Paradise Isle, Sissy, Pt. 01

But before he could form a question, the nurse prompted him with a string of queries of her own. How did he feel? Did he have a headache? Any other areas of pain? And so on. Each time he answered one, there was another.

Finally, satisfied, with all of his responses, she slid right out the door, leaving the two of them alone in the room.

"What did they do?" he asked Logan, now that he had the opportunity.

"Well, my dear, they performed a fascinating procedure called a 'perineal urethrostomy'. It's a fairly unique, but relatively simple surgery that I'm certain is perfect for you, and that I'll just love."

The name meant nothing to him. He was sure his Mistress would love whatever it was, she'd arranged for it, but he wasn't so sure he would. And where it hurt him, and the presence of a catheter petrified him.

"Do I still have my cock and balls?" he asked with a quiver in his voice.

She chuckled, "of course, you do, my love. What a silly question. I'd never do that to you. And you know how much I love your cock. I'd never deprive either of us of that!"

And to emphasize her point she leaned over and gave him a loving kiss. It made him feel a lot better, and relieved. At least he was still whole, down there.

When she stood back up, he sighed and restated his question, "what, then?"

"Well, that procedure is also known as a 'urethral reroute'. It's a simple modification for boys like you."

"Huh?" with growing fear.

"What they've done is rerouted your urethra so that it exits through your perineum, that area behind your balls and in front of your anus. From now on, my love, your pee, and your sperm too for that matter, will exit from there. Not form your penis."

He was stunned. Absolutely horrified. And she could tell.

"Don't worry, you'll still get hard and you'll still orgasm, but you won't fill me with cum anymore. And of course, you'll sit to pee, just like a girl." And again, she bent down to kiss him, but he was unable and unwilling to kiss her back.

"But why?" he finally mumbled, as she stood back up.

"Dylan, and that's with a 'y', I did it for two reasons. "I want you to be more of a girl. That's why you have breasts, and now you'll pee like one too. And second, I want to use your cock, and even suck on it too, without worrying about your nasty cum squirting out the end. Your prick is now not much different from a strap-on dildo. It will be perfect for me.

"Now get some rest, you need to recover so we can enjoy the resort, together."

She gave him one more kiss, and then walked out, leaving him there to assess his new situation.

He was stunned and confused by both his new plumbing, and by his lover's attitude. She seemed to want him to be a girl. But not a real girl, as she apparently loved his cock. Now he'd be more of a sissy than ever. Or actually, more of a girl than a boy.

More than ever before, he felt like she was just toying with him. Of course, that's the way he'd felt before, when she had insisted that he only wear women's clothes, and in particular the maid's outfits. But that had been a game that he too enjoyed.

But now, with breasts, and a pee hole down between his legs, and a cock that was only a dildo for her to play with, he didn't know what he was. A doll? A pet? A girl?

Certainly, no longer a man. Or perhaps even a sissy.

And he wasn't Dilan anymore, either. To his lover, and here on the island, as well, he was Dylan, a girl.

By then he was crying, so very confused, upset, and uncertain about his future.

Eventually, though he drifted off to sleep, his body and mind exhausted and in need of recovery.

When Dylan finally woke up it was again morning, and he no longer felt any pain, only the discomfort of the catheter that stuck out of his body's new hole. His pee hole. Damn!

And he was starving, too.

So, he rang the button for the nurse.

And while he waited, again contemplated his new situation, he was surprised to realize that while he'd slept, his mind had somehow come to terms with his new body and soul. It wasn't really all that bad. Not that different than before.

He still had Logan. She still loved him, and he certainly still adored her. And his life would remain the same. He'd still be her lady's maid, living with her and serving her.

And he'd still be able to work around the house, and at his job, from home. Those things wouldn't change.

Dealing with his new breasts wouldn't be all that difficult. He knew they'd look luscious when he wore his maid's uniforms, just like Yvette's. And he got a charge out of that. He felt his cock get hard, and when he reached own beneath the sheets and grabbed himself, it didn't feel any different. It was hard and sensitive and felt good, just like it always did.

That set his mind off on a tangent, wondering how it would be when Logan made love to him.

But that thrill was short lived, as he then started dwelling on his new plumbing arrangement. He'd no longer be peeing like a man. He'd have to sit and pee like a girl, a real woman. And he wouldn't be cumming out of his cock anymore? How would that feel? He wondered. Orgasming, but not feeling the pumping and squirting. Damn!

