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cupid-styles · 10 days

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a helping hand*

in which y/n can't orgasm and harry is a helpful ex-friend with benefits.

word count: 3.3k

content warnings: mentions of depression/mental health and anti-depressants, discussions of reduced libido, smut (phone sex, mentions of sex toys, dirty talk, description of group sex and mmf threesomes)

this one goes out to all the besties on anti-depressants

masterlist | talk to me

. . .

“No.”

“But—”

“No.”

Harry sighs in frustration before crossing his arms over his chest. If he pursed his raspberry lips into a pout, he’d look more like a petulant child than the young adult Y/N’s known for the past few years. With a roll of her eyes, she lifts her glass to her mouth and takes a healthy swig of her coke and rum. She allows herself to scan the interior of the bar — it’s just barely 6 pm on a Wednesday so she’s not surprised that it’s primarily filled with locals and teams of corporate offices decompressing after a long day.

“I could always make you come when we hooked up and I bet you I could still do it.”

“Christ, Harry, give it a rest,” Y/N replies, narrowing her eyes at the curly haired brunette. “It’s not just with partners, it’s me, too.”

He quirks an eyebrow and settles his elbows on the sticky table. She huffs when she realizes she’s only piqued his attention even more now that she’s revealed another inkling of her… problem.

“Can you just tell me what’s going on, then? You know, when I texted you for our semiannual catch up, I didn’t think we’d be getting into your sudden inability to orgasm, but—”

“Can you lower your voice?” Y/N hisses with wide eyes. “I didn’t think we would talk about this either but you’re the one who asked if I’m seeing anyone—”

“Yeah, seeing anyone, not coming for anyone—”

“Just shut up!” she mutters, nearly knocking over her almost-finished drink. “If I tell you, you have to drop it.”

“I can’t promise that.”

“Harry…”

“As your ex-friend with benefits, I have no duty to keep secrets that aren’t about our bedroom-related rendezvouses.”

“There hasn’t been a ‘rendezvous’ in five years.”

“There could be.”

She sighs and presses her fingertips to her temples. This is why she and Harry never worked out. They’re total opposites — he has the energy of a rowdy golden retriever and she exudes a calm, monotone nature. (She thinks she’s borderline boring if you ask her, but that’s something she’s been saving for therapy.)

At parties in college, he was always the one working the room, chatting with everyone while she stood in the corner and clutched her solo cup for dear life.

He had a million contacts in his phone and people remembered him, even if they knew each other from something as small as working together on a project in a class three semesters ago.

Meanwhile, Y/N could spend two years straight working in the same office and someone would still ask her when she started working there because she looked “new”.

(Seriously. It happened last month, and she had to rush to the bathroom to cry.)

Despite their opposing personalities, they did work for a while, but only as friends with benefits. To begin with, Y/N never wanted anything more — when they started hooking up, they were nearing their senior year of college, and she didn’t want to be tied down to anyone or anything when making decisions about her future. But secretly, she knew feelings for Harry would inevitably pop up. How could they not? Although he was an annoying ball of energy sometimes, bouncing off the walls of her apartment before they even made it to her bedroom, he was kind. He had a good heart — he still does after all these years, otherwise Y/N would never bother meeting up with him without the intention of hooking up — and he was funny, and he made Y/N feel all warm and gooey inside. He was a good fuck, too, and as much as she wanted to widdle his presence down to being purely physical, she wasn’t strong enough for that.

She was grateful, albeit heartbroken, when six months after their arrangement began, Harry very sweetly told her he had a crush on a girl in his advanced sculpture class and wanted to go for it. As she swallowed a lump in her throat, she told him that was perfectly fine, that she was glad he told her, and that she hoped things worked out between him and Emily.

(They did. For two and a half years. Y/N had never been so thankful when graduation arrived and she could run as far away as possible from the couple.)

Harry tried his best to keep in touch, even after graduating while he was dating Emily — always commenting on her Instagram posts and responding to her stories, even occasionally texting her to wish her well on her birthday or major holidays. Y/N kept him at an arm’s length for as long as she could. That is, until he moved to her city last year.

