Caught in a New Life

Chapter 8

The following morning Monroe was woken up abruptly by the sound of the bell ringing. It was not even 8 o'clock yet, who the hell could that be. With a groan he put on a pair of sweatpants and a t-shirt, groaning when he noticed that chastity cage again. He was still angry after what had happened yesterday. That stupid maid would pay for this. Now this bullshit. Whoever it was could probably expect a cold welcome.

Stomping his way downstairs Monroe was surprised to hear the door open and hear his wife welcome someone called Ms. Thompson. What the hell was a strange woman addressed with her family name by his wife doing in his house this early in the morning. While he didn't want to upset his wife even further this was still his house and he was going to give this woman a piece of his mind.

Entering the hallway he spotted that his wife was fully dressed up already, accompanied by a woman who was only slightly shorter than his wife was. About 5'10" if he had to guess. She was clearly a lot older than they were. She was lean, her face was rather wrinkled, her eyes hazel in colour and she had a blond short bob cut which was obviously just coloured blonde.

The woman was dressed In a conservative white summer dress with a pair of sheer nude nylons and black flats. While not quite dressed like a grandma the outfit wasn't sexy either. Not that Monroe minded. Just thinking about this woman in something sexy made him shudder in disgust.

Her body was actually in quite a good shape considering what her age must be given away by her wrinkles. Monroe estimated she must be somewhere in her mid to late sixties yet she certainly didn't look like the grandmotherly type. She looked more like a stern disciplinarian. Seeing that Monroe was about to make a fuss she instantly interrupted him before he could get a word out.

"Ah this must be your unruly husband I was told about. I can already see the problem, well let's get this introduction out of the way so we can carry on. I'm Ms. Thompson, but you can call me Nanny. I'll be living here for the foreseeable future." She said confidently without even a moment of hesitation. Monroe went completely pale in shock and even Lena who had know why this woman was here was taken a back from her directness.

While Monroe's face quickly turned red in anger Lena just grew a big smile. This woman was going to be perfect for the job. Ever since she had caught her husband watching that porn and had locked him up the true asshole in him had gotten exposed. Up until then she had always turned a blind eye to it and it hadn't been apparent either. After yesterday she just knew something drastic needed to happen.

Looking angrily between his wife and this woman with her unwavering stern expression he burst out in an angry rant. "Who the hell do you think you fucking are, coming in my house on such an early time, talking to me like this?! This is fucking absurd, ridiculous even you have no right, be here and if you don't leave right fucking now I'll be calling the cops and you can shove that nanny bullshit where the sun doesn't shine!" Monroe screamed at the top of his lungs.

Ms. Thompson's facial expression remained very calm, but her actions didn't. Almost immediately she gave him a surprisingly hard slap landed across his cheek. "Don't you ever talk back to me like that ever again! I'll deal with your punishment later. Now apologise and maybe I'll consider a lighter punishment." She warned shocking Monroe and Lena yet again.

"You're unbelievable you know that? I hired Ms. Thompson exactly because of behaviour like this. After how you treated the maid or should I say the poor girl you threatened into coming here yesterday and now this, I clearly made the right call. Ms. Thompson will be your Nanny as she so elegantly called it for the foreseeable future." Lena firmly stated taking Ms. Thompson's side.

"What the hell Lena, this is fucking absurd! You can't be serious and I won't stand it and neither will I stand this fucking bitch you hired! This has gone way too far and I demand it stops right here and now! You'll take this cage off right now and end this bullshit!" Monroe demanded getting him another slap across his other cheek now. He was about to lash out, but Lena interrupted.

"If you hadn't watched that porn I could have trust you without that cage! If you hadn't been such a complete dick yesterday then I wouldn't have had to hire you a fucking Nanny, but it's clear that you can't even be left alone for a minute so deal with it! I'm not going to change my mind, especially not after how you just reacted! If you act like a fucking baby you get a Nanny, simple as that!" Lena said raising her voice.

