Catia Becomes a Ladyboy Escort

"Well don't worry, I'll look after you." They then slept in each other's arms, both very contented.

The next morning they woke up and started chatting like old friends. Isabela said she would strongly recommend that the agency take Cátia on, but Miss Ferreira would still want to do a final interview.

Whilst waiting to be summoned by Miss Ferreira, Cátia attended 'Mrs Coelho's Academy for Young Ladies'. She was expected to wear the 'school uniform' of a blazer, tie, white satin shirt, a very short pleated skirt and a straw boater. Mrs Coelho had previously taught at a convent and had been hired to rapidly teach Cátia how to be a lady. She trained her in makeup, deportment, etiquette, elocution and hair styling. The lessons were held in an old class room and lasted for about four hours each day. For makeup and hair styling, Cátia would strip down to her underwear and join Mrs Coelho in her bedroom. They got on well, but if Cátia broke any of the 'school rules' Mrs Coelho would punish her using a ruler on her bare bottom. Something she evidently enjoyed doing. Tough though it was, Cátia became more feminine by the day.

After a hard day at school, Cátia was thinking of how she could impress Miss Ferreira with her enthusiasm to work for her agency. She tried to paraphrase President Kennedy with, 'I shall suck any penis, bear any humiliation, meet any client, spread my legs for any man, fuck any woman, to assure my survival and success as an escort.' But worried Miss Ferreira might find this frivolous. Joking aside she was desperate to join the agency.

A few days later Mrs Ribeiro arranged for Cátia and Miss Ferreira to meet over lunch. She stressed how important the meeting was and told Cátia to dress in her school uniform and be respectful. They agreed to meet in a bar beforehand and arrive at the fashionable restaurant on Rua Garcia D'Avila together. Mrs Ribeiro was clearly nervous about losing a large fee and very ill at ease. She had made a real effort with her appearance, spoilt Cátia noticed by grossly overdoing her makeup.

Arriving at the restaurant Mrs Ribeiro did the introductions. Cátia was struck by Miss Ferreira's confidence and natural elegance. She took her time looking at Cátia before inviting her to sit down. Cátia felt very self-conscious in her unsophisticated uniform and ultra-short skirt. A perceptive person might have been able to feel the tension in the air, but to most they looked for all the world like two 'ladies who lunch' and a 'favourite niece', exchanging the latest gossip. They ordered tiny, vastly overpriced salads (the only thing Cátia was allowed at lunch) and made painful small talk until the waiter served the food. Miss Ferreira then got down to business. She started interrogating Cátia on her experience and the sexual services she might be prepared to offer if she came to work for her agency. Cátia knowing she had to impress Miss Ferreira, pretty well agreed to everything, saying she was very excited about the prospect of working as a ladyboy. Miss Ferreira seemed satisfied and complemented Cátia on her looks and congratulated her on the success of the operation. After seeing her in the flesh she was happy to represent her for a year. Over coffee Miss Ferreira passed Cátia a formal contract asking her to read it and sign if she was happy. Cátia did so, formally becoming an escort and consigning her life as Mateus to history.

After the meal, Miss Ferreira offered Cátia a lift to the villa, saying her personal possessions could be sent on later. They drove to a village just outside Armação dos Búzios and from there through some high security gates to a magnificent villa. Cátia was amazed at the size of the place. It was an ultra-modern construction, with huge windows and open airy spaces. Although it looked out onto the sea, it still had a large swimming pool that snaked all the way into the main living room. The décor was minimalist, but reeked of sophistication and wealth.

Cátia saw dozens of devilishly attractive boys and girls lounging around the pool. Miss Ferreira briefly announced Cátia's arrival and that she would introduce her formally before dinner. Cátia was reassured by the genuine looking smiles and the words of welcome. She just felt so humiliated in her school uniform. What would they think of her? She almost felt like stripping-off then and there. She was an escort not a naïve schoolgirl.

