Transsexual people are those whose individual self-perception of their own gender is not typically associated with their assigned sex. Some transsexual people pursue means (e.g., hormone replacement, plastic surgery, or "The Operation") to make their bodies match their self-identified gender, but others do not. Transsexual people are not a new group; there are documented examples going back at least as far as the Roman Empire. Transsexual characters can be a source of interesting Conflict in a story, and may have a lot of parallels to a coming out story for a homosexual or bisexual person, but with a lot more visual representation of change. note With respects to the Rule of Cautious Editing Judgement, see The Other Wiki for more details on transsexual people.
Now for some definitions:
Homosexuality is a completely separate issue. Transsexuality is not gayness turnedUp to Eleven, as convenient as that would be. A strictly gay man would generally not be attracted to an MtF transsexual, for example. The "T" is in "LGBT" because transphobia and homophobia have similar motives - both defy the main idea of what a man or a woman "is" or "should be" - but they are separate, distinct groups, although there is a fair contingent within the trans community that places rigid ideas roles on how genders should be to establish how to self-assess and transition, with one odd, surprisingly common example being that F-to-M people should abandon personal hygiene, including handwashing. It's also a myth that all trans people are heterosexual (attracted to the gender opposite to their identity). Trans people run the full gamut of sexual orientation, just like anyone else.
"Transgender" is generally used as an umbrella term for people whose identified gender does not match the gender they were assigned at birth. Within the trans community there is actually debate about "transsexual" v. "transgender". As can be seen just in the identifications on this page, transsexuals, transgenders, and transvestites are frequently confused.
Insisting that a transgender person's gender is not real for any reason, or will not be real until they've done hormone therapy/surgery is considered incredibly rude, since not every trans* person wants or is able to do these things.
"Androgynenote A gender identity found "in between" male and female. Can be in the center or closer to one of the "edges". Some may move between the extremes- see "genderfluid".", "Agendernote A gender identity that is lacking an innate sense of their gender. Note that this does not necessarily mean that this person does not experience gender dysphoria.", "Gender Variantnote A catch-all term for variations in gender apart from male or female", and "Genderqueernote Similar to gender variant, but you're relatively more likely to run into someone who self-identifies as genderqueer, and this isn't an umbrella term." are various terms used for different types of people who reject the gender binary entirely. It is important to note that this is not the same as someone transitioning from one sex to the other; s/he doesn't reject the gender binary so much as feel that s/he was assigned to the wrong side of it. This is why comments implying they are some sort of "third gender" or that they have "the best of both worlds" can be highly offensive to some (but not all) trans people. There has been very little research on this group by either psychologists or neurologists, but most qualitative research on the expression of these phenomena suggests that they are more based on philosophy than something inherent.
Genderfluid, Bi-gender, or Tri-gender refers to people whose gender changes over time, whether between many identities or just two or three. This can be as often as daily or as rarely as once in a decade, and can have triggers or happen on its own. If these people's identities end up matching up to their birth-assigned gender at some points, they may consider themselves "part cis". Not to be confused with multiple personality disorder.
AFABnote Assigned Female At Birth/FAABnote Female Assigned At Birth/CAFABnote Coercively Assigned Female At Birth, AMABnote Assigned Male At Birth/MAABnote Male Assigned At Birth/CAMABnote :Coercively Assigned Male At Birth and UABnote Unassigned At Birth refers to the "birth gender" of a person. Some trans* people prefer this, as terms like FtM/MtF exclude non-binaries or intersex people. Also, because calling a someone's body "a girl body", for instance, because it has ovaries and whatnot can be offensive - it doesn't belong to a girl, therefore, it is not a girl's body and its actual contents are irrelevant to that fact. (The same obviously goes for "male" bodies).
"Crossdresser" and "Transvestite" refer to wearing the clothing of the opposite sex. They may or may not be used interchangeably and do not necessarily entail either cross-gender identification or homosexuality (although they also do not preclude either.) That other wiki has an entry for "transvestic fetishism".
"Intersex" (inaccurately "Hermaphrodite") refers to atypical physical development and is more common than you think; it is not related to the above but may occasionally lead to them if the doctors decided for the newborn before surgically assigning sex organs. There's a small but growing tendency to go with the phenotype and identify as intersexed. A few subtopics:
There is a small but growing body of evidence to suggest that some transsexuals (sex and gender, like sexuality, are far too complicated for single bullet theories to be credible) may have a neurological intersex condition, though there is still no definitive neurological ruling on the matter.
There is also a subset of intersex people called chimeras, who have a mix of male and female genomes in their bodies. Some manifest as transsexuals, only to have the chimerism discovered in adulthood, often during baseline testing for hormone therapy. Imagine having that bridge(t) dropped on you, and trying to reassess your personal identity after.
Finally, there is Klinefelter's Syndrome, when the very karyotype is XXY, technically male due to the Y chromosome, but also female due to the XX. Two variants are XXXY and XXYY.
Cissexual, Cisgender or just Cis is the opposite of transsexual, the majority: someone whose gender identity matches up with their birth sex note "Cis" is a Latin prefix that is the opposite of "trans," meaning "not across," as in chemistry or "cisatlantic/transatlantic." "Non-trans" is also used, but just saying "normal" or "real" or just "man"/"woman" as opposed to "transman"/"transwoman" is a guaranteed way to irritate trans people (and their cis allies) no end.
The term "trans*" is often used as an umbrella term for all non-cissexuals; the asterisk represents the various endings (transgender, transsexual, transvestite, etc.) though it includes people with identities that don't start with the "trans-" prefix, like the aforementioned genderqueer or agender.
Any and all of the above may be characterized as transsexuality. Sometimes accurately, sometimes as a sign the author didn't do the research. Confused yet?
Most transsexuals in TV and the Media are male-to-female (MtF, trans women). Female-to-male (FtM, trans men) transsexuals are much less common in mainstream fiction, but statistically are about as common in Real Life (Current estimates are somewhere in the vicinity of 1 in 200 for social transition.) Trans men may have mastectomies to remove their breasts and phalloplasty to construct penises for them.
Many recent portrayals of transpeople tend to be fairly sympathetic. However, bigoted and inaccurate "trans panic" jokes that portray transpeople (usually women) as deceptive cross-dressers ("Oh no, the hot chick is really a man!") are still common — and as this line of reasoning is often a motivefor murder in real life, this type of humor goes beyond mere Unfortunate Implications.
Contrast Gender Bender, which is about men and women changing their physical sex through magic or Applied Phlebotinum (though occasionally such stories also involve transsexual characters.) Also contrast Easy Sex Change, which is this trope plus They Just Didn't Care. Unlike Gender Bender, the Easy Sex Change has at least a pretense of realism, but minimizes or ignores many physical, psychological, and/or social complications of the sex change.
For another common example of They Just Didn't Care as applied to this trope, see Trans Equals Gay.
Has nothing to do with Transhumans; the shared root Trans note Latin for "across", "beyond" or "on the opposite side" is the only commonality, and even then both terms use different definitions of it. The root Trans here means "opposite" roughly.
This trope has a Useful Notes page here.
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In a Sprite ad for Latin-America, a guy reunites with his school friends, and each encounter finishes with "[insert friend's childhood nickname], eeeeeeeh!" and a hug/group hug. The last one, nicknamed "Oso" ("bear" in Spanish), turns out to have transitioned from male to female; we only see her from the back but she's clearly using heels and a minidress. What do her friends do? "Oso...? [blinkblink] OSO!! EEEEEEEH! [group hug]".
