It was Monday morning, and Simon had spent an embarrassing weekend with Sarah making him dress completely in female clothing and punishing him with lines, not to mention adding further days to his chastity clock. He had also had an awkward encounter with a young neighbour and then, to top it all, had learnt that his former girlfriend, Emma, had destroyed his passport and driving licence, meaning he couldn't visit the bank today to order new cards. Sarah's suggestion that he should ask Payroll to credit her account with his monthly salary had appalled him, but he saw no way of avoiding it. With escape routes cut off, he had reluctantly decided that his least bad option was to remain with Sarah and hope that he could survive her tormenting for the next twelve months. Nonetheless, he was perturbed when she told him that she intended to push him to his limits--and beyond.

He'd been woken up at around 4 AM, yet again, by a throbbing erection. His penis was a slow learner and showed no signs of accepting that his chastity cage prevented tumescence--he wondered if it ever would. After showering and making sure he was hairless from the neck down, apart from his landing strip of pubic hair, he had got dressed in the way that Sarah had specified. This meant that, beneath his business suit, he was wearing panties, a bra, a camisole, tights and a feminine blouse. At least he didn't need to insert fillers into his bra but, nonetheless, it was bad enough that he would have to keep his suit jacket buttoned, and he was well aware that the weather was warming up now it was springtime. One concession Sarah had made, which he was truly grateful for, was telling him he didn't need to call her Miss in the office. That was one discomfort avoided, although he suspected it was more to save her from embarrassment than him.

After a quick breakfast, he had undertaken some chores before taking Sarah's breakfast up to her bedroom at 7 AM. By 8:45 AM, the pair of them set off to drive to the office, but, on the way, they passed Emma's house, and he was instructed to push his lines from the previous evening through her letterbox. Sarah had thoughtfully sealed them in an envelope for convenience and had written on the outside, 'Simone's punishment lines for Miss Robinson's approval'. He delivered them as quietly as he could because he most certainly didn't wish for Emma to come to the door while he was on the other side.

He climbed back in the car, and Sarah drove them the remaining distance to the office. Already, following his ordeal of recent weeks, the gossip in the office was that he and Sarah were once again an item. As they pulled into the car park, one of their colleagues witnessed them getting out of the vehicle together, which would only serve to fuel this rumour. Sure enough, news spread like wildfire and, as they entered their department, the conversation instantly stopped, confirming to Simon, and probably to Sarah as well, that they had been the subject of the discussion.

They both grabbed a coffee from the machine in the department's small kitchen and then went off to their desks, but not before Sarah had whispered to Simon. "You need to go to Payroll--now!"

This was a reminder, not that it was needed, that he had to change his bank details. One part of him was hoping that the Payroll administrator might disallow a change of bank, but it proved surprisingly straightforward. There was just a simple form to complete, and no questions were asked, yet he was certain that the girl who had checked the information would have been intrigued to see that the new account was in the name of Miss Sarah Jones. This was all grist to the rumour mill.

He made his way back to his department and was surprised--concerned, more like--to learn that Sarah was in Ms Deacon's office and that the door was shut. How did he know this? Well, one of the older women in the office, believing the tale that they were boyfriend and girlfriend, had taken it upon herself to update him on Sarah's whereabouts in case he was pining for her.

But what were they doing in there? It was most unusual for Sarah to spend time with Ms Deacon and even more unusual for the door to be closed when she did. He looked at his watch and went to his desk in his small office next to the typing pool. From there, he could see his manager's door, and while she and Sarah were in there, he found it impossible to concentrate on his in-tray. Repeatedly, he checked the time and it was thirty minutes before Sarah emerged, looking pleased with herself, which set alarm bells ringing, especially when she glanced in his direction with a smirk.

He thought she might come to see him, but she went to her own desk and turned on her PC. Alarmingly, he then saw Ms Deacon advancing in his direction. She entered his office and closed the door behind her.

"Morning, Simon," she called out, cheerfully.

"Er, good morning, Ms Deacon," he replied, sounding bewildered and suspicious.

She pulled a chair up so they were sitting on opposite sides of his desk. "I've been talking to your girlfriend, and she's explained everything."

He felt himself going crimson because he had no idea what Sarah had told her. And had Sarah really referred to herself as his girlfriend? He had to be careful what he said, otherwise, he might dig himself into a deeper hole.

"Umm ... what did she tell you?"

"Well, obviously that you want to transition, Simon. That you want to change gender." His eyes shot up and his mouth fell open. He was speechless and didn't know how to respond. Fortunately, she gave him thinking time by continuing. "Sarah said you were too embarrassed to tell me yourself, and you'd asked her to tell me."

"Er ..."

"That's right, isn't it? She said you're already wearing a lot of female attire, but you're still nervous about coming into the office fully dressed as a woman. You thought I might get angry with you."

"Er ..."

"Come on, Simon. I'm not here to tear a strip off you. I'm sympathetic. I should have been told this weeks ago because it explains so much of why you have been behaving strangely and underperforming recently. Sarah says she's fully supporting your transition, and so am I. We both think you're very brave."

