Transsexualism

Transsexual people are those whose individual self-perception of their own gender is not typically associated with their biological sex. Some transsexual people pursue means (e.g., hormone replacement, plastic surgery, "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.

Now for some definitions:
 * Homosexuality is a completely separate issue. Transsexuality is not gayness turned Up 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. 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".
 * 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.
 * "Androgyne ", "Agender ", "Gender Variant ", and "Genderqueer " 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.
 * 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".
 * AFAB /FAAB /CAFAB, AMAB /MAAB /CAMAB and UAB 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".
 * Drag Queens and Kings are performers who dress as caricatures of the opposite gender, but most of them identify as their biological sex in their mundane lives. They tend to be Camp Gay men and Butch Lesbians gender-bending to entertain, hence the mistaken notion that a transsexual is "super" gay. Only a few drag performers are trans, many of whom leave the drag world behind after transitioning.
 * "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.
 * "Shemale," "He-She," "Trap," "Tranny," etc. are considered deadly insults if they come from anyone without N-Word Privileges.
 * Also, calling a trans person, an intersexed person or any person whose gender you can't identify "it" is one of the worst things you can do. At the same time, it's rude to try and assume what gender they are -- if you aren't sure, it's better to just ask them what pronouns they prefer.
 * However, some gender-fluid folks will prefer discarding the 'he/she' system completely. They may ask you to alternate between pronouns, or want you to call them 'it', 'they', or 'ze'. Once again, its always best to ask.
 * Cissexual, Cisgender or just Cis is the opposite of transsexual, the majority: someone whose gender identity matches up with their birth sex "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 Did Not 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 (between 1 in 500 and 1 in 2,500.) 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 motive for murder in real life, this type of humor goes beyond mere Unfortunate Implications.

Contrast Gender Bender, which is about men and women swapping physical sex through Applied Phlebotinum (but occasionally, such stories may also involve transsexual characters.) Also contrast Easy Sex Change, which is this trope plus Did Not Do the Research or They Just Didn't Care. Unlike Gender Bender, there's at least a pretense of realism, but many physical, psychological, or social aspects of the sex change are minimized or ignored. Has nothing to do with Transhumans; the shared root Trans is the only commonality, and even then both terms use different definitions of it. The root Trans here means "opposite" roughly.

See also: Transgender.

Anime and Manga
"Masaki: How did you... know I'm a... girl...?
 * 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,  is a  transman. In this character's case,  . Towards the end of the manga,.
 * Angel Sanctuary also has, 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   usually looks very much like a wounded Femme Fatale. In the purely biological sense,  . 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   and as proof of his/her devotion,   S/he even seduces   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 . 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'.
 * . While she laments to have been . Although she seems to embrace her true self in the end, she still has gender issues. Meanwhile, her brother
 * 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 Oh, and given how 'effeminate' the main character is, he ends up in drag just about every other storyline.
 * from Lovely Complex.
 * 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 (MtF) and Yoshino (FtM) from Wandering Son. Also their adult friend Yuki, who is implied to have had a full physical transition.
 * Oozora Hibari 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  and.
 * 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
 * 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.
 * Hana in Tokyo Godfathers says, "I am a mistake made by God. In my heart, I am a woman."
 * No Bra is about a male high school student and his relationship towards the biologically male Yuki, who at first appears to be a crossdresser, but later in the series, Yuki also doesn't seem to like having to act like a boy, and often said stuff that sounded like she is transsexual.
 * The BL light novel and anime Sukisho has Team Mom Nanami, who is practically a transgender Yamato Nadeshiko.
 * 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.
 * The Yuri anthology Mermaid Line has a Slice of Life story where a male to female transsexual and her (apparently bisexual) fiancé decide what to do about her transition.
 * 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  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.
 * Arisugawa "Alice" Kintarou from Mariasama ga Miteru.
 * 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 Little Sister 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.
 * Watarase Jun from Happiness. Dresses as a girl, participates in the girls' sports instead of with the boys, and is overjoyed when magic accidentally turns her into a physical girl.
 * 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 a 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 some to think she's just 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.

