A Gentleman's Dilemma

Chapter Four - Synthesis

Notes: And here it is, the end. I wanted to get this out yesterday, but I've learned to never update on a monday when the show is airing because everything will be lost during the squee.

This has been a real joy to write. Granted, there's a lot of sex in this story, but it's stemmed from much more than that. Since I first started watching the show, I have had this canon in my head about Jane's sexuality and gender identity. While the story I've presented here deals with one aspect of it, this was more my attempt to represent what I feel a lot of masculine women (and genderqueer individuals, and even those on the transmasculine spectrum who identify as male but are female bodied and went though a period of questioning) go through as they try to figure themselves out.

Gender isn't easy and it isn't simple. There's no right way or wrong way to be a boy, girl, or something else entirely. I've gotten some comments from people who really just don't get what I'm trying to do with this story, and for you folks all I can say is: please educate yourself. Gender theory is fascinating and it's really good to understand it and how gendered society as a whole is.

Thank you everyone for reading this story.

there is a small reference to a They Might be Giants song in this chapter.

Warnings for a lot of gender dysphoria.

Jane doesn't know how she's done this for as long as she has. How Maura Isles has managed to fucking insert herself into every aspect of her Jane's life and how Jane doesn't give a shit about it. Maura is nice, easy, and uncomplicated. Maura understands far more than she lets on about Jane. Jane likes that; it makes her feel safe enough to be herself.

She's been doing a lot of thinking in her downtime, away from work and from Maura. Well, away as she will ever be from either of those two driving forces in her life.

Maura has managed to coax emotions out of nothing from Jane. She cannot be Jay anymore, not around Maura, as Maura is with Jane just as often as she is with Jay. There's a blend there, one that Jane cannot explain in any way other than that Maura has forced Jane to put herself back together.

She hadn't meant to fall in love when she went out to that bar that night in September.

She hadn't meant to do a lot of things.

Jane sits, legs haphazardly sprawled across the couch and frowns, deep in thought. She knows that she shouldn't feel this way – that she isn't designed to feel this way about anyone.

And yet here she is, debating things, wondering if she could truly be with Maura.

Be naked with her, all defenses gone.

She's let Maura touch her, let Maura make her come. She's fucked Maura with her fingers and her tongue – her cock always there to finish the job because she's so goddamn afraid that it'll make her gay or some shit if she enjoys doing it like a lesbian would too much.

Maura told her that she was probably heterosexual, that she was somewhere on a spectrum of masculinity that did include those who are female in body. That she chooses to express herself sexually in a masculine sort of way. Jane doesn't fucking get it. If she likes fucking women, she's gay, but she doesn't fucking feel gay. Most of the time she's not even attracted to women, it's just that sometimes there's a girl and Jane is so captivated that she can't look away.

She hates that she even has to fucking think about this shit.

Why can't she just be normal?

There's whiskey, good Irish stuff, in the glass before her and Jane contemplates the amber liquid. She watches as the ice in it starts to melt, and condensation starts to form on the glass. She should be using a coaster, Maura would be insistent.

Jane turns, pulling one out from deep within the reaches of the couch, and sets her glass on it. There. Now Maura can't be snippy.

Jane doesn't know why she's thinking about Maura anyway. She's not even coming over today. She's gone to New York to attend a three day seminar. This is day two of her absence.

Jane hates that she's not here. She's almost used to her presence and the guys are work are calling her fucking lovesick because she's fucking pining and she can't hide it.

Heaving a frustrated sigh, Jane flips back on the couch, staring sullenly into nothingness. She thinks she understands, even if her brain wants her to pretend for as long as possible that she doesn't get it. Maura is right, she feels good and right when they're fucking, when she's got her cock and Maura's screaming her name – she feels male and she is happy in that moment.

But Jane Rizzoli can't be male, at least not all the time.

They've talked about this, Jane has told Maura that she'd rather be with Maura and be very genderqueer than be alone and oscillating between two extremes in an unhealthy pattern that Maura had just so happened to come along at the right time and interrupt. Jane knew that she could not keep going out and fucking women like that. She would get caught, she'd catch something – her mother would somehow find out.

