manly_crossdresser best from all time

Time frame

Tags

manly crossdresser

2boys aladdin aladdin_(character) anal anal_penetration anal_sex arab_male arabian arched_back arm_around_neck ass back back_muscles back_view balls bara big_ass big_butt black_hair boy_rape bubble_ass bubble_butt closed_mouth color cowgirl_position crossdressing dat_ass digital_media_(artwork) disney disney_prince disney_villains duo erection evil_grin eye_contact eyes facial_hair forced forced_yaoi gay glowing_eyes goatee grin hair hand_on_ass human human_only hypnosis hypnotized jafar light-skinned_male light_skin loincloth loincloth_only looking_at_another male male/male male_only male_penetrated male_penetrating male_rape_victim manly_crossdresser mind_control mostly_nude multiple_boys muscle muscles muscular muscular_back muscular_male pecs pectorals penetration penis pink_loincloth rape red_eyes see-through see-through_clothing sex sitting_on_penis smile staff testicles thick_ass thick_thighs turban uncensored uni0421 url vein veins veiny veiny_muscles yetigo
2boys aladdin aladdin_(character) anal anal_penetration anal_sex arab_male arabian arched_back arm_around_neck ass back back_muscles back_view balls bara big_ass big_butt black_hair boy_rape bubble_ass bubble_butt closed_mouth color cowgirl_position crossdressing dat_ass digital_media_(artwork) disney disney_prince disney_villains duo erection evil_grin eye_contact eyes facial_hair forced forced_yaoi gay glowing_eyes goatee grin hair hand_on_ass human human_only hypnosis hypnotized jafar light-skinned_male light_skin loincloth loincloth_only looking_at_another male male/male male_only male_penetrated male_penetrating male_rape_victim manly_crossdresser mind_control mostly_nude multiple_boys muscle muscles muscular muscular_back muscular_male pecs pectorals penetration penis pink_loincloth rape red_eyes see-through see-through_clothing sex sitting_on_penis smile staff testicles thick_ass thick_thighs turban uncensored uni0421 url vein veins veiny veiny_muscles yetigo
2boys balls bondage corset crossdressing cum cum_on_body cum_on_face cummitus gaping_anus gay holding_legs league_of_legends legs_apart legs_up maid maid_apron maid_headdress maid_outfit maid_uniform male male_only malesub manly_crossdresser muscular muscular_arms muscular_male on_back pecs post_orgasm sett thick_arms thighhighs yaoi
2boys balls bondage corset crossdressing cum cum_on_body cum_on_face cummitus gaping_anus gay holding_legs league_of_legends legs_apart legs_up maid maid_apron maid_headdress maid_outfit maid_uniform male male_only malesub manly_crossdresser muscular muscular_arms muscular_male on_back pecs post_orgasm sett thick_arms thighhighs yaoi
ambush_(trap) androgynous ass belly belly_button big_pecs big_penis big_thighs cat_ears cat_tail catboy collar crossdressing cute cute_male feet femboy gasaiv gloves grin hands_on_shoulders kodogasai light-skinned_male light_skin male male_focus male_only manly_crossdresser muscle muscles muscular muscular_male nipples opera_gloves pecs pink_eyes short_hair smile socks solo squatting stockings thick_thighs thighhighs thighs thong trap white_hair yaoi
ambush_(trap) androgynous ass belly belly_button big_pecs big_penis big_thighs cat_ears cat_tail catboy collar crossdressing cute cute_male feet femboy gasaiv gloves grin hands_on_shoulders kodogasai light-skinned_male light_skin male male_focus male_only manly_crossdresser muscle muscles muscular muscular_male nipples opera_gloves pecs pink_eyes short_hair smile socks solo squatting stockings thick_thighs thighhighs thighs thong trap white_hair yaoi
