Paradise Isle, StepSister Pt. 02

Paradise Isle, StepSister Pt 02

(Cross-dressing, TF, lesbian, reluctant, fetish) Loving Roommates

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 part of StepSister, first.

Aubrey called a rideshare service to take them to the club, and the Lady's night party. All three of them squeezed cozily into the car's back seat, and the guy took off.

Of course, Jess sat in the middle, and as soon as the driver hit the road, she felt a hand from each of her girlfriends, resting on her thighs, and then sliding up under her skirt to caress the exposed skin, above her stocking tops.

When she tried to push them away, Aubrey and Denver resisted, and just giggled.

Jess's cock tried to grow, but it was held tight and squeezed between her thighs. It hurt! And it got worse, when Denver began massaging one thigh, while Aubrey, giggling tickled the other one. The more she reacted, the more the other two giggled, and drew the attention of the driver, who kept trying to see what was going on, via his rear-view mirror.

Jess worried about an accident. Winding up in an emergency room with no ID and in drag. A nightmare.

With Saturday night traffic, it took almost an hour to get to the club, and the place was crowded. It seemed that every lesbian, or would be lesbian in town was there. Most were dressed for clubbing, while a few looked to Jeff sort of rough and dykey.

And it seemed like every girl there busily checked out every other girl there. Jess had hoped she'd just be an insignificant member of the crowd, but there was no hiding.

As they walked through the mob, Aubrey and Denver both whispered encouragements. Jess scanned the women they passed, but didn't make any eye contact. She was just too frightened.

Eventually, relieved, they found their way to an empty table and slid into the seats.

"Damn. This is cold on my bare ass," Aubrey exclaimed as she sat down, and her skirt rose up.

Jess couldn't help but laugh.

Denver saw it as a good sign. Jess was starting to loosen up, at least a little. Aubrey reached over to hold Jess' hand, and that helped her too.

Slowly Jess began sitting up, and looking around. She quickly realized that no one was paying her any particular attention. And then she began admiring all the women around her. Some sitting drinking and eating. Others dancing, and many of them just watching like she was doing.

About every fifth girl she saw was attractive, if not beautiful. Even a larger percentage were prettily or sexily dressed.

The more she looked, the more uncomfortable she became as her cock was trying to get hard, and tucked as it was, that was impossible, not to mention painful.

A waitress came by, looking for drink orders, and Denver requested glasses of Chablis for all three of them. Jason wasn't a wine drinker, but apparently Jess was.

The three of them sat there, simply drinking, chatting and ogling for almost an hour before a woman came over and greeted Denver and Aubrey as an old friend would.

Aubrey immediately jumped up. "Winona! Haven't seen you in forever." The two of them hugged and kissed, affectionately.

Jess looked over at Denver, who smiled and nodded. She apparently knew and understood.

Jess took a better look at the woman. She was decidedly older, but well preserved, and nicely dressed.

Finishing with their affectionate greeting Aubrey introduced Denver, who Winona had apparently met before. The two of them hugged and kissed. First friendly-like on the cheek, but then Winona wrapped a hand behind Denver's head and held her for a kiss on the mouth. Jess could see that Denver was surprised, but after only a moment she kissed the woman back.

A minute later she broke it off with a chuckle. "I do like you, Denver. You and Aubrey make such a great couple." She muttered, as she stepped away.

And then Aubrey directed her friend to Jess. "This is my step-sister, Jess, she's just moved down here to join us."

Winona stepped over and as Jess stood up, they hugged and kissed on the cheek. Jess was relieved when the woman didn't do anything more.

Introductions over, Winona settled into the empty chair at their table, and made herself comfortable.

"Jess. You seem nervous. Relax, we're all friends here," Winona said, and she reached over to rest her hand on top of Jess'.

"Oh, she's still trying to get used to her new environment," Aubrey replied, off-handedly.

Denver laughed, and was tempted to explain how different Jess' new environment was, but she knew that would ruin everything.

Jess blushed when Winona squeezed her hand affectionately. "You'll be happy with this pair, I'm sure. And if you're looking for a lover, I'd be happy to show you around. There are plenty of girls here who would be happy to hook-up."

Jeff, sputtered a thanks, and was relieved when Aubrey came to his rescue.

"Oh, she's with us. We make a happy threesome, don't we Jess?"

That he could answer, truthfully. "Yes, we do. I love them."

"That's good."

"Winona's the unofficial leader of our gay community. Our Queen." Aubrey explained, happily.

"I prefer 'princess', it makes me sound younger," Winona said, laughing.

Jess got nervous when Winona turned to her, shifting her grip to actually hold hands.

Then she surprised all three of them. "You do look good, Jess dear, but not good enough. I have no problem with trans gurls joining our parties." She then turned to look pointedly at Aubrey, and then Denver before continuing. "But she needs much more practice before she can fit in, comfortably amongst us."

Then she turned back to Jess. "I think you've got potential, but work more on your feminine side and I'll see you at our next get together, two months from now, agreed?"

"Um, yes." Jess replied, hesitantly.

"Yes, what?"

"I'll practice."

"And?"

"I'll see you in two months?"

"Definitely."

Then Winona looked again at Aubrey, who smiled and nodded. Denver laughed, delightedly, thinking, 'this will be fun.'

Standing up, Winona pulled Jess to her feet, as well. "Stand up and let me get a better look at you." she said, taking a step back, but still holding hands.

