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 email@example.com and please don't waste her valuable time asking "where / how can I find a Mistress?"
Dear Mistress Alison
I have been a fascinated reader of your publication for over a year now and always read your advice column first as it has been a mine of useful information. This began when my steady boyfriend of two years asked me if he could ask me something, when I told him he could he confessed if that's the right word to having long term fantasies about being made (my italics) to wear women's clothes by what he called a stern and intimidating lady and would I allow him to do this? At first I thought it was a joke but soon realised he was deadly serious. I've always liked to think of myself as being broadminded but this was something else. I told him I'd need time to think about it.
I read everything I could find on the subject and though he didn't mention it again I could tell he was like a cat on hot bricks while waiting for my decision. It actually took me less than a week to decode to give it a try but I made him wait a month before telling him I was prepared to try it out. But I also warned him that if I didn't like anything about it then that would be it, it would be over, finished, and he would never mention the subject again. His eyes lit up as he readily agreed and he told me he had been terrified I might chuck him when he first mentioned it, I was reminded of this when I read the excellent letter from Cassie and Jacqueline in the March issue. Then he thanked me fulsomely and told me I wouldn't regret it. He was right, it was the best decision I ever made and I have not one scintilla of regret over the way things have turned out, though I very much doubt he feels the same way.
I told him to get the things he needed and he said, "Well actually I already have some of them." I told him to show me and he went off returning a few minutes later dressed in just a pair of knickers and a matching garter belt holding up a pair of black stockings. I could clearly see the bulge in the front of his knickers. He stood there and then twirled round then waited for my reaction. I said, "Well you're a dark horse, how long have you had these things?" He said, "Since before I asked you about wearing them," and then he looked down. I said, "Not just a dark horse but a naughty boy as well, or should that be a naughty girl? Come here. Now!" He walked forward and I pulled down his knickers and tutted at his erection before saying, "Well I think the correct form is that naughty boys, or girls, get punished, don't they? Get over my lap." He obediently bent across my lap and I gave his bottom a few gentle slaps, I would have given him more but suddenly he gasped and then ejaculated all over my legs.
I pushed him off and stood up shouting "You disgusting pig. How dare you mess over me, and without my permission too. You deserve to have that cut off or at the very least locked up." He looked up and said, "Well actually I do have the necessary item." For a wild instant I thought he meant for cutting off his penis then realised he was talking about chastity. I told him to fetch it immediately but as he went out I called after him, "Wash yourself thoroughly first." He called back, "Yes Mistress." This was the first time he addressed me as Mistress and ever since I've insisted that he calls me nothing else. He was soon back and after quite a bit of trial and error with the spacers I locked him securely in chastity and put the keys safely in my pocket. In case you're wondering I did think he might have had some extra keys cut before giving it to me so I changed it for a different item of my own choosing within a fortnight. I asked him how it felt and he replied, "A little strange and heavy but oddly satisfying." I asked how so and he said, "Very secure. I suppose I mean safe." I said, "Good because you'd better get used to it." At that time I was still thinking in terms of an experiment and though bossing him around and having him obey me was very satisfying I didn't realise at the time how much it was going to change both our lives.
At first he made all the running; it was him that advised me to check out your website. He bought a great deal more underwear for himself and simply couldn't do enough for me. He always was very good about things like cooking and keeping my place tidy and cleaning it whenever he visited (at that time we weren't living together), but now he was insisting that I take things easy while he did all the housework and with every passing day I got to like it more. Like Cassie I got a particularly buzz out of watching him struggle with his chastity while satisfying my own sexual desires. Apart from his lack of what he called relief he seemed very happy with the arrangement and a sissymaid's uniform, wig and shoes soon appeared.
Then the inevitable happened and he did something to annoy me, I forget what exactly, and I caned his bottom. He was perfectly okay with the first few strokes, as it was the first time I'd caned anybody I was probably going too lightly, then he suddenly said, "Hey, that's enough, it really hurt. I mean really hurt." In a tone of feigned surprise I said, "Did it?" Then in a much firmer voice said, "Well guess what, that's the whole idea. It's meant to and if you know what's good for you'll shut up and keep still." He said, "Sorry, Mistress," and apart from whimpers, gasps and finally tears and cries of pain said nothing more throughout his punishment. For me it was an epiphany.
