Jeremy's Best Holiday - Ever. A Staycation Competition entry

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JEREMY'S BEST HOLIDAY - EVER

by Bronwen Welsh


A Staycation Story Competition entry

Jeremy waved as he watched the taxi bearing his parents to the airport, travel down the road and turn the corner. He had the house to himself for a whole week! His father worked for a large multi-national company that held an annual conference in a different state each year. He had mentioned to Jeremy's mother that most of the delegates took along their wives, and there was even a special program designed for them, including outings and shopping trips. Jeremy's mother had always declined until now, saying that Jeremy was too young to leave on his own and there were no other relatives to look after him. She was also concerned about leaving the house empty 'in case of burglars'. However, Jeremy was now sixteen and in his father's eyes, old enough to look after himself for a week.

Jeremy's mum reluctantly agreed, but only after cooking and freezing enough meals to feed a small army, let alone a rather slight boy, easily the shortest and skinniest in his class and typically the one who was always chosen last when picking teams for sporting contests like football. Jeremy didn't mind because he preferred other things.

Mr Disney, the school's arts and drama teacher produced an annual show to which parents were invited. It was a boys-only school with an aging headmaster who was also a bachelor clergyman and viewed the female gender with a suspicion amounting to paranoia. Mr Disney's tentative suggestion about asking the local girls' school to provide cast members was met with a stinging rebuff. It seemed that with the exception of parents, no female below the age of sixty was to be allowed on the school premises. What damage they were likely to do was never explained, just darkly hinted at.

This restricted Mr Disney's choice of dramatic works. There were very few plays where the entire cast was male and of those, none was suitable for a school, especially one where the headmaster insisted on checking the script before giving approval. This left only one option, boys had to play the female rôles. It might have been thought that the Headmaster would look upon this as the worst sort of perversion, but he was rather fond of Shakespeare and other playwrights of the Middle Ages, and knew that boys and young men played the female parts in those days. If it was good enough for Shakespeare it was good enough for the Rev Adrian Sparks, MA(Hons),DD, known to all the boys as 'Old Sparky'.

Mr Disney had always wanted to stage “The Wizard of Oz”, but of course he had a problem. If a boy was to play 'Dorothy' he had to be convincing, and up until now, none of his students was suitable, but then along had come Jeremy. He had been cast as a girl and acquitted himself very well in a short play written by Mr Disney himself, which the boys had rehearsed and performed to an audience of the other students. Although he would never have admitted it, the main aim of that play was to see which members of the class were good enough to perform in the annual play to which parents and other relatives were invited. Mr Disney knew that Jeremy would perform 'Dorothy' well, and if he missed this chance, another one might not come along for years. For form's sake, Jeremy expressed reluctance at playing the part, but was finally 'persuaded for the good of the school'. Secretly, he was thrilled of course.

Mr Disney's confidence in Jeremy was not misplaced; the play was a huge success, and 'Dorothy' received a standing ovation. Mr Disney had been a teacher for a long time and knew how boys are always on the lookout for ways to tease or bully other boys, so he waited until he could speak to Jeremy on his own.

“I have a great compliment to pass on to you, Jeremy. Two of the parents came up to me after the show and said how pleased they were to see that Reverend Sparks had finally relented and allowed a girl from another school to play 'Dorothy'. When I told them it was actually a boy, one of our students, they could hardly believe it, and said you could act professionally.”

Jeremy blushed and said 'thank you', but in a way he was not totally surprised, because Jeremy had a secret, he loved dressing as a girl. Indeed the one disappointment of playing 'Dorothy' was that while he wore a pretty dress with petticoats to make the skirt full and which peeped out below the hem, pink bobby socks, Mary Jane shoes, makeup and a wig, he had to wear his own boy's underpants and no bra. He had toyed with the idea of telling Mr Disney that he could perform the part better if he was wearing girl's panties and a bra, but he decided that it might raise awkward questions that would be difficult to answer, so it might be more diplomatic to go along with what had been decided.

Jeremy's mother had attended the performance, but his father had made an excuse that he had a lot of work to catch up on. When his mum had also complimented him on his performance he said: “I'm thinking I might like to be a professional actor, Mum, so I thought if I could play a girl convincingly, how much easier it would be to play boys' parts.” His mum agreed with him.

As Jeremy walked back inside the house and locked the door, he could hardly contain his excitement. Jeremy had an elder sister, Stephanie, who was quite a 'girly' girl. She loved wearing skirts and dresses, along with slips, stockings and heels, while most of her contemporaries had abandoned skirts as something only children wore and now walked around in trousers or jeans and boots resembling those that builder's labourers wore. One thing Steph noticed was that when she travelled by public transport, she was the one that the men looked at, not the girls who dressed like tradesmen.

