Pre-emptive Measures Part 2

 

Daniel padded over to the glass wall of the hotel balcony and found that he couldn't help but walk on his toes, so much had he become accustomed to walking in heels. He caught a flash of his reflection in the divider and almost didn't recognise himself. With Alice's guidance, he had become skilled with the makeup brush and his new diet had crafted a slender figure that fit easily into outfits such as the semi-transparent pink negligee he was wearing.

The sun beat down over the luxury resort below and the ocean stretched off to infinity ahead of him. He imagined Raphael out there somewhere on a yacht baking in the sun in a tiny string bikini. It was typical, Daniel thought bitterly, they had worked together to sell LoanRanger inside trading secrets and it was always Raphael that got to swan off to the exotic locations and rub shoulders with the money – even now. Not that he envied him in this instance.

“I bet your pal, Raphael is out there somewhere,” Alice spoke from behind him as if reading his mind. “I can just see him lying there as some pool boy rubs lotion into his big silicone tits while he desperately tries to think up ways to sell our products to the rich businessmen on board.” Alice laughed cruelly. “Guys like that only respond to one thing... Maybe the answer is to provide them with more of it. You'd look great in a g-string bikini, Daniel. Once we have given you the ass for it, anyway...”

“No...” Daniel could only groan with despair. He raised the bottle of Champagne to his fat pink lips and took a slug. He knew the other foot was about to drop. Alice didn't just bring him out here to make idle threats, she wanted something, but if the alternative was being pumped with silicone and thrown on a yacht to be a billionaire's plaything, he wasn't sure he wanted to hear her offer. She had paraded him around this resort for two days now and he still had no idea why. What was she waiting for? She had all the evidence of his collaboration with Raphael by now. She held all the cards, so when was she going to play her hand?

“You will make a very good toy, you know Daniel?” Alice said softly. “For someone...” She approached him from behind and placed her hands on his shoulders. They felt surprisingly strong on his sunkissed skin. “You should know, you're getting the full works either way – tits, facial reconstruction, an ass to die for – but you still have a choice. Option one – we do the surgeries and take you bikini shopping. You will be lying on a sun lounger giving a billionaire a handjob faster than you can say 'Pamela fucking Anderson'. Option two...” she pushed back his long grown out hair so she could whisper in his ear, “we give you a long comfortable recovery and you and I continue to visit exotic locations like this one together from time to time. The choice is yours...but don't keep me waiting. I don't like to wait once I know what I want!”

Pre-emptive Measures Part 1

 This is a continuation of my LoanRanger series. All related captions are on my index page.

Alice leafed through papers from her position in the LoanRanger boardroom, using a fountain pen to check each document line by line before adding her signature to the bottom of the page. To her left sat Vivienne, the company's owner and CEO since the hostile takeover from her ex-husband Saul.

The sound of the office door opening caused both women to look up to see a slender figure entering the room holding a folder. She had long dark hair that cascaded down her back and wore a tight fitted blouse over a flat chest with a pink micro-skirt and glossy nylon pantyhose. The woman walked over to the desk and put the folder down in front of Alice before placing both hands down flat seemingly in an effort to take the weight off her towering heels.

“That will be all, Daniel,” Alice said with a dismissive wave and they watched the feminised man totter out of the boardroom.

“One of yours?” Vivienne raised an eyebrow to her legal council beside her.

“No...” said Alice thoughtfully. “Daniel used to be Raphael's assistant. You know, the scheming Sales Manager who was taking bribes in exchange for insider trading tips, and is now the jiggling platinum blonde with the great rack who takes trips on private yachts wearing micro-kinis to court new clients? We caught Raphael through using a private investigator to audit our expenditure, but he never turned up anything on Daniel. Except, now I am thinking...”

“Now, you're thinking if Daniel really didn't know anything about what Raphael was doing, why did he just come into our boardroom dressed like Erin Brockovich?” Vivienne finished.

“Exactly,” said Alice. “I think he knows something. And for some reason, he thinks we know he knows something, but he also thinks that if gets hair extensions and throws on a pair of heels anyway, we won't look too hard for what that is.” Alice placed her pen down and looked at her boss. “What Daniel doesn't realise is that I am not the kind of lawyer that is going to be satisfied with a couple of socks stuffed into a bra. If Daniel really does know something, and I am betting he does, I am going to find out what that is and when I am though with him, Daniel is going to have substantially bigger assets to be extorted...if you catch my drift...”

