out the sliding glass doors onto the patio and took the path leading down to the workshop.

Alex opened the door to the workshop half-expecting to find Carlos masturbating but he was standing at the workbench working on a power tool of some type. He had his shirt off and she couldn’t help but admire his thick tanned torso and as he turned her eyes were drawn to his hairy chest. His blue eyes flashed at her briefly then he looked away.

“Miss Alex; can I help you with something?” Carlos pretended to work on the grass trimmer.

Alex looked at Carlos’ big hands covered in grease as he delicately worked on small screws and springs. For a second she imagined them holding her tight, leaving dirty marks on her pristine white swimsuit. She shook her head to clear it.

“I wanted to thank you for saving me in the pool today Carlos. I was stupid to drink so much wine and then go near the water,” Alex said, her voice sounded raspy.

“You are welcome Miss Alex and I would once again like to apologise for my actions. I misread your signals,” Carlos replied, his voice gruff.

“Signals?” Alex stiffened.

“Yes, signals,” Carlos bristled.

This spoiled teenage brat knew what he was talking about.

“What do you mean by signals?” Alex tapped her foot.

Alex knew exactly what Carlos meant but she would not be spoken to this way by the help.

“You know exactly what I mean,” Carlos’ anger was broiling.

The bitch was playing dumb and using her power over him as her employer to embarrass him.

“Laying around all day nearly naked in that skin-tight swimsuit flashing your tits, ass and coño at me. Doing your yoga on the ornamental lawn, showing off your body and legs in your tights. Even now you come down here dressed like a puta in your little skirt, your makeup and high heels! Those fucking signals!” Carlos glowered and then turned his back and began to tinker with the grass trimmer.

Any conciliatory thoughts that Alex had vanished immediately. How dare he talk to her like that? How dare he be so right!

She took a step closer and she could smell the sweat and engine oil on him; he reeked of manliness.

“And another thing! How many times do you have to be told not to block the cars in the garage?” Alex said in whiney tone that even she found abrasive.

Carlos ignored her and continued to fidget with the power tool.

“Look at me when I’m talking to you!” Alex put her hand on his shoulder and squeezed.

Her delicate little fingers with their long painted nails grasped his hard muscled flesh.

Carlos spun around; his nostrils flared, his eyes blazing.

“Shut up you spoiled little brat. You little Lolita! You fucking precocious prick tease,” Carlos hissed, his face inches from hers.

Alex recoiled and took a step back.

“You’re fired!” Alex screamed at him; she had finally lost control of her temper.

“Good. Now I can do this,” Carlos reached out and pulled Alex into a bear hug.

He smashed his mouth against hers and drove his tongue into her mouth; one hand went to her ass and squeezed it brutally while the other held her close.

Alex was stunned and at first she went limp and then she began to struggle violently. She squirmed in his grasp but was unable to move very much. Carlos was so powerful and he radiated masculinity and Alex felt like a princess being ravished by an ogre. Somewhere deep inside she liked it but she continued struggle even as Carlos kisses became less fervent and more tender.

He relaxed his grip a little so that he was no longer crushing her but was holding her close. His hand stopped squeezing her buttocks but remained there and began to stroke them and caress them. Alex could probably have extracted herself from his embrace at that point but she didn’t. But she was not responsive either. She allowed him to kiss and fondle her but she took no active part.

Carlos inhaled her perfume while he kissed her, his lips soft on hers, his tongue gently probing, his cock uncoiling as he held her close and felt the delicate femininity of her. He knew who she was. He knew what she was. And it excited him, fuelling his ardour and his need for her.

He knew he had crossed a line. His future employment was doubtful and if Alex complained he could be in serious trouble with the law but he didn’t care. He kissed her softly, cupping her face in his hands. He broke the kiss and looked into her emerald green eyes.

“You are beautiful. Irresistible. I know that I shouldn’t but I want you… I need you,” Carlos whispered.

He kissed her again, his lips full. Hers felt bruised but Alex thought it was the most wonderful kiss she had ever experienced. She could sense the passion, the yearning and the adoration in that kiss. She opened her mouth and reciprocated, slipping her tongue into Carlos mouth and tasting the spiciness of him.