When she saw Monroe was about to react again she quickly interrupted him. "Of course if you are fucking serious about not standing for this anymore then be my guest. This is indeed still your house for the time being and both me and Ms. Thompson will get out if you really insist but then the next time I'll see you will be in a courtroom with that video I made that one night. You can forget about me giving you the key to your cage as well. You can claim that back in court as well. Oh and I bet the owner of our maid hiring company plus our two maids will want to testify against extortion, blackmail, racism and sexual harassment. Is what I'm doing blackmail as well? Perhaps, but who is going to testify for you? Which of your lawyer buddies will take a case with these odds and which ones will still take it after reviewing all the evidence?" Lena asked rubbing in the facts and the power she had over him. He had way more to lose than she did and they both knew it.

Monroe's face had gone from red anger to pale shock once more. "Now fucking apologise to your Nanny. She'll be watching over you at all times from now on and I'd better hear no complaints. She is allowed to punish you however she sees fit and your next orgasm is entirely dependant on her evaluations. The three-day rule still applies, but now her evaluations will decide whether or not you've earned a day of progress. If your behaviour keeps getting worse however I'll see you in court anyways. I wonder if maybe one of your lawyer buddies will want to defend me after a little bit of charm and a glimpse at the evidence." Lean spoke menacingly meaning every word of it as she let Monroe grasp the severity of the situation.

A small smirk spread across the face of Ms. Thompson. This was going to be a delicious break in task for sure. This little introduction had proven exactly the kind of asshole Monroe was, one just like the assholes that had hurt her son so much in the past. Oh she was going to truly enjoy this, but there would be no waiting like was initially the plan. This required immediate intervention.

"Well Monroe, I'm waiting on that apology of yours, but I warn you my patience is wearing thin." Ms. Thompson said calmly, tapping her foot impatiently.

"You can fuck off, I don't have to do what you say, you're both crazy!" Monroe shouted defiantly.

Ms. Thompson could see Lena was about to react but she quickly took action before she could. With her left hand she was going quickly towards Monroe's cheek, something he by now anticipated and dodges, but what he didn't notice was the right hand going straight towards his crotch, grabbing his balls in a tight vice like grip through his sweatpants. "Don't mind him dear. I've managed more than one unruly boy in the past. I'm sure I'll be able to handle myself from here on out. You just go and have some fun, do some shopping or something. I can see you need to put your mind off of this." Ms. Thompson said while she made Monroe yelp with a hard squeeze.

Lena was amazed at her actions, but this woman was right, she really needed away from her husband for a while. "Alright, I guess I'll be going then. I won't be back until the late afternoon or evening. If anything were about to happen you have my number. And you asshole, you better behave yourself if you ever want out of that cage again." Lena said shortly before leaving the house, leaving Monroe with his face contorted in pain at the mercy of this crazy woman. His hands were trying to break her grip, but it only hurt his balls more. She was surprisingly strong for her age.

"Now while your wife is taking a well deserved break we have some time for your re-education. I wasn't supposed to intervene this quickly but you forced my hand. The correct answer would have been. 'Yes Nanny, I'm sorry. It will never happen again.' Anyways that's beside the point now. You've had your chance and you spoiled it. I'm sure you'll reconsider spoiling future chances though." Ms. Thompson said.

She then proceeded to lead Monroe outside still by his balls much to his shock and fear. Sure their front yard was rather big and this was a quiet neighbourhood, but still what if anyone happened to pass by? She dragged him all the way to a spacious but modest looking car, opening the large trunk to reveal five big suitcases. Opening one up she pulled out something then without warning lowered his pants and boxers.

Before he could react she shut a metal ring around his scrotum right above his testicles so it couldn't slide off. Mortified of anyone seeing him like this or worse even his chastity cage or this weird ring Monroe quickly pulled his pants back up. As he was doing so however he fell down to his knees in pain having received a harsh painful shock to his balls.

"So that works. I wasn't actually planning on putting that on you, but the way in which you dodged my slap earlier, its clear that you're a fast learner, plus with how unruly you are I need something that can intervene quickly and at a distance. That shock was only the base level. It can go much higher than that, but I actually hope I won't have to use it. Like everything it will depend entirely on you though and if you're just as fast a learner on other fronts then I'm sure you will be fine." Ms. Thompson said with a smirk smiling down at the pained kneeling man while she casually strapped a watch like thing with buttons around her wrist.

