Paradise Isle Sissy Pt 02

Paradise Isle, Sissy, Pt 2

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

Dylan's new body

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.

Read part one of 'Paradise Isle, Sissy, first.

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

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.

Each night, Logan and Dylan made love. Logan would ride her dildo, Dylan's ex cock, and gently play with her lover's big breasts. And they'd both orgasm happily, together.

"I do wish our dildo would stay hard, longer. If it was a plastic one, I could easily ride it longer and have more lovely O's." Logan sighed.

"I'm sorry Mistress." Dylan said, chuckling. "But that's just the way guys cocks are." But she stopped when she realized the mistake she'd just made.

When she looked up, she could see that Logan was annoyed. "I'm sorry Mistress." She quickly whispered.

Logan said, angrily. "That thing used to be a cock, when fluids used to spurt from it. But now it's my dildo and it always will be. You can't forget that."

Then she sighed, "I have to find ways to punish you, when you're bad, don't I?"

"Yes Mistress." Submissively.

She still couldn't believe what Logan had done to her cock. Turning it into her dildo. From a practical standpoint it wasn't that terrible. She missed being able to pee standing up, but having to sit was only an inconvenience. What bothered her was the mutilation of her body, the permanence, and the shame. He was now more of a sissy than ever. She thought she never would have agreed to it, had she been asked. But then she realized that for Logan she would do anything, allow anything. Damn!

For the time being, they were stuck waiting, day-after-day for Dylan to recover from her breast surgery. The doctors wanted her to wear a support bra at all times to ensure that her implants settled properly. The procedures they used ensured that process would take only a couple weeks instead of months. But Logan and Dylan, like all guests at Paradise Isle, were anxious to get out and show off.

While they tried to be patient, and counted the days, Logan made an appointment for them at the spa, and dragged Dylan over there one morning.

"You'll love this my dear." She said as they made their way to the building.

"What have you arranged for me?" Dylan asked, not really expecting an answer. Her lover enjoyed surprising her with treatments and procedures that Dylan often didn't enjoy as much as her mistress did.

"Oh, you'll see, just remember. No protests of arguments. You're mine."

"Yes Mistress."

Upon arrival they were greeted by the friendly staff, and Dylan was escorted into a small hair salon treatment room. Logan had required her sissy to grow his brown hair long and full, and back at home he always kept it secured behind his head in a pony tail or a man-bun.

On the island she had insisted that Dylan, the girl, leave it long and loose and she was pleased that it now reached down to Dylan's shoulders, even a little beyond. Since their arrival, each morning Logan had brushed it out and arranged it to look more feminine on her girl.

After Dylan had been seated in the chair, Logan took the stylist aside and, whispering so Dylan couldn't hear, explained what she wanted.

The stylist, Carla, smiled and nodded, and came over to begin whatever process Logan had requested.

Dylan wasn't consulted or informed. She just lounged in the chair and allowed what was to happen, happen.

A couple of hours later she was shown the results, and the vision was indeed a surprise. She was now a blonde, with a cute bob haircut that curled into her neck all around, and bangs that draped over her left eye.

Her first reaction was to reach up and push the long strands back away from her eye, so she could see better. And it made Logan chuckle.

"What?"

"That's such a girlish move, and you pulled it off beautifully."

"You mean pushing my hair out from in front of my eye? It blocks my vision. And it's annoying."

"Hah, but it's also very sexy. You'll get used to your hair hiding your eye, coyly, and that little brush back is a sure-fire way to attract a guy's attention."

"But, I..."

"I know," Logan interrupted. "You don't like guys, but they'll like you. And I love that look on you. It's perfect. And I also like that little swipe. You'll get good at it, with practice, and look so cute doing it."

"Yes Mistress." Dylan replied automatically, before realizing that Carla was standing behind her, listening and chuckling.

Dylan watched herself blush in the mirror. Damn!

Next the two of them were taken over to the nail stations, where they were seated next to each other. Of course, Logan picked out the colors for both their toes and their nails deep red for her, and bright pink for Dylan.

