Sarah decided that Simon had had enough time away from his chores for one day, and so, despite Claire being keen to see him in his new outfits and to teach him how to apply makeup, Simon spent the rest of Saturday working in the garden. As he knew from experience, gardening is a never-ending task and there is always something to be done.
At 7 PM, just as the light was starting to fade, Simon was called in for dinner. As he had expected, it was a hearty meal that he shared with Sarah. This was an area of his new life where Sarah was true to her word that she would take care of him. The only thing he missed was a glass of wine as she had decided, at the outset, that Simon should not consume alcohol. He could only look on longingly as she savoured the wine she poured for herself, sometimes, in a mean way, licking her lips and teasing him about how good it was. After they had eaten, and Simon had washed the dishes, she reminded him that he had lines to write following his outburst in the department store earlier in the day. He hated writing lines but obediently fetched his pad and pen and began writing out a sentence that Sarah dictated to him; "Childish tantrums will result in punishment".
"Write that out two hundred times before bed," she instructed. "Think about the sentence as you write it and don't make any mistakes ... or else." She didn't explain what 'or else' meant, but it had to refer to something unpleasant and best avoided.
With the first line written as a template, he set about completing the remainder, calculating that this would require six pages of A4. So far, this was the greatest number of lines he'd had to write, and he counted his blessings that the sentence was short. Nonetheless, he knew that a monotonous time lay ahead, perhaps as long as two hours.
As he worked his way down the first page, he made the fatal error of losing concentration and allowing his mind to drift. He thought to himself, Why should I be writing lines like a child? This is ridiculous.
For a few moments, he considered rebelling. After all, Claire had expressed surprise that he hadn't resisted his new lifestyle before she concluded that he was deriving pleasure from it. It was true that he did enjoy some aspects of being a submissive but, presumably like other submissives, there were other aspects of his new life that he despised. Line writing was one of them, and dressing as a woman in public was another. Surely, he thought to himself, there should be some give and take with Sarah. As far as he could tell, she was deriving immense pleasure from all aspects of their new relationship and he was doing his utmost to keep her happy, at his own expense. Was it unreasonable to expect, in return, that Sarah should make some concessions that suited him? That way, they might both enjoy their new lifestyle.
Simon then remembered what Claire had told him that morning. His relationship with Sarah was for real and it wasn't some game of kinky sex with limits and safe words. Therefore, why should Sarah make concessions to enhance his enjoyment? As a submissive, should he not take the rough with the smooth, gaining enjoyment where he could, which was paid for by the elements he detested?
He looked down at the paper and his stomach sank as he realised he had made a mistake. Damn! He had discovered the cardinal rule of line writing, which is to stay focused and not go on autopilot. He had let his thoughts wander, and now he had made a mistake. Silently, he cursed himself for his stupidity.
For a few seconds, he considered overwriting his error or perhaps crossing that one line through and writing it out again. However, he remembered Sarah's threat of 'or else'. He therefore took the bold step of screwing the offending page into a ball and lobbing it into the bin. Feeling downhearted, he started again, determined to concentrate on the task in hand, no matter how tedious, and not to let his thoughts drift.
Two hours later he was finished and suppressed a sigh of relief as Sarah approved his work. "Good girl, Simone," she said, condescendingly. "I hope you've learnt your lesson because outbursts will not be tolerated. Now it's bedtime for you."
oooOOooo
Simon slept well and considered himself fortunate that he only suffered a mild nocturnal arousal. It was painful but not as bad as some previous nights. Sarah had suggested to him that Sunday mornings were when he should spend most time taking care of his body, and, in particular, making sure he was hairless from the neck down. This required careful attention to detail and he spent a long time in the bathroom, but being careful not to take so long as to be late taking up Sarah's breakfast at 8:30 AM.
As she sat up in bed to eat, she told him that Claire would be returning at 10 AM. In the meanwhile, he was to get on with indoor chores. Sure enough, at ten o'clock on the dot, Claire rang the doorbell and Simon hastily went to let her in. "Morning, sweetie," she announced, before pushing past him and making her way to the lounge.
"Where's Miss Jones?" she asked.
"She's having her shower, Miss, and will be down shortly. Would you like a coffee, while we wait?"
"Nah, I don't think so. But why don't you go and face the wall? I love obedient men."
Simon was certainly obedient, so he did what she said, placing his hands on his head.
"Did I tell you to put your hands on your head, sweetie?"
"Er, no, Miss. Sorry, Miss."
