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 mistress-alison@ petticoated.com and please don't write asking "where / how can I find a Mistress?"
Dear Mistress Alison,
My question doesn't concern castration so I hope it's permissible to ask. My Mistress and I are quite new to petticoat discipline. About three months ago, Laura, my wife of just over a year, who always was very bossy even before we were married, announced out of the blue that being in an FLR (what I now know to mean a female led relationship) and having me under her thumb as a hen pecked husband was simply insufficient for her needs and that henceforth she would become my Mistress I would become her slave. There was no "unless you comply it's over," or "my way or the highway" just a plain statement of fact. I love my wife, now my Mistress, very much and would do anything to make her happy, but even so I was shocked. However she was adamant, and despite my initial protests I was locked into a chastity device and told any disobedience or dissent would be punished. Shortly after that my Mistress discovered your internet magazine and informed me that petticoat discipline would be good for me and from now on be an integral part of my training. All my male underwear was discarded and replaced with frilly female undies, and within a matter of weeks I was transformed into her sissymaid answering first to the name of Michele until she decided that such a pretty name was inappropriate for a servant girl and changed it to Milly, as in Milly maid. In order to please her I went along with it, not that I had any option, thinking it was a phase that might pass, but have now come to accept that it is a permanent arrangement. So the moment I get in from work I have to change into a maid's uniform although my Mistress doesn't want me to wear a wig or make up as she wants me to look like a sissified male rather than a real woman. Though recently she has hinted that these privileges (as she calls them) might be earned in the future through good behaviour. Once changed I have to get on with housework, the laundry or work through a list of domestic chores, and any mistakes or perceived lack of application result in her caning my bottom, which hurts a lot more than I ever imagined it would. I can't say for a second that I enjoy any of it, but I have accepted it and it does seem to make my Mistress very happy, which does give me a certain sense of satisfaction because as I said I do love her.
My Mistress now wishes to go further and use a strap on dildo on me, or in me, and I am a very nervous about this. My questions are these: are there any health risks, do I need to empty my bowel beforehand and since I guess it's essential to use a lubricant which one would you recommend? I realise the answers are probably obvious to you but they aren't to me. I know could look on the internet but I think that much of what one reads there is fiction or fantasy and I want to get this right for my Mistress so I would rather ask a reliable source.
Thank you in advance.
Firstly, congratulations on becoming a sissymaid, your Mistress has very wisely made a decision that I'm sure neither of you will regret. It may feel a little strange at first, all change can be uncomfortable until the new becomes routine, but reading between the lines of your letter I get the distinct impression that you already had a strong submissive streak and may even have secretly wanted your wife to become your Mistress, or at least been sending out signals, possibly at a subliminal level, that you wanted her to dominate you. Well now she has, so all you have to remember are the following; Mistress is always right and she takes all the decisions, you must always obey her instantly and without question, make sure you are always correctly and impeccably turned out in your uniform, smile to show her how happy you are to be her sissymaid, curtsy whenever entering or leaving her presence and when she speaks to you, and thank her every time she punishes you. Follow those simple rules and you won't go far wrong. Remember the acronym ODD: obedience, dress, demeanour and you may yet earn the privilege of really looking the part.
It is entirely natural for you to feel nervous. As an anal virgin it is only to be expected and of course you also want to make your first time very special, both for your Mistress and yourself. You probably felt exactly the same the first time you had vanilla sex with her and this is no different. Now to your specific questions. Firstly, there is no human activity that is entirely free of risk, every breath you take has a tiny element of risk attached to it, but while I've heard of people injuring themselves in all manner of bizarre ways I've never heard of anyone coming to harm through using a strap on. Every year thousands of people attend casualty departments to have a truly wondrous assortment of objects removed from their bottoms, invariably as a result of their own stupidity, but this generally causes them no more than some degree of embarrassment. With any anal activity just use your common sense, a good maxim being if you wouldn't put it in your mouth don't put it anywhere else. Personally, I wouldn't insert anything made of glass due to the tiny but nevertheless real possibility of it breaking, though glass dildos and plugs are made and many people use them without problems. Secondly, whether you empty your bowel prior to taking a dildo is purely a matter of personal choice, if you are feeling very full then it might make you more comfortable to visit the lavatory first, but then your Mistress may want some degree of discomfort to be part of the experience, and as always it is her choice. Why not try it both ways and see which she prefers? Lastly, if your Mistress wishes to make it very painful for you then you can get by without using a lubricant, but it helps enormously, especially for nervous first timers. Some people mange with salvia, usually the recipient is required to give the strap on "deep throat" before insertion, so the better job they do the more easily it slips in, but most use a commercial lube. The most popular lubricant is probably KY jelly because it is easily available from any chemist and most large supermarkets. There are also specialist lubricants like "Liquid Silk" "Fist It" and "Anal Reflex Gel" which are available on the internet. Once again, experiment and find what best suits your particular situation.
