I am a woman in my early 30's and in recent years I realised there were these new desires I had. Desires to have a man be second to me and only be there to assist in enriching my life. Pairing these thought were visions of him forced to wear female clothing against his will to humble him into the role. A curious internet search for male maids one day led me to learn about forced feminization and sissy maids. I discovered petticoated.com and was very entertained. I had found like minded people and felt relieved I wasn't the only one.
I was fascinated to the point I decided I wanted my very own sissy maid to serve me. This would benefit me greatly not having to worry about chores after work or on the weekend. Lots of free time to unwind and torment my little plaything. The thoughts became desire and desire became determination. The exciting prospect of a grown man grovelling before me, forced to wear delicate prissy dresses, something an actual woman would never wear. I've never felt so passionate about something.
My plan was to start the male in my life with a period of chastity training before introducing chores and dresses. From what I've heard, chastity is a powerful tool for taming and controlling a male which means it's essential for a sissy maids in training. I purchased a cheap silicone cage, no point investing too much into something that's not a sure thing. I also purchased a black maid costume meant for Halloween and such, which again, was nothing fancy but a nice start. If my plans went accordingly, this would be a nice starting dress to ease them into it.
I had a boyfriend the entire time I was discovering and planning for the lifestyle. I reeeaaally wanted to make him my sissy maid, it would have been perfect and I fantasized about if often, dropping subtle little hints and questions hoping he'd be intrigued or willing enough to try chastity. He thought I was being weird and was put off. One day I just outright sprang the idea of chastity on him. After a whole lot convincing, he reluctantly agreed. I began training him, denying him sex and orgasms whilst having him orally provide mine on demand and hoping he'll get desperate enough for release that he'd be willing to do much more.
After a few days however, he changed his mind and handed me the cage. I was shocked, I didn't think the cage could be removed so easily. I asked him how? He said it just stretches off. I didn't want it to be like this, this was not good. I got serious and demanded he put it back on right now! He told me it's not happening forget about it and walked off. I followed him and I started to... not panic but like I had a feeling of losing options, a now or never kinda thing. Without thinking I just went for broke, and tried to force the cage back on him on the very unlikely chance he'd let me. I realised I would have looked insane and obsessed, he defiantly saw me in a different light and I understand why he was scared off. I was just as upset. He decided I was too obsessed with this 'crazy idea' and I decided I didn't want a man who wasn't willing to do this for me. I let him walk away and we never spoke again.
A little time passed and I had been put off finding a suitable partner for the moment. My desire to obtain a sissy maid was not lost but my failed attempt left a bitter taste. I was disappointed in myself. But I eventually reignited my determination. I did my research, revamped my plans and got better organised for the next attempt. I would be selecting a male I thought would be far more likely to comply. But before I could find this ideal guy, a phone call with my mother changed everything. She mentioned that my Aunt and my cousin moved to her boyfriend's house but they soon kicked my cousin out leaving him homeless.
Apparently he and my cousin don't see eye to eye. Stubborn 19 year old males don't take too kindly to their mother's boyfriend I guess. He was always trying to break them up and my aunt had had enough of it herself. She tried to explain she felt a little bad as none of the his limited friends or family, had any means or desire to house him and apparently he spent the past nights wandering the streets and sleeping on buses. She mentioned that he was jobless, broke and couldn't pay rent. His mother had had enough feeding him her boyfriend's money he only wasted.
Then an idea crossed my mind. Could I use this opportunity to obtain myself a sissy maid? Who said my ideal sissy maid couldn't be my own flesh and blood? Better yet, someone who was in a desperate situation and couldn't refuse my ultimatum. I said to my mother, "You know what? I'll take him in, he can come live with me." She said " Oh really? Are you sure you wanna do that?" I said sure why not, someone's got help him out and set him right. Mother knew I didn't take crap, perhaps I could be the one to straighten him out. Mother warned he couldn't pay me rent but I told her not to worry, I'll make sure he earns his keep. My Aunt then called later and confirmed I was okay with it and thanked me a lot somewhat relieved.
My aunt called me back after telling him. Apparently he was all to happy to have a roof and food even if it was with a somewhat estranged relative. He was told I'd have rules and expectations but hey, it can't be worse than living with his mother's boyfriend right? Rent free too? Seemed too good to be true. But once he agrees to my terms, that's it! No going back! This was my chance to do it right this time and ensure this he will be fully transformed and helpless.
