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Flavia's Secret

By: TimT1972



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. 


Flavia's Secret



After a blessed fifteen minutes of silence, Suzana said, "I hope you slept well. I didn't want to disturb you but someone has been calling all morning." Flavia picked up her phone and looked at the missed calls. It was the same number at 7.35, 7.48, 8.10 and so on, every fifteen or twenty minutes. Her landlady must have called a dozen times already. Mrs Relvas was not phoning to ask about her health. She had obviously seen her in her dress and she wanted to voice her disapproval very forcefully. Flávia couldn't face it.

Suzana watched her new friend, "What do you say to me going over and picking up your stuff?"

"Suzana, that would be so kind. I really don't want to impose on you. I promise I'll try to find another flat as soon as I can."

"Don't be silly. You're welcome here." She paused and added, "If you are wondering, nothing happened between the two of us last night."

By the time Suzana returned, Flávia was feeling almost human. As she unpacked her few possessions, she realised for the first time in her life she didn't need to hide her female clothes. It was an incredible relief. In fact the only 'rule' Suzana had was that she had to wear feminine attire 24/7.

It was only later that evening that Flávia got around to opening her 'brown envelope'. She found she had earned more the previous night than she would normally make in a fortnight at the shop. She scribbled out a letter of resignation, there and then. She hated the place, anyway she was sure Mrs Relvas would have told her boss what she had seen.

The next day Suzana and Flávia shopped for underwear, just like something out of one of Flávia's fantasies. She felt a shiver go down her spine as she felt one silky pair of knickers after the next. They were besieged by eager young shop assistants only too keen to serve these wealthy, elegant ladies. It was just wonderful. After a light lunch, Suzana encouraged Flávia to get her ears pierced, as she had to get used to wearing earrings. During the afternoon there was more shopping to do. As they went from one shop to another, Flávia's fear of exposure waned but the thrill of walking around in a short dress if anything increased. By the time they ordered an expensive bottle of white burgundy in the of the city's rooftop bars, Flávia was almost boiling with desire.

Each evening for the rest of the week, they snuggled down with old copies of Vogue and Marie Claire and planned Flávia's 'look'. She decided to grow her hair so it was just off the shoulders, but to keep her centre parting for the time being. She desperately needed more female clothes and they both knew they would have a lot of fun walking around Rio's best boutiques.

Suzana took Flávia under her wing. She seemed to take pleasure in explaining how she should shave her legs, apply nail varnish and do her makeup. Flávia had not done a bad job on her own, but under Suzana's supervision rapidly became an expert.

~

Flávia and Suzana went off that Friday to do their stint at the Club almost inseparable friends. This time Flávia was much more confident and mixed easily with her fellow t-girls. She soon began to enjoy flirting with the customers, relishing the stray hands which went up her dress, knowing that this could only add to her tips. The highlight, or otherwise, of the evening was when a very well built female client ordered Flávia to take off her panties and bend over her knee. Flávia felt humiliated, but found stripping in front of the whole bar deeply erotic. The subsequent spanking hurt, hurt a lot, but seemed to greatly increase her popularity as a hostess.

When Mr Pereira came to give Flávia her 'envelope', he told her that Tomaz would like to meet her privately. He said he could organise an appointment if she wanted. Two nights in the Club had cured her of any of her residual naivety, she knew exactly what Tomaz wanted and had little doubt that he would be prepared to pay handsomely for the privilege. She realised from the gossip that most of the girls 'entertained' clients. Mr Pereira applied the pressure on her to do so very subtly. She genuinely liked Tomaz, so in the end she agreed to the date. Mr Pereira then explained what she was expected to do and the fee he had agreed with the client.

When Flávia woke up the next morning she wondered if she had done the right thing in agreeing to see Tomaz. Allowing men to ogle her and stroke bottom was one thing, but prostituting herself was something else entirely. Her fantasises had always centred on skimpy underwear, short skirts and looking like a girl, not sex. But now she was living as a girl full-time she knew she would be pressured into having intercourse. This meant giving blowjobs and anal sex. It was frightening. She wondered if in the heat of the moment she would dare go through with it. Could she really put a man's cock in her mouth? It was against all her ingrained conditioning. Flávia shared her fears with Suzana over breakfast. Asking her friend what she should do and if Mr Pereira would sack her, if she refused to go through with the date. The older woman tried to reassure her that she would enjoy the experience and it was best to do it the first time with a genuinely nice guy like Tomaz rather than some random punter. She admitted penetration would hurt, but she argued this was the only way to complete her transformation into a girl. Flávia had to be brave and simply 'go for it'.

