Caught in a New Life

Chapter 20

While the ride home was long it was luckily uneventful for Monroe, a real big relief after the horrendous stressful day he had had, going out dressed like this only to get this extreme makeover before visiting that overcrowded store. Finally he was given a moment of peace and quiet, a moment without getting ogled and a moment to rest his very sore feet and legs after strutting around in these heels for way too long.

His rest if you could call it that lasted until Ms. Thompson stopped the car in the driveway, not even bothering to pull it into the garage which Monroe could only guess was a deliberate choice on her part. After all she always seemed to go out of her way to humiliate him, so he doubted this was any different. "Alright Pansy, I'll open the front door for you, now you be a good sissy and put all the groceries where they belong and then you can start making us a quick late lunch." She said, just standing off to the side to keep an eye on him obviously without the intend to lift a finger herself.

Despite what little groceries they had brought along, unloading them ended up being a rather time consuming task. Walking all the way to the front door and through the house into the kitchen was quite a trip in these heels, especially since the stones leading from the driveway to the front door weren't all that smooth a surface, and there were a couple of steps to take as well. Besides the difficult terrain there was also the stress that some neighbour might see him. Sure the driveway was quite long and the neighbourhood very calm, but it was still slightly visible from the street if one cared to look close enough. It made him stress every time he left the front door which was quite often as all the struggles forced him to take only one or two items at the time making him make numerous trips instead of carrying it all at once. There was simply no way he would manage to keep his balance if he carried too much.

Finally after taking twice as long and enduring countless times the stress he would have had to endure had Ms. Thompson parked in the garage instead, he was finished unloading the groceries. The fact that she had watched it all and had now lazily sat down at the table with a smug smile just added insult to injury. No one had caught him, at least not that he was aware of which was a huge relief, but that was about it as he donned his apron to start on the light lunch that wouldn't be enough to fully sate his hunger. He couldn't help but think about how the apron now went perfectly with his new look. He still couldn't believe he had really been made over to look as dainty as this horrid apron.

Aside from having to work his ass off as some outdated housewife, serving the woman who had turned his life into a series of humiliations under the threat of punishment. Lunch passed by rather quickly. He was really getting the hang of his household duties including cooking, setting the table, clearing the table and doing the dishes.

By the time all was said and done it was mid afternoon and Monroe couldn't help but worry what other task Ms. Thompson would have for him now that he was putting away the last dishes he had just dried. Nothing could have prepared him for what followed though. "Ah good, I see you've finished the dishes I told your wife all about your new clothes and the makeover and she is dying to see the results. She has asked to meet her down town so hang your apron back on its hook and mince that pansy ass of you back to the car." She grinned.

Monroe's expression instantly turned to one of horrified shock as he heard what Ms. Thompson had to say. He had expected to be instructed to clean some room or the other, or to be educated on yet another task or personal care routine like massage techniques. All things he didn't like one bit, but that had become his new normal. Leaving the house, especially now after his makeover was so much more dreadful than any of those other chores. It Instantly brought him on edge. "Nanny with all due respect, but isn't there a lot of work yet to be done around the house? Maybe I could prepare some snacks or something like that so Miss Lena can relax and take in my new look when she gets back home." He tried with a wide but obviously nervous smile. Out right refusing wouldn't do him any good and he knew it so trying to persuade her was his only option.

"My my, so eager to do your chores. It looks like your new style has really set you on the right track to becoming a proper sissy housewife pansy, but the answer is no. Your wife wanted you to meet her down town so that's where we are going, so get that ass into gear and mince to the car unless you want some more motivation that is." Ms. Thompson replied with a delighted smirk. She really loved the progress she was making with Monroe, he was no longer fighting her on every call, instead trying to find ways to please her that were more beneficial to him.

