Caught in a New Life

Chapter 24

Given how yesterday had gone the drive into the city where he had been put through so much shame got Monroe right on edge. The goal that was shopping for more of these horrible outfits didn't put him at ease at all, he could only dread the kind of shop that carried such clothes, it was probably in the same vein as that horrid salon from the day before. Not only that, but being out in public was downright devastating as well. Wearing all this frilly colourful garbage was embarrassing enough without anyone able to see him, it was such a huge eye catcher that it was impossible not to be seen by anyone around though.

A strong shudder ran up his spine when they eventually stopped in front of a boutique called CC's, one that looked a little bit familiar for some reason. It wasn't in a bad part of town, yet not on the main shopping street either. It was moderately crowded, but at least there weren't any scary gangsters around this time. One look at the store's windows only further fuelled his dread, looking at the outfits on the flat chested mannequins it was quite clear that this was indeed the store his clothes had come from. There were no somewhat vintage looking dresses like he wore now on display, but every single one of the dresses matched his in sheer frilliness and colourfulness. He already dreaded thinking what he would be made to go home with.

"Alright Molly, listen carefully, Linda is a very good friend of mine so I want you on your absolute best sissy behaviour. I don't want you to embarrass me, I want your behaviour to be a good reflection of how well I've taught you up until now, I'm only going to warn you this once, but Linda like me has no tolerance for an unruly sissy and she won't hesitate to bend you over her lap the moment she deems it necessary. I promise you now that if she ends up punishing you, you can expect the same punishment twice over from me when we get home, understood?" Ms. Thompson asked sternly as Monroe gave her a frightened nod. He didn't know this Linda woman, but he was already scared of her, getting punished by yet another woman he didn't know was the last thing his crushed ego could use right now.

"Good, I'm glad we've come to an understanding here. Now I want you to head in in front of me, make sure to use your best possible mince, put on your brightest smile and when you see Linda I want you to drop into a perfect curtesy. You're going to introduce yourself to her as sissy Molly and you are going to tell her how much you love this outfit and how you couldn't wait to come here once I told you we'd come here to shop for more outfits just like this one. It goes without saying that you should use your perfect sissy voice when doing so. Now go!" Ms. Thompson instructed firmly as she remained seated in the car for just a bit longer.

Nervous and embarrassed out of his mind Monroe unbuckled his seatbelt and got out of the car trying to manage his skirt and petticoats as well as he possibly could. He really didn't want to get out, but all his time with Ms. Thompson had made it very clear that she wasn't known for her patience and he really didn't want to try her out, knowing it would make things so much worse for him if he did. As predicted just about every eye on the street turned to him, his outrageous hairdo, the colourful frilly dress and his sheer height in these heels really a sight to behold. It made him want to walk as normal as he possibly could, wanting to avoid further chuckles, gasps and whispered comments about his look from those within earshot. Walking completely normal in these heels was impossible though and he knew he couldn't neglect his mince with Ms. Thompson watching his every move from the car, he didn't put it beyond her to make him mince up and down the street a couple of times if he refused to mince properly for the relatively short distance from the car to the front door of the shop.

The stares and giggles he had to endure for the minute it took him to reach the door was intense, he couldn't even blame people considering how he looked. Much like yesterday this trip was shaping up to be one big embarrassment once more, and it didn't get any better when he reached the door and read the sign taped to the glass. "CC's sissy vintage fashion show, today at 10:30 a.m. Free entrance and refreshments." Given how he was dressed and how this show was supposed to start in thirty minutes, Monroe had a very bad feeling about this. Would he have to run in that show? The thought alone made him shudder to the point where he considered running. A thought he quickly banished, where could he go dressed like this? Hell he would never be able to out run Ms. Thompson either, and all she needed to do was press a button to send him to the ground in pain, if this show was for him to run in then he was screwed, he thought as he stepped into the door with a deep breath.