Suzana knew the first 'client' for any girl was nerve wracking experience and was determined to give Flávia all the help she needed to prepare for her date with Tomaz. So after a late lunch, she first sent her friend off to have a long shower and then shave. Done, she told her to stand naked in the bathroom, legs well apart and hands on her head. Flávia obeyed. As she waited, she gazed at her body, proud of her flat stomach and toned legs. She still felt humiliated at being ordered around in such a demeaning way, but knew her friend must have a good reason. When Suzana returned she gently swept her hands over Flávia's naked body, feeling for any stray hairs or stubble. She wanted her to be totally smooth. When she had shaved any areas in 'hard to reach' places notably the area between Flávia's cock and anus, she instructed her to lean over on the basin, spread her legs and push her buttocks out. Flávia winced with embarrassment but obeyed. She then felt Suzana begin to massage some cold gel against her anus. 

"I know it is difficult, but try to relax." Flávia tried, and felt Suzana ease the gel into her rectum, "This is lubricant. Whenever you are going to have sex, you must remember to do this. Otherwise being entered can really hurt."

Another lesson learned. When Suzana was satisfied, she took the still naked Flávia to her room to do her makeup. Flávia was fairly proficient by now, but was still grateful for Suzana's help. Now it was time to choose some clothes. This is what Flávia really enjoyed. They agreed on white underwear as this seemed appropriate for Flávia's 'first time'. So Suzana recommended a tight silk basque to give her something of the proverbial 'hourglass' figure. Then her best silk panties and suspender belt. The panties had to be tight, but Flávia was now adept at easing her cock between her legs so there was no obvious protrusion. Normally she would not risk spoiling something this expensive, but the first date was special. The spotless white silk looked great against Flávia's lightly tanned skin.

After some debate, they agreed on a very short, pleated skirt and white silk shirt. Suzana advised skirts were useful if the client was nervous or over enthusiastic as they were very easy to discard. Flávia was now ready. She felt proud of her appearance, still nervous, but she was looking forward to this important stage in becoming a fully-fledged ladyboy.

Suzana was truly proud of what they had done, Flávia looked simply adorable. She just hoped she could perform. She had done her best to prepare her friend for what she should expect, but the poor girl unsurprisingly looked petrified. Suzana gave her a final hug and handed her a beautifully wrapped box containing some small diamond earrings. Flávia was deeply touched. She promised herself she would not let Suzana down.

Suzana knew she had done all she could and it was down to her friend to satisfy her first client. So she kissed her promising she would be in her bedroom and if there was a problem Flávia should shout 'red' and Suzana would be out wielding her trusty baseball bat. 

As 3pm approached, Suzana made herself scarce. As the minutes ticked by, Flávia became ever more nervous, checking and rechecking that everything was in its place. She almost had a heart attack when the bell finally went. After another quick look in the mirror to practice her best smile, she opened the door to reveal Tomaz. He was holding huge bunch of roses. She let him kiss her and took him through to the living room. The roses produced a welcome distraction as Flávia found a vase and arranged them. As she did so, she bent over to give Tomaz the best view of her pert bottom. Flávia then offered him a drink and sat down beside him, letting her skirt rise up to reveal her panties. As they spoke she massaged Tomaz's rapidly hardening penis. She knew things couldn't be delayed forever, so summoning all her courage, she gently took Tomaz's hand and led him to her bedroom. Looking at him, it dawned on her he was almost as nervous as she was. He sat on her bed, leant back and looked at her. Flávia stood as if she was being inspected; eyes demurely lowered and hands behind her back.

"Roberto says this is your first time. Are you sure you are comfortable doing this? If you are not, we can just chat and have a drink as we did in the Club."

Flávia looked at him and said with all sincerity, "No, I really want to do it. I want you to be the first to fuck me. I know I'm inexperienced, but I'm fresh and enthusiastic and will do absolutely anything you want." When Tomaz smiled, she giggled and said, "Come on, we'll have fun. Let me help you undress."

