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6 months after being discovered Crossdressing by my grandmother at the age of 16,and under her rigourous Feminisation training after she told my mother i should move in with her instead, I wake to find a note on the kitchen side when i begin my morning cleaning.
"Debbie, Today you will have the Day off chores, Aslong as you make the living room spotless. Then You shall bring my my breakfast earlier then normal, and Run yourself a Bath. I will let you know why On Arrival of my Breakfast.
Love, Grandma."
Slightly curious as to what the big suprise was, as instructed i go into the living room, dusting, polishing, Vaccuming, Fluffing cushions, and general tidying away. Then back to the kitchen to prepare Grandmas breakfast, 2 slices of toast, lightly done, With a bowl of cereal.
Carrying the Tray and Carefully as i can, in my Maid outfit Heels, up the stairs, and into my Grandmothers Bed chamber. Where she laid, almost expectantly, Sitting up, in her silk pyjamas, hair already neat, Looking me dead in the eye as i mince into the room, and place the tray on her lap.
"Debbie, Sit beside me on the bed"
"Yes Grammy", as i do so, i smooth out the underneath of my skirt, like Grandma taught me, many months before.
"Debbie Today is 6 months to the day youve been under my instruction, and i think we have made magnificent progress, Accordingly, i think its time we celebrated, So tonight we shall be having a party."
"Oooo yay" i excitedly giggle.
"I have already invited all the guests, Many of the girls i play bridge with, some old friends of mine, and some people from the social club i like to go to, All coming here to meet my wonderfull little Granddaughter. So for Today, You will Bathe, Have a Nap, And then we will begin getting you ready for the evening, Understood Debbie?"
"Yes Grammy" i say with a smile creeping across my Rosy cheeks.
"Well then go get into your bath and i will be there once i have finished my breakfast"
"Yes Grammy", as i stand up off the bed, and tiptoe out of the bedroom and across to the bathroom, Removing my Right Maids corset, Tights, Skirt, and Heels, and sink into the bathtub. With Lavenda filling my senses.
Before long Grandma had finished her Breakfast and Came to wash me in the bath, Rubbing me the the girliest fragrances we had, Washing my hair,making sure im fully shaved, and giving me a very sweet smelling enema, before putting in the routine buttplug, and removing me from the bath.
"Good girl Debbie, Now you know the routine for Naptime." She whispered as she led me by the hand to my bedroom, or for better words, Nursery.
With no prompting, i slid the adult diaper up my soft smooth legs, put the pacifier in my mouth, got onto my knees infront of grammy, so she could tie the ribbons behind my head. Then then also brushed my hair for me, and put it into Pigtails, before she motioned me towards the adult sized Crib, Tucking me in, and locking the bars, she wound up the mobile, and left the room.
The gentle chimes sending me softly to sleep.
........
"Debbie!"
My eyes slowly open to see Grandma over my crib.
"Time to begin getting ready hun, Come on, Chop chop" With that she lowered the bars of my Crib, and untucked my sheets so i could get out. I then get out of my crib and bend over on it, so she can check my diaper.
"Oh Debbie, Bad girl, Wetting yourself before your big party, no matter, I thought it may happen and prepared for it.", She pulled me by the hand and changed me, Still with the Pacifier in my mouth, so i am unable to speak.
Wiped, Powered, and put into a Fresh diaper, Grandma sits me up and Unties the pacifier.Shortly replacing it with an oversized baby bottle.
"Drink up debbie, youll need it for the party later"
Baffled by what she meant that i will need it, i guzzled it all down, to then be burped, and led to my closet.
"Since it is a special day for you Debbie, Grandma has bought you a new outfit, as she pulled out a Zipped up coat hanger. "But i want it to be a suprise, so for now debbie you must wear this", pulling out a eye mask that says "Sissy" in soft script writing across a fluffy hot pink background.
Slipping it on, my world goes dark, and all i feel is grandmas hands guiding me into an outfit.
I feel panties going over my diaper...
Then a pair of thigh high socks or stockings, its hard to tell with the mask on...
Arms foward, so Grandma can strap a bra on me...
Then lifting up my arms, i feel the softest dress fall down my body, before i feel the middle being pulled in tight by ribbons at the back...
Finaly i get sat down on a little stool as Grandma slides my feet into some heels. They are very uncomofrtable, and feel almost the highest ive ever worn, Again grandma does them up really tight.
Finnaly i feel Grandma tie something behind my neck, and she pulls off the mask.
My eyes now blurry as they begin to focus , i look down, to see a cover over my clothes, like what you wear at the hairdressers, but it goes all the way to the floor.
