A Holiday Job



Paul stirred briefly in bed as his twin, Anne, called out as she dashed from their holiday apartment. Paul glanced at his watch; it would be a rush but she should make it to the airport in time for her flight back to England.

They had been on holiday at a popular Mediterranean resort for a week. Anne had to return for her job was starting, but jobless Paul was staying for another week. As he lay there Paul reflected on his sister's frantic rushing that morning, since they had both overslept badly.

'I wonder what she will have forgotten?' he mused as he fell into a deep sleep. So deep that he didn't notice the phone when it rang a few minutes later, nor the second and third times it rang.

At the airport Anne cursed her sleepyhead brother and put down the phone. There was no time for her to ring again; she now had some things to do before the flight.

By the time Paul woke, Anne was waiting for a train back in England, thanking her lucky stars that the customs staff had not been too efficient!

Paul final woke and wandered about the flat. On the table was his sister's bum bag. Paul saw it and laughed. 'I knew she'd forget something!' A thought struck him. He opened the bag. Inside were his sister's passport and a few pounds sterling. That was odd. How had she caught the plane he wondered?

Unconcerned for the moment he went to fetch some clothes from his case. 'Wrong case again!' he thought as he opened it to find bras, panties and dresses. This had happened so many times in the small apartment he just shut it and looked for his case.

His case? His bum bag? Anne had a case and a bum bag when she left, but her stuff was still in the apartment. The penny dropped. 'She's got all my stuff!' he exclaimed out loud.

A search of the apartment showed that this was true. In her haste (and in the dark, since Paul had complained when she had tried to turn on the light) she must have taken the wrong bags. Instead of his clothes, his passport and a weeks spending money all Paul was left with was his sister's clothes and passport and no local currency! He also had a sick feeling in his stomach.

He sat and thought, piecing together what must have happened. Last night he had come in later than his sister and he could remember moving his case to get something. He must have put it back in the wrong place. He could also guess how Anne had managed to get home.

The previous winter at a fancy dress party for New Year, he and his sister had swapped roles. He had gone in the naughty schoolgirl outfit and she had worn the tuxedo and gone as a spy. Everyone had been taken in, since they looked and sounded so alike. His sister must have pretended to be him for the flight home. Slowly Paul realised that he would have to become his sister, at least for the flight home and probably for the whole week!

His main problem was money. He had no local currency at all. The hotel did a buffet breakfast, but not lunch or dinner. They had eaten out in the evenings. He couldn't survive for a week on breakfast rolls! If only I was Anne, he thought, then I could take up that offer of a job as a waitress in Nico's Bar. (Nico's Bar was a popular local bar, always full of tourists and always looking for waitresses. Nico, the owner, had offered Anne a job every night they had gone there in spite of her constant refusals.) Paul formed a plan. He would pretend to be his sister, see if he could get the job for a week and use the money to live on. It wouldn't be too bad, he reflected. He had quite enjoyed his evening as Anne; a week might even be fun!

He set about transforming himself. In the shower he carefully shaved his chest and legs. Using the hairdryer in the room he styled his hair in as feminine way as possible. Luckily he had shoulder length hair so he was able to do quite a good job. Next he began to dress. He slipped on a pair of white panties, tucking his cock between his legs. He put on a matching bra, stuffing some of Anne's stockings into the cups. Over this he selected a pastel striped t-shirt and a short pink skirt to wear. He did consider wearing his sister's jeans, but decided that he had to look as feminine as possible. To complete the outfit he slipped into a pair of strappy white high heels. He walked round the apartment for a while getting used to walking in the high heels and wearing a skirt. Last he went to work on his face. Painfully he plucked his eyebrows and then shaved his face. All the time he had spent waiting for his sister the previous week, watching her do her make-up, now proved to have been time well spent. The transformation complete he viewed his reflection in the mirror.

Not bad, he thought. I can tell it is me, but … he left the thought hanging. Hopefully everyone else would be fooled.

Driven by hunger he had to venture out. In the pockets of Anne's jeans he had found some coins, enough to buy a sandwich and a drink at a local café. Bravely he shut the door behind him and walked down the corridor. The first time someone passed him he was terrified and nearly pee-ed himself. The woman said nothing and his confidence grew. As he walked through the lobby and into the street he even noticed a couple of guys checking him out.

