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: fluff, nerves, angst, drunk!reader, kissing

Part WC: ± 4.8K

Sweet as Sugar Masterlist

Y/N is in her favourite dress. Her favourite of the three Jensen had bought for their date that ended up being casual wear and mini golf. Y/N particularly likes this one because it fits her like a glove and accentuates her best features and hides her worst. It’s fairly formal and glamorous, and never in a million years did she think that she’d even attend somewhere that required such a formal dress, let alone own the dress to wear there. Nerves dance around her stomach as she stares at herself in the mirror and turns left to right, making sure every inch is perfect. Jensen had insisted that she go to a salon and have her hair styled and her makeup done professionally for the occasion, and she’d begrudgingly agreed. This is a big night for Jensen, and Y/N doesn’t want to ruin it by looking bad in any way. Jensen had called her a few days before and invited her to the formal business party on his private yacht, there were going to be some important business partners there, and while he didn’t go into great detail about it all, he did let her know that he wanted people to think she was his girlfriend, for the sake of appearances.

The two of them had discussed what level of physical affection was acceptable between them, and Y/N had surprised herself when she considered just how physical she’d let Jensen be if he wanted to be. After their flirty date at mini golf, and then ice skating a week later, and after that, the one weekend when Y/N was so crammed with college work that Jensen had just come over, they’d ordered take out, and watched a movie, and all their even flirtier texts and phone calls in between those weekends, Y/N had been getting increasingly comfortable with Jensen. Maybe too comfortable. Who is she kidding? She might actually be developing feelings for Jensen – romantic feelings. She’d been fond of Jensen from very early on, because he’s such a lovely guy, but the money being involved had always kept her grounded before. He gives her money and wants some companionship in return, that’s as far as his feelings go. He doesn’t want a relationship, he’s too busy for that, these are the relationships that work for him. 

And Y/N has never wanted to mix money and love or sex. She’d been crystal clear on that with Jensen and herself when this started. But as the weeks go by, she’s getting more and more used to Jensen throwing money at her, and she’s just starting to learn to catch. She doesn’t protest as much when he offers to buy her things, and she doesn’t hesitate for so long asking for money for things she needs. She’s starting to get used to it. So maybe that’s why the lines are blurring for her. But she needs to step back and reassess it. Her and Jensen are on the same page – no romance, no sex. Tonight is an act, he only wants to keep up appearances, and Y/N can’t blame him for that. And she’ll play the part of his girlfriend as well as he wants her to. But she also doesn’t want to come across as too affectionate and make him uncomfortable, so she’s more than willing to take his lead tonight. 

She twirls a curl around her finger to make sure it’s perfect, and then hears the knock on the door. She steps up to the door and opens it to reveal Jensen in a very smart, well fitted suit with a bow tie. 

“Wow.” Y/N’s voice mixes with Jensen’s as they say the same thing and Y/N instantly feels herself blushing. 

“You look beautiful, Y/N,” he tells her fondly. 

“And look at you, you scrub up well,” she compliments, trying to shift the focus onto him. Jensen scoffs slightly, reaching up to tweak his bow tie and then smooth his hand down his front. 

“It’ll do,” he tells her. Y/N cocks an eyebrow at his nonchalance, wondering how he can look at himself in the mirror looking like that and think it’ll do. 

“Let me just grab my purse,” she tells him, moving and reaching for it on the side. “Okay, I’m ready.” 

As they walk the hall of her apartment complex, Y/N can see Jensen turning and looking at her now and then out of her peripheral vision. 

“You really do look so beautiful,” Jensen tells her once more, “I’ll be honoured to have you on my arm tonight.” 

“It’s amazing what money can do. That make up artist worked a miracle,” she jokes. 

“No, it’s not your makeup,” Jensen disagrees, stopping just before the door that leads outside, and Y/N stops too, turning to look at him as she clutches her purse a little tighter. “I mean, your makeup looks great, and your hair is really pretty like that, and the dress…” Jensen trails off, and Y/N is feeling more and more flustered by the second. 

