Paradise Isle, Sissy, Pt. 03

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

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 parts one and two of Sissy, first.

Logan and Dilan headed home from their island adventure anxious to get home and to bed. It had been a long and exhausting trip.

As Dilan was back in what classified for him as ‘street clothes’ – women’s slacks and blouse, he was immediately pegged as a phenomenal sissy, or perhaps a man in a woman’s body.

His makeup was lightly applied, as Logan required, so his face looked the part.

He had done his best to wrap his breasts, with materials bought at the resort. It was effective to a point, and decidedly uncomfortable. It had made for a miserable flight, even though they were in first class.

Of course, as they moved around the airport Dilan drew stares from people in the concourse, and the luggage area, and from the Uber driver who carried them home. Dilan ignored them all. Much of it was due to his outfit. He was back to wearing a woman’s slacks and shoes, and a blouse that was stretched over his new breasts. But his face, was no longer made up like a girl’s.

The Uber driver did his best to ignore him, but he did spend time admiring Logan in his rear-view mirror. She paid him no attention.

Finally in the door, they quickly stripped off their clothes, donned nightgowns and went to bed, to sleep off the jet lag.

When Dilan woke up, Logan was already up and out, and per usual, one of his French Maids uniforms was all laid out for him.

He took a quick shower, applied some light makeup, brushed his hair into the bob, he’d become used to, and then slipped on panties, and stockings, laced himself into one of his corsets, slipped on the uniform with its insanely short skirt and petticoats, added pumps with four-inch spikes and buckled their ankle straps, and then, finally, examined himself in the big wall mirror in their bedroom.

He looked almost as he used to, before their trip. Except for the girlish blonde hair, and the dangly earrings, and the polished fingernails. His new breasts weren’t visible beneath the top of the uniform. The bra and breast forms he used to wear weren’t suitable for display, so his maid’s uniforms weren’t low cut to reveal massive amounts of cleavage, like Yvette’s.

Now that he had the breasts for it, he assumed Logan would insist on a replacement wardrobe – a more revealing one.

Making sure all was perfect, he headed down to the kitchen to find his lover and get something to eat.

Thankfully, it was a Sunday so he didn’t have to do engage in any company work. But he knew he had numerous chores to perform around the house.

“Good morning, Mistress” he said happily, as he walked into the kitchen to see her sitting at the counter on her computer, catching up on emails.

“Good morning my love. It’s great to see you back to normal. And I do like your hair like that.”

Unconsciously he brushed it out of his eye, like he’d learned to do. And that brought a smile to Logan’s lips.

“Thanks, but I’ll have to put it into a pony-tail or a man-bun when I’m on a work call or I go out.”

“I suppose,” she said, disappointed. “I suppose you’re right, that’s definitely a girl’s look, not a sissy boy’s.”

“Yes Mistress.”

“Why don’t you make us breakfast while I catch up?”

“I will. I’m starved and I imagine you are as well.”

After they’d eaten, Dilan started on his chores. He spent the morning unpacking and working his way through the wash. Then he prepared lunch.

“So, what’s on your agenda for this afternoon?” Logan asked as they were finishing their meal.

“Well, I must go grocery shopping, the refrigerator and the cupboards are bare. At least for anything that would spoil. I unloaded those things before we left. That should take a couple of hours.”

“Good, then I’ll call Laverne and see if she can’t come over around four to measure you for your new uniforms and corsets.”

Laverne was a friend, and an expert seamstress. She and Logan had met at the hospital where Logan operated on, and saved her invalid husband’s life. They’d become great friends, even though there was almost a thirty-year age difference. It was Laverne who custom made all of Dilan’s corsets and uniforms. They fit him perfectly and she never commented on his boy’s body.

“New corsets too?” he asked. He hated the uncomfortable and restrictive things, and was afraid new ones would be even less palatable.

“Of course, corsets. We talked about it. Not only do you need new ones to better support your breasts, but we also want to reduce your waist to give you a better shape.”

When Dilan didn’t respond immediately, she prompted him, “right?”

“Yes türbanlı seks hikayeleri Mistress.”

