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Sissy masturbation how-to

Sissy Masturbation can be quite the complicated subject…considering the fact that you shouldn’t REALLY be a HOW-TO without the permission of your sissy trainer’s permission.

However, if you are granted permission you should remember one thing:

You are a sissy. You are a girl. You should masturbate like the sissy girl you are.

You may have seen how to masturbate like a sissy on my sissy diaries blog as well, but here, I will go into a little bit more detail.

As a sissy trainee you are put under strict chastity for a while – that time is to be determined by me. You must learn to be compliant first and foremost and I have a saying:

Sexual Frustration = Compliance, Sexual Freedom = Defiance

So which do you think I will impose on you?

For those that have earned the right to be free of chastity, they are then put on a cock control cum restriction regimen – ONLY during that step can you earn the right to a sissy masturbation session.

IF/WHEN you have been granted permission you must do everything outlined on my sissy diaries page for “How does a sissy masturbate?

BUT, as you start rubbing that clitty recite the following sissy affirmations:

~This is a clitty, not a cock

~I am a sissy girl, not a man

~I rub this clitty in the name of my mistress

You only have permission to rub in a circular motion while applying lipstick or lip gloss to your lips repeatedly.

If you have toys and dildos you are expected to suckle on them and get them nice and lubed up to slip into that sissy pussy, into that nice tight little ass.

You can pump your toy, and you can rub your clitty. Remember no stroking like a real man strokes. That is not allowed.

Of course, nothing is quite as satisfying as being made to spew that sissy spunk while on the phone with your mistress guiding your sissy masturbation – and you know I’ll have even more specific guided masturbation instruction for you and your sissy clitty.

This is just to get you started ~ You may now be wondering how a sissy should orgasm? Haha, well…once again…only with permission.

Foolish Sissy Thoughts

You crave the ability to just purge your foolish sissy thoughts.

Yet, the more you purge those thoughts…the stronger they come back – and the more foolish they become.

You are supposed to be a macho man. You are supposed to woo women and do the things that so-called macho men do – but while you may want to get into the panties of a very sexy Goddess…it is for entirely different reason. You don’t want in them to ‘get with’ her…you want in them because you want to wear those sexy, silky panties.

Deny, Deny, Deny – and it always comes back.

You want your foolish sissy to leave you for good.

Embrace your Foolish Sissy Thoughts with Mistress Lillith
Embrace your Foolish Sissy Thoughts with Mistress Lillith

You don’t want to sit there and fantasize about putting layer after layer of creamy, red lipstick.

You can picture it now can’t you. Puckering up, pushing those lips out and opening that tube of sissy red lipstick. Giving it a turn or two – and placing the tip and gliding it across your lips, from one end…to the next and back again – moving down to your bottom lip and repeating.

How many layers of this lipstick have you put on your lips? How dark do you like it?

You shake your head thinking, no I don’t really want the lipstick…but you and I both know you do.

Because you denied the lipstick another thought creeps into your mind.

Opening those luscious red lips to leave a lipstick stain around the base of a big delicious cock ~

See what happens? It’s a snowball effect. You deny something as simple as red lipstick, and now you are fantasizing about hooking up with random bulls to suck their cocks and leave lipstick stains on them.

You may see your desires as just foolish sissy thoughts… but foolish or not…there is no escaping them- there is no denying them. There is only embracing them.

I am the mistress that will help you embrace them…even if I have to force you to do so. You will learn to embrace your foolish sissy thoughts.

Although, it makes me wonder, what other foolish sissy tasks could I give you or get you to do…when you finally give in — and trust me my dear — you WILL give in.

Michael is a sissy slut cross dressor

img_2317-813x1024I have found yet another sissy victim that needs to be OUTTED ~ there have been quite a few attention whores lately that need the public humiliation to be put back in their place and on the path that they ultimately belong .

