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Paradise Isle, StepSister Pt. 08

Paradise Isle, StepSister Pt. 08

(Trans, transformed, lesbian, reluctant) Happy life.

By ChangeYourPassword

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 the previous parts of StepSister, first.

The long trip home, as Jess had expected, and Aubrey had looked forward to, was indeed an adventure in being ogled, admired and occasionally harassed.

On the ferry, in the terminals and on the airplanes, they drew a lot of attention.

After several hours on sea and in the air, they made it back to the US, ready for the final flight that would take them back to the West coast.

Boarding the plane in Miami, Jess became worried when one of the flight attendants gave them dirty looks, and commented on their 'inappropriate' attire. After they'd settled into their first-class seats, Jess watched the woman bring out one of the pilots to have a look.Paradise Isle, StepSister Pt. 08 фото

"Shit," she whispered to Aubrey. "That stewardess ratted us out to the pilot."

"For what?"

"Our clothes, of course."

Aubrey scoffed.

They watched as the pilot casually wandered down the aisle, smiling while he examined his passengers.

When he arrived at their row, he only paused for a moment, and Aubrey looked up at him with a pleasant smile.

Jess sitting in the aisle seat, almost giggled when she noticed the bulge forming in his pants. It was right in front of her nose.

The guy smiled back at Aubrey, mumbled, "morning ladies," and then passed on by. He turned around a moment later and went straight back to his cockpit. He muttered something to the evil stewardess, who frowned, but didn't bother them any further.

Aubrey giggled and leaned over. "He wanted us."

Jess laughed, "he almost poked my eye out with the bulge in his pants."

Aubrey laughed, too. "The power of big boobs."

Apart from that amusing demonstration of Aubrey's new power, the flight was just long, and trying.

Jess had a difficult time getting comfortable while wearing her restrictive corset. Mid-flight she asked Aubrey if she could remove her corset, but she refused to consider it. "You look too good, to ruin things."

Aubrey continued to be amused by the reactions of the people they encountered.

Jess considered them lucky in that throughout the long day they were never assaulted, or raped. She couldn't imagine how disgusting that would have been.

She knew how traumatizing it had been for Aubrey, and she worried that a repeat occurrence would be worse for her.

It did make her wonder why Aubrie was risking it, by dressing as she was. But that wasn't a concern she wanted to pursue with her lover.

They both breathed a sigh of relief when the plane landed in San Diego - almost home.

As they shuffled off the plane, the pilot, standing in the cockpit door, smiled at them like every other man they'd encountered and thanked them for flying with him.

Aubrey, paused in front of him and chuckled. "I hope you enjoyed it as much as we did."

He blushed, but laughed. "Oh, I did."

Jess just shook her head, and as they walked down the tunnel she mumbled, "flirt."

Aubrey laughed delightedly. "Fun, eh?"

After one last parade through the airport, they grabbed a limo that took them home. What a relief...

They both sighed happily when the car pulled up in front of the house.

The driver took one long, and lascivious look before he drove away, leaving them giggling.

Inside the front door, they barely had the energy to strip off the sweaty latex, take a quick shower, and collapse into their bed. Their own bed, in their own home.

They slept until the sun woke them up, and then they made love.

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

There wasn't much to eat for breakfast, but they were in no mood to go out to some eatery, so they made do with whatever they could find.

"We'll have to go out grocery shopping this morning," Jess commented.

"And I have to go out clothes shopping," Aubrey replied. "I need new tops, at least. And new dresses that will fit and properly display my new cleavage," she added, laughing.

"Slutty things? And what about bras?" Jess asked, chuckling.

"Not slutty, just sexy. And I do intend to pick up a few bras."

"A few?"

Aubery smiled provocatively, "I will wear them, on occasion."

Jess chuckled. "You'll bounce out of your top! Like I said, slutty."

Aubrey laughed and punched her lover on the shoulder.

"Ouch!"

"Well, stop calling me names. I'm just a girl blessed with big boobs."

Finished with their meager breakfast they got dressed in casual and baggy clothes, to go shopping.

They were heading out when Aubrey noticed the pile of latex still strewn around the entrance hall.

Sighing. she turned and began picking things up. Jess joined in.

"I did enjoy these things," Aubrey muttered as she picked up the rubber dress she'd worn for the trip. It had been lying in a heap since yesterday.

"You looked sexy, that's for sure. But it was uncomfortable and hot."

"Everybody liked the sight of us, so I didn't mind that much. The way it fit so snugly actually felt nice. I think I might try more of it." Aubrey replied.

"I was afraid of that," Jess said, shaking her head, sadly. She knew that if Aubrey got more into it, she'd probably have to, as well.

They spent the rest of the morning in the grocery store, filling two carts, and then in a butcher shop for quality meats. Finally, they stopped by a liquor store for booze and wine.

It took them another hour, back at home, to put it all away.

Tired and hungry, they immediately dug out the makings for sandwiches and sat down, to eat.

"I need a nap," Aubrey moaned as she finished her lunch. "I'm still screwed up from the jet lag."

Jess nodded, and laughed. "I need a one too. And then I want to get screwed."

"You and your new puss. Always horny."

"Guilty, as charged." Jess replied, laughing again.

They took a two-hour nap, and then made love for another hour. Kissing, caressing, fondling and fingering. No pussy licking that time, and no toys either. Just a pair of lovely orgasms.

After they'd taken some time to recover, Aubrey climbed out of the bed. "Can we go out and buy me some clothes now? You need some new bras and tops, too."

"It can't wait until tomorrow?"

"No, it can't. I have nothing to wear."

"Nothing?" Jess asked, skeptically.

"Nothing that fits and shows off my new shape. You love your new pussy, and I love my new boobs."

She leaned over and poked her lover. "You just had your fun, now get moving so I can have mine."

"You didn't enjoy the sex?"

