Flavia's Secret

Filipe had always yearned to wear satin knickers. He loved the idea of wearing tight, little briefs made of sensuous silky material. He simply could not see why boys should not be able to wear silks or satins instead of plain cotton. But at home he had no opportunity to satisfy his desires. His mother would be sure to find any illicit underwear and then there would be all hell to pay. When he moved into flat with his friends, he bought a couple of pairs of brief satin panties, which he kept securely locked in his cash box. He only really managed to wear them in his own room or on rare occasions around the house when he was absolutely sure his flatmates would not be home. The prospect of being caught was an ongoing nightmare.

It was only when Filipe got his own flat that he had the privacy to actually act out his desires. The internet was a great boon for this. He simply bought ladies clothes in the name of 'F.Pinto'. With the curtains securely closed, Filipe began to dress for whole evenings as a girl. After a shower he would put on some panties and a silk camisole. Wearing stockings was a particular pleasure, he enjoyed sliding them over his calves, then stretching and smoothing the fine gauze over his thighs before attaching them to his suspender belt. He would then lay on his bed and slowly massage his cock through the fine silk of his panties, thriving on the sexual high.

Filipe was lucky in that he was naturally slim and had never really 'filled out'. He had a fine-featured somewhat androgynous face, so with a little makeup he looked truly convincing. Soon he began to model his looks on slimmer version of Thays Schiavinato, with her blonde hair and centre parting. He desperately wanted to become a girl, so practiced walking in high heels and started to train his voice to speak in feminine tones by listening to women reading books on CD. He even started shaving his armpits and trimming his pubic hair, but much though he yearned to do so, he didn't dare shave his legs. Dressing up like this gave him huge emotional and sexual satisfaction. Looking at himself in the mirror he was proud of his appearance, but still he had a nagging and terribly risky desire to go out in public dressed as a girl. He wanted men's lust and admiration. He had a recurring dream of walking into a high-end lingerie shop and discussing different types of bikini with a sweet, female shop assistant. Then having a coffee, letting his skirt ride up his thigh so guys on the next door table could see his stocking tops. Sometimes it ended with him performing a slow erotic strip. But although the urge was almost unbearably strong, he knew he would never dare go through with his fantasy.

Even though he lived alone he still took the greatest care with his security precautions; double locking the door when he dressed in his lingerie, using complex passwords on his computer, and always locking away all his stuff in a suitcase whenever he went out. He didn't trust his landlady so if he left the flat for any length of time he poured dust from the vacuum cleaner over the case to make it look unused.

When he went on-line he called himself 'Flávia' and claimed to live in a totally different part of town. On principle, he never posted pictures of himself. As time went on he spent longer and longer in ladyboy chatrooms. He found it fun swapping makeup tips and recommendations for where to buy clothes. But he never let his guard down, being very sceptical of who some of other members really were. Many of the pictures they posted, he was sure were of real women. He simply hated the thought that they were cheap voyeurs.

As time went on Filipe found himself in a terrible struggle between his desires and the absolute need to keep them secret. It seemed being able to talk anonymously about his feelings was a relief, perhaps the only thing that kept him sane. He would write about his needs and the deep frustration of not being able to satisfy them. Some of the chatroom members had clearly been through the same conflict and their sympathy and advice was a comfort. He 'friended' one or two these, but he still kept his distance. Even so, he realised the more he poured his heart out, the more he relied on their support. So eventually he took a risk and did end up swapping photos with a few of these 'friends'. He was deeply touched by some of the complements he received about how attractive he looked in his lingerie. These were a real boost to his very fragile confidence.

One evening Filipe came home to a private message from a particular friend saying, "Flávia, There is waitress job going next Tuesday at a club, I know. It will be a great opportunity for you go out in public in a safe environment and to meet other t-girls. Lots of cash. I promise no one will recognise you. Let me know if you are interested. Be brave! Love Suzana."

Filipe was excited, but scared. He couldn't think of anything else all day, and dreamt about it all night. He debated accepting from every conceivable angle. He vividly imagined how badly things could go wrong. He thought that Suzana might be luring him out to rape or beat him up. What would happen if one of his friends spotted him? But however awful his thoughts, he kept coming back to the thrilling prospect of going out in public, chaperoned by another ladyboy. He didn't reply that night, or the next. But the temptation was too great so eventually he wrote, "Suzana, I really appreciate the offer. My whole body has been tingling with desire since I read your message. I would really like to accept. But will you meet me before for a drink beforehand? Love Flávia."

