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The Best Way To Milk Your Chaste Sissy Maid
The Best Way To Milk Your Chaste Sissy Maid


Sissy Milking or Prostate Milking is the generic name for a number of different  techniques designed to ensure the removal of backed up Sissy Milk (sperm) from a sissy, in chastity, whilst at the same time ensuring that there is no possibility of the sissy deriving any sexual pleasure from the experience. The primary functions of Sissy Milking can therefore be summarized as follows:

To maintain prostate health;

To ensure that the sissy does not unintentional receive pleasure by way of night time wet dreams or spontaneous emissions caused by the aforementioned backlog;

To help to reinforce in the sissy’s mind that they are no longer a sexual being but are rather nothing more than a living tool designed to ensure the continued comfort, pleasure and well being of their Mistress.

An Introduction to Prostate Milking
A doctor explains what is involved in prostate message
The do’s and rthe don’t and tips on how beginners should
Should proceed if they haven’t milked a prostrate before

What follows is an examination of the various ways in which Sissy Milking can be performed, an assessment of the various pros and cons of each technique and a number of audio visual demonstrations of Sissy Milking taking place.

In addition there will be a number of scenarios described that may be implemented to ensure that, not only, is the sissy deprived of any sexual satisfaction during the milking process but also suffers maximum humiliation at the same time. Humiliation, discipline and chastity being the key components in creating a useful functioning sissy dedicated only to the furtherance of its mistress’s needs and desires.

It is sincerely hoped that this report will prove most especially helpful to

The Most Beautiful, Powerful and Dominant Female Master

Aiding in ensuring that her most pathetic sissy: Chastity Sissy Connie Pickle
ALWAYS experiences the most sensationless, sexless and humiliating Sissy Milkings that it is possible for any sissy to experience and that this, combined with various other techniques, will thereby bring fully home to the said empty headed sissy that her enslavement, servitude, chastity and total devotion to her Mistress's needs are all that the future holds in store for her.

This report will proceed to an examination and discussion of the specific ways in which a Sissy Milking may be performed addressing first the very important topic of:

Relaxing the Sissy Vagina

A Sissy Milking occurs when an appropriate object (usually a dildo or custom designed prostate massager) is inserted into the sissy’s vagina (anus) and moved until it is in contact with the sissy’s prostate gland. The object is then used to stimulate this gland causing it to start to spasm and eject the unwanted Sissy Milk without the need for any form of penile stimulation. The object of the exercise is simply to flush out the unwanted Sissy Milk without the sissy experiencing any form of sexual satisfaction. It is therefore essential, before any other activity may take place, that the object can be easily inserted into the sissy vagina and directed to the appropriate place without damaging the sissy or requiring any unnecessary effort on the part of sissy’s Mistress or anyone one else she might designate to perform this necessary chore.

For example it might be made considerable more embarrassing if sissy’s Mistress were able, perhaps, to procure the services of a mature overweight unattractive lady to carry out this task. Then, instead of gaining even the smallest amount of pleasure from seeing her beloved Mistress milking her little sissy clit all sissy would see would be this awful, disinterested, overweight unattractive woman mechanically lubing up the milking dildo prior to inserting it and then coldly and unemotionally milking away the unwanted Sissy Milk. Perhaps she might even be the one who fed it to her on completion.  

Knowing now just how important it is to have a nice relaxed easily accessible sissy vagina, in order to ensure that milking is carried out as quickly and as easily as possible; allowing sissy more rapidly to return to being At Service, what are the best methods for achieving this very desirable outcome? The methods range for the most simple to the quite complex. Let's start off with the simple and work our way down the list:

