Caught in a New Life

Chapter 23

It was very early in the morning when Monroe got woken up by Ms. Thompson's alarm, earlier than usual even. All Monroe could do was groan loudly, there was prickling all over his scalp, something was kind of making the skin on his face feel weird, his legs were rather stiff, his cock hurt feeling awfully restrained and there was the stale taste of cum in his mouth. Not only that, but something seemed to be stuck up his ass as well. It took Monroe a few seconds, to realise where all those feelings came from through his sleep clouded mind, but when he did, he could only groan even louder. A groan that was quickly followed by a loud gulp when Ms. Thompson appeared at his bedside in nothing but her sleep dress and some comfortable slippers.

"Good morning Molly, time to wake up. I know it's a little early, but a look as elaborate as yours requires lots of work and time, so I'm afraid this will be a regular thing. After all you want to look perfect for your wife and make sure to have her breakfast ready for her don't you Molly? You wouldn't want her to file for a divorce so I'd have to find you another partner would you? Now don't worry, I'm sure once you get the hang of your new routine you might be able to sleep a little longer in the future, but for now practice is a key word. Now get up, don't forget your heels or you'll get punished. This extra time doesn't mean we have time to waste." Ms. Thompson grinned down at the sleeping sissy, looking exactly like some cartoon caricature of a housewife with that green goop and all the curlers. Her project was coming along nicely.

With another loud groan Monroe pushed himself to get up from his mattress, fearing that if he took too long he might get another zap to his balls or some different punishment. A punishment like what Ms. Thompson had described the day before, sending him out to be the wife of that friend of hers. He couldn't help but shudder at the thought? Lena wouldn't really allow that would she? Then again he was almost certain that Ms. Thompson could convince her and it was scaring him to his core. As bad as this was he needed to be perfectly behaved so his wife wouldn't abandon him. Then he needed to be well enough behaved to get rid of Ms. Thompson and then hopefully he would be able to convince Lena to go back to the way things were, or at least to some sense of normality again, but one thing was clear he wasn't getting out of this on his own no matter how much he wanted it. It was far too late for that with how things had gotten out of hand.

While his legs were still sore from all the walking the day before, he knew better than to not wear his mules, especially since Ms. Thompson had explicitly told him to put them on. He felt absolutely ridiculous mincing towards the bathroom, the stiffness in his legs causing him trouble as heels were the exact reason they were stiff in the first place. Like every morning Monroe was about to wait outside of the bathroom for Ms. Thompson to finish up, only this time she quickly grabbed his hand and pulled him in alongside her. "There's no need to be shy any longer Molly, now that we've become somewhat more intimate, we can share the bathroom and win some time. Besides, you aren't going to settle in your new routines without supervision and guidance." Ms. Thompson smirked as she stripped out of her nightgown, throwing it in the hamper and revealing her old body in it's full naked glory to her sissy ward.

Monroe was incredibly disturbed by the sight, the old woman anything but appealing to him, especially as it gave him horrid flashbacks to last night's oral. He didn't like this new development one bit, then again it paled compared to his new outfit and look. As worrying as it was it simply wasn't his main worry as he stood there sheepishly, not really knowing wat to do as Ms. Thompson casually walked to the toilet to relieve herself, having no hang-ups whatsoever much to Monroe's horror. "Well don't just stand there molly, prepare your bath, then strip down, the toilet will be free in a minute." She ordered him.

Sighing deeply Monroe got out of the delicate lingerie, careful with his stockings like he was taught to be, but even naked, with his cage on one end, and that horrid string on the other, he remained on his heels as he minced over to the tub to prepare his bath like Ms. Thompson had shown him the day before as the room filled up with the strong scent of the various products. He was just done with that when Ms. Thompson got up. "Alright Molly your turn on the toilet. Since you are wearing tampons you should know that you can just throw those in the toilet. You have to pull them out, a strong tug should do it, wrap them into a bit of paper for modesty's sake and throw them in the trash instead." She gleefully exclaimed as a mortified Monroe headed for the toilet.