Filipe still did not know if he was going to turn up. It would be very easy to back out. He could just write a quick lie that he had been kept late at work and then 'de-friend' Suzana. It would hardly be the end of the world. In the end he left work early and started to get ready almost two hours before he was due to meet Suzana. Half a dozen times he told himself it was too much of a risk and went to send her his apologies, but somehow he could never quite hit the 'send' button.

He shaved his chest and armpits and agonised over his legs, in the end he decided to do it and hang the consequences. Shaved for the first time, they felt wonderfully smooth. He loved the feeling as his stockings slipped up his legs. He felt incredibly aroused as he looked through his collection of lingerie. After much deliberation he pulled on a waspie to improve his 'figure', his favourite sky-blue knickers and matching camisole. Filipe had done this many times before, but the prospect of going out in public made this evening truly special. With increasing confidence, he did his hair and makeup. Finally he chose a figure-hugging black dress and a discreet leather handbag. He was ready.

Filipe looked in the mirror and thought, or perhaps just hoped, he would easily pass for a girl. Now the thing that was worrying him was how to leave the building without his landlady seeing him. Mrs Relvas would have been considered old fashioned in the 1920s. If she even suspected what he was getting up to, he would be out on his ear in a minute.

In the end he put on a large overcoat, took his high-heels in his hands and made a dash for it. As he got to the front door he heard the bitch shouting his name, but he pretended not to hear and was out in the street in a second. He ran to the end of the road before he put on his heels and hailing a taxi. During the trip he studiously looked out of the window and for once the driver didn't seem to want to talk. When they got to the bar, Filipe saw Suzana, dressed in a smart suit, waiting outside. To his surprise her photo had been real. He would never have guessed she was a ladyboy. She was blonde, medium height, largish breasts with a pretty, 'sympathetic' face. Filipe guessed she was in her late thirties, but was still very attractive.

She seemed pleased to see him, "Flávia, I didn't think you were going to show."

"I nearly didn't. I'm nervous as hell. This is my first time out, so can we have that drink? I really need one."

As they kissed Suzana whispered, "Don't worry, you look great." She led Filipe to table at the back of the bar and went to get some drinks. Initially he felt that everyone was looking at him, but he gradually relaxed. No one was staring or hurling abuse. He plucked up the courage and took off his overcoat. Now he was really out in public in a skimpy dress. Something he had fantasised about for years. As he waited for Suzana to return he did his lipstick and touched up his makeup.

Suzana placed the drinks on the table and clasped Filipe's hand, "You look really good. I knew from your posts that you were dying to come out in public. Just 'relax and enjoy'. Tonight's going to be a lot of fun and you will feel great tomorrow." Filipe tried to smile but part of him still could not believe he had got this far.

Suzana continued, "Let me explain, we are going to a club where all the waitresses are ladyboys. The manager is a friend and has already said if you look like your photo you can have the job. We work for tips, but if you don't mind being groped you can make three thousand a night."

"Three thousand?"

"More if you go on 'dates'."

Filipe almost choked on his drink. Waitressing was one thing, did Suzana take him as whore? Suzana tried to reassure Filipe, or Flávia as she always called him, that these were entirely optional.

After about half an hour, Suzana said they had better be leaving. She took Flávia by the arm and almost marched her to the Club, where she introduced her to the manager, Mr Pereira. Flávia perched himself on a bar stool revealing as much thigh as she dared and smiled shyly. After coming this far, she desperately wanted to be allowed to work at the Club. The man must have been in his sixties, but had a comforting old-world charm. He explained how she was to work as both a waitress and hostess. There was also no salary but she kept her tips and got a 25% commission on any drinks a customer bought whilst she was acting as a hostess. He made it plain she was not permitted to give out her telephone number or leave with a customer. Any 'dates' had to be organised by the Club. Breaking this rule would mean instant dismissal.