But Cátia knew she didn't have the courage, so meekly said 'hello' and followed Miss Ferreira, who proceeded to showed her to her room. It was wonderful, it was positively palatial with a great view of the sea. It was a million miles from the shanty town that had been her home up to now. One thing Cátia did notice was how feminine it was, although the walls and carpet were beige or light yellow all the accessories were pale pink. The most obvious being the large double bed covered in pale pink satin sheets, but the colour scheme also ran to the sofa, chairs, bathroom and towels. Miss Ferreira briefly showed Cátia the closets, saying they had taken the liberty of getting her some evening dresses, bikinis and underwear to be getting on with. Cátia would be given a clothes allowance so she could choose her own clothes in future. She also showed Cátia her computer, which would allow her to stay in contact with her family but more importantly act as her electronic diary for 'dates'.

Cátia was made to feel welcome. She found she had been put in the girls' wing and as soon as Miss Ferreira left a dozen of them piled into her room. She was immediately the focus of attention as they asked about how she became a ladyboy. They were fascinated. Cátia learned she was the first ladyboy who had ever been employed at Búzios and the girls became very possessive of her. Each one had some advice and stressed that Cátia could call on them night or day.

Cátia's next-door neighbour was a stunning girl who introduced herself as 'Safira'. She readily took Cátia under her wing showing her around the villa, introducing her to everyone and generally explaining what to expect of life as an escort. She even went through the list of sexual services Cátia had promised Miss Ferreira she would perform. Cátia wished she had thought more carefully before agreeing to some of these things. The pain and humiliation would be indescribable. But she had signed and there was getting out of it.

Each evening Cátia checked her computer to find out her schedule for the following day, only to discover she only had more makeup, deportment and elocution lessons. So much of the girls' gossip revolved around clients, their foibles and the presents they gave, that Cátia almost inevitably felt left out. She was nervous about prostituting herself, but anxious to start all the same.

Now that Cátia's tits were totally healed, Miss Ferreira decided that she needed to get some high quality photographs done for her webpage. She introduced her to the firm's photographer, Chiara Salvadori. Cátia was struck by her bohemian elegance, but also a little frightened at her severe manner. She was dressed entirely in black and had her hair pulled back in a tight ponytail. She had an aggressively professional approach and made it plain that she expected Cátia to do exactly what she was told. They went to Cátia's room and Chiara went through her draws selecting the clothes she wanted Cátia to wear. The first shots were in the main living room with Cátia in one of her short figure-hugging dresses, holding a glass of what was meant to look like champagne. Cátia then stripped down to her beloved pink bikini and lay by the pool for more photographs. Chiara tried to persuade, but finally had to order, Cátia to remove her top. Despite Cátia's reluctance the photos were a success.

Chiara then took Cátia to her bedroom where she photographed her in stockings, panties and suspenders. She had thought that there would be an obtrusive 'bulge' between Cátia's legs but was surprised at the girl's skill in concealing this when required. Chiara admired her body and got her to strip down to a brief black thong. She had a fresh, healthy look that Chiara liked in her models. Cátia needed some encouragement to pose totally naked. But Chiara started by photographing her lying on her front on her bed with just her bottom and the tops of her breasts on show, then encouraged her to rise until Cátia was kneeling in the 'full frontal' pose. Once naked, Chiara forced 'the slut' to pose for a number of increasingly compromising photos. The final pictures showed a visibly excited Cátia, with her legs spread, playing with a large dildo.

Cátia had been finding it hard to consider her tits genuinely part of her and not an alien addition. It was only when she saw Chiara's photos they she realised how natural she looked as a girl and began to be proud of her body.

~

Eventually Cátia saw she was booked for her first date. She was almost impossibly nervous. The girls could give her advice, but when it came to it she was on her own. Cátia started preparing almost two hours before the date. She couldn't help but be aroused as she stood naked going through her lingerie draw, examining one tiny pair of lace knickers after another. The silk felt so soft against her skin. Miss Ferreira had been generous, so there was a huge amount to choose from. Eventually she decided on a bra, panties, suspenders set in bright pink satin edged in black lace. Cátia carefully laid this out on her bed and went to have a long bath. She massaged herself with her favourite bath gel, so no matter how frantic the 'action' she hoped she would smell perfectly fresh. She then shaved for the second time that day and sat down to do her hair and makeup.