  1. Taking a hot shower or bath before a prostate massage will help you relax plus make sure that the environment you're in is warm and comfortable;
  1. Because the anus includes a great number of nerve endings, it can be the cause of pain when mistreated. When penetration happens, the anal muscle tissue enters into spasm, as though being afraid of an attack and so a vibrator may serve as a tremendous help to relax the rectal muscle. When the vibrator is slimmer as compared to the penis, that is also much better, since the anus starts to adjust little by little to the new guest;
  1. Perhaps the single biggest factor is to trust that your Mistress doesn’t intend to hurt you (this is about your chastity and not a punishment intended to cause sissy pain) just simply wants to milk away ALL your unwanted Sissy Milk. Mistress expects you to learn to relax but will initially accept that things have to go slowly so that you can adjust to the fact that YOUR SISSY VAGINA HAS REPLACED YOUR SISSY CLIT AS YOUR PRIMARY SEXUAL ORGAN!
  2. Rimming - where a partner licks and sucks around your anus - is another great relaxation technique. Obviously a Mistress would never sully herself by performing such a task on her sissy but if there’s another sissy present this may be a viable option. This also has the additional pleasant side effect of adding to the embrasement of the hetrosexual sissy when they realise that they are getting their sissy vagina relaxed, for their milking, via the tongue of another former man!

Milking The Sissy

With the sissy vagina relaxed and able to accept the insertion of the milking dildo we need to consider the various positions in which the sissy may be placed in order for the sissy milking to be carried out. Again in order to ensure that the sissy remains relaxed this entails ensuring that they are comfortable. Yes there are times when a sissy must be subjected to pain in order to better learn to be an obedient sissy but this has no place in the sissy milking routine. Sissy milking is about the Mistress ensuring that the sissy remains chaste, unrelieved, humiliated and desexualised. Pain would simply distract the sissy from realising that all his sissy milk has humiliatingly been removed by the Mistress without sissy experiencing the slightest sexual relief. It should be crystal clear in the sissy’s tiny airheaded brain that should Mistress so choose she could ensure that sissy was always milked in future and so would NEVER again experience any sexual release of any kind EVER! Unless Mistress chooses to reward sissy for absolute obedience and perfect service at some point in the future then sissy would effectively become a Eunuch. Knowing this will motivate sissy to strive ever harder to become perfectly obedient and absolutely and utterly devoted to Mistress. To in fact become THE PERFECT SISSY.

With regard to positioning there are really only two viable options available. In summary these are either face to face milking or facing away milking. Let's examine each in turn and explore what variations each provides always bearing in mind that our objectives must always remain that sissy milking should be easy, convenient and enjoyable for Mistress and totally draining, frustrating and humiliating for her sissy.

Face to Face


Whilst under normal circumstances a sissy’s comfort or discomfort would be a matter of complete indifference to Mistress when it comes to milking a sissy of ALL it’s unwanted and useless Sissy Milk comfort is important. An uncomfortable sissy will not be able to retain a relaxed sissy vagina and this will make the milking more difficult and irksome for Mistress.  So if Mistress chooses the face to face position some thought must be given to the actual positioning of your pathetic little airheaded cum slut if the best results are to be obtained. Sissy’s only have tiny sissy brains which are obsessed with dominance, service, obeying Mistress, makeup, high heels and pretty clothes. They are not equipped with the kind of brains that are able to deal with a lot of stress. After all if they were they’d be real men and not need the firm guidance of their dominant Mistress in order to put any purpose in their silly pathetic littles lives.  So sissy must be comfortable, not out of kindness, but simply as a matter of practical necessity.

Sissy should be in a seated position. Sissy’s back should be supported by a large and firm pillow, and sissy’s back should be reclined. Once in position sissy should pull her knees towards her chest and angle somewhat outwards. In this position Mistress has easy access to sissy’s sissy vagina and should have little or no problem inserting her milking dildo.

Mistress’s position should be comfortable for sissy and also enable Mistress to have unfettered access to and an unobstructed view of sissy’s sissy clit and sissy vagina. Mistress may choose to kneel or sit cross-legged in front of sissy as either one of these positions should give her easy access to the pathetic cum slut’s clit and vagina.

If this is the first time sissy has been milked or if she is still relatively new to the procedure then as a method of continuing sissy’s relaxation Mistress may massage sissy’s lower extremities. Sissy may decide to close her eye to relax but this is NEVER allowed under any circumstances.

Eye Contact

From the moment Mistress begins until the very last drop of Sissy Milk has been drained from her sissy clit sissy must retain eye contact with Mistress. Sissy must look into Mistress’s eyes for every single second and understand that Mistress is draining her, keeping her chastity intact and is totally in control of her former sexuality .As the milking goes into its progressive stages, it is vital that both Mistress and sissy maintain eye contact.

