Annie

Jill found the robe that her sister had left her and threw it on as she flew through the bedroom door, eager to see who was up and do what had to be done.

There was Annie, her curly black hair frizzled from sleep, wearing a white spaghetti-strapped undershirt and pair of baggy gray sweat pants. She didn't see Jill walk up behind her as she bend over, peeking her head into the fridge.

And Jill smiled at the sight of her sister's cute ass pointed in her direction. Jill felt herself starting to get a bit moist.

Old Jill would have been shocked to know she'd be thinking of her sister in that way. But that all changed one night three months ago.

Jill had been out at her local bar clad in a short tight dress, panty-less, looking for a good lay for the night and had focused her attention on Diego, a handsome young Latin man with dark chiseled features. But when it came time to seal the deal he shocked Jill by balking.

"I'd love to go home with you." he said, his smooth voice melting around Jill, "But I'm here with my sister and I'm he ride."

So Jill met Daniella, his sister, more of a slightly pretty, shy, short-haired girl than a sultry Latina. But they got along well and soon Daniella was just tipsy enough to want to help her big brother get laid. Jill offered her a room for the night at her apartment and she eagerly agreed. "I'll be a good wingman for ya'" she said to her brother as she gave him a friendly punch in the arm.

And the three made their way down the street to Jill's place and opened a bottle of wine. When it soon became apparent that a separate room wouldn't be needed.

Jill hadn't meant to stoke the flames, just be a bit playful when she said to Daniella, "You know your brother is incredibly hot? To think, you probably could have had him any time you wanted."

"I don't think I would have done that" Daniella had drunkenly insisted. "He's my brother."

"Still..." Jill almost couldn't help but go on. "I bet if he ever saw what was hiding under that little sweater of yours, he wouldn't be able to help himself."

And a minute later, Daniella's sweater was up and over her head, her bra on the ground and her little nude breasts presented to her brother. Moments later their mouths were pressed tightly together.

"Just a little tongue" Jill said and the siblings acquiesced as if they couldn't help but obey.

The rest came naturally. Jill was never more proud of herself then as she held her hand gently onto the back of Daniella's head and slowly guided the girl's lips forward around her own brother's hard cock.

It turned out the three of then didn't need any bedroom. They woke up the next morning on the floor together in various states of undress. Jill gave them her number and told them that she was up for it any time they were. Though they dressed and scurried off quickly, awkwardly, seeming a little afraid at what had happened the night before. Or maybe just afraid that they'd liked it. "Diego & Daniella - #506, 507"

Jill was not afraid, and since that day had started thinking of her own family occasionally when she masturbated. She thought of her older sister Annie and her younger brother Isaac. She thought of her mom and dad. They had both passed a few years ago, but in her fantasy she was lying in her old bedroom at home, awakened on her eighteenth birthday by her mom whispering "Good morning darling. Now that you're a grown woman, your father and I are going to teach you some things." And quickly they'd peel off her pajamas.

So what Jill was about to try tonight was something she'd fantasized about often, but never really believed would happen. The only question was how easy would Annie be to seduce.

"Oh Jilly! I didn't see you there" Annie said as she turned from the fridge, a carton of milk in her hand. "I was just getting an... um... drink."

Jill's robe hung open, her smooth pussy exposed in the dark. Annie glanced at her sister up and down for a moment and grimaced. So far, not open to seduction.

Jill knew just how to play this. "I thought I heard you get up and I wanted to say... well I wanted to say 'I'm sorry."

Annie sparked a little smile.

"I never wanted to upset you. But this is my life now and I'm so happy with it. I thought you'd want me to be happy too."

"I do Jilly" Annie answered trying to avert her eyes from Jill's crotch.

Jill went on. "I guess I would have reacted exactly the same way you had ten months ago. But I feel so much more free now. Does that make sense?"

Annie chewed on her lip. "I guess... I don't know."

"I mean I'm not hurting anyone right?" Jill started to get insistent. "In fact I'm bringing people pleasure. I'm bringing myself pleasure. I mean cumming makes everyone happy right? So why not do it every day?"

"I um... I guess..." Annie trailed off, seemingly uninterested in the conversation and Jill wondered why. She'd expected perhaps a bit of a fight. And then it hit her. But it couldn't be, could it? And suddenly it was Jill who felt pity for her big sister.

"Annie?" Jill asked. "Can I ask you something."

"Sure." Annie whispered frozen with the carton of milk still in her hand.

"Have you ever had an orgasm?" It was out in the open now and Annie couldn't deny it.

"That's not really... I mean I don't want to...." Tears built in Annie's eyes.

Jill stepped closer to her big sister. "I've had hundreds of them in the past few months alone and you've never had one." And Jill laid her fingertips on Annie's soft pale shoulders.

"Jilly..." Annie squeaked.

"Shhh... I want to help you." Jill whispered back.