"Life isn't all about sex. Now, who's the slut?" she asked, giggling, as she dragged Jess off the mattress.

"I'm not a slut. A nymphomaniac maybe, but..."

They both laughed, and started pulling on some clothes.

Jess agreed it was a needed task, but she wasn't as thrilled by the expedition as her lover. She hadn't come to enjoy clothes shopping as much as her girlfriends did. When Denver was around, she had selected all of Jess' clothes, and all she had to do was model and wear them. And they were always revealing and sexy.

Now, she'd have to pick things out for herself, with Aubrey's help of course, but it still seemed like more of a chore than a pleasure.

Aubrey led Jess through better than a dozen women's stores in two different malls, and they examined what seemed like hundreds of dresses and outfits. She had a lot of fun selecting things that would fit and display her new chest, while Jess struggled to keep up, and pick out a few things for herself.

After a while Jess was relieved when Aubrey took it upon herself to select clothes for her, and her choices weren't quite as sexy as the ones her ex- lover had demanded Jess wear. All good...

Aubrey did like her in sexy lingerie, though. So, she still wound up with stockings high heels, garter belts and waist cinchers, as well.

Actually, Jess didn't really mind. Clothes like that had been part of Jason's dreams. Now she got to wear them, and look good in them.

Finally, the back seat full of bags and boxes, they headed home. Aubrey was delighted by all the things she'd purchased and couldn't wait to unpack and reexamine everything, but Jess, was just tired and bored.

Aubrey noticed. "Jess, my love, I'm afraid you don't understand the importance of beautiful clothes. We girls love dressing pretty, and displaying ourselves. Making other girls, and boys, envious and excited.

"It's another aspect of womanhood that you need to learn." She paused to giggle. "In some respects, you're still just a dumb guy."

Jess' first instinct was to protest. Her body was certainly all girl, but when she thought about it, she still had a boy's brain. Hopefully that would evolve.

Back home they unloaded and did start unpackaging and putting things away, but after only a short time their pace slowed. It had been a hectic day, and they were still suffering from the change in time zones.

When Aubrey yawned, and began stripping, Jess did the same.

Naked, tired and happy, they crawled into bed, and fell asleep in each other's arms. Happy to be back home, settled and ready to resume their normal lives.

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

Aubrey and Jess spent the next few days getting caught up with money management tasks. On their third day back, they met up with their little team in the conference room at Morgan's office, as they usually did, to go over the books and discuss plans. They'd been gone for a month but not all that much had changed.

Aubrey couldn't help but giggle when she walked into the conference room to meet with the crew.

Morgan, Theresa and Quinn sat stunned by the sight of her new chest.

Jess laughed at their expressions. "Yes, ladies they're real."

"What have you done, Aubrey?" Morgan asked, surprised, and sounding concerned.

Aubrey chuckled. "Well, I decided to truly fulfill my fantasy. I was always jealous of the big-chested girls. So, I took care of it, there on the island. Simple really, just an injection of their magical little nanites."

Theresa's expression changed to being interested. "How much did it cost? If you don't mind..."

"Just a few thousand. But, of course that's on top of the vacation itself," Aubrey replied honestly.

"Hmmm."

"Jess also got an injection and added a cup size." Aubrey added.

Jess blushed at the change of attention. "Only a little increase."

"You look great. Both of you," Morgan said, and her colleagues nodded their agreement.

Jess wasn't that sure that they were being totally honest. She knew from experience that the male of the species appreciated big breasts more than the average female. Even gay females. But Theresa sure seemed interested. Jess' imagination went to work picturing her with bigger breasts - nice.

Jess was shocked, and embarrassed when Aubrey made the big announcement.

"The best news, is that Jess is now one-hundred percent female."

She paused while she awaited their cheers, but all she saw was confusion. Disappointed, she explained in more detail. "She now has a very nice pussy."

"Oh..." Morgan said brightening. "No more cock, no more chastity cover?"

Quinn also reacted positively, happily, but Theresa had never been in on the secret, so she remained mystified.

Aubrey glanced at Jess as if she expected her to add something, but she was too embarrassed to speak.

"Yes, girls, Jess is all girl now, my stepsister, my lover, and soon to be my wife."

That announcement caused chaos. All three of their team members jumped up and ran around the table to congratulate the happy pair.

Jess quickly moved past the embarrassment over her new plumbing, and accepted the hugs and kisses, she received.

She jumped, and squeaked though, when during Morgan's hug, and more than friendly kiss, she felt the woman's hand squirm between her legs to fondle her pussy.

Morgan giggled. "Just checking. I'd love to see more."

"Um..."

"Perhaps, some other time."

"Perhaps."

After they'd fielded all the normal questions about when and where, Jess did her best to call the meeting to order. It took a while for everyone to calm down and settle in around the table.

The rest of the meeting, dedicated to business, went well. Apparently, their absence hadn't been missed, and Aubrey's millions were doing well - growing steadily now that all the expenses form the new house had been covered.

After all the boring details had been addressed, they all went out to lunch to celebrate. Just a bunch of rowdy girls partying over a 'working' lunch.

Aubrey and Jess came away feeling happy and content.

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

That night, while they were lounging naked in front of the television; they still did that often, having become comfortable with the practice during their first trip to Paradise Isle, Jess was lying with her head in Aubrey's lap, when she turned to look up, past her lover's large breasts. They were big, but also fun...

"Hey, when do you want to marry me?"

Aubrey giggled. "You in a hurry?"

"Absolutely. You know I've always dreamed of making you my wife."

"Hah, those dreams involved you as my husband."

"Well, yes," Jess muttered, hesitantly. She couldn't believe how much had changed. Man to woman. Stepbrother to stepsister. Lovers, not to mention rich.

"Now, you'll be my wife." Aubrey said as she pulled her up into a hug and a loving kiss. There was a little struggle there, as her boobs got in the way, but they managed.

They cuddled and kissed for quite a while, their hands roaming all over each other.