Penile Stimulation Yes or No?

Once the sissy is relaxed Mistress should slip on a latex glove and then lubricate sissy’s sissy vagina. The process of lubricating the sissy vagina should be symbolic and not rushed establishing a pattern for future Sissy Milkings. The more that there’s a set routine the more quickly and easily the sissy’s sissy vagina will relax with each and every instance of milking Mistress should take her time at first until this pattern is established and sissy’s sissy vagina will start to relax reflexively. Mistress should begin by applying a generous amount of water based lubricant to the sissy’s pussy and then with some circular motions she strokes the opening of sissy’s sissy vagina. The idea here is to relax and pleasure the nervous opening. Mistress should, of course, be wearing a pair of latex gloves and after a little time has passed and the sissy’s opening has relaxed she should gently insert first one and then a second finger into the nervous sissy’s trembling opening! Mistress should never use her finger to poke sissy’s pussy rather she should gently apply some pressure using her finger tips. All through this process Mistress should continuously add lubrication as you can never have too much lubrication. Sissy vagina’s unlike superior female vaginas are incapable of self lubrication and Mistress should supply what nature cannot. Mistress gently inserts her finger(s) when Sissy’s pussy is ready. With some patience and time things will begin to move a lot faster as sissy is programme into how to relax and prepare for her regular milking.

When Mistress feels that the sissy is ready to be milked she will slowly and gently insert the milking dildo locate the sissy love button (prostate) and proceed to milk her sissy of all it’s pent up Sissy Milk.

At this point Mistress must decide whether or not sisy’s milking will or will not include any penile stimulation.  There are three options open to Mistress

Sissy is Milked in chastity
Sissy is Milked with her chastity removed but with her sissy clit remaining untouched
Sissy is Milked with her chastity removed and her sissy clit receives some form of stimulation.

Each of the above methods has their various pros and cons.

For all intents and purposes options one and two give virtually identical results. The sissy clit remains untouched whether freed or locked and the milking is utterly devoid of any sexual stimulation for sissy. Sissy is effectively rendered sexless when this procedure is employed but on the downside this lack of clitty stimulation will lengthen the time the milking operation takes to perform.

If Mistress chooses to stimulate the sissy clit during the milking process this can make matters quicker but comes at a price. Although sissy will not orgasm if this is done correctly sissy will experience sexual pleasure due to the touching of her clitty … much as in the way she might when Mistress ties her spread eagled to her bed and drives her insane with a prolonged tease and denial session. The end result will be pure frustration but the sissy will invariably experience some pleasure during the procedure. Of course the greatest risk of all is that if Mistress misjudges the amount of stimulation then there is a chance of accidently permitting the sissy to orgasm. With practice this should become less likely but it will always remain a risk where clitty stimulation is practiced.

So to stimulate or not is a decision that is entirely in the hands (or not as the case may be) of Mistress because as all sissies know

Facing Away

The “facing away” position requires sissy to be kneeling with knees apart, the buttocks elevated and the elbows resting on a surface. Sissy should be in a comfortable and stable position.
Mistress should kneel or sit spread legged behind the sissy. That way she has a perfect view of and easy access to the anus. This position also allows Mistress to reach in between the legs of sissy thus allowing sissy clit stimulation if this is permitted. The options here are exactly the same as those stated above (caged, uncaged/untouched uncaged/touched) as are the pros and cons.
Similarly, Mistress would now follow the procedure given in “face to face” technique and she will be equally successful when milking the sissy of it’s unwanted and pathetic Sissy Milk.

Best techniques for self-milking in front of an audience (a sissy performs for her Female Master’s Lady Friends)

Normally a sissy in chastity would never be allowed to self milk themselves anymore than they are allowed to milk their caged sissy clitty. However the key difference here is the addition of “in front of an audience”. This can be an exquisitely humiliating procedure for the sissy to undergo that further reinforces Mistress’s authority and which forces them to put their pathetic sissification and chastity status on display for the world at large (or at least for the invited audience of Mistress’s female friends).