Only a few mincing steps in he was met with a tall gorgeous red haired woman who came to look at why the bell had rung. Her curvy figure and her classy black and white outfit which showed off some nice cleavage and plenty of her stocking clad legs only made her look all the more appealing in his eyes, nevertheless rather than turned on he felt intimidated by her, this woman, unlike most women he met was actually as tall as him, and there was just something unsettling about the way she sized him up as her next meal, giving him a smirk rather than a smile. Her beauty gave off a real danger vibe to him, much like the beauty of a poisonous frog. "Hello sissy, I'm Linda, the owner of this boutique, and you are?" She asked slyly, looking amused when he trembled a little.

Knowing what he had to do, Monroe hid his fear and embarrassment behind a huge fake smile, his teeth looking all the whiter past his fire engine red painted lips, not as immaculate as the day before, but passable for a quick inspection. With that he dipped into a by now rather well practiced curtesy. "Pleased to meet you Miss Linda, I'm sissy Molly. I just adore this outfit I was told came from here and when my Nanny told me we would come here to shop for more outfits just like it, I just couldn't wait." Monroe rattled off in his higher pitched sing song voice like he had been taught. He couldn't help but feel like a complete and utter fool introducing himself like this. It was so much more painful than being called a sissy by others.

His shame got fuelled even further when Linda started laughing and clapping. "Well it's my pleasure sissy, I've designed all of these dresses and outfits myself. I just love bringing out the frilliest most dainty parts of any sissy, and can I just say that you look like the most perfectly pathetic sissy ever, that dress certainly suits you so well." Linda taunted him with great delight, further driving home his intense shame. He couldn't even disagree, he really looked like a pathetic sissy and this dress fitted his look more than any of his old clothes ever could. Even without the elaborate makeup, his bleached hairdo was just to much to pull off with anything other than a dress, he thought as he suddenly got startled by the sound of a bell from behind him as Ms. Thompson walked through the door.

"Ah Doris, there you are, its so good to see you again, and can I just say now that you did an amazing job with this sissy right here? I got the politest curtesy and introduction. You're a real miracle worker, please come on through, I've put everything we need behind the curtain so the sissy can try on her new clothes, after all you can't buy something without making sure it fits, especially considering how expensive these outfits are." Linda smiled addressing Ms. Thompson while completely ignoring Monroe, it made him all the more embarrassed, like he couldn't talk for himself. He knew better than to object though, so when Ms. Thompson gave him a mild shove, he knew he needed to follow Linda shortly as he minced behind her, growing increasingly nervous as he took in the sights of this vast amount of sissy outfits. Although a lot of the outfits followed way different themes than his did, it was hard to spot anything better in the collection, just like it was hard to spot something worse, they were all equally terrible.

When they ended up reaching the very back of the store Monroe's worst fear became a reality, the only curtain he could see was the one at the back of the stage they had installed there. One with a couple of comfortable chairs in front of it and a couple of folding chairs to create more seats. Piecing everything together there was just no other way than that he would have to give that fashion show as promoted on the door. A fear that was soon confirmed when Linda spoke up again. "So Doris, since you are here to help Molly buy up my whole Stepford sissy collection I thought it would be nice to make a small fashion show with some interested people out of it, Molly needs to try everything on for sizes anyways, and it will be good mincing practice as well. Besides hearing how much she adores this new collection I'd say she wants to show it off the world."

Fashion shows were a new marketing idea for Linda now that she was starting to get some clients she could pressure into it along with a second sissy at home it was doable. She didn't plan to widely advertise them though, after all she didn't want to attract some perverts looking for some live sissy porn, no the paper at the front door would assure that only people who passed by her boutique here in the shopping street and showed some kind of interest in it would show up. The perfect public for a maybe future client base. If not then the people who showed up would have an amusing time here at the expense of the sissy on show which was also a goal in and of its own.

"Oh Linda, how absolutely thoughtful of you. I bet Molly can hardly wait to try on those dresses and what good is a new wardrobe if you have no one to show it to? Go ahead Molly, why don't you give Linda a proper thank you for allowing you to show the world just how much of a big pathetic sissy you are." Ms. Thompson instructed, using this opportunity to further drive home the deep shame he was constantly dealing with. She had already pretty much destroyed his ego, but her job wasn't done until he believed he was truly nothing but a sissy who should be happy to serve under her Mistress.

