BIG changes happen on Fridays ;)

Friday 11/4/07

Started as any other day up at 5am give myself an enema put make up on (not too much just as Mistress Isabella likes it)then get dressed today i will be wearing hot pink lace bra and panties black leggings and a pink Vest Top with 4 inch black pumps i was also instructed to wear my hair up.
Downstairs i start getting Mistress Isabella’s breakfast and work clothes ready for 7.15am. Standing at the end of her bed at 7.15am i place a cup of coffee at her bedside move to the end of the bed and lift the sheets (it is a rule of Mistress Isabella that all days start and end well) and gaze at the women i have devoted my life to my Mistress is an athletic toned and tanned goddess with a shaven pussy with small lips and small clit.
I run my soft feminine hands up her inner thy feeling a small movement in my panties (very small) as my penis strains against my chastity device the dull ache is all to familiar to me now I move my hands to her uppermost thy and gentle part her legs the smell of her pussy intoxicates me I start by gentle kissing the top of her clit sucking and blowing on it then use the tip of my tongue directly on her clit suddenly I feel her hand forcing my face right into her crotch she then starts grinding herself against my face until she comes to orgasm once she settles down I begin cleaning her with my mouth then wipe the peach lip gloss off her lips.
As I stand up Mistress Isabella snaps her fingers and points to the stool in the room I immediately assume the position I always do at the time of day and pull my leggings and panties down straight away I feel an instant wetness as she applies lubricant to my anus and proceeds to insert a 5 inch long stainless steel butt plug inside of me (it meets little resistance) she leans over and kisses my ear very gently and says good morning Kara how is my little whore doing today? Very well Mistress Isabella how are you? unable to stop my voice quivering from excitement as I speak she says nothing as if I didn’t even exist and walks to the bathroom I quickly pull my panties and leggings up and sashay’ after her she sits on the loo with her legs spread and I eagerly sit at her feet she relives herself and I do my duty because it is a gift and privilege to drink from a Mistress.
As Mistress Isabella is showering and getting ready I move downstairs to start my house choirs I have to clean the windows today put a washing on hoover and spend an hour on the treadmill before Mistress comes home.
As I sort out the first part of laundry Mistress Isabella walks into the kitchen with a very large purple dildo in her hand (10 inch) places it on the table and beckons me over (I am not worried as she rode rather hard the night before and she likes me to heal up as she puts it between sessions so I was safe until at least tea time tonight) she f***efully grabs and gropes my small breasts (barely an A cup) she looks gorgeous in her tailored work suit and 5 inch court shoes So Kara these little things are coming along nicely aren’t they ? Yes Mistress thank you Mistress and I suppose you look passable don’t you I think it’s time you had a real man in your life what do you think? yes Mistress I live to please you Mistress very well then my friend Jason will be coming round tonight and to get him in the mood for fucking my brains out I thought he could break you in so you do exactly as he says as if it came from my lips do you understand ? yes Mistress good now fuck off and get to work and before I forget Jason can be rather difficult to accommodate so you may have open yourself up a bit (pointing at the large dildo on the table) yes Mistress.
I stood in the kitchen with my heart racing and my cock throbbing in its cage Mistress had left over 20 minutes ago but I couldn’t move how have the events in my life led up to this? Why did I enjoy this so much? To answer those questions I started to go over the events in recent years.
I was 18 years old when I met Mistress Isabella (10 years her junior at the time) working at a PR firm as a temp she was stunning perfectly dressed at all time and very flirty over the course of a few weeks she had completely seduced me she would call me into her office and make me go down on her on one occasion she made me take of my trousers I did as I was asked as she was my boss after all to reveal black lace panties and black hold up stockings I also had my toenails painted red that day (I have always been very effeminate my whole life but never had the courage to tell another person so this was the first person I had ever came out to someone and it felt very liberating to say the least) she looked me up and down and started to write on a piece of paper on her desk she handed me the note stood up and went face to face with me and said be here 8 sharp tonight or your are fired now fuck off and get back to work I pulled up my trousers and sheepishly left her office.
That night I went to the address it was a very large town house in the city centre I knocked on the door she answered the door wearing a red and black pvc cat suit with knee high boots and her hair in a tight ponytail she stood in the door way hands on her hips and pushing her ample chest out and in a very strict voice said if you step into my home tonight you will become mine completely mine I will do as i wish with you because I will be your Mistress now step forward and enter or fuck off and stop wasting my time.
Needless to say I stepped forward and so my real life began I quit my job change my name to Kara and began the long and painful road to feminizing myself for Mistress Isabella over the next year and half I would begin corset training learn how to dress as a female spend 3months at a time in chastity only to be denied release and spend another 3 months locked up (my record is 8 months 6days at the time of writing this) and learn how to please my Mistress.
Back in the kitchen on that Friday morning I was still shaking from what my Mistress had said to me because although I live to be fucked in my ass and love gagging on big dildos I did not want to admit to myself that I craved a real cock inside of me I trembled at the thought.
I tried to get on with my day as best I could try to think what I would ware for the first time with a man or if Mistress Isabella had already picked something out for me? And I started to imagine what Jason was going to be like would he speak to me at all? Would I be the first Trans girl he had been with? Was he really as big as Mistress hinted at? well its 1pm I have roughly 6 hours to process this then it’s going to happen whether I want it or not.

Love Kara xxx

100% (6/0)
Categories: BDSMFetishShemales
Posted by Sissy_Kara
9 months ago    Views: 914
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8 months ago
Youre so lucky to such a good Mistress to train you
8 months ago
Excellent story!
9 months ago
love this story