“The urm, makeup artist asked me what look I wanted, and I didn’t know what you’d want, so I said neutral tones, I hope that’s okay. I’m sorry if you wanted something else. I’ve never had my makeup done before, and I know I always do the same look on myself which is obviously not what you wanted for tonight, so I thought I’d have something different–”

A small frown etches onto Jensen’s brow for a second. “Wait, sweetheart, why did you think I wanted you to get your hair and makeup done?” he asks. 

“Urm, so that I look better? So I look good enough for your party, right? You want people to think I’m your girlfriend.” Jensen laughs softly and reaches out for her arm, running his fingers down it until he’s holding her hand. 

“No, I wanted you to have a pamper and feel spoiled and special. You’ve been working so hard with college recently, and tonight’s party was the perfect excuse for you to let me treat you,” he explains gently. 

“Oh.” Y/N suddenly doesn’t know what to say as she looks down at her feet and clears her throat. 

“And yes, I want people to think that you’re my girlfriend, but that has nothing to do with the salon,” Jensen confirms, squeezing her hand a little harder. Y/N just nods slightly. “Does that make you uncomfortable? Pretending to be my girlfriend tonight? You don’t have to do this,” he tells her, like he’s giving her an out. “We can keep the affection to a minimum if you’d prefer.” 

“It’s not that,” Y/N reassures him, gripping his hand when he seems to want to pull it away. If anything, the affection might help her relax a little. “I’m just worried that I don’t look rich or good enough to be your girlfriend, you know? What if people see through it or I say the wrong thing and ruin something important for you?” Jensen gives her a relieved smile and lifts the hand of hers he’s holding to her chest. 

“Sweetheart,” he starts, reaching up and pushing a curl out of her face, “I don’t want you for one second to ever think that you’re not enough of anything because you are perfect. If anything, people are gonna look at you and wonder what a girl as beautiful as you is doing with an old man like me,” he smirks. 

“I think they’ll have a pretty good guess,” Y/N smirks back, trying to lighten the mood. “They’ll think I’m some gold digging whore.” 

“The last thing you look like is a whore,” Jensen insists, “And anyway, most of the men there tonight have actual gold digging ‘whores’. Not every man is as lucky as me to know a girl like you.” He lifts her hand to his mouth and kisses her palm, before placing it back down on his chest. Y/N giggles slightly, feeling the buzz from his kiss on her skin, and Jensen just stares at her for a long moment. “I just want you to be yourself, okay? I wouldn’t have asked you to come if I’d have thought that you’d mess it up or make me look bad. So relax, have fun, and everyone will love you like I do.” Y/N can feel his heart beating a little harder under her hand as he continues to hold it there and she’s pretty sure her cheeks are burning her makeup off of her face. Jensen clears his throat and steps back, leaving Y/N feeling just a little colder out of his embrace. “Shall we go?” he asks. Y/N nods her head and Jensen holds the door open for her, so she steps outside into the pleasant evening air and heads towards the chauffeur car. 

–

“Robert, so glad you could make it, this is my girlfriend, Y/N,” Jensen smiles warmly, referring to her at his side.

“Pleasure to meet you,” she tells him politely, offering her hand for him to shake. He takes it delicately and kisses the top of her hand.

“Pleasure is mine,” he replies, before moving further onto the yacht where there are waiters taking jackets and offering champagne. 

“Oh, this is George Lambert, you know those gold digging whores you were talking about earlier?” Jensen whispers, leaning in a little closer to her, giving her a waft of his aftershave. “That girl on his arm? Younger than you, European. He met her online four months ago, married her one month later. No doubt for the green card.” 

“Really?” Y/N whispers back as they slowly get closer. George is a bigger guy, so it takes him longer to ascend the stairs to the deck than most. 

“If anyone screams gold digging whore this is her,” Jensen jokes.

