It was Sunday evening and Simon was sitting on the sofa, phone in hand, reflecting on what he had just done. He had decided—impulsively—that he could not tolerate further humiliation at the hands of Sarah and her neighbour, Claire. They had pushed him to his limits and beyond. The thought of going into the office, the following morning, in a ridiculously short skirt, stockings, a transparent blouse, lacy underwear and what he assumed would be badly applied makeup, horrified him. He would, to put it bluntly, look like a tart. It was ludicrous to believe he could pull it off.
Despite assurances she had received from Claire, he suspected that Sarah had reservations about how he would be dressed, yet she had not put a halt to this impending farce, instead putting her faith in Claire, in the preposterous belief Claire knew what she was doing because she'd done a module at college on male-to-female transitioning. It was sheer madness to accept Claire's reassurances, especially as Claire was revelling in her newfound role of being an apprentice dominatrix.
Sure, some of the time he'd spent with Sarah in private had been exciting—sexually arousing, was a more accurate term—but she had pushed him too far out of his comfort zone and things were only destined to become worse now that Claire was involved. Claire took delight in the idea of dominating and humiliating him, and she and Sarah together were likely to form a synergistic partnership. He had therefore decided that escape was his only option and his former football buddy, James, had agreed to pick him up at 1 AM.
Simon knew he had already jumped from the frying pan into the fire and he now intended to jump from the fire before it consumed him. But where he would land, he had no idea. He expected that problems and difficulties would lie ahead, so he was not relaxed about his decision. He also had no funds and no ID, he owed Sarah a lot of money, and he was locked in a chastity device. Oh, and he might find that he's out of a job if (when?) Claire handed his letter of resignation to Ms Deacon.
He looked over at Sarah. She was still absorbed in her film, unaware of the series of messages that Simon had exchanged with James. He needed to keep his fingers crossed that nothing happened between now and one o'clock to raise her suspicions.
At nine-thirty, he went up to bed, as he was expected to do at that time, but not before checking there was nothing Sarah needed. It was important, at this point, to maintain an air of normality—if his current lifestyle could be called anything like normal.
Upstairs, he collected together the few items he planned to take. These included his toothbrush and shaver, along with several pairs of pink cotton knickers, his jeans, socks, trainers and a few T-shirts. Equally important were the things he was leaving behind, which included all his bras and everything that had been purchased for him on Saturday, namely his sexy undies, stockings, blouses and business suits. Of course, none of the clothing he was taking was male because all of that was locked in Sarah's shed, but at least what he was taking was more androgynous-looking than what had been purchased for him the day before.
Needless to say, he would have to depart wearing his chastity device since that was locked in place. One of his first tasks would be to somehow force open the padlock, praying that he didn't dismember himself in the process.
Patiently and quietly he stayed in his room, with the light off. He listened and, at around 11:30 PM, he heard Sarah climb the stairs. After spending some time in the bathroom, she then entered her bedroom. He hoped that she would quickly fall asleep. In the dark, he waited as the minutes ticked by. After a while he heard soft snoring coming from her room, confirming she had succumbed to sleep. He still lay motionless on his bed until, shortly before one, he got up and slipped on the clothes he had sorted out.
But he left his trainers off and proceeded to tiptoe downstairs, carrying his possessions in a plastic shopping bag. Only when he was in the hallway, did he slip on his footwear. He then unlocked the front door, stepped out into the cool night air, and quietly pulled the door shut behind him. Quickly, he locked it and pushed the key through the letterbox. Only then did he allow himself a sigh of relief. He was free! Even if Sarah heard him now, and came rushing downstairs, there was nothing she could do to persuade him to return—not even threats would work.
Simon stood on the pavement waiting for James to arrive. His initial euphoria of having escaped Sarah's clutches was replaced by growing anxiety when there was no sign of James. Fifteen minutes passed, and he started to wonder if he would have to phone Sarah and beg her to let him back inside. He had no idea how he would explain to her that he was locked out of her house, braless, and carrying a small bag of his possessions.
Panic was starting to set in when, suddenly, he saw headlights turning the corner. It was James—true to his word, he had come to pick him up. Not wasting a moment, Simon jumped into the passenger seat and made a point of slamming the door shut as hard as he could.
"Keep the noise down, you idiot. People are sleeping," hissed James.
"Not now," replied Simon, smiling to himself.
"Haven't you got a suitcase?"
"Er, no. I'll explain everything to you once we get to your place. Thanks for helping me, James," he told his friend. "I owe you one."
"More than one, I reckon! You're certainly going to have to tell me what's going on, Simon, but in the morning, not tonight. It's too late. I'm going to feel wrecked from lack of sleep, so I'll be throwing a sickie tomorrow. Are you going to work?"
"Erm, no, best I don't, James," replied Simon. Quite possibly, he wouldn't have a job to go to, but, whatever, he didn't fancy the inevitable awkwardness of turning up at the office in a few hours' time.
