Mistress Lady Penelope Services:

Mistress Lady Penelope with her 4 sissy maids

Sissy Maid Training


French Maid Training


Prissy Sissy Training Service And Sissification For Mincing Sissies


Crossdressing Service, Dressing Service, Forced Feminisation

And Transformation For Crossdressers


Corsetry And Tight Laced Corset Training


Traditional Corporal Punishment And Discipline For Wayward Boys

By


Supreme Mistress Lady Penelope


Medway Kent UK M2 J4


Telephone For Appointment on: 07970183024

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Staying Overnight

Mistress Lady Penelope has had many requests from clients for overnight stays. Mistress has now decided to grant these requests and will offer clients an opportunity to stay overnight before their appointment, or stay the night after their appointment.

You will be staying downstairs with Mistress Lady Penelope’s 24/7 Live-in Maid Sissy Barbie, to experience a little of the life of Mistress’ 24/7 Live-in Maid.

If you stay the night before your appointment with Mistress Lady Penelope, on the following morning you will be dressed downstairs in your female attire as chosen by Mistress beforehand. Once you have finished downstairs and ready for your appointment with Mistress Lady Penelope, you will come upstairs and will receive your make over from Mistress.

If you are staying overnight after your appointment, then once your appointment with Mistress Lady Penelope has finished, 24/7 Live-in Maid Sissy Barbie will take you downstairs to the maid’s quarters. 

Whether staying before or after your appointment, you will be expected to perform some light duties. You will cook and serve 24/7 Live-in Maid Sissy Barbie’s evening meal and the same meal for yourself. Head maid Sissy Barbie will decide on the meal but previously notified dietary/allergy requirement may be taken into account.

The next morning you will serve 24/7 Live-in Maid Barbie her Breakfast in bed, on a breakfast tray. Breakfast will be offered to you too.

You will leave at 9am in the morning. In order for 24/7 Live-in Maid Sissy Barbie to resume her duties for her Mistress Lady Penelope.

There will be a supplementary charge for your accommodation and food.

Opportunities For Skilled People With Mistress Lady Penelope

Mistress Lady Penelope is looking for a client who is a builder come painter and decorator. In return for Mistress’ services, they can do certain work in Mistress’ residence.

Lady Penelope would also like a client who can do web design in WordPress and search engine optimisation.

Mistress Lady Penelope is located in Rainham in Kent.

Please contact Mistress if you are interested. Either by telephone on: 07970183024 or by email:

mistressladypenelope 666@gmail.com.

If the above URL appears on one line, then please remove the space before 666 as it is only there for narrow screen mobile phones.

Strictly Virtuous Services Only

Be warned Mistress Lady Penelope offers only virtuous services.

Any client attending one of Mistress Lady Penelope’s sessions, who makes any immoral request to Mistress or her Sissy Maids during their visit, will be asked to leave the premises immediately, will forfeit their tribute, You will be automatically banished.

Public View Of Crossdressers

Attitudes Towards Crossdressing And TVs have changed over the Years, only bigoted vanilla people have the wrong concept of people who like to Crossdress, believing they are Perverts. You tell me, What is the Norm these days. I would really like to know?

Crossdressing has been going on for centuries. Achilles dressed as a girl to avoid going to the Trojan war. King Henri III of France sat on his throne in ball gowns. From the mid 16th century to the early 20th century, boys up to eight wore gowns or dresses.


I have always admired the artist Sir Grayson Perry, when he accepted the 2003 Turner Prize award in a satin daisy-sprigged dress, embroidered with the word Sissy. Sir Grayson (or his femme name Clair) contacted me through my email address, as he wanted to personally speak with me on the telephone. My Head Maid at the time Madam FiFi, informed me that Sir Grayson wanted to speak with me on the telephone, my Head Maid arranged a mutual day and time for me to speak to Sir Grayson. Sir Grayson personally congratulated me on my hard work, in creating Prissy Sissy art into life form Prissy Sissies, we had a wonderful long discussion.