He was more than glad to finally get rid of that horrible tampon, but reaching between his legs and pulling that string was incredibly humiliating. It felt weird having that tampon move around in his bottom with every tug, as he needed more than one, surprised at how firmly it was stuck up there. Once he had finally managed to pull it out he was all too glad to wrap the shameful memory up into some toilet paper to throw it away simply so he wouldn't have to see it again. Done on the toilet Monroe was horrified when he heard the next instruction. "Alright Molly, now that that's taken care off you can have another enema and then it's time for your bath." She spoke with delight, just loving that shocked look on his face.

"Nanny with all due respect, but, uhm I'm not planning on having any sexual intercourse so is that really necessary?" Monroe stammered completely embarrassed as he didn't want to have a repeat of last night's horror that had been that enema, he never wanted one of those again, or at the very least keep them to a bare minimum. Having some energy again now that he was at least rested, he just had to speak up about it, doubting he would change Ms. Thompson's mind, but he had to try. He also just hated the fact that he still had to call this demented woman Nanny, it had always been embarrassing, but it was especially embarrassing now that she had made him look like some damn mature housewife, someone who would never call anyone Nanny, maybe at the most be called nanny herself.

"Yes Molly, it is absolutely necessary, unless of course you aren't sexually active which is broader than just planning to have sexual intercourse right away. You can't be sexually active on and off, either you are or you aren't when you plan to abstain for a very long time. You'd need to be sexually active if you want to work on the issues you and your wife have in the bedroom, after all none of my help to make you last longer can work if there is no sexual aspect involved, and if you aren't trying to resolve your issue and train to last longer, then I guess I should tell Lena that you have given up and she should file for divorce. Don't worry, I think my friend is the marrying type, at least if you manage to please him which I'm sure you would. He can be very demanding. So are you sexually active meaning you'll have your enema, or not?" Ms. Thompson asked with a big smirk, already knowing the answer judging from the horror on Monroe's face as she once again threatened with divorce and her friend.

Monroe just looked at her in shock for a few minutes, trying to bring up an argument against the horrible shameful, invasive and uncomfortable act that was getting an enema, but he couldn't think of anything. All he could think off was how he needed to avoid the consequences of not getting one. He needed Lena more than ever as Ms. Thompson had made it very clear that she could escalate things way further out of control, not that things with his wife were looking on the up after their conversation last night. Hanging his head he went to fetch his enema bag and prepared it the way Ms. Thompson had shown him the day before.

Hanging it up he was about to take control of nozzle, hoping to get away with inserting only the very tip, the bare minimum, but Ms. Thompson got in the way again. "Hand me the nozzle and get down Molly. Since I have to be here anyways, I might as well kill some time by insuring it is delivered properly." Ms. Thompson spoke sternly, she needed some patience and a threatening look, but eventually Molly bowed her head and reluctantly complied once more. She didn't want to give over control of that nozzle, especially not after how she had used it last night, but she was in no position to fight it.

Ms. Thompson was very happy to seize control over the nozzle though as she quickly lubed it up and put it to good use on Molly's ass, skilfully fucking her sissy ward with it to the edge of a climax before releasing the water into Molly's bowls. All the wile Molly was getting filled she kept on stimulating her prostate. It had taken quite a bit longer to get Molly to that edge this time, but then again, that was to be expected given how her last orgasm had been hours ago rather than days. It made this morning edge all the more important though as it would ensure Molly would be frustrated all day making her way easier to tip over the edge tonight.

While Ms. Thompson was thoroughly enjoying herself, all this part of her bigger plan, Monroe could only think in the short term. More specifically to the end of his current ordeal. Through many moans, groans and grunts he suffered through this until he got the go signal to go and relief herself. A feeling that after all the cramps felt nearly as great as an orgasm. At least until the cramps faded and all that was left was an empty feeling and intense shame, shame only amplified by the tampon he was made to insert afterwards, and that so shortly after discarding the first. He couldn't belief he was actually wearing tampons on the regular right now. Hell if this kept up, more regular than any woman even.