However the most important factor in whether your first time is a success isn't any of the things you've asked about, but choosing the right size of strap on. The commonest and most natural error is to pick one too small, remember your Mistress will want to stretch you both physically and mentally. The human body is wonderfully elastic; in order for you to be here a woman's vagina had to stretch far enough for your head to pass down it and your rectum is made of the same type of tissue. If you choose a 1 inch diameter tiddler you and your Mistress will very rapidly grow dissatisfied as your sphincter will offer so little resistance that you will both barely feel it, but if you go too large you may find insertion difficult and it could put you off further experimentation. I suggest as a starting point you measure your penis (use a tailors tape measure or piece of string around the widest part and divide by three to get the diameter) then multiply that figure by 1.5 ( or 2 if you're feeling adventurous) then choose the size closest to the resulting figure. If it falls between two available sizes go for the larger. As a rule of thumb I would say a 10 inch long 3 inch diameter would be about right for a beginner. They do come in all sizes, you can get them more than 30 inches long and 8 inches in diameter but such things are strictly for the very experienced. Your mistress might also wish to consider a double ended strap on where a shorter dildo goes inside her and rubs against her clitoris with every thrust meaning she can give herself an orgasm as you submit to her.
Remember this is all about submission; you are giving yourself to her for her pleasure and as a demonstration of your complete trust in her. The natural reaction, especially for first timers, is to tense up, but you have to show that trust by relaxing. She may wish to make your first time loving and gentle; an expression of the fact that that although she is your Mistress whose word is law she also cares deeply about you and your welfare. Or she may wish to underline her dominance by making it rough and brutal, almost like rape; once again it's her choice and you have to take it. Whatever happens of one thing I'm certain, it's something she will want to do it again and again, and once you've learned to relax it's something you will want her to do to you again and again and with larger and larger dildos. In time she will probably acquire a range of them in different lengths and diameters to suit all occasions. As she becomes more dominant and you more submissive you will probably want to try other anal toys and experiences, but that's for the future.
When it's all over don't forget to thank your Mistress profusely and make sure you clean the strap on thoroughly, wash it in warm soapy water, rinse and dry it, give it a light dusting of French chalk or talc (my sissymaid uses baby powder) and put it away carefully and with reverence.
I wish both of you good luck.
An additional comment from my sissymaid, kitty
Dear sissymaid milly
Welcome to the wonderful world of sissydom. I think you are incredibly fortunate because instead of wasting the best years of your lives together wandering unsatisfied and unfulfilled in the vanilla wilderness your Mistress has decided to take you firmly in hand and lead you on a glorious odyssey through the sunlit uplands of submission. As I have written before in PDQ becoming a sissymaid is a vocation and there is no higher calling than devoting your life to the service of the woman you love, your Mistress. Your role is to serve her, to smooth her path through life, to look after her, to care for her, to worship her, in short to cherish her. As you have discovered this can often be painful, sometimes very painful, but never was the expression no pain no gain more apposite than when applied to being a sissymaid. However, as you will also discover that pain has a purpose and the rewards that come from the unique bond twixt Mistress and her sissymaid far outweigh any physical suffering. In time your Mistress will almost certainly acquire an array of disciplinary instruments and you will come to find their afterglow as much a part of being her sissymaid as wearing panties, the gentle tug of your suspenders, the click-clack of your heels on the floor or the soft rustling of your petticoats. As a token of your submission you might like to present your Mistress with new instruments from time to time (leaving them on her pillow tied with a big pink bow adds a nice romantic touch) as it will signal to her that you've accepted your new role in life and acknowledge her absolute right to punish you whenever and however she chooses. I would suggest the minimum core requirement for any Mistress is a cane, a riding crop, a tawse, a multi tailed flogger and a paddle, but doubtless your Mistress will want to add to these over time. I would offer you three pieces of general advice.
