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Jane, Alone

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“I just don't know how.”


The words are out before she can think better of it. This is a bad idea. A terrible one, even. Jane may work at a magazine that prides itself on its sex positivity, but she thinks talking to her boss about masturbating might be taking it a step too far.


Jacqueline doesn't sound uncomfortable, thank god. But then again, Jane can't really examine her reaction from the phone. She's not even capable of getting a read on her when they're face to face.


“Tell me how this is for you,” Jacqueline says. 


She's encouraging her. 


Jane takes a shaky breath. That's good. It means that, while she's crossing so many lines that she'd rather not think about, she's not disregarding Jacqueline's boundaries.


Except that it's completely possible for this to be inappropriate only in Jane's head. Jacqueline doesn't care — it's sex. It's nothing to her, yet it always manages to freeze Jane's blood. Sexuality doesn't come easily to her, not like it seems to do to everyone but her. She can't talk about masturbation, and orgasms, and sex positions without her skin turning a little bit pink.


It's ridiculous, really, that Jane is worrying so much about this when Jacqueline talks about it like it's the weather.


“Well, it's-” she croaks, then clears her throat. “It's not like I haven't...tried.” Those six words are enough to fill her with a sense of wrongness. Jacqueline doesn't say anything, just patiently waits for Jane to continue. “I have. A lot,” she says, then shuts her eyes to mentally kick herself. She doesn't need to see Jacqueline to know she's raising her eyebrows. “Not a lot, just- I've never been all that good at letting go.”


A beat of quiet, then Jacqueline speaks up. “What have you tried?”


“Oh, um… Porn. I didn't really like it, so… A yoni egg, too, but that didn't end well,” she winces. She refuses to elaborate on those experiences. Just mentioning them is embarrassing enough. “I feel like I can't get out of my head. Every time I feel like I'm...y'know, my head pulls me out of it.”


“It looks like you might need help losing control, am I wrong?” Jacqueline tells her softly, her voice soothing away her concerns.


“No, you aren't,” Jane lets out a humorless laugh. “I-”


She quickly shuts her mouth, shaking that thought away. The line is silent for one pregnant minute, and Jane hopes her breathing isn't as loud as it feels.


“Jane?” Jacqueline tests, when she doesn't finish her sentence. “Are you still there?”


“Yes, yes,” she sighs. Better to get it over with fast. “Sometimes I wish someone could just come to me and- and give me all the answers — tell me exactly what I need to do. But at the same time, it feels stupid that I can't figure this out on my own. Everyone else does.”


“It's not stupid,” Jacqueline argues, her voice leaving no room for discussion. “It takes a lot of exploration to know what truly works for you, Jane.”




“Maybe-” She stops herself before she could voice her thoughts.


It confuses Jane, who can't think of Jacqueline as anything other than decisive. She has never heard her stutter in her five years at Scarlet.




“Where are you?” Jacqueline finally speaks. There's a nervous inflection to her voice that throws Jane off even more.


“At home.”




“...Yes. I mean, alone in my bedroom, but Sutton is sleeping in the other room.”


“And you're in bed,” Jacqueline says. It's not a question, and she's not wrong anyway. “Are you comfortable?”


Jane breathes in deeply. There's something about Jacqueline's tone that is making her shift in her place. It's unsettling, though not in a bad way.


“I am,” she exhales.


“You say you would like someone to guide you,” Jacqueline says. She pauses briefly, giving Jane enough time to feel her heart trying to beat its way out of her chest. “Would you like my help, Jane?”


Jane is pretty sure her heart stopped working entirely. She chastises herself immediately. She reminds herself that what she's thinking it's probably not what Jacqueline is offering. She's overreacting — there's nothing flustering about your boss giving you masturbation tips. Or, at least, it shouldn't be flustering.


Female sexuality and empowerment are very healthy things that Jane should strive to achieve. Like Jacqueline, who is talking smoothly to her, unaffected by the conversation topic, even as her voice does sound somewhat lower than usual. Jane blames it on the phone.


