Prompts Post 7 - (Summer Heights High - Tinker Tailor Soldier Spy)

[queer_fest_mods]

Summer Heights High, MtF!Ja'mie King, she knows what it's like to be the one everyone makes fun of, but she'll never tell anyone, not now, not when she's got so much to lose.

Supernatural PRF, Jensen/Jared, Jared says, "He's supposed to be my fuck buddy. I'm not supposed to see him on his knees praying by my bed when I walk into the room."
Supernatural PRF, Jensen/Jared, The Lord is my Shepherd and he knows I'm gay. ~Troy Perry
Supernatural, Becky Rosen, She's always been attracted to very femme women - until Sam Winchester.
Supernatural, Bobby/Rufus, the hunting community (especially in the seventies and eighties) is mostly macho men who don't approve of people having gay sex.
Supernatural, Castiel, After seeing how Gabriel and Balthazar reveled in life on earth and enjoyed human sex, Castiel wonders if there's something wrong with him. He feels great affection for Dean, but sex?
Supernatural, Castiel, Dean is trying to teach Castiel to be a heterosexual cisgender man, which would be easier if Castiel were not agender, asexual, or romantically attracted to Dean.
Supernatural, Castiel. He's sexually attracted to one person but romantically attracted to another. For angels this isn't a problem because they live in flocks. Humans, however, seem to have a problem with this idea. amor_remanet
Supernatural, Castiel. Trying to figure out human sexuality is difficult and confusing when you've just fallen and become human yourself.
Supernatural, Chuck Shurley, Being God means that you're not like the other boys.
Supernatural, Dean ?/ newly!human!Cas, Dean is helping Cas figure out human society, but when Cas tries to figure out his sexuality (bisexual or gay), Dean struggles with how to explain sexual identity and society in a way that doesn't pass down the homophobic crap that he himself internalized (Dean is bisexual)
Supernatural, Dean Winchester and Castiel, Just because Dean's in a relationship with Castiel now doesn't mean that he's into LGBT politics/issues.
Supernatural, Dean Winchester, After Sam leaves for Stanford and Dad starts letting Dean hunt alone, Dean decides it's time to be honest to herself and stop living up to Dad's expectations of a macho son. The family's already broken as it is, right, so why shouldn't she be who she knows she really is? And besides, who ever said that a girl couldn't be a hero and a hunter? Author's choice of how John reacts. When she finds out that he's disappeared, Deanna decides it's finally time to see Sam again, but she's secretly scared to death about how he's going to react to the fact that she's transitioned.
Supernatural, Dean Winchester, ever since Rhonda Hurley and the silk panties, Dean just thought he was kinky and had a thing for women's underwear - that's what the strange, warm, right feeling in his gut was about. He never knew anything about LGBT issues - Sam's the one who went to college; hunting is a man's man's world and besides, there are more important things when the world's about to end. But when he moves in with Lisa and meets some of her friends and learns about the "normal" world, something starts to click. Being brought back into hunting a year later, there are more issues than Sam being alive a whole year without any contact: how is Dean going tell Sam that Sam might actually have a butch sister instead of a macho brother, and what is Dean going to do with the fact that Castiel could have looked into Dean's soul and brought Dean back as a woman after Hell but didn't?
Supernatural, Dean Winchester, Forced to attend another fan convention, Dean attends a panel on queerness in the books by mistake. Suddenly 50 women are energetically talking about how he's obviously bisexual and what a fantastic portrayal it is of queerness being normal and not something to make a big deal out of. Well, it's a big deal to him - because suddenly he realizes they might be right.
Supernatural, Dean, Dean is a trans man. It's not normally an issue - his (extended) family know and accept him, demons and angels know in that supernatural way they can tell all about a person and his one night stands don't care. But now Dean faces telling someone important (Lisa?).
Supernatural, Dean, Deanna was named after her maternal grandmother, but after the death of her mother, her father raises her as a boy to make her tougher/more likely to survive.