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.
 * from Level E is female-to-male and has felt male since he was four..
 * 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, 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 almost , 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.
 * The protagonist of After School Nightmare is intersexed, gender male. The first page in the manga has him averting No Periods, Period, much to his discomfort.
 * From Ludwig Kakumei, the Goose-Girl in the Well,
 * In Sorcerer Stabber Orphen, we have . Orphen explains to Majik and Cleao that   Cleao and Majic are rather surprised when Orphen tells them (and in fact, Cleao wonders if   knows), but Orphen himself seems to be pretty nonchalant about the whole deal and it's never discussed again.
 * Murakami's Kafka on the Shore has Oshima, a gay trans man.
 * 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.
 * Nathan Seymore of Tiger and Bunny is confirmed in supplementary sources to be agendered.

Comic Books

 * 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 a case of Did Not Do the 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 Leader Jane's World has
 * 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 ), 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).

Film
"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 excellent film Breakfast On Pluto is all about the life of an 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. Hedwig spends the movie dealing with essentially having become an MtF transsexual, until
 * Angel Dumott Schunard, Rent. Angel is played by a male actor, referred to (mostly) by the female pronoun and in a relationship with a gay man. It's not quite clear whether she is MtF or genderqueer.
 * Angel is a Drag Queen. Referring to him as "she" was probably because of that.
 * Transamerica is a film centering on a transsexual woman.
 * The Crying Game.
 * 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;.
 * 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 . Hilary Swank plays the role very believably.
 * Bernadette in Priscilla Queen of the Desert is a transwoman (rather than a drag queen like her two companions). One guaranteed way to make her angry is to call her "Ralph"...
 * 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
 * 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 from To Wong Fu, Thanks for Everything! Julie Newmar gives Chi-Chi a rundown of genderqueer types, doubling as a "The Reason You Suck" Speech.


 * 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 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.
 * Played for Laughs with Stan/Loretta from Life of Brian.
 * There's a German film called Romeos where a gay transman falls for someone.
 * The 2011 French film Tomboy is about a 10 year old girl who moves to a new neighborhood and decides to live as a boy.
 * The World According To Garp features John Lithgow as Roberta Muldoon.
 * 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".

Literature

 * 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 . 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.
 * in The Saga of Tuck is a teenager who is . A number of minor characters are also transgender, and several more are Transvestites.
 * 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 . 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, 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.
 * in Maria V. Snyder's Study trilogy.
 * 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.
 * Diana Comet
 * 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 Backstory.  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 Culture 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.
 * 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 their abusive father. Their Mamma supports them devotedly, though, and they gets some solace in their Inter generational friendships with La Señora and Eva.
 * 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.

Live Action TV
"Daniel: Don't call him my brother. My only brother is my sister, Alexis."
 * 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.
 * Ugly Betty has Alexis Meade, who lives as a woman after faking her death. Of course, her brother didn't know until after he starts hitting on her...
 * In a later episode in which Daniel is displeased by his long-lost half-brother:

"Female Agent: Does he still like it rough?
 * One of the reasons why the Argentinian telenovela Los Rold Ã¡n 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.

Housewife: Yes, as a matter of fact, I do."

"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.'"
 * 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" episodes of Doctor Who 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, so being trans is one of the least notable things about her.
 * 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 an episode of Law and Order Special Victims Unit, 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,.
 * An episode of CSI 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:

""Yes it was, and it took a lot of balls... which I no longer have!""
 * 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 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.
 * However Trailers Always Spoil, this was heavily hinted in the promo for Season 10 to be the case. The one thing that did help matters, the actress playing Adam is named Jordan Todosey. So the opening credits didn't also spoil, unless you have seen other Canadian teen shows.
 * 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.


 * 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.

Music

 * 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.
 * The Velvet Underground's "Lady Godiva's Operation," focusing on an MtF transsexual first going under the knife. Things don't really work out.
 * 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.

