crossdressing_female best from all time

Time frame

Tags

crossdressing female

1boy 1boy1girl 1girl 1girls 2020s 2024 :o adult_boy adult_male anime areolae arms_up belly_button black_hair blush blushing breast_grab breasts breasts_out brown_eyes clothed crossdressing crossdressing_female dumbbell_nan_kilo_moteru? duo empty_eyes eyebrows_visible_through_hair female grabbing_another's_breasts groping groping_breasts groping_from_behind hands_behind_head haruduki hypnosis lifted_top light-skinned_female light_skin male manga medium_breasts mind_control moderate_tomboy navel nipples open_mouth shiny_hair shiny_skin shirt shirt_up short_hair shorts sitting striped_bottomwear t-shirt tachibana_satomi_(dumbbell_nan_kilo_moteru?) teenage_girl teenager thighs tomboy two_tone_bottomwear two_tone_bottomwear_(blackandwhite) white_topwear
1boy 1boy1girl 1girl 1girls 2020s 2024 :o adult_boy adult_male anime areolae arms_up belly_button black_hair blush blushing breast_grab breasts breasts_out brown_eyes clothed crossdressing crossdressing_female dumbbell_nan_kilo_moteru? duo empty_eyes eyebrows_visible_through_hair female grabbing_another's_breasts groping groping_breasts groping_from_behind hands_behind_head haruduki hypnosis lifted_top light-skinned_female light_skin male manga medium_breasts mind_control moderate_tomboy navel nipples open_mouth shiny_hair shiny_skin shirt shirt_up short_hair shorts sitting striped_bottomwear t-shirt tachibana_satomi_(dumbbell_nan_kilo_moteru?) teenage_girl teenager thighs tomboy two_tone_bottomwear two_tone_bottomwear_(blackandwhite) white_topwear
1girls :o arms_behind_back bangs black_ribbon blonde_hair breasts collarbone crossdressing crossdressing_female drawstring female flippers gradient_hair groin hair_between_eyes hair_flaps hair_ornament hair_ribbon hairclip highres kantai_collection long_hair looking_at_viewer male_swimwear male_swimwear_challenge medium_breasts mens_swimsuit_challenge nagi_(shunsuke-manage) navel nipples red_eyes remodel_(kantai_collection) ribbon scuba_gear signature simple_background solo stomach swim_trunks topless very_long_hair wet white_background yuudachi_(kantai_collection)
1girls :o arms_behind_back bangs black_ribbon blonde_hair breasts collarbone crossdressing crossdressing_female drawstring female flippers gradient_hair groin hair_between_eyes hair_flaps hair_ornament hair_ribbon hairclip highres kantai_collection long_hair looking_at_viewer male_swimwear male_swimwear_challenge medium_breasts mens_swimsuit_challenge nagi_(shunsuke-manage) navel nipples red_eyes remodel_(kantai_collection) ribbon scuba_gear signature simple_background solo stomach swim_trunks topless very_long_hair wet white_background yuudachi_(kantai_collection)
absurd_res ai_generated ass ass ass_cleavage ass_focus asscheeks beach beach_background blush blush cameltoe crossdressing crossdressing_female curly_hair curvy_figure exhibitionism exhibitionist furrowed_eyebrows large_ass leaning_on_rock looking_at_viewer luz_noceda male_swimwear male_swimwear_challenge nervous_smile nervous_sweat round_ass round_butt short_hair swimming_trunks the_owl_house tomboy topless topless_female wavy_mouth wiggle_lines wiggling_ass
absurd_res ai_generated ass ass ass_cleavage ass_focus asscheeks beach beach_background blush blush cameltoe crossdressing crossdressing_female curly_hair curvy_figure exhibitionism exhibitionist furrowed_eyebrows large_ass leaning_on_rock looking_at_viewer luz_noceda male_swimwear male_swimwear_challenge nervous_smile nervous_sweat round_ass round_butt short_hair swimming_trunks the_owl_house tomboy topless topless_female wavy_mouth wiggle_lines wiggling_ass
anthro baggy_clothing beach blush brown_body brown_fur clothed clothing crossdressing crossdressing_female domestic_cat embarrassed embarrassed_nude_exposure embarrassed_nude_female exhibitionism felid feline felis female fur green_hair green_nipples hair hammock hi_res kiwi_(disambiguation) kiwi_cutie male_swimwear male_swimwear_challenge mammal mens_swimsuit_challenge nipples public_nudity sea seaside solo swimming_trunks swimwear water
anthro baggy_clothing beach blush brown_body brown_fur clothed clothing crossdressing crossdressing_female domestic_cat embarrassed embarrassed_nude_exposure embarrassed_nude_female exhibitionism felid feline felis female fur green_hair green_nipples hair hammock hi_res kiwi_(disambiguation) kiwi_cutie male_swimwear male_swimwear_challenge mammal mens_swimsuit_challenge nipples public_nudity sea seaside solo swimming_trunks swimwear water
