Ai Shimai IV Kuyashikute Kimochi Yokatta Nante Ienai

愛姉妹IV 悔しくて気持ち良かったなんて言えない

Ai Shimai IV Kuyashikute Kimochi Yokatta Nante Ienai
TitleAi Shimai IV Kuyashikute Kimochi Yokatta Nante Ienai
Original title愛姉妹IV 悔しくて気持ち良かったなんて言えない
LengthLong (30 - 50 hours)
Publishers Silky's
Same series
Ai Shimai ~Docchi ni Suru no!!~


Kenji Nishiyama is a fat ugly man that wastes all his money with prostitutes. After losing his job (and money), he decided to blackmail a woman to start a secret sex life with him under the threat of showing her daughters a picture of her husband talking to a prostitute.

Heroine with Tights 3.0 Harem Ending 3.0 Villainous Protagonist 3.0 Perverted Protagonist 3.0 Blackmail 3.0 Harem Ending with Theme 3.0 Pregnancy Ending 2.7 Netori 2.7 Impregnation 2.7 Rape with Blackmail 2.5 Group Sex of One Male and Several Females 2.3 Early Sexual Content 2.0 Pregnant Sex 2.0 Heroine with Zettai Ryouiki 2.0 Heroine with Sexual Experience 2.0 Adult Heroine 2.0 Married Heroine 2.0 Kyonyuu Heroine 2.0 Tsundere Heroine 2.0 Childishly Violent Heroine 2.0 Hotblooded Heroine 2.0 Medical Doctor Heroine 2.0 Protagonist with Sexual Experience 2.0 Urination Fetish 2.0 Vibrators 2.0 Defloration 2.0 Anal Plug Tail 2.0 Coodere Heroine 2.0 Male Protagonist 2.0 Adult Protagonist 2.0 Multiple Endings 2.0 Lolicon 2.0 Teacher Heroine 2.0 Heroine with Glasses 2.0 Nukige 2.0 High Sexual Content 2.0 Student Heroine 2.0 Bad Endings with Story 2.0 Missionary Position 2.0 Sounds of Copulation 2.0 Blowjob 2.0 Hint Corner 2.0 Long Sexual Scenes 2.0 Chubby Protagonist 2.0 Ugly Protagonist 2.0 Romancing a Family 2.0 Doggy Style 2.0 Female Ejaculation 2.0 Fingering 2.0 Threesome Ending 2.0 Defloration During Common Route 2.0 Piledriver 2.0 Rape Involving Drugs 2.0 Love Hotel 2.0 Heroine's Mother as a Heroine 2.0 Heroine with Children 2.0 Orgasm Denial 2.0 Anal Fingering 2.0 Save Memo Function 2.0 Music Recollection 2.0 Threesome 2.0 Heroine Sisters 2.0 NEET Protagonist 2.0 ADV 2.0 Side Images 2.0 Footjob 2.0 No Common Sense Heroine 2.0 Sex in Public Places 1.0 Ejaculation Choice 1.0 Anal Sex 1.0 Naked Sprites 1.0 Condoms 1.0 Bathroom Sex 1.0 Twin Tail Heroine 1.0 Heroine with Tan Lines 1.0 Kissing Scene 1.0 Sex with Sleepers 1.0 Voice Replay 1.0 Handjob 1.0 Anal Toys 1.0 Twin Blowjob 1.0 Cowgirl 1.0 Breaking the Fourth Wall 1.0 Reverse Cowgirl 1.0 Bukkake 1.0 Anilingus 1.0 Poor Protagonist 1.0 Erotic Spanking 1.0 Production of Pornography (Professional) 1.0 Group Sex of One Female and Several Males 1.0 Comedy 1.0 Enema 1.0 Standing Sex 1.0 Seventh Posture 1.0


Nishiyama Kenji
Nishiyama Kenji西山 健二 
Hair, Short
Body, Overweight, Ugly, Young-adult
Role, Unemployed
Engages in, Blackmail, Netori
Engages in (Sexual), Anal Fingering, Cunnilingus, Group Sex, Masturbation, Outdoor Sex, Peeing on Others, Pregnant Sex, Sex in Classroom, Vaginal Fingering
Subject of (Sexual), Adult Breast Feeding, Blowjob, Boobjob, Handjob, Triple Blowjob, Twin Blowjob


Ugly and fat, a guy almost 30 years old when he was fired and is now unemployed.
Hobby is make use of prostitutes to satisfy his unequalled sex drive, watch TV and clean the room.
Has good muscles but is weak, dislikes fighting and is bullied since was a student even to this day in society.
For such a good-for-nothing Kenji, the encounter with Eriko and her daughters can be the first big chance?

Main characters

Fujimura Eriko
Fujimura Eriko藤村 江利子 A
MeasurementsHeight: 158cm, Weight: 60kg, Bust-Waist-Hips: 99-64-95cm
Hair, Brown, Shoulder-length, Straight
Eyes, Amber
Body, Adult, H to M Cup, Pale, Slim
Clothes, Crotchless Panties, Earrings, Open Cup Bra, Pantyhose, Skirt Suit
Personality, Hardworker, Serious
Role, Medical Doctor, Mother
Engages in, Infidelity
Subject of, Blackmail, Pregnancy, Rape
Engages in (Sexual), Bathroom Sex, Boobjob, Group Sex, Pregnant Sex, Sex in Public Places
Subject of (Sexual), Anal Fingering, Anal Sex, Bukkake, Butterfly, Butt Plug, Doggy Style, Double Penetration (Group Sex), Peeing, Piledriver, Piss Drinking, Spit-roast, Standing Sex, Vaginal Fingering, Vibrator
Voiced byItou Sara


A beautiful female doctor working in a big hospital.
Even though being almost 40 years old has a beautiful and shine skin, and because of her plump, bouncy body is often the target of mischiveous pranks by the patients.
Became a doctor while still young, had a smooth sailing life of mutual love with the husband, because of an opportunity was raped by that bastard ugly guy Kenji.

