Most Painful hentai comics

[Tousoku Chokusen Undou (Pain)] Hadaka no Ou-sama (Boku No Hero Academia)

[Himitsu Kessha M (Kitahara Aki)] Sweet～GOOD-BYE MY SWEET PAIN～ (The King of Braves GaoGaiGar)

(C93) [Tsurutsuru Pain (Pikeru)] MahoEri wa Dashitagari (Girls und Panzer)

[Rain dog clothes] I opened my chunk and became a woman and feel a painful Mesuiki experience

Kagirinaku Toumei ni Chikai B.B - Almost Transparent B,B

Doki Doki Penguin Bathroom

(AC2) [Tsurutsuru Pain (pikeru)] Hotaru-chan to Roshutsu Date shite mita. (Non Non Biyori)

Yuna A La Mode 7 Xanarkand Debut 3

Yuna A La Mode 8 Xanarkand Debut 4

(C96) [Selvage Fisheries (Uo Denim)] Kagirinaku Toumei ni Chikai B.B - Almost Transparent B,B (Fate/Grand Order) [Chinese] [空中貓製作室 & 不咕鸟汉化组]

[Anthology] Josou Shounen Anthology – Mushiro, Gohoubi 2

Angel Pain 5 -The AF Servant-

Sekaiichi Tooi Otonari-san | Most Distant Neighbor

Twinkle☆Crusaders Kurukuru Most Secret Booklet

[Yawaraka Onikudan (Oniku Danchou, Yuuyuu)] Docchika Nante Kimeraren! | I Can't Choose! (Metal Gear Solid V: The Phantom Pain) [English]

(C80) [S Shoten (Sani)] Most Muscular (THE IDOLM@STER)

(C73) [Cool Brain (Kitani Sai)] ANGEL PAIN Extra 5 -NATSUTSUKA- [English]

[Pecan (Makunouchi)] Monzetsu! Mix Fight | Painful KO! Mixed Fighting [English] [Tigoris Translates]

[Aotokage (Aoto Kage)] Tri mostri [Digital]

Mottomo Yasashii Koroshikata - The most gentle how to kill.

What Do You Love Most? Prologue

(Renai Jaws 4) [Enka karushiumu (Takeda)] Sekai de ichiban kimi ga suki! | The One I Love The Most In This World Is You! (Free!) [English] [Carrot-Bunny]

[Narusawa Kio] Mottomo Yasashii Koroshikata - The most gentle how to kill. 1 | 最溫柔的殺人方法 [Chinese] [莉赛特汉化组]

SWEET PAIN Pt. 1

Toromeki Shoujo

(C95) [Tsurutsuru Pain (Pikeru)] Exhibitionism V (Boku wa Tomodachi ga Sukunai)

[St. Rio] Yuna A La Mode 08 (Final Fantasy 10-2)

[Earl LUMINES] PAIN ABSORBER 13 part1

RecentGirlsPlusAppend

[Kanoh Hollow] Sweet Pain

Honjitsu wa Nama Biyori

(COMIC1☆2) [Noritama-gozen (Noritama)] Guilty Pain (Mahou Shoujo Lyrical Nanoha)

Itou Pleasure and Pain 6 - Infidelity

(COMIC1☆3) [TRICKorTREAT (Kagura Tsukune)] Slow Pain (Mahou Shoujo Lyrical Nanoha)

[Itou] Kaikan to Kutsuu - Pleasure and Pain [English] [SaHa]

(CCOsaka47) [Bonnou Denshi Garou (Chimoto Chie)] SWEET PAIN 02 (Final Fantasy VII)

1 x 1 = 2

Tri mostri

(C58) [Cool Brain (Kitani Sai)] Angel Pain 3 Ninamori Senka (FLCL) [English] {doujins.com}

(COMIC1☆3) [SSB (Maririn)] SWEET PAIN Pt. 1 [weekend] (Toradora!)