She pressed her soft body against his muscled frame and felt the bulge of his cock on her belly. She wrapped her arms around him and Carlos lifted her off her feet and sat her on the workbench. Alex didn’t care that her designer skirt was resting on a filthy wooden bench. She wrapped her legs around Carlos' waist and pulled him in closer.

Carlos liked the feel of Gloria’s pantyhose on his flesh but she wore cheap practical Kmart hosiery, the feel of Alex’s gossamer silken hose on his flesh felt wonderful. He began to unbutton Alex’s blouse.

“There is nothing in there,” Alex whispered sorrowfully; ashamed that she was a sham of a woman.

“Shut up,” Carlos said firmly but lovingly.

He opened her blouse and kissed Alexis’ shoulder and she gasped at the feel of his raspy face on her tender flesh. His lips and tongue followed the hollow of her neck and then down her sternum. His hands rested on her thighs, stroking her diaphanous-sheathed skin, relishing the feel of it, sending little ripples of divine pleasure up Alexis’s legs.

His mouth came to the top of her lace bra and Carlos took a hand from Alexis’s thigh and unclipped her brassiere. He tossed the ‘chicken-fillet’ breast enhancers into the corner and lowered his face to her meagre little buds. Alex gasped as Carlos suckled her nipple, using his lips and his tongue to nurse her swollen teats whilst nipping at them gently with his teeth. Alex moaned and when Carlos began to stroke her legs and snake his hands under skirt she shuddered with lust.

Alex entwined her fingers in Carlos chest hair; she kissed the top of his head as he tended to her meagre breasts. He expertly suckled her nipples while his hands moved further and further along her nyloned-thighs until they reached her panties where the fingers of one hand circled her satiny pubis while the other stroked the top her left thigh. Pleasure radiated though her body and Alex threw back her head and moaned.

She snaked her hand down his body and struggled with his shorts until they fell down to his ankles. She eagerly slipped a hand inside his briefs and extracted his thick meaty cock and bulging scrotum. Carlos growled as Alex began to stoke him. His shank was so big that her fingers didn’t close fully around it and she slowly worked her fingers along the veiny, steel-like shaft.

Carlos kissed Alex, this time with more passion, his tongue insistent. His fingers slipped inside her panties and Alex panicked and slapped at his hand.

“Don’t. Please don’t. I’m ashamed,” Alex whimpered.

Carlos shut her up by kissing her and prying away her hand from his. He found her penis and freed it, squeezing it gently though her pantyhose and Alex shuddered with desire.

She stroked Carlos’ hard rod, using the dribbles of precum to lubricate it while Carlos caressed her engorged penis through her pantyhose, feeling the silky fabric become damp as she leaked pre-ejaculate. Alexis’s cock was sensitive; rings of pleasure radiated form it. Her mouth was on fire from Carlos’ kisses. She hooked her ankles around his legs trying to pull him closer but he wanted to see what he was doing to her.

He lifted her up quickly and flicked her dress out of the way exposing her panties and then he dropped her down on the bench. He could see the bulge in her panties, the shape of his hand inside them as he caressed her cock through her pantyhose. He felt Alex stroking him, teasing him with her fingers. She had a featherlight touch and he was glad; if she gripped him too hard he was afraid that he would climax.

Carlos alternated long languid kisses followed by periods where he stared down at her pantied cock and she looked down too, impressed by his huge manhood. Carlos pushed his cock onto her panties and rubbed it on her pubis, leaving a smear of pre-seminal fluid that soaked into the slinky satin. Alex felt the girth of his cock on hers as he did it. It was similar to what she had felt when Brad did it but Carlos’ cock was so much bigger.

Carlos desperately wanted to fuck this pretty young travestida but he had no idea if she was virgin or not. As far he knew there hadn't been any boys around during the day but who knew what she got up to at night.