Imagine sissy locked in her room dreading the sound of the footsteps on the stairs that announce that the time has come for her pathetic sissified status to be humiliating put on display in front of a group of total strangers. A group of powerful assertive women who will regard her with nothing but contempt and who will take great pleasure in witnessing and indeed furthering her humiliation and final slide into the permanent sissification that she will never ever ever be able to escape from. Once her humiliation has been witnessed by others then there’s no going back for a sissy. THEIR FATE IS SEALED FOREVER!

This afternoon Mistress took sissy to her room sat her at her vanity table and for the first time revealed the terrible awful truth.

“Sissy” she said “tonight I’m entertaining some friends and I thought I better perhaps finally let you know (so you’ll have time to think about Mistress though evilly) that not only is tonight to be that first public outing that you’ve been so so dreading but in addition to your very first public exposure but you’ll also be providing the entertainment tonight at my little gathering” “A star is born sissy a star is born”
“Perhaps somewhere inside your silly tiny sissy brain you’ve been wondering why I’ve been teaching you the technique of, and making you practice, prostate self stimulation?”
“Well wonder no more my pathetic little airheaded frilly little girly toy” she laughed “in just a few hours time, in front of 12 beautiful and powerful women you, my little fluffy Bunnykins, are going to be on your hands and knees on the coffee table showing the lovely ladies how cleverly you can milk you own tiny locked up never to be touched ever ever again little baby sized sissy clit”. “ Won’t that be ever so much fun my little feminised bimbo fuck toy?” “Well it certainly will be so much fun for me but for you my fluffy one perhaps not so much but don't worry this will be your first such performance but it most certainly not your last” “Just think my sweet sissy in certain circles you’ll be a star of stage screen and coffee table!” “Now my lovely blonde haired little beauty I’m a very fair Mistress so I thought I’d explain exactly what’s going to happen and , because it’s going to be a long and exhausting evening for you I thought I’d give the afternoon off from you cleaning schedule, which by the way you’ll make up tomorrow, so you could have a few quiet hours alone in your lovely girlie room to have a nice rest” Wearing a smile almost as wide as that of the legendary cheshire cat, Mistress left the room locking the door behind her whilst inside a very scared sissy began to think about what was in store for her this coming evening. Time flew by and dragged at the same time. Sissy couldn’t sleep, as Mistress well knew, she paced back and forth trying to think of a way out …. But there was none! Soon so so soon she’d be on her hands and knees on the coffee table dressed in her frilliest sissy Sunday best demonstrating to a group of laughing strangers how she could now do a sissy wank and milk her own prostate.
She heard the first footfall on the stair and her heart sank. What could she do what could she do? She could refuse to leave her room maybe  Mistress was bigger than her but if she really fought she’d never be able to drag her out of the room. Yes sissy though I can’t face this I’ll fight.
The key turned in the lock and the door swung open. Standing framed in the doorway way dressed all in polished skintight black latex rubber was her Mistress … and besides her two of the biggest women sissy had ever seen in her life!!! “Look Pumkin” said Mistress “ I’ve brought you an escort to accompany you to your very first and so so special cumming out party” “How kind am I sissy… nothing but the best for my little girly boy” Something finally broke inside sissy some last residue of manhood left her body and departed for places unknown. She finally accepted her fate knowing there was nothing whatsoever she could do to escape it. Mistress went to the wardrobe unlocked the door and removed a costume sissy had never seen before. “But before we go down stairs and meet my guests sissy” said Mistress with a cruel smile “we must first get you dressed in this lovely new cumming out ball gown I’ve got you”. Ten minutes later Sissy walked toward the two escorts that her mistress had provided and began the long journey toward the lounge and her final awful humiliation!!!

