sssy slaveboy gets trapped & trained Pt 4

So my new life as Empresses "girl" was cemented and had begun...
The Depo Provera had been injected a week ago to the day and the effects had taken hold in a big way.
Empress had not been in touch since that fateful day of my chemical castration and was clearly leaving me to accept my new role and what the future held for me.
My chest was beginning to swell and the hair on my body was changing and thinning out by the day.
The most noticeable effect was that my "cock" was now limp and lifeless and was now just a "clit". No amount of wanking or stimulation would get so much of a twitch from my once manly dick of which i had once been so proud.
My thoughts were no longer filled with sexual content and i had become more "girly" as each day passed since the jab.
It was clear Empress had done her research and i was now pretty much the impotent sissy she had intended to make me.
I also knew that many of these side effects would become ever more permanent with each injection that followed to the point where i would be a permanent enuch who would never have the pleasure of an erect cock ever again.
I logged onto my emails later that evening to see an email from Empress entitled "It's time slut".
I tentatively clicked the mail with fear building inside me knowing that this was not going to be something i wanted to read!
The email read as follows...

"Good evening my little sissy whore, i trust you have enjoyed your first week as a woman and i trust the Depo is doing it's job as i'd hoped.
I have given you a week to let the severity of the situation get through that stupid little sissy head of yours and to fully accept and embrace the new you.
I think it only right to give you a new name under the circumstances so from this moment on you will be renamed Annabel. This is the name you will use in any correspondence with me and it is what i and others will know you as from now on.
Annabel. such a prissy, sissy name for such a sissy little bitch.
Well Annabel you may be wondering what i've been doing all week so i will tell you!
As you well know you are now 110% fucked and owned by ME and will remain so for the forseeable future untill i tire of you or sell you on.
With that in ind i have spent the week working out how best to utilise my new asset (annabel) so she can best serve her Empress and fall deeper and deeper into submission.
You know by now that in the coming weeks, months and years that you will be pimped and whored out by ME to provide me with a steady source of income which is what i deserve.
To make sure you are fully ready for this i have been a busy Mistress this week organising your first step on that road.
This week i have been busy advertising a gloryhole session which will take place at my flat where lots of men will be arriving expecting to get the cocks sucked to completion and their cum eaten by a dirty cumslut. That cumslut is YOU annabel.
Saturday morning you WILL be here at 9am to be prepared for a long day at the hole.
You will be further feminised by ME and secured to a chair in the hallway. Infront of that chair is a large wooden board with a gloryhole cut out at cock height through which you will be sucking cock.
So far there are 23 confirmed booking between 10am and 6pm, that's a minimum of 8hrs sucking REAL men for my profit and amusement.
The adverts are still live however and i expect that number to increase significantly before Saturday so as you can see you will be sucking a lot of dick and eating a LOT of spunk.
I have only charged a very minor fee this time to ensure MY annabel builds up a good customer base before i push her deeper and further into her new role.
You my dear annabel will remain firmly chained and bound to the chair for the whole day with a large butt plug inserted deep into MY sissy ass.
Oh and one last thing... i have set the video camera up on your side of the gloryhole to ensure the whole days events are captured for posterity.
See you at 9am annabel, DON'T be late whatever you do..."

That was like a bolt of lightning through my now sissified body and i knew this was the beginning of Empresses plan unfolding before my eyes.
I briefly thought "no way, i'm not doing it" then i realised that it was no longer optional and there was no way i couldn't turn up without my life being as good as over... I really was screwed and i really was about to be whored out and my mouth rented to a string of horny men with balls full of hot sperm.
I had 24hrs to get my head around the idea and it was the longest 24hrs of my sissy life...

