Working Holiday

"Where are off to for your holidays again," a colleague asked? I was waiting for this question as I packed up for my last day at work before a fortnight away. I knew few would ask it as my colleagues are not inquisitive, thank goodness, but I had rehearsed my answers if I was asked. "I'm having a few days at home and then spending a week with friends," came my reply, hopefully giving them enough information to satisfy their curiosity and prevent further questions. The actual answer probably would have shocked.

Before I continue to tell you about my actual holiday plans it is worth telling you a bit about myself and Carla. I was born male and spend my vanilla life in male mode. Carla is my alter ego, a woman I become at home and at crossdressing social events at weekends. Carla was born when I was in my twenties, when I discovered the pleasures of dressing en femme and transitioning into a woman. Carla's wardrobe soon outgrew mine and I now I only buy essential clothes for myself and spend a much higher amount on keeping Carla clothed and accessorised.

As I progressed through that decade of my life I spent more and more time as Carla and started to meet like-minded people. These encounters led to meets and eventually sex where I discovered my love of cock, but not men, and my desire to be sub and a bottom. Further play led to me discovering the pleasures of the BDSM lifestyle and my preference for punishment play and light bondage.

Carla has meant I live alone as whilst I would love to spend my vanilla life with a woman, finding one who is willing to accept Carla or whose vanilla habits and kinks I can tolerate is very hard. I do like the single life but I do dread holidays as being ripped off with single supplements and having to travel either alone or with a group of people I've never met doesn't really appeal, hence my delight when someone offered me a holiday with a difference.

At a recent social event I was introduced to and started speaking to Sophie and Philip/Philippa. They were both in their thirties like me and I found their company very pleasant as we chatted about our vanilla lives. Chat eventually moved onto our kink lives and later they asked if I had any holiday plans. I said I didn't which made them look at each and other and smiled before Sophie continued.

She told me that they manage a private hotel for its owner, a discrete establishment not advertised or listed on any websites. Guests could only stay at the hotel following an application process and when they were invited. The hotel was regularly full and themed weekends often had a wait list. The reason for privacy and discretion was that the hotel catered for more broad minded guests. As they knew about my sub tendencies they asked if I would consider being one of their guest staff members, guests who were paid for their time but also got to enjoy the play and sex on offer. I was curious to know more and so they invited Carla to come and stay for a night as a guest as a taster.

The hotel was actually a large private country house and they were right about it being discrete. The location was well hidden behind a row of tall hedges bordering the nearby road and entry was through a pair of solid gates. Only a small sign on the road with the house name assured me I was at the right place. Upon arrival I was greeted by Sophie who looked very elegant dressed in her Manager's uniform comprising a well tailored skirt suit with close fitting white cotton blouse. She had high heels on too and I was very jealous of how smart she looked as I followed behind her to my room. Inside she told me Philippa wouldn't be joining us until tomorrow. She then told me she would see me again for a drink before lunch in half an hour.

I sat down for a few minutes savouring the luxury of the room, the nicest hotel room I had ever stayed in. I was in a bit of daydream enjoying it when I realised I needed to get changed into Carla. I selected a blouse, jumper, short pleated leather skirt, thick tights and ankle boots for the spring weather. I then headed down to meet my host.

As I walked into the day room I was greeted by a cross dressed maid offering me a glass of Champagne. Sophie was talking to other guests but excused herself when she saw me. I started to relax as I noticed one other cross dressed guest and returned the discrete acknowledgement of my presence from her. The other guests gave me discrete but enquiring looks and I started to feel more at ease. The Champagne really relaxed me and loosened my tongue a little over lunch.

Sophie and I ate lunch together and she told me a lot more about the hotel. "About half the staff are permanent and the rest are guests like you, coming to enjoy themselves and fulfil their sub fantasies," she told me. She continued with her expectations of the guest staff and that they liked cross dressers to work in the hotel as they proved popular with the guests. All of what she told me about the work sounded very appealing but I also wanted to know more about the sexual play that took place and after lunch she talked about that during a tour of the house and grounds.

The hotel was a very relaxed place without the formality of a large hotel but still felt like it was run very professionally. The decoration of the ground floor and bedrooms was mostly vanilla but a couple had been decorated with a kink theme and contained BDSM furniture and paraphernalia. The cellar also contained a dungeon. Outside was a pool area where some guests were enjoying the hot tub and beyond was an old stable block which had been converted into a BDSM dungeon. "This is where most of our group play takes place," Sophie told me.

