Paradise Isle, Sissy, Pt. 02

Jenna smiled, "they're lovely, and on your boyish figure they look larger. Logan, do you have any plans to further expand them? With your boy's tiny hips, I think F-cups would look wonderfully obscene." And she added a witchy cackle.

Logan laughed. "Well at home she wears a strict corset, that gives her a better shape, and I'm sure it will help emphasize her breasts, but I am considering it."

"Oh, please do."

Dylan was relieved when they all focused on their meals, and the conversation died out. She hoped that was the end of it.

For the next while, they all ate and shared reviews of their meals. Even Billy joined in, tentatively. And for a few minutes, while their mistresses talked, Billy and Dylan chatted about some of the sights.

But then things took another turn for the worst, at least as far as Dylan was concerned.

"So, tell me about Billy's cage. I've considered chastity for my Dylan, but it doesn't seem necessary. At least in our relationship." Logan asked.

Jenna smiled proudly. "He's been wearing it for a little better than a year now. The thing is custom made, and inescapable. I had him pierced with a Prince Albert, so when I insert the hook, and lock the cage to its's ring, it's inescapable. And it's made out of some super hard alloy that will be awfully difficult to cut."

She took a couple of bites of her fish, before continuing. "I'm afraid his cock isn't very big; actually, it's kind of tiny, and the cage was designed to secure it in an almost microscopic state." And she giggled, delightedly, while Billy blushed.

"Don't you think that's mean?" Logan said, but she was actually intrigued.

"Oh please. My Billy was always docile. But with that thing he's also wonderfully obedient, horny and hopeful. And of course, he loves me, totally."

Logan looked at her for a moment, deep in thought, but then, deciding that it would be fun, she spoke up. "My Dylan has a unique cock, too."

"Oh?"

"Yes, she has a permanent phallus, just like a strap-on."

"I don't understand. You said she's really a guy, so she has a cock, right?"

"Well, yes and no. She pees like a girl, from between her legs. And when she orgasms, her cum comes out there, too. So, her cock is just a big dildo, that doesn't squirt anything. It only exists to give me pleasure."

"Doesn't he, er she, feel anything?"

"Oh yes, she still enjoys herself, but she never pumps out any sperm from that thing."

Of course, while her lover, described her new plumbing arrangement, Dylan was dying inside. How could she? She was thinking, shocked that her lover was telling about her most humiliating modification, and making fun of her at the same time.

"Please, oh please, I have to see this!" Jenna begged, excitedly and with a chuckle.

"That procedure may be a perfect gift for my Billy." She added.

Dylan glanced over at the slave boy when his mistress made that comment, and the boy's terrified expression made her smile. Misery loves company, she decided.

Her hopes that Logan would refuse the request for a very personal examination were dashed when her Mistress agreed to accompany their two new friends over to their suite for what Dylan expected to be a porn show where she would be the star attraction. Shit!

After a hurriedly finished meal, Logan and Dylan followed Jenna and her pet boy to their room.

As they followed along, Dylan realized that Billy was completely hairless, everywhere. Not only around his caged cock. That Dylan had noted when they were first introduced. But now she noted that just like her, Billy's hair had been removed from his entire body.

Well, we have that in common, along with our two very controlling Mistresses.

Inside their suite, the two women plotted for just a few minutes before declaring that the best method for Jenna to learn about Dylan's dildo, was for a live demonstration.

Their plans left Dylan dejected and Billy excited. He hoped that he'd be able to get his rocks off. It had been weeks!

After that, the women wasted no time on niceties or fore-play.

They positioned Billy on his back with a pillow propping up his head and his arms secured by straps to the head-board. He lost his enthusiasm when he understood his positioning.

"Nice accessories." Logan said with a chuckle.

Jenna laughed. "I like them. They're available on request from housekeeping, you know."

"I didn't. Interesting."

After a short discussion between the two Mistresses, Dylan was placed on his knees straddling Billy's chest and shoulders with his dildo standing over bossy Jenna's pet's head.

That way, with Dylan leaning forward on all fours, with his legs spread, the girls crouching at the foot of the bed, could see his cock, balls, and pee hole.

Jenna laughed uproariously as Logan explained more details of her Dylan's dildo, and why it was far better than a cock.

Finally, they were ready and Billy and Dylan were ordered to proceed with the show.

