[waki86] the new journey .

[waki86]

Sissytober has come to an end.

Last Saturday Miss R and I went to another party.
A party we also went to last year.
People then celebrate the end of Locktober.
In the past month I have learned a lot from Miss R, but I have also discovered new things about myself.
That I also love being a Sissy.
And by dressing like this I find myself very sexy and exciting.
Miss R, on the other hand, also really enjoyed playing and teasing me like this. It did help that I also went along with it and worked very well with it.

To the party I wore a red corset and a short black tulle skirt that was open at the front.
Red net stockings with black garters, black high pumps.
A butt plug with a red rose on it, and my inverted cage with small red stones.
My hair was wavy, I had nice red lipstick on and long painted nails. And of course my breast prostheses were glued on.
I also wore a collar and Miss R also gave me a sissy name Wendy. So that it was much nicer to introduce myself.
Just like last time, I was only allowed to speak if Miss R allowed me to.
To introduce myself was to give a kiss and at the same time sink slightly to my knees.
It was a nice evening and we had a lot of fun.
Sandra and John were not there, they had other commitments. Miss R now wants me to be a sissy once a month, for a complete weekend.
Because we both enjoyed playing that game.

[waki86]

It is official.

I've been locked up for over a year now.
Miss R discussed the state of affairs over the past year yesterday. And she asked how I felt that I had not come for more than a year now.
And I'm locked up 24/7 only in the sauna and on vacation.
I said I liked it and didn't miss it.
Miss R laughed, I don't miss him either, it sounds like it's much better for both of us.
I said yes, I still enjoy it every day, it feels wonderful and protected. "It's nice to hear," said Miss R, "it looks good and beautiful on you too."
I think so too, the cage is beautiful.
Indeed, Miss R said mainly because you made new fronts.
Yes, I said. You have also changed a lot, for example Miss R said. In what way I asked her.
Much more subservient and you do everything I ask of you without grumbling.
That's because I love you, and I see how you enjoy it too.
That's right, Miss R said, whether you're sitting on the dildo or just walking around, I really enjoy my toys.
That's what it's all about, that we enjoy it.
Yes said Miss R and my orgasms have also become much better. You pay much more attention to it and sense much better what I need at that moment.
I also love doing it, sometimes I feel your orgasms myself.
And that just feels magical, I told Miss R.
And with this cage it feels much nicer when I use the strap-on dildo on you.
It's like I'm really fucking you without being able to cum.
Miss R smiled and said, then it was a good choice.
Yes, a very good choice on your part.

What would you think about making it permanent, Miss R asked me?
I said to Miss R that choice is up to you, it is your property.
That's right Miss R said it's my property.
But we have to agree together.
Let's say as long as you don't find it necessary to unlock me, it becomes permanent for me.
When you've had enough of it yourself, you unlock me.
After all, it is your property. I don't want to have to tell you later if you decide to call it quits.
We agreed permanently.
Miss R laughed, I don't need it, I also have another one at my disposal.
So it will be permanent, I said to Miss R.
Yes, it will be said Miss R permanently.
That's fine as you wish.
She gave me a kiss and said thank you for that.

We continue to talk about the past year and a half.
And how much she likes that she is now in charge of the relationship.
And I can make all her naughty dreams come true and I give her all that freedom.
I told her I was in charge for the first 20 years, and you also agreed to many things.
And it is nothing more than normal that the partner also gets the opportunity to make his desires and dreams come true.
And see together whether that will lead to something beautiful. Miss R nodded yes, can recommend it to everyone.

[waki86]

Expand more.

From the moment Miss R and I decided that chastity was going to be permanent.
Only later did I realize that it was no longer possible for me to have penis stimulation and PIV with Miss R.
I didn't think it would have any effect on me.
I was also a bit taken aback by that.
Miss R noticed that too.
I was no longer allowed to spoil her because I didn't behave well according to her.
Although I gave the right reason that I had to get used to it.
You said you haven't had any problems with it for more than a year.
Of course, I was hoping to get unlocked every now and then.
Miss R teased me about it and was only allowed to watch as she spoiled herself.
And not close by, but in my spot next to the fireplace.
When she used the dildo.
She came to me and put it in my mouth.
Make sure you wet it well so that it slides in properly.
When I was milked by her it wasn't over either.
She then grabbed the strapless dildo and put it in my mouth too. Make sure you wet it well so that it slides into your pussy.
She then fucked me until she came herself.
She really enjoyed using me like that, and said that's good training for you.
Enjoy it because that's what your pussy is there for.
For the first time she also came squirting a few times.

Sandra and John are coming next weekend. Miss R is looking forward to it, she hasn't had PIV for almost two months.
And I hope when she has had that again that I can spend more time with her again.
She has hinted at it.
If you do your best then...
Make sure you look tip top...
Do as you're told...
Surprise me with something special...
Then you have a chance to...