Devastated Monroe hung his head, he really didn't want to go out, but after this morning's punishments to get him going he really didn't want Ms. Thompson to go over to giving him some more motivation as she called it. It was clear that she had made up her mind and he sadly knew that meant it was going to happen no matter what he did or said. Reluctantly he hung up his apron and started mincing back to the front door, his nerves once again soaring sky high as he took a moment to brace himself before leaving the house. His sluggish reluctant pace soon turned into a hurried mince as he tried to make it to the relative safety of the car. As a slight reward for not putting up a fight Ms. Thompson unlocked the door for him the moment he reached it, despite still being a few paces behind herself.

Once she got in the car she instantly drove off to wherever it was they were going as Monroe was left to wonder, outrageously nervous about yet another public outing. He probably would be the centre of attention yet again and he dreaded it to no end. Especially cause this time would probably be even worse as his wife's reaction would bring on even more attention. How would she react? He really hoped that she would see that this had gone way too far and help him undo all this mess, yet with how she had loved all the horrid changes Ms. Thompson had made so far he wasn't all too hopeful.

While Monroe had already been insanely nervous during this whole car ride it got so much worse when they finally stopped and he saw the place she had pulled up to, right in front of an LGBT+ club. This couldn't be the place right? Why the hell would Lena hang out in a place like this? Was this another one of Ms. Thompson's twisted ideas? To force him into a club with all those freaks? Freaks he feared would be more interested in him than ever now that he definitely looked like the biggest freak out there? Just the thought of getting hit on by them sent his stomach into knots.

"Alright pansy, so here is how this is going to go, you will walk into that club alone and look for your wife. I will be a little behind, but I want to see if your wife will even recognise you and if I walked in with you that would be a dead give away. Now get your ass moving!" Ms. Thompson eagerly instructed as Monroe remained frozen in his seat. There was no fucking way he was going any closer to that place than he already was he thought. He knew Ms. Thompson wouldn't yield, but he simply couldn't get himself to move.

"If you don't get moving in the next ten second I will go inside myself and ask if anyone feels like escorting a shy pathetic sissy to nervous to say hi to the community. You can also count on it that I will give you a spanking to remember in the middle of the club if it comes to that, now get your ass out of the car!" Ms. Thompson instructed firmly, taking on a tone that wasn't to be messed with. Monroe knew very well that she would do exactly, the threat of things getting infinitely worse the only thing able to convince him to reluctantly get out of the car.

He didn't like this one bit, but like everything in his life since Ms. Thompson's arrival all choices were made for him, his only choice was how hard he would make it on himself before he complied and Ms. Thompson's threat was the worst one yet. Just the thought of being introduced not only as a sissy, but as a very submissive one to all these people he considered perverts was just terrible. He didn't even want to think what they might try to do to him. In that case. Not that the odds were stacked in his favour right now, he could feel his heart sink in his stomach more and more with each small delicate step he took in his restricting skirt and tall pumps. He couldn't even slouch because of his rigid corset.

By the time he reached the door he was in full fledged panic mode, but a quick light zap to his balls when he took too long reminded him that Ms. Thompson was watching closely. Taking a deep breath trying to brace himself Monroe eventually opened to door to what he considered a den of depravity. The club had a kind of luxurious retro interior. There was a kind of stage with an open dancefloor around it in the very middle of the club while relatively private looking booths were set up in a U shape all around it, the far wall was occupied by a large bar. Right now since it was still early, the place was well lit and looked more like a diner than a night club.

Much to Monroe's surprise he first caught the attention of a table filled with women. One he considered really pretty wearing a lot of makeup and an elegant flirty dress while the other four he considered butch and not at all his type. They were obviously checking him out, and making comments to one another, one such comment causing a brief moment of surprise on all of their face. He could only guess that it was a comment figuring out that he wasn't really a woman. Nevertheless that didn't stop them from staring, only one of them seemed to lose interest while the others seemed rather amused and intrigued.