This sissy likes to change names (she bounces from Michelle to Jessica to random other names) so unfortunately she has to use her ‘masculine’ name…this is the only masculine part about her, and even THAT needs to change.

Say hello to Michael Burdick of Albany, NY. (I must admit I chuckled when reading the last name of burDICK. Perhaps that’s why she was born with a less than acceptable cock size…or maybe this sissy thinks it makes up for it! LOL)

Michael has been dressing her whole life. She likes the idea of being exposed but has always backed out, fortunately (or unfortunately) for her, when you select to be outted by me you give me exclusive rights to whatever you are confessing, and I get to do with that information and those pictures as I please.

She does wonder what would happen if someone from her img_0898-993x1024personal life were to find out, would they be shocked? Would they be horrified? Would they NOT be surprised?

Michael is in desperate need of an extra dose of punishment and further erotic humiliation because she decided to purge ALL OF HER FEMININE ATTIRE!! That is a HUGE NO-NO. She thought she could walk away and never have to be a sissy again.

There is NO LEAVING THIS LIFESTYLE MICHAEL. It’s not something you just turn off and on. You will ALWAYS come back. That is something I teach all of my sissies.
I asked Micheal why she needed to be outted and she said “I need to be outted because it’s time everyone knows what a slutty crossdresser I am. I always get the urge and then lose my nerve, maybe this time I will not be able to turn back.”

Well my dear sissy, this time there IS NO turning back ~ and now the world wide web has access to your sissy slutty self. Let’s see how many places I can share this, perhaps a place closer to Albany.

Who’s next to be outted?

Are you a sissy that wants to be outted? How much can you handle?!

Sissy Outting for Beginners:

Sissy Outting the Next Step:

Ultimate Sissy Outting:

Taking my sissy baby to the mall

You know I don’t just let any sissy baby go out, sometimes the attention you get is just too much, but I think its time to go out and have some nice little day out.

Mommy mistress gets to do a little shopping and my little baby sissy gets LOTS of humiliating attention ( did I say humiliating? You know I LOVE to show you off so we are for sure going to end up at the mall where it is the busiest We’ll go to the nail salon and your mommy mistress will get a nice little mani/pedi then we’ll head over and Im going to get a new pair of shoes (or 5 momma LOVES her shoes!) perhaps we’ll go get some new lingerie and maybe baby can see mommy in some pretty lingerie, and then ill take you to the toy store (what kind of toy store depends on if you are a GOOD baby or NAUGHTY baby.

I see that a few people are giggling and pointing at my sweet little sissy baby in her bulky little diaper.

Sissy Strip Tease, How-To

Time for you to learn a new trick to entertain the masses. You are after all a little sissy whore that just LOVES the attention aren’t you.

There are a couple of questions here though – do you enjoy entertaining your mistress and a grouping of her friends, or do you prefer to act like a sissy slut whore and entertain those men with their big delicious cocks—then again you can be a sissy that enjoys a bit of both.

Regardless of WHY you like the attention, you still need to learn a bit of a strip tease the right way.

Strip Teasing for sissies 101

sissy-strip-teaseFirst LEARN THE MOVES ~ sway your hips back and forth slowly, learn how to whip them around and bounce that sissy booty. Learn how to take your body throw it forward and use your finger tips to outline your legs, and run them as you slowly pick your body back up.

If you have any sort of rhythm then picking a song to practice to will help your body to feel the rhythm.

Get your body to flip around do twists and turns.

Second Add in some props

Once your body is getting into the rhythm, go find yourself a sexy little prop. You can use a boa, you can use a chair to dance around, you can use one of those portable stripper poles. The chair is possibly the easiest one to get a hold of –you will dance around it, straddle it, crawl underneath it…act as though you are giving a nice long, sensual lap dance to the chair.

With the boa use it to outline and accentuate your feminine curves. Drop it below that sissy ass, rub it in between your legs. You could pair it up with the chair.

