Sitting in her bedroom, Chloe watched herself in the mirror and admired what she could see. Long blonde hair provided by the expensive wig she had just bought topped her pale skinned body while a pair of false J cup breasts were hidden under a lacey white top and bra. While on her lower half she wore a denim mini skirt, white over the knee socks and white stiletto heels.

She felt nervous with her look, always had done but it also thrilled even if it was only in the presence of her own flat that Chloe was able to reveal her inner self. The rest of the time Chloe lived as Nick, a plain, skinny guy in his mid-20’s who nobody ever paid any attention to. In fact, despite liking women as well as men, when it came to women and men Nick was still a virgin. At least as Chloe, Nick got to savour the pleasure of a serious of hung male callers who would come to the flat purely for the chance to fuck the nasty whore they got to meet through a series of online dating apps.

It was not ideal for Chloe, she wanted to have conversation and wanted to have a long-term lover but given the choice between being completely alone and being a slut for strangers? Chloe knew exactly which of the two options she preferred.

Tonight, it was going to be the chance of Anthony, a slightly overweight business man who was nearly 40 and married but whom enjoyed the company of cross dressers and t-girls when he was away on business. They had fucked before, twice in reality as on their previous meeting Anthony had not been able to contain himself and shot his load only a couple of minutes after Chloe had started to suck his cock. After an hour of working it Chloe had finally managed to get him hard again and this time Anthony had managed to enter her arse. Though, just like on the first attempt, a few minutes of semi-vigorous fucking had meant he had spilled his seed into her and this time he was left too drained to try a repeat.

Chloe was desperate though, she had not been able to hook up with anybody for a whole week and needed to get some action, even if it was two strokes and a splutter of cum. As she thought about the evening ahead, Chloe wondered about how Anthony had managed to find himself a wife and had come to the realisation that the world was full of sexually frustrated women. “No wonder the Internet is full of videos showing big black cocks fucking eager women,” she thought to herself.

There was a knock at the door and Chloe rose from her bed and smoothed her clothes down. She had bought an entire new outfit earlier in the week and thrilled at how much of a slut it made her look like. Stepping carefully in heels she was not used to, Chloe walked towards the hallway and another date with her destiny as a frustrated sissy.

Checking through the spy hole, Chloe could see that Anthony was waiting on the other side and, placing a hand on the door knob she gently turned it. The door opened with a click and licking her red painted lips, Chloe smiled at her soon to be lover, “hi, it’s wonderful to see you again,” she purred.

“Hi Chloe, I hope you don’t mind but I brought a friend with me this time?”

The question caught Chloe off guard, and she hesitated in the doorway, unsure what to say. While she had thought of having sex with multiple people in truth, Chloe had never experienced it and feared that she would be unable to perform. Then again, she reasoned, would there be any point in performing if Anthony’s friend was as much of a disaster as he had been.

Unable to decide what to do, Chloe found that the answer was provided for the friend stepped into view. He had been standing to the side, hidden from the view of the door and as he appeared Chloe knew that she had to say yes. Tall and muscular, Anthony’s friend had skin that was as black as night. The t-shirt and trousers he wore seemed to only accentuate how powerfully built he was. There was one thing that Chloe thought was unusual though, the friend appeared to have no hair, he was bald, but it was more than that. He also appeared to have no eyebrows or beard stubble.

“This is Craig,” offered Anthony, “I met him at a business meeting this afternoon and he realised that I have a little craving for girls like you and asked if he could tag along?” Standing to one side, Chloe allowed the two men to enter her flat, now she felt even more nervous and worried about what was to happen but at the same time the presence of Craig thrilled her.

Having been in the flat before, Anthony guided himself through to the small living room and Craig followed while Chloe closed the door and locked it. The last thing she needed was somebody disturbing the fun that she was about to have, and her mother was prone to visiting at times.

“Can I get either of you a drink?” Chloe offered the two men as they sat in the only two seats in the room.

“Have you got any beer?” Anthony asked and Chloe confirmed that she did.

“How about you?”

