Best try on Chrome browser.
Chapter 19
Monroe was a true nerve wreck as he was pushed out of the salon. While he hated that horrid place going out looking like he did in this shady neighbourhood was absolutely terrifying. It had been horrible the first time, but now with this outrageous makeover it had only gotten worse. He didn’t even want to think about what these thugs thought about as they ogled him. It could be nothing good, especially not with how he could hardly recognise himself as anything but a very outdated delicate housewife. He was almost sure that they were having rather lewd thoughts and it made him shudder, he wasn’t gay, he didn’t want to give any man any kind of ideas or fantasies about him. Especially not in an area with so many dangerous looking alleyways.
Out of the door he rushed out to the car mincing as fast as he could possibly manage which still wasn’t all that fast. Still despite his restrictions Ms. Thompson was even slower than he was, taking it easy as she walked around to the driver’s side where she looked through her purse in search of the keys for an obnoxiously long time. Monroe was certain she was dragging this out on purpose, but fearing that he would just distract her if he complained making it take even longer he just shut up and kept his delicate looking gloved hand on the door handle ready to get in at the earliest possible time. As he nervously waited he couldn’t help but look around and see all the thugs he could spot look at him with lust filled gazes, some even pulled at their cocks a little to regain their comfort in their pants.
When the door finally opened it took Monroe mere seconds to get into the car and shut the door, taking most of him away from view and into relative safety. Eventually and completely at ease Ms. Thompson followed with a loud laugh. “Oh my, it looks like some pansy is eager to go shopping and show his new outfit and look off to a whole store. You’ll certainly look the part. After all there is no better place for a delicate housewife like you other than at home in the kitchen.” Ms. Thompson grinned loving the distraught look on his face as she taunted him. She seemed set on making him adhere to values of the time he looked to be coming from and it was devastating.
Monroe just hung his head in defeat, silently holding his clutch purse into his skirt covered lap. First this outfit and now this makeover had only further hit his confidence to try and stand up to Ms. Thompson. Besides arguing with her was no use anyway, the only use it had was trying to convince himself that it wasn’t true, but even with his eyes cast down seeing his delicate hands holding the elegant purse in his satin covered lap there was no getting away from how feminine he looked.
“Now pansy, while we drive over to the store I want you to study this list here. It has everything we’ll need today at the store. Study it well as I’ll take it away before we leave the car. For every item you forget you’ll get five spanks once we get back home. Of course since every item on that list is a necessity we’ll have to make a trip back to the store as well to get them.” Ms. Thompson smirked giving him the proper motivation to know that list by heart, a trick that worked wonders as Monroe instantly got started with the list not knowing what prospect was worse, even more spanks to his very sore bottom? Or was it the prospect of a second trip to the store? He didn’t really have to pick a worst, both were terrible enough to know he couldn’t afford a screw up under any circumstance.
The list wasn’t terribly long and Monroe was pretty certain he could memorise it well enough which was a good thing, but he also realised it wasn’t so much of a good thing at all. The relatively short list filled with mostly fresh products meant that it probably wouldn’t take a week before they needed more groceries again. He had really hoped they could just buy stuff that was good for a long time, and buy a ton of it, but Ms. Thompson clearly had other ideas. Sure it was most likely healthier, and health was important, but dressed as he was, he cared more about minimising his exposure than he did about eating extremely healthy. Like always Ms. Thompson’s ideas didn’t line up with his own.
They drove about half an hour to a very busy grocery store at the edge of the city. It was far removed from the upscale community he lived at and the chances of running into anyone he knew would be pretty much zero. Even if he did the chances of anyone recognising him were also pretty much zero, his figure was well concealed by his outfit, he stood much taller in his heels, his facial structure looked completely different with the makeup and there was nothing about his hair that even looked similar to his previous style and colour. While no one might recognise him, one thing was certain he would stand out like a sore thumb no matter what and it made him terribly nervous.