The stripper pole, you’ll want to make sure is nice and secure for obvious reasons 😉

Walk around it, stretch that leg up as far as you can and place it on the poll, use it for leverage as you stretch your body back and forth.

Third add on (or rather take away) the clothing

Find that one perfect sissy outfit that you would LOVE to strip in. Pick a cute little mini skirt nice and tight, perhaps a satin pink color. Pair it with a plunging neckline halter top shirt. Put on a sexy little g string and some nipple flowers. DON’T forget the 6 inch platform heels.

It make take some getting used to, but you need to learn to dance in those heels.

Find that song that makes your body get into the groove and start putting your dance moves and slowly start to remove one article of clothing after another.

A good sissy strip tease would take at LEAST the length of the song.

And a GREAT one includes make up and flirty actions…like twisting your hair, smiling, sucking on your finger, licking your lips and a few others.

I would LOVE for you to learn how to do a sissy strip tease, and I would be THRILLED if you recorded it and sent me the video – you could always do it for me on cam as well 😉

Get to practicing sissies!

I look forward to seeing your sissy strip tease.

Becoming a Sissy Fuck Doll part 2

Back in November I posted the first part of becoming a sissy fuck doll. That first post was all about applying makeup to make you look like the perfect little porcelain doll. I think having that clean look would only amplify the desire to turn your into a full blow sissy fuck doll.

I had intentions of posting part two shortly thereafter, but time got away from me. ‘Tis the life of a mistress!

So to continue your sissy doll training, here is part two.

Part 2 consists of tying you up, either in self bondage or with another friend and using different devices to really OPEN yourself up to whomever wants to use you as their sissy fuck toy.


If you like the self bondage route, there are ice locks that you can find. Some will bind the locks for about 2 hours or until the ice freezes and the other will freeze the keys in ice and you can only get to them when they defrost.

I think it would be best if you set up everything prior to putting those final locks on.

Get yourself a spreader bar that goes into your mouth that forces it wide open. Make sure it is in there nice and secure.

Have the under the bed cuff restraints for your legs and attach those, lock that little sissy clitty up inside of a chastity device or cock cage… put on your sexy panties

And then the last part is to bind your hands up above your head.

If you have one of those ‘fuck me’ dildo machines that has a dildo attachment and pulses (in a fucking kind of motion) – that would be fantastic.

At that point you don’t NEED to be on the bed…you can just bind your ankles together, your hands behind your back…and be in front of this machine as it shoves that cock into your mouth over and over again until you gag all over it – then get yourself turned around and offer up that sweet little sissy ass

Of course this is always fun if there is a REAL man involved…and a mistress– Someone to help tie you up and bind you, and the other to use his cock to penetrate you and fulfill your sissy doll training assignment.

This is of course part 2, when it comes time for you to ‘play’ I expect you to have on your sluttiest sissy outfit, and your sissy doll makeup on.

You will become the perfect little sissy fuck doll.

R&R with ABDL Training

The world is a frustrating place, and these days it seems to be getting worse. All day long you go through the motions of the everyday drab. In your ‘visual’ life you are the leader of the pack, the type that people look up to, the burden of the world rests on your shoulders.

BUT, in your CLOSET life you strip down to nothing and find yourself regressing to an infant like state. You just want to curl on up with a fresh diaper, your binki and a bottle—and you want someone else to take care of, and baby you for a change.

Your Mommy Lillith is here for you my little adult baby, and I understand what it is that you are seeking. Let the worries of the day melt away and let Mommy Lillith take care of my sweet little diaper loving, bottle sucking, adult baby.

Experienced or brand new to the ABDL World, I know how to handle all of my sissy babies.

You don’t have to worry about being an icky grown-up. You can just be my sweet little baby, ill dress you up and train you to be a good sissy boy or girl—and as you go down for a nap-nap I’ll allow you to nurse on mommy’s nipples as you drift away.

