15 Sexiest Prostitution Hentai Of All Time

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15 Sexiest Prostitution Hentai Of All Time

Last Updated: Oct 18, 2021

You know you have to relax somehow when you’re stuck up, sad, angry, or bored. And what is best to do that than watching some great hentai series. What exactly is prostitution? Basically, it’s a job or practice where you have to perform sexual favors for money.

In hentai, prostitution is a popular topic among girls who enjoy sex. It doesn’t matter if she’s trying to pay for her rent or just wants to have some extra spending money; there are many options for prostitution hentai. The hentai below will meet your needs if you want to watch beautiful ladies having sex for money.

It is no secret that these ladies enjoy sex and how they use that fact to their advantage. You shouldn’t be surprised by these prostitutes if you are tired of watching women being exploited. This list includes everything from cute girls making money to tricking men into satisfying their nymphomaniac fantasies.

In addition to having plenty of fun sex, prostitution hentai usually indulges in a few other fetishes. We selected the Top 15 Prostitution Hentai for you.

15. Taimanin Yukikaze (Episodes: 3- Air date: November 2013 to January 2016)

Taimanin Yukikaze

Five years before the events of Taimanin Yukikaze, Yukikaze’s mother, Mizuki Shiranui, goes missing on a mission, which motivates Yukikaze and her friends Rinko and Taturou to become powerful Taimanin to one day find her again.

Yukikaze, now a student at a ninja training academy, learns new demon-fighting techniques. One day, she and her friend Akiyama Rinko decide to infiltrate an evil organization in hopes of finding Yukikaze’s mother; however, to do so, there is a great price they have to pay.

The three episodes break down into the standard formula you’d expect. An episode each for the breaking and enslaving of Yukikaze and Rinko and the third episode culminating in the outcome of what has transpired.

This anime has a nice art style, the characters are nicely done, and the animation makes the whole thing enjoyable. The way the plot progresses is quite expected from a hentai of this genre, but then again, it’s hentai, so it’s not really surprising. The main characters in this hentai are quite likable; they make this hentai what it is.

The h-scenes are what you’d expect, and they’re highly enjoyable. Overall, this is a pretty good hentai to watch, and you should definitely add it to your watch list.

14. Enkou JK Bitch Gyaru: Oji-san to Nama Pako Seikatsu (Episodes: 2 – Air date: February 2018 – March 2018)

Enkou JK Bitch Gyaru Oji-san to Nama PakoSeikatsu

Enkou JK Bitch Gyaru is a prostitution hentai anime about a lonely salaryman who decides to pay some beautiful girls for sex. The two girls love sex and have decided to use their favorite hobby to make a little extra spending money while on a boat. They target the salaryman and make him a sexy offer he can’t refuse.

The plot is exactly what you’d expect from a prostitution hentai, but that makes it easy to follow without focusing too much on it. Young girls making some money off older lonely men isn’t a new concept, but it’s still a well-liked one.

This hentai has great art and animation, and the characters are pleasing to look at. Surprisingly, the lonely man isn’t an ugly old man that you’d generally expect from this kind of hentai; he’s actually not that bad looking. The girls, of course, are really attractive; they’re what makes this hentai enjoyable and worth watching.

The h-scenes in this hentai are enjoyable, with the man enjoying with both the girls and satisfying them. Overall, this is a great prostitution hentai to watch if you enjoy the genre; it has everything you would expect it to have while not making it too cliche.

13. Taimanin Asagi (Episodes: 4 – Air date: February 2007 – August 2008)

Taimanin Asagi

The city avenues of Tokyo are more risky than they’ve at any point been previously. People and devils exist one next to the other, with a sworn trust that they won’t hurt one another.

However, a few people have dismissed these sacrosanct vows and have collaborated with evil presences to frame gatherings and associations, bowed on death, obliteration, and unholy human disaster.

12. Enkou Shoujo: Rikujoubu Yukky no BaaiThe Animation (Episodes: 1 – Air date: August 2016)

EnkouShoujo Rikujoubu Yukky no BaaiThe Animation

A pair of girls enter the world of prostitution after realizing how much money they could make simply by having sex. They have been friends since childhood and, after a confrontation with a pushy man, decided to go into business together.

Yuuki is convinced to do her first prostitution gig by her friend Mako. The two agree to do a double rate for a customer and head to a nearby hotel room. The girls also take several suggestive pictures for the man earning them a huge paycheck. Prostitution at its best.