He started to remove them. "No! Keep them there. You used your initiative, which I like in a man. Well done, sweetie."
He stood there, pleased she couldn't see his red face. As he often did when facing the wall, he tried counting seconds to relieve the boredom. Then he attempted some mental arithmetic to stay sane. Neither, though, worked, and tedium soon set in. Surely Claire, with her bubbly personality, couldn't stay quiet for long?
Sure enough, after about five minutes, Claire felt compelled to say something. "I'm bored, sitting here," she sighed.
She's bored? What about poor Simon?
"Talk to me, sweetie. I bet you can't wait for the fashion show this morning. You'll get to put on your sexy undies and your business outfits. You're going to become very aroused, I reckon. I will see it in your face, sweetie, as the discomfort from your cage distresses you. What do you think?"
"Er, yes, probably, Miss." He knew full well that it was a hundred percent certainty that he would become aroused wearing flimsy lingerie in front of two gorgeous girls.
"How on earth will you manage in the office?" she sniggered. "Life might be one all-day arousal fest!"
"I don't think so, Miss. Wearing female clothes in the office is very different to wearing them here, in the home. I'm not looking forward to it, Miss."
"Well, never mind. Everything comes at a price. If you want to enjoy wearing frilly stuff in private then you have to pay for that privilege by wearing it to the office. I'm right, aren't I?"
"Yes, Miss, I can understand what you're saying."
"Anyhow, I'll be showing you how to apply makeup to help you pass as a woman. I'm dying to see the final results!"
How that was to help him, he had no idea. Fortunately, at that moment, Sarah walked into the room, fresh from her shower. She wasn't surprised to find Simon facing the wall with his hands on his head.
After greeting Claire, she told Simon to join them. He turned to see they were sitting side by side on the sofa and memories of how this ended up yesterday flooded his mind. Immediately, he felt his penis starting to swell.
"Where are all the clothes you bought yesterday?" asked Sarah.
"Upstairs, Miss," he replied.
"Well, they're no use there, you numbskull. Go and fetch them, all of them. And come down naked."
The two girls smirked at each other as he hurried upstairs to comply with Sarah's instructions. He returned a few minutes later, wearing nothing apart from his chastity device, and carrying his bags of shopping. To say that he was embarrassed would be an understatement. Parts of him had gone red that he didn't think could go red.
"Stand in front of us, sweetie, with your hands on your head," instructed Claire, who then looked him over. "Wow, she has a beautiful figure. Well-toned but not overly muscular and no belly fat. You're so lucky, Sarah."
Sarah smiled, looking pleased with herself. She stood up and emptied his bags, spreading the contents across the floor so she and Claire could decide what he should try on first. Simon couldn't prevent his eyes from drifting towards the collection.
"Eyes front, sweetie," commanded Claire. "We know you're dying to try stuff on but have some self-control, for pity's sake."
The two girls look through the pile. "Hmmm," pondered Claire. "How about the pale blue undies?"
"Sounds good to me," agreed Sarah.
Sarah threw him a pair of thong panties. He dropped his hands from his head and caught them. Looking at them, he was left wondering how they could possibly cover his chastity device. He started to put a foot through a leg hole.
"No!" hissed Claire. "What are you doing, sweetie?"
"Er, I'm putting on the knickers, Miss," he answered, sounding puzzled.
"What about the suspender belt? Good grief! You've watched too much porn, sweetie, where the suspender belt is worn over panties. If you do that, then it will be difficult to go to the loo because you won't be able to pull your knickers down far enough. Put the belt on first, and then the knickers." She shook her head as if she couldn't understand how someone could be so stupid. Sarah just giggled at his embarrassment.
Sarah passed him the complementary suspender belt and, feeling very self-conscious, for the first time ever, he put on a suspender belt and followed that with the thong. He couldn't believe it was the right size and, as he'd expected, it did nothing to support his heavy chastity cage which was in danger of falling out of the flimsy garment. To add to his woes, the fabric at the back had given him an uncomfortable wedgie.
"I hope your bum's clean," mocked Sarah, to Claire's amusement.
Next came the matching bra which he expertly fastened up by reaching behind his back. This impressed Claire, who whooped for joy at his dexterity.
The bra was unlike the plain T-shirt ones he had purchased at Emma's insistence. This was lacy and had an attractive design. It was amazingly delicate, almost gossamer thin, and weighed next to nothing. Moreover, it was largely transparent apart from a small section in each cup designed to obscure the nipples of women who chose to wear it. He, of course, had to place his falsies inside the cups which, by themselves, covered up his nipples.