She gently helped remove his clothes, kissing him as she took each piece. When he was naked, she then got him to lay in the middle of the bed. Flávia got to her knees, and massaged his inner thighs, before gingerly taking his rapidly stiffening penis in her hands. She had thought about the next act for hours. Could she or couldn't she place a man's cock in her mouth? She knew she had to go through with it. So hesitantly she opened her mouth and placed her lips around Tomaz's shaft. She then sucked without feeling the expected revulsion. Now the boundary had been crossed, she knew she would be fine. She licked the head as if it was the most important thing on the world. Then as Tomaz became fully erect she took his cock as far down her throat as she could. God she was so desperate to please him. She knew that this simple act broke multiple taboos, not only was this her first gay experience she was also now a prostitute. But she knew she really wanted to do this. More than anything. She gradually increased the pressure on his shaft and started to suck with ever more vigour. Flávia found she was enjoying it, and was also getting excited. Tomaz was now very hard and groaned with evident pleasure. Flávia redoubled her efforts. Just before he was about to cum, he eased Flávia off him. He then pulled her up and kissed her. Flávia allowed herself to be held in his powerful arms. Her slight frame overwhelmed by his strength. When Tomaz released her, he slowly eased her onto her front. Flávia was now eager to be properly fucked, slowly pulled down her knickers and knelt on the bed. Pulling up her skirt, she smiled, "Please take me. I really want to do this."

Tomaz thought she looked so sweet. He stroked her naked bottom, watching her inch her legs further apart. Her cock was gradually stiffening. She really seemed to be genuinely keen to have sex. He knelt on the bed and gripping her thighs, slowly entered her. Tomaz really didn't want to hurt her. He cautiously thrust forward. She was very tight. He thought Roberto might have actually been telling the truth (for the first time in living memory) when he said Flávia was a virgin. Despite Tomaz trying to be gentle, Flávia felt as if she was being stretched to breaking point. She bit her lip and couldn't help squealing with pain, vainly hoping it sounded as if she was enjoying her ordeal. Tomaz kept thrusting slowly. He didn't need frantic sex, the whole scenario of fucking such a cute ladyboy was more stimulating than he could possibly have imagined. She looked so bloody sexy. He gradually increased the speed and pressure. However hard he tried to be gentle, it still felt to Flávia as if she was being skewered by a rod of iron. As he approached climax he gave into his animal passion and began to thrust with all his might. Tomaz was in a state of bliss and when he finally came, his orgasm was impossibly pleasurable. He lay exhausted on the bed. Flávia in turn took a few minutes to collect herself. She wiped the tears from her eyes, then turned to her client with a smile. She brushed the hair from Tomaz's face and kissed his cheek, "Thank you so much for taking me. I have wanted to do this for ages. Is there anything else I can do for you? I've got the whole afternoon if you want to stay."

Tomaz was amazed, his limited experience of whores said that once the business was complete they were dying to get rid of clients. He had a 5.30 meeting but was keen to spend more time with this little cutie. She looked so damned feminine except for her penis, but this wasn't huge and as she had totally shaved her pubic area, it looked quite natural. Tomaz had often wondered if he liked the idea of a ladyboy because he wanted gay sex and someone like Flávia provided this is such an appealing physical package. Perhaps, all he knew is he had had a wonderful time. They chatted mainly about Flávia's experiences as ladyboy. By now she was being totally honest. She enjoyed unburdening herself to a sympathetic listener. As they chatted Tomaz played with Flávia's cock. He had never touched a penis so wonderfully smooth. She soon became erect and let him take her repeatedly to the verge of orgasm. This amused him no end. 

Eventually Tomaz announced he really had to go. He was amazed Flávia seemed genuinely unhappy. She insisted on giving him one final blowjob. The minx as ever got her way. She looked so damned cute as she lay between his legs. She started to lick and suck his cock in such a gentle way it was almost torture, but as soon as she had him fully erect rapidly increased the pressure, before bringing him to a wonderful orgasm. She swallowed and licked him clean. This done, she escorted him to the door, naked except for her corset. Tomaz was amazed at how relaxed she looked. Her movements were light and feminine as if she had been doing this for years. She kissed him goodbye, promising to be at the Club that Friday.