Another example is boys dressing in ladies clothes in Thailand. Crossdressing clubs are in the majority of towns. Crossdressing is often on television. Canal Street in Manchester is famous for cross dressers. I have found the older generation today, are very narrow minded biassed people. The younger generation are not bothered. In today’s society, what is the norm now?

What is a Mistress?

Firstly it must be said that miss is an abbreviation for mistress but is unmarried, however ‘mistress’ originally meant a woman who was in charge, usually of a house, often a great house.

What is a true Mistress in the 21st century?

In modern day usage, Mistress with capital M is different from a mistress with a small m. Just to clarify, a mistress is a woman in an ongoing sexual relationship with a married man who is not her husband, whereas Mistresses are Dominant women in charge of subservient people, often males but not always.

Mistresses are powerful women and are born dominant, it is not something which can be taught. A Mistress commands her subordinates and they obey. A Mistress uses the ‘voice of command’, the tone of a Mistress’ voice leaves nobody in any doubt that she must be obeyed, just like a drill sergeant on a military parade ground.

Often subservient males are dressed in female clothes, such as a maid uniform. This emphasises that the society norm, that males are mainly in charge does not apply. However Mistresses do not dress in male clothes, indeed their subservient males, while dressed as females, lust after and are often in love with their Mistress, but are never allowed to bring their desires to fruition. A part of courtship is that men desire women, but as soon as a man fulfils his desire he often loses his respect for the woman. A Mistress never ever allows this to happen.

As a prime example of this, Mistress Lady Penelope not only speaks powerfully, she acts powerfully too, such as when Mistress entered into a noisy country public house and slammed her handbag down on a table. Immediately silence descended on the whole place, this all without saying a word.

After a short pause, the silence was broken by the landlord meekly walking over and asking ‘What can I get you Madam?’. A man turned to Mistress’ chauffeur and said ‘I can see who is in charge.’ Wherever Mistress goes, this always happens, men notice the allure of Mistress Lady Penelope. Even when Mistress is accompanied by a man, some more daring men, sometimes famous men, will come over and try to introduce themselves to Mistress.

Introducing You To The Supreme Mistress Lady Penelope


Welcome to Mistress Lady Penelope’s home page. I am sure you will find Mistress Lady Penelope’s website very informative.

Mistress Lady Penelope has had clients from all over the world to pay respects to Mistress. Mistress Lady Penelope is very well known over New Zealand, Australia and America. It appears that Mistress Lady Penelope has a big cult following in these countries and of course the UK.

You will notice Mistress Lady Penelope refuses to exhibit herself all over Mistress’ website. Mistress Lady Penelope prefers to remain totally discreet and aloof, until you finally have an audience with the forceful infamous formidable powerful mesmerising captivating Mistress Lady Penelope, who is an intelligent and creative Mistress. You only can hear Mistress Lady Penelope’s commanding voice on YouTube videos, Mistress training her Mincing Sissy Maids in to submission or you will take the consequences wont you, my pathetic Mincing Sissy Maids and Mincing Prissy Sissies.

Mistress Lady Penelope is a creative Mistress who can make your fantasies into reality. There are of course a huge variety of fantasies. You will need to inform Mistress Lady Penelope the details before you come along for your appointment with Mistress Lady Penelope and Mistress’ Mincing Sissy maid can be prepared for your visit. Hence Mistress valuable time and your finances will not be wasted.


Many clients are submissive beta males. If that is you, once you cross the house’s threshold, you also cross a mental threshold, whereby you submit totally to Mistress Lady Penelope’s considerable willpower. You will become Mistress’ property, for her to do with as she desires. You will be forced  to do as she instructs, make you dress in whatever way pleases Mistress Lady Penelope chooses for you, behave in whatever way pleases Mistress etc. Do expect to be totally and utterly humiliated. Mistress Lady Penelope adores humiliating you.


Some clients only desire physical pain Corporal Punishment service is for them. It can be combined with any of the other services if the client wishes. For instance you might want to wear a girl’s school uniform. You might like to be dressed as Mistress’ young niece who has misbehaved and needs spanking.