“I’ll just have a glass of water, thanks.” As she absorbed his answer, Chloe thought to herself about how, for such a good looking and powerfully built man. Craig seemed to be very gentle and kind in the way he spoke and carried himself. Chloe also liked the thought that one of her lovers for the night was not going to smell of beer. So many of the men who fucked her had to be drunk or semi-drunk to deal with the guilt and feelings of disgust that their actions brought in themselves.

Stepping into the kitchen, Chloe opened the fridge and removed a bottle of beer before stepping over to the sink and picking up an upturned glass from the drainer. She ran the water for a moment until it was cold and then filled the glass with a quick burst of water. Collecting the bottle opener from the drawer, Chloe opened the container and then took both drinks back into the living room.

Holding out her hand with the beer towards Anthony he took hold of it, savouring the cold sensation of the glass before taking a swig from the bottle. As he did so, Chloe realised that Anthony was swaying slightly in his seat as if already drunk.

“So I take it you have been to the pub before you got here?”

“We have,” it was Anthony who replied as the bottle of beer that Chloe had given to Anthony seemed to send him over the edge. He blinked slowly before burping through puffy cheeks. “I think Anthony has had too much whereas I have been on soft drinks all evening.”

“I’ve not had too much,” Anthony slurred his words as he tried to argue the point but instead, he fell backwards in the seat and while the bottle stayed perfectly upright his eyes closed for a moment. Suddenly, as if the realisation he had fallen asleep was a shock, Anthony’s eyes shot open and he sat back upright. Struggling to focus, he stared at the bottle in his hand before lifting it to his lips and taking a swig from it. Instead of connecting with his lips though, Anthony missed and started to pour beer down the front of his shirt.

Chloe moved to stop Anthony from drenching the chair in beer, but Anthony was quicker and jumped out of the chair and caught the bottle mid pour. Pulling it away from Anthony, he held it for a moment before entering the kitchen. Meanwhile, Chloe stroked Anthony’s head until he settled back into the seat and closed his eyes.

It did not take long and by the time Craig had returned from the kitchen, his hands now empty having disposed of the bottle. Anthony was already fast asleep, a loud snoring sound escaping through his lips as he slumbered.

Comfortable that Anthony would now not stir, Chloe pulled away from his sleeping form to see Craig holding out his hand towards her. She looked at it before lifting her head and meeting Craig’s gaze, “shall we go to your bedroom?” he offered, and Chloe smiled.

Taking hold of the offered hand, she held the fingers softly between her own before the two of them interlocked fingers for a moment.  Chloe’s, long, red, false nails wrapping round into the hand of her soon to be lover. Then, she tugged gently as she led the way to the bedroom.

As the door to the bedroom swung open, Craig spun Chloe round and pulled her into his arms. They kissed deeply, his tongue searching her mouth as he guided her backwards through the door. Giving a swing of a hand, the door closed over to ensure that they had privacy if Anthony was to stir. “Are they false breasts?” Craig asked and Chloe nodded sheepishly, “do you like having your real breasts played with?”

“Yes, I love it, I have sensitive nipples, but the real breasts are just two tiny mounds of flesh in reality.”

Lifting a finger, Craig placed it onto Chloe’s lips, “don’t worry about that now, learn to embrace the real woman, not the fake being that you are using to increase your femininity.”

“But without them I am not female,” Chloe replied, her voice belying the stress that she felt at the point that Craig was making.

“You are though, you walk like a woman, you carry yourself as a woman and when I kiss you, I can feel the woman in your soul trying to get out.”

For the moment, Chloe decided to stop resisting and she could only watch as Craig removed her top and then undid the bra and remove the false breasts. Topless, in front of such a man, Chloe realised that she still felt female and the two of them embraced again.

Sensing the source of her femininity was inside rather than in the clothes, Chloe was more passionate now and she embraced the moment with a renewed excitement. Craig raised a hand and touched one of Chloe’s nipples with her fingers before cupping the rest of the breast in his palm. It was the first time that Chloe had allowed somebody touch her nipples and the sensation excited her.

Under Craig’s touch, Chloe submitted completely, in a deeper and more meaningful way that she had managed in the past. Until this moment, Chloe had used dressing as a woman, as a way, to have sex with men but now, there was an inner feeling of this being more than a method of seduction. Chloe was, in some internal way, feeling like a woman and as she embraced it, she lost all desire to experience sex as a man.

