A Gentleman's Dilemma

Chapter one (of four) - Dysphoria

Notes: This was not intended to be anything other than a thought experiment – a study in how repressed Jane is if you will. I debated the pronoun usage in this story for a long time before I started writing it, and I still don't know if I made the best call here. Feedback on this would be welcome.

Before you ask – why did you write Jane as trans/genderfucked or queer/ambiguous/stone butch – I wrote it because I was trying to conceive a release for Jane from stress and tension that did not involve killing people or hitting things and it just sort of worked.

Warnings for a lot of gender dysphoria.

It is raining. It has been raining on and off all week and Jane Rizzoli hates it. She hates the case she's just closed and hates the weather outside. It is late September, still warm enough to not have to worry about autumn's quick approach, but there's a bitter chill in the air that she can't help but shiver as she glances towards the rain lashing against the window.

The lockbox is in her hands.

She's supposed to keep her department-issue firearm in the box any time she is at home and not cleaning it, but Jane Rizzoli isn't prepared to leave herself vulnerable like that. Her gun sits on her bedside table next to her badge and an empty glass from last night's three-am run to the kitchen for a drink.

No, the lockbox protects something far more precious. Jane is almost afraid to open it, to key in her older brother's birthday into the mechanism and pull it out.

She's ready though, more ready than she's been in a long time. She can go through with it. She has the confidence to do it.

She moves the dial in the familiar pattern, three clicks to the right, seven to the left and then two to the right, and exhales before pulling the lock down and open.

Jane needs this. The week has been hell, the case had fucking kids and the kids are fucking dead and there isn't anything Jane could have done to save them. They all knew that going in, when the Medical Examiner had told them that this, his last case with them before his replacement came in next week, was going to be a terrible one. She's still considered a rookie in the department, despite passing the test with flying colors, she hates it.

She didn't know what else she had expected, rolling out of bed at four a.m. on Sunday to the call of murdered children. Jane has been working all week, straight through for two days and then today she did all the paperwork she'd neglected during the actual investigation.

She needs the release.

The lock falls lifeless onto the kitchen counter, trapped in an open position. Jane smiles, her hand pulling open the top of the lockbox and staring at its contents.

The contents had cost her, but the experience was worth it each and every time. Jane fingers the soft leather of the harness, the firm hardness of what will be her release tonight and grins. She is ready.

She unbuttons her jeans and unzips the fly, shimmying out of them and haphazardly tossing them into the hamper as she passes it. The jeans she wants for tonight are buried deep in her closet (far enough back that her mother will not find them, should she look). They're Levi's – a slim men's cut that accentuates what she has and hides what she doesn't want seen. Hips and ass vanish in these jeans, and all that is visible is the length of her legs, and the soft bulge that Jane will affix there when the time is right.

She finds the underwear tucked into the pocket of the jeans, where she left them. She has to be careful, they cannot know, no one can know about this depraved way that Jane seeks out the release she cannot grant herself.

She's naked from the waist down and she doesn't look in the mirror that hangs on the back of her closet door. She very purposefully moves so that it is out of her line of sight as she pulls off her work shirt and bra.

The sports bra is a size too small and doesn't have to be hidden. It's sitting, innocently enough, on top of her three other ones that she wears to the gym. The gym is not the purpose of this one, it is to flatten, to help Jane blend. She slips it on, and then pulls on a tanktop from the drawer below it. The starched (her mother's doing) white collared shirt comes next. Jane pulls it on and stares down at herself, inhaling and exhaling slowly.

It is time.

Her stride is purposeful, full of a swagger she doesn't dare use at work. They'd never shut up about it if they saw her walking like this, like a man.

This is the way she wants to be.

The harness is in her hand and the cock feels cold under her fingertips as she carefully tests its position in the harness before stepping into it. Everything is right and good when she's doing this, when she's not letting the constant demand to be a fucking damsel in distress get to her.

She tightens the straps and heads back into her bedroom, picking up the underwear and adjusting herself once she's got them on.

