A sissy must always wear heels

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Sissy maid types

Here's the thing, sissy maids are about service. Yes, our kink involves dressing up really frilly and for me passable femme and stockings/tights are a must but after that part of the negotiation with our owners (masters or mistresses) it is out of your control. Your role is about service and pleasing others not about yourself and your needs and wants.

Trust me. I'd rather be played with and tied up all day every day but I have chores and things to do. If you don't do them properly your owner will hurt you. And they should hurt you badly enough that you don't want to repeat that behavior. That is the main difference between erotic punishment and being punished for doing something wrong.

So, that being said, lets discuss the roles of maids that you'd end up having to partake. There are a lot o different types of servants and you'll end up picking up a lot of these roles as you get trained. Unless your owner has the money to have multiple maids, which is unlikely to happen and that sucks, you'll have to do most if not all of these jobs. Even though it's a lot of work, especially in heels, is that you're making your owner happy and that should make your clitty hard in your cage. I hope it does. I'm having difficulty writing this while thinking about it.

This list comes from here. Notes: I've removed some of the more specific ones and cleaned up the text.

Types
Lady's maid
A senior servant who reports directly to the lady of the house, but still ranked beneath the Housekeeper, and accompanied her lady on travel.

Housemaid
A generic term for maids whose function was chiefly 'above stairs', and were therefore usually a little older, and better paid; where a household included multiple House Maids they were often sub-divided as below:

• Head house-maid: The senior house maid, reporting directly to the Housekeeper. (Also called "House parlor maid" in an establishment with only one or two upstairs maids).
• Parlor maid: The parlor maids cleaned and tidied reception rooms and living areas by morning, and often served refreshments at afternoon tea, and sometimes also dinner. They tidied studies and libraries, and answered bells calling for service.
• Chamber maid: The chamber maids cleaned and maintained the bedrooms, ensured fires were lit in fireplaces, and supplied hot water.
• Laundry maid: The laundry maids maintained the bedding and towels, and also washed, dried, and ironed clothes for the whole household, including the servants.
• Under house parlor maid: The general deputy to the house parlor maid in a small establishment which had only two upstairs maids.

Nursery maid
Reports to the Nanny rather than the Housekeeper. Works in the children's nursery, maintaining fires, cleanliness, and good order.

Kitchen & Head kitchen maid
A maid who reports to the Cook and assists in the running of the kitchen(s). Where multiple kitchen maids are employed the Head kitchen maid is effectively a deputy to the Cook, engaged largely in the plainer and simpler cooking. Sometimes cooking the servants' meals.

• Under kitchen maid: Where multiple kitchen maids were employed these were the staff who prepared vegetables, peeled potatoes, and assisted in presentation of finished cooking for serving.
• Scullery maid: The lowest grade of 'below stairs' maid, reporting to the Cook, the Scullery Maids were responsible for washing up cutlery, crockery, and glassware, and scrubbing kitchen floors, as well as monitoring ovens whilst Kitchen Maids ate their own supper.
• Between maid: Roughly equivalent in status to scullery maids, and often paid less, the Between Maids in a large household waited on the senior servants (Butler, Housekeeper, Cook) and were therefore answerable to all three department heads, often leading to friction in their employment.

Still room maid
Junior maid employed in the still room; as the work involved the supply of alcohol, cosmetics, medicines, and cooking ingredients across all departments of the house, the still room maids were part of the 'between staff', jointly answerable to all three department heads, Butler, Housekeeper, and Cook.

Conclusion
In more more modern and realistic households a single Maid-of-all-work, you, will handle all of this work. Your owner has other things to do (work, fuck someone else, torture or humiliate you to release their tension, to go to a party et al) and they wont have time to do some or any of this work. That is the whole point in owning a sissy maid slave.

Your pleasure is always going to be put last but never never. You have work to do so get to it.

Do well and you'll make your owner so happy that they'll give you so much of what you want.

*curtsey*

A milking as either a demonstration or in private

This is purely from my own wild imagination. Excuse me if this is not as grammatically correct, keeping proper tense or as coherent as I'd normally like [or anything else]. Also, I will be moving rather quickly through this and it won't be as thorough as I'd like but I wanted to get a gist down before I forgot it. I would also like to apologize for not writing as often as I or anyone else would like. Life and that. Something is better than nothing? I guess? Anyway, forward and onward.

We all know that a sissy is to be in chastity. Whatever it takes to get her into permanent chastity. We all know that milking is simply to keep the plumbing from getting backed up. We also know that a sissy should always eat her cum. Those are a given. Another given is how much we obsess over looking great, doing the housework and taking a fat cock in the ass. Ahem, please excuse my language.