Whenever he had a chance, Jeremy went into Stephanie's room and dressed in her clothes. He usually only had a couple of hours at most, but now Steph was overseas on a student exchange, so there was nobody to disturb him. He stepped into Steph's room and looked around, his heart pumping. For a whole week, he was going to be a girl, and it could start right away.

He opened Steph's wardrobe and ran his hand lightly along the row of dresses and skirts hanging there, enjoying the sensation of the soft silky materials of which they were made. He knew from experience that he could fit into all her clothes, so all he had to do was make a choice. He finally settled on a 'retro' dress with a full skirt. Hanging next to it was a stiffened petticoat which would complement the skirt perfectly.

Then Jeremy turned to his favourite items in Steph's lingerie drawers. Again, there was so much to choose from. Some time ago, Jeremy had selected two pairs of satin panties with lace trim and hidden them in his own room. Steph had so many, he reasoned, that she would never miss two. Now he selected a white lacy bra and a matching suspender belt, together with a full slip with French lace around the hem and bust. He placed these items on the bed. The final selections were sheer tan stockings, and light brown court shoes with three-inch heels.

Jeremy went to his own room, collected a pair of white satin panties from their hiding place and returned to Steph's bedroom. He stripped off his clothes and decided to take a shower. He was already so excited that he was sweating a little, and had developed a partial erection. By the time he had showered and dried himself, it had subsided.

Now he began to dress, enjoying every minute of the sensual feeling of the silky materials against his skin, including the feel of nylon stockings as he carefully drew them up his largely hair-free legs, and attached them to the suspender belt. He would love to have shaved his legs, but he was a cautious boy and didn't want to give away what he had been doing. He already knew that women were very observant about such matters. Anyway, he had fair hair so without close inspection it was probably undetectable.

He slipped his arms through the bra straps and reaching behind his back clipped the bra together, something which would have shown an observer if there had been one, that he was quite experienced in this area. He rolled up some stockings and placed them in the cups to give the bra shape. Then he lifted the full silk slip over his head and released it, letting the material flow down over his body. Surprisingly, he now felt so girly that his erection didn't return. It couldn't get much better than this.

Once he was wearing all the lingerie and the stockings, he sat down at the dressing table and began to apply makeup. While he had been acting in the play, an older woman had arrived to apply makeup to all the cast. Jeremy had expressed an interest in what she was doing, explaining how he was thinking of becoming an actor and knew that he would have to apply his own makeup one day. The woman patiently explained to him what she was doing, and perhaps she suspected more than Jeremy thought because she said things like: “Of course this is stage makeup, if I was applying normal makeup to a woman's face, I'd do this”, or “I'd do that.” Jeremy committed every bit of information to memory, and now he was using his learned skills to make up his face as a woman would and doing an excellent job of it. “Less is more,” the makeup woman had said, and he followed her advice.

There was really only one thing missing, and that was long hair. As soon as Jeremy knew his parents were going on their trip, he had done his best to time his haircuts so that at the start of the holidays, his hair was fair and as long as he could reasonably leave it without his father saying: “Isn't it time you got a haircut, son?” Now he set about brushing it and finally achieved what looked like an acceptable short hairstyle for a girl.

Stephanie had a couple of pairs of earrings left from the time before she had pierced ears, and Jeremy selected the prettiest pair with imitation pearls and diamonds, and carefully attached them to his earlobes.

The only thing left to do was step into the dress, ease it up his body and put his arms through the sleeves. He reached behind him and being quite athletic, without too much effort pulled up the zip. Then he stepped into the petticoat, lifted up his skirt and pulled it up so that the elastic top was firmly around his waist. Finally, he smoothed the skirt over the petticoat, and finally sat down and put on the shoes. The final act was a twirl in front of the full-length mirror, admiring how he had transformed himself into a pretty girl.

Jeremy started to daydream that he was now a girl called Jessica who had just got ready for her date with one of the football hunks at her school. She imagined the look on his face when she opened the door. He was so handsome, dressed in a suit and holding a bouquet of flowers for her. Suddenly the loud ringing of the doorbell jerked Jeremy out of his daydream. Who could possibly be calling? Was it one of the nosy neighbours? One thing was sure, he couldn't open the door dressed as he was!

Thanks to his mum's paranoia about burglars, Jeremy's dad had installed a sophisticated burglar alarm and a number of security cameras covering the interior and exterior of the house. Jeremy hurried to his father's study where the screens were installed and switched to the camera covering the front porch. To his surprise, a couple of elderly ladies were standing there holding what looked like magazines. Of course, it must be those ladies who went door to door, distributing religious tracts and trying to save souls. He decided to keep quiet and wait for them to go away, but then he suddenly had a cheeky thought; Mr Disney had said that some of the audience at the play were convinced that he was a girl, so why didn't he see if the two old ladies were also fooled? If they weren't, then he would just say he was practicing for a play.

