The Live-in Landlord Pt. 02

On the day before my first day of work, I had a trial run on being in public.

The day started as usual, and Michelle told me about what we would be doing as I dried her with the towel. "You need to put some of that training into practice, so we're going to go to the supermarket and a coffee shop to get you used to being a girl in public, okay?" I nodded along, my focus, as usual, being on Michelle's body as I dried her.

For my first outing, I paid careful attention to every item of clothing that Michelle had decided I should wear. Over my freshly shaved legs, I pulled on a pink lace thong, complete with a large pink bow on the front, and a matching A-cup bra. Over my lingerie, I wore a tight fitting light pink skater dress, which was very short, and ended well above my knee. I also slipped on some light pink heels on my feet, with open-toes, showing off my bright pink painted nails. I also took time with my make-up, wearing lots of foundation, light eye shadow, mascara and some glitter around my eyes too. I wore pink lipstick to complete the look, and contrast with the long flowing blonde wig which I wore.

I was much more used to being dressed like this following my training of the last two weeks, but knowing people other than Michelle would see me made me incredibly nervous. I tried to imagine telling myself from a few weeks previous what I would be doing, and realised I wouldn't believe this. It was still hard to believe how deep I was into this, but I kept telling myself it was the only way, I owed so much money I just had to do this. Of course, an increasing part of me was also starting to enjoy myself as well, yes I was nervous, but I was having such a good time being close to Michelle, and she had made me look so good. I didn't ever want to look like this before, but I knew I looked very... pretty, and it felt amazing.

I admired myself in the mirror, but kept touching up my make-up, rearranging my bra under my dress, every little detail had to be perfect. I knew that I looked good, but I was still worried somebody would notice me.

"Time to leave Charlotte!" Michelle called. Another development that morning, was my name. Michelle reassured me I could still go by Charlie, but I would have an easier time responding to Charlotte at first. I took her advice, wanting to pass more than anything.

"Yes Miss." I responded, grabbing my clutch bag. This was one of the stranger feelings, no pockets, and having to keep hold of a handbag in order to carry my phone around. I also fit into my clutch bag some lipstick for touch-ups, a romance novel I was reading, and a body spray covered in pink flowers.

I was incredibly nervous, but also felt a thrill. As I walked outside to Michelle's car, the feel of fresh air on my smooth legs felt incredible, though I had to be careful as my dress fluttered around my upper thighs. There was more to think about in public.

***

Michelle parked up at the supermarket, and killed the engine. "Okay, time to remember all of your training, i'm sure you will be great." Michelle said encouragingly. I exited the car, and walked beside Michelle, remembering my heels and walking training, swaying my hips as I moved.

There were other people around as we walked in, but nobody immediately pointed and laughed at me, which eased my worries. We walked around the store, and I grew more confident with each step. I noticed a few men staring at me, but I quickly realised it was more checking me out in admiration, rather than me being an imposter, which further boosted my confidence. I guess I just needed to get used to longer lingering looks from men.

We continued through the store, Michelle picking up luxury items, including steaks, lobster and fancy cheese. "I'll pick the items this time, but next time, I want you to take over the cooking and preparation fully, no more recipes, you should have learned what I like by now." I nodded along, mainly focusing on my appearance. "It should be easy, you only need to think about me, you can stick to your shakes."

We finished in the store, and headed to the checkout. I even received a compliment on my dress from the woman on the checkout, which added a further spring to my step. I felt amazing as I was walking out of the store and back to the car.

***

Michelle drove us straight to the coffee shop, ordering a latte for herself, and a glass of water for me. We sat down on a small table near the entrance.

"Well done, I told you that we would pull it off didn't I?" Michelle told me proudly.

"Yes Miss, thank you." I replied quietly, trying to avoid anybody overhearing.

