Paradise Isle, Sissy, Pt. 01

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"A support bra, but only for the next week," said doctor. "Then you can start going without, for increasing periods of time, if you want."

"Won't I need one always, to hold them up and stop them from bouncing around?"

"Lover, they're firmly artificial. They won't sag. They'll move wonderfully under your tops. And your corsets will hold them up and provide some support, too. So, no bras for you."

That idea bothered and confused her too. At home, the corsets were a part of her maid's outfit. She wore them always. They were more like cinchers, pulling in her tummy, and giving her a slightly more feminine waist. And when she wore her other clothes, outside the home, she simply left off her bra and breast forms, and the tight corsets were mostly invisible.

But what could she do now? If Logan required her to wear full corsets to support her tits and help her back. If they were anything like what she imagined, it would be really difficult to hide her breasts with elastic bandages, as she'd expected.

Damn! She was so screwed.

A short discussion on care and recovery followed. Then they thoughtfully provided her with several ugly and functional support bras, one of which she wore under her dress as they departed the clinic and headed back to their suite.

Alma, spent much of their short shuttle ride congratulating Dylan on her new breasts; how they looked and how feminine she now appeared. All Dylan did was smile, nod and accept the praise. She was still a bit in shock, and felling uncomfortable with her new body.

Logan held back while they rode in the van, but as soon as they exited, said farewell to Alma, and started on the walk back to their suite, she couldn't hold back any longer. "I just love your new chest. You'll look so good in your uniforms, and I think they'll be lovely to play with in bed, and during sex. Don't you?"

"I guess," Dylan mumbled.

Apparently, that wasn't the right answer.

Dylan stopped dead, grabbed Dylan by the shoulders and turned her so they stood face-to-face. "Dylan, my love. You need to get with the program, here. I know it's a shock. But it's my gift to you, and for us. And you need to accept it and enjoy it."

Dylan looked at her for a moment, "Yes Mistress, but there's so much I have to get used to."

"I understand. But one more thing you have to get used to is always being my happy companion and lover. You are what you are, and there's no going back. So, enjoy it."

Dylan thought she understood. And taking a deep breath, she forced a smile. "Yes Mistress, I do want you to be happy and proud of me."

"Excellent. Now come along. I want sex with my big-titted girlfriend." And she grabbed Dylan's hand and led her in a jog to their door.

It was the first time Dylan had run with her new breasts, and despite the bra, the things bounced on her chest and when she looked down, she could see them moving erotically under her dress.

For some reason the sight made her smile, and Logan's dildo started to get hard and push against her panties.

Inside, in only seconds they were both naked in their bed. As always Dylan laid on her back, but this time, for the first time, her big breasts laid heavily on her chest, moving enticingly up and down as she panted excitedly.

Logan giggled as she lowered herself down onto her dildo, and then reached out to gently grope her lover's wonderful new tits.

"This is so cool." She mumbled, as she began pumping up and down on her lover's other key feature.

"How do they feel?" Logan asked as she massaged the two mounds.

"Um, good, and strange. But your dildo feels really good." Dylan replied as she began pushing up while her lover pushed down.

Their rhythm soon got them to their peak and they both orgasmed. And Dylan's sperm dribbled out and down and onto the sheets.

"Damn!" He mumbled, panting and still thrusting away. "We forgot the towel. I'm making a mess."

Logan chuckled, "messy girl! I should punish you for that."

As she was still enjoying the last of her orgasm, it took Dylan a few minutes to respond. "Punish me?"

Logan giggled, "you mean, punish me, Mistress?"

Dylan smiled at the game. "Yes, of course, you want to punish me, my Mistress? What did you have in mind?"

Logan stopped pumping for a moment, thinking. "You know, my love, I've never before even thought about punishing you. You've always been such a perfect lover. But I'm sure I can come up with something."

Dylan giggled. "No need, my love. I'll always be your good little sissy."

"Yes, you will. Now go and clean up and bring something back to clean up the bed, too." And she lifted herself off of her shrunken dildo and collapsed over onto the mattress, onto a spot not stained by cum.

For the next week, Dylan wore a support bra, with a bikini bottom and a pool wrap whenever they went out. And they did go out, much more often than before. Either for meals, or just for exercise,

Of course, the dildo was always tucked back between her legs. And she got used to both that and her new breasts.

And even covered as she was, Dylan drew stares, at her healthy chest.

Of course, she was well made-up each time they went out. Logan required it.

IT was often a struggle, though, as the sights were frequently arousing and the dildo kept wanting to push itself free. Dylan had to play every game she knew to focus her attention elsewhere, and calm her libido.

One night, after they'd made love, Dylan was lying in bed next to her lover, once again pensively reviewing her current state. She realized that she was so used to dressing, peeing, and when she looked in the mirror, seeing herself as a girl, that she was actually thinking of herself as a girl. It was kind of spooky. All of her years as Dilan, he'd never dreamed of being a woman. He'd idolized them. And dreamed of sex with them. And admired their beauty and power. But never fantasized about being one.

But now, here she (not 'he') was, under Logan's complete control, with a body closer to a girl's than a guy's and living as a woman.

What an extraordinary life she was living. But she was in love and happy.

To be continued...

From the Author: Please comment on my stories. All thoughts, positive or negative are welcome. If negative, please extend the courtesy of providing constructive criticism. Thanks.

If you do comment, check back in a few days, as I do try and post replies.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
12 Comments
BriannaPrincessBriannaPrincess7 days ago

I like this story so far. I'm glad I read 'The Beginning' first, it really does set the stage. Dylan seems to be in a 'no way out' situation with Logan. I love that and hope Logan's control over 'her' continues to strengthen :).

LauraWestLauraWestover 1 year ago

I love this story! Thank you for writing it. 'm envious of Dylan!

Laura

AnonymousAnonymousover 1 year ago

You don’t know how much we appreciate your comments as the author, in response to our comments. We really do like your writings. But this chapter to this story caught us off guard on Logan bypassing his input about bypassing his/her cock, not on your writings..

ChangeYourPasswordChangeYourPasswordover 1 year agoAuthor
I appreciate the comments

I understand this tale is more edgy (abusive?) than many of my others. I picture Logan as a strong, accomplished and dominant woman, and Dilan is very much the submissive. Their relationship is based on him always saying ‘yes’. To him, women are to be worshiped.

As to the Danni story, I’m afraid I wouldn’t know where else to take him/her. This Sissy story, is almost too similar (repetitive?) I already feel like I need to write something totally different; once I finish Sissy.

In any case – Thanks again for the feedback.

AnonymousAnonymousover 1 year ago

One of the only story lines that I disagree with how she cheated him of having an input in what she did to his cock, if he had been informed up front then agreed that would have been ok, but not this way. How can he trust her now? Maybe if she had the doctors reversed the procedure, he could trust her again.

Please go back to PARADISE ISLE - DANNI REMODELED and write another chapter on that story instead, please..

I really have loved all of your other stories, just not this one, but please keep writing..

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

"Sissified": 12 Days of Sissy-mas Straight man is turned into a submissive sissy by...in Transgender & Crossdressers
Sissification 101: Ch. 01 Straight guy is caught watching sissy porn and…in Fetish
A Harmless Favor A young wife assists her young husband to become a sissy.in Transgender & Crossdressers
A Boiled Frog Pt. 01 Wife slowly brings husband into feminine lifestyle.in Transgender & Crossdressers
Shemale Surprise A married man is seduced and taken by a friend of his wife's.in Transgender & Crossdressers
More Stories