Oh jesus her mother.

Maura had met Jane's mother, they had had a rather nice few minutes of (incredibly inappropriate) conversation before Jane had shut it down and had dragged Maura off to the lunch that they were about to share. Frankie is just getting out of the academy, her mother is still fucking annoying and clingy and had wanted to make sure that he's situated at his new job.

Jane could really, really do without her mother stopping by her workplace on a daily basis.

Korsak seems to understand and just smiles at her when she is buzzed to go downstairs and explain to her mother that no, she can't come in to see her workplace, that's it's restricted and not for civilians. Crowe and Hawkins are assholes about it and tease her even though her mother is clearly there for Frankie. Jane tells them to fuck off for what it's worth, but it doesn't do much.

She doesn't know how to tell her mother that she's in love with another woman. She doesn't even feel gay, so she can't come out to her mom about it because it wouldn't be the truth. Jane has so much trouble comprehending her own gender identity that she doesn't think that trying to explain it to someone else, especially her mother, is a particularly good idea.

So why can't she just lie, come out to her mother – say she likes women and that she's dating Maura – a fucking doctor?

Because it isn't true.

Without her cock she feels nothing for anyone, no matter their gender presentation. She feels stirrings of things for Maura, and she's fairly sure that in the heat of the moment she could act on such feelings, but it isn't the same as it is with her cock. There is no lustful desire, or passion in her actions without her cock. It's a fucking shield, a protection against everything that's fucked up about her.

Jane sits up, drains the rest of her whiskey and winces as it burns on its way down. She knows that drinking won't solve her problems, but it's making it a little easier to come to the conclusion that she knows she should have come to a long time ago.

She has to leave her cock in its lockbox.

Or else she will never truly know if she can find a way out of this gentleman's dilemma.


Jane picks Maura up at Logan on a Thursday night. Her weekend is Friday-Saturday this week and she's exhausted after a nine-day workweek. There's a hearing in court tomorrow morning that she's debating going to despite having the day off, but as she drives out towards the airport, Jane is seriously contemplating skipping. She just wants to curl up next to Maura and sleep.

This week has been awful. Maura goes home as often as she spends the night still, but Jane hasn't been able to sleep knowing she's far away.

Not that New York is far away, but rather an evil place that Jane would rather never, ever, think about except when it comes to beating the Yankees every goddamn time they play next season. This year the track record had not been so good.

Maura's waiting for her on the curb, her carry-on slung over one shoulder and her (sensibly) small suitcase right beside her. She's got a plastic bag in her hands and a rather innocent looking smile on her face.

Jane is instantly worried. Innocent smiles from Maura suggest deviousness on the highest level. Jane has learned that the hard way.

"Hey," she says, putting the car in park and hopping out of the car. She opens the trunk and Maura hands her the suitcase and then her carry-on.

There's a moment of hesitation, but then Jane leans forward, pecking Maura on the (rather surprised) cheek. She does it not because she feels obligated, but rather because she genuinely wants to. She's missed Maura.

She can see Maura's cheeks flush in the early December cold and Jane knows by the ache in her hands that it'll probably at least snow a little tonight.

"Hey," Maura says back and Jane grins at her, eying the bag in her hands with some trepidation.

A gust of wind blows by them then and Jane shivers, "Shit, get in the car, it's too cold for reunions here and that security guard looks like he's 'bout to come over here."

They clamber into the car and Jane cuts off the Boston College basketball game she was listening to on the radio (they're gunna beat BU anyway, but still, it is good to keep track) and turns to Maura, who has that grin on her face again.

"Wicked cold," Maura says, fingering the plastic bag in her lap.

"Wicked cold indeed," Jane pulls out of the loading zone. "It warmer in Satan's backyard?"

"Jane, the Yankees are not playing currently, the least you could do was respect the city for being a cultural mecca, not to mention one of the largest in the world during the off season," Maura sighs and adjusts the air vents.

"Can't, Jets're still playing." Jane's being annoying on purpose and she thinks that Maura knows it.

"You're impossible," Maura mumbles. Jane wonders if she's going to point out that the Jets (and the Giants for that matter) actually play in New Jersey.

