Caught in a New Life Pt. 08

Chapter 11

The following morning this horrid new routine repeated. Ms. Thompson's loud alarm sounded through the room waking him up way too early once more. "Wakey wakey pansy. You know the drill while I'm in the shower you better stay very close to that door. If not, well then I guess you'll quickly crawl back to it." Ms. Thompson said as she didn't even wait for a reply. Without further notice she headed into the bathroom. Monroe who had learned better than to complain quickly followed behind standing at attention right next to the door.

First Ms. Thompson showered, then he got his 15 minutes. In which he ended up strongly smelling of lavender yet again, just like Ms. Thompson. With a pink towel wrapped around his chest, just like a girl he was led to the room that held his clothes, or at least the little he was permitted to wear. Upon opening the door his jaw dropped in shock.

He had expected that there would be something extra for him to wear, given how he had first gotten panties then socks there was not much more to give in sense of underwear right? He figured that he would be getting a pair of pants or a shirt to cover things up at least a little more. To preserve more of his dignity. Instead the knee high socks were gone. Not that he minded one bit he didn't want to wear such things panties alone were bad enough as it was. What bothered him most however was that in their place he found packages of pantyhose. A couple of pairs in sheer black, a couple ones in sheer nude and a few in sheer tan.

"What the hell are those? Where are those stupid socks from yesterday. I thought I would be getting pants or at least a fucking shirt this is ridiculous." Monroe instantly blurted out in anger, not even thinking about what he was saying or the potential consequences.

"I advise you tread very carefully here pansy. You have on chance to rephrase that question in a more suitable tone and manner otherwise,... Well I guess you can guess what'll follow otherwise. Be polite and I might just provide you with an answer since I'm kind like that." Ms. Thompson instantly replied harshly and cold.

It was a tone that instantly struck Monroe with fear. Fear of punishment which he had gotten too many times from this bitch. Each one more painful and embarrassing than he could have imagined. Shit he needed to fix this before that punishment would come. "What I meant to ask nanny is where my socks have gone and what these are and why they are in my closet? I was expecting that I would get some pants or a shirt given how I already had all the underwear I needed." Monroe rephrased in a polite tone. It was embarrassing, but less so than being bent over this woman's lap or whatever other wicked idea she might have.

"Well pansy since you didn't want to wear your socks yesterday I just figured that you didn't like them as footwear. Then when you looked at your wives legs so lustfully when she was dressed to go out I figured you might like nylons better as foot wear which is why I got you these pantyhose. Also you would have gotten something more towards a complete outfit if you had worn your socks yesterday. You can't earn new clothes if you don't appreciate the most complete outfit already available to you. In that case I just figure you don't need anything else." Ms. Thompson explained her reasoning to a stunned Monroe with a big smirk.

"Like I said pansy, the choice what you wear from this closet is entirely yours, but so are the consequences of those choices. Your fridge seems stocked enough to manage until next week, but after that we'll need to go to the store again. We won't bother your wife with such things and I can't let you go out of my sight so no matter how many clothes you have earned by then you'll be coming with me." Ms. Thompson explained putting even more pressure on Monroe.

Not knowing what to say or do Monroe just stared back at her in complete and utter disbelieve and shock. "So what are you waiting for? Are you going to get dressed or don't you want to wear panties anymore either? In that case I could take away the pantyhose."

"No please Nanny. I... I just much prefer those socks so please can we just go back to those? I promise I'll wear them. I like them much better than pantyhose I swear, I just, I mean on Lena, I... never mind, can I please just go back to socks?" Monroe stammered. This couldn't be happening. He always liked when his wife wore nylons because they made her legs look so sexy, but damn nylons were so much worse than just knee high socks. A man could wear those under the guise of compression socks for sports or under pants they would look pretty normal. Pantyhose on the other were things a man couldn't pull off at all, at least not in his mind and certainly not these sheer ones.

"Well you had your chance to wear those yesterday? So what's it going to be? Are you going to pick your outfit for today or do you want to go naked? The choice is yours, but we don't have a lot of time to waste anymore as we need to prepare your wife's breakfast." Ms. Thompson said in a tone that made it clear she wasn't going to accept any back talk on this topic. Monroe just wanted to scream at her, that this was ridiculous, that those were damn woman's clothes, and she couldn't be serious.

