A brief introduction is in order; Mistress Alison is a good friend and a very knowledgeable and experienced Mistress, she has also been a frequent contributor to PDQ. She is now available to answer questions from both Mistress and sissies alike, assuming a respectful tone of course. These email conversations may well be included at some future date in PDQ though a request for privacy would be respected. Feel free to write her at firstname.lastname@example.org and please don't waste her valuable time asking "where / how can I find a Mistress?"
Dear Mistress Alison,
My son introduced petticoated.com to me several months ago for me to give some thought to. Yes, it was something I had heard of years ago yet never thought a son of mine would ask me to petticoat train him. Sure when he was younger there were many times that type of training would have been appropriate. The more I looked into it the more it sounded like something that was possible. To test my son he was instructed to buy a few garments of my choice on his own. I gave him the sizes after some careful measuring then off he went shopping. To be honest watching him leave with a shopping list had me laughing to myself. It took him a couple of days to get the courage to buy all of the items and he did get them.
Over the next few weeks my son wore the items purchased when I told him to do so. If he couldn't follow simple instructions how could any training be effective without some punishments.
Jumping ahead my son has been outfitted with a maid uniform and a sissy dress for starters. I'm quite liking how things have progressed however not sure how far to go. Should I completely feminize him to the point there is not much masculine in him anymore? One of my girlfriends advised locking his penis in a cage and throwing away the key. I'm just not sure what is acceptable and what is crossing the line.
Can you offer some suggestions Mistress Alison?
The short answer to your question is that you are now in charge and you can takes things as far you wish; you don’t have to do anything you don’t want to, nor should you hold back from doing anything because you feel it is too outrageous. It’s your choice. However, as I have told many others power is addictive and can also be erotic, having a man kneeling at your feet and knowing you can make him do absolutely anything you chose with a snap of your fingers is something the majority of women come to relish. Also the relationship between a Mistress and her maid tends to be progressive and like all healthy relationship grows and matures with time; and what seems too extreme now might well seem rather tame in two years time. Who knows what the future holds for any of us?
Some Mistresses prefer to keep as many of their maid’s obviously male characteristics as possible so he looks just what he is, a petticoated male, while others prefer them to look as feminine as possible. I belong to the latter group because I believe the more softly feminine a sissymaid looks the more submissively feminine they will feel, and I like to have pretty things around me. It is also good training for them to have to go through a regular beauty routine of waxing and moisturising and maintaining their make up throughout the working day, this helps them appreciate the old adage, il faut souffrir pour être belle. I also insist that my 24/7 sissymaid, has her period at the same time I have mine. This helps her understand what we have to endure to ensure the continuation of the human race.
I firmly believe that all males, and especially sissymaids, should locked in chastity but do not, repeat not, throw away the key. The device should be regularly removed for cleaning and inspection. Far better to wear it around your neck on a gold chain as an outward symbol of your authority and power over your maid.
If you have not already done so I suggest you read the advice I gave to Hannah about petticoating her son (August 2019 and June 2020) and possible also what I wrote to Catherine (December 2019) and to Pippa (August 2020) about FLRs.
I hope you find this useful but please write again if you need more advice or further information, or send us an update on your son’s progress.
I wish you both well for the future.
Dear Mistress Alison
Thank you very much for the detailed response to my email questions.
I do understand how things will change as time goes on. It just made sense as any relationship grows so will this one which to be honest I never thought of happening. There is so much to learn for my new sissymaid and of course myself as his new Mistress. Funny you mentioned the snap of my fingers. It would have been nice to have my brother in that situation when we grew up instead of being picked on as most girls were.
Oh yes the chastity device and key comment. My girlfriend was kidding me so I never took throwing the key away literally. The women at the adult store gave me some good advice last night when I picked up a CB6000. She too talked about hygiene and it's importance for long term wear.
Alison, I too like pretty things being a girly girl so my sissymaid will have the same. Although it will be a lot of work to make my son look feminine the reward will be all mine.
Finally later on today I will indeed read the advice you gave Hannah and Catherine.
You are most welcome. I’m always happy to help.
One other piece of advice. It’s important to start as you mean to go on and your son must appreciate he is no longer your son and you are no longer his mother, you are now her Mistress and she is now your sissymaid and your word is therefore law; and it is her job to wait upon you hand and foot, jump to your command and naturally always put you first. All sissymaids, no matter how well trained, how obedient and how diligent require regular gentle correction and the occasional sharp reminder of just who is the Mistress and who is the maid. She must be made to realise that any disobedience, dissent, idleness, disrespect, or, worst of all, defiance. will result in punishment. She must be made to realise this from day one.
