Caught in a New Life Pt.9 (Patreon)

Chapter 12

The arrival of yet another day was set in by another groan from Monroe as he was rudely awoken by Ms. Thompson’s loud blaring alarm. By now he didn’t need to be told what to do anymore as he made is way through his morning routine, smelling strongly of lavender just like Ms. Thompson when he came out of the bathroom. His mind was more on what his closet would bring this morning than the fragrant soap and shampoo.

Making his way across the hall naked under the watchful eye of his nanny Monroe cast his eye down the hall to the master bedroom, It was just a closed door, but he knew that behind that door his wife was still fast asleep in his bed. The bed he hadn’t shared with her for what felt like ages, in a big part this seemed longer due to how badly his cock was throbbing and leaking in his cage. Damn he really needed some relief, but to do that he had to get Ms. Thompson’s approval two more days.

His life had been so much easier back when he still slept in that room, no alarms, sex whenever he wanted and no horrid old hag to constantly watch over him. “Get moving pansy!” Came the sharp sound from behind him as Ms. Thompson made him snap out of his day dream to move into the guestroom that now held his closet.

Opening up the closet for the grand reveal of his new outfit Monroe looked confused. There were the panties, the pantyhose and some weird shimmery long things in black, white, cream and nude. The top looked way to narrow to be a dress, yet the item looked way to long to be a skirt.

Seeing his confusion Ms. Thompson explained. “Those are underskirts pansy. For you clothing progression they will count as a real skirt but for now this will do, unless of course you are planning to go somewhere.  Now what are you waiting for? Don’t you appreciate your new clothes pansy? I can just take it away again if you like. Just remember you will be going to the store with me no matter how you are dressed.” She said sharply.

“No, Nanny, I… I will wear it.” Monroe said, he felt so pathetic, but the more clothes he got the better. He had been hoping for a t-shirt though, or some pants, not this weird skirt. He couldn’t go out in a skirt. His pantyhose and panties might be hidden underneath his regular clothes, but if he wore such outerwear as well he would surely get noticed. Still it would be better than being dragged out in only his underwear. After this he only needed shoes and something to wear on top right, with five days left there were still chances for him to get pants before they went out to the store right?

Reluctantly he got dressed in what clothes he had for now. It was the only way of earning anything new, and while he felt nearly certain Ms. Thompson couldn’t find anything worse than this strange skirt for him to wear. He didn’t want to take the chance. The bitch certainly seemed resourceful enough. Slipping on his panties was easy, the pantyhose once again gave him trouble. He barely dared to touch the delicate material, afraid of damaging it and receiving another punishment. Just like before the thin soft nylon felt amazing on his legs though.

Ms. Thompson smirked rather than being annoyed as Monroe took his time with his nylons. He was careful just like she had demanded and it was a joy to see him slide them up his legs with such concentration. Putting on ones nylons was such a girly task, it instantly made him look like a great big sissy.

After the nylons came the skirt he had gone with nude nylons hoping to get them as invisible as possible once more. The skirt however was black, it somehow felt like his least worst colour option although the garment in and of its own was terrible. As horrible as it was, he had to admit it felt amazing to the point of his cock uncomfortably throbbing in it’s cage. The slippery satin moving over the soft nylon was pretty much as electrifying as the movement of nylon against nylon.

As he slid the skirt further up his legs it became pretty clear that he would feel this a lot. The skirt fit awfully tight around his legs, pressing them together and keeping them together as the fabric didn’t stretch much. When he pulled it up all the way the waist band rested just underneath his belly button, soon clinging his hips and butt tightly as Ms. Thompson zipped up the back. From there it hugged his legs all the way down to his ankles where there was a little slack, but only enough to move one foot right in front of the other and no more.

“Uhm Nanny, I don’t mean to be a bother and I do want to earn new clothing today. Is there any way I could get something other than this thing though? I mean I can’t move in this, it’s way too tight and way too long.” Monroe pleaded trying to make a case for himself.

