The train was just pulling out of London’s Euston Station and Tom was not looking forward to the journey. His parents were packing ready to fly out so Tom had made his own way to Euston for the 21.15 sleeper service to Inverness. Given that he wouldn’t reach Inverness until after 8am, and it would be gone two in the afternoon before he reached his final destination of Thurso, all in all this was not the most desirable of journeys on British trains. Tom had at least secured a single cabin and a first class ticket.

His parents had money and had decided when he was eight years old that he would be sent to a boarding school, the original argument was to give him the best education possible, although his father frequently worked overseas with his mother in tow.

He had made this journey far too often, previously with a guardian but on his own since his sixteenth birthday. On this occasion he’d managed a few days in London with his parents during the autumn half-term break but couldn’t travel back at the last possible moment as his parents were flying off somewhere on the Friday morning, Hallowe’en. Even if waiting to travel on the Saturday was possible he wouldn’t have obtained a ticket, Scotland were playing an international game at Murrayfield, Australia or New Zealand he thought.

Tom settled in his single cabin, not wishing to use the expensive lounge car, and eventually dozed off with his mp3 player still churning out tracks. He stirred several times in the night, not least when they reached Crewe, the orange station lighting piercing through the blind. By the time the steward came to Tom’s cabin with breakfast he’d managed several hours sleep but knew he needed several more, there was also another seven hours before he reached Thurso. Leaving the coffee alone he managed a glass of OJ and that favourite Scottish pastry, a croissant.

The train hadn’t yet passed Aviemore, wrongly believed by many to be Scotland’s highest mountain, but the dawn was finally appearing out of the window. Tom’s mp3 player was still going so he put his headphones back on for the last hour of this train ride.

Tom left the train at Inverness just after eight thirty but had two hours to kill before his next train. He was now feeling hungry so had a choice of microwave bacon bun on the station or a decent breakfast in a nearby cafe. He also picked up a copy of The Scotsman, the paper confirmed the date was Friday 31st October.

Suitably refreshed Tom returned to the station to catch the Thurso service. Once settled he waited for the guard to come around before he dozed off again, confident that he didn’t need to wake until almost the end of the line.

The train had other ideas however and sputtered to a halt not far past Invergordon. An announcement said that the locomotive had a failure and an alternative would come from Aberdeen within an hour, rather optimistic as it turned out. It did eventually arrive but the train had been without heat in the interval and the air-con did not come back on once they were moving again. A curt announcement apologised for this inconvenience. Tom drifted off to sleep, hugging himself for warmth.

Thurso is the nearest station to John O’Groats, the most northerly point on the British mainland. It has fierce landscape but is best known for the wild seascapes. A vast fleet of Russian floating fish factories are based here throughout the harse winter.

Tom was equally frozen when stepped off the train, pulling his bags. He was expecting to see the minibus waiting for him, but it was now almost six. He’d tried to phone the school but couldn’t get a signal from the train. He was stood at the station entrance wondering what to do next. The school was normally very efficient, it was run on military lines.

Tom was not the military sort, but he kept his head down and did the minimum to be accepted by the staff and his peers. His soft features hadn’t changed from the time he arrived there until now but this was only an issue for the lower years who didn’t know him, not the staff or Tom’s friends. He did however have to keep strong to avoid the occasional barb and survive the very physical exercise. It was this strength that meant he did not panic.

Tom pulled out his mobile again and dialed the school. It rang once and then was cut off. He went to dial once more and the battery failed. He’d have to find a phone and try again shortly but needed cover, he was shivering it was definitely not a good time to be outside very long.

There was a pub across the road and although he had been told not to venture into such places, now he was eighteen there was nothing in law to stop him. Plus, there was nowhere else to go right now.

“Hello laddie. What are you after?”

“I’d like a coke please.”

“One coke it will be, although you might need something stronger. What are you doing in Thurso?”

Tom missed the subtle comment about the drink as he was getting out of his coat.

“I’m trying to get to my school. The minibus wasn’t at the station.”

“Would that be St Andrews? We’ll phone them for you, don’t worry laddie. You look cold, put your bags in the corner and go sit by the fire in that armchair. I’ll bring your drink over. What’s your name?”

“Thomas Smart, but the school knows me as Tom Smart.”

The barman put a drop of scotch in the glass. It should have been a single malt but for a soft southerner a cheap blended scotch would do. He put the glass to the optic a second time then added coke before taking the glass over.

“Thank you.”

He coughed as he sank the first mouthful and felt something was wrong.

“What did you put in my coke?”

“Just something to warm you up.”

Tom had drank scotch before, at family parties but never quite this strong, in fact usually he’d had half a shot, poured carefully by his father. And then only on special occasions when a toast was mandatory for all males over 16.

He sipped the first glass and was about to get up when the barman came over with a second glass.

“I didn’t order that.”

“No, it’s on the house. You still need to warm up, this will help you. I’m just going to try the school again.”

