The more I look at the D/s relationship between Mistress and sissy, the more I realize that chastity is a must. It really is. I've come 180 on this where I'm concerned. In my own case, I've never been ruled by my urges. Lately, if it does get excited, I don't usually play with it. I just let it go away. I don't care that much.
But, that may not matter to a Mistress, should I submit to Her. I'll have to remember, She will know how to deal with me. A good Mistress can get inside the head of the sissy, and She might get me thinking about an orgasm. Forcing me to play with myself and then locking me up. I may not think it would make a difference to me, but She may find a way. Certainly, I understand many Mistresses expect to lock a sissy into chastity.
There are many reasons for it, but the first is to completely submit to Her. I believe Her pleasure should come first to a sissy. That means more than just in the bedroom too. Sure, it definitely matters there. You must please Her, and I believe that means if you aren't into oral, you better learn to love it. You will put your tongue where She tells you to, and be grateful She told you to. You will become tuned to what it takes you please Her as much as She requires.
It's not just that. You Will likely be asked to give Her a massage. Maybe Her feet, maybe Her back. Maybe you give Her a full body massage. You will do what it takes. Being so close to a Goddess is bound to get you exited, and She can't have that. You must tend to Her and be focused on Her needs in that moment.
When She tells you to do anything, you must be focused on the task. You must do your best for Her at all times. Thinking about your pleasure is not as important as Hers, but it can be a motivating factor. You can focus on doing your best in the hopes that She will grant you permission for your own release. It matters not how much She may humiliate you when She grants it, you need to please Her.
Submitting to chastity for as long as She deems necessary should be expected of every sissy. A day, a week or a month. You'll go as long as it takes and be grateful. It's the ultimate act of submission to grant Her the control over your pleasure without question. You have given Her a gift, and She has taken it from you. Now that She has it, it's up to Her what comes next. You will concentrate on making Her happy. By putting Her first, you prove how committed you are to Her. You may be rewarded for your complete devotion to Her.
Some Mistresses can step it up a notch with their sissy. She will lock sissy up, and then She will show sissy what it's like to have a feminine orgasm, or as close as a sissy will ever get. You're locked away, so you can't touch it. Mistress puts on Her strap on and makes you submit to it. You will feel a wide range of feelings as She goes on, and you will feel the pleasure building up.
But, your clitty is locked away. You can't touch it. How ever will you get release now, sissy? Mistress knows. She's going to make you work for it. You will become desperate for it, and you will start to feel where the pleasure builds the most. Mistress will tease you. She will threaten to stop. Maybe She will demand you tell Her how much you love what She is doing.
Whatever She asks, you will do without question, because you need this badly. Mistress knows what is best for you, and this is part of how She makes you more of a little sissy. You are now Her little sissy slut. This is the way you prefer it. Mistress has shown you the way. But, She's not just gonna give it to you. What are you gonna do to make Her happy? What will you do to take care of Her needs?
When you are locked in chastity under the control of Mistress, you will do what She tells you without question. You have to. And it's not even about earning your pleasure anymore. You do it to make Her happy, because Her happiness makes you happy. You know that the D/s relationship between Mistress and sissy is all about trust. So, if you are on the fence about chastity, my dear sissy, don't be. To truly prove your devotion to Her, you must be locked away for however long She deems necessary.
Working to create a place for CD's/Sissies/T-Girls and the Women who love them
Playtime
Mind
Friday, September 27, 2013
Chastity For The Obedient Sissy
Labels:
CD Wardrobe,
cross dresser,
cross dresser Wardrobe,
crossdresser,
crossdresser shopping,
crossdressing,
Domme,
dress up,
dressup,
femdom,
feminization,
Mistress,
sissies,
sissy,
T-Girls,
transgender
Thursday, September 26, 2013
A Sissy's Lingerie Collection
When you start down your path to self feminization, you are thinking about what it is you want to do. You see the girls out there living it, and you are back at square one. You have so much to learn, and it's overwhelming. You wonder if you will ever get there, but you shouldn't. We all get there one step at a time, and that's what you will do.