Chloe fell back onto the bed, her skirt riding up in the process and revealing to Craig that she was not wearing knickers as the tip of her cock poked out under the hem. He climbed on top, positioning himself between her legs and their lips met again. Eager hands pulled at his t-shirt and Chloe pulled the t-shirt up and over Craig’s head so that she could admire his taut and muscular chest.

She drew her fingers across the skin and in response Craig grabbed Chloe by the wrists and hoisting her hands, he pinned them over her head. Chloe wriggled under the grip but made no serious attempt to escape as she felt the rush of desire flow through her.

“I want you to take me,” Chloe said breathlessly and almost in a whisper and as Craig restrained her wrists with one hand she saw and felt him move the other so that he could open his trousers. Then, his cock released from its constraints Chloe felt her bum being lifted and rolled up slightly.  Luckily, she had prepared herself earlier so that she was well lubricated but then she was also not expecting this experience.

The tip of Craig’s cock pushed against her hole which welcomed him in. She found that Craig was bigger than any man she had ever taken and also shocked that she had let him in without insisting he wore a condom first. They fucked, Chloe rocking back and fore as Craig pounded himself into her. Her arse welcomed the penetration and Chloe found herself developing a desire to orgasm, something that had never happened to her before, while being fucked.

A groan emitted from her lips followed by a high-pitched squeal as inside Chloe felt like her body was pulling itself apart. At the same time, Craig also reached his climax and Chloe gasped as thick, hot, streams of cum squirted deep into her.

Spent, Craig rolled off Chloe and they lay there on the bed together, holding each other in their arms. “Thank you,” whispered Chloe, “I have enjoyed sex with men on many occasions but that is the greatest fuck I have ever had.”

“That is because you discovered more about your inner self,” Craig replied before kissing Chloe gentle on the cheek. The two of them continued to lay there, Chloe resting her head on Craig’s chest as he placed a muscular and loving arm around her. In reality though, it was Chloe’s first internal orgasm, the most powerful orgasm she had ever felt, and the result was that within minutes she fell asleep.

When she woke again, the room was completely dark, and reaching out an arm to both side, Chloe found herself sleeping alone. Still dressed as she had been at the point she had first fallen asleep. Rolling over until her feet swung off the bed, she struggled to stand in her heels and had to reach for the wall for balance. Finding herself finally able to stand, Chloe crept carefully around the bed until she found the light switch next to the door. Pressing it, the room and Chloe suddenly became bathed in an intense brightness which made her squeeze her eyes shut in shock and pain.

Moments passed before, eyes fully adjusted to the brightness, Chloe was able to open them again. Finally, able to see, she opened the bedroom door only to find the sound of snoring was escaping from the living room. “Anthony,” she though to herself and she stepped out into the hallway and turned towards the sound of the sleeping drunk. Taking two steps, Chloe realised that she was unable to creep around the house in her heels and using the door frame as support she carefully lifted each foot, removing the shoes in the process.

Barefoot, Chloe crept towards the living room and stepped inside. The stench of alcohol immediately hit her nostrils and she had to catch a small amount of vomit in her throat. “I cannot deal with this right now,” she thought to herself and holding her breath Chloe quickly skipped through into the kitchen. Pouring herself a glass of water, she repeated her journey back through the living room until she was able to close the living room door and seal her occasional lover inside. A quick check of the rest of the apartment revealed to Chloe that her and Anthony were the only two occupants and she headed to the bathroom.

Chloe stripped naked and tidied herself up, removing the last of the leaking cum from her ass in the process. As she did so she switched from Chloe and back into Nick, the reserved, shy, virgin that shaped most of her life.

Picking up Chloe’s clothes, Nick dashed back through the hallway to his bedroom. Closing the door and locking it with the turn of a key, he dropped the clothes on the floor next to the laundry basket. Then, climbing back onto the bed, Nick picked up the phone that he shared with his alter ego and studied it. As the screen came to light, Nick noticed that there was a message flashing on the phone. Opening it, his breath caught in his throat, it was from Craig, “See you in the café on the High Street at 11am in two day’s time.” The message thrilled its recipient and he fell back to sleep, his mind whirring with happy thoughts.

