Sissy Training

Sissy Training;

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Clip: Slut School Sissy Training

Welcome to Slut School, Have you ever thought about dick? I’m going to teach you allll about it. You’re eager to learn aren’t you? I’m sure you’ll make a good student once my big dick is inside you. Have you ever put anything inside you? I’m sure you’ve thought about it. After I’m done with you, you’re going to be a pro!

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Femdom Erotica – Traveler gets Locked in Chastity

Seattle Chastity Mistress Ruby Enraylls, Cuckolding dominatrix

It’s been a long week already but you’ve had your email to distract you. Normally you hate the airport, the waiting, the delays and all the people. This time it just gives you time to build up tension. Her emails, texts and photos have kept you on edge the entire time and you can’t wait to see what awaits you on the other end of your flight. She reads you like a book but your Mistress is so mysterious to you. That always works to her advantage. This time she says she has a surprise for you, given what she knows about you… You can only imagine what it could be. Oh well, time to board and shut down.

You’re on your toes the entire flight, you can’t manage to get a lick of work done. Ugh. Hopefully you’ll have your wits about you later.

You land and you get one text that says simply “Surprise is at the hotel. Meet at the usual spot.” A shiver runs down your spine and your cheeks burn. Holy shit, what did she send to the hotel? Fuck. Your mind is racing and the obnoxious hum of the Uber driver’s too loud-not your taste music fades away into the background. You are too fixated on what awaits you at the hotel and then later, in her clutches.

The lobby seems entirely too bright when you walk in and you float over to the check in desk. “Hi, um..” you stammer. “I’d like to check in. I believe you have something for me too..?” The woman behind the desk smiles brightly and acknowledges you, taps her keyboard then hands you two key cards and a shipped box. “Can I help you with anything else?” she queries but you are completely lost to the world.

Oh fuck oh fuck oh fuck. She sent it. She actually sent it. You feel your excitement starting to build. You suddenly snap back to reality and the check in desk girl is staring at you. “Uh, sorry.” You blurt out. “Long flight.” She shrugs and repeats her question. You decline, thank her and excuse yourself quickly. Being careful to hold your personal items in such a way to not disclose your excitement to any casual passers by.

Up in your hotel room you are brimming with anticipation, staring at your box. Yet you don’t dare open it without permission from your Mistress. You fired off a text as soon as you were in the elevator but it feels like every second is taking an eternity. Finally, a reply. “Yes, open it. You’ll know what I want you to do with it.” The text is almost too much for you but you steady yourself and tear into the box.

Of course. Packed neatly inside the discreet box is your very own chastity device. You gulp, you were on edge before you got on the plane and now you know you’ll be in for more torment. You get so compliant and obedient when you’re locked. She knows just how to push your buttons, you can’t help but comply. The device is snug but it fits just right, you can’t help but obey and put it on. With a click, it locks securely. For a moment, you feel panic and decide to back out. Unfortunately, there’s no key in the box. Fuck. Your phone lights up… It’s a text. “Freaking out yet? You’ll have to earn that key back… This is going to be a fun trip!”

You feel yourself strain against the cage. Oh. Fuck…

Sizing Corsets for Sissies, Feminization, and Crossdressing

Seattle Strapon and corset dominatrix ruby

Corset training can be an excellent part of any feminization routine or a wonderful set of sissy tasks. If you want to make your body more feminine, it’s a great way to do it without any big changes, so it’s a great option for a man, sissy or casual player to explore. They can range from cheap to very pricey depending on your needs, budget and how fancy you want to be. That being said, you can often get what you need for your closet without breaking the bank.

I’m going to answer some basic questions that you may have about how to fit a corset, this is part one about picking a corset. I’m briefly touching on several other topics I’m going to cover later such as body types, corset styles and fabrics. If you would like an individual consultation about sizing any type of clothing or shoes or selecting make up based on your skin, please feel free to contact me. Moving along..

How do I measure for a corset?

You need to measure your natural waist size in order to size a corset. You can measure your natural waist size one inch above your belly button.