Anime and Manga
In the manga adaption of Welcome to the NHK, Yamazaki befriends a pre-op transsexual, and even gets a job to pay for her operation. Unfortunately, this charity offends her, and she ends the friendship
Maho, one of the two main characters in the manga Double House, is a transwoman, as are a number of the secondary characters.
Isabella in Paradise Kiss seems to be a non-operative transgender woman.
The Trigun Maximum manga has Elendira the Crimsonnail, although she is presented as a transvestite. Vash is the only one who briefly recognizes her as female, and then only to insult her. She glared and said 'a woman like you' out of Wolfwood when he called her a guy one time. Apart from Meryl categorizing her as a transvestite (and complimenting her figure) after she falls out of the sky, it doesn't really come up otherwise; people are busy. The actual question is how everyone can tell by looking at her.
Arakune / Arachnee in Angel Sanctuary. In her case, she doesn't have reassignment surgery because it'd mean she would lose some of her strength.
Also, Laila/Sevoth-Tart/Sevy/Sebi is a sort-of? transman. In this character's case, it isn't because she identifies as male but as a result of the trauma of being gang-raped. Because of this, 'she' lives in denial of her previous existence as Laila, and even goes as far as undergoing treatment to inhibit her breasts. She also wears a machine that makes her voice sound 'masculine'.. Towards the end of the manga, 'she' is discovered and goes back to being female; she even becomes pregnant after Sandalphon rapes her.
Angel Sanctuary also has Belial, the Mad Hatter, who explicitly identifies as neither male nor female and deliberately resorts to genderfuck clothing and make-up to play on his/her androgynous appearance. Some scenes shows her/him as more masculine or feminine than other ones, though; in the presence of Kira or of Lucifer, Belial usually looks very much like a wounded Femme Fatale. In the purely biological sense, s/he is a breastless female. To make this powerful Trickster character even more complex in terms of gender and sexuality, Kaori Yuki also makes him/her omnisexual. For example, s/he is madly in love with Lucifer and as proof of his/her devotion, sacrifices to him 1,000 virgin women that s/he loved. S/he even seduces Kurai partly by taking the appearance of one of her male suitors and generally acting like a campy male, with the result that she is dumbfounded when she discovers that Belial is biologically female. This character is truly as genderqueer as you can possibly get.
Kurai herself has some trouble in identifying as female, although it's probably partly because she starts off as a young teenager. She seems to have less trouble with her gender identity once she 'develops' at an extremely quick rate. However, she explicitly compares herself to Arachne, mentioning that their families had problems with Arachne being what they thought was a 'transvestite' and Kurai being a 'tomboy'.
Alexiel and Rosiel, anyone?. While she laments to have been born female, because she had too many feelings to deal with and wished to be reborn as male (which led to her reincarnation as Setsuna). Although she seems to embrace her true self in the end, she still has gender issues. Meanwhile, her brother wants to be her, he has her beauty/face and even pretends to be female once.
Family Compo has so many Transsexuals and Crossdressers that it's hard to count. The main character's adoptive parents (both of them — that is, the dad is biologically female, the mom is biologically male. Both are non-operative transsexuals.), his adoptive father's assistants (all transsexuals, some post-op, some not), several dozen bit characters, and one of the character's love interests — his adoptive sister — may or may not be a biological male, given that about every 6 months she'd switch genders as she was growing up ( It's never explained in the manga, and in the end, the character realizes it doesn't really matter anyway.) Oh, and given how 'effeminate' the main character is, he ends up in drag just about every other storyline.
Akari in Samurai Deeper Kyo was raised as a woman to make her shamanic powers stronger, and it stuck.
The series mostly ignores the implications of transgenderism (except as gag fodder) and makes her the strongest of Kyo's followers and, therefore, a complete Badass.
Commander Teral from God Sigma is literally a woman in a fairly masculine man's body. Ironically, she's the noble prince-type of the story despite being one of the main villains. She gets very little snark, which is pretty open-minded for an early 80s show.
Shuuichi Nitori (MtF) and Yoshino Takatsuki (FtM) from Wandering Son. Also their adult friend Yuki Yoshida (MtF), who is implied to have had a full physical transition, as well as Nitori's classmate Makoto Ariga (MtF).
Hibari Oozora of Stop! Hibari-kun, who has loudly voiced her disappointment in the fact that she doesn't have breasts and plans to eventually marry Kousaku. The anime also avoids ever showing her naked chest despite the fact that she doesn't have anything to hide there.
There's also a random island girl that looks almost exactly like Hibari (resulting in another Unsettling Gender Reveal moment for Kousaku and a girlfriend of Ibari's — one whom he doesn't know is trans.
The protagonist of Riyoko Ikeda's Claudine, Claudine de Montesse. He's a very woobie-like female-to-male transman with a sensitive heart and horrible luck, who ever since he was a child was sure that he was a male, and in the end commits suicide after his lover Sirene gets engaged to his eldest brother Andre. His doctor (who doubles as Narrator All Along) reminiscences about Claudine's case, and concludes that he was right into identifying as a male.
Futaba Aoi from You're Under Arrest!, one of the prettier woman officers. In an episode in the second season where she asks for help with a date with a man, Aoi says, "I have the body of a man, but the heart of a woman".
It may have been confirmed, though without saying any transgender related terms. "Aoi-chan" is thought of as being female almost all of the time, and transsexuality tropes have appeared relating to her. Episode 6 all but goes out and says "transsexual"; A character says that her "natural flow" leads toward her being a woman, and goes on to say that he doesn't care if she's male or female (signifying she's a girl instead of a crossdresser). The original manga implies she had interests in crossdressing and feminine thoughts before becoming a police officer too.
Grencia Mars Elijah Guo Eckener aka Gren from Cowboy Bebop. He was originally biologically male, but was given experimental drugs that affected his hormones in a similar way to gender reassignment, feminizing his body. Although he generally presents as a man, he can pass for a woman.
Hana in Tokyo Godfathers says, "I am a mistake made by God. In my heart, I am a woman."
The Day Of Revolution is a two volume manga series about an intersex but genetically female high school boy who elects (under pressure from his family) to become a girl because he sees it as a choice between being an 'incomplete man' or a 'complete woman'. he quickly finds that letting go of his old male identity isn't going to be easy or simple.
Criff/Cliff from Infinite Ryvius is a male to female transsexual who transitioned a good time before the series started. You'd never know if it weren't for Word Of God statements and a blink-and-you-will-miss-it line from her sister.
One of the stories in Pet Shop of Horrors has Leon investigating the murder of who turned out to be a transgender man with a beautiful female alternate persona, who kept rooms of aquariums of transgender fish and a virtual pet of a beautiful female fish. She was killed by the bartender who had a crush on her when he found out.
And in the Tokyo version Count D and a friend visit a club for transvestites and transsexual women, all of whom are portrayed very sympathetically. The bartender/owner comments that they're just women looking for husbands and also makes reference to a place a floor up where men can meet other likeminded men. Count D is apparently on good terms with some of them and has tea with the group on a regular basis.
Strange Mansion features a Stalker with a Crush who moves into the title apartment to be near her bishounen classmate. She discovers that her crush became a woman to be with his/her love interest (he was a bit disappointed that his first declaration of love came from a man but handled it calmly), which causes a Heroic BSOD. Of course, the MtF character's wealthy conservative parents know nothing.
A story from Junji Ito features an entire transgender family of serial killers. Revealing their physical sex seems to be their Berserk Button (the daughter kills her new friend when she discovers; the mother has a breakdown when her five o'clock shadow becomes obvious).Dear oh dear.
The main character from Ai No Shintairiku, Nikotama Sara, is a male-to-female transsexual.
