A Safe Space Ch. 03

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

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

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
12 Comments
newford9bnewford9b4 months ago

A brilliant tale by a brilliant storyteller

ashlandlitashlandlitover 1 year ago

This story was quite hot and I enjoyed all of it.

UmraojiUmraojialmost 2 years ago
Classic!

Touched the proper points to perfection.

jrrtolkien420jrrtolkien420almost 2 years ago

Another fantastic tale. I loved it.

Show More
Share this Story

READ MORE OF THIS SERIES

A Safe Space Series Info

Similar Stories

"Sissified": 12 Days of Sissy-mas Straight man is turned into a submissive sissy by...in Transgender & Crossdressers
The New Girl Ch. 01 A straight boy learns to submit to girlcock.in Transgender & Crossdressers
All The Pretty Girls Ch. 01 Penelope Bishop returns to hunt a man stalking trans women.in Transgender & Crossdressers
My New Life in a Frat Theme party leads to a new lifestyle.in Transgender & Crossdressers
Delving Dungeons, Discovering Dicks A young man seeking treasure braves The Dungeon.in Transgender & Crossdressers
More Stories