Paradise Isle Sissy Pt 01

Paradise Isle - Sissy, Pt 1

(fetish, sissy, feminization, modification, consensual, reluctant, FLR)

By ChangeYourPassword He is what she wants

Author's Note: This is a work of fiction. It is a story of sexual fantasies and fetishes. These sexual practices are not for everyone, but those of us who delve into them understand the allure. The characters in the story certainly do. If you enjoy this story and the fetishes involved, great. If not, please forget the whole thing.

This tale is a stand-alone story of an adventure at Paradise Isle. Please read at least the first section of my story '

Paradise Isle, The Beginning',

for background on the wonderful island and its sexual vacation orientation. It sets the stage for this and other stories of sexual pleasures enjoyed at that glorious resort local.

Warning: this story includes a surgical procedure that, while medically possible, is clearly distasteful.

As soon as they stepped off the boat, Alma, their personal concierge, met them at the arrivals desk and explained her role. Then, checking her paperwork, she confirmed Logan's plans for their stay.

"I see you'll be staying with us for an entire month. Excellent, I'm sure you two will have a wonderful time. Although for the first few weeks I'm afraid Dilan, will spend most of his time recovering from the procedures. By the way. Is it Dilan with an 'I' or Dylan with a 'y'? I do want to be accurate and sensitive to your desires."

Logan, spoke up before he could respond. He'd been asked that question before and always explained that he was born a male so 'i' was appropriate.

"Go with a 'y', please," she said, surprising him, by suggesting the female spelling of his name. Based on their relationship and his lifestyle, he shouldn't have been.

"Excellent. So, Dylan, your first appointment is tomorrow morning. The clinic does their best to complete all of our guests' procedures as quickly as possible, and their techniques are state of the art, which leads to phenomenally short recovery times. You two will have more than a week to enjoy your vacation together, after the healing is complete."

She paused for a moment before focusing on Logan, "and I'm certain that you, my dear, will be able to keep yourself entertained while your girl recovers."

Dylan heard the 'girl' and blushed. Dressed as he was, he understood the confusion.

"I'm sure I will." Logan said with a broad smile.

Alma then took them through one final step, before they boarded the shuttle that would take them to the resort, Dylan received an orange wrist band, while Logan received a black one. They were headed for the more erotic, fetish resort and he was identified as 'feminized'.

Dilan understood his lover's games, the things she wanted from him, and that made him very nervousness. He suspected what he was here for, and although it admittedly made his dick hard, it also scared the hell out of him.

Dilan had come to accept that Logan had turned him into what everyone else would call a sissy. He'd realized in school that he could fit that category. He was effeminate, but not gay. He had always been short and slight of build and although he was fit, not fat, he wasn't athletic at all. He was intelligent enough, and personable too. And he adored women, not only their beauty, and sexuality, but also their power and the way they could wield it with their bodies, clothing and makeup.

Whenever he was around a well-dressed woman, he found himself wilting under her enchantment. He'd get weak in the knees, feeling powerless and horny as hell. He couldn't help himself. Pretty women always 'put a spell on him', as the old song implied.

And Logan certainly had him under her spell. And he loved it.

Clearly, she did too.

She'd always been the epitome of the strong, pretty and independent female. A poster-child of the woman's movement. And her career and success were all-important to her happiness. Only secondarily, was she into men, and sex, and relationships. She was a rock, and didn't need a strong male companion, or even a family, to make her feel whole.

When she stumbled onto Dilan, she realized that he could be a valuable and entertaining playmate. Someone to fill her quiet times and make her life easier. An actual companion, and based on his personality and behavior, even a servant. And he wasn't bad looking either, in a feminine sort of way.

So, she took him under her wing, as if he was a little bird, and began molding him into the boy of her dreams.

And enchanted by her, and with her, he submitted to whatever she required of him. He became her friend, and companion when she needed one. And her helper, assistant and humble servant whenever she asked. Only occasionally did she have to demand anything of him. And on those occasions, even though he might feel anxious, he surrendered and performed as she required.