"She does look pretty good. Nice shape and pretty legs," she said glancing down at Aubrey and Denver who were watching intently.

Jess, blushed, again, embarrassed by the examination.

"I think you'll do, Jess dear.

"You can sit back down. I have to move along," and she finally released her hand.

"I'll see you all again at the next party," she called over her shoulder. as she walked away.

Jess sat down, only just remembering to smooth her skirt as she did. Then she breathed a huge sigh of relief.

Denver giggled. "You passed Winona's test. Congratulations."

"I'm proud of you, sis." Aubrey told him, happily.

He smiled weakly and nodded.

The rest of the night was relatively uneventful. Several times other women, or couples stopped by to say 'hi', and none of them gave any impression that they suspected that Jess wasn't just another girl.

One single visitor actually tried to pick Jess up, inviting her to accompany her home. The girl was pretty and friendly, but Jess declined, certain that the woman wouldn't be all that impressed by the cock stuffed back between her legs.

Denver got a huge laugh out of the situation. She wanted video...

It was late when Aubrey suggested they head for home. Jess was ready, she'd had enough, but Denver wanted to stick around for more fun. She'd been harassing Jeff to join her on the dance floor all evening, but she had refused.

"I can't dance, especially in heels and a dress." She repeated over and over again.

Finally, frustrated, Denver gave her a threatening look. "We'll fix that before the next party."

Jess didn't like the thought of that.

Making their way out of the place, around two AM, was one final ordeal. Aubrey and Denver stopped several times to chat for a moment with more women they knew, and introduce their 'sister', Jess.

Each time she was afraid of discovery, especially with all the hugging and kissing, and on one occasion ass pinching from some drunk and horny girl.

But they left the place with nothing other than good wishes.

In the Uber car, on the way home, Aubrey, giggling, harassed her new sister. "So, you now have a commitment with Winona for the next party. We'll have to make sure you're ready for it."

"Forget it."

"Oh, now sis, you don't want to disappoint her."

"This was a one-time thing." She replied stubbornly.

"Oh, come on. I think you had fun. It'll be even more fun next time."

Denver giggled. "I think a proper manicure is in order, and higher heels to make your legs and ass look better. And we need to get you dancing."

"Admit it. You enjoyed the company, tonight." Aubrey insisted, now getting more serious. She wrapped an arm around her and gave her an encouraging kiss on the cheek.

Jess almost lied and said no, but instead he sighed resignedly, and mumbled. "yes". He must have been the alcohol talking, he told himself.

Aubrey chuckled and kissed him again. "I knew it."

"But I'm not gay!" he protested, to make that point perfectly clear.

"I know!" Denver said, happily, and she ran her hand along his nylon-covered thigh, making him shiver.

++++++++++

They arrived at their front door around three in the morning. What a night!

"You make a wonderful girlfriend. I do like you better this way, as Jess, than as Aubrey's brilliant yet grubby brother Jason." Denver said giggling and slurring, as they stumbled inside. She then pulled him into a hug and gave him a passionate, toe-curling kiss on the mouth.

When she backed away, he was breathless, and pleased. She winked at him, patted his flat crotch, and then turned to Aubrey.

"He's not 'grubby', but I have to admit, I like Jess, too." Aubrey confessed before Denver grabbed her, and the two of them hugged and kissed, lovingly, as he stood there watching and trying to analyze their admitted feelings for Jess.

Finishing their kiss, Denver simply twirled, staggered a bit, and then went off to her and Aubrey's bedroom.

"What was that?" he asked Aubrey. Denver had never kissed him, especially like that before, and it had shocked him - even sobered him up a bit.

She chuckled, understanding his confusion. "She likes you as a guy, and I know she likes to use your cock on occasion. But clearly, she adores you as a girl."

"I guess so," he muttered.

"I like you as a girl too, by the way. It was fun tonight, wasn't it?"

When he blushed rather than answer, she asked again. "Wasn't it?

"Don't try and tell me you didn't have a good time. I could see that you wound up enjoying yourself."

She then took her turn to kiss him, and it was far from a sisterly kiss.

He loved it, a lot. So, when she broke it off, he admitted, "yes, I did."

"Well, then..." she said as she walked into the kitchen. Mumbling about a need for a Coke. He remembered that was her personal solution to combatting hangovers.

He stood still for a moment wondering. Would it be all that bad? Could he actually live with them as Jess? It sure seemed like they would prefer things that way. The crazy idea was both frightening and exciting. It brought back some old memories...

After a moment he followed her, appreciating how very drunk he was, himself. He also realized that he was still dressed as Jess, and it didn't bother him.

"You still believe in Coke to alleviate hangovers?" he asked as he joined her, collapsing into a chair at the little table. It occurred to him that he hadn't smoothed his skirt before he sat. Bad girl...

She took a big sip from the can. "Yes, it's got sugar and water, things the body needs to offset the alcohol."

"Sure, if you say so," he replied skeptically.

Aubrey took a big drink from the can, and then belched, making both of them laugh.

"So, tell me sis, "she paused to giggle. "What would YOU do with all of the money?" she asked. "We've already covered what I'd like to do, over and over. And we're working on those things; thank you very much.

"I want to hear what you've always dreamed of."

It was true, they'd never discussed that before. All of the focus had been on what she wanted, or she and Denver. She was the big winner, after all.

