BDSM

Maid For The Job

Desperate to keep his job, Alex agrees to bizarre conditions.

Spankmasters
Jul 5, 2024
20 min read
femdomlight to extremereluctantMaid For The Jobcrossdressingsissification
Maid For The Job
Maid For The Job

Maid For The Job

Calm yourself.

The quiet voice sounded in my mind through the pandemonium of panic and anxiety, bringing with it blissful silence. I checked my reflection in the bathroom mirror, thankful no one else was in the office's toilets to see my mini-meltdown. My grey face stared blankly back at me, not far from being devoid of life and emotion, it was hard to believe that I was only in my early twenties, the face staring back at me looked like it had aged a fair bit more than the twenty-one years that I had lived. I slumped, leaning on the counter as I rinsed my face with cold water, hoping the shock would liven me up a little. My suit looked equally tired, but I could barely afford to survive, let alone buy new clothes.

My life wasn't always this tragic. Barely five years ago, I signed a youth contract with an English Premier League football club. It had been a dream come true; I had the body of an athlete, healthy support from family and friends, and a lucrative future ahead of me; that was all until tragedy struck in an under-eighteen game for the club I had signed a contract to play for.

Rumours were that the first team manager, a worldwide renowned character within the sport, planned to show up and watch, and I was fired up for the game and ready to impress. The game started well, confidence flowed through me with a fluidity that I produced on the pitch, and every time I skilled past an opponent, I grew more arrogant, teasing the defender at his inability to stop me. The fourth time I humiliated the defender, and passed him with ease, he'd had enough with my attitude and he lashed out with a dangerous tackle, severely breaking my ankle in the process.

From that moment on, my life fell downhill rapidly. The decline started with an addiction to the strong pain medication that the club's doctor prescribed. To deal with the depression of not being able to play football, I started drinking and smoking weed, and despite the best efforts from Alice, my girlfriend at the time, to motivate me and aid me on the road to recovery, my addictions spiralled to include drinking, gambling and taking 'Class A' drugs. The club caught wind of my activities and terminated my contract for breach of conduct. It was funny, despite being the architect of my downfall, there was no support from the club on how to handle becoming incredibly wealthy, so suddenly, at a young age.

Exasperated, Alice left me, feeling hopeless in her inability to help me return to being the person she fell in love with. It probably didn't help that I stole money from her to fuel my growing addictions, and cheated on her numerous times. After Alice left, the addictions continued to take control of my life. I jumped from relationship to relationship, desperately trying to replicate what I had with Alice before the injury. The money from the lucrative contract was rapidly diminishing, and I soon had to remortgage the house I was still paying for. I ended up having to rent a run-down flat in a bad part of the city,

So, that was why I found myself nervously standing in the bathroom of a shared office building, rueing the day I had an abundance of charisma and charm that would have seen me nail this interview. I was only applying for the role of a part-time cleaner, since I didn't finish even my basic qualifications because of my aspiration of becoming a professional footballer there weren't a lot of options open to me. I was hoping that a less popular and lower-paid role like this would also stop them from looking too closely into my background since there were convictions on my file for drug possession and drunk and disorderly behaviour. If I didn't get a job soon, I'd end up homeless, and due to my excessive gambling, I owed some seriously nasty people a whole lot of money.

I tidied myself up to the best of my ability, took a deep breath, and then tried to push my chest out confidently as I exited the bathroom and took the lift to where the company was based. The large complex housed over twenty businesses, each sharing the space for a lower rent solution to getting started in their field. AAC Designs, the company I applied to was based on the sixth floor of the building. Specialising in interior and exterior designs, AAC Designs was growing exponentially and had recently moved into the largest office space available in this building. Although the number of people the company employed was rising quickly, the work kept coming as they became further renowned for the quality of their work. Although I doubted I would be asked what I knew about the company while applying for the role of a cleaner, I was sure it wouldn't hurt to look them up before the interview.

It was quarter-to-eight when I strolled into AAC Designs office, fifteen minutes before they were due to close for the evening. Just a quarter of an hour to try and make a start to try and fix my broken life before it was too late. I walked up to the reception desk, manned by an attractive young woman, and a young employee in a suit attempting to flirt with her. The guy was good-looking, but it was clear the receptionist would make him earn the date. As I approached the desk, they both appeared irritated that I had interrupted them. I felt the receptionist's gaze as she judged my ragged appearance. She then made a quick phone call and guided me to a separate room with glass windows at the back of the office.

"Sorry, Miss Cadell. This is Alex Fletcher, your last interview candidate."