Well, here is a position, that I thought of this evening and didn't want to forget, how your mistress can milk her sissy.

Sissy should be dressed up in all her regalia. That is part of the kink so we can't forget it. Lets say that it would be.

The sissy all dressed up

• Wig (if needed)
• Makeup
• Satin gloves
• Corset (for posture and curves)
• Maid's dress
• Very puffy petticoat
• Fully fashioned stockings
• Garter
• Lockable heels (A sissy should forever be in heels)

A side note, I should make a garment blog or something so that I can point to it instead of always writing it here. 

Now, we will want to sit our sissy on a chair in reverse. Think AC Slater sitting in a chair.

Yeah, this is it.

Except we'll be tying our sissy up and she won't look like brute like this guy. Sheesh!

She's all tied up

Actually, it's best if I give an example:

Oh my, I'm getting flustered. 

Tie her just like that. You may want to put her arms in a binder for speed's sake and I love that. I love your ideas. Her legs are two columns that should be tied. Her ankles can be tied to the chair's legs or to a spreader bar. Just make it so that she can't wiggle or rock about because she will want to.

Next, put a harness on her. One with an open gag. A panel is okay but it defeats some of the purpose of this unless, of course, you make her wait till the end and have a full volume. I think I know you know where I'm going with this.

Yes, this one, perfect.

Take some rope and tie the top of the head to the spreader bar so that her head is forced back. Not too much because this milking demonstration is going to take awhile. 2 hours if we're all lucky kinksters.

From here her little clitty should be out. Now, you can do this in front of people or in private. In private you get to go about your business and leaving the sissy immobile in between milkings. She gets all the humiliation and depravity that comes with being a made except the excitement of being humiliated in front of friends. Kink friends not just some people you know. You don't want to completely ruin careers.

If you do it in front of some kink friends, and I recommend this because of all the excitement that goes along with public humiliation, you'll have to "put on a show". Or, at the very least, but most likely, you'll have to be a host. It is a party after all.

Here's what happens

Vibrate her little clitty while it's still in the cage

Like the title says. Make sure to collect everything. Explain why you're doing it. You want her to cum but not to be released from her chastity. This allows you to have dominion over here even more so than chastity because she's in complete bondage. You OWN her. You BULLY her. Her orgasm is yours and yours alone as she is YOUR PROPERTY. Saying this aloud to others will enforce it. Her belly will drop a little and she will feel abused and used. This is intentional and what you want. It is a demonstration after all. 

The fact that she came while inside her cage reinforces the fact that she is not even allowed a pleasurable orgasm outside of her cage. She also knows the consequences. She has to drink her sissy juice. 

If you want her to have it now then make her either hold it in her mouth before she swallows or to roll it with her tongue first. If not collect it for later.

Ruin an orgasm or 10

No matter what we say we LOVE ruined orgasms. You're touching our penis. You're playing with it. You're putting it in your mouth and your about to make us cum ... but then you don't. I won't lie that part is not actually fun. It's rather painful and can sometimes make us feel bad. I don't get it either but at least it isn't every time.

Do the same as before. Oh, don't forget the post orgasm torture. Keep rubbing her little clitty while she's in that bondage and can't possibly try to stop you. Slap her in the face when she gets too rowdy.

Cock & Ball Torture

As always be careful because lasting damage can occur but I will assume that you've done this before. You can flick the balls, smash the clitty or whatever you would like.

She should suck a cock

Optional but wow this would be great. Lets assume that you have male kinksters that you're friends with and they wouldn't mind this and your sissy has either trained for this or has done it before. Either way, take off that gag and let him jam his cock down her throat. Make sure she has something to stand on and that she won't fall over too easily.

If you three, or anyone in the group, is into the cuckold scene now is the time to make a scene of it. She'll be here watching all of you have a grand ole time while she's there with a throbbing clitty. Put a lubeless condom on her. We don't want anything to get away.

In closing

Oh, yeah, I almost forget, put a plug in her or something that will oscillate in and out of her ass. If it's another sissy or one of your bulls then make sure she gets her ass fucked.

Lets never forget. A sissy's role is to assist her mistress or master in whatever they want. Cleaning the house of their cocks swathed in cum. If those jobs are done then she's there for their amusement and her humiliation. She doesn't have a say.

*curtsey*

Having a sissy in chastity is a lot like having a rechargeable battery.

Orgasms for your sissy? No Mas.

Sounds funny I'm sure but there is rhyme to my reason.