Her feet are shoulder width apart, like they made them keep them at the academy, and Jane finally allows herself to look in the mirror. She shifts, tugging and pulling at her cock, getting it situated perfectly and reaching for the dark – almost black jeans on the bed. She pulls them on and buttons the fly, the zipper is pulled up and Jane is ready.

She's picked a new place this time, four stops on the T uptown and away from anyone who could possibly know her. She had heard about this place from a college student they interviewed who said the scene was classy, if queer.

Jane likes queer – she does not know how to describe herself any other way.

She certainly isn't a lesbian, even if her end goal tonight is to find a woman willing to let Jane fuck her long into the night until they both forgot anything but that moment.

Jane needs to forget that that is always the goal, that she's always trying to make herself forget how everything about what's she's doing is oh so wrong, and yet oh so wonderfully right.

She never lets them touch her; she throws them out before she comes.

Her keys are in her pocket and she's thrown on her suit jacket from work to complete her fucked-up image. She's a boy – he's a girl. Jane doesn't know what the fuck she is, but she feels right as she heads into the rain, up the road and down the steps to the T.


It's a Friday night, but the bar itself is quiet. Most of the bar's patrons have drifted off to the dance floor upstairs, but Jane doesn't particularly feel like dancing. She doesn't like dancing, it feels too much like sex and there's people touching her places she doesn't want to be touched and it's honestly not worth fucking with her own hang-ups to find a hook-up.

There's a woman at the bar in a little black dress, a tan raincoat slung over the stool next to her as though she's saving it for someone and fuck, she's wearing the most amazing red pumps Jane has ever seen.

That is the woman that Jane is taking home.

It is what that confidence that Jane sidles up to the woman and taps her on the shoulder before sliding into the space next to her. "Hey," she says, eyes cast low and voice pitched even lower. She's had way too much practice with this, she has the ritual almost down to a science. "What's your name?"

The fun is in the chase, Jane thinks, as a pair of inquisitive hazel eyes look her up and down once before settling back on her face. Jane can tell they're lingering on her pants, on her lack of defined breasts, but she does not care. It's not about their perception, but rather her own. This is her night to be a man, to take as men do.

The woman purses her lips as though thinking, and Jane hopes she's not going to run. It's hard to change targets once she's picked one. "Maura," she says quietly, and Jane leans in closer, smelling expensive perfume and catching just the barest hint of a freckled cleavage hidden just underneath the silken neckline of the woman's dress.

Jane licks her lips and she can see Maura's eyes darken even in the dim light of the bar.

"What is your name?" Maura asks and Jane curses her luck. Usually they just roll with it.

"Jay," She says quietly. She's used the name before, a lot actually. She likes it, likes how it rolls off the tongue so similarly to her own name, and yet without the female connotation.

Distract before she asks anything else.

Jane turns and gestures for the bartender, asking for a vodka, double on the rocks. Liquid courage for what she's about to do. "Anything for you?"

Maura gestures to a half- full wine glass and Jane inclines her head.

Her fingers brush along Maura's thigh and she can tell by the way that Maura's breath hitches that she's doing this right – that Maura wants it as much as she does.

Maura's eyes are lingering on her crotch, on the bugle of her cock and Jane pushes her hips forward just a little – rolling them as though she's fucking the air in front of her.

Eyes widening, Maura's cheeks turn bright red and Jane gives her a self-satisfied smile before taking a sip of her vodka.

"Has anyone ever told you," she asks swallowing and preparing herself to not wince as it burns going down. "That you are exceptionally pretty?"

"Not in so many words, no," there's an odd truthfulness in Maura's voice that Jane finds endearing as she allows her hand to move upwards, her touch now more bold as she's pushing Maura's dress up and touching the warm skin underneath it.

Jane leans in as close as she dares, her voice quiet and as laden with sex as she can imagine. "You'd look even better in my bed – with your sexy shoes and your lips wrapped around my cock."

She might have gone too far with that last comment, but there's a red flush on Maura's cheeks and her chest is raising and falling rapidly. "Really?" she asks quietly, her voice a little shaky.