The last thing Mr Pereira wanted was a prude, so he always ended interviews in the same way, "Right now, strip down to your underwear."

Flávia was shocked but slowly, and she hoped erotically, slipped out of her dress. Mr Pereira stared, impressed by her lithe body. No tits, but Suzana had warned him about this. Many of the bar staff stopped work and watched. Flávia smiled and tried to look natural, seeking to hide the fact that this was the first time anyone had ever seen her in female underwear. Eventually Mr Pereira nodded and told her to pick up her dress and follow him to the dressing rooms. There he gave Flávia her uniform, telling her to be ready by nine.

As soon as Mr Pereira left, Suzana came in, evidently pleased that her new friend had passed the interview. After a quick hug, Flávia examined the skimpy French maid's outfit she had been given to wear. It was a close fitting, black, satin dress, with puff sleeves edged in white lace. Almost inevitably it was very short. Flávia took a deep breath and started to get ready. There was next to no privacy and she was naturally embarrassed about getting undressed in front of all the other 'girls'. In truth most of them were too occupied with their own makeup and clothes to take much notice of her. As she looked around and was amazed at the beauty of some of them. All were t-girls, and most of them had had breast implants. But Flávia was intimidated by their sheer confidence. How she wished she be like that.

Dressed and make up done, Flávia retied her small satin apron as Suzana began to give her some practical advice. She explained how she should bend over to give customers a good view of her arse and flirt for all she was worth. She should prepare herself for hands to go up her skirt as many customers liked to stuff tips into the sides of their panties. But the compensation was that by the time she finished her two hour shift she might have half a dozen hundred Real notes in her knickers. It was a little uncomfortable at times, but frankly for that money she thought they could put it anywhere they liked.

Suzana kept up constant barrage of chat until they were due to go out. Flávia realised this had been intentional to stop her having time to be frightened or chicken out. Suzana led her to the main dining room and told her to 'circulate'. She did and almost immediately a guest raised his hand to get her attention. She smiled as she stood before his table, terribly conscious of the lascivious smile on his face and the fact he was staring at her legs. But she quickly took his order and then rushed off. Soon she was looking after five tables and didn't have time to think. She was running all over the place. The first time she bent over to pour some drinks, she felt a customer's hand rise between her legs. Flávia fought her natural instincts to slap the bastard and continued to serve the wine. She soon began to 'play the game', coquettishly raising her dress to allow customers to tip her. As the evening wore on, she started to enjoy herself, her natural exhibitionist side coming to the fore. Even so, she was exhausted by the time she was relieved after two hours.

Flávia then had a thirty minute break before going out to 'hostess' at the bar. This was even more frightening. Would anyone want to talk to her? Flávia knew her face looked pretty and her legs were good, but nothing could hide her lack of a cleavage. She was very nervous as she perched on a bar stool. She pulled up her dress to reveal the tops of her stockings and tried to make eye contact with one of the customers. She had been there for almost fifteen minutes before she was approached. He was elegant man in his forties. He introduced himself as 'Tomaz' and smiled as Flávia suggested they share a bottle of Champagne, replying, "Don't be nervous. I know the score." The waiter put the vastly overpriced bottle in an ice bucket on the bar and winked as he notched up her first success. The man to her surprise was excellent company. He soon had Flávia laughing away, completely forgetting that this was a job. As they spoke she constantly filled his glass as she had been instructed to do and he discreetly poured most of it into the ice bucket. He asked her about herself and Flávia lied about where she lived and went to school but other than that was pretty honest. He seemed fascinated by her urge to become a ladyboy.

When she had ordered their second bottle, Flávia snuggled closer and let Tomaz stroke her thigh. She spread her legs and felt him reach for her tight panties. He eased her penis out and started to stroke it. She could not help but get excited. Soon she was so stimulated she could barely talk. Every time she thought she was about to cum, Tomaz eased off. She stretched her legs even wider, desperate for relief. This was bliss. Flávia didn't know how far she should let Tomaz go. Suzana had said she should do everything except sex and full nudity. Tomaz was now clearly very excited. What should she do if he asked for a blowjob? Was it sex? Could she really take a man's penis in her mouth? She was so turned-on she wanted to take it further regardless of the rules.