"Boston born and bred," Jane retorts with a bright grin. "Was it warmer in the city?"

"A bit, the wind was terrible and I had to go into the subway," Maura gives Jane a completely horrified look and Jane grins. Maura can handle the T because she's been riding it on and off for years. She knows which stations to avoid and how to not touch anything that will potentially have germy disgustingness on it. The subway in New York is different, alien to her. Completely out of Maura's element.

Not to mention completely and utterly disgusting. Much like the rest of New York.

"That must have been awful," Jane says, her tone as sympathetic as she can make it.

"It was. I spent the money and took a cab back to the airport this afternoon. To avoid doing that again." Maura grins at Jane who is attempting to make a left and getting cut off by assholes running the light. "It did give me a few moments at the JFK giftshop however. I got you a present."

Jane's agitated, people are assholes and it's starting to snow already. The road is slick and they're driving like morons. She's got very precious cargo in the car. "Oh?" She turns when she's next stopped at a light and raises her eyebrow at Maura.

Maura unwraps the contents of the bag and Jane wants to groan when she sees the navy blue back of a baseball cap. "I know you don't much care for the Yankees, so I got you a Mets hat. I hope I got the size right."

"Seven and three quarters," Jane secretly hopes that she doesn't have to wear this hat to work, ever. Or in public, ever.

"Oh perfect," Maura leans over and sticks the hat, tags and all, on Jane's head. "I guessed correctly."

Jane is committing all sorts of sins against the city of Boston, but Maura's smiling at her and she's grinning right back, stupid Mets hat and all. "Thanks babe." Her tone isn't sarcastic, even though she feels like it should be. Jane is genuinely pleased and grateful. It's a nice gesture.


Maura Isles didn't want a relationship going into this. She had wanted a puzzle and had found one in the form of Jane Rizzoli. She still called Jane Jay on occasion, but the frequency had quieted, she understood that Jane could not be Jay all the time. Jay is an expression of everything that Jane has kept suppressed, everything Jane cannot allow to come to the surface.

But now, as Maura finds herself in a relationship that she very much wants, she realizes that Jane and Jay truly are the same person. That Jane is Jay privately, publicly, and in every aspect of her life. She doesn't know how her initial hypothesis could have been so off base. There are so many facets to a person's identity, and if there are moments when Jane Rizzoli wants to be a man, then that is totally fine.

It works for them.

Jane is probably mad at her for buying her a Mets hat, and for making her wear it. Maura's not sure she likes it when Jane's mad at her, but this is the good natured sort of mad that Maura's pretty sure she understands.

She also grew up in Boston, after all. Certain things are simply not done.

"I did some thinking, while you were away," Jane says, apropo of nothing, as she closes the apartment door and slides the deadbolt and chain into place.

"Oh?" Maura raises an eyebrow as she shrugs off her coat and hangs it in the closet. "What about?"

She's pretty sure she already knows, but she won't hazard a guess. She doesn't have enough evidence to make an informed hypothesis.

"Us, well, me." Jane runs long fingers through her hair and heads into the kitchen. "Want a beer?"

"No, thank you," Maura says. She sees the half-gone bottle of wine that they'd started the previous weekend tucked in the corner next to Jane's three different bottles of olive oil. She follows Jane, taking down a glass and pulling the cork out of the wine bottle. A tentative sniff tells her that the wine is still good, and she pours it while watching Jane use the countertop as a bottle opener. Maura doesn't wince, she really doesn't, but on the inside she cringes.

Jane. Is. So. Uncouth. There's a bottle opener lying out on the counter too. Maura twitches.

"So what have you been thinking about?" Maura knows that sometimes it takes Jane a little while to get start these conversations.

Jane laughs, harsh and barking. "Honestly, I've been thinking about my cock."

Maura shakes her head. Men.

"It's like… a defense mechanism, you know? I know I'm not gay, despite all outward appearances, and I guess it gives me… I don't fucking know, a way of being myself without actually dealing with things." Jane is pacing, roaming up and down space between the kitchen and the couch, beer clutched like a lifeline in one hand.