Action Pizazz 2021-06

(C59) [Cool Brain (Kitani Sai)] Angel Pain 5 (Love Hina) [English] [HoshiManga]

(CR27) [Cool Brain (Kitani Sai)] ANGEL PAIN 2-The Angel of Back Scuttle- (Turn A Gundam)

Sekai de Ichiban Suteki na Kanojo Manaka | The Most Lovely Girlfriend In The World

[Earl LUMINES] PAIN ABSORBER 9

[Kusano Takayuki] Yuu Mama - Painful Love

(C69) [Cool Brain (Kitani Sai)] ANGEL PAIN Extra 2 -Bloomer Scatology-

[Earl LUMINES] PAIN ABSORBER 4

Multiple Paizuri (mostly) in Manga/Hentai/Western comics

ANGEL PAIN Extra 2 -Bloomer Scatology- by Ceru & AppleGirl

Gohan o Taberu Hon 3

[Homare] Ma-Gui -DEATH GIRL- Pain Hen (COMIC Anthurium 015 2014-07) [Chinese] [里界漢化組] [Digital]

Taisetsuna Futari o Uragiru NTR | Being uNTRue to the Two She Loved the Most

[THERMOSTAT (Neji)] Hyacinth wa Aishiau [Chinese] [加帕里汉化组] [Digital]

Naked King

(C76) [Brain Dead (Eiji)] Hayate no Taihen na Soushuuhen | Hayate’s Most Risqué Compilation (Hayate no Gotoku!) [English] [The Chrysanthemum Translations]

(C64) [Aruto-ya (Suzuna Aruto)] Mikicy Vol. 3 (Final Fantasy X-2)

The One I Love the Most

[Momoyama Jirou] Hitsuji-tachi no Monzetsu - Sheeps's Faint in Pain

Kagirinaku Toumei ni Chikai B.B - Almost Transparent B,B

Natsu Wa Sugu Soko! | It's almost summer!

[Cool Brain (Kitani Sai)] ANGEL PAIN Extra 5 -NATSUTSUKA- [Digital]

(CR33) [Majimeya (isao)] Play Soft (Final Fantasy X-2) [English] [SaHa]

Kanojo no Okaa-san wa Kimochi Ii...

ANGEL PAIN 14

SWEET PAIN Pt.01

Pain Room

ANGEL PAIN 11

GirlsPutOut! scene.04

[Moritake(モリタケ)] The World's Most Wanted to Receive Health Class [English]

Taisetsu na Hito | My most precious person

[Tsurutsuru Pain (Pikeru)] GirlsPutOut! scene.01 (Amagi Brilliant Park)

most disliking

(C58) [Cool Brain (Kitani Sai)] Angel Pain 3 Ninamori Senka (FLCL)

(SC56) [Aroma Gaeru (Numahana)] Saikyou Controller | Most Powerful Controller (Mouretsu Pirates) [English] [EHCOVE]

Hitsuji-tachi no Monzetsu | Sheeps' Faint in Pain

(C64) [Cool Brain (Kitani Sai)] ANGEL PAIN-Extra- (Final Fantasy X-2)

(COMIC1☆11) [Hobukuro! (Bekotarou)] Watashi no Ichiban Hazukashii Tokoro. | My Most Embarrassing Place [English] {Doujins.com}

(J.GARDEN 32) [Kyuushiki (Ogawa Chise)] Ienai Itami o Daiteiru | An Unspeakable Pain [English] [Cocobees]

Kagirinaku Toumei ni Chikai B.B - Almost Transparent B,B

(SC40) [D.N.A.Lab. (Miyasu Risa)] MY HEART (LUX-PAIN)

(C64) [Cool Brain (Kitani Sai)] Angel Pain 11 (Gundam SEED)

(C82) [Aspergillus (Okara)] Noblesse Pain (Toaru Kagaku no Railgun)

[Ohtado (Oota Takeshi)] White Passion Milky Pain [Digital]

(C63) [Cool Brain (Kitani Sai)] Angel Pain 10 (Dead or Alive Xtreme Beach Volleyball)

Setsunai Omoi - Painful feelings

(C71) [Cool Brain (Kitani Sai)] ANGEL PAIN Extra 3 -LoveLove Scatology-

(C57) [Cool Brain (Kitani Sai)] Angel Pain (Angels of the Stars: Angel Links) [English] [EHCOVE]

What Do You Love Most? Epilogue

[Tousoku Chokusen Undou (Pain)] Gohan o Taberu Hon 2 (Dragon Ball Z) [English] [Digital]

Karami Zakari Bangaihen

Itou Pleasure and Pain 2 - Accomplice

[Unagiyasan (Hanamiya Natsuka)] Onii-chan wa Sekai de 2-banme ni Daisuki | I love Onii-chan second most in the world [English] [LoliAce] [Digital]