Of course, he had thought about it. Fantasized about what he'd want, but he'd never said anything. He wasn't about to ask her for some donation to satisfy his own dreams. She was already paying him big bucks for his help.

"I, um..."

She frowned at him. "Come on, tell me. And I want the truth. Don't you dare just echo what I've been talking about."

He chuckled. "I'm sorry but a lot of it would be the same.

"A nice big house, here. A place in Europe, not Paris though, probably Amsterdam. A Porsche."

"Boring!" she said, giggling. "What specifically for you. For Jason. I already told you that I wanted bigger boobs." And she laughed again, drunkenly.

"And Denver wants a nose job."

"Really?"

"Yes, it's always bothered her."

"It's not that bad. She's beautiful," he gushed.

"Not to her.

"But forget that. Think and be perfectly honest. What have you always dreamed of, for YOU."

He sat there for a while, and she waited patiently.

The first thing that occurred to him was that he was too drunk for this conversation.

But as he sat there quietly, alone with her, it struck him that he loved her so very much. He always had. When they were younger it just didn't seem right. And he wasn't her type.

And now that he knew about her dislike for guys, and why, he knew he couldn't have her.

And then it occurred to his muddled mind the other aspect that, back then, he had always envied, and been fascinated by.

She was still waiting, looking as good as ever, so he took a deep breath and overriding all of his fears, and misgivings, confessed.

"Okay, okay, but you have to swear, never to mention this ever again, to anyone. And I never thought I'd ever tell you."

She stared at him, now more curious than ever. And he could also see the love there. Damn she was wonderful!

He sighed and sat back, trying to work up the courage to continue.

Realizing that he was serious, she focused on him, pushed aside the alcohol daze, and looked him in the eye. "I swear to keep your secret."

"Good," he mumbled. But still, he didn't speak up.

She grew impatient, waiting. "Well?"

He took a deep breath, "Um, well, I've always dreamed of being with you and like you."

"Huh?"

Damn! he hadn't meant to admit to his love for her. They were talking about what he wanted for himself, so he just carried on with his personal dream.

"Back when we lived together, I wanted you and I wanted to be like you. I dreamed of being pretty and fun, and a girl," he mumbled, now terrified about what he'd just admitted to - it was so embarrassing...

She sat stunned for a moment, thinking, trying to come to terms with what he'd just said - be like me. But then understanding dawned. She leaned in and began whispering. "You want to be a girl? As in transgender?"

She was clearly shocked by his admission. But she wasn't freaking out either.

Blushing furiously, and unable to look her in the eye he mumbled, "well, yes. But I'm not gay. Not into men. I just always admired pretty women, their beauty, their clothes, their makeup, and their power to get what they wanted using their charm and sexuality."

"But you don't want a man?"

"No, not at all. Just like you, I want to be with a woman."

"So, you'd spend your fortune to change? To transition?"

"Maybe," he sighed. Now totally humiliated by what he had admitted to. And wishing that he hadn't. He must be drunker than he thought...

She could see how embarrassed he was. And she was still confused and surprised. All she could think to do was shift over and hug him, tightly, lovingly.

And they stayed like that for quite a while, and he loved her for it.

When she leaned away, he was crying, silently, and her heart skipped a beat. "Have you always felt that way?" she asked softly.

"Yes," he moaned. "But I never, ever, thought it would happen."

She nodded. "All the way back when we lived together with our parents?"

Since he'd already let the cat out of the bag, and she hadn't over-reacted, he was feeling a little braver. He wiped his eyes. "Yes, I used to watch you, and envy you so. Your makeup, your hair, clothes and shoes. You always looked so good, and were so happy."

He paused to chuckle, nervously. "Girls have all the fun."

She continued to stare at him, still having trouble believing. "I never knew..."

"I was afraid you did."

"Why, how?" she asked, still stunned.

He blushed again, but continued his confession. "I used to sample some of your things, when no one was around. A couple of times you commented that your drawers were messed up, undies were out of order. That was me."

"Oh God, Jason. Really, I never knew, or suspected. I'm so sorry."

"Why are you sorry? It was me."

"If I'd known, I could have been more supportive."

"Aubrey, I came to terms with who I am a long time ago. It's just a fantasy. I'm fine. Don't worry about me."

Still stunned, and confused, she started to feel sorry for him. He had hidden his feelings for so long. And he loved her, too.

She again pulled him into a hug. And then it dawned on her. "You didn't mind going out tonight at all, did you? You enjoyed it," she murmured into his ear.

Sheepishly, "yes. After I realized that I could pass."

"Wow," she said. Now more amazed, than confused. "That's actually pretty cool."

"Huh?"

"We both learned something tonight. Important things. I need to think about this, when I'm more sober."

Although she seemed excited, he was now feeling depressed - afraid that nothing good could possibly come from his stupid confession.

"It would probably be better if you just forgot all about it. You have enough to deal with, and I'm happy with the way things are."

She thought for a moment and frowned a little. "Let's just go to bed." And she stood up leaned over and gave him a quick kiss on the cheek and then unsteadily wandered away, down the hall toward the bedrooms.

He sat there for a few minutes, wondering 'what have I done', before he turned off the lights and walked to his room. He wasn't feeling so very drunk, now. His admission had sobered him up.

Damn!

In his bedroom, he realized he had a lot of work to do before he could collapse into his bed. He had to strip off all his girl clothes, and wash off all his makeup before he could sleep off both the alcohol, and his confession.