Jane pulls her wallet out of her pocket and lays down seven dollars for her drink and a tip. She brushes her lips against Maura's ear as she whispers, "I'm taking the T home, orange line south-bound." Her lips linger for a moment longer than necessary, but Jane drains her drink in two long pulls and turns to head out of the bar, very aware of the rustling behind her. It is soon followed by the steady click of heels on pavement as Jane walks the two blocks to the T station.


The pressure against her jeans is almost too much and Jane already knows that she's not going to be kind to Maura tonight. Her keys jingle in the lock at her door as she eyes Maura, wide-eyed and rather hesitant in her body language, over her shoulder.

"I've never…" Maura begins, but Jane lays a finger on her lips and pulls her inside. She slides the locks back into place and toes off the boots that she was wearing.

Maura stands here in her living room looking awkward and highly uncomfortable. Jane likes that, it gives her the control she needs and craves.

Her jacket is discarded, tossed over the back of the couch, but she lays Maura's out more nicely, folding it a bit and fingering the fabric. It's expensive feeling.

She wants to touch Maura. She's pretty sure she'll feel as expensive as the jacket.

She's making herself wait.

Maura's biting her lip, still clearly turned on by this whole situation and Jane contemplates drawing it out longer, offering her another drink. There's just something about this girl, about how easily she'd come along – for a girl as pretty as her, Jane usually had to work much harder to get to this point – that bothered Jane.

She's leaning against the island of her kitchen, watching as Maura moves about the room, picking up knickknacks and inspecting them, before she's had enough. "Come here," she says quietly and Maura obeys without question.

Jane likes obedience, it makes doing this less awful and more real.

Maura's skin is so soft under her fingers; Jane cups the other woman's cheeks and pulls her in, kissing her roughly. Her tongue pushes forward against Maura's still-closed lips once, twice, and then Maura gasps and Jane is granted access. She pushes her tongue in again and again, spinning them so Maura is pressed up against the island and Jane has one leg thrust between Maura's.

Her hands brush against the front of Maura's oh so sexy dress, feeling for the sensitive nipples she knows will be there. The dress is backless, Maura isn't wearing a bra.

Her nipples are hard.

Jane smiles, satisfied and smug into the kiss and pinches both of them. She revels in the little noise Maura makes at the back of her throat as Jane rolls her fingers around the sensitive skin she's found.

Maura's fingers are pulling at her shirt, tugging on the buttons. Jane can't have that. Can't be touched, can't be seen. It isn't about her, it's about how she makes them feel – how she blurs the line. How she's as good as any man.

Her fingers close roughly on Maura's shoulders and she pushes down, their kiss breaking. "Get on your knees," she says. It sounds almost like a suggestion, but both parties know that it is a request that must be obeyed or this all will end.

Maura's fingers fall slack and she hesitates for just a moment, eyes searching Jane's own for the unspoken reassurance that Jane will not hurt her, that's she'll stop if asked. Jane gives her the barest of nods before moving her fingers down, tugging at her belt and undoing the buckle. She pops the button but leaves the fly zipped.

The bulge of her cock, hard and ready and always prepared for this is obvious, straining against its confines. Jane exhales, "Take it out."

Short, practical nails where not what she expected from Maura, but they were just that. Jane swallows, hips almost subconsciously bucking forward as Maura pulls the zipper on jeans down. She can see, in the bright light of her kitchen, Maura's fingers close around her cock and she hisses in pleasure just watching such a beautiful woman handle her like this.

"Oh Jay," Jane wants to moan, just listening to that breathy voice say her fake name – the androgynous one that she actually rather likes. She bites it back, not giving Maura the satisfaction of knowing she got a reaction. Jane can't show, can't feel. It isn't about that. "It's so big," Maura adds, as if she's surprised Jane was hiding that much in her pants.

Modesty was never really her thing.

Jane's fingers tangle in Maura's hair and she finds herself almost growling. "Suck it. That's what you came here to do, isn't it?"

She likes to talk, while she does this, she thinks it adds to the experience. Maura seems to like it, for she's doing exactly what Jane says, her lips brushing against Jane's cock, licking, kissing, not sucking, not yet. She likes to draw it out, she's like Jane then.