Here I will explain the various services of Mistress Lady Penelope, so that you can decide which if any you are interested in, before you contact the Supreme Mistress.


Outlined below are Mistress Lady Penelope’s services to allow you to choose which you desire. For a more in depth look, use the menu at the top of the page. This takes you to a separate page for each service, but please read the general information below all the individual sections on this page before contacting Mistress.


It is possible to customise your session in some ways if you request this in advance. For instance you could ask not to be disciplined is certain ways. To set limits or to combine aspects of two different services.

Remote vs in person training. Real time sessions are far more preferable but Mistress Lady Penelope also offers video Skype sessions and even telephone sessions to clients who cannot attend in person.

Naturally some things cannot be done remotely, like adult corporal punishment for instance. There is of course no access to Mistress’ huge range of clothes, shoes and accessories. Mistress cannot do a makeover remotely but can instruct you how to apply your makeup to achieve the desired feminine appearance. Mistress can also advise on the best makeup products which should be used. Clients must provide any clothes, shoes and accessories themselves but again Mistress can offer advice, encouragement and if you do wrong, can verbally rebuke you.

Some clients might like Mistress to be keyholder for their chastity device remotely and use the postal service to transport keys. Most locks come with two or more keys so one can be posted first and when it arrives safely the other can be sent, just in case one gets lost in the post, leaving the client the unenviable task of either going to a locksmith or breaking into their own chastity device.


Sissy Maid Training And French Maid Training By Mistress Lady Penelope

French Maid being corrected by Head Maid.


Mistress Lady Penelope is extremely passionate about Sissy Maid / French Maid Training. Mistress totally adores humiliating her little Sissy snivelling wimps.

It is such a privilege for you to be trained by the renowned Supreme Mistress Lady Penelope. Mistress will mould you into the Mincing Sissy little Maid you have desired. You will quickly submit to Mistress or suffer the humiliating consequences wont you?

How does Mistress Lady Penelope train her, snivelling little Sissy Maids?

Mistress Lady Penelope will train you to a very high standard. Mistress is renowned for this, so you have been duly warned my Sissy Mincing Maids.

As far as Mistress lady Penelope is concerned, you will duly submit yourself to Mistress’ demands. You do not have the privilege of being called by a Sissy name. You are just a Maid wearing a numbered badge. The badge has been drawn by yourself out of  Mistress’ red velvet pouch served on a silver tray. The tray held by her 24/7 live in Mincing Sissy Maid Sissy Barbie. Whatever numbered badge you have drawn, you will automatically receive the same number of strokes. The strokes will be entered into Mistress Lady Penelope’s red velvet book, for future use.


Do expect my Mincing Sissy/French Maid to have intense Sissy Maid Training at all times. If not you will suffer the full consequences.

Sisssy Maid/French Maid Training Begins With The Supreme Mistress Lady Penelope

Head Maid Sissy Barbie will teach all aspiring Maids etiquette, curtseying, bobbing and standing at attention. When you have learnt those to Mistress Lady Penelope’s satisfaction, you will proceed to the next step. Sissy Barbie will present you to Mistress in her private lounge.

Mistress Lady Penelope will inspect you and your Sissy/French Maid’s uniform. Mistress will test you. To check that you have properly learnt and retained what you have been taught. Many find being in the presence of formidable Mistress Lady Penelope drives what they have learnt a few minutes earlier from their mind. They will suffer the consequences of their lapse of memory. Those who cannot learn normally, have to have their lesson driven hard into them.

Mistress Lady Penelope’s First Royal Command To You

Mistress Lady Penelope will allocate the numbered Maid a task she must carry out. Her Mincing Sissy Maid will obey Mistress’ command to Mistress’ satisfaction or the consequences are inevitable.

For instance it is a great privilege to clean Mistress Lady Penelope’s personal bedroom and en-suite. You will be watched by a secret camera at all times, which are hidden around Mistress’ home. You may have seen an old picture of a Maid’s head being held down a W.C. bowl. That was for failing to adequately clean under the rim.

