Summary: Jensen’s not like the other sugar daddies – he doesn’t want to mix money with sex. But meeting Y/N might have him changing his mind.

Part Tags: None really, bit of nerves, mentions of sex, fluff, teasing, flirting

Part WC: ± 5.7K

Sweet as Sugar Masterlist

The nerves are dancing around Y/N’s stomach as she steps up to the dock. The boat is up some steps, and the breeze is cool after such a humid day. It’s so quiet on the dock, but Y/N isn’t sure they’re going to stay in one place. She gets to the top and notices a waiter standing at the entrance, greeting her with a polite smile. 

“Urm, Y/N,” she tells him nervously, tugging her fingers in front of her anxiously. 

“Right this way, Miss Y/L/N.” He smiles politely at her and leads the way. She steps onto the boat and lets the waiter lead her to the front of the large boat. The view from the deck spans the whole ocean ahead, including the setting sun that’s giving everything an orange glow, and the whole place takes her breath away. There’s a man standing at the bow, leaning on the railings and enjoying the view, and Y/N bites her bottom lip anxiously, trying to be careful not to ruin her fresh lipstick as she draws closer.

The man turns around and smiles warmly when he sees her approaching.

“Thank you, Justin,” he smiles, nodding at the waiter who steps away. “Y/N?” he asks, bringing his attention to her.

“Yes, you must be Jensen,” she replies quietly. 

“Don’t be nervous, sweetheart, I promise there’s nothing to be afraid of.” Y/N nods a little, and another waiter approaches her side with a tray, two champagne flutes filled with golden liquid inside. “Champagne?” he offers. Y/N hesitates, a little conscious that she shouldn’t just take a drink from a stranger. And whilst Jensen isn’t exactly a stranger, since they’ve talked over text, and she’s been set up with him through a friend, she’s still never met him in person before. It’s easy to lie on the phone. But she trusts Katie’s judgement, and Katie told her that Jensen was a good, trustworthy man. 

Y/N reaches for the glass she’s being offered and smiles politely, taking a small sip. He watches for a second and then sips his own. 

“So, we’ve been talking about college but you never told me what you study,” Jensen points out, guiding her over to a plush looking couch. 

“Right, of course, I’m studying English,” she smiles softly. 

“And it’s your first year?” he checks.

“Yeah.” Y/N notices that Jensen sits a respectable distance from her, and she relaxes slightly. “I’m enjoying it so far,” she adds. 

“That’s good. Are you busy with it?” For the first time that night, Jensen’s question makes her remember why she’s even here. 

“It’s manageable,” she replies with a soft nod. 

“And that’s how you know Katie, right?” he asks next. 

“Yeah, sort of. She’s from my hometown, but she happened to go to UTD too. She’s a school friend’s older sister, and when she found out I’d be coming to Texas we got talking and got close.” 

“How did you meet Katie?” She pries. Jensen smiles softly.

“I was on one of those apps. I hated it, Katie was the only good thing to come out of it.” 

“So you’re not on an app anymore?” Y/N asks, just to make conversation. 

“No, that’s why I was glad that Katie put us in touch with each other.” Y/N feels herself blush, and lifts her drink to take a sip. “I’m gonna miss Katie a lot, me and her got very close, but I’m really happy for her, and I’m glad that she’s found someone she wants to spend her life with.” 

Jensen looks out at the view for a moment, and Y/N does the same, and she notices they’ve started to move, she’s assuming they’re going a little further into the ocean. 

“Is this boat yours?” she asks.
“It is,” he confirms. “Being on the water is one of my favourite things.” 

“So what exactly do you do, if you don’t mind me asking?” She looks at him and he licks his lips. 

“Well I opened a brewery about fifteen years ago, and then we expanded and opened several more around the country, and from there I started investing in properties too,” he explains. Y/N nods her understanding. Katie had told her Jensen was well off, but she’d never imagined owning his own large boat kind of rich. This thing probably cost him more than her entire apartment complex. 

