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,
Last year I wrote to you about my younger son (Aug 2019) and have since followed the advice you gave me. Initially he reacted pretty much as you predicted, telling me he preferred the feel of female underwear but otherwise he really didn't know why he wanted to do it. He also confessed to feeling very ashamed about wanting to wear girls' clothes and I reassured him it was nothing to be ashamed of and told him I would help him dress the way he wanted but it would have to be on my terms and there would be no more "borrowing" his brother's punishment clothes. I also followed your other suggestion about telling him that the price for being allowed to dress the way he would prefer was doing more around the house to help me. At first he seemed very unsure about this but once he got over his initial reluctance he became a willing, if rather inexpert, helper.
For Christmas last year I bought him a maid's uniform which I now insist he wears only when he is doing housework, otherwise I think he would wear it 24/7. In addition to cleaning his own bedroom I made him solely responsible for cleaning the bathroom and now when I go in there the taps are always shining and the mirror no longer has splashes of toothpaste on it.
Things were going very well until last week when he asked me if he could ask me something serious. Obviously I said yes and after some beating around the bush he said he thought he needed to be locked up in chastity! Trying to stay calm I asked him where he had got such an idea from and how come he knew anything about chastity in the first place. Well, it seems I had been less than thorough in deleting my browsing history and when he was using my computer to research a school project he came across the short cut to the Petticoat Discipline Quarterly website, which didn't trigger the parental lock, so he browsed. Fortunately the back numbers didn't go back as far as August, but he read everything from October onwards. I then asked if he knew the primary purpose of enforced chastity and he replied, "To prevent masturbation," which rather shocked me. So I asked him if had been masturbating and he answered, "No. But I have touched myself a lot and I am being tempted to try and I don't know for how long I might be able to resist that temptation." I asked him if that was his only motivation and he answered, "No, being in chastity will help me become more of a properly petticoated male like those I've read about."
While I have no objection in principle to his being kept in chastity I can foresee all manner of practical problems. I shudder to think of the consequences if anyone at his school, pupil or teacher, were to find out. I am also concerned about him closing down other options at such an early stage. He is just discovering his sexuality and ideally I would like him to be learning the art of making significant relationships in the wider world. I don't want him to concentrate all his energies in one particular sphere of activity, just as I don't want either of my sons to spend all their spare time staring at screens. That's the main reason they don't have their own computers, so I can limit their on screen time and monitor their activities, although in the case of my younger son I've rather been hoist with my own petard.
I put this and other arguments to my son saying he should wait until he was older and didn't have to do things like change for games at school. I also pointed out that he might well change his mind during the next couple of years when he would be effectively transitioning from adolescence to adulthood. I even suggested a scenario where he had a serious accident and was taken to hospital where all would be discovered and his being in chastity might prevent the doctors gaining access to treat the injury. He was not to be persuaded and I was going to use the old standby of, "No, because I say so and you'll do as you're told," when he deployed a killer argument. He said, "Mistress Alison says that all males should be kept in chastity for their own good, and she should know."
I am really not sure how best to proceed now that control of the situation is slipping away from me and once again I would appreciate your advice on how to handle this.
I am pleased you found my previous advice helpful.
I am not in the least surprised that your son wishes to progress to the next logical stage of petticoating. As I wrote before I doubted very much if it was just a passing phase and he seems to have a very firm idea of the direction he wants his future life to take.
As I also wrote before he is still a minor living under your roof and so the bottom line is that he should do as you tell him. The fact he is almost certainly naturally submissive and therefore even more than usually susceptible to female authority should make it much easier to forbid him from doing anything further about chastity, if that is what you wish. However, I do not believe this would be a wise course of action, banning young people from doing anything tends to lend that thing glamour and the additional allure of forbidden fruit. It is far better that he takes his first steps into chastity under your control and guidance than experiment on his own in secret.
There are certainly practical problems with wearing chastity but none of them is insurmountable with a little ingenuity. I suggest you obtain a suitable device, I'm attaching a list of ones I think most suitable for a young beginner, and start by locking him into it for a weekend. You may want him to shave off any pubic hair growth first. He will then experience some of the inconveniences associated with chastity and it is possible, though in my opinion unlikely, that he will find they outweigh what he thought the advantages/benefits would be. If there are no problems and he is still keen them have him wear it during the evenings as well. It is important that he puts it on (or you do it for him) from the moment he arrives home and takes it off just before leaving the following morning. Establish a routine and stick to it rigorously. Then consider having him wear it on those schooldays when he doesn't have to change for games. As he becomes more accustomed to wearing it and adept at concealing the fact from others you can make it permanent.
