First Time Crossdresser

(COMITIA124) [Rico-ba (Rico)] Loli Succubus no Oshokuji Time | Loli Succubus' Mealtime [English] {Mistvern}

[SHAGWELL (Isshiki Nishiki)] M-butterfly ad libitum 1 (Sentimental Graffiti)

(CR23) [Ginrinkyuu (Aimu Yuu)] Setsu na Kute (Sentimental Graffiti)

C9-33 Megami-sama no Hajimete Ereshkigal no Baai The Goddess’s First Time_ The Tale of Ereshkigal

[Tamon] Dokidoki Time Paradise ~Sawari Houdai Ire Houdai~ 4

[250ponoroji (Horochi)] Saimin Onsei de Hajimete Ikasareta Watashi no 60-punkan | My 60 Minutes Being Made to Cum for the First Time by a Hypnosis File [English] [estradiol]

(C95) [Kenja Time (MANA)] Fate/Gentle Order 4 "Alter" (Fate/Grand Order)

[MANA-KO] Hajimete no Okaimono | My First Time Shopping (Ragunagu) [English] [desudesu]

Porno First ~Yuriko Shichou no H na Kaikaku~ | Porno First ~Mayor Yuriko's Sexy Reform~ Ch. 1-5

Hatsukoi wa Daiichi Ouji - First Love Is... the First Prince!

[Kenja Time (MANA)] Gentle Master (THE IDOLM@STER CINDERELLA GIRLS) [Digital]

(C91) [Kenja Time (MANA)] Gentle Blue Fantasy 4 (Granblue Fantasy) [English] [q91]

(C95) [Kenja Time (MANA)] Fate/Gentle Order 4 "Lily" (Fate/Grand Order) [Chinese] [谜之汉化组X·Alter&无毒気汉化组]

[Shiha_ra] Shouta-kun First Time (Kobayashi-san-chi no Maid Dragon)

(C93) [Kenja Time (MANA)] Fate/Gentle Order 2 (Fate/Grand Order) [Chinese] [性趣之门&无毒汉化组]

[Murasame Masumi] Mama no Fudeoroshi | First Time with Mother (COMIC MUJIN 2009-04) [English] [Decensored]

[Polorinken (Polorinken)] Menu 23 God Only Knows (Sentimental Graffiti)

[TNC. (Lunch)] FIRST TIME × LAST TIME (THE iDOLM@STER) [Chinese] [无毒汉化组]

Helping Hand For His First Time

(C52) [First Class (Kazuneko)] W-MIND 2 (Mahou Shoujo Pretty Sammy)

(C90) [listless time (ment)] Watashi no Ookami-san (THE IDOLM@STER CINDERELLA GIRLS)

Josou OL Tadaima Onanie Zangyouchuu | Cross-Dressing Office Worker Is On Masturbation Overtime

Their First Time

(C58) [Timest (Mugi Tokisaka)] Uchi, Saikin Bra ga Kitsuiccha. (Urusei Yatsura)

Time Stopper Naokata-kun no Jikan Teishi Nikki Ch. 1 - JK Futari

[Milk Pie, No Limit] Time STOP! ~Jikan wo Tomete Osananajimi Sanshimai to Yaritai Houdai~ 1

(C55) [Rocket Kyoudai] Aitai... COLLECTION (Sentimental Graffiti) [Incomplete]

The confession of crossdressed teacher

Futanari! Oshioki Time 4.5

[Oshiruko Kan (Piririnegi)] Futanari! Oshioki Time 4 ~Josou Shounen Kakusei Hen~ [Digital]

[Tamon] Dokidoki Time Paradise 1-3 [Chinese] [Den個人漢化]

Dressed up!, crossdress in modern times

[Polorinken (Polorinken)] Mizuiro no Koi (Sentimental Graffiti)

Big Titted Swimsuit Babes Are Just A Timestop Click Away

Hajimete wa Megami-sama | My First Time Was With a Goddess

[Saryuu] Hatsutaiken wa (Lolibabaa) Yuukaku de | My first time at the (lolibabaa) red light district (Towako San) [English] {CapableScoutMan & bigk40k} [Digital]

(C57) [Hiyotama Goten (Nagase Makoto)] Sentimental Window Vol 4 (front cover version 1) (Sentimental Graffiti)