The receptionist held the door open for me to enter. The room was a mess of unfiled paperwork, with scrumpled bits of paper all over the floor. The rubbish bins hadn't been emptied, there were filing cabinets open and out of sorts. Outside the office, other workers were working at their desks, looking equally cluttered.

"Thank you, Felicity. Can you handle the end-of-day procedure with the staff so we can leave on time?"

The voice awakened something within my mind, A nearly forgotten memory of when I was excited about my future. Curiously, I looked towards the woman hidden behind the computer screen. When she stood to greet me, my eyes widened in recognition. The slender, leggy blonde in front of me was Alice. Three years had passed since I last saw her, but she looked virtually the same, if not better than I remembered. I could tell from her face as she studied my face, that she was noting the many differences from when she had last seen me. Years of alcohol and drug abuse had taken their toll, and while I had been incredibly handsome when we were together, the signs of my addictions were evident now.

"Alex, it's been a while. I hope you are well?"

Any optimism I held for this interview being a success was rapidly diminishing, Alice had a lot of valid reasons not to employ me.

"Alice." I smiled weakly, my hand shaking as I shook her hand, my legs turning to jelly as I took the seat opposite her. She remained entirely professional as she conducted the interview, seemingly not allowing her feelings and opinions to get in the way of what she was doing.

"Look, Alex. We both know you have had issues in the past with alcohol and drugs. Can you guarantee me that all of that is behind you now?"

Alice couldn't hide the sadness she felt inside any longer, and I watched her wipe a tear from her eye. I had betrayed this woman's trust time after time when she was the only one offering me support for my bad decisions. The truth was, however, that they weren't. I struggled to remain sober, and although I needed the money desperately, there was still a chance I'd spend some of it on drugs and alcohol.

"Yes." I lied. My whole body was stiff, waiting for Alice to see through me. She sighed, sat down, and then offered me the job. I would be on a probationary contract for the first three months and paid weekly, working twelve hours an evening from just after the company closed at eight. Things were finally starting to look up for me.

The first two weeks at the job went very well. I never met any of the staff, other than Alice who briefed what she expected done throughout the evening. My enthusiasm for improving my life was slowly beginning to wane through the boredom and loneliness I experienced. I was used to a life of luxury and partying, not kneeling under desks of people I didn't even know removing cobwebs for minimum wage.

Scored some coke mate, want to party?

I looked at the text from Lee, my oldest friend. He had been at the academy with me when I was signed professionally. Unfortunately, he didn't make it, mostly due to his partying lifestyle. Unlike me, Lee fell on his feet, working his way up until he became an owner of a chain of prestigious clubs across the capital. From time to time, he remembered how I had helped him out in the past and reached out with a gift of a promise of a night like this. I smiled, putting my cleaning equipment on the floor; no fun-loving person said no to a party night with Lee.

When I woke the next day, my head started spinning the moment I sat upright, and I threw up a little in my mouth. A sharp pain seared through my head as it replayed broken memories like a buffering video running off of dial-up internet; an erratic compilation of excessive drinking, drug consumption, sex, and gambling with money that wasn't mine. As always, it had been one hell of a night, but it was something I really shouldn't have done. The true cost of last night would make itself clear when I found out how much more money I had borrowed from people I shouldn't be borrowing money from.

When I felt steady enough to move, I noticed that it was only half an hour before my shift was due to start at Alice's place. Shit, I couldn't phone in sick, not while I was on a probationary contract. The reflection in the mirror looked just as rough as I felt while I lethargically put on the same set of clothes I had worn the day before yesterday and stumbled out of the flat. Despite my best efforts, I was half an hour late to work, and the building was empty, apart from Alice, waiting for me at the reception. Even from outside the door, I could see the anger and disappointment etched on her face.

"Give me one more chance, Alice, I beg of you." I pleaded with Alice, suddenly fully aware of the consequences of my actions once she told me she couldn't trust me with the job.

"I was an idiot to believe that you had changed, Alex."

"I can change..." My words faded with the lack of belief I had in them. I couldn't change, I had been unable to resist the lure of my vices and addictions back when I had a modicum of self-control, I was barely a fraction of the person I was back then.

"You left work early to party, don't even try to lie because I can smell the alcohol and see it on your face. Not only that, you didn't lock up, leaving the office completely insecure. This is after just two weeks Alex? How can I help you when you can't even help yourself?"

Alice appeared devoid of hope, and she was right, perhaps I was a lost cause. Seeing the pure disappointment on her face, the hurt and pain of what I had put her through both then and now awoke something inside of me. I could do better, I needed to be better for her.