Lingerie is the best place to start. When you are in your own home, or at least your own room, you can dress as girlie as you want to be. Panties are the best place to start. Once you figure out a size, all you need to do is pick the style and color you want. There are so many to choose from too. You can get them just about anywhere, and you really don't have to worry about where you buy them from. Don't worry, your money is as good as the genetic woman's.
Now that you've got panties, a nightie is a must. Two or three is even better. Get nighties that go with your panties, because you will want them to match colors. You will want to sleep in a nightie and panties. You may have a problem with the urge to pleasure yourself first, but that's okay. Once you take care of your sissy needs, you can focus on the other feelings of femininity you get while wearing your nighties and panties.
If you are looking for a third option, get some bras too. At least one, and make sure you have it match your panties. Two or three bras is even better, because a girl can never have too many choices. Even if you are only wearing them at home, so what? Does it make you happy? Good girl. Of course, you will get the urge to go out with panties and bra underneath your clothes. You should be in those panties anyway, but the bra may be another challenge. A pretty camisole under your shirt is easier to get away with. You can do it once in awhile when you feel comfortable trying.
A good lingerie collection is important to a sissy. Even if this is just you at home, you want to feel like a woman, right? Well, women like to have pretty choices in their wardrobe so they can wear something different. You are a lingerie sissy, so it stands to reason you should have choices too. Now, you may want to do more, but this is a good place for you to start. You'll be exploring ideas on the internet and will make a plan for what to do next. If you want it bad enough, you can do it too.
While at home in your lingerie, there are things you can do to make it more exciting for you. Get some lipstick, and make sure you have more than one choice. Nail polish and remover, because even a closeted sissy can paint those toe nails, which will be covered by shoes outside. Nail polish remover makes picking a pretty color a must, because you can take it off fast if needed. A splash of pretty perfume. And a toy or two for when you want to explore your girlie feelings even more while dressed up.
But if you want it bad enough, you can be a lingerie sissy. It is very easy to do, but it is up to you. Once you get started, you will want to build that collection up bigger and bigger. There are sites out there to help you find your size in women's clothes or for finding your bra size.
Lingerie is the best place to start. When you are in your own home, or at least your own room, you can dress as girlie as you want to be. Panties are the best place to start. Once you figure out a size, all you need to do is pick the style and color you want. There are so many to choose from too. You can get them just about anywhere, and you really don't have to worry about where you buy them from. Don't worry, your money is as good as the genetic woman's.
Now that you've got panties, a nightie is a must. Two or three is even better. Get nighties that go with your panties, because you will want them to match colors. You will want to sleep in a nightie and panties. You may have a problem with the urge to pleasure yourself first, but that's okay. Once you take care of your sissy needs, you can focus on the other feelings of femininity you get while wearing your nighties and panties.
If you are looking for a third option, get some bras too. At least one, and make sure you have it match your panties. Two or three bras is even better, because a girl can never have too many choices. Even if you are only wearing them at home, so what? Does it make you happy? Good girl. Of course, you will get the urge to go out with panties and bra underneath your clothes. You should be in those panties anyway, but the bra may be another challenge. A pretty camisole under your shirt is easier to get away with. You can do it once in awhile when you feel comfortable trying.
A good lingerie collection is important to a sissy. Even if this is just you at home, you want to feel like a woman, right? Well, women like to have pretty choices in their wardrobe so they can wear something different. You are a lingerie sissy, so it stands to reason you should have choices too. Now, you may want to do more, but this is a good place for you to start. You'll be exploring ideas on the internet and will make a plan for what to do next. If you want it bad enough, you can do it too.
While at home in your lingerie, there are things you can do to make it more exciting for you. Get some lipstick, and make sure you have more than one choice. Nail polish and remover, because even a closeted sissy can paint those toe nails, which will be covered by shoes outside. Nail polish remover makes picking a pretty color a must, because you can take it off fast if needed. A splash of pretty perfume. And a toy or two for when you want to explore your girlie feelings even more while dressed up.
But if you want it bad enough, you can be a lingerie sissy. It is very easy to do, but it is up to you. Once you get started, you will want to build that collection up bigger and bigger. There are sites out there to help you find your size in women's clothes or for finding your bra size.