“Jensen! Stop!” she giggles, shoving him away softly. Jensen flashes her a wink. 

“George! So lovely to see you. And this must be your wife, Katya? Congratulations on the marriage,” Jensen tells him enthusiastically. Y/N offers the ‘wife’ a smile, but she doesn’t return it, and Y/N suddenly realises that George is just staring at her. “This is my girlfriend, Y/N,” Jensen explains. Y/N doesn’t offer George her hand to shake – or more than likely to kiss – instead she just smiles politely. George and Jensen briefly talk, and Jensen tells him he’ll catch up with him later in the night, which thankfully gets rid of the couple. Y/N did not like the way Katya was staring at her or Jensen. As she watches them go, Jensen mutters something about George being a ‘poor bastard’ and Y/N can’t help the words that slip out of her mouth. 

“How am I any different to her?” 

Jensen turns fully to her and glances down the stairs to see there’s no one else arriving just now. He takes her arm and softly guides her away from the entrance and to the stern, where it’s empty and a little darker. 

“Do you really think you’re anything like her?” Jensen asks her honestly. 

“Well, aren’t I? You give me money, that’s why I’m here, that’s why we even know each other.”

“But I am fully aware that you want my money, and I am more than happy to give it to you. You don’t pretend to love me, you don’t pretend to want to be with me and trick me into giving you money. What we have is a transparent agreement. George thinks that girl is in love with him – he’s convinced they’re soul mates. I’m not under the same delusion.” Y/N suddenly feels a little strange. What if she is developing feelings for Jensen, and she can never do anything about it because he thinks she’s just doing what Katya is doing to George? Is this why he doesn’t have real relationships? “Okay?” Jensen confirms. Y/N just nods her head, her mind still spinning. “Do you need a moment? You look like you need a moment,” he adds. 

“Yeah, I just need the bathroom.” Jensen nods, and kisses her cheek softly. 

“Okay, I’ll be at the entrance to greet people when you return.”

Y/N heads to the bathroom and places her purse down on the counter as she takes a deep breath. She doesn’t want to splash water on her face and ruin her makeup, even though she could really do with the cold shock right now. She’s not in love with Jensen anyway, he’s a great guy, and he’s kind and sweet and funny, and he says the nicest things to her that no other man has ever said before, and he makes her feel so special. But like he said, they have a transparent agreement. She’s just getting confused, because no guy has ever been this nice to her before without wanting something for it, so Y/N is probably just convincing herself that she’s in love with him. Yeah, that’s gotta be it. As she steps out of the bathroom, feeling a little more relieved, she sees Katya in the hall. 

“Hi,” Y/N smiles, attempting to be friendly. Katya doesn’t even try to fake a smile. “I’m sorry, if we’ve got off on the wrong foot somehow, even though we literally haven’t spoken to each other before,” Y/N laughs awkwardly. Katya is still just staring at Y/N like she’s offended her somehow. Y/N racks her brain for what she could’ve done wrong, and then remembers the way George looked at her. “Listen, I’m not interested in your husband,” she confirms. 

Katya finally scoffs, “Please, I don’t care if you are.” She’s Russian, by the sounds of her accent. “I’m just lucky he can’t get it up.” Y/N laughs nervously more than anything, a little shocked by her bluntness. “Guess we cannot all be blessed with sugar daddies like yours.” 

“Oh, Jensen is my boyfriend,” Y/N lies, praying Katya believes her so that word doesn’t get out to everyone and make Jensen out to be a liar. 

“Of course,” Katya smiles, even though it’s forced and her face doesn’t move. “Like I said, we can’t all be lucky like you.” Katya pushes past Y/N for the bathroom and Y/N watches her disappear behind the door with an open mouth, realising that Katya must be jealous of the fact that Jensen is so much better looking than George, and that actually makes Y/N feel a little better. 