Mincing Sissy Maid may be tasked with serving lunch for Mistress Lady Penelope. Whilst Mistress is eating her lunch, you will stand by Mistress Lady Penelope’s side. You will stand stiffly at attention like a statue at all times. Once Mistress has finished her lunch, you will clear away and resume your domestic duties.


Mincing Prissy Sissy Doll Training For Sissies And Petticoat Punishment/Discipline By The Supreme Mistress Lady Penelope


If you select Mincing Sissy doll training, you will become Mistress Lady Penelope’s life style Sissy Doll. Mistress’ Maid will dress you in the frilliest most Sissy satin dresses. Lots of giant sized satin bows and 100 yards of organza petticoat. Mistress enjoys doing the make up herself, transforming  your face into a Sissy doll. Your face will be framed with a Sissy blonde curly wig. Maybe topped with a Sissy tiara. Your crowning glory.

Mistress Lady Penelope has a vast choice of bespoke Sissy dresses for Mistress to choose from. Including ones inspired by Prim and Prissy’s wonderful illustrations. These make the two dimensional images into three dimensional reality with you inside them.

Mincing Prissy Sissy Correction


If you fail to learn Mincing Sissy mannerisms, Mistress Lady Penelope will decide on correction. Maybe put you in a Sissy pink posture collar. Perhaps pink leather fetters to restrict your Mincing Sissy walking, whist you carry out your duties. Possibly Mistress will put her Mincing Sissy doll into pink leather manacles, or both. Even better Mistress might choose to put you into her Sissy bright pink straight jacket. The wording on the straight jacket “Property of Mistress Lady Penelope”. How humiliating is this to her little Mincing Sissy doll, the Sissy straight jacket completely restricts all arm movements.

Conceivably a leather white or Sissy pink arm-binder. Arm-binders can be extremely painful, depending on how long Mistress Lady Penelope decides you are to wear it. My Mincing Sissies will obey Mistress Lady Penelope’s order. Prime example, Mistress may ask for you to sing or dance for Mistress’ amusement and pleasure. My Sissies will have to speak with a Sissy lisp, or should I say a thitthy withp. Any dolly who misbehaves will of course be spanked. Either with Mistress’ leather gloved hand or a hairbrush.


Mistress Lady Penelope will make you into her lisping Mincing, crying walking, squealing squawking, living doll.

Petticoat Punishment And Petticoat Discipline For Naughty Little Prissy Sissies


For those who dream of petticoat punishment or petticoat discipline, it will be carried out to the extreme.


You think dressing as a female is punishment? You clearly regard females as inferior. Your temerity is an insult to every woman including Mistress Lady Penelope. Mistress will punish you on behalf of all women. You are clearly a little boy, never forget this. You will be caged in a chastity device. Kept under lock and key, even when you sit down to have a tinkle. Maybe you will be dressed in a girl’s school uniform if this pleases Mistress. Possibly a pretty party satin dress with plenty of large satin bows. In your hair, wrists, ankles, waist or wherever, as if to attend a party. Perhaps some other apparel, whatever way Mistress Lady Penelope chooses for you.


You will behave yourself, act demurely, keep your knees together. Failure to do this, will result in punishment. Corner time with your nose to the wall. Your hands on top of your head. Mistress may decide to spank you. Maybe you will suffer a more serious punishment.


Cross Dressing Service, Transformation, Forced Feminisation For Crossdressers And TVs By Mistress Lady Penelope


If you select Mistress Lady Penelope’s crossdressing service, feminisation and transformation service, then the same applies. They all begin with Mistress giving you a make over. Mistress Lady Penelope will ask you what look you wish to achieve. Normally Mistress will select what you are going to wear. In some cases clients bring along your own feminine clothes. Other clients may have asked for Mistress to buy clothes on their behalf. They have selected items online and requested Mistress do the actual purchasing for them. They will be have done a bank transfer for their clothing or lingerie.