And it was a lot more work than he'd ever had to deal with before, with his men's things.

The tiny buckles on his shoes gave him trouble, and undoing the garter clips, too. Unhooking the cincher was difficult, and reaching behind to undo the bra was frustrating, but he finally got it. He dumped everything into an empty drawer, not sure what else to do with it all.

Stripping off all the makeup was also a difficult battle. There were none of the typical removal lotions in his bathroom, and he wasn't about to knock on Aubrey's door to beg for some. So, he had to scrub, repeatedly with simple soap.

But eventually his face looked clean.

His hair was a sweaty mess, from spending the evening in the wig, and he didn't want to go to bed like that, so resignedly, he delayed sleep while he stepped into the shower. And immediately remembered that he was now hairless, everywhere.

That worked out well, when he was a girl, but now he wasn't all that pleased by the condition.

Under the warm spray he was tempted to whack off. His poor cock had been bent back between his legs for so long it was a huge relief to have it free once again, and it got hard under the spray. But he was tired and had too much on his mind for self-activated sex.

He finished with his nails still painted pink. In the morning he'd have to ask to borrow some nail-polish remover.

It was almost daylight when he at last climbed under the sheets.

Lying in bed, he only reviewed the evening's adventures, and his admission to Aubrey, for a short while before exhaustion took over and he passed out.

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

Jason was relieved when nothing was said about his secret, the next day. He had been nervous when he walked into the kitchen, mid-morning, to find the two girls eating breakfast and chatting, but everything seemed normal.

Perhaps I just imagined that event, he thought, and hoped. I was pretty drunk. Maybe it never happened.

Aubreya and Denver were still talking and laughing about the party, and he was able to join in, commenting on all the women he'd met.

They discussed Winona for a while. Aubrey adored her, and Denver liked her as well. He admitted to being intimidated by her. "I almost fell out of my chair when she so easily recognized me as a guy in drag," he admitted, with a groan.

"She's good, and has been around for a long time. And she's nobody to trifle with. She's some hot-shot lawyer, you know. Civil rights and personal freedoms, that sort of thing." Denver explained.

Eventually, finished with their food, they all agreed that they needed more sleep, so they headed back toward their bedrooms.

In the hallway, he asked about nail-polish remover.

Denver laughed. "I suppose you can't really walk around like that."

He was relieved when she didn't harass him, or refuse to provide assistance. He got a bottle and a bag of cotton pads to take to his room.

Cleaning his nails could wait until after his nap, though...

When he woke up a couple hours later, he felt better and decided he needed a run. It would allow him to ignore last night and burn the last of the alcohol from his poor body.

But first he had to wipe the silly polish from his fingernails. That took a while, and by the time he was finished, he was really ready for some serious exercise.

For the first mile his legs felt unusually stiff, and that confused him until he remembered he'd spent the night wearing high heels. And that memory distracted him and got him thinking once again about the crazy night and his admission to Aubrey.

Damn!

But as the miles ticked by, he was able to relax his concerns, and just focus on the road ahead.

Back at the house, he cleaned up and ate alone in the kitchen, there was no sign of the girls, and that was fine with him. Finished with his early lunch, he retreated back to his room and settled in to watch a game on the TV.

Dinner, all together, was a quietly normal event. They moved on from the party and chatted about their plans, the money and the house - their favorite topic.

That was again a relief. He wanted all of the events from Saturday to be forgotten.

+++++++++++

They spent Monday like all the other workdays, dealing with plans and issues and finances. If he wasn't on the phone, Jason was focused on his computer, and it all kept him too busy to worry about the secret he'd shared.

After the long workday, the three of them ate dinner as they usually did, gathered around the kitchen table, watching the news. After cleaning up the kitchen, they relocating to the family room's couch, and watched a couple of favorite comedy shows before they performed their normal good-night hugs and kisses and headed off to their bedrooms.

When he walked into his room, late, he found a brand-new packet of women's bikini panties setting on the dresser. He stared at them for several minutes, shocked but awkwardly intrigued.

He knew he should just dump them in a bottom drawer and forget them. But the temptation was so very strong. He wondered who had placed them there. Audrey or Denver, or were they both playing with him?

Had Aubrey shared his secret with her lover? That too was disturbing.

Finally, he mumbled "damn it all," and with a sudden resolve tore open the package.

There were three pairs inside, all satin with delicate lace borders, in black, red and pink.

Shit! He was so tempted...

They were pretty, and sexy, and he was alone...

After a session in the bathroom, he resignedly surrendered to the desire, and tried the black pair on. They felt wonderful, and when his cock got hard, it peaked out of the top. Kind of gross - certainly not ladylike. He chuckled as he crammed his prick back under the material.

Enjoying the feel, he wore them to bed and tried to sleep, but couldn't - too distracted.

Eventually, unable to control himself, he got up stripped off his panties and slid into the bathroom shower. There, he cranked up the hot water and got himself off. That helped...

I wonder if they can hear, and guess what I did, he asked himself, afterwards.

Relieved, and dry, he hesitantly pulled his panties back on and crawled back into bed. He laid for another hour, analyzing the appearance of the panties in his room; wondering what would come of it.

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

"Which pair are you wearing?" Audrey asked, casually the next morning, while they were eating breakfast.