Once measured, always choose a corset 2-4 inches smaller than your natural waist to achieve the ‘hourglass’ effect. The amount you “size down” is how tight the corset will close and depending on your shape and the shape of the corset you should size accordingly. Always read size guides.

Some fashion corsets may not come with traditional sizing, in which case I would refer to my previous sizing guide.

Where is my waist?

Your waist is the smallest part of your abdomen. Usually one inch above your belly button but it varies on some people. Take a fabric tape measure and pull it somewhat right around your waist, where does it gather to? (When measuring don’t cinch tightly, hold the tape loosely.) This also gives you information about your body shape. However, that is for a different post.

Can I use corsets designed for female bodies?

Yes! But they all fit differently. There is a simple over bust and under bust as far as length but there are also long line (for long torso which come in both under and over,) cinchers, waspies and corset belts. All in descending order of coverage.

You also want to pay attention to how much curve a corset has. Most “real” corsets have some kind of metal boning in them but fashion corsets which have the least support use plastic and are the most forgiving. A real corset will have corded laces or strings of some sort (like a shoe lace,) not generally ribbon or zippers as they will break easily with repeated lacing/zipping

Tight lacing cotton corset
Product: Cotton Tight lacing Corset from Mystic City Corsets
A tight lacing or hourglass corset is more on extreme end and is usually not for beginners but is incredible for creating a perfect curve. Tight lacing is the technique used to create a well defined hourglass figure.

Another thing to think about is the type of fabric used. Is it mesh, leather, satin, cotton, brocade? They all wear, sit, fit and stretch differently.

For example, a mesh corset will breath more which is better for wearing under clothes but it is less usable for tighter lacing (waist reduction) and will break down faster. Alternatively, you could wear it over your clothes for an alternative look.
Mesh Waspie Corset
Product:

A satin corset looks prettier on the outside (and would make a great sissy corset) but may get lots of runs in the fabric or stain easily depending on the color. Satin, cotton and brocade tend to be fairly default when it comes to corsets. PVC, leather and latex are more speciality fabrics.

Satin underbust corset
Product: Satin underbust corset from Orchard Corset

Will wearing a corset change the shape of my body?

Over time repeated and consistent wear of a corset can change your shape but such pursuits should be undertaken with caution. If you only wear a corset occasionally, your body will return back to its original shape once you remove your corset. If you desire to change your waist size through corset training, it requires dedication

References:
https://www.orchardcorset.com/pages/corset-sizing
https://www.rebelsmarket.com/blog/posts/types-of-corsets-how-to-wear-them
https://www.leaf.tv/9749781/does-your-body-go-back-to-normal-when-you-take-off-a-corset/

Sizing Women’s Clothes for Sissies, Feminization & Crossdressing

womens clothing sissy size guide

All around the world, women lament the chore of trying to divinate the size of their clothes.

When trying to figure out your size in women’s clothes as a Sissy, for feminization or crossdressing it gets a bit more complicated.

0 here, 12 there, 40 over there. It makes no sense. That’s just crossing countries. Try crossing brands. If I look into my jeans drawer I can find 26, 27, 28, 29, 2, 4, 6, xx small, small, medium and one size fits all. Who could possibly figure out how to order pants when you’re coming from a world of waist by length? I guess what I’m saying here is that no brand is standard in sizing when it comes to women’s clothing and the material and cut makes a huge difference in the fit. You never really know how something will fit until you have it on but usually size guides for sites will lend some help.

The trick comes in several parts.

This is an important tool you’ll need, however.

Know your measurements
However you’re planning on dressing, you better take your bust, waist and hip. The bust is the biggest part of your chest, waist is the smallest, hip is the biggest part of your hips/butt.

For bonus points, measure your neck, around your thigh, your bicep, the width of your shoulders, the length of your arm and the length of your leg. Now you can get fitted for anything!

Read size charts
Seriously. If the site you’re ordering from doesn’t have one, try to google one for the brand. It will save you a lot of time.