As he walked along the street the cool breeze fluttered the hem of the skirt, a truly wonderful feeling for Paul. He was feeling very calm and very liberated by his new appearance. He sat down at an outside table at the café and a waiter came over.

"What can I get you Signorina?" he asked, flashing a smile that Paul had only seen Anne receive before. He ordered and felt another surge of confidence as the waiter left without comment. With his food and drink he received another flashing smile and a question.

"Where is your brother today?"

"He had to fly home, I'm staying for another week."

"Very good. I am Jorge and I hope you'll be back again."

"Thank you Jorge. I'm Anne" Paul replied, thrilling at the first public use of his new name.

"Anne – a pretty name for a pretty lady" said Jorge smoothly and then he went to serve on another table.

Paul spent the rest of the afternoon at the hotel, topping up his tan. On the balcony of the apartment he could sunbathe unseen. He decided to get some suitable tan lines, so he wore a bikini!

Tanned but fortunately not burnt, Paul got ready for the evening. He had another shower and an all over shave, before reapplying his make-up. For his visit to Nico's he selected a black shirt-dress, belted at the waist and buttoned down the front and black high heels. His make up was a little more adventurous as befitted an evening out.

The bar was already quite crowded, but Paul walked confidently in, finding it easier and easier to copy his sister's walk. Nico was behind the bar and Paul walked over to him.

"Good evening Anne, what can I get you?"

"Um, it's a bit embarrassing Nico, I wondered if I could talk to you?"

"Of course!" Nico shouted over to the other bar man in Spanish. "Come this way."

Nico came out from behind the bar and guided him to the office at the rear. Paul was conscious of the gentle but firm hand Nico placed on his back to steer him through the crowd. In the office Paul, as Anne lunched into her prepared story, which was that Paul had taken the flight home (a friend was very ill) and she had managed to get a second week of holiday and was staying in his place. Nico listened attentively

"The only thing is Paul took all the money by mistake," Paul continued, "so I really need some and I was wondering if that job you offered me was still open?"

"For you my dear Anne of course. You can start tonight, if you want"

"I can! That's great."

Nico left and returned with some clothes draped over his arm. "Try the uniform on now," he said.

"Ok" said Paul, "where shall I change?"

"Right here, you're not shy are you?"

Paul so needed the job that he just shook his head and began to undress. He managed to turn his body to hide his stuffed bra as he slipped on the short black Pareo and the tight white t-shirt that the girls all wore. The pareo was a sort of short sarong that was virtually open to the waist on one side.

"Very nice" said Nico admiringly. "It suits you Anne."

Paul caught a glimpse of his reflection in a mirror. It did suit him in a tarty sort of a way.

"Now the standard conditions are these. You'll get paid at the end of the week, but any tips you get are yours to keep."

"The end of the week? But I'm broke"

Nico laughed. "What do you think I am, a charity?"

After a pause he added, "but I'm sure we could come to some arrangement."

Paul was worried now. As Nico was a man who made waitresses wear skimpy uniforms and even change into them in front of him, he had a bad feeling about the 'arrangement'.

"Remember when you were drinking in the bar with that American?"

Paul searched his mind. He could vaguely remember his sister being chatted up by some American.

"Yeah" he said cautiously.

"Well I'd like to see, and feel for myself."

"Sorry Nico, I was a bit drunk, what did I say that night?" Paul asked playing for time.

Nico moved from his seat and perched on the desk in front of Paul. He unfastened his zipper and took out his cock.

"You said that you gave fantastic blow jobs."

Inwardly Paul cursed his sister for having said that. "I was very drunk."

Nico shrugged and threw a few notes down on the desk.

"If you want it, you know what to do."

As if in a daze, Paul knelt down before the bar owner and reached for his cock. He moved his head towards it. He reminded himself how desperate he was for the money as he ran his tongue along the stiffening cock he held in his hand. Nico's moans suggested that he was doing a good job and oddly this inspired him. Slowly he took it a little way into his mouth, teasing the tip with his tongue, tasting the pre-cum dripping from the now erect cock. He sucked hard and once more Nico moaned.

Then Nico took control. Holding the back of his victim's head he pulled it towards him. The erect cock was thrust right into Paul's mouth, making him gag. Nico was relentless, sliding his cock backwards and forwards, as Paul sucked, trying to do a good job to please his new boss. Eventually Paul felt the bloated cock twitch and shoot its load. He had no choice but to swallow the cum.