A little known manga titled Gender Identity Disorder follows the life of an FtM transsexual. It begins with his childhood (telling his father he wants Santa to give him a penis for Christmas), and ends with him transitioned and leading a successful life, reconciling with his father before he dies.
Subverted (yes, subverted) with Nuriko from Fushigi Yuugi, who is presented for quite some time as being a perfectly normal woman until the bizarre and unnecessary reveal or retcon that Nuriko actually dresses like a woman due to dead relative issues. Because it's okay to be a mess of Norman Bates-y psychological issues, but a trannie? That would just be weird. Be careful where and when you bring this up, though.
Weirdly enough, there is a very freudian theory about transsexuality which actually goes like this - the theory is that people are trans because they lost - or became too close to - their opposite sex parent/other family member, and they end up wanting to be the opposite gender due to wanting to "keep them alive". Again, this is the sort of theory which a lot of people disagree with/think is bullshit, so it's best not to discuss this either.
Yoshiki Kitazawa from the manga Gravitation is an MtF transsexual. In the first series, she's only had hormones to encourage breast growth but her lower half is still physically male. In the sequel, EX, she finishes her surgery on her lower half as well, like she's wanted to since she was 14-15 as stated in the fanbook.
Izumi Nachi/Lady Nachi in Mugen Densetsu Takamagahara: Dream Saga is pre-operative in Nakatsukuni, and post-operative in Takamagahara. She takes full advantage of her female form, attempting to become the perfect girlfriend]that she could never be in Nakatsukuni because of societal expectations... to a guy that didn't want her. The rest of Nachi's evolution goes from Clingy Jealous Girl to I Want My Beloved to Be Happy.
One episode of Dirty Pair featured a wealthy business owner framing his son's fiance for kidnapping when really they were trying to elope. It's eventually revealed that the reason he objects to their marriage is because the fiance used to be a man and had a sex change (there was nothing to suggest this other than the woman was tall). After a moment of surprise, Kei and Yuri respond: "So what? That's so closed-minded!" and "In these days, one out of every ten people has had a sex change!"
Grell from Black Butler is male-to-female transsexual, as Toboso Yana eventually made clear. As the series is set in Victorian Britain, she's necessarily non-operative, which has led many to think she's a flamboyantly gay man.
Celebrity stylist Nao from Ice Revolution, who forgives uber-Tomboy Masaki for destroying her favorite scissors, gives a makeover that makes her appear truly feminine "on camera" for the first time, and even leaves the fee for later. Notably, she is the only person outside of Masaki's friends and family who can tell she's a girl at first sight.
Masaki: How did you... know I'm a... girl...? Nao: Isn't it obvious? Masaki: (is completely mystified)
After The Reveal that Nao is a male to female transsexual, Nao tells Masaki that they're Not So Different: both of them had a hyper-aggressive male appearance that they're no longer comfortable with.
Mikihisa from Level E is female-to-male and has felt male since he was four. After much tribulation, the alien princess who's in love with him gives him a really high-tech sex reassignment. With some other modifications to weed out the Depopulation Bomb virus in the princess' body, they live happily ever after.
Mitsuko, the main characters' sidekick in Leviathan, is a transwoman, and while her characterization in itself is fine, her friends take every opportunity to point out that she's not a real woman and use mildly offensive terms to refer to her. And this is all supposed to be played for laughs.
A chapter of the manga How I Became a Pokémon Card is about a FtM named Akari, who has to wear a female school uniform since he's entering middle school. He gets a Pikachu for his birthday, which he's mad about since it's not a "cool" Pokemon but a "cute" one. He eventually got over it and learned that it doesn't matter what a Pokemon looks like, that they all can be cool.
Genkaku Picasso has YosukeHishida, who is explicitly described as suffering from Gender identity disorder. She puts on a good show of acting like a normal boy, so this causes some problems when she's caught in the girls' bathroom. She's almost Driven to Suicide, but when Sugiura saves her and offers to listen to her troubles, Picasso (who has been inside the sketch of her heart) rallies the class to go to where she is and listen to her. When they do, they apologize for how they treated her and rally to let her wear the girls' uniform.
From Ludwig Kakumei, the Goose-Girl in the Well, Princess Julianna, whom we know for most of the series as Lui's "step-brother" Prince Julius. She very explicitly states that she doesn't identify as a man (or almost does before she cuts herself off), despite having a male body, but everyone else seems to think of her as a crossdresser of some nature or another.
In Sorcerer Stabber Orphen, we have the local Cool Big Sis and Orphen's first travel partner, Stephanie. Orphen explains to Majik and Cleao that she used to be a male-bodied magic user named Stephan until few years ago, when she was seriously injured and her male body was horribly torn apart. During her recovery, she asked the healers if they could turn said male body into a female one; they accepted, and now Stephanie has a female body that she's very comfortable with. Cleao and Majic are rather surprised when Orphen tells them (and in fact, Cleao wonders if Stephanie's boyfriend Tim knows), but Orphen himself seems to be pretty nonchalant about the whole deal and it's never discussed again.
In most versions of Ghost in the Shell it's implied that Major Kusanagi may have been a man before becoming a female-styled full-body cyborg, though the TV series balked at this and featured a flashback episode were she was a little girl.
Chaplin from Deadman Wonderland is transgender. The first time she used her Branch Of Sin was when she was living as a male. Her lover was using her as a source of money. She got mad at the woman he was sleeping with and accidentally stabbed her.
The third story in the oneshot manga Mascara Blues revolves around a trans girl who falls for a boy.
Ren's sister in Sazanami Cherry is revealed to be transsexual in the second to last chapter. Ren may be transsexual too but it's hard to tell.
In "A Game of You", a Story Arc in The Sandman, the protagonist, Barbie, is friends with a non-operative transsexual named Wanda.
In Y: The Last Man FtM transsexuals are widely accepted in the post-Gendercide world as a way of avoiding Sit Sexuality (except by the man-hating Daughters of the Amazon who are likely to kill them on sight). The eponymous protagonist is often mistaken for one at first glance, due to his situation. MtF transsexuals presumably died when the men did, since it was based on possession of a Y chromosome, but it's never brought up.
Of course, in the Real World, some men have XX chromosomes and some women have XY chromosomes, though it does not happen very often.
DC's Doom Patrol had a relatively short lived MtF character named Coagula (real name Kate Godwin, birth name Clark Godwin). The character was created by transsexual science fiction writer Rachel Pollack.
Grant Morrison's The Invisibles features a character called Lord Fanny who blurs the line of several types of transgenderism, her origin and things she says throughout the series suggesting that she has identified (or simultaneously identifies) as transsexual, transvestite, and drag queen. The contradictory nature of this may have been done on purpose, or more likely was sloppy research.
Alison Bechdel's Dykes To Watch Out For started by introducing an MtF character named Jillian who hung out for a few strips. Later, an FtM character named Jerry was introduced; Lois developed a crush on him, which later moved on to a fairly durable friendship. Finally, Jasmine's child Jonas became more and more insistent about identifying as a girl, and eventually started living full-time, taking hormones, and identifying as Janis, with Lois's support.
DTWF Follow the LeaderJane's World has Chelle's mother, a transman (so only biologically her mother). A female trucker who fell in love with him decided she was gay after learning the truth.
Marisa Rahm, the lead character of Milestone Comics' Deathwish miniseries, is a realistically-portrayed MtF transsexual police detective. The series was written by Maddie Blaustein (better known as the voice of Meowth from Pokémonnote Dat's right!), who was transgender herself.