He snaked a finger inside her pantyhose and snagged the crotch. He ripped it open and took her hard cock into his hand and stroked it, feeling the bare flesh of her penis for the first time. Alex looked down and saw her penis sticking out of her panties lying in Carlos’ huge calloused paw. His fingers were rough but somehow that seemed appropriate. He was such a brute of a man he should manhandle her and be a little brutal. She’d had a sensual feminine encounter with her sister and a gentle canoodling session with Brad. Now she wanted to be ravished by a real man.

It was a form of self-justification. She had no choice. She was coerced, misused, unwilling, beguiled by this brute. She kissed him passionately and squeezed his cock until it released a dribble of precum and she smiled around the kiss.

She stopped smiling when Carlos removed her hand from his cock and pushed it inside her panties.

“What are you doing?” Alex was suddenly cautious.

“I’m going to fuck you,” Carlos’ said nonchalantly.

“Not you’re not,” Alex grinned at him, scooting back away from away from him.

Carlos dipped his hand in a tin of grease on the bench and generously slathered it on his huge member. Alex was struggling again, trying to slew her ass away from him on the table but Carlos held her tight with one arm around her waist. He kicked her legs open and scooched her toward him, her panties picking up spinsters from the table.

“Stop it you brute!” Alex hammered her fists on his shoulders but Carlos ignored them.

He pulled the crotch of her panties aside exposing her puckered bud inside the torn pantyhose. He pressed the huge purple glans of his cock into the wrinkled aperture and began to push.

“God no! You’ll kill me!” Alex screamed but there was no one to hear her.

She had watched plenty of crossdresser and transvestite porn online and they seemed to enjoy being taken anally. She had used her vibrator on herself almost daily, thrusting it in out of her anus and enjoyed it. But the thought of Carlos’ enormous penis ripping open her asshole was terrifying.

Carlos pushed again and this time he entered her.

Alex nearly fainted with the pain of it.

“Stop! Stop! Stop!” she whimpered; tears running down her face.

And Carlos did stop. But he didn’t take it out. He left the first third of his manhood buried in Alexis’ anus and leaned into her and kissed her. She’d stopped struggling because that only made it hurt more and now the pain was tolerable. She felt Carlos take her penis in his hand and begin to stroke it. Amazingly it had remained erect during the assault on her asshole and Carlos’ passionate kisses and his gentle manipulation of her penis contrasted with the burning pain coming from her sphincter.

Carlos took a chance and pushed another inch inside Alex and she gasped but didn’t scream. She felt stretched to breaking point and fuller than she had ever felt but she also felt something else through the burning pain. She felt little ringlets of pleasure radiating from her distended sphincter. Alex concentrated on relaxing her anal muscles as Carlos kissed her and stroked her trembling penis.

Carols sensed her compliance and pushed a little harder, sliding the last of his engorged manhood into Alex’s distended anus. Alex felt his pubis slam into hers and his scrotum slap against her ass as his cock lay nestled deep inside her.

She put her arms around his neck and legs around his waist and hung onto Carlos, returning his kisses as he slowly began to fuck her. She couldn’t control herself and semen began to dribble from the eye of her cock immediately Carlos gripped her hips and drove his cock slowly in and out of her stretched anus. The feel of her tight tunnel clasping his bloated penis was unbelievable. He could feel her shaking as a prolonged orgasm wracked her body. She clung to him with her arms and legs, her silken-sheathed limbs caressing his flanks, her heels scratching his back. He looked down briefly and was amazed by the continual flow of semen dribbling from her cock but she pulled his face to hers and kissed him frenetically.

Alex was in total bliss. Carlos’ bloated cock was distending her sphincter and her anus, his glans pressing on her prostate, his lips crushing hers his tongue slithering in her mouth as he began to fuck her harder. It hurt but it hurt wonderfully and her prolonged orgasm finally peaked and she felt magnificently filled and content.

Carlos felt his climax approaching and there was no stopping it. He slipped his hands under Alexis’ buttocks and lifted her off the table and began to jackhammer his cock in out of her tight hole and she clung to him moaning and sighing. She didn’t think Carlos cock could get any bigger but she felt it suddenly expand and then begin to pulsate as he filled her back passage with his load. His scalding semen filled her and dribbled from her tight ring, running down the crack of her ass and her thighs. Another orgasm washed over Alex; this one intense and earthshattering.