Nothing more was said in the car and soon they arrived at James's house. They went inside and, for the first time, James saw Simon in the light. "What the bloody hell are you wearing, mate?" he asked, in exasperation. He shook his head in despair, concluding, "Oh, never mind, explain to me in the morning. I need to go to bed. You'll have to sleep here, on the sofa, I'm afraid."
"No problem, James. I'm just grateful you're helping me."
oooOOooo
Without bothering to get undressed, Simon crashed on the sofa, but he didn't sleep well, despite having gained his freedom. His mind was troubled by the inevitable difficulties that lay ahead. It was probably a couple of hours of tossing and turning before he fell into a disturbed slumber, frequently disrupted by nightmares involving Sarah and Claire. Then, suddenly, he found himself being shaken awake.
"Wake up, Simon! It's morning, so wake up," encouraged a voice.
It took his brain several seconds to realise that the voice was that of a girl and for a few moments, he thought it must be one of his tormentors. He was instantly wide-eyed, looking up at whoever was shaking him. He felt an enormous sense of relief when he saw it was Nicola, James's girlfriend.
"Sorry, Nicky," he found himself saying, using the familiar form of her name.
"No worries, petal. James said he'd picked you up. But what the hell has happened to you? Why are you dressed like that?"
"Er..." It hadn't occurred to Simon that James didn't live alone, so it had been a shock to see Nicky. He'd met her on a few occasions but knew little about her, except that she was a nursing sister in the Accident and Emergency Department at the town's hospital. "Sorry!"
"Stop saying sorry!" she replied, with a smile. "Just tell us what's been going on." She had been joined by James.
"Yes, you owe us an explanation, Simon," he added. "I'll get you a coffee and then you can tell us what's happened."
Simon struggled to his feet and the three of them moved to sit around the kitchen table. The coffee was good and just what Simon needed. He savoured it, wondering how to start his story and, more importantly, what to include and what to omit.
James and Nicky were growing impatient. "Come on. For a start, where are all your clothes? Why are you dressed in girl's jeans, and that T-shirt looks a bit girly?" observed James.
"Er..."
"For goodness sake, Simon!" snapped James. "You've asked for our help, so you owe us an explanation."
"Yes, er, I do. But would it be OK if I spoke to James alone, Nicky?"
"No, it wouldn't!" replied James, adamantly. "Apart from anything else, that would be bloody rude."
"Yes, yes, sorry, you're right," Simon responded, feeling chastened.
"Come on, honey, I'm used to listening to tales of woe. Nothing you say will shock me."
Simon wasn't so sure, but he continued, "Well... do you remember a few weeks back when I bumped into you, James, while shopping?"
"Er, yes, we were both shopping for frilly stuff, yeah?"
"Yes, we were... except you were shopping for Nicky and I was, erm, shopping for myself."
James stared at Simon with an open mouth. Simon suspected that Nicky was also taken aback by what she'd heard, but being a medical professional she put on a blank expression, as if nothing could faze her.
"Uh? What? But? Er? What on earth are you talking about?" asked James, his face screwed up in bewilderment.
Simon had now turned crimson and looked at the other two. James's expression was one of confusion, while Nicky's face now bore a countenance of empathetic understanding.
"Emma had, er, sent me out to buy stuff for myself."
"Uh?" uttered James, still puzzled.
"I'd, er, borrowed some of Emma's stuff to try on and she, er... wasn't happy."
For the first time, Nicky gave a reaction and her eyebrows involuntarily rose up, but she said nothing, quickly regaining her benign composure.
James snorted, commenting, "Is Nicky going to have to lock her stuff up, Simon?"
"No! Honestly, I won't, er, you know, touch your, er, stuff, Nicky... God, this is so embarrassing."
"I know you won't, petal," she replied softly, while tenderly laying her hand over his. "I can see you're upset, but please carry on, because I'm sure there's more to tell."
Simon went on to relate how Emma, on discovering what he'd done, decided to kill two birds with one stone, both punishing him and attempting to cure him of his penchant for lingerie. She did this by making him wear female underwear for four weeks. And this included when going into the office, not just at home. Simon went on to explain how Emma had engaged the services of his former lover and co-worker, Sarah, to keep an eye on him during working hours. Sarah, for her part, had relished this assignment, and took great pleasure in humiliating him. He explained to James and Nicky how, when the four weeks were up, he discovered that he had misunderstood Emma—he avoided saying she had lied to him, despite being of that opinion. Instead of his life returning to normal, Emma had kicked him out, dumping all his possessions in a skip outside her house.
"Ooooh! That's awful," exclaimed Nicky, shaking her head. "How could she do such a thing?"
"But worse than that, I had no money. I'd destroyed my bank cards as part of the deal with Emma."
"Couldn't you use your phone, like a normal person?" asked James, incredulously.
"No, I've never trusted online banking or contactless payments," replied Simon, shaking his head. "A big mistake on my part, with hindsight."
"You're right to be cautious about online security, petal," comforted Nicky, glaring at James.