Logan nodded. “I really want to see you in uniforms that show off your cleavage, like your dream girl Yvette. And the sooner Laverne gets your new measurements, the sooner you’ll be more like the sexy French maid you dreamt of.”

After cleaning up the kitchen Dilan changed to go out. He couldn’t wear his maids uniform out in public, it would be too embarrassing, even for him. So, he took out one of his street clothes outfits. A woman’s yellow blouse, black stretch slacks with a flat front and zipper up the back, and simple black, wedgie pumps with two-inch heels. He’d wear those things over his corset, panties and stockings.

He used to simply take off his bra and breast forms, so he could at least look like a flat-chested guy, in shirt and pants, even though they were all feminine cuts.

But now he had to hide his breasts. And find a more comfortable and successful method than the make-shift solution he’d used for the flight home.

He’d had time during their trip to develop a plan for the situation. He searched through Logan’s extensive collection of medical supplies until he found two, wide rolls of stretchy bandages. And then he laboriously began wrapping them around his chest, flattening his new breasts.

It was difficult to manage, and difficult to accomplish. Twisting and wrapping the bandages was a challenge especially in his corset. And pulling them tight enough to crush his big tits flat was again both painful and almost impossible. The implants were huge and resisted being squashed.

When he had finally gotten the wrappings in place, and his chest as flat as he thought possible, he slipped on his blouse and was disappointed and frightened by the result. He still had breasts, and his blouse was obviously over-stretched covering them. Damn!

It was bad enough that his dildo tented his tight slacks bulging out their flat front. Embarrassingly so when he was at all excited. But his breasts were just too obvious, despite his best efforts.

Unable to think of a solution he finished dressing tied his hair back and self-consciously walked downstair to find his lover.

“Logan, I don’t see how I can go out like this. I have to get new tops, or find some better way to flatten my breasts.” He said as he walked into her office.

Logan looked up from her laptop.

She stared for a moment, then twirled a finger, signaling him to twirl so she could see more of him.

He spun, slowly like a model on the runway.

“Well, I can see what you mean. We will have to get you some new tops. Ones cut for a small chested woman. That one just calls attention to your chesty form. We might also have to get you an A-cup bra to go under it.”

“But that would show too, wouldn’t it?”

“Probably, yes. But you’d look better than you look now.”

Even more feminine, Dilan thought, but he didn’t say anything.

“I’ll order some things, while you’re out. They should get here tomorrow or the next day.” She said as she went back to focusing her attention on her computer.

Dilan was stuck, standing there undecided about what to do. They needed groceries, now, today. But how could he go out looking like this?

Logan, realizing that he was still standing there, looked up, annoyed. “Well, what are you waiting for? Go do your shopping.”

He went out, but drove many miles away to a different neighborhood so he could shop where nobody would know him.

And he put up with a lot of stares, and derisive laughter, and insulting, ribald comments. But in the end, he succeeded in picking up everything he needed.

Back at home, he quickly put away those items that went into the refrigerator before he headed upstairs to put his maid’s uniform back on. It was a requirement and a relief. As of a few months ago, Logan had begun demanding that he always wear a uniform while he was in the house, and now it felt wonderful to free his breasts from their wrappings.

He was just finishing up putting away the rest of his purchases when Laverne arrived. She and Logan visited for a while before Logan retrieved him for his measurement session with the seamstress.

She had him strip down to his panties so she could measure his new breasts and recheck his waist.

“Those are large.” Was her first comment. “A little over a standard D-cup, I believe.”

“But, aren’t they lovely?” Logan asked, happily.

“Yes, they are.

“And according to my tape, the corseting over these last six months has shrunken his waist by a couple of inches.” Laverne added.

“Oh my. That’s great, I hadn’t really noticed.”

“Yes, he’s at twenty-nine inches now.”

“Well then, we really need new corsets for him. Not only to support his new breasts but to take his waist down to an even more girlish size. How small do you think we can take him?”

Laverne thought for a few minutes. “You know the normal target is a four-inch reduction, so we could take him to twenty-five. But if you really want to, I think we could shrink him to twenty-three, but it would be difficult for him.”