This hentai does a lot of things right; you will not only enjoy the h-scenes but also the plot of this hentai, which isn’t the case for a lot of hentai titles out there.

The story is really intriguing and makes it worth watching; the h-scenes don’t just start out of the blue, there’s always a build-up to them, and you aren’t left confused about how the characters ended up in that situation.

The art and animation in this hentai are really well-done. The delivery of the hentai makes it really enjoyable. The characters are enjoyable, and the transition of the main character doesn’t feel forced at all; it isn’t your typical situation.

11. Makai Kishi Ingrid (Episodes: 4 – Air date: June 2009 – August 2010)

Makai Kishi Ingrid

Tokyo, the diabolic city, was being invaded by dark existences. Darkness begins the action behind the success of the ninjas of justice called Taimanin. Hell knight Ingrid revealed a diabolic doctor, Sabato Kiryuu, who belonged to the group of darkness Kanomado, betrayed her. He managed to escape from the spot.

However, Kiryuu counterattacks her in a certain hideous church, and she becomes a captive. Kiryuu attempts to destroy Ingrid’s noble soul and deceive Edwin Black, the vampire, into saving her with vengeance. To disgrace Ingrid, he encourages a group of monsters bent on revenge against her.

Many hentai that has either no story or a terrible story, compared to most, this one does have a relatively good although archetypal story. This hentai can be considered a masterpiece.

The art is a standout enjoyment in this series, with Ingrid and Murasaki’s character designs being simply amazing. They are both full-figured and very attractive. All the characters have good and distinct personalities.

The only two characters that matter are Ingrid and Murasaki. Both are introduced as girls with a fighting spirit, which quickly withers away as they are taken captive by the antagonist of the series.

10. Nariyuki→Papakatsu Girls!! The Animation (Episodes: 4 – Air date: February 2018 – June 2018)

Nariyuki→Papakatsu Girls!! The Animation

Chihiro is working a low-paying job at a fast-food shop, and her sex life is less than desirable. When she complains to her friend Eri though, she learns of the world of paid sex. Thrilled at the thought of making money while going on passion-filled dates, Chihiro quickly agrees to the proposition.

Without wasting any time, the hentai quickly cuts to a scene of Chihiro watching Eri sucking a man off. As she finds herself getting turned on, Eri hops on top of the man to ride him.

Soon enough, Chihiro finds herself on all fours sucking the man off before he plunges deep inside her wet. Before long, both girls learn how wonderful the man feels and take turns getting pounded for money.

Our show features two schoolgirls and an unattractive man, which is pretty standard for a hentai of this genre. These cute, well-detailed girls are an absolute jackpot for cute schoolgirl fans.

The only development here is turning the shy girl into a prostitute, and it doesn’t take long, but the process is pretty straightforward. The friend does a great job at putting the attention on the shy girl, and the dialogs between the two are pretty enjoyable.

9. Soukou Kijo Iris (Episodes: 4 – Air date: November 2007 – September 2009)

Soukou Kijo Iris

The human race has left Earth and moved into the vast reaches of space, joining the interspecies collective known as the Space Federation. As a result, the Soviet Security Force (SSF) was formed to establish humanity’s presence throughout the galaxy.

One of the many divisions of the SSF is the Special Armored Company (SAC) #101. In the name of justice, these female enforcers use mobile humanoids called “Armored Knights” to deal with corrupt officials, crime lords, and other villainous forces.

The story follows Iris Rebel, a lieutenant of SAC #101, as her squad investigates reports of trafficking on the planet Left. As Iris narrowly escapes an ambush and loses consciousness, her Elven partner Mei Li Naceri suddenly disappears in action.

She’s captured by Orcs and taken to an underground slave auction where she is humiliated by gleeful bidders before being sold for a high price to Bozuk, the owner of the most renowned brothel in Dark Town. Now forced into prostitution, Iris must find a partner before the pleasures brought to her by her clients drive her insane.

Probably one of the more enjoyable hentai you’ll ever watch. It has a decent storyline for a hentai series.

8. Sei Yariman Gakuen Enkou Nikki (Episodes: 1 – Air date: February 2013)

Sei Yariman Gakuen Enkou Nikki

A salaryman ends up being left by his family and feeling lonely. Luckily for him, a beautiful young woman has appeared in his life with a proposition. All he needs to do is pay her, and he can use her body to fulfill his primal urges.