And soon their passion led their hands to their crotches, and they began thinking of sex, but Jess wanted an answer.

"So, when can we do it?" Jess asked again, clearly anxious to become a wife.

"Make love?" Aubrey giggled, playing with her. "Right now."

"I'll be happy to, but I was asking about our wedding, silly."

Abrey decided to get serious. She sat up straighter and leaned away. "I'd think in about three months, or so."

"That long? Why not next week?" Jess replied, surprised and disappointed.

"You're still thinking like someone with XY chromosomes," Aubrey said with a laugh. It was better than saying 'like a man.'

"Jess, my love, planning and arranging the most important day of our lives takes time. I want to do this right. Even though we'll marry and celebrate right here, with only a small ceremony, we need to plan it out so it'll be prefect. And our guests need to have the time to plan, also."

Jess had to think about it for a few minutes. She understood it was an important day for the both of them. But she'd never dreamed of wedding ceremonies. Guys never did anyway.

"Olay, I understand."

"Just think how gorgeous you'll look in a wedding gown." Aubrey said, excitedly.

"I'd rather think about how beautiful you'll look."

"Well, you have to remember that we'll be dressing for each other. I want to look lovely for you, and you need to look the same for me."

Jess had never thought about it that way. But it did make sense, especially when the wedding was between two women.

"In the meantime, we can go find ourselves matching wedding ring sets." Aubrey added. And that sounded like fun to both of them.

They kissed some more before Aubrey nudged Jess off and led her down the hall to their bedroom, where they made love once again. Only this time there was a bit more passion as both of them thought about becoming wives.

Afterwards, laying in each other's arms.

Jess retuned to thinking about getting married to the girl she adored.

"So, you're planning on having it here?"

"What?" Aubrey asked, chuckling.

"Um, our wedding!"

They both giggled. And kissed again.

"Of course. Here at the house, on the patio if it's nice. I don't expect it to be a big thing. Maybe a dozen of our friends.

"Unless you have a longer list. Old friends from up North, maybe?" Aubrey asked, working hard to act casual and maintain a straight face.

"You're kidding, right? I can't invite any of my old guy friends. Half would freak, and the other half would disown me."

"Kind of prejudiced?"

"Not really. Just straight, and with no clue about my fantasy. They don't know anything about my transition."

"You're awfully attractive. I bet they'd want to do you." Aubrey said, chuckling, sounding impish.

"Oh, ick," Jess replied, laughing and poking her in the ribs.

Aubrey squirmed and squeaked. "Hey, most girls love the feel of a cock, you know. Straight ones, anyway."

"Not this girl." Jess replied, disgusted by the thought.

Aubrey, accepted that. She hated the idea herself, but she wondered if Her lover might be missing out on a good feeling. Especially if the nanites were there to provide extra enjoyment.

"You're mine in any case," she said to confirm that fact. "So, we're just talking about people from around here; women you've met as a girl, along with a couple old friends of mine."

"Fine."

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

They did a lot of shopping over the next couple weeks. The house still needed a lot of decorating - too many empty walls and cabinets.

And Aubrey wanted to continue her efforts to rebuild her wardrobe with things that would fit and show off her new chest.

Jess needed some things too, as her larger breasts overstretched some of her dresses and tops. And Aubrey wanted her to show off more herself.

All-in-all it was a lot of fun. Each day they returned from their excursions tired, but excited by their purchases.

Slowly, Aubrey replaced a substantial part of her wardrobe, with outfits that delightfully showed off her new chest.

On occasion Jess would protest over some extremely low-cut dress. In response Aubrey would giggle and ask. "What would the old Jason, think?"

And Jess, would sadly and honestly admit that guy would have loved the look and gotten a hard-on.

She'd laugh and buy the thing, commenting something like, 'that's the idea.'

They also visited several jewelry stores until they found a matching pair of wedding rings, sets actually.

They were both, anxious to don engagement rings, with large diamonds. The matching bands themselves were pretty and feminine.

From that point on it was official. They would be wives.

Aubrey did all the wedding planning, while Jess watched from the sidelines. She had no idea of how to plan a wedding - it was a girl thing...

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

After their clothes shopping spree, they still had much to do to finish their home. A million little things. The house was actually too large. There was too much space that needed to be filled.

"We could leave those two extra guest rooms empty, you know." Jess suggested.

"I'm not sure why we wound up with four of them, but I don't want to just leave them empty to collect dust, or junk." Aubrey replied.

"Actually, I think Denver planned on turning them into play rooms," she added.

"Play rooms?" jess asked confused.

"Adult play rooms, silly.

"Orgy rooms. Perhaps even a dungeon."

"Oh. I can see her with a dungeon. At least now I can." Jess said, with a bit of fear in her voice.

Aubrey pulled her into a hug. "Yes, she's gone a bit crazy. But she has her slave girl partner now."

After a moment's thought, Jess muttered, "I hope she's happy."

"Me too.

"But in any case, we need to buy furniture for those two rooms. Nice bedroom suites. You never know when we might need them for sleep-overs."

Jess paused and looked at her, speculatively. "Did you have something in mind?"

Aubrey laughed. "You never know."

Jess didn't know how she felt about that. Of course, they had been a threesome when Denver was around. But there was a real relationship there and then.

 

When she thought about a bunch of pretty girls 'playing' together, she kind of liked the idea, but she didn't say anything. She was happy enough with sex with Aubrey.

Just a few minutes later, Aubrey chuckled.

"What?"

"We could set them up as play rooms. Nothing sinister, but I'm sure we could get creative. You've been awfully interested in sex lately. Making up for lost time?" Aubrey said laughing

"I was locked away for quite a while." Jess said defensively, while smiling.

"Your poor dick? Denver screwed you once in a while."

"That helped, but I wanted you. I always wanted you."

Aubrey's heart swelled and her eyes watered.

