Natalie and Jill Pt 1 (2024)

Cora sat across from Natalie, thoughtfully sipping her beer. They were discussing the possible ways for Natalie to make the next move in her and Jill’s relationship.

“I mean, we’ve been on six dates in the last two weeks. I think we’ve established fairly well that we want to be more than just friends, plus the amount of times we’ve ended up in bed together during those six dates would certainly corroborate that…” Natalie said laughing before taking a deep gulp of her whiskey sour. Cora smiled and rolled her eyes.
“Okay so what’s the next step though? Are you willing to start a relationship with her before you talk about…you know?” Cora asked gently. Natalie took a minute to answer, obviously struggling with the question.
“I mean, yes and no. I really do like her, but I’ve learned in the last five or so years that the other thing is a pretty important factor for me in relationships. I should probably discuss it with her before we get too much further into this. I wish it was as easy as it was for you and Emery” she said, sighing a little.
Cora laughed and shrugged. “What can I say, the brats just gravitate towards me. But seriously, considering how much she knows about the whole thing from Emery and I being around, it won’t be like explaining it to someone who has no familiarity whatsoever. You have at least a small step up. She’ll know the basics of what it entails.”
“That’s true. Do you think I should have the conversation with her alone or would it be helpful for you two to be there?”
“Definitely alone. She should feel that this is something between the two of you, not all four of us. I’m sure she’ll have questions that she might feel more comfortable asking Emery but the initial conversation should come just from you.”
“Good call. Alright, that’s the plan then. We were going to get together later tonight so I might as well bring it up. No time like the present, right?” She quipped, draining the remainder of her drink and standing up to slip her jacket on.
“Thank you for this. I already paid the tab, but you can get us next time” Natalie said, winking. “Are you gonna make it home okay? Want to share my Uber for part of the way?” She asked as Cora stood up too, stretching.
“Well thank you for paying! Yeah I’ll make it home just fine, I’ll hop on the light rail. Let me know how it goes, okay?” She said, giving Natalie a quick side hug as they parted ways outside the restaurant.

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Natalie knocked softly at the front door of Jill and Cora’s apartment and took a deep calming breath. She knew she would have to have this conversation eventually, because it truthfully was very important to her. But there had been a few girls she’d tried to broach the subject with that did not take it well and more than one who had called her a freak. But as she got older, she’d learned that this really was a “deal breaker” situation for her, so she had to stick to her guns.

Jill answered the door and grinned, opening it wider to let Natalie come in.

“Hey, come on in! I don’t know what you wanna do today, but I haven’t managed to come up with anything” Jill said, shrugging.

“Actually, I was hoping we could chat for a bit. Is your room okay?” Natalie asked, smiling so that Jill could see this wasn’t necessarily a “break-up talk.”

“Sure! Um, lemme get some coffee first. Want some?” She asked heading off to the kitchen to put a pod in the keurig.

“No, thank you” Natalie said, watching patiently. Eventually they headed off to Jill’s room and closed the door. They both sat on Jill’s big king sized bed, Jill struggling slightly to get up without spilling her coffee.

“Maybe you shouldn’t drink coffee in bed?” Natalie said, helping her up and laughing. Jill scrunched her nose and shook her head before taking a big gulp of her coffee. She then sighed and looked into her mug.

“So…what is it you wanted to talk about?” Jill asked softly, her nerves getting the better of her despite herself.

“Well, this is something that was going to come up eventually so I’m sure you’ve thought about it a time or two. But you know the kind of relationship that Cora and Emery have? The…different aspect of it?” Natalie said, pausing. Jill only nodded, a slight blush appearing across her cheeks.

“Well that’s how I know Cora, because we’re both what you would call Tops. We’re both a part of the domestic discipline community. Do you know what that is?”

“Well, no. But I could guess?” Jill said, still looking directly into her mug.

“Okay. Well we both strongly believe in incorporating discipline into our relationships, just the way that you’ve seen. This is something I’ve known about myself since I was fairly young, though it took some time to really iron it out. So I wanted to talk to you about this, because I’ve also learned that this is something I’m not necessarily willing to compromise on. I do care for you greatly, and I would like to progress in our relationship. I would really like to ask you to be my girlfriend, but I needed you to know that beforehand. I absolutely understand if you’re hesitant or scared or just flat out opposed. But I need to know exactly what you think about the whole thing,” Natalie said, sighing as she finished talking. She wanted to take Jill’s hand but she didn’t want any outside factors to feel like manipulation into a certain answer.

