Sissy

Sissyとは女性らしく振る舞う、受動的な男性のこと。

Illustrations and Manga (315)

sissy, maletofemale, transformation / Worse than a monkey's paw Worse than a monkey's paw
Velvet-Peach
fanart, game, commission / Just listen to me! Just listen to me!
NungMeeNui
4
fanart, game, TexasChainsawMassacre / Sissy always wifey material Sissy always wifey material
NungMeeNui
sketch, stream, patreon / Suggestion Stream Drawings: Pret Suggestion Stream Drawings: Pret
Lunarcey
sissy / [Commission] Bunny Catalina ! / November 9th, 2023 [Commission] Bunny Catalina !
PurpleAnart
humiliation, diaper, loser / Superchu Beat by Libre (Comm) Superchu Beat by Libre (Comm)
SDCharm
TexasChainsawMassacre, Johnny, sissy / Johnny and Sissy Johnny and Sissy
NungMeeNui
sissy, trap, blonde / Fairy femboy Fairy femboy
Oniblonde
humiliation, SONIC, Tails / Red Rage: Dominance, Pt.2 (Comm) Red Rage: Dominance, Pt.2 (Comm)
SDCharm
my_little_pony, Equestria_Girls, MLP / Make me pretty Make me pretty
excelso
Carrie, CarrieFilm, CarrieMovie / Carrie White Carrie White
Zenovand
sissy, CrossDresser, crossdressing / Zelda crossplay Zelda crossplay
Velvet-Peach
2
fanart, game, TexasChainsawMassacre / Julie Crawford and Sissy Julie Crawford and Sissy
NungMeeNui
game, fanart, drawing / Sissy my sweet girl Sissy my sweet girl
NungMeeNui
AI
19
sissy / 可愛いお姫様 / October 20th, 2023 可愛いお姫様
リヨウ
Furry, sissy / uni gift / October 16th, 2023 uni gift
maryfurry
AI
sissy / no and how do you think / October 10th, 2023 no and how do you think
maryfurry
2
game, Fanmade, txchainsaw / Sissy Anthophile Outfit Sissy Anthophile Outfit
NungMeeNui
fluttershy, mylittlepony, diaper / Intober 1 Intober 1
Maxicoon
2
fanart, game, drawing / Sissy sketch Sissy sketch
NungMeeNui
AI
7
cd, crossdress, feminization / Ben Date Page 6 Ben Date Page 6
Mecha.XJ
3
Orange, kemonomimi, sissy / Misc Orange Art Misc Orange Art
NormalDeviant
reaper, femboy, sissy / Femboy Reaper Sissy OC Fantasy Femboy Reaper Sissy OC Fantasy
zversnow
AI
5
BEN10, crossdressing, cd / Ben 10 - First Date Page 3/? Ben 10 - First Date Page 3/?
Mecha.XJ
my_little_pony, Equestria_Girls, MLP / Adora-overalls Adora-overalls
excelso
9
pokemon, gary, feminization / Gary's hourney Page 9 Gary's hourney Page 9
Flechitas
sissy, game, videogame / My little tiny Sissy My little tiny Sissy
NungMeeNui
10
pokemon, trap, crossdressing / Gary's Journey part9 Gary's Journey part9
Flechitas
Texas, txchainsaw, leatherface / Sissy wifey material Sissy wifey material
NungMeeNui
bimbo, sissy, femboy / ゼロツーダンス九十九くん/Zero Two Dance 99 ゼロツーダンス九十九くん/Zero Two Dance 99
けい
game, fanart, Texas / Sissy and Nugget Sissy and Nugget
NungMeeNui
diaperboy, Stan, Marsh / Stan? More like stannly Stan? More like stannly
cartoon heart
diaper, abdl, babyfur / Darn Letters. Darn Letters.
Maxicoon
my_little_pony, Equestria_Girls, MLP / Modeling V2 Modeling V2
excelso
drawing, videogame, Texas / Sissy - Sawyer family Sissy - Sawyer family
NungMeeNui
AI
2
GyozaMix, ShinySissy / Detached sleeves / May 29th, 2023 Detached sleeves
Yamata
sissy / Untitled / May 18th, 2023 Untitled
maryfurry
humiliation, diaper, Rolereversal / Led by the Hand (Comm/STORY) Led by the Hand (Comm/STORY)
SDCharm
sissy, sky / sissy sky / April 23rd, 2023 sissy sky
ふたば
humiliation, underwear, SONIC / Battle of Brotherhood (Comm) Battle of Brotherhood (Comm)
SDCharm
diapers, diaperboy, sissy / Such pretty little boy Such pretty little boy
cartoon heart
3
Police, Toy, Sincity / Arrested on Sunday night. Arrested on Sunday night.
sissitrix
Furry, sissy / tender cub / April 12th, 2023 tender cub
maryfurry
AI
breast, boob, sissy / Untitled Untitled
Lia Sissy
diaperboy, craigtucker, softpinkdiapers / Check out this cutie! Check out this cutie!
cartoon heart
2
sissy / Vegas baby （2 version） / March 17th, 2023 Vegas baby （2 version）
AMY
humiliation, underwear, Juvenile_Jenga / Juvenile Jenga - #62 Juvenile Jenga - #62
SDCharm
AI
maid, girl, cute / Lia Maid Lia Maid
Lia Sissy
18
sissy / Bad End: Wilted or Blooming / March 9th, 2023 Bad End: Wilted or Blooming
Xros☆Reflection
sissy / a costume for carnival / February 22nd, 2023 a costume for carnival
maryfurry
AI
18
StableDiffusion, sissy / バスケットボールするはずだった男の娘 / February 21st, 2023 バスケットボールするはずだった男の娘
Jsis
humiliation, sissy, toy / Pumping and milking Pumping and milking
sissitrix
my_little_pony, my_little_ponyEquestria_Girlsf, sissy / Fluttershy Wins the Bet Fluttershy Wins the Bet
excelso
crossdress, crossdressing, femboy / Boy Maid Boy Maid
PurpleAnart
diaper, cosplay, crossdressing / 12-01-2022 12-01-2022
BabyMouseyBoy
AI
2
sissy, Furry / Change of panties / November 23rd, 2022 Change of panties
maryfurry
diaper, sissy, Deltarune / 11-20-2022 11-20-2022
BabyMouseyBoy
humiliation, SONIC, diaper / Old Patreon Pic - #32 Old Patreon Pic - #32
SDCharm
diaper, humiliation, abdl / Diaper Boy Gets Pansted Diaper Boy Gets Pansted
Paddedskater
AI
2
Furry, sissy / A night in Panties / November 8th, 2022 A night in Panties
maryfurry

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