–

Jensen wraps his arm around Y/N’s waist and pulls her closer into him, kissing her forehead and she smiles softly and then laughs appropriately when someone important makes a bad joke. It’s all very boring, this business stuff, and Y/N’s feet are hurting in her heels, but she doesn’t complain because she doesn’t want to ruin anything for Jensen. She’s been feeling awkward so she’s been grabbing champagne every time it passes to give her something to hold and something to drink so she doesn’t have to talk very much. But now, it’s all going to her head, and she’s afraid of saying anything in case she sounds drunk, which she definitely is at this point. She shudders a little as the wind gets colder the later it gets, and Jensen pulls away and shrugs his suit jacket off, wrapping it around her shoulders. She’s suddenly engulfed in his scent and she hums happily to herself. Clearly not quietly enough for him not to hear, because he chuckles softly and breaks them away from the gathering of people talking. 

“Are you okay, sweetheart?” he asks softly.
“My feet kinda hurt,” she complains, hearing the definite slur in her voice now. 

“Why didn’t you tell me? Do you want to sit down?” Jensen fusses. 

“No, no, you have to… network,” she stresses. 

“I’ve been networking all night, now I need to look after you, c’mon,” he commands firmly but sweetly. He guides her further towards the stern again, and then opens a door she’s not been through before. He turns the lights on to reveal a modest double bedroom. 

“Well, this is very forward,” she smirks, giggling at her own joke. Jensen laughs softly and guides her towards the bed. “I know I’m your girlfriend tonight, but some champagne and a fancy suit isn’t going to make me take off this very nice and very expensive dress, you know, Mr. Ackles?” Jensen smirks at her, pushing the hair back out of her face. 

“Yeah, I know,” he tells her. “Sit, your feet are hurting.” 

“They are,” Y/N agrees, Jensen guiding her to sit at the foot of the bed. 

Jensen drops to his knees on the floor and lifts her one foot, helping to remove her shoe. Y/N goes to protest, but she is grateful for the help, considering if she bent forward she’d probably fall off of the bed. He puts the shoes to one side and gently rubs over her aching feet a little. 

“Better?” he checks. 

“Much,” Y/N sighs happily. 

“I’ll book you a foot massage tomorrow,” he tells her with a chuckle, getting up to sit alongside her. 

“You’re too good to me,” Y/N tells him, falling against him and resting her head on his shoulder. “Katya’s jealous of me, y’know? Said we can’t all be as lucky as me to have someone like you. And she’s right, I am lucky.” 

“Well that makes two of us,” Jensen tells her, wrapping his arm around her and stroking her arm softly. Y/N scoffs loudly. 

“Please, I’m a nobody, I just take your money.” 

Jensen sighs and pulls away, turning to face her better and then reaches up to grip her chin so she’s forced to look at him. 

“You are most certainly not a nobody. I felt pretty damn lucky having you on my arm tonight,” he tells her. Y/N doesn’t reply, because she doesn’t know what to say to that. God he is handsome though, she’s never stared at him this close up for so long before. 

“Was your ex a Katya?” Y/N asks. 

“Yeah, kinda,” Jensen confirms softly. “Guess I don’t wanna make that mistake again, I’m done being hurt.” Y/N feels a pang of sadness in her chest that Jensen’s closed himself off like that. He deserves love – real love – and he won’t even look for it. 

“You could walk into any room and have any girl in it, you know?” Y/N asks him, “Even if you were poor.” 

“Well I don’t want any other girl in any other room,” Jensen replies quietly. Other. 

Y/N doesn’t really know what comes over her, but suddenly her lips are on Jensen’s and he’s actually kissing back. His fingers move from gripping her chin to splaying out along her jaw instead, and Y/N licks softly at his plump bottom lip, and Jensen parts them and the kiss deepens a little. It could be the champagne, but there’s a buzzing around Y/N’s entire body as she reaches up and grips Jensen’s shirt. She can feel his heartbeat thudding beneath her fingers, like it was earlier that night, and it’s like she’s finally letting herself feel every feeling she’s tried to ignore for the green eyed man in front of her. The sensations of them all flooding in at once is almost overwhelming, but she pours it into the kiss, right up until Jensen pulls back. 