Jill took several moments to gather her courage before clearing her throat. She finally looked up from her mug.

“Well like you said, I have thought about it. I’ve talked to Emery about it a lot too. I won’t lie, I am scared of it. But from what I’ve seen, I think it’s something that could be helpful to me. I can’t exactly say I’m 100% in it, because I haven’t experienced it. But…I’m…yeah” she finished, her blush deepening.

“Okay. Well just know that you can change your mind. We can explore whatever you want to make you get a better feeling for it. What are you feeling?” Natalie asked, taking Jill’s hand finally. Jill looked at her and bit her lip. Almost two full minutes went by before she finally managed to speak.

“I um…I got written up at work yesterday for climbing the stockroom shelves. I got in trouble once before for doing it instead of using a ladder because I fell off the shelf I was on. They um…they said I’d get fired if I did it again. But I did it again today without getting caught. Maybe…?” She started and then lost her confidence. She looked down at her hands and waited.

“Maybe you deserve to be put across my knee and spanked for being reckless and imprudent? I’d say yes, you do. Sounds like there’s no better time than now to see how you feel about domestic discipline. I’ll only ask this once, but are you sure?” Natalie asked, tilting Jill’s chin up to force her to look her in the eyes. Jill nodded and sniffled lightly.

“Okay. Well because this is a trial run of sorts, you can have a safe word. You can use it if you’ve changed your mind or if you need me to stop for any reason. Will you remember strawberry?”

“Strawberry. Yeah I can remember that, I’m allergic to those” Jill said, laughing awkwardly.

“Alright. Then stand up” Natalie said, looking around the room to assess the chair situation. The only chair available was a big fluffy looking reading chair in the corner, but it would do. Jill had gotten to her feet and set her mostly empty mug on the dresser, waiting nervously for Natalie to give her more instructions. Natalie made her way around the bed and then sat in the chair. From her position, she could reach out and touch Jill. She tugged her closer by her two front belt loops. Jill’s hands automatically went on the offensive and tried to pull her hands off.

“Jill, move your hands. I’m taking these down. You can keep your underwear on for right now but these jeans are coming off. Move” she said sternly, enjoying the small whimper that escaped Jill’s lips. Natalie managed to unbutton her jeans and then wrestled them down the girl’s legs.

“Step out” she said, holding onto Jill’s hips to keep her steady. Jill obeyed, and then found herself quickly being tugged down across Natalie’s thighs.

“Wait!” Jill groaned, adjusting herself as much as she could.

“Yes?” Natalie asked, one hand on Jill’s back and the other on her leg. This had all happened rather fast and she’d understand if Jill changed her mind.

“I don’t know…I’m just scared. Is it going to hurt?” Jill asked, her hands flat on the floor. She could feel a slight breeze on the underside of her cheeks where her underwear didn’t quite cover.

“Yes, sweetheart. It’s going to hurt a lot. It is a punishment, so that’s what it’s meant to do. It’s going to sting and then eventually burn. It’ll feel like someone is slowly giving you a sunburn, and then is smacking that sunburn. Generally, I would decide when you’ve learned your lesson. But because this is your first time and it’s not exactly the same, you have your safe word. I want you to get a feel for what a real spanking will be like, so that’s what I’m going to give you. But know that you are absolutely in control right now and I will stop the second you say strawberry. Okay?” Natalie said, rubbing Jill’s back in slow gentle circles.

“Okay. Alright. I uh…okay. I do want this. And if Emery can do this, I sure as hell can. Alright, I’m ready” she said, bracing herself a little. Natalie gave her another few seconds before lifting her hand and bringing it down swiftly on the girl’s right cheek, then repeating the movement on her left cheek. Jill made no noise, but clenched her cheeks and fists.

“You need to relax, Jill. If you keep your bottom like that, it’s going to bruise way more quickly. Relax” Natalie said, giving her a moment. Jill groaned but did what she was told. She was almost immediately rewarded both with a hard smack to her right cheek, and a soft spoken ‘good girl.’ The spanking continued, the volley of smacks almost rhythmic. After a minute or so, Jill began to squirm and whine. It wasn’t so bad at first but it was really starting to hurt.