He supposed his cum would just dribble out between his legs. Messy and gross!

That thought got him crying once again.

And the tears were still running when the nurse came in with his breakfast tray.

For a moment she was stunned, and uncomfortable, but then she set aside the tray and came over to sit on the edge of the bed and console the poor girl.

"Dylan, you'll be okay, the pain will be gone soon, and we'll take out the catheter, tomorrow. You'll be out of here a couple of days after that, and only few more days and the bandages will come off of your lovely new breasts. Won't that be nice?"

Dylan sniffed, and wiped at her eyes. "Yes," she mumbled.

"Good. Now I'm sure you're hungry. I ordered you a double breakfast. So be a good girl and dig in before it gets cold." And she set up the tray table so Dylan could eat.

"I'll call your lover for you, and I'm sure she'll be right over, so you two can talk, and relax."

Dylan began eating as the nurse left the room.

While he ate, it occurred to him that the nurse considered him to be a girl. Perhaps he was...

He was just finishing with his meal when Logan came bustling into the room.

She kissed him long and passionately, before asking, "how are you feeling my love?"

"Better."

"Good, they tell me that you're doing well. I can't wait to get you out of here, over to the suite, and rid of all of those bandages. Before you know it, we'll be able to go out and enjoy this place, together. It's absolutely lovely and there's so much fun to be had at the resort, and so many sights to see, too. I spend hours people watching. And I have to tell you, there are a lot of beautiful and very kinky people around here."

Dylan had to laugh. Logan was so very excited, and happy, and at least she was enjoying herself. While he laid around uncomfortably in his hospital bed.

He was glad to see her though. He did love her, and just the sight of her made him feel better.

They chatted for the next hour. Logan did most of the talking, telling him about the resorts and the people she'd seen. It all sounded so very exotic and erotic. It got him excited.

"Sounds wonderful, and horny too." He finally told her.

She laughed, "it is. I 'm really looking forward to taking you out there with me. And like I said, everyone out there, wears only their swim suits, if that, and the women don't bother with their bikini tops, either."

Oh shit! Dylan thought. How in the hell was he going to go out? A man with big boobs? "Logan. How can I go out like that?" He asked, distressed by his mind's picture.

"Oh, don't worry. With your new breasts everyone will see you as a girl, and you can wear a bikini bottom."

"But my cock will show!"

"Not if we push it down between your legs. You know, tuck it. That will give you a flat front, and no one will notice."

"But if I get hard...."

"Well, you won't be able to. Will you? You'll just have to control yourself."

"Out there? From what you tell me, that will be impossible!"

"Well, my love. You'll just have to learn to behave yourself."

He just harumphed in response. And she giggled.

"With makeup and your nice long hair, you'll fit right in with me and the other girls."

He groaned, at that. "But I'm a guy," he whined. Then added, sadly, "But, hell! Even the nurse thinks I'm a girl."

"Dylan, can't you tell? I like that idea. And besides you haven't been a real guy since we became lovers, and you became my sissy."

"What?" She'd never actually called him a 'sissy' before and now she liked him as a girl?

"Dylan with a 'y', silly. From now on, I want you to be a girl, and think of yourself as a girl." And before he could protest, she held up her hand. "Stop! Don't fight me on this. I love the idea, and you dress for me like a girl, and now you have breasts like a girl, and you even pee like a girl, or you will once the catheter is removed. So, get used to it. You're a girl, from now on. Clear?"

It took him a while to answer, but he finally did. "Yes Mistress."

"Good. Now I'll leave you to rest. I understand that tomorrow they'll remove your catheter, and you can start learning to pee sitting down like the girl you are."

She kissed him again, before heading out.

Dylan spent the rest of the day, alone in her room, watching the television, and playing on her tablet, outside of visits from nurses for checkups and meals.

But all day he was distracted as his mind focused on his fate, and the fact that now he was now supposed to be a she. She knew she had no choice in the matter, that was part of their relationship. She did whatever Logan demanded of her. Logan was her Mistress, after all. That was the life Dilan had been living already.

And she was used to obeying her lover, and dressing in her silly French maid's outfits most of the time. And in women's clothes the rest of the time, too.

So, she really was a girl, more or less.

