Before the Nazis took over
Magnus Hirschfeld was not popular.

Shock troop with whistles. We read in “Vorwärts”: The “Hamburger Echo” publishes the following invitation that was sent to it: Hamburg, the 12th of September 1920. Good Lord! On the 16th of September the Jew Dr. Magnus Hirschfeld will give a lecture in The Convent Garden. You are kindly requested to arrive there on time with a whistle and useful utensils. Please gather on the right side of the hall!
The shock troop of the German ethnic leagues The 16th "Scheiding" is now over and we don't know whether the brave shock troop managed to kill Doctor Hirschseld. The Hamburg data cruisers show their deep understanding of all areas of culture; Moissi (Aleksandër Moisiu) encountered them at an artistic lecture and now it's the turn of 20th century science!
He was a very prominent figure in trying to decriminalise homosexuality, as previously mentioned. As early as 1907 his house got vandalised with the slogan ""Dr. Hirschfeld eine öffentliche Gefahr – die Juden sind unser Unglück!" - "Dr. Hirschfeld is a public danger - the Jews are our misfortune!". He was criticised by the gay movement for having "Oriental" views on sexuality, he was criticised by sexologists for misusing sexology to promote homosexuality, he was criticised by large swathes of the public for promoting sexology and talking about sex so openly. He was labelled the Jew that brought the scourge of "Eulenburgism" to Germany.
The Eulenburg affair was basically a scandal that rocked Germany in 1908 when a lot of Kaiser Wilheim's inner circle were exposed as gay, and Hirschfeld (who'd already tried to get homosexuality decriminalised in the 1890s) acted as an expert witness for the defence (who were Jewish lawyers, possibly gay Jewish lawyers). Germans felt the gays (and Jews) had made Germany look bad internationally, and later during WW1, felt the gays (and Jews) had basically stabbed Germany in the back and that's why they lost. Hirschfeld appeared playing himself in the 1919 film Anders als die Andern (Different From The Others) which was basically a melodrama about two gay violinists who fall in love while Hirschfeld lectures the audience about how there's nothing wrong with homosexuality and it's terrible that gay people are persecuted, ending with a hand crossing out Paragraph 175 (the law that criminalised homosexuality). The reception of this film was so extreme that Weimar Germany literally introduced cinema censorship laws specifically to ban this film.
By the early 1920s his lectures - which, by the way, were mostly on Steinach's ball transplantation science but also contained defences of homosexuality and arguments for decriminalisation - were frequently disrupted by gangs of youths. On October 4th 1920 this escalated and he was pelted with stones and very nearly killed - in fact some papers actually reported he had been killed (he'd been knocked unconscious and dragged to hospital). The "Miesbacher Anzeiger" condemned negative reporting in other countries, noting that if Hirschfeld had exhibited a tenth of the shamelessness of his lecture in America, he'd have been tarred and feathered - calling him an apostle of sodomy and the Berlin Jews were all "spinach boys" (basically euphemistically "arse fuckers") who wanted to undermine Germany. Hitler himself made comment on Hirschfeld's attack, accusing him of the "spiritual murder" of thousands of Germans, of being anti-Aryan, and saying if he'd been in Munich at the time he'd have personally punched the "dirty old Jew" in the face as he was offering the vilest mockery of science and the attack on him represented the healthy resisting the unhealthy. It cannot be emphasised enough that people hated Hirschfeld because he was a gay Jew who was using Jewish trickery to undermine Germany by promoting gayness, and he came to be a symbol for all the excesses of Weimar sexual decadence. The Nazis increasingly targeted him in their publications framing him and his institute as public enemy number 1, highlighting his anti-volk undeutschen Geist (Un-German thinking) attitudes around homosexuality (and also promoting marital planning and contraception, which they characterised as the Jew trying to encourage the German volk to stop reproducing, to undermine them).
By the late 1920s Hirschfeld had basically stopped lecturing at all in Germany, and in 1930 he left Germany for good, because the Nazis made it clear they'd kill him if he stepped foot on German soil again. He tried to run his Institute from afar, but was not very successful at it.
After the Nazis took over
By late 1932 the Institute had started to crumble - the Prussian government was attempting to revoke its non-profit status, because whatever was left of the administrative staff hadn't filed any of the financial paperwork.