Tom sipped the drink and felt warmed by it. The barman called from behind the bar.

“Tommy, the school says it sent a message that they have closed due to illness. You should have got a message.”

Tom knew that his parents were away for the next week, and their mobile numbers were stored in his dead phone. He also knew that the next train South wasn’t until the morning but of course his parents were not at home.

He had brought enough cash for the journey and, thanks to his slumber on the train, had avoided the expensive trolley and lounge services. He had about thirty quid in his pocket, plus his debit card with access to several hundred and it looked like he would have to use that. At least he had a return train ticket, and that wasn’t cheap.

Next time he’d fly.

Tom considered all this and wondered how to get out of the problem. Perhaps the school would only be closed for a few days, he could find lodgings while he waited. Although he’d been to Thurso regularly for the past ten years he did not know the town beyond a few shops, his bank and the station.

“Is there somewhere I can stay?”

“We have rooms here. How long do you think you need to stay?”

“Until Monday. If the school isn’t open by then I’ll head South.”

He didn’t know where he’d go, and there was another, as yet unspoken, problem.

“I’ll bring your bags. Follow me.”

Tom went up the stairs after the barman, apparently no formalities were needed and there was no question of the price. He hadn’t paid for the drink yet either. The barman put his bags down.

“There you are, here’s your key. It opens the rear door downstairs in case the bar is closed, although it rarely is. We’ll sort your bill out when you leave. Now, there’s a dance tonight in the hall across the road, you’ll be there? It’s a ceilidh. do you have a kilt with you?

“No, it’s at the school.”

“I’ll see what I can do. What size are you?”

“Twenty six inch waist.”

“That could be a problem. I’ll get back to you. Get sorted and I’ll see you in the bar.”

Tom sat on the bed. The room was typical for an inn. He’d stayed in a few with his parents when there was nothing else available. His mother was seemingly never impressed with anything less than five star hotels so grumbled continuously in lesser premises.

His bags sat on the floor. One bag had a simple change of clothes that his mother insisted he took, otherwise it contained his books and homework. Just because he was on holiday didn’t mean that the school didn’t want work out of him. He’d need those clothes tomorrow, most likely. At least there was a shower in the room so he could keep clean. He looked in the bag for his clean set of underwear but his mother had overlooked that.

Of course, that wouldn’t normally be a problem. The school kept his clothes clean and smart, there were staff for that, and during the holiday they went through his wardrobe and drawers to wash then iron anything that was less than perfect. His room was also cleaned from top to bottom.

That created a regular problem for Tom.

He stared at the other bag, then gingerly opened it. On the top were his lingerie and tops, under that his skirts and finally a tartan dress. He was holding it up, ready to put it on a hanger when the door opened suddenly.

“I’ve not been able to … well look what we have here!”

“It’s not mine.”

Tom tried to think of an excuse. He’d dreaded this moment.

“It looks like it will fit perfectly. Just as well, as James McDonald didn’t have a partner for the ceilidh. You can dance, can’t you?”

“Yes, but …”

The barman left, Tom was left shaking. He hung the dress up and contemplated what to do next.

There was a soft knock on the door. Without waiting for a reply, a woman walked in.

“My husband said you’d make a good lassie. Let me have a look at that dress, what shoes do you have?”

Tom was visibly shaking and couldn’t say a thing. Without a word the woman left and returned five minutes later with a small glass and a jug of water. Tom hadn’t moved.

“Now, calm down. It isn’t that bad. I’ve brought you some single malt, not that lousy blended stuff my husband poured for you.”

She poured a splash of water in it and handed him the glass. He hesitated then sipped. He’d expected it to be harsh on the tongue but found it to be soft, he thought he could detect the smell of peat.

“That’s it, now don’t drink it all at once. I don’t want to know the details but do you dress as a girl often?”

Tom nodded.

“What do you call yourself?”


“That’s nice but hardly appropriate for tonight. How about we call you Tamara? I don’t think your voice will be a problem, you’ve got a soft Scottish accent. I presume you’ve picked it up at school.”

Tom nodded.

“Now, Tom, Tamara, my husband was correct about James McDonald, he is short of a partner. He’s also not the tallest, if you get my drift, so you’ll be perfect. You only have two hours to get ready, and I have to get ready myself, so I want you in the bar within the hour. Do you have a set of underwear?”

Tamara reached over to the pile of clothes on the bed and found knickers, tights, a half slip and a bra. Buried in the bag were his breast forms.

“Ahhh, that’s perfect.”

She reached over and took one of the forms, then put it down.

“B cup. That suits you. Now, get your cute behind in that shower young lady. I’m not going anywhere so don’t have any ideas of running away.”

Tom considered his options. If he left then he had no clothes. His wallet, containing his debit card and train ticket, as well as cash, was lying on the bedside cabinet and not within reach. He felt frightened, thrilled and beaten at the same time. He shrugged and disposed of his clothes before walking into the shower. The school still had communal showers so any pretense of embarrassment lasted seconds.