He felt very vulnerable standing there in his skimpy underwear yet, at the time, he found it arousing and he was aware of growing discomfort as his penis attempted to swell. If he was just wearing this ensemble around the house he wouldn't mind, but the thought of going into work with it on was terrifying, not that his penis was registering what his brain was telling him. In its ignorance, it simply continued to expand.
Neither girl missed the changed expression on Simon's face as he coped with increasing agony, but neither chose to comment, preferring instead to smile knowingly at him.
He was then instructed to put on a pair of black stockings, another first for him. As he was well-versed in dressing in tights, this wasn't especially difficult, but he was alarmed to see that the stocking tops barely reached above midthigh. Attaching the suspender clips hitched them up a little more, but not by much.
Even Sarah looked concerned. "Hmm," she remarked, "this might be a trifle embarrassing because I don't think her skirt will reach much below her stockings."
"She'll just have to be careful then, won't she?" stated Claire.
"Yes, but if she starts showing stocking tops my boss, Vicky, is going to blame me. She'll say that I should have given Simone better advice on what to wear."
"Well, see how it goes, Sarah. If she embarrasses you then you'll have to punish her when you get home. She's going to learn. Anyhow, I think she looks good, and she'll look even better when I've done her makeup... Put the blouse on, sweetie, the pale blue one."
Simon picked up the blouse that Claire required. It weighed no more than a feather because it was virtually transparent. Looking down, he couldn't just see the outline of his bra—no, he could see the details of its intricate pattern. It hid nothing.
"This could be embarrassing for me as well, Claire. Vicky going to think I'm dressing her up like a tart."
"She'll be fine, Sarah. Stop worrying. Besides, she's got a jacket to wear... Put the royal blue skirt on, sweetie."
Simon stepped into the skirt. Like everything else purchased for him, it was a perfect fit, except in length. As Simon and Sarah expected, it was so short that it barely reached more than a couple of inches below his stocking tops. He could see the look of consternation on her face and thought this was the time to add his own views. "I don't think these clothes are suitable for the office, Miss Jones," he commented. "I think I'll get into trouble with Ms Deacon and you might as well, Miss."
Sarah looked deep in thought. For once, she didn't immediately slap him down. No, that honour fell to Claire. "Stop whining, Simone. What you're wearing is beautiful and very feminine. But it would help if you did it justice by behaving like a female. If you go strutting around like a stereotypical man, with your knuckles grazing the floor, then, yes, you'll reveal things you shouldn't. Just think about what you're doing and everything will be OK."
"I'm not sure," opined Sarah.
"Please! At least give it a try, Sarah!" Claire impatiently exclaimed.
Sarah thought for a few moments before concluding, "OK, then, but I'll be livid if she embarrasses me in front of my co-workers." She glared at Simon to hammer the point home.
"Good! That's settled," decided Claire. "Now she just needs to try on the jacket and then I'll give her a makeup lesson."
The jacket, like the rest of the ensemble, was a good fit. The final step in his transformation was the application of makeup and Claire suggested that Simon should strip completely naked to avoid the possibility of makeup soiling his clothes.
Once he had removed everything, he was instructed to sit on a chair at the kitchen table. Claire brought through the makeup that she had selected the previous day and sat on another chair alongside him. Sarah produced a large mirror which she propped up on the table so that Simon could follow the instructions Claire was to give him.
"Right, sweetie!" Claire announced. "I'm going to apply makeup in layers and the objective is to use smoke and mirrors to make your face look more feminine. I'll be emphasising certain features and, where those features don't exist, I will use the makeup to create them."
It sounded so simple and, with her plan outlined, she set to work. Simon followed progress in the mirror, while Sarah looked on from the other side of the table. It was soon evident that Claire knew her trade and she expertly applied a dash of this and a smudge of that. Step by step, Simon's face took on a more feminine appearance and by the time she'd finished even he thought he bore a strong resemblance to a cis woman.
"Wow!" exclaimed Sarah. "That's good. It's really good!"
Claire looked pleased. "Absolutely! If she does this every morning it will boost her confidence no end."
The problem, though, was that it had taken Claire twenty minutes to work her miracle. Simon wondered how long it would take him and whether he would achieve anything like the example she'd set. It wouldn't help that he would be working from a mirror which was bound to make the job more difficult. Besides which, he had struggled to follow which concoction she had applied where and in what order. It had all the makings of a disaster. The expression on his face, beneath his makeover, spoke of his concerns.