"Good, now that we've gotten this more painful introduction out of the way you can pull your pants back up and move my suitcases up to the guestroom." Ms. Thompson said in a no-nonsense kind of way, not even bothering help as a shocked Monroe wanted to protest, but out of fear of his balls he complied. The suitcases were rather heavy, making him wonder how long this woman planned to stay.

"The correct answer when I give you an order is 'Yes Nanny' now do you want to try or are you going to remain stubborn?" She asked holding up the watch with shock buttons menacingly.

Monroe badly wanted to yell at her to fuck off, but after the memory of the shock fresh in his mind he forced himself to swallow his pride. "Yes Nanny." He said softly before starting to wrestle two of the suitcases upstairs while Ms. Thompson just followed behind not bothering to take one herself.

"That'll do for now, but next time you'll better answer a little more enthusiastically." Ms. Thompson said as she followed him back and forth from the car to one of the guestrooms, following Monroe's every move as he had to make three trips to move all the suitcases.

Then all of a sudden she spotted an open door a bit further down the hall. Looking inside she instantly realised this had to be the room Monroe slept in. "Oh Monroe, move my suitcases from that room to this one here. I think I'll sleep here instead." She casually said.

Without thinking Monroe exclaimed. "But that's where I sleep already. Isn't it much easier to move in an unoccupied room? Otherwise it'll take even longer to get you set up." He replied through gritted teeth.

"Nonsense, in fact it'll be even less work. I'll be sleeping with you in a room from now on. Your wife told me that you can't be trusted alone for even a moment. After what I've seen and heard so far I can only agree and since I take my job seriously I won't leave you alone not even at night. Hell if I notice you can't even handle the freedom of going to the toilet alone I'll accompany you there too is that clear?" Ms. Thompson asked calm yet stern.

"What?! No way, I won't be sleeping with an old hag like you, not even in your dreams! You're crazy, this madness has to end now!" Monroe exclaimed, his shock over Ms. Thompson's statement making him forget about the shocker ring around his balls. Something Ms. Thompson was all too happy to remind him off as she gave his balls a zap with a quick tap on the watch that served as a controller for the ring, sending him down to his knees in agony.

Before he could recuperate from the shock Ms. Thompson took a firm hold of his ear and drug him over to the side of the bed where she roughly bend him over her lap, holding him down with one hand in the small of his back and yanking down his sweat pants and boxers before starting to rain down hard stinging blows across his bottom without warning. "My my, such a very smooth bottom you have, now try again what would have been a more appropriate answer? I'll only stop spanking you after you have given me the more appropriate answer ten times in a row after each spank." Ms. Thompson explained already giving him 10 spanks in the process of her explanation.

"Fuck you!" Came Monroes answer. He knew it was wrong, he knew the appropriate answer probably was 'Yes Nanny' but he wouldn't give her the pleasure of saying it, no way. Instead he just kept repeating his first answer after his first spank. He persisted for about 16 spanks doing so, but as Ms. Thompson didn't even show a sign of slowing down his protest answer slowly started losing resolve.

He hadn't want to give in to her, not in a million years, he had hoped that this old woman's arm would tire quickly before the pain would get too bad. The pain only continued increasing though as his bottom was getting more and more tender with each slap making the next one hurt more. Ms. Thompson was clearly in very good shape as she didn't even slow down slightly.

It took him a while to realise that it was he who would have to give in. By the time he did realise it, he was already at the point of where he could barely take any more. "Yes Nanny!" He eventually screamed out in a quivering voice doing his best not to break down, having to say this was already hard enough, he didn't want to give Ms. Thompson the pleasure of seeing him break down on top of it.

A big smile spread across Ms. Thompsons face. She could barely feel her arm anymore after what had to be more than 50 spanks already, but she knew giving in could be devastating for her future authority. Monroe was tougher than she had given him credit for, but in the end he had given in. She had to admit that she loved the struggle though, she loved her subjects to fight back at least a little. It made breaking them so much more fun. This wasn't the held back approach she would have preferred going for first, but it was definitely the necessary approach.

