When Alison first heard her little brother had a date, she was shocked. Tommy was still just a baby, wasn’t he? What Jezebel would ask out a baby?

But no, it wasn’t like that. He had asked out her – Zoe, a girl from his chemistry class. He hadn’t completely expected her to say yes, but she had, and now he came to his trusted big sister with questions. Questions about how to dress, how to act, what to talk about. As he kept going – and as he took notes on Alison’s answers – she had to admit it to herself.

He wasn’t a baby anymore. He was a boy, a teenaged boy, and more thoughtful and mature than some she’d dated herself. He was almost ready to date.

Almost. But he still stuttered, he still fidgeted, he was still nervous. Alison wasn’t going to let that bird out of the nest, wasn’t going to throw him to the wolves that were other girls, until she was 100% certain.

That led them straight to their plan: a practice date.

They would use the kitchen table for it, after dinner and after everyone else had gone to bed. It was just roleplaying, so they wouldn’t actually go out together. But they did dress up.

As Tommy stepped out of his bedroom, he was still arranging his tie – but still, wow. Neatly pressed slacks and tucked-in button shirt, simple but classic. They helped his green tie stand out, and emphasised how well it matched his eyes. He’d brushed out his usually-dishevelled brown hair, showing that he could tame it. Her littler brother looked handsome. When she’d been his age, she wouldn’t have minded dating a boy who put in that kind of effort, who cleaned up that nicely.

And his cute green eyes went wide when he saw her. “D-Did you really have to wear that dress?”

Alison arched an eyebrow at him, hands on her hips. “First lesson: you don’t greet your date by asking her, ‘did you have to wear that’. C’mon, try again.”

He whined like a puppy, but he knew what he was supposed to do. “You look great, Alison. That dress is very...” He struggled for the right word. “ ... flattering.”

Damn right it was. It was Alison’s favourite little black dress, with cap sleeves, a scooping neckline, and a short skirt. She twirled her way towards the table. “Much better. And yes, I had to dress like this. If this Zoe is as into you as she should be, she’ll dress up. You need to be able to handle cleavage.”

Tommy hurried ahead of her to the table and pulled her chair out. “Not cleavage like yours. Zoe isn’t that b-busty.”

He sweet little brother noticed how busty she was. Alison wasn’t sure quite how she should feel about that ... but she found it put a grin on her face as she settled into her seat. “Then if you can chill out about my boobs, you can definitely chill out about hers.”

He pouted behind his blush as he sat opposite her. “A date isn’t just about boobs. It’s about ... about spending quality time together and getting to know each other. Or that’s what the website said.”

She had to laugh. So conscientious. Of course he’d done research. “Well, that website is right. So go on, get to know me.” She grinned. “The best dates are basically a tug-of-war where you’re both trying to get each other to keep talking. To get things started, it’s good to ask about her interests.”

“Alright.” He smiled at her. “Played any good action games lately?”

Oh, that wasn’t fair. He already knew she loved her superheroes. But it still worked. With his encouragement, she launched into stories about her new speedster game – running on walls, dodging and catching bullets, outrunning bullets to save civilians from them. And Tommy listened, his eyes bright and engaged. He asked questions – he even got her to go back and elaborate about the time she tricked a rival speedster in front of a laser cannon, just before it fired. God, that had been fun.

Eventually, she had to stop to get a sip of water. “Okay, so you’re not bad at that. But you need to be ready to talk too.” She grinned like she was about to take vengeance. “How’s that RPG of yours going?”

He took a bit more prodding; he wasn’t used to talking openly about his solo interests. But as he gained momentum, he grew animated. It was beautiful to see. He talked about the characters like he was telling a story about his friends – just friends who led very interesting lives, fighting dark gods and their indoctrinated followers. She didn’t like story-heavy games as much as he did, but the way he talked drew her in. She leaned in closer, just as engaged as he was.

Then his words started to stumble as his eyes began to slip. She didn’t need to follow his gaze to know where he was looking.

She had to giggle, but she also felt a faint blush on her cheeks. Her little brother was looking right at her boobs. But... It’s okay, she told herself. It’s just looking.

Emboldened, she adjusted herself a little to show off better. Most of her hair was bound up in a chignon, but she had two locks left free – one of natural light brown and one from her purple-dyed streak. She nudged them to fall right in front of her chest, framing it, while she leaned more fully forward. “I’m sorry, am I distracting you?”