Understand fabrics
The stretchier the fabric the more give it has and the more you can fudge measurements. So look at materials and Google that if you are unsure, same with reviews. Common stretchy fabric names are lycra, elastane and spandex.

Now you are all set to order some clothes! If you need some one on one consulting, feel free to contact me and I would be happy to help you.

Clip: Weaklings Suck My Big Black Strapon



Hey slut! Are you ready for a new adventure? It’s time for you to learn to suck a cock.
First, I’m going to tease you – aren’t I nice?
Isn’t it better to suck the cock of someone who has tits?
It’s a big one, too?
You’re going to be a good slut for me, aren’t you?
You’re going to take the whole thing.
I like sluts that suck cock well.
It’s a good use of a mouth.
Why let that hole of yours go to waste talking when it could be pleasing me instead?
Look how close you are to my pussy. If you’re lucky you might get to smell it.
But of course you’ll never get to taste it. Your place in this world is a cocksucker now.
What a good slut! You’re learning to suck cock very well, aren’t you?
You’ll be a good little cock whore for your mistress very soon, won’t you?
I’ll train you to suck tons of cock for me, then I’ll whore you out.
I bet you’re sluttier than you think you are, you little whore.
I bet you like to wear panties for me, don’t you?
How does my cock taste?
It’s good because it’s mine, isn’t it?
How does it feel knowing you’re turning more and more into a whore for me?
Pussy’s not for you any more is it? Only cock from now on. So take it.
Slurp it down nice and deep down that little slutty hole of yours.
Soon you’ll be begging for cum instead of cock.
In strange hotel rooms with strange men.
Show me what you can do with a real cock.
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Endza Sucks Her Mistress & Receives Punishment











































“You look nervous now.” Says Mistress Ruby to Endza, her strapon cock now fitted and tightly affixed to her curvy frame which is accented by a tight corset. Ruby grabs the rope leading from Endza’s collar and yanks her around by it, forcing her head down onto her cock. “See? Now I have a handle!” See says with a grin “It’s effective.” Endza sucks her cock with vigor and great desire to please her Mistress.

Suddenly, Ruby yanks Endza’s head back by her hair and spits in her face causing her to flinch. “It’s messy..” Endza murmurs with disdain. “I’ll clean you up” replies Mistress Ruby with a sneer, wiping the saliva all over her face causing a shudder. Mistress Ruby smiles with delight and reaches down her shirt to pinch her nipples. “Hmm…” She says, thinking. Then with some minor adjustments, pulls down Endza’s top. “Now you look like a damsel in distress.” Ruby says before wrapping her hand around Endza’s throat.

Part Two of Three
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The post Endza Sucks Her Mistress & Receives Punishment appeared first on Seattle Dominatrix Ruby Enraylls.

Sissy Slut Shopping List


























































Hello, my little sissy in training. Today, we’re starting with a little shopping trip for some new toys!
If you’re going to be a good little sissy faggot for me, that means you’ll be sucking cocks.
That means, you need something to practice on and work your little mouth out! So for your first outing, you are to go to a sex toy store and pick up a nice dildo for you to practice sucking on.

Next. you’re going to get nice and dolled up for me and that means shopping for slutty clothes! Get a wig to make you look all nice & pretty for me. Then get a pair of stockings, as well. Don’t forget to get a pair of slutty panties, or a bunch from Victoria’s Secret.

I want you to wear them regularly under your normal clothes to remind you how much of a pussy you are for me. Get a bra or a bustier – some little slutty thing to wear with the rest of your outfit.
No clashing colors! Make sure they match! Get a pair of heels. You’ll be needing them if you’re going to suck cock for me.

Now it’s time for your face. Go to either Sephora or a drug store.
Obviously I don’t shop at a drugstore because you can’t look this good shopping at a drugstore.
For makeup, you will go in person and buy:
Because I want you to suck cock for me and no one wants a nasty man sucking cock.
First, a primer
Then a foundation to cover up all your stubble so you don’t look like a man.
Then a setting powder
Then eyeshadow and an eyeshadow primer
Maybe a concealer.
Lipstick.
Mascara.
You’re just a baby, so you don’t need false eyelashes yet.
Eyeliner.
Then I will teach you how to put it all on. Your first few attempts will be pitiful because you’re just transitioning into being a slut for me, aren’t you?
I’ll teach you how to suck cocks, too.
Soon you’ll be my little daughter slut, won’t you?
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The post Sissy Slut Shopping List appeared first on Seattle Dominatrix Ruby Enraylls.