Over time he became her slave, not reluctantly, or in chains, but willingly in whatever form she liked. And the term, 'slave' was never used.

Of course, there were times when late at night, after she used him for sex, when he understood that it was going a bit too far. That he was often little more than a toy to her. But he couldn't help but love her, dearly, and with his whole being.

But he wasn't really sure she loved him.

Their relationship certainly wasn't a classic one, like they portrayed in movies on the Hallmark channel. But he always concluded, that he was okay with that. He'd always dreamed of life with a woman he worshiped, and that's what he had.

Sometimes, though, it was hard. To be in love with Logan. And be her captive.

The more time they spent together, the more controlling and demanding she became with the games she played with him. And he could see that she was encouraging him to become her very own sissy.

And that was clear whenever he looked at himself in a mirror. Around the house these days, he wore humiliatingly sexy French maid's outfits, with corseted waists, short skirts, black stockings and pumps with difficult, but sexy, ten-centimeter heels.

Who but a pussy-whipped sissy would be caught dead in such a get-up?

That attire was, to some extent his own fault. One night after a considerable amount of wine, they happened onto a broadcast of the movie 'Clue', and he had commented on now sexy Yvette the maid looked in her skimpy uniform.

Logan had immediately jumped on his admission. He wasn't sure if she was upset or intrigued, but the more she interrogated him on what was so interesting, the deeper the hole he had dug for himself became.

Just a few days later his first uniform had arrived. And it mimicked sexy Yvette's skimpy French maid's outfit perfectly.

Of course, it came with a pair of breast forms and a bra, and unlike Yvette's the revealing low-cut top that showed off her beautiful big breasts so wonderfully, a sheer flesh-colored insert hid the falsies.

The corset and the very high heels were difficult for him to live with, but over time he grew accustomed to the tight, restrictive shapewear and the painful shoes.

But he decided, somehow, that it was worth it, as Logan professed to absolutely love how he looked, and she confessed that when he wore his uniform, he became her perfect lady's maid. And that made her very happy.

He did find wearing it both humiliating and arousing. Regardless, he enjoyed playing the maid's role for his lover, and taking care of her personal needs and wants, both sexually and as her servant, all the while wearing the silly, sexy costume.

And over time, at her insistence, it became his standard apparel, worn around her house. Not just on weekends, or on weekends and weeknights, but always.

He knew it was crazy. But he also knew that it kept him insanely horny too.

And that wardrobe grew, mainly in the colors involved. Of course, the black and white uniforms were the standard, and he had several of them, but his closet also included red, pink, baby-blue, navy blue, white, yellow mint-green and dark green ones too.

Each morning, after they climbed out of her bed, Logan picked out his uniform of the day. And after he cleaned up, he always put it on. No matter how silly or humiliating it seemed.

Logan also kept after him to look his best in his uniforms. She required him to keep his legs hairless, first by shaving, and then when she decided that he wasn't doing a good enough job, she dragged him to a salon and had the hair on his legs lasered off.

It did make his life easier. And it wasn't like anyone else saw his hairless legs. So, he suffered through the embarrassment of the procedure and was happy that Logan was pleased.

But then a month later, she took him back to have the rest of his body hair removed. What little he had on his chest, and everything around his crotch!

Now that was embarrassing! But by then their relationship had already progressed to the point where he was calling Logan, 'Mistress', at least in the bedroom.

And again, he was happy at how much his lover adored his hairless body, when she rode him to climax.

Still later, when she asked him to have his beard removed in a similar fashion, as it was all too often scratchy when they kissed and cuddled, he sighed resignedly and agreed to the procedure. It wasn't nearly as humiliating.

Compared to those procedures, getting his ears pierced had been easy. And after they'd healed, she'd presented him with expensive diamond studs to wear in his lobes. Some guys wore such things so he didn't find them too humiliating. And, of course, his lover adored them.

Before things had actually gotten to that point, they had agreed that a long-term relationship was worth pursuing. He, of course was overjoyed by the prospect.

He had also happily agreed to move in with her. After all his home was small and cramped while hers was gorgeous.