“What are you trying to say pansy? You would rather be a complete slut and prance around in a micro mini skirt? I might consider that for the future, this skirt isn’t to show off however, it fits perfectly as intended. I mean you CAN move in it, just not in the boorish way you have been moving up until now. It’ll take some getting used to, but you’ll get the hang of it eventually. Just be careful when you step, don’t try to over step, just take small dainty steps like an elegant pansy and you’ll be fine. Now walk with me.” Ms. Thompson taunted as she grabbed his arm to support him while taking a step forward.

Monroe nearly tripped as he tried to match her step, immediately getting scolded by Ms. Thompson who kept him upright. “Small dainty steps pansy!” she said before immediately trying this again, taking a for her normal step forward once more. In order to follow Monroe had to roll his leg in front of the other as the skirt didn’t permit both forward and sideway movement at the same time. He could keep his feet next to one another or right in front of one another. This rolling motion made his hips roll along, his butt wiggling obscenely as he needed to take three steps to match Ms. Thompson’s one.

It took a lot of concentration for him to pull off without tripping only to have to repeat it right away after finally catching up with Ms. Thompson who promptly took another step with Monroe taking three more quick minces hobbled by his skirt. While walking required his utmost concentration it was a very distracting thing to do. The inside of his smooth nylon legs constantly rubbed over one another while the satin skirt rubbed over the outside of his legs in a very intense thrilling sensation that made him whimper as his cock tried growing in its cage.

Ms. Thompson ended up taking him for about three tours around the room before finally trusting he had the hang of it enough to move on his own without support. “Alright pansy, let go down to the kitchen, you have work to do. Lead the way and when it comes to the stairs you’ll need to take one step at a time and you’ll be fine. Now keep your back straight and get that mince going. One more tip, if you want to keep your balance more easily just tuck your elbows against your waist and keep your under arms out straight. It’ll help trust me.” Ms. Thompson said as she gave him a pat on his butt to get him going.

After his near fall when he had started out taking his first steps Monroe was very nervous to get moving. Although he didn’t like the sound of Ms. Thompson’s tip as it would make him look like such a pansy, he needed all the help he could get. Besides, it was not like he was anything but a complete pansy in her eyes to begin with. Completely embarrassed Monroe tucked his elbows at his waist and held out his underarms just like his nanny had described as he made his way to the kitchen.

Following behind closely Ms. Thompson had a broad smirk on her face. The hobble skirt she had given Monroe gave him a very pronounced dainty wiggle, the arms on the other hand transformed this into a real sissy mince. Especially with how much concentration his walking took up, it prevented him from paying too much attention to how exactly he was holding his arms making his wrists hang limply.

All in all it looked a little too clumsy with too much looking down to be perfectly elegant. Ms. Thompson was none to bothered by it though, this skirt would prevent Monroe from doing anything but mincing and like they said practice made perfect. The arms while they didn’t do too much they offered a thought of more security. In time he wouldn’t even think about how he held them, it would all become a habit.

Her job could be so easy and satisfying some time, just one piece of clothing and her work was done for her, already she was reaping the rewards. By the time they made it to the kitchen Monroe was already starting to look a little less clumsy. Apart from his new walk the daily routine carried on like usual. Monroe put on his apron and started preparing breakfast.

During the preparations he found out about yet another restriction the new skirt posed. He needed to reach something rather low, but he couldn’t really figure out how to get to it without falling over. Not until Ms. Thompson gave him some advice at least. “If you need to stoop down it’s best if you just bend at the waist. You can move your butt back a little to keep balance if you must.” She casually informed him. Blushing fiercely Monroe followed her suggestion finding out that it really did work. He didn’t like how it raised his butt high up in the air however. Until he was out of this skirt he’d have no choice though.