Under the Influence Part 8

 16/25

Brody stuffed yet another pillow into its case and cursed under his breath as one of the stupid acrylic nails his sister had glued to him caught on the coarse fabric. Finally freeing himself, he swore again and tossed the pillow onto the bed. He had spent countless hours humiliating himself, all the time putting money in Claire's bank account, and yet in a way, this was somehow worse. Not the least of his problems was the ridiculous uniform he had been given to wear. Sure, it was befitting of the role he was fulfilling, but it was not befitting of his body. He may have slender curves and soft skin from the hormones his sister had been feeding him, but he still maintained his average male height and as a result the flimsy skirt of the maid's outfit flipped over his pantied ass every time he raised his arms.

The meagre money he had stuffed into his purse upon escaping from his apartment had barely covered two nights in a hotel, leaving him absolutely nothing for the guys' clothing he craved so much. Two days of hiding in his room passed excruciatingly slowly. The only times he dared slip outside was to get his fill of the breakfast buffet and he spent the entire time scanning the dining hall in fear of spotting a leather-clad dominatrix, whip in hand, stalking her prey. Still, the large purse he had brought with him came in handy as he was able to fill it with pastries to keep him full for the rest of the day. No-one suspected the delicate blonde woman in the gaudy dresses of trying to steal food.

By the time checkout arrived, Brody still didn't have a plan and desperation set in. That is how he became the newest member of the Rest-Eze Hotel's housekeeping staff. Management agreed to let him continue to stay in his room as long as he spent the day cleaning and preparing bed linens. It wasn't clear if that was the only job available, or if the leering manager just wanted to see what the blonde creature with glowing skin and plump lips would look like as a French Maid, but one thing was for sure – the flimsy uniform he was given simply wasn't up to the task.

Brody threw a duvet cover over the bed and the familiar swish of the dress exposing his ass instantly made him regret it. The phone tucked into his apron vibrated and he removed it to see he had a message from his sister. Probably she wanted to know where he was hiding. To his horror the screen simply read “REST-EZE HOTEL, MAIN STREET”. Another one popped up instantly. “WHAT YOU THOUGHT I DIDN'T EXPECT YOU TO MAKE A RUN FOR IT AT SOME POINT? I PUT A TRACKER UNDER ONE OF YOUR NAILS.” And then finally, “I ALSO POSTED A LINK TO IT ON YOUR ONLYFEMMES PAGE. JUST IN CASE.”

Before he could scream, the door flew open and a sneering figure blocked his exit. Brody stood there in heels dumbly, the duvet still in his hands as Lady Radius snapped the riding crop into her palm.

Whatever Happened to Britt? (...is You!)

 The original caption of this story is here

“That Bitch!!” Britt groaned removing the remaining wrapping paper from the present. Bearing a big bow and a tag with his name, the gift had been sitting innocently beneath the tree with the rest of them. No-one could have guessed what it really was – a grenade filled with with red velvet and fur. An explosion set to go off and ruin Britt's life all over again. How could she do this to him? After all these years... After all he had been through to get here... All his hard work... He allowed the dress to slip through his hands to the floor knowing it would inevitably encase his body before the end of the night. “Melanie, haven't you had your pound of flesh already?” He put his head in his hands.

Ten years ago Britt had experienced a Christmas countdown like no other. His girlfriend, Melanie was away at college and he had organised to shower her with twelve days of gifts to prime her for romance during the holiday break. In return, Melanie had arranged a countdown of her own. Starting with a self-help hypnosis course named 'Be the Perfect Partner with the Guru Self Hypnosis', Britt had been unsuspectingly subjected to hypnotic self-feminisation and Melanie had followed up this initial 'gift' with all the tools Britt needed to complete his own transformation. And why? Simply an elaborate way for Melanie to break up with him and see other people.