She clung to Carlos like a limpet to a rock while he ravaged her anus with his huge cock. It bruised her and battered her innards but it felt wonderful; circlets of pleasure pervaded her prostate, her sphincter was on fire her cock pressed against his hard belly and was spewing forth her spend.

Carlos felt her warm seed on his belly but he was not repulsed; on the contrary it amplified his own pleasure as he continued to ejaculate; Alexis’ pulsating anus milking him of every drop of his spend. He dropped Alex back on the table and drove his cock all the in her as far as it would go until she screamed. He stifled her scream with a passionate kiss and she scratched his flesh with her nails and drummed her heels on his back as his climax peaked and subsided. Her aching anus stretched, bleeding and sore but still emitting weak pulses of pleasure and delight.

Carlos thought his cock was going to split open it was so bloated, gripped tightly by Alexis’ anus but as the last of his issue dribbled from the eye it slowly began to shrink.

The lovers clung to each other, mated like a bitch and a dog. Carlos scared he would prolapse her anus if he pulled out while his cock was still hard. They mewed and kissed and fondled; neither of them saying anything coherent, both lost in post coital bliss until finally Carlos’ penis plopped from her anus like a cork from a bottle releasing a flood of semen, grease and blood.

Alex gently pushed Carlos away and he stepped back from her but he helped her down from the bench. Alex felt like her ass was on fire and her legs were shaking. She did the best she could to rearrange her panties and pantyhose so that they absorbed the mess dribbling from her sphincter. She hooked her bra and buttoned her blouse. Carlos pulled up his underwear and his shorts and reached for his shirt. He handed Alex the silicon breast enhancers he had thrown in the corner and she tucked them into her bra.

Try as she might to tidy herself up she still looked a shambles. Her hair was a bird’s nest, her makeup ruined, her lips bruised and her clothing dishevelled. She could hardly walk and she gingerly made her way to the door and stopped and glanced back at Carlos who was looking at her thoughtfully.

“You’re not fired,” Alex smiled wanly at him.

“And?” he asked expectantly.

“And… I don’t know. I’m confused. I’m not angry so you don’t need to worry about that, but I’m not sure what I have just done,” Alex said honestly.

“Did you like it?” Carlos grinned at her a little salaciously.

Alex just smiled meekly at him and limped away.


Alex Dupree stayed in her bedroom for next two days, coming out only after the help had left for the day. She needed the time to heal. She felt like someone had driven an express train through her ass. Gloria fussed over her asking repeatedly if she was ok through the closed bedroom door, leaving snacks and drinks that Alex didn’t touch.

Carlos fretted. Fucking the young trans woman had been delightful but it might have cost him his job and jeopardised any future employment, at least in the Sydney Metro area. He didn’t tell Gloria what had happened, even when he fucked her on same work bench where he had fucked Alex. Try as he might he just couldn’t conjure up visions of Alex while he was fucking Gloria in her pseudo-sexy housemaid’s uniform. His lust for Alex had dissipated and had been replaced by fear.

Alex thought long and hard and made some decisions. There was no doubt that she had felt different all of her life. Her inseparability with Monika was not just because they were twins. Alex realised that all along she had really seen Monika and herself as sisters not as brother and sister. Her androgyny, her fascination with women’s fashion, her pursuit of feminine activities, her secret crossdressing and more importantly the way she felt when she was with Bradley and Carlos, were all indicative to her that she was indeed a transgender woman.

Alex also realised that she had been using alcohol to try to supress her real feelings. As much as she loved presenting as femme she was scared to make a whole of life commitment to womanhood and decided that she would take affirmative action to remedy the situation.

At eighteen years of age she was young but she was still legally an adult and could make her own life changing decisions. She was extremely lucky that she had almost limitless resources and had a gap year before she started university and she would take advantage of that.