I lived across the country from my small group of relatives, moved a couple years back when offered a good opportunity for my career. I've only seen my cousin a handful of times at various stages growing up. That last time I saw him must have been around when he was 13. The last financial favour his mother did for him was send him on a 6 hour flight, then a 50 minute cab drive to my door. She could enjoy her relationship peacefully now with him far away. He looked exhausted and I warmly greeted him. He was shy and quiet in this new situation. Needless to say, he has grown quite a bit. He is a tall boy, I'm guessing about 6 feet but I wasn't going to let his size intimidate me, after all I'm 5'9 myself. On the plus side he's also very skinny and has little body hair to deal with.
It was late afternoon/early evening and I had a hearty, hot dinner cooking... he was noticeably pleased with the smell. I suggested he have a nice shower after which he looked much more lively and fresh. He was very polite, or at least acting so. We talked for a bit about his situation. I lent a sympathetic ear but my mind kept straying and picturing him in the dress, wishing I could put it on him right now but I thought it best to let him sleep this night, get settled in safe and comfortable again. I would be taking the next 2 days before the weekend off sick so I could have 4 days to set this up.
My apartment is a nice recent build but is only one bedroom so he'd be sleeping on the couch, with the promise of buying a pull out sofa. There's no way I'd let such a thing take place had I not planned what was coming. Heck, he wouldn't even be here had I not plans for him. His sleeping arrangement is quite different now, as I'll explain later. Anyway as he slept, I took his suitcase to my room and removed all his clothing, then snuck out to stash them in the boot of my car. I keep them there just in case (but as far as he knows, they've all been donated. I then placed the maid costume inside and returned the case. He woke up much later than I, yelling out whilst I revised plans in my room.
Him: "What is this? Where are my clothes?
Me: *yelling back I can't hear him.
He walked into my room wearing nothing but his boxers holding the dress in one hand like a towel looking angry and concerned. I smiled and cleverly said to him "You didn't expect to just live here rent free did you?"
He was stunned: Enough's enough, give me back my clothes, this isn't funny!
Me: Oh I think this is very funny.
Him: It's not! I want my clothes now!
Me changing my tone: Excuse me? Who do you think you're talking to? This is my place remember? My couch. My shower. My food. And you are my guest here, you don't get to make demands. I suggest you abide by my rules if you wanna stay and not live on the streets."
He quickly humbled and quietened down.
Him: S-so... you want me to wear this?
Me: *nods and says Yep!
Him: H-how long?
Me: Well your old clothes are gone so I guess... until I buy you more dresses." I laughed
Him: You're joking
Me: Nope! I'm completely serious. So whatta you say? It's either this or I kick you out on the streets.
Him: "How do I put it on?"
Me: "Well first, we'll get you out of those boys undies and into a pair of my panties.
I began pulling down his boxers. He grabbed the waist and pulled them up shocked at what I was doing saying he could get changed in the bathroom. I told him "Oh no, you better get used to being naked in front of me" and grabbed them again to pull them down all the way. He quickly covered his himself with his hands. I slapped them, then pulled them out of the way. "Oh grow up, it's nothing I haven't seen before. Hands on head" I ordered. I put him in a pair of white panties, they actually fitted quite nicely.
Also there is a situation regarding the panties I'll to explain further down. I told him "Arms up, lean forward." as I lowered the dress on him, buttoned him up and tied the sash at the back. For his footwear, some old ballet flats which were a bit of a tight squeeze but would do for now until I buy some suitable heels. He simply looked adorable, I particularly liked the way his long skinny legs looked coming out of the skirt and the cute little puffs covering his shoulders, like an anime maid. I grabbed his hand and led him to the mirror to get a look at himself. His mouth fell agape and brows turned upset.
Me: Don't you look nice. Did you notice what kind of costume this is?
Him: A maid?
Me: And you know what maids are for... housework! That is your role here. THAT is how you will pay your rent.
He agreed as for now a few chores seemed to be the least of his worries.
He asked concerned: Does mum and her boyfriend know about this?
Me: No. And they don't have to. This can be our little secret.
He seemed relived.
Me: I think you look really nice what do you think?
He said "No? I mean... I dunno" looking defeated, obviously ashamed and revolted at what he'd let happen to him. "Do I really have to do this?"
Me: 'fraid so. I've been looking for a guy to dress up as my maid and do my dirty work. When I heard about your situation, I saw my opportunity. That's the only reason I agreed to take you in. Don't forget that.
I took some photo's of him in his new outfit with my phone.
Him: You're not going to show anyone are you?
Me: That depends. Just a bit of extra insurance in case you think of trying something stupid. I'm sure we wouldn't want your mother's boyfriend seeing these now would we?
He cringed at the thought.