It wasn't the first mani-pedi for Dylan. Logan had introduced her sissy to the process a couple months into their relationship. Of course, Dilan had been embarrassed, back then. But now she was used to the procedure. But Logan had never asked for any color on her sissy's fingers before.

And just as the women began working on their finger nails, Logan interrupted them. "Please, could you also add acrylic extensions to both of us. Say just one centimeter beyond the fingertip? Oval for her and coffin shaped for me."

Oh, lord, Dylan thought. I'll have real woman's nails. She always loved long nails on Logan's pretty hands. They were sexy and when she used them to gently scratch around Dilan's crotch, it drove him wild.

But she had never expected to have nails like that. Or bright pink nails either, for that matter.

For the next hour, she sat there watching as her fingers became those of a sexy girl.

"Be very careful with those. I don't want you to ruin them. They look lovely and very feminine." Logan warned her as they were walking back to their suite.

"Yes Mistress, I'll be careful. But I'm worried. I've never had nails like this before."

"Like I said, just be careful until you get used to them. I think you'll keep those. They'll help with your sissy persona when we get home."

She couldn't help herself, "really?"

"Yes, really!"

Dylan knew not to protest any further. She dreaded how, at home, her nails would really mark her as a sissy boy. And she was certain that she'd get even more harassment about being a screaming gay fairy, too.

And the following day, Logan went even farther. She took Dylan to the resort's main store, which was much larger than the average vacation hotel's shop, and included a sizeable jewelry department. There she had Dylan's ears pierced twice more. Dilan's ears had also been pierced early in their relationship. Logan had thought he would look better, by her definition, if he had pierced ears with pretty studs. So, he wound up with piercings in each lobe.

The piercer had added another hole a centimeter farther up, and a third hole another centimeter above that, in each ear.

Logan then picked out three pairs of golden rings in graduated sizes. The smallest went into the top hole, the mid-sized in the center, and the largest, around 5cm (2 inches), went into her original piercing.

They were just getting ready to pay, when the jeweler, sensing their relationship, suggested they string short, dangly chains between the three rings. Logan loved the idea. The chains would jiggle and sparkle as Dylan moved, and draw attention to her pretty piercings.

Of course, Dylan wasn't pleased. She had to admit that her ears looked cute, for a girl. But she again expected that they'd be big trouble once she reverted to being a guy. If she returned to being a guy.

She assumed that the way Logan was acting, she'd want Dilan, the sissy to keep the jewelry in place.

As Dylan thought about all of the changes being made to her body, she first had to admit that as a girl they were sexy and fun. And Logan certainly loved them, and she clearly enjoyed transforming her; expanding on her feminine look. But Dylan wasn't looking forward to her return home. If Logan made Dilan the sissy wear them out in public, they'd be hell. And Dilan certainly couldn't let the people at work see them during video calls. Damn!

Over the next couple days, Dylan got used to her cumbersome nails, her admittedly pretty blonde hair, and the jewelry in her ears, too. And with Logan's constant goading she also mastered the little finger brush back of the hair in her eye.

In fact, for an hour on that first day, Logan made her practice the move in front of a mirror.

It became a game for her, at all times of the day, she'd catch Dylan's eye and flick a finger, and Dylan knew she had to perform the cute little brush-back.

And much to Dylan's chagrin, it became such a habit for her, she began performing the move thoughtlessly, throughout the day. And on those occasions when she realized what she was doing, she was always flabbergasted, and even though it was a little thing, she wondered, what am I becoming?

The most enjoyable part of the whole day was Logan's new nails. Back at home she only wore extensions on occasion, for special events. And it always delighted Dilan when she used them to scratch, tickle and torture his cock and balls. He'd squirm and giggle and moan, and get very hard, when she applied the sharp edges to the delicate and sensitive skin of his groin.

Now, she seemed to take extra joy in using them on her dildo and the attached balls. And Dylan loved it.

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

At last, after yet another trip to the clinic, Dylan received permission to sleep without her support bra and to begin going out without the ugly thing covering her beautiful new breasts.

The Doctor had declared her sufficiently healed to return to a more normal life, with big breasts, of course.

It was late when they arrived back at their suite, so Logan decided to just stay in and eat a room-service dinner, so she could enjoy and celebrate her lover's new body in private.