4boys belt black_background black_hair blush breasts clenched_teeth collar collarbone crossdressing crossdressing_female female fingernails game_cg glaring highres multiple_boys navel nipples original pink_lips purple_eyes red_collar restrained reverse_trap scowl short_hair teeth tomboy undressing uniform unko_man
4boys belt black_background black_hair blush breasts clenched_teeth collar collarbone crossdressing crossdressing_female female fingernails game_cg glaring highres multiple_boys navel nipples original pink_lips purple_eyes red_collar restrained reverse_trap scowl short_hair teeth tomboy undressing uniform unko_man
1girls 2024 2024s against_tree ai_generated anthro anthro_only black_eyes blush boots brown_fur canine canine_pussy coat crossdressing crossdressing_female debruff_sampson dog_ears dog_girl female female_focus female_only furry furry_female looking_at_viewer looking_down looking_down_at_viewer low-angle_view outdoors pants pants_down pups_of_liberty pussy pussy_juice rough_collie shy simple_eyes soldier spreading_pussy standing tree uniform waistcoat white_fur
1girls 2024 2024s against_tree ai_generated anthro anthro_only black_eyes blush boots brown_fur canine canine_pussy coat crossdressing crossdressing_female debruff_sampson dog_ears dog_girl female female_focus female_only furry furry_female looking_at_viewer looking_down looking_down_at_viewer low-angle_view outdoors pants pants_down pups_of_liberty pussy pussy_juice rough_collie shy simple_eyes soldier spreading_pussy standing tree uniform waistcoat white_fur
1boy 2girls big_penis blush breasts breasts_out collaborative_fellatio crossdressing crossdressing_female cum cumshot fellatio female gyakuten_saiban haori_murasame hat licking male mosaic_censoring penis pov pov_eye_contact rei_membami ryutaro_naruhodo saliva school_uniform susato_mikotoba tongue uniform
1boy 2girls big_penis blush breasts breasts_out collaborative_fellatio crossdressing crossdressing_female cum cumshot fellatio female gyakuten_saiban haori_murasame hat licking male mosaic_censoring penis pov pov_eye_contact rei_membami ryutaro_naruhodo saliva school_uniform susato_mikotoba tongue uniform
1boy 1girl 1girls 2010s 2012 black_bra blush boxer_briefs boxers bra bra_lift breasts brown_eyes brown_hair censored cowgirl_position crossdressing crossdressing_female duo exposed_breasts female female_dominating_male female_on_male femdom girl_on_top grinding hand_holding holding_hands indoors interlocked_fingers light-skinned_female light-skinned_male light_skin long_hair male male_underwear manga midriff mis_res moderate_tomboy navel nipples open_clothes open_mouth open_shirt original outercourse penis shirt_lift smile straddle straight tomboy translation_request trembling two_tone_underwear two_tone_underwear_(blackandpink) underwear white_shirt white_topwear
1boy 1girl 1girls 2010s 2012 black_bra blush boxer_briefs boxers bra bra_lift breasts brown_eyes brown_hair censored cowgirl_position crossdressing crossdressing_female duo exposed_breasts female female_dominating_male female_on_male femdom girl_on_top grinding hand_holding holding_hands indoors interlocked_fingers light-skinned_female light-skinned_male light_skin long_hair male male_underwear manga midriff mis_res moderate_tomboy navel nipples open_clothes open_mouth open_shirt original outercourse penis shirt_lift smile straddle straight tomboy translation_request trembling two_tone_underwear two_tone_underwear_(blackandpink) underwear white_shirt white_topwear
1boy 1boy1girl 1girls 2024 2024s ai_generated anthro anthro_on_human blowjob blush boots brown_fur cabin canine canine_humanoid closed_eyes clothed coat crossdressing crossdressing_female cum cum_in_mouth curtains debruff_sampson disguise dog_ears dog_girl dog_tail faceless_male female female_focus furry furry_female human human_on_anthro indoors kneeling long_hair male male/female on_knees pants penis penis_in_mouth penis_out pups_of_liberty saliva saliva_on_face saliva_on_penis saliva_trail sex side_view soldier standing suit tail tongue tricorne uniform waistcoat warm_lighting white_fur window
1boy 1boy1girl 1girls 2024 2024s ai_generated anthro anthro_on_human blowjob blush boots brown_fur cabin canine canine_humanoid closed_eyes clothed coat crossdressing crossdressing_female cum cum_in_mouth curtains debruff_sampson disguise dog_ears dog_girl dog_tail faceless_male female female_focus furry furry_female human human_on_anthro indoors kneeling long_hair male male/female on_knees pants penis penis_in_mouth penis_out pups_of_liberty saliva saliva_on_face saliva_on_penis saliva_trail sex side_view soldier standing suit tail tongue tricorne uniform waistcoat warm_lighting white_fur window