Worse than those Butch lesbians by far were the guys who's eyes he caught, some just looked not giving him a second glance until someone at their booth noticed he was a guy in a dress. It made some look extremely interested while others remained completely uninterested. He tried his hardest not to look back as he scanned the bar for Lena, walking deeper and deeper inside until he finally spotted her at the bar, talking to her friend Ben. He didn't like the look of it at all, but it explained why she was here.

Mincing right over to where Lena was sitting Monroe was growing more and more nervous. Ben had noticed him a long time ago, spotting everyone who entered his club, but he didn't pay Monroe much attention until his approach. He had just considered him another client and besides such delicate sissies weren't really his type. It wasn't until Monroe was right at the bar, standing next to Lena and squirming nervously not knowing how to approach this situation that he decided to address him. "Excuse me Miss, but can I help you with something? If you're here for food or drinks, you can take place in a booth and someone will be right with you." Ben spoke clearly not recognising him which made Monroe feel even worse. Especially when Lena turned to him in the meantime, not recognising him either.

At least not for a few long seconds, when it finally dawned on her that this delicate looking woman was her husband, her jaw dropped in sheer shock. Sure she had seen him in heels, skirts and blouses, but this outfit and just about everything about his new look was just so different. Even knowing him for years and sharing a bed with him it was hard to see his subtly present facial features under those thick layers of makeup. "Monroe, is that you?!" She cried out in shock, loud enough for the whole club to hear as Ben's polite smile turned to a big shit eating grin.

"Shhhh not so loud or some of these fre... people might take notice. Look what Ms. Thompson has done to me, she has taken this way too far, you have to put a stop to her and all this madness." Monroe hissed in a soft whispering tone, not wanting to drag any more attention than his wife and his outfit had already put on him as he was only barely able to correct himself in the hope of not pouring more oil on the fire.

It didn't work, she clearly knew what he had been about to say and as a result Lena's eyes narrowed as an angry look washed over her face. "What were you going to say Sissy?! If there is any freak around here that's you! You also should know better than to call me anything but Miss Lena, and where the hell is that pretty voice you practiced so hard on or your Nanny for that matter?" Lena shouted clearly pissed as they now had the attention from everyone in the bar. All of them looked kind of angry having overheard the freak part as Monroe went into full fledged panic mode.

He couldn't believe that his wife didn't support him in this lesson that had clearly gone too far, aside from that everyone now knew his true colours and they were pissed. Shit how was he even going to leave this place now? Some of those people looked really mean and tough. As if things weren't bad enough already Ms. Thompson also entered the club, a big smirk on her face as she saw all the angry attention pointed towards her sissy ward.

Whatever he had said he had clearly killed what sympathy his wife had for him which was fantastic as she had feared this drastic change may have need some convincing that it was necessary. After all she didn't want Lena to take pity on Monroe and let him revert back to his old ways. The moment she had been hired she had made it her mission to turn Monroe in a full fledged sissy and for that she did need the support of Lena. She had done a good job convincing Lena to stay on this course and clearly Monroe had now done an even better job to solidify that.

"What kind of trouble has our pansy gotten himself into this time?! I'm behind for a couple of moments and she is already running into trouble! I can't believe it and all that while she has been so good during her makeover at the salon and the grocery shopping that followed! Is she once again trying to claim she isn't a sissy? Because her porn history and the awe she had in her eyes when she saw her new look certainly told another story." Ms. Thompsons shouted loud enough for the whole bar to hear what was going on as she quickly closed the distance towards Monroe and Lena. She lied, knowing a little lie now would help her cause big time. It would be word against word if he denied it and her word clearly carried more weight. Suzan would also be more than glad to back her up if it came down to it.

"Yes that, and she failed to call me Miss or use her proper voice, but the worst thing of all was that she had the nerve to call the people in here freaks. She clearly hasn't learned a thing yet!" Lena replied angrily leaving Monroe stuck between his angry wife and determined Nanny in the middle of a crowd that didn't know whether to be angry or amused.