The two ladies had turned and were halfway down the path when Jeremy opened the door and called out: ”Can I help you, ladies?”

They both turned around to look at the pretty girl standing in the doorway, and they walked back.

“Good morning my dear, I'm Muriel and this is my friend Millicent. We're both Heaven's Witnesses, doing God's work, spreading the 'Word'.”

“How very interesting,” said Jessica. “Would you like to come in for a cup of tea and tell me all about it?”

Muriel and Millicent looked at each other. To be honest, they were more used to at best, not getting past the doorstep, and at worst being told to 'Buggeroff', so this was an unexpected invitation.

“Well, err, yes, that is very kind of you my dear,” said Muriel, and they both followed Jessica down the hallway and into the living room.

“Your mother's not in?” said Millicent. “We've met her before, such a nice woman.”

Jessica laughed: “She's not my mother, she's my aunt. The whole family is away on holiday, so she asked my Mum if I could house-sit for a week during my school holidays. I didn't have anything else to do, so I agreed. Now, who's for tea and who's for coffee?”

They both selected tea, and Jessica walked into the kitchen to put on the kettle and find some biscuits to put on a plate. In the next room she could hear Millicent talking to Muriel:

“What a sweet girl, and so prettily dressed. She could teach my granddaughters a thing or two, they both dress like lorry drivers.”

Muriel laughed: “My granddaughter is just the same, it's not like it was when I was a girl. We dressed like young ladies then, and the young men appreciated it.”

Jessica walked back into the room, carrying a tray with three cups and saucers, small plates, napkins and a plate of mixed sweet biscuits which she set down on a small table between the armchairs where the two ladies were sitting. Then she went back to the kitchen and returned with another tray with a pot of tea, hot water, milk and sugar.

“Shall I be 'mother',” she enquired.

The two ladies laughed out loud. “How many years is it since I heard that expression?” said Muriel. They both elected to have weak tea and Jessica poured it for them and a cup for herself, letting them add milk and sugar to their taste. Then she drew up a chair and sat down carefully smoothing out her skirt and crossing her legs at the ankles. The two older women looked at her approvingly.

“What a lovely cup of tea, is it 'English Breakfast'?” said Millicent.

“Oh yes, I'm afraid we are not Earl Grey drinkers here,” said Jessica. The two ladies beamed.

“We've brought some more of our magazines. There are some very interesting articles in them,” said Muriel. “I hope you don't mind me asking, but have you been 'saved'?”

“I do hope so,” said Jessica. “Mummy and I attend church regularly. We're Church of England and Daddy is the Vicar at St John's.”

The two ladies looked slightly disappointed, and Jessica assumed that was because they were hoping to make a convert, and now realised that it was unlikely.

Muriel managed a smile. “We all worship in our own way,” she said.

The conversation moved on to other things.

“That's a very pretty dress you're wearing,” said Millicent. “It reminds me a little of one I wore once.”

“I like wearing dresses,” said Jessica. “I know it's considered a bit 'retro' nowadays, but I think every girl should have her own style.”

“'Retro'?” said Muriel, looking puzzled.

“Yes, sort of vintage you know? So many girls now dress like boys, but I think if you're a girl you should dress like a girl,” said Jessica.

“I quite agree, my dear,” said Millicent. “You could teach our granddaughters a thing or two. I imagine you get many admiring glances from young men?”

Jessica felt herself blushing, which pleased her: “As a matter of fact, I do get the occasional one, but I don't encourage them of course.”

“Of course,” chorused Muriel and Millicent. They didn't believe a word of it.

They continued to chat for a while and then Muriel glanced at her watch and said: “Milli, we've still got three more streets to visit! I hope you'll excuse us my dear, it's been so nice chatting with you.”

With that they got up to leave and Jessica escorted them to the front door and waved them goodbye as they walked down the drive.

When she closed the door, Jessica smiled to herself. “Passed with flying colours!” she said.

The rest of the week passed very pleasantly. Jeremy was Jessica for the whole twenty-four hours a day, wearing a nightdress to bed, and another pretty dress and lingerie during the day. She did the housework that Jeremy had always been so reluctant to do, and the house gleamed.

Midway through the week, Jeremy had to revert to boy mode to go out and buy fresh bread, milk, and a few groceries. He had considered going to the local store dressed as Jessica but decided it was too risky since all the staff knew him. One thing he did realise was that though he had to be Jeremy on the outside, there was no reason why he couldn't be Jessica underneath. He smiled as he stepped into his panties and put on a lacy camisole before putting on shorts and a tee shirt over them. Wouldn't the staff have a shock if they knew what he was wearing!