That scary red button around her wrist and the fact that even sex with his wife depended on her judgement of him made him change his mind though. As much as he hated this bitch and everything she imposed on him he had no choice but to do as she asked. Hell even his search to find the key to get him out of this cage, this shock ring and all blackmail they had on him was halted because of her ever presence. If he just could get some time to figure out a plan to kick both her and his wife out and reclaim his life.

He should have acted way earlier as he was getting more and more trapped, but Lena had been a way crueller bitch than he imagined. He would have never given her credit for playing things this hard. He would have never thought she would bring his secret out to all his fucking friends and pretty much everyone he knew. Little did he know that all of it had happened because he had been an asshole to too many people. If he hadn't been one to Ben Lena would probably never had met Linda and Ms. Thompson would have never arrived here. His wife would have been mad, but she would have eventually forgiven him, not with their influence though.

"I...I'll wear these." Monroe eventually said picking out a package of nude coloured pantyhose he hoped would be unnoticeable enough along with another pair of his panties. As much as he hated it he couldn't risk this bitch actually dragging him out in just panties something he was rather certain she would do if her treatment of him had taught him one thing so far.

"Good, then what are you waiting for? Get dressed!" Ms. Thompson shouted just standing there her arms crossed over one another as she looked at him sternly. Groaning lightly Monroe resigned to his fate, sliding the plain white panties in place to at least hide his embarrassing chastity cage before dropping his towel and unwrapping the package of pantyhose. He shuddered as they unrolled from the carton that held them, looking so sheer and delicate.

God he couldn't wear these could he? At least his panties somewhat resembled briefs, but this? The look on Ms. Thompson's face told him that he'd better get to it though. Leaving him not much of a choice but to wear these things. How the hell was he even supposed to put these on? Knowing no better he opened up one of the legs and jammed his foot in it just like he was used to doing with socks. It worked rather well until he was about two thirds of the way down and holding it open wasn't enough to provide safe passage anymore and the strain put on the delicate nylon material caused it to rip.

"Congratulations pansy, you ruined your first pair of pantyhose. You'll get punished for this later but right now we have no more time to waste take another pair and put it on." Ms. Thompson said sharply keeping her stern stance.

Punished for this? It was not his fault this material was so dam fragile. All he wanted was to scream at Ms. Thompson yet again, but he forced himself to stop knowing that it wouldn't get him anywhere. "I'm sorry nanny, but this is unfair. How else was I supposed to do this, it's not my fault that these things are so fragile. Maybe it would be better to switch back to socks, nothing would happen with those." He complained hoping that being polite would get him out of his punishment.

"Oh so that's why you put your pretty pantyhose on like a brute? All because I didn't want to switch back to socks for you. Oh you're going to be in so much more trouble now you manipulative pansy. I should have known you were just out to rip them." Ms. Thompson said viciously, raising her hand threateningly as she approached Monroe.

"No, I didn't, I didn't know how to put them on. I just assumed I would be okay to stick my foot in it like I was with socks." Monroe blurted out, desperate to escape this punishment. Apparently despite being polite he had fucked up.

Much to his surprise and relief however Ms. Thompson did lower her hand and her face softened lightly. "I don't know if I should, but I do believe you. You'll still get punished for ripping your pantyhose, but you'll escape the punishment for being a complete and utter manipulative bastard. After all you did put them on in the worst possible way and not knowing how to put on such delicate fabric is no excuse. Especially not since you could always ask your nanny politely and she will be glad to teach you. Your nanny is here to help and you can ask her anything." Ms. Thompson said with a big smirk as she handed him a new package.

Asking his nanny? Ridiculous. Monroe hated that term with all his being. Yet he really was clueless about how to put these way to delicate things on and as such he had no choice. He needed to earn more clothes and he had to avoid screwing this up if he didn't want even more punishment. Forced to push his pride aside he eventually spoke up. "Nanny could you please teach me how to put on pantyhose." He asked softly hating himself to ask to be taught such a feminine thing.