"Alice, you're right. I can't apologise enough for what I did last night, let alone what I put you through when we were together. I beg of you, please give me one more chance, but remove the temptation for me, make it hard for me to want to leave here."

"Alex, you're not my responsibility anymore."

"I know, but without this, I'm finished, Alice. I can't stress to you how badly I need this. I will do anything."

Alice sighed and slumped against the desk, clearly tired of the amount of chances she'd given me. I could see the determination in her face to cut me off completely, and truthfully, I deserved it.

"Look, Alex, if I give you one more chance, I need to guarantee you won't do anything to fuck with my company."

"Anything, Alice, I promise."

"At the start of every shift, you hand over any money or cards you have in your possession, keys and phone. If you're fully serious about this, you will change into a new uniform that I choose, no matter how ridiculous, for the duration of your shift, and I will take your clothes away until I return before the end of your shift the next day."

"I agree Alice. Thank you for this."

Alice affirmed that any further mistakes would terminate my employment here, and I should go home tonight, clean myself up and return tomorrow, fresh-faced and ready to go.

Following Alice's instructions, I went to bed as soon as I got home yesterday and woke up today a good four hours before my shift was due to begin. Using my first week's wages, I visited the barbers for a fresh haircut and a clean shave and bought a few toiletries I had been neglecting recently due to favouring alcohol and drugs.

I arrived at work a little earlier than usual and introduced myself properly to some of the staff who weren't too busy to speak. When they had all left, I approached Alice in her office.

"Are you sure you fully agree to my terms, Alex?"

I nodded, feeling optimistic in my ability to change for the first time. Alice had been my backbone for so long, supporting me when I had been a lost cause. She was my rock, and although I didn't deserve her, I would repay the faith she had shown in me.

"Good, because I think you'll recognise the outfit I chose for you to ensure you won't leave until I come back."

Alice beamed proudly as she retrieved a maid's costume from her bag, and she was right, I did recognise it. Back when we were together, and things were good in my life, we had a very active sex life. One of the outfits I enjoyed her wearing was an identical copy of what she was holding up now. I couldn't help but laugh; did she really expect me to wear this? Alice's expression showed however that she was deadly serious. My future here at the company relied on keeping her happy, so if she wanted me to wear the maid's outfit, that's exactly what I would do for my twelve-hour shift.

Alice passed me the outfit and walked out of her office to give me some privacy whilst I got changed; she didn't need to, she'd seen It all before. Sighing to myself, I undressed and then laid out the outfit on her desk, along with her written instructions on how to dress myself. The first clothing to put on were the black, floral, lace panties, stockings topped with a white frilly material, and suspenders. I started by stepping into the panties, amazed that they actually fit. They felt surprisingly soft and comfortable against my skin, and I followed up on Alice's next instruction to gently roll up the stockings on my leg, being ultra-careful not to tear them. These didn't feel as comfortable against my hairy legs, but I rolled them up until there were no creases, and then placed the suspender around my waist, clipping it to the top of the stockings.

The main part of the outfit came in two parts, a black mini-skirt, hemmed with a frilly white which when I stepped into it barely covered my ass, and then a bra which wrapped around my neck. The final pieces to the outfit were a frilly white material collar type thing that fitted around my neck, and a pair of small heels.

I stumbled out of the office, struggling to keep my balance with the high heels. Alice covered her mouth as she giggled uncontrollably at my appearance, and took the bag of clothes I arrived in from me.

"You're quite the sight, Alex."

It wasn't until after Alice left that I went to check myself out in the mirror. I looked ridiculous; my hairy tummy, bloated from the recent night of binge drinking and junk eating stuck out, and I looked terrible. It wasn't too long ago that I had an amazing body, a toned midriff, and muscular legs and arms; it went to show what a few years of neglect did for your image. As much as my reflection disgusted me, I kept the outfit on and pushed on with my work. It was time I made the right impression, so I worked hard throughout my shift, adjusting to wearing heels as I hoovered and cleaned the entire office. I was thankful that the building opposite this one seemed empty for the night, otherwise, they would have had a surprising view when they saw me.

By the time my shift was coming to an end, my calves were in pain from the unfamiliarity of wearing high heels. I had genuinely worked hard, clearing rubbish and tidying the piles of paperwork haphazardly strewn across the desks, tidying the floors, wiping the glass, and emptying the bins into a bigger bin that would be picked up during the week by the building's staff.

The sound of a key being turned inside the main door startled me while I was finishing up at the reception desk, and I turned to see Alice walk in. The surprise etched onto her face on the improvement I made to the office cleanliness made the effort worthwhile, though, not quite as worthwhile as the paycheck would be when it came through next.