The Highland Laddie arc of The Boys had a secondary character known as Big Bobby, first met in a pub wearing heels, a frock, makeup and a wig, the 6+ foot Big Guy self-identifies as a lesbian, although he was pre-op at the time. The storyline sees him emasculated by a fat psychotic lady with a pair of hedgeclippers. Bobby takes this in stride, and asks the doctors not to sew the severed genitalia back on, but to treat it as the first stage in gender-reassignment surgery. Played very sympathetically, with nary a Bridget joke in sight (initial surprise on the part of Wee Hughie, who hadn't seen Bobby for several years; Bobby is referred to by male pronouns, although not when present. There is one genital mutilation gag near the end, but one that is only slightly insensitive).
The excellent film Breakfast on Pluto, based on a novel of the same name, is all about the life of fictional Irish transsexual Kitten Braden.
One of the most unlikely transformations is found in the 1970 film Myra Breckinridge, in which Myron Breckinridge (played by film critic Rex Reed, of all people) goes under the knife and becomes Myra (played by Racquel Welch).
Hedwig of Hedwig and the Angry Inch, a gay male who got the operation on the spur of the moment to qualify for a Citizenship Marriage with his lover. Predictably, the shady doctor screwed up, and the vagina didn't form properly, leaving him/her with nothing but a urethra, the titular "angry inch", and a scar. (In Real Life, surgeons generally invert and alter the penis, so this probably would not happen.) Hedwig spends the movie dealing with essentially having become an MtF transsexual, until at the end he comes, at least in the film version, to embrace a masculinity identity.
Different for Girls is the story of a post-op transsexual woman meeting up with her male punk friend and protector from high school, ten years later. At first, the male friend is revolted, then accepting, then aroused in the end; they decide that they don't do too well apart, and become lovers. They are both unemployed, but sell the story of their relationship to a tabloid for a sick amount of money.
This is the whole plot of the movie Boys Don't Cry in which a young transman uses a combination of haircut, bandages holding down his breasts and leaving his hometown to express himself properly as a man: Brandon Teena. He even manages to have sex with a girl without her noticing sort of. Confusion might arise for some viewers as to whether or not Brandon was actually a transman due to his own claims that he was a hermaphrodite, but he was in a women's prison at the time and trying to keep his secret from the woman he loved, so this was pretty obviously a lie. Especially when taking into account the shower scene after his violent and traumatic rape.. Hilary Swank plays the role very believably.
Judy Squires in Better Than Chocolate. She's also a singer at a local lesbian nightclub, and gets a rather tart musical number explaining the differences between drag queens and transwomen.
Ace Ventura: Pet Detective features one of the less flattering parodies of The Crying Game, revealing that the villain is actually Lt. Lois Einhorn, who this whole time was really the missing football player Ray Finkle, having gone through complete transition (but remaining non-op), adopted the identity of a missing hiker, and became a police lieutenant, seemingly all in the sake of the perfect disguise for his revenge on the Dolphins and Marino. Roger Podacter, who was attracted to Einhorn, discovered this, finding "Captain Winkie" during a romantic encounter with her and getting murdered for it, in an exact reversal of how things happen inReal Life.
Tom from The Cement Garden is a boy who would rather be a girl, believing that girls wouldn't get bullied. His sisters eventually give him a makeover, and his best friend William takes on a new interest in him...
The French/Belgian movie Ma vie en rose ("My Life In Pink") is a very tasteful presentation of a young MtF transsexual and her dilemmas. A possibly FtM youngster appears near the end of the movie as well.
Noxeema: When a straight man puts on a dress to get his sexual kicks, he is a transvestite. When a man is a woman trapped in a man's body and has the little operation, he is a transsexual. When a gay man has waaay too much fashion sense for one gender, he is a Drag Queen. And when a tired little Latin boy puts on a dress, he is simply a boy in a dress.
The main character in Rainer Werner Fassbinder's film In a Year of 13 Moons is a male homosexual who gets a sex change to be more appealing to his lover. Somewhat subverted as the character did not consider himself a woman pre-surgery. This and the fact that he kills himself at the end has earned it the ire of critics who say it paints transsexuality in an inaccurate and unfavorable light.
Open, an independent film by Jake Yuzna showed a positive same-gender relationship between a gay male pair: one cisgender, one transgender. Possibly no feature-length fiction film had shown such a relationship before.
Elvis & Madonna, a Brazilian film, is a positive depiction of a cisgender lesbian and a bisexual trans woman falling in love.
The Thai film Beautiful Boxer is a biopic about the famous male-to-female transsexual and former Muay Thai boxer, Nong Thoom. Thailand is known for its "kathoey" (literally "third gender") of male-to-female transsexuals.
German movie Zettl (Spiritual Successor to Kir Royal) has the mayor of Berlin as this. Might be a parody on the Real Life gay mayor, one of the first openly gay ones. Completely with a billionaire who has a thing for pre-op transsexuals. And is pissed off when she finally does the operation (in the Cuban embassy, of all places) since this makes her "a totally ordinary woman!"
Sam from Gutterballs. After being killed, BBK adds insult to injury by bisecting her penis to create a "mangina".
Michelle Cliff's No Telephone to Heaven has the trans/genderqueer character Harry/Harriet (also known as H/H), who is biologically male but identifies as a blend of male and female. At the beginning of the novel, s/he has a totally masculine appearance but wears bikinis, puts on feminine make-up, and occasionally dresses in the genderfuck style (for example with both a tuxedo and very campy make-up. Hilarity Ensues as this impish black Jamaican character passes for an African man to fool an American tourist, who really thinks he has just met "King Badnigga of Benin!"). Towards the end of the novel, H/H starts living and presumably identifying as Harriet, a white nurse, which involves double 'passing'. H/H is very aware that even as 'she' is respected as a generous nurse, s/he could literally get lynched for being trans and for passing for white, but makes this choice because a black man couldn't become a nurse. This character plays a huge role in the development of the very confused main character Clare Savage, a white-looking middle-class mixed-race Jamaican woman who questions the racist standards of her formerly slave-owning family and might further be bisexual. His/her ability to transcend social binaries and to fool racists and homophobes/transphobes is part of his/her attributes as a Trickster figure.
Zoe Marriott's Shadows on the Moon has Akira who was born male but who identifies as female. When she became the Shadow Bride she should have been killed when her sex was revealed, but the prince understood and described her as having a female heart.
David Thomas's Girl is about Bradley, a macho, working class, rugby playing young man who accidentally goes through sexual reassignment surgery (and simultaneous breast augmentation) through a hospital error. It is actually quite sensitive and sweet, even if it is a bit of a stretch that the (almost stereotypically) blokish Bradley decides to commit himself to becoming a woman so quickly, ending up as a sweet-natured, pretty (thanks to hormones and plastic surgery) and content young woman named Jackie.
In Lois McMaster Bujold's A Civil Campaign, the dashing and unconventional Lady Donna Vorrutyer undergoes gender reassignment at age 40 to become Lord Dono. As this is SF, Lord Dono's transformation is perfect - he's even fertile. Lady Donna chooses this course so that she can prevent a corrupt male relative from inheriting her dead brother's countship and its attendant responsibilities. Barrayaran law doesn't allow women to inherit countships, but neither is it exactly set up to deal with transsexuals - in the end Dono prevails. And ends up engaged to be married. One assumes Donna was originally bisexual. Elsewhere in the Vorkosigan series, it's stated that people who choose to have their brains transferred to younger clones often choose to change sex when they do. How you can have a clone of the opposite sex isn't explained.