"Well, you did have a good bit of anonymous sex too," Maura raises an eyebrow, and knows from the look on Jane's face that her delivery is flawless.

Jane grins at her, "Yeah, that too." She flops down on the couch. "I was thinkin'… maybe we could try leaving it off?"

Maura nearly drops her wine glass. She regains her composure quickly, shifting her weight to lean against the island that separates Jane's kitchen from living room and inhaling slowly. Yoga has done this for her, given her the ability to bring her concentration back from a moment of complete and utter distraction.

"Would you feel comfortable?" The unspoken question of: 'do you trust me enough' lingers and Maura bites her lip, watching Jane.

Jane looks at her hands, the beer is dewing on the table and Jane isn't using a coaster.

"Honestly. No." Jane looks up at Maura then, eyes dark and full of trepidation. "But I want to do it anyway. I have to try, for you."


Jane has never been completely naked with Maura. She's been nearly there plenty of times, especially recently, but this is completely new. Maura's eyes are on her body and Jane is very aware of how her anatomy doesn't match how she feels – on fucking display with nothing to show for it. She shifts, uncomfortable, but Maura's kissing her, hands resting on her hips.

Jane likes Maura's kisses, even if they are tentative and too fucking polite. She's not made of glass.

"We don't have to do this," Maura whispers as she pulls away.

"No, I want to." Jane puts her arms around Maura's shoulders and kisses her again. "I have to try at least."

Maura's eyes flick towards the closet. "Do you want me to at least have it ready?"

Jane shakes her head in the negative. She knows that if she has it, she'll use it and if it's just not there, she'll have to work around not having it. She wants to take Maura, to see her rise up and to see her come from nothing but Jane herself. No tools and no shields. "Maura, I love you, I'm going to do this."

She hasn't said it yet. She's been wanting to, for a long time now, and the way that Maura stiffens underneath her and the breathy way that Maura says her name, her real name, makes Jane smile smugly. It is very nice leaving Maura Isles speechless. She kisses Maura then, tongue pushing forward, hard and insistent. She nips at Maura's lower lip and allows Maura to push her own tongue forward eventually, sucking on it with reverence.

This woman deserves to be worshiped, she's so goddamn fucking amazing.

Maura's hands are on her breasts, lingering longer than they've ever lingered, fingers rolling over Jane's nipples. It is a nice feeling, a little alien, but Jane isn't opposed to it. Men have nipples after all, and her skin is sensitive.

Jane growls and pulls on Maura's shirt.

She's wearing too damn many clothes. She understands Maura likes clothes, likes to look good (amazing, beautiful, hot as hell), but there are so goddamn many buttons and zippers on this fucking jacket and shirt and pants that Jane is going nuts trying to undo them all to get Maura out of her clothes.
Jane moves her hands downward, resting them hesitantly on Maura's hips. She's always the one in charge, always the one setting the pace, even when Maura's touching her. Jane likes being in control, but now, as she feels so completely out of control and vulnerable, her pace is hesitant and shaky. She's not sure that she can do this.

Her fingers curl around the swell of Maura's ass, pushing her pants down with the motion. Maura squeaks and they tumble backwards onto the bed. Jane ends up sprawled beneath Maura and they're kissing again. This time it is slow, Jane rolling her hips against Maura's leg and Maura's hands are roaming over Jane's body in a way that Jane has never let her before.

"Jane," Maura whispers, lips pulling away as Jane finally manages to undo her shirt enough to get it off. There's a moment of a clothing barrier between their faces, Maura's hair is all fluffy and flutters around her face as Jane successfully pulls her shirt off and throws it away. She's smiling, Jane is grinning back. "Jane, you're beautiful."

She wants to blush, she wants to tell Maura that she is handsome, thank you. She knows that it will ruin the moment, that Maura is doing this for Jane's benefit and for her own. Jane doesn't say anything, she just cranes her neck upwards, wrapping her arms around Maura and pulls them together as tightly as she can.

Maura kicks off her pants and they're naked, pressed against each other.

Everything stops.