The remaining time to the second meeting with Craig passed quickly, the following morning Nick had woken and prepared for work. Kicking a very hungover Anthony out of the door the visitor did not even have the decency to apologise for getting drunk and falling asleep. Instead he called Nick a slut for what Anthony saw as his disgusting attitude. There, in that moment, Nick made a decision that Anthony would never get a chance to bed Chloe again and he would block all further contact with him.

For the rest of the day, his trip to work, his day at work, which was normally filled with mindless boredom and his lonely night were met with a broad grin. Excited but what had happened, Nick fell back to sleep on the eve of his second meeting with Anthony, his mind whirling with happy thoughts.

The following day, Nick got to the café early and entered to find that Craig had not yet arrived. It was busy and Nick had to wait until he could find table, luckily it was a small, two-person table tucked into the corner where others would not be able to hear the conversation. Sitting, Nick ordered a coffee from the only serving staff, a young waitress and as he waited for Anthony to arrive, he watched her. The waitress wore a tight top which her well presented, though average sized boobs almost fell out of. While her lower half consisted of a tight skirt which pulled taut over her small yet well rounded bum and from which her smooth, bare legs extended. As Nick watched, she approached two men of a similar age who were sat in a booth which only he had a view of from his position. The waitress stood there, writing on the small pad that she held to take orders while the two men clearly flirted with her. Nick found himself excited at the thought of being in her place as she openly returned the flirtation.

Suddenly, Nick’s heart leapt into this throat as he watched the one man move himself so that he could grab his cock outside of his trousers. He was clearly enticing the waitress to pleasure him and as he did so his friend, who was sat right next to her put his hand up the inside of her thigh until it disappeared under her skirt. The waitress gasped but made no effort to push the hand away and Nick realised that the man must have been fingering her.

Her lips moved but from his position Nick could not see what she said, then the waitress leaned in and kissed both men before pulling away. As she left her cheeks blushed red and her eyes darted around with fear of being caught. Seeing that Nick had been watching the waitress blushed even brighter before almost running to the front of the café in shame.

Nick watched her moved and enjoyed the jiggle of her ass before freezing in shock as she almost bumped into the next customer as they entered through the front door. It was Craig, wearing a smart suit and Nick felt a spark of excitement on seeing him. Raising a hand, he waved to catch the attention of his black lover as Craig scanned the room. Seeing Nick, he smiled and headed over to the table where he took a seat.

“Hello Chloe,” Anthony said his face grinning broadly, “you are Chloe aren’t you?”

Nick nodded his head, “yes, I am Chloe, but dressed like this I am called Nick.”

“Hmm,” Craig said, his eyes casting up as he absorbed the t-shirt and jeans that Nick was wearing. “I was hoping you would be presenting as Chloe.”

Putting a hand to his face, Nick felt his cheeks turn red and hot as memories of the night he had spent with Craig flooded his thoughts. “I’ve never dressed in public, never had the courage to and until…” his voice tailed off as he considered whether he wanted to make such an admission.

“Until?” Craig had picked up on the fact that Nick had stopped talking mid-sentence and was clearly interested in finding out what was not being said.

“It doesn’t matter, I’ve only just met you, you don’t need my whole sob story.”

Craig smiled at the comment, “shall I fill the rest in for you?” Nick felt uncomfortable at the comment but instead of saying something he remained silent. “You’re tempted to say no, I can see that but… but you also realise that you want to give yourself to me and you wonder if you really can.”

Silence filled the room as Craig stopped talking to attract the attention of the waitress who hesitantly approached the table. “I’ll have a coffee,” he asked the waitress before turning his attention to Nick, “do you want anything Chloe?”

Nick jumped at the mention of his alter ego’s name and stared at the waitress in fright. “Have you ever gone black?” Craig asked the waitress and she shook her head in response. Her face filled with a mixture of fear and excitement at the thought and Craig gave her a sympathetic smile. “Chloe has gone black,” Craig indicated towards Nick again, “and now she is nervous as before she thought dressing as a woman was just a bit of fun but now, she wonders if she needs to do it full time.”