Hitler became Chancellor in January 1933. This reduced the need for Ernst Röhm's paramilitary brownshirts - Röhm was gay and his influence in the party meant homosexuality had been somewhat (slightly) tolerated, but his influence had been waning for some time. Immediately after the Reichstag Fire in February 1933, Hitler and his cabinet issued a decree that was signed into law by President von Hindenburg, which suspended habeas corpus, ended freedom of assembly, freedom of thought, freedom of expression, freedom of the presses and the right to privacy. Searches and property seizures were authorised to prevent activity that might endanger the state. At this point all well known gay bars were shut down and all gay publications and gay groups were banned (although it took them a while to work through them all, so many burned their membership lists). In March 1933, the "Enabling Act" was signed, allowing Hitler to make laws without the Reichstag's approval. In April, the Civil Service (including everything from teachers to judges) began to get purged of non-Aryans and people who could not be trusted to support the state - at universities, the emphasis was on professors who misused the scientific method to correspond to their own liberal views. April is also approximately when the Institute stopped operating, although presumably they'd already stopped offering their gay affirming therapy by this point - Bernard Schapiro wrote to Hirschfeld suggesting appointing an Aryan Director to see if they'd be able to carry on; regardless there were still a fair few people living there. The Gestapo visited several times during this period, apparently hoping to get their hands on something, but Hirshfeld's partner Karl Geise had already sent the most important personal records, documents and publications to Hirschfeld in Switzerland. It's speculated these included a variety of patient notes on prominent Nazis who'd received treatment there, which is something Ludwig Levy-Lenz suggested - he said they'd treated quite a few and they could be juicy blackmail material. Certainly some of their staff were Nazis or Nazi sympathisers; the head receptionist (who it has to be noted, didn't actually work there - she just turned up one day and started acting as the receptionist and set up a desk in the foyer, and everyone just went along with it - Hirschfeld never paid her) worked to help identify some of their homosexual patients.
Continuing on in April, The Boycott of Jewish businesses was announced, and The Twelve Theses Against Un-German Thought was published by the German Students Union. These theses basically argued that the German people needed to uphold purity of the German language, and because Jews can only think Jewishly and can't think Germanly, everything they wrote was a lie. The German Students Union were organised into groups and local chapters to purge academia of anti-German thought, to the point they started erecting pillories in universities. Students were then given blacklists of authors and directed to search their homes and the homes of friends for "corrosive literature", then search their university libraries for it. This was all in effort to have a mass burning of these books on May the 10th. On May 5th, students at the University of Rostock jumped the gun a little bit and piled up books they'd found from the "8 most evil authors" - Hirschfeld, Kurt Tucholsky (a satirist and outspoken critic of the Nazis), Stefan Zweig, Lion Feuchtwanger, Vicki Baum (Jewish authors accused of writing "asphalt literature" - basically globalist - also all critics of the Nazis), Erich Remarque (the pacifist who wrote "All Quiet On The Western Front"), Emil Ludwig (a Jewish biographer and journalist who was critical of the Nazis in the international press) and Die Weltbühne (an arts magazine that was openly critical of the Nazis).
This intensified on May the 6th, when "Aktion wider den undeutschen Geist" (action against un-German thought) occurred. Students across Germany organised themselves into shock troops, forcing their way into bookstores and public libraries. They had a long and ever growing list - Ernest Hemingway, James Joyce, Oscar Wilde, F. Scott Fitzgerald, Victor Hugo, Dostoyevsky, D.H. Lawrence, Jack London, H.G. Wells, art books containing lithographs of Henri de Toulouse-Lautrec or Paul Klee, sheet music of Mendelssohn compositions, anything communist, anything Jewish, anything obscene, anything that promoted neuroticism (a lot of psychiatry books including Freud). Also "Writings on sexuality and sexual education which serve the egocentric pleasure of the individual and thus, completely destroy the principles of race and Volk". So that included the works of Margaret Sanger, birth control advocate, but also very obviously included Hirschfeld's works (although he obviously was already on the list for being Jewish) and much of his library.