"With pleasure pansy." Ms. Thompson stated as she took Monroe's hand and led him to the bedframe in this guest room. Without hesitation she kicked of her heels, hiked up her dress and slid off her own support hose. They were thicker than Monroe's pantyhose but the method of putting them on was the same. Monroe just looked at her a little disgusted as she once again stripped in front of him.

Sitting down on the bedframe Ms. Thompson carefully rolled the legs of her hosiery into doughnuts then slipped her toes into one foot, rolling it up to her knee before doing the other foot. With her support hose now pulled up to her knees she stood up and continued rolling it all the way up until the waistband settled a little above her bellybutton. "So that's how you put on pantyhose pansy. Now it's your turn. Remember ruin them and pay the price." She said a she put her shoes back on and straightened out her dress.

Monroe just stood there shifting a little uneasily. Pulling on pantyhose appeared to be way harder than pulling on socks, or at least way more work. The whole thing seemed like such a feminine delicate ritual that made his skin crawl, but with Ms. Thompson's stern look he knew he'd better get to it right away.

Resigned to his fate he sat down on the bed then as careful as he could he started rolling the legs of these sheer pantyhose into doughnuts like he was just shown. Sliding his foot into the delicate material he carefully rolled it up to his knee, then repeated the process. This soft nylon felt so weird on his smooth skin, much to his embarrassment it felt weird in a wonderful way. The soft sheer yet clingy touch was unlike everything he had ever felt before.

Getting up from the bed he carried on putting the pantyhose in place. The touch getting increasingly intense as his whole legs got covered in the sensual fabric. It was especially intense when it travel over his way more sensitive inner thighs. Much to his ever growing embarrassment he let out a grunt as his cock was straining to harden in its cage. How the hell could he get turned on by this? This was so wrong.

It was especially wrong as he looked down, his legs now having a subtle yet clear glossy shine to them making them look outrageously girly. Ms. Thompson smirked wickedly. She knew exactly what that grunt had been for and she didn't want to miss this shot to rub it in hard. "I see I was right and you like delicate nylons way better than socks. It just proves how big a pansy you really are." She grinned delivering another blow to Monroe's ego as he just looked at her shocked.

"Anyways it's time to prepare breakfast we have already been losing enough time as it is. So chop chop hurry down to the kitchen and put on that apron." Ms. Thompson ordered before Monroe could get anymore protests in or even deny it. Hanging his head he eventually followed her order and started to head down stairs.

Much to his dismay walking caused his smooth nylon legs to brush together resulting in that same electrifying thrill he had felt wen she put them on, getting another grunt out of him. Sure he had always like how nylons felt when his wife wore stockings, and put her legs on his shoulders while they fucked. He had just never imagined they could feel this good, so shamefully good. He should hate these things and yet they turned him on.

Maybe that was just because he had been without sex for too long. Yes, that had to be it, the only reasonable explanation. He was just overly aroused due to it being so long since his last orgasm. Then again feeling this way because of his pantyhose was just plain embarrassing and since his next orgasm was still a while away due to his wife and this bitch of a Ms. Thompson's schemes he would probably do good to try and avoid arousal as much as possible.

His way to achieve that resulted in him adopting a somewhat awkward more wide legged walk to avoid as much friction as possible. It was wildly inelegant and while Ms. Thompson was none too happy with it she choose not to say a thing about it. Carrying himself like a proper sissy would be one of the things she would teach him and she knew the exact thing to help in that. Until she introduced it she would allow this. Besides it was a good way to keep him aware of what he was wearing anyways which was the biggest point of it all.

Down in the kitchen the same routine as yesterday followed, Monroe had to prepare his wife's breakfast as well as Ms. Thompson's while she just supervised. It was so unfair, he had to do all the work and that bitch of a woman wouldn't even lend a hand. It seemed like all she was here for was to berate and punish him if he made even one misstep. Between the potential of getting a shock, the punishment that was already awaiting him for ripping his first pair of pantyhose and the threat of his already urgent orgasm being delayed yet again Monroe tried not to screw up.