Labels:
CD Wardrobe,
cross dresser,
cross dresser Wardrobe,
crossdresser,
crossdresser shopping,
crossdressing,
Domme,
dress up,
dressup,
femdom,
feminization,
Mistress,
sissies,
sissy,
T-Girls,
transgender
Monday, September 23, 2013
A Poem: Ode To A Secret Sissy
Ode To A Secret Sissy
Tell me how it feels to sleep securely gagged and bound
You can't portray the macho man. He's nowhere to be found
You struggle to keep sissy feelings buried deep within
But this is not a fight that you are ever gonna win
To all outside this special place, you are the manly dom
But dressed up in such frilly things, that manly man is gone
Your Mistress now is here for you, so much to your delight
But you know what that really means, you'll be her bitch tonight
Your girlie dreams won't go away, not matter how you try
That manly man facade you have is nothing but a lie
Your Mistress has secured you now, you're tied up to a chair
Her dildo shoved right in your face, you suck without a care
You worry what your peers would think if they could have a look
The life you've built now gone away, and this is all it took
You beg and plea for her to stop, "Please sissy, leave me now"
But all she hears is, "Welcome back dear sissy, take a bow"
With Chasity and anal plug, and you so cute in white
Your Mommy Domme has dressed you up. You're really quite a sight
You feel the guilt and all the shame, but is it such a crime
Deep down inside you know you wish that she could be full time
Your Mistress tells you to your face your noting but her bitch
The macho Dom is just a lie. You are a sissy switch
She takes the gag out of your mouth, "Now tell me what you want"
Desperation as you cry, "Use my ass as a cunt"
She moves you over to the bed, your ass up in the air
You beg your Mistress, "Do me now. Please stick it inside there"
She asks "What will you do for me? You're selfish, there's no doubt"
You know what she wants as you say, "Please let me eat you out"
She holds your words against you as she says you have no class
"I'll tell you want my sissy pet, I'll let you eat my ass"
Where is that manly man right now, he seems so far away
You stick your tongue into Her hole to prove that you'll obey
Your sissy tongue works all around Her sexy, tight back door
To make sure that you know your place, She taunts Her sissy whore
The cruel words that she says to you cause you humiliation
To earn the right to taste her pussy is your inspiration
She says "You have done well for me, and I will tell you what
Eat my pussy, do it right and I will take your butt
But that is all that you can have, for I will keep you locked"
You hoped that you could get inside, but you have just been blocked
The sissy that you are right now is starting of grow stronger
If only you could have your way, this moment would last longer
With Mistress fully satisfied, she tells you it's your turn
"I'm gonna make you cum this time. It's high time that you learn"
She drills your hole relentlessly. That's how it's meant to be
She makes you have a sissy cum locked up in chastity
The sun comes rising up again to start another day
You put the sissy up once more, still wishing she could stay
Cheer up Mr. Sissy Macho Man. Nobody knows
One day you can be out and proud as was always meant to be
Tell me how it feels to sleep securely gagged and bound
You can't portray the macho man. He's nowhere to be found
You struggle to keep sissy feelings buried deep within
But this is not a fight that you are ever gonna win
To all outside this special place, you are the manly dom
But dressed up in such frilly things, that manly man is gone
Your Mistress now is here for you, so much to your delight
But you know what that really means, you'll be her bitch tonight
Your girlie dreams won't go away, not matter how you try
That manly man facade you have is nothing but a lie
Your Mistress has secured you now, you're tied up to a chair
Her dildo shoved right in your face, you suck without a care
You worry what your peers would think if they could have a look
The life you've built now gone away, and this is all it took
You beg and plea for her to stop, "Please sissy, leave me now"
But all she hears is, "Welcome back dear sissy, take a bow"
With Chasity and anal plug, and you so cute in white
Your Mommy Domme has dressed you up. You're really quite a sight
You feel the guilt and all the shame, but is it such a crime
Deep down inside you know you wish that she could be full time
Your Mistress tells you to your face your noting but her bitch
The macho Dom is just a lie. You are a sissy switch
She takes the gag out of your mouth, "Now tell me what you want"