Supernatural, Dean, fluid sexuality, shifting from sleep-with-any-willing-woman to demisexual without his being quite aware of the change. (Lydia from 7x13 excepted. Maybe he deliberately slept with someone he wasn't attracted to as a way of putting a good face on things per 7x11, or, given the plot of 7x13, maybe she enspelled him. 7x13 being such a crappy episode, this need not be the focus of the fic.) Dean being straight is fine, Dean being bi is fine, Dean shifting from straight to bi or straight to only being attracted to Lisa and either Castiel or Sam is fine.
Supernatural, Dean, trans woman in very deep denial.
Supernatural, Dean, when Dean was raised from hell, he was re-hymenated. Which was surprising as he didn't have one before. At first he hides his new female body but eventually Sam & Bobby find out and they seek answers. Cas explains that Dean was given the body she wanted. amor_remanet
Supernatural, Dean/Castiel, Cas doesn't care, so Dean just wants Sam to shut up about this "you should come out" business.
Supernatural, Dean/Castiel, Dean says, "He's supposed to be my fuck buddy. I'm not supposed to see him on his knees praying by my bed when I walk into the room."
Supernatural, Dean/Castiel, Okay, so Dean has screwed around with guys once or twice but he's always made sure it's with guys he'll never see again so he doesn't have to think about it. Waking up in bed with Cas kind of blows that plan out of the water. xrai_namere
Supernatural, Gwen Campbell, It's hard enough being a hunter who's a woman, but coming out as a lesbian when you're a member of the infamous Campbell clan? Is it worth trying to do when the world's ending? amor_remanet
Supernatural, John, he's attracted to Mary and to anyone who reminds him of Mary, but mostly he's attracted to men.
Supernatural, John/Bill(/Ellen), John knows why Bill Harvelle really died and it had nothing to do with monsters. At least not supernatural ones. Homophobia in the hunter community. (poly relationship preferred.)
Supernatural, Mary, John's the only man she's ever been attracted to but far from the only person. Bonus points for Mary/Ellen.
Supernatural, Meg in 2x14, strong female gender identity in conflict with male body.
Supernatural, Michael the Archangel, the reason why it took Michael so long to come and talk to Dean in person, like Lucifer did with Sam, is that Michael is sick and tired of God giving her male vessels. Michael has always been female, but no one, not even God, seems to understand.
Supernatural, Raphael, reevaluating gender identity in light of the difference between the male vessel and the female vessel. Or fluid gender identity, shifting with the vessel ze's in. Or no gender identity at all.
Supernatural, Ruby, the reason she went to hell in the first place was to save her lover's life. Her female lover. Sex with the very male Sam is not at all appealing to her.
Supernatural, Sam and Dean, Sam didn't even realize Dean was into dudes, until that very male siren shows up (season 4 ep. 14) How does Sam react? Would prefer no Wincest, but I can deal.
Supernatural, Sam and Dean, the first time (ep 3x11) Dean finds a bra in Sam's bag, he laughs it off. The second time (ep 4x01), he's curious. By the third time, Dean wants answers and he isn't letting it go.
Supernatural, Sam Winchester. Why is it that the fans assume that Dean's the queer one? Just because Jessica was The One and he had something you might call a relationship with Ruby doesn't mean he's heterosexual.
Supernatural, Sam, Dean, and John (at least one of whom is queer), five conversations about sex. chasingtides
Supernatural, Sam, she really wishes she could tell her brother that she is not in fact a guy, penis notwithstanding, and is also not gay, attraction to people with penises notwithstanding. Bonus points for Sam/Brady at Stanford (maybe before Sam/Jess, or maybe Brady pinned himself to the ceiling) and/or Sam/Ruby where Ruby's wearing a male host.
Supernatural: Sam and Dean (can be Sam/Dean, if you want), Sam and Dean are both bisexual, but both grow up with completely different experiences of and responses to their sexuality. downjune
Supernatural: Sam and Dean, Sam/Dean, that ugly terrifying conversation about what it means that you're in love with your brother.