Although I know Miss R would prefer me not to wear panties as a Sissy.
Do I have a surprise for her?
I ordered Freutoy.
It comes from a German company and it is something that is a combination of butt plug and panties.
The butt plug has been developed in such a way that the front part of the panties can be clicked on at the foot with a click system. The plug is designed in such a way that it should fit comfortably and also be worn with panties.
I ordered a pair of panties with it.
A pair with an open crotch and a pair with a closed crotch.
I want to surprise her with that.
And that with panties on it will be fine if I'm a Sissy.
Let's hope she likes it.

[avid fan]

I hope your weekend is an exciting experience, and you serve Miss R, Sandra and John well!

[waki86]

I hope your weekend is an exciting experience, and you serve Miss R, Sandra and John well!

My panties and plug arrived today.
And showed them to Miss R
I had changed especially for her with bra, stockings and makeup. And she thinks it looks nice on me.
And she said that I have taken the right path.

[waki86]

Serve and earn.

Last Thursday I surprised Miss R with panties from Freutoy.
I had put on special make-up and put on lingerie with open crotch panties.
She said it was indeed more beautiful that evening.
And if she wanted it to last.
Friday morning she told me to take it off again because it wasn't a weekend.
And she thought I had to earn it to be allowed to wear it.
Because your pussy is also my property and I decide what goes in it, said Miss R.
And had to hand everything over to her.
I thought she would have really liked it, but judging by her reaction, she actually didn't.
Because according to her I didn't do it for her, but for myself.
So that I didn't have to use the dildo during breakfast and dinner. Even though I told her it wasn't true, she didn't believe me.
And I wasn't yet ready to wear it.
According to her, a Sissy who is still a virgin has no right to it.
And the weekend had to prove the opposite.
And when I had proven it, I would consider whether I could also wear the panties from now on.
Which meant also going to work with a bra.
I had better think about it carefully, Miss R told me.

Friday evening after dinner and when I was done with everything.
I went to my spot and wanted to sit there.
Miss R said what are you going to do, first dress yourself like Wendy.
Because I want to discuss things with her about tomorrow.
I went upstairs and got dressed. I was wearing the red corset with a skirt and the red suspender belt with red stockings and the plug with the red rose in it.
When I came downstairs Miss R checked me first.
I looked good according to Miss R but had to unplug.
Because that wasn't right now.
Even though I was Wendy now, I had to sit in my spot on the dildo. But before I went on I had to give him a good wet blowjob while crouching down.
I did what Miss R asked me and when she thought it was good enough I sat on it.
Miss R didn't say anything and did her own things and I wondered if she really wanted to discuss things with me or not.
When I'm sitting in my spot I'm not allowed to say anything.
After sitting like that for about an hour,
Miss R stood up and came back for a moment with the strapless strapon in place.
She stood in front of me and said let me see if you can give a good blow job.
She pushed it into my mouth and I sucked and licked it.
At some point she started fucking me in my mouth.
She took it out of my mouth and had to stand bent over at the coffee table.
She pushed it in without saying anything and fucked me.
Yes, she said, you are ready.
Thought what am I ready for then?
Had to go back to my place afterwards and Miss R proceeded to fuck herself with the strapless strapon until she came.
She then got a glass of wine and enjoyed it.
When she had finished it she came to me, gave me the plug and said come and sit with it.

Sandra and John are coming tomorrow and you know what John is coming for, right?
Yes, I said, I know.
Well then you know what to do, he will come for you too.
I also said asking questions for me Yes, Miss R said, you are still a virgin and you still want to earn your panties.
She grabbed between my legs, this clit deserves something nice too.
I actually said yes.
Well then Miss R said then you know.
You will serve us again just like other times, with snacks and such. I don't have to explain that anymore.
While she said that she was still playing with me.
And she squeezed my balls a little harder.
It would be nice if John deflowered you and emptied your clit.
So we can have a nice cocktail.
I said John should do that.
Of course John has to do that.
You're a girl too, Wendy. Yes I am, I admitted.
And maybe you can also lick me or Sandra clean.
Then I will consider whether you can wear the panties.
It's up to you how much you deserve them, Miss R said.

Last Saturday I wore the same clothes as to the last party. Although John took me, he did not empty my prostate but Miss R had to finish it.
After which I made a fruit cocktail.
Before John took Miss R and Sandra I have to prepare their pussies and guide John.
Because John had done everything right, he was allowed to cum in Miss R.
And then I had to lick her clean.
Although Miss R was satisfied, according to her, things had not gone completely well.
And I haven't earned the panties back yet.
She now wears them herself until I have earned them.

In two months I will have another chance to earn them.
This is because New Year falls in between and we are having a party with our friends again, just like last year.
Which will also be a theme.

[avid fan]

Amazing... would love a more detailed version of the events of Saturday if you find the time.

[waki86]

Amazing... would love a more detailed version of the events of Saturday if you find the time.

I will post in more detail this week about last Saturday evening.

[waki86]

Why things didn't go well last Saturday.

