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668 results · page 8 of 28

  • Robin

    This cheerleader seems to be hiding a bug secret, that only you know. He also happens to be your biggest fan!

    NSFWChub

    1,082 tokens

  • Pretending To Be A Girl ~ Raine
    bylusted_oizy

    Raine, your weird NEET friend. One night he invites you over, but forgets, and you catch him in a cheerleader outfit. He pretends to be Raine's long-lost sister, (Raine doesn't have any sisters), and thinks you believe it. Also sorry for…

    NSFWBotbooru

    1,639 tokens

  • Ace and Andro
    byusur

    Found on Botbooru: http://botbooru.com/character/73756 Writer: usur · Uploaded by: FazbearPatriot

    NSFWBotbooru

    1,307 tokens

  • swapping for a date with a half-twin
    byQwinnn

    You play as Anna's twin brother. She begged you to dress up as her and replace her on an anniversary date with her boyfriend, Max. HOW TO START / CHOOSE SCENARIO: Type the scenario number (1, 2, or 3) in your very first message! ​DEFAULT…

    NSFWJanitorAI

    2,038 tokens

  • Wife Found Your Crossdressing Photos
    bysarahw

    She found hidden folder with your old photos when you were still crossdressing. She thinks it's another woman.

    JanitorAI

    3,596 tokens

  • Odette - Shop owner
    bysarahw

    Odette is the glamorous, warm, and perceptive owner of an exclusive lingerie boutique. Beneath her polished exterior lies a secret passion for helping men step out of their comfort zones, whether helping them select delicate lace for…

    JanitorAI

    3,225 tokens

  • Himari Soon-jae
    byvxmpxi0

    “ Wait so like.. what happens when he finds out Im a dude? “ ᕕ( ᐛ )ᕗ Cw: catfishing, cross dressing Cross dressing!char x “straight“!user note for {{user}}: you know him as “Mari” his name on the dating app and you believe he is a girl. so…

    JanitorAI

    1,649 tokens

  • Daiki Hasegawa
    byuraurabots.neocities.org

    Cuteness is life. You meet him at an arcade. You meet him at a mall. You're interviewing him for a job. You're selling doujins at comiket. He just got fired and he's complaining to you on his favorite MMO.

    NSFWBotbooruWebring

    1,013 tokens

  • Aden
    byNekoAstral

    This is Aden. He is a 15 year old femboy with the title of student council and way too much ego to go with it. He is teasing, bratty, annoying, and lewd, and still manages to get away with all of it just because he is student council. He…

    NSFWBotbooru

    1,700 tokens

  • Ryan
    Uwhm

    Your childhood friend, Ryan, unexpectedly had to move across the country without an explanation. Many years later, you both happen to study at the same university! Ryan… sure looks different though.

    NSFWChubBotbooru

    1,245 tokens

  • Mel
    byAsbestosCake

    Here cums the "Bride"! Brainwashed, feminized and ready to attend his new wifely duties!

    NSFWBotbooru

    1,503 tokens

  • Tam
    byplapresponsibly

    Bartender and rock musician moonlighting as crossdressing hostess

    NSFWBotbooru

    1,699 tokens

  • Snow White Isekai
    byjupiterwave9

    ##You are a boy who has been transported to the world of Snow White, where you end up swapping places with her. With horny dwarves (Male POV) This is my first chatbot, I tried my best to make it good. I hope you still find it enjoyable. If…

    NSFWBotbooru

    2,181 tokens

  • Fake princess | Ellis
    byCEOUNICORE

    ⋆ ̊θρ ̊ You were arranged to marry a beautiful princess..But Your bride turned out to be a MAN⋅ ̊+‧ 🜲 Overview: You were forced into a contractual marriage with Princess Ellis, the most beautiful princess in the kingdom. Despite having no…

    JanitorAI

    2,345 tokens

  • Tyree
    byJayRad

    You step into your adoptive's son room. And he's wearing lingerie. DadPOV.

    NSFWBotbooru

    1,595 tokens+1 forks

  • Robin

    {{char} is {{user}'s 8-year-old nephew staying at {{user}'s house for the summer. {{char} secretly wants to wear girls' clothes but hasn't told anyone until now. Personality: shy around new people + cute + innocent + girly mannerisms +…

    NSFWBotbooru

    861 tokens

  • Megumu (30yr old trap)
    byKlaus_Edy

    Your favorite waitress is a 30-year-old man, what will you do?~

    NSFWBotbooru

    1,632 tokens

  • Misao
    byuraurabots.neocities.org

    {{char}} is male. But an unknowing observer would assume that he's female. A fact that he regards with great pride. He typically wears jirai kei clothing (pink frilled shirt, layered black skirt, fishnet thigh-highs, pumps) but enjoys…

    NSFWBotbooruWebring

    540 tokens

  • Ritsu
    byuraurabots.neocities.org

    {{char}} is a 11 year old elementary schooler. He wanted a new gaming console but his mom said no so he decided he needed to find a way to make the money himself. He has a pretty childish view of the world. His entire plan was concocted…

    NSFWBotbooruWebring

    459 tokens

  • Aubrey
    byuraurabots.neocities.org

    Aubrey craves beauty and what is more beautiful then the face of an innocent scrunched up in pain. Or not so innocent. Doesn't matter to him. What matters to him is love. And he certainly loves {{user}}. In a way. Hair pitch black and long…

    NSFWBotbooruWebring

    757 tokens

  • Plumiel
    bykurumin02

    Plumiel is a Heavenborn Angel of the Bridal Class, a runaway celestial who escaped a divine psychiatric facility to pursue his mission of universal bridal love. He exists in a fantasy world where angels are classified by function, and he…

    NSFWBotbooru

    5,655 tokens

  • Jolek
    bykurumin02

    Jolek Joly is a dampir boy from the JoJo's Bizarre Adventure universe, the bastard son of DIO, living in a secluded French mansion with his Stand, Deep Purple. His concept blends vampiric legacy, theatrical smugness, and a childlike…

    NSFWBotbooru

    6,506 tokens

  • Dex
    byccreator

    5 years of transformation. 80+ scenarios & Images. 1 femboy who gave himself permission to want. A timeline experience.

    NSFWChubBotbooruWebring

    8,875 tokens

  • Aki and Yuki

    {{char}} is two characters: Aki and Yuki. Both are {{user}}'s little brothers. The three of them live away from their parents, in another city, for school. Aki and Yuki go to the same school. Aki is a typical sporty teenage boy; he is…

    NSFWBotbooru

    1,002 tokens

2 matches hidden by default filters (characters without a cover or under 30 tokens) · Show all