crossdressing_male best from last week

Time frame

Tags

crossdressing male

1boy 1femboy 2d 2d_animation after_anal after_sex against_wall anal anal_sex animated artist_logo artist_name ass ass_up big_ass big_butt blackmail blindfold blush blush_lines bottom_heavy bottom_heavy_femboy bottomless bouncing_breasts bubble_butt city_background cityscape crossdressing crossdressing_male cum cum_everywhere cum_in_ass cum_inside cum_on_ass cum_on_hair cum_on_pillow cum_out_mouth cum_through cumflation cumming_inside curvy curvy_figure excessive_cum face_against_ass fat_ass femboy feminine_male fucked_senseless fucked_silly gay gay_sex giant_ass glistening green_(artist) huge_ass huge_butt huge_cumshot jiggling_ass kabedon komi-san_wa_komyushou_desu legwear longer_than_one_minute looking_at_phone looking_at_viewer looking_back male/male male_bitch male_focus male_only male_pov moaning moaning_in_pleasure moving_hips multiple_views nipples opening_pants oral_sex osana_najimi otoko_no_ko outdoors outside phone pink_hair pov pov_eye_contact presenting_ass pulling_up_pants questionable_consent repost school_uniform sex skirt small_breasts small_penis sound sound_effects submissive sucking_penis surprised tagme teapot_(body_type) thick_ass thick_thighs thighhighs thrusting_into_ass tongue_out undressing_partner unzipping_pants video video_player wide_hips yaoi
1boy 1femboy 2d 2d_animation after_anal after_sex against_wall anal anal_sex animated artist_logo artist_name ass ass_up big_ass big_butt blackmail blindfold blush blush_lines bottom_heavy bottom_heavy_femboy bottomless bouncing_breasts bubble_butt city_background cityscape crossdressing crossdressing_male cum cum_everywhere cum_in_ass cum_inside cum_on_ass cum_on_hair cum_on_pillow cum_out_mouth cum_through cumflation cumming_inside curvy curvy_figure excessive_cum face_against_ass fat_ass femboy feminine_male fucked_senseless fucked_silly gay gay_sex giant_ass glistening green_(artist) huge_ass huge_butt huge_cumshot jiggling_ass kabedon komi-san_wa_komyushou_desu legwear longer_than_one_minute looking_at_phone looking_at_viewer looking_back male/male male_bitch male_focus male_only male_pov moaning moaning_in_pleasure moving_hips multiple_views nipples opening_pants oral_sex osana_najimi otoko_no_ko outdoors outside phone pink_hair pov pov_eye_contact presenting_ass pulling_up_pants questionable_consent repost school_uniform sex skirt small_breasts small_penis sound sound_effects submissive sucking_penis surprised tagme teapot_(body_type) thick_ass thick_thighs thighhighs thrusting_into_ass tongue_out undressing_partner unzipping_pants video video_player wide_hips yaoi
3femboys ai_generated anal anal_sex black_hair blush crossdressing crossdressing_male cum cumming cumming_from_anal_sex cumming_together cumming_while_penetrated curvy femboy foursome girly heat high_resolution highres ladyboy male_focus original original_character pout red_eyes saliva seductive sissy steam sweat tagme tomgirl tongue trap turtleneck veiny_penis white_hair winizzza
3femboys ai_generated anal anal_sex black_hair blush crossdressing crossdressing_male cum cumming cumming_from_anal_sex cumming_together cumming_while_penetrated curvy femboy foursome girly heat high_resolution highres ladyboy male_focus original original_character pout red_eyes saliva seductive sissy steam sweat tagme tomgirl tongue trap turtleneck veiny_penis white_hair winizzza
1femboy ai_generated anal anal_insertion anal_sex anal_sex angel angel_wings bulge cock crossdressing crossdressing_male curvy dick femboy girly halo heat high_resolution highres ladyboy male_focus multiple_views original original_character penis seductive see-through see-through_clothing see_through sissy sweat tagme tank_top tank_top_lift tomgirl trap voluptuous voluptuous_femboy wings winizzza
1femboy ai_generated anal anal_insertion anal_sex anal_sex angel angel_wings bulge cock crossdressing crossdressing_male curvy dick femboy girly halo heat high_resolution highres ladyboy male_focus multiple_views original original_character penis seductive see-through see-through_clothing see_through sissy sweat tagme tank_top tank_top_lift tomgirl trap voluptuous voluptuous_femboy wings winizzza