He'd just thrown on a T-shirt and a pair of shorts to go down for food, and he didn't want to answer, too embarrassed.

"Come on, give. We have a bet." Denver said, impatiently.

"The black ones." He mumbled. He had kept them on all night and simply pulled on his casual clothes, when he woke up.

"I knew it!" Aubrie, laughed. "I win!"

"I expected the pink pair." Denver said, sadly.

Without thinking, and feeling offended, he frowned at her. "I'm not that girly!"

When the two women laughed at him, he smiled sheepishly and then joined them, laughing. It all seemed so unbelievably absurd.

He was relieved when there was no further discussion of his under garments. He did wonder if Denver now knew about his fantasy, or if the whole panties thing was just the result of their dress-up games form the party.

Their breakfast was hurried, in any case. No time for fun. A series of conference call meetings were scheduled to discuss various aspects of the newest investment plans.

And after those, there were reports to study.

That day, they never left the house. So, he never changed his clothes.

+++++++++++

That night he almost wore his panties to bed, but decided against it, he was used to the freedom of boxers.

And it was a good thing, as that night Denver decided to pay him another visit.

He was, of course, delighted to see her. And he was relieved that he wasn't wearing women's panties to enjoy sex with this beautiful woman.

She crawled into his bed with him and settled on top to kiss and cuddle before the main event.

When they got serious, she slid off his men's underwear and tossed them aside without comment, before settling down between his legs to suck on his cock.

But after just a single kiss and lick she paused to sigh and mumble, "so soft and smooth," before resuming her tongueing, driving him crazy.

But as she liked to do, she only kept that up until he was ready to explode. Then she stopped.

She giggled. "I'd carry on a little longer, but if I do, I'm afraid you'd waste all that wonderful cum. So, I think it's best you do me now. After you give me a nice 'O', we can fuck for real."

She then slithered up the bed and sprawled onto her back, legs spread. He didn't want to upset things, by complaining. He hated the interruption to his pleasure, but he did feel he owed her her own enjoyment.

He crawled down the mattress to settle in between her long legs, and began kissing and licking at her pussy. It was already damp and it got wetter as he continued. After a while, she was squirming a but, so he shifted his focus to her clit and the inside, using his tongue, and that started her moaning. He kept at it, even pushing gently with his teeth padded by his upper lip, against her clit.

With a shudder and a chirp, her orgasm hit and he had to hold her down with hands on her hips, so he could keep applying his tongue and help her enjoy the feelings.

As she came down from her sexual high, he gently resumed kissing and licking her sex. She sighed happily, and he lifted his face off, wiping his cheeks with a hand.

"Mission accomplished," he chuckled as he crawled back up to lay next to her, head on the pillow.

She rolled onto her side to give him a thank you kiss. But only held it for a moment, before she got up onto her hands and knees to crawl down to straddle him and lower herself down onto his pole. It was still hard enough to slide in, and it grew harder and longer in only seconds.

She rode him hard, until he began cumming and she orgasmed again from the pleasure of it all.

When she was finished, she sprawled on top of him until his shrunken cock slid out of her.

That was the way she liked her sex with him, and he had no complaints.

When she rolled off, she settled in on her side facing him.

"I love your body, now." She said as she lightly ran her fingers up and down his bare chest.

"Because I'm hairless?"

"Yes. You need to keep it this way."

"Um, I don't think so."

"Why not?"

"I am a guy. Men are hairy."

She grabbed his shrunken cock and squeezed. He jumped and groaned. "Hey!"

"Hush. Now you listen to me. You will keep yourself hairless. I don't want a furry cock, or a hairy man."

He was surprised by her demand. She'd never actually given him orders before. And he didn't know how to respond.

"Understand?" she prompted him, while still holding onto him. "I don't like getting pubes in my mouth."

"Yes," he muttered.

She released her hold and gently kissed him on the cheek. "If you enjoy it when I suck on you, you need to keep yourself bare."

"Okay."

"Good."

Then she resumed gently scratching his chest, for a few more minutes before she stirred, and slid off the bed.

"That was nice," she said as she leaned back down to give him one more kiss.

"I liked it too." He said, smiling up at her.

"Wear the red ones tomorrow," she said as she was heading for the door.

He knew exactly what she meant, but played dumb. "What?"

She chuckled, "you know, silly boy, the red panties. Wear them."

Then she opened the door and walked out before he could argue.

When he got out of bed the next day, he slipped on the red panties. He did like them, and Denver wanted them.

++++++++++

Later that morning, they had their first complete team meeting. Denver half-jokingly, had started calling them 'Aubrey Incorporated'.

It was only after their gathering that Jason realized that he was the sole male in the group. Besides accountant Morgan, there was Theresa the attorney and Quinn the Investment manager.

Brianna, the real estate agent, was the only straight woman in the bunch. She had a husband, but she was only a part-timer on the team.

Everyone knew that Denver was her partner, and Aubrey made it clear that he was now her right-hand man, literally and figuratively.

In any case, among all those strong and competent women, mostly gay, he definitely felt like the token male. But he was wearing women's underwear like all the others.

The meeting went well, and he and Aubrey walked away afterwards, confident that her millions were in the best of hands.

+++++++++++

The rest of that week was just more of the same - work, intermixed with (not enough) play.

But Jason felt that their relationship, their threesome, had begun to change, and it made him a bit uneasy.