Chastity, like many other things, isn't a magical pill that will fix all your problems. Diet pills while they will work to remove pounds if you aren't careful you'll gain it all back. You'll need to do maintenance after the fact to keep the weight off and it is something that most people do not do. That ab blaster is not going to give you abs w/o the proper diet to rid the fat from your belly.

The basis for orgasm control/denial is founded, in part, on the idea that while the male is interested in pursuing sexual release he will be more solicitous of the lady’s pleasure, and in general more amenable to various services for her. For some, an additional motive is that more time between his releases will make them more powerful and pleasurable. However, the truth is that these effects are a complex mix of psychological and physiological effects, created by repeated “teasings” or other arousal which engage his desires and build at an emotional level.

So chastity isn't, on it's own, going to make the sissy (I always talk sissy on this site but this can also relate to your male submissive/slave), become more submissive or sexually frustrated. There is work on both ends that needs to be done in order to achieve this goal.

If you do not make sure that your sissy is sexually frustrated then it will not have the affect that you nor your sissy are hoping for. It'll just be another thing that is in your lives. It's an attachment on her body.

This is where the seed of the rechargeable batteries analogy flowers.

Pray tell how?

I said that in order to keep the game moving forward you must make sure that they are sexually frustrated but you may ask "How in Sam heck am I to do that?" It is very simple actually. There are three things that you'd want to do and I'll enumerate them here.

1. Teasing and Denial
2. Ruined Orgasms, CBT, Post Orgasm Torture
3. Prostate Milking

Essentially do you not want your sissy to have a pleasant orgasm. If you can just do ever let them have one again so long as there are no medical issues, of course. If you can keep her from having a satisfying orgasm you'll keep your sissy at the height of her erotic energy and she will not be able to resist your charms. Or whims or beatings or humiliations or cuckolding.

Tease & Denial

This is where you want to start. T&D is the easiest thing you can do and can be so powerful that the other two aspects of this game can be done sparingly. The T&D will make your little sissy/slave want to explode. There isn't much that you need to do and it's different for each sissy. Whatever the trigger is for your sissy is what you'll want to focus on.

For instance, me, it's about dressing and cuckolding. If my mistress talks about how exciting or fun it is for her to see me in sissy garb with a nice pair of stockings/pantyhose that is enough for my clitty to want to break out of it's metal cage. If she touches me or teases oral sex it will hurt but it's enough to make my little dicklet's balls begin to fill. Serving, bondage, humiliation et al are all things that excite me and I'm sure some or most if not all of these things and more will do it for your sissy. 

Perhaps if she's like me then she'll love to underdress. When you go out for a dinner together have her wear her corset and stockings and a butt plug jewel under her boy clothes. Sure, she'll have to wear boy clothes every once in awhile and it's best when she's dressed up like a little slut but it doesn't mean that she can't be dressed underneath :)

Have her train to suck/take a cock and eat cum. I'm sure that'll really make her dicklet hard. Or, if it's in chastity as it should be, then it will try to get hard.

Ruined Orgasms, CBT, Post Orgasm Torture

These techniques are different from the other two headings. You'll have to remove the chastity cage for most things in here to properly spike that erotic energy.

Ruined Orgasms

This one is cruel and so much fun. For you. I promise you that every sissy dreams of mostly the same thing and Ruined Orgasms & CBT are two topics that will show up in their fantasy list.

A ruined orgasm is simply an orgasm that isn't pleasurable. That means that you can put post orgasm torture because it diminishes the pleasure received from an orgasm it can be done before, after or including any of the other methods so I will discuss that one later.

There are many techniques that you can use to ruin an orgasm and one of the most popular is the release method. Once your sissy is going to have her orgasm just release right at the point of no return. She'll spurt but with no extra friction or pressure it is completely unsatisfying and, if you're lucky, she'll want to cry. You can even demand that she tells you when she is about to cum so that she is the orchestrator of the demise of her orgasm. It adds a little to the humiliation but also, simply put, it's funny.

There is the "stop gap" method. Instead of releasing you pinch the tip or close it with your thumb and do not let anything out. It's painful and humiliating. There are plenty of other methods that you can find online. 

Using a vibrator while your sissy is still in chastity and allowing her to cum is beautiful and merciful. It is also great because your sissy is still in clitty bondage and there is that reminder that while she came she still had to come in a cage.

Using a vibrator while your sissy is still in chastity and still ruining it is sublime.

CBT

CBT is shorthand for Cock & Ball Torture. Use humblers, flick the balls, squish the balls or put weights on them. All this and more. I'm sure that her clitty will be righteously hard.