In the September issue you told a correspondent called Debbie that having power would change her and that having a fully sissified male kneeling in front of her with eyes respectfully lowered and knowing that with a snap of her fingers she could make him do absolutely anything she chose is one of the most erotic experiences there is, and it's addictive. Well I can endorse that 100%. In that moment I realised I could make him do anything I wished and knew that there would be no going back, for either of us. The thought of being in total control not just of my own life but his as well and that from now on he was going to do exactly as I decreed and devote his life to my pleasure was just amazing, it was almost orgasmic.
Several days later I told him he would be moving in with me as my 24/7 sissymaid. He would still go to work of course to earn money but at all other times he would live and work as my maid. His reaction didn't surprise me; he said that he was grateful to me for having cooperated but had decided that this lifestyle wasn't for him after all and could we please go back to the way things were before. I answered, "Not a chance. Not a cat in hell's chance, you asked for this and now you've got it and you're going to keep on getting it, and if I hear one more word of complaint, now or at any time in the future, you'll get a caning that'll make the last one seem like a tickle with a feather duster. Now quit whining and do as you're told." He looked horrified as he replied simply, "Yes Mistress." He has been my live in sissymaid ever since and has had many punishments with my ever expanding collection of what you term instruments. I don't like to think of myself as a sadist but I may well be turning into one as exercising the power I have over him is by far the most sexually arousing thing I have yet experienced and I have absolutely no intention of giving it up.
I apologise for the overlong preamble but I thought some background would be helpful before I ask my three specific questions.
Although since he became my sissymaid I have allowed him the occasional privilege of sex with me I am thinking of having him castrated (I know you disapprove of such things) and taking lovers as and when I need them, do you think it would be better for me to visit them and have him lick me clean afterwards or for them to visit me and have him witness them enjoying what he never will again?
To celebrate Christmas I wish to find how exactly how much physical pain he take and want to really push him to his limits and beyond, what do think is the most painful of all disciplinary instruments?
When giving a punishment using multiple instruments is there an optimum order in which to use them and if so what is it?
Thank you for kind comments about PDQ and my small part of it in particular. I'm delighted that the advice I've given to others has been useful to you and even more delighted to read that yet another strong minded woman has taken control of a relationship and is now the proud possessor of a sissymaid.
As you've obviously read what I've previously written regarding castration and know my views on the subject I won't go over old ground again except to say such a drastic step would be demanding a total lifelong commitment from him and commitment should cut both ways. The question of whether you should take a lover, or lovers, and where you should have sex with them is more of a moral question and therefore outside my remit. I assume you are still not married to the sissymaid you refer to as your boyfriend so you would not be breaking any vows so it rather depends on what sort of relationship you had before; and more importantly the precise nature of the relationship as Mistress and sissymaid you are seeking to have in future. Put simply, this boils down to the questions; do you still have feelings for him now he has become she, and do you want her to obey you out of fear or out of love? It is easy to assume that this lifestyle is simply a case of the Mistress gives the orders and the sissymaid obeys, or else she gets punished. However nothing in life is quite that simple and there are just as many subtle variations on the relationship between a Mistress and her sissymaid as there are in the vanilla world, and few if any of them make much sense to outsiders. Before making any decision about this I suggest you ask yourself how you would feel if you discovered that your sissymaid was moonlighting for another Mistress and what you might do about it.