Sweeney Todd, Johanna Barker/Anthony Hope, Anthony knows there's a reason Johanna feels safe with him - she knows he'll never touch her.

The Adventures of Lano & Woodley, Colin Lane/Frank Woodley, Col goes out of his way to date women in a bid to pretend he's not in love with Frank. He thinks Frank doesn't realise this, but when Frank goes all out one Valentine's day to show him this isn't the case, Col finds himself scared, rather than eager.

The Amazing Adventures of Kavalier & Clay -- Michael Chabon, Sam Clay, 'Sammy had been having lunch, on and off, with a dozen men over the past dozen years or so.' (p.565) Sam's life balancing marriage and bringing up a child with being gay in an unfriendly time.

The Big Bang Theory, Amy Farrah Fowler, Amy thought for years that she was asexual. Now that alluring Love Goddess, Penny, is making her re-think that hypothesis.
The Big Bang Theory, Amy Farrah Fowler/Sheldon Cooper, Amy and Sheldon are perfectly satisfied with their asexual relationship - but both soon discover that asexual, in their case, does not mean aromantic. How do they deal with the sudden onslought of that thing called love, while juggling the expectations of everyone around them to be a "conventional" couple?
The Big Bang Theory, any relevant character(s), Being bullied because you're a nerd is different than being bullied because you're queer. muir_wolf
The Big Bang Theory, Bernadette Rostenkowski, It's a bit of a cliché realization for a good Catholic girl to come to, isn't it? jenni_snake
The Big Bang Theory, Bernadette Rostenkowski, She mentioned homosexuals as one of the things not to mention to her dad. She didn't tell Howard she learned that the hard way. notalwaysweak
The Big Bang Theory, Bernadette Rostenkowski(/Howard Wolowitz), She does love him with all her heart. Just maybe not all her body.
The Big Bang Theory, Howard Wolowitz, He knows exactly what George Takei was doing in his messed-up fantasy. (And Takei's back-and-forth with Katee Sackhoff is a pretty prudent metaphor too.) jenni_snake
The Big Bang Theory, Howard Wolowitz, Maybe he was wrong. Maybe he really is "that kind" of confused.
The Big Bang Theory, Howard Wolowitz/Raj Koothrappali, Coming out to friends who already treat your closeness as a punchline.
The Big Bang Theory, Sheldon Cooper/Amy Farrah Fowler, He's asexual, and she's quite possibly a lesbian, but somehow their arrangement works. quietbang

The Breakfast Club: Allison Reynolds, She sits through a makeover and kisses a boy just to see what it feels like to be normal.

The Butterfly Effect, in one of Evan's alternate timelines, he's gay, and with Tommy Miller. How does he cope with a small change altering what feels like his entire personality?

The Charioteer, Alec Deacon, he's perfectly happy with Sandy, and he was perfectly happy with Ralph; it's just that he doesn't think his promiscuity has anything to do with his long-term relationships.
The Charioteer, Hazel, coming to terms with his sexuality takes time and effort after that early shock; he keeps remembering Lanyon's disgust.
The Charioteer, Sandy Reid, Sandy has never much changed his ideas of a happy home with a spouse because he's gay; it's a rude shock when Alec's ex pitches up and starts living with them: the reminisces are worse.

The Colbert Report: "Stephanie Colbert", Jon Stewart. Stephanie's a closet lesbian who has spent years implying to everyone that she is in a One True Love That Can Never Be with her boss. Then she gets her own show, they're on equal footing, and Jon is asking her out to dinner. How far can Stephanie take this? How long before Jon realizes there's something up?
The Colbert Report: "Stephanie Colbert"(/any female character, including other genderswapped male characters). Stephanie's convinced it's not masturbation(/sex) if there's no penetration.
The Colbert Report: "Stephen Colbert". Stephen's freshly back from an invigorating two-week vacation...at an ex-gay treatment center.
The Colbert Report: "Stephen Colbert". The whole "repressed homosexual urges" schtick is an elaborate ruse. If people assume he's gay, at least it'll be something fixable. But Stephen has never felt sexual towards anyone at all, and there don't seem to be any treatment centers for that.
The Colbert Report: "Stephen Colbert"(/Jon Stewart or other). In the alternate universe shown in the December 10, 2008 ThreatDown, Stephen is always happy. He's also asexual (and, true to form, sees no reason to be concerned about it, much less pretend to be otherwise). Put these things together, and people tend to come to the conclusion that he's a childlike naïf. Sometimes he surprises them.
The Colbert Report: "Stephen Colbert"/any male character. Stephen's convinced it's not gay if one of you is wearing a skirt.
The Colbert Report: "Stephen Colbert"/Bobby. Stephen routinely forces Bobby to dress up in strange but elaborate outfits on-camera. Bobby's starting to suspect there's a kink involved.
The Colbert Report: "Stephen Colbert"/Dan Savage. Dan is openly gay and in an open relationship; Stephen is so far in the closet he's halfway to Narnia. Stephen is painfully conflicted about That Thing We Did In The Green Room About Which We Will Not Talk; Dan is just, well, Dan. phonemonkey
The Colbert Report: "Stephen Colbert"/Jo(a)n Stewart, college or young-adult AU. Stephen is thrilled to be dating someone female-bodied; maybe now he can shake some of those pesky rumors. Jon is pre-op, pre-T, pre-everything, and presenting as female to most of the world - so he's equally thrilled to find someone who doesn't have any hesitation about treating him as male in bed.