Inside the playroom she moved to one of the spanking benches and paused there before asking if I would like to play. I didn't hesitate, I had actually already come just seeing the range of BDSM furniture and desperately wanted to try it out for myself. I eagerly removed my skirt and pulled down my pants and tights giving her full access to my bare bottom. I leant over the bench and enjoyed the physical feeling of being roughly pulled as she tied my wrists and ankles to the metal loops at the base of the legs.

She warmed me up and then gave me ten strokes with a wide leather paddle followed by ten with a cane. Each was harder than the one before as from the corner of my eye I saw her standing legs apart and pulling the tool high up before bringing it down onto my bare flesh. When she released me I was shaky but full of endorphins and she cuddled me placing my head against the soft cotton of her blouse and pressing it against one of her breasts. I enjoyed her post-play tenderness and after recovering I excused myself and went back to my room for a rest.

Dinner was a formal affair allowing me to wear an evening dress from Carla's wardrobe. All the guests and our host sat at a large table and it was nice to start with vanilla chat where I could talk openly about myself before the conversation soon moved onto kink. Hearing others confess to their fetishes and desires made me realise all my forbidden thoughts could be shared quite openly in a forum of like-minded individuals like this. We enjoyed some post dinner play with me watching this time as opposed to taking part. I took myself off to bed later changing into a new silk slip I had bought for my stay and fell asleep quickly after the very busy day.

I woke up the next morning and soon had an erection remembering the enjoyable events of the day before. I felt it would be a shame to let it go to waste and so I wanked myself to a climax before getting up and heading down for breakfast. After breakfast I met with Sophie and Philippa for morning coffee where she put forward a proposition for me.

"We would be interested in you joining the staff of the hotel when you have some time off." Sophie asked with a smile. I replied that I would love to without hesitation. She had one final request and that was to prove how skilled I was sexually. We went upstairs where I fellated Philippa's cock swallowing her load when she climaxed and then shot my own load into her rectum, not something I usually do as I am nearly always the bottom. Afterwards they thanked me and said I would need more practice but that it wasn't a problem.

A few days later a beautiful handwritten letter was delivered offering dates for when I could work in the hotel and asking that I attend some training sessions for some weekends before my work. I was delighted as it meant I could spend more time as Carla in the company of others and so booked a fortnight's leave at work and replied by letter.

I attended my first training session a few weeks later. This time I entered the house through the staff entrance at the back and was introduced to Emma, the head of housekeeping, who would train me. Emma was a very good looking woman and the male me would liked to have spent more time with her ending up in bed. I knew those thoughts wouldn't be tolerated this weekend. Emma gave me my uniform which was a beautifully tailored Italian dress in dark purple with a white apron and hat. I went to my room in the staff quarters and changed into Carla putting the maid's dress on. I kept my make-up much simpler and tied my wig hair back and out the cap on top.

After presenting myself to Emma for inspection she made some minor adjustments to my clothing and finally told me to look in the mirror to admire how beautiful I looked. "This is about you enjoying yourself too," she replied in soft and friendly tones. She reiterated that this experience wasn't a boot camp or some form of modern slavery but was about me enjoying my femme and sub sides just as much as the guests enjoyed their stay. I laughed as I admitted that was loving every minute so far as the experience had introduced some nice order into my life and I looked forward to the training.

The training was divided into two parts, the Saturdays were spent learning how to perform my maid's duties including waiting on guests and housekeeping and Sunday's were spent teaching me how to be better at sexual intercourse with other cross dressers and Domme women. I enjoyed it all as it was delivered in a way to help rather than show up my failures. I was allowed to join Sophie and Philippa for a private dinner on the Saturday nights and we would then enjoy spending time with the other guests in the play areas before going to bed, sometimes alone, other times not.

I completed three weekends of training before they finally said they felt I was ready and would like ask me to work for one of their longer stays. Four times a year they offered a week's holiday to players who wanted more than just a weekend's fun. The hotel was usually fully booked for these weeks and a waiting list soon started. Preparations started in the week before with rooms to be cleaned, beds to be made and food to be prepared. I arrived at the start of this period and really enjoyed the the three days of frenetic activity as we prepared the place alongside two other crossdressing and two genetic girl maids.

