0 comments/ 189588 views/ 19 favorites A Holiday Job By: Misslexia 'Bye!' 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?" "Nothing." "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." "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... A Holiday Job Ch. 02 “Anne” was stunned by Nico’s offer. When Paul had discovered that his sister had left taking the wrong suitcase, the idea of becoming her for a week had been very appealing. The job in the bar, the innocent flirtation with Jorge the cute waiter over lunch had all been very enjoyable, but could it continue? “I can tell you Anne, the customers love you and the way you move around the bar is very sexy. You are getting good tips.’ encouraged Nico. ‘I have a room in one of my apartment blocks where you could stay for a small rent; if we come to an arrangement.’ Nico smiled and Paul felt a sick feeling of déjà vu. He knew the kind of arrangement Nico had in mind. ‘Now?’ ‘Not tonight, Anne, when I show you the room tomorrow.’ Nico, I have a question.’ ‘Go ahead.’ ‘You said you could tell almost right away. Who else knows do you think?’ Nico laughed. ‘Don’t worry, in my youth I worked as a barman in a hotel that attracted a lot of cross-dressers and trans-sexuals. I am almost an expert, one might say. You are as good as the very best so don’t worry your pretty little head. No-one will know, unless you tell them.’ The next day Nico took Anne to the room. It was small, but clean. A bed-sit, with a washbasin, the only major downside was the need to share the toilet and shower room. And, of course, the ‘arrangement’ for the rent. For the second time Anne (in his head Paul was thinking of himself as Anne) knelt before Nico as he lowered his zipper. Reluctantly, but less clumsily than last time, he coaxed the cock into hardness and began to lick, brushing the exposed tip with his lips and tongue… Nico left and Paul/Anne cleaned up. The question now was what to do about Jorge. There was a definite frisson of chemistry between them. The fact that Paul could feel this for a man was a bit of a shock, but how would Jorge react? Paul decided it was best to try to avoid him for now. And so began the second week of Paul’s life as Anne. He quickly formed a routine that seemed to work. Every trip out was preceded by a close shave and fresh makeup. Consciously avoiding the restaurant where Jorge worked, trips out included the local shops, always buying obviously feminine things, and the local park. Anne avoided the beach, too touristy for one thing and she would look out of place unless she was skimpily clothed for another. Before starting work in the evening’s Anne liked to sit in the shade and quiet of the local park. She became quite well known. In the bar, Anne continued to get used to life as a waitress. The flirting was fun; the being groped less so, but the other girls were nice and friendly and they were pleased she had chosen to stay. For a few days Paul really believed this could work. Then Jorge came to the bar and waited for Anne after work. This was a moment Paul had been dreading. ‘So, Anne, you have stayed and yet I am the last to know? How do you think that makes me feel?’ said Jorge harshly. ‘I’m sorry Jorge, I didn’t want to hurt your feelings, but it is rather complicated.’ ‘And I wouldn’t understand? What is his name?’ ‘His name?’ ‘The one about who you now feel so guilty.’ ‘Oh gosh he thinks I have a boyfriend at home’ thought Paul. He grabbed at this straw. ‘He’s called Paul. I couldn’t do this too him, but I didn’t want to hurt your feelings.’ ‘Well you have. Not all of us waiters are looking for casual sex, I thought you liked me.’ Paul felt ashamed. ‘I’m sorry.’ He called out as Jorge walked off. Still in her uniform Anne headed for home. Towards her came some of the drunken English lads from the bar. They had been very attentive asking her why she wouldn’t do what Linda did. (Linda was well known for sucking customers’ cocks to get big tips.) They gathered round Anne. They started pushing and grabbing, calling her ‘stuck up cow’, ‘a bitch’ and worst of all ‘a fucking prick teaser.’ ‘Lets see how stuck up you are with my cock inside you!’ shouted the ringleader. Terrified Anne was helpless as they ripped her blouse and tore at her skirt. In her head the worry about what they would do when they discovered ‘her’ secret was worse than being so roughly handled. Tears streamed down her face as her skirt was ripped off. Suddenly there was a scuffle and shouting. Anne lay there terrified, sobbing bitterly. A hand touched her shoulder and she flinched still terrified. ‘Hey Anne. It’s ok. It’s me. Jorge. I sorted them out for you. I’ll look after you.’ Filled with happiness they hugged. Jorge handed Anne her skirt and she slipped it back on before he walked her home. Jorge insisted on coming in. ‘Jorge I am so grateful and after what happened earlier, you’re a saint.’ ‘Maybe.’ He shrugged. ‘Now I will tell you something and you will answer me truthfully. OK?’ Anne nodded. ‘When I rescued you and while we walked home I noticed things. I noticed a breast that seemed to be falling off. I noticed a very un-ladylike bulge in your pretty panties as you lay there. So the truth, please.’ He deserved the truth. As the tears flowed once again, between sobs the truth poured out. The suitcase mix-up, the feeling of friendship Anne felt for Jorge, the fear of telling him the truth. ‘So now you know. I’m sorry.’ ‘Was it a joke, to make me look stupid?’ ‘No I really felt we were friends, but I didn’t know what to say.’ ‘Who else knows?’ ‘Just Nico and you.’ ‘OK I will keep your secret on one condition.’ ‘What’s that?’ ‘You will be my girlfriend.’ ‘Girlfriend?’ Jorge explained that unless Anne/Paul became his ‘girlfriend’ she might be vulnerable to the attentions of other men. Also it would damage Jorge’s reputation if anyone knew he had fallen for a man-in-a-dress. There was one more thing. ‘Even now I know your secret Anne, I still cant get rid of the feeling I have for you. So long as you don’t change the way you treat me I would like to look after you.’ They both smiled and hugged. The next day Jorge and Anne walked around own together. He met her after work, where she was careful not to overdo the flirting. He walked her home. He came in. ‘Tonight I make you mine’ he whispered. And they began to make love. Tenderly Jorge caressed and stroked his girlfriend’s body. Nervously at first Anne responded. Gently they undressed. Paul felt very self-conscious with the breasts still attached and his cock beginning to respond, but Jorge was careful to avoid his cock as he ran his hands up and down. Soon his hands were stroking Anne’s bum, sliding a finger along between the cheeks. The part of Anne that thought as Paul fought with fear and revulsion. The part of Paul that thought as Anne submitted willingly to her lover’s touch. Anne felt the cold touch of the lubricated finger at the puckered hole of her arse. She felt the gentle pressure as it circled round, sliding, almost imperceptibly, further inside. Anne moaned with pleasure. Encouraged, Jorge began to slide his finger in and out, further each time, varying the pace and depth of each movement. He pulled out his finger. Anne felt a twinge of disappointment. Then the finger was replaced by something much thicker. Anne willed herself to take it, to take it all as far as she could. Gently Jorge eased his cock into Anne’s tight arse. H gripped her hips tightly, thrusting forward, moaning with pleasure as her tight hole gripped his cock. Anne became almost numb, like a rag-doll, being tossed about. Noisily Jorge reached his climax, shooting his cum up Anne’s bum. He pulled out, kissed her tenderly and left, saying ‘I’ll see you tomorrow.’ Anne lay there, with cum dribbling from her arse and cried, because he had gone. Paul lay there, with cum dribbling from his arse and cried from confusion.