The Count of Monte Cristo, Eugénie Danglars/Louise d'Armilly, What does a butch/femme dynamic look like in 19th-century France?

The Devil Wears Prada, any female character, in fashion only the men are allowed to be gay. She's determined to change that.
The Devil Wears Prada, Emily or Andy, the gradual shift from identifying as straight, to bi, to lesbian
The Devil Wears Prada, Emily, she was assigned male at birth
The Devil Wears Prada, Miranda, it's tough to be asexual in a world where your private life is public
The Devil Wears Prada, Miranda, the media publishes a kiss and tell from her first lover - a girlfriend back when Miranda was a teen in the Midwest. How does she react?
The Devil Wears Prada, Miranda/Andy, just because Andy is younger, it doesn't make it any easier to reconcile her sexuality with the way she was raised.
The Devil Wears Prada, Miranda/Andy, so gay marriage is legal in New York - does that change anything in their relationship.
The Devil Wears Prada, Miranda/Andy, staying in the closet is Miranda's choice to make; but how to make Andy understand that?
The Devil Wears Prada, Miranda/Andy, the twins already have two parents and Andy wants to raise a child of her own along with Miranda. Adoption, surrogacy - you decide. What adjustments, if any, will they make for the child being raised by same-sex parents? damelola
The Devil Wears Prada, Miranda/Andy, they both identify as bisexual, so it's particularly annoying when the media constantly refers to them as a lesbian couple. How do they correct everyone and make it stick?
The Devil Wears Prada, Nigel, no editorial meeting has ever come close to the nerves involved in planning his wedding

The Dick Van Dyke Show, Jerry Helper/Millie Helper, Jerry and Millie enjoy a mutually satisfactory arrangement in early ‘60s suburbia: he’s gay and she’s lesbian, but they’ve covered that with a heterosexual marriage, two kids, and their best friends as the neighbors next door…except that Rob and Laura Petrie are awfully attractive…and tempting.
The Dick Van Dyke Show, Sally Rogers, Sally is always on the look-out ‘for a fella’ but it’s a good cover, because she prefers the ladies.

The Fast Show, Ted/Ralph, Ted tries to adjust to a new self-understanding as an older man, after having always thought of himself as straight.

The Five Fists of Science, Nikola Tesla, It's not that Tesla doesn't love people. He's got all sorts of romantic attachments, in his way. It's just that sexual contact is unnecessarily messy and takes away from time he could be spending on science. misura

The Giver, any or original characters, Sameness vs. gender identity: GO. What does it mean to identify as trans when everyone is called 'a male' and 'a female' and the only sex-specific occupation is Birthmother? Is there a place in the community's rigid rules for people who don't identify with their assigned gender?
The Giver, any or original characters, The scientists who were working on Sameness never did figure out what to do about same-sex attraction, but assumed the hormone-suppressing pills given to everyone at the onset of puberty would do the trick just fine. After Jonas leaves, a handful of people in the community stop taking the pills - and are confronted with feelings that fall outside of what they've come to expect in more ways than one.

The Help, Skeeter, "Would it really be so terrible if I never met a husband?" It turns out never meeting a husband is just fine because when she gets to NYC she meets a woman and finally falls in love.
The Help, Skeeter, Skeeter realizes the reason she reacted so strongly to her Momma's question about women is because she's wondering if her Momma might have been right.

