Top 10 Crossdress Hentai Anime Of All Time – 2022

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Top 10 Crossdress Hentai Anime Of All Time - 2022

Cross-dressing is the act of wearing clothing that is not typically associated with one’s gender. In modern times and throughout history, crossdressing has been utilized for camouflage, comfort, comedy, and self-expression.

Throughout history, nearly every society has had a set of conventions, views, guidelines, or laws governing how people dress and what is proper for each sex. Crossdressing is a way in which someone may wish to challenge these societal norms.

In many countries throughout the world, it’s acceptable for women to wear men’s trousers and shirts, and it’s not seen as crossdressing. However, there’s still a heavy stigma around boys and men who wish to wear feminine clothing. Let’s destroy these gender restrictions with this list of ten cross-dressing anime!

Playing around with gender roles can be an unbelievably erotic experience for men, women, and those yet to make up their minds.

1. Skirt no Naka wa Kedamono Deshita

Skirt no Naka wa Kedamono Deshita

Shizuka Kominami is a shy college student who, despite her bashful demeanor, attends a college mixer. There, she meets Ryou Kirishima, a beautiful, confident woman whom she quickly befriends. After leaving the mixer together, the two spend the night talking and drinking.

But when an inebriated Shizuka ends up at Ryou’s apartment, one thing leads to another, and she finds herself being seduced by her new friend. And what’s more, Ryou is actually a cross-dressing man!

After a passion-filled night, Shizuka awakens to a note left by Ryou, promising more erotic moments between them later. How will Shizuka’s newfound relationship with Ryou unfold?

Checking out an anime series with a story of a girl who is uncomfortable around men but slowly falls in love with a guy who crossdresses as a woman is indeed interesting. In the first few episodes, Shizuka and Ryou’s relationship is nothing more than sexual pleasure. True romantic feelings evolved when the two returned to basics.

The episodes are short, but it’s a pretty good watch for fans of this genre of hentai.

2. Kyonyuu Dosukebe Gakuen

Kyonyuu Dosukebe Gakuen

At the protagonist’s school, there is a famous club of girls said to bully and target men, breaking them down with sex until they are like lifeless husks before moving on to the next victim. One rumor says all of them combined have had over 200 sex partners.

One day on the train, the protagonist is able to hear a conversation between college girls and the club girls. Turns out they are all virgins who have never had sex before. Unlucky, or lucky, for the protagonist, he is caught eavesdropping. That is the day they decide to silence the protagonist by finally living up to rumors by making him their target at the club.

All of the girls in this club are beautiful and pleasing to the eye. You can’t take your eyes off the screen because they’re all taking their turns with the protagonist, and there isn’t a single girl that you can miss. Each girl is different, so the hentai doesn’t get stale either.

3. Otoko no Ko Delivery

Otoko no Ko Delivery

Aoi and Shun are two high school students who share the same secret. They both work as cross-dressing prostitutes! The brothel service they both work for operates on a first-come-first-serve basis. So when Aoi arrives at the location to meet his very first customer, Shun has already beaten him to it.

Aoi goes to confront him the next day about it but is suddenly interrupted when Shun kisses him. He decides to show Aoi the ropes since he’s clearly new at this. After teaching him a few penis pleasing techniques, they go to meet their customer. It’s the same gentleman from the night before, happy to spend an evening with two pretty boys.

The enjoyment factor in this hentai is through the roof. If you love crossdressing and yaoi, this hentai is a must on your to watch list. Not a lot of hentai can be rewatched without it feeling boring, but this one is highly rewatchable. Aoi is clearly a newbie at the start of it, but by the end, he’s a pro.

4. Otome*Domain: The Animation

Otome Domain The Animation

Since the death of his grandmother, Minato now has to work as a cleaner while also attending a prestigious school. His employer and fellow student, Hinata, insists that due to this being an all-girls school, he has to pass himself off as a girl.

He soon adapts to his new way of life. He enjoys getting to know his fellow students while he works; the only trouble is they’re a little too comfortable around him.

Thinking he’s just one of the girls, they frequently strip off their clothes in front of him, walk around in their underwear, or join him in the bathroom! It doesn’t take long before he becomes so pent up with arousal that he can’t get his erection to go down. Hinata, the only one who knows his secret, decides to help the poor guy out with some satisfying fellatio action.

This hentai isn’t crazy over the top, but that isn’t to say that this isn’t enjoyable.

5. Furyou Ni Hamerarete Jusei Suru Kyonyuu Okaasan The Animation

Furyou Ni Hamerarete Jusei Suru Kyonyuu Okaasan The Animation

A doting mother, Kyoko, realizes she has sexual feelings toward her son. She starts out just bathing with the boy, but very quickly, she starts craving him. He feels the same way towards his mother but is too intimidated to actually have sex with her. Eventually, her inner pervert becomes unlocked after her son’s friend, Shin, rapes her.