"But I understood your feelings about men. And I loved you so much."

"I'm sorry."

"Don't be. It all worked out, wonderfully." Jess wrapped her arms around her and kissed her long passionately.

It made Aubrey feel a lot better.

They wound up making love again.

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

When Aubrey was invited to attend a baby shower for an old friend, Jess begged off, not wanting to join in with a bunch of strangers, especially attending a party where she had no experience or knowledge of the goings-on at things like that.

Home alone for the first time in weeks, she relaxed for a while and then decided on a shower.

While enjoying the spray, she began exploring her new sex. She was certainly familiar with it by then, but she'd never gotten herself off before, at least not with a vagina. Jason, of course, had a lot of experience whacking off with his cock, but all of her orgasms to date, had come with participation from Aubrey.

Her fingers were experienced at getting Aubrey, and Denver off, so they knew what to do, and it didn't take them long to start her panting, and squirming, while she sat on the bench in the stall, with the nice warm water keeping her hot.

And when she came, it felt fantastic. Not as nice as when the love was delivered by Aubrey, but it still made her whole body shudder with pleasure.

And a few minutes later she gave herself another lovely orgasm.

How cool was that!

"A gal can get addicted to this!" she said out loud to no one.

+++++++++++

When they attended the next scheduled team meeting, Quinn was the first one to notice the rings, and after verifying that they were both wearing them, and that they matched, she excitedly pointed it out to the others.

Morgan and Theresa were as pleased as she was by the jewelry, and with all thoughts of business forgotten, the meeting became a party. The five of them abandoned the office and relocated to a nearby bar, where they drank away the afternoon.

At one point Morgan leaned in and whispered to Jess, "I'll give up all hope of making you mine. Now that you're officially Aubrey's."

Jeff, surprised, just chuckled. She knew that Morgan, and Quinn as well, had both harbored an attraction. But she thought it was just because she was so different - a unique conquest. But now she realized that Morgan had been seriously interested.

She liked her a lot. Although Morgan was several years older, she was a strong and intelligent woman, yet caring, almost motherly...

Eventually they called off their impromptu engagement party and called for Uber rides to their homes. Abandoning their cars in the office garage for pickup tomorrow.

A very happy Aubrey and Jess returned home and collapsed in the family room. They wound up spending the evening and night there, dozing, snacking and sleeping it off.

In the morning, only slightly hung-over, Jess drove Aubrey over to retrieve her car.

"We never did discuss the status of your investments, yesterday," she said as they were stopped at a light.

"Who cares. We had more important things to deal with," Aubrey replied laughing.

"True."

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

The following week, they went to ladies' night at the club.

Winona, the acknowledged queen of the lesbian community, had called and insisted, and Aubrey agreed they'd attend. It would be fun, and she could show off.

"How about we wear our latex traveling outfits?" Aubrey suggested when they started preparing on party night.

"No way! They show too much, and my corset is too uncomfortable."

"But we looked fabulous, and your tiny waist was fantastic."

"What's come over you? You've become such a slut." Jess declared, adding a chuckle to soften the complaint.

"Jess, my love. I'm just enjoying life. I'm rich, in love, and I have the tits I've always wanted."

Jess laughed, "those are your three life priorities?"

Aubrey laughed, too. "Pretty much."

They hugged and kissed, before Jess smiled sheepishly, "If you're happy, I'm happy. And I admit, I now have the breasts I've always wanted., and the body and face, and clothes, too."

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

Rather than take a ride-share, Aubrey decided to drive, promising not to consume too much alcohol during the party.

They dressed nicely, sexily, with Aubrey in one of her new dresses, that showed off her new chest. She had insisted that Jess dress as she always had, in the sexy and feminine things that Denver had always insisted upon.

Aubrey liked that tradition, and Jess secretly admitted that she enjoyed the sexy lingerie beneath her short and tight dresses.

Along the way, fighting through the traffic Jess asked, "Should we mention our engagement?"

"The first thing Winona, and everyone else will notice, silly, is our engagement rings," Aubrey replied happily.

"And then they'll notice your big boobs," Jess said with a laugh.

"Yup."

Traffic was terrible that night, some stupid protest blocking the streets, so they arrived late. The club was already packed. Lady's night was becoming more and more popular.

While they were unsuccessfully looking for somewhere to settle, Winona spotted them. She was, as always wandering the room, visiting, performing her duties as the communities' leader.

She made her way over and greeted them with "welcome back! Was the island as wonderful as I've heard?" she asked as she hugged and kissed Aubrey.

"We had a great time."

Jess was uncomfortable when Winona grabbed her and pulled her into a hug, and gave he a kiss, on the lips. Surprised, Jess kissed her back.

After releasing her hold on Jess, Winona turned back to Aubrey and looked pointedly at her chest. "And what did you do?"

Aubrey giggled. "I went all bimbo boobs. It seemed like a good idea at the time. And I'm loving it."

"You do look spectacular. You're far too intelligent to go all Barbie bimbo, though." Then she laughed and wrapped her arms around Aubrey; and she kissed her like she had Jess.

When she broke off, she reached up to cop a feel. "You're gorgeous. I love 'em."

Aubrey laughed. "Thanks. I do too."

It was then that Winona, giving them one more examination, that she noticed the ring. First on Aubrey, then on Jess, and she reacted just as predicted.

Gushing happily, she initiated another round of hugs and kisses. Aubrey and Jess laughed and accepted the very friendly congratulations.

For a couple more minutes they talked about dates and plans, and Aubrey assured her that of course, she would be invited. Winona was very pleased about that.

"Now, I'm even happier you two came tonight," she said happily, before preparing to wander off.

But Aubrey stopped her. "We were looking for a couple of available chairs, but no luck." she complained.

Winona nodded and glanced around. "Well, the place is packed, but I do know where there are a couple of openings."

Aubrey sensed a bit of mischief in the way Winona delivered the news.