I fetched a new chastity cage, one I had bought in the re-evaluation of my plans. Unlike the weak, silicone one my ex boyfriend so easily pulled off, this was a nice and secure metal one with multiple sized rings for convenience. I'm glad I had practised assembling it before hand otherwise this may have taken a while. I had him hold up his skirt as I slid down his panties: "Now there's the little matter of your peeny." As I gave it a poke. "There's no way I'm letting you jack off under my roof. As a sissy maid, you have no right to self pleasure, so it needs to be kept locked up."
He looked puzzled and shocked by the weird device. I told him to relax as I assembled it on him, looking very put off by his cousin handling his now not-so privates. "With this, there will be no more wanking and spurting for you. You won't even be able to get fully hard. A genius thing don't you think? Oh and the curved tube means you'll have to pee sitting down.
He was appalled by what I was explaining.
Him: How long do I have to wear this?
Me: That's not for you to worry about. If sissy maids behave and please their mistresses, then they get release. If they don't, they need to be kept locked up longer. It's not gonna be an easy thing to earn but If you do, I promise I'll let you out for a wank. Sound good?
Him: I think so.
Great! So ready for your new life as my maid?
Him: I guess I don' t have a choice.
Me: No, you really don't but hey, remember the warm shower, the roof over your head, the nice meals... which you'll soon learn to cook. Now think of the cold and hard dangerous streets. I think I know which one your prefer.
He said with a pout: Let's just do this.
So the weekend's training commenced. I told him there will be no half-assing the work, he'll be putting in serious effort. I showed him exactly how I wanted things done, having him practice things he had little to no prior experience in such as scrubbing, wiping and folding. I had him working hard and got caught up on all the neglected work. I began teaching him the skill of applying his own makeup. It was funny watching his unskilled hand struggling to follow my instructions for correct application. I could tell he also struggled having to, by his own hand, contribute to his feminization. I enjoyed this blow to his ego. He actually looks quite pretty once made up properly and could perhaps even pass as a young woman.
I asked him "Don't you feel nice now? You've put effort in to make yourself look pretty." I even supervised his showers. It was my responsibility to ensure my servant was properly cleaning himself even intervening when he failed to wash his caged cock properly. It's also important that I regularly inspect the cage whether it is too small and sliding or too tight and irritable. I wasn't too concerned about the way he carried himself at the moment but eventually, some serious poise training would be needed. I now enforce a strict, disciplined and obedient movements and positions sort of like stereotypical classic maid features. My rules for form are:
*Correct posture, straight back and neck.
*Overly feminine steps, heel in front of toe.
*Provocative hip and butt sways.
*Curtsy's and Yes Ma'am's when accepting orders.
*Keep legs and knees straight when bending over.
*Keep arms stiff to the sides with fingers pointed out like a doll.
He was only doing about as well as I expected considering it was only his first few days but persistence pays off and he is ever improving, especially thanks to a little encouragement spanking. When he needs correcting, I simply have him bend over, hands on the couch or bed and use a big wooden spatula to paddle his cheeks. A mere 5-10 whacks is enough to have him whimpering and moaning but 20 whacks has him sobbing and begging. This as a result gets him right back in form eager to avoid another. He must have a sensitive bottom... or I have a really hard strike. I try to avoid the spanking as much as possible however only resorting to it if he's really not getting a certain lesson through his head. This is usually due to him thinking he can get away with doing the task his way or half-assed... or not at all.
I'd like to take a moment to explain the aforementioned situation regarding my panties and also his sleeping situation. First, I've only enough panties for the week (about 9 pairs) yet him wearing a pair is a must. Financially, I do well on my own but with another person to feed and clothe (in sissy clothing), it puts a strain on things. I guess you can consider it as paying for a maid. I'm trying not to live beyond my means, saving as much on bills as I can which means washing day remains as it always has, once a week... except for his dress which really should at least have a quick wash every few days. My temporary solution is we share panties. I of course wear a pair first one day and he wears the same worn pair the next. This means we both get to wear panties and there is no extra clothing, which means no extra washing water.
At the end of the week, he must hand wash them and I expect them returned in my drawer starting the cycle over again. The first thing he knows he must do in the morning is step into my worn panties from yesterday on the floor and pull them up, wincing with disgust as he does. I could have bought him his own panties but honestly it would just be a waste as I was saving to buy him proper sissy ones soon. I am not worried about him stretching or ruining them as they are all due for replacement anyway. Could I replace them now? I could but this is more fun don't you think. He absolutely hates it but that only makes me enjoy it more.