Jane's hips roll forward, she can't help herself. There's a beautiful woman with the sexiest shade of lipstick she's seen in weeks sucking on her cock and she's done with trying to pretend that this isn't who she is.

Maura's fingers press hard into her hips, Jane can feel them through the layers of denim and cotton she's wearing. The pain is good, but it is better when Maura's head begins to bob, moving up and down, taking in as much as she can with each pull.

"That's it, that's a good girl," Jane mutters. She can barely think; her body has all but taken over her emotions and she's so fucking happy she decided to do this. Maura is fucking hot as hell and Jane wants to fuck her so bad.

She pulls Maura's hair, groaning and thrusting into her mouth, not caring that it's probably uncomfortable, that it most likely doesn't feel nearly as good for her as it does for Jane. She's the man, this she takes without question.

Maura pulls away, eyes half-lidded and Jane is intrigued as she sits there, contemplating Jane's cock. "We should have intercourse."

Moment. Killed.

Jane wonders how someone could say something so completely and utterly unsexy, and yet here it is, right in front of her. She groans, running a hand through her hair, angry it's so long, but knowing that she will never cut it. Her cock aches for the attention that Maura was giving it just a moment before, but Maura has gone and said something colossally dumb and now Jane isn't sure if she wants to throw her out or gag her.

"How about this," She says, bending offering Maura her hand and pulling her to unsteady feet. "You don't say anything at all?"

Maura thinks about this for a moment before shrugging. "After a certain period of time during intercourse I cannot control-"

"That's good talk," Jane says, cutting her off before she can get started. She's pulling Maura towards her bedroom, she doesn't care about the moment that Maura ruined. She has to fuck her, has to be in her, has to take her dress off and touch those breasts she's barely touched enough. "Using clinical descriptions of shit? Bad talk."

This takes a minute to settle in and Jane knows she's walking a bit bowlegged because she's too turned on and Maura has left her standing at attention.

It isn't real, but she likes to tell herself it is.

Maura's hand is on her back, touching, holding her steady. Jane spins away from the touch, pressing insistent lips against Maura's neck, pulling at her dress.

She's so warm, she feels so good, Jane is going to fuck her with her clothes still on and she's so fucking hard just thinking about it. She's that fucking good, she doesn't even need to make concessions to get Maura to go along with it.

Jane pulls away just far enough to whisper against Maura's lips, "How do you like it?" She doesn't know how much of a response she's going to get, Maura's breathless and obviously preoccupied with how Jane has got her hands on Maura's ass. She's squeezing and kneading and Maura is whimpering against her lips.

"How do you want me to fuck you?" She asks again, grip tightening and voice hard. She doesn't like not getting an answer. It's a carryover from work, she knows it, but she doesn't care. She's not thinking with her brain anymore anyway.

Maura's response isn't one that she anticipated. Fingers brush against the starched fabric of Jane's shirt and Maura pushes her backwards onto the bed. Jane yelps as she falls backwards, landing in a tangled mess of jeans and shirt and too-long limbs.

She's struggling to sit up, taken aback by Maura's sudden aggression. She doesn't like it, it isn't part of her plan for the evening, but oh god, Maura is taking off her dress. And suddenly Jane can't think of anything better that she has to be doing.

Maura pulls her dress over her head, letting it fall to the floor and stepping out of it carefully. She's still got those fucking hot shoes on and Jane swallows visibly, watching as Maura pulls off the thin bit of lace that can hardly be called underwear. It falls out of long fingers, Jane watching as Maura gives it a disinterested glance before she climbs on top of Jane and hovers, right above her cock.

"I like to be on top," Maura says quietly, biting her lip. An adorable flush covers her cheeks and chest as she sits there, Jane's hands now firmly latched onto her hips.

Jane wants to be in her – just like this, to be able to see those fucking amazing breasts bounce up and down as Maura rides her.

This wasn't what she had planned.

The conflict that Jane's very existence is based upon is about perception. She wants to let Maura do this to her, and she's in concert with herself about how this would be completely and utterly hot. She can't let it happen though. Because this is not about Maura, or how fucking amazing Maura's tits are. This is about how she can't decide what the fuck she is.