Jess, not knowing the woman well enough, missed it. "Where, we'll head right over and grab them. My feet are already killing me."

With a barely suppressed giggle, Winona pointed to a distant, back corner, where Jess could barely make out a big round, banquet table.

"There are two openings at the 'tail table'. Aubrey, you know a couple of those girls, don't you?"

Hesitantly Aubrey answered. "I do, but I'm not a fan of their games."

"What games?" Jess asked, curiously.

Winona though ignored her, and giggling happily pulled Aubrey over in that direction.

As she pulled them along Winona chuckled. "I understand Jess might really get a thrill out of it."

"Where did you hear that?" Aubrey asked, dismayed.

"Oh, I think Denver mentioned it some time ago, right after you three returned from the island. You know how devilish she can be."

Jess, following behind, only heard bits and pieces of their talking, and grew worried when she heard Denver's name. But she couldn't really make out anything more.

As they drew closer to the big table, Jess saw that there were indeed two empty chairs, with the other eight occupied by an assortment of women, all chatting, drinking and enjoying themselves.

For a moment she wondered why there was room there, with everything else packed. She couldn't see anything to explain why those seats were still available. Odd...

Winona stepped right up and spoke loud enough to attract the table's attention. "Girls this is Aubrey and Jess, they can't find seats anywhere, so I suggested they join your little group, even though they don't comply with your ground rules.

"I assume you can help them out and take care of them. Right?" Winona said happily as she scanned the seated collection of women.

Several of the women replied, 'yes', and then began introducing themselves and the other women at the table. Of course, the names came too fast for Aubrey and Jess to record them, but no matter, everyone was welcoming and pleasant.

Jess was surprised when a couple of them called out greetings to Aubrey. They must already know her. One of them added sympathetic condolences for Denver's departure, and then welcomed Jess to their group.

The woman sitting closest, Paula, grabbed Aubrey's hand. "Aubrey and Jess, I'm not sure if you understand our game, but in case you're not aware, all of us enjoy being tailed." And she giggled.

"That's why this is called the 'tailed table'," Winona inserted.

Jess looked from one to the other, confused.

Paula then stood up, turned and lifted her skirt to flash them, and Jess could see that she had a racoon tail hanging from her ass. She realized, stunned, that it must have been mounted on a butt plug in her butt hole!

Standing there giggling she swayed her hips making her tail swish back-and forth suggestively.

"Please join us. You'll have fun, I promise." Paula finished, as she sat back down, arranging her tail as she did so.

"We all love it." Someone else at the table said, pleasantly.

Winona had been standing there, behind them as they listened to the girls' sales pitch. "Oh, relax you two. Go with it, I'm pretty sure you'll enjoy the experience."

With a giggle, she gently ushered them forward. Then she leaned in close to Jess' ear and whispered, "And since you have a pussy now, you don't have to be worried about any of these lovely gay women flipping out over what's beneath your dress."

Jess, freaked! She tried to turn but Winona held her in place. How did she know? How much did she know?

Aubrey noticed and turned her head to look at the two of them, questioningly.

Winona laughed and spoke just loud enough for both of them to hear. "I spoke to Denver yesterday. She filled me in about you, and her new pet. They may stop by later."

Aubrey moaned, quietly. "Yes, we bumped into them on Paradise Isle.

"So, you know everything?" she then asked quietly.

"I think so," Winona said pleasantly, but then her expression changed, became darker. "Jess dear, you need to be careful around her, I got the impression that she still blames you for her split from Aubrey. And she's not at all happy about that."

"It wasn't Jess' fault," Aubrey protested.

"I understand. I'm just making an observation."

Then she wrapped her arms around the two of them. giving each kisses on the cheek. "Now, please just relax and enjoy the tailed table. There's really nothing else you can do. Nowhere else you can sit."

Jess wasn't sure if that was an order, or just a friendly suggestion. She didn't want anything like that plug up her ass, or an attention-grabbing tail dangling and signaling to the world that she was plugged.

Aubrey shook her head resignedly and smiled weakly, but agreed. "Okay, we'll join you, but we don't have tail plugs."

Kendra jumped up from her chair in the back corner. "That's no problem. We're always ready to initiate new members to our little club.

"Olivia always brings spares, and lube, just in case someone new comes along."

Aubrey, caught Jess' eye, and shrugged, as if to say, 'I tried'. Jess groaned quietly and shook her head, sadly.

Olivia stood up and displayed a big purse. "Come along girls we'll get you outfitted, then you can grab your chairs and we can all get back to the party."

As she turned Jess caught sight of a long fuzzy fox tail dangling from beneath her short skirt. It did look sexy and it was clear to her, and she was certain everyone else, that the woman had a plug up her ass to hold the thing; one large enough to keep it in place as she moved around.

"You'll really enjoy sitting on your tails. We all do," one of the other girls said, giggling, and wiggling her ass on the hard chair beneath her.

Olivia waved Aubrey over. Jess breathed a sigh of relief, not wanting to be the first.

Aubrey looked around. "In the ladies room?"

"No need," Kendra replied. "I'll take care of you. Just slide around back here, in the corner, and bend over my chairback."

"Really?" Aubrey protested.

Kendra laughed, grabbed her arm, and pulled her in the required direction. Aubrey moved hesitantly. Thinking, I'm not that big an exhibitionist...

"Relax Aubrey, that's why we're in this back corner. It's private and no one can see your behind."

Jess stood there appalled, watching as Aubrey was gently moved around and positioned, her butt facing the back wall.

Aubrey was calmed a little when a couple of the other women stood up to help block the view as she was bent over, behind the chair, facing the room.

The party was in full swing, and it did seem like nobody was paying them any undue attention.

She rested her arms and her chest on the chair as Olivia and Kendra lifted her skirt.

"Oh, panties, what a waste. You won't need these anymore." Kendra said with a laugh. She stripped them down Aubrey's legs and tossed them aside.