Desperation as you cry, "Use my ass as a cunt"
She moves you over to the bed, your ass up in the air
You beg your Mistress, "Do me now. Please stick it inside there"
She asks "What will you do for me? You're selfish, there's no doubt"
You know what she wants as you say, "Please let me eat you out"
She holds your words against you as she says you have no class
"I'll tell you want my sissy pet, I'll let you eat my ass"
Where is that manly man right now, he seems so far away
You stick your tongue into Her hole to prove that you'll obey
Your sissy tongue works all around Her sexy, tight back door
To make sure that you know your place, She taunts Her sissy whore
The cruel words that she says to you cause you humiliation
To earn the right to taste her pussy is your inspiration
She says "You have done well for me, and I will tell you what
Eat my pussy, do it right and I will take your butt
But that is all that you can have, for I will keep you locked"
You hoped that you could get inside, but you have just been blocked
The sissy that you are right now is starting of grow stronger
If only you could have your way, this moment would last longer
With Mistress fully satisfied, she tells you it's your turn
"I'm gonna make you cum this time. It's high time that you learn"
She drills your hole relentlessly. That's how it's meant to be
She makes you have a sissy cum locked up in chastity
The sun comes rising up again to start another day
You put the sissy up once more, still wishing she could stay
Cheer up Mr. Sissy Macho Man. Nobody knows
One day you can be out and proud as was always meant to be
Labels:
CD Wardrobe,
cross dresser,
cross dresser Wardrobe,
crossdresser,
crossdresser shopping,
crossdressing,
Domme,
dress up,
dressup,
femdom,
feminization,
Mistress,
sissies,
sissy,
T-Girls,
transgender
Sunday, September 22, 2013
A Poem: A Sissy's Dilemma
A Sissy's Dilemma
A captured sissy's view
You have my hands tied behind my back.
You've taken all the power that I lack.
To win your heart, was my only goal.
And now you've managed to take control
All I ever wanted was to be there for you,
to help you make all your dreams come true.
But since the day you got back on your feet,
your secret master plan is finally complete.
You have a unique talent that fits a special niche.
And when you want to let Her out, She is a bossy bitch.
And now it seems that I am trapped within the game you play.
The only option that I have is that I must obey.
You tell me how it's gonna be, and that I have no choice.
I'd answer you defiantly. It seems I've lost my voice.
You drugged me and then tied me up securely to a chair.
And with a ball gag in my mouth, I sit in such despair.
You say you want a sissy sub, and I will soon be it.
You'll lock me into chastity for what you call my clit.
The punishment will be severe if I do not obey.
With ball gag still inside my mouth, there's little I can say.
I really should have shut my mouth with my sissy desires.
For once you heard the things I said, you took time to conspire.
This was the moment that you knew that I would soon be yours.
Obedient 'lil sissy sub at home to do your chores.
You tell me of the spankings coming if I dare talk back.
To drive that point right home to me, my face receives a smack.
You tell me that no longer will I wear my male clothes.
Pretty female clothing is the life you will impose.
One point that you drive home to me, time and time again.
I will perform "services" for you and all your friends.
Intercourse with you I will not get. I'm out of luck.
That's the fate I must accept. I am your sissy cuck.
You tell me life won't be so bad if I will just give in.
the sissy who will serve you right will be your bestest friend.
Make no mistake your sissy sub will need to know her place.
For what she does reflects on you, I must not bring disgrace.
You tell me I must sit and think while tied down to that chair.
And you have something you must do, so you will not be there.
The thoughts come fast and furious. I know now what to do.
When you come back, I start to cry and say I will serve you.
A captured sissy's view
You have my hands tied behind my back.
You've taken all the power that I lack.
To win your heart, was my only goal.
And now you've managed to take control
All I ever wanted was to be there for you,
to help you make all your dreams come true.
But since the day you got back on your feet,
your secret master plan is finally complete.
You have a unique talent that fits a special niche.
And when you want to let Her out, She is a bossy bitch.
And now it seems that I am trapped within the game you play.