"I need to send a few emails, so why don't you read your book?" Michelle pulled out her laptop, and started tapping away at the keyboard. I reached into my clutch bag and pulled out the novel. I was a little embarrassed to be reading this in public, it was called 'The Forbidden Lord' and had a picture of a hunk with his shirt off on the front, grasping a woman in basically a princess dress on the front. I would never have been caught dead reading this as a guy, but in my own pink dress, it felt more acceptable. Whilst at first I started reading the books that Michelle provided me out of sheer boredom at having nothing else to do, I really started to unironically enjoy them. I found myself empathising with the women in the book, and getting caught up in their stories, even finding the men alluring. I convinced myself that was just because of the way the book was written.

I finished a chapter, and headed to the bathroom, only to realise I was on unfamiliar ground. I walked on instinct into the men's bathroom, and realised my mistake quickly, but too late. A man was just finishing washing his hands and turned to see me walk in, "Wrong door honey." he looked at me, speaking with familiarity. He was probably 20 years older than me, dark hair but showing signs of grey, and at least 6'3. I blushed, and turned around quickly, though heard him follow. I felt him grab my waist from behind, and he held tight, guiding me over to the women's bathroom, "there you go", his hand left my waist, but as his grip loosened he allowed his hand to softly trace down my back and over my ass.

"Thank you." was all I felt able to reply, and I quickly rushed in. I opened a stall, and proceeded to pee, making sure to dry my clit before pulling my panties back up. I smoothed down my dress, and made sure I still looked presentable in the mirror. Another woman walked in and smiled at me, she stood next to me applying lipstick. My heart fluttered at this moment, knowing I belonged. It was such a small moment, but I felt like a woman, and a lot of feelings dawned on me at once, mainly, that I was no longer being dragged along by this, I was enjoying myself, this was right.

I left the bathroom and returned to my seat, pushing on with my novel as Michelle worked.

We spent over an hour in the shop, focused on my novel the whole time. Just as Michelle closed her laptop, I felt a hand on my shoulder, firmly pressed with the fingers reaching forward towards my chest. It was the man from the bathroom earlier, with his other hand he dropped a small napkin in front of me with some digits on it, clearly his phone number. Before I could reply or speak, he walked away out of the front door. Michelle looked up at me and smiled, "I knew you would be a natural."

***

I was exhausted the night following my first outing. Normally at my 8pm bedtime I continued reading the women's magazines or romance novels in my bedroom for an hour or so until I started to fall asleep, always having to hand my phone back to Michelle before my bedtime. However, I was getting more used to my schedule, and the intensity of that day in public really tired me out, and I fell asleep in my satin pink babydoll and matching thong panties as soon as I climbed into bed.

My schedule changed with the first day of my new job, I still woke early, with my first job showering, shaving and moisturising my body. I took care each day to ensure I was fully hairless, but today I wanted to make sure I got every last inch. I had noticed small changes to my body each day with the pills and shakes that Michelle had me taking, but today I couldn't help but notice the swell of my breasts. They were still very small for a woman, probably somewhere between an 'A' or 'B' cup, but this was the first time I really noticed them. I was shocked, and started to get a little nervous, how deep was I into this? I couldn't help but also feel grateful at the same time, knowing it would only help me pass as a woman.

I then proceeded to my wardrobe where Michelle had selected my outfit for the day. I pulled on my pink lace panties, in a 'tanga' style which still had plenty of material around my butt and hips, but rode up like a thong. I then put on my matching bra, noticing my breasts comfortably filling the small cups, and almost slightly spilling over. I then pulled on some stockings with a garter, and fixed them into place, before gently stepping into my black dress. I had to admire Michelle's selection, the dress was professional looking but still revealing, it was black and figure-hugging, with a small belt around the centre to accentuate my hips. The material covered the shoulders, hiding my pink bra straps, but left the arms exposed, and there was a narrow slit from the neck plunging down to show a small amount of my developing cleavage. The bottom of the dress went down to just above my knees, but there was a long slit in the side to reveal my shiny smooth legs. Next to the dress was a small black clutch bag and shiny black heels to go with my dress, I made note to put them on once I woke Michelle.

