I'm all going on my Summer Holiday

Why is it that when you are just looking for a bit of piece and quiet, things conspire to wreck all your carefully laid plans.

It all started out perfectly, the weather forecast was good, a secluded cottage rented for a week, the car checked over and packed. Everything was set as I drove away from home that fateful Friday lunchtime.

Who am I? Well, my name is Thomas Carlyle. If you are from Scotland, that name will sound very familiar. My far more famous namesake lived in the 19th Century and was a lawyer and a very controversial social commentator and staunch Calvanist.

As far as I know, I am no relation to him but my father was named Thomas, as was his father before him. Legend has it that when he lost his faith, he went wild and perhaps, just perhaps sired an illegitimate son. I don’t know and only a DNA test would tell. But I digress.

As I said, I’m Tom Carlyle.
Age? 28.
Marital status? Divorced (she took me to the cleaners and back for more to pay for her lawyer whom she promptly married).
Occupation? Accountant (self employed, well I got laid off last year and this was all that was left to me…)
Place of Residence? Rented 2-bed flat in Wood Green, North London about fifteen minutes walk to the Tube on a good day.

Self-Employed or not, I’m off on holiday this fine May weekend. I’d booked a cottage in West Somerset, a few miles inland from Porlock.

I’m going alone so that I can indulge myself in what some people may think of a filthy if not downright disgusting habit, namely dressing in women’s clothes and living as a woman.

There I’ve said it. I’m a tranny. If you don’t like them please stop reading right now. I love wearing women’s clothes but I have no intention of ever living as a woman full time so don’t even ask. It is not like I don’t ever dream of being a full time woman but that isn’t really me. Don’t get me wrong, I love wearing clothes, makeup and everything but I know in my own mind that if I tried to do it all the time I’d end up going mad but for four or five weeks a year and I’m in heaven. Well, that was the plan anyway.

This is the story of my holiday or well it would have been if things had not conspired…

Friday May 21st.
The sun shone and the shy was blue all the way as I drove down to Somerset and stopped in Minehead at the letting agents to pick up the keys to my home for the next week. The journey was so nice that I had visions of me driving a convertible with the top down and me looking gorgeous with long flowing blonde hair! I was totally chilled out and that was good.

The journey had taken me 4 hours door to door which I didn’t consider too bad as the M25 was its usual car park from the M1 junction right round to my exit at junction 12 for the M3.

I stopped off in Minehead to collect the keys to the cottage and headed out of town towards Porlock. As I did so, my excitement level rose considerably.

The cottage I’d chosen to rent was pretty large. 3 bedrooms, thatched roof lots of flowers in the garden. Add to that, its location. It is situated right at the end of a narrow unclassified road on the edge of Exmoor.

As I drove towards it, my mind got wandering again as I passed ‘Lorna Doone Farm’.

I was so distracted with the surroundings that I missed my turning. It was only rumbling over the cattle grid as I came up onto the moor that I came to my senses, stopped and turned back.

As I approached the cottage, it appeared to be everything I’d wished for, picturesque and remote. It was just perfect for my week living as a woman.

I settled in and stowed everything away and then I got changed.
I became Roberta and until I leave here in nine days time I put my ‘male’ clothes and personality away until it was time be leave for home.

The back garden of the cottage is very private. It has high fences and hedging all around ensure that I’ve got the privacy I wanted. I can just chill out and be the woman I should have been born as for a whole week without any peeping toms getting their kicks from seeing me.

I have been allowing myself this indulgence every year. Well, every year since I got divorced.

In the end, my ex wife Sonia turned out to be a complete bitch as she didn’t even try to understand me and why I wanted to expose my feminine side. Inevitably we got divorced and took me to the cleaners in the process. I gave in to her demands and threats rather than have my so-called ‘perversion’ splashed all over the newspapers. It wouldn’t have looked good with my surname and all that it implies.

Not long after everything had been finalised, I found out she’d been two timing me for almost all of our brief and stormy marriage that lasted in all just under 4 years and to make matters a whole lot worse, the affair was with her slimy, greasy Lawyer.

Consequently, I became a free person again nearly five years ago. Hmmm. I perhaps I should crack open that bottle of bubbly on the 25th? That would 5 years to the day since my divorce was finalised.

Once I’d got everything stowed away, I opened a bottle of beer and went outside to enjoy the early evening Sun. Because it was warm or perhaps I was the effect of the beer but in any event, I fell asleep for nearly an hour. I woke feel rather refreshed as a result but decidedly hungry so I decided to go and get dinner prepared.

On the menu was Spanish Chicken and Chorizo with a Green Salad. I’d put a nice bottle of ‘Entre de Mers’ to chill in the fridge. I thought it was a perfect accompaniment to the main course.