Every day now, he wore feminine panties beneath his clothes. Several additional packages had been placed in his room, and on Wednesday night, when he went to grab a pair of boxers to sleep in, that drawer was empty.

One or both of the girls had removed them, leaving only women's underwear for him to wear.

On Thursday night he was again thrilled when Denver came to visit. When she crawled under the sheets with him, she realized that he was naked.

"Where's your underwear?" she asked, sounding a little disappointed.

"Well, I used to sleep in comfortable boxers. But they disappeared."

"You wear panties, now." It was a statement, not a question.

She climbed back out of bed, searched through his drawers until she found a pair of yellow bikini panties and then tossed them to him.

Still lying there, he caught them.

"Put them on, please."

"Why?" He asked. Why put them on, when he'd just be taking them off?

He held the sheet up and open inviting her back in to screw.

"I want you in them when I come for you."

He looked at her, perplexed.

"Humor me. I'll enjoy taking them off you. And you must wear panties always."

When he didn't move fast enough, she turned and walked toward the door.

"Okay, okay. Come back, please."

His cock was hard and he was too horny to let her get away now. He began hurriedly sliding the things up his legs.

She paused and turned and watched as he pulled them up over his ass and over the top of his cock. They barely covered it.

"Always?" she asked.

He sighed. "Yes. I have been wearing them under my clothes. I have nothing else."

"I know. But from now on, always."

"Yes, ma'am."

She giggled. "Good. I like that."

She hurried back and crawled into the bed, to lay on top of him, pressing his cock between them. She wasn't wearing any panties, but now he was.

They kissed and cuddled for a while; he enjoyed that part. He really did love her. He also admitted to himself that he liked the way she took charge and fucked him. He only had to lay and enjoy.

When she was ready, she peeled his panties off, kissing and licking his cock as it became available.

Then they screwed, and she orgasmed as he came inside her. And it was wonderful.

They cuddled while they recovered and then as always, she left him in bed with one final kiss.

As she prepared to leave his room, she simply reminded him, "put your lovely panties back on, my girl."

After he cleaned up, he slid them back into place, and went to sleep, bothered by her parting, 'my girl.'

From that point on he wore panties beneath his clothes, and in bed. He justified it to some extent, because he had no other option. But when he was being completely honest with himself, he admitted he relished the feel and the implication of his sexy panties.

He did have a problem with wearing them when he went out running in his flimsy gym-shorts, though. The shorts were purposefully loose, and he was afraid that his bright, pastel girl's underwear might show. But he had no other option so he ran along just hoping...

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

Another change in their relationship centered on how casual they became with each other. And Denver began treating him like one of the girls.

One quiet afternoon, he and Aubrey were in the office finalizing a couple deals, when Denver came prancing in, with a bag of new clothes from Nordstrom's. She'd been out shopping and apparently scored some things she liked.

"Check these out." She said happily as she began pulling clothes out and laying them on the tabletop.

Then she stripped off the dress she was wearing. Underneath she wore a tiny thong and a sexy bra, that made her tits look huge and adorable.

Without any sign of shyness, she picked up a new dress, it was deep-blue, thin and stretchy, and began slithering into it starting over her head and pulling it down.

Jason's jaw dropped.

He'd certainly seen her naked, in his bedroom, but she'd never put on a performance like this before.

Aubrey wasn't impressed. "For Christ's sake, Den," she scolded, as she pointed to her brother, "look what you're doing to him."

Denver looked over at him, confused for a moment, before she noticed the look on his face and the bulge in his pants. Then she giggled.

"I forgot he's not just one of us girls."

"He's not a girl" Aubrie screamed.

Denver giggled. "I'm sorry, only joking. But he is family, and he's certainly seen me before."

"Denver!"

She finished straightening her dress, and he thought she looked fantastically sexy in it, then she walked over and crawled onto his lap.

"Oh, poor boy. I'm sorry. But do you like my new dress? I'd like a boy's opinion."

Jason blushed and squirmed as his cock was being pressed by her ass.

Aubrey groaned. "You're such a slut."

"But you love me, and so does your brother, don't you Jason."

He moaned, "yes. I love both of you."

"See?" Denver said glancing victoriously over at Aubrey.

She growled, frustrated, but couldn't help but giggle. "I wish you'd save your affection for me, and stop torturing my poor brother."

"I have enough love in me for the both of you. And I'm having too much fun to stop."

"Well, have some consideration for us. You're making me jealous, and practically killing him.

"And I need him alive and functional to take care of my money - our money."

Denver, clearly didn't appreciate the rebuke, she picked up her things and stormed out of the room.

"I didn't mind," Jason said after she'd left.

"She can be mean to boyfriends," Ambr replied. "She delights in toying with them." Then she chuckled. "Of course, she hasn't played with boys since we moved in together."

Then she pulled him over and gave him a nice kiss, and when she finished, she added. "And you are almost one of us girls."

He shrugged, noncommittally, unsure what she meant by that comment.

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

As the days had passed, he had begun counting the nights, waiting for what had become a regular, weekly visit from Denver. He couldn't help himself. Each night he went to bed, in his panties, hoping for the little tap on the bedroom door, and the sex that followed. She could show up any night, but she did happily show up regularly now.

To some extent it ruined his sleep, as he spent too much time anxiously wondering if tonight was the night.

That same night, after the striptease, he was lying there watching the late-night news, when the tap startled him and the door opened so a naked Denver could glide into his room. She was smiling broadly and giggling happily as she closed the door behind her.