Mistress Lady Penelope has a vast amount of designer clothes and lingerie. All manner of stockings, including seamed Cuban heeled stockings. Many variety of dresses, skirts, blouses for her to choose from. This includes night dresses and peignoirs. All this in a large range of sizes from UK 14 to 32. Shoes from size 3 1/2 up to size 14. Heel heights from flats to towering heels and styles from fluffy slippers to the most elegant evening shoes. Handbags of many types. Practical handbags. Evening clutch bags barely large enough to hold the essential makeup a lady needs to maintain her appearance. Boxes and boxes of all types of jewellery, wigs, fascinators, hats and underwear.

Mistress Lady Penelope Will Improve your figure Or Else?

Mistress has Corsets to reduce your waist, also bras and breast forms, full petticoats. Breast-forms and a bra increase your size above your waist and fluffy bouffant petticoats increase your size below. Hence your waist looks even smaller in comparison. Holding in your waist with a corset as well can achieve an ultra feminine hour glass silhouette which many real girls would love to have. It makes you look amazing.

Props like fans, feather boas and parasols are also available. Once you are completely en-femme you can choose to go for another change of outfit. Most cross dressers like to be on their own for a while in my dressing room admiring themselves. They cannot believe how convincing they are with total transformation. A lot of men look better than females.


Mistress Lady Penelope will invite you to chat in her private lounge. Maid Sissy Barbie will serve you tea and cake. At times Mistress Lady Penelope would ask you, would you like to be a model for her website. If you agree Mistress will do a photo shoot. Normally, clients who come attend a crossdressing service appointment do not want corporal punishment. Unlike all other services of Mistress Lady Penelope’s. However, if you wish to combine it with your cross dressing service, you should request this in advance.


If you wish to learn how to put on your makeup, Mistress is open to doing this for you. It does however, naturally, take longer.


Traditional Corporal Punishment, Correction And Discipline for Wayward Boys By The Supreme Mistress Lady Penelope


If you select corporal punishment, normally you will get marks from your punishment. If you wish not to show any marks, you must inform Mistress Lady Penelope on the telephone. Many others they say the harder the better.


Mistress Lady Penelope is renown for her skill, the strength of Mistress’ strokes. Masters have sent their subs along to be given a good traditional thrashing. Mistress Lady Penelope can also be accommodate wimps who enjoy mild corporal punishment. Maybe like their mother hand spanked them or used mother’s hairbrush. Mistress Lady Penelope will choose from her vast selection of implements to inflict the pain you crave. Many clients wish to retain male clothes. Some wish to crossdress and be treated like naughty girls. Others like to be restrained or gagged during corporal punishment. Some enjoy the anticipation of the pain to come. You can be left for a while restrained and/or gagged, dreading what is to come.


Mistress Lady Penelope ‘s General Information For All Categories


During your stay with Mistress Lady Penelope, if you feel overwhelmed, you are free to leave. This may be genuine. However if Mistress feels it is not, you will never be granted another appointment. You will never darken Mistress Lady Penelope’s property again.


Mistress has an extraordinary memory for people, especially voices on the telephone. This also applies to clients who book an appointment, but are too scared to turn up. Such time wasters are remembered. Their phone numbers are blocked. Even if they use another phone, Mistress will recognise their voice and block them again.

Mistress Lady Penelope routinely ignores calls with withheld telephone numbers. If you fail to arrive for your appointment with Mistress Lady Penelope, you will forfeit your deposit money. During your session, if you ask to leave you will forfeit your tribute. You must inform Mistress Lady Penelope at the earliest opportunity if you are unable to attend. If there is a reasonable reason why, you should explain it. Informing well in advance is to avoid wasting Mistress’ time and her Sissy Maid’s time. Preparing for your appointment, only to have all the preparation time wasted. Then wasting more time putting away everything prepared for your visit with Mistress Lady Penelope.

End Of Your Session With The Supreme Mistress Lady Penelope

At the end of the session you will remove make-up and the clothes you were wearing in your session with Mistress Lady Penelope. You will probably find removing high heeled shoes a massive relief, corset too. However, you will probably also feel regret in doing so, and wish you could continue to wear them. It can be a huge anti climax, you may look forward to booking another session with your Mistress.