1boy 1girl 1girls 2010s 2012 blush boxer_briefs boxers breasts brown_eyes brown_hair censored crossdressing crossdressing_female duo exposed_breasts female_dominating_male female_on_male girl_on_top grinding holding_hands indoors light-skinned_female light-skinned_male light_skin long_hair male_underwear manga midriff mis_res moderate_tomboy navel nipples open_clothes open_shirt original outercourse penis pink_underwear shirt_lift smile straight tomboy two_tone_underwear two_tone_underwear_(blackandpink) underwear white_topwear
1boy 1girl 1girls 2010s 2012 blush boxer_briefs boxers breasts brown_eyes brown_hair censored crossdressing crossdressing_female duo exposed_breasts female_dominating_male female_on_male girl_on_top grinding holding_hands indoors light-skinned_female light-skinned_male light_skin long_hair male_underwear manga midriff mis_res moderate_tomboy navel nipples open_clothes open_shirt original outercourse penis pink_underwear shirt_lift smile straight tomboy two_tone_underwear two_tone_underwear_(blackandpink) underwear white_topwear
2020 2020s 2girls al_azif anus_outline ass bandaids_on_nipples barefoot blue_hair blush blushing boxer_briefs butt_crack_outline cameltoe crossdressing crossdressing_female demonbane eyebrows_visible_through_hair fang green_underwear long_hair long_hair_female looking_back male_underwear manga mild_tomboy moderate_tomboy multiple_girls nipple_covers on_back oni_draws pasties peace_sign pink_hair plaster puffy_pussy rear_view saya saya_no_uta tomboys topless topless_female
2020 2020s 2girls al_azif anus_outline ass bandaids_on_nipples barefoot blue_hair blush blushing boxer_briefs butt_crack_outline cameltoe crossdressing crossdressing_female demonbane eyebrows_visible_through_hair fang green_underwear long_hair long_hair_female looking_back male_underwear manga mild_tomboy moderate_tomboy multiple_girls nipple_covers on_back oni_draws pasties peace_sign pink_hair plaster puffy_pussy rear_view saya saya_no_uta tomboys topless topless_female
1boy1girl 1girls animate_inanimate applying_makeup breasts cigarette completely_nude_female couple crossdressing crossdressing_female cuphead_(game) demon fake_mustache feet female humanoid imp king_dice loodles no_sex object_head object_humanoid pussy rule_63 smoking the_devil_(cuphead) unusual_nipples
1boy1girl 1girls animate_inanimate applying_makeup breasts cigarette completely_nude_female couple crossdressing crossdressing_female cuphead_(game) demon fake_mustache feet female humanoid imp king_dice loodles no_sex object_head object_humanoid pussy rule_63 smoking the_devil_(cuphead) unusual_nipples
1boy 1girls blush clothed clothing_swap costume_switch crossdressing crossdressing_female crossdressing_male female final_fantasy final_fantasy_vii final_fantasy_vii_remake male muscular muscular_male rude_(final_fantasy_vii) smooth_skin tifa_lockhart tifa_lockhart_(cosplay)
1boy 1girls blush clothed clothing_swap costume_switch crossdressing crossdressing_female crossdressing_male female final_fantasy final_fantasy_vii final_fantasy_vii_remake male muscular muscular_male rude_(final_fantasy_vii) smooth_skin tifa_lockhart tifa_lockhart_(cosplay)
absurdres bangs black_pantyhose black_suit crossdressing_female fate/grand_order fate_(series) female formal fujimaru_ritsuka_(female) highres ke_zhongxiao_niao pantyhose red_hair simple_background smile suit white_background yellow_eyes
absurdres bangs black_pantyhose black_suit crossdressing_female fate/grand_order fate_(series) female formal fujimaru_ritsuka_(female) highres ke_zhongxiao_niao pantyhose red_hair simple_background smile suit white_background yellow_eyes
asian braless brown_hair clothing crossdressing crossdressing_female denim_clothing dialogue female jaiden_animations jaidenanimations nipple_slip one_breast_out overalls short_hair solo tan_body tomboy wardrobe_malfunction youtube youtuber
asian braless brown_hair clothing crossdressing crossdressing_female denim_clothing dialogue female jaiden_animations jaidenanimations nipple_slip one_breast_out overalls short_hair solo tan_body tomboy wardrobe_malfunction youtube youtuber
art_of_fighting crossdressing crossdressing_female effineffer embarrassed king_(snk) king_of_fighters reverse_trap tomboy
art_of_fighting crossdressing crossdressing_female effineffer embarrassed king_(snk) king_of_fighters reverse_trap tomboy