Of course, she looked magnificent, and he was instantly turned on.

It had only been two days since her last visit, so he was surprised and wasn't sure if this was for real. "Helooo" he mumbled as he blinked rapidly, am I dreaming?

"I came to apologize, and to make it up to you. I'm not a tease, not trying to torture you. I'm just so comfortable with you, these days."

"No apologies necessary. I enjoyed the show." he replied. He was overjoyed to see her.

She chuckled. "That's good. You know I love you, and consider you part of the family. Aubrie, me and you."

"We make a lovely family," he sighed as she climbed into his bed.

She settled in on top and kissed him, and he enjoyed it, as always.

They kept at the foreplay longer than usual that night, and after she'd stripped off his panties, she immediately climbed aboard and settled onto his cock to ride him. No blow job that night. He certainly didn't mind.

What she did do, was scratch his chest, more vigorously than she normally did. He groaned and squirmed, as she hurt him. But she just giggled. "Hush," she whispered, as she scratched him again, with a wicked smile. A look that he hadn't seen before.

But that little hurt didn't stop him from cumming, and her orgasm was perhaps even a little more passionate.

And when she finished, and laid down on top of him, he felt the pain again. He groaned, and she giggled in response.

"What's the matter boy, did I hurt you or pleasure you?"

"Yes," he muttered. He wasn't about to admit to being hurt by her fiery love-making.

She laughed. "You'll heal before next time."

"I hope so."

She chuckled and kissed him again, before rolling off, to lay next to him.

They were still laying together under the sheets, recovering and feeling happy, when there was a knock on the door and it opened, revealing Aubrey standing there in a T-shirt and panties.

Jason was again surprised - shocked really. Aubrey had never interrupted them before. He felt a little guilty. Almost adulterous.

Aubrey laughed. "Relax, bro, don't have a stroke, I just wanted to make sure everything went well."

Denver chuckled and reached down to pat his shrunken cock. He jumped at the touch.

"It went splendidly." She said. "He's a loving and considerate boy. No testosterone overload here. We had a very nice time."

"Good. You two look comfy." Audrey sighed. Then as if she'd just made a decision, she stepped forward and slid into bed next to Denver, on the opposite side from him.

Holy shit! Jason thought, his brain and emotions still in an uproar. I just might have that stroke, he decided.

Denver rolled onto her side, nudging him with her sweet ass, so she and Aubrey could kiss. And it was a long and very passionate kiss. If his balls weren't so empty, his cock would have been hard as a rock. In fact, he felt it stirring despite the recent sex.

He was terribly disappointed when nothing else happened. Aubrey and Denver cuddled there together, beside him, but he was ignored. No invitation, or even acknowledgement.

A short time later, the two girls settled in together, comfortably and quietly, and dozed off, there right beside him. In his bed.

There was no way he could relax and doze off. He laid there listening to their breathing, longing for their attention. He'd had Denver, but now he really wanted Aubrey.

If his sister was put off by his cock, still harboring her hatred for penises, why was she there in his bed? Could she be jealous of Denver and him, and staking her claim to her lover. He couldn't guess.

What he did know was that he wished with all his heart that she was cuddling with him.

He spent the rest of the night sleeping fitfully, painfully aware of the two beauties there next to him; dreaming of sex with Aubrey, or with the pair of them.

In the morning, the two girls left to get cleaned up and prepare breakfast. Both of them did give him a kiss before departing. And both kisses were loving, but only Denver's included a groping of his cock.

Over breakfast there was no mention of their night together.

Jason remained confused, and vexed. He loved them both, and enjoyed sex with Denver, but he wanted Aubrey, and she apparently didn't want sex with him.

After breakfast, while they were cleaning up the kitchen, Denver wrapped her arm around him. "How's your chest, lover? Any permanent damage? I didn't carve my initials in you, did I?"

He gave her a dirty look, and kept on rinsing the dishes.

"What did you do to him?" Aubrey asked curious and concerned.

"Just left my mark on him," she replied, offhandedly. "Only scratches."

Aubrey turned to Jason, questioningly.

He shrugged, not wanting to make a big deal out of it. "Just scratches, I'm fine."

Aubrey wasn't sure she believed them. Either of them.

Denver was on her way out the door, when Aubrey grumbled at her. "Don't you dare get bitchy with our man."

Denver laughed as she exited.

"I warned you, she can get mean sometimes, with her men."

He turned to her. And pulled her into a hug, kissing her lovingly. He was delighted when she kissed him back.

"I'll be fine." He assured her as they walked together out and toward the office. Time for work.

++++++++++

It was an easy day for the team. No meetings to attend or high priority business tasks that needed immediate attention, so the three of them wound up just lounging around, taking care of some housework and laundry.

Jason had to wash his panties, which he always took care of himself. It still seemed just a little too humiliatingly personal to perform that simple domestic task in front of the girls.

++++++++++

After dinner that night, they settled in to relax in front of the television. Jason wasn't always thrilled by what the girls liked watching. Some of the romantic movies were okay, but the silly 'bimbo housewives of Boston' type shows were terrible, in his opinion. He watched them begrudgingly, only because he liked the company.

"We need to practice for the next Girl's night, it's only a few weeks away," Aubrey mentioned during a commercial break.

"Four weeks," he mumbled.

"Whatever."