Jeremy picked up the supplies he needed, still feeling quite girly, but as soon as he got home, he stripped off the boy outer clothes and selected lingerie, stockings and another of Stephanie's dresses to wear. He applied makeup and brushed his hair – he was in Jessica mode again!

Towards the end of the week, Jessica was feeling a bit housebound and longed to go out. She had passed most successfully with the Witness ladies, so why not go out for a short while? It was a warm day, so in the evening, she put on her favourite dress and petticoat, the ones she had worn when the Witnesses called. She wore them over her lingerie which included a full silk slip, a suspender belt, and stockings. She had graduated to four-inch heels now and felt a thrill of excitement as she stepped out of the front door, carefully locking it and placing the key in her handbag. She had left lights and the television on so that the house looked occupied, not that she intended to be out for long.

As she closed the front gate behind her and stepped out onto the pavement, she felt like she was in full girl sensory overload. The warm breeze tugged against her skirt and brushed it, the petticoat and the slip against her nylon-clad legs. The feeling was thrilling, as was the sound of her heels tapping on the pavement. Not for the first time, she wondered if girls felt this way, and if so, why did they now seem to prefer wearing trousers or jeans? It didn't make sense.

She was so full of these thoughts that when she reached the crossroads, she stepped onto the road without thinking. A screech of tyres brought her back to reality and looking up she saw the front of the car only a few feet away. It had been a close shave. The driver was a man in his fifties, and he was obviously very shocked and angry by what had so very nearly happened. His face seemed to soften at the sight of the pretty girl who looked at him with wide startled eyes.

“Sorry!” mouthed Jessica at him. He shrugged his shoulders and after she stepped back onto the pavement, he slowly drove off. Jessica realised another advantage of being a girl. If she had been a boy, it was quite possible that the driver would have got out and had a few very direct words face to face, even though a few passers-by had now stopped.

“You were lucky there, young lady,” said an older woman.

“I know, I feel so stupid, daydreaming,” said Jessica. “I won't do that again.”

For the rest of her walk, Jessica was very careful to be aware of her surroundings.

The week passed all too quickly, and soon it was the day before his parents were due to return. Reluctantly, Jeremy made sure that all of Stephanie's clothes were put back exactly as he had found them, and all her lingerie was washed, dried and ironed where necessary. Back to wearing his boy clothes, Jeremy felt quite miserable. The week had told him something about himself which in a way he had always known, but now there was no denying it.

Jeremy's parents arrived back to their sparkling house and were totally amazed. In the taxi driving back from the airport, Jeremy's mum had said to her husband: “Don't be surprised if the house is in a bit of a mess, you know what teenage boys are like. I'll soon have it cleaned up.”

The taxi drew up at the house and Jeremy, who had been watching for them, opened the front door. His mum and dad entered the house and looked around them in astonishment, especially his mother.

“Jeremy, this is wonderful. Did you spend the whole week cleaning the house?” said his mum.

“Not the whole week, Mum. I did a lot of reading and played some video games on my computer,” said Jeremy. He wanted to say more, but didn't know how she would take it, so said nothing.

The school holidays were over, and Jeremy was back at school. He wondered if Mr Disney would be planning another play soon. If so, he hoped there was a good girl part for him to play.

It was two weeks later that Jeremy came home from school one day. His mum was working part-time and this was one of her days off.

“Jeremy, I had some visitors today,” she said. “Two of the Heaven's Witnesses ladies called by. They told me how they called while your Dad and I were at the conference and were invited in by a charming young lady, about your age, who said her name was Jessica, my sister's daughter. She made them a cup of tea and they all had a good chat. They also mentioned how feminine she was, so prettily dressed and so polite.

“Now you and I know that my sister doesn't have a daughter. Would you like to tell me what was going on?” She raised an eyebrow.

Jeremy knew his cheeks were glowing. He took a deep breath: “Mum, we need to talk.”

THE END

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Comments

“Mum, we need to talk”

Monique S's picture

Precious!

They sure do. I hope mum doesn't sink into despair. Jessica will need a lot of support for confronting her dad, not even to mention school!

Nice little story, Bronwen, thank you.

Monique S

"Mom, we have to talk"

Nice to see a short story from you again Bron. Bet Jeremy doesn't want Dad there for this talk.

Around here, they're called Jehova's Witnesses, and if you make them tea, they are like the stray dog you feed,and never leaves.

oops?

TheCropredyKid's picture

[nt]

 
 
 
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