One thing I don’t like about staying in a cottage this old is the low door height. It makes wearing heels a risky business. I’ve already banged my head three times in the first four hours. Still, I’m not taking them off until I leave next Sunday. Just before going to bed I glued my false breasts on. The grand plan was to leave them on until I get home.

Saturday 22nd May.

The sunlight streaming through the bedroom window woke me before 5am. I didn’t mind in the slightest as I’m a bit of a morning person. I got up, dressed, put my wig on, slung a cardigan over my shoulder and went out into the garden.

Oh silly me. There had been some rain in the night. My stiletto heels sank into the grass. Still, it was a nice feeling to be out in the cool air without any knickers on. The birds were singing and all was at peace with the world.

This prompted me to sit in the garden until nearly 8am. Then I came inside and made myself some breakfast.

I spent the morning busying myself in the cottage. I find cleaning very therapeutic. My job involves a lot of thinking and mental agility. I find I can switch off by doing some chores like polishing the silver or cleaning the bathroom.

After lunch, I put on my belt. Yes, a chastity belt. It helps to keep my horrid male parts hidden away.

It is nice and comfy after wearing it for most of the last three years. I put the keys into a padded envelope. My plan was to go into Porlock the following morning and post it home ‘2nd class’.

Then I did my nails and then spent the rest of the afternoon sunbathing in the back garden. I’d already put on a one-piece bathing suit that covered both my belt and my false breasts. The lower part had a nice frilly skirt part.

The hot sun and the wine at lunchtime conspired to send me to sleep. Luckily I was under the umbrella. I don’t tan. I just burn to a frazzle. I had bright red hair underneath my wig so as a child so that probably explains it.

I’d just woken up when I heard a car coming up the lane.
“Probably got lost”, I thought. There was a turning space near where I’d parked my car. Whoever it was could turn around there.

The car stopped and the engine stopped. I started to panic. Who would be coming up here this late on a Saturday afternoon?
I was at the far end of the garden so there was nowhere for me to go. The side gate led right into the back garden. There was nothing more but to stay put and hope they didn’t see me.

My heart stopped when the gate opened. It was the woman from the Agents’ in Minehead. What did she want at this time on a Saturday Afternoon?

I racked my brains trying to remember her name.
I got it just about the same time she saw me.

Olivia. That was her name. She’d been wearing a name-tag when I was at the agents office.

She saw me and stopped dead in her tracks.
She did a double take. Then she called out.
“Mr Carlyle?”
She waved at me.

There was nothing for it. I waved her over.

I sat back and waited for the barrage. It was something I’d thought about when I first thought about taking a whole holiday ‘en-femme’ so to speak.

“Mr Carlyle? Is that you?”
“Yes. That’s me.”

She had trouble stopping herself from sniggering as she walked along the garden path towards him.

“Please take a seat. Olivia isn’t it?”
“Yes. Yes it is.”

She sat down.

“What do I owe you the pleasure of your company this time on a Saturday afternoon?”

“Mr Carlyle…?”

“Roberta please.”

“Roberta… I’ve come to tell you that there has been a horrendous mix-up over the bookings for the cottage. I’m afraid we have double booked the place for this week.”

I felt shocked.

“Are you trying to tell me that I’ve got to leave? After all, I was here first?”

“Yes. Yes you are. The problem is that the other booking is for relatives of the owners. We’ve made a mistake and for that we are prepared to refund all your money and find you a replacement place to stay.”

This really hit home hard. I was totally lost for words.

“When do you expect me to leave?”

Olivia couldn’t look me in the face.

“As soon as possible. The Owners family will be arriving in less than an hour.”

“An hour? Where do you expect me to stay tonight?”

“We have arranged a cottage in Porlock for you. You can stay there for the rest of your holiday.”

This something I’d not wanted to happen. I could take her visiting me but I’d spent hours looking at cottages all over the South West Peninsular trying to find the right place. A private place. This was it. Nowhere else was suitable. None. Nada. Zilch.

I slowly got to my feet.

“I’d better get packed then.”

“Can I help?” asked Olivia.

I thought for a second.

“Yes please. I’ve bought enough food for the week. I’ll be dammed if I’m going to leave it here for these interlopers.”

Olivia smiled back at me.

“Are you going to… get changed?”

I smiled back.

“Fraid not. These beauties will take at least half an hour to remove. Then there is the little matter of my nails. I think I had better stay as I am don’t you?”

She didn’t answer that. I was thankful that she didn’t.

Some Fifty-Five fraught minutes later, I was packed and my car loaded up.

