Where it all began for me and Madame S

It all began when I met Mistress (that was about 5 years ago); in the beginning W/we were a vanilla couple. Then one week-end W/we start talking about bondage (I said I liked it when I was all tied-up and being at Her mercy) and fetish clothing (mostly latex). W/we start by tying each other by turn then I started to ask a little more from Her. W/we went shopping and got some more ropes, ball gag, butt plug with tail, collar and leach, mostly for me. Thats what was happening mostly the first 4 years.
After 4 years I started to ask to go further and to treat me as a dog/puppy for an entire week-end. She did and told me that She liked it, the way She could control me but didnt understood yet why I was doing it and why I liked it to be controlled like that. She was open to try new things and was delighted when I was asking for some play time because of the power She had over me during those play time.

Then Halloween came and She dressed me as a gothic lady vampire with a very mini skirt + lady panty and all the make-up + fake boobs + Halloween wig (with the skirt so short I felt naked, She told me that now I know what women are feeling when men ask them to wear very sexy mini-skirt with a g-string and that I should get use to it sooner than later.) and She took pictures to show everyone that didnt see me that night and She sent a few of those pictures to my parents, family and friends (it was fun and humiliating at the same time, everyone on the street were looking at me and I had to go get candies.). After that I tried almost all of Her clothes in front of Her, She said the part She like the most was when I tried Her g-string and Her clothes fitted me like a charm since I have a thin body and Im small. Her clothes are size small and x-small. Even my own clothes are small size. She said thats because I have a feminine figure. Not too muscular, not too skeletal either, She says I have nice curves.

 

W/we started talking a little bit more about puppy play and the fact to dress me as a gurl; I look around on the internet and discover BDSM. I was looking at some BDSM practice and I realize that W/we were doing it.

A few days after Halloween, I started talking to Her about me submitting myself to Her completely so She’ll have complete control over me. One night I was looking at the CB6000 and She asked what it was for, I told Her about chastity and then She ordered me to buy the CB. After receiving the CB6000 and wearing it for a few days, She asked me to look for more chastity devices and I found one that She love and asked me to start saving to buy it. It’s the Neosteel she-male waist belt and a few accessories. She-male belt because it’ll be more discrete under clothes, especially woman clothes.

One day W/we went to a sex shop to look around and She bough a crop. I had to go and get some books and lub at the sex shop a few days later.

Later I talked to Her about some ideas about D/s. The next morning She cut with scissor my underwear and W/we went shopping for some nice panties and later more sexy panties (g-string and tong) and bras. I became Her little slut that day and She like to call me Her little slut and She named me Cherry. So I’m Her Cherry little slut.
Since that day I have to wear panties and bras everyday even at work since I don’t have anymore male underwear except maybe a few socks.

I stared looking for piercings and tattoos, then She decided of a tattoo and the place it will be. Then I asked Her if She wants me to have more tattoo or piercing. She said to make a list of all the piercing available for me. I showed Her the list and decided ears (I already have 3 holes in my left ear), navel, guiche and PA. My first tattoo, Guiche piercing and PA piercing are done but She wants to do something special on my right ear. Since ears piercings are visible, W/we put a hold on it/them because of work. W/we are now looking for the navel piercing, maybe multiple navel piercings so I could wear a special jewelry. She already knows the next tattoo I’ll get but not now, later. For my piercings W/we decided GA10 slave ring for the guiche and a GA8 curved barbell and a GA8 slave ring for the PA piercing.

I got my hand on the flat2fem program and W/we decided I was to try it. It’s only natural herbs, so little risk there, then She asked me when I’ll be like 65+ years old (I’m 32 now) what about my boobs/breast, I said what about them? I’ll still play with them.
So far after 3 months I’ve grow about 2.5”, they seems fuller and firmer than before. When I started I was about 34” and now I’m 36.5” and still growing. I have started this program very slowly, the first 4 weeks I was only doing the chi massage without the cream and no natural herbs after that I gradually start to take natural herbs while doing the chi massage without the cream a few times a day and I’m using a snake bite kit on my nipples. I’m preparing my fenugreek extract to add cream to my chi massage eventually.

 

Mistress is now looking for a pony suit, head harness, 4 hooves, saddle and more She wants to ride me and train me.
She asked me to start buying parts to build a DIY milking machine after seeing the plan on the forum.
She said that the milking machine will serve Her well and She plan to use it while I’ll be in full pony gear and all tied up like an animal.
She told me that She has a few plans this summer concerning a few events for me to go as a gurl with a nice dress, high heels, wig, make-up and more.
She asked me a few weeks ago to start looking for 1 strap-on. 1 for Her to use on me. For some ass play and maybe torture, since I kind of like pain and She likes to give it to me. She uses a crop, cane, ruler and so on for some butt whipping.