“We shouldn’t be doing this,” he whispers. Y/N freezes, realising he’s pulling back even further and standing up, scrubbing her lipstick off of his mouth. “Fuck, urm, just stay here – If you want to, I mean. You know, if you wanna rest, but I need to head back out there.” Y/N can tell he’s flustered. 

“Jensen, I’m sorry,” she blurts out instantly. “I’m sorry I didn’t mean – fuck, I swear I’m not a Katya.” Jensen looks back at her and then rushes over to her, dropping to his knees in front of her. 

“I’d never think that,” he reassures her, holding her face in his hands. He leans forward and kisses her forehead. “I need to go back out there, but stay in here and rest as long as you need to.” Y/N reaches up and helps him get the last smudge of lipstick off of his lips, and she knows she can’t – they shouldn’t – but she wants to kiss him again. Jensen’s eyes drop to her lips and then he pulls back. She watches him leave the room and then sighs, flopping back on the bed and staring up at the ceiling. She should feel guilty that she’s just broken their biggest rule of not mixing money with love or sex, but she doesn’t. 

Y/N blinks her eyes open and finds herself in a bed that isn’t hers. She sits up, and realises she’s under the covers of the bed on the yacht. The bed she’d kissed Jensen on. Fuck. Her head spins a little as she looks for him, but he’s not there, and what would be his side of the bed is made. She realises she’s still in her dress too and breathes out a sigh of relief. At least they didn’t sleep together. But she did kiss him, and that’s an issue. She wanted to kiss him, that much she remembers. She still wants to kiss him. This isn’t good. Last night had been different, it hadn’t been about the money side of her relationship with Jensen, it had solely been about the companionship. She had been there for him, to give him someone to show off. This is what Jensen had always talked about when he’d told her that she gave him plenty in return. She gave him company. Real company. And then she went and fucked it all up by kissing him. 

God, he probably hates her, probably wants to cut her off. She’d broken his number one rule, she’d played on his insecurities of girls only wanting him for one thing. She didn’t want him to think that she was anything like that Katya girl. Because what if he thinks she’s just pretending? Y/N sighs heavily and hides her face in her hands. She’s screwed this all up. And she’s not even sad about the prospect of losing the money – she’ll survive, she always has done before – she’s sad about the prospect of losing Jensen. 

She climbs out of bed, intent on finding him and making this right, but before she can go anywhere, on the side table she sees a pile of clothes and a note on top. 

Morning beautiful, 

Thought you’d like a change of clothing. Meet me on the top deck when you’re ready, no rush

J x

Y/N drops the note and sees the jeans and comfortable sweater underneath. The tags are still on, so she can only assume Jensen had them bought especially for this morning, which is extremely thoughtful of him. Maybe he doesn’t hate her, after all. Y/N is grateful for the change of clothes, and soon makes her way towards the top deck, a little nervous to see Jensen after what had happened the night before. As she climbs the steps, the fresh morning air hits her and she inhales deeply, needing that refreshment. 

“There you are, morning sleepyhead,” Jensen chuckles. “Coffee?” he asks, already approaching her with a mug. She takes it from him and thanks him quietly, sipping it immediately and pleasantly surprised to feel it’s hot. Jensen moves back, stepping towards the bow and Y/N follows. They lean on the railings and both look out at the ocean ahead of them. The deck below is back to its usual spotless way, like no party had ever taken place twelve hours before. 

“I’m sorry I fell asleep,” Y/N tells him, “I didn’t realise how much I’d drunk.” 

“It’s fine, you looked peaceful, I didn’t want to disturb you. It’s been a while since I’ve slept here, anyway.” 

“Where did you sleep?” Y/N asks immediately. 

