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47 posts under the crossdressing tag — a growing gallery on Rule34world.

Also see: femboymalegayanalmale onlyanal sexyaoigay sex2boyssissytrapmoaning
michinoku komaro, otori-tan, terui arisu #17220
00:00
michinoku komaro, otori-tan, terui arisu
Player
big ass, big balls, big butt #16760
01:48
big ass, big balls, big butt
Player
big ass, big balls, big butt #16003
01:12
big ass, big balls, big butt
Player
generation 4 pokemon, lucario, pokemon (species) #15563
00:41
generation 4 pokemon, lucario, pokemon (species)
Player
big ass, big balls, big butt #15290
01:42
big ass, big balls, big butt
Player
narukami yu, teddie (persona), persona #15051
00:12
narukami yu, teddie (persona), persona
Player
astolfo (fate), astolfo (sailor paladin) (fate), jeanne d'arc (fate) #14830
00:39
astolfo (fate), astolfo (sailor paladin) (fate), jeanne d'arc (fate)
Player
big ass, big balls, big butt #14430
01:05
big ass, big balls, big butt
Player
anon, anonymous character, anonymous male #12568
00:06
anon, anonymous character, anonymous male
Player
big ass, big balls, big butt #12513
01:30
big ass, big balls, big butt
Player
bridget, ramlethal valentine, guilty gear #12230
00:28
bridget, ramlethal valentine, guilty gear
Player
roxanne (dross), female, 1girl #12060
09:00
roxanne (dross), female, 1girl
Player
big ass, big balls, big butt #11971
01:30
big ass, big balls, big butt
Player
virtamate, 1boy, 1femboy #11741
00:11
virtamate, 1boy, 1femboy
Player
wendy's, 1boy, 1femboy #11738
00:14
wendy's, 1boy, 1femboy
Player
big ass, big balls, big butt #10436
02:21
big ass, big balls, big butt
Player
anal, blackmail, blowjob #8907
31:08
anal, blackmail, blowjob
Player
ash (ashdiary), dr. k, dr.k (changed) #8772
04:03
ash (ashdiary), dr. k, dr.k (changed)
Player
virtamate, 1femboy, 2boys #8670
01:52
virtamate, 1femboy, 2boys
Player
anon, anonymous male, gerudo link #8290
00:06
anon, anonymous male, gerudo link
Player
aka6, anus, big balls #8224
00:15
aka6, anus, big balls
Player
femboy hooters, hooters, virtamate #7278
05:29
femboy hooters, hooters, virtamate
Player
femboy hooters, hooters, virtamate #7277
05:35
femboy hooters, hooters, virtamate
Player
virtamate, 1femboy, 2boys #7275
05:04
virtamate, 1femboy, 2boys
Player
virtamate, 1femboy, 2boys #7274
04:50
virtamate, 1femboy, 2boys
Player
astolfo (fate), fate/apocrypha, fate (series) #6789
00:01
astolfo (fate), fate/apocrypha, fate (series)
Player
virtamate, 1femboy, 2boys #6614
01:22
virtamate, 1femboy, 2boys
Player
bridget, may (guilty gear), female #5829
00:08
bridget, may (guilty gear), female
Player
cloud strife, blacked, final fantasy #5487
00:10
cloud strife, blacked, final fantasy
Player
anal, anilingus, big penis #5381
06:16
anal, anilingus, big penis
Player
krillin, kuririn, son goku #5293
00:21
krillin, kuririn, son goku
Player
milan morgenstern, oc, original character #5255
00:14
milan morgenstern, oc, original character
Player
blacked, 2boys, anal #4675
00:21
blacked, 2boys, anal
Player
skyrim, the elder scrolls, 1femboy #4078
02:42
skyrim, the elder scrolls, 1femboy
Player
cloud strife, final fantasy, final fantasy vii #3871
00:07
cloud strife, final fantasy, final fantasy vii
Player
virtamate, 1femboy, 2boys #3865
00:08
virtamate, 1femboy, 2boys
Player
anal, chastity cage, crossdressing #3850
00:51
anal, chastity cage, crossdressing
Player
blacked, anal, crossdressing #3847
02:42
blacked, anal, crossdressing
Player
original character, original, virtamate #3346
03:01
original character, original, virtamate
Player
mona (genshin impact) (cosplay), scaramouche (genshin impact), genshin impact #3040
02:13
mona (genshin impact) (cosplay), scaramouche (genshin impact), genshin impact
Player