It would be weird if the institute wasn't raided - and it certainly wasn't targeted in isolation, despite the claims that one of the first act of the Nazis was to destroy the "trans clinic". So while students across Germany were raiding bookstores, in Berlin students from the Veterinary College and the PE Teacher College turned up, alongside brownshirts and a big brass band, and ransacked the place. Interestingly the brownshirts apparently told them to leave the case files alone (including all the surveys people did to get diagnosed with various conditions) because those didn't count as un-German. A lot of books were loaded into a truck, that would take them to Opernplatz to join all the other books seized from across Berlin to be burned on May the 10th - but the library was massive.

As I mentioned, a lot of it didn't get burned. You can see a student and a Nazi officer looking through it here, and there's lots of copies of a porn magazine called Die Ehe ("Marriage") that they're rifling through. Some of the archive was auctioned off and some was transferred to the Prussian State Library - large libraries kept "poison chests" of banned books so Party members could study their enemy and combat them more effectively, but also some of the library no doubt was just legitimately useful medical research and scientific journals. The students also found a bust of Hirschfeld and added it to their wagon, so they could chuck it on their big Nazi bonfire - this later got found by a street cleaner (because it was made of metal and obviously didn't burn) and is displayed in the Hirschfeld institute today. A separate plaster bust made its way to the Nazi Revolution Museum, where it was displayed with a sign "Der schöne Magnus Hirschfeld , das grösste Rübenschwein des 20. Jahrhunderts" - "The beautiful Magnus Hirschfeld, the greatest turnip pig of the 20th century" (Rübenschwein was used as slang during WWI to refer to a coward who never raised his head above the parapet and hid on the ground, like a rooting pig). Hirschfeld attempted to set up a new institute in Paris, but it failed due to lack of interest, so instead he wrote his thoughts on the Nazi ideology. In doing so he wrote that race was a social construct, and ideas of other races being primitive were made up to justify colonialism, and that racial purity was a bad idea and race mixing was good. He also accused them of misusing eugenics which he still maintained was a good thing (including involuntary castrations of the genetically undesirable) and he invented the word racism.
What happened to transvestites
So after the night of the long knives killed Ernst Röhm, nothing was stopping Himmler doing everything he could to eradicate homosexuality. Unlike Hirschfeld, the Nazis viewed homosexuality as a contagious illness that potentially could be cured. In 1934 they refined the code criminalising homosexuality from sodomy to "lewdness with men", which mean flirtation or even glances could be used for an arrest. They later expanded their approach to include forced castration of homosexual men (Dr Warnekros, the Lili Elbe surgeon, performed many such castrations on gay men) and Himmler pondered introducing the death penalty. It is worth noting that a conviction of homosexuality was not a guaranteed ticket to the ovens - most homosexuals were arrested and put in regular prisons, and released after finishing their sentence. Initially the only homosexuals who went to concentration camps were prostitutes and "seducers of youth" (child molesters), and then also people who were already on thin ice for something else (so a trade unionist might not be sent, but a gay trade unionist would be). This did later expand to include gay men who'd been proven to have had sex with more than one man and repeat offenders. The camps were sometimes temporary sentences designed to "educate" them not to be gay. However, if they got sent to the camp they'd often be worked to death or tortured by guards - the death rate was about 60% (far higher than other groups). They were also more likely to be selected for medical experimentation, such as the hypothermia experiments performed by Dr Gohrbandt (the vaginoplasty guy). Himmler allowed Dr. Carl Værnet to specifically see if he could cure gay concentration camp prisoners by injecting them with testosterone or implanting an artificial testicle into them, in a manner directly feeding off Steinach's research and very similar to Hirschfeld's own efforts in the 1920s.
They weren't as concerned with lesbians, although lesbians could be labelled "asocial" and if they were convicted of a political crime, would be more likely to face harsher sentences. But it was gay men Himmler wanted to eradicate and police would investigate effeminate men. Naturally this included the transvestite pass holders. But if they weren't gay, then no crime had been committed (unless they were doing something else like "causing distress".
There's a really long case history here about Gerd R. who was an unhinged masochist who kept hiding naked in his neighbour's bin. The gestapo cut his hair and forced him to live as a man, but as he was not homosexual, they attempted to rehabilitate his impulsive masochism in a sanatorium.