Before long, the young woman takes the salaryman back to her room, where she begins to strip. He then reveals himself to her, and she begins licking it passionately. After getting him a bit excited, she gets unto bed a rolls onto her back while spreading her legs.

The girl encourages him to go in raw, and the two begin to have passionate sex. Soon enough, the man becomes more comfortable with his arrangement and starts to pound the woman from behind.

There isn’t a lot going on plot and character-wise, but for what it is, it’s quite enjoyable. Being just one episode long, there isn’t a lot of time for the characters or the plot to develop, but that’s fine considering it mostly focuses on the h-scenes.

If you’re looking for a hentai title that is plot-driven, then this isn’t for you, but if you want to watch a hentai title with a hot female mc, and lots of sexy h-scenes, then you’ll enjoy this.

7. Subarashiki Kokka no Kizukikata (Episodes: 2 – September 2019)

SubarashikiKokka no Kizukikata

Sybarashiki brings in a bit of fantasy elements to the prostitution list. Aridane just became the princess of a country in deep debt. In order to help save her beloved country, she decrees that the country should focus on sex and becomes a royal prostitute.

The first scene shows a royal servant, Ruruka, dressed in a cat costume, ready to suck her first customer off. Ruruka lets him have her way with her. Later on, the princess meets her first client, who is more than excited to shove his face in between her boobs. The princess ends up letting several men inside her through the episode.

This is a hentai that combines fantasy and prostitution and does it well. It gives us a princess that’s willing to become a prostitute just for the sake of her country and to help bring up their economy.

This is a hentai with great art and visuals that makes it nice to watch. The princess is quite likable, and so are the other characters. What is a hentai anime without hot female characters in the forefront? And this hentai definitely delivers on that. With great h-scenes and great characters, this prostitution hentai is a pretty good watch.

6. Shin Sei Yariman Gakuen Enkou Nikki The Animation (Episodes: 1 – June 2014)

Shin SeiYarimanGakuenEnkou Nikki The Animation

Saiki Yasuo is 45 years old and works as an office worker. He was left by his wife after 20 years of marriage. After drinking alone all night, he is depressed when a girl from the St. Marian Academy approaches him seeking a client. Saiki agrees and soon learns to love his life again.

The couple heads to a karaoke bar where they end up having sex, and they even end up getting caught in the act, only adding to Saiki’s excitement. This hentai acts as a sequel to Sei Yariman Gakuen Enkou Nikki, which means more old men and school girls action! The animation is overall smooth and nice, the attention to detail for small things is great.

There isn’t a lot going on plot and character-wise, but for what it is, it’s quite enjoyable. Being just one episode long, there isn’t a lot of time for the characters or the plot to develop, but that’s fine considering it mostly focuses on the h-scenes.

If you’re looking for a hentai title that is plot-driven, then this isn’t for you, but if you want to watch a hentai title with a hot female mc, and lots of sexy h-scenes, then you’ll enjoy this.

5. Kanojo wa Dare to demo Sex Suru. (Episodes: 2–February 2015 – Mach 2015)

Kanojo wa Dare to demo Sex Suru

Kazuhiro Sayama finally gathers the courage to confess to his crush, Erika Sakurai. She responds by immediately having sex with their gym teacher in front of him. It turns out that the girl of his dreams is a voracious sex addict, and she’s especially into exhibitionism.

The two strike a deal: Kazuhiro will become Erika’s personal cameraman, filming every one of her sexual encounters. He gets to watch the girl he likes in every lewd situation imaginable, with only one catch—he himself may not have sex with her. Will Kazuhiro be content with their arrangement, or will he shoot for something more?

The hentai starts out with Erika being roughly fondled by the Gym teacher in the library. He makes sure to tease her in front of Kazuhiro. Kazuhiro watches as the man grasps onto Erikas hips and starts to ravage her body violently. Erika continues her sexcapades as the anime progresses.

The main focus of the show, Erika, enjoys being filmed on camera having sex, which is quite a normal kink. She lacks any emotions aside from horniness, and as the show carries on, this is further supported. Overall, this is a great hentai with great art; it’s really enjoyable and should definitely be on your watch list.

4. Discipline Zero (Episodes: 2 – January 2010 – June 2010)

Discipline Zero

The hit series Discipline is revived with this new original story set prior to the coming of Hayami Takuro, protagonist of the first series.