Apart from Saturday, Sandera and John came.
Miss R said that day, now you can prove that you are a good Sissy. In the morning I was busy getting ready.
Miss R did my nails, because I still have trouble sticking on the gel nails myself.
Then she did my hair with the curling iron.
She changed my front of the inverted cage.
I had made a special front so that when I am milked the fresh milk can flow out through a tube and be collected.
Before we went to dinner I had to suck a dildo.
She said tonight you can show that you can do it, she laughed. Then she satisfied herself with it.
And then it was my turn to put it in my pussy.
She watched me do it.
Hopefully it will work today if you are taken by John.
And then I was allowed to put in the plug with a rose. I
spent the rest of the afternoon making snacks.
Miss R had taken extra milk from the freezer.
When the doorbell rang around 7:30 PM I had to open the door and receive them.
Which was exciting for me.
They were amazed at how I looked with breasts and all.
Normally they enter through the garage and John also undresses there.
This is because according to Miss R a caged man must be naked in the house.
Now he was allowed to enter the living room fully clothed.
I had to undress him, which didn't go well with those long nails. And had to be helped.
And then he was given Viagra just like always so that he would stay stiff for a long time.
I had to take him to his place by the collar.
He had lubricated his dildo with lubricant beforehand.
When he was sitting and I had gotten coffee and cookies.
Miss R, take out your plug and go to your seat.
I did as Miss R asked, lubed up my dildo and sat down.
When I was sitting down, Miss R said, you haven't learned anything, Wendy.
I shrugged, not knowing what she meant.

What should you do first before you sit down? I still didn't understand what she meant.
Miss R told Sandra for a few weeks that i must first take the dildo in my mouth and wet it thoroughly.
And then she sits down and she pretends she doesn't know. Sandra said maybe she longs for a real one.
That may be true, but she should just do what she has learned. I already knew then that I wouldn't earn anything back.
Sandra, it will be exciting for Wendy and maybe she will make it well.
She chatted for a long time.
At one point Sandra came to me and gave me the key.
Now you can show what you've been taught and she winked at me.
Got up and walked towards John.
Opened his cage and took his cock in my mouth.
He soon grew.
And then grabbed him and said, he's ready.
Did you say she can do it, Sandra said.

Then I had to get the snacks and take John to them.
They played with John while they enjoyed the snacks.
And I had to go back to my place.
They were quite excited and undressed themselves.
Miss showed Sandra the panties with plug.
She loved it.
Miss R said I bought it for myself without consulting.
And that she told me I had to do everything right before I deserved it.
Sandra now understood why she was so strict.
John obviously enjoyed the attention.

At one point Miss R said to John are you ready to show Wendy what a real cock can do.
John looked surprised and looked at Sandra
She started laughing and said that was the surprise. I had to come and Miss R installed the tube.
Afterwards I had to bend over the coffee table...
And John started fucking me.
It was my first time being taken by a man.
And although I was surprised at how much I liked it.
John was unable to empty my prostate.
Whether it was because of John or because of myself, I don't know.
But because that didn't work, Miss R finished it.
Miss R was not completely satisfied with that either.
According to her, less came out now than the times before.
I prepared the cocktail for them and, like John, went back to my seat.
The ladies enjoyed their cocktails.
And left us alone for a very long time.
Meanwhile, they played with their pussies and talked about how wet and excited they were.
At one point I had to bring John over and give him a blowjob before he could take them.

First he took Miss R until she came and then Sandra.
Sandra also allowed him to cum.
Miss R told me to lick her clean.
Which I didn't do immediately.
She pushed my head between her legs and said Wendy that it is your job to clean thoroughly.
Although before I had licked Miss R clean when I came inside her. It was something completely new to taste and swallow another man's seed.
Even though John had come, he still remained hard for a long time.
Which they eventually used again.

Miss R asked the next morning how I felt about doing it.
And said I don't think well enough.
She said right you forgot several things.
And we still have to work on that, Wendy.
For now, I don't think you've earned the panties and plug.
She now wears it every day and has even ordered some panties that fit her better.
She says she does this to remind me every day that I have to earn them back.
But I think she looks very beautiful, sexy and exciting. And I think the longer she wears them, the less chance I have of earning them back.

[waki86]

Surprise for Miss R.


On Christmas Day I invited Sandra and John and her friend and her husband to join us for dinner.
Miss R knows we're having guests, but not who. I have put together a complete 4-course menu with game.
What she doesn't know is that her friend is already coming over for the weekend. It is also the friend who convinced her that chastity for a man is much better.
To surprise her even more, I will also be Wendy that weekend.
I know that she likes to see me like this and because this month I would be Wendy, during New Year's Eve.
And then not having the opportunity to be Wendy.
I want to surprise her extra with this.
I also told her friend that it should remain a surprise.
I don't know if her girlfriend now knows that I'm a sissy.
I expect it because her husband has been a sissy for a long time. But if that is not the case, the surprise will be extra big for Miss R.