The Shy One

Debt

It was almost noon when Brad stumbled down the stairs into the kitchen. He was still groggy from oversleeping. Everyone seemed to be out, which was fine with him, except for Cassie, who was sitting with Lisa at the table, holding her hand. Brad glared first at their intertwined fingers, then at both of them.

"Hi," Lisa said brightly.

Brad didn't feel bright himself. He was already in a bad mood from too little sleep, then sleeping too late. Seeing his little sister holding hands with Lisa, immediately after they'd just spent an entire night together, set him off. She'd made inspired love to his cock, he'd come into his little sister's mouth, then they fell asleep, she awoke in his arms like an angel, then she came down here to show affection to Lisa.

He thought they had broken up.

Brad leaned against the wall and closed his eyes, trying to think things though. He couldn't get past his jealousy. It angered him to see them holding hands, more than it should, he knew, but he couldn't fight back the feelings. He stormed over to them and made a show of pulling their hands apart, then went to the refrigerator to find something cold to drink.

"I should go," he heard Lisa say, presumably to Cassie.

"I'll join you," Cassie answered unexpectedly, angering him more.

Brad scowled into the refrigerator as he listened to them leave.

* * *

It was another hour before Brad decided to head down to the boat and go sailing alone. When he got to the dock, Cassie and Lisa were there first, already getting ready to cast off.

He stopped a distance away, not wishing to seem like he was following them, but wanting to intrude anyway. Lisa saw him and waved him over. Cassie looked, too, giving him a thin, timid smile. If she hadn't done that, he would have turned and left. Instead he approached warily, trying to think of a smooth excuse to leave if things got more awkward.

"We were just heading out to the island to let me collect my debt," Lisa said with a smirk. "You really should come, too. To be fair, I think you should pay part of it."

This all confused Brad, and obviously it was meant to. Cassie sat in the boat smirking too as Lisa walked forward to release the dock line at the bow. He didn't like the thought of them going to their island together. Brad thought of it as he and Cassie's private refuge. But the mention of a debt was baffling. Lisa's lighthearted, laughing tone didn't fit the situation, either.

"I don't want to get in your way," Brad said, releasing the line at the stern.

"Look," Lisa said over her shoulder, suddenly showing a hint of anger. "We were just holding hands, okay? It was nothing. We're girls. Girls do that kind of thing. We were sharing a heartfelt moment, and we touched each other. Get over it."

"Girls don't usually fuck each other. I thought you said you were breaking up," Brad said as he stepped into the cockpit. "I thought you sluts had broken up."

Cassie slapped him, hard, across the face. It came out of nowhere. She'd never, ever raised a hand to anyone that he could remember. His face stung. The tingling spread and intensified as he looked at her in confusion and shock.

She glared at him, then instantly softened. She flung her arms around his neck, burying her face in his chest. She felt so good there, Brad thought. A moment later she lifted her mouth to his to give him a deep, soulful kiss, quickly forcing her tongue between his lips to hunt for his. He responded only hesitantly, but couldn't hold back for long. She kissed too well.

Her lips were just like she was, soft and shy, but clever and mischievous, and warm and pleasant and irresistible.

When Cassie had had enough, she pulled away and put her face back in his chest, holding him tightly. Brad kept his own eyes squeezed closed, enjoying the warm, fragile feel of her frame in his arms. He felt the boat begin to slide away from the dock as Lisa pushed it off on her own.

"Hey, lovebirds, wanna help?" she called as she went to the mast to raise the jib.

Brad's mood lightened at her choice of words. He liked the thought of he and Cassie as lovebirds. Thinking now about Lisa's tone, and Cassie's behavior, it looked like he had been being a jerk, maybe a big jerk, although he didn't understand much of what was going on.

* * *

Tara had watched her younger brother and sister hold their tight embrace as the sailboat slipped smoothly away from the dock, with Lisa at the helm. She kept replaying their kiss in her head. She'd never seen a couple so into each other.

They did make a cute couple, she had to admit. A cute incestuous couple, though. She and Aimee had to do something to get them under control.

Tara headed back to the house, to tell Aimee that Brad and Cassie had already taken the boat, so hey couldn't go sailing now. Then she'd tell her everything else she'd seen.

* * *

Once the boat was well clear of shore and under way, Brad sat close to Cassie. She immediately leaned on his shoulder. He put his arm around her, comfortably, pulling her closer. She felt good under his arm, too. She felt good anywhere, as long as she was touching him.