“Okay stop. It hurts Nat!” Jill whimpered, kicking her feet. Natalie stopped but made no move to let her up.

“You have a safe word, young lady. If you need me to stop for real, that is what you need to say. If you’re just saying stop for the sake of saying it, you need to stop kicking and fighting” Natalie said calmly and slowly. Jill caught her breath and relaxed her body.

“Kay” she said quietly, wrapping one hand around Natalie’s ankle. Natalie nodded and resumed spanking. After maybe 30 seconds, she decided it was time for the underwear to come down. She slipped her fingers into the waistband on either side and slid them over Jill’s cheeks and down her legs. Jill said nothing, but groaned in embarrassment. She had seen Emery get spanked, and figured she’d end up getting it on the bare bottom too. She just didn’t want to think about exactly what Natalie could see of her upturned, exposed butt.

“So tell me why you think it’s okay to climb things that aren’t meant to be climbed, and to blatantly do something you were told you’d be fired for doing” Natalie said, her hands raining down harder blows to the bare, reddening cheeks before her.

“Ow! Well I-owww! I just don’t like to-ow! I don’t like to go get a ladder and I can climb it perfectly fine. Owww Nat please, I’m sorry!” She sniffled, tears flooding her eyes.

“You cannot climb them perfectly fine. You told me you fell off. And even if you hadn’t, it was still an incredibly dangerous and petulant thing to do” Natalie replied, beginning a new onslaught of spanks to Jill’s upper thighs. The resulting wail was impressive, definitely alerting Emery down the hall if she hadn’t already heard.

“Owwww ow yes okay alright! I shouldn’t have done it! It was stupid and I won’t do it again!” She cried, throwing her hand back to cover her sensitive thighs. Natalie swiftly took Jill’s wrist in her hand and pinned it to her back.

“You’re damn right you won’t do it again. If it does happen again you’ll be right here, back across my knee getting your little butt blistered. Do you understand me?” Natalie asked, slowing her smacks to Jill’s cheeks, but increasing the intensity. These were the smacks that ensured Jill would be remembering this over the next day every time she sat down.

“Yes, Nat please! Please Natalie I understand, I’m sorry!” She wailed, tears flowing freely down her face, her wiggling completely ceased. She’d finally given in to the punishment, allowing herself to be thoroughly spanked. After a moment, Natalie stopped. She let Jill cry while she rubbed circles on her back.

“Shhhh sweetheart it’s okay. It’s all over. You’re forgiven, and it’s all done with. You’re okay, Jill, you’re okay” she whispered as Jill composed herself.

“May I stand up please?” Jill asked with a sniffle. Natalie helped her up, and stood up too. She wrapped the girl in her arms, pulling her close against her chest.

“You did so well, gorgeous girl. You did wonderful. And it’s all over now” she said, kissing the top of Jill’s head. Jill said nothing for a moment, then laughed quietly.

“What’s so funny?” Natalie asked with a smirk.

“It’s just…I was thinking about how I never got spanked as a kid. But then my next thought was ‘well that explains some things’” she said, laughing even more.

“Well yes, maybe it does. But I believe spankings are more helpful for adults. I don’t believe in spanking kids. Just little brats like yourself” Natalie said, squeezing the girl in a tighter hug. Jill snuggled close and smiled.

“I um…I wouldn’t mind if you keep doing it. In the future, I mean. I guess it is kinda helpful, even if it totally sucks” Jill said softly, embarrassed to be saying that she’d be okay with getting spanked again.

“Are you sure? You don’t have to decide to do this just for me. It’s not for everyone…” Natalie said, smiling despite herself.

“I’m sure. Just…maybe not another one right now because I’m fairly certain my ass will fall off if you do it again” she said, laughing freely. Natalie rolled her eyes and chucked.

“Don’t give me a reason to spank you twice in one day, and I won’t ever have to” she said, before bending down to pick up Jill’s underwear and handing them to her.

“Alright, you can put these back on now. I want to talk more about everything but I won’t be able to concentrate with a half naked gorgeous girl” Natalie said, flopping onto Jill’s bed and stretching her aching shoulders. Jill obliged, though her pants were significantly less comfortable than they had been just 20 minutes prior. There was a lot to talk about though, so she figured she could probably suffer through it, if only for Natalie.

Natalie and Jill Pt 1 (2024)

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