Suzana had been listening and as soon as Tomaz had gone, came out of her room and threw her arms around Flávia congratulating her on her success. Flávia was very sore but truly elated. She had survived and even enjoyed her first sexual experience as a girl. There was no going back now to her 'vanilla' existence. She recognised sleeping with Tomaz as an important rite of passage. She was proud that he had asked to see her again and wrote his name in her 'little black book' with pride.

~

Flávia and Suzana enjoyed being flat mates. They started doing everything together, going hostessing at the Club on the same nights, shopping at the same clothes shops and using the same salons. To begin with Flávia was terribly nervous about going out, thinking she would be recognised by friends or spotted as a t-girl. She continually searched people's faces for the merest hint of recognition. Suzana told her repeatedly she looked like a girl, an attractive one at that and she shouldn't worry. If men were staring it was because they wanted to take her to bed. Eventually she was forced to concede her friend was right. What had once been a carefully staged act was now simply instinctive. 

When in the flat, the friends were sensitive enough to give each other their own space. Suzana did a certain amount of escorting and in the beginning was happy enough to pass on clients to Flávia. But soon Flávia had built up her own short, but loyal client list. The cash was nice, but what was more important to her was the knowledge that people not only valued her, but were prepared to pay handsomely to be with her.

As Flávia became ever more relaxed at living and being treated as a woman, she knew she had to go the whole hog and get some breast implants. This was her way of irrevocably severing any links with her old male life. She had no end of fun with Suzana debating the size and shape she should go for. Due to her delicate frame, she resisted the temptation to go for over large tits and plumped for a pert 31C bust. Decision made, Suzana introduced her to a doctor who had successfully performed the operation for a number of the girls at the Club. He seemed nice and more importantly appeared to understand why having breasts was so emotionally important to her. After a long discussion they also agreed he would remove her Adam's apple and perform some facial surgery at the same time. The countdown to full femininity had begun.

On D-day minus one, Flávia went into the clinic, frightened but determined. The formalities were a little embarrassing when she had to explain her lifestyle. Then she had to endure a very unsettled night before the operation, which was scheduled for 10am the next morning. But she knew there was no going back. On waking she was served an anaesthetic instead of her normal coffee. Three hours later she recovered consciousness, looking like an Egyptian mummy and very sore. Over the next few days she tormented herself that she had made a terrible mistake and that she was going to be horribly scarred for life. A monster. So the feeling of relief was incredible when the bandages came off. Flávia was simply overjoyed at her transformation. The surgery to her forehead and chin had been subtle, but undoubtedly added to her femininity. Her tits were simply great, she was so proud of them. They were very sensitive but looked wonderful, more natural than many of the plastic creations sported by many models. The girls from the Club came on an almost daily basis during her week's recuperation, bringing her flowers, fruit and even her favourite dildo.

The night Flávia left the clinic, Suzana took her to dinner and on getting home, handed her a present. Flávia greedily unwrapped it, to find a divine Versace bikini. Flávia stripped off in an instant to try it on. She had wanted to wear a bikini for years. As she admired herself in the mirror she knew this moment was the culmination of her struggle to become a girl.

When Flávia returned to the Club, she was met by a rousing round of applause from all the girls. They seemed genuinely happy that she had taken the 'plunge'. When waitressing and hostessing she was continually greeted by customers with their personal congratulations. She was forever raising her dress to allow them to slip bank notes down her thong. It was easily the most lucrative night she had ever had. Tomaz was there and although she had to tell him she was still too sore for sex, she promised him he would be the first to sample her new body. 

~

However much she enjoyed her new feminine self, she still wanted to explore her full sexuality. So about a month later, on a whim, she advertised herself as a dominatrix on Backpage.com. Mere minutes after the ad went live, she started to receive calls from potential clients. Some were time wasters, others she simply didn't take a liking to. Eventually she agreed to see a guy calling himself 'Alvaro'. He was polite and Flávia thought he was sincere when he said he really 'needed' to be dominated by a ladyboy. He also offered her a lot of money.