After Monroe gave her ten loud and clear "Yes Nanny!" exclamations Ms. Thompson finally stopped the spanking, much to the relieve of them both. Ms. Thompson couldn't show that she was having a hard time keeping up as well though and so she forced herself to not sound out of breath. "Now get off my lap and get my suitcases in here." Ms. Thompson said as she remained seated on Monroe's bed.

She saw how Monroe was about to pull his boxers and sweatpants back up, but she instantly stopped him. His bottom was looking more blue than red and he would probably have trouble sitting for a few days to come. In other words now was the right time to move up his feminisation to the next step. There was no way he was going to question her authority right now. "Don't pull you pants back up. In fact take them off completely and your t-shirt as well then bring my suitcases right here right now!" She said sharply.

Monroe wanted nothing more than to cover up his embarrassment over being spanked by this old lady, but after what just happened her tone struck fear deep within him. He just didn't dare oppose her, definitely not now. So instead of making a fuss out of having to get naked he removed his clothes as fast as he possibly could. He then dashed naked across the hall and brought the five suitcases to his room as fast as possible.

When he was bringing over the last of the suitcases Ms. Thompson was already rummaging around in the first one. She pulled out a package of what looked like brand-new panties. They were plain white cotton full cut ones with a tiny pink satin bow at the front. If not for that they would have been granny panties, but now they looked more juvenile than anything else. Monroe didn't think much of it, as far as he knew she was just unpacking.

What was curious though was that she didn't just move with the package to is the dresser which held a few of his spare clothes, the main bulk still being in the master bedroom. Instead she opened it and held up one pair so he could get a better look. "Here Monroe put these on. After how disrespectful towards women you have been especially to those maids, I think it would be good if you spend a day in their shoes, or well at least panties. Obviously with your cage you won't be getting in anyone's panties unless literally getting into these panties which are yours now." Ms. Thompson stated.

Monroe wanted to scream, this couldn't be happening right? It was happening though, and the impatient tapping of Ms. Thompsons foot made him nervous about getting punished again. Reluctantly he stepped over to where she was still sitting and grabbed onto the panties. To his surprise she wouldn't let go of them however. "Shouldn't you say something when I tell you to do something?" She asked slightly raising her voice.

God he wanted to just disappear into thin air right now, so embarrassed was he. Did she really have to make this so much harder than it had to be? The answer was yes, the stern look in her eyes told him all he needed to know. "Yes Nanny." He reluctantly said in a soft tone, trying to take the panties again, but Ms. Thompson still wouldn't let go of them.

"Where are your manners Monroe? What do you say when someone gives something to you?" Ms. Thompson asked still not satisfied with his answer, she would show who was boss and Monroe was going to acknowledge it willing or not.

"Thank you." He meekly said, but as he could see she still wasn't satisfied he quickly changed that to. "Thank you Nanny." He hated having to address this crazy bitch in such a juvenile way, he hated these panties, but with the spanking and the zap to his balls fresh in his mind he didn't dare step out of line. Not with Ms. Thompson so close by, clearly looking for an excuse to punish him again.

Finally Ms. Thompson let go of the panties, and with a smirk on her face she watched how Monroe quickly put them on. She knew he wasn't happy about this at all, he couldn't be, but this battle was one she had won and she loved seeing him in those simple yet juvenile panties, especially after how aggressive he had been earlier.

"Good, now as I remember hearing from your wife you pressured a poor girl into coming here to do the cleaning task she had told you to do. The living room might be clean now, but this room could definitely use a good vacuuming. You're also going to change the bed sheets as I'm not sleeping on a bed you have already soiled and slept in. Then depending on where you want to sleep you can get a single person bed, or a mattress in here. Frankly I don't really care. For all I care you'll just be sleeping on the floor tonight, but you are sleeping in this room and there is no way I'm sleeping with someone like you." Ms. Thompson said giving Monroe some quick instructions that would probably keep him occupied for most of the morning.