"Alright Molly, now that you are squeaky clean on the inside, it's time to clean you up on the outside. Go and hop on in the tub. Use the hand mirror to peel off your mask, but don't forget your shower cap. We wouldn't want your hair to get wet. Once you're done with the mask you can scrub your body clean and soak a little more. I'll have myself a shower in the meantime." Ms. Thompson smirked as she watched Monroe eagerly getting into the tub, glad to hide his body under the soapy water despite how fragrant it was. He didn't like baths, but this was by far one of his favourite things to do out of all the things he had gotten to do since he had been branded Molly. While there was work to be done, it was also kind of relaxing, the warm water soothing, and he could lay down. As much as his body relaxed however, his mind kept going over to the dreadful things that probably awaited him today.

The water may be relaxing, but between scrubbing his smooth soft body, and peeling off that mask, Monroe didn't have time to relax a lot. The worst thing by far was peeling off that mask. He had to use a hand mirror and even though bit by bit he was revealing his own face from under that green goop, he still couldn't help but feel mortified. Without any makeup on, his face was very clearly his own yet even now he looked way too feminine. With his chin resting on the bubbles and the large pink bonnet holding his curlers in everything around his face was so feminine. Not only that, but even without all the makeup, his heavily thinned and arched brows changed his face drastically. There was not even a shadow to be seen where his beard used to be and with all the lotions and the night time mask, his skin was incredibly soft. His hand holding the mirror looking so very slender with the long red nails wasn't helping him either. Looking so effeminate even while naked and makeup free was even more devastating than it was when he was fully dressed and made up. It made him feel like he couldn't pass like a man anymore, not even if he wanted to. It was a painful realisation.

One that got interrupted rather quickly when Ms. Thompson luckily fully dressed now cleared her throat. "Someone is obviously enjoying her new look Molly, I'm so glad to see you like it so much, but I'm afraid it's time to finish getting ready now, but don't you worry, you'll get to look in the mirror more than often enough so you won't have to miss that look for too long, besides it will only get better once you put on your proper face of makeup." Ms. Thompson gleefully interrupted his thoughts enjoying his horrified look as he stared into the mirror while she held out a large pink towel for him.

Monroe couldn't believe thirty minutes had already passed, but between the very thorough scrubbing of his body, the peeling of his mask and the horrid staring time had passed quickly. He couldn't believe he had been caught staring into that mirror like some vain woman, and while what he had done wasn't anything close to admiring, but it wasn't worth correcting Ms. Thompson for, not by a long shot. Besides there was no way it would work anyways he figured as he put the mirror down and stepped out of the tub, drying himself, only to slide right back into his high heeled mules, warned by one of Ms. Thompson's stern looks and a nod towards them.

"Good, now that you're dry it's time for your daily lotions, used this one for your face, and this one here for the rest of your body. Make sure not to skip a single bit okay Molly?" Ms. Thompson asked rhetorical as she handed him some hydrating lotions which along with the scrubbing he used should turn his skin baby soft in time, the skin off a pampered high maintenance lady. It was subtle enough, but would add to the overall look. Besides it was a nice ritual and the creams carried a pretty strong scent as well. Monroe would leave a strong lavender scent wherever he went, just like a woman who wore too much perfume, but that was for later. Right now she just enjoyed seeing the sissy massage the lotions thoroughly into his skin, giving it a nice sheen all over, the small rope hanging from between his butt cheeks was a nice touch.

"Alright now that you're cleaned and moisturised for the day lets get you dressed and ready Molly. Today you'll exceptionally get to wear your clothes from yesterday again even though they aren't washed again. We'll go pick up a more extensive wardrobe later, but for now that will have to do." Ms. Thompson explained as she signalled to yesterday's clothes which she had put out on the bed for him. Monroe didn't like the idea of picking up more clothes like that horrid dress he had had to wear the day before one bit, but he started getting dressed in it anyways, groaning as Ms. Thompson pulled the corset awfully tight again. Much to his shame, the other more delicate sensual undies made his cage get uncomfortably tight instead.