Monroe badly wanted to protest this whole thing, the last thing he wanted was to be put on a stage like this, or in many more outfits just like this one. The idea alone was enough to make him shudder, yet even the slightest refusal would lead to big trouble with his Nanny who wasn't to shy to spank him wherever they were and if he could believe her which he definitely could when it was about something bad for him, then Linda was just like her. Stuck between these two intimidating women there wasn't a chance he could say anything even resembling a no, it was devastating. It really did make him feel like the sissy they called him as he took a deep breath to try and calm himself a little. He just needed to put up with this until this horrible Ms. Thompson was out of his life, then he could finally work on making his wife believe he had really changed and hopefully be allowed to return to some semblance of normal over time. It was his only hope it felt like as for now he complied and dropped in a curtesy once more. "Thank you Miss Linda for allowing me to show off my dresses and show the whole world what a big pathetic sissy I am." He spoke defeatedly in his high sing song voice.

"Wonderful, you are very welcome Molly. Seeing you now I can say with absolute certainty that I made the right call convincing your wife that you were a sissy at heart after she came to me for answers, having found my store through the ads on the site of that sissy you jerked off too, one of my first clients. I mean look at you, no self respecting man would ever look like this. Now follow me so I may introduce you to my stepsissy Stephanie. She will be your stylist for your little fashion show. You will cooperate with her like you do with me understood? Stephanie has gotten strict instructions and if you don't cooperate with her, you'll have to deal with me and your Nanny." Linda firmly instructed, loving the look of stunned disbelief on his face. She wanted him to know that his sissy life was her design, while she gave him a look that dared him to step out of line.

Linda's comment made everything become clear to Monroe. Now he knew why Lena had been so hell bent on sissifying him, how she had been convinced that this was the right thing and to let Ms. Thompson in their home. It all made sense and he could feel his blood boil just looking at this woman. He was so mad that he almost lashed out, but there was something so paralyzingly intimidating about the predatory smirk she fixed him with that he couldn't bring himself to act on his anger instantly. A second guess was all that was needed for him to realise that aside from knowing how it had happened, nothing had really changed, he wasn't in any better position to help himself out of this mess. They could easily shut him down the moment he lashed out so all Monroe could really do was hang his head in defeat, mourning that he would let the woman who had created this mess push him even deeper. The chuckle Linda let out in response only added insult to injury. "See, nothing but a pathetic sissy, follow me." She spoke, as if she really wanted to get a reason to punish him. Resisting giving her one wasn't making him feel any better though as she started to sulk along.

His sulking earned him an instant scolding by his Nanny. "Molly, I thought I've taught you better than that, keep that back straight, that chin up and put a smile on your face. You aren't acting worthy of the sissy you are so change that this instance or find yourself over my lap, I won't allow another transgression, if you slip on stage I won't hesitate to march up there and put you over my lap, remember that very well." She scolded sternly as Monroe complied in rapid fashion, knowing what awaited him if he didn't comply. It only served to deliver yet another harsh blow to his already significantly hurting ego. He really felt like the pathetic sissy he had been made to call himself and it pained him to no end. With a perfect posture and a simpering smile he followed a still chuckling Linda to the back of the stage only to take the few steps up to move behind the curtain where he was met with a pretty petite redhead dressed in a frillier version of Linda's outfit. He could only assume it was Stephanie and he could hardly believe she was a sissy.

"Molly this here is my stepsissy and trusty employee Stephanie. Stephanie, this is our client for the stepford sissy fashion show Molly, why don't you give her a big sissy greeting before getting her ready for the first outfit. If at any point she fails to cooperate, you'll walk up to the front of the stage yourself and announce that Molly here is being naughty, do you understand?" Linda asked with a big smile as she made an introduction between the two sissies while simultaneously making it very clear to Monroe what was going to happen if he didn't behave perfectly.