Despite her overall awkwardness, Jane finds that she would like Jacqueline's help very much, in whatever form it might come. Jacqueline always makes her feel less lost, grounded even.


“Are you…?” She stops herself from saying something that might as well make Jacqueline regret her offer. “Okay.”


“Are you sure, Jane? If this is making you uncomfortable in any way-”


“No, no,” she rushes to interrupt her. “I want your help. It's- You're very…” She doesn't even know what she's trying to say. “What did you have in mind?” She asks instead.


“Oh, a few things,” Jacqueline drawls. Her low tone makes Jane shiver, for reasons she doesn't quite understand. “Let's start slow, okay?”


“Okay,” she nods, even though Jacqueline can't see her.


“Put a hand between your legs, over your underwear.”


Jane bites her lips to stop her breathing from getting any louder. Looking down to her body, she notices her chest is moving noticeably at the rhythm of her heart beat. She feels her face heating up at the thought of having her hand on her pussy while she's on the phone with Jacqueline. This is not what she expected her help would be, though she can't bring herself to put a stop to it.


She lowers her hand down her body, pausing as she reaches the hem of her pajama pants. She slips her fingers inside. She traces a light line over her underwear, feeling the heat coming from her pussy.


Oh, wow. She's actually getting turned on by this. 


“Yes?” She says to Jacqueline.


“Now brush your fingers over your clitoris. Don't put too much pressure on it. Just touch it softly over your panties. Can you do that for me, Jane?”


Jane's mouth opens silently. It's Jacqueline's voice, the way she's speaking to her with gentle command, that is affecting her the most. She closes her mouth again, swallowing. “Yes," she says again and complies.


“Good, good,” she hears Jacqueline muttering. “How does that feel, Jane? What is it doing to you?”


“Well, I-” Jane stammers. She's not sure how to tell her boss that she's hornier than she's been in a long time, that the feeling of her finger tracing slow circles around her clit is becoming maddening, more than she's come to expect from the last few times she has tried to do this on her own. She certainly doesn't know how she's supposed to tell her that listening to her voice is turning her on more than any of her fantasies ever has.


“Take your time,” Jacqueline soothes.


“It feels… good,” she says, all other words suddenly disappearing from her head. She feels a little apprehensive about saying what she's thinking, instinctively blocking any private thought around Jacqueline. She's also a little embarrassed, she admits to herself. Before she loses her nerve, she adds, “But… I need more.”


“You do, don't you?” Jacqueline hums, the sound warm in her ear. She gets the impression that Jacqueline was expecting that response from her. “Not yet, sweet thing. Keep rubbing just like that.”


Jacqueline's soft words make her blood rush downwards.


“Ookay,” Jane exhales, the air released shakily. 


Her fingers twitch with the urge to press harder, faster. She probably could, it's not like Jacqueline would know. And yet, the thought feels wrong, like she would be disappointing Jacqueline by going against her direction. 


“Jacqueline-” she gasps out, just as she begins to lose her sanity.


“Tell me.”


“Can I- I need-”


“Full sentences, Jane,” she reprimands.


Jane mouths an oh my god to herself. She clears her throat, because there are no doubts in her mind that she won't be able to speak a full sentence without her voice cracking. “C-can I press harder?" She says. “I'm losing my mind here.”


Jane swears she hears Jacqueline chuckle, like she's enjoying this. 


“Go ahead,” she allows.


Jane immediately presses her finger more firmly, releasing a sigh as she does. The extra friction is both relieving and frustrating, as she's filled with an insatiable need for more . A soft moan breaks past her lips before she can swallow it down. 


As she realizes that noise came from her, her face heats up with mortification. Jacqueline heard that. She bites her tongue, refusing to let that happen again, and focuses on the feeling of the heat of her pussy against her fingers.


“Why so quiet?” Jacqueline notices, because of course she does. “You were moaning so prettily just a second ago.”