If a chastity device was provided for you, the key will be given to you so you can return it. Then you will don the clothes you arrived in. If you have a deadline, such as a train you must be on, you must inform Mistress Lady Penelope beforehand. Her Sissy Mincing Maid can book you a taxi to the train station or you can arrange it yourself. When they arrive home, many men find an outlet for their pent up frustration. That is of course unless your own chastity device is still locked on.

Vital Statistics For Crossdressing With The Supreme Mistress Lady Penelope.


For all clients who wish to crossdress in any of the above ways, you will need to state your sizes before your appointment. You must inform Mistress Lady Penelope on the telephone or by email. The required sizes being of your waist, chest and shoe sizes. You must also say whether you are able to wear high heels, medium heels, kitten heels or can only manage flats. As someone once said “High heels are like the elevator of beauty. In a flat sole, you can feel beautiful, but a high heel changes your mood, how you move – like a wild, beautiful animal. The idea is always to follow your clothes and desires.”

The majority of Mistress Lady Penelope’s stock of clothes are worn with bras and breast forms. Mistress also caters for clients who wish to be innocent Sissy young girls who have not yet grown breasts. Their dresses are flat chested, often with frills where the breasts would be on a grown up dress.

Subcategories Of Services With Supreme Mistress Lady Penelope

Your fantasy might be to voluntarily crossdress or simply be ordered to do so. You may require forced feminisation, where you are compelled in some way you preselect. Maybe petticoat punishment or petticoat discipline. In those a naughty boy is forced to dress as a girl. The humiliation makes him more civilised. Indeed many crossdressers adore humiliation. Some do not even realise how much they enjoy humiliation until they experience deep humiliation for themselves.

Sissy discipline is much the same as petticoat punishment and petticoat discipline, but without any pretence of being juvenile. Mincing Sissy training is often voluntary, of course involves ultra Sissy clothing. Clothes which a modern woman would not be seen dead in.

‘Ordinary’ crossdressing on the other hand involves dresses which a modern woman would wear. Maybe to a wedding or party or a less formal skirt and top. Sometimes the stylish dresses from the 1950s or other decades. The exact choice of clothes will be decided by Mistress Lady Penelope but you are welcome to state your preferences before your appointment. To please her you will put on whatever Mistress has chosen for you. You have submitted, you have no choice but to obey her.


Some clients like to combine their chosen service with bondage maybe being a damsel in distress in some way.

Feminine Mannerisms.

Teaching feminine mannerisms is part of your training. Some things come naturally, a client wearing precariously high heels will find it impossible to walk with manly steps. For those who cannot wear such high heels, they might be trained to take Mincing steps under threat of punishment. Alternatively a set of fetters or a hobble skirt will force a shorter stride.

You will be taught to keep your elbows back and in to your waist. Keeping your palms facing forward can help with this. Other mannerisms can be taught as in a finishing school. Some are part of training to be a humble, respectful and submissive Mincing Sissy Maid, curtseying for instance. Smoothing a satin skirt before sitting avoids creasing. Making sure a long skirt is clear of your feet when standing up avoids both stumbling and ripping your skirt. Other such mannerism can also be taught.

The most difficult female mannerism to remember is keeping your knees and ankles together. No male wants to hurt his private parts and naturally stands and sits with legs akimbo. This is extremely unladylike. You should remind yourself all the time you are en-femme. If you forget Mistress Lady Penelope will award punishment points.

Steps

If wearing a floor length dress, you will be trained to hitch up your skirt when climbing a step. In high heels you will be trained to lead with your toes when climbing a step. If you later forget you may miss the step with your heel and stumble or fall. Falling is punishment in itself. Punishment will only be needed if you step on your skirt and rip it. Similarly leading with the heel when descending steps will be taught. Failing to do so can also cause a fall if the sole of your shoe misses the step. Wearing a full petticoat does mean you cannot see your feet so mistakes are even more likely.

Returning to male mannerism.