I wish you every happiness in your new role of Mistress.
Dear Mistress Alison
Sorry for the delayed reply while I was out shopping. The term mother and son are about to leave our relationship as soon as I have HER in chastity. There are a number of rules to be implemented immediately following the clicking of the lock. I did tell her that if I was to take on a Mistress role and she my sissymaid that it would be under my terms. She is also aware that punishment will be necessary to enforce my role as her Mistress and hers as my sissymaid. That being said I did let her know punishments would not be abused although they would be harsh when administered.
Alison, my sissymaid has no real idea what is in store for her. I do hope she has done as much homework as I have in the last 24 hours. We are younger in age than some who partake in this life which will provide me with many years of entertainment. Do you use your hand on a bare bum or use a paddle? I watched a few spanking videos and oh my some of those boy's bums get awfully red by the end of it all.
Alright there is much to do so until next time have a lovely day Alison.
I’m sorry this has to be brief, but I am just off to a long meting which I can’t avoid.
Keep your sissymaid in ignorance of your plans, it is good for them not to know what is coming. You have exactly the right attitude, a key function of any sissymaid is to entertain and amuse her Mistress. Being a Mistress is largely about having fun and doing things simply because you can. You will grow to love that power.
I use a whole range of punishment implements, including my bare hand, my gloved hand and a special pair of gloves with spiked palms which leave a lovely pattern of red dots. Don’t worry about reddening the skin, it looks a lot worse than it actually is. For a basic set of punishment tools I would suggest a riding crop (see my comments to Catherine and Pippa) a plain leather paddle, a tawse, and a school cane. You can add further tools to your armoury as go along. As a general rule I start with the paddle and when the recipient is nicely warmed up i.e. feels hot to the touch move on to either the cane, crop or tawse for the serious punishment. Each feels very different and you will become accustomed to the results they produce. Always continue until the tears are flowing freely, ignore all pleas and promises and afterwards make her stand in the corner holding her skirt and petticoat(s) up so her bottom is visible. If her arms begin to flag threaten her with a repeat punishment.
Have you assigned her a new femme name? It would be a good time to rename her as you click her chastity shut.
Good luck and happy Mistressing.
In my haste yesterday evening I neglected to mention two other types of punishment ideal for dealing with errant sissymaids. Stress positions and mouth soaping.
Two basic stress positions. Have your sissymaid stand with her feet 18 inches apart and 12 inches away from a wall, these distances can be increased to make the punishment more severe, and keep a coin pressed against the wall with her nose while keeping her hands in the small of her back. Alternatively have her kneel down, preferably on a hard floor, with her feet straight out behind, then sit her bottom down on her heels with her hands in the small of her back and a book balanced on her head. They sound easy, but believe me she will soon be regretting whatever has caused her to be placed in either of these positions.
For mouth soaping cut a slice off a bar of soap, carbolic or Wrights Coal Tar are both good though my sissymaid kitty informs me that old fashion green Fairy soap tastes the foulest, and place it under her tongue. Have her stand in the corner until it is all dissolved. A step up from this is to hold her nose and smear her tongue with mustard before banishing her to the corner. English mustard mixed from powder about 20 minutes before application is the best.
The two things your sissymaid should also be practising are her deportment and her curtsy. When in your presence she should stand facing you with her heels 12 inches apart with her back straight and head up but with her eyes respectfully lowered, her hands horizontal in the small of her back palms outwards with the right hand on top of the left. In this position no more than 2 inches of her petticoat should be showing beneath the hem of her uniform skirt, and naturally her stocking seams must be perfectly straight. If you speak to her she should raise her eyes and curtsy to acknowledge that you have spoken, and if you have given her an instruction then she should to answer “Yes, Mistress,” and curtsy again before complying. Naturally she should curtsy whenever entering or leaving your presence and always before speaking.