"Okay, now what's this about a debt?" Brad asked. He'd tried for some time to sort it out for himself, but couldn't.

"Last summer, I made Cassie an offer. There was a certain guy she really wanted to get in bed with, and I said I'd arrange it," Lisa explained. "It took a while, but I delivered, and now Cassie has to pay her part of the bargain."

Brad looked back and forth between the two of them. Cassie was beaming a smile at him. Lisa was grinning at him over the tiller.

"You arranged for me to fuck Cassie? Everything? From the very start?" he asked. He knew she'd had a big hand in getting them together, and that she'd been manipulating him. That was obvious. But he'd assumed it had all just sort of happened, that one thing simply lead to the next.

He also thought Lisa had done it for her own warped entertainment, and for him. He never thought that Cassie was in on it since before she'd learned that he'd been her anonymous lover.

"Since last summer, yes," Lisa answered.

"You've wanted to fuck me since last summer?" he asked Cassie. She smiled back at him, then looked down into his chest as she admitted to her shame with a quick nod. When she looked back into his eyes he leaned forward to kiss her again, softly and simply.

"Since long before last summer," Cassie told him, the moment his lips released her. She breathed the words straight into Brad's mouth. "But last summer it got serious. Unbearable."

"She had wanted you to be her first," Lisa added. "But I told her she should get some experience."

Brad was quietly grateful. He liked, loved, the idea of being Cassie's first, but he knew he'd never have been able to handle the guilt. "Raping" her as a virgin would have been too much for him to handle.

"She told me everything at the end of last summer. We had played a game of truth or dare, one with no rules or limits. I told her my secret, that I was bisexual, with a strong leaning toward women, and she told me her secret, which was that she wanted to fuck her brother. So I made her an offer. If I could get you into her, she'd give me something in return."

Lisa paused, letting the story sink in, letting Brad think through all of the events of the summer, and put it all together.

"There's more to it now, though," Lisa continued. "Little Cassie's ambitions have changed since last summer, haven't they, sweetie? Actually fucking her brother has opened her eyes to new horizons. She's learned now that she wants to be more than just her brother's lover."

Brad waited for Lisa, or Cassie, to elaborate. It was all unraveling so quickly and unexpectedly, he had completely lost his bearings. He couldn't anticipate any part of this conversation. He had no idea where they were going now. He looked patiently at Cassie's face.

"I want to be your whore," Cassie said softly into the floor of the cockpit.

Brad paused to try to work that out, too.

"Meaning what?" he asked, looking between the two girls, awaiting an answer from either.

Lisa grinned at him more. Cassie kept her head hung low, seemingly embarrassed and ashamed. She wasn't going to say any more herself.

"Does it mean I have to pay to fuck Cassie, now?" Brad asked.

Cassie punched him hard in the chest, or at least as hard as she could. Brad feigned pain. Cassie repentantly rubbed the spot for him, then leaned on him, burying her face in his upper arm while holding it tightly with both hands. He wasn't sure if it was an act of apology, or just a way to hide her face in her embarrassment.

"It means she has to do whatever you want, whenever you want, where ever you want," Lisa said, looking ahead toward the island. She shifted the tiller to adjust their course and to better fill the sails.

"She has to fuck you," she continued. "You can go into her room at four AM and fuck her without even bothering to wake her up. You can walk over to her while she's reading and jerk off on her face. You can have her sit on your cock and quietly fuck you during one of the evening bon fires, right in front of everyone."

Lisa paused to look at Brad. He tried to act cool, knowing his face betrayed him completely. Lisa smirked at him.

"You can indulge your wildest urges." Lisa's voice took on a low, hungry, sexual tone. "You can whip out your cock in the back seat of your car, while your mom is driving, then grab Cassie by the hair and make her suck it. And she has to do it, and she has to like it, because she wants to be your whore."

Brad tipped his head downward to look at Cassie. She still had her face buried in his biceps. He could feel her shame. He kissed the top of her head, then lifted her chin with his hand to kiss her lips softly. She looked at him, more than a little scared, as if any of this would make him think less of her. Or as if he might refuse.

"And you can say anything you want to her. You can tell her she loves your cock. You can tell her she's a whore. You have to tell her she's a whore. Or your little sister slut. She wants you to. She wants to hear what a good little whore she is, all the time. At the beach. At lunch. And especially when the rest of your family is around, though probably not loud enough for them to hear it."