It is essential to maintain scrupulous hygiene and it should be removed at least once a week for cleaning and inspection. Look out for any signs of chaffing (often a problem with cheaper or ill fitting devices) or infection. I don't think tampering is likely to be a problem in his case, but it is worth bearing in mind. In case of emergencies, whenever he leaves the house have him carry a spare key sealed in an envelope which both of you have signed over the flap. This should be presented for your inspection at regular intervals.
Your letter does pose another and probably more important question. Wither do you want this to go and how far? If, as I think, he has made up his mind where his future lies then he will probably want to start wearing a wig, proper shoes and make up, maybe even adopt a femme name. This is the classic behaviour pattern and you should prepare yourself for it. If you think it is a step too far then you must tell him so firmly but gently, though I believe you will only be delaying the inevitable. He is now less than four years away from legal majority and I can assure you it will seem like the blink of an eye when it arrives. Much as he might like the idea you cannot remain the female authority figure in his life forever, so between now and then you should discuss and plan what he intends to do and how he plans to live his life as an adult. Though more often than not the best laid schemes of mice and men gang agley and in his case the most likely reason will be meeting a girl/woman, Mother Nature being the most unrelenting Mistress of us all.
Do write again if you need any more information or advice.
Additional comment from sissymaid kitty
Your son sounds remarkably similar to myself at that age, though I was not fortunate enough to have an understanding mother and resorted to stealing underwear from washing lines and dressing in secret while being racked with guilt. My mother was a religious zealot who wanted me to become a priest and for some considerable time I thought my best option was to undergo gender reassignment (i.e. have a sex change) and become a nun, but fortunately fate intervened and I became a sissymaid instead and found my true vocation in life.
It is glaringly obvious to me that your son is a natural submissive who, like me, expresses his submissiveness through cross dressing. Mistress Alison used the words almost certain, but I would say there is no almost about it and that it is a cast iron certainty. You yourself wrote that he would wear his maid's uniform 24/7 if you didn't stipulate he should wear it only when doing housework, something I first thought was a cunning ploy to encourage him to do more of it. By allowing him to display his true nature and encouraging him to do what he needs (a word I chose deliberately over wants) you will forge an immensely strong bond between the two of you. This bond will enable you to gently steer him in any direction you wish because as he goes deeper into his new role he will willingly give you more and more power, so instead of teen rebellion you will have willingly obedience and a very special kind of love. Mistress Alison has often written of the scared bond between Mistress and sissymaid as being similar to that between mother and child. What you are in effect doing is going through the rearing process again, bringing him up to be a different person.
Mistress Alison advised you about the natural progression of that process and as part of that progression you will probably need to devise a system of rewards and punishments to suit your particular situation. Another of Mistress Alison's mantras is "All sissymaids need regular gentle correction and the occasional sharp reminder of who is the Mistress and who is the maid." Punishments do not necessarily have to involve physical chastisement or pain, they just need to be unpleasant. When I was beginning my journey into sissydom the punishment I hated most above all things was the pointless, and seemingly endless, tedium of writing lines. A punishment that I resented for being childish as much as I loathed for its monotony. Today the worst punishment (other than the ultimate of being dismissed from Mistress's service) would be being deprived of my femininity, forfeiting the privilege of wearing soft silky underwear and my lovely smart uniform, wig, make up and heels and being made to dig the garden in a horrible rough boiler suit. Just writing those words makes me shudder.
Mistress Alison also wrote about planning for the longer term and what I might term an exit strategy. Obviously, the ideal would be to find him a suitably strong minded woman of approximately his own age who will appreciate having a sissyfied male in her life and can take over the reins when you are ready to relinquish them. However, not everybody is that lucky and it is therefore important that you ensure he maintains social contact with a wide range of people of suitable age. If he finds someone he thinks he wants to share his life with then you should be prepared to take on the role of mentoring her. The second most common letter Mistress Alison receives is one that says "I've discovered my partner/husband is a closet cross dresser, what should I do?" Or something very similar. Almost without exception those who go on to capitalise on it say their lives have improved dramatically and wish they known earlier or done it from the very beginning. When it comes to marriage a man who is also an obedient and efficient sissymaid should be seen as a prize catch rather than someone hiding a dirty secret to be rejected out of hand.