Your second question is probably the most complex and difficult to answer. Philosophers and scientists have been studying the nature of pain since the dawn of time, there is even a scientific unit of pain intensity called the dol, and they have only begun to scratch the surface. As I told an earlier correspondent, David, in the November issue, pain is an intensely personal thing and it is important to understand that just as we don't see with our eyes, which are merely receptors, but with our brains; so likewise do we feel pain, not with our nerves but with our brains and there are many psychological factors which contribute to the overall sensation we experience. Kitty, my own sissymaid, tells me that any punishment is "at least ten times more painful" if she feels she's done something really bad or that I'm very angry with her rather than it being for some minor lapse. The lady who was my mentor as a Mistress always used to say that, "All sissymaids require regular gentle correction and the occasional sharp reminder of who is Mistress and who is the maid." Kitty may be an extremely well trained and dedicated sissymaid who worships me, but she still gets regular punishments. If I'm testing a new instrument on her for the first time she will steel herself to take as many strokes as possible without complaint and give me a running commentary on its effects and then be happy that's she's pushed herself as far she possibly can for me. If she's receiving say ten strokes of the medium cane for having a crooked stocking seam she will take them with complete equanimity and afterwards thank me with a bright smile and a curtsy, but if I'm using the same cane for something more serious she will be crying well before I've reached the tenth stroke.
Returning to the purely physical, pain is caused when energy is transferred from the punishment instrument to the recipient's body. The energy contained in any moving body is given by the equation E = ½mv² where m is the mass, for all practical purposes the same as weight, and v is the velocity. Because the velocity component is squared, doubling the speed at which the instrument is moving quadruples the energy it delivers. The other factor is the area over which that energy is dissipated; think of a needle, very light pressure will produce a sharp pain but the same pressure applied with a blunt pencil almost no pain at all. So a thin fast moving instrument will produce a more intense pain, generally termed sting, that a heavier slower moving one. The reason that long single tailed whips, usually and incorrectly called bullwhips, can be cracked is that the tip of the whip is moving so fast it breaks the sound barrier producing a mini sonic boom.
So in theory the long single tail should be the most painful, but although I possess two they are impractical for indoor use and I seldom use them and even when I do kitty reports that they are far from being my most painful instrument. Neither is the 4ft 6 rhino hide sjambok, another instrument with a deservedly fearsome reputation. The two instruments she says are the most painful are a 60cms x 8cms leather strap known as a priest's belt which is constructed of three layers each 5 mm thick but the middle layer has wide holes punch in the last third of its length into which lead discs have been inserted giving it extra weight at the business end. Just a few strokes will raise spectacular bruises and welts and it is ideal for tenderising bottoms prior to the application of other instruments. Top of her pain list is my carriage whip, it has a slightly stiff carbon fibre handle about 60cms long, which is like a whippy cane or perhaps a fishing rod, and then a 3mm diameter plaited leather lash 145cms long. It needs a practiced hand to wield it effectively and care needs to be taken to avoid the eyes and breaking the skin, but it certainly does the business.
Another factor to consider is position or stance. The reason those about to be punished are traditionally told to bend over is that this brings the nerve endings closer to the surface while simultaneously stretching the skin, thereby reducing the thickness of the protective layer it provides. So a flogging delivered to a standing recipient with his weight on the heels will be less severe than if he were lifted on to his toes and having his entire weight taken from the wrists would be more severe still. Also important is the point of impact, the traditional areas of bottom, thighs, back have widely spaced nerve endings and so are relatively insensitive compared to say the palms or soles of the feet, the backs of the knees or more intimate parts. Half a dozen rapid gentle strokes with a light cane applied to the soles of the feet will be far more painful than twenty with a heavier cane across the more traditional backside. An instrument applied across the fingers will have a different effect to when it is used across the palms and so on.
There is also the matter of technique. If you take a crop, thin cane or single tail whip and swing it sharply backwards and upwards as in preparation to deliver a stroke then at the top of the swing you'll feel the tip continuing to move due to inertia and the flexibility of the instrument. This flexure is storing energy, the energy you've put into it by virtue of having swung it, known as kinetic energy. If at that instant you do as many do when administering punishments and stop to wait for the right psychological moment then that energy will be lost. If on the other hand you immediately begin the down stroke while the tip is still moving backwards then the flexure increases and more energy will be stored to be released on impact causing a higher level of physical pain. The choice of whether the extra pain causes more distress than the anticipation of waiting for it or vice versa only you can decide through experimentation.