Olivia had meanwhile dug into her bag and pulled on a surgical glove and opened a tube of lubricant.

Aubrey squealed when she felt the goop being applied outside and inside her ass.

"Have you been plugged before? Tell me this isn't anything new for you."

"It's not. I've played at anal before," Aubrey admitted.

"But you haven't been tailed before?"

"No."

"You'll love it. The feel of your soft fuzzy tail tickling the backs of your thighs is amazing." One of the girls said encouragingly.

Jess stood with Winona quietly terrified, knowing she'd be next. She might have run, if she weren't blocked by the queen.

Seemingly understanding, Winona wrapped an arm around Jess' waist from behind and gave her a kiss on the neck. "These girls love it; they'll make sure you have a good time. Just be a good, new girl and go with it."

"Have you ever tried it?" Jess grumbled.

"As a matter of fact, I have. And I did enjoy it. Sometimes I join this table."

"Oh."

Aubrey grunted as she felt the plug being pushed up her rear. It seemed huge, probably had to be to hold the tail inside. The ones at home, that she and Denver had played with had been small in comparison and easily inserted.

Kendra ran a hand up and down her back calmingly as Olivia slowly worked the thing deeper and deeper. Finally, the head slipped in and the plug hit bottom.

She was able to breathe a sigh of relief. She had a tail.

Just then she felt a hand reach between her legs to tickle her pussy. She jumped and squirmed. Olivia had slipped her hand all the way down!

"Feels nice, eh?" she whispered in Aubrey's ear, while giggling.

Aubrey, grunted, and swiped the arm away.

"Part of the service, my dear," Olivia said chuckling as she stepped away. But she gave the tail a gentle tug, drawing one more groan from Aubrey.

She stood up and waddled slightly as she stepped away. Several of the others congratulated her and complimented her on her pretty new appendage as she made her way toward one of the empty chairs.

AS she moved, the thing in her ass moved as well., and she was a bit surprised that with every step it felt less intrusive, and more agreeable.

Then it was Jess' turn.

All of the girls turned to her, and Winona gave her a little push toward the corner.

"I'll leave you girls to it, then, see you later," she said pleasantly as she turned and walked out into the crowd, her good deed done.

Jess allowed herself to be passed around and into the corner where the procedure would take place. She knew she should have refused, but with everyone there ganging up on her, and Aubrey already tailed, she just couldn't fight it. Maybe it would be okay.

With Jess in position, Olivia took charge and pushed her down to lean over the chairback, just like Aubrey had.

It was Kendra this time who slipped on a glove and reached for the lube. She'd take her turn at inserting.

When Kendra lifted Jess's skirt, she paused and whistled.

"Wow, Jess, you're a sexy little thing. Stockings and garters, girls," she announced. Jess blushed redder than she already was, if that was possible.

"You need to lose those panties too, my dear. At least you wear them properly, outside your garters."

"Easier access," one of the others giggled.

"Slut," another girl laughed.

"Hey, she's my lover," Aubrey protested on her behalf, and the other girls all laughed.

Jess glanced over to see Aubrey sitting gingerly on one of the chairs, across the table. She was smiling encouragingly at her.

Forced to step out of her panties, Jess stood for a moment, before she felt the cool jelly being smeared around her ass hole. She squirmed and moaned, and reached back toward her behind, but one of the girls leaned in and pushed her hand away.

"We don't need any help, my dear. We've got this." Olivia said, happily.

Kendra, then shifted to pushing a finger into Jess's hole, making her squeal.

"Awfully tight, Jess. Is this your first time?"

"No," she muttered through clenched teeth.

"Oh? Are you sure? How often? How many times?"

When she didn't answer. Kendra pushed in a second finger, making Jess squirm and groan.

"More than, just a little test?"

"No." Jess whispered.

Kendra giggled. "Well, no wonder. I'll be gentler then."

Olivia then spoke up. "I'll dig out the special tail for poor Jess, here."

"Really? She's an anal virgin?" somebody asked loudly. Olivia turned to Aubrey for confirmation.

Aubrey shrugged. "I tried to teach her, but she doesn't like the idea."

Jess grunted, and squirmed, not appreciating the fingers up her ass, nor the discussion going on around her.

Despite being terribly distracted, Jess heard Aubrey ask, "special tail?"

One of the others replied. "Virgins get a long, beautifully full, white and fluffy tail. It's theirs to keep as a memento."

Aubrey tried to come to her defense. "Well, she's not a full virgin. She has tried it."

Olvia chuckled. "Not good enough. By our standards she's still virginal."

Someone else at the table called out "I second the motion!"

Jess heard several others vote their agreement. She just closed her eyes and blushed furiously.

A minute later she groaned, again. But a moment later she was shocked to realize that instead of pain, she was now sensing a stirring. A pleasant feeling in her belly, and pussy. It felt surprisingly good.

Unbelievable.

When Kendra removed her fingers, Jess was again flabbergasted by the empty feeling, but then she felt the head of the plug begin pushing at her asshole and she returned to being pained and disgusted.

 

All the while, Aubrey sat watching the changing emotions on her lover's face. Initially she was worried by the anguish she observed, but then she saw surprise and then slowly, signs of pleasure. She almost laughed out loud. Jess was actually learning to enjoy being buggered!

Jess groaned and shivered as Kendra pushed and pumped the plug into her. It felt huge and it hurt! Nothing that big had ever been inserted there before. The thin dildos and vibrators that Aubrey had introduced her to had slid in easily. Her body now resisted the intrusion of the much larger plug.

While Kendra pushed, Olivia leaned over onto her and began nibbling at her pointy ear, whispering encouragement. It tickled and her warm breath felt nice. Jess was distracted for a moment. "You'll love this," Olivia muttered. "Relax, and enjoy the penetration. It may not be as nice as in your pussy, but you can get off on it. Believe me."