She decides to punish her disappointing child by dressing him in a maid’s outfit and chaining him up, humiliating him. Lifting his skirt, she inserts a double-headed dildo inside herself and then her son. Overcome with madness and desire, she thrusts vigorously into her child, making him regret not taking the initiative with his mother back when he had the chance.

This is hentai that a lot of genre lovers will enjoy; it gives everything it’s supposed to and more. You won’t be able to take your eyes off the screen; Kyoko is the perfect milf, and watching her do stuff is extremely enjoyable. Definitely, hentai that you can’t pass upon.

6. Shounen Maid Kuuro-Kun

Shounen Maid Kuuro-Kun

Kuuro-kun is made to take over the debts of his father and forced to pay them off by being sold into servitude as a boy maid.

This is hentai without much plot. What little plot there is, is to explain how Kuuro finds himself in the situation he’s in, serving as a maid in a pervert’s house. It’s essentially a story where the protagonist is made to pay with their body for the poor choices their parents made in the past. But, what it lacks in the plot, it makes up with everything else.

The art and animation in this hentai is pretty great, the main character Kuuro, however, fits into the trope of a guy mistaken as a girl because he actually looks like a girl, which is seen in quite a bit of hentai, yaoi, and shounen-ai manga and anime in general, so if you like hentai like Boku no Pico for example, this is one that you’ll enjoy.

7. Shinkyoku no Grimoire The Animation

Shinkyoku no Grimoire The Animation

A girl named Eva becomes tempted by the power of the Grimoire of Greed. She and her brother, Adam, work together to collect mana for their dark master by raping people! Adam uses the book’s power to transform his appearance into that of a female. He lures an unsuspecting man into having sex with him.

Afterward, his magically created vagina disappears, and he reveals the surprise hidden underneath his dress. After all, is a boy’s ass really all that different from a vagina? The poor guy is about to find out as Adam climbs on top of him and rides him hard!

We’ve seen a plot like this before, and no matter how many times it’s been done, it’s always an enjoyable watch. It’s fun to see Adam and Eva’s shenanigans after they get power from the Grimoire of Greed, which does exactly what it sounds like, makes them greedy for lots of sex! The sex scenes are extremely enjoyable, and the art and animation are extremely well done as well.

8. Panchira Teacher

Panchira Teacher

Machiko Natsukawa is not in her teaching position long before she finds herself being blackmailed by a student. The student in question has Machiko’s underwear and, by refusing to give them back, manages to draw Machiko into a sex orgy filled with the school’s worst delinquents. This became her worst nightmare.

The students are unphased as this sort of bullying behavior is commonplace. One student, Atsasuki, is also on the receiving end of such bullying. After school, two other students force him to dress as a girl and demand that he sexually gratify them.

Panchira Teacher is one of that hentai that will engross you not only in the sex scenes but also in the storyline! The plot of Panchira Teacher is simple to follow, but it does not cross the line into being too cheesy.

The animation, while somewhat limited, is still very good, especially for the time this was made. The sex scenes are also well made and not overused in the slightest. Overall, this is stellar hentai.

9. Konna Ni Yasashiku Sareta No

Konna Ni Yasashiku Sareta No

It’s the day before Valentine’s Day, and a smitten high school student is busy in the kitchen making homemade chocolate to give as a gift to her beloved senpai. Suddenly, her older sister, Akira, barges in, violently knocking her to the floor with her chocolate. Akira starts yelling at her sister, calling her a disgusting pervert who gets aroused from dressing as a girl.

Akira lifts up her sister’s skirt to reveal that she’s actually a boy! It turns out that Hiromi has always wanted to be a girl and is incredibly jealous of his sister’s large breasts.

Akira then tries to prove Hiromi’s perversion by making him cum using her foot, but he quickly turns the tables on her. He fights back and discovers that she is the one who is sexually aroused by the sight of her brother in a dress.

You can’t really go wrong with hentai like this. The sex scenes are really well done as well.

10. Boku no Pico

Boku no Pico

Pico, who is upbeat and effeminate, is spending the summer at his grandfather’s coffee shop, Café Bebe. Tamotsu is a white-collar worker looking for an escape from the mundanity of his everyday life. When they meet at the café, they are quickly drawn together by sparks of love and lust.

Conventional notions of age, gender, and sexuality are broken down as the pair seeks carnal gratification in one another’s company. But do the pleasures of flesh equate to a connection between hearts?

If you’ve been in the anime community long enough, you’ve probably heard this name before. It has been infamous for a long time. But that aside, this is one of the best shota hentai out there.

The plot is not the strongest point of this hentai, which is quite common when it comes to hentai. But what is enjoyable is the sex scenes; the series takes its time showing scenery and building up to the sex scenes, which makes it way more enjoyable when you finally get to them. Boku No Pico is a very well-animated shota with lots of sex scenes.

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