The clinical staff took good care of her, treating her with attention and affection, and made no comment on her cock, as the next day they removed the terrible catheter.

And she was overjoyed to be rid of the thing. So much so that she didn't mind sitting to pee, or wiping herself with a wad of paper, afterwards.

It did feel weird, at first. Releasing her bladder, while she sat and hearing the urine splash beneath her, while not worrying about her cock.

And each time, based on the instructions provided by the nurse, after wiping she applied some ointment they provided, to her new urine exit hole.

Damn! This is weird. Not to mention depressing. My cock is now only good for sex. For satisfying my mistress.

She's wasn't allowed a shower, as she still can't get the incisions on her chest wet, so that evening, alone in her room, she took a bath. And in the soapy water, she rubbed her cock to full hardness, and it felt good.

It was a huge relief. I can still enjoy sex! And she actually giggled.

She continued to sit and rub herself until she finally climaxed. But the orgasm was unlike the ones she'd felt in the past. It didn't seem to be anywhere near as intense, or enjoyable. She missed the feeling of her cum pulsing through her hard prick, and out the end of her cock. It wasn't the same, at all. In the tub she didn't even feel her cum exiting her body through her pee hole, and into the water.

Damn!

She slept fitfully, that night. Saddened and disappointed in her inability to fully enjoy her orgasm, and hoping that it would improve over time.

Logan showed up the next morning, after breakfast, to take her back to their room. She looked spectacular in a tiny bikini. When she noticed Dylan staring, she chuckled. "Everyone around here wears a minimum of coverings. It's a very kinky place.

"You like?"

"You look spectacular. I love you so." Dylan replied, feeling good for the first time in days. Looking at her, all he could think about was sex, and love.

Logan leaned in and gave her a passionate kiss, that got her cock even more aroused.

But then she backed away and dug into a bag and pulled out a colorful and light little dress. "Look what I brought for you to wear," she said happily.

"Oh, Logan. Really?" Dylan said, sadly.

"Now Dylan, my love. We talked about this. And you can't wear a bikini until the bandages come off your tits. So, you'll wear this, and look cute.

"And I've also brought along some makeup. I'll pretty up your face, so everyone will see you as a girl. Not a sissy and certainly not a boy."

When she refused to respond, Logan stared at her, angrily.

"I thought you'd be happy. I could have brought a maid's costume, and made you wear that for the day. Without makeup. How would that have made you feel? How humiliating would that have been for a sissy, like you used to be?"

Picturing that, Dylan realized that it would have been indeed worse. She never wore her maid's outfits out in public, and didn't want to, ever. At least in a dress, and with make-up, she could pass for a girl, not a man in a slutty fetish outfit; a sissy.

"Well?" Logan asked, impatiently.

Dylan sighed. "I'm sorry Mistress. I'll be happy to wear a dress and makeup."

"Good. Let's get going."

Dylan stripped off her hospital gown, leaving her in just her wrapped-up breasts - she hadn't bothered with any underwear, so that wasn't an issue, and with Logan's help she slipped the sun dress on over her head. It was tight around her chest, but otherwise fit her well. Looking in a mirror, she realized how short it was. It barely covered her ass, and her dangling cock!

But when Logan exclaimed, "you look lovely." She realized that voicing her concerns was useless.

Next, Logan handed her a pair of high-heeled sandals.

Used to the tall pumps that went with her maid's outfits, Dylan had no problems standing for her lover's inspection.

"Excellent, but we'll have to get your toenails colored. In fact, I think a mani-pedi is in order."

Oh joy, Dylan thought. She'd been through that process before. Logan had taken Dilan, the sissy, to her manicurist, several times, to get his nails done in pale, girly colors, and he'd hated the humiliation. Now, though, she realized, that she'd fit right in, so it wouldn't be that bad.

"Now we can brush out your hair, and work on your face. I'll add a hair styling to your appointment when we go to the spa for our nails."

"Yes, Mistress," she replied, as she could tell that Logan was expecting a response.

Logan spent the next half-hour applying make-up to Dylan's face. It was another procedure that she was familiar with, as on occasion, back home Logan had, for the fun of it, applied light makeup to her sissy, before she took him out to a movie or a late dinner. He had gone along with it, despite his embarrassment, as it was always after dark, and the indoor lighting was always dim.