Another example, of a married transvestite from Annaberg who was seen by neighbours dressed as a woman:
No files have been issued against [him] and no incidents or previous convictions are known. Intercourse with homosexuals could not be proven. There are no known fetishists here with whom he might have been in contact. Given the circumstances, Obenauf is probably an outspoken onanist and transvestite. He did not commit his actions publicly. He has not committed any criminal offenses. However, he was thoroughly instructed about his reprehensible behaviour and warned not to continue - he promised to stop.
Remember how a lot of the heterosexual transvestites didn't want to associate with homosexuals, and formed their own support networks? This became relevant. Helia Knabe ran a mail order transvetite business, making corsets for men, custom lingerie, wearable breasts and what was called a "jockstrap genitalis". She also produced a periodical featuring writings from other transvestites - she did all this because her husband was a transvestite. Incredibly she carried on advertising in public newspapers throughout the 1930s, which is how she eventually got caught.
Despite a long transvestite career, Richard Knabe had no previous convictions. He not only assisted his wife in dealing with customer mail, but also provided legal assistance by writing letters to the public prosecutor, Dr. Arthur Richter, the Minister of Justice Franz Gürtner and the Prussian Prime Minister, Field Marshal Hermann Göring. Finally, he offered himself as "guarantee" to go to prison instead of his wife. He stressed his wife had started her business as a result of his inclinations. Both made no secret of this, neither before nor after 1933, and even aggressively supported transvestites during the course of the trial. To this end, they tried to awaken the Minister of Justice's understanding of their own and the collective fate of this morally completely harmless but deeply unhappy class of people - [who] have already had to suffer a lot". He eventually got sentenced for distributing illegal materials, but faced no punishment for crossdressing. The judge conceded “He is a transvestite, but only wears women's clothing and women's underwear at home, not on the street. He is married and also has two underage children." George Dehmel was convicted because the writings he copied had indecent content and were capable of hurting the sense of shame and modesty of the normally sensitive reader," but no punishment for being a transvestite. The police conducted a thorough search of everyone on the mailing list.
There was a report about a married office worker living in Mannheim: He was definitely a geriatric fetishist, and also a budding masochist. He had women's underwear in his apartment kept to which he idolized shows adoration. [...] However, it was not possible to prove that he had committed a criminal offense. Nothing negative has come to light." LAB A Rep. 35802 No. 116782, special volume II: 31.
Another married transvestite living in Quedlinburg sent in a letter, after a search-and-seize, demanding the return of his clothing and books (besides any that were banned by the Reich) insisting he'd done nothing wrong and didn't deserve to be treated like a criminal. The police agreed and returned them.
Anton Maier was a trained locomotive driver who, due to an eye problem, because as. Road roller driver worked on various construction sites in southern Germany. During his first interrogation he stated: “My urge for wearing women's clothing dates back to my early youth," so he "can't resist it at times." In public, Maier only wore women's clothing at carnival time; otherwise, he sometimes wore them in his room before going to bed in the evenings. "He had no criminal record and has never given rise to any complaints". He was released without charge.
A doctor's note on a case that recommends allowing full time crossdressing:
His behaviour is much more rude in men's clothing than in women's clothing. Given the integrity of his character, which I had plenty of opportunity to judge, there is no danger that he will engage in any abuse with transvestites. As a pure transvestite, he has absolutely no tendency to approach other people in an erotic manner of any kind. Rather, the real transvestite lives out his instinctual life in transvestiture, i.e. moving and acting in the role of the opposite sex. The real transvestite feels humanly worthy only in transvestiture. If he is constantly hindered by this, life will lose all charm and joy for him. In fact, all transvestites become severely depressed when crossdressing is made impossible for them. They then feel as unworthy as a normal man who is forced to wear women's clothing. In this particular case, from a medical point of view, I consider it justified if the authorities do not cause any problems for Mr. M. regarding his women's clothes and their wearing, since, based on my detailed knowledge of Mr. M.'s personality, it can be expected that he will not cause offense by doing so. Dr. Weigel.