When we came back into the room, wearing a towel, two things were obvious. Firstly he could see an ironing board and his dress was being pressed; his slip was hung, already pressed. Secondly there was a set of hairdressing tools on the bed and a chair had been put ready.

“Hey, I never agreed to anything.” He’d gained some bravado whilst in the shower, but it was more a show. He knew he was beaten.

She hung up the dress then handed him a pair of knickers and bra. He went to turn but she grabbed the towel and left him stood there, bare. He hurriedly pulled on the underwear. She then directed him to the chair. He expected her to pick up the scissors but she went to the door and called for Jane. Who was Jane?

A girl, about nineteen, came into the room.

“Right, Tamara, sit tight and we’ll sort out this mess.”

She worked quickly, talking all the time, but Tom wasn’t listening. This was way outside any fantasy he’d had whilst sitting in his room at school pretending to be Tammy, now renamed Tamara.

She muttered about needing more time and how highlights would look good, and could it have been a little longer. She put the scissors down then used a spray on his head to dampen it before picking up a hair drier he hadn’t seen. Five minutes later she was sufficiently satisfied and showed him in a mirror.

He wasn’t convinced. Yes, his hair was very girly but it was still him in the mirror.

“Right, let’s get on with it. She reached for a make-up set and set about his nails, a bright red. His face followed while his nails dried. More than once he went to scratch his nose but his hand was slapped away. When she was finished, Jane withdrew and the older woman returned, Jane called her Diane.

“Right, up you get.”

He stood and she moved the chair out the way. He was instructed to put on the tights then she picked up the slip and had him step into it. The breast forms followed, then the dress was carefully dropped over his head. She turned him towards the mirror on the wardrobe door. He’d experimented with make-up but could never have achieved this look. Because he daren’t let anyone press his dress, it never looked as good as it did now.

A bag was lying on the bed, the contents of his wallet in a purse within. The empty shell of his wallet was next to the bag. A pair of short-heeled court shoes were on the floor. Diane picked up the glass and had him drain the remaining scotch then had Tom sit back on the bed. A mild sedative was in the scotch, in fact there had been very little scotch in the glass. Tom was now completely compliant.

“Your name is no longer Tom. You are Tamara and will answer to Tamara. You are a young lady.”

Diane spoke for several more minutes, making suggestions to him. Then led her down to the bar. Tamara was left by the fire with an orange juice in her hand. No point giving her any more alcohol just yet. The customers in the bar, many more by now, just stared at the young woman who was sat there sipping her drink, obviously not focussed.

A young man sat next to her.

“Good evening Tamara, my name is James McDonald. I believe you are my date for the evening.”

“Good evening James.”

Tamara was speaking but Tom was locked away inside, simply observing but unable to respond. Regardless of this, the drinks had now worked their way through to the bladder and Tamara needed the toilet. Instinct would have taken Tom to the Gents but Tamara gently stepped through the door of the Ladies, bag in hand. She emerged five minutes later to resume her place on the couch, beside James. His hand slid onto her knee and he lent over to kiss her lightly on the cheek. Tamara was thrilled but Tom was frightened. This had never been part of his fantasies.

Diane arrived shortly after with a coat. Tamara and James left the pub, holding hands, for the short walk over the road to the hall. As the door opened, the traditional music started the next dance. Tamara’s coat was taken and she was whisked onto the dance floor. Tom knew the dances and had often danced the female parts at school, due to the lack of young ladies at an all boys school. The dancing came easy for Tamara.

What wasn’t easy was James’ obvious amorous, indeed lecherous, intentions. When they rested between dances he would not let her go. She was introduced to many of the dancers, all in kilts or dresses. Tom however was very stressed, he hated parties and disliked meeting strangers, preferring to sit in a corner out of the way. Tonight however Tamara was the centre of attention as she was the stranger at the ceilidh.

The dance finished just before midnight. James led Tamara to his car, parked across the road. Tamara noted that she hadn’t seen him drink more than water all evening so at least he was safe to drive.

James’ hand rested on Tamara’s knee for most of the journey to his house, just out of town. Whilst it was a modest house it was obviously not cheap to maintain. Inside was spectacular. Tamara was open eyed. Tom was suspicious. James led her to a couch in front of the open fire.

“Tamara, I have been waiting for a girl like you to find me. Now my dreams have been answered.”

He leaned over and kissed Tamara full on the lips. He started gently and Tamara responded. She began to get a little excited. Tom was now petrified. The passion continued to rise as the kissing became just the first course of the meal. Tom had never imagined this would happen and struggled to break through. He tried to yell, he had to get away. His heart sped up in his panic.

Tamara screamed in ecstasy.

The whistle sounded repeatedly as the train pulled into Thurso, Tom woke suddenly, sweating on the warm train. He rubbed his eyes and spied the minibus on the station forecourt before leaving the train. Once sat in the minibus, with several other pupils off the same train, he patted the bag next to him – just not the one containing his books.