Y/N doesn’t want to explicitly bring up exactly why she’s here, even though she has a million questions, so she stays quiet and waits for him to ask his own. He’s the one with the experience after all. The boat seems to have stopped, and Jensen stands up, holding his hand out for her. She takes it carefully and he helps her to her feet. He lets go once she’s standing, and leads her over to a different part of the deck where there’s a table for two laid out. The sun is setting even lower now, the orange even deeper as night draws in, and there are fairy lights wrapped around the railings of the deck. It’s like something out of a movie that Y/N never dreamed she’d be part of. Jensen pulls Y/N’s chair out for her, and she takes her seat, watching as he rounds to his side of the table and sits down too. He takes another sip of his drink and then sits back, linking his fingers together. 

“So, what has Katie told you about me, exactly?” Jensen finally asks. Y/N feels herself blush just thinking about the fact they’re starting to talk about the arrangement, and clears her throat. 

“Well she told me that you’re kind and sweet and funny,” Y/N starts, but she knows what Jensen really meant, and she takes a deep breath. “And she told me that you – urm – gave her money, and took her places.” She glances at Jensen and then quickly back down at her plate. Jensen’s smiling softly, clearly a little amused by her embarrassment. 

“You’ve never done something like this before, have you?” he asks gently. 

“No, if I’m honest, I’m only doing it now because I need money for college stuff, and Katie trusted you, and I trust Katie.” Jensen nods his understanding. 

“You’ve never been interested in being a Sugar Baby before?” he asks next. Y/N shakes her head, now even more nervous that the elephant in the room has been addressed. 

“No, I always assumed there was sex involved so I never considered it, but… well, Katie said it wasn’t like that with you.” She glances up at him, seeing him shake his head in confirmation. 

“No, no sex and no photos or videos either. I don’t mix that stuff with money.” The conversation is halted when the waiter approaches with their starters; prawn cocktail. “Thank you, Ollie,” Jensen smiles. Y/N smiles herself. Jensen seems to know the name of everyone on this boat. He doesn’t seem stuck up or like he thinks he’s more important than the staff, which she likes to see. 

“So, if you don’t mind me asking… why do you do this?” Y/N finds herself asking, curiosity getting the better of her. 

Jensen sighs slightly and looks out at the view, “I’m too busy for a relationship, and I’ve got a hell of a lot of money just sitting there. I figured, why not help someone who needs it? I like feeling like I’m helping someone out, and I quite enjoy spoiling someone. And I’m going to be honest, sometimes I just like to have some company. A lot of the time I’m just surrounded by businessmen.” 

“It just seems strange to me that you’d pay me to do things I want to do and buy me things I want, and yet you’d not get anything out of it,” Y/N confesses.

“Sure I would. I’d get to know that I’m making someone very happy, and helping them out. And I’d get someone to talk to and get close to. My money isn’t going to do anything for me when I’m dead.”

Y/N picks at her food, but she doesn’t feel that hungry. She looks across at Jensen and he’s watching her carefully. 

“So, I’d be like a girlfriend, but no sex?” she asks. Katie had told her that that had always been the deal with Jensen. He’d never been inappropriate, he’d never even tried anything with her. They’d sometimes hold hands or he’d put his arm around her when they were out, just to look like a normal couple, but she’d assured Y/N that he was always respectful and that she had always wanted to do those things. Katie seemed to love Jensen, and the way Jensen’s been talking about Katie, he seemed to love her too, but something tells Y/N that it’s nothing romantic and never has been. 

“I guess you could look at it like that. I like to keep in touch with my girls, and talk to them daily, make sure they’re happy and have everything they need. I like to look after them, financially and emotionally.” 

“Girls? You have more than one?” she pries. 

“No, I like to focus on only one girl at a time, make sure she’s getting everything she needs from me. I was talking about past relationships.” Y/N nods, understanding.

“What number girl am I?” Y/N can’t help but ask. 

“Three,” he replies without hesitation. “My first girl, Lily, didn’t last long. We were both new to it, and after a few months, she decided it wasn’t really what she was looking for so we agreed to call it off. A few months later I met Katie, and obviously, she met Tom a few months back, so we had to end that.” 