Post Orgasm Torture

Post orgasm torture is quite simple. It doesn't need to be done with a ruined orgasm but it makes the experience so much more regrettable for your sissy if you do. This is a sub-facet of CBT since you are definitely torturing the cock and balls.

After she spurts many things happens to a male's biology once they do. They drop in dopamine making them not want to continue having sex or partaking in the affair. All that erotic energy goes away like magic and all those things that they said that they wanted they will not. Their little clitty also becomes extraordinarily sensitive. This is the important part.

When you keep touching, but more importantly here, stroking, that extra sensitive clitty it will be enormously painful for her. She will flail, she will fight, she will plead and she will do anything to stop you from stroking her. This is post orgasm torture.

Just be careful and have her tied up if you plan to do this. She may mistakenly hit you because she can't handle herself.

Prostate Milking

This one is the most humiliating. Once you have learned to do this you'll want to just, well, milk her. You massage her prostate and it'll dribble out in buckets (not in literal buckets but more than she normally does) and all without having to touch her filthy useless clitty.

Think of it as maintenance of the pipes. Or maintenance of your plaything/toy.

You've teased and denied her and you want her balls to be smaller because they are just too annoying. Or she's having more difficulty walking around and doing the tasks that she needs to accomplish to make you happy. You also do not want her to orgasm because that would mean that you'd have to start from scratch with chastity. And a ruined orgasm gives her a little bit of pleasure.

Well, a prostate massage gives her no pleasure if done correctly AND you empty out her worthless balls. Win-win-win-win-win. If you make sure that she enjoys her product all the better.

Some information on Prostate Milking.

Where do I go from here?

Keep teasing, keep denying orgasm, keep ruining her orgasms and milk as needed. If you can do it throughout the day.

It's what she wants so why not comply? Besides, keeping her in a high state of arousal is of great benefit to you :)

*curtsey*

Sissy challenge: Unlock & Orgasm

Here's a nasty little scene that you can try with your sissy that should give you a hour or more of enjoyment and laughter. It is preferable if you do this with an audience and on her milking/orgasm day.

Toys you'll need

• Electro anal bulb
• Sissy in chastity
• A sussied up sissy (dress, corset, stockings, ballet shoes, makeup, wig)
• Key in ice
• Heat gun (preferably is constant on or use rubber bands)
• Heat gun stand
• Dead Man switch or Pressure switch
• Oodles of rope
• Electrical tape
• Chastity key in ice

Some preparations

The preparations are simple. After you've hobbled your sissy into the play area you'll want to do a few things.

• Frog tie her
• Tie up her balls and take a long piece of rope and tie that to an anchor
• Tape up her hands
• Ice block with the key in the center. Hopefully it is 5 inches down.
• Put the ice block under the stand with the heat gun there.
• The heat gun should be plugged into the switch. It should be close enough to her so that she she reaches for it she'll pull on her balls.
• The bulb goes into the sissy's ass and have the switch ready
• Flesh light and mount

The Rules

The sissy has 1 hour to melt the ice block, get unlocked and have an orgasm. Sissy is not guaranteed an orgasm nor a pleasurable one. Sissy may be harassed, humiliated and of course tortured on her mini quest to get her orgasm. Per the usual sissy will clean up with her tongue afterwards and possibly service any other audience members if they so choose.

The game

It will be painful for the sissy to crawl/drag herself close enough to the switch to hit it. The closer she gets or the longer she hits the switch the more pain she should feel in her little sissy balls.

Every 1/10th of the ice that melts you get to move the switch 2 inches. By the time the key can be retrieved the switch should have been moved 10 inches and your little sissy should be in serious pain to hit the switch.

Since your little sissy's hands are taped up it is you that unlocks her chastity. Feel free to tease and make this take longer than it should.

The anal plug is not for her pleasure it's for you to switch the electricity on at random intervals for a length of time that you feel is most entertaining for yourself and possibly your audience.

Mistress may also decide to spank or prod her sissy while she is making her way to the key. For instance, taking off her ballet shoes to tickle her or pinching her nipples etc.

If sissy does get unlocked in time then sissy is allowed to fuck the mounted fleshlight while still in bondage. Either way Mistress may decide to do post orgasm torture if sissy finishes.

There you have it. Have fun and post any comments as to how I can put in more detail or modify the game.

Reference Images

This is a beautiful tie that you could use on your sissy.

The panel gag is perfection and her muffled cries from electric play would be, well, delightful.

A great tie to use but she should be on her tummy.