Fujimura Kiyomi
Fujimura Kiyomi藤村 清美 A
MeasurementsHeight: 154cm, Weight: 42kg, Bust-Waist-Hips: 78-55-82cm
Hair, Brown, Shoulder-length
Eyes, Brown
Body, Average Height, C Cup, Pale, Slim, Teen
Clothes, Glasses, Pantyhose, School Uniform, Slave Collar
Personality, Reserved, Smart
Role, High School Student
Engages in, Cosplay
Subject of, Pregnancy
Engages in (Sexual), Bathroom Sex, Blowjob, Group Sex, Outdoor Sex, Pregnant Sex, Sex in Classroom, Triple Blowjob, Twin Blowjob, Virgin Sex
Subject of (Sexual), Anal Plug Tail, Anal Sex, Butterfly, Butt Plug, Cowgirl, Doggy Style, Hidden Vibrator, Multiple Penetration, Quickie Fix, Seventh Posture, Sitting Sex, Tominagi, Vaginal Fingering, Vibrator
Voiced byAoi Miu


In contrast to her hot-blooded sister, is a serious and cool girl that loves to study.
It may seems to look camly at things, but in reality is often absentminded.
Once she decides something is stubborn and never backs down, and once something exceeds the amount of things she can understand she can get confused and burst into tears.
Believes in the lies of the protagonist, Kenji, that he is her mother's, Eriko, lover and gives her pure body in other to break them apart....

Fujimura Manami
Fujimura Manami藤村 愛美 B
MeasurementsHeight: 157cm, Weight: 49kg, Bust-Waist-Hips: 88-52-90cm
Hair, Brown, Pubic Hair, Twin Tails, Waist Length+
Eyes, Amber
Body, Average Height, E+ Cup, Pale, Slim, Teen
Clothes, School Uniform, Thigh-high Stockings, Wedding Dress
Personality, Carefree, Childishly Violent, Hotblooded, Mischievous
Role, High School Student
Engages in, Wedding
Subject of, Pregnancy
Engages in (Sexual), Blowjob, Boobjob, Facesitting, Group Sex, Handjob, Sex in Classroom, Triple Blowjob, Twin Blowjob, Virgin Sex
Subject of (Sexual), Anal Sex, Bukkake, Butterfly, Cunnilingus, Doggy Style, Enema, Erotic Spanking, Piledriver, Quickie Fix, Reverse Cowgirl, Standing Sex, Tominagi, Vaginal Fingering, Vibrator
Voiced byNakano Shino


Breats sway only by walking, even though is slender has plumb limbs.
In the first meeting with the protagonist, Kenji, she hits him, has a very impertinent attitude, she must want to discipline every man instinctively about sex.
While being such a violent person, is very capable of accepting a partner with a frank, honest personality....
Will Kenji's view on life dramatically change being caught in such a strong personality?

Hasegawa Junko
Hasegawa Junko長谷川 順子 O
MeasurementsHeight: 160cm, Bust-Waist-Hips: 101-79-96cm
Hair, Blond, Curly, Shoulder-length
Eyes, Teal
Body, Average Height, H to M Cup, Pale, Slim, Teen
Clothes, Fishnet Stockings
Personality, Airhead, Honest, Kind, Naive, Shy
Engages in, Cosplay, Lactation
Subject of, Pregnancy
Engages in (Sexual), Adult Breast Feeding, Boobjob, Drunk Sex, Group Sex, Handjob, Pregnant Sex, Virgin Sex
Subject of (Sexual), Butterfly, Doggy Style, Quickie Fix, Sitting Sex, Spoons, Vaginal Fingering, Vibrator
Voiced byHarumura Sayuna


New teacher of arts in the school of the Fujimura sisters, the students gave her the nickname of "plump/chubby girl" 'Pochako'
Extremely bad at socializing, have the TV and clay as her friends.
A woman that painfully cannot read the atmosphere around her and others.
Junko does thing at her own pace too much, she's already at the mercy of Kenji on their fist meeting!?

Takamine Nanako
Takamine Nanako高峰 奈々子 AB
MeasurementsHeight: 134cm, Weight: 33kg, Bust-Waist-Hips: 68-52-70cm
Hair, Grey, Ringlet, Short, Spiky Bangs, Twin Tails
Eyes, Violet
Body, Pale, Short, Slim, Tanline, Teen
Clothes, School Uniform
Personality, Blunt, Pervert, Third Person
Role, High School Student
Subject of, Pregnancy
Engages in (Sexual), Blowjob, Group Sex, Mutual Masturbation, Outdoor Sex, Pregnant Sex, Sex in Classroom, Sex in Public Places, Triple Blowjob
Subject of (Sexual), Doggy Style, Piledriver, Seventh Posture, Sitting Sex, Tominagi, Vibrator
Voiced byAnzu Hana


An innocent girl who calls Kiyomi "Mitti".
When first encoutered Kenji, had no hesitation in talking with him, a frank rich girl who is considerate of Kiyomi and is her best friend.
More interessed in ecchi than the sisters, do you want to do it once?

Side character

Fujimura Keisuke
Fujimura Keisuke藤村 佳祐 B
Hair, Grey, Short
Eyes, Kitsuneme
Body, Adult
Personality, Timid
Role, Father, Househusband, Husband
Engages in, Infidelity
Subject of, Infidelity, Netorare


His blood type can also be AB but is believe B is more likely.