"She doesn't look happy, Claire," intoned Sarah, stating the obvious.
"Oh, for goodness sake, Sarah, she'll get used to it. I suggest she goes upstairs, removes this lot and then we watch her do it herself from scratch."
Simon, armed with makeup remover and cotton pads took himself upstairs. Removing the makeup took as long as applying it but, after an age, he made his way downstairs. With the two girls watching, he attempted to reconstruct what Claire had achieved. The result was disappointing, and that was being polite. Even with Claire telling him which tube to use, and where to apply it, he still failed miserably. He might even have passed as a dame in pantomime.
"Oh, dear," sighed Claire, "I didn't realise she was unable to follow simple instructions." She shook her head in the direction of Sarah before turning to Simon and saying, "Off you go upstairs to take it all off again so you can try again."
His second attempt was slightly better and a third attempt was almost passable. A fourth attempt was needed but Sarah had had enough and intervened, saying, "She's got chores to be doing, so we'll have to call it a day."
Simon was both relieved and distressed—relieved because he was tired of trying, and distressed because he knew that the following morning he would need to apply the makeup for real. He could not see that being successful.
He was instructed to put on his gardening clothes, namely his jeans and T-shirt, worn over his plain underwear, and then he was sent outside to get some work done. Even while busying himself in the garden, he was unable to forget the intense anxiety he felt about what the following day would bring. He worked until 7 PM when Sarah called him in to eat. As they ate, he felt the urge to raise the concerns he had with her. "Er, Miss," he ventured. "I'm sorry but I'm scared witless about going into the office wearing those clothes. I just can't do it. Please don't make me."
Sarah stared at him for a few moments and clenched her jaw. He thought she might be about to agree with him. "Miss Fraser says you'll be OK and she's done a module at college on this. She's the expert, so do what she says and you'll be fine."
"It could cause you embarrassment, Miss," he interjected, in a last ditch effort to stave off utter humiliation.
"Miss Fraser says it will be OK—subject closed!"
oooOOooo
After dinner, Simon had free time and he sat in the lounge with Sarah. She was watching some soppy film while he was worrying about how he would cope at work the next day. Not only would he be wearing an ultrashort skirt and stockings, but also an almost transparent blouse which would do nothing to obscure his fancy bra. Not even the cis woman in the office wore clothes like that. Most wore trousers and those in skirts usually chose a longer length. And the older women were extremely modest in how they dressed and he felt certain they would take him to task for wearing clothes that were so revealing. On top of all this, he also had to wear makeup and he very much doubted that he would apply it convincingly. Consequently, not only was he worried, but he was also becoming depressed. He suspected that Sarah shared some of his concerns, yet she had refused to back down, instead referring back to Claire's insistence that all would be well. Simon doubted that very much. He had known for some time that he had jumped from the frying pan into the fire, but where was there to jump to from the fire? Nowhere, it seemed. Yet he had to do something.
Reaching into his pocket, he withdrew his phone. Sarah had put software on it to restrict what he could do, but he knew that she had not deleted his contact numbers. This was probably an oversight but it could give him the escape route he needed. He looked up James's number. [Readers may recall that it was James whom Simon had encountered while shopping for lingerie under instructions from Emma. He and James had been on the same football team and James had pulled his leg about him purchasing plain underwear, saying he couldn't imagine Emma appreciating it. Of course, James had been completely unaware of the truth.]
He looked over at Sarah, who was still absorbed in her film, and he deftly typed a text message. He hesitated for several seconds, aware that if he continued he would be burning his bridges. He pressed send, which initiated a conversation with James.
S: Hi James
J: Not heard from you for ages, mate. Thought you were dead. LOL!
S: I might as well be. I'm in big trouble
J: Police?
S: NO!!!! Girlfriend
J: Emma? Your fiancée?
S: No, we split up. I'm with Sarah
J: Scary Sarah? I remember her. Is she pregnant?
S: NO!!!! But I need to escape
J: What you talking about?
S: Can I stay with you for a few nights?
J: I suppose so. YES!
S: Including tonight?
J: What???? I guess so. You're going to have to tell me what's going on, mate
S: I will. Can you pick me up at 1 AM when Sarah will be asleep?
J: That's the middle of the bloody night! OK! I'll pick you up. Where are you?
Simon gave James the address of Sarah's house and told him he'd be waiting outside. He had taken a decision and a plan was formulating in his mind. He now had to execute the plan and pray that Sarah didn't get wind of what was going on.