The Hobbit, any dwarf character(s). One or more of the thirteen dwarves is female. It is incredibly important to that particular dwarf (or those particular dwarves) that they remain hidden in male garments, as they are not attracted to males but are on a quest where the males greatly outnumber the females and therefore fear rape. Bilbo accidentally finds out, but keeps their secret safe.
The Hobbit, Bilbo Baggins, Bilbo saw a lot of things on his journey that made him question all sorts of things about hobbit life and himself.

The Hollowmen, Phillip/Warren, when they finally decide to come out at work, they are surprised to discover no one seems to mind. They aren't sure how to deal with this.

The Hurricanes, (any Character), they aren't like any other football team (and I know I am probably the only person who even remembers this cartoon)
The Hurricanes, Cal Casey/Napper Thompson, whatever the author wants, I just want some Hurricanes fan fiction.

The Inbetweeners, Jay coming out to the group

The Incredible Hulk (1978), Jack McGee(/David Banner), Jack comes to realize that the obsession he harbors for his John Doe isn't all about finding out the truth or getting the story. No, it goes a lot deeper than that.

The Incredibles, Mirage, It's easier to fade into the background than to come out... but she's tired of hiding.

The King's Speech : Bertie, Being right handed wasn't the only thing forced upon him due to the strict customs of Edwardian society and expectations of the throne.

The L Word, Alice/Tasha, Alice is so used to being out and proud that it's hard for her to navigate her relationship with Tasha who must abide by the rules of DADT. So how does she stay true to her principles and not out her lover and avoid the guilt that comes along with knowing she might?

The Mentalist : Grace Van Pelt, Van Pelt has a crush on Lisbon and can't decide which one is worse - being attracted to her boss or being attracted to a woman.
The Mentalist : Madeline Hightower, What if the CHP officer that she had an affair with had been a woman?
The Mentalist : Patrick Jane, Becoming a father was the best moment of his life, but what he'd always really wanted was to be a mother.
The Mentalist : Patrick Jane/Kimball Cho, Cho fears that Jane is only with him because having sex with a man doesn't count as cheating on his wife.
The Mentalist : Teresa Lisbon, Despite the rumours otherwise, Lisbon does have a life outside CBI - she just doesn't want anyone to know about her girlfriend because in her position just being a woman is difficult enough.
The Mentalist: Patrick Jane/Kimball Cho, Cho doesn't like it when Jane uses homophobic language to get a rise out of a bigoted suspect. Jane doesn't see what the problem is.

The Mummy, Ardeth Bay/Jonathon Carnahan, rules of the desert
The Mummy, Jonathon Carnahan, How exactly did Jonathon ruin his career?
The Mummy: Ardeth Bay/Jonathon Carnahan, The life of Medjai is no life for a woman. Ardeth isn't even sure it's the life for an Englishmen

The New Adventures of Tek Jansen: Braina/Tek (requited or not). Ze doesn't actually have a gender, but ze hoped that putting a bow on hir head would be enough to convince Tek otherwise...
The New Adventures of Tek Jansen: Meangarr(/Nebula), Tek. Okay, so Meangarr was lying about the whole "asexual" thing. In her defense, she wasn't expecting the universe's most notorious lothario to miss the fact that she's female.
The New Adventures of Tek Jansen: Tek, any female character. Sure, the beautiful woman whose life Tek just saved claims she's not interested in men, but Tek is still convinced he can win her over. If she's not swayed by his usual hypermasculine charms, well, he'll just have to try another angle.
The New Adventures of Tek Jansen: Tek, ensemble. A bit of futuristic tech puts our hero in a female body. Everyone around him braces for the freakout...until they realize that Tek seems to have adjusted to the new curves without a second thought.
The New Adventures of Tek Jansen: Tek, female!Tek. An accidental transportation to a different universe has Tek meeting a genderswapped alternate version of himself...who, as it turns out, has also had hundreds of girlfriends.
The New Adventures of Tek Jansen: Tek(/various female characters). When Tek was co-opted into Alpha Squad, a round of injections bulked up his muscles and put hair on his chest, not to mention a very imposing bulge in his pants. What they didn't give him was a Y chromosome.
The New Adventures of Tek Jansen: Tek/any male character(s). The best way to motivate Tek when sending him on a mission is to tell him there's a beautiful woman in need of rescue. Sometimes the rescuee turns out to be a man. Tek generally sleeps with them anyway, just to stay in practice.
The New Adventures of Tek Jansen: Tek/anyone. When it comes out that Tek slept with a male-bodied rescuee, rumors begin to swirl about his sexuality. For once, Tek's obliviousness is for all the right reasons: she was female, after all, so why would there be a problem?
The New Adventures of Tek Jansen: Tek/various. Different species of aliens have wildly varying concepts of gender. How does Tek decide whether someone is eligible for his "hundreds of girlfriends" list? Is it whether their gender bears children? Is it how closely they resemble female humans? And how often does it overlap with the way they themselves identify?