She likes when I worship Her feet, when I kiss them and even lick them but She still doesn’t have the reflex to ask for things like that.

In one of the book I bought, there are a few ideas to build our own toys. W/we went to the leather store and bought a few items. Now I have the task to build my own leather cuffs. I already bought locks 8 smalls and 8 a little bigger for a total of 16 locks.

W/we start buying toys and W/we use them regularly. The toy She like the most is the leather straitjacket. She likes it when I’m all tied up and can’t defend myself.

I must be careful what I show Her, because She always asks me to get the one I’m the most afraid of. Because of that She started to do some CBT and more cropping.

She has a few toys plans/projects for me to build, like a bondage pony, a St-Andrew cross, spreader bars, yoke and more…

When W/we started officially our new way of life (24/7 D/s relationship) a few months ago and set the rules She decided that I have to take care of the chores like laundry, dishes, floors, bathroom cleaning and taking out the trash. Then She set a few restrictions like bathroom control (I must ask permission before going to the bathroom and I have to pee like a gurl, I must sit down and leave the seat down), clothes choosing, soft-drinks limits and She even decide when I have a treat like chocolate.
When She cut my underwear, She start dressing me with more feminine clothes like some t-shirts, panties, bra and now some women jeans and leggings. Sure I have a few skirts and dresses, but I don’t wear those outside, I mean the women jeans are now part of my regular wardrobe.

 

I remember the first time I talked to Her about this way of life, She said that W/we’ll try for a few weeks and see. After 2 months I asked Her if She wanted to stop having a slave/sub and go back to the way W/we were before. She replied: “The answer is you’ll be my slave forever and if you ask that question again I don’t know what I’ll do yet but you’ll regret it, it’ll hurt so much and be so humiliating that just thinking about it will make you shiver with so much pain that you’ll regret thinking about it. Is that clear?” “Yes Madame.” Was my answer. Just to make sure She sent me one night to buy Her a chocolate candy bar all dressed as a gurl with only lipstick for make-up and I was dressed with one of Her Skirt with pantyhose, wig, woman handbag, woman shirt and a pair of too small woman shoes, so when I came back home my feet were hurting like hell and my nails even short cut my toes and I was bleeding, hopefully not too much. She said to me that night that I passed Her first test of obedience and that I was a good gurl.

One night I was asking Her what to do with my hair, She said that She didn’t knew, so as a joke I told Her to shave my head and eyebrows with a razor. So She did and She said that was the last time I was to cut my hair and that I have to let them grow as long as I can with maybe a change in my hair color, something maybe more feminine.

One of the things She likes the most about my change is my French maid costume and I do some of my chores in it. That’s part of my feminization and I like it. I’m only missing a pair of high heels but W/we’re going to order some soon, a pair with a lock at the ankle. I do have a pair of ballet shoes and She likes it when I’m wearing them but I still can’t walk in them, so I have ordered foot trainers with locks to add to the torture.
Since She starts feminizing me I have to shave my body hair and I’m looking for a home electrolysis kit for permanent hair removal.

W/we’re beginners and W/we’re always looking for new ideas and new ways to torture me either with pain, bondage, chastity or mental and new ways to control me. I have to make nearly all of the research for my own torture and misery. That’s the best way to feel inferior, humiliated and controlled (doing the research and building the toys). W/we don’t really know any others like U/us personally and W/we haven’t gone to any fetish event yet but its plan for some events this summer. Neither of U/us have experience in a D/s lifestyle but She still surprises me once in a while with something I wasn’t expecting like once She asked to go with Her to the bathroom and asked me to lie down on the floor fully naked then She almost sit on my face with no panties and She said “Oh, you’ll have to clean the floor.” And the first thing I knew I had the privilege to receive my first golden shower and scrubbing the bathroom floor while still being naked and all wet from the golden shower, so every time the floor was clean I had to clean it again until I was dry and scrubbing for the last time the floor right before She said it’s time for the shower and then I took a cold shower (too cold for my taste) to clean myself.
I have a strong character and She said that She’ll enjoy to break me and to make me Her bitch. She still enjoys a nice and long bondage session every now and then.

 

More to come...

If you have any comments, don't hesitate to ask!

:loveCM:

 

Thank you Miss D.

It's easy for me to accept my feminization since I have accept my feminine side but it gets harder for some traits or modifications because of my job.

W/we want to pierces my right ear, let my hair grow and change color, maybe some corseting and a few other things.

I have a slim and feminine body, I'm 5'9", 130 Lbs and 34-28-34.

Edit: about the maid pictures, it shouldn't take long because I have no high-heels and I'm missing some make-up.
Don't worry W/we're going to take some soon because W/we want to change my avatar for a picture of my french maid costume.