“Okay, so no bad exes, no sex, and you seem nice enough… so what’s the catch?” Y/N asks with a tiny smirk. “Are you going to decide a couple of months down the line that I owe you something? Start pressuring me for more?” 

Jensen frowns at the very comment. 

“No, that would make me an asshole,” he scoffs. “I’m serious about the no sex thing. I’m not like most sugar daddies. I mean, I barely even consider myself to be one, but I guess I am, and if it makes you more comfortable, then that’s what you can call me.” Y/N giggles softly. She’d never considered being a sugar baby, not before Katie encouraged her. 

“You want me to call you Daddy?” she presses. Jensen laughs softly.

“If it would make you happy,” Jensen agrees. Y/N giggles, just the idea of not only having a sugar daddy, but then calling him Daddy seems ridiculous. “But you don’t have to, I honestly don’t care,” he adds. 

It’s quiet again for a moment, and then Jensen speaks up once more. 

“So you’ve not asked me how much money I’m offering,” he notes. Y/N feels her cheeks heat up and she clears her throat. Katie had never discussed how much money Jensen gave her, but she always had enough to have her hair and nails done and buy whatever it was she wanted. 

“I didn’t want to seem rude,” she explains. 

“It’s not rude. You’ll have to get used to not being embarrassed about money around me,” Jensen tells her softly. “So I’m willing to give you two thousand.” Y/N eyes widen, and she clears her throat. 

“Wait, two thousand a month?!” Y/N chokes out, thinking about what she could do with that amount of money every month.

“No, sweetheart,” Jensen laughs, shaking his head. “Two thousand a week.” 

Y/N nearly falls out of her chair as she stares at him with an open mouth. 

“What?” she whispers out. 

“I’m happy to give you two thousand dollars a week. You can spend it on whatever you want really, I don’t mind. I do like to see where my money is going, so I appreciate photos of things you might buy with it, but-” 

“Jensen,” Y/N cuts him off finally, swallowing hard. “I don’t need that much, that’s… too much. I just wanted enough for some college books and to help pay some bills.”  

“Okay, so how much would you like?” he asks. Y/N licks her lips and grabs her champagne, needing the courage. 

“I was thinking, like, a grand a month,” she tells him honestly. Jensen smiles softly and nods his head.

“Okay, but then you’d just be getting by, right? Don’t you want money for shopping and to get your nails done or buy nice things?” he asks.

“I don’t need any of that, just my school books and bills.” 

“Well, you have to consider the time you’re going to be giving to me too. You need to value that. I like to have weekly date nights. I’ll pay for everything, of course, and we can do whatever you want. Bowling, movies, dinner, whatever you like. And then once a month, I’d like to take you away for a weekend. Either on my boat or on the jet to somewhere else. That’s if your college work isn’t keeping you too busy.” 

“I’ll have enough time,” you confirm. “If I don’t have to work at the bar, then it gives me more time to give to you.” She knows she must sound crazy, arguing with him about giving her less money, but she wouldn’t feel right taking so much from him. “Honestly, a grand a month is plenty.” 

Jensen nods and purses his lips. “Sweetheart, you’ve got to value yourself, I’m more than happy to spend money on you, that’s what I want to do.” 

“Is that what gets you off?” The question is out of Y/N’s mouth before she can stop it. Jensen laughs, thankfully, and shakes his head. 

“Like I said before, it’s not about sex.” Y/N nods slowly and finishes her drink. The waiter from earlier, Ollie – she thinks – comes back and is quick to refill her glass. “So why won’t you accept more?” Jensen asks like he’s genuinely curious. “I’ve gotta say, I’ve never had to argue with a girl about wanting to give her more before. 

“Honestly?” Y/N asks, playing with her fork. “I’d feel like I owed you, that I was obligated to have sex with you.” 

“You’d be giving me something much more valuable than sex, baby girl.” 

Y/N stares at him for a moment, and there’s no trace on his face that he doesn’t believe his own words. 