Sissy entered the room and heads swivelled to gaze upon the strange  creature that had just entered the room. “Ladies let me present sissy who tonight, for you entertainment, will demonstrate to us all how a once former man can be turned into a self milking pantywaisted sissy” “Ladies it gives me the greatest of pleasure to present to you all:

Sissy Connie Pickles the Amazing Self Milking Sissy””

[Image: WFwET1Z8D15BfHcGw4j6X1JYNTeORKiMg8YU1cKo...GrUH-8YqDa]
After everyone had come over and teased and mocked sissy and pulled up her skirt pulled down her bloomers and examined the tight little chastity belt that was inescapably locked around her “balls and held her tiny baby sized penis in it’s permanent prison. Finally she was stripped of her bloomers placed on the coffee table on all fours, her ankles were fitted with a spreader bar that kept her legs spread wide and finally Mistress passed her the special milking dildo she was to use to bring about her own ultimate humiliation! Mistress looked over made and held eye contact for a few moments, noted and enjoyed the sight of the single tear rolling down sissy’s cheek nodded and finally, in a loud and clear voice commanded

“Ready Sissy, Steady Sissy,  Milk Sissy Milk!”

Once the spreader bar had been put in place Mistress had squirted a generous amount of lube into sissy’s pussy and so as sissy reached back ward, awkwardly balancing one one hand she slippe, with practiced ease, the milking dildo into her sissy vagina located her prostate and began slowly to move the dildo backward and forwards. Mistress had instructed her to go very slowly, after all she was the entertainment, and so needed to put on a good show. Ten minutes later she began to feel as if she needed to pee and she realised that the process had started; that her Sissy Milk was on its way and was soon to fill the plastic container that Mistress had placed beneath her exposed chastity. As Mistress had instructed her she called out in her best high pitched sissy voice “Ladies ladies come look come see Sissy’s Sissy Milk is about to appear please come share this wonderful time with me ladies please please please come see my Sissy Milk.” As her Sissy Milk began to fill the waiting container sissy found herself surrounded by 12 grinning ladies each of whom tried to out do the other by making the most cutting and humiliating comments they could devise.
“Oh My God I never knew they could be that small”
“Oh she’s too tiny to satisfy a Barbie Doll”
“My clit’s bigger than that”
Sissy kept massaging and her Sissy Milk keep erupting as she felt herself being to swoon from the overload of humiliation being sent her way.
Five minutes later Sissy stood before the assembled superior ladies and raised the glass, that Mistress had just passed to her, to her lips.“
Dearest ladies I thank you from the bottom of my heart for attending my milking and I sincerely look forward to seeing you at many many more” and with that sissy raised her glass and toasted the superior ladies by drinking down every single drop of her thick, salty, warm and creamy Sissy Milk. Poor sissy never realised that Mistress had just seen a new video and she’d decided that it was time that sissy learned a new way to self milk that he was going to demonstrate her next party get together.
Self Milking Sissy's New Technique
I’ve included this video to show how easy it can be not only to make
Your sissy ejaculate only through milking in the future but how with
With a little initial effort Mistress should never ever need to waste her
valuable time and effort doing so. Sissy Self Milking it’s The Future

The end.


Do not insert any fingers into the sissy’s sissy vagina without wearing well lubricated latex gloves as sharp nails can cause cuts and not only are these very painful but there’s also the possibility of cross infection should one or other party be carrying an infection that can be transmitted directly into the bloodstream!

If you’re milking sissy downstairs in the lounge during the day before commencing remember to close the curtains to avoid frightening any passing women, children and/or horses.

A sissy in chastity must always remember to wear a maxi-pad when uniformed and in service to avoid getting any disgusting Sissy Milk stains on her delightful feminine panties. Panties being an intimate item of feminine apparel may indeed be worn by sissy as a declaration of their desire to be as much of a faux girl as they possibly can be but they are still far to feminine an item to be profaned by being contaminated with the stains caused by sissy’s foul and loathsome milk. Similarly when not at service a sissy must at all times wear a panty pad to absorb their sad and pathetic drippings.

Remember that any sissy milk that is removed, by whatever means, from sissy must be consumed in its entirety by sissy. Failure to perform this act of submission would be a gross insult to sissy’s divine Mistress and as such would be an offence deserving of the most severe punishment.

Embarrasing Your Sissy

Everyday sissy must present her Sissy Clit for inspection by her Mistress who may well remark that there seems to be definite progress and that her tiny little thing is definitely getting more and more like a real clit everyday.