As for sleeping, I don't trust him not to get up or possibly cause trouble in the middle of the night. The first couple nights I hadn't much choice but to wrap a couple lines of duct tape around him, arms at his side and legs together then to lay him down on a yoga mat and pillow on the floor next to my bed. I was realising how unprepared I was for this. I needed a few items for a solution I concocted. First I had to return to the local sex toy boutique where I bought the silicone cage and bought a pair of buckle handcuffs. The second item I went out to buy was a sleeping bag, one that covers the head as well, like a cocoon. The third items were 2 large men's belts. So first I have him naked and secure the cuffs. He then slides into the bag and I zip him up. Finally I wrap the belts around and buckle them tightly where his elbows and hips are trapping his forearms and hands. He is unable to reach past the belt for the zip or lift upward with the tightness of the belted bag. He is rested on the floor immobile at the side of my bed. I love knowing he's right there and sleep soundly knowing he's nice and secure. I even have a fun way to greet him in the morning; he wakes up to my feet in his face.
Come Sunday night I told him I would be at work all day tomorrow and he would have a list of chores to complete. Having caught up on the chores the past 4 days, there was simply nothing left to do but he wasn't just gonna sit around all day. He needed practice and what better way than some make-work. I told him to time each chore, he'd be spending hours at a time practising a certain chore. For example, I had him dusting everything over and over again despite no dust. I watched as he made my bed to perfection then removed all the sheets and remade it all once again.
I had him remove clothing from my closet and drawers, unfold them all, then refold them and return them into their correct place. I even had him practice his sissy walk and composure. I warned him I will see whether or not he's doing as he's supposed to pointing out the set of nanny cams I have in place. There is one in the main room and one in my bedroom. They cover most the scope of the room and I can watch it live from my phone whilst at work so he isn't be able to drop the act. That Monday morning, I said goodbye for the day and he responded with a curtsy. I had a big smile of satisfaction on my face all the drive to work. I took some moments to check the stream during work day and was delighted when I saw him hard at work. Upon my return he had done... I'd say a fairly decent job of what i asked him to. Not bad for a beginner but he has since upped his game. I told him I had been watching him and complimented his behaviour.
I'm proud to say now after a few weeks it looks like he's doing his best to please me and earn my approval. I mentioned to him it looks like he is taking pride in his work and he reacted with gratitude. In the mornings I release him from his bag and he gets dressed and made up while I shower. He lays my selected outfit for the day and then we make breakfast. Upon my return, my apartment is clean and we'll start preparing dinner. He hasn't mastered cooking yet but we'll get there. I don't trust him to cook alone and always supervise. He's always struck me as not the brightest and I'm afraid he'll accidentally chop off a finger or start a fire.
Once the kitchen is cleaned, it's time for a nice relaxing foot massage on the couch or to use him as a foot stool for a couple of hours while I watch TV. So nice after a long days work! When I have friends coming over, I give him the option of either staying out, humiliated serving and entertaining us or hide in my closet bored for a few hours if he doesn't want them to know. Both times they've been round so far, he's opted for the closet. Perhaps one day I won't give him a choice. After all, I'm sure it's quite the challenge staying still and quite for a few hours hoping to not be discovered. I'm also quite proud of my little project and am almost certain I will show him to my mother at some point. She'll no doubt be surprised at first but I'm sure she'll be amused and proud of me, impressed of how I made a purpose for him. She will not doubt inform his once suffering mother and her boyfriend too. I better be careful, they may actually want him back!
These past few weeks he is progressing nicely. This is actually happening! My dream of owning a sissy maid is finally coming true. Only I can't believe it was my cousin who ended up falling into my lap and taking up the role. The cheap maids costume was never gonna do though, it was always meant to be a temporary first step. I've taken his measurements for some proper sissy maid dresses. What kept standing out to me most were the PVC items. My tastes have defiantly changed and are currently drawn to that. I think it will suit him nicely in white black or pink I honestly haven't decided as I can only really afford one dress at the moment.
I want the skirt to be way too short as to fully expose matching panties! Perhaps also some nice petticoating we'll see. Also PVC gloves will be essential however matching stockings and maid bonnets may have to wait. Eventually I want him covered in shiny PVC from head to toe! Truly make him feel submissive. I will subtract the numbers by a few on his measurements for the outfits as I want them to be tight. I want him to feel trapped with every movement and constantly reminded of what's on him. I've been having quite the time selecting possible new items and can't wait to see him model them in action. He thinks he's feminine now, he has no idea what's coming.
In retrospect, my past vision for a sissy maid was flawed and undecided. I have much clearer goals now and am more confident and determined than ever using my cousin as my template. He'll look and act exactly like I think a sissy maid should. It will be divine, my dream is being realised and I very much looking forward to a future with my very own sissy maid.
Thank you for your letter Kate. I very much found it a delight to read and congratulate you on your acquisition of your sissymaid. Your cousin being in dire straights provided the perfect opportunity and along with your determination and willpower I'm sure you will be successful in having the perfect PVC sissymaid at your feet in no time. We would love an update at some point.