Flavia's Secret



Flávia still found it deeply erotic getting dressed before her dates. After a hot shower she shaved, paying particular attention to her pubic area, ensuring it was perfectly smooth. She then took time to admire her naked body, knowing it had really benefitted from Suzana's insistence on their dieting and regular gym sessions. For her top she had chosen a PVC basque that fitted her new tits perfectly and left her flat stomach bare. Then she pulled on the cutest pair of brief, skin-tight leather shorts. It was now almost instinctive to ease her cock between her legs. The soft leather felt wonderful. Lastly came some wonderful patent leather boots. They laced all the way up to her thighs and had an impressive five inch heel. These gave her an incredible feeling of power. Her only accessories were her favourite pearl choker and a riding crop. Flávia stared at herself in the mirror. OK she looked like a tart, but a very sexy one. She felt great. The outfit gave her a supreme confidence. She knew was really going to enjoy this. Still she psyched herself up to appear aggressive and dominating. With most of her dates she was 'passive' but this time she was going to act the alpha female. 

Her date, Alvaro turned up visibly shaking with nerves. She thought he was probably in his forties, shaved head, well dressed and not ugly. Her heels ensured she looked down on him, enhancing her dominance. After taking his cash, Flávia ordered him to strip and kneel in the centre of the living room with his legs spread and hands behind his back. She wanted him to feel as insecure as possible, so ensured that the curtains were open and the sun streamed into the room.

Flávia made him wait. Eventually she returned and stood in front of him, "You are now my slave and will call me 'Mistress'. For the next hour you will do exactly what I say, otherwise you will be punished. You know you are paying for this, but you must understand what we do will be solely for my enjoyment. Now put on your collar." She watched as Alvaro obeyed. His hands were shaking so much, he could barely buckle on the collar. Flávia wondered if he would have the courage to go through with the session. She would soon find out.

Flávia sat down and tapped her riding crop against her calf, "Kiss my boots."

Alvaro immediately leant forward and started licking the warm patent leather. His body was nicely toned and his arse looked so inviting that she could not help swatting it with her whip. She slowly lifted her foot, so he could properly suck her stiletto heel, roughly forcing it into his mouth. Alvaro gradually moved up her right leg kissing each eyelet in turn, until his head was mere inches away from Flávia's crotch. As he reached the top of her boot, he kissed her inner thigh. It felt wonderful, but Flávia knew she had to impose some discipline on her new slave. So she bent over and attached a leash to his collar and yanked him to his feet. He would have to endure a great deal of pain before she would allow him any relief. As they walked along the corridor, Suzana opened her door. She was wearing the shortest of white satin robes and playing with a school cane.

Alvaro tried to cover his crotch with her hands. Flávia noticed and feigning irritation said, "Kneel. Hands behind your back."

Suzana smiled, "Who's this?"

"My new slave."

Flávia looked down at Alvaro and barked, "Slave, show some respect. Kiss Mistress Suzana's feet." Alvaro bent forward and obediently kissed them.

Suzana giggled and curious said, "Let me see."

Flávia tugged on the leash and Alvaro stood. Suzana walked behind him tapped his naked bottom with her cane. Then opening her robe, pressed her semi erect cock between his buttocks, "He's cute."

"I am just about to find out if he is competent sexually. If he is, I let you have a 'play'."

"Have fun."

"I will. He won't."

Flávia pulled on Alvaro's leash and guided the now thoroughly humiliation guy to her bedroom. Her soft pinks did not make much of a dungeon, but she had dimmed the lights and hung a picture of a dominatrix above the bed to set the scene. Anyway a good beating would soon concentrate Alvaro's mind. Another hard tug got him on his knees. He now looked genuinely scared.

Flávia massaged her breasts. They felt wonderful below the tight latex, "Does my slave want to see my puppies?"

"Yes, Mistress."

"Beg."

"Please Mistress, let your insignificant slave worship your perfect body. I'll do anything for you, anything at all."

Silence.

"I beg you Mistress, please let me be your slut."

A good start. Flávia still found it hugely thrilling to show off her new tits. She took the zip that ran down the centre of the basque and very slowly pulled it down, pulled it up, then slowly down again. She was going to tease him. Alvaro was mesmerised. Eventually she let the basque fall open, but immediately covered her tits with her hands. She then slowly rubbed them, always just hiding her nipples with her fingers. As she did so, she slowly swayed as if to some silent music. Until finally she revealed her breasts in their glory.