Homosexual transvestites would be charged and the transvestite behaviour often resulted in them receiving the harsher penalty associated with homosexual prostitution, as it was believed gay prostitutes crossdressed. They seemed to be aware of this and frequently mounted defences that although they crossdressed, they were straight - only to be brought down either by a former sexual partner admitting it, or because they were overly honest and said something like "ok, I jerked off a couple of guys one time but besides that I'm straight". The police did also seem to consider two transvestites hooking up with each other as gay, since they were both men (as that's what they were checking for, although no known cases of t4t transbians actually getting punished for it).
Amazingly, some homosexual transvestites (or meta-attracted heterosexual transvestites) did manage to get away with it. Henriette B was arrested on July 21, 1941 in Vienna on suspicion of being a prostitute. During the medical examination it turned out that he was a "normally developed man" who was born on August 5, 1908 and whose real name was Heinrich Wilheim (Huelke 1949: 91). Therefore, a case was immediately filed for "evading military service". He admitted having sex with men and an investigation was thus launched. He stated during his interrogation that he had always felt attracted to men and had never been interested in girls - but he insisted he had never once had sex with a homosexual. Instead, all his partners were heterosexual and viewed him as a woman - and when he provided names and the police followed up, they all concurred that they viewed him as a woman.
Heinich had started working at age 17 as a maid, and had only worn women's clothing since. At around age 24, he had sexual contact with a man for the first time and considered self-castration, because "he felt like a woman and wanted to be one". The senior criminal inspector Hans-Heinrich Huelke distinguishes this and similar cases from “normal homosexuality”:
While the homosexual's social harmfulness lies primarily in the fact that he supports other people in living out their degenerate sexual drive, [...] this component of danger to the community does not exist in the case of the accused. His sexual partners believed that he was a woman and were not homosexuals. The accused therefore did not have a demoralizing effect on those around him due to his feminine attitude and therefore appears less dangerous to the public than a homosexual who appears in men's clothing (ibid.: 92).
B. was sentenced to six months in prison by the Vienna Regional Court for failing to register for military service. When he returned to Hanover after serving his sentence, he was emasculated at his own request in 1943, whereby "the health department [...] deemed emasculation necessary because B. had often come into conflict with the law and morals" (ibid.). At his insistence after his castration, he also got his penis removed. After that, B. applied to change his male first name to a female one, and no objections were raised. I think Heinrich is the transvestite who was then admitted to the Nazi Mutterschule and was allowed to foster a child
Another case of attempted transition is the aircraft manufacturer W. D., born in 1908, a married father of two daughters. His efforts “always focused on the desire to be completely female, to have female breasts and genitals” (Voss 1938: 22). W. D. had been trying for a long time to feminize his physique with the hormone preparation “Progynon”. . Since this did not lead to success, inspired by newspaper reports of cases of gender reassignment that had taken place (likely Lili Elbe) he repeatedly and stubbornly expressed his wish to have ovaries implanted" (ibid.: 26). His sister and his wife offered to donate one ovary each (ibid.: 32 f.). In order to achieve gender reassignment, W.D. initially contacted the Hamburg health authorities, who, however, only made him aware of the annoying paragraph (paragraph 183 of the penal code, which regulated causing public nuisance)" (ibid.: 27). He was probably aware of this, because when it comes to living out his transvestite inclinations it is said: "Fear of (going out in public) is only because of police concerns that lately he has had to give up taking his evening walks in women's clothes" As a next step, W. D. applied for approval from the Reich's Health Department. "I request castration and the implantation of a uterus and ovaries because I have felt the need to dress as a woman since my early youth, and my whole attitude is closer to the female sex than to the male."
On January 3rd In 1936 this request was rejected on the grounds that !there was no possibility of complying with it" (ibid.: 28). He now turned to the Reich Health Office. To add weight to the request, he added as justification "because I suffer a lot from it in my current condition and only recently had to leave my job because of it, but I also don't want to accept being fed by the state indefinitely" (ibid.: 28). He was suspected of being a homosexual and investigated, but despite his extended family being questioned, there was no evidence of any homosexual activity whatsoever. Therefore he wasn't charged.
There's more! But this post is far too long already. There's a really funny anecdote about a lesbian apple-seller who argued she needed to gradually reduce crossdressing or else her customers would freak out, but it'd be way better for a separate post specifically on women in this era.