(C93) [Crazy9 (Ichitaka)] C9-33 Megami-sama no Hajimete Ereshkigal no Baai | The Goddess’s First Time: The Tale of Ereshkigal (Fate/Grand Order) [English] {darknight}

Married Woman Working Part Time

[Polorinken (Polorinken)] Young, Alive, in Love (Sentimental Graffiti)

[MoTaro, Murayamamon] Time Stopyu! ~Jikan wo Tomete Rea-Juu Hamehame~ (1-2) [English]

(C63) [Glamour Works (Shadi Biin)] Sentimental Boobs 01 - Keiyaku (Sentimental Graffiti)

[MoTaro, Murayamamon] Time Stopyu! ~Jikan wo Tomete Rea-Juu Hamehame~ (1~2) [Chinese] [Den個人漢化]

Tryout Show Time

[Ozaki Akira] Porno First ~Yuriko Shichou no H na Kaikaku~ | Porno First ~Mayor Yuriko's Sexy Reform~ Ch. 1-9 [English] [erc] [Digital]

[The Monthly Istanbul (Ahugan Sugita)] Kasshoku Oneesan no Fudeoroshi Ver. 3 | Brown Lady Takes His First Time Ver. 3 [English] [vaasi] [Decensored] [Digital]

[The Monthly Istanbul (Ahugan Sugita)] Kasshoku Oneesan no Fudeoroshi Ver. 3 | Brown Lady Takes His First Time Ver. 3 [English] [vaasi] [Digital]

[Porori] My First Time is with.... My Little Sister?! Ch.07

[DryR (Urakuso)] Dosukebe Josou Kyoushi | Super-Pervy Crossdressing Teacher [English] {risette translations} [Digital]

(Comic Castle 13) [First Class] Pemo Pemo (Mahou Shoujo Pretty Sammy)

HERO DAY TIME 01-07

Crossdressing Teacher Gets Molested by Female Students

Kasshoku Oneesan no Fudeoroshi Ver. 3 | Brown Lady Takes His First Time Ver. 3

[Chinzuriina] Boku ga Josoushita Riyuu | The Reason I Crossdress (Chin☆COMPLETE) [English]

All of my first love

First Time Ch6

Baio Keihou

Exorcise Time

[Kishinosato Satoshi] The boy who loved crossdressing (from Yamete! Oneechan) (English)

(C87) [Time-Leap (Aoiro Ichigou)] Japans Yobai!? (Kantai Collection -KanColle-)

[pastime774] Obtained a unique job [Uncle Seeding] Chapter 1

(C91) [Kenja Time (MANA)] Gentle Blue Fantasy 4 (Granblue Fantasy)

[Oshiruko Kan (Piririnegi)] Futanari! Oshioki Time 4.5 ~Shokuzai & Onedari Hen~ [English] [ForbiddenTranslations] [Digital]

[MagicalFlight (Juujou Tatami)] Honoka no Anal Kaikin | Honoka's First Time Anal (Love Live!) [English] [Digital]

[yumoteliuce] Yokkyuu Fuman no Time Keeper - Frustration Time Keeper (COMIC BAVEL 2016-01) [Chinese]

Hitorijime - First Come First Served

Hajimete no Koto Our First Time

(C76) [Polorinken (Polorinken)] BRAND NEW SEASON (Sentimental Graffiti)

(C92) [Kenja Time (MANA)] Fate/Gentle Order (Fate/Grand Order)

(Douyara Deban no Youda! 8) [ecru (Kinari Kanny)] Loss Time Loss Time (Boku no Hero Academia)

[Haitokukan] Jikan Teishi no Otoko | The journal of the man who could stop time (COMIC Tenma 2015-11) [English] [naxusnl]

First time

[Kinokotei (Nekotsuki Izumi)] [CK] Tokiona (The Girl Who Leapt Through Time) [Digital]

[Lunch Time (Hiruandon)] Usotsuki Hanayome (Danganronpa) [Digital]

(C71) [S-G.H. (Oona Mitsutoshi)] SUICIDA DESESPERACION (Coyote Ragtime Show)

[Chijoku An] Crossdressing Knight [English] =LWB=

Dokidoki Time Paradise 5 ~Sawari Houdai Ire Houdai~

(C90) [Kenja Time (MANA)] Gentle Blue Fantasy 3 (Granblue Fantasy)

(COMITIA114) [Watanuki Shinguten (Watanuki Ron)] in the first person

Kyousei! Oshioki Time Vol. 04