Resignedly Dylan shifted up and Billy opened his mouth to accept the dildo, while Jenna squatted down to watch, and Logan joined her, wrapping her arm around her as they bent over the mattress, hip-to-hip.

"Did I see a plug in Billy's ass?" Logan asked.

"Yes, of course. It reminds him of his status, and as he moves, it massages his prostate, and that makes him even hornier."

"Oh, my."

"And sometimes when he's bad and I'm in the mood, I use a dildo up there and milk him. He comes, despite his cage, but he doesn't enjoy it much."

Billy was apparently experienced, and not at all hesitant about sucking on a cock, and Dylan quickly began to enjoy the feelings emanating from her dildo.

Soon they were pumping away, and Dylan was panting and occasionally moaning.

In that position, on his hands and knees, Dylan really felt the weight of her breasts as gravity pulled them down and her pumping made them sway and jiggle beneath her. She could feel their mass pulling on her chest and back. When she dropped her head and looked, all she could see was boob. They completely blocked her view of Billy's head and her dildo. It all seemed so bizarre.

"Billy, don't you dare make him cum yet. You keep him on the edge until I tell you to. I want to make sure I see him dribble." Jenna ordered.

"Her. Not him." Logan reminded, with a smile.

"Sorry."

Billy, in response to his Mistress' orders, slowed his efforts and even lightly bit the cock in his mouth, making Dylan jump and groan, and slow his own pumping action.

The women giggled.

Billy maintained the slow-motion sucking for several minutes, and it drove Dylan mad! But by then Jenna was getting bored. "Okay Billy, you can finish him off, now."

The women watched as Billy picked up his pace and Dylan reacted as expected.

Only moments later he reached his tipping point and the women giggled as they watched his cum dribble out and land on Billy's neck and chest.

"That's wonderful!" Jenna said enthusiastically as the dripping came to an end, and Dylan slowed and sighed.

Billy slowed down as well, realizing that Dylan was finished, and his cock shrinking.

"Alright Dylan, you can back off now. You're through and I'm sure Billy needs to clean all of your cum off his chest." Logan said as she stood to get out of the way.

Jenna stood also. "Logan, you really should keep a plug in that sweet little ass hole of hers. It would encourage your girl to feel even more feminine."

"I'll think about it. We've never played any anal games."

"You should. It's a lot of fun to milk a boy to orgasm using a dildo up the ass. And keeping a plug rubbing inside their behind, keeps them interested in that game."

Logan nodded, but she had been distracted by another idea for their entertainment.

"Dylan, I've just had a brilliant idea." Logan said. "Actually, it might just be more diabolical, at least where you're concerned.

"Yes Mistress?" she replied, nervously.

"We've talked about the need for some sort of punishment for you. You've always been such a good boy that it was never necessary."

Then she turned to Jenna, "Lately, though, she's slipped up a couple of times, and she and I agreed that a punishment is in order. So, I've decided that the perfect way for her to learn her lesson would be for her to return the favor with your Billy. If you'd unlock him, I'll punish my Dylan by making him suck that real cock."

Logan then looked around the room.

Dylan was horrified. Billy was excited, and Jenna was thoughtful.

"I'm not sure my Billy has earned a release." Jenna said, as she looked at her lover.

"Well, I can assure you that my Dylan will hate every minute of it. So, it should be entertaining. You see, she's never blown a guy before. She only loves women. Strong women like you and me."

Jenna shifted her gaze from her boy to Dylan, and his expression made her laugh. "Oh, I can see that it would be an excellent punishment. One she'll never forget. And I suppose my Billy would be happy to assist in your sissy's correction. Wouldn't you Billy?"

"Oh yes, Mistress. Please allow me to help out with Dylan's punishment." Billy said, happily.

When they all looked back at Dylan, her expression hadn't changed. She clearly hated the idea. And she was already crying. "Please, Mistress." She mumbled.

"Oh, no! You deserve a punishment, and this one will be a perfect reminder to you of the difference between a dildo and a cock, and how messy real cocks are."

Logan then pulled Dylan in close so she could whisper in her ear. "My love, this is for your own good. You will do this for me. You have to do this for me. Remember, you are mine."

Dylan knew she had no choice. "Yes Mistress," he whispered back.

At that, Jenna chuckled and went over to her purse to retrieve her key to Billy's happiness.

Returning she gestured to her boy, "sit on the bed, legs wide."

Smiling happily, he sat down on the foot of the bed, in the center of the mattress.