I looked back at the cottage and felt sad. I’d looked forward to this week for nearly 8 months. Less than a day and my dreams were shattered.

I shook my head and got into my car. I kicked off my heels and started the engine.

I followed Olivia down the lane back to the village of Porlock.

My feelings of dread about the future of my holiday were soon realised. The ‘Cottage’ the agency had arranged for me was not only pokey, but to my dismay the garden was overlooked on all sides.

“This is hardly what I had in mind Miss….”

“Please just call me Olivia.”

“Well Olivia?”

She looked around the one bedroom place.

“I see what you mean.”

She looked at her watch.

“It is getting late. Far too late to find you another place tonight.”

I’d thought as much.

“Well I think I’d better go home and call this week a total loss.”

She saw I was serious.

“Please stay. I’m sure we can find you somewhere tomorrow.”

I shook my head.

“You really don’t have to bother. I’m resigned to this holiday being a total wash-out.”

I did look rather sad.

“Look Roberta, why don’t you come and stay at my place?”

“I couldn’t impose. Besides look at me? A silly man who wanted to spend the week indulging in his habit of dressing up as a faux woman. No. Sorry Olivia. It is kind of you to offer but you really don’t want someone like me cluttering up you place looking like something the cat dragged home.”

Olivia smiled.

“At least you are honest.”

She smiled back.

“Please come and stay. I’ll take a few days off and I’ll show you the area.”

This offer shocked me.

“Looking like this? You have to be kidding?”

“Look Roberta. No promises or anything but I recon I can make you passable. But no funny business ok?”

I couldn’t stop myself. I started to laugh.

“What’s so funny?”

“The ‘no funny business’ bit.”

She looked very serious.

“Don’t worry Olivia. There won’t be any funny business. I can assure you of that”, I replied with a straight face.

She had this look of ‘do I believe you or not?’

I saw this.

“If there is no funny business as you call it, then you can take me out to dinner on the last night I’m here. If I try anything then I’ll take you out.”

Olivia realised that Roberta was serious, very serious.

“Very well. Deal,” I replied with hardly any enthusiasm.

Olivia led our convoy of two cars out of Porlock and along the coast road to the small hamlet of Worthy, then she turned off onto the driveway to a large house.

Roberta was shocked by the size of the place.
Olivia pulled up outside and opened the front door.

“This is a huge place. Is it yours?”

“Mine? No way. I’m sort of house sitting for the owner. I get to live here for ten months of the year free of charge in return for looking after the place. The owners won’t be back until the beginning of July.”

She helped me unload my car.

“You can take the room second on the left at the top of the stairs,” said Olivia as she took the food I’d bought into the spacious kitchen.

I carried my things upstairs and into the room she’d assigned to me. It looked pretty comfortable. I went back downstairs to find Olivia. She was finishing putting the things away.

“All settled in?”

I chuckled.

“I haven’t unpacked everything if that is what you mean?”

She smiled back.

“I’ll rustle up something for us to eat.”

“Thanks,” I said as I sat down.

“Can I help?”

“No, you are my guest so stay where you are and entertain me.”

“Entertain you? What do you mean?”

“Tell me about your self. What you are really doing down here.”

I laughed at her request. Nevertheless, I began,
“I was on holiday. Trying to spend a week being myself.”

Olivia sniggered.

“What’s so funny?”

“I’ve never met anyone like you. You seem so relaxed about me finding you like dressed like that.”

“I didn’t have much choice in the matter did I? So I sort of just accepted that I’d been found out and got on with it.”

I smiled back.

“To be honest with you, I thought long and hard about being ‘found out’ when I first started taking holidays en-femme. I realised that if it happened then so be it. I’d be in a place that was a long way from my home and work so why get hung up about it. Besides, I’d be gone in a short while so what does it really matter?”

“Wow. You seem to have thought of everything.”

I shook my head.

“Not quite. I didn’t plan on getting turfed out my holiday home at less than an hours notice after one day.”


Olivia had by now prepared something for us to eat. My only contribution was to open one of the bottles of wine I’d brought with me. We continued talking during the meal.
Despite the chat, I found out very little about her. She seemed very adept at subtly changing the subject as she talked.
It was getting late by the time we’d cleared things away.

“I think I’ll go to bed now. Thanks for the meal and giving me somewhere to sleep tonight.”

“Ok. Goodnight. There are sheets and bedding in the Wardrobe in your room,” she replied in an almost dismissive manner.

Sleep was hard to come by that night. I kept thinking about what I should do. In the end I decided that it would be best if I went home as soon as possible the next morning.

Sunday 24th May

In the end, it was the smell of fresh coffee coming up from downstairs that woke me. I looked at my watch. It was almost 9:00am.