 

Small update.

Mistress decided that She wanted to have some fun tonight with me and my ass.
First She cuffs me with my hand behind my back then blindfolded me and add a ball gag.
She previously asked me to prepare the bed, to cover it with a black PVC sheet.
Then She ask me to get in the bed on my knees then She uses the collar and leach on me then push me on the bed face down. And now with my butt up She uses a lot of lub and Her vibrating dildo...

Ouf... So after about 40 min of pounding my ass and slapping my balls just before I had the chance for an orgasm... She stop and left me in bed all tied up, She puts Her wet panty on my head with the wet part on my nose...

After 30 min in bed She comes and told me to put this update on Chastity mansion.

But just before untying me She removes Her wet panty from my face, turn me on my back, removes the ball gag and sit on my face so I can clean up Her nice wet and juicy pussy.

Wow... Nice teasing session, I was on the edge of an orgasm then She stops, leaves me there and come back 30 min later to tease me again with Her nice juicy pussy in my face but still blindfold.

She says I'm gonna get it this week-end...
I'll keep you post if I have enough liberty....

Sissy Cherry

 

I had to take a few pictures of Mistress in Her latex outfit for Her profile this afternoon.

Then I had to edit and put them on Her profile as private (to friends only).

After that I was allowed a little spanking.

 

ouf... what a week. Mistress kept me very busy all week.
It all started last Saturday, in the afternoon She looked at me and told me to go get my collar and leach. Here goes the little puppy for the week-end. I slept at Her feet. Sunday morning She removes my collar and told me to do my chores. I had to do my chores and some extra cleaning all week.

Nothing much to report for now...

I'll keep you update...

 

WOW... what a week-end Mistress put me trought...
First Saturday morning She put me in my Straitjacket then She tied a rope from my straitjacket to the wall and She was naked on the couch in front of me and start playing with Herself to tease me...

After a few minutes She gave me a viagra pill and wait until it start to take effect.
Then She removes my straitjacket and started playing with me, She was teasing me to the max until I was on the verge of exploding then She stop.
She then told me to follow Her to the bedroom and get in the bed...
I was allowed inside Her to please Her until She had enough without cumming of course.
She play with me and teased me so much that when She said I could have an orgasm, I did had an orgasm but I didn't came... so it looked more like a female orgasm.

She said "good gurl, it'll be easy to clean. Hope you had fun!"

And Sunday came... She left me at home very hard and horny while She went shopping with Her sister.

I need a lot of rest from my week-end.

Cherry

 

I'm all alone now...

Mistress took the week off with Her family, they went camping and She left me home with a very long list of chores to do...

Yesterday I was walking downtown and came across a small shop with high-heels with locks, so today I'm going to go and get them...
It'll be a big surprise for Mistress when She returns.
It's one of the few items I don't have and Mistress asked me to buy.

Cherry

 

Thank you Miss D, I went to the shop for the high-heels and they didn't had my size... the saleman told me he could order my size but he needs a deposit... The thing is the shop is very small, I didn't trust it to order the shoes since they had a sing in the window of the shop saying for rent...


And don't worry about playing with myself, I don't have the time for that... too much chores to do! when Mistress left, She said since I don't have my cb, She trust me and if I'm a bad boy I'll regret it but if I good I'll get a reward.

-Cherry

 

For the PA, Mistress told me it was not very different, a little more sensation... but I read somewhere that with a bigger gauge ring She'll have more sensation and pleasure.

If your Mistress don't like it then you could remove it when having sex and putting it back on after.

My Mistress like my PA not only for the sex part but also all the other things She can do like a leash, tying me with ropes and passing one end through my PA just to make sure I won't try to escape... there's a 1001 usage you can do with a PA other than sex related...

She likes to tease me while playing with my PA ring only...
She can use your PA to secure a CB.

My Mistress says She's having more fun playing with my PA ring than having sex, because of all the control She gets... She can attach a leash and pull me by my clitty to follow Her and do everything She says... She can lock my PA with a small lock to a chair or something else and leave me there alone while She's doing something else.

And while Mistress was away I tried my CB with my ring. It was nice to have it back on again but my PA ring is large (18 or 20mm) and was interferring with my CB-6000, couldn't keep it more than 24 hours.

-Cherry

 

Last week-end W/we found a nice pair of black patent 5" heels for my size...
I've spent a few hours in them each day since I got them, it's not easy walking in high heel.
I had a promotion last week and now I'm working more and I must invest some of my time when I'm home. Mistress is please even if She's not able to tie me when I get home, I have my chores to do and invest a little time during the week for my job. At least I have my week-end free.

-Cherry