Do not worry about continuing to do them after the session in your normal life. It is the female clothes and shoes etc which trigger this behaviour. In your male clothes you will almost certainly find the mannerism go away until you are back en-femme once more. In the 1960s I never saw a girl hitch up her mini skirt when climbing onto a bus, but I bet the same era girls in a long skirt would do so. They would know there is a danger of stepping on the hem of a long skirt. The danger being either tripping, or ripping the skirt.

Points Always Mean Punishment. You All Have Been Duly Warned Haven’t You?


If you fail Mistress Lady Penelope in any way, points will be awarded. At the end of the session, before you are released, any points earned will be converted into corporal punishment. Very occasionally, points may be deducted for exemplary behaviour during the session. If excessive points are earned they may be converted during the session itself. Maybe into time spent standing at attention in the corner of the room facing a blank wall. Perhaps extra bondage to enforce correct behaviour.

Makeovers In The Dressing Room


Nearly all clients (other that corporal punishment ones) will be given a makeover by Mistress Lady Penelope. You can be taught what makeup to use and how to apply it, if you ask and time permits. The makeover and dressing can sometimes take up to two hours. The minimum appointment with Mistress with makeover is three hours. This leaves an hour or less for training, photo-shoots, admiring yourself in the mirror, changes of clothes etc. As the preparation time is a fixed overhead, it makes sense to book a 4 hour appointment or more.

Photography


You may bring a still camera or a compact movie camera for Mistress Lady Penelope to do a photo shoot. Mistress can use her own equipment. Some like to bring their own as they feel their privacy is guaranteed, though this is not really necessary. Mistress never ever uses client pictures or movies without that client’s permission. Be assured, what happens in Mistress Lady Penelope’s house stays in Mistress’ house. Some clients do request to have their photos placed on Mistress’ web site. If they are realistic, they go on to  Mistress Lady Penelope’s website. Good photography takes time. You will need to book a longer session for anything more than a couple of quick stills.

Chastity Devices And Key-holding

You may well want to wear a chastity device or Mistress Lady Penelope may insist on one anyway. This specially for Mincing Sissy Maids. If you wish to extend your submission outside the session itself you can buy your own one. You might put it on at home and hand the key over on arrival. The key will be placed onto a silver tray. Mistress’ Maid will check your device is securely locked as she dresses you. At the end of the session your key will normally be returned to you.

Mistress Lady Penelope can hold your key outside of your session by prior arrangement. This can be between sessions for instance or prior to a session (posting it to Mistress). You submit days or weeks before, making you very eager to be a good girl. If you fail , it will result in Mistress Lady Penelope retaining the key. You will remain frustrated until Mistress can provide you with another session in her busy schedule. Then you will have to try to do better to earn the key back. If you succeed, the key will be handed to you as you leave Mistress Lady Penelope’s house. You will probably not be able to unlock yourself until you arrive home.

Unavailable Services

Mistress Lady Penelope no longer offers the Victorian cross dressing service nor the bridal dressing service. This has allowed Mistress to specialise in the services which Mistress Lady Penelope enjoys the most, Mincing Sissy Maid training, Prissy Sissy training for sissies, cross dressing service, forced feminisation, transformation, corsetry, tight laced corset training, traditional corporal punishment and correction for wayward boys.

Despite many requests, Mistress Lady Penelope does not train wives or others how to be dominant. If you have not been born dominant that is it. Mistress cannot teach it and suspects nobody else can do so either.

Mistress does not teach others how to manage a Sissy Maid. This might become a topic for a forthcoming blog. However it will be from the perspective of a Maid, her experiences of how Mistress Lady Penelope controls her, if it happens at all.

For New Clients

For first time clients, Mistress Lady Penelope will interview you on the telephone, before your total submission. During the interview  you can request limits, express your preferences as to what is to happen in your session with Mistress. Alternatively you may email Mistress Lady Penelope prior to your appointment.

Making Appointment With The Supreme Mistress Lady Penelope


Mistress Lady Penelope does not do appointments on a daily basis. Mistress has her own personal business to run. Weekend appointments may be available providing you give Mistress Lady Penelope advanced notice. Weekend appointments will incur a supplementary charge.