ahoge ai_generated ass_grab ass_worship aura_bella_fiora balls_in_panties balls_under_clothes blue_eye crossdressing crossdressing_female crossdressing_male elf elf_ears femboy gloves green_eyes heart-shaped_pupils heterochromia leather_gloves mare_bello_fiore microskirt overlord_(maruyama) panties panties_bulge panty_bulge plaid_skirt pointy_ears saliva tomboy vest white_panties white_vest
ahoge ai_generated ass_grab ass_worship aura_bella_fiora balls_in_panties balls_under_clothes blue_eye crossdressing crossdressing_female crossdressing_male elf elf_ears femboy gloves green_eyes heart-shaped_pupils heterochromia leather_gloves mare_bello_fiore microskirt overlord_(maruyama) panties panties_bulge panty_bulge plaid_skirt pointy_ears saliva tomboy vest white_panties white_vest
1femboy ai_generated anal anal_insertion anal_sex blue_hair bruise bruised bruises cock crossdressing crossdressing_male curvy dick domination femboy flaccid flaccid_penis flaccid_while_penetrated girly heat high_resolution highres ladyboy male_focus male_penetrated muscular muscular_male orange_eyes original original_character rough_sex saliva seductive sissy snot suplex sweat tagme tears tomgirl trap winizzza
1femboy ai_generated anal anal_insertion anal_sex blue_hair bruise bruised bruises cock crossdressing crossdressing_male curvy dick domination femboy flaccid flaccid_penis flaccid_while_penetrated girly heat high_resolution highres ladyboy male_focus male_penetrated muscular muscular_male orange_eyes original original_character rough_sex saliva seductive sissy snot suplex sweat tagme tears tomgirl trap winizzza
1boy 1femboy 2boys 3d abs abuse abused african african_male afroking ai_generated anime_style athletic athletic_male black_body black_hair bra bulge caption castration castration_threat cheerleader cheerleader_outfit cheerleader_uniform choker clothed clothing crop_top crossdressing crossdressing_male cruelty dark-skinned_male domestic_violence english_text eyeliner facial_hair father father_and_son femboy feminine_male feminization fit fit_male flat_chest flat_chested forced gay humiliated humiliation humiliation_fetish incest interracial jeans lipstick long_hair makeup male male/male male_only miniskirt muscles muscular muscular_male orange_eyes pale-skinned_male pale_skin pantyhose scared scared_expression serious short_hair sissy skirt text twink violence white_hair white_pantyhose white_skin white_skinned_male yaoi
1boy 1femboy 2boys 3d abs abuse abused african african_male afroking ai_generated anime_style athletic athletic_male black_body black_hair bra bulge caption castration castration_threat cheerleader cheerleader_outfit cheerleader_uniform choker clothed clothing crop_top crossdressing crossdressing_male cruelty dark-skinned_male domestic_violence english_text eyeliner facial_hair father father_and_son femboy feminine_male feminization fit fit_male flat_chest flat_chested forced gay humiliated humiliation humiliation_fetish incest interracial jeans lipstick long_hair makeup male male/male male_only miniskirt muscles muscular muscular_male orange_eyes pale-skinned_male pale_skin pantyhose scared scared_expression serious short_hair sissy skirt text twink violence white_hair white_pantyhose white_skin white_skinned_male yaoi
1boy ai_generated blonde_hair blue_eyes bra bra_peek bulge civitai color crossdressing crossdressing_male femboy feminine_male from_above girly high_heels jimojo long_sleeves looking_at_viewer male male_chest office_lady pectoral_cleavage pencil_skirt pony_diffusion_xl secretary short_skirt skirt thighs
1boy ai_generated blonde_hair blue_eyes bra bra_peek bulge civitai color crossdressing crossdressing_male femboy feminine_male from_above girly high_heels jimojo long_sleeves looking_at_viewer male male_chest office_lady pectoral_cleavage pencil_skirt pony_diffusion_xl secretary short_skirt skirt thighs
4boys balls big_penis blacked blonde_femboy blonde_hair blowbang blowjob blue_eyes body_writing crossdressing_male dark-skinned_male dark_skin fellatio femboy gangbang hirakumutw interracial licking licking_penis light-skinned_femboy light-skinned_male light_skin link long_nails male_pregnancy male_with_breasts mpreg nipple_piercing nipple_rings nipples nsfw passive_male penis_size_difference pink_nails pink_nipples small_breasts small_penis the_legend_of_zelda