Her place was beautiful and large, and located in a well-off suburb, where full acre lots were the norm. She was a successful heart surgeon, highly skilled and well paid, while he could work from a home office, anywhere, as he provided technical support for a high-flying computer company.

His employer had always been pleased to allow the staff to work from home, most of their department were virtual. He was able to interact with both his customers and his managers via the phone or video conferences - where only his head was visible to the camera lens.

He left most of his belongings in his home, and they set up a workspace for him in a spare bedroom.

Over the next few months, they had begun building his maid's wardrobe.

And as they settled into a routine, she had taken things another step farther.

She begun insisting that when he wasn't at home, wearing his pretty maid's outfit, she wanted him to don things she selected and purchased for him, from women's clothing stores and departments. She didn't pick out dresses and skirts. Just blouses, slacks and jackets that cold at least appear to be men's attire.

At first, he resisted her requests. He had accepted the feminine look, while in the privacy and intimacy of her house. But he wasn't prepared to appear even more of a sissy when he was out among the masses. She kept after him, though, and wore him down. And eventually she simply threw out his men's clothes, while he was busy in his office.

When he realized what she'd done, he threw a tantrum, which she quickly and firmly shut down. AS if he was a child, and she was a strict parent.

From then on, resigned to his fate, he wore whatever she selected for him, at all times, including when he went out for errands or they went out on a date.

Most of the time, he could pass for what was once called a 'metrosexual', but all too often he was just considered to be a screamingly gay man. Dilan was okay with the former but hated the latter labeling. He loved women, one in particular. And he was dressed that way for her.

They had been together for eight months, when Logan informed him that they would be taking an extended vacation to a beautiful Caribbean Island. He immediately got excited. It sounded like great fun. And when he looked up the place, he became even more excited. The entire island was known for its focus on sex in all of its forms. He figured that he'd be fine there, and that they'd have a wonderful and rowdy time together at a place like that.

Two months later, on the appointed date, they departed for their vacation, happy and excited. The only challenge was the length of the trip, but first-class seats made it easier to deal with. Dilan, in his sissy attire, was even able to ignore the looks, sniggers and crass comments tossed his way by the people in the terminal and passengers on the plane. Who cares, they were on their way to Paradise.

++++++++++++

So now, as they finally climbed aboard the shuttle that would take them to their suite at the resort, he was wearing wrinkled navy-blue, skin-tight women's slacks, a sheer white blouse over his usual corset and women's penny-loafers with low heels.

At least when he was with his lover, he knew that people wouldn't think of him as gay.

While they rode along, he once again reviewed his existence. These days, throughout all of his waking hours, as well as in his dreams and fantasies, he was Logan's boy. He adored her and served her, lived in her house, slept in her bed, and as she demanded, wore women's clothes, and mostly the French Maid costumes, he'd once admitted to admiring.

He was her sissy, and he was okay with that.

Their suite at the resort was large and elegant, and the first thing they did was collapse onto the big bed and fall asleep, as after the long trip they were completely exhausted.

That night they just cuddled on the big mattress, ate a room service meal, and then made love. And when she rode him to orgasm, it was wonderful, as always.

The bright sunlight woke them, and they laid together for a while before Logan got on the phone and ordered herself breakfast.

"Nothing for you, I'm afraid, my love. This morning you get your new breasts. Real ones. I'm so excited for you, and for me." She said, giving Dilan a kiss.

Distressed, he leaned away, "but Mistress..."

"Don't 'but Mistress' me." She said, cutting him off. "I'm really looking forward to this, it's all arranged, and I won't change it."

He was looking at her stricken; tears forming.

She sighed, sadly. "Dylan, you're the one who loved those girly, slutty French maid costumes. I've really come to enjoy the way you look in them, all silly and pornographic, but it was your fetish. They're the dreams of teen-aged perverts. But since you like them, and now I like them, I want you to look perfect in them.

"And in order to look your best in those outfits, you need to have real breasts to fill them out. So nice big breasts, you'll get.

"Now answer me properly."

Dilan hesitated for only a moment; he knew he had no option. "Yes Mistress, I'll get nice big breasts." And he bowed her head in resigned submission.