The waitress looked at Nick and smiled sympathetically, “does Chloe need a girl to help guide her journey?” It was an open question and Nick found himself nodding his head gently. Then, turning her attention back to Craig the waitress looked lustfully at the chocolate skin, licking her lips before forming her question. “And would sir like to fuck said friend of Chloe?”

“You understand me completely,” Craig grinned, and the waitress cast a glance back over her shoulder towards the two men who had been playing with her only moments before.

“I shall get your drinks and we can talk later,” she said with a hint of nerves in her voice, “my boyfriend and his mate will not like me flirting with you.”

With a nod of his head, Craig indicated that he understood and at the same time made it clear that he was dismissing the waitress. As she walked away, Nick leaned forward in his chair, “what do you think you are doing, pulling in front of me?”

Taking a moment to let the other man’s anger subside, Craig acknowledged the confusion that Nick was showing. “You thought a man like me would stay faithful to one girl?” he asked once he was certain that Nick was ready to hear the question, “yes I want to date you as Chloe but I will fuck others as I please and you will do as I please as well…”

“OK,” Nick replied cautiously.

“You will dress as Chloe to see me, even in public, you will present as Chloe more and more to please me and if Chloe takes over your life then you will thank me for it.”

The waitress returned with the order and placed it on the table as Nick considered what had been said. He watched as the waitress also placed the bill down with the drink and Craig picked it up and studied it carefully. Light caught on the paper and for a moment Nick was able to read through it enough to see that it was not a bill but a telephone number.

“Thank you,” Craig said with a nod to the waitress, “I look forward to your assistance and to enjoying you as well.” The waitress giggled at the comment and carried on with her work, leaving Nick and Craig to continue their discussion in private.

“So, Chloe, what do you think, will you give yourself to me, learn about being a girl while I continue to have fun?”

“You never want to see me as a man ever again?”

“Never, you are Chloe and I will transform you bit by bit until you fully embrace your natural femininity.”

Nick nodded in acknowledgement, “I think I need some time to consider this fact.”

“Fine, I shall message you tomorrow,” replied Craig and downing his drink he rose from his seat and stopping at the till to pay the bill he left the café.

Nick stared at what was left of his drink and the waitress approached him as he stared forlornly into the bottom of the cup. The café had emptied a bit and there were no customers waiting as she took a seat opposite Nick. “I had a male friend who became a woman,” she said bluntly. “I helped him learn about moving and dressing correctly and she has never been happier.”

“Are you saying you will help me?”

“Of course.”

“I don’t know, until today this was just a bit of occasional fun.” Nick smiled at the waitress but in many ways, it was a grimace more than an indication of happiness. “I need time to think,” he said before standing and thanking the waitress for her support. The walk home could not end quick enough Nick reflected.

The following morning Nick woke to a banging that echoed through the hallway of the apartment. Climbing from his bed, he pulled a dressing gown around his shoulders and staggered towards the noise. As he approached the living room, he realised that the sound was that of someone knocking on the door to the apartment. Carefully, checking through the spy hole, Nick could see that it was the waitress who was stood on the other side. Taking care to remove all the locks, he opened the door enough to look out into the hallway, “what do you want?”

“Let me in, Craig has given me a job with you.”

Nick frowned at the comment but obediently he opened the door and allowed the attractive young woman to enter into the hallway. His eyes popped out of his head as he took in the sight presented to him. Away from work, the waitress switched from wearing sexy clothing to slutty clothing, the short skirt of the day before giving way to a micro, mini skirt that only just covered her ass. Meanwhile, on her upper body she wore a fishnet crop top under which only a black bra provided any form of modesty.

“We didn’t meet properly yesterday, I’m Leanne,” said the waitress holding out a delicate hand for Nick to take hold of.

“Ni… Chloe,” Nick replied, “I guess I am Chloe from now on.”

“That you are, and I can see why you want to give yourself to Craig, I spent last night with him and I’m still not sure I can walk properly.”

“You slept with Craig last night?”

“Yes, you lucky thing, I’m just a conquest to him but he wants to turn you into something special.”

“Ummm,” said Nick but he found himself completely dumbstruck by the comment.

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