Jenna bent over and unlocked and removed his cage, allowing his cock to spring out and up. It was almost instantly hard.

She then sat down next to him, on his left, while Logan moved over and sat on his right-hand side. After she was settled, she looked at Dylan and simply pointed to a spot on the floor in between the slave's legs.

"And she will swallow, too, won't she?" Jenna asked, pleasantly.

Logan answered. "Of course, she will. She needs to learn how messy that stuff is. And why it's so nice when it just dribbles out of a pee hole."

Listening to her lover, Dylan thought for the first time ever, she can be very mean.

Dylan stood motionless for only a moment, looking at Billy and his cock. At least, the thing was hairless, and not any larger than the one Dilan used to have, before it became Logan's dildo.

Resignedly, she took a step forward and sank down to her knees directly in front of the guy. In that position it seemed that all she could see was cock. Hard, red and dripping.

She closed her eyes, leaned forward, opened her mouth and slowly slid it over the hard rod in front of her. She tried to think of it as a dildo, a real plastic one, but it was too soft and warm for that.

Immediately she tasted pre-cum for the first time. And she had to admit that it wasn't terrible. So, she wasn't put off by that.

Now that she'd crossed the first line and had a cock in her mouth, she was dreading the taste of real cum, and having to swallow it.

Knowing from experience what was expected of her, Dylan began tonguing, sucking and pumping her head up and down the shaft.

She heard Billy moaning in pleasure and that seemed to make things worse for her, even more humiliating and revolting. But she kept at it. Logan was watching.

"You can cup his balls." Jenna interjected.

"Nice touch." Logan said giggling.

So, Dylan reached out and gently wrapped her fingers around the guy's hanging balls. It was another first for her, she'd never handled anyone else's. She knew to be careful.

After only a couple of minutes Billy began to squirm and thrust and moan.

"He's so horny all of the time, he always loses it and comes far too quickly. That's why I find it hardly ever worth it to unlock him." Jenna told them.

And then Billy tensed, pushed his cock all the way into Dylan's mouth and began spurting cum down her throat.

And Dylan choked, both because of the cockhead tickling the back of her throat, and because of the flow of sperm running down and into her stomach.

She had to hold her breath, until Billy finally stopped squirting.

When Dylan started to lean back, Jenna reached over to stop her, holding the back of her head, onto her boy's cock. It was still pulsing slightly, not completely empty.

"You need to learn. Don't release that cock in your mouth. Just lean back enough to swallow and then take a breath, then wrap those lips around it and suck it completely dry. That will also give you a better taste of his lovely cum."

Bitch! Dylan thought, but she did as she was told.

She took a big gulp of air, pushed back onto his cock and did taste the male sperm. And it was thicker, salty and more bitter than the pre-cum. Not terrible, but not pleasant for her either.

And, as Billy's cock was still firm in her mouth she resumed slowly pumping as she sucked the thing dry.

He was panting and moaning quietly, clearly enjoying the last bit of his release. He even reached up and ran his fingers lovingly through Dylan's hair.

For a moment Dylan enjoyed that touch; it reminded her of Logan's, but then she realized it was the culmination of the blow job she'd just given a guy. And her thoughts turned to disgust, sadness and embarrassment.

Dylan kept it up until the cock in her mouth had shrunken enough to almost fall out.

"You can let him go, now, and go rinse out your mouth, now, Dylan." Logan told him.

With a sigh, she let the thing slide out from between her lips and staggered to her feet.

As she walked to the bathroom, all she could think about was the slimy coating inside her mouth and throat. Disgusting! And humiliating too.

She couldn't believe that she'd just sucked a guy's cock dry.

Inside the bathroom she repeatedly rinsed out her mouth until the taste was completely gone. She wished there was some mouthwash...

When she turned to head back into the room, Jenna was standing in the door, smiling condescendingly. "I bet your lipstick needs freshening," she said with a chuckle. And she pushed Dylan back until her ass hit the counter.

Holding her there with a hand on a breast, pinching a nipple, she leaned over and picked up a tube of bright red color. Then she stood back in front of Dylan and gently painted her lips.

As she did, rather kindly she murmured to her, "that wasn't so bad, was it? All girls should know how to suck on cocks. Right?"

Dylan wanted to say, 'no'. And she wanted to protest that she wasn't a girl. Or even that she was a lesbian, who didn't like men. But she knew that wouldn't cut it. So, she answered as she knew she must.