Logan smiled. “Oh, but I bet he’d look wonderful with a twenty-three-inch waist. And it would make him look like he actually has hips. I love that idea. Don’t you, my love?”

The idea scared the hell out of him, but he knew that Logan wanted it, so she’d get it.

“Yes Mistress.”

Logan smiled happily again. “That’s my boy. And just think how good you’ll look at our wedding.”

“Wedding?” Laverne asked, jumping in excitedly.

Logan slapped her hand over her mouth, theatrically. Then lowered it sheepishly.

“Yes, we’re engaged. We haven’t set a date yet. We haven’t even bought rings yet. But my Dilan will be my husband, sometime soon. And you’ll be invited.”

Laverne nodded and smiled, “I’d love to attend.” Then she reached over to grab Logan’s hand, “and I’d be delighted to make you your dress.” And then she turned to look at Dilan, who was still standing there in just his panties. “And I’d enjoy making you an outfit too.”

“Oh, that would be fantastic!” Logan said, excitedly. “I’ve been thinking about my Dilan’s outfit since we decided to get hitched. But we can discuss that over lunch later this week.”

“That sounds good.”

Dilan had just been standing quietly while the two women planned his future attire. It made him nervous, but he was used to Logan making all of the decisions, including those about what he would wear, and look like, and how he should behave, so nothing unusual there.

Eventually Laverne finished collecting his new dimensions, and said her goodbyes, promising to return in a week with the first delivery of products. Several others would be arriving after that. Eventually all of her Maid’s outfits would be replaced with the new, cleavage-revealing ones, and all of her corsets with the newer smaller-waist ones, oh joy!

In the days that followed Logan easily slid back into her previous work and home-life routines, while Dilan struggled to get used to his new body. Although the breasts weighed on his chest and shoulders, and pulled on his back, he had suffered similarly when he wore the breast forms, before the trip.

Sitting to pee was an oddity that bothered him primarily because of his permanently adjusted plumbing. Each time he used the toilet, it reminded him of how different he now was. Even less of a man, more like a girl and certainly more of a sissy.

It wasn’t that bad around the house, but going out remained a problem. Even after a collection of new blouses arrived, along with several tight and relatively unobtrusive A-cup bras, when he went out people stared at the sissy with the vaguely feminine chest.

His hair and his nails and his jewelry also added to his challenges. They too attracted unwanted attention and scorn, as people noticed them. Standing in the cashier line at the grocery store was the worst. There everyone had an opportunity to study him, up close, and the cashiers themselves often snickered and commented on his nails as they exchanged monies.

Each morning, he continued to apply his makeup in full, like he had learned to do back on the island. Just as a woman would. Of course, it always took time, and when for his job, he had to join a video conference call, a regular occurrence, he had to strip it all off beforehand, and then reapply it afterwards.

And he has to deal with the cosmetics even more whenever he leaves the house. Then, he has to strip off his feminine face, apply the light makeup appropriate for a sissy, and then reapply his heavier makeup when he puts his maid’s uniform back on.

But Logan encourages it, and loves it, so he performs those tasks regularly. It makes him wonder though if Logan really prefers it when he’s a girl. Dylan with a ‘y’. And he dejectedly asks himself why she wanted him to return to his sissy life when they returned. Did she just enjoy the humiliation he suffered with his new body?

On Saturday, Logan had him dress for going out, and she took him to several jewelry stores to select engagement and wedding rings.

He just followed along as she scanned the display cases looking for just the right symbols of their love for one another.

Although he wasn’t all that surprised, the salesmen and women were clearly shocked when she explained that she wanted two identical sets, one for her and one for her husband, indicating Dilan, next to her.

The staff’s expressions were actually quite funny, but Dilan wasn’t in the mood to laugh at them. He was picturing the diamond ring setting and solid bands that his lover was electing as yet another humiliation he’d have to endure when he went out in public. A guy wearing a woman’s engagement ring on his left ring finger.

Finally, Logan selected a pretty, gold set and had them mount, eye-catching three-karat diamonds in the primary mount. Two pairs of red rubies framed the diamond to attract even more attention.