“Spare room,” he tells her, smirking softly. She just nods her head and then takes another sip of coffee. Looking down at the mug in her hands she bites her bottom lip anxiously. 

“Jensen, I’m really sorry about last night, if I embarrassed you with your guests, or overstepped any lines–”

“You have absolutely nothing to apologise for,” Jensen reassures her. 

“Are you sure?” she checks, not wanting to have to explicitly bring up the kiss, but knowing they do need to talk about it. 

“I’m sure, if anything, I should be apologising to you. Not only was the party probably incredibly boring for you, but if anyone overstepped a line, it was me.” 

“You?” Y/N asks, ludicrously, “no way.” 

“You were pretty drunk,” he defends. 

“I started it,” she replies. Jensen nods softly, agreeing with her on that at least. 

“You were pretty drunk,” he repeats. “So I’m sorry.” 

“You don’t need to apologise,” she tells him honestly. “It was all on me, I didn’t mean to… I’m not Katya.” Jensen turns to face her, leaning sideways against the railing. 

“What’s this obsession with Katya all of a sudden?” he pries. Y/N sighs and shrugs. 

“I don’t want to be like her. I don’t want you to think that…” 

“What could I possibly think, Y/N?” Jensen pries, “I’m already giving you money, and you got drunk and kissed me, probably by accident.”

Y/N wants to let Jensen believe the lie, because that’s easier. But she can’t bring herself to let that go. 

“It wasn’t an accident.” It’s painfully silent, so Y/N continues. “I wanted to kiss you, Jensen. Have for a while. It’s just last night I was drunk, so I didn’t care about breaking the rules.” 

“I see,” Jensen replies quietly. 

“I get it, you wanna call this off. I can return everything you bought me.” Y/N turns to leave, not even wanting to look at him and see the disappointment, but she feels a hand wrap around her wrist and stops. 

“Where are you going?” he asks her. 

“Home.” 

“Y/N, let’s talk about this.” 

Y/N finally looks at him, frowning slightly. “What’s there to talk about? You don’t want to mix feelings with money, and I get it, I really do. I’m nothing like Katya and I don’t want to be.” 

“Exactly, you’re nothing like her, so what are you worried about?” Y/N frowns again, confused by his question. “You being in love with me has never been a condition of me giving you money, so why would it be now? I know that’s not what this is for you.” 

“You do?” Y/N checks, slightly relieved to hear it. Jensen nods, his thumb stroking along her wrist. “You said you didn’t want a relationship, didn’t want to mix the two things,” she repeats. 

“Well, maybe I was wrong. Maybe there are exceptions,” Jensen ponders. “If you want me to make them, that is,” he adds. Y/N’s heart is beating harder. Is Jensen really saying that he likes her too? Fuck – he likes her too. 

“I want to take it slow,” she blurts out. “Wanna make sure we’re both not doing this for the wrong reason. I don’t want you to think I’m gonna leave if you don’t give me this,” she tells him honestly. 

“I don’t think that, but I agree, slow is good,” he nods. 

“And no sex,” she adds, a little more confidently, given that he’s been understanding so far. “I mean, for now. It… it’s still uncomfortable to me the thought of you giving me money if there’s sex involved.”

“I agree,” he nods. “We should keep things the way they are, but not stop anything from happening if it wants to,” he concludes. “Romantic or otherwise. We can just play it by ear.” Y/N smiles a little, still feeling the remainder of her nerves in her stomach, and nods her head. 

“Yeah, okay,” Y/N agrees. 

“Great, well breakfast is ready, and you have a foot massage in an hour.” 

“Oh, no Jensen, I don’t need a foot massage,” Y/N argues, and Jensen laughs softly. 

“You wanted one last night,” he smirks. “It’s booked now.” Y/N glares at him playfully, and Jensen steps forward and kisses her forward. “C’mon, sweetheart, let me pamper you. I’m still your Daddy, after all.”