But her thoughts were interrupted by the intrusive ring of Tomaz's phone. After a brief conversation he apologised profusely but said he really had to go. He then pulled out his wallet and stuffed a few notes down the side of her panties and left. Flávia was simultaneously deeply frustrated, as she had been really enjoying Tomaz's attention and elated at her success with her first 'client'. Before she had thought her desire to dress up in women's clothes was deviant, now she found that not only did people like her but they were prepared to pay handsomely for her company. Flávia had never felt so good. She left the bar about ten minutes before her shift officially ended and went back to the dressing room and stared at the mirror. This was great, just great. She was so pleased she had taken the risk. It was only as she was going out for her second shift on the tables that she raised her dress to see that Tomaz had given her a five hundred Real tip. She left the notes where they were as it made her feel deeply horny.

It was four o'clock by the time the last customers left. Once they had locked the door, Mr Pereira went around distributing thick brown envelopes to the girls. When he got to Flávia he clasped her arm and congratulated her on her first evening. Flávia felt an incredible sense of relief as she flopped down with a very welcome beer. Suzana sat down beside her and asked how she was. Flávia felt tears well up, so she could barely talk, "I have wanted to do this for so long. Now I feel so liberated. I'm really happy. Thank you so much for getting me to take the risk." As she wiped a tear away from her eye she sniffed and said, "It's so silly ..."

"I felt exactly the same. Instead of a safe place like this, I went to a bar in Alemão and almost got raped. But I still remember how good I felt the next morning."

They chatted, but Suzana felt there was something Flávia was not telling her. Eventually Flávia admitted she thought that her landlady had seen her coming out in a dress and she would be thrown out of her flat.

Suzana smiled, "I'm not a Girl Guide, but I may be able to do you a second good deed in a day. I need a flat-mate. What do you think? Pay me half what you are paying at the moment."

Flávia seemed surprised, so Suzana quickly continued, "I promise I am not trying to seduce you. I just think it would be fun to share again."

Flávia was too tired to argue, so agreed to go back with Suzana to at least look at the room. Suzana's flat was in one of the nicest parts of Ipanema. Even to Flávia's tired eyes it looked immaculate. There was a large living room, a wonderful kitchen and two equally beautiful bedrooms. It was in a different class to Flávia's current flat. The girls stood silently looking at each other. Although they had only just met, they seemed to know each other intimately. Suzana slowly leant over and lightly kissed Flávia on the lips. She had a sweet innocence that Suzana found quite beguiling. Flávia responded and the kiss lingered. Suzana pulled Flávia close, hugging her new friend. After what seemed like an age, Suzana reluctantly pulled away. With a final peck on her cheek, she wished Flávia good night. So much had happened over the last few hours, Flávia couldn't begin to analyse her emotions. All she knew is that she was intensely happy. She threw herself on the offered bed and slept the sleep of the just.

It took Flávia a few minutes to work out where she was the next morning. The room was larger than her flat, done out tastefully and at some expense in pastel pinks. Her first reaction was to luxuriate in the feeling of the soft silk duvet against her naked skin. Flávia thought back to the previous evening. She remembered wearing a really cute maid's outfit at the Club. Being accepted as a girl and almost giving herself to Tomaz. She was so proud that she had finally 'come out'. But as the minutes passed, she began to worry. She had come back with a girl who she had barely met. Then she had almost no memory of what had happened after they got back to the flat. Had she taken her own clothes off or had Suzana? Although she was naked, she was pretty sure she had not been taken advantage of. But had they got up to anything together in bed before she went to sleep? She had a slightly sore throat, so had she given Suzana a blowjob? Would she expect more?

Eventually Flávia got out of bed. She found Suzana had left out some toiletries, cosmetics and some very brief, pink, silk panties. There were no male clothes so Flávia had no choice but to pull on her, now rather creased, dress. The 'little black number' was ideal for a night on the tiles but seemed deeply inappropriate for breakfast. After spending ten minutes doing her makeup, she gingerly opened the door and walked through to the kitchen. She was amazed that Suzana was looking quite immaculate. Suzana affectionately kissed Flávia on the cheek. But seeing her friend's tender state, she then merely handed her a newspaper and a cup of coffee that would have raised Lazarus.