"I'm impressed, good job!"

Alice was almost speechless, and I beamed, feeling elated from her praise. It had been a long time since someone had shown any pride in something I'd done, I forgot how good it felt. She passed me my bag of clothes and I got changed in her office as we spoke casually while she waited outside the office.

"Although you've done well today, and I really am proud of what you've done, I need to know that you're gonna be good for the long term, Alex. Take home your new uniform, clean it at a low temperature and bring it with you for your shift tonight. For now, good job, go home and rest."

Amazingly, my newly-found enthusiasm continued for the next week. I had managed to avoid drinking any alcohol or taking any drugs, but I was starting to struggle once again at containing my addiction. The desperation I felt to drink or to take a line of cocaine surged through me, and my body started shaking. I tried to find a distraction, and it came in the form of preparing for work. After a few shifts of wearing the stockings, I decided to shave my legs so that they felt less irritating at work, and while I was at it, I gave myself a little trim around my private parts and my ass.

I left for work early, fearful that if I had too much free time, I would end up drinking or getting hold of drugs. As I arrived at the office, the receptionist, and the guy often seen flirting with her both nodded in my direction. Everyone knew me now, but thankfully, Alice hadn't told them of my troubles. I knocked at Alice's door and handed her my phone before sitting with her quietly for half an hour while she made a few calls. At least with the phone in her possession, I couldn't call or message anyone to acquire drugs.

Once Alice's employees left the building, I stepped into Alice's office to change into my uniform. In the few shifts I had worn the new uniform I was becoming competent at getting dressed with the delicate clothing. It was made even easier today after I had shaved my legs.

"Alice, I'm not sure how much longer I can keep this up, I'm starting to struggle." I decided honesty was the best policy once I was fully dressed and stepped out to face Alice. Her face softened after she had done her usual check-over of my uniform.

"You're doing great so far, but at the moment you're only getting support while you are here working, have you thought to seek external help?"

"I have, but not only would I struggle to afford to, I would be too embarrassed to open up about my issues."

"I can't help you during my working hours, what I can do, is try to tire you out. Normally, I complete an intense workout at home before going to work. If you feel up to it after your twelve-hour shift, I can do the workout here instead with you joining in. I guarantee, that in your current shape, you'll be too tired to think, let alone take part in a drinking session."

I agreed, not ready to give up on my chance to change, although doing just that and enjoying a few cold beers was so very tempting.

When Alice left, I worked as usual, though I felt more distracted than normal. I wasn't sure whether it was because I had a little trim down there earlier, but the feel of the lace panties rubbing against my cock was exciting me a little. Curious, I rubbed my hand against my cock through the panties, revelling in the way the soft panties felt. After years of meaningless, drink and drug-fuelled sex, it was weird to feel excitement at something new.

Satisfied that I had done most of my work already, I slipped into Alice's office and sat in her chair, stroking myself through the panties as I looked at a picture on her desk of her and a friend. For the first time in years, my imagination ran wild, drawing vivid images in my head of Alice and me together. I imagined my hands running over her soft skin as she stroked my cock through the panties and gently teased my nipples. This felt so good, and I felt myself getting carried away, feeling my cock throbbing as it got close to the point of no return.

A sharp moment of clarity and I stopped touching myself, despite the desire to continue. As good as this felt, explaining a cum stain on Alice's office chair wouldn't show that I was getting much work done. Unfortunately, that excitement didn't fade, and I had to cope working most of the remainder of the shift with my cock throbbing for more attention. As the hours changed to minutes until Alice was due to arrive, I found myself unable to resist occasionally stopping to stroke myself some more before stopping, and continuing my work.

Alice arrived two hours earlier than normal, and once she'd checked that my work was satisfactory, she laid two rubber mats, set up a Bluetooth speaker, and asked if I wanted to get changed before I started. I decided to strip down to just the bra, panties, and mini-skirt; the stockings, heels, and suspenders would have limited my movement. I could change into my normal clothes after the workout, I knew there was a shower room in the office, maybe Alice would allow me to use it.

For the next hour and a half, I tried to keep up with Alice as she went through a range of cardio and aerobic exercises. I was used to tough workouts from football days, but her exercises focussed heavily on the abs and glutes. It wasn't long before I regretted staying in the panties since they rubbed more with the extra movement and seeing Alice in her workout gear, her smooth skin lightly glistening with sweat, I was starting to get a little excited.