The only option that I have is that I must obey.
You tell me how it's gonna be, and that I have no choice.
I'd answer you defiantly. It seems I've lost my voice.
You drugged me and then tied me up securely to a chair.
And with a ball gag in my mouth, I sit in such despair.
You say you want a sissy sub, and I will soon be it.
You'll lock me into chastity for what you call my clit.
The punishment will be severe if I do not obey.
With ball gag still inside my mouth, there's little I can say.
I really should have shut my mouth with my sissy desires.
For once you heard the things I said, you took time to conspire.
This was the moment that you knew that I would soon be yours.
Obedient 'lil sissy sub at home to do your chores.
You tell me of the spankings coming if I dare talk back.
To drive that point right home to me, my face receives a smack.
You tell me that no longer will I wear my male clothes.
Pretty female clothing is the life you will impose.
One point that you drive home to me, time and time again.
I will perform "services" for you and all your friends.
Intercourse with you I will not get. I'm out of luck.
That's the fate I must accept. I am your sissy cuck.
You tell me life won't be so bad if I will just give in.
the sissy who will serve you right will be your bestest friend.
Make no mistake your sissy sub will need to know her place.
For what she does reflects on you, I must not bring disgrace.
You tell me I must sit and think while tied down to that chair.
And you have something you must do, so you will not be there.
The thoughts come fast and furious. I know now what to do.
When you come back, I start to cry and say I will serve you.
Labels:
CD Wardrobe,
cross dresser,
cross dresser Wardrobe,
crossdresser,
crossdresser shopping,
crossdressing,
Domme,
dress up,
dressup,
femdom,
feminization,
Mistress,
sissies,
sissy,
T-Girls,
transgender
Sunday, September 15, 2013
A Response To A New Mistress Looking For Ideas
I happened to write a lot over at Club Sissy in response to a new Mistress looking for ideas of what to do with Her sissy. First, Miss Rachel's post:
Hey all! I have been with my sissy boy for about 3 months now. I am completely new to this whole sissy/mistress thing. I feel like I need some new material/scenarios/story ideas or just about anything. Here are some things that my sissy and I enjoy...
Talking about dressing up/make up
Stories about pimping her slutty ass out on the street corner
She LOVEESS cum so a lot of talk about that
She loves her pussy (asshole) fingered and fucked like a dirty whore
Compliments about how pretty she is
Loves black men
Talk about getting used like a slutty fuck toy
Etc etc
There's a lot more but can't think of all of it right now. I just feel like I need more material. I'm planning on getting a strap on and buying a collar and leash...I'm gonna glam up the collar and write "sissy cum whore" on it...
But anyone have any other ideas based on what I wrote?? Thanks!
So a sensual Mistress? What a lucky Sissy. Maybe I'm not really in a position to answer too much here. I may be entering into a D/s relationship, and it's causing me to analyze things so I know how we would both proceed. I'm new to it, but I have written about it and respect the lifestyle. A lot of things are running through my mind now.
Back to your post, since it sounds like you are beginners and that's what I will be. Writing fantasy doesn't count... ;)
Chastity. I personally don't have the problem of being controlled by what's inside my panties, but I'll submit to this nonetheless. It's an act of submission and devotion to Mistress. Sissy's cum should be controlled by Mistress. The pleasure of Mistress comes first, always.
Plug your sissy. She needs to be ready for that strap on, so a small or medium butt plug to start with.
While she's locked, she needs to learn to be attentive to Your needs. This means she should become a good oral sissy for You.
Have her do things for you. Go get you a drink, fix you something to eat, massage your feet. She needs to learn to be attentive Your needs.
Additionally, get her a Maid's Uniform and make her serve you and clean house from time to time. Maybe have a guest over who is into this, just to show what a good sissy she is.
Light bondage. Not everybody's thing. Maybe start with arms restrained to the bed or something. Hand cuffs. Nothing too severe. But she's not going anywhere while you are gone. You can take it up a notch if you both like it.
Add to the excitement by plugging her and locking her in chastity first. Then, go where you need to go.