With breakfast prepared Monroe headed up the stairs to serve his wife breakfast on bed again and just like last morning he was instructed to dive straight under the covers to give his wife her morning orgasm. She didn't even thank him after she reached her second orgasm this morning with his tongue, she just got out of bed not even bothering to tell him he could stop. By the time he was out from under the covers his wife was already in the bathroom and he was left with a face coated in her juices and a plate with only some left overs and dirty dishes. He really felt like a tool, just there to be used.

Things didn't get much better when he got downstairs again, Ms. Thompson just added more dishes to his plate before allowing him to get his own meagre breakfast compared to what she and Lena had gotten. He was just finishing up his breakfast when his wife arrived down stairs, once again in full workout gear, but this time with a foam mat under her arm. "I'm off to yoga with some of my friends, oh and nice pantyhose Monroe, or should I say pansyhose?" Lena laughed as she left an embarrassed Monroe behind.

Ms. Thompson was very pleased, clearly Lena was getting the hang of humiliating him. It was perfect, if she learned not to pity him then there was no way out of this for Monroe. He didn't deserve a way out to begin with, Lena had already been way too kind and forgiving on him. "Alright pansy, time for you to do the dishes, then we can go about your punishment for ripping those pantyhose." Ms. Thompson instructed as Monroe just sighed and jumped into action, doing the dishes while dreading what his punishment was going to be.

It apparently came in the form of another spanking, simple, painful, embarrassing and efficient. The moment he had put the pink rubber gloves away Ms. Thompson had simply grabbed his earlobe and pulled him towards the couch where she guided him over her lap, flipping up his apron, but not bothering to pull down his pantyhose or panties. They didn't form much of an obstruction anyways and they were way more effective while staying on.

"Here we are Pansy, I'm going to give you twenty spanks and after each one you will repeat, I'm sorry for ripping my pretty pantyhose Nanny. Mess up and we'll start all over again." Ms. Thompson smirked as his nylon thighs and crotch area settled on her own nylon covered lap. It was bound to create some of the friction he had been avoiding with his awkward walk.

Without hesitation Ms. Thompson landed a first harsh blow to his nylon and cotton covered bottom, the force making him squirm a little on her lap which had the horrifying effect of sending that exact thrill he had been avoiding, that sensual feel of nylon sliding over nylon straight up his thighs making his caged cock react by trying to swell in its tight cage making him grunt as he forced out the words. "I'm sorry for ripping my pretty pantyhose Nanny."

"Are you getting off on being spanked pansy? Do you like being bent over your Nanny's lap and being treated like the naughty pansy you are? Maybe I should tell your wife about this. I bet she'd love to hear about how you love being spanked." Ms. Thompson taunted turning his face beet red faster than her spanks did his bottom.

"Please Nanny, don't tell my wife I beg you." He pleaded mortified beyond believe. How could his cock grow in a situation this mortifying. As if getting spanked over this way older woman's lap wasn't bad enough he also had to call these stupid things that were the cause of all this pretty and his to make matters worse. They were the only reason his cock grew which only made him even more ashamed.

"Oops, looks like you screwed up pansy. Time to start over again with your punishment, although I guess that's what you wanted isn't it you naughty sissy." Ms. Thompson laughed, starting to count from one again as gave Monroe his second first spank which was more like the fifth blow by now.

She hadn't given him an answer to his pleading, and afraid that this punishment would keep going on for ages Monroe stopped his pleading and just repeated what he had to to get this ordeal over with. As the pain in his bottom slowly started growing the feeling of nylon rubbing against nylon faded to the back, as his cock stopped straining to try and escape. By the time The spanking was finally over his bottom looked as red as his face did, a sharp contrast to the white of his panties.

"There we are. You can thank me now for teaching a valuable lesson about taking care of your dainty and delicate clothes. You need to be way more mindful and careful when wearing pantyhose full time. As good as they might feel they snag easily and you will be punished for every snagged pair." Ms. Thompson explained as Monroe hurried off her lap. Being mindful of his clothes was bound to get him to act more like the sissy she wanted to turn him into.