Morimoto Leona and Otokawa Saori are newly arrived boarding students at St. Alcadia Academy. Morimoto Leona desires to subjugate every person within the school, severely punishing those who are of no use to her.

Even the teachers are not spared. Fellow boarders Yuuki, Ruri, and Maiko, who are oblivious of the situation, fall prey to the limitless sexual desires of the male students.

This hentai has great art and animation, really similar to Discipline, but even better. The concept as well is even more erotic. The characters are as one would expect from the source material: well-drawn, with most sex scenes in the OVA’s two episodes being extremely detailed.

This hentai serves as a backstory to Discipline, and it does a great job at it. Giving us more insight to how the school was before the main characters of the first series arrived to the school.

With the series being as short as it is, there isn’t a lot going on in terms of plot and character development, but that’s ok since it doesn’t take away from the enjoyment, and this hentai achieves what it sought out to do.

3. JK Bitch ni Shiboraretai (Episodes: 2 – August 2016 – September 2016)

JK Bitch niShiboraretai

JK Bitch ni Shiboraretai is another entry in the JK prostitution series. This time the story starts off when a gal shows her privates to a boy in her class. She reveals that she forgot her lunch money and will have sex with him in exchange for food.

The first sex scenes show several different angles of the main character being stroked and sucked off. Before long, the gal even rolls onto her back, spreading herself for him. The young man takes the opportunity and, within seconds, plunges himself into her. As the episodes progress, the duo continues to have more and more explicit sex on the school grounds.

There is no real story, but unlike other hentai who try hard and give us a meaningful plot, this one cuts straight to the chase. The art is quite good. The way facial expressions are drawn are great, breasts look realistic, although they’re too big for a high school girl, but hey, no one cares if they’re too big, as long they’re drawn beautifully like they are in this hentai.

The characters are great; they’re simple and straight to the point. Extremely enjoyable hentai with plenty erotic scenes and beautiful drawing of characters.

2. Enkou JK Bitch Gyaru Oji-san to Nama PakoSeikatsu 2 (Episodes: 2 – February 2018 – March 2018)

Enkou JK Bitch Gyaru Oji-san to Nama PakoSeikatsu 2

Part two of Enkou JK is all about the same girls who have become a lot more doting on their salaryman. Part two is a lot more aggressive and features more fetishes for you to enjoy.

Part two starts off with one of the girls in a school P.E. uniform riding the salaryman with her tits out. Shortly after, the show cuts to the man sitting out a table while the second gal sucks him off underneath.

After she finishes, she angles herself so that she can back into him. The show once again cuts quickly to a love hotel where he is ravaging the thighs of the first girl.

The plot is exactly what you’d expect from a prostitution hentai, but that makes it easy to follow without focusing too much on it. Young girls making some money off older lonely men isn’t a new concept, but it’s still a well-liked one.

This hentai has great art and animation, and the characters are pleasing to look at. Surprisingly, the lonely man isn’t an ugly old man that you’d generally expect from this kind of hentai; he’s actually not that bad looking. The girls, of course, are really attractive; they’re what makes this hentai enjoyable and worth watching.

1. Kyonyuu JK ga Ojisan Chinpo to Jupo Jupo Iyarashii Sex Shitemasu (Episodes: 2 – October 2018 – November 2018)

Kyonyuu JK gaOjisanChinpo to JupoJupoIyarashii Sex Shitemasu

Kyonyuu is a mix of tales about beautiful women having sex with men in positions of power. While these men think they are getting the better end of the deals, these ladies are using them to fulfill their own goals.

The first scene starts with the student vice-president spreading her legs across for the principal. Noticing that he will be tough to convince, she then gets down on all fours to spread her back legs revealing her panties. Unable to resist, the man gives in to his own desires when he starts to fondle her huge tits.

The girl soon takes further advantage of him. The hentai focuses mainly on the same girls, but a couple other old guys join in the fun halfway in.

This anime has a nice art style, the characters are nicely done, and the animation makes the whole thing enjoyable. The way the plot progresses is quite expected from a hentai of this genre. Young hot women with old ugly men is kind of a given when it comes to prostitution hentai, but it’s a plotline that always works to get the viewers hooked.

Overall, this is one of the best when it comes to this genre of hentai, so it should be on your watch list.

These women realize that they like sex and utilize that reality furthering their potential benefit. In case you’re worn out on watching ladies being exploited them, these whores are for you. From charming young ladies making going through cash to fooling men into fulfilling their nymphomaniac needs, this rundown has everything.

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