Things were only seeming to get worse and more restricting for him. He should really put an end to this, but with Ms. Thompson constantly watching him he couldn’t step out of line at all. All he could do was swallow his pride or suffer the consequences, consequences which had moved from losing his reputation and being publicly humiliated to getting his orgasm postponed and getting spanked. With the ability of Ms. Thompson to fry his balls at a moments notice he simply couldn’t escape.

Eventually Monroe had his wife and Ms. Thompson’s breakfast prepared. Every move he had made up until now he had had his arms to help steady him, but that little help now disappeared as he had to carry a tray with his wife’s breakfast. All of a sudden all the progress he had made in his mince disappeared as he moved a lot more uncertain and clumsy than before while making his way up to Lena’s room.

While he was being pushed further and further into feminity and the role of servant Lena’s status on the other hand was closer to royalty than anything else. More so even as Monroe was once again forced under the sheets after serving Lena her breakfast on bed. With a full stomach and satisfied from her multiple orgasms Lena moved into the bathroom completely ignoring Monroe otherwise as he cleaned up and minced back down with a plate full of dishes and face smelling of pussy.

Down in the kitchen he put everything including Ms. Thompson’s dishes away to be washed before getting to his own meagre breakfast. Ms. Thompson was very glad to see how Monroe’s arms instantly moved back to the position she had hinted at to keep balance. Right now he might be doing it on purpose, but in time it would grow into a habit, she would make sure of that. All she really needed to do was prevent him from feeling absolutely certain about his balance and she knew just the way to do so.

Just like with stooping down and walking the skirt forced Monroe to adopt a new way of sitting. There was no more man spreading, no crossing his legs. He could only sit with his legs tightly tucked together. It was uncomfortable, Monroe never sat like this, he was just not used to it, but the skirt gave him no choice. Unbeknownst to him it would help a great deal with making him seem like he was very used to wearing skirts once he was allowed a looser skirt. A woman, especially a woman wearing a skirt didn’t sit with their legs wide open.

It was during his breakfast that Lena arrived down in the kitchen, refreshed from her shower, while her cheeks were still glowing from her orgasm. Seeing her husband sitting there so daintily at the table she couldn’t help but giggle. With Monroe spending most of his time in the master bedroom which she guessed was now her room instead of theirs, under the sheets she hadn’t really seen what he was wearing. “Oh my god, you’re wearing a skirt?!” Lena laughed making Monroe turn bright red.

“Yes he is, Monroe, why don’t you get that butt of yours off your seat and show your wife your skirt properly? Make twirl for her, walk up and down to the sink, just let her get a good look at that skirt of yours.” Ms. Thompson rapidly snapped as the mortified guy got off his seat.

He hadn’t even dared look at Lena yet, but now that he did he felt even more embarrassed. She stood before him in a skin tight white dress without sleeves and a very short skirt. On her feet were a pair of white knee high compression socks and white sneakers. Her hair was pulled back in a tight high ponytail and judging from the bag she carried she was about to head out for a round of tennis. A sport they usually played together. It hurt that she hadn’t even asked, then again with all his clothes missing the last thing he wanted was to go out in public. The most painful part however was that she looked so stunning while he felt like a clow.

Nevertheless he followed Ms. Thompson’s commands to the letter, getting up in this awkward restrictive skirt and performing a twirl for his wife. Doing so with what little movement the skirt allowed was down right scary. He desperately needed his arms to help in his balance, just the way Ms. Thompson had shown him. It only caused Lara to laugh harder as he then proceeded to mince back and forth in the kitchen, his elbows tucked at his waist, his underarms sticking out and his wrists limp. Lena suspected that Ms. Thompson was behind this ridiculous pose for his arms, a pose that paired with the heel to toe step the skirt forced him in really made him look like a huge sissy. She figured it for his need of balance, but there were other ways to do that. Still Lena chose not to burst that bubble.