Jane is acutely aware of how Maura feels against her, she's felt her many times before, but as Maura begins to trail kisses down her body, Jane wants to stop. She knows that she can say no at any time, and that she probably will before this is over, but she wants to see if she can get caught up enough in the sensations to just forget how fucking weird this shit feels.

Maura's lips close around Jane's nipple, fingers rolling the other. Jane gasps, she likes this.

It isn't that she hasn't had sex before. She has, real full-on touching sex with both men and women. She was a lot younger then, before a lot of this discomfort with her own body and gender identity had fully manifested. Jane hates that she's been so repressed for so long that her one release was to basically become a potential victim. She watches the women she sometimes sees come across her desk, dead, identity unknown; all because they happened to go out with the wrong stranger.

That could have fucking been her.

Maura saved her, brought the taboo of her being back and held it up before the light.

Jane is hard, fuck it, she's not.

She's wet and as Maura's hand slips down to cross the final boundary of their relationship, Jane realizes just how much of this she's kept pent up.

"Don't…" she begins, her voice hoarse and hardly above a whisper.

Maura's hand freezes. Questioning hazel eyes stare into Jane's and Jane shakes her head.

"Don't go inside. I don't think I'm ready for that."

"I'll only do what you're comfortable with." Maura promises, but now her mouth is moving lower too. Jane watches with wide eyes as Maura trails kisses along her stomach, fingers now splayed out across her inner thigh.

Jane has seen this many times before, it is the hottest fucking thing.

Maura is about to give her head and Jane's mind puts two and two together, everything tumbling into place.

This isn't any different.

She wants it just as much.

Mechanics are mechanics, and the plumbing's not quite right, but Jane is a plumber's daughter and she knows her way around pipes.

"You okay?" Maura's voice is quiet, muffled. She is breathing heavily, Jane can hear it and feel it rather than see it.


And then Maura's tongue is on her and Jane can't think of anything else. She loves the feeling of Maura's lips on her, her hot mouth and those pretty lips. Jane loves Maura's lips, she could stare at them for hours, kiss them for hours.

Maura's lips can pull her out of her dysphoria, pull her into the moment.

She twists, gasping, embarrassed as how she's reacting to Maura's touch. She can't stay still. It's awful, she's so out of control, she wants more.

Jane's fingers tangle in Maura's hair, and she pushes against the comforting weight of Maura's hands on her hips, holding her in place.

She's not sure she can come like this, it's been years since anyone went down on her.

Fuck this feeling is so intense. Jane twists, groaning Maura's name, telling her harder, faster. The ache in her is building, she needs something, she doesn't know what – just a longing that she can't quite place.

Maura's tongue chances downwards, away from Jane's center and towards the place Jane instructed her to avoid and Jane lets out a low hiss of approval.

Your mind says no, Jane thinks, trying not to think too hard about it, Your body definitely says yes.

She comes hard, hardly aware that she was that close when Maura pushes her tongue up and into her. Jane can't stand herself, and yet she wants more, she lets Maura coax the orgasm out of her, pulling her up when it's over, holding her close, telling her again and again that she's the best thing that's ever happened to Jane.

"I love you," Maura mutters, fingers smoothing hair away from Jane's forehead. "I love that you trust me enough to do that with you."

Jane smiles at her. "Glad we're on the same page."


Sometimes, Jane is Jay. When he is Jay, he talks shit with the guys at the station and at the bar where they go to watch the Pats play. When he is Jay he fucks Maura like she is the only woman alive and clings to her in sleep as if she was his one lifeline to safety. Jay loves Maura for loving him even though most of the time Jay doesn't want to be Jay at all.

Most of the time, Jane is just Jane. She's a detective, a woman who is married to her job and probably a little too close to the chief ME down at HQ. She goes to yoga (grudgingly) with Maura and sometimes babysits her partner's foster animal of the week. She fights with her mother, tries to be a good role model for her little brother, and is head over heels in love with Maura Isles.

Maura Isles, the woman who created unity out of chaos.


I wanted to comment on the content of this story, briefly. I have a lot of experience with what Jane and Maura are going through in this story. I'm on Maura's end of this, however - but I felt like my personal experiences would translate well into a story like this.