The Price of Salt, Therese Belivet/Carol Aird, Their take on the Stonewall riots and burgeoning gay rights movement.

The Real Inspector Hound, Moon, Moon discovers Queer Theory.

The Simpsons, Lenny Leonard/Carl Carlson, Getting married wasn't the bad idea so much as part where they were getting married by Homer. On the upside negotiating married life has to be easier than that. And have fewer fireballs.

The Skin I Live In, Vicente, what happens now?

The Talented Mr Ripley, Freddie Miles/Dickie Greenleaf, Freddie's worried that Dickie's 'converted' to something else, but since Dickie slept with both sexes all along, why would Tom Ripley be anything different to him?

The Two Noble Kinsmen, Emilia, After growing up among her fellow Amazons, Emilia finds it difficult to navigate the court of Athens.

The Vampire Diaries, Anna has a weakness for puppy dog eyes and overempathy, regardless of gender. (Maybe an AU where the Salvatores don't come to town, and she stalks Elena instead of Jeremy?)

The View from Saturday, the four main characters, It's hard enough being the unpopular smart kids, but one or more of them is also LGBT. How do they deal with this together as a group?

The West Wing, any characters, One of the main staffers is outed in the media. How do they (and their colleagues) cope/react/change/remain the same? quietbang
The West Wing, Huck Wyatt-Ziegler, "There is something about the idea of transformation and becoming/inhabiting the body that you were meant to that seems obviously eschatological" -- [info]wisdomeagle. It might only be the end of the world in Huck's head, but most days that doesn't seem to matter much. How a trans life might be related to a theory of eschatology, and how you can have a good (if not necessarily happy) ending anyway. (Huck is FtM)
The West Wing, Huck Wyatt-Ziegler, Huck is not at all surprised that he can't even be 'normal' as a trans man, since he is gay, femme-leaning guy who is in love with a guy who doesn't know he exists.
The West Wing, Josh Lyman, Josh thinks the wrong sister died in the fire, particularly since he's not a sister at all. (FtM!Josh)
The West Wing, Molly Wyatt-Ziegler, Molly doesn't feel like she fits any label -- gay, straight, male, female -- in any of the 'approved' ways. She just wants to work out who she is.
The West Wing, Sam Seaborn, He's never lied, he's just never been asked and has never found 'the right moment' to tell. He knows he has nothing to be ashamed of, but that isn't how he feels, and when he realises that he's in love with a cissexual man who he's always assumed to be as straight as a die, he thinks maybe the time to be brave has arrived. (Sam is a gay trans man.)
The West Wing, Sam Seaborn, It surprises his friends when he moves away from California, runs away from everything, and goes to "live the cliche" (Toby's words) on a farm in the Midwest. But what surprises them more are his reasons, and his shame. (Sam is gay and closeted.) raedbard
The West Wing, am Seaborn, Toby Ziegler, Andy Wyatt, Sam is closeted and in love with Toby, who's in love with Andy, who isn't interested. One-sided queer relationships and how they might be negotiated with regard to reputation, humiliation, sacrifice, identity, experimentation, and the desire to get your boss (and your ex-wife) re-elected
The West Wing, Toby Ziegler & Sam Seaborn, The tensions of negotiating a relationship in which one partner possesses the traditional 'healthy' libido, but is not so okay about his attraction to men (or his ability to communicate feelings of any kind), and the other partner is perfectly fine about his love for men but, as a demisexual, finds the whole thing hard to explain in terms his partner understands.
The West Wing, Toby Ziegler, He's the one no-one ever thought could be queer. Existing as a bisexual man outside the current norms of gay/bi identity.
The West Wing, Toby Ziegler, post-series, During the time that Toby is a Professor at Columbia one of the kids he teaches, to Toby's surprise, comes out to him about being gay and needing help. Toby, who is currently in a long-distance same-sex 'thing' that some might call a relationship and wondering how the hell this is what his life became, muses on the ways people can be coded queer without anything overt being said, and whether or not he wants to do anything about it. raedbard
The West Wing, Toby Ziegler/CJ Cregg, "[A friend said] that she could not possibly be a woman, since she had a big belly, hairy arms, and a penis. I responded that that was exactly the kind of woman I liked." - Riki Ann Wichins.