4boys balls big_penis blacked blonde_femboy blonde_hair blowbang blowjob blue_eyes body_writing crossdressing_male dark-skinned_male dark_skin fellatio femboy gangbang hirakumutw interracial licking licking_penis light-skinned_femboy light-skinned_male light_skin link long_nails male_pregnancy male_with_breasts mpreg nipple_piercing nipple_rings nipples nsfw passive_male penis_size_difference pink_nails pink_nipples small_breasts small_penis the_legend_of_zelda
1boy ai_generated blonde_hair blue blue_bra blue_eyes bra bra_visible_through_clothes civitai color crossdressing crossdressing_male eyelashes femboy feminine_male girly high_heels jimojo kneeling male male_chest male_cleavage miniskirt office_clothing office_lady panty_bulge panty_peek pectoral_cleavage pencil_skirt pink_panties pony_diffusion_xl red_panties secretary short_hair short_skirt simple_background sitting sitting_on_desk skirt sleeves_rolled_up thighs transparent_clothing
1boy ai_generated blonde_hair blue blue_bra blue_eyes bra bra_visible_through_clothes civitai color crossdressing crossdressing_male eyelashes femboy feminine_male girly high_heels jimojo kneeling male male_chest male_cleavage miniskirt office_clothing office_lady panty_bulge panty_peek pectoral_cleavage pencil_skirt pink_panties pony_diffusion_xl red_panties secretary short_hair short_skirt simple_background sitting sitting_on_desk skirt sleeves_rolled_up thighs transparent_clothing
1boy ai_generated blonde_hair blue_eyes bra_peek bulge civitai clipboard color crossdressing crossdressing_male femboy feminine_male girly high_heels holding_clipboard jimojo male miniskirt office_lady pencil_skirt pony_diffusion_xl secretary short_skirt simple_background skirt sleeves_rolled_up standing steamy_breath thighs
1boy ai_generated blonde_hair blue_eyes bra_peek bulge civitai clipboard color crossdressing crossdressing_male femboy feminine_male girly high_heels holding_clipboard jimojo male miniskirt office_lady pencil_skirt pony_diffusion_xl secretary short_skirt simple_background skirt sleeves_rolled_up standing steamy_breath thighs
1boy 1girls age_difference ai_generated antenna_hair areola areolae arms_behind_back asymmetrical_docking bare_shoulders big_breasts black_gloves black_hair black_legwear black_thighhighs bondage breasts bulge capcom clothing collar collar_and_leash cowboy_shot crossdressing crossdressing_male crossover curvy_female elbow_gloves eteeming facing_viewer female femboy femsub hair_intakes large_breasts leash legs_together looking_at_viewer maledom microskirt milf miniskirt navel nipples older_woman_and_younger_boy open_mouth open_shirt open_smile osana_najimi panties partially_clothed pleated_skirt pubic_hair purple_eyes purple_hair pussy rebecca_chambers resident_evil short_hair simple_background size_difference skirt small_dom_big_sub smaller_male smile sparse_pubic_hair standing straight thick_thighs thighhighs uncensored voluptuous wide_hips
1boy 1girls age_difference ai_generated antenna_hair areola areolae arms_behind_back asymmetrical_docking bare_shoulders big_breasts black_gloves black_hair black_legwear black_thighhighs bondage breasts bulge capcom clothing collar collar_and_leash cowboy_shot crossdressing crossdressing_male crossover curvy_female elbow_gloves eteeming facing_viewer female femboy femsub hair_intakes large_breasts leash legs_together looking_at_viewer maledom microskirt milf miniskirt navel nipples older_woman_and_younger_boy open_mouth open_shirt open_smile osana_najimi panties partially_clothed pleated_skirt pubic_hair purple_eyes purple_hair pussy rebecca_chambers resident_evil short_hair simple_background size_difference skirt small_dom_big_sub smaller_male smile sparse_pubic_hair standing straight thick_thighs thighhighs uncensored voluptuous wide_hips
2boys 2femboys afroking ai_generated anime_style athletic athletic_male black_pantyhose blonde_hair blue_eyes brown_eyes bulge caption choker clothed crossdressing crossdressing_male dressed dyed_hair english_text femboy feminine_male fit fit_male flat_chest flat_chested fully_clothed gay jumper lipstick makeup male male_only males_only messy_hair pale-skinned_male pale_skin pantyhose posing red_lipstick short_hair sissy standing text twink white_body white_hair white_pantyhose white_skin yaoi