Saturday morning arrived and my alarm clock rang out at 7am. I stirred from my slumber and then the realisation of the day hit me.
I jumped out of bed, showered, cleaned out my ass and got ready for the big day.
I arrived early at Empresses and sat outside for 10mins so as not to annoy her by being too early. At five to 9 i walked to the door and knelt as that was what she had come to expect.
The door opened at 9am exactly and i was dragged in by the hair as i stumbled on my knees to follow Empress down the hall.
I immediately saw the large false wall in the hallway which was set to one side to allow passage down the side prior to the arrival of callers.
There was a hole at waist height and my heart skipped a beat as i realise that in one hour the first cock would be poking through it and into my sissy mouth.
I was dragged into the spare room and Empress simply pointed at the clothing laid out and left the room.
I undressed and put on the items she had laid out which consisted of black seamed stockings, suspenders, a black basque, red high heels and a blonde wig.
I looked in the mirror and saw a true slut staring back at me and realised what i had become..
Empress came back in and pushed me to the bed on my bum.
She got to work with some heavy make up which was topped off with some purple eye shadow and heavy deep red lipstick.
"there annabel, ow you are ready to work for me. Keep the lippy to hand as it will need to be reapplied after each load of cum you eat today, understand?"
"Yes Empress" i managed to whimper from my shame.
I was collared and led to the chair in the hallway where i saw a large fat butt plug sat in the centre of the seat.
Mistress pointed out the lube on the floor and said "lube yourself up and sit on the plug annabel".
I took a large glob of lube and rubbed it around my hole then some more over the plug. I turned and backed down onto the plug slowly but firmly.
It was a HUGE plug and i eased it gently inside moaning as it inched my asshole further open and felt like it was going to tear me apart.
Finally Empress tired of my complaints and pushed me of balance hard onto the plug. It popped as it secreted itself deep inside my ass and i gritted my teeth whilst adjusting to the sudden invasion of my ass.
Empress then tied each of my stockinged legs to the legs of the chair with gaffa tape and also bound me round the waist to the chair. She left my hands free knowing i would need them within the next ten minutes when the first cock arrived.
Empress left me in situ and went off for a coffee awaiting the first guest. I heard her casually watchin television whilst i sat femmed, plugged and bound behind the gloryhole contemplating sucking my first ever cock.
About five past ten the door knocked firmly and i heard Empress go to the door but could not see her as the board had been moved now obscuring my vision down the hallway.
I heard Empress talking to a guy and knew that this was it.
I saw her hand reach around the board and click record on the video camera.
"Enjoy" she said to the man "and just let yourself out when you're done".
I heard the lounge door shut as she retired to watch TV and head the man undoing his trousers behind the board.
With that a semi erect black cock was pushed through the hole and and i looked at it in fear and total shame.
I glanced at the camera lens and knew what i had to do...
I reached forward and took the cock into my nervous mouth and began to stroke it and suck it to full erection..
It was now official. I was the working girl of Empress and a pimped sissy whore.
I concentrated on the cock and continued to suck it and lick it until i felt the guy building to orgasm.
Then without warning his cock twitched and pulsed and he let out a small groan as he emptied his big fat balls into my mouth. I gulped greedily trying to eat the cum and swallowed hard as the first ever load slid down my throat and into annabels belly. The cock stayed there and i realised he wanted me to clean him before he left so i lapped up all the cum from around his shaft and sucked his bell end clean.
With that the cock withdrew and he zipped up and left the flat.
This carried on for 8hrs and i lost count of the number of cocks that i sucked that day and the amount of cum i'd eaten.
Each time i'd reapply my lipstick as per my orders and prepare for the next dick.
My ass was broken and sore and my jaw was aching form being stretched and used by cocks of all sizes shapes and colours.
At 7.15pm Empress moved the board and turned of the video camera.
"Well annabel you did well for your first day. 37 cocks in one day at £10 a go.... not bad at all MY slut"
I looked up at her a broken sissy with spunk all over my face, dripping off my chin and my stockings and heels covered in sticky jizz.
"thankyou Empress" i replied in a soft tone, she knew i was broken and at her mercy.
She untied my legs from the chair and stood me up to regain some feeling in my legs which took a few moments.
With that Empress handed me my car keys and ushered me to the front door.
"Bye annabel, oh and i forgot to say, same time tomorrow".
With that she opened the door and pushed me out into the cold dark evening air.
I was in heels, stockings and no underwear with a large butt plug still embedded in my ass. I was dripping in spunk and the door slammed shut locking my male attire inside the flat.
I quietly crept down the stairwell in a state of total disgrace and ran swiftly to my car in heels as best i could.
I drove home glad it was dark and pondering what i had just done for Empress. I knew that no matter what i thought it would all begin again at 10am in the morning and i sobbed quietly as i arrived home and ran indoors...
I was Empresses cumwhore and this was just day one....

to be continued..
85% (15/3)
 
Categories: BDSMFetishTaboo
Posted by kinkyandfun
3 years ago    Views: 450
Comments (6)
Reply for:
Reply text
Please login or register to post comments.
9 months ago
Delicious story, cum eating. Yummm
1 year ago
great story
2 years ago
Love the story! I wish there was someone who gave me the same experience!
2 years ago
I love that story. I wish there is an EMpress to offer me the chance to do such Glory Hole work
2 years ago
I really love this story! Annabel is such a lucky sissy slaveboy! Wish I was the sissy cumwhore of Empress!
2 years ago
The best story ever! Annbel is such a lucky sissy cumwhore! Really wish I was the sissy slaveboy of Empress!