“Alright pansy, before we get out of the car I want you to put these in. I won’t stay close to you, but observe from a distance. These will ensure that you can still hear me when I say something and just in case you would get ideas, distance now won’t mean shit when we get back home.” Ms. Thompson sharply said as she gave him a pair of inconspicuous looking wireless earbuds. They would be pretty much invisible when worn yet Monroe didn’t hesitate for a second as he put them in while Ms. Thompson took away his list. After all having her speak right into his ear where no one would be any wiser was way preferable to other people potentially hearing her boss him around. His look was bad enough as it was.
“Good, now put this in your purse and get your ass out of the car. There should be a coin in there to get yourself a cart which is your first task.” Ms. Thompson spoke as she handed him a small white leather wallet with a golden delicate heart shaped clip. It held his card to check things out along with a few coins in various sizes. Reluctantly Monroe clasped open his clutch purse and slipped the wallet in. It was the first time since getting it that he had opened it up and he was mortified as he saw the contents. Inside were a couple of pink wrapped condoms that looked rather small, a small package of tissues and three tampons. With the wallet now inside the purse was nearly full, there was space for maybe a few more small items, but nothing big for certain. While no one would see the contents of his purse, it certainly was a huge added indignity to be carrying such feminine things. Even the condoms with his own cock locked up had a horrid connotation.
It took Monroe quite a while to brace himself and steel his nerves to make it out of the car, but the sooner he got this over with the better. After all he had already gotten a few strange looks from people passing by in the parking lot, waiting here just meant more people seeing him in the end and risking a punishment on top of all that. While this parking lot sure felt a lot safer than the neighbourhood of the salon, his shame hit him way worse. After all he didn’t have to care about what people here might do to him, but only what they would think of him and none of the things he could come up with were any good in his mind. Not only that, but there were also just a lot more people around here than there were around the salon.
With Monroe out of the car Ms. Thompson quickly left as well, closing the doors and cutting off his only path to relative privacy. From here on out there only was one option for Monroe and that was to get his shopping done. There wasn’t even any need of threats as he soon minced his way to the carts, taken the small heel to toe steps with a apt swaying bottom like the restricting underskirt forced him into. His elbows were neatly tucked at his sides and his underarms sticking straight out for support in his tallest heels just like Ms. Thompson had taught him to manage his balance. It was all he could do to have some confidence not to fall. He didn’t even realise just how ridiculous prissy that looked, no woman walked like that, and now that he had had his manicure, wearing those gloves and clutching that purse in one hand it only looked more delicate.
For Monroe it was a necessity though as he was slightly shaking from nervousness as everyone got to have a look at his outfit in its full glory, from his hat all the way down to his heels, not helping his confidence in his balance at all. The fact that he got plenty of justification to being this nervous only made it worse. The entire way to the carts everyone he passed went completely silent and stared at him, only to break out in animated gossiping and giggling behind his back. He was certain that it was all directed at him.
While those reactions were terrible, the worst once came from the men who obviously checked him out. He even had to endure a wolf whistle and that while he had only been out for a minute or two so far. It was simply devastating, not that he could blame them, if he had seen a woman dressed like this he would have certainly stared and even gawked himself. The colours and the frills were just a magnet of attention, and his outfit was certainly a lot more appealing that that of a lot of women wearing just regular jeans and tshirts these day. If only he could wear those, even if they were women’s jeans and tshirt. The crisp points of his bullet bra and the seamed stockings sadly hinted at just as elaborate lingerie which made the men day dream away.
As terrible as this was, there was no other option than to get his shopping done as quickly and efficiently with as little mistakes as possible. Running, even if Ms. Thompson wouldn’t intervene from a distance would be even worse than shopping. He for one couldn’t go very fast in these heels, he had no phone to call a cab and he was a long way from home. Walking was simply not an option making the only viable option walking until he could wave a cab over or taking public transport, all which would take a lot longer than just this grocery run. Even if he got home Ms. Thompson would probably just punish him then and drag him right back out here anyways.