Mistress Lady Penelope is unavailable on Mondays, Mistress has business meetings throughout the day. If you do require an appointment it will be from Tuesdays to Fridays, by advance notice from you, you would need to give Mistress Lady Penelope a telephone call, text message, WhatsApp or send an email to Mistress Lady Penelope’s 24/7Live-in Maid Sissy Barbie. Appointment commence between the hours of 10am to 4pm, the longest appointment is six hours, except by very special exception if you can convince Mistress Lady Penelope to extend your appointment for an extra hour or two.


Mistress Lady Penelope has been fascinated and intrigued with this scene but has limited spare time to see you. If you require an appointment you need to book well in advance, on Mistress Lady Penelope’s mobile phone 07970183024. Once you have made contact with Mistress, please have a definite date and time in mind. Then Mistress Lady Penelope can check her personal diary, to see if Mistress is able to fit you in. If you need an appointment urgently, particularly for corporal punishment, do call first thing in the morning. There is a slim chance Mistress Lady Penelope may have a gap in her schedule.


If you feel awkward by speaking to Mistress Lady Penelope on the telephone, you can alternatively email Mistress’ 24/7 Live-in Maid Sissy Barbie:  mistressladypenelope666 @gmail.com

All appointments are at Mistress Lady Penelope’s private exclusive abode in a country lane which is situated within a 3 minute drive of M2 Junction 4. There is sufficient parking within a very short walk. Alternatively the nearest railway station is 4 miles away in Rainham (Kent) from which you can get a taxi.

Disclosures When Making An Appointment With The Supreme Mistress Lady Penelope


Clients should disclose any medical condition or poor health to Mistress Lady Penelope when they make their appointment. Likewise any medication needed to be taken to treat it. If due to of a client’s failure to divulge this information, consequences arise, Mistress will not responsible.

Any client who books an appointment with Mistress Lady Penelope attends on their own volition.

If a session is to span over a meal time, you must inform Mistress Lady Penelope beforehand of any special dietary requirements. It might be possible for you to bring a small meal with you. However, it must be consumed quickly, and only after Mistress has eaten. For a Maid, this will be a meal you have prepared and served to Mistress Lady Penelope.

Reservation Deposit For Your Appointment With The Supreme Mistress Lady Penelope

Mistress Lady Penelope is requesting a £100 deposit from her clients. Mistress has to take a day off from her own personal business, to attend her appointment with you. The deposit is non refundable if you cancel your appointment or fail to turn up. Your appointment has been booked in advance, denying other clients the chance to book. As previously stated, Mistress doesn’t offer daily appointments to her clients. It is impossible for Mistress Lady Penelope to reallocate your cancelled appointment to someone else. This is due to the fact Mistress has to make appointments way in advance.

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Mistress Lady Penelope is located in
Medway in Kent
off the M2 Exit 4, or the M20 Exit 6.

By rail to Rainham, 55m from Victoria or Paddington

Appointments Tuesday,
Wednesday, Thursday or
Friday 10am to 4pm.

Free parking available nearby.

This is strictly by appointment
only, please telephone
Mistress Lady Penelope on:
07970183024 but do not
withhold your number.

Email: mistressladypenelope666 @gmail.com
or use the form on the contact us page but
please type your email address carefully
otherwise I will be unable to reply to you.
The ‘Contact Us’ page can be
accessed via the page menu at
the top of this page.

For clients who are overseas or unable to travel to attend in person,
Mistress Lady Penelope has decided to provide telephone or Skype video training.

There are clients who adore total and utter humiliation to
whom Mistress Lady Penelope can offer the same service.

Mistress can also offer novice crossdressers
advice on how to measure and where to purchase clothing etc.

If any client is interested, you can send an email to
mistressladypenelope666 @gmail.com to discuss
your requirements, your tribute and when you are
available to book a session with Mistress Lady Penelope.

I would like to point out that Mistress Lady
Penelope does not work daily on her hobby as
Mistress has a business to run and business meetings to attend to.