I hope you find my remarks helpful and wish you both well.
Dear Mistress Alison
Your words have turned out to be prophetic.
I did obtain a chastity tube for my son and told him that he could wear it at weekends, for a trial period only and that after a few weeks I would review the situation and possibly extend the times when it could be worn. To say he was pleased would be a gargantuan understatement, I think his actual words when I locked it place were, "At last I feel I'm making true progress." I asked him progress towards what and he immediately replied, "To becoming a proper sissymaid. You know like the ones you've read about." I told him we needed to have a serious talk and as quietly and calmly as I could told him I thought he was a bit young to be making irrevocable decisions about his future and he should keep as many options open as possible. He then said something that I couldn't argue with, "If I had told you I was gay, would you be trying to persuade me that I shouldn't be, that I should be normal, whatever normal is, and start going out with girls." I could only answer that I would have advised him that many boys went through different stages during the development of their sexual selves and that he shouldn't burn any boats.
For the first three weeks I let him wear it from the time he came home from school on Friday afternoon until the Monday morning of the following week, and I heard not one word of complaint. Several times I asked him if it was making him sore or uncomfortable and each time he said, "No. Mum, I'm fine." Then came the great lockdown and the closure of all schools. I don't know why I assumed that his chastity routine wouldn't change, but it did and dramatically. On Monday morning of the first week of lockdown I woke up to hear the sound of the washing machine running. I went down to the kitchen and found him dressed in his maids uniform, doing a wash load and cleaning out all the kitchen cupboards. When I asked him what he doing he answered, "Spring cleaning, since there's no school I thought I would make myself useful." I asked him why he was wearing the maid's uniform and he said, "What else would I wear to do the spring cleaning?" There was no answer to that, at least I didn't have one.
He went to resume what he'd been doing and I stopped him saying that I wanted to discuss it with him first, but he was obviously prepared for my reaction. He said, "There isn't anything to discuss, Richard (his brother) and I talked this over and we've decided we should both do more to help around the house. This lockdown looks like going on a long time and it isn't going to be easy for anyone. We can't go to school and we can't meet friends so the best thing we can do is take some of the weight off your shoulders. Look, you've done your bit, and in difficult circumstances you've given us both a loving upbringing so now it's payback time. Go and put your feet up and as soon as I've finished this I'll put the kettle on." I didn't know whether to feel proud or grateful or alarmed, or all three, but then came the sting in the tail, "Oh, by the way from now on I'd like to be known as Suzy, as in Suzanne with a z not Susan with an s. At least until I have to go back to school." Then he turned back to his cleaning, leaving me reeling.
For the first few days most of his "help" was more of a hindrance and I had to redo most the jobs after he'd gone to bed. But by the second week of lockdown he'd improved dramatically and I'd almost got used to seeing him dressed as a maid and his brother calling him Suzy. He (Richard) seems to be far less bothered by his brother's transformation than I am and he is also trying to more to help me. Both of them have been reading recipe books and have tried their hand at cooking, with what I will charitably call mixed results.
My son seems very happy as Suzy and now "she" has become more proficient in things like washing and ironing I can see some advantages to the situation, but my overall feeling is concern for the future, his future. Will he want to return to being a normal schoolboy, and if lockdown lasts for months as many are predicting will he even be able to. Is this going to do him long term emotional or psychological damage? Have I created a monster I can no longer control?
It is obvious from your son's words that you have made an excellent job of rearing both your sons and your love for them is reciprocated so there is absolutely no need to reproach yourself about anything. You have not created a monster or indeed anything else; as I wrote in my earlier e mails this is something which was always there deep within him and sooner or later it was going to come out. You may have been able to delay the process, which probably would have made him miserable, but you could never stop it. It is part of who he is. In my reply to your initial enquiry I mentioned the guilt button that all mothers have, and I suspect that yours has recently been working overtime.