“My my, you look really precious in your skirt Monroe. In any case, I should get going now, I have a tennis match to attend. Oh Ms. Thompson I do have a request. You know how if he is good today, he only needs to be on his best behaviour one more day to get unlocked so we can have sex again right? Well in the light of that I would like to spend tomorrow, the day he is supposed to be unlocked if he is good here at home. I imagine something like a spa day of sorts, I think it can be great foreplay working up to a climax later that evening, IF he deserves it. Would you mind teaching him some things that could make for a fun spa day?” Lena casually requested.

Monroe couldn’t believe what he was hearing? Lena was telling this old hag so openly about what remained of their sex live, well it was kind of logical since whether he would get to have sex or not was up to Ms. Thompson’s judgement of how good he was. He had kind of accepted that fate already, but Lena openly requesting her to teach him something, something as embarrassing as skills to give a spa treatment came as a whole new shock.

He desperately wanted to object to how these women were casually discussing what skills to teach him. Yet like Lena had said, he only needed to be good two more days and they would get to have sex with his wife again and hopefully reclaim some of his manhood. He wanted nothing more than to fuck Lena’s brains out to the point where she wouldn’t want to lock up his cock again, but then again after what happened last time, he wasn’t so sure that was even realistic. Proving himself that it was a one time thing and that he wasn’t a premature ejaculator was a bigger priority.

One thing was for certain though, he did not want to get his orgasm postponed again. He could already feel his balls growing uncomfortably full. Something that had only gotten worse with how he wore these sheer nylons all the time. They felt so sensual on his smooth skin, especially when rubbing together which was a constant problem with this skirt. He couldn’t believe he actually got off on wearing such feminine garments. Whatever the cause he desperately needed his orgasm so instead of protesting he remained silent.

“That sounds like a lovely idea Lena. By the way before you leave, are you coming home for lunch today or shouldn’t we wait on you?” Ms. Thompson asked with a bright smirk. She loved the idea of teaching Monroe about personal grooming both on himself and others. She was also loving the way Lena was starting to take a more active role in his training or at least demanding what he was trained in. It showed her that she was succeeding in convincing Lena to see and treat her husband more and more of a servant.

“I do plan to have lunch here yes, I think I will be home at around twelve thirty. I have plans for the afternoon as well however.” Lena said continuing the trend of staying out of the house and away from Monroe. Although this time it wasn’t really planned. Linda had asked her to come in for an evaluation of Ms. Thompson’s services. With that Lena said her goodbyes and left for her tennis match leaving Monroe alone with Ms. Thompson again.

Much to Monroe’s disappointment that was a very regular occurrence these days. Ever since Ms. Thompson’s arrival she had taken over his life completely. He barely saw his wife anymore, except when it was to service her both with his tongue and otherwise. Ms. Thompson however was with him for at least 20 hours a day, usually more even. He hated the old bitch, but he had no choice in the matter. With his wife gone he just went to finish his own breakfast.

It was followed by his usual routine of doing the dishes and cleaning the master bedroom, picking up his wife’s dirty laundry and making her bed for her. It was followed by doing laundry, one of the tasks he dreaded most in any given day. Handling both his own, his wife, but especially Ms. Thompson’s delicates, being forced to get familiar, with all their scents was both humbling and disgusting beyond belief.

Once he was done with those tasks Ms. Thompson changed into her workout clothes and took him along to the gym. Unlike last time however she didn’t require him to be her towel boy, instead she ordered him on the treadmill which she set up for an hour, specifying it to start at a slow walking pace only to over the course of the hour move up to a brisk walking pace. The constantly heightening pace was bound to keep him searching for his balance constantly, keeping his arms at his sides like she had thought him. Besides the more he walked the more ingrained this new way of walking would get. While less humbling than being her towel boy it was bound to keep him busy.