"Come here slave. Kiss them."

Alvaro rose and let his lips lightly touch her breasts. He wasn't sure what to expect, but the soft, smooth skin felt wonderful. Flávia's scent was intoxicating. Her warmth and blatant sexuality was almost too much. But she still exuded a sense of superiority. A certain hardness and steeliness. So Alvaro knew if he took liberties, the woman would take pleasure in punishing him.

Flávia enjoyed the feel as Alvaro licked then sucked her tits. She also liked his uncertainty. He really was scared of her. As he licked, Flávia tapped his rapidly stiffening prick with her riding crop. He was now totally in her power. It was time to have some real fun. She pushed him back to his knees.

With her hand clasped firmly between her legs, Flávia slowly unzipped one side of her shorts. As they fell open, Flávia rubbed her cock ever harder. Now, ever so slowly, she began to unzip the other side. It seemed to take an age, but eventually she let the soft leather fall to the ground, revealing her perfectly shaved cock. Thoroughly enjoying herself, she spun around and spreading her legs, bent over. She pulled her buttocks apart and ordered, "Rim me, slave."

Flávia thought that there was no better way of humiliating Alvaro than making him lick a prostitutes' arse. Alvaro could barely believe what he was hearing, he hated himself but knew he had never been so excited in his life. So he leant over so his tongue was barely touching Flávia's (scrupulously clean) anus. After some vigorous encouragement, he licked rather more enthusiastically. Flávia shuddered with delight. She simply loved the feeling of a tongue massaging the ultra-sensitive area between her legs. Somehow she controlled herself. She was now fully erect and wanted more, much more. So she stood up and turned around to view her slave.

Flávia was naked, except for her thigh high boots, and had never felt so absolutely in control. She was proud of her body and her transformation. She looked at Alvaro and growled, "You are going to have to submit to your Mistress. Like it or not." She stroked her penis, approached Alvaro and ordered him to, "Suck."

On the phone Alvaro had said he had never done anything like this before and Flávia saw the look of deep uncertainty in his eyes. It was a big thing for a guy to suck cock. Many may fantasise about it, but this was real. The delay seemed to go on forever, but in reality it was probably only a few seconds. As Flávia stared at her slave, she saw him inch forward and felt his lips clasp her penis. A wave of pleasure rippled through her body. Quickly erect, she clutched Alvaro's hair and forced his head firmly between her legs. Then pulled back and repeated the process even harder. Flávia forced her cock as far down his throat as she could, almost choking her slave. She felt his tongue franticly massaging her cock, for a beginner he was not bad. He was obviously desperate to please her, attempting to take her full length down his throat. This was bliss, sheer bliss. She pulled him away and made him suck her balls. Then as Flávia's desire became almost irresistible she held his head and began to fuck his mouth. Flávia thrust with an almost manic energy. She felt incredible pleasure as her cock hit the back of his throat. When she felt she could not hold on much longer, she pushed him back on the carpet. Her sex slave cowered at her feet, frightened that he had offended her. 

With all the severity she could muster, she ordered him to lay spread eagle on her bed, stomach on a pillow in the centre. Then she began to tie his wrists and ankles to the four corners. Flávia was now shaking with desire, she wanted to fuck him so badly. It felt glorious to have her own slave at her mercy. But she somehow concentrated on the task in hand and tightened the ropes, so Alvaro was stretched taut against the pink satin sheets. He was now totally defenceless. On a whim, she picked up some of her old knickers and stuffed them into his mouth. 

Fully secure, she knelt on the bed and felt Alvaro's prostrate body. She gently massaged him, kissing his neck and back before softly stroking his inner thigh and lightly touching his cock. He was quickly becoming erect. As she slid her hands down his back, she suddenly dug her long nails into him. She felt him tense with pain. The deep red scratches looked wonderful. They would be a fine memento of his slavery.

Flávia got up and retrieved her riding crop and got to work. She had been looking forward to this for days. She eased her riding crop down his thigh, before rubbing his penis. She tapped his balls, right and left, hard enough so he knew he was at her total mercy. She felt huge satisfaction as the crop crashed into his inner thigh. Alvaro screamed and for a second Flávia thought she had hit him too hard, but he relaxed, so she decided to continue. Flávia flicked his other thigh, then his calves. Sometimes she hit Alvaro hard other times quite softly. It was the feeling of power that was intoxicating. Finally, she gritted her teeth and struck him hard, very hard, six times across the buttocks, leaving some bright, vivid red lines. He struggled one way then the other, but there was no escape, she could do anything she wanted. 

