Top 10 Crossdress Hentai Anime [Best Recommendations]

Nearly every society throughout history has had a set of norms, views, guidelines, or laws, regarding the wearing of clothing and what is appropriate 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 crossdressing anime!

10. Natsuyasumi

  • Episodes: 3
  • Aired: January 2013 - July 2013

Yuu is spending his uneventful summer days fishing for crayfish. Suddenly he meets a beautiful girl named Natsuki. While talking to her, he accidentally glances down the top of her dress getting a good glimpse of her nipple. She catches him staring and starts to giggle. She offers him the opportunity to see even more of her. First, he has to show himself to her though. Impressed with what she sees, Natsuki slowly sucks his cock. Afterwards she says that it's her turn and lifts her skirt to reveal she has a penis! Horrified, Yuu turns tail and runs away from her. However he cannot get her out of his mind, even appearing in his dreams.


9. Boku no Pico

  • Episodes: 1
  • Aired: September 2006

A young boy named Pico is working part-time at his grandfather's cafe over the summer. One day he finds himself in a passionate sexual relationship with a customer, an older man named Tamotsu. After spending a pleasant day in the park together, it starts to pour down with rain. They head back to Tamotsu's place to change out of their wet clothes. Pico asks if there are any clothes he can wear and Tamotsu presents him with a special outfit he bought just for Pico. A girl's outfit. He tries on the clothes, complete with cute headband and choker. Seeing how cute he looks, Tamotsu is unable to contain himself. He gently lies Pico on the bed, removing his own clothes. It doesn't take long for Pico's new outfit to get covered in stains.


8. Shounen Maid Kuro-Kun

  • Episodes: 1
  • Aired: September 2010

After the death of his mother, Kuro's father amassed a large debt and disappeared. One day he is summoned to a luxurious mansion where the master of the house, Miisu, wants him to work as his personal maid. Since working off his father's debt seems preferable to getting beaten by debt collectors, Kuro agrees. First, he is provided with a "traditional" uniform, a girly French maid outfit with a very short skirt! Kuro is embarrassed, but wears it begrudgingly. He quickly settles into his role as a sex slave, hoping this will help pay off his debt faster. Yet Miisu keeps finding reasons to punish Kuro. Before long, Kuro finds himself inside his master's dungeon wearing nothing but a corset and stockings, chained to the wall. His master punishes him some more, but this time entices him with the prospect of freedom. So which will Kuro choose, to go...or come?


7. Shinkyoku no Grimoire The Animation [Episode 2]

  • Episodes: 2
  • Aired: November 2014 - December 2015

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. Afterwards, his magically created pussy 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 his cock, hard!


6. Panchira Teacher [Episode 2] (Panty Flash Teacher)

  • Episodes: 2
  • Aired: November 2004 - February 2005

A new teacher fails to make a good impression on her students when one of them tries to sexually assault her in front of the class. The students are unphased as this sort of bullying behaviour 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.

When he refuses, they humiliate him further by tugging on his foreskin. This causes him to become fully erect, showing off his impressive size. Feeling threatened in comparison to this girly boy, the male bully asserts his dominance by spraying his semen onto Atsasuki's face!


5. Konna Ni Yasashiku Sareta No [Episode 1]

  • Episodes: 3
  • Aired: June 2014 - November 2014

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. Wait...what?
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.


4. Furyou Ni Hamerarete Jusei Suru Kyonyuu Okaasan: The Animation

  • Episodes: 2
  • Aired: May 2013 - August 2013

Doting mother, Kyoko, realises she has sexual feelings towards her son. She starts out just bathing with the boy, but very quickly she starts craving his cock. 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 rapes her. She decides to punish him by dressing him in a maid's outfit and chaining him up. Lifting his skirt, she inserts a double-headed dildo inside herself and then her son. She thrusts vigorously into her child, making him regret not taking the initiative earlier when he had the chance.


3. Otome*Domain: The Animation

  • Episodes: 1
  • Aired: September 2017

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-girl's 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, 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.


2. Otoko no Ko Delivery

Otome-Domain-The-Animation-Capture-3-560x357 Top 10 Crossdress Hentai Anime [Best Recommendations]

  • Episodes: ___content1___
  • Aired: ___content2___

Aoi and Shun are two high school students who share the same secret. They both work as crossdressing 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.


1. Skirt no Naka wa Kedamono Deshita.

Otome-Domain-The-Animation-Capture-3-560x357 Top 10 Crossdress Hentai Anime [Best Recommendations]

  • Episodes: 12
  • Aired: July 2017 - September 2017

Shizuka is persuaded into going to a singles night by a friend. Unfortunately, she's really shy around men. She quickly excuses herself to use the bathroom, where she meets a beautiful lady named Ryou. She feels much more at ease talking to another woman and they decide to go for drinks together. They chat back and forth about each other and seem to really hit it off. Shizuka asks if Ryou has a boyfriend and she explains that she's not interested in finding one. She invites the innocent Shizuka back to her place, passionately kissing her on the bed. Shizuka is confused to discover that Ryou's voice has suddenly become deeper and...something hard is pressing against her!


Final Thoughts

Playing around with gender roles can be an unbelievably erotic experience for men, women and those yet to make up their minds. So now we want to hear from you lovely people in the comments! What fashion choices tickle your fancy?

by J. McGowan