“Okay, how about I set up a standing order for one thousand a week, and then if you ever need more, or if there’s anything you want to buy, then let me know.” 

“Okay, but I have some questions first,” Y/N tells him, feeling a little more confident than before. 

“Of course,” Jensen agrees. 

“So if there’s no sex, does that mean that, urm-”

“Yeah, you can sleep with other men,” Jensen confirms before she can finish her question. “Your life is still yours, and what you do outside of our time together isn’t my business. As long as it doesn’t interfere with our time together – within reason.” 

“Okay, so does that mean that you’ll also be with other women?” Y/N asks awkwardly. 

“Maybe, that’s not a problem is it?” he asks. 

“No, of course not, I just want to make sure we’re on the same page,” Y/N agrees. Jensen nods, and then Ollie clears away their starters, and leaves them alone. “So these dates, are they like a romantic thing?” 

“Not necessarily. We’d just hang out, get to know each other and spend time together.” 

“Like tonight?” 

“Sure, just less twenty questions and more being relaxed, having a good time. People probably will assume that we’re together, so if you don’t want to look like you’re dating an old man…” Y/N giggles as Jensen smirks at her, and then drinks some more champagne. “So what are you thinking? Do you want to give this a go?” he asks. “Do you want time to think about it?” Y/N looks across at him. There are far worse people she could be mistaken for dating. He might be old enough to be her father, but he’s very attractive. Y/N is shocked that he’s not married. 

“One more question,” Y/N tells him. It’s personal, but she needs to know. Jensen lifts his hand as if to tell her to go ahead. “Why isn’t there a Mrs. Ackles?” 

Jensen purses his lips for a moment. 

“There almost was many years ago. But she only wanted my money, and ironically, I didn’t like that. What the two of us would be doing is different. You’re not pretending to love me, I’m under no illusions that you will or that you want me in that way. There’s no sex, there’s no blurred lines. Just like sex, I don’t mix love with money either. I guess she just made it hard for me to trust women again, and I’m too busy for a real relationship anyway, an arrangement like this works better.” Y/N bites her lip and nods her head. 

“Okay,” she smiles softly. 

“Okay, my answer is satisfactory?” Jensen teases with a chuckle. 

“No, I meant okay – let’s do this.” 

– – – – – – – 

Y/N sighs heavily as she holds her head in her hands and reads through her textbook. It’s late, and she’s got another thousand words to write before she can call it a night. She rubs her temples and takes a deep breath, pulling her laptop closer after previously shoving it away in frustration. Her cell buzzes beside her, so she abandons her pursuit for her laptop for that instead, much preferring the idea of procrastinating. She sees Jensen’s name and smiles softly, sitting back in her chair. It’s been a few weeks since her and Jensen decided to try this arrangement, and whilst the money is a great bonus, because now she doesn’t have to worry about paying her bills and still affording stuff for school, the thing she’s enjoying most is getting to know him. He’s actually a really great guy. He makes her laugh and he’s sweet and kind. 

Y/N is waiting for the other shoe to drop at some point. Something has to be wrong, this situation she’s found herself in is far too “perfect”. She’s getting all her bills and expenses paid for her, she doesn’t have to work a shitty job to survive college, and she doesn’t even have to have sex with the very lovely and very attractive man who’s giving her all this money. There has to be a catch. Maybe Jensen will want sex eventually, Maybe Katie never mentioned that part because she’s ashamed. But honestly? The idea doesn’t bother Y/N as much as she thought it would. Jensen is hot, why wouldn’t she want to sleep with him? It’s only because there’s money involved that it makes her uncomfortable. She’s not an escort. She doesn’t put a price on those things. Those things are invaluable. 

Jensen: Hey sweetheart, how’s your day been? Just landed in Hawaii 

Y/N: I’m so tired, and college is kicking my ass. I’m so jealous right now 🙁

Jensen: Oh shit, only just realised you’re 5 hours ahead. It’s late there now! How are you still up? Get some sleep, sweetheart. I’d love to bring you here one day. Maybe when college is quieter

Y/N: That sounds amazing. I would sleep but I’ve gotta finish this paper, so at least I’ve got you for company <3

Jensen: Well don’t work too hard, don’t want you burning out. 

