Playing with her Brother

If Cindy had received this offer in other circumstances, like during a calm lunch break where she was sipping tea and at peace with the world, she might have taken more time to consider her options. To carefully run through the pros and cons of various approaches, to imagine tests she might undertake to tell if this license was legitimate or she was being fucked with.

But Cindy was not in other circumstances. Cindy was in her brother's room, watching a screen full of naked men with hard cocks mindlessly thrusting and tugging, hearing the sound of her own brother jacking off beside her. The air in the room smelt like sweat and leather and some other scent she couldn't quite identify but felt like she could get drunk off of. Earlier, walking out of here had seemed like the immediate urgent option, the most sensible thing in the world.

Now, she wasn't sure if she could even if she wanted to.

She might have had more reservations about what she was trying to attempt if she'd ever had much of a sibling life with her brother. But functionally speaking they'd always largely been strangers who shared a house, attending different schools and living different lives. He'd been polite, but not familiar. They'd never exactly been close. Distant was a better word for her brother: distant, and distractingly hot.

Besides that, she'd already shared everything about herself with this Jane Doe person, who definitely had more important things to worry about. One more item on the pile of humiliation wouldn't hurt.

"Can..." Cindy swallowed, her throat dry. "Can you turn my brother back on, please?"

The speakers clicked back online. "I think he's pretty turned on already, let's both be honest here."

Cindy flushed red, and the owner laughed. "Kidding! Kidding. Hey, uh..."

"Roy."

A bitcrushed snap of her fingers. "Roy! That's it. Roy, wake up and pay attention to the image your sister is about to show you."

Roy didn't so much wake up as he simply came back into awareness, no yawning or slow rise to be seen. He didn't stop masturbating, but did smile easily as he saw Cindy, even as the warmth of his smile didn't extend to his eyes. "Hey! What's up? Did you have something for me?"

Cindy chewed on her nail. It was make or break time here. But she wasn't sure she had it in herself to-

"Need anything else from me, or can I get back to my boytoys?"

Fuck, that was right. Cindy shook her head before remembering she should probably try and be more polite. She didn't want to lose the license before she even got to use it. "No! No. Everything is fine. Thank you so much. I can handle it from here. In fact..."

Cindy scrabbled for the mouse and frantically clicked the red cross at the topmost left corner of the screen. It was only when the server window shut down and the wall of men was gone that she felt like she could breathe. While she was there she also turned the volume all the way down and lowered the brightness: she didn't want any more interruptions.

Steeling herself, she turned back to Ray, and without another word brandished her phone at him with the image pulled up.

He screwed his eyes up for a moment to see in the darkened room. She could pinpoint the moment that understanding dawned. "Damn. Well. I guess that's that. So what? Want me to do all the chores? Give you some of my paycheck? I'm not sure I see the angle here."

Cindy breathed out. She could do this. She was in control.

She reached down and unbuttoned her shorts, letting them fall down around her legs and stepping out of them towards her brother's chair. The fact he was still trying to look composed and put together while naked and jerking himself off really helped sell that this wasn't some trick or joke, that this was real and about to get a lot realer. Next came her underwear, functional cotton briefs she'd brought on sale in bulk.

That was when her brother seemed to get the message. "Wow. Guess you're more freaky than I thought. Can't say I ever thought about doing it with you, but if that's what floats your boat-"

"Shut up. Just shut up. Stop talking." Cindy ground a palm into her forehead. "Your voice is so annoying. And stop fucking jerking off!"

His mouth didn't close, but words did stop coming out. He also rested his hands onto his thighs, cock still standing proudly in the air and quivering back and forth.

Finally. Quiet. She could think.

That let her realise that he'd been ordered to jack off earlier by the owner. What she'd just said went against that. This license was real, and in all likelihood would work on any men she met. The world was open to her.

But best to focus on just the one man for now.

She plodded over to her brother, not bothering with any kind of sexy strut or showing off her body in the process. She didn't need him to be turned on when he was this hard already, and she wasn't doing this for his pleasure. She knew for a fact he'd had a girlfriend or three in his time, had heard the end results of their "home dates" through the walls more than once and sometimes ended up getting off to them. He'd always been luckier than her in every respect.

This was just payback.