While these are abnormal times and in the claustrophobic atmosphere of lockdown problems can appear intractable, what your son is doing is typical of all teenagers; he is pushing boundaries. Children do this from a very early age, try things out and see what happens, it's the way they learn; but when they get to a certain stage, usually around puberty, it becomes more about what they can get away with, and what taboos they can break without repercussions. You told your son he could wear his maid uniform only when he was doing housework, he wants to wear it more often so he has taken it upon himself to do more housework, so for him it's a win, win; he can wear the uniform while claiming to be acting out of altruism. How could you possibly complain? He may well believe he is acting purely from selfless motives, but at the very least he is getting something he wants and wants badly. You didn't object so he's pushed the boundary a little further by telling you he now wishes to be addressed as Suzy and again he got away with it; his brother now addresses him by his femme name and you have in effect rewarded him by letting him cook. Even your attitude to him being Suzy is beginning to change because you say you can now see the advantages.
What you need to do is take back control and reset the boundaries, though they don't necessarily have to the same as before. Fortunately, the one thing all those who actually desire to become sissymaids are seeking in their lives is discipline. It is always possible that your son, whom I shall refer to hereinafter as Suzy, is deliberately pushing the boundaries in order to goad you into imposing that discipline. It is important not to confuse discipline with punishment, which is quite different though the two are often sloppily and inaccurately used synonymously. Discipline is about order, authority, and control, it is essentially training someone, or oneself and many would claim the only true discipline is self-discipline, to do things that they wouldn't otherwise do voluntarily, even when you are not present. Suzy says she wishes to become a proper sissymaid so she needs to learn that the first tenet of the sissymaid's creed is obedience. Sissymaids don't decide when, what or how for themselves, they do as they are told. Always and without exception.
In her codicil to my last e mail kitty gave you a strong hint on how to drive home this most basic of lessons. She said that for her the worst punishment (other than dismissal) would be being deprived of her femininity and forfeiting the privilege of wearing her lovely smart uniform. I suggest that you practice a form of reverse petticoat punishment and tell Suzy that being allowed to wear the uniform is a privilege which can be withdrawn if she abuses it. You have to mean it and if necessary carry out your threat, though I strongly suspect that once Suzy realises you are serious you won't ever have to do so. I am most definitely not advocating that you morph into an ogress, merely that you become stricter with Suzy.
A question I often pose correspondents is, "where's the harm," as in "Where's the harm if your partner likes wearing pink panties under his trousers?" So I'll ask you, "Where's the harm in your son wearing the maid's uniform all day, every day, during lockdown since nobody else is going to see him. The obvious answer, and to me the only serious one, is that she might be tempted to neglect her school work.
I therefore advise that you devise a timetable for when Suzy must spend time on her school work dressed as a boy and when, and only when, it has been completed to your satisfaction may Suzy the schoolboy be permitted to change her clothes and become sissymaid Suzy. If she is tries to persuade you to allow her to do her schoolwork in her femme incarnation tell her that just as a butterfly has to spend a long period as a dull pupa before emerging in all its glory, she must spend a similar period in "drab" before she can emerge as a sissymaid and it will make her value her status as one more highly.
Set a rota of domestic chores for her to do each day, say cleaning one particular room from top to bottom or doing all the washing and ironing. Inspect her work afterwards and if it is not satisfactory make her redo it or make her change back into school uniform (not ordinary house clothes) and write punishment lines. Something like: "Sissymaids are at all times obedient, demure and respectful, they never argue, challenge, sulk or show resentment and always carry out their assigned duties cheerfully, with good grace and to the best of their ability, substandard or slipshod work is never acceptable." If the lines are not written to an acceptable standard reject them and insist she start again and possibly increase the number to be written.
Once she has become used to the new regime, and it may take time for both of you to adjust, you should have no more serious problems. When lockdown ends and it is time for her return to school she should have acquired the mindset of an obedient sissymaid, you simply tell her what is going to happen and she does it. If you think she might object to returning to her former identity during the school week then remind her that the privilege of wearing her uniform can be withdrawn at any moment and for her the choice is a simple one: return to school willingly as her male persona and be a sissymaid in the evenings and at weekends; or be made to return unwillingly and wave goodbye to being a sissymaid, full stop. I think she will be extremely reluctant to abandon all the progress she's made and accept that it is really no different from wearing a school tie she wouldn't dream of wearing anywhere but at school.
Finally, I should prepare yourself for more requests, and anything other than respectful requests should be refused out of hand, for a greater degree of feminisation, a wig, shoes etc. Whether you grant them is a matter of personal choice, but I would advise requiring some quid pro quo from her, reminding her that additional privileges must be earned and can also be withdrawn.
I hope this proves useful and that the remainder of the lockdown is not too onerous for either Suzy or yourself.