Five Easy Daily Slave Tasks

Seattle Dominatrix Ruby Enraylls the Ultimate Femdom rules the world from her beautiful seattle dungeon, no slave can resist a tempting seattle mistress like Ruby Enraylls

You are here because you want to earn my favour.
How gracious and kind of me to give you the opportunity.
It’s not every day I allow you to win a place in my stable.
I’m going to give you 5 easy tasks that will slowly over time build our bond.

1 – You must have a picture of me somewhere in your house or as a wallpaper on your device.

The idea is that I will be watching you all the time.
Partners do this all the time – I’m your mistress; it’s one in the same.

2 – Five days a week, at least, you are to get down on all fours (or at least sit on the ground) and pray to me, or at least think of me, for five minutes.

Mornings are best, that’s what my other slaves say.

3 – It’s a punishment of sorts. You will write 20 lines daily.

For every mistake you make, add an extra 10 lines.

4 – You will be allowed only one orgasm per week. It must be while you are watching my videos.

You can have more if I give you explicit permission in a video.
But only once per video. No re-watching – that’s cheating.

5 – I expect you to wear a collar for me.

It is a symbol of your bond to me.
What matters is that it has my name on it.
Watch this video multiple times so that you are sure you have got it all.
If you have questions, ask me.

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Please Me? You Can Beg!

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Hmmm.. That’s right, I’m ignoring you, my little peon. You don’t get any say. You just get to watch while I tease you with what you want. That’s right, I know what you want. You little boys all claim you want it, don’t you?

You beg, you plead, you whine.

I don’t mind your whining, unless it gets annoying, in which case it’s just irritating.
You can almost see everything you want, but you can’t have it. It’s not for you.
What lies between Mistresses’ legs is not for a slave, is it?

But you can beg.

I like this game… looking down on you while showing you what you can never have.
You’re not worthy, are you? You’ll never be. You’d love to be my #1 slave. I bet you can smell what’s between my legs, can’t you?

I bet you’re dreaming of it.

You’re dreaming of what I might let you see… what I might let you do. But you know I’ll never actually let you near me, I just like teasing pathetic little fucks like you. You’re only good for licking my shoes, aren’t you?

I like watching you whine and plead.

Beg really pathetically and maybe I’ll let you cum.
If you’re not touching yourself to this video, you’re not even worth my time.
I bet your dick is smaller than my clit.

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The post Please Me? You Can Beg! appeared first on Seattle Dominatrix Ruby Enraylls.

Hypno-Sissy Training Clip: Succubus Sissy Mind Control

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Good little boy, Watch the shiny. It’s time for you to be transformed for me, your GODDESS. The longer you stay in this dream, the harder it will be for you to resist my suggestions. You know that, deep down you want to be here, don’t fight it. There is no point. You’ve had fantasies about being a sissy. You’ve had fantasies about sucking cocks.

When you wake up, you’re going to go out and do something you never thought you’d be capable of. The longer you stay here, the harder it will be to resist the fantasy of putting on frilly panties and opening your mouth for a big cock. You want to be that and more, for your GODDESS. You want that, don’t you? Good slut. What a good slut you’ll be. You’ve long fantasized about it.
The pendulum is your reality. Keep watching, that’s very good.

You’ll pull other men’s pants down… with vigor. Wet, slurping, sucking, anticipating.. You want to be humiliated in front of a woman, don’t you? You want us to ignore your existence. You got sucked in by a demon who has powers you didn’t know were real. All that matters is the sound of my voice and the pendulum.

Think about how long you’ve longed to be a sissy. Everything has to be acted out eventually. How much longer can you hold out and wait to act this dream out?
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