Tommy grumbled, pulling his eyes off her and onto the wall. “No fair. Putting things in front of me that I’m not allowed to look at.”

“It’s not that you’re not allowed to look.” She nudged his shoulder. “You’re not allowed to stare. It’s about balance. Look at my face, look at my chest, look at the wall or your glass or whatever. Not just staring at one place.”

His eyes widened. He had explicit permission to look at cleavage. Even if it was his sister’s, that was a siren song no teenage boy could resist. At first his balance was off, and he did stare for a solid for seconds.

But eventually, he got past that, and looking at her body just became a component of their pseudo-date. They chatted, they drank, and he sometimes looked at her boobs. Just enough that she could feel his boyish attraction, could know he liked her body ... and, strangely, that was a nice feeling. She was beautiful, and her brother knew it.

Alison had fun. If she’d had a date like this with any other boy, he’d get a second date for sure. But when Tommy yawned three times in one sentence, she knew they should call it quits. “Okay, okay,” she said. “I think it’s time for you to walk me to my door.”

His smile widened as he giggled, looking past her to the hallway. “What, like your bedroom door?”

She poked out her tongue. “Yes. It still counts. Come on, it’s a classic rom—” She paused. She wasn’t so sure about being romantic with him. “ ... it’s a classic date move,” she amended.

He knew what she’d almost said. It sent a fresh blush over his cheeks, but he didn’t back down. “Alright, then.” He pulled her chair back to help her get out. “Lead the way. And, um, how did I do?”

She walked slowly, trying to milk the hallway for as long as a driveway. “Pretty good. Good conversation, could balance. You could have touched me more, though.”

“Wait, what? Touched you?” His eyes dipped.

And hers rolled. “Not those. I just mean light stuff. On the shoulder, or the arm.” She demonstrated, fingers running along Tommy’s sleeve.

“Oh, right. Or maybe, like, your hair?” While they lingered by the door, he ran his fingers along that free, dyed lock.

Alison’s breath caught in her throat. That touch, so gently affectionate... “Yeah, that’s good.”

“But...” He hesitated. “What if Zoe doesn’t want me touching her like that?”

That was right. Alison wasn’t just training him in her own tastes; she was getting him ready for Zoe, for some other girl who was going to steal him away. She took deep breaths to calm and control the jealous fury in her chest, and gave him a sweet smile. “That’s why you keep it light. If you touch her arm and she doesn’t like it, read the signals and stop. But ... be gentle, just like that, and any girl should like it.”

Any girl. He knew that meant her, too. Both his hands fidgeted in front of him as they stood by her bedroom door. “So, uh, how do you say goodbye at the end of a date?”

Yes. There was still one more thing he had to learn. Their date wasn’t done yet. “You don’t says goodbye, you say goodnight. And if you’ve showed her a good time ... it might go something like this.” It’s okay, she told herself as she leaned down and puckered her lips forward. It’s just a kiss.

Except it wasn’t even that. Tommy didn’t close the distance. He just stood there, staring, wide-eyed. Damn it, she’d have to teach him out of leaving a girl hang—

He kissed her.

It was clumsy, his lower lip on her chin more than her mouth. It was too soft and hesitant. And it was almost far too soon.

Alison almost said goodnight then and there. But... It’s okay, she thought. It’s just a proper kiss this time. “Not like that. You kiss her like you mean it. Like you want it. More like this.” She sealed her mouth over his, tight and greedy.

At first, he just let her take his breath away. Then he joined in, his eagerness making up for his clumsy inexperience. Eagerness? Was he just kissing her like she’d told him to, or did he really want her?

When the kiss broke, her head was spinning with possibilities. They still had so much date left. It filled her mind so tightly, she didn’t even think to make justifications. She just opened the door behind her. “And if you’re really lucky ... she’ll invite you in.”

With the door closed behind them, she gave her brother more kissing practice. Plenty more. She wasn’t sure whether she’d got his first kiss period, but she absolutely got his first French kiss, in a breathless tangle of tongues.

Heat. Feeling him kiss her, hearing his soft and boyish whines of pleasure, her body grew hot. Too hot to be comfortable with clothing. First, she let her hair down, brunette and purple curls tumbling to her chest. Next went her dress. Even once she’d unzipped it, it fit so tightly that it took some peeling and wriggling to get it off. Then she found she was uncomfortable with his clothing, too, and worked open his shirt’s buttons.