Judging by what happened with Mark Vorkosigan, I would say that they do it by making a normal same-gender clone and then giving it a sex change like Lord Dono's. The result would apparently be indistinguishable from a real Opposite-Sex Clone.
Commander Ambrose in Maria V. Snyder's Study trilogy. As it turns out, the Commander has both a female and male personality within a female-gendered body due to magic — his mother died giving birth to him and her spirit entered his body (and apparently changed his genitalia). The female personality is allowed out whenever the Commander leaves the country, and is officially an ambassador.
Angela Carter's The Passion Of New Eve (1977) is a novel about a British man, Evelyn, who is, well, castrated by Militant Feminists and made into "a New Eve". It's a satire on Feminism in general, Freudianism, and all other sorts of things. Also features a Dystopic America in the process of caving in on itself.
Coydt Van Haaz, the women-hating Big Bad of Jack Chalker's Empires of Flux & Anchor, turns out to be an FtM transsexual with a very tragic Back Story. Turns out he was biologically male originally, until he was castrated and then given an involuntary (and irreversible) MtF Gender Bender as a teen. He wants his manhood back and he wants it bad. Since that's not possible he wants to make all women suffer for what happened to him. This is very unusual in a 'verse where Easy Sex Changes are canon.
In John Varley's Eight Worlds series, sex changes have become so easy and common that anyone who goes through their entire lives as the same sex is considered a little weird, and population control laws have boiled down to "one person, one child."
In an odd twist, Gurgeh (from The Player of Games by Iain M. Banks) is regarded as being a bit odd because, although changing sex is the norm for most (human) citizens of the Culture, he has never done so. The strong implication is that Gurgeh regards everything as a game and at some level regards being a receptive sexual partner as losing. At the start of the book, it's mentioned that a distinct majority (six in ten?) of his ex-lovers have become, and stayed, FtM.
Lady Dela from Alison Goodman's fantasy Eon: Dragoneye Reborn is a played straight and rather awesome version of this trope. The varied views of prejudice and acceptance surrounding her are also interesting, as the people of the Asian-inspired universe of the book seem to regard her either with respect for being a sacred "twin-soul", or a freak because they think she's a man living as a woman.
Luna by Julie Anne Peters is about an MtF transsexual's teenage sister, Regan. Regan often has to lend Luna clothes or cover up for her, because their parents do not know.
Parrotfish by Ellen Wittlinger is about an FtM transsexual, Grady Katz-McNair. At the beginning of the book, Grady decides he wants to officially come out and change his name from Angela to Grady. The title of the book comes from his nerdy friend, who points out that female parrotfish often change to males.
Neil Gaiman's short story Changes concerns the accidental creation of a drug that allows an Easy Sex Change and the ramifications of said drug on the global society. Gender identities are blurred as the drug takes on a recreational use, and in the end (as with every conflict of generations) it's seen as something ordinary (if mildly dirty) by the young and disgusting by the old.
David Nobbs's Sex and Other Changes is about a transsexual married couple, both of whom transition in the course of the novel.
Anna Madrigal from Armistead Maupin's Tales of the City and its sequels, along with the television mini-series adaptations.
A character in Tamora Pierce's book Bloodhound is a male-to-female transsexual called Okha/Amber. In that world, it's apparently referred to as being 'tapped in the womb by the Trickster God'.
The Bone Palace by Amanda Downum has Savedra Severos, the transsexual mistress of the Crown Prince, as its second viewpoint character. Transsexuality is only marginally accepted in this culture; it has a long history in the open, but most hijra (the "third sex", encompassing all varieties of transgender and agender people) live apart in the company of their own. Most are either in the priesthood, are mystics and fortune-tellers, or work in prostitution. Savedra is lucky; she was born wealthy and her mother and family members accept her. Despite the magic of the setting, nothing seems to give any kind of Easy Sex Change; Savedra at one point laments her Adam's apple and her small breasts, and she retains functional male genitalia, so physical sex reassignment does not appear to be possible.
One novel — about a yuppie Latina in San Francisco working under the mayor's wife — features an MtF transsexual as a supporting character. She met her boyfriend in a gay men's dance troupe, meaning the author sadly missed the part about gays and transsexuals not being one and the same.
There's a children's book named 10000 Dresses, by Marcus Ewert and Rex Ray, about a young MtF who wants to wear dresses but isn't accepted by her parents.
The excellent novel by David Ebershoff called The Danish Girl is a fictionalized account of the first widely publicized gender reassignment surgery ever performed. The subject of the novel, Einar Wegener, begins to confront his body and sexuality issues after being asked by his wife to pose in a dress so that she may finish a commissioned portrait of a friend of the young couple. Einar is then moved by this experience to begin identifying himself as Lili. The novel explores the situations of both Lili and the ever-loving and supportive Greta as they come to terms with Lili's transformation. A film adapation allegedly staring Nicole Kidman as Einar Wegener/Lili is currently in Development Hell.
The title character from I Am J by Cris Beam, a Jewish, Puerto Rican, FtM teenager who is deeply insulted by being called a lesbian, or even by his confused parents calling him "my daughter".
In Brian Katcher's Almost Perfect, the main character meets, and falls in love with the new girl, who happens to be Mt F. He struggles to accept her, and eventually does so in a well thought-out manner, based in part on the author's interviews with young transgender people.
Isabel Allende's Eva Luna has Melecio, an Italian teacher who ever since young identified as a girl, much to the ire of her abusive father. Her Mammasupports them devotedly, though, and she get some solace in her Inter generational friendships with La Seńora and Eva. When Eva returns to the capital after spending several years in a small village, she finds out that after a full-blown Break the Cutie process (which included politically-based incarceration, rape, torture, illness and many other terrible things), Melecio now openly can identify as female and has renamed herself as Mimi. She's still working on rebuilding her life alongside going through reassignment therapy by that time; after the meeting, she pretty much adopts Eva into her household as they retake their Inter Generational Friendship, then with time she both becomes a TV star AND finds the love of her life. When Eva gets her the chance to go through the final operation, however, Mimi rejects it: she's squicked out by the surgery in itself and she doesn't think it's necessary, as her boyfriend (the local Da Editor Aravena) loves her the way just she is.
F2M: The Boy Within by Hazel Edwards and Ryan Kennedy is about a FtM teenage boy named Finn. He's also a part of a punk rock band called "Chronic Cramps".
There's a children's book called When Kathy is Keith by Dr. Wallace Wong, who works with transgender youth. It's about a trans* boy named Kathy who no one believes is really a boy.
Recently revealed to be the case for The Princess in Velveteen Vs via origin story.
Live Action TV
Nip/Tuck seems to have a bit of a fascination with transsexuality (understandably, as the show is largely concerned with sex and plastic surgery); the most notable of these is Ava Moore (played by Famke Janssen), whom main character Christian calls "the goddamn Hope Diamond of transsexuals."
The Education Of Max Bickford had a reasonably realistic transsexual character for its first season or so, who was an old school chum of Max's.
It only ran one season; the show's creators were fired by the network halfway through its run, and the transwoman (well played by Helen Shaver) was never again seen.
Coronation Street has a realistic and extremely sympathetic transsexual woman, whose marriage to another long-time regular character was one of the highlights of recent seasons.
All My Children has introduced a transsexual character in the process of transitioning. Is in a relationship with a lesbian.
The L Word has had a drag king as a recurring character, and a transsexual man as a member of the main cast.
One of the reasons why the Argentinian telenovela Los RoldĂˇn was so succesful? The fun-loving transsexual character played by actress Florencia de la V, who is a male-to-female transsexual in Real Life.