2boys 2femboys afroking ai_generated anime_style athletic athletic_male black_pantyhose blonde_hair blue_eyes brown_eyes bulge caption choker clothed crossdressing crossdressing_male dressed dyed_hair english_text femboy feminine_male fit fit_male flat_chest flat_chested fully_clothed gay jumper lipstick makeup male male_only males_only messy_hair pale-skinned_male pale_skin pantyhose posing red_lipstick short_hair sissy standing text twink white_body white_hair white_pantyhose white_skin yaoi
1boy ai_generated blonde_hair blue_bra blue_eyes bra bra_visible_through_clothes bulge civitai color crossdressing crossdressing_male femboy feminine_male girly high_heels jimojo long_sleeves looking_at_viewer male male_cleavage miniskirt office_lady pectoral_cleavage pencil_skirt pony_diffusion_xl secretary short_skirt skirt standing thighs translucent_clothing
1boy ai_generated blonde_hair blue_bra blue_eyes bra bra_visible_through_clothes bulge civitai color crossdressing crossdressing_male femboy feminine_male girly high_heels jimojo long_sleeves looking_at_viewer male male_cleavage miniskirt office_lady pectoral_cleavage pencil_skirt pony_diffusion_xl secretary short_skirt skirt standing thighs translucent_clothing
1boy ai_generated blonde_hair blue_eyes bulge civitai color crossdressing crossdressing_male femboy feminine_male from_below girly high_heels jimojo male male_chest miniskirt office_lady overhead_view pectoral_cleavage pencil_skirt pony_diffusion_xl rolled_up_sleeves secretary short_hair short_skirt simple_background skirt sleeves_rolled_up standing thighs top_view
1boy ai_generated blonde_hair blue_eyes bulge civitai color crossdressing crossdressing_male femboy feminine_male from_below girly high_heels jimojo male male_chest miniskirt office_lady overhead_view pectoral_cleavage pencil_skirt pony_diffusion_xl rolled_up_sleeves secretary short_hair short_skirt simple_background skirt sleeves_rolled_up standing thighs top_view
1boy 1girls age_difference ai_generated antenna_hair areola areolae arms_behind_back asymmetrical_docking bare_shoulders big_breasts black_gloves black_hair black_legwear black_thighhighs bondage breasts bulge capcom clothing collar collar_and_leash cowboy_shot crossdressing crossdressing_male crossover curvy_female elbow_gloves eteeming facing_viewer female femboy femsub hair_intakes large_breasts leash legs_together looking_at_viewer maledom microskirt milf miniskirt navel nipples older_woman_and_younger_boy open_mouth open_shirt open_smile osana_najimi panties partially_clothed pleated_skirt pubic_hair purple_eyes purple_hair pussy rebecca_chambers resident_evil short_hair simple_background size_difference skirt small_dom_big_sub smaller_male smile sparse_pubic_hair standing straight thick_thighs thighhighs uncensored voluptuous wide_hips
1boy 1girls age_difference ai_generated antenna_hair areola areolae arms_behind_back asymmetrical_docking bare_shoulders big_breasts black_gloves black_hair black_legwear black_thighhighs bondage breasts bulge capcom clothing collar collar_and_leash cowboy_shot crossdressing crossdressing_male crossover curvy_female elbow_gloves eteeming facing_viewer female femboy femsub hair_intakes large_breasts leash legs_together looking_at_viewer maledom microskirt milf miniskirt navel nipples older_woman_and_younger_boy open_mouth open_shirt open_smile osana_najimi panties partially_clothed pleated_skirt pubic_hair purple_eyes purple_hair pussy rebecca_chambers resident_evil short_hair simple_background size_difference skirt small_dom_big_sub smaller_male smile sparse_pubic_hair standing straight thick_thighs thighhighs uncensored voluptuous wide_hips
1boy ai_generated blonde_hair blue_eyes book_stack books bra_peek bulge civitai color crossdressing crossdressing_male desk femboy feminine_male girly high_heels jimojo male male_chest male_cleavage office_lady pectoral_cleavage pencil_skirt pink_bra pony_diffusion_xl red_bra secretary short_hair short_skirt skirt sleeves_rolled_up thighs
1boy ai_generated blonde_hair blue_eyes book_stack books bra_peek bulge civitai color crossdressing crossdressing_male desk femboy feminine_male girly high_heels jimojo male male_chest male_cleavage office_lady pectoral_cleavage pencil_skirt pink_bra pony_diffusion_xl red_bra secretary short_hair short_skirt skirt sleeves_rolled_up thighs