Discipline your sissy. Does not have to be hard pain. A nice spanking here or there. Add some verbal reinforcement to it to make your point clear. She needs to learn how to please Mistress and not to disappoint Her.
Various degrees of humiliation, start light. Maybe a few comments here and there in pubic. Maybe she has lipstick on when you go somewhere or some female clothing. This does not need to be near home if you worry about being seen. Then take it from there.
Another level. This isn't everybody's cup of tea. Not sure how I would feel about some of it...
Take sissy to a truck stop or adult book store or some place dressed up and make her orally service a man. If you are already talking about it, why not?
Mistress may need a man to please Her while Sissy gets to watch in chastity. Sissy attends to whatever Mistress and Her man need, and that includes oral or more if requested.
Most importantly, talk this stuff out before you start a scene. It must be understood that Mistress calls the shots once the scene is in play. No topping from the bottom, or sissy trying to change the rules mid scene. This is about BOTH of your happiness, not just sissy.
I hope something here helps, and best of luck to both of you.
I assume sissy still portrays as a man in public, due to work obligations? I'm out full time dressed.
Other ideas
1-Sissy wears panties and cami underneath male clothes. Cami may not be as easily detectable as a bra, but Sissy will be reminded of her place. Stockings and garters can be added.
2-Paint her toe nails. A pretty pink or red should do nicely. She will have shoes on, but she will know. A ritual will be for her to take her shoes and socks off immediately upon coming home.
In fact, painted toe humiliation can come into play if you want, where she wears flip flops from time to time in public.
3-Take her shopping with you for female clothes for both of you. Get her to participate in it. When you pick something, ask her what she thinks, why she thinks that. This can be done a town over from where you live if needed, but it can be a good D/s bonding experience I think.
3a-Mistresses have been known to tie a sissy up, go out and buy an outfit for the sissy, making sissy wait plugged and in chastity for quite some time.
4-Send her to the store for an errand with a plug inserted. It will be a reminder to her who is in charge, and she won't dawdle. She'll be sure to get what you want and get home.
4a-Take it up a notch by having her buy your feminine hygiene products or makeup or other items while plugged and with lingerie underneath her clothing.
5-Make her wear lingerie to bed if she doesn't already. She is a sissy after all.
6-Make her smooth all over, A full body wax, shaving, hair removal creme. Unless she is in a spot where she really can't, and these days men go hairless too. What this does is heightens her sissiness and makes her silky feminine under clothing feel that much better to her.
7-If she doesn't have a feminine name, give her one. Maybe you both discuss it, or maybe you pick one. If you are feeling nice, you can let her pick one.
Since you are in a sense bringing a new sissy into the world, it's only fair you name her.
8-What do you want from this? Sissy is loving this treatment I bet, so what do you want her to do for You?
Tease and denial, meaning no cum for Your sissy. Having sissy paint Your nails for You. Really, the only limit is what you two want to do.
This is mostly pretty mild stuff compared to where it can go, but that's for each D/s couple to determine. There's NO wrong way if you are both enjoying it.
Hey all! I have been with my sissy boy for about 3 months now. I am completely new to this whole sissy/mistress thing. I feel like I need some new material/scenarios/story ideas or just about anything. Here are some things that my sissy and I enjoy...
Talking about dressing up/make up
Stories about pimping her slutty ass out on the street corner
She LOVEESS cum so a lot of talk about that
She loves her pussy (asshole) fingered and fucked like a dirty whore
Compliments about how pretty she is
Loves black men
Talk about getting used like a slutty fuck toy
Etc etc
There's a lot more but can't think of all of it right now. I just feel like I need more material. I'm planning on getting a strap on and buying a collar and leash...I'm gonna glam up the collar and write "sissy cum whore" on it...
But anyone have any other ideas based on what I wrote?? Thanks!
Of
course, I had a lengthy response.
So a sensual Mistress? What a lucky Sissy. Maybe I'm not really in a position to answer too much here. I may be entering into a D/s relationship, and it's causing me to analyze things so I know how we would both proceed. I'm new to it, but I have written about it and respect the lifestyle. A lot of things are running through my mind now.