"Of course, you will."

An hour later Alma delivered them to the island's large and modern clinic, and they were ushered into an exam room where a doctor and his assistant waited.

They spent an hour asking and answering questions, going over the procedure, the recovery, and filling in all of the forms. Logan did most of the talking, while Dilan simply agreed to what she committed him to.

Finally, he was ushered into the surgical suite where he was prepped for the procedure, and given a sedative. He lost consciousness, thinking about breasts.

And that afternoon Dilan woke up in a recovery room, with Logan and the doctor standing over him, smiling happily.

He was still numb, from the anesthesia, and his chest was heavy and wrapped in gauze and bandages, but he was surprisingly able to listen and even talk.

The doctor started his briefing, speaking mainly to Logan, after he ensured Dylan was aware and paying attention. "We were only able to take her to a D-cup. Else, there could be problems with stretching her skin. Not just stretch marks, but the possibility of tearing. In a few months we could take her to a larger size, if you want to return."

Logan nodded. "We'll see." She said ominously. At least Dilan saw it that way. Although he liked big boobs, like most guys, he'd heard stories of how much trouble girls had with bigger breasts, and he didn't want those issues. Hell! He didn't really want breasts at all.

The doctor then droned on about aftercare and timelines, but Dilan didn't listen. He knew that Logan would take care of him.

He was more focused on the weight on his chest. He had breasts! Big D-cup ones! It was so bizarre.

Finally, the doctor left them alone. Warning that in an hour she'd be taken to a room, where she could rest and recover.

Alone for the moment, Logan leaned in and kissed him. "Now you'll be able to fill out your pretty uniforms." Logan said happily. "I'm so proud of you. You'll be my perfect maid."

"But Logan, how can I ever go out as a guy?" He whined.

"Well, if you really feel the need, you can always bind your breasts. Women who want to impersonate men, do it that way.

"And Dylan, my girl, remember, here on the island it's 'Mistress', always."

"Yes, Mistress," he said. He realized that it was too late to argue, he had breasts now, and Logan, his Mistress, loved them. So, he had no choice. He'd have to learn to live with them.

Now he really was her sissy. But that was okay with him - or should it be 'her', he wondered. What was the proper pronoun for a sissy with tits?

In the days that followed, Dylan just laid around the suite, eating room-service meals. About half that time Logan was out, at the beach or a restaurant or a bar. And she'd come back with tales of the erotic, kinky or slutty sights she'd seen out and around the resort's grounds.

They'd laugh, but it also made both of them horny. So, a couple of times, she carefully mounted him and rode him until they both came.

Those were the highlights of his week, so far. He was counting the days until the wrappings would come off, and he'd be free to join his lover in adventures around the resort.

But the days passed slowly. And it left him with time to imagine how his life would be, back home. A guy with big breasts, wearing women's clothes. It won't be that bad, he told himself. And he'd look wonderfully sexy in the new French Maid's uniforms that Logan had already ordered for him.

He'd just be more of a sissy than ever...

++++++++++++++++++

It was a full week later, and he was nervous. His chest was still wrapped in bandages that weren't scheduled to come off for another couple of days, but the pain was pretty much gone.

Logan, though had informed him that he was to go back to the clinic for another surgical procedure. She described it as a special surprise just for her. As if the breasts weren't just for her also. But he couldn't challenge her, he never could, and the staff was also tight lipped about what was to come.

What now? He asked himself, over and over again.

At the clinic, without any consultation with the doctor, he was once again sedated and taken into a surgery room by the nursing staff.

This time, when he woke up, it seemed like he'd been out for days. Perhaps he had been.

He was pleased to see Logan, standing on one side of his bed. And he noticed a nurse on the other side. She tilted his bed up and held a glass of water with a straw up for him to suck on. The water felt wonderful on his dry throat.

"I hurt, in my crotch." Was the first thing he said, as the pain was of immediate concern.

"That's to be expected." The nurse said. "It will fade with time, and the catheter will come out in a couple of days."

Catheter? He thought, panicky.