That stirred me into action. So much for the early start I’d hoped for.

I started by applying the solvent to the glue that was holding my false breasts in place. I had to be patient. If I wasn’t then I could tear my skin. I’d done that once before and it was not something I wanted to repeat. While I waited for the solvent to work, I removed the nail polish I’d so painstakingly applied the previous day.

Despite my attempting to rush, it was nearly half an hour before I put on my ‘Robert’ clothes and headed downstairs.

Olivia was busy with something in the oven when I walked into the kitchen.

“Good morning. There is coffee in the pot. I’m just cooking some rolls for breakfast.”

“Thanks,” I muttered.

I turned my back on her and began to pour some coffee.
The next thing I heard was the crash of a metal tin hitting the stone floor.

I turned to see Olivia staring open mouthed at me.

“You’ve changed?”

I bent down and gingerly picked up the hot rolls from the floor.

When I’d done I stood up.

“Yes. Yes I have. I spent a lot of time giving the whole thing a lot of thought and I’ve decided to go home sooner rather than later.”

Olivia looked at me with a very sad expression on her face.

“But… I’ve just arranged to take the week off!”

“Look Olivia, I’m grateful for your hospitality but I think it is better if I leave now.”

“Are you chickening out? Wasn’t I going to try to make you passable today?”

“Yes you were and I really appreciate your kindness and everything but I’m really a very private person. I’m not sure if Roberta is anywhere near ready to go out into the big bad world.”

Olivia sat down and poured herself some coffee.

I decided to change the subject.

“These rolls smell good. Did you bake them yourself?”

She managed a small smile.

“Yes and no. They are part baked. I just put them in the oven for 10 minutes.”
“Still fresh bread is just the job for a Sunday Morning. All that’s missing is some freshly grilled bacon.”

“Eh? Aren’t you Jewish? Weren’t you wearing a Star of David necklace yesterday?”

“That was very observant of you. Yes, I was born a Jew but I’ve not been to the Synagogue since my Bar Mitzvah. I don’t practice Judaism any more. I’m actually a Christian. My Grandmother gave me the necklace when I was five years old. I wear it to remember her.”

Olivia looked sad.

“Why so sad?”

“I was just getting used to being with someone like you. It’s a very unique experience for me.”

She hesitated.

“One that I was starting to enjoy.”

I smiled back.

“Don’t let one evening fool you. I’m a rather boring person really”

“Who says so?”

“My ex wife and a number of girl friends since that who”

“Are they saying that to Thomas or Roberta?”

Se had me there.

“Thomas” I replied quietly.

“Well, I found Roberta to be a very engaging person”

I smiled back.

“That still does not change the fact that I’m going home.”

“What are you going to do when you get home? Probably mope around your flat or even worse start working?”

I shrugged my shoulders.


“So? Why do that when you could be here enjoying my sparkling wit and company?”

I felt somewhat backed into a corner.

“What about you? What about your boyfriend?”

She grinned back.

“I’m not that way inclined.”

“Eh? Are you saying that you are a lesbian?”

“Sort of…”

She drank some of her coffee.

“I’ve had a few bad experiences with men over the years. As a result, I’ve been experimenting with female company.”

I smiled back.

“Well that counts me out. I’m definitely not a woman,” I said hoping that I might escape her clutches.

“I know and that’s what is…”

She looked at me.

“What is puzzling me?”

She looked down at the floor.

“Oh sod it. Look Robert, Roberta or whatever, when I saw you in the cottage garden, I said to myself, I fancy her. When it turned out that you were a man and one who didn’t come onto me, it didn’t seem to matter.”

I felt rather flattered but I still wasn’t convinced to stay.

“I’m flattered to hear that but it does not change things. I’m still going home.”

Olivia looked disappointed.

“Look I’m sorry Olivia. It’s my holiday that got ruined. All I wanted was a quiet week being myself on my own. I can’t have than so my next best thing is to go home.”

“But Robert…”

“I’m sorry Olivia. That is how it must be. I’m going to get my things and go home. You can keep all the food I bought as a thank you for the hospitality last night.”

With that I left her alone in the kitchen and went upstairs.
I quickly packed my things and returned downstairs.
Olivia was nowhere to be seen.

I found some paper and wrote a note.

Dear Olivia,
Thanks for everything. You were a real star.

I loaded the car and drove home with more than a tinge of regret about what might have been.

[Continued in Part 2]

[Note] The title is a bit of a play on words with the first line of the song 'Summer Holiday' by Cliff Richard. I'm old enough to remember going to see it at the Embassy Cinema, the 'flea' pit from my childhood.

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