They made love as always, and after they'd enjoyed their orgasms, Logan stretched out and laid on top of her girl, feeling their breasts mesh as they kissed, and enjoyed the feelings.

After a while she slithered down so she could nibble on Dylan's nipples and cup her girl's lovely breasts with her hands.

"I do love these," she admitted, happily. "Now I know why some studs are 'breast men'. I think I'll become a 'breast woman'.

Dylan, feeling very good after the sex, smiled, feebly. "Well, my Mistress, they were your idea, just like my dildo, they're yours."

Logan laughed. "Oh, no. I have my own breasts. These new ones are yours to keep."

They laid like that for quite a while. Until Logan yawned and rolled off to the side. "You'd better go clean off, and get that scummy towel out of here. We need to get some sleep. Tomorrow is a big day. We can go out topless, together."

"Oh, right." Dylan mumbled, not nearly as enthusiastic as her lover.

"Oh, come on! It will be fantastic fun. You'll enjoy it." And she grabbed Dylan's hand as he began sliding off the bed. "Remember, get with the program." She added sternly.

"Yes Mistress," Dylan replied dutifully.

When she returned, and began climbing into the bed, Logan opened her eyes. "It's so nice not to have to clean myself out after we make love. I just adore our new dildo." She sighed. But before Dylan could say anything, Logan lifted her arm and pointed, "Think carefully about how you should respond."

Dylan understood. So, after a moment's thought she smiled pleasantly and told her, "I'm happy to clean myself and your dildo, Mistress."

Logan giggled, "Good girl. That dildo is such an improvement over that thing you used to be saddled with. Now come to bed, I want to cuddle."

Dylan climbed in, and laid on her back, as she usually did. Logan then rolled onto her side, up close to her lover with her head on her lovely breasts.

"These make for a wonderful pillow," she sighed, before falling asleep.

And that became her nightly habit. She'd sleep with her head on her lover's chest, with an arm up and cupping the beautiful breasts. And Dylan would wrap her arm around and hold her, lovingly.

In the morning, Logan was excited, to be going out with her girl to show off her big, new tits, and Dylan was both excited and nervous. They went out together, in just their bikini bottoms, after Dylan had carefully tucked her dildo back between her legs. Her nervousness helped by keeping it small.

Out in public, although Logan's breasts were beautiful, Dylan's much larger, artificial ones drew all of the attention, especially on her slight and boyish body. Her slim waist and hips made them look even larger and she appeared very top-heavy.

Dylan had a difficult time accepting and ignoring all of the attention.

And at least initially, she was physically uncomfortable, with her breasts swaying on her chest with every movement. Their weight pulling on her, and throwing off her balance.

But as she got used to the things, it became less physically and more mentally uncomfortable. It was embarrassing. She just couldn't get used to the stares. And the lascivious looks from all the men, and some of the women, as well. Actually, she didn't really mind the women.

If I'm now a girl, I'm definitely a lesbian. She thought, and it made her giggle.

"What are you giggling about?" Logan asked. They were walking along one of the pathways, on their way to lunch at a bar, and up to that point, Dylan had been quiet.

"Oh, it just occurred to me that I'm a lesbian. I love girls, not guys."

Logan laughed. "Of course, you love women. One woman, in particular. And you not only love her, you adore her and serve her, and are under her complete control. Right?"

"Yes, Mistress." She replied, and from the tone of her voice, she was clearly happy with her situation.

"Oh, that's lovely."

They both paused and looked behind them, surprised by a woman's voice coming from close behind.

"I'm sorry, but I couldn't help but overhear."

Logan and Dylan saw a couple walking along behind them. A pretty, slightly older woman and a younger man. Like everyone else she was in only a bikini bottom, but the man, clearly her man, was naked, except for a chastity cage, secured around his genitals.

Very interesting, Logan thought. She'd contemplated something like that for Dilan, on several occasions, but had decided it was unnecessary as she already had complete control over her lover. And now, that Dylan was a girl with a permanent dildo. She really saw no need.

"I'm Jenna and my pet boy here, is Billy. And he adores me as much as your girl does you."