Monroe was nervous beyond belief as the treadmill started moving underneath his nylon feet. He couldn’t afford to trip on here as unlike the floor this thing kept moving. It pretty much forced his hands at his side as he tried to keep up with the pace. He felt like such a sissy performing the small heel to toe steps the skirt forced him in. the faster the belt of the treadmill moved the more vigorously his hips ended up swaying as he had trouble keeping up with the pace. Making matters even more difficult was the vigorous pace at which his nylon legs moved over one another, keeping his cock try to grow in the uncomfortably tall cage.

By the time Ms. Thompson was done with her workout she was just in time to witness Monroe walking at the fastest pace. It was hilarious, as his hips were swaying obnoxiously wide, his wrists flapping with every step. They had to come awfully fast one after the other to keep up with the machine. After all the skirt didn’t allow bigger steps, only faster ones, a good training in learning the boundaries his skirt allowed. Slowly but surely from that climax the treadmill slowed down to eventually come to a stop, leaving Monroe completely exhausted.

“I see you enjoyed a pretty intense workout yourself sissy? Well so did I so get your ass over here and dab my sweat dry.” Ms. Thompson instructed. Without the regular dryings in between, the sweat was really pearling on her skin.

Groaning loudly Monroe minced off of the treadmill and walked over to his Nanny. He was pretty exhausted and warm himself, but with his Nanny ordering to be dried off, he had no choice but to comply. It ended up making his time in the home gym just as humbling as yesterday had been, only more exhausting after an hour on the treadmill instead of doing a few squats.

“There’s a good sissy, now lets head upstairs to go get changed for your little spa training. I think it’s an amazing idea your wife had, a real good way of bonding it will be amazing. While I’ve never experienced it before myself, I can see how some sensual personal grooming and pampering can work up a sexy mood.” Ms. Thompson said with a wink that made Monroe shudder. He really hoped that wink wasn’t any sort of hint.

As they went up to what he guessed was now officially their room his worries only grew. Like always Ms. Thompson had no qualms at all about stripping in front of him. In fact Monroe was the one troubled by it as he didn’t want to see this vicious old woman naked at all. He turned his gaze away as Ms. Thompson put on nothing but a white satin bathrobe, she didn’t even put on panties having stripped out of everything. The worst part about it was that she made him wash her workout clothes right away, forcing him to press his nose against each item while sniffing audibly. It made Monroe gag.

“Hmmm still haven’t come to terms with appreciating femineity in all its forms have you sissy. Maybe today will help though. Since your wife plans to use the spa as a kind of foreplay I think we’ll need to get really up close and personal. After all I want to prepare you as well as I can to perform according to your wife’s expectations. I think a good measure to how well you’re doing will be how wet you manage to make me.” Ms. Thompson said with a grin confirming Monroe’s worries.

He simply couldn’t believe what he was hearing, just the thought of turning this woman on was making him shudder in disgust. Having to share a room with her, sniffing her dirty laundry, it was all horrible as it was, but having to actually get intimate with this woman was so much worse. Seeing her naked grossed him out enough already.

“Nanny, with all due respect, but I really don’t think my wife will like that very much. I mean isn’t turning another woman on considered cheating? Maybe we should call her just to be sure.” He said trying to safe his skin. He didn’t dare to stand up to Ms. Thompson, but being considerate for his wife was the perfect excuse. If she wanted him to be perfect for his wife then surely she couldn’t be mad about this. He was fairly certain that Lena would see things his way, that she would agree and tell Ms. Thompson not to do this.

“That’s a fair point sissy, still it wouldn’t be very considerate to interrupt her in the middle of her tennis match. Tell you what sissy, not every pampering I imagine would fit nicely in a spa day is as sensual as the other, besides like any good foreplay I imagine building up is very important. I don’t think anything too personal will happen before lunch. We can ask Lena when she gets here.” Ms. Thompson replied with a smirk.