Y/N: You’re so sweet when you worry about me, but I’ll be fine. You do enough for me as it is

Jensen: I want to do as much as I can. Talking of more, how are you doing for money this month? Now you’ve bought all your college books.

Y/N purses her lips. Jensen gives her enough, enough that she doesn’t have to pay for anything that she needs, so she doesn’t need more, even though he offers it regularly. She just doesn’t want to take advantage, or make him think she only likes him for his money, because already that really isn’t the case. It’s stupid, she knows it is, because technically he’s her Sugar Daddy and that’s what they do. 

Y/N: I’ve paid all my bills too, so I’m fine thank you <3

Jensen: Okay, so your bills are paid, but do you want anything?

Y/N: No, I’m fine honestly. I have everything I could need. 

Jensen: I didn’t say need I said want 😉 

Y/N rolls her eyes at how stubborn he is and sighs. 

Y/N: If it’ll shut you up you can buy me a new phone case, this one is getting old. 

Jensen: Done. I’ll send you enough money for it. Anything else? 

She hesitates, there’s plenty of things she could ask for like new clothes or makeup or shoes, or even ask him to pay to get her car serviced to make sure everything still works. But she doesn’t want or need that stuff. 

Jensen: We have a date on Saturday, what are you going to wear? 

Y/N: You flirt 😉 

Jensen: Well? What are you going to wear? 

Y/N smirks at her phone and then seriously questions it. She’s already exhausted the three smart dresses she owns on the three dates they’ve been on together. Jensen always takes her to really nice restaurants or fancy bars, so she’s got to look the part. She can’t rock up in jeans and a shirt. 

Y/N: Clothes 😉 Or would you rather I’m naked?

Y/N laughs hard at her own reply. She’s grown quite comfortable around Jensen, and she’s loved flirting with him harmlessly. Their first date after meeting him on his boat was much like the first time they met; dinner and polite conversation as they continued to get to know each other. The second was to a bar where they both had a couple of drinks and just hung out like friends, and the last date which was only a few days ago, was to a show that she’d been wanting to see. Each time Jensen had been respectful and gentle with her, only putting his hand on her lower back when they walked, but never in a possessive or overbearing way. He was always the perfect gentleman. Each time he’d picked her up in his chauffeur car, and there were no expenses spared when it came to paying for whatever would ensure they had a good time. More than anything, Y/N had been enjoying the company and the excuse to have time away from college work. 

Her phone buzzes in her hand again and she sees that she’s received money. When she opens her bank to check, Jensen’s sent another $500. Before she can text him and complain that he’s sent far too much for a phone case, he’s text her again. 

Jensen: For your phone case and something nice to wear on Saturday. 

Y/N rolls her eyes at her screen. She knows it’s pointless arguing with him about it, because he won’t take it back, and it does now mean she can buy something new, and not wear something he’s already seen her in. 

Y/N: You didn’t have to, but thank you, Jensen <3

Jensen: Anytime, baby girl, that’s what I’m here for

Y/N: You’re here for more than that. You’re not just my Daddy. 

Jensen: Thought you didn’t want to call me Daddy? 😉

Y/N: Shut up 😛 

Jensen: I mean, I don’t mind. 

Y/N: You want me to call you Daddy? I’ll call you Daddy if you’d like. I’ll call you whatever you want. 

Jensen: I want you to call me slave. 

Y/N’s eyes widen at her screen, and she can’t help but burst out laughing. 

Jensen: That was definitely a joke, do not call me slave. 

Y/N: Okay, Daddy it is. 

Y/N changes his name in her phone, putting a money emoji next to it as a joke, and takes a screenshot to send to him. 

Y/N: There. Done. Now stop distracting me from my paper, Daddy. I’m very busy and it’s very late. 

Jensen: Okay okay, I’ll leave you alone. Buy that phone case and a dress, and let me know if you need more. Don’t stay up too late and text me tomorrow. 