Cátia was so nervous she found it hard to keep her hands steady when applying the cosmetics. She wondered at what she was about to do. She was going to give herself to a stranger. She had lied to Isabela about having numerous homosexual partners. In fact Cátia had never even touched a man, still less allowed one to kiss and fuck her. Safira had tried to prepare her, explaining how she should give a blowjob and take a fucking. The answer to the latter seemed to be to relax and use loads of lube. Easier said than done. She not only had to sleep with a man, she had to make it look as if she was enjoying herself. Could she go through with this? Could she really put a penis in her mouth? Miss Ferreira said the client wanted 'an over-sexed minx'. Would she be frigid and back out? Despite the fear Cátia knew part of her was looking forward to the date.

Returning to her bedroom, Cátia stood in front of the full length mirror and put on her suspender belt. She shuddered with desire as she felt the soft silk against her naked body. Then she pulled on her stockings over her perfectly smooth legs. Next she stepped in to the delicate silk panties she had chosen. The elasticated lace sides felt snug as she carefully eased her cock between her legs. Safira advised her to do it this way round as she said 'gentlemen' often liked girls to keep their stockings on, during sex. Lastly came her bra, enclosing her ample breasts. After getting into some high-heels, she squeezed her tits together and pouted at the mirror. The diet was worth it and she had to admit the surgeon had done a wonderful job. It was now almost time, so she took herself down to reception and waited for her date.

She knew she would do anything, absolutely anything that the guy wanted. She simply had to prove to Miss Ferreira and Isabela that she could be a success as an escort. Cátia flicked through a copy of Cosmo, but was quite incapable of reading even its limited prose. She felt very self-conscious being out in public in such provocative underwear and tried to avoid eye contact with the other boys and girls as they passed through the lobby.

The date, a banker called Rafael, was late and Cátia debated on how long to wait before finding out if she had been stood up. Five minutes passed, then ten. Just as she was about to get up to do something or at least ask someone what to do, he came through the door. Cátia sprung to her feet and went to greet him, smiling broadly, kissing him on both cheeks.

The man was reasonable to look at without being positively handsome, overweight without being fat and his hair was thinning without him appearing bald. He was several inches taller than Cátia despite her high-heels and must have been forty kilos heavier. He took his time to look at Cátia.

"So you are my ladyboy?"

"Yes Sir. My name is Cátia and I'm here to fulfil your deepest desires."

He nodded and she took him by the hand and led him to her bedroom. As he followed her up the stairs, all Rafael could do was stare at her pert arse covered in such a tight little pair of panties.

When she opened the door, her whole mind seemed to go blank. What had Safira said she should do first? A drink, or should she get him naked to stop him backing out. She couldn't remember. In the end she led him to the couch, sat him down and snuggled up beside him. She turned her body so her mouth was inches away from his and her tits rested on his arm. Cátia stroked his cheek as she asked if his trip had been alright. As they chatted she realised that the poor guy seemed almost as nervous as she was. Relieved by the growing bulge in his trousers she went off to get some wine. As they talked Cátia gently rubbed her hand between Rafael's legs. Cooing about how lucky she was to get such a handsome gentleman all to herself.

"Oh Rafael, I can't resist you any longer. Let me take your clothes off."

Rafael was almost incoherent, but did not protest as Cátia got to her knees to remove his socks and shoes and then unbuckled his belt and slowly lowered first his trousers then his boxers. She straddled him, with her knees each side of his thighs, leant forward and kissed him. All the while unbuttoning his shirt. The kiss started as a chaste peck, but gradually she eased her tongue into his mouth and kissed him hard, very hard. She rubbed herself against his crotch, whispering, "Come on, take your little slut and give her a good seeing to."

She pulled her now naked date across the room to her bed and lay him down, legs wide apart. Cátia then knelt down and began to give him a blowjob. She had never had a man's penis in her mouth before, having always practiced on dildos and was unsure if she could go through with it. Her determination to be a good whore overcame her instinctive revulsion. Before she could have second thoughts, Cátia she placed her lips around his erect penis. It felt unnatural but she knew she could and must do this. Cátia realised she had broken an important taboo, not only was this her first sexual experience with a man, but she was now a prostitute. The thoughts flitted through her head and in a second she was concentrating on giving Rafael pleasure. She licked the head of his cock and remembered Safira had told her to stroke a guy's balls. Now he was fully erect, she sucked with all her might, desperate to please her first client. Her actions almost seemed instinctive, as she went down again and again. As he approached climax she withdrew and started nibbling his balls. Rafael was squealing with ecstasy. She wanted to extend is pleasure, so now moved from 'active' to 'passive'. She pulled down her knickers and got down on all fours on the bed, crying, "Come on Sir. Fuck me, fuck me hard. I want you so badly."