She stood above him, a rare experience thanks to his height advantage. She bent over, resting her hands on the armrests of his fancy padded chair, and pressed her lips to his. For a few moments it was just their lips pressing together, until she opened her mouth and pressed her tongue into his. He responded by fighting back, extending his own tongue, cupping his hands to the side of her face-

"Stop."

He stopped immediately, freezing in place.

"You still aren't getting it. You do not do anything I do not specifically ask for. Do not reciprocate, do not take the lead, do not show me how it is done." Cindy realised her voice had dropped an octave. She wasn't aware she could do that. "Just sit there and let me do what I want to do."

No response from her brother. Good. He was learning.

Cindy went back to kissing him.

That sustained her attention for an embarrassing amount of time. She'd always understood why couples kissed in the abstract, but it felt amazing in a way that nobody had ever really gotten across to her. She could feel her whole body heating up just from dragging her tongue around the inside of her brother's mouth.

But eventually, that proved to not be enough. She had to have more, and this chair was not the place to have it. The mattress in the corner might have been cramped, but that worked just fine for her purposes. She was tempted to ask him to move with her over to the bed, but on a whim she instead just grabbed a handful of short curly hair and pulled him up. She wasn't strong enough to move him by ****, obviously, but in response to the tug on his head he staggered to his feet under his own power.

She "dragged" him over to the corner and "threw" him onto the bed. He sat slumped against the wall, but a couple of deliberate pushes and pulls had his head in the centre of the mattress and his lower body hanging off the edge of it. She'd already gotten rid of her bottoms and didn't seen any reason not to keep her shirt on. It was comfortable. So instead, she just carefully stepped onto the bed, straddled his head with her thighs on either side, and slowly lowered herself until her pussy was pressed against his mouth.

For a moment, she felt disappointment. For what was supposedly some height of female pleasure, it basically felt like rubbing herself off on a soft and bumpy surface. Then she realised there was a reason for that: he was just lying there with his face frozen, not doing anything.

On the one hand, good on him for listening. On the other hand, she expected some effort. So with a strange kind of sarcastic happiness, Cindy repeated something she'd said long ago to her brother and had never thought she'd seriously repeat.

"Eat me."

He got to work immediately. Split second worries of sharp teeth and biting vanished as he began to delicately lick: it turned out toys were capable of understanding nuance. She moved back and forth slowly, making him bend his head this way and that to keep up the good work. And it felt phenomenal. She could tell that he wasn't the best at this, that he was largely just licking based on secondhand descriptions of what felt good to the point he hadn't bothered touching her clit once, but for someone as new to all this as she was it still felt incredible.

While he got to work on her, she decided to examine him. His cock was impressively large, at least to her eyes, especially since it was still standing straight as an arrow up from his crotch even minutes after he'd finished jacking off. Some residual instruction from the owner, she was guessing. She tapped it a couple of times, and couldn't help giggling slightly at the texture, hard yet spongy at the same time. She wrapped a hand around it, finding it difficult to touch her forefinger and thumb around the girth. This thing was going to break her in half unless she warmed herself up first.

Speaking of which, while Ray ate her out, she was kind of curious to see what all the fuss with blowjobs was about. She knew men loved them, but had also heard bits and pieces about some women enjoying them. It could be worth a try if there were no consequences, right?

She leaned down and, sticking her tongue out, did her best to insert her brother's cock into her mouth.

Three seconds later she was hacking and gagging onto the floor. She'd barely fit the tip into her mouth and it had been awful, tasting of old sweat and piss and some unpleasant meaty aftertaste that wasn't leaving her mouth no matter how much she tried. That had been awful. Getting the whole thing down her throat wasn't just impossible, it was senseless. Why did anyone put themselves through that?

No more giving head. Cindy's sexual journey might have just been beginning, but she felt fully confident in making that choice. Leave it to the men to use their mouths on her.

Speaking of which, despite his ineptness he was actually getting her quite warmed up. Another ten minutes of this and she might even cum. But she wasn't wasting her first orgasm by way of another person, or at least a toy, on shitty oral. She wanted the real deal.

She sat up and shuffled off of Ray, then changed his positioning again until the mattress was stretched out vertically and he was lying on it with his arms tucked into his sides, cock standing proudly in the air. Cindy would have preferred lube, but she was turned on enough that it probably wouldn't matter either way. Planting her thighs beside his hips this time, she braced herself against his chest as she used one hand to get his cock into position. She just had to get the angle right so that if she pressed down...