It had taken almost an entire year of intense therapy and subliminal suggestion for Britt to break the pink satin chains the course's addiction had trussed him with. Session after session of humiliation to unpick his obsession with becoming the alter-ego Melanie had forced upon him. He had become a joke to family and friends who couldn't fathom that his new compulsion was anything other than a fetish. Even years later, an unfortunate cue, the wrong kind of trigger, and Britt would relapse once again and his feminine side would emerge. He would gather up the cosmetics, the underwear, the wigs that his alter-ego had stashed in places he would never find, and his feminine side would emerge once more. Evidently, Melanie knew all this.

In was hours later and Britt found himself in the park. He was vaguely aware that what he was doing was against his will and embarrassing, but he had slipped into the velvet dress all the same. He had pulled up those long socks and put on the fur hat, waxed his body and painted his face in total obedience to his long dormant programming. It was snowing and he held his hands out to catch some flakes, aware of the picture of beauty he must be painting. As much as he got good at fighting his female urges, he couldn't deny that when they got the better of him, they did a sterling job.

“There you are!” Melanie stepped out from between the trees. She was older now but still stunningly attractive. “I always liked this side of you. I was just too young and stupid to know what I had. I am so glad I can still bring out your feminine side. I think I am going to be seeing a lot more of it from now on!”

The Purest Gift Part 4

 

By the time Laurence had completed a working day in Esme's shoes, not to mention her body and vibrating panties, he had come seven times. His underwear was soaked and chaffed his ass at least as painfully as Gloria's catsuit had. Every time he felt the heat start to grow in his loins, his cheeks flushed with humiliation and though he averted his eyes from his co-workers, he knew they knew. Is this how Esme had felt every time? She had a world class business mind and he had treated her like nothing more than a toy. He hadn't made her wear a buttplug – that seemed to have been some kind of transference from his experience as Gloria, but like the actress, he had used her shamelessly. Laurence wasn't sure if this was all real, but the guilt sure was.

“Well done, Laurence!” The waif's voice reverberated in his head. “You have faced your guilt. You have cleansed yourself of the pain your past actions have caused. You are pure once more. You are now ready to receive the Gift!” Laurence's heart thudded in his chest as once more the walls swirled like the filmed edge of a bubble and began to close on him. When they washed through him, the world went black.

Laurence regained consciousness to find himself outside in the hot sun. He looked around himself at the yellow rock and realised he was at the entrance of the cave, where his adventure had began. Raising his arms to check for cuts and bruises, his breath caught in his throat. They were soft and slender and slightly sun-kissed. A gold bracelet clasped his narrow wrist. Frantically, he assessed the rest of himself. He was still in Esme's body. Gone was the humiliating office attire and in its place was an elegant figure hugging white dress, but her curves remained – her pinched waist, long limbs and round breasts all remained.

“Congratulations on receiving the Gift!” The ethereal voice beamed down on him with the sun. “Your absolution! You are forgiven! You are pure once more! No longer will you carry the crimes of the pain you caused others – for you have faced them and come out the other side...transformed!” Indeed, when Laurence searched his feelings and thought about what he had done to Gloria and Esme, he felt nothing. He felt no guilt, no pain...he was cleansed...but he was also a woman! He looked around wildly for...what?! Anything! This couldn't be the gift!? It just couldn't!? “What's wrong?” The voice asked. “Don't be ungrateful, Laurence! Forgiveness is the greatest Gift a man can receive. But it is not one given lightly. Your transgressions were particularly cold and so you needed a reminder to stay pure...a permanent reminder. There is one more thing...well, two actually!” The voice paused and Laurence yelped as he felt the cold steel of a buttplug growing inside his ass, splitting his newly pert backside in half, and on cue, panties he didn't even know he was wearing started to vibrate furiously. “If you ever slip from your purity,” the voice continued, “I reserve these two reminders to keep you so. These are my gifts...to myself.” The waif's laughter floated away on the breeze.

The Purest Gift Part 3

 

It took Laurence what felt like an eternity to traverse the snowy countryside. He didn't know if time existed in this place, whatever it was, but his ass rubbed raw by the latex catsuit and invaded by the steel of the buttplug definitely acknowledged its passing. This is what Gloria had endured that day he realised as he approached the lodge where they had spent the night. And how had he rewarded her? By demanding she suck him off in front of the fireplace and never calling her in spite of the promises he had made to enhance her acting career. Shame washed over him and not just because of the degrading situation he found himself in.