"You don't want to piss off Winona," a grinning Denver added.

"The Queen?" he replied, mockingly.

"Hey, bro. She's a wonderful person and my friend." Aubrey scolded.

"Sorry."

"And you admitted enjoyed the last session."

"He did?" Denver asked, surprised.

Aubrie stared at him, preventing him from denying it, "he did."

Denver saw the look her lover gave to her step-brother and started to wonder if something was going on. At times they did act like true siblings with some uncanny telepathic connection.

It started to dawn on her when Aubrey, chuckled and carried on. "Jess may whine, but she'll love going to the next party. Won't you sis?"

Jason, blushed self-consciously, as he stared back at his sister.

"He does love wearing his pretty panties," Denver said, almost to herself.

He heard, and got up. "I'm going to go watch the game on my TV. Good night, ladies." He gave each of them a kiss before departing.

After he'd left, Denver reached over and grabbed Aubrey's hand, demanding her full attention. "Aubrey, my love, does your brother have a secret fantasy? Is he into cross-dressing? Is that why he enjoyed Lady's night?"

Aubrey sighed. She did hate keeping secrets from her partner. It always wound up poorly, whenever she tried.

She leaned in closer, and whispered back. "He has trouble admitting it, but I believe he's a repressed trans. He'd rather be a girl. But I'm pretty sure he'd be a lesbian too, if he could."

"Wait, what?" Denver muttered, stunned.

"He confessed to me, after the party, that he'd always fantasized about being a girl, doing girl things, with another girl."

Denver thought for a minute. "And that other girl would be you?"

Aubrey sighed, again. "Yes."

Then she sat back to let the news sink in.

"He is a very nice guy. And he's got a good cock." Denver mused, almost to herself."

"Denver!"

"I know, sorry. I know how you feel.

"He's also good with his mouth. Licking pussy. Almost as good as a girl."

Aubrey groaned. She never liked talking about the particulars of sex. "Denver, we have to be careful with him. I do love him, you know."

"But as a brother," Denver added.

"Yes."

They sat quietly for a while, watching the show, and thinking. Denver especially - contemplating the implications and the possibilities.

"I thought your games with the panties was just for fun. Just Sister-brother antics. You screwing with his head, but it wasn't, was it?"

Aubrey smiled sheepishly. "No. I wanted to give him a little thrill. Test his feelings. See if he was really serious."

"And he is, since he's been wearing them."

"Yes."

They resumed watching the show, until Denver interrupted again. "I like him as a boy with a lovely cock to ride every once in a while. I have you and your sweet puss for the real love making." Denver muttered, happily.

Aubrey laughed. "You're such a slut. But I love you."

"And I love you. I suppose though that Jess could be fun too. She'd more easily fit in with the two of us."

"It might be weird," Aubrey replied, hesitantly.

"Why, you'd just have a sister, instead of a brother, and she wouldn't have a nasty old cock to get in the way."

"There is that," Aubrie mused, intrigued.

The show ended a couple minutes later and they hugged and kissed, for several minutes, before they got up and arm-in-arm, strolled up to their bedroom to enjoy sex with each other.

But as they walked, Denver was thinking; holy shit! Jason. Now that makes things really interesting...

++++++++++

Much later that night Denver arrived in Jason's room, again unexpectedly.

He certainly wasn't upset when she showed up at his door, with her usual little knock before entering, but he wondered why she was there so soon after their last session.

He forgot that question when as she always did, she climbed into the bed with him and slithered on top of him, to cuddle and kiss.

And some twenty minutes later she slid down between his legs to lay and focus on his cock.

She was sucking on him, and it was feeling wonderful, when she paused and lifted her head to stare up at him.

He didn't appreciate the interruption; he was hard and getting close.

"So, confirm it for me, you enjoy dressing as a woman."

When he didn't answer she leaned over and picked the head of his cock with her teeth.

"Ouch!

"Yes, I do," he admitted.

"Always have?" she asked as she gave his cock a lick, making him shiver.

He sighed, "since I was a teen."

"But you wanted Aubrey," she challenged him.

He groaned at the interrogation. "Yes, and I wanted to be like her."

"Ah. I think I understand. You two lived together then with your parents, didn't you? And you spent a lot of time together, real sister and brother time."

"Yes." he mumbled.

Now what? He wondered. Aubrey had accepted his admission, would she? She was bi, after all, so perhaps it wouldn't matter to her. She did love his cock.

His admission did seem to satisfy her because she went back to sucking on his cock. And when he was close to exploding, she replaced her mouth with her pussy, by climbing up and straddling him as she liked to do.

He was relieved that the conversation was over, and happy that she had moved on, and it was feeling so very good.

But a few minutes later while she was riding him, and as he was ready to explode, she again suddenly stopped, and just sat there looking down at him, speculatively.

He moaned, "Oh, God, don't stop."

"Just one more question. Do you want to dress like a girl or actually be a girl?"

He groaned. He wanted to cum, and didn't want to admit to his fantasies and desires.

"Yes," he whispered.

"Yes, you want to be a girl?" and she smiled, encouragingly at him.

"Yes."

She giggled, and resumed pumping up and down on him. "Good, I'm glad we got that settled. Now I can get my orgasm."

And I can cum, he thought, before he started losing his mind, and climaxed.

"Good night, sweet Jason. See you in the morning." She said a she left him that night.

To be continued...

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