This may even be better than a frog tie. It's all up to you (Mistress) of course.

*curtsey*

Recommended Annual Orgasms Chart

I simply couldn't help myself. I couldn't bear with the evilness, and short sightedness, of the original Recommended Annual Ejaculations Chart.

The things that I disliked so much about that chart was that it only expected ejaculations. Ejaculations do not an orgasm make. If you've played with tantric sex, and I'm specifically speaking to the men (former men also) you'll know that this is the case.

There is so much you can do with the semen too and it saddens me that this is put out there. I know it's most likely a fantasy, and maybe even created while in the heat of fantasy from being in chastity for so long, but I wouldn't use it even as a suggestion. It does give me some good ideas so I decided to create my own. Essentially there is is only one difference but it's major in abstract.

This is recommended orgasms per year. I much more prefer this one over the other one. Now you have the option of ruining orgasms to keep the erotic battery levels high. The ruined orgasm still gives them some pleasure, with most of it coming from you touching their penis, but they do not get enough. It's not complete. Their frustrating is yet even higher. Hint: Keep stroking to assert dominance and buckets of pain.

You also have the option to prostate milk your sissy. Milking them is such a good way to get the semen out and with skilled fingers they will not feel an micron of pleasure. They are so, incredibly, crazily horny and they derive no pleasure from the ejaculation  when they normally would. How hot is that? How humiliating is that? 

For many people, sissies like me included, chastity is a very big part of our humiliation and bondage that we oh so crave. Honestly, if you are a potential mistress or player of the game, you need to understand that this is sexy for many of us because of the humiliation aspect. You don't need to force us to wear the getup or get into chastity. The fact that you're willing to do it and help us break the chains of our normal routine and societal bonds is such a big show of love for us. We want, love, CRAVE this because it is absolutely and a complete 180% turn on everything that is is to be a traditional alpha male. All the things that is normally meant for men such as not showing emotions, not having anything attractive to wear, our fashions rarely changing but instead being updated, not being able to show our emotions, not being able to show love openly, not being able to submit to someone else and god forbid that master be a woman is a giant change for us. That change we crave is part of the humiliation. It eventually, and hopefully, grows on us and we become more open but just the fact that the humiliation aspect is there is important.

So, with that humiliation aspect somewhat, but I should go into greater detail in yet another blog post, you can see why doing even more with the semen is not only an enormous turn on but also should necessitate the excretion of the fluid but not include an orgasm.

I'm sorry I rambled and I'm sure that this is a lot to take in and I"m also very sure that I didn't make the greatest amount of sense. I just hope that I can separate the silly fantasy from real and rational play.

The greatest of luck <3

*curtsey*

Recommended annual ejaculations chart

I was on reddit as on one of the sub-reddits I found an interesting image. It's title is Recommended annual ejaculations chart:

This is somewhat fantastic. It means that, for myself, at the time of this writing, I would get 8 orgasms per year. I'm 33 years old with a 6 inch penis.

Clearly this is written for sissies, cuckolds and chastised men. Also, it's very ambiguous to what the ejaculation should be. I like the idea of milking for maintenance and ruined orgasms for that erotic energy up but if this means ejaculations then that would mean that these two activities constitute as ejaculations and that scares me. It also means that your sissy's balls would be enormous throughout the year. I think that would hurt and, in my opinion, may be very unfair to your little girl. It would be great fun for you.

So I think that the chart should be about orgasms and not ejaculations. If you limit it to just spilling seed then that really puts a divide between the mistress and the maid. Most maids are attached to a mistress that is their wife and having not intimacy between these two parties really saddens my heart. It goes from being a fun game to a clinical and professional relationship. This may be what you want but it is far from what I want from my Mistress. So 8 (preferably 6 or less) orgasms a year would be ideal. Ejaculations per years should be unlimited.

Seriously, if mistress ever decides to loan me out to as a maid or a sexy she-girl to another domme, dom or to a group to be fucked or to server (and thusly be fucked) I will be all dressed up and in chastity. When you don't get to cum from penile activity it is highly likely you can from anal activity. Though I'm not sure if it's an orgasm or just, yet another, prostate ejaculation. I don't think that should could.

Lastly, it doesn't say but I think that this chart is good for the first year of chastity. Then from there on out you cut out 1/3 of the orgasms. So in a few months for me I would suggest 6-4 orgasms per year instead of the 8. 

When it all is said and done it doesn't truly matter what I, a lowly sissy maid, thinks as it's the sissy's position, her whole existence is to serve so if her lady wants her to not ejaculate for more than 3 months then so be it.