The only reason why Y/N had a heads up is because of an Instagram story he posted. In his typical overly excited way, he posted a picture of his dog in his new apartment with one of those tacky, premade location tags. (She’s allowed to think they’re ugly — she’s a graphic designer.) So, it didn’t come as a surprise when a week or two later, a text popped up from an unknown number: Hey Y/N! Not sure if this is still your number or if you still have mine, but it’s Harry :) I just moved to your city and was wondering if we could get together! It would be great to see you.

Thus began the tradition of Harry and Y/N’s semiannual meetups.

It was an unsaid routine they followed — every six months or so, one of them would text the other for drinks or coffee or lunch. They only ever met up in public and they didn’t talk much outside of their scheduled hangouts, though Harry was much more prone to messaging her stupid memes and, on occasion, a picture of his dog, a husky named Fish.

Much to Y/N’s dismay, the chemistry between her and Harry was still very much there. It had been apparent from their first meetup last February. It was difficult not to flirt, especially when he brought up their past (she would happily pretend none of it ever happened if it meant Harry Styles never made her blush ever again). The thing is, though, is it was fine as long as nothing ever came of it.

Until now.

Because as Y/N sits across from Harry in the worn booth of a dive bar a block away from her apartment, she can’t believe she’s seriously considering letting him back in her bed.

“Can you just tell me what you think the problem is?” Harry asks. He slides his elbow onto the table and presses his knuckles up against his cheek, like they’re best friends giggling over some silly gossip. It makes Y/N want to elbow him in the ribs.

“It’s a biological issue,” she mutters, “Like I said, nothing you could fix. Even if I wanted you to.”

“Just spit it out, blossom.”

She narrows her eyes, though she finds it difficult to ignore the way her stomach flips at the familiar nickname. “You’re not allowed to call me that anymore.”

“Tell me what the issue is and I won’t call you that,” he replies easily. “C’mon, it’s me. Remember all the times I helped you pee when you were too drunk to sit up straight? We’ve definitely seen each other in more embarrassing situations before.”

Y/N sighs loudly. He has a point — there was a time where Harry knew her better than anyone else in the world. And frankly, she hasn’t talked to anyone about her problem.

Scooching her body forward, she attempts to close most of the gap between them. Harry leans closer and she rolls her eyes. To an outsider's perspective, they probably looked like they were performing some kind of sketchy drug deal or like little girls swapping secrets at a slumber party.

“Remember how I struggled with, um… getting pretty sad?”

Harry’s eyebrows draw together and he nods.

“Right, so it got… worse when I moved here. And I needed to find help, so I started seeing a psychiatrist who put me on antidepressants. They’ve helped a ton — I feel better, and the depression that I do feel is a lot less intense.”

“That’s great, Y/N,” he says, and she can tell he means it by the genuine tone to his voice. “What does that have to do with you not orgasming, though?”

She swallows tightly. “Well, my doctor increased my medication over the winter, and one of the side effects is…y’know. Decreased libido and whatnot.”

His eyes widen. “Oh, shit.”

“Yeah,” she snorts, leaning back against the cracked leather of the seat. “Oh, shit.”

“And you’ve tried vibrators and stuff?”

“Of course I have, I’m not an idiot.”

“So how long has it been?”

She nibbles on her bottom lip as she thinks. Even with flings that she’s had over the past few months, they all gave up at a certain point. The sex was still fun, but she was just the only one who wasn’t coming.

“Well, I can give them to myself if I… work at it,” she mumbles, folding her hands in her lap. “But with a partner? Probably… six months.”

“Six months?!”

The look on Harry’s face is dramatic and theatrical, as if she just told him she was moving halfway across the world and participating in some kind of 90 Day Fiance situation.

“Shut. Up.” she says through grit teeth, sending him a harsh look. “I don’t need a reminder of how shitty it is.”

“Who the hell are you letting in your bed?” he demands sharply.

“It can take me an hour, Harry, I don’t expect every person I sleep with to be that patient.”

“They should be, Y/N.”