Her grip on Maura's hips tightens and Jane pulls her down, roughly, onto her cock. Her hips rock up to meet Maura's downward motion and Jane groans long and loud. She's so fucking hard – she has to get off and this position might actually do it for her.

She can't come – not when Maura's here and wanting to see her come like a fucking girl.

She isn't a girl, she doesn't know what the fuck she is.

Maura's pretty hazel eyes are screwed up in an expression of bliss and Jane can't help but turn her head and look away. She doesn't want it like this, she has to change it. Maura's riding her cock and it's hot as hell, but it isn't right. It wasn't planned.

Jane can't stand this.

"Get off," She mutters, her hips halting their motion.

"Jay?" Maura asks. Her cheeks are flushed and her body is covered in sweat.

"Lie down, I can't do it this way anymore."

She's pliant, at least, and her skin is soft and she smells good. Jane is used to picking up women when she's had a bad week and taking them like this, but Maura is making it hard for her to do it. She wants to treat her right, and not throw her out as soon as she's calm enough to walk after Jane is through with her.

Jane knows that that will take some time at least.

She's also a cocky son of a bitch and likes to fashion herself to be the best they've ever had.

She's been told enough that it's the case that she's probably not tooting her own horn that much.

Maura's legs wrap around Jane's waist, her hot-ass shoes still on, and Jane pushes back into her. Maura is tight and wet and Jane groans as she pushes back into her. She begins slowly, eyes trained on Maura's face, watching as she bites her lips and inhales sharply with every thrust.

"Jay…" Maura begins, fingers clawing at Jane through her starched shirt and too-tight sports bra. She's almost completely masculine around her chest now, and Jane likes it. She wants to know what Maura's fingers would do to her back, if she could bring herself to allow Maura to touch her skin.

She can't. No one can. That isn't how this works.

Jane bites her tongue and goes faster. Everything is in this moment now, her mouth on Maura's neck, breath coming in short pants. Maura moaning.

She moves her hand, resting awkwardly on one arm. Her fingers brush against Maura's breasts, against her stomach, and then in between their rocking hips. This is one reason that Jane's always been so grateful that she at least understand female anatomy better than most guys, she can twist her fingers against Maura's clit – push her over the edge in a few drawn-out seconds rather than risk her not being one of those women who can come from normal sex.

That's a laugh, normal sex.

Nothing about this shit is normal.

Maura's babbling incoherently at her now, and Jane knows that she's close. She slows her pace, pushing her cock in and out of Maura, drawing it out for as long as she can.

"Just do it," Maura says, breathless. Jane wonders if she knows what's coming.

Her hips are going to be bruised in the morning, but she locks her hands in place on Maura's hips and fucks her until she can't any more – when Maura is coming too hard for her to move in and out with ease.

The fake name that Jane gave her is on Maura's lips, her voice is loud and breathy and fucking hot as hell.

Her neighbors are going to worry about her, but they know she's a fucking cop and has a gun and will shoot any motherfucker who tries to rape her. Jane Rizzoli has the most ridiculous sex, they'll say.

If Jane gets to see Maura come like that, she's tempted to say let them talk. Until it gets back to her mother, and then she'll fucking kill anyone who even looks at her funny.

"Should I be using male pronouns when I refer to you?" Maura has apparently calmed down enough to say completely ridiculous things.

"What the fuck… No!" Jane growled, scowling and standing. Maura's already worked her way down under the covers and is apparently settling down for the night. "Why would you even ask that?"

What the fuck, Jane never said she could stay.

"Because it is a logical question to ask. You clearly do not completely identify as female, and I wanted to know if you would be less fidgety if I used male pronouns," Maura's face is pressed into Jane's pillow, hand curled and body contorted so she can still watch Jane. There's tiredness in her eyes, Jane can see that, and she's glad. If Maura's going to insist on staying, she must be asleep soon, as the ache that Jane can barely contain between her legs is growing more and more pronounced with every moment she stares at Maura's naked form.

"I don't know," Jane says, standing. She picks up the t-shirt and shorts she's been sleeping in and walks out of the room, "I don't like thinking about it."