Ms. Thompson for her part was loving this trip, Suzan’s work was just precious, even better than she had hoped and seeing all the fruits of her labour was magnificent. Just like Monroe she was very aware of all the stares he was getting, but walking ways behind she was actually in earshot to hear all the gossip behind his back and she loved it. Most of it was just sheer wonder, wonder as to who that woman was, why she was dressed like this, why she walked so ridiculous,, if she just came from a shoot for some retro calendar? Some even questioned whether or not Monroe was a woman, the sheer over the top fashion in which he was dressed paired with how he walked and his height certainly rose questions. He might pass well enough as a woman, but neither his dress nor mannerism would ever allow him to pass unnoticed.
By the time Monroe finally arrived at the carts he was confronted with another issue. He might have been able to handle his heels quite well without tripping for the time being, but simply opening his purse was a nightmare of its own. Handling that daisy clasp was very difficult with his awkwardly long nails and the shaking of his hands out of sheer nerves didn’t help one bit either. Opening it up just gave him a new worry as he now had trouble opening the tiny zip on his new wallet, and once he got that open there was a whole plethora of coins a lot of which simply wouldn’t fit. He really had to dig through them to try and find a right one which only dragged out his struggle and that while he stood in one of the busiest places, the place almost everyone had to go to to either fetch or return a cart.
He had been standing there fumbling with the various layers that hid his coins for well over a minute when he suddenly got shocked out of his concentration by a low male voice right at his side. “Here Miss, let me help you with that. I always hate those coin slots, often having a hard time finding the right one myself luckily I got myself a double today.” An older looking man in his sixties, holding out a coin to him spoke while being none too subtle with how he checked Monroe out, making him die a little inside. He felt so dirty getting obviously stared at right in his face. He didn’t even seem to realise that he wasn’t a woman, and he probably wouldn’t from staring at her pointed bust like he did. While passing was the goal to make this whole trip smoother, it wasn’t any less devastating to his male ego.
Ms. Thompson who had seen the man approach long before he addressed Monroe was having a blast. Given the way Monroe was made up and dressed he probably had a fair bit of nostalgia checking him out, this was better than she could have hoped for. Sure she had expected the fumble, but not this. Taking her hidden microphone she spoke right up. “Be sure to thank that man profusely, and call him Sir. Don’t forget your voice either Pansy, you wouldn’t want him to see through your disguise and make a scene right here and now would you?” She simply ordered.
The last thing Monroe wanted to do was speak to this man, he had been so close to fishing out that damn coin, but now he was trapped. Whether he accepted or refused he would have to talk with so he might as well take the easiest route and accept, doing as Ms. Thompson had ordered. “Thank you Sir, that’s very kind of you. You’re a life saver.” Monroe spoke in the best soft feminine voice he could manage after all his training, ending on a high note just like Ms. Thompson required.
“Oh it’s my pleasure Miss, it wouldn’t be right not to help such a sophisticated lady in need. Have a lovely day.” The man said putting the coin into his elegant looking gloved hand, before taking a cart himself and marching off. Monroe was left behind completely stunned and mortified, but he did have a right coin now and so he quickly took a cart of his own, fumbling a minute longer to get his wallet and purse neatly closed up again. Now with a cart in hand he had a much easier time walking to the store. The handle gave him support, boosting his confidence in his stride a lot. At least he didn’t have to worry about falling anymore as he carried on with a swish in his hip, taking small heel to toe steps like the skirt forced him into.
“I bet you have never been as popular as you are right now Pansy, all eyes are on you like you are some kind of celebrity. Just look at all those women admiring your look, some look envious, some even jealous, and you can’t really blame them can you? After all many of their husbands and boyfriends love your look as well judging from the tents in their pants. Now put a nice good wiggle in that ass of yours as you walk or I’m going to make you thank the next person who helps you with a little kiss. I bet that man at the carts would have loved a kiss.” His Nanny taunted as she watched her mortified ward put an extra wiggle in his hips as he headed to the store as fast as his small steps could carry him. Her threat was working most effectively.