Rafael saw Cátia's pert little arse and dangling penis and wondered as to how ladyboys could look so cute. He knelt behind her and stroked her bottom. He was fascinated by Cátia's cock and asked, "Can I touch it?"

"Of course, I'm your slut."

He eagerly stroked her stiffening shaft. Rafael then felt Cátia's balls. Cátia felt herself get hard. This was the first time a man had touched her and she was enjoying it! He positioned her on all fours and eased her buttocks apart. Now she knew she would earn her money. This was the ultimate boundary. Could she allow herself to be sodomised? He gingerly inserted his penis into her sphincter. Cátia tried to relax, knowing the most important part of the date was about to begin and she had to satisfy her 'man'. She felt the pressure on her anus. Despite the lubricant she started to feel the pain as his penis began to stretch her. Cátia's winced, but Rafael continued his pressure and soon he had fully inserted his penis. She gritted her teeth as he slowly extracted his cock. Now in, he began to pump hard. Her cries to pain sounded like pleasure to Rafael. Even if he had known her discomfort he had no intention of stopping. He had paid his money and the whore was going to give value. Value involved throwing Cátia around as he fucked her in one position after another. He gave her no respite as he took his pleasure. The first time he came he exploded in her arse, the second he sprayed over her face and tits. Cátia was shell-shocked at her treatment, but also proud that she had succeeded in giving her first customer so much pleasure.

When Rafael was fully satisfied, Cátia helped him dress and putting on a brief silk robe escorted him to the front door. Despite her exhaustion she ran to Safira's room, knowing she didn't have a date, and poured out her relief at having successfully sold herself for the first time. She explained how she had brought Rafael to two orgasms and all the tricks she used to heighten his pleasure as if she was talking to a virgin not a lady who slept with nigh on a thousand men a year. The adrenalin rush masked the pain she would soon feel from losing her anal virginity.

The girls always went out to celebrate one of their number's first date. So the following lunchtime they all dressed up and went to a local restaurant to toast Cátia's success and make her feel 'one of the gang'. Although her arse hurt like hell, Cátia was terribly grateful to them for accepting her. As Lúcia said, they felt a ladyboy was a lady first and a boy very much second.

The girls were always running around naked as they prepared for dates, borrowing lingerie, clothes and condoms as necessary. As they thought of Cátia as a girl they never dreamt of covering themselves when she entered the room. A privilege none of the boys ever enjoyed. In fact they were pretty well banned from the girls' wing unless a client asked for a 'duo'.

After this success, Miss Ferreira allowed Cátia to lay by the pool like all the other girls. She was the only one allowed to wear a bright pink bikini so customers would know what to expect. In the summer she pretty well lived in the bikini.

Cátia had a rapid education on the duties of an escort. When it came to the bedroom she became used to spreading her legs, sometimes the customers would want her on her front, sometimes kneeling on the bed, others laying on her back, legs pressed against her shoulders. She had soon been fucked in every position imaginable. She became used to the pain and feigning the pleasure they wanted. Being 'active' was more difficult, Cátia was told that she would have to train herself to be able to get and retain an erection in an instant, regardless of her mood. As Isabela put it she was a 'fucking machine' and had to get used to screwing every orifice the customer wanted.

Cátia had both male and female clients, all of them wanting something new, relishing 'forbidden fruit'. Most of the time clients wanted Cátia as the sophisticated young lady, who could seamlessly move from making clever conversation in the drawing room to kinky sex in the bedroom. But sometimes they wanted to see a simple tart, so Cátia's closet also contained tight PVC miniskirts, thigh-high boots and leather knickers.

Every week Isabela would summon Cátia to her room. She would make her strip naked. Isabela would then review her feedback, commenting and warning Cátia about her future performance. Isabela would proceed to walk around the girl feeling her naked body, after which she would revise Cátia's diet or fitness regime. Cátia found being humiliated like this hugely erotic and loved being Isabela's 'pet'. She willingly became her personal servant, dressing up in a very short, satin maid's uniform and performing whatever tasks her Mistress wanted, menial or sexual.