1boy 2022 abs action_pose ass ass_focus bara bare_pectorals bare_shoulders beard black_hair blush boots briefs brown_eyes brown_skin bulge bulge_through_clothing bush carlos_oliveira chest_hair chest_harness clothes_lift crossdressing dark-skinned_male dark_skin dialogue digital_media_(artwork) erection facial_hair gay green_male_underwear gun hairy hairy_armpits hairy_arms hairy_chest hairy_legs hairy_male hairy_thighs harness headgear headphones headpiece highres large_pectorals licker licker_(resident_evil) male male_focus male_only male_pubic_hair male_underwear manly_crossdresser mature_male multiple_poses multiple_positions muscles muscular muscular_arms muscular_legs muscular_male muscular_thighs navel navel_hair nipples panties pectorals penis pink_background pink_panties pubes pubic_hair resident_evil resident_evil_3 shirt_lift short_hair short_shorts shorts skimpy skimpy_clothes skimpy_outfit smutssmith socks solo solo_focus solo_male spread_legs stomach straps stubble taint tan_skin tentacle tentacle_on_male testicle_peek thick_thighs thighs uncensored underwear unzipped unzipped_pants vest yaoi
1boy 2022 abs action_pose ass ass_focus bara bare_pectorals bare_shoulders beard black_hair blush boots briefs brown_eyes brown_skin bulge bulge_through_clothing bush carlos_oliveira chest_hair chest_harness clothes_lift crossdressing dark-skinned_male dark_skin dialogue digital_media_(artwork) erection facial_hair gay green_male_underwear gun hairy hairy_armpits hairy_arms hairy_chest hairy_legs hairy_male hairy_thighs harness headgear headphones headpiece highres large_pectorals licker licker_(resident_evil) male male_focus male_only male_pubic_hair male_underwear manly_crossdresser mature_male multiple_poses multiple_positions muscles muscular muscular_arms muscular_legs muscular_male muscular_thighs navel navel_hair nipples panties pectorals penis pink_background pink_panties pubes pubic_hair resident_evil resident_evil_3 shirt_lift short_hair short_shorts shorts skimpy skimpy_clothes skimpy_outfit smutssmith socks solo solo_focus solo_male spread_legs stomach straps stubble taint tan_skin tentacle tentacle_on_male testicle_peek thick_thighs thighs uncensored underwear unzipped unzipped_pants vest yaoi
alex_(stardew_valley) ass asshole balls big_penis brunet bunny_boy bunny_costume bunny_ears bunnysuit carrot cartoon cock condom condom_on_penis condoms crossdressing dick foreskin fucked_silly garter_straps gay group group_picture group_sex human kiddeathx_(artist) leaking leaking_cum lingerie male male/male male_only males manly_crossdresser onlyfans orgy slut stardew_valley thong yaoi
alex_(stardew_valley) ass asshole balls big_penis brunet bunny_boy bunny_costume bunny_ears bunnysuit carrot cartoon cock condom condom_on_penis condoms crossdressing dick foreskin fucked_silly garter_straps gay group group_picture group_sex human kiddeathx_(artist) leaking leaking_cum lingerie male male/male male_only males manly_crossdresser onlyfans orgy slut stardew_valley thong yaoi
1boy ambush_(trap) blush collar crossdressing femboy gay golden_bikini guilty_gear humiliation krekk0v ky_kiske male_only manly_crossdresser nipples royalty submissive submissive_male sweat text
1boy ambush_(trap) blush collar crossdressing femboy gay golden_bikini guilty_gear humiliation krekk0v ky_kiske male_only manly_crossdresser nipples royalty submissive submissive_male sweat text
1boy balls bikini black_clothing black_legwear black_thighhighs blackheart_xi brown_eyes brown_skin buttplug collar color colored crossdressing dark-skinned_femboy dark-skinned_male dark_skin docfriend facemask fat_ass freckles freckles_on_ass leggings manly_crossdresser mask masked muscular muscular_femboy muscular_male presenting presenting_ass sitting solo testicles text thighhighs
1boy balls bikini black_clothing black_legwear black_thighhighs blackheart_xi brown_eyes brown_skin buttplug collar color colored crossdressing dark-skinned_femboy dark-skinned_male dark_skin docfriend facemask fat_ass freckles freckles_on_ass leggings manly_crossdresser mask masked muscular muscular_femboy muscular_male presenting presenting_ass sitting solo testicles text thighhighs