Pornography

 * The trope is extremely common in porn, but, being porn, nearly always the character is portrayed as male-to-female transsexual, having a fully female identity, a pre-operated body (keeping the fully functional genitalia), a lusty disposition and ability to have sex in either form with males, females and everything else. Which would be fine on screen and raise plenty of Unfortunate Implications in Real Life - and not only the brutal kind of homophobic or transphobic Unfortunate Implications people would imagine at first glance, but also plenty of unwanted attention from those who believe in the idea of a perpetual lusty creature.
 * Queer porn is becoming more popular, and with it female-assigned-at-birth genderqueer individuals and female-to-male transsexuals are becoming more apparent.

Tabletop Games

 * 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.

Theater

 * Sweetie in Bombay Dreams, a beautiful transwoman who just wants her childhood friend and longtime crush Akaash to live his dreams and get what he wants, to the point of eventually performing a Heroic Sacrifice.
 * As mentioned above, Angel from Rent.

Video Games

 * In Persona3, during "Operation Babe Hunt" Junpei, Akihiko, and your protagonist are victims of Dropped a Bridget On Him when the only woman who actually is interested in you three seems rather suspiciously eager and vulgar minded. The reveal is when
 * 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.
 * The amusing fact is that this whole situation actually arose out of trying to prevent censorship. Capcom of Japan knew that it was not kosher to depict violence against women - so their excuse was that the characters weren't born as women in the first place. They have gone further on record that Poison's status is post-op in America and pre-op in Japan.
 * (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.
 * 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  of Cute Knight Kingdom appears to be transgender female-to-male.
 * It's a hot point of debate in the Persona 4 fandom whether this character is  or, but one can make a pretty strong case for
 * This interpretation doesn't hold much water, since  very clearly states that she accepts her gender:

"Husky Dwarf: I've got a little something for everybody."
 * And in the spin-off novel,  has grown her hair very long and now looks very feminine.
 * Examples from Dept Heaven's "Union" games:
 * 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.
 * in Catherine. Notably, The Reveal is not treated as anything especially dramatic - it's mentioned rather nonchalantly in the Lovers True Ending,  is happily in a relationship with   (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  . 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.


 * 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.

Visual Novels

 * 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 he simply happens to also be gay.

Webcomics

 * 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).
 * Katie Lynne Sapphe: The Webcomic is a very irregularly updated Diary Comic by a transsexual woman going through transition as a college student.
 * 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.
 * Ash from Misfile acts more like a genuinely transgender teen than the usual Man, I Feel Like a Woman protagonist of a Gender Bender webcomic.
 * Marius from My Life in Blue.
 * 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.
 * in 5ideways.
 * Word of God is that of Concession identifies as female, but since  it's unclear in the comic.
 * 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.)
 * The minor character Aubrey in Boy Meets Boy is a pre-op 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.
 * Z from the Slice of Life Journal Comic Gemini. An interesting case, as her body is not just her own; she shares it with a cis man.
 * Casually mentioned in Dominic Deegan Oracle For Hire; 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.
 * Karabear Comics Unlimited debuted Eiderdown, an MTF superhero, in issue 3.
 * Acchan from the cub comic, The Neon Children.

Web Original

 * Gender-bending is a common element of the Paradise setting. Some (not all) gender-bent characters are Wish Fulfillment Author Avatars for transgender individuals in real life.
 * Jade Sinclair (nee Jared Reilley) of the Whateley Universe. Toni too, before she got her wish through Gender Bending (She was born Tony).
 * 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.

Western Animation

 * 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 a Bridget Drop, 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.
 * Seth MacFarlane then further infuriated the LGBT community by saying that he thought the character was "probably the most sympathetic portrayal of a transexual character that has ever been on television." Many took this to be proof that MacFarlane had never seen a transsexual character on TV.
 * 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 Dropped a Bridget On Him joke tucked in.
 * Alice in Superjail is a male-to-female transsexual, though it's played for laughs because she is very clearly masculine. Also clearly pre-operative given the always-noticeable bulge in her skirt.
 * Recess (of all shows!) gave us Mikey mentioning his Uncle Mary. Vince is confused to why Mikey's uncle's named Mary, and Gretchen just tells him not to ask.