"Hmmm, I see. I was afraid something like this might happen. It comes with the territory of the sissy trying to deny their true sissy selves. Beating down on all deviating from the identity they try to maintain just to try and cope. It's toxic and I hoped that it would have diminished now that we fully brought the sissy out, sadly I appear to have been wrong. I guess that means a punishment is in order as we can't tolerate this behaviour." Ms. Thompson calmly explained, spinning the narrative away from feminisation being the punishment, but a good and necessary way to stop Monroe from being an asshole. Making it sound like something he secretly craved making it easier for Lena to refuse letting him go back to his old self.

With that Ms. Thompson turned to Ben acting as if they had never spoken before. "Sir would you mind if I took a chair and took that stage you have in the middle of your lovely establishment to punish this sissy here? Since she offended everyone, I think it's only fair if everyone gets to see her getting punished so they can rest assured that it isn't tolerated and dealt with accordingly." Ms. Thompson asked as Monroe looked completely horrified. This crazy bitch couldn't be serious right? She couldn't spank him in the middle of a bar with so many people around could she? He feared that he knew the answer to those questions, but he didn't like them one bit. Looking at his wife he only saw anger and a slight amusement, a tell tale sign that he wasn't getting any help there and he knew for certain that Ben would happily agree, they had always hated each other.

"Be my guest Ma'am, this sissy had it coming for a long time and I'm glad something is finally being done about it. Want me to dim the lights and put on a spotlight for you? It'll still be pretty bright with the light from outside flowing in, but it should have some effect." Ben offered with a smile much to Monroe's horror, this was way worse than the simple yes he had been expecting.

"Oh yes please, that sounds like a great idea, just what I was aiming for when I wanted to move this on stage. Hear that pansy, you are going to be the star of the club. Now could anyone please help us out with a chair. At my age I'm not the best at carrying things anymore and this delicate flower her just isn't capable of doing any heavy lifting. Back at the supermarket she even had to use her charm to get a guy to help her out lifting the milk." Ms. Thompson said with a bright smile as everyone had a good laugh at Monroe's expense. The anger having turned to general delight over his humiliation.

"Sure I can help. After all I can imagine such a darling sissy housewife needs the help of a strong woman in her life to take care of the heavy lifting for her." A rather athletic looking woman with a colourful pixie cut, more than a few piercings, wearing a simple crop top, cargo pants and combat boots spoke as she got up and easily grabbed a chair with an elaborate flair much to the joy and amusement from everyone around as they gave her a loud applause.

While this woman was putting on her show Ms. Thompson took a firm hold of Monroe's upper arm and hissed in his ear. "You better thank that woman in your prettiest voice and give her a nice curtesy while you are at it when we make it up on the stage. Also when I spank you I better hear you count and thank me for each and everyone of those spanks. Fail and I'll be starting over spanking you with your shock button, understood? Hell I'll even invite everyone who wants to dish out a spanking up on stage after me, just try me." With that she simply gave him a shove towards the stage and put on a bright smile as her extremely nervous sissy ward minced towards the stage, terrified of Ms. Thompson's threat.

By the time he made it onto the stage, right in front of the woman who had just put the chair down for Ms. Thompson Monroe wished the ground would just swallow him whole. Since that wasn't going to happen he had to do everything in his power to make sure Ms. Thompson wouldn't follow through on her horrid threat. Completely mortified he dipped into a clumsy curtesy in front of the smirking woman who just started laughing in reply. "Thank you for bringing up that chair for me Miss." He spoke in his well practiced feminine voice, cringing as the whole bar including his wife burst into loud laughter that seemed never ending.

"You're welcome pansy. That curtesy could use some practice though." The woman laughed, giving him a limp wristed wave while Monroe's beat up pride bled further, getting teased on his delicateness by a woman way tougher than he was, was down right terrible. At least she did move off stage back to her friends who all gave her high fives while Ms. Thompson simply moved on stage and sat down, waiting for the crowd to calm down a little before she would carry on.