Jess didn't actually believe her, until it really did start to feel tingly pleasant in her crotch, up her belly and even in her pussy, like it had back when Aubrey had persuaded her to try the toys, way back when.

Jess was confused by the pleasure until in a moment of clarity she remembered the nanites were probably doing their thing, enhancing the pleasure from anal sex.

She was still struggling with the idea of enjoying anal sex, when she suddenly felt the giant head of the damned plug slip past her sphincter, and fully up into her behind.

The base pushed against her stretched and sore hole, and she thought she felt the fuzzy tail tickling her butt and thighs.

"Oh, God!" she moaned.

Kendra giggled. "Good, eh?"

Jess didn't answer; she was too busy trying to come to terms with the mix of pleasure and pain, the full feeling in her ass, and humiliation of being plugged and tailed.

Suddenly, she felt Kendra shift behind her and then give her resounding slap on the ass. Jess screeched, and tried to stand but the woman leaned onto her back and held her down. Then she reached around and poked a finger into her pussy!

"Reward," She whispered as she laughed. Kendra then pinched her clit, before removing her hand and moving up and away.

It was Olivia who helped Jess stand, holding her and helping her calm down.

All the girls cheered and applauded, drawing the attention of the women at surrounding tables.

Jess kept her head bowed, terribly embarrassed.

She reached back to pull her skirt back into place, and in the process felt her furry tail hanging down beneath the hem of her dress.

Of course, she was also feeling the huge rubber thing embedded in her ass.

Kendra made it even worse, by grabbing her shoulders and surprising her by spinning her around so everyone could see the virginal white tail hanging down almost to the floor between her legs.

The girls at the table cheered again, and called out their congratulations.

Jess was totally mortified, but there was still a sexual tingling emanating from her ass into her pussy and up her body.

For a moment she was terrified that the feeling might bloom into an honest-to-God orgasm. How humiliating would that be? Hell no!

Trying to gain some control, and hide, she shuffled around the table, accepting the pats and hugs of a couple other tailed girls, but hurrying along until she came to Aubrey and the empty chair next to her.

Aubrey stood to hug her and kiss her, and Jess paused to enjoy her lover, but only for a moment. Then she broke away, pulled out her chair and collapsed onto it.

And she immediately squealed as she felt her tail bend beneath her and the plug pushed deeper into her behind!

"I tried to warn you," Aubrey said as she grabbed her shoulders and prevented her from jumping back up to her feet. "Just sit. You'll get used to it.," she said soothingly.

Jess realized she'd already made enough of a scene, and didn't want any more humiliation, so she gritted her teeth, groaned, and tried to settle and get comfortable.

It took her a while, but with Aubrey's gentle encouragement she learned to accept the feelings.

Slowly the party resumed around them. The other girls resumed their chatter, sipped their drinks and eventually they all ordered food.

After she'd gotten used to the plug, as much as she could, Jess reached around to arrange her tail more comfortably beneath her and then pulled it around to take a look. It was long enough for her to get a good look at the bottom half. It was indeed white, and furry-fluffy. On a big dog it would have been lovely. Hanging from her ass, not so much.

But she couldn't shake the pleasurable feelings the nanites were forcing upon her - at least she blamed it on them. Every time she moved or shifted on the chair the plug gave her little electric shocks, that continued to remind her of the feelings she'd enjoyed when Aubrey screwed her behind with a dildo.

She had to stop herself from admitting that the thing in her ass was pleasurable.

Jess and Aubrey sat with the group for the rest of the evening. The other tailed girls were interesting, entertaining and friendly, and despite their kink, fun.

When the band started playing and the dance floor began to fill, several of the women paired up and headed for the dance floor, their tails swaying gracefully and attractively behind them.

Heather, one of the women who had already known Aubrey dragged her off to the floor, and Jess watched intrigued by the sight of her lover's cute tail moving along. She did look sexy, and alluring and Jess found herself aroused and wanting her, soon.

The plug in her ass, was making her even hornier.

A couple minutes later Kendra returned from the dance floor, but instead of heading for her chair, she stepped over and, grabbed Jess' hand. "Come dance with me Jess."

Jess tried to decline the invitation, but Kendra refused to be put off. And just as before, her strength won out. She dragged Jess to her feet, and then pulled her into her hip, to stand side-by-side. Then she reached around behind and grabbed the white tail where it showed just beneath her skirt.

"These things make great leashes too," she muttered into Jess' ear, as she gave a gentle tug, that jerked the plug in her ass. It sent a tingle up her spine that took her breath away. Damn she was horny!

Maintaining her grip, Kendra maneuvered Jess out onto the floor. There she finally released her hold and grabbed Jess' hands.

Smiling she began dancing, encouraging Jess to join in. She did her best.

As Jess moved to the music's rhythm she felt the tail brushing against her legs, and the plug moving inside her ass, and it excited her even more. She again tried to blame it on the nanites, but she wasn't quite certain any more if it was the little robots, or her own body on its own.

Kendra kept her on the floor, for a second and then a third song. Twice she refused when someone tried to cut in.

Jess had never enjoyed dancing and she knew she wasn't very good at it. Aubrey and Denver had made her practice and she was now reasonably adequate at it. She moved enough like a girl to at least be acceptable.

Now, as she danced the plug in her ass kept her aroused, and the tail tickled her thighs and legs. And she even began to enjoy the dancing.

A couple of times someone in the crowd surreptitiously grabbed her tail and gave it a tug, making her jump and squeal. It always surprised her and hurt a bit, and ruined her excitement.

When the band switched to a slow song, Kendra wrapped her arms around her and after a while she leaned in and kissed her. Jess was surprised, but she kissed her back. Kendra chuckled happily, and pulled her closer, tighter. "I like your ears too. They're permanent, aren't they?" she asked.

"Yes, Aubrey likes them."