With a shake of her head, she glances down at her phone on the table. Everything has always seemed so simple for Harry — he’s one of those people where things just come easily for him, no pun intended. A part of her wishes they never delved into the subject matter. Vulnerability somehow always bit her in the ass and this instance was no exception.

“I’m gonna get going,” she says, pushing her empty glass to the center of the table. “Thank you for the drink, H. It was good to see you.”

His eyes soften as she begins to scooch her way out of the booth. Quickly, he throws a few bills down on the table and gets up to follow her.

“Can I walk you out, please?” he asks, swallowing as his stomach brims with nerves. She nods, though he’s unsure if it’s a reluctant response. Silently, they leave the bar together, and he nibbles on his bottom lip as she pushes the front door open. The spring air is a welcomed breeze from the sticky interior of the establishment, and she shifts on her feet as she turns around to face him. She parts her lips as if she’s readying herself to bid him a final goodbye, but he beats her to it.

“I’m sorry if I made you uncomfortable,” he says as he stuffs his hands in the pockets of his trousers. “I just meant— like, you deserve better, is all. Someone who will be patient and care to learn your body.”

Y/N nods slowly. “Right. And you’re that person.”

Her tone teeters on mocking and it sends a harsh hit straight to Harry’s chest. He shrugs.

“If you wanted me to be.”

She doesn’t reply to that, but she doesn’t make a move to leave, either.

“I’ll think about it,” she finally says, and Harry’s eyebrows shoot up in shock. “My hand cramps up when I’ve been at it for too long. Maybe it’ll be nice to have someone else try.”

He huffs out a breathy laugh. “Just let me know and I’m there.”

. . .

A few days later, when Harry is at a friend’s house, he receives a text from Y/N: Are you free right now?

In all honesty, he’s surprised that she’s — assumingly — taking him up on his offer. Y/N remains to be one of the most stubborn people he’s ever known (one time she spent an entire week trying to put together a desk she’d purchased before asking anyone for help. The only reason why Harry was able to do it for her is because she’d called him over for a “destress fuck” and he finished it while she slept).

He swipes down on her message, his other hand occupied by some shitty IPA Lizzy’s new boyfriend had bought. He keeps asking Harry if he likes it and he has to lie about tasting the hints of citrus, even though it tastes like every other crappy beer he’s consumed.

At a friend’s house, he quickly types back, Why? Is your hand cramping?

He can basically feel her rolling her eyes as he bites back a smile, watching as the three dots appear to signal her impending response.

Yes. I was wondering if you wanted to come over.

He’s unsurprised by the casual invitation on a Friday night at 9:40 p.m. (it seems that, as far as hookups go, Y/N hasn’t changed much since college). Nibbling on his bottom lip, he uses his free hand to type a response.

I’m sorry, I would if I could. I’m trapped at this “apartment-warming” party for my friend. Apparently people host housewarmings even if they’re just renting a new place.

Y/N immediately types back: As much as I’d love to debate that with you, I’m really just looking for an orgasm. So if you’re busy, I’ll go back to buzzing at my numb clit.

Harry snorts at that before placing his beer on a coaster and excusing himself to the bathroom. Once he’s locked the door, he’s quick to pull up Y/N’s contact and press the pad of his thumb to her number.

“Hello?”

She sounds confused and frustrated when she answers and Harry smirks at that.

“Hey,” he greets, leaning back against the white porcelain sink. “I’m calling about your orgasm.”

“You’re seriously not trying to have phone sex with me right now.”

Her tone is as deadpan as it gets, and the monotone nature is enough to make a small bit of insecurity crawl into Harry’s stomach.

“Well, I was planning on talking you through it. ‘S not really phone sex if only one person’s getting off, I think.”

She lets out a noisy sigh and there’s some rustling on the other side. He waits for her response and is surprised when she agrees.

“Fine,” she huffs, and he can envision the way her eyebrow raises just slightly when she’s decided to give into something, “Let’s give it a try. Porn is getting boring anyway.”

“What were you watching?”

“Well, when you’ve been trying to come for 40 minutes, you end up in some… odd places,” she says. “I started out with lesbian porn, then found my way into threesomes, and somehow I ended up at double penetration.”