The days were tiring but fun and we were well looked after by our hosts. The preparation time allowed me to spend my whole time as Carla and I had been forbidden to bring any other male attire other than the clothes I wore to travel to and from the hotel. I also got to chat to the other crossdressers and learn about them and realised that we were quite similar.

When the preparations were over we had one final briefing where we were told which rooms and the guests we would be looking after and shortly afterwards they started arriving. I was assigned a couple which included a crossdressing husband and a woman who described herself as an almost mythical creature, a swinging unicorn, a single female happy to join in the fun of others. They were all nice people and I looked forward to getting to know them.

We then settled into a routine of the stay. My days were spent in maid mode but as guest staff we were encouraged to mingle with the guests to get to know them so that they could find out if they wanted to play with us. The hosts had circulated pen portraits of all the guests and staff listing their kinks and soon I was asked to play the sub role in other's Domme fantasies. I went to bed most nights either with a sore bottom or full of cum and if I was sleeping alone I would touch the livid areas whilst wanking myself to a very satisfying climax.

There are too many play sessions to talk about here and so I will just talk about the most memorable of the whole week. It started when I was given a note by my hosts and told to read it during my break and in private. I finished my morning chores and then broke away to read it. The note was from the couple with the cross dressing husband I had been assigned to look after. They had booked the cellar dungeon for some post dinner play. The note told me to dress in sub style.

I selected a Japanese schoolgirl uniform I had recently bought. It was an expensive outfit but well worth it as it showed off my slim figure and the tailored blouse shows off the gentle curve of my fake breasts. I made my way down to the dungeon where I was met by the couple and then play got under way.

The couple came towards me and used their hands to touch me whilst the woman started kissing me. The woman led me over to a frame and started securing me to it. She gently guided my wrists up towards some hooks at the top. She used a rope to bind my wrists and the then looped the ends through a ring pulling my arms above my head. I was struggling as I was stretched but I was loving it. She then slipped a gag over my head placing the large ball in my mouth and finally applied a blindfold. I was now completely helpless and had handed over complete control.

My senses were heightened as I felt multiple hands touching me and removing my pants. With my genitals exposed I felt hands touch me and stimulate me making my already hardening cock even harder. I felt a hand I assume was female touching it and then slowly starting to wank me before I felt the warm wetness of it being guided inside a mouth. More hands caressed my bottom and circled my bumhole before a lubricated finger slipped inside.

I was being stimulated through my cock and bumhole and so it was hardly surprising that I soon felt my climax build. I held it off as long as possible but finally my balls erupted and sent a torrent of cum through to my cock where it shot inside the enveloping mouth.

I was soon released from my bonds and the blindfold removed. As I started to see again I saw the woman with a very satisfied look on her face wiping my cum off her lips. I was completely spent and they after a bit of post play care from the woman I left to return to my room where I changed into my femme nightwear and climbed into bed.

A few minutes later I heard a gentle knock on the door. I got up and opened it to see the Swinging Unicorn standing there in a beautiful fur trimmed silk gown. She came in to the room allowing her gown to fall to the floor exposing her naked body which did look rather delicious. She continued climbing into the bed and beckoning for me to join her. Suddenly, I felt quite awake.

In bed she removed my slip and wig and pulled me onto her. Back in male mode I craved her and we eagerly kissed exploring each other's mouths with our tongues and our hands moving over each other's bodies. I stimulated her between her legs with my hands while she slowly wanked my now hard cock and then she moved down to take me in her mouth. I wanted to savour my climax and broke off when I was close and pushed her onto her back parting her legs allowing me to enter her. My climax soon came and I filled her with my own juices mixing with her own abundant nectar.

We soon slept holding each other and chatted more the following morning where she confessed that she was a staff member like me. "Our hosts struggle to find women like me to stay and so it is easier to employ me for these weeks." As we chatted more we found we had lots in common and I found I was starting to really like her.

After the guests had departed I stayed on to help tidy up and enjoyed one more night with the other guests and staff before heading home. There was one nice surprise for me as I left as I was handed two envelopes by my hosts after they thanked me for my time and good work. One contained money and was handed over with the words, "this is your pay for your time here and the tips we received from guests." The envelope was full of cash and a lot more than I earn in a normal week's work. The second contained a hand written note asking me out on a date and signed by the Swinging Unicorn.

"How was your holiday," a colleague asked when I returned to work. I replied that it was very nice and left it at that. I knew that would satisfy them and no other questions would be asked. I wanted to confess all to someone about the time, hence writing it all down for others to share.