A transman features in Two and a Half Men when Evelyn's new boyfriend turns out to be one of Charlie's old girlfriends. Once the obligatory torrent of puerile jokes are through, the episode is surprisingly sensitive.
One episode of Tales from the Crypt ("The Assassin") had a team of government assassins invade the home of a very stereotypical suburban Housewife because they're convinced her husband is a rogue former agent who used Magic Plastic Surgery to radically alter his appearance before going underground. Nothing she says can convince them otherwise so she turns the tables on them and easily kills them all. It turns out she was their rogue former agent after quite a bit more plastic surgery than even they had been prepared to believe.
Female Agent: Does he still like it rough?
Housewife: Yes, as a matter of fact, I do.
This is also the twist of a later episode, "Last Respects", where a female lawyer hired by a dying rich man turns out to be the man's long-lost son. Her father doesn't learn this until after he attempts to seduce her, prompting her to disrobe for him.
The victim in one episode of Bones turns out to be a postoperative transsexual woman. This is handled with surprising sensitivity, and despite the title of the episode that status is not the focus of the plot.
An episode of Night Court had an old university friend of Dan Fielding show up as a post-op MtF transsexual, in the process of getting married; with Dan naturally playing the role of rabid homo/transphobe. The show being what it was, this was mostly played for laughs; but also a Crowning Moment of Heartwarming as well.
Cassandra from the "The End Of The World" and "New Earth" is a trans woman. She's also thousands of years old and had so much plastic surgery that she's now only a face on a very thin layer of skin or at least until she begins to possess Rose's, the Doctor's and ultimately her caretaker's bodies, so being trans is one of the least notable things about her.
"A Town Called Mercy" features a transsexual horse. His name is Susan and he would like you to respect his life choices.
Mark in Ally McBeal found out that his girlfriend (played by the lovely Lisa Edelstein) was a MtF pre-op transsexual. They tried to make it work anyway, but he was just too freaked out.
In an episode of St. Elsewhere, one of Dr. Craig's old pals shows up at the hospital. All goes well until he happens to mention that he's having sexual reassignment surgery. After having a trademark freakout for most of the episode, Craig finally accepts the situation.
One episode of The Sarah Connor Chronicles features Sarah searching for a man on the run from Skynet, only to find out he's been hiding his identity by living as a woman. None of this is played for laughs, and with zero amount of freaking out or any talk about sex. Alan/Eileen later admits to being strangely grateful for the opportunity to live as her true self, despite being hunted.
In one episode of Rab C. Nesbitt a new barmaid at Rab's local pub is a pre-op MtF transsexual (played by David Tennant, no less!). At the end of the episode she helps Rab and Mary to get revenge on Mary's extremely sleazy new boss (who has been sexually harrassing her from her first day in the job) by taking Mary's place at work one day and seducing him in the broom cupboard, leading to a spectacularly horrified reaction when he discovers certain unexpected items...
In one episode, the Victim of the Week, Cheryl (played by Kate Moennig), is on trial for beating a man to death. As the investigation continues, it's discovered that she is a pre-op transsexual woman, and she acted in self defense. Long story short, she was put in a men's prison, and after her trial, she is gang-raped.
"Transitions" involved a pre-teen transwoman whose father refuses to let her start hormone therapy and transition. The episode treats the young girl quite sensitively, with most characters accepting and using her preferred identity and her father eventually coming around (even after being brutally attacked.)
An episode of CSI: Crime Scene Investigation featured a well-intentioned doctor who did back-alley sex-change operations. It also revealed that some show girls weren't born girls.
In another CSI episode, the victim was a pre-op transsexual woman, killed by an actor after he goes to bed with her, discovers her sexual identity and freaks out about the fact damaging his carreer. It ended with Grissom saying:
There's an old rule of showbusiness that says 'Never be caught with a dead woman or a live man. He was caught with both.'
A similar case happens in CSI: New York, where a MtF transsexual (who was still transitioning) is found dead in the men's toilets of a very posh hotel that happened to have been running a political rally/party at the time. The initial suspect was a governor who had raped the woman's sister, but the murderer was actually a man who she'd made out with earlier that evening - finding out that she was biologically a man enraged him (made worse by the fact that his friends knew, and found it hilarious that he'd kissed a man), and he flipped out when he saw that she was using the men's room "like a normal man".
Two episodes (that I recall) of NCIS had transsexual characters. One became a (brief) running joke after Tony made out with her, and whilst the subject wasn't dealt with insensitively, it wasn't amazing either. The other was a character who was dead by the time the episode really began (suicide), and was dealt with a lot better, even if there was the obligatory "he... she... he-she" moment.
An episode of The Listener, "Lisa Says," had a transsexual character. Well dealt with and reasonably unusual because the character was FtM.
Inverted on Will and Grace. Jack (a gay man) finds himself sexually aroused by a female stripper giving him a lap dance and starts to question his existence, but is relieved to find out that she is a pre-op transsexual and he was just aroused by the feeling of her penis.
Adam in Degrassi The Next Generation is introduced as a New Transfer Student, and we find out his secret at the same time as everyone in the school does. His grandmother still doesn't know. As a bonus, the character also has the title of the first fictional, transgender, teenaged character in the history of scripted television.
In the French-Canadian series Un Gars Une Fille, Guy and Sylvie participate in a gay pride parade alongside Guy's lesbian half-sister. There, they encounter an old high school hockey teammate of Guy's, who has transitioned into a woman. A humorous line happens when Sylvie asks her if it was a difficult process.
"Yes it was, and it took a lot of balls... which I no longer have!"
Jasmine/Jason of Holly Oaks is an FtM transexual...whose male side gets framed for murder by a Psycho Lesbian so he has to carry on living as a girl. It's...complicated.
The episode "Boy Crazy" in Cold Case features a young FtM transsexual in the 1960's murdered for dressing and acting like a boy.
An episode of ER called "Next Of Kin" stars a child named Morgan. The episode doesn't end well, since she's forced to live like a boy after moving in with her mom when her dad dies; apparently due to the fact her step-dad would not accept her as a girl.
One of the dozens of subplots in Dirty Sexy Money revolves around Patrick Darling's relationship with a post-op transsexual woman named Carmelita, which he attempts to maintain despite (a) being married to someone else and (b) running for the U.S. Senate.
One episode of Dark Angel has Jam Pony's resident square Normal get into a relationship with a transsexual woman. When he finds out, he's still quite willing to go out with her, but she dumps him and expresses interest in resident lesbian Original Cindy, who is repulsed.
Mrs. Hudson from Elementary. Interestingly, little has been made of it — she hasn't been treated differently, joked about, or anything really.
Suzanne Vega song "As Girls Go" about a male to female transsexual.
The Cliks are the first band with a trans* frontman to be signed to a major label. Apparently their leader, Luacs Silveira, abstained from testosterone injections to preserve his singing voice.
Dolly Parton's "Travelin' Thru" was written with the process of transition in mind. It is played at the credits of the movie Transamerica.
The appropriately named Scorpions hit "He's A Woman, She's A Man".
The most common interpretation of the song "For Today I Am A Boy" by Antony & The Johnsons is that it's about a transgender person. The songs "You Are My Sister" and "I Fell In Love With A Dead Boy" have the same interpretations.
Punk band Against Me! announced in February 2012 they were recording a new album. Fast-forward to May and the album's title is released: Transgender Dysphoria Blues... along with news that their lead singer is also transgender.
UTA Uloid/Vipperloid Yokune Ruko is an intersex chimera of 90% male/10% female, according to his/her creator. Due to Ruko's very feminine appearance (as well as her expansive bust), many fans (and sadly, as a result, Fan Dumb) treat the 'loid as female for the purposes of non-sexualised fan works ... despite the fact that the whole point of him/her is that they have 'both a male and a female voicebank.