The Wild Wild West, Jim West/Artemus Gordon, After watching Jim wearing those impossibly-tight pants of his and frequently going shirtless in front of him, Artie decides it’s time to make his move. Of course, if Jim doesn’t have the same desire for men that he does, that could be a problem.
The Wild Wild West, Jim West/Artemus Gordon, When an old war buddy visits Jim, Artie finds out that they had an affair, surprising but encouraging Artie to see if he kindle something between him and Jim. The problem is: how does a Victorian gentleman go about expressing his desires to his long-time working partner? Once they arrive in Washington, D.C., Artie has the solution: bring Jim to a unique brothel that only employs male prostitutues.

The Wizard of Oz: Glinda, pairings of author's choice. Glinda's Magic Book keeps a record of everything that happens in Oz as it happens, right? So let's hear about some of the sex written of in its pages. Any pairings (gay, straight, mixed, unclassifiable), but all with pansexual Glinda as a secret voyeur.

The X-Files, Fox Mulder, Mulder's getting tired of hearing snide remarks about his sexual orientation when he tells people that he and Scully are only friends. Well, he is queer (interpret that however you like), but it really shouldn't be any of their business.
The X-Files, Fox Mulder, Pre-XF. Mulder decides to start dating his friend and coworker, Diana Fowley, because he's afraid of being more of a disappointment to his parents if they find out he isn't straight (interpret that however you like). Eventually, the difficulty of pretending to be someone he's not and maintaining the fake relationship takes its toll and he realizes he has to give it up.

The Young Ones, Vyvyan, meshing being a violent punk who loathes 'soppiness' and 'girliness' with his sexuality

Tiger & Bunny, Ivan Karelin - Ivan was born Ivana but shapeshifted to a male form as a child or adolescent.
Tiger & Bunny, Nathan and Pao-Lin - Nathan has spent years trying to get it across to people that no, she really is a straight woman, not a gay man. It's validating on a deep level that someone as innocent as Pao-lin understands that without ever needing to be told.

Tinker Tailor Soldier Spy (film), any character, retirement and adapting to civillian life is always difficult, but doubly so when you're finally free to explore your sexual (or gender) identity.
Tinker Tailor Soldier Spy (film), any character, you know that when you die, you'll be outed as trans, and it bothers you. But can you trust anyone enough to enlist their help, when the inevitable happens?
Tinker Tailor Soldier Spy (film), Peter Guillam, he's not the only man in the Circus who has sex with men, but he feels like he's the only one who isn't content with one night stands or flings. A long term relationship is extremely difficult to maintain even for straight agents; every time Peter has tried, it has failed disastrously, and he's afraid to try again.
Tinker Tailor Soldier Spy (film), Peter Guillam, passing for straight is just another part of the job; taking on a role. Peter sometimes goes as far as sleeping with women, just to keep his cover.
Tinker Tailor Soldier Spy (film), Peter Guillam, when he's asked to pretend to be gay as part of a mission, Peter isn't sure how best to handle the situation without outing himself.
Tinker, Tailor, Soldier, Spy (2011 film), Peter Guillam, Jim Prideaux, and/or Bill Haydon, They know how to throw their colleagues off: flirt with a pretty auditor, excel at sports, seduce a man's wife. But for these spies, duplicity isn't just a job skill. It's a way of life.