"Yes Mistress."

Jenna paused and stared at her, just like her Mistress did when she required a better answer.

"Yes, Mistress, all girls need to know how to suck on cocks."

"Excellent." Jenna replied as she finished up painting Dylan's lips with the bright color.

The two of them then walked out to join the other pair.

Dylan saw that Billy's cock was already locked back up; Jenna must have done that before she ambushed her in the bathroom.

Logan was standing, and she came over and hugged, and kissed her. Then stood back and reached up to caress her cheek, lovingly.

"Did you learn your lesson?"

After her discussion with Jenna, Dylan wasn't sure which lesson her Mistress was referring to. But she answered anyway, "yes Mistress."

"Good. I think that was the perfect punishment for you. I'm sure you know I'm not the type of mistress who would spank or whip you. I'm not into inflicting physical pain. But I'm sure that was a punishment that left its mark. Am I right?"

"Yes Mistress."

"And you know, I won't hesitate to use that same method of punishment, again, if I think it's necessary."

That really frightened the already hurt and humiliated Dylan. "Yes Mistress."

Jenna, the more dominant woman, spoke up. "I'm not sure if the next time will be so difficult for her. Now that she's an experienced cock-sucker." And she turned to her Billy. "She was pretty good, wasn't she?"

"Yes Mistress, she is a good cock-sucker," he responded, with a very satisfied smile.

You prick! Dylan thought. No honor among men...

Logan nodded and smiled, "In any case, thanks for helping me discipline my lover. I think, though that it's time for us to head home. It's been a distinct pleasure."

"Oh, the pleasure has been all ours. Your girl is fascinating." Jenni said as she leaned in and gave first logan and then Dylan kisses.

"And thanks for doing her lipstick," Logan added, "I like that shade of red on her. She usually wears a more girlish shade of pink."

"You're quite welcome."

It only took a minute for the two of them to pull on their bikini bottoms, and for Dylan to tuck her shrunken dildo back between her legs. The move drew another giggle from Jenna.

Logan then led Dylan out the door and down the path in the direction of their building. Neither of them said anything, as they walked along.

Instead of taking her straight home, Logan steered them into the first bar they came upon, and they sat down at a little table in a corner.

"I bet you need a drink." She said, smiling lovingly.

Dylan just nodded.

Logan ordered a couple glasses of wine, and they sat quietly watching the sites until their drinks were delivered

After a long drink from her glass, Dylan finally spoke up. "Why?"

Logan reached over to hold her hand, resting on the table. "Because you needed a punishment, not because of making a mess, or a slip of the tongue, but because you need to do better at behaving as my happy little girl, or sissy, or lover, or spouse."

Dylan choked on her drink! After she finished coughing, she asked, "spouse?"

Logan giggled, "yes silly. When we get home, I'm going to start planning our wedding. I want to make an honest man out of you."

Dylan, now happy, chuckled, "or girl, or sissy."

Logan laughed, "or dildo holder."

"That too." And then laughing delightedly they leaned over and hugged and kissed passionately. And several of the other guests watched appreciatively at the love the two of them showed.

When they finally settled back into their chairs to catch their breaths, Logan took a sip of her wine and asked, "well?"

"Well, what?"

"Do you accept?"

Dylan laughed. "Of course, I do. I have no real choice in the matter anyway. Do I?"

"No, you don't." Logan said with a smile.

"Logan, my love, I'm yours, forever. And I'll be your wife, as well as your sissy, your girl, or slave, or sex object. Anything you want."

Logan chuckled. "I kind of like, 'sex object'."

And they laughed together.

After another round of drinks, they headed back to their suite, holding each other close as they walked along.

"Did you hate the cock-sucking? Logan asked, casually. "Was it a meaningful punishment?"

"It was a terribly mean one."

"But did you learn a lesson?"

"Yes Mistress."

"And it wasn't that terrible, was it? Admit it. Girls do it all of the time."

Dylan sighed, she hadn't liked it one bit, but she had to admit that it was neither difficult nor painful. Just humiliating and gross.

"It wasn't that difficult. But I don't want to do it ever again."

"Then don't make me punish you again."

"I won't."

"Good. Now come along, I need sex." And she hurried Dylan along. She followed, breasts bouncing. It was another new feeling for her, and again an uncomfortable one.

As they arrived at their door, Logan sighed sadly, "I'd really like to use my dildo. But I know it's empty and soft."