"Yes Mommy, understood. Welcome Molly, I am so looking forward to getting you dressed in all these fine outfits. This is going to be a wonderful morning." Stephanie gushed in a high pitched voice with a terrible lisp that shocked Monroe. There was just no way he could take this sissy seriously like this. His shock only grew when Stephanie took him in a tight hug only to give him an air kiss to each cheek, never actually touching. It was mortifying to Monroe, but he knew he couldn't squirm his way out of this one. There was a time he would have loved to meet a submissive enthusiastic sissy like Stephanie, but now that he was one of them, he had lost all interest. Especially since he was in no position for the kind of fun a sissy had appealed to him.

"Wonderful, then I'll leave the two of you to it." Linda spoke cheerfully before simply turning on her heel and leaving the sissies alone. With nothing but a curtain shielding them from view there wasn't a lot that could go wrong so she wasn't worried at all as she went ahead to talk to her old friend. Monroe in the meantime wasn't given any time at all to feel relieved that the two worst women he had ever met were finally out of view. Breaking the hug Stephanie took his hand only to mince him right over to a sort of changing area off to the side where a rack full of colourful dresses was hanging preselected for him. It was hard to make out just how many were there through the sheer mass of colours, and frills, but that alone was more than enough for Monroe to know that a dreadful time was awaiting him. He couldn't see a single thing that was even remotely close to something he might feel comfortable in, but that wasn't stopping Stephanie from stepping up behind him and starting to help him out of his current outfit.

Although he was getting undressed in front of an attractive sissy, attractive enough to give his caged cock trouble rather than in front of the horrible Ms. Thompson, it still was more devastating to Monroe than stripping in front of his Nanny was. Especially when it came down to his lingerie and then finally out of his lingerie altogether. After all Stephanie was yet another person to see him in his most embarrassing caged state, the outfit everyone saw was horrible enough already, but the cage was a true sign that he was being owned. The fact that Stephanie was being very gentle and even downright sensual with how she undressed him didn't help his caged plight one bit. It made his cage really hurt.

It wasn't only his nakedness that bothered Monroe though, but also the simple fact that he was literally being pushed around by another sissy, someone who looked weak and submissive in their own right in Monroe's eyes, yet he was taking her instructions nevertheless, scared of what would happen if he didn't. It was another blow in a series of so many to his already beaten ego and although out of his heels and corset he had his mobility back to fight this sissy with ease, being taller and he was pretty sure way stronger than her. She also didn't have a button to shock him with and yet he didn't feel like he could do anything here, not even with Stephanie in charge. Linda and his Nanny were right behind the curtain after all.

Unlike his Nanny, Miss Linda, or pretty much anyone else in his life Stephanie didn't look like she was phased at all by how he looked. There was no judgement in her eyes, no mockery, no taunts, even the cage didn't get any reaction out of her leading Monroe to believe she was in one herself. As mortifying as it was to be pushed around by Stephanie, Monroe was at least grateful that the fellow sissy seemed to want to make it as easy as possible on her while her Nanny would have certainly tried to make it as embarrassing as possible. Then again given by the muffled talking he could hear behind the curtain his Nanny had better things to do like catching up with Linda.

While Stephanie was trying not to make things worse Monroe's nerves were shot as she started dressing him in a new and equally horrible outfit. Unlike the lime green outfit he had just worn this one's main colour was a soft pink satin following a very similar design to his pervious outfit. The panties high waisted and made out of a soft pink satin that had red lace trimming the leg holes and waist band along with a heart shaped hole in the front of the panties for his cage to fit through. The fit was very snug, yet they fit perfectly.

The corset was an under bust one, just like the one he had just worn had six garter straps each ending in a heart shaped tab. The main body of the corset was made of a soft pink satin. A heart shape red lace overlay decorated the front at the very centre of Monroe's stomach. In the back it laced with a red satin ribbon that was tied off in a big elegant bow. A pair of sheer red nylons with a soft pink sole, back seam and tops were smoothed up his legs and clipped to the garters. As an added accessory he was told to put on a pair of red nylon ankle socks with a soft pink ruffled lace trim and a satin bow tied in the back only for his feet to be slid in a pair of four inch tall soft pink lacquered leather heels with a red bow decorating the tips.