Back to your post, since it sounds like you are beginners and that's what I will be. Writing fantasy doesn't count... ;)
Chastity. I personally don't have the problem of being controlled by what's inside my panties, but I'll submit to this nonetheless. It's an act of submission and devotion to Mistress. Sissy's cum should be controlled by Mistress. The pleasure of Mistress comes first, always.
Plug your sissy. She needs to be ready for that strap on, so a small or medium butt plug to start with.
While she's locked, she needs to learn to be attentive to Your needs. This means she should become a good oral sissy for You.
Have her do things for you. Go get you a drink, fix you something to eat, massage your feet. She needs to learn to be attentive Your needs.
Additionally, get her a Maid's Uniform and make her serve you and clean house from time to time. Maybe have a guest over who is into this, just to show what a good sissy she is.
Light bondage. Not everybody's thing. Maybe start with arms restrained to the bed or something. Hand cuffs. Nothing too severe. But she's not going anywhere while you are gone. You can take it up a notch if you both like it.
Add to the excitement by plugging her and locking her in chastity first. Then, go where you need to go.
Discipline your sissy. Does not have to be hard pain. A nice spanking here or there. Add some verbal reinforcement to it to make your point clear. She needs to learn how to please Mistress and not to disappoint Her.
Various degrees of humiliation, start light. Maybe a few comments here and there in pubic. Maybe she has lipstick on when you go somewhere or some female clothing. This does not need to be near home if you worry about being seen. Then take it from there.
Another level. This isn't everybody's cup of tea. Not sure how I would feel about some of it...
Take sissy to a truck stop or adult book store or some place dressed up and make her orally service a man. If you are already talking about it, why not?
Mistress may need a man to please Her while Sissy gets to watch in chastity. Sissy attends to whatever Mistress and Her man need, and that includes oral or more if requested.
Most importantly, talk this stuff out before you start a scene. It must be understood that Mistress calls the shots once the scene is in play. No topping from the bottom, or sissy trying to change the rules mid scene. This is about BOTH of your happiness, not just sissy.
I hope something here helps, and best of luck to both of you.
And I added in the next post
I assume sissy still portrays as a man in public, due to work obligations? I'm out full time dressed.
Other ideas
1-Sissy wears panties and cami underneath male clothes. Cami may not be as easily detectable as a bra, but Sissy will be reminded of her place. Stockings and garters can be added.
2-Paint her toe nails. A pretty pink or red should do nicely. She will have shoes on, but she will know. A ritual will be for her to take her shoes and socks off immediately upon coming home.
In fact, painted toe humiliation can come into play if you want, where she wears flip flops from time to time in public.
3-Take her shopping with you for female clothes for both of you. Get her to participate in it. When you pick something, ask her what she thinks, why she thinks that. This can be done a town over from where you live if needed, but it can be a good D/s bonding experience I think.
3a-Mistresses have been known to tie a sissy up, go out and buy an outfit for the sissy, making sissy wait plugged and in chastity for quite some time.
4-Send her to the store for an errand with a plug inserted. It will be a reminder to her who is in charge, and she won't dawdle. She'll be sure to get what you want and get home.
4a-Take it up a notch by having her buy your feminine hygiene products or makeup or other items while plugged and with lingerie underneath her clothing.
5-Make her wear lingerie to bed if she doesn't already. She is a sissy after all.
6-Make her smooth all over, A full body wax, shaving, hair removal creme. Unless she is in a spot where she really can't, and these days men go hairless too. What this does is heightens her sissiness and makes her silky feminine under clothing feel that much better to her.
7-If she doesn't have a feminine name, give her one. Maybe you both discuss it, or maybe you pick one. If you are feeling nice, you can let her pick one.
Since you are in a sense bringing a new sissy into the world, it's only fair you name her.
8-What do you want from this? Sissy is loving this treatment I bet, so what do you want her to do for You?
Tease and denial, meaning no cum for Your sissy. Having sissy paint Your nails for You. Really, the only limit is what you two want to do.
This is mostly pretty mild stuff compared to where it can go, but that's for each D/s couple to determine. There's NO wrong way if you are both enjoying it.
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