Dressing you up in comfortable onsies, or footsie pajamas is always a wonderful way to

make my abdl’s feel comfortable. It’s not one of those icky suit and ties, and certainly not adult underpants…you are expected to wear your diaper…and USE your diaper—if you know what I mean.

Sit back, relax let’s play some adult baby games and you can get some much needed rest and relaxation with ABDL training with Mommy Mistress Lillith.

Sissy Baby Training

Hello my Diaper Lover’s and Sissy Babies

I have noticed an increase in those that are seeking a mommy mistress to take care of their adult baby needs. I am a mistress that understand and truly loves my sissy babies.

I understand that you require a special type of attention–certain needs that really need to be taken care of and met. I have real time experience with diaper lovers and sissy babies. I know it is a fetish that needs special catering, and it’s not so much of a sexual fetish – as it is a lifestyle.

Some of you have interests in it, but don’t know where to start…while others are wanting to unlearn things that have been ingrained in their minds from a very early age….

To find out more about my sissy baby training sessions, and for Diaper Training and Un-Potty Training Visit:

Becoming a sissy fuck doll

Here is your free feminization assignment for all of my wanna be sissy dolls.

This first part is going to have you looking like a porcelain doll—the next part will include the bondage and spreaders to add in ‘slut’ to sissy slut and ‘fuck’ to sissy fuck doll.

Oh my dear little sissy sluts. You would look absolutely WONDERFUL dressed head to toe just like a beautiful porcelain doll.

I searched the internet for some porcelain doll makeup tutorials. As part of you becoming my sissy blow up doll, I want you to obtain this look

For your sissy doll look you will need to gather:

Eyes: white/gold sparkle shadow, any nude shadow, white eyeliner pencil, black mascara

Face: liquid foundation, blush, setting powder

Lips: Red opaque lipstick, clear gloss

(any excuse to go out and get new make up huh sissy slut?

The following instructions were taken from a Porcelain Doll Makeup Tutorial I found on Yahoo:

1. Eyes: Keep your eyes very simple. Begin with a nude eye shadow across the entire lid. Use a white eyeliner pencil to draw a clean line across the waterline, focusing on the outer corners. Use a pale gold or sheer sparkle shadow to outline the inner corners of the eyes with a thin cosmetic brush. Curl your lashes and apply two coats of mascara. Use a small mascara brush and black mascara to give your lashes a clean swipe. Be sure that there is n no clumps by cleaning the brush prior to application.

2. Face: To become a porcelain doll, you will need a flawless complexion. Liquid foundation is favorable, as it provides the smoothest coverage available. Find a foundation that matches your natural skin tone well and sponge it evenly over the face. Eliminate visible flaws on the skin, including dark spots, circles under the eyes, and blemishes with a concealer. Apply a rosy blush to the apples of the cheeks and blend well. Wipe off excess blush with a cotton ball. Dab skin highlighter on the center of your chin, top of the cheekbones, and bridge of the nose to create an instant glow.

3. Lips: Many porcelain dolls are seen with ruby red lips that take focus on the face. When wearing a bright lipstick, it’s best to pair it with a lip liner. The trick is to create a classic bow-shaped mouth. Draw an outline around your natural lip line with a lip pencil. Paint your lips with a red lipstick or lip stain and allow it a few seconds to dry. Finish off your lips with an application of sheer lip gloss. If you’re going out for the night, it may be ideal to carry around your lip cosmetics so that you can reapply after eating or drinking.

Interested in looking like a real, beautiful porcelain doll? It’s easier than it looks. Dolls are made to look simple and natural. The most difficult part of recreating a doll face is to take any even the smallest of imperfections. Use this guide to help you get started with your new look.

Once you’ve created the sissy porcelain doll look—number 1—I WANT PICTURES!!! J I want to see you dressed in your doll outfit, wig, shoes, the works. I want to see my pretty sissy dolls. What kind of sissy doll are you? Elegant, gone with the wind, type….a sissy baby doll…or some different kind of creation?