As Nico tucked his now limp cock back into his pants and did up his zipper, Paul felt a trickle of cum running from the side of his mouth. Swiftly he picked up the money.

"Not bad, not bad at all. Do that again on payday and this will be a bonus for you and not a sum I deduct from your wages." He slapped Paul's bum. "Now Anne, fix your make-up and get to work."

The work was fairly easy. It consisted of going round the tables, collecting glasses and bottles and taking orders for fresh drinks. The customers were a nightmare, however, assuming that buying a drink gave them the right to a feel of the waitresses' bum or legs. At first Paul tried to shy away, but as the evening went on he noticed something. The waitresses, who encouraged the mauling and even appeared to enjoy it, got better tips.

'Oh well, I've already swallowed cum, I can swallow a bit more of my pride' thought Paul.

He began to flirt as outrageously as the other girls, allowing the guys to stroke his leg and bum as they ordered the drinks. At one point he even sat on a customers lap, wiggling his bum provocatively as he felt the customers cock begin to harden. It worked, he got a good tip.

At the end of the evening he was cleaning up with another English waitress, called Linda. She had a huge amount of tips.

"How did you get that much?" asked Paul.

"Well, it's easy if you like sucking cock, which I do."

Linda explained that it was a regular thing for the waitresses to follow the customers into the toilets and give them blowjobs for extra large tips.

"The thing is," Linda, explained, "I only pick fit blokes and I'd do it for nothing anyway with them, so getting paid is a bonus. See you tomorrow."

The next day Paul spent some of his 'bonus' and tips on lunch, again Jorge greeted him warmly and they chatted for a while. Jorge was really quite charming.

Back at the bar, Paul threw himself into the fray once again. Flirting from the start, he couldn't bring himself to go as far as Linda, but he did all right. Back in the hotel room he was surprised to found how quickly he had got used to his new role. He liked the attention and even some of the touching. It confirmed how good he looked and he liked that. The week passed quickly.

His flight home was on Saturday afternoon. Friday would be his last night in the bar. At lunch he chatted to Jorge.

"I will be calling into Nico's tonight, Anne, and I hope I will see you there."

"I'll look out for you."

Oddly Paul felt very flattered that Jorge was going to come and see him.

The evening arrived. Paul was as flirtatious as ever and the tips were piling up. Around 9pm Jorge arrived with a group of his mates. Paul felt the urge to put on a good show for Jorge and gave him a big hug and a peck on the cheek. He allowed Jorge to hold and stroke him when he took their order, but it felt different. The other guys touched him like he was a piece of meat. Jorge's touch showed gentleness and tenderness and this gave Paul a warm feeling inside. At the expense of tips from other tables he spent a lot of time with Jorge group. Although he didn't really understand what they said in Spanish, Jorge would translate for him.

One time Paul saw Jorge blushing. "What's the matter?"


"Tell me, something is up, you are blushing."

"Well my former friend here," he said shooting a mock angry glance across the table, "reckons that I have the 'hots' for you."

Paul bent down, and placed his hand on Jorge's crotch. His eyes widened and he turned to stare at Jorge. His cock was hard and erect, bulging against his trousers. He moved his hand stroking the cock through the thin material. Jorge put his hand on top.

"Not here Anne, not like this," he whispered.

Paul stopped, moved by the intensity of his words. He struggled to concentrate for the rest of the shift, and didn't even notice Jorge and his friends leave. At the end of the evening, Nico called him into the office.

"Well Anne have you enjoyed your week?"

"Yes I have Nico, thanks for helping me out like that."

They hugged.

"Here is your salary, and here is another bonus." He handed Paul an envelope and a large box. "Go ahead, open it now," he urged.

Curious, Paul opened the box. In it was a pair of false boobs. Paul looked up sharply, his face red. Nico was smiling.

"I guessed that first day in my office." He said. "There was something not quite right, so I kept a close eye on you. You're very good."


"Yes, I wasn't completely sure until you looked up just now and it was there in your eyes."

"What are the boobs for?"

"Well I think you would get more tips and be more popular if you had bigger tits. These stick on and feel very realistic. You'd look great and Jorge would like it too."

"Jorge? Why?"

"Don't you think I noticed? You feel something for him, don't you?"

"Well, I do like him yeah," Paul, confessed a little embarrassed.

"So stay. Continue working here at Nico's."

To be continued...

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