2023 2boys abs anal anal_sex ass_focus ass_up bara blush blush_lines bow bra bra_down bush call_of_duty choker choking crossdressing cum cum_in_ass cum_in_pussy cum_inside cumshot dialogue digital_media_(artwork) eyeroll eyes_rolling_back facial_hair gay gay_sex ghost_(modern ghost_(modern_warfare_2) gloves grabbing grabbing_hips grabbing_neck half-dressed hand_on_hip hand_on_neck happy_trail john_mactavish lace laying_down leaking leaking_cum lingerie lingerie_only looking_at_another looking_at_partner majormelon1 male male/male male_lingerie male_only male_pubic_hair manly_crossdresser mask military moaning mohawk multiple_boys muscle muscles muscular muscular_male open_mouth panties partially_clothed pecs pubic_hair rolling_eyes scar scars scars_all_over simon_riley smile soap_(modern_warfare_2) stubble sweat sweatdrop sweating tattoo tattoos warfare wet_panties yaoi_eye
2023 2boys abs anal anal_sex ass_focus ass_up bara blush blush_lines bow bra bra_down bush call_of_duty choker choking crossdressing cum cum_in_ass cum_in_pussy cum_inside cumshot dialogue digital_media_(artwork) eyeroll eyes_rolling_back facial_hair gay gay_sex ghost_(modern ghost_(modern_warfare_2) gloves grabbing grabbing_hips grabbing_neck half-dressed hand_on_hip hand_on_neck happy_trail john_mactavish lace laying_down leaking leaking_cum lingerie lingerie_only looking_at_another looking_at_partner majormelon1 male male/male male_lingerie male_only male_pubic_hair manly_crossdresser mask military moaning mohawk multiple_boys muscle muscles muscular muscular_male open_mouth panties partially_clothed pecs pubic_hair rolling_eyes scar scars scars_all_over simon_riley smile soap_(modern_warfare_2) stubble sweat sweatdrop sweating tattoo tattoos warfare wet_panties yaoi_eye
1boy abs ambush_(trap) beard bell bell_collar big_pecs bikini blush blushing bra collar cow_costume cow_ears cow_horns cowbell crossdressing cum facial_hair femboy gay gold_eyes human human_only kokochari leon_(pokemon) lingerie looking_at_viewer maemoooo male male_only manly_crossdresser milk milking miltank muscles muscular muscular_male muscular_trap panties pecs pokemon pokemon_ss purple_hair simple_background solo solo_male trap yaoi yellow_eyes
1boy abs ambush_(trap) beard bell bell_collar big_pecs bikini blush blushing bra collar cow_costume cow_ears cow_horns cowbell crossdressing cum facial_hair femboy gay gold_eyes human human_only kokochari leon_(pokemon) lingerie looking_at_viewer maemoooo male male_only manly_crossdresser milk milking miltank muscles muscular muscular_male muscular_trap panties pecs pokemon pokemon_ss purple_hair simple_background solo solo_male trap yaoi yellow_eyes
2boys anal anal_fingering blonde_hair blue_eyes bottomless cloud_strife color crossdressing eilinna femboy final_fantasy final_fantasy_vii fingering girly green_eyes hair_ornament half-erect japanese_clothes kimono light-skinned_femboy light-skinned_male light_skin long_hair long_sleeves loose_clothes male male/male male_only manly_crossdresser muscular muscular_male partially_clothed sephiroth smirk spiky_hair spread_legs square_enix tagme trap twink white_hair worried yaoi
2boys anal anal_fingering blonde_hair blue_eyes bottomless cloud_strife color crossdressing eilinna femboy final_fantasy final_fantasy_vii fingering girly green_eyes hair_ornament half-erect japanese_clothes kimono light-skinned_femboy light-skinned_male light_skin long_hair long_sleeves loose_clothes male male/male male_only manly_crossdresser muscular muscular_male partially_clothed sephiroth smirk spiky_hair spread_legs square_enix tagme trap twink white_hair worried yaoi
1boy armpit armpit_fetish armpit_hair armpit_peek armpits blonde_hair blonde_male bludwing blue_eyes blush blushing_at_viewer cloud_strife crossdressing embarrassed embarrassed_nude_exposure embarrassed_nude_male final_fantasy final_fantasy_vii flushed flustered gay hairy hairy_armpits hairy_legs hairy_male happy_trail male_focus male_only male_pubic_hair manly_crossdresser penis_peek pubic_hair sweat sweatdrop sweating sweaty sweaty_armpits sweaty_balls sweaty_body sweaty_genitalia yaoi