It struck Dylan that he should have realized back then, that his lover enjoyed dressing him as her dolly.

When Logan declared her finished, and Dylan got a good look at herself in the mirror, she was surprised, that she did look like a girl. For the first time, Dilan's slightly feminine features were an advantage, as with the makeup she really did look like a girl. Not a particularly pretty one, but nonetheless, in her dress, and with her breasts, she felt she could pass.

Logan certainly thought so. She was smiling happily and proudly.

"We'll work on this in the days to come. I really want you to look the part, and not worry about being 'outed'. Besides, you can't really walk around with your sexy new breasts looking like a boy, can you?"

"Yes, Mistress. No, Mistress."

Logan giggled.

"Good girl. Now let's check out with the nurse, and catch the shuttle back to the resort."

"But Logan. Without any underwear, I'm afraid my cock will show beneath this flimsy skirt." Dylan protested. She was terrified that someone would notice and cause a scene. It would be hard enough to behave like a girl in a dress, out in public, let alone handle the risk of flashing her cock.

Logan scowled at her. "Like I said before, you're just going to have to learn to control that thing, and behave like a lady. Making sure you don't display your ugly manhood to anyone around you. I love your dildo for sex, but I don't want my girl to display it. Understand?"

"Yes Mistress." Dylan responded automatically. But then she couldn't help but ask, "dildo?"

Logan chuckled. "Well, my girl, that thing between your legs doesn't pee, or squirt cum like a guy's cock does. Now does it?"

"No," hesitantly and sadly.

Logan smiled. "And when it's hard, it's the perfect thing to insert into my pussy, and get me off, isn't it?"

"Yes."

"Yes, what?" Logan responded with a glare.

"Yes, Mistress. It's perfect for getting you off."

"Just like a dildo." She said happily, and leaned in to give her girl a kiss, before concluding the discussion. "So, I like that term, now. My girl doesn't have a cock between her legs, she has a dildo to please me with.

"Now come on. Let's talk to the nurse and be on our way."

Logan stuck her head out of the door, and signaled the nurse, who came in and provided instructions, advice and more paperwork. She finished up with, "You just take it easy and get used to your new body. We'll see you back in a few more days to strip the wrappings off of your new breasts. Won't that be wonderful?"

"Yes," Dylan said. That event, at least, would be a happy time for her.

Dylan was careful to hide her cock as they climbed into and out of the shuttle van, as well as when they walked through the resort back to their suite. For the first time she began watching and examining the other guests, as they followed the pathway to their suite.

She hadn't realized how many people there were, how good looking they were, and how erotic, exotic they all seemed.

And as most of them were nearly, or fully naked, she really felt overdressed.

Back in their suite, Dylan collapsed into a chair with a sigh of relief. She'd succeeded in not showing the world her cock, Logan's dildo, that is. And just wanted to relax, and get used to being a girl in a dress.

But Logan had other ideas.

"Are you hungry? Because I'm ready for some lunch."

"Can't we just relax for a while? It's kind of early for lunch."

"No, like I said, I'm hungry. And I want to enjoy a meal out with my girl. We haven't eaten out together in ages."

Dylan sighed. She didn't want to go out like she was. "Can I put on some underwear, first? Please Mistress"

Logan looked at her for a moment. "All right, but first I think you need to pee. And I'd like to see it."

"Oh, Logan..."

"Now!" Logan ordered. And she reached out and grabbed her hand, pulled Dylan to her feet and pointed her toward the bathroom. "Pee, then panties and tuck. Then we'll go out as two girlfriends for lunch."

As always, Dylan did as she was told.

She stepped to the toilet, lifted her dress just a little and sat down on the seat, and with Logan watching and smiling contentedly, Dylan released her bladder.

The sound was unmistakable and while it made Dylan blush, Logan chuckled. "You sound just like me."

Finished, Dylan wiped herself, and then stepped over to dig out the tube of ointment she had to use to help keep herself clean down there.

While she did, Logan stepped out and returned with a pair of pink, nylon, bikini style panties.

"I'd love to see you in a thong, but I'm not sure if you could tuck my dildo in undies that tiny."

Dylan blushed yet again. Hearing his cock described as just a dildo, was a painful reminder of what his penis had become.

Logan again watched, smiling as she stuffed her dildo back in between her legs.