Y/N: Wow, just because I called you Daddy doesn’t mean you get to turn into my father. 

Jensen: Ha. 

Y/N: Talk to you tomorrow…. Daddy 😉 x

Holding her cell phone a little higher, Y/N takes the photo of her in the floor length red dress and then sends it to Jensen. It’s her least favourite of the three she’s selected, but as the price tag is triple figures and Jensen is footing the bill, she’s happy to wear whatever he decides. She waits patiently for him to read the message, and look at the other two photos she’s sent him too. The ticks turn blue, and then Jensen begins to reply. 

Jensen: Which is your favorite?

Y/N: I don’t mind, whichever you like 🙂

It’s a lie, but Y/N’s favourite is the most expensive of the three, and she feels rude choosing that one. 

Jensen: Well I think you look beautiful in all three, so it’s really your choice. Do you have enough for them? 

Y/N: Yeah, one of them. Don’t send any more money!! 

Jensen: What about shoes and accessories?

Y/N: I have shoes at home. Just pick a dress, the store assistant is gonna think I’m stealing them! 

Jensen: All three. I’ll send over more money. 

Y/N: Jensen, no! 

–

Y/N begrudgingly hangs all three dresses in her closet when she gets home, and she sighs as she places her hands on her hips and stares at the three zipped up bags. At least she can wear her favourite one tomorrow night for their date. Her cell rings and she sees that it’s Jensen. 

“I’m not talking to you,” she tells him, playfully upset. 

“Well that’s the first time I’ve had a girl upset with me for giving her money,” Jensen notes casually. 

“Jensen, we talked about this, I feel bad taking so much, you’ve already given me more than I need,” she insists. Jensen just laughs easily. 

“And I’ve already told you, I like spending money on you, sweetheart. I like spoiling you, there’s no need to feel bad, okay?” Y/N sighs and rolls her eyes. “I won’t send you any more money this month, unless you need it. You don’t have to buy anything else on my request, I promise.” 

“Okay,” she agrees. “Thank you for the dresses, I don’t want to seem ungrateful. This is all still new to me, I’ve barely been on a date where he pays for the full meal.” 

“Well you need to get used to it, I’ve got a hell of a lot of money, sweetheart, what I’m giving you really isn’t much to me,” he insists, “and what you’re giving me in return is more than worth it.” 

“I don’t bore you?” she checks, chuckling softly. 

“Oh far from it, you’re great fun,” he tells her. Y/N smirks at the confirmation. 

“Well I’m glad you approve of me, Daddy,” she teases. Jensen laughs on the other end of the phone. “What? We agreed, you’re Daddy now.” 

“Well I’m not used to it being said like that,” he defends. 

“Sorry, do I need to be more sexy?” 

“Not at all, you’re sexy enough.” The line falls quiet for a moment, and Jensen clears his throat. 

“So tomorrow night, I’ll pick you up at seven. What would you like to do?” he asks. 

“Well, I’d actually like to do something fun,” she tells him. 

“Okay, anything in mind?” he asks. 

“I’m not sure,” she replies, biting her bottom lip. 

“Okay, I’ll think of something, wear something less formal than those dresses, though.” 

“You mean the dresses you spent almost a grand on today?” 

“Those are the ones, you can always wear them again, but tomorrow it’s gonna be fun, so something comfortable,” he orders. 

“Okay, Daddy, whatever you say.” 

–

Y/N feels underdressed compared to usual as she waits for Jensen to pick her up, and when there’s a knock on the door, she rushes to answer it. Jensen’s also in jeans, coupling it with a plaid shirt, which makes her feel a little more comfortable about her outfit of choice. He smiles widely at her as soon as he sees her. 

“You look beautiful,” he compliments, stepping forward to kiss her cheek softly. Y/N feels herself blushing, and thanks him quietly. 

“So what are we doing tonight?” she asks, locking her apartment door and heading down the steps towards his car. 

“Surprise,” he smirks, opening the door for her. Y/N climbs in, and Jensen follows behind her, and once the door is closed his chauffeur pulls away. 