Brad took a while to let it all settle in. Then he put it to the test. He gripped Cassie's shoulders. He pushed her away from him, gently but firmly. His hands slid down her shoulders to brush her breasts. Cassie closed her eyes, tensely sucking air in through her teeth.

"Take your top off," he ordered. He kept his tone soft and tender.

She kept her eyes closed, but did as she was told, pulling her shirt over her head.

"Bikini top, too," he commanded, a bit more harshly.

Eyes still closed, she reached back and undid the clasp, then shyly slid the straps off. She folded her arms, covering her tits.

"Show me your pretty little sister tits, Cassie," he commanded, warming to his role, trying to sound stern and arrogant. "Now."

Cassie dropped her hands, stiffly but obediently, to her sides.

"Open your pretty little blue eyes," he commanded.

She opened her eyes, but looked up at the sky, avoiding eye contact with him. He left her that last shred of self defense.

Brad stared at her breasts for a long time, feeling Cassie grow more and more uneasy. When it seemed he'd tormented her for too long, he reached forward with both hands. He was gentle, first running the backs of his fingers around the edges and across her nipples. He took each nipple between a thumb and forefinger to pinch them, ever so softly. Cassie's gaze dropped down now to watch her brother's hands fondling her.

One strong hand slipped behind her neck, to hold her in place, as his other hand cupped her breast, then squeezed it, softly at first, then more firmly. Her entire tit fit easily into his single hand. Cassie let out a long, soft moan as he did it. He leaned forward to kiss her, aggressively forcing his tongue into her mouth, while squeezing her tit harder, almost as hard as he could. She moaned again into his mouth, then let the moan rise into a squeal.

He broke the kiss.

"I've always, always loved your tits, Cassie," he said hoarsely. "I've wanted to do this for years, and you keep hiding them from me. Now they're mine. I want to see them all the time."

Cassie whimpered once at his words.

Then he lowered his mouth to one tit. His lips and tongue tasted her flesh. He sucked it as hard as he could. It was so small that he took almost all of it at once, sucking in to cover as much of it as he could with his wet mouth. His tongue made quick circles around her nipple as her hands came up to pull his head into her chest. He continued kneading her other tit with his hand. The combined pressure forced her backwards onto the cockpit seat.

He played with her tits for a long while before rising and beginning to unbuckle his belt. Cassie looked up at him in anticipation.

"Sorry, but you don't have time for that now," Lisa said.

Brad looked at her.

"My debt, remember?" she said to them both. "We're nearing the island."

Brad looked at Cassie's tits again, then back to Lisa. He reluctantly slipped away. Cassie immediately moved under his arm, quickly guiding his hand back to one breast. She rested there while he kissed her hair, fondled her, and looked at Lisa again.

"So you teased me all summer, on purpose, to get me to want to fuck her? You maneuvered everything?" Brad asked.

"We were never even 'dating'," Lisa elaborated. "That was all, or mostly, just a ploy to set you up, to make you jealous. Every guy wants the girl he can't have, especially if he knows that someone else can."

"I saw you two together. I heard you," Brad argued.

"Oh, we played the game well. Don't think I didn't enjoy my part. Cassie is absolutely a hot little fuck, and I did like making her come, and she really did come for me. That part wasn't pretend," Lisa went on. "Except I think she was imagining you with her every time."

Cassie smiled at her. Brad looked at Cassie. His expression was at once harsh and tender.

"I thought I was raping you," he said. He let the annoyance show in his voice.

"I want you to rape me."

The anger left him as soon as Cassie said it. She was his whore. She wanted him to rape her, so it wasn't strictly rape. When he had thought that he was tricking her into fucking him, it was he that was being tricked. She knew it was him all along. When he thought she would die if she knew her brother was fucking her, she did know and she relished it instead.

When he had rammed his cock into her cunt, into her mouth, each and every time, it was exactly what she wanted, no more. He had never raped her. He'd felt all that guilt for nothing. Perhaps not all of it, he thought, but it was worse than it had to be.

He was going to fuck her again, now, as hard as he could. Brad started to undo his belt again.

"Debt," Lisa scolded, halting him again.

"Okay, so what's the debt?" Brad asked.

"Cassie has to finally, really lick my pussy. And as long as you're here, and clearly benefiting from the whole deal, you have to help. She's never done it before, so you have to make sure she gets it right. I want to experience the kind of orgasms she's been having all summer."