Now for the finale, Flávia stroked her penis, until it was fully erect. She then knelt on the bed and massaged his buttocks apart. When she touched one of the welts, Alvaro winced as if he had been electrocuted. She clasped his thighs and forced herself into him. She was meant to be aggressive and sadistic, but she entered him quite gently. She knew this would hurt if he was a virgin. Her first few thrusts were equally gentle, but from then on she speeded up and almost instinctively thrust harder. What started as an experiment was now truly pleasurable. His muffled cries were rather cute. She clutched his thighs revelling in her power. The pleasure was incredible, as she fucked and fucked again. Eventually she came with an explosive energy. Flávia pumped several more times, extracting all the pleasure she could from her slave. Tired, she lay on top of her client and kissed his neck. She took a few moments to recover. When she did, she untied him and told him to kneel.

Flávia walked around her slave. She simply loved the feeling of power that the riding crop and the thigh high boots gave her. It was such fun to find such a cute submissive. She stroked Alvaro's hair and pulled her panties from his mouth. Dropping them on his lap, she said, "You will wear these next time you visit your Mistress." She had enjoyed the session immensely. She wondered what complex thoughts were going through his mind.

Bracing her legs a mere inch or two in front of her slave she ordered, "Suck me clean, boy." Alvaro did so. Flávia's penis felt so very sensitive as he licked away the cum. She watched as he carefully took the shaft into his mouth, then sucked her balls. She loved the feeling of his tongue as it gently massaged the bottom of her penis. His expression revealed an impenetrable mixture of lust and humiliation. Determined not to cum again, she reluctantly pushed him away. She wondered if she should give the poor guy a quick 'handjob'. But no, if he really was her slave this session should solely be for her enjoyment. Let him go away frustrated. 

Alone, she pulled on her basque and shorts and posed in front of her full-length mirror. The look and feeling of superiority was deeply, deeply erotic. She knew it was role-play but dominating Alvaro had given her huge satisfaction. It seemed a lifetime ago that she would only dare to wear panties in her own room with the door securely locked. Her transformation to a proud and attractive t-girl had easily been the most satisfying journey of her life.

As Flávia escorted Alvaro to the door, she gently took his arm and lightly kissed him on the cheek, "I really enjoyed that. I hope we can do this again soon."

He replied, "I would be honoured to serve you, Mistress."

Flávia had always imagined that being a girl would mean being passive, effectively spreading her legs and being fucked in any way a man wanted. The session with Alvaro had opened up a whole new vista of pleasure. Whilst she had found it deeply erotic dominating and humiliating him, fucking him had been simply wonderful.

Since moving in with Suzana, Flávia had avoided her school friends. But she was honest enough to admit that she still yearned for their company. So when her oldest friend, Dimas, gave her a call to get her along for some drinks she accepted. She was going to see them and face the consequences. She couldn't hide forever. The evening almost ended in disaster as at the last minute an important client booked her for an afternoon out-call session. So when she finally arrived half an hour late at the pub, she was dressed a very short Lourenco dress, a much more provocative outfit that she had planned. The first moments were comic, as she approached their table, Ramiro and Fabio both jumped to their feet rushing to get this ultra glamourous stranger a seat. 

It took some time for Flávia to convince them that she was their friend 'Filipe'. When she did, there was silence, real and prolonged silence, as the boys examined their nails and drank their beer. Finally Fabio showed why he was the unacknowledged leader of the group, "Flávia, you have been my friend for the last seven years, and I hope you will always be so. But only if ... you buy the next round." This broke the ice and suddenly everyone else claimed that they were about to say the same. Flávia almost cried with relief. By the end of the evening they were ribbing her about eating 'rabbit food' and saying how she would really wobble in her high heels after the next boys' night out. In short, she was back. Flávia never specifically admitted she was an escort, but most of the boys must have guessed she was. Even so, they were soon as protective of her as if she was their communal younger sister.