“Ah,” Harry nods, “Sounds like you’re having some sort of craving for group sex, then?”

A pause. And then: “I guess. I’ve never tried it, I just think it’s hot.”

“What’s hot about it for you?”

He thinks he hears her swallow, but he can’t be completely sure.

“I just like the idea of pleasing more than one person. I think that’s how I got to double penetration stuff.”

“Oh, I see. You want to be used.”

It’s blunt and it’s to the point, but he’s not wrong — he knows he’s not, because he slept with her for six months straight.

“I guess,” she replies non-committedly, “I guess it’s like… a fantasy of getting two people off and them feeling that way because of me. Through oral or… being inside of me, or whatever.”

“So what’s your threesome fantasy, then?” Harry pushes, though his tone teeters are near carelessness at this point, “Girl/boy? Boy/boy? Maybe it doesn’t matter. Who do you want to be between?”

Y/N exhales shakily, “I’ve never thought about it.”

“Well, now you are.”

She doesn’t immediately reply, but he knows she responds well to the calloused persona he suddenly obtains. She’s always been this way — submissive and good, always looking to please him intimately. It’s too easy for him to put the pieces together and solve the puzzle.

“I guess I like the idea of being with two guys, but it doesn’t matter much to me.” she eventually decides.

“Okay. And in your deepest fantasies, what are these two men doing to you?”

Another pause, though he thinks he hears a shuttered sigh on the line. He doesn’t mention it — not yet at least.

“Maybe… maybe one’s inside of me and the other one’s in my mouth.”

“And how is he fucking you? Is he on top of you, missionary style, or are you on your hands and knees while he fucks you from behind?”

A breathy whimper departs Y/N’s lips and this time it’s loud enough for both of them to hear. He smirks at the sound of it.

“I like the idea of him behind me. A-and the other one fucking my mouth.”

Harry hums, almost as if he’s praising her. “Close your eyes and envision it, then. Think about how you’re letting two men take advantage of you and use your body, just so they can get off. One’s fucking into you from behind, spanking your ass and grabbing your hips like you’re just some kind of toy to him. And the other one is thrusting deep into your mouth, making you choke, getting you all drooly for him. You’re nothing but a set of holes for them, honey. Isn’t that sweet?”

On the other line, all Harry hears is a series of shattered moans and low curses. Even though it’s been years, he can imagine the way her muscles are all tensed up, her pussy clenching around a dildo or her fingers. He wishes he would’ve asked so he could envision it, too.

“I-I think I’m gonna cum,” she whimpers out, and Harry palms himself through his trousers at the sound of her high-pitched mewls.

“There you go, blossom. Atta girl, just let go. ‘S easy, let it go for me,” his voice is a near coo and it makes Y/N’s eyes roll back into her skull. It’s like he knows how easy it is for her brain to ping pong to other far less sexier thoughts — like the dirty plates in the dishwasher or the unfolded laundry in the corner of her bedroom — so he continues crooning through the receiver, his low, soft voice guiding her through every bump and ridge of her impending orgasm.

When she comes, she comes hard, considering it’s been a solid two weeks since she’s been able to give herself an orgasm. It shoots through her entire body and, even with her eyes shut tight, the fantasy she created still plays through her brain — except now, it’s not two mystery men. Now, it’s just Harry fucking into her, all tan muscles and sweat pearling at his hairline.

She’s boneless and exhausted when she finishes, her throat dry from the involuntary moans she let go. She only remembers she’s still on the phone with Harry when she hears him clear his throat, followed by a call of her name.

“Hey, sorry,” she mumbles as her cheeks flush a deep red hue, “T-that was good. Thank you.”

“Yeah? You finished?”

If she had more energy, she would roll her eyes. Of course she finished. The entire neighborhood knows she finished.

“Yeah.” she mutters shortly. “Have a good time at your apartment-warming party.”

Harry huffs a laugh, “Yeah, ‘cos that’s what I’ll be thinking about for the rest of the night.”

She doesn’t have a chance to ask him what he means before he’s bidding her goodbye: “Let me know when you wanna do this again. I’m around this weekend.”

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