She was pretty certain Lena wouldn’t mind, not with the apathy towards her husband she had been eagerly nourishing. In fact she imagined with the way she was going over his orgasms now that Monroe wasn’t satisfying her anymore. In time having to get her husband off when he was let out of the cage due to good behaviour would most likely become a burden. She would be all too happy to sweep in and pick up those duties. Shame and punishment were great motivators to make someone do your bidding, but nothing was quite as efficient to manipulate a person than going through their sexuality and pleasure.

Either way this opportunity Lena had given her was a perfect start for another thing she wanted to work on with Monroe. She wanted to teach him to respect and worship of all ages and in all shapes and forms. Ms. Thompson knew full well that she wasn’t attractive to Monroe, but that was a good thing. She wanted his focus to be on serving her and her pleasure without ulterior motives. On top of that teaching him certain things about how to pamper a woman could come in very handy, they were great skills to have whether it was to please a Mistress or actually get a job in a spa. She could already imagine it, the rich asshole feminised and pampering women in a spa for a minimum wage.

“Now let’s head down to the living room so we can get started shall we?” Ms. Thompson asked as she pushed a bag into Monroe’s arms who meekly followed her down with a groan. Even though Ms. Thompson had told him things wouldn’t get too personal just yet he really didn’t look forward to pampering this mean old witch it was just another embarrassment he had to deal with.

Sitting herself down on the couch Ms. Thompson smirked up at Monroe. “Alright Monroe, for this first step I am going to need you to take off your skirt and pantyhose remember, if I see as much as a little snag in them you are going over my lap, now get to it.” She instructed making Monroe balk.

“I thought thing wouldn’t get too up close and personal yet.” He cried out.

“They won’t, we’re going to start with a nice relaxing pedicure. Nothing is better to start of the spa experience than a relaxing, yet functional pamper session for the feet. It’s going to include painting nails and since I don’t want you to ruin mine you’ll get some practice on yours first now strip sissy.” Ms. Thompson said firmly amused at his reluctance. Nothing was more satisfying than bending a reluctant sissy to her will.

Monroe groaned. While he was happy to get out of the very restrictive skirt and the pantyhose that made his cock throb in his cage he wasn’t at all happy with the reason why. The thought of painting his nails made him shudder, yet another indignity. “Good, now look through that bag and get out the pumice stone, you can start by working the calluses on your feet away.” Ms Thompson instructed as Monroe was force to kneel to even get started. Reluctantly he started working his soles with the stone until his Nanny was satisfied.

“Alright sissy, for the nails you can use the deep red polish, same as mine. I think we’re going to look so cute with matching nails.” Ms. Thompson smirked as she went into detail on how to go about painting his nails. She went over every step with him, barking a new order the moment he was done with one step. Once he finally finished painted his nails Monroe was mortified. They made his feet look so effeminate in an instant.

He wanted nothing more than to just scrub off this nail polish and much to his surprise that was exactly what Ms. Thompson told him to do. “That’s good for a first try, but no where near close enough to where they need to be. You’re going to take the acetone, clean off that polish and start again. Be careful not to get any polish on your skin next time. It’s minimal but too much. “ She said informing him that he hadn’t passed her inspection.

It ended up taking four tries until Ms. Thompson was satisfied with his results. Much to his disappointment she didn’t let him clean it off this time instead telling him to put his pantyhose and skirt back on. As he carefully did so he was mortified to see his bright red nails shine clearly through the sheer nylon fabric that once again wrapped his feet, further feminising his look.

“Good, now you may give me a face massage, apply a facial mask which you should find in the bag and put a slice of cucumber over my eyes. The mask needs time to work so we’ll give it that time during the pedicure you give me. You may start my pedicure with the pumice stone, then clean my nails and repaint them. Blow them dry between each coating. Once they are done you may give me a good foot rub with the hydrating cream, and before you get any ideas about doing something stupid while I can’t see you, if I even suspect something is off I will be pressing this button here.” Ms. Thompson said as she held the button to the shock ring around his balls in her hand, her button on the trigger to be pressed at any minute. Nervous beyond believe Monroe went to work.