All dressed up in the obnoxiously colourful, frilly and delicate outfit Monroe had worn the day before with the exception of the head and sunglasses, still wearing that bonnet and curlers, Monroe watched how Ms. Thompson pulled the chair in front of the vanity table back. "By all means Molly, please have a seat. I still need to show you how to take care of that new hairdo of yours and of course how to put on your new face. You might look pretty good all natural, but a splash of colour would definitely make you look even better. Besides you can't wear such an elaborate outfit without an equally elaborate face of makeup. It just wouldn't match." Ms. Thompson gleefully spoke, ready to show her sissy ward the last step of her getting ready routine. The step that would require most practice by far. Having little choice Monroe reluctantly minced over, keeping the steps small and perfect after last nights harsh training and sat down somewhat daintily like he had been shown before.

"Lets get started with getting that sleeping bonnet off and those curlers out shall we? Why don't you take off the bonnet and I'll show you how to take them out with the first one." Ms. Thompson explained as Monroe was all too happy to oblige, finally able to get that hideous pink bonnet off, and even more important, those horrible rollers that had tormented his scalp all night out. That whole sentiment changed however when he did in fact take the bonnet off, revealing his platinum blonde hair all tightly held to his scalp by those horrid curls. It reminded him that while naked it wasn't his face that would give away his femininity, but that horribly coloured hair that would stand out in any crowd. It didn't get any better either as Ms. Thompson grabbed one of the curlers and slowly but surely unrolled it, pulling it away from the rest of the curlers, stretching out the full length of his platinum coloured hair only to let it snap back to the tight curl it had been permed in, reinforced by spending the night rolled up.

"Good, now it's your turn, be careful not to get the roller tangled with the others or the rest of your hair otherwise you'll make a mess of it." Ms. Thompson warned as Monroe wanted nothing more than to cover his hair back up, even if it was with that horrid bonnet. He knew that wasn't an option with Ms. Thompson in the room however so instead he grabbed a second roller and slowly but surely started rolling it outwards until that strand too snapped back in a curl. Roller after Roller Monroe released his new blonde hair, until he was left with a somehow slightly curlier messier version of yesterday's hairstyle, the rollers standing in a row on the vanity table.

"There we go, now that those curls are nicely retightened again, it's time to brush them out, get a little bit of that spring out of them while you thoroughly untangle any messy hairs that might have crept in. Try to shape your curls into yesterday's hairdo while you are at it Molly, give it more volume, pile it up on your head a little more." Ms. Thompson gleefully instructed as she put an ornately decorated brush into one of Monroe's daintily gloved perfectly manicured hands. It was just too precious to see him obey and brush out his hair, cringing with every stroke of the brush as it was quite a bit of work unlike what he was used to. Such elegant work as well. He needed a few pointers on where and how to brush, but eventually he was left with a hairstyle that was a near perfect copy of yesterday's hair.

"Fantastic Molly, that looks just perfect, I can see you'll get the hang of caring for your hair shortly. Now it would be a downright shame to let all that work droop down a little flatter during the day so just to be sure give it a good dosing of this all over, and keep in mind Molly, when it comes to a sissy like you, too much is better than too little." Ms. Thompson grinned as she handed Monroe a pink can of sweet smelling hairspray which he saw himself forced to liberally apply all over his hair, firmly cementing the elaborate hairdo in place for at least the next twelve hours. It could be pressed down a little with enough force, but would spring right back in shape when released.

"Now let's get started on the trickiest part of your morning routine shall we Molly? Your makeup! This is going to be so much fun, and it is an integral part of your look so pay attention. To get started I'll do half your face and explain every step, then you'll do the other half, check, clean up and repeat. I don't expect a flawless look, but in the seven times you'll reapply it this morning I expect you to at least create something passable from afar. You'll get plenty of practice opportunities after that though, so I'm certain you'll be a pro in no time." Ms. Thompson exclaimed as excited as he was embarrassed as she put out a bunch of products on the vanity table, more than he ever thought one could need to make up their face, but he was wrong as she carefully gave a brief explanation for all of them.