Also when the body experiences pain it releases natural analgesic substances called endorphins. When these endorphins reach a certain level in the bloodstream the person's perception of pain suddenly toggles and they go into what the S&M fraternity calls "subspace" and going into subspace is every masochist's holy grail. Kitty once described subspace thus: "Suddenly all your other senses shut down and nothing else in the universe exists except the pain and Mistress and you. The three of you are alone in your own private paradise, all you are conscious of is her and the exquisite gift of her pain. It still hurts but you are dancing on the moon and feel you can reach out and fill your pockets with the stars. It is the most sublime state imaginable this side of heaven and you want it to last forever. But of course it doesn't and when you come out of subspace it happens very rapidly, it's like jumping off a cliff, and suddenly you feel like you spent the last few hours in a cement mixer." As you can see she has the soul of a poet.
There is a very old expression, "There's no substitute for experience," and I suggest you spend your time between Christmas and the New Year experimenting with the implements you have and gauging your sissymaid's reaction to each. Remember that after the first session she will be pre sensitised so I also suggest you concentrate on one area of her body on one day and move on to another the next, this will give her time to recover before you try something new on a part of her body that has already received your attention. Put at its simplest the most effective punishment instrument is the one your sissymaid fears most at the point in time when you are considering punishing her and this may change.
Your third question is much easier to answer though it will naturally be more a reflection of my own opinions based on my particular experience than hard scientific fact and others may have other ideas. Just like an athlete or a dancer neither you nor your sissymaid can give of your best unless you are properly warmed up so the first rule is start gently and work up. For this reason I would advise never punishing in anger, tempting though it often is, because if you do the tendency is to forget this basic truth leading both of you to burn out early. The exact procedure I use depends on whether I have a clear idea of what I'm going to do and how many strokes with what instruments I'm going to give in what order or whether I'm going to see how my mood and kitty's reactions take me. I might just be trying out a new acquisition in which case the start gently and work up applies even more.
Generally I start with a gentle paddling to the buttocks, alternating swats to the left and right cheeks. About thirty is usually enough to turn them a nice shade of pink and produce a warm glow to the touch. Then move on to either to a cane or my favourite dressage crop, either will produce contrasting darker stripes against the pink. It is important to pace yourself and leave enough time between strokes for the pain to build and the stripes to develop. This also increases the effect of anticipation on your sissymaid, a few swishes in the air may be added if you wish to tease her a little and increase this effect. Ideally you'll be aiming (excuse the pun) to get all the stroke as close as possible to each other, if possible precisely over the previous one. This will concentrate the pain in one area and intensify it. After you've applied the desired number of strokes either move to another area or choose a broader instrument. Half a dozen strokes from your tawse over the stripes left by the crop or cane will really have your sissymaid jumping and unless she's remarkable resilient is probably enough for a relative beginner. You can always come back to her bottom later.
With the back and shoulders the same principles apply. Start with a multi tail with relatively wide and or soft falls and apply the lashes over a wide area. Use lateral strokes, either forehand or backhand or a figure of eight configuration which results in diagonal strokes. Then increase the weight of the flogger or the use one with thinner falls or a combination leather/rubber, leather/chain type flogger before moving on to something like a single tail. One of my favourites is a thin single tail plaited for about 4 feet and then splitting into a pair of thin square section 15 inch long tailets. This has an excellent wrap around, and with careful positioning and technique I can get it to land on her left flank, wrap around across her back and right flank and the tip of one the tails to touch a nipple. It is not for the ham fisted to use or the faint hearted to receive and I use it sparingly and with care as it will easily break the skin.
Whatever you do to and with your sissy remember this is not some academic exercise in pain and she is not a just a "subject" or a lump of meat. She is a sentient human being whose life you now control and whose welfare is now in your hands. As her Mistress you have a care of care to your sissymaid and you should always be aware of the possibility that something you are contemplating might cause her physical or emotional harm. She has given you power but you should use it wisely as you grow into your respective roles together.
I wish you both a very Happy New Year and well for the future.