Have her practise curtsying to her reflection in a mirror and make curtsy practice for a specific period of time part of her daily routine. Tell your sissymaid that a well trained sissymaid should be able to walk to the foot of a flight of stairs, curtsy, ascend the stairs, curtsy, turn round curtsy and descend again, all while keeping a book balanced on her head. We both know that descending stairs in four inch heels without looking down is an incredibly dangerous thing to do, but your sissymaid won’t know that and setting her unachievable tasks is good mental training for her. Having her practise her deportment and curtsy in front of you in her highest heels with a book on her head while you relax watching television or listening to music is a pleasant way to while away the long winter evenings.
Hello Mistress Alison,
Sorry for the delay in getting back to you. Things were pretty busy here the last week with painting and preparing my new sissymaid's room. She did most of the work while I watched and gave orders. The power of taking charge of my son has perked my interest more and more.
Last we talked about punishments along with the tools to do so. Thanks to Amazon I now have the paddle and a pair of gloves to protect my hands. A cane is on the way. Do you enjoy giving put punishments? Well I have to admit I do. In fact the other night I took her over my knee then let her have it until my hand hurt. Needless to say her little bum was a nice shade of red with a few dark areas. She got the point to be on her best behaviour ever since.
Alison, how feminine would you go with a young sissymaid? Do you support breast implants as some other mothers and wives have done? It's something I'm quite interested in looking into for my sissymaid.
To answer your question on a feminine name, well of course she has a new name. The name Isabella came to mind after a late aunt of mine who I only met a few times years ago. My Isabella has grown used to me calling her by her new name.
Alright there is much to do today before going back to work in the morning. Have a wonderful day or rest of the weekend.
Please don’t worry about the delay.
As I have written before exercising real power is both erotic and addictive and very few women who experience it ever want to relinquish it. I don’t particularly enjoy inflicting pain, I was never a sadist, but I do enjoy having the power to get kitty to do absolutely anything I order her to, and I do mean anything. If I told her to put her hand in the fire she would do it without hesitation, but of course I would never do any such thing. This means that the usual outcome of giving kitty a severe punishment while she lies perfectly still and takes it for me is that I get very damp down below.
Regular correction will keep Isabella on her toes and on her best behaviour, which is exactly where you want her, so don’t spare the rod when it arrives. Remember a cane is not just for a sissymaid’s bottom, don’t neglect her palms, the insides of her thighs, soles of her feet, and the backs of her knees, a particularly sensitive area. When caning her bottom try and get some of the strokes to land at the point where the thighs meet the buttocks, it’s very sensitive and she will feel the effects with every step she takes for some considerable time afterwards.
I recommend you keep a cane or crop hanging up where Isabella can see it as she goes about her duties, it will be a powerful reminder of her place in the scheme of things and of your power and authority over her, even when you not physically present in the room.
I don’t personally wish to take any steps with any of my sissymaids that are irreversible so I wouldn’t go down the route of implants or hormones. However, that’s no reason you shouldn’t do either if that’s what you wish. Remember this all about you doing what you want and having fun; what anybody else (and particularly Isabella) thinks or wants is immaterial. If you think it will improve her then go for it.
Hello Mistress Alison,
I have to agree the power Isabella has lost and I have gained is exciting for me. Spanking is so much fun although no other type of beating takes place here. After all Isabella was once my son so no beating just some good spanking with paddle and canes. The odd time she was struck in the thighs was due to my bad aim. The paddle hangs in the living room so she can see it quite often through the day. She asked why so I let her know just in case I need it and so she can see it there as a reminder.
I understand your position on implants and hormones for sissymaids. Hormones are not something on my mind at this time although breast implants are worth looking into. Even if my sissy goes for the appointment to talk about having breast implants without ever going all the way she will be so embarrassed. That in itself is worth it to me. I plan to slowly break her down to be a true sissy. Anyways back to breast implants, I placed a few calls to get her an appointment. Next Tuesday we go see about the procedure. Now Isabella doesn't have a clue at this stage. Mind games are so much fun.
I'm off to work Alison.
Have a wonderful day.
I can see you seem to have all the characteristics of a Mistress, and are already ahead of my advice. I know you are going to enjoy breaking your former son down, curing him of all his old, bad and naughty ways and turning him into obedient little Isabella, the perfect sissy.
Embarrassment and humiliation are powerful tools in this process, and mind games are a perfect form of entertainment. Will Isabella be going to her appointment in uniform, or in drab? You could always tell her that if she’s a very good sissy you’ll get her a super frilly party dress to wear whenever you have visitors. I’m sure her old friends would be delighted to see her dance for them.