Once dressed, I proceeded to apply my make-up, following all the lessons I had learned from Michelle. I applied concealer and foundation for adding a base colour of rose eyeshadow on my eyelid, and a deeper pink eyeshadow above my eyelid. I finished my eyes with a liquid liner along my top lash line, and finally added two coats of mascara. Moving on, I applied a light coloured blush at the top of my cheek and along the cheekbone before using a darker shade of blusher to apply in the hollows and sweep upward, using the blending technique I had been taught. To complete the look I finished with the lipliner and a muted red lipstick. I admired myself in the mirror once completed, feeling incredibly accomplished after struggling with this process during the week. I couldn't believe how good I looked, my heart began to flutter. I really did look like a professional woman ready for work.

Once I had finished on my own look, my next task was to prepare for Michelle. I first ironed and laid out her outfit for the day, before then making her breakfast. I was now much more used to just having my shakes and pills through the day, and making a delicious breakfast for Michelle no longer felt like I was missing out, but only that I was serving and treating Michelle. I felt good rushing around the kitchen in my tight black dress, conscious of my modest cleavage in front of me.

As I woke Michelle, she complimented me on my look and my confidence grew greater. Once she finished her breakfast, I prepared her morning bath.

"You haven't had a little accident for over a week now, do you think it's safe to keep your nice work clothes on for this?" Michelle asked me as she was undressing. It was true, for the last week or so, I had not cum whilst drying Michelle, in fact, it dawned on me that I barely had an erection for a few days. I still loved drying Michelle, and I found it just as intense as that first time, but my body wasn't reacting the same way. I started to wonder whether the pills and shakes were impacting me in that way too, I suppose it made sense. I know I would have been incredibly frustrated by that before, but on learning it at that point, I felt accepting. My clit was so small anyway that it probably just made things easier. "Maybe change your panties, just in case." Michelle added after my silence, trapped in my own thoughts.

I automatically proceeded to pick up Michelle's discarded leopard print and red-lace trim panties from the floor, ready to briefly swap them with my own. However, as I started to pull down my pink lace panties, I realised it wouldn't be so easy with the garter I had on over the top. Michelle noticed my predicament, "That's a lesson for you, always wear a thong with your garter, and always wear it on the top, there are so many reasons you might want quick access..." she said shaking her head. I nodded along, and returned to my bedroom to quickly sort myself out whilst Michelle bathed.

I returned with Michelle's still warm leopard print panties on, and proceeded to dry her as she stood. I enjoyed the process as much as ever, but did pay attention to the complete lack of reaction from my clit, knowing now that it was even more useless. Part of my old brain was screaming out, saying that this was a problem, that I was going too deep into this situation. However, at the front of my mind, all I could think about was how much easier it would make wearing panties, how it made my clit more like other women's, and how it might please Michelle. I felt any resistance slowly drip away.

"Good girl." Michelle said once I was done, and I felt good, ready for my day.

***

I was even more nervous than the previous day in the card ride to Michelle's office.

Michelle led me into the building, both of our heels clacking as we walked along the pavement outside. Inside was a room of around 5 desks, one right next to the door, the others further back into the room facing each other. Two women were around the desks towards the back of the room.

"Hi girls, this is Charlotte." Michelle announced, pointing to me.

"Hey." the two women said in unison, they seemed excited to meet me. Michelle took me over, and introduced me to both of them. The desk on the left was occupied by Rachel, she was probably early-40s, with shoulder length dark hair, on the chubbier side and wearing a colourful blouse which clearly contained huge breasts. Sat opposite her was Emily, she was much younger, long straight blonde hair and impressive make-up, wearing a plain white shirt over her slender body. They both seemed really friendly, and I started to calm down a little.

Michelle then took me over to the desk by the door, telling me it would be my desk. She ran me through the various tasks I needed to do, including greeting people as they entered, and that Rachel would tell me what to do as the day went on.

I settled down, smoothing the dress over my legs as I sat down to the desk, and took my surroundings in. I would have struggled to believe the position that I found myself in two weeks ago, but I was looking like a sexy professional woman, earning money and working in an office. Most surprisingly of all, it felt right.