Cindy let out a low gasp as the tip pushed into her.

There it was. She'd broken her hymen masturbating a long time ago, so it slipped in without issue at first. But pretty quickly she found herself coming up against the sheer length of the thing, knowing that if she was going to take it down to the base she'd have to brace herself and push through some tight territory.

But then again...

Why was she bothering? She didn't have anything to prove by taking it all, and how he felt about it didn't matter. What she had here wasn't a partner, but a sex toy with a lot of useless peripherals and a cock that she'd accidentally gotten in too large a size. Why would she care how it felt? She'd use as much of its length as felt comfortable to get off, and anything else didn't matter at all.

She pushed herself back and forth on his cock, shallow thrusts that stretched her open nonetheless. She was smaller than she'd thought she was going into this. Good to keep that in mind. Still, she was able to get enough of it in that she could spare a hand to feel herself up, to grope a tit and reach down to rub at her clit. It felt incredible, far better than the improvised dildos she'd used over the years, all warm and hard and the exact right shape and size to hit the spots that drove her wild.

Still, that didn't mean she could just give in to the pleasure quite yet. She felt Ray twitching beneath her and immediately stopped, staring at him quizically. "What are you doing?"

No response. She sighed. She'd have to be more specific with her orders in future. "You can talk."

He managed to grunt out a single word. "Cumming."

And that was an ice cold bucket of reality. She couldn't believe she'd forgotten about that, hadn't even bothered with birth control or a condom. She had to figure out a quick fix. And if this level of control was really as crazy as the owner said it was...

"I don't want any weird **** babies. I don't actually want any babies, period. So don't cum, alright? No semen. Just let me enjoy myself."

And with that, she went back to bouncing back and forth on her toy brother.

It didn't take long after that. Part of it was how good her brother felt, but most of it was the final fulfilment of a fantasy she'd held ever since she'd started thinking about sex in concrete terms. This was it. She was doing what she wanted, how she wanted it, at her own pace, and she didn't need to give a shit what the man thought. It was intoxicating.

She came with a serious of low moans, legs clenching together and muscles locking up, feeling the heat flower deep in her belly. Far more powerful than anything she'd gotten before with her own fingers. She rolled off her brother and stared at the ceiling for a moment, legs open and eyes wide.

She'd gotten it. Fucking her brother hadn't exactly been a number one fantasy, but that hadn't mattered in the moment. And she could give the same treatment to any guy she felt like. She had plenty of work left to do.

But that could come after. For now, Cindy had to get the hell out of her brother's room.

And that was when she noticed a message from the chatroom appear on his desktop.

Hey, Cindy! So, quick thing. If you want to actually close a group chat like that, you can't just press the x button. That only minimises it.

Cindy had been flushed before. Now, she was outright blushing. That meant that everyone in the groupchat, including the owner, had seen-

Hey. Calm down. It's not the end of the world. Plus I did way weirder shit on my first day. You go for it, alright?

A brief pause before one final message.

Anyway, I'll let him go from the server for now. You can keep exclusive access. So long as he keeps posting nudes to his socials I'm happy. So keep on enjoying your gift! And make sure to play well. It's what you deserve.

With careful hands, Cindy reached up to shut off the computer. That was enough of that for one day.

She was almost out of the room when Ray spoke.

"Can I cum?"

She looked back at him to find him still lying on the bed, still rock hard. "I thought I said you couldn't speak."

"You said I was allowed to again as well. Please. I've been edging for hours, and that felt really good."

She could have pity on him and let him get off. Not with her body, obviously, but he could masturbate by himself if he felt like it. But something about the way he'd looked at her earlier, the attitude he'd had around the house. She felt as if this newfound power meant she was going to have to make a choice about how far she was willing to take it sooner or later.

Best for it to be sooner. That, and she'd obviously meant for him to stay silent afterwards. He was following the letter of the rules instead of the spirit, and she didn't appreciate it. So with that in mind...

"No. No getting yourself off while you still live with me either. In fact, stay that hard all the time unless it's a health risk or whatever. Go to your lectures like that. And if anyone asks, say it's over your sister."

Ray nodded understanding. No sadness, no anguish. No injustice. Just an acknowledgement that she wanted something, so as the toy he was going to do it. That was all there was to it.

Cindy could get used to this.

And for the rest of the day, she planned to.