1boy armpit armpit_fetish armpit_hair armpit_peek armpits blonde_hair blonde_male bludwing blue_eyes blush blushing_at_viewer cloud_strife crossdressing embarrassed embarrassed_nude_exposure embarrassed_nude_male final_fantasy final_fantasy_vii flushed flustered gay hairy hairy_armpits hairy_legs hairy_male happy_trail male_focus male_only male_pubic_hair manly_crossdresser penis_peek pubic_hair sweat sweatdrop sweating sweaty sweaty_armpits sweaty_balls sweaty_body sweaty_genitalia yaoi
<3 1boy abs anal anal_insertion anal_object_insertion anal_tail ass balls balls_in_panties belka_dog big_ass big_penis black_hair blue_eyes blushing boner butt buttplug capcom cat_ears cat_tail catboy choker circumcised color crossdressing cuccoking cute devil_may_cry devil_may_cry_5 emo english english_text erect_nipples erect_penis erection fake_animal_ears fake_tail gay genitals hair heart horny human human_only long_socks male male_only male_penetrated malesub manly_crossdresser medium_hair muscular muscular_male nipples panties pecs penis penis_out plug_tail rings seductive sex_toy sex_toy_in_ass signature solo solo_focus solo_male submissive submissive_male sweat tail tail_plug tattoo text tits v_(devil_may_cry) veiny_penis video_game_character video_games yaoi
<3 1boy abs anal anal_insertion anal_object_insertion anal_tail ass balls balls_in_panties belka_dog big_ass big_penis black_hair blue_eyes blushing boner butt buttplug capcom cat_ears cat_tail catboy choker circumcised color crossdressing cuccoking cute devil_may_cry devil_may_cry_5 emo english english_text erect_nipples erect_penis erection fake_animal_ears fake_tail gay genitals hair heart horny human human_only long_socks male male_only male_penetrated malesub manly_crossdresser medium_hair muscular muscular_male nipples panties pecs penis penis_out plug_tail rings seductive sex_toy sex_toy_in_ass signature solo solo_focus solo_male submissive submissive_male sweat tail tail_plug tattoo text tits v_(devil_may_cry) veiny_penis video_game_character video_games yaoi
2023 2boys abs after_fellatio after_oral ambush_(trap) androgynous arms_behind_back artist_name ass balls ballsack big_pecs bishonen blush blushing chain_leash cloud_strife collar color commission crossdressing cum cum_drip cum_in_mouth cum_on_body cum_on_face cumshot dark_background dildo dildo_in_ass dildo_sitting dominant_male ear_piercing earrings erect_nipples erect_penis erection femboy feminine_male final_fantasy final_fantasy_vii functionally_nude gay green_eyes hand_on_another's_chin hand_on_chin heart-shaped_pupils high_ponytail holding_leash implied_fellatio implied_oral leash light-skinned_male light_skin lingerie long_hair looking_at_another looking_at_partner looking_pleasured looking_up maid_headdress maid_uniform male male/male male_focus male_only maledom malesub man_boobs manly_crossdresser moobs muscular muscular_male muscular_thighs naked nipple_bulge nipple_piercing nipples nude parted_bangs partially_clothed penis pink_dildo ponytail rope rope_bondage sephiroth silver_hair sitting_on_dildo square_enix squatting squatting_cowgirl_position submissive submissive_male tagme thick_thighs thighhighs tied_arms tied_hair tied_up tongue tongue_out unnocturnal very_long_hair vibrator vibrator_on_penis x-ray yaoi
2023 2boys abs after_fellatio after_oral ambush_(trap) androgynous arms_behind_back artist_name ass balls ballsack big_pecs bishonen blush blushing chain_leash cloud_strife collar color commission crossdressing cum cum_drip cum_in_mouth cum_on_body cum_on_face cumshot dark_background dildo dildo_in_ass dildo_sitting dominant_male ear_piercing earrings erect_nipples erect_penis erection femboy feminine_male final_fantasy final_fantasy_vii functionally_nude gay green_eyes hand_on_another's_chin hand_on_chin heart-shaped_pupils high_ponytail holding_leash implied_fellatio implied_oral leash light-skinned_male light_skin lingerie long_hair looking_at_another looking_at_partner looking_pleasured looking_up maid_headdress maid_uniform male male/male male_focus male_only maledom malesub man_boobs manly_crossdresser moobs muscular muscular_male muscular_thighs naked nipple_bulge nipple_piercing nipples nude parted_bangs partially_clothed penis pink_dildo ponytail rope rope_bondage sephiroth silver_hair sitting_on_dildo square_enix squatting squatting_cowgirl_position submissive submissive_male tagme thick_thighs thighhighs tied_arms tied_hair tied_up tongue tongue_out unnocturnal very_long_hair vibrator vibrator_on_penis x-ray yaoi
