A Life in Service

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How a crossdresser's dream career started.
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Someone said to me a while ago that their life had been a series of happy coincidences and I feel I can agree. It was one of those moments of luck that led to where I am today and I wanted to share the story with others.

I was in my mid-twenties and working in a hairdressers when I saw a job advert that changed the direction I was meant to travel in. A customer had left a paper behind and as I had some time before my next customer I started flicking through it. In the Situations Vacant section I saw an advert that intrigued me. "Wanted - live in maid to perform cleaning and waitressing duties," the advert read. I tore it out of the paper and placed it in my bag and thought about it for the rest of the day. Later, at home I showed it to my mum and sister and both felt I should apply.

At this point it is worth telling you a bit more about me. I was born male and back then spent most of my time with others in my male persona. However, for most of my time at home and occasionally in the company of close friends I transitioned into my female persona. My mother and sister knew this from when I was in my teens and actively encouraged it helping me with buying clothing and assisting with giving me advice on applying make-up and styling the wigs I wear. At home I dressed en-femme and slept in ladies nightwear.

I was honest in my application letter and sent it off wondering how it would be received. A week later I received a letter inviting me for an interview. The address was for a country house and it was quite a way from where we lived and so my mother agreed to drive me there and I dressed in my male persona. The interview went well, they asked about my experience and said they would offer training but they were more interested in my female persona and quizzed me for some time on it. At the end they said they would be in touch.

A week later they wrote again inviting me for a second interview likely to take all day. They wanted me to come on my own and transition into my female persona as part of the day. I took the train and was collected from the station by the housekeeper who had interviewed me before. At the house I was given time to change and out on my make-up. They had provided a maid's dress and underwear which I have to admit was quite sexy. I also had to wear high heels.

Upon my arrival, back in the hall I was introduced to the couple who owned the house. I was inspected and comments provided on my dress and make-up. "There's room for improvement," came the replies and then they set me to work. They wanted to see how I could wait at table and again they told me I would need more training but the atmosphere remained pleasant.

After more demonstrations of my ability they told me to change back into my male persona and asked me to come and join them in the office. They told me they wanted to offer me the job but there was also something I needed to know and that I was sworn not to divulge it.

"We run a club that caters for people's alternative sexual tastes," was the first statement. They went on to tell me that they ran regular parties catering for people who wished to indulge in swinging, gang bangs, same sex intercourse, cross dressing and BDSM. Our house is a safe haven for people who feel they can't indulge in their sexual fetishes elsewhere. "We would want you to attend these parties in your capacity as a maid and want to make sure you would be comfortable with this," they finished with.

It was a lot to take in and after some thought I said yes. Then came their conditions of employment. The job was a live in position with one day off per week. I was to transition into my female persona full time and allow my hair to grow longer and be styled in a female way. I was only allowed one set of male clothing and the remainder of my wardrobe would be entirely en-femme as would all my toiletries.

My mother and sister were delighted I was finally going to love life as they wanted. I quit the hairdressers and started the new role a couple of weeks later and soon settled into life as a housemaid. I experienced my first party a few nights later from the sidelines and I got incredibly aroused watching the sexual play taking place. I had to admit my favourite were the BDSM parties and I did envy the subs being tied up and beaten by their merciless and very sexy looking female Dommes.

A few weeks after starting I was invited in for a performance review. They told me my work was good and I was quick to learn and that my position would be made permanent. They also asked me about my reaction to the parties and I did manage to confess that I had been aroused by watching the D/s acts and feeling envious of the subs. They then asked, "would you like to take part in the next BDSM party? I said yes straight away and got excited as the date approached.

For the party I changed from my usual maid's outfit into a latex dress. At the party I was introduced at the start of the evening as the slut maid and mingled while I handed out drinks. About halfway through the evening the hostess came over and asked if I was ready to play. I nodded eagerly and she took my hand and led me to one of the dungeons. Inside she removed my panties and tied me to a spanking bench. She then blindfolded me and I heard the door open. Soon afterwards I felt a cock proving my bum hole and another against my lips. As my bottom dilated I opened my mouth and both cocks slid inside me, spit roasting me. I was fucked in both holes simultaneously, an experience I had never tried but always secretly wanted to. Eventually both climaxes took place filling me with hot sticky cum. My mouth struggled and so plenty spilt out onto my chin and dripped onto the floor below.

Soon afterwards the blindfold was removed and I was released from my prison. The hostess asked, "how was it?" I struggled to speak but my large smile told her how much I had enjoyed it. I took part in most parties afterwards as a sex slave or human sex toy regularly having both holes fucked and learning to enjoy the taste of hot spunk.

That was thirty years ago. Since then I have risen through the ranks of the house's hierarchy and I am now housekeeper. I have switched from being a sub to a Domme and spend most of my time organising the parties I willingly volunteered to take part in. As I said at the start life is a series of happy coincidences and seeing that job advert back then turned into one of the happiest of my life.

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  • COMMENTS
2 Comments
RachelPrRachelProver 1 year ago

I would luv to be a part of that as I've been spit roasted before and loved it!🌹🧚‍♂️

TeriLeighTeriLeighalmost 2 years ago

Hi loved the story. If it is a true one I'd love an invite to a party. At 62 I am beginning my transition M2F. I've been a bottom for only a few years and want to experience so much more.

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