"I told you debbie, its a suprise, Any peeking, and you know the punishment Debbie, Now go back to your room, and get the makeup bag out, Theres a few more bits i need to sort out"
"Yes Grammy", struggling to walk in such high heels, with a cloth infront of them... i slowly made my way to my nursery/bedroom, sat at the dresser, and got all the makeup bags out of the drawers, and patiently waited.
Grandma soon returned, with a few things in her hands which i couldnt see, placing them on the dresser. She then turned me facing away from the mirror, so i couldnt see myself, and processed to do my makeup...
Rosy red Cheeks.
Bright red lips.
Heavy mascara to bring out my eyes
And light pink eyeshadow.
She then trimmed, filed and painted my fingernails the same shade of pink as the eyeshadow i saw her put on..
"Thankyou Grammy" i said, as she started packing away.
"Your welcome debbie, now time to do your hair she said, grabbing the hairbrush, she took it out of pigtails, reburshed it all, and did it, almost exactly the same however this time, she gave me a small block fringe..
"Perfect" she said just as she finished..."Now for the finishing touch" she said reaching to the dresser behind me, grabbing the object she had brought into the room with her. she then pushed it around my neck, and i heard it click at the back.
She then turned me around in my dresser, and there sat the prettiest girl, with Rosy cheecks, Long blond Pigtails, tied in tight little pink hairbands... with a little block fringe...
And around her neck, almost like a dog collar... in pink. My eyes drew to it in the mirror, Grandma noticing says
"It says 'Sissy Debbie, Owned by her Grandma, Does as she is told' Isnt that right Debbie"
"Yes Grandma" i squeeled in excitement
"Good girl, Now Debbie, before the party, i shall let you know the rules.
Although this is your party, You will be serving all the guests tonight. You will address them women as "mummies" and the men as "daddies", They are allowed anything to eat or drink as they wish, wheras you may only have what i give you, Understand so far Debbie?"
"Yes Grammy"
"Good girl, i knew you would. Also, You will be the evenings entertainment. I've told them all how well behaved you are, and all about your little routine. Alot of the women have said how they would love to change your diaper, so its likely that will happen. As for the men, Well they have different tastes. But you will give the guests whatever they desire, is that understood Debbie?"
"Yes Grammy, i will be a good girl, and serve all the mummies and daddies, everything they want."
"Good girl, while you were napping, ive prepared the food, and some of the drinks, They will be arriving Very soon, so we need to hurry, you will wait in the living room, Tray in hand, Ready to welcome the guests. On your way you may remove the cloak, and look at your outfit in the mirror in your closet. But dont take too long, grammy is off to get ready herself now."
As instructed, i went to my closet, and undid the cloak, letting it drop to the floor, i saw the most gorgeous outfit you have ever imagined. Bright baby pink dress, with Satin, And Gingham pattern all over, with bows, and ruffles, and a skirt that stuck almost straight out from the thick petticoat underneath. Just enough to show the bottom of my panties, also covered in ruffles and bows, and across the Bum, said "Cum drinker"
Now my eyes were as wide as a deer in headlamps. Never had Grammy made me wear something that said something to obscene and naughty.
I knew if i were to remove it, i would be punished... so i had to leave it on and hope to heavens noone would see what words i had across my bottom.
As i did one last twirl in the mirrow, i noticed something at the back of my dress.. edging closer to the mirrow i again, paniced...
It was a padlock... I was locked in this dress until Grammy said otherwise...
Now i didnt mind that too much, since it was a beautiful dress, However, the thought crossed my mind, if she lost the keys, and i would never leave it....
But i took a deep breathe and went and awaited my Grammy, and guests in the living room holding a silver tray of nibbles, ad gracefully as could be.
There was only one problem, my Tummy had began to Rumble..
Grammy then floated into the living room wearing a long black dress, her hair done niely in a sort of Bun, and had beautiful diamond earings...
"Well debbie do you like the outfit?"
"Yes grammy, i love it.... but...."
"But what debbie?"
"The panties say something naughty on them grammy..."
"Yes debbie, i thought you may ge funny with that, but its to amuse the man at the party you see, as i said, they have different desires to the women, and you will be serving all of them"
"Yes grammy"
"Also, my little angel, how is your tummy feeling?"
"A little rumbly Grammy.."
"Good, that bottle i gave you is doing its job then.... With all those women wanting to change your diapers, i couldnt let them waste clean diapers, so i laced your morning bottle feed, with laxatives... just in time for them to kick in soon, but it seems its already taking affect, no matter how bad your cramps get debbie, you will be a good girl wont you"
"Yes grammy" i said, panicing at what my body was soon to experiene, but before i could go deeper into any thought, The doorbell had rung, The guests were here....
As i said in my last story, i am new to writing, so brutal criticism is honestly welcome, i wish to improve, Also, if i do continue it, i would love to hear suggestions and ideas... This is a forum, its here for ideas.
Love..
Sissy Lil-Debbie
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