Queer porn is becoming more popular, and with it female-assigned-at-birth genderqueer individuals and female-to-male transsexuals are becoming more apparent.
Exalted has two examples. The Tya are woman in the West, who after getting intricate tattoos and drinking a tonic that sterilizes them, are legally considered males, and can sail without fear of Storm Mothers, who destroy any ship that has a woman more beautiful then them, which includes pretty much any woman. The Dereth are Delzhan who wear a special gray sash and are legally and culturally recognized as the opposite gender.
The Lunar Exalt Silver Python is agender. As a form of homage to Luna, who's associated with gender fluidity, zhe regularly switches genders every twenty years, and no longer remembers or cares which zhe started out as.
Of all franchises, the World of Warcraft Tabletop RPG actually touched on this one, by explaining how quilboar- a race of warthog-like humanoids, who are Always Chaotic Evil in the MMO but are given a somewhat more sympathetic portrayal in the tabletop game- operate under a strict Stay in the Kitchen rule, but if a female proves herself to be a strong and capable warrior, then she is declared to be a male by the tribe's shaman, and will live as a male and even take wives from that point forward.
In Persona3, during "Operation Babe Hunt" Junpei, Akihiko, and your protagonist are victims of Unsettling Gender Reveal when the only woman who actually is interested in you three seems rather suspiciously eager and vulgar minded. The reveal is when Akihiko realizes she has some hair on her chin and she outs herself, and given how disappointed she was that you figured out "her" secret, and that she wanted you guys as "boytoys" anyway, this actually is a a case of Trans Equals Gay being correct.
Poison and Roxy from Final Fight, both male-to-female. They didn't make it Stateside in the console versions, though (thank you very much, Nintendo Standards and Practices). In fact, Poison doesn't reappear until Final Fight Revenge. From that point forward, she sticks around as Hugo Andore's manager/bodyguard/bickering best friend, i.e. that's how we see her in Street Fighter III.
(As this in-depth documentary points out,) Poison and Roxy are both labeled as "newhalf" in their concept art and Poison has the term in the original Japanese instruction booklets for the first two games in the series. As the booklet came out two years in Japan before it hit Stateside, it is unlikely that Capcom made this change simply to accommodate Nintendo. While Capcom may not have considered them to be women, they were still "newhalves" from the very beginning.
Another example of the term "new-half" appearing in videogames is the Frozen Half, an ice magician described as such in Castlevania Symphony Of The Night. The Dracula X Chronicles rerelease changed the term to "transvestite". In both games the enemy is described as serving Galamoth, and it indeed first appeared in Kid Dracula, though wearing ice skates and looking far less convincing.
Perhaps the most famous video game example is Birdo, who was described in the manual of her first appearance as "wanting to be called Birdetta" and "wanting to be a girl". Although she started as a crossdressing male, more recent appearances have hinted (Captain Rainbow provided more concrete... evidence) that she has since had "the operation", and transitioned to a female body.
Magypisies look like this. They actually have no real gender.
It's slightly ambiguous, but Robin of Cute Knight Kingdom appears to be transgender female-to-male.
Lethal Joke Character Eater from Blaze Union has two personalities, one of which is male. Eater is biologically female, but when the male half is in control, he is treated by all other characters and by the game system itself (which has different unit formations based on gender) as a man who just so happens to be running around in the girly clothes his other personality put on in the morning.
Gloria Union has Kyra, who identifies (and is treated by the game's system itself) as intergender.
Erica, formerly Eric in Catherine. Notably, The Reveal is not treated as anything especially dramatic - it's mentioned rather nonchalantly in the Lovers True Ending, Toby is happily in a relationship with her (or at least one with a lot of mutual snarking), and Vincent, Johnny, and Orlando knew all along as he went to high school with her. In hindsight, there's a lot of foreshadowing for it.
Played gratingly for "laughs" in Dragon Age: Origins and slightly less gratingly in Dragon Age II. In the former, at the Pearl, the PC has the option of saying "surprise me" and getting a very obviously male dwarf prostitute in a female costume. In the latter, at the Blooming Rose, the transgender elven prostitute at least has a female body model even if her voice is male.
Husky Dwarf: I've got a little something for everybody.
There were transgender elven prostitutes in Origins as well, with such lines as "You have to slay the dragon before you can get to the princess". Also, the "surprise me" option can lead to a whole number of encounters, from the crossdressing dwarf to a room full of nugs- think a pig crossed with a naked mole-rat.
Subaru Kujou in the fifth Sakura Taisen game is pretty clearly genderqueer; zie always uses gender-neutral speech (at least in the Japanese version), refuses to indentify as male or female, and dresses in both masculine and feminine attire.
Jean Armstrong from "Recipe for Turnabout," the third case of Phoenix Wright: Ace Attorney: Trials and Tribulations is an unusual case in that he is a very masculine man physically (is burly and has FACIAL HAIR), but has a very effeminate character and identifies himself as a woman on multiple occasions.
Kaine in A Profile. It's handled pretty tactfully and pointed out that it makes things pretty difficult for him. He reacts poorly to the issue when it is mentioned. However, despite mostly being handled well there appears to have been some confusion on the part of the writers between this and homosexuality. Though it may just be his own inadequate understanding of the issue and that Kaine simply happens to also be attracted to women. Kaine is biologically female, however, but never felt like one. So he/she started going to school in male clothing and took male hormones to be more masculine. Despite being transsexual, Kaine continues to be treated as a male. He gets more female attention than Masayuki despite being pretty open about it.
Venus Envy is all about a male-to-female transsexual teenager, who, at the beginning of the comic, has recently switched schools as she moves to living as a full-time female. She also has a friend the same age who is a transitioning FtM transsexual too.
One of the lead characters in Closetspace is a transgender woman, who struggled with the decision of whether to undergo SRS, later regretting the surgery, but retaining her female identity. The other lead is also transgender, just starting her life as a woman.
The main subject of Trans Girl Diaries as it involves a main cast of transsexual characters. Also its fan sequel to Venus Envy, "This is Your Life."
In Jennifer Diane Reitz' series Unicorn Jelly, Wai Wai Ngo is eventually revealed to be a transgender man. This is a serious issue, as gender deviation is punished by death in the society of the time, and furthermore, this is discovered at a point After the End when everyone is obligated to have children due to the small surviving gene pool. In the Alternate Universe series To Save Her, we see a younger Wai struggling to get his father to recognize him as male; later, during their travels, he is given sex-reassignment surgery to become fully male (the medical science in the Splay they went to being highly advanced).
Tom and Charlie from Khaos Komix Tom being a FtM and Charlie being a MtF. The author also identifies as "Trans".
Natani of Two Kinds went from merely wishing she was male (instead of just pretending, due to her profession as an assassin) to actively believing it (due to her soul being merged with her brother's in order to save her from a dark curse). Though Natani lets her brother refer to her as "Sis" with minimal grumbling. Whether Natani counts as a "true" transsexual or is just a self-loathing misogynist is probably deliberately left open.
Minor character Riley from Errant Story is intersexed, which has caused chaos at least once.
While Dr Pegasus in Umlaut House is a fairly typical Gender Bender in the current stories, there have been a few hints that she had to deal with the problems typical of a Real Life transsexual before that.
Emerald, formerly Richard in 5ideways.
Word Of God is that Chelsie Warner of Concession identifies as female, but since she's ten years old and, going by her behaviour, suffering from a LOT of sex-related issues it's unclear in the comic. The Where Are They Now epilogue shows her at the age of eighteen, fully transitioned and apparently recovering from her traumatic childhood.