Simon was trying to think on his feet but without too much success. On the one hand, he could see that if he denied wanting to become female, then he would land himself in a lot of trouble with Sarah, who had engineered this morning's bombshell to cause him maximum embarrassment. (Wow! Talk about pushing him to his limits and beyond.) On the other hand, Sarah had lost one of her aces, namely his undated letter of resignation to Ms Deacon. He couldn't see how that would carry any weight now. But she still had three other aces--the key to his chastity device, the key to the shed where most of his possessions were stored, and, as of this morning, access to his salary.

He had a split second to decide how to reply to Ms Deacon. "Er, er, thank you, Ms Deacon. I appreciate your support but what about all the others in the department? They won't like it."

"Won't like what?" she answered, looking puzzled.

"Me, dressing as a woman."

"Nonsense! Why on earth don't you think they'll be supportive?"

"Er ... I don't know. I just think it's unfair to flaunt around dressed as a woman and embarrass them. It would be a distraction and I'm sure you don't want distractions in the workplace." He gave an embarrassed laugh to lighten the atmosphere before adding, "Besides, I don't look very much like a woman."

She laughed. "Have you forgotten that Sarah has promised to get you help from a beautician and fashion expert?"

"Er ... no, I'd not forgotten," he lied, wondering who this might be. Surely it wouldn't be their young neighbour, Claire. "But they'll have their work cut out." He feigned a giggle which simply confirmed his embarrassment.

"Stop belittling yourself. In some lights, you have quite feminine features. You would pass as a tomboy with no trouble." Tomboy? That was a word not used much nowadays. He was trying to process what she meant as she continued, "With the right hairstyle, some make-up and shaving twice a day you could easily pass as female. Have more confidence in yourself."

"Er ... yes, I'll try to. Thank you."

"Good! I'm now going to have a quiet word with others in the department and when I've done it I'll let you know and then you can unbutton your jacket and take it off."

"Er ... I don't know about that!"

"Don't be silly. You need to make the plunge. You'll feel better for having done so."

"Hmmm ... OK, yes, thank you."

"It's my pleasure ... Simone. That's a lovely name, isn't it?" She smiled and stood up. "Stay strong, Simone, you won't regret this and I think you owe Sarah a big thank you for the help she's giving you. Not many girlfriends would be so understanding and so unselfish. She's a true friend, so treasure her."

With that, Ms Deacon left his office, leaving him feeling devastated and dreading what was lying in store for him. He was furious with Sarah's mendacity but how he was going to tackle her on the subject was open to question. If he wasn't careful, he could easily see his period of abstinence increased further with more lines to write.

Concentrating on his job proved nigh on impossible. He was aware of Ms Deacon going from one person to another briefing them on his supposed transition. Actually, she didn't need to tell many as he could see that the news was spreading like a forest fire. He knew this because of the furtive glances that colleagues were making in his direction.

Ms Deacon's department was a couple of dozen strong but apart from Simon there was only one other male, John, and he was gay. The rest of the staff were female, ranging in age from office juniors much younger than him to middle-aged matron types. He had no idea how any of them would react to this development.

Around 11 AM, Ms Deacon popped her head around his door, gave him a thumbs up and remarked, "All sorted, Simone. Everyone I spoke to was very encouraging and think you're very courageous. You'll have their full backing. So it's time to come out of your office--or the closet if you prefer!" She gave him a huge smile. Nervously, he unbuttoned his suit jacket, removed it and then stepped out of his office to be met with an enormous round of applause led by Ms Deacon and Sarah. He wanted the ground to swallow him up.

The rest of the day was spent with girls and women coming up to him. Some congratulated him on his bravery and honesty, while others offered practical advice on what he should be wearing to the office or how he should be styling his hair. Several, on deducing that he was nervous, were quick to point out that we're in the twenty-first century when everyone's free to choose their own identity.

Even John came up to him, but he was keener to arrange a date rather than offer open support or advice. He seemed miffed when Simon said he wasn't interested in going out with a man. "Ooooh! Well, if you change your mind, you know where I am?" he said.

oooOOooo

The journey home to Sarah's house was spent in silence. Simon so wished to let rip and give Sarah a piece of his mind yet feared the consequences. Sarah also wanted Simon to start an argument so that she could savour his humiliation and inflict more punishment for being quarrelsome. Only when the car had stopped outside her house did he say anything. "Er, Miss. Please explain to me why you've done this?"

"Done what?" she replied, pretending to be baffled by his question.

"Told Ms Deacon that I'm transitioning. You know it's not true?"

"Do I?" She shook her head while looking bewildered. "You've been wearing female underwear 24/7 for the past month and, before that, you seemed to take every opportunity you could to take pleasure with it or in it. You even did the gardening yesterday en femme. It seems self-evident that you long to be a woman but are afraid to admit it. I've done you a favour." Her smile told him she didn't believe a word of what she was saying, not that this was much help to him.

"But it's not true! I'm being forced to wear women's clothes ..."

"What?! You're saying that you were forced to wear my undies before I kicked you out five years ago. And are you pretending you were forced to wear Miss Robinson's underwear?" She shook her head in mock disbelief.