“Your cleansing is going well!” The ethereal voice whistled with the swirling snow. “But there is more to be done!” Laurence realised that the sky seemed to be closing in on him...like a bubble shrinking. Soon it was just above his head and then it engulfed him covering his face and he suddenly remembered how he had finished on Gloria's face on that day he just experienced. Unknown to her, it would be their goodbye.

When the world reappeared Laurence found himself bending forward, barely holding his balance. He was back inside at least – somewhere he recognised in fact. It was his offices back in Manhattan, noisy and bustling with people. He was face to face with a filing cabinet and he was overbalanced because he was wearing a pair of towering heels. The steel of the buttplug was still clenched between his ass but it felt different somehow. He felt different, and not because he was no longer wearing the ridiculous latex outfit. A chill breathed against the backs of his thighs – a gap left by the different materials of his dress – the polyester of an obscenely short skirt and the nylon of a pair of stockings. At once he knew who he was.

Esme was his office manager. She was hugely overqualified for the role, boasting a phD and an IQ pushing 150 but he had promised a future that included a boardroom position to obtain someone of her exquisite beauty to run his office. Once she was onboard, he had gleefully moved the goalposts to test her ambitions, insisting on scandalous office-wear – skirts that failed to cover her sculpted ass, lip-fillers and.... Laurence crashed into the cabinet as the vibrating panties suddenly activated. He clutched the metal gasping as the underwear buzzed relentlessly, teasing his body to its limit. A moan escaped his lips and he imagined the busy office stopping to watch his debasement. The trigger, he knew, was in his desk drawer. He had kept it near him for almost a year until Esme had finally tired of waiting for the promotion that would never come. She had been a genius and he had used her as a toy.

The panties went up a gear and Laurence was barely able to stay standing. He wanted to sit but feared inadvertently driving the buttplug even further up his ass. Instead, he clung to the drawers with his ass stuck out and only half-covered by the tiny skirt, grunting through gritted teeth as the entire office watched his first female orgasm.

The Purest Gift Part 2

 

“To be worthy of the Gift, you must be pure! To be pure, you must face your past transgressions!. You must endure... Will you endure. Laurence?” The voice echoed and expanded into a hollow whistle, and Laurence's bubble expanded with it. Growing until it filled the cavern, it seemed to paint the walls with sky and the ground with snow until with a shrill pop, he realised he was outside.

Laurence scanned the horizon of endless farmland covered in snow. He knew this place. He'd been here years ago. Switzerland... Suddenly, he realised why his reflection in the bubble had been so familiar...Gloria!

Laurence tried to move forward and almost fell head first into the snow. The skis attached to his feet having not been there seconds before, felt alien and only the poles that had appeared from nowhere in his hands, saved him. There was a squeaky crackle and the shiny material of his snow-suit rubbed painfully across his body...up his legs, over his ass...his breasts. No, this was wrong!? How could he be Gloria?!

Gloria had been a young tv soap actress Laurence had a brief fling with years before. She had been a whirlwind of energy and ambition, but she had also been desperate...insecure. Laurence had told her he could use his power to open doors for her. All she had to do for him was...

The details of the trip to Switzerland formed in Laurence's memory. The latex ski-suit he had picked out for Gloria – him insisting she be completely naked underneath. She had done as he asked of course and Laurence had ignored her forced smile to stare at her ass all day as she uncomfortably shifted from one ski to another. Laurence's mouth went dry as he remembered the other thing he had insisted on.

The steel buttplug made him feel fuller than he had ever been in his life. It was if were being split in two. He groaned low and feminine and steam blew from his pink lips. He had made Gloria ski 20 miles in nothing but a latex catsuit with a plug jammed up her ass, and never given her the fame she wanted. And now he was Gloria? Was this the cleansing the waif spoke about? Would he have to make the same journey? He tried to push himself forward over the white powder and it was immediately apparent that he was far weaker that he was used to. Gloria's slender frame held a fraction of the strength of his toned body. He managed five meters before dropping his poles to the snow and putting his hands on his rubber clad knees with exhaustion. As he did so, the buttplug shifter awkwardly in his ass. Holy shit, the Gift better be worth it, he thought gritting his teeth.