Michelle left me in the office, clearly allowing the place to mostly take care of itself. I noticed she checked her emails a lot, and made calls through the day, but she didn't need to be physically here a lot of the time. I suppose having a team of people to keep up all of her properties allowed her a lot of time away.

Rachel walked over to me, I noted that she wore simple black trousers and pumps as she appeared from behind her desk. She asked me some friendly questions, and proceeded to give me some tasks to get started. She let me know the most usual reasons for people entering the office (tenants with issues and contractors asking for direction), and told me what I needed to get on with otherwise.

The morning went by very quickly, I needed to respond to a lot of basic emails, and do some filing for Rachel. Only one person entered the office, which I was thankful for, a young woman collecting the keys for her apartment, she was friendly and only stayed briefly. That relaxed me for future visitors.

At lunch, Emily asked if I wanted to join her, and I jumped at the chance. Of course, I would stick to my shake and pills, but I told Emily that I would appreciate a walk with her and a chat. She guided me on a walk to the local sandwich shop.

"So you're living with Michelle?" Emily asked as we walked.

"Yeah." I replied, not knowing exactly how much she had been told, and what to say my relation was to her.

"She's your Aunt right?"

I jumped on that chance, a convenient backstory that Michelle had clearly prepared, "Yeah, i'm living with her for a while, she helped me get some work."

"Ah, that's cool. So what do you think of Rachel?"

"She seems nice." I replied.

"Yeah, she's friendly most of the time, but sometimes she can be a total bitch." I raised my eyebrows. "Just, she's my boss, and if I ever get anything wrong she will go on and on, and make you stay late, stuff like that. Just a warning."

"Ah, thanks, good to know!"

We continued walking, thankfully Emily didn't question too much about my shake and pills, or why I wasn't eating. She even commented on my dress, and I returned the favour, particularly liking the pencil skirt she wore with her white shirt. I found myself struggling to believe I was making a girl friend, and she didn't seem to suspect anything was amiss. I was starting to enjoy myself!

The afternoon was mostly uneventful, though at one point a couple of builders came in, asking for the keys to a house which they were booked to do some work inside. However, the two men, wearing dust-covered overalls and high-vis jackets leaned over the desk and looked down at me.

"Haven't seen you here before love," one with scraggly hair said.

"No, it's my first day." I replied, forcing a smile.

"Well, what's your name, i'm looking forward to getting to know you a bit more."

"Charlotte."

"My name's Mike." the scraggly haired man continued, "looking forward to working with you." he smiled as he looked to his friend with a shaved head.

I handed the keys over, and the shaved haired man held my hand a bit more than he needed to, and for a bit longer than necessary when taking them, "My name's Gavin." he said. I could see him catching a glimpse towards my cleavage, and started to blush a little.

They left quite quickly once they handed the keys, laughing with each other.

Emily left at 5pm, chatting with me as she did, before Michelle arrived shortly afterwards to pick me up and drive me home. She chatted with Rachel for a while at the back of the office before returning to me, and gesturing for me to join her as we exited, and headed home.

***

[A handwritten letter]

Dear Miss Michelle,

Thank you so much for providing me with an opportunity to work for you. I have worked so hard in training, and I appreciated the clothes and make-up you have provided to me.

The girls at work commented on how great I looked, and that is all down to your teaching.

I have noticed the pills have started to give me breasts, which I know you were really proud of. Thank you for doing this for me. I am a little bit worried that it is also affecting my clit, but I trust that you know best for me, is there anything I should do?

Also, would I sometimes be able to watch some TV shows with you?

Thank you so much,

Love Charlotte

[A large selection of love heart stickers, glitter and lipstick kisses were placed around the page]

***

The week continued, and I felt more and more comfortable heading into the office.

On the Wednesday evening after work, Michelle sat me down and talked to me. "Thank you for the letter Charlotte, you're becoming a very polite girl, but I know you have some questions about your little clit." I blushed a little, forgetting the letter I wrote and left for Michelle the previous evening. "There's nothing to worry about, but I need to teach you about periods. I'm due tomorrow, and I think it's only right you share it with me."