"No, Miss," he exclaimed. "That was different. I ... I didn't choose to wear female underwear to the office ..."

"Um! Well, you didn't put up much of a fight when Miss Robinson asked you to. You even went out shopping to buy stuff your size."

"It was because I didn't want to lose her, so I agreed to do what she wanted."

"That's ridiculous, Simone. I don't believe what you're saying. You can't make someone do something like that unless they're willing. You made no fuss yesterday putting on the jeans and Prosecco T-shirt."

"That's because I was scared you would punish me, Miss."

"Oh, for heaven's sake! You're bigger and more powerful than me, so how can I make you do anything you don't want to--deep down that is, in your subconscious."

"But I'm locked in this device, Miss,"

"Yes, and you closed the padlock, not me, Simone--you did that!"

"But I had no choice, Miss. My stuff is locked up and I've no money or bank cards."

"Listen to yourself. If you wanted to, you could be all macho and break the shed door down. You could purloin a file and destroy the lock on your chastity device. And you could have begged a friend to have lent you money. But you like being submissive to women. You enjoy being controlled, humiliated and punished by women. Admit it, for goodness sake!"

He was stunned listening to this. What she was saying was largely true.

"And don't try to tell me that you've not fantasised about parading around in public dressed entirely in women's clothes. It's taken me to push your dream into reality. And what thanks do I get? None!"

She was right that he had dreamt of being dressed completely as a woman. And, what's more, his vivid imagination had conjured up scenarios where he had been forced to dress like that by a strong, determined woman--someone like Sarah. Yet he also knew that what his brain was able to conjure up while in a frenzy of sexual excitement was very different to living that life in the real world. He didn't know how he would cope living as a female, 24/7, for a year.

He didn't say anymore and Sarah could see that he was defeated and dejected. "We need to get inside because you've got chores to do. No more wasting time out here, Simone. Get out of the car. Now!"

Faithfully, he complied with instructions and, once in the house, set about doing cleaning and laundry while she cooked dinner. At 7 PM, he was told to stop and shortly afterwards they sat down to eat. With the meal eaten, and the dishes washed, she remarked, in an almost off-the-cuff way, "Are you getting frustrated? Do you need relief?"

His eyes shot open on hearing this. Yes, he was desperate for relief yet knew that he was not yet due to be released, not least because of the penalty days he had been awarded over the weekend. He suspected a trap, but replied, "Yes, Miss. Please, I do need to release the pressure. I'll be so grateful if you would unlock me, just for a few minutes, while I can ... er, you know, do what I need to do."

Sarah could tell exactly what he meant and gave him a faint smile. "Hmmm ... well, first I want you to write another undated letter of resignation to Ms Deacon to replace the first one." His stomach fell but, like so many men, his actions were governed by his penis, not his brain. He feared that he would write the letter and then discover that Sarah's definition of 'relief' would not be the same as his. Perhaps she had in mind a prostate milking. "Erm, what do you mean by relief, Miss?" he enquired.

"For goodness sake, what do you think I mean? Are you dense? I'll unlock you and give you a handjob, Simone, and it will be a good one, I promise. And you can do something for me at the same time because I'm getting frustrated as well. Come on, I need a decision."

What she was promising, if she was being truthful, exceeded his expectations. "Erm, OK, Miss, I will write another letter." Even as he said it, his logical brain was telling him not to be a fool, but it was overridden by his desperate need to be unlocked. Just being unlocked, allowing his penis to expand to its full size, would be pleasurable and whatever followed would be a bonus. Furthermore, once unlocked maybe he might somehow avoid being relocked again. No, even thinking that was being ridiculous!

Presented with a pen and paper he wrote what Sarah dictated:

Dear Ms Deacon, I want to thank you for the enormous support you and everyone in the department have given me after I confirmed to you that I was in the process of transitioning to become female. However, after careful consideration, I have decided it is best that I resign with immediate effect so as not to be a disruptive influence within the department. Leaving will also allow me space and time to focus on managing my transition. Please do not try to persuade me to change my mind as it is made up. Sarah is still supporting me and agrees that resigning is for the best. Thank you for all you've done. Yours sincerely, Simon Smith

He read what he wrote, and for an instant thought of tearing it up, but he was desperate to empty the build-up of semen inside him. Sarah took the letter from him and left the kitchen to hide it away somewhere. When she returned he was instructed to strip naked. He did so earnestly and was soon standing in front of her wearing nothing but his chastity device. Any embarrassment was countered by the thought that he should soon experience some freedom and already his penis was straining at the leash.

"You do know that I shouldn't be doing this now, don't you? You're not due for release yet. But as you've written the letter I will let you ejaculate but you're not to think I'm a soft touch. Don't expect me to do this every few days, but I have promised to take care of you, as long as you're obedient, and you've been obedient this evening."

"I understand, Miss," he replied. Whether he did understand is a different matter but he was growing excited as Sarah reached into the drawer of her bedside table. When he saw what she had in her hand, his jaw dropped...