tagTranssexuals & CrossdressersA Holiday Job Ch. 02

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.’


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.

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