2boys barefoot blonde_hair blush character_request cropped_torso crossdressing cum cum_in_mouth cum_on_tongue darkmode_proxy doppelganger dual_persona english_text fellatio gay gay_sex gloves highres homelander long_sleeves male_focus manly_crossdresser multiple_boys muscular muscular_male nipples oral red_gloves selfcest shiny_skin short_hair sitting speech_bubble teeth the_boys tongue tongue_out trembling white_background yaoi
2boys barefoot blonde_hair blush character_request cropped_torso crossdressing cum cum_in_mouth cum_on_tongue darkmode_proxy doppelganger dual_persona english_text fellatio gay gay_sex gloves highres homelander long_sleeves male_focus manly_crossdresser multiple_boys muscular muscular_male nipples oral red_gloves selfcest shiny_skin short_hair sitting speech_bubble teeth the_boys tongue tongue_out trembling white_background yaoi
2boys age_difference alex_(stardew_valley) all_fours ass_grab bara barely_clothed barely_covered big_penis blonde_hair blonde_male brown_hair bubble_ass bubble_butt cheerleader cheerleader_costume cheerleader_outfit cheerleader_uniform crossdressing dad_and_friend_of_son dad_and_sons_friend daddy daydreamerjim dilf doggy_style doggy_style_position domination erect_penis father_and_son's_friend football_player football_uniform fraternity friends_dad gay gay_domination gay_sex grabbing_another's_ass grabbing_ass grabbing_from_behind human human_male human_only implied_anal jock jockstrap kent_(stardew_valley) lad looking_pleasured looking_satisfied male male/male male_only manly_crossdresser masculine_bottom mature_male muscular muscular_arms muscular_ass muscular_bottom muscular_legs muscular_male muscular_thighs older_male older_man_and_teenage_boy older_man_and_younger_boy older_penetrated older_sub on_all_fours partially_clothed partially_nude partially_undressed penis pleasure_face pleasured_face pounding_ass provocative red_skirt roleplay rugby_uniform satisfied_look satisfied_smile sex six_pack size_difference skimpy_clothes skimpy_costume slutty_clothing slutty_daddy slutty_outfit small_dom_big_sub small_top_big_bottom smaller_penetrating_bigger smile smiling smiling_at_partner spreading stardew_valley thick_ass thick_butt thick_thighs thrusting thrusting_into_ass tight_clothes tight_clothing tight_pants tight_shirt white_background white_socks yaoi young_top_older_bottom younger_dom_older_sub younger_dominant younger_male younger_penetrating younger_penetrating_older
2boys age_difference alex_(stardew_valley) all_fours ass_grab bara barely_clothed barely_covered big_penis blonde_hair blonde_male brown_hair bubble_ass bubble_butt cheerleader cheerleader_costume cheerleader_outfit cheerleader_uniform crossdressing dad_and_friend_of_son dad_and_sons_friend daddy daydreamerjim dilf doggy_style doggy_style_position domination erect_penis father_and_son's_friend football_player football_uniform fraternity friends_dad gay gay_domination gay_sex grabbing_another's_ass grabbing_ass grabbing_from_behind human human_male human_only implied_anal jock jockstrap kent_(stardew_valley) lad looking_pleasured looking_satisfied male male/male male_only manly_crossdresser masculine_bottom mature_male muscular muscular_arms muscular_ass muscular_bottom muscular_legs muscular_male muscular_thighs older_male older_man_and_teenage_boy older_man_and_younger_boy older_penetrated older_sub on_all_fours partially_clothed partially_nude partially_undressed penis pleasure_face pleasured_face pounding_ass provocative red_skirt roleplay rugby_uniform satisfied_look satisfied_smile sex six_pack size_difference skimpy_clothes skimpy_costume slutty_clothing slutty_daddy slutty_outfit small_dom_big_sub small_top_big_bottom smaller_penetrating_bigger smile smiling smiling_at_partner spreading stardew_valley thick_ass thick_butt thick_thighs thrusting thrusting_into_ass tight_clothes tight_clothing tight_pants tight_shirt white_background white_socks yaoi young_top_older_bottom younger_dom_older_sub younger_dominant younger_male younger_penetrating younger_penetrating_older
