tagTransgender & CrossdressersThe Holiday Pt. 01

The Holiday Pt. 01


My name use to be Frank its now Helen sissyslut and I was surfing web looking at crossdressing sites on my computer when this holiday competition came up. For some reason may be my wife had left me after finding me dressed up like a hooker! I decided to enter the competition not really expecting to winner a free 4 weeks holiday in South of France.

Two weeks after I had entered I got a email telling me I had won holiday and the details for trip. I put on a pair of black silk tap pants with black silk cami top and black stay up stocking with blue long pants and blue polo shirt over them was met at airport in South of France by very sexy woman called Linda, she was 5" 6" with 38 C breasts covered by white t shirt you could see her nipples making an impression a short white skirt with nude stockings held up by garter belt with 4" white sandals and deep red lipstick lips. Just looking at her made my dick hard in my panties. She walked in front while I followed behind looking at her sexy rear. She took me to a White Limo that took me to port. We then took a boat to the holiday resort site through a high walled compound up from beach and jetty on island off coast.

A french maid in a pink satin maid dress met the boat at the jetty. She did a curtsey to Linda which I found very sexy. Then the maid looking very sexy with her pink satin panties showing as she walked in front in 5" heels to take us to my apartment inside estate up from beach at which we had landed.

Inside the apartment Linda gave me a drink of one from bar there. Next thing I knew was that I was nude with no body hair and tied to hospital bed. Mistress Linda and Doctor June were checking me over before Doctor June injected me with a new sissy juice. Which would grew my breasts to 36C and transform the rest of my body into sissy slut and reduce my clit to 1" size and make my balls become nut size.

For next two days I was subjected to brain washing to become a sissyslut who needed to service big dicks and worship dominant women. Who would love making out with other sissy sluts. Once Doctor June was happy with my progress having pushed my much smaller balls back into me body. Doctor June also pierced my nipples and put in golden rings I was told that my sissy training would start under Mistress Linda.

Mistress Linda started on walking like a sissyslut in 4" heels black stocking held up by black garter belt black satin panties and matching bar and cami, she used a crop to correct my walking. In the afternoon I was taught to suck her 8" strap on after putting on pink lipstick on my now bigger slutty lips. After sucking her cock for what felt like hours. She had my bend over pull down my panties and beg to be fucked by her cock! Instead she put on latex glove and played with my boy cunt putting 1 then 2 fingers up it saying it needed to be opened up more! So She put in a small butt plug which would be changed for bigger one next day.

By the third day my sissy cunt was ready to be taken by Mistress Linda's strap on it felt so big slowing going in and a bit painful but once it was fully in and She started to really fuck me I was so turned on cum came out of my clit that I had to lick up after I had to lick clean her strap on and thank her for fucking me.

Now that I was being fucked with strap on daily my Mistress started me to learn body worship of female. This covered ass worship rimming licking and putting my tongue into her ass hole. How to worship her pussy and bring her to a series of organisms. Being a body servant licking her clean after She pissed either in a toilet or down my mouth. Running a bath or and to dry her after a shower or bath. How to dress and undress her in a suitable manner. I was taught how to do my make up in different styles and look after my wigs.

Once I was able to do this I was put into black satin maid uniform with matching black satin corset to give me a better figure with black stocking held up by clips on corset with black satin ruffled panties over my small clitty. I got to wear black page boy wig after having my head shaved since some people liked to see a nude head on sissy.

Then i had a pink collar fixed around my neck with a disc hanging from silver ring at the front it had sissy 44 on the disc. i would be now starting room cleaning tasks under the supervision of senior maid in a pink uniform. She would ensure my dress was correct and that i did a good job of cleaning 6 suites that female guests stayed in. She could spank me on bum or use cane if i had been very bad.

We started our tasks by getting our cleaning trolley from basement area and started to clean our area of the building. Knock on the door and use pass key that we had to collect daily from Cleaning Mistress and return it when we had finished working. We had to call out cleaning maids and do curtsey and wait to get permission to start our work. If no one was in suite we started in bed room with king size bed into living area and on to bathroom. Restock the bar and snack food in the fridge.

Sometimes we had to carry out service requirements of a guest Mistress. This included all the personal services we had been trained to give from running a bath, drying a Mistress. Dressing her in clothing she wanted to wear, getting a drink. Some guests wanted to punish a maid because we had not done a task to her liking. Often that led to me having to pull down my panties and left the back of dress so the Mistress could punishment me with her hand,hairbrush or cane often until my bum was red and sore then i would have to stand in passage way for 1 hour to display my bum to anyone passing by.

After being on this duty for month i was moved to service team. This require serving breakfast, lunch and dinner to guests. i started doing breakfast shift which including providing breakfast to 3 suites using service trolley to bring food to the guest's suite. Again it could include other services for guests.You never knew what could be asked of you besides the delivery of breakfast and laying the food out and collecting leftovers later. Again each maid had a senior pink maid along to ensure the maid did the work correctly.

After month of this work i moved to lunch and dinner team that served meals in main dinning room for most guests and room service if required. During these meals maids who had gained demerits from their supervisor or guests got punished in a public setting. This could be turned into piece furniture for 6-12 hours or physical punishment which any guest getting to give part of punishment often 3 licks of cane when 6 or so guests all did this maid had a very sore bum. Another punishment was for maid to wear weights from her nipple rings while being bare on top and only very short red skirt that did't cover her clit red stay up stockings and 6" heels. The maid dressed like that would red bum all day as guests would make sure it stayed red.

For what seemed like a break after doing these jobs a maid was moved to ironing and laundry work. You had to take care of guests washing and resorts towels etc. You would be punished if the work was not done to a high standard.

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by Anonymous

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by Brian7005/21/18

Sissy Juice

Please tell me more about the Sissy Juice. Where can I get it? It sounds wonderful! Xoxoxo : )

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by Anonymous05/11/18

Needed help

Was a very hard read. You skipped details on the sissification. Spelling and flow of story needs a lot of help. Good concept though

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