Monroe couldn’t help but agree with his Nanny on that front that guy would have loved a kiss with how openly he had ogled him. It was something he needed to avoid at all costs. Just the though of kissing a man, even just a peck on the cheek and that on the cheek of some old pervert no less just made him shudder in disgust. Wiggling his hips as much as he hated it with how much attention he already dragged his way was at least preferable. This horrible trip couldn’t be over fast enough for him, but rushing wasn’t helping him one bit. The closer he got to the store the more crowded things became and once inside the store was buzzing with life. It was packed, especially compared to the high end store in their neighbourhood which was way over priced, but spacious and exclusive making it rather quiet and relaxed for a grocery store. Here he might be seen by a lot more people, but at least the ones seeing him weren’t as damaging as running into neighbours.
While he couldn’t really see his Nanny anymore in the crowd, he knew for sure she was following him at a distance. It might be very hard for him to keep track of her in the crowd, but she undoubtedly had an easy job keeping track of him. He really stood out like a sore thumb, but even if that didn’t work all she really needed to do was follow the eyes of everyone present and they would lead her right to him.
Most of Monroe’s time was spent in the fruits and vegetable aisle where he easily managed to pick up two thirds of his grocery list. For a moment he actually though that this was going to be over faster than expected. Running over the list in his mind and searching for the items actually offered a light distraction away from all the eyes pointed at him. It was only of little help, but at least it was better than heading for the entrance and focusing on all the stares and looks he got.
His Nanny also seemed to be leaving him alone which was a huge help or at least not a huge added worry like he had feared. All was going as well as it could given his situation until he arrived at the cucumbers. He had to pick one up so like with the rest of his products he just grabbed the first one at hand trying to do things as efficiently as possible. When he was about to turn around to put it in his cart Ms. Thompson’s voice suddenly cracked through his earbuds. “Don’t put that in your cart just yet Pansy, I want you to look through the crate for a bigger one, and when you do I want you to hold it up next to the old one just to be sure. When you do you are going to bite your bottom lip and put the smaller one away again. You are going to find three consecutively larger cucumbers and at the end you’ll put the largest one in your cart Pansy. Do a good job cause you wouldn’t want me to make you collapse in the middle of the store now would you? Just imagine all the men rushing to aid the wildly dressed up damsel in distress.” She taunted before once again going quiet.
Monroe knew exactly how it would look if he did as he was told. It would look like he was intending to use that cucumber as a toy, and like he was a slut for big toys. Nevertheless it was better than the alternative as he shuddered thinking about most of the men present surrounding him and touching him to help him get back up on his heels. With a soft inward groan he turned back to the cucumber crate, scanning it for one that looked slightly bigger. It took only a few seconds to spot one, and as demanded he held it up to the one he was currently holding, smiling and biting his bottom lip only to put the first one away again.
With all eyes in the area already on him people instantly took notice of what he was doing and much to his horror he could instantly hear whispers about him behind his back. “Oh god for such a proper lady she sure seems to be a huge slut inside.” Or “The poor dear, her husband probably isn’t able to give her as much as she needs and if her outdated look and choice of toys is anything to go off I bet she doesn’t own a proper toy either.”
When Monroe did the exact same thing again it was followed by more shocked gasps and whispers, but the third time was the absolute worst. Finding a bigger cucumber the second time had taken a bit, but to find a third even larger one was nearly impossible. Monroe had to rummage through the entire crate to find one, much to the curiosity of new people who had entered this area of the store and when he did find one and repeated his lip bite compare people seemed to be even more shocked. “What a size queen.” “I hurt just thinking of using such a monster. “or “Damn, she might be pretty, but that pussy is probably loose as fuck.” Monroe overheard as it really looked like he had searched long and hard for the biggest cucumber to take home with him. He was so very relieved when he was finally allowed to move on.
ero