I couldn't finish the exercise and sat down, panting heavily and rubbing my sore muscles while Alice powered through, looking incredible the whole way through. She looked even more beautiful now than back when we were together, I was a fool to treat her the way I did back then. A part of me wondered if she still had feelings for me, but I had hurt her too much. I was barely half the man I was back then, physically, and mentally.

After showering, and getting dressed in my normal clothes, I thanked Alice and lethargically made my way home before crashing into my bed. Alice had been right, I was far too tired to do anything, and the moment I hit the bad, I drifted off.

My muscles ached significantly more than the night before when I woke, though, despite the pain, I was in a positive mood. The pain made me feel like I had achieved something, and I felt pride in myself. Today was a day off, and I promised myself to have a productive day, feeling inspired by Alice. The first positive step was to speak to some of the shady people I owed money to. I paid a little off my bill, promising that I'd keep paying until it's done and there was no reason for them to chase me with baseball bats.

Enjoying how my legs felt shaven, I took the bizarre decision to get my body waxed. I found a cheap place in Camden that offered a full body service, and a small, older Asian woman with an emotionless face got to work applying the hot wax to my body. As soon as the wax was ready, I thought I spotted the corner of her lips curl as my cry of pain sounded in the room when she ripped off the wax. I reevaluated my choices, wondering if I would be able to handle the rest of the wax coming off, but the pain cleared my mind of any thoughts of my addiction; mentally preparing myself for the next bout of pain focussed my mind. When the woman moved on to my more private areas, I dreaded how bad it would feel. I gritted my teeth to brace myself and then cried out when the deed was done. I covered myself quickly in a towel as soon as the woman had finished waxing me. Amazingly, either her presence, or the pain had caused me to grow erect, and I didn't want the lady to see that.

That erection stayed with me until I got back home, and after the frustration of stopping myself from coming last night, I had to have some release. After a shower where I moisturised my freshly waxed skin, I sat down and started stroking my cock. After a moment, my curiosity got the better of me and I put on the freshly-washed panties that I wore with my uniform to see how they felt against my now smooth skin. As I predicted, it felt amazing, and I brought up images of Alice as she worked out this morning as I got off. It wasn't long before I felt that pressure grow and I passed the point of no return, spewing my cum inside the panties. I guess I was going to need to wash the panties again.

The next couple of months passed in the blink of an eye as I settled into the routine of going to work, working out with Alice at the end of my shift, and then going home. A part of me wondered whether Alice trusted me enough to stop wearing the maid's uniform yet, but judging by the lingering looks I received from her when I wore it, I think she was beginning to enjoy the sight of me wearing it. To be fair to her, I hadn't asked her to stop wearing the outfit either, and I wasn't sure I was going to. At this point, I didn't mind wearing it at all, and I had to admit, it felt great against my skin the first few weeks after being waxed.

The addictions were still present, like personal demons chained to me, threatening to consume me, but working and exercising with Alice helped me keep them at bay. I had to admit, after a couple of months, I was nearly able to keep up with Alice in her workouts, and my body was starting to look much more toned, especially in my abs and glutes.

Tonight at work proved to be a bit of a challenge. Whether it was because I had improved my fitness, or because I wasn't drinking or taking drugs, my cock was feeling very sensitive to every brush of the lace panties. I had to stop working numerous times to stroke myself through the panties, but I stopped myself from cumming every time. I really couldn't work the remainder of the shift with cum-filled pants. When Alice came in and we started the workout, my lust felt insatiable, and I was transfixed by her body the whole time we worked out.

Alice went off to shower first today, and I noticed she left her panties on the floor outside the shower room. Knowing that she usually took a while to enjoy the shower, so although it was risky, I knew I had a minute or two. I crept up to the door, picked up her panties, and went with my initial instinct to hold them to my face. I breathed in her musky scent, and instantly started stroking myself through the panties again. Her scent heightened my arousal and I got so lost in the moment that I didn't hear the door open as Alice walked out wrapped in a towel.

The expression on Alice's face was somewhere between shock and delight as she looked down at me with her panties in one hand, and my other hand stroking my cock.

"Don't stop on my account."

In the maid's outfit, I felt a strange sense of embarrassment and humiliation, but I reminded myself that it was a means to an end. (containing: 'Maid For The Job', 'sissification')

Alice's unexpected request for crossdressing went from being an unexpected twist to a necessary step in my journey towards sobriety and responsibility. (containing: 'Maid For The Job', 'crossdressing')

Despite the light to extreme level of humiliation, I was determined to stick to my commitment to Alice, hoping it would help me turn my life around. (containing: 'Maid For The Job', 'reluctant', 'femdom')

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