16:10 anthro bodily_fluids bondage bound briefs clothing crossdressing_female cum cum_on_face english_text equid equine female female_focus fluttershy_(mlp) friendship_is_magic genital_fluids hair_on_head hasbro hi_res horse mammal my_little_pony offscreen_character pegasus pony quakehoof solo_focus text underwear widescreen wings
16:10 anthro bodily_fluids bondage bound briefs clothing crossdressing_female cum cum_on_face english_text equid equine female female_focus fluttershy_(mlp) friendship_is_magic genital_fluids hair_on_head hasbro hi_res horse mammal my_little_pony offscreen_character pegasus pony quakehoof solo_focus text underwear widescreen wings
1boy1girl blue_eyes crossdressing crossdressing_female dominant_female erection freckles freckles_on_face freckles_on_shoulders hot_pants hot_pants_(jjba) hotpants johnny_joestar jojo's_bizarre_adventure lipstick male/female nail_polish nipples orange_hair pegging pink_hair precum red_hair riding riding_dildo steel_ball_run strap-on submissive_male tomboy
1boy1girl blue_eyes crossdressing crossdressing_female dominant_female erection freckles freckles_on_face freckles_on_shoulders hot_pants hot_pants_(jjba) hotpants johnny_joestar jojo's_bizarre_adventure lipstick male/female nail_polish nipples orange_hair pegging pink_hair precum red_hair riding riding_dildo steel_ball_run strap-on submissive_male tomboy
abs beach bedroom_eyes cameltoe clitoris_outline clothed clothing crossdressing crossdressing_female dessert dialogue digital_media_(artwork) dragon eating female food grey_body hi_res ice_cream lizard looking_at_viewer male_swimwear_challenge muscular narrowed_eyes piercing presenting presenting_crotch pussy_outline queen_(scalesindark) red_eyes reptile sand scalesindark scalie seaside seductive swimming_trunks swimwear tongue top_less topless
abs beach bedroom_eyes cameltoe clitoris_outline clothed clothing crossdressing crossdressing_female dessert dialogue digital_media_(artwork) dragon eating female food grey_body hi_res ice_cream lizard looking_at_viewer male_swimwear_challenge muscular narrowed_eyes piercing presenting presenting_crotch pussy_outline queen_(scalesindark) red_eyes reptile sand scalesindark scalie seaside seductive swimming_trunks swimwear tongue top_less topless
bad_anatomy brother brother_and_sister color crossdressing crossdressing_female dave_strider eating_pussy female homestuck incest licking_pussy male naughtyvixens on_knees oral request rose_lalonde short_hair short_hair_female short_hair_male sister sister_and_brother sketch sketchy suit woman_in_suit
bad_anatomy brother brother_and_sister color crossdressing crossdressing_female dave_strider eating_pussy female homestuck incest licking_pussy male naughtyvixens on_knees oral request rose_lalonde short_hair short_hair_female short_hair_male sister sister_and_brother sketch sketchy suit woman_in_suit
crossdressing_female masculine_female masturbation short_hair solo tagme tomboy
crossdressing_female masculine_female masturbation short_hair solo tagme tomboy
blue_eyes crossdressing_female konoe_subaru looking_at_viewer mayo_chiki! no_bra open_shirt opening_shirt orange_hair pink_panties pointy_chin red_tie sad small_breasts subaru_konoe
blue_eyes crossdressing_female konoe_subaru looking_at_viewer mayo_chiki! no_bra open_shirt opening_shirt orange_hair pink_panties pointy_chin red_tie sad small_breasts subaru_konoe
2007 bandages bare_shoulders black_hair blush canon_crossdressing crossdressing crossdressing_female doujin_cover eye_patch female female_only flat_chest flowers full_body gintama long_hair off_shoulder open_clothes open_jacket panties ponytail sakurazawa_izumi samurai sarashi sitting socks solo suggestive_fluid tomboy white_panties yagyuu_kyuubei yellow_eyes
2007 bandages bare_shoulders black_hair blush canon_crossdressing crossdressing crossdressing_female doujin_cover eye_patch female female_only flat_chest flowers full_body gintama long_hair off_shoulder open_clothes open_jacket panties ponytail sakurazawa_izumi samurai sarashi sitting socks solo suggestive_fluid tomboy white_panties yagyuu_kyuubei yellow_eyes
anal anal_sex bandages blonde_hair blue_eyes crossdressing_female dominant_female erect_penis freckles freckles_on_face hotpants johnny_joestar jojo's_bizarre_adventure lipstick male/female muscular_female nail_polish pegging pink_hair steel_ball_run strap-on strapon
anal anal_sex bandages blonde_hair blue_eyes crossdressing_female dominant_female erect_penis freckles freckles_on_face hotpants johnny_joestar jojo's_bizarre_adventure lipstick male/female muscular_female nail_polish pegging pink_hair steel_ball_run strap-on strapon