Kendra giggled. "I understand. They look so cute on you. Just like your tail. They go well together. You should wear your tail all the time."

Jess shook her head. No way! "Do you wear your tail all the time?" she challenged, cattily.

"As a matter of fact, I do. I have a much shorter one that I wear beneath my clothes. It doesn't show below any of my skirts. It keeps me excited. I enjoy the feelings."

Jess was surprised. Kandra hadn't seemed that kinky. She couldn't imagine wearing a plug all the time, especially one with a tail, even a small one, dangling constantly from her ass.

She remembered seeing ponygirls and reindeer with tails, permanently attached to their tailbones on the island, but those girls were in-way too-deep, fetish freaks.

She did know that a lot of women enjoyed having their asses filled with plugs of various sizes, but still...

Of course, here she was, wearing a plug and a tail for several hours now. And enjoying it. But only because of the nanites.

After that dance, Kendra finally returned her to her chair, where once again she forgot her plug and sat down, poking herself in the ass.

Aubrey noticed and laughed. "You have to remember that thing is back there."

The girl sitting on the other side of Jess, laughed. "She'll get used to it, the more she wears her pretty tail.

"You two just need more practice."

Then she turned to the table and rose her voice. "Ladies. Don't you think Aubrey and Jess need to join us here next girl's night?"

'Absolutely,' was the unanimous consensus.

"You two fit right in, and you look lovely in your tails. I'll make sure Winona knows that you're part of the tailed table from now on."

"And that will make it official," Kendra added, happily.

When Aubrey tried to graciously refuse the 'invitation'. She was voted down by the whole crew.

"And I'll pick out another tail for you Jess. You won't need to wear the white one next time." Olivia added.

"She does look lovely with that one, though," someone said.

Olivis nodded and smiled. "Keep your tails. They're yours, our gift."

"Wear them home. You'll find them delightful, especially if you take bumpy roads," another girl said, giggling.

Aubrey glanced over at Jess and shrugged. She'd tried. She wasn't sure if she liked the deal. She had enjoyed the night with the tailed group. They were fun, and none of them were mean or unattractive.

And she hadn't even minded the plug and tail that much. The plug had kept her happily entertained, and she was anxious to get home and make love to Jess. She might even keep the thing in place for the session.

Slowly, after that had been settled, the girls of the tailed table began departing for home. Aubrey watched as the pairs sauntered out, tails swaying behind them, as if it was a natural thing. Perhaps it was.

She wanted to leave as well, but just as she was starting to stand, Winona stopped by on her final rounds before heading out herself.

And of course, the remaining girls made it clear that Aubrey and Jess were now part of their little group, and that they'd be back for the next party, with their tails.

Again, Aubrey tried to back out, and again her attempt was squashed, so Winona went along and congratulated them on their new commitment.

Aubrey planned on calling Winona later, to talk her way out of it.

Finally, around two in the morning the pair made their way out the door, tails waving.

Getting into Aubrey's car was an adventure for both of them. They each groaned as the plugs pushed inside even more uncomfortably on the soft cushions. And that started both of them laugh at themselves.

They didn't talk much on the ride home. Aubrey had to concentrate on her driving. It was late, they were tired and tipsy from the alcohol they'd consumed.

"I sure as hell don't want to get pulled over with a tail hanging out of my ass," she said as she pulled out of the parking lot.

"Me either," Jess agreed. "We could stop somewhere and take them out."

"And then what? They'd be messy. And we don't have any underwear."

"Oh, yah, right."

During the drive, they did feel every bump, like they'd been warned.

As humiliated and uncomfortable as Jess was, she couldn't deny that the damn thing in her ass continued to turn her on, all the way home. And the potholes they hit were actually thrilling.

Arriving safe and sound, Aubrey turned off the ignition after pushing the button to close the garage door.

When she slid out of the car, Jess was shocked when she lost all control, and staggered under a surprise orgasm. She lost her balance and had to hold onto the car door with one hand while she held her pussy with the other,

Her groans drew Aubrey's attention, and she quickly figured out what was happening.

"You dirty slut!" she screamed, laughing.

Jess ignored her, as she was too wrapped up in her sexual feelings.

After she'd caught her breath and was able to stand rather than stagger, she groaned. "I couldn't help it. The nanites."

"Yah, right," Aubrey replied with a derisive laugh. "Come on in, and make it up to me. I'm horny too.

"And you can sure as shit keep that tail in place.

"In fact, you'll wear it until morning for surrendering to the thing and being such a slut." She laughed, but she meant it, too.

Jess moaned, sadly, but didn't argue.

Aubrey grabbed her hand and led her straight toward their bedroom.

After they had both used the toilet, careful not to dip their tails, they crawled into bed, and into each other's arms.

As they moved, and depending on their positions their tails tickled, poked and thrilled them. Aubrey was entertained by the feelings and the game, while Jess was at times pleased, and at other moments, uncomfortable and frustrated.

Both of them though, orgasmed happily, before swiftly drifting off to sleep.

And neither of them removed their pretty tails.

In the morning, Jess' ass was irritated and sore, and she was happy to remove the thing to relieve herself before showering.

While Jess was in the stall, Aubrey took the time to wash the two plugs before she brushed them out and then stashed them away in a drawer.

"We'll need them for the next Girl's Night," she explained as she joined her lover under the warm spray. They adored showering together. It often led to wonderful and wet sex.

Jess hugged her but mumbled, "no thanks."

"Oh, come now. You know you loved it." She paused to giggle. "Hell, you came, standing in the garage!"

Jess blushed, embarrassed.

"And don't you dare blame the nanites. It wasn't them. It was you.

"So, we will go to the next party, and sit at the tailed table."

It was only after voicing that commitment, that Aubrey realized that she'd made it, and that she too had enjoyed the experience.

She wouldn't be calling Winona and begging off, after all.

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.

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Rate the story «Paradise Isle, StepSister Pt. 08»

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