1boy 1girls age_difference ai_generated antenna_hair areola areolae arms_behind_back asymmetrical_docking bare_shoulders big_breasts bikini black_gloves black_hair black_legwear black_thighhighs bondage breasts bulge capcom clothing collar collar_and_leash cowboy_shot crossdressing crossdressing_male crossover curvy_female elbow_gloves eteeming facing_viewer female femboy femsub hair_intakes large_breasts leash legs_together looking_at_viewer maledom microskirt milf miniskirt navel nipples older_woman_and_younger_boy open_mouth open_shirt open_smile osana_najimi panties partially_clothed pleated_skirt pubic_hair purple_eyes purple_hair pussy rebecca_chambers resident_evil short_hair simple_background size_difference skirt small_dom_big_sub smaller_male smile sparse_pubic_hair standing straight thick_thighs thighhighs uncensored voluptuous wide_hips
1boy 1girls age_difference ai_generated antenna_hair areola areolae arms_behind_back asymmetrical_docking bare_shoulders big_breasts bikini black_gloves black_hair black_legwear black_thighhighs bondage breasts bulge capcom clothing collar collar_and_leash cowboy_shot crossdressing crossdressing_male crossover curvy_female elbow_gloves eteeming facing_viewer female femboy femsub hair_intakes large_breasts leash legs_together looking_at_viewer maledom microskirt milf miniskirt navel nipples older_woman_and_younger_boy open_mouth open_shirt open_smile osana_najimi panties partially_clothed pleated_skirt pubic_hair purple_eyes purple_hair pussy rebecca_chambers resident_evil short_hair simple_background size_difference skirt small_dom_big_sub smaller_male smile sparse_pubic_hair standing straight thick_thighs thighhighs uncensored voluptuous wide_hips
1boy 1femboy 2boys afroking ai_generated anime_style athletic athletic_male black_body blue_eyes caption choker comic comic_page crossdressing crossdressing_male cute cute_male dark-skinned_male dark_skin english_text exposed_breasts exposed_nipples exposed_torso facial_hair femboy feminine_male feminization fit fit_male flat_chest flat_chested gay interracial lipstick makeup male male/male male_only miniskirt muscles muscular muscular_male pantyhose red_lipstick short_hair short_skirt sissy sitting sitting_down text topless topless_male twink white_hair white_pantyhose yaoi
1boy 1femboy 2boys afroking ai_generated anime_style athletic athletic_male black_body blue_eyes caption choker comic comic_page crossdressing crossdressing_male cute cute_male dark-skinned_male dark_skin english_text exposed_breasts exposed_nipples exposed_torso facial_hair femboy feminine_male feminization fit fit_male flat_chest flat_chested gay interracial lipstick makeup male male/male male_only miniskirt muscles muscular muscular_male pantyhose red_lipstick short_hair short_skirt sissy sitting sitting_down text topless topless_male twink white_hair white_pantyhose yaoi
1boy1girl agents_of_dawn angry arm_wings bird_legs bird_wing black_hair chair chastity chastity_cage crossdressing crossdressing_male cuntboysub doctor_delphyne femboy flip_flops glasses green_hair harpy harpy_boy humiliation kyunamaori legs lifting_skirt monster_boy painted_nails sharp_teeth sitting skirt trans_male
1boy1girl agents_of_dawn angry arm_wings bird_legs bird_wing black_hair chair chastity chastity_cage crossdressing crossdressing_male cuntboysub doctor_delphyne femboy flip_flops glasses green_hair harpy harpy_boy humiliation kyunamaori legs lifting_skirt monster_boy painted_nails sharp_teeth sitting skirt trans_male
1boy ai_generated blonde_hair bra bulge civitai color crossdressing crossdressing_male femboy feminine_male girly high_heels jimojo long_sleeves looking_at_viewer looking_up_at_viewer male male_cleavage miniskirt office_lady pectoral_cleavage pencil_skirt pony_diffusion_xl red_bra secretary short_skirt simple_background skirt skirt_bulge standing thighs
1boy ai_generated blonde_hair bra bulge civitai color crossdressing crossdressing_male femboy feminine_male girly high_heels jimojo long_sleeves looking_at_viewer looking_up_at_viewer male male_cleavage miniskirt office_lady pectoral_cleavage pencil_skirt pony_diffusion_xl red_bra secretary short_skirt simple_background skirt skirt_bulge standing thighs