2boys age_difference balls balls_deep black_and_white blonde_hair crossdressing cum_in_ass cum_inside dirty_talk domination english english_text fucked_senseless fucked_silly full_nelson gay head_grab heart-shaped_pupils heroes_of_olympus jason_grace lingerie male_only manly_crossdresser mind_break panties percy_jackson_and_the_olympians slutboy soynutts spread_legs stockings verbal verbal_abuse verbal_consent verbal_degradation verbal_degredation verbal_domination verbal_submission yaoi
2boys age_difference balls balls_deep black_and_white blonde_hair crossdressing cum_in_ass cum_inside dirty_talk domination english english_text fucked_senseless fucked_silly full_nelson gay head_grab heart-shaped_pupils heroes_of_olympus jason_grace lingerie male_only manly_crossdresser mind_break panties percy_jackson_and_the_olympians slutboy soynutts spread_legs stockings verbal verbal_abuse verbal_consent verbal_degradation verbal_degredation verbal_domination verbal_submission yaoi
2boys abs ahe_gao ahegao anal anal_penetration anal_sex artist_name ass athletic athletic_male bara blur_censor blurry_background bottomless captain_hook censored collar color corset crossdressing crossover digital_media_(artwork) disney disney_prince duo english_text erect_nipples erection exposed_nipples flower from_above fucked_silly garikaliev garter gay hairy hairy_armpits hairy_balls hairy_chest hairy_male hook human human_only leaning_on_object leash_and_collar leash_pull legs_up male/male male_only male_penetrating male_pubic_hair manly_crossdresser moustache muscular muscular_male open_shirt pants_removed pecs penis penis_size_difference peter_pan_(disney) pirate pirate_captain pirate_crew pirate_hat pirate_ship pointless_censoring precum prince_eric public restrained sex speech_bubble spread_legs spreading stockings tagme the_little_mermaid tied tied_hands white_stockings yaoi
2boys abs ahe_gao ahegao anal anal_penetration anal_sex artist_name ass athletic athletic_male bara blur_censor blurry_background bottomless captain_hook censored collar color corset crossdressing crossover digital_media_(artwork) disney disney_prince duo english_text erect_nipples erection exposed_nipples flower from_above fucked_silly garikaliev garter gay hairy hairy_armpits hairy_balls hairy_chest hairy_male hook human human_only leaning_on_object leash_and_collar leash_pull legs_up male/male male_only male_penetrating male_pubic_hair manly_crossdresser moustache muscular muscular_male open_shirt pants_removed pecs penis penis_size_difference peter_pan_(disney) pirate pirate_captain pirate_crew pirate_hat pirate_ship pointless_censoring precum prince_eric public restrained sex speech_bubble spread_legs spreading stockings tagme the_little_mermaid tied tied_hands white_stockings yaoi
1boy 2d 2d_(artwork) abs ambush_(trap) balls big_penis blonde_hair bloody_roar blue_eyes crossdressing femboy fingerless_gloves fox_(bloody_roar) hans_taubemann huge_balls huge_cock large_penis light-skinned_male long_penis male male_only manly_crossdresser muscles muscular muscular_femboy pectorals pink_fingerless_gloves precum rampage0118 solo tagme testicles tied_hair vein veiny_penis video_games
1boy 2d 2d_(artwork) abs ambush_(trap) balls big_penis blonde_hair bloody_roar blue_eyes crossdressing femboy fingerless_gloves fox_(bloody_roar) hans_taubemann huge_balls huge_cock large_penis light-skinned_male long_penis male male_only manly_crossdresser muscles muscular muscular_femboy pectorals pink_fingerless_gloves precum rampage0118 solo tagme testicles tied_hair vein veiny_penis video_games