Molly Ricketts in Rule, Britannia is transgender, although it's said early on that none of the other characters are sure whether he's MtF or FtM (He's later revealed to be FtM.)
A transsexual character receives a surprisingly sympathetic treatment in Exiern, a comic which normally plays its gender benders for laughs, when one of a group of gender-bent priests is shown to view it less as a curse and more as a liberation, and her backstory clearly describes someone who entered the priesthood primarily because she was unhappy with her birth gender.
Rain is the title character of a slice-of-life dramedy webcomic that tells the story of a young transsexual girl who is just starting out her senior year of high school and hoping to fit in and find her way as a woman.
The Dragon Queen features the eponymous hero, the city's "first and only transvestite super-hero" who was born Bradley Bartlett but currently dresses female, identifies as Brandywine Bartlett, and has the people around hir use female pronouns.
In Tales Of A Gay Asian, there is a MtF transsexual sengchou who has stubble and gets further surgery to look like Lady Gaga.
In The Dragon Doctors, there are plenty of Gender Benders, but one actual (FtM) transsexual does show up in Mori's backstory chapter. In a setting where magic can easily change your gender, this might not seem to be a big issue, but Lem came from a country where magic was strongly discouraged. Worse, Lem was self-medicating with cheap, temporary Gender Bender potions that had a toxic after-effect, and he nearly died from it.
Casually mentioned in Dominic Deegan; the "alterist" (magical plastic surgeon/fertility doctor) Dominic and Luna go to see gives herself as an example of the non-Mad Scientist applications of alterist magic when Dominic gets freaked out. She looks entirely like an average biological woman (even allowing for the Only Six Faces artstyle), her status doesn't matter to the story, and the situation isn't played for either laughs or angst.
The protagonist of What's Normal Anyway? is a FtM, and the webcomic mainly revolves around gags related to him.
The now apparently defunct Trane-generation comic was a bunch of gag comics revolving around transgender issues, mainly FtM ones.
One of the leading characters in Mr. Normal is a closeted MtF trying to not be MtF.
In Greg, Greg is hit on by the same transsexual in multiple strips despite his unwillingness to engage. An example here.
Several characters in Unity and its spin-off stories:
Juni Melrose, main character in Unity, identifies as neutrois (although their neural clone Zero seems to identify as more feminine, or uses feminine pronouns at least, and also refers to Juni retroactively as female). Juni also seems to get into relationships with other genderqueer characters, such as Sam Roarke. Later, Tanya Harris implies a potential neutrois identification.
Alda Henning in the Breeder sub-story
In Blackout, Min is implied to be female-identified but has a male's spurs
The Princess revolves around a young trans girl named Sarah. Compared to the others it has a considerably lighter tone, being like a children's comic.
Early on in Webcomic/8BitTheater, Red Mage was shown to have various gender identity issues. Later subverted when it was revealed that he wasn't transgender at all, but that Thief had simply been playing headgames with him to make him think he was, for no apparent reason other than Thief's amusement at the emotional distress this caused him.
Ghastly's Ghastly Comic featured Freddy, a woman with a penis and a male name whom the author referred to as "s/he": "I feel s/he transcends all normal concepts of gender. S/he's not gender dysphoric, s/he's gender euphoric."
The title character in The Saga Of Tuck is a teenager who is physically intersexed, and (possibly) bi-gender. A number of minor characters are also transgender, and several more are Transvestites.
Gender-bending is a common element of the Paradise setting. Some (not all) gender-bent characters are Wish FulfillmentAuthor Avatars for transgender individuals in real life. Perspectives being a mini-series in that universe about how a transwoman would have lived her teenage life if her best friend and not her had suffered Body Dysphoria instead.
Gender-bending is even more common in FreeRIDErs which was created by the same person, in background material it was mentioned that many who tested out the Gender Bender Nanites in the earlier days of RIDE Development had signed up for it to cure their Gender Dysphoria. Paul Reverbek from the story "As A Woman I RIDE" is an Earth Boy who steals a RIDE to finally be free of her GID, it's written in first person perspective and she's played very sympathetically. On Earth where they don't have RID Es, people can be scanned for Gender Identity Disorder and if they have it they are given nanites to make their bodies match their minds. There are those on Earth who are peeved because it is illegal to change someone with nanites unless they have GID, one gender-curious man without GID actually goes to Zharus just to see what being a woman is like. Finally it is noted that people who use RID Es of the opposite sex that they are have their brains modified by the nanites as well as their bodies to ensure they don't develop Gender Dysphoria... though some RID Es intentionally sabotage themselves or are sabotaged by others in order to give their humans Gender Dysphoria.
Tales Of Mu features Steff, a MtF half-elf. In addition, the culture of the subterranean elves features an "ornamental" third gender of MtFs called "halfkind," who undergo a magical transformation that enhances both breasts and male organs, and who serve mostly as a status symbol for their families. Steff eventually is given the halfkind potion by a subterranean friend.
Twinfools of YouTube's "Fighting Dreamers Productions" Cosplay Group was very open about his transition on his own channel, but did not carry it into the groups main content. He remains the driving force behind the group playing a majority of the characters and as the main source of the funny.
In a Family Guy episode, Quagmire's Navy war hero father, Dan, undergoes surgery to become Ida, much to Quagmire's chagrin. Having bungled a Gay Aesop in a previous episode, the writers tried to make the character sympathetic, but still trotted out the old jokes (including an Unsettling Gender Reveal), and earned the ire of quite a few LGBT people. It didn't help that, when she wasn't acting stereotypical, Ida was a Flat Character at best.
The film Stewie Griffin: The Untold Story also had future-Meg going to college and getting a sex change, becoming a man called Ron.
Done once on The Cleveland Show but pulled off with even less tact than the Family Guy example above. The episode doesn't even try to portray Auntie Mama (yes, that's the character's name) in a positive light, portraying her as somone who "manipulates" straight men into loving her and being called a "guy pretending to be a woman." At least with Family Guy there was an attempt at sensitivity and understanding, however clumsy.
In Bob's Burgers, a positive example of transvestites comes in with "Cabs, Bob? Sheesh!". No hamfisted aesop attatched, just a trio of friendly, funny transvestites (one being a pre-op MtF) who befriend Bob on his taxi route, and their only negative attribute is the fact that they're implied to be crackwhores. They even help him out in the climax and only one blink-and-you-miss-it Unsettling Gender Reveal joke tucked in.
Alice in Superjail is a male-to-female transsexual, though it's played for laughs because she is very clearly masculine (which has lead to some controversy around the character and her implications). Also, clearly pre-operative given the always-noticeable bulge in her skirt, and (censored) depictions of her oversized genitalia. The Warden lusts after her and is initially unaware of this, though it appears he either forgets about seeing her genitalia at the end of season 2 (due to Negative Continuity) or doesn't mind it.
Bruce is the reverse of Alice and portrayed as overweight and lisping, with an aggressive temper. His personality is delved into less than hers, though he constantly tries to challenge and one-up her in his appearances.
Recess(of all shows!) gave us Mikey mentioning his Uncle Mary. Vince is confused to why Mikey's uncle is named Mary, and Gretchen just tells him not to ask.
Adventure Time impressively went there with the "Princess Cookie" episode. Whether Baby Snaps was supposed to be transsexual or just wanted the role of princess is slightly unclear, but the episode, with its unusually serious themes of bullying and suicide, works as an "It Gets Better" message for gender-variant youth, except for the part where he's interred in an asylum.