If sent shopping for clothes sissy should be require to ask shop assistants (usually female and therefore automatically her superiors) embarrassing questions such as:

Do you have this bra in my size?

What tampons would you recommend for a sissy that’s just starting on her periods?

“You're a lesbian?” “I do so wish that I was a real girl and not a pathetic panywaisted sissy in chastity because I think you're very pretty.”

Sissy should buy all her pads and panty liners twice a year and should take all these and no other items of shopping to a manned check out. When the checkout girl raises an eyebrow sissy should acknowledge the silent question and respond by saying “I know I just can’t believe just how quickly I get through them”.

At the chemist;
“ What kind of condoms can you recommend would be the strongest for use on my Mistress’s strapon?”
“I’d like a deodorant that is especially designed for getting rid of any lingering man smells I might still have; what would you suggest Miss?”
“I need to buy an new dummy please I’ve lost mine”

Two video links

Milking a sissy can require a lot of time and effort on Mistress’s part, time that she could more profitably spend elsewhere enhancing her life and enjoyment rather than waste it milking her sissy to ensure that their chastity remains unrelieved. Therefore it is essential that sissy should be taught to take care of this necessity herself. This could be done in one of two ways:

  1. A trusted Sissy could be taught how to fuck herself with a normal dildo and a properly trained well disciplined sissy so instructed would never betray their Mistress by failing to obey her command. In such cases the video below demonstrates a tried and tested technique that can be used by the trusted sissy to perform their own monthly (or whenever schedule they are on) milking and is included here for that reason. A Trusted Sissy Self Milks Video
  1. However not all sissies may be trusted or perhaps they have not yet been At Service for long enough to have earned Mistress’s trust. If Mistress wants to save her precious time she could entrust someone else with the responsibility of performing her sissy’s regular Sissy Milk draining regime or she could turn to technology and employ a mechanical milking device to take care of this time consuming task. If Mistress used a machine like the one shown here Sissy Milked By Huge Fucking Machine she could just leave sissy tied to the bed put the machine in place press the on switch and pop into town for a day's shopping knowing full well that by the time she returns there won’t be the slightest drop of sissy milk remaining inside sissy’s drained shrunken balls.

Miscellaneous Sissy Milking Related Videos

Hot Strapon femdom fucks

Male Milking Machine



Dearest Most Divine Goddess and All Powerful Female Master.

I would like to thank you for setting me Sissy Connie Pickle this first written sissy assignment and I hope that my meager efforts meet with your approval (although of course nothing I could ever do could ever come close to anything that you did.). I hope that what I have been able to find and record will in some small measure help to ensure that all my future milking meet the required standard and that they do not afford me any sexual pleasure but simple drain away my filthy unwanted Sissy Milk so that you may have the pleasurable experience of making me eat it in order to show just what a pathetic cum guzzling sissy whore I am.
If this report does, in any small way, meet with your approval then I can only hope that you will entrust me with the task of carrying out many similar  assignments in the future.
Mistress, may I say just once more, it has been an absolute privilege and joy to labour upon your behalf and to carry out this assignment for you. I, of course, fully acknowledge responsibility for any errors which are entirely mine and understand that as a result of any such errors I am fully deserving of any punishment that you might see fit to impose upon me.

I Am Mistress you’re devoted Chaste Sissy Maid

Chastity Sissy Connie Pickle
Connie Pickle, what an incredible essay/post!
Thank You :-)
very interesting report, very sobering and demeaning, is that supposed to be?
sissy caja
(07-02-2018, 06:31 PM)sissy caja Wrote: very interesting report, very sobering and demeaning, is that supposed to be?

Is that supposed to be? Supposed to be what? Don't understand? Sorry :-(
it's supposed to milk a sissy the way you described it. Sorry for my unclear expression
sissy caja
(07-02-2018, 09:17 PM)sissy caja Wrote: it's supposed to milk a sissy the way you described it. Sorry for my unclear expression

Thank you for clarifying that. Once again I've proved that we pathetic males have tiny brains and are fit only to be Sissies under the control of our far more intelligent Female Masters.

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