Alex studied gender reassignment online and made some decisions. She was booked into an exclusive medical facility in Manila to undertake breast and buttock augmentation and a tracheal shave. She would also begin feminising hormone therapy. She would convalesce between surgeries at a luxury hotel.

Having unlimited access to money and the Dupree name meant bypassing the requisite mental health screening and psychotherapy. She had already applied online to the NSW Registry of Births, Deaths & Marriages to legally change her name from Alexander to Alexis. This was a simple process and cost a pittance.

Alexis had taken the bold step to come out to her mother. The conversation wasn’t as brutal as she’d thought it would be. Susan Dupree told Alex that she had always known that her son was different and suspected that there might be some deep underlying issue that caused Alex to pursue a lifestyle that was unconventional. Alex suspected that the truth was that her mother saw another opportunity to use her children as an advertisement for how progressive she was as a mother. It was very de rigueur to have a transgender progeny at the moment and Susan never missed the opportunity to exploit a fad.

She decided that she would not come out to her father until she had recovered from her surgery but she told Monika of her intent and Monika was over the moon. She would join Alexis in Manila and nurse her through her procedures.

For the first time in her life Alexis Dupree felt truly content and happy within herself. Having made some life changing and life affirming decisions she was ready to face the world.

When she emerged from her room she was dressed in her dazzling white swimsuit and a transparent beach robe. Her hair and makeup were perfect and her heels click-clacked on the sandstone patio as she strode purposely to where Carlos was trimming the ornamental hedges. She had her handbag slung over her shoulder and was carrying an espresso.

Carlos turned and looked at the little teenage goddess and appreciated her but his lust for her was spent. He had tasted the forbidden fruit and as much as he had enjoyed it he was not prepared to pay the price if the snake turned and bit him.

“Come with me,” Alex strode past Carlos purposely and he dutifully followed her with his head down waiting to be sacked.

Alex stopped and sat on a stone bench in a small arbour that gave magnificent views of Sydney Harbour. She didn’t invite Carlos to sit.

“First off I want you to know that if you keep what happened between us a secret your job is safe,” Alex took cigarettes from her handbag.

“Of course…” Carlos tried to reply but Alex held up a finger and stopped him.

“One little hint that anyone knows what happened between us and you're fired and you will never work in Sydney again. Gloria is probably going to be suspicious; she’s quite nosey but she’s kept our family secrets for years. I know that you two are fucking and I don’t really care; just make sure that my moral integrity remains intact,” Alex lit her cigarette and blew out smoke.

Carlos was about to reply but Alex sipped her espresso and glared at him and he remained silent.

“Don’t get me wrong I enjoyed what we did in your little shed but that’s the problem. I don’t want to make a habit of it. I’m not Lady Chatterley and you are no Oliver Mellors, nor am I going to play Lolita to your Humbert Humbert,” Alex took another sip of coffee and smiled at the bemused look on Carlo’s face as he tried to decipher the literary references.

“We will no longer be fucking,” she said dryly to answer his unanswered question.

“Keep your distance from me and show me the respect I deserve and I will no longer go out of my way to provoke you. As I said, I enjoyed what we did, there will be no repercussions I assure you but it will not be happening again,” Alex blew smoke out towards the vista of the harbour and stood.

Carlos nodded silently, his head bowed.

Alex crushed out her cigarette on the sandstone flagstone and left her coffee cup on the bench. Carlos would pick up the butt and Gloria would collect the cup. They were the help and she was the lady of the house after all.

The End… for now.

Author’s Note: I hope you liked my little tale. Alexis, like most of my protagonists, is nowhere near perfect. In fact she’s quite the little rich bitch but I like her. Maybe we will visit her again sometime down the line.

As always I welcome your comments and critiques.

Michele Nylons, June 2022

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A Climax

joannebarbarella's picture

Of the kind that only Michele Nylons can write. I could be very jealous of Alexis.

good story

i like this story and i really dont mean to be horrible but does not cassie forever on instagram know that your using one of her pictures ?

only just found this!

Another brilliant story from the Michelle Nylons factory. The only thing that bothered me was the Grease- now was it nice clean white silicone grease or black and sticky axle grease, giggle