Later that day, when they returned to pick up their rings, sliding them on their respective fingers right there in the shop, everyone agreed that Logan’s ring looked absolutely gorgeous, on her finger. And they all told him how nice the ring looked on his.

From that point on, the ring never left his finger.

Dilan went back to work, in his home office with his telephone and big monitor. He was always careful to ensure that the camera used for hie steady stream of video conference calls, several per day, only showed his head, and not what he was wearing.

He had begged Logan for permission to remove his earrings, with their dangling connecting chains that he constantly wore, while he was on video calls. In the past, he had always removed any makeup he wore, and tied his hair into a pony-tail during his calls, so he could at least appear to be a guy.

His fiancé had begrudgingly given him permission to do just that, but had stipulated that he return everything to the way it was, after the call. It was an annoying task, especially with several calls per day, but he couldn’t refuse her.

After work, they resumed their old routines. Dilan prepared their evening meal to be ready when Logan came home from her long days at the medical center. And they sat together, watching the TV news while they ate and reviewed their days, and discussed current events. Like any other loving couple. Except for the sissy’s costume and looks, of course.

Afterwards Dilan would clen up and then they’d curl up together on the couch to watch a few sitcoms before bed.

Often, they’d have sex. With Logan riding her dildo to her orgasm while Dilan enjoyed the feelings and came onto the towel positioned beneath his ass.

It seemed that her orgasms were always much better than his.

And afterwards, Logan continued to enjoy sleeping with her head resting on his chest. “These are the best pillows I’ve ever had,” she comments, often. Dilan doesn’t mind at all. He appreciates the intimacy, and the love.

And when Logan idly massages his breasts, before she nods off, it feels lovely and he gets excited, and that feels good too.

Sometimes though, her hand leaves his breast and slides down to his dildo, her dildo. And she massages that part of him. And it really gets him aroused. But when it doesn’t lead to anything, and she just falls asleep, it’s frustrating as all hell.

It was during their second week back, that the first shipment of uniforms and corsets arrives, three of each.

To Logan it was like Christmas, new and fun things to handle and enjoy with her mate, but to Dilan it was a time of fear and worry.

Everything was certainly pretty, and clearly well made, but as far as he could see, they would all make his life more difficult.

Not only are the new corsets tighter, they’re more heavily boned as well. He hadn’t expected that.

The boning made it almost impossible for him to twist or bend at the waist.

But Logan loved them and the effect they had on his posture and movements.

Even with Logan’s assistance he wasn’t able to lace them completely closed for the first several months, but eventually he succeeded, and Logan was delighted at his twenty-three-inch waist.

He was absolutely forced to shallow breaths, from the upper part of his chest, and he often became breathless when he had to do any heavy lifting.

But the things absolutely delighted Logan. She adored his new shape as well as the restrictions on his movements, and the breathless heaving’s of his chest, too.

They also found that Laverne had included a couple additional corsets, with a little note that described it as a ‘sleeping corset’, something to be worn in bed to ensure that during the night the improvements in his shape didn’t relax and fade.

“That’s wonderful,” Logan cried happily. We’ll get your waist down to a more feminine shape in no time.


“What?” Sternly.

“That will be nice, Mistress,” meekly.

“I agree.”

As he expected, the new uniforms were so low cut and tight across his chest that he was afraid his big boobs were going to explode up and out at any moment. As he didn’t have a woman’s large areolas, Laverne was able to cut the tops even lower, to ensure that his breasts were on full display. He had to admit they looked magnificent. Better than Yvette’s ever did. And sexier than many of the red-carpet vixens did, too.

So now, his beautiful breasts were always in full view, as he labored around the house, either while he worked at his job, or as Logan’s maid, cook and lover.

He also discovered how much they got in the way. Not only blocking his vision but some of his arm movements, too. And at the same time the new corsets were even more difficult to deal with. It was their stiffness that was the most troublesome. Twisting and bending were exceptionally difficult. That didn’t pose too big a problem when he was sitting at his desk, although it did force him to sit up very straight. The restriction did make it much harder to perform his chores around the house. Those Real maid’s tasks, that he was dressed for.

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