Logan, pulled Dylan into a hug, as they stood side-by-side to talk to the other couple. "Hi. We're Logan and Dylan." And after giving Billy a quick but obvious examination, she added, "And I like your boy."

"Thank you. He's very well trained, and as you can see, his cock is under my strict control. It keeps him docile and obedient, and incredibly horny. He'll do anything I ask, in the hopes of being freed for just a few minutes, so he can cum."

"How long do you keep him deprived?" Logan asked, with a chuckle.

"Too long," Billy mumbled, with a smile.

"Hush. Oh, I only unlock him about once a month." Jenna replied, with a sardonic smile.

"But in between, he gives me wonderful orgasms with his manly tongue." And she laughed, while Billy blushed and looked miserable.

Jenna then reached over and down and cupped her boy's cock and balls in her hand, while he just stood frozen. "He's such a good boy. Aren't you, my pet? I love him dearly."

"Yes Mistress." Billy answered, meekly.

"See, and that's why I interrupted you two in your walk. I heard Dylan."

Logan smiled, "well it seems we both have loving subs."

"Yes, we do. We were just on our way to lunch, how about you?" Jenna asked, pleasantly.

"We were, too. Want to make it a foursome?"

"Absolutely."

The four of them found an empty table in a quiet corner of one of the resort's nicer restaurants and settled in. They ordered drinks, and chatted easily while they studied their menus.

Actually, Jenna, Logan and Dylan reviewed their menus, while Billy sat quietly.

When the server returned, Jenna ordered for the two of them. Clearly, Billy was very submissive.

While they waited for their food, Jenna and Logan began exchanging their histories, and the stories of their relationships.

Jenna and Billy had been married for four years, and apparently through a slow process she had turned her husband into a full-time pet, or sex slave, depending on your definition. He always wore his cage, at home and at work, and he catered to his wife's every whim.

Jenna loved being the one in command, and Billy now accepted his life as her husband and pet

After listening in on Jenna's description of her relationship, Dylan was feeling better about her life, as Logan's woman's maid. It wasn't all that bad, and like Logan reminded her, constantly, it was her idea - sort of.

But, when Logan launched into their story, Dylan got nervous. She didn't want to be outed to these strangers. Especially to Jenna, who sounded kind of mean.

But there was little she could do to interfere with Logan's story.

"Actually, we're not so very different. My Dylan has a cock, just like your Billy. But instead of enslaving him, like you've done so well with your boy. I've converted my boy to my sissy maid."

Logan paused for a moment, enjoying the expressions of surprise on both Jenna's and Bill's faces. Dylan blushed as both of them turned to examine her more closely.

"At home she wears the cutest, and sexiest French maid outfits, all of the time. And her lovely breasts are new, and designed to help her fill out her tops, and show off her cleavage. Just as a slutty servant should. Isn't that right my girl?"

Dylan muttered, "yes, Mistress."

"I'm sorry, give us a better answer." Logan ordered.

To Dylan it was clear that her lover was showing off. But she still knew she had to answer.

"Yes, Mistress, that's correct. I wear my sexy French Maid's uniforms almost all of the time at home."

"Much better. And when you're not in one of your pretty uniforms?" Logan prompted her.

"Then I wear outfits from women's clothing stores."

Logan then turned to Jenna. "We select those outfits, to allow her to look somewhere between a male and a female. Because back home she's still trying to pass as a man. But it's going to be harder now that she has such a nice rack."

Dylan was feeling terribly humiliated. So, she sat quietly studying his wine glass. He was relieved when the server returned with their food, and began the process of handing out their plates.

Dylan happened to glance over at Billy, who he saw was sitting staring at her, curiously. It made her feel even worse.

While the waitress was still serving them, Jenna continued with their conversation. "So, Dylan, your breasts are new? How big are they?"

Dylan blushed as she looked at the server, who was now surreptitiously checking out her breasts.

"Dylan, answer her, please," Logan ordered.

"They're D-cups." She muttered. But when Logan cleared her throat, significantly, she added, "Mistress".

Dylan thought she heard the waitress giggling as she walked away, her tasks completed.