She watches the street lights go past as they drive to wherever it is they’re going, and it’s quiet but comfortable for most of the journey. They arrive at a movie theatre, and Jensen gets out of the car, holding out his hand for Y/N to take, which she does. 

“What movie are we seeing?” she asks, and Jensen smirks. 

“You’re not that clever, baby girl,” he teases. His hand lands flat on her lower back as he guides her towards the entrance, and then holds the door for her to walk through. As they head towards the back of the place, Y/N notes how it’s becoming strangely quiet for a Saturday night, and when Jensen leads them to the entrance to the mini golf, Y/N quickly realises that it’s empty. 

“You said fun, mini golf is fun, right?” Jensen checks. 

“Yeah, but it looks closed,” Y/N points out. 

“Not closed, fully booked,” he smirks. 

“You booked out the entire course for just us two? Really?” Y/N asks, wanting to be surprised, but she isn’t. 

“I just didn’t want to subject so many people to my terrible golf skills,” he chuckles. Jensen leads them to the counter, and they’re given their sticks and a ball each, with a score sheet and pen. It doesn’t take them long to get started, and even less time for Y/N to figure that Jensen’s actually fairly decent at playing golf. Apparently, he plays the real thing in his free time. Y/N can’t say she’s surprised, she can imagine him in golf gear on a Sunday afternoon. Jensen might be doing an okay job, but Y/N however, sucks. 

“C’mere,” Jensen chuckles, stepping up to her. He grips her hips and pulls them back. “Shift your weight a little, there we go… now you want to hold the stick…” Jensen’s words trail off as he instead decides to show Y/N where to place her hands. “Okay, look at the ball and follow through,” he instructs. Y/N does as she’s told, and whilst the ball doesn’t go exactly where she wants it, it does get closer to the hole. Jensen steps back, leaving a draft on Y/N’s back that makes her miss him, and she clears her throat and thanks him, which he responds to by flashing her a wink. 

Five holes in, and Y/N’s ball is stuck, and she’s too proud to put the ball back on the course like Jensen has told her to do. But after a few attempts to get it over the rock, she gives up, and Jensen has to try and stop laughing to help knock it out for her. 

“It’s not funny, I really suck at this game,” she pouts, and Jensen wraps an arm around her, hugging her into him and kissing her forehead softly. 

“I’m having fun, aren’t you?” he checks. 

“Yeah,” she agrees, biting her bottom lip and nodding her head. 

“Then it’s a great night.” Y/N finds herself blushing again, still feeling the slight damp from his lips on her forehead, and she watches as Jensen lines up to take his shot.

He just seems to get more and more handsome, and it’s not really fair. Jensen catches her looking and smirks softly. 

“That’s it sweetheart, watch and learn,” he teases. 

“Oh shut up,” she sasses back, crinkling her nose. Jensen only laughs harder, and it makes Y/N chuckle too. “You’re cheating anyway, you can play golf,” she reminds him. 

“Mini golf and real golf are very different,” he tells her. 

“Still cheating,” she shrugs. “Next time we’re gonna go ice skating, because I bet you’ll fall on your ass, and then I’ll get to laugh at you,” she smirks. 

“You know there’s a rink in the building, so don’t threaten me with a good time,” Jensen flirts. 

“Oh I’ll threaten you with whatever I want,” Y/N giggles, poking out her tongue. 

“Are you flirting with me, missy?” Y/N feels her cheeks heat up, and she bites her bottom lip, not sure what to say, because she’s pretty sure she was flirting with him. 

“So what if I am, Daddy?” she asks, jokingly. Jensen smirks, stepping closer to her, bringing his face right up to hers, his eyes dropping to her lips for a moment. Y/N’s breath catches in her throat as she thinks that he might kiss her, and there’s butterflies in her stomach all of a sudden. 

“It’s your turn, sweetheart,” he tells her quietly. He steps away, and Y/N lets out a breath. She can’t kiss Jensen, anyway, both of them have been clear about the rules, it’ll never be like that between them. And that’s fine by her – at least she thinks it is.