The comment makes her blush. “I…”


She seems to sense Jane's embarrassment. She clicks her tongue in disapproval. “Don't hold back, Jane. I want to hear you.”


The words stay with Jane for a moment. Jacqueline wants to hear her. Particularly, she wants to hear her moan. That knowledge alone gets a groan out of her.


“That's good,” she praises. Jane's whole body warms up. “Just relax.”


She nods. “I'm relaxed,” she says with a shaky voice.


Her hips roll instinctively, trying to increase the friction. Jane moans, even as she actively has to fight the instinct to hold back. She knows Jacqueline would notice, like she always does.


“How are you feeling, Jane? You want to keep going?” Jacqueline questions her.


“Yes!” She responds a little too quickly. “Yes, I'm good,” she repeats with more calm as she breathes slowly.


“Great. Now it's time to take off your underwear.”


Jane gulps. “Give me a second,” she says, putting the phone down. Grabbing the hem of both her pants and panties, she pulls them down at once, her motions slightly desperate. She throws them to the floor with little care. 


Her hand halts before it reaches the phone again, her gaze flickering to the door. She stands up and checks in on Sutton, relieved to find her sound sleep. Getting back to the bed, she picks up her phone.


“I'm back.”


“Are you ready?”


“Uh huh.”


“Open your legs.”


Jane does as she's told. “Yes?”


“Now touch yourself. Nice and slow, like before. Tell me,” she says, then her voice lowers considerably. “Are you wet, Jane?”


As Jane makes contact with the warm wetness between her legs, she hisses. “Yes, very much.”


Jacqueline inhales sharply. “Focus on your clitoris,” she tells her.


Jane's eyes roll to the back of her head as she feels her folds with her fingers. They're nice and lubricated, so much so that she's taken aback that she's actually capable of getting this soaked. “And now?”


“Keep touching yourself, Jane. Tell me how you feel.”


“I feel…” Jane takes a deep breath, contemplating her answer. “Hot. And so wet. I feel like if I stop touching myself I might die, and my fingers-”


She loses that train of thought as she releases a low moan. 


“Hmm, you're such a precious thing,” Jacqueline purrs, and Jane feels her clit throbbing in response. “You're doing so well. Can you go faster for me?”


“Yes, yes-”


As she circles her fingers around her clit and moves them down to her entrance, lingering outside before rising back up, Jane whines softly at the feeling. She shuts her eyes tightly on instinct.


“Oh, god,” she moans, her fingers moving faster and faster as she gets closer to the edge. She hears Jacqueline's voice again, low and sinful, telling her something along the lines of keep doing it just like that, but Jane can't bring herself to focus on her words. “I think I'm close.”


“Then come, Jane. Let go.”


Jacqueline's soft command is enough to bring her over the edge as her fingers move frantically, losing all sign of a pattern. She bites her own hand as her moans grow louder, somehow conscious enough to keep them from reaching Sutton. Her body sags as she releases all the tension in it, her chest rising and falling with the rhythm of her breathing leveling out. 


“Jacqueline?” She speaks up after a moment of silence, her tone bashful. Her mind is clear now that she is no longer aroused.


“I'm here,” she assures. Jane sighs. She had feared that Jacqueline had decided to hang up on her now that she was done. “You did so good, Jane.”


“Yeah?” She can't help the smile that tugs at her lips. 


Jacqueline hums as a confirmation.


“Thank you, Jacqueline,” she says, and hopes that Jacqueline realizes she's referring to her help, not to the praise. Although that is nice as well.


“You're… welcome,” Jacqueline sounds uncharacteristically shy. Possibly because she's being thanked for helping her to get her first orgasm. (Now that Jane thinks about it like that, she winces. This could make her relationship with Jacqueline very awkward.) “I should probably hang up now. It's late.”


“Oh. Yeah, okay.”


“I'll see you tomorrow.”




“Goodnight, Jane.”


As the call ends, Jane stares at the screen of her phone for a minute. Turning to lie on her stomach, Jane buries her face on the pillow and smiles.


Holy shit, she just had an orgasm.