First, you are both embarking on a voyage of discovery, but one with no ultimate destination. There is no right way to go or wrong turnings, just new and exciting experiences; so don't be put off trying anything because you think it's not for you or it's too extreme or way over the top. Life as a sissymaid is full of surprises and both of you will discover things you never dreamed you would ever enjoy and a few things that once tried are best forgotten.
Second, the more wholeheartedly you throw yourself into your new lifestyle the more you will get out of it. You are doing this to please the most important person in your world, your Mistress; and you will find pleasing her will give you more satisfaction and pleasure than anything else. It won't be easy, but it will be worth it and the sooner you grow into your role the sooner you will get to wear a lovely wig and all that feminine make up, both of which will help you feel more submissive and more determined to serve and please your Mistress.
Lastly, as you will by now have realised wearing high heels is very tiring on the feet, ankles, and calves so one of the things a sissymaid should excel at is foot massage. So when your Mistress comes in after a long day in heels, I suggest that after paying her the required obeisance, you sit her down, give her favourite evening drink, then kneel down slip off her shoes and get to work massaging her feet and lower legs. Nothing is more conducive to putting her in a good mood for the rest of the evening, and who knows how high she might allow your hands? It is also a good time to talk to her about anything that may be on your mind, you have a captive audience and if you are doing your job properly a receptive one. I hope becoming a sissymaid brings you the same true joy and contentment that it has brought me.
Dear Mistress Alison
Thank you for the swiftness of your reply and the wealth of information and advice. I'm afraid I didn't phrase my question accurately enough; when I said health risks I really meant long term effects such as incontinence in later life caused by the stretching of the sphincter muscles.
Also I would be eternally gratefully if your sissymaid didn't put ideas regarding punishment implements in my Mistress's head, she has control of my computer and checks all my e mails. I find it difficult enough coping with the cane, often being unable to hold back tears and I just don't think I could take anything more severe. My Mistress calls me a cry baby and since reading the articles about dummy discipline in your Christmas issue has said that if I can't handle adult discipline then maybe I should be put into nappies until such time as I can. The prospect of having to poo in a nappy and then be left in it is just too awful to contemplate.
Perhaps you need to spend time in nappies until you have learned to read. What part of "Mistress is always right and she takes all the decisions, you must always obey her instantly and without question" do you not understand? Similarly in my original article what part of "Never forget that physical punishments must contain two elements, pain and loss of dignity. They must hurt, a lot," and "long before any such punishment is over your sissymaid should be in tears, not just a few sobs but weeping uncontrollably, yelling in pain at each stroke, begging for mercy and promising never to be naughty again," do you fail to comprehend. Once again I recommend you think of the acronym ODD.
However, as you are new to this I am prepared to be gracious and merely suggest that you tell your Mistress you deserve punishment for your lapse. When you say you don't think I could take anything more severe than the cane what you actually mean is that you need help in the form of restraint. There is no shame in this, always provided you ask in the correct manner. Even kitty needs to be firmly restrained in order to take the more effective of my disciplinary instruments. There are a wide range of items available ranging from purpose designed whipping benches costing hundreds of pound, to simple folding A frames and I suggest you peruse the internet and buy one as a present for your Mistress. In the short term with a set of wrist and ankle cuffs, some rope (old stockings make an excellent substitute for proper bondage rope as they are strong yet will not cut into or abrade the skin) a table and a little ingenuity your Mistress should be able to restrain you securely while leaving the most important target areas exposed. Do not forget to thank her afterwards.