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male virginity loss

1boy 1girls :d assertive_female blonde_hair blush breasts censored completely_nude cowgirl_position crystal cucked_by_sister excited female flandre_scarlet full_body fusu_(a95101221) hair_between_eyes half-closed_eyes hands_on_another's_chest happy_female hat hat_ribbon indoors japanese_text leaning_forward male_virginity_loss medium_hair motion_lines navel nipples nude on_bed penis pussy red_eyes ribbon sex side_ponytail small_breasts smile solo_focus spread_legs squatting squatting_cowgirl_position straddling straight touhou translated translation_request vaginal_penetration wings
1boy 1girls :d assertive_female blonde_hair blush breasts censored completely_nude cowgirl_position crystal cucked_by_sister excited female flandre_scarlet full_body fusu_(a95101221) hair_between_eyes half-closed_eyes hands_on_another's_chest happy_female hat hat_ribbon indoors japanese_text leaning_forward male_virginity_loss medium_hair motion_lines navel nipples nude on_bed penis pussy red_eyes ribbon sex side_ponytail small_breasts smile solo_focus spread_legs squatting squatting_cowgirl_position straddling straight touhou translated translation_request vaginal_penetration wings
1boy 1girls 2010s 2011 adorable adorable_face affection affectionate after_fellatio after_oral after_orgasm after_sex after_shower after_vaginal age_difference animated anus assertive_female ballsack bed bed_sheet bedroom belt big_breasts blonde_hair blowjob blue_eyes blue_jeans blue_veins blush blush_line blush_lines blushing boobies bouncing bouncing_breasts breasts butt caught_masturbating cicada_(animal) cleaning_cum cleavage clitoral_stimulation clitoris closed_eyes cowgirl_position cross cross_earrings cum cum_in_pussy cum_inside cum_leaking_out_of_pussy cumdrip cumshot cunnilingus dark_penis dialogue dialogue_box dialogue_options dreaming drool drool_string drooling ear earrings ears eating_cum eating_pussy ejaculation erect_nipples erection eyebrows eyebrows_visible_through_hair eyelashes eyeliner facial fantasizing fapping fat_mons feet fellatio female fingering fingering_partner foot french_kiss french_kissing game_cg green_veins hairy_testicles handjob hands_on_another's_chest hands_on_chest hanging_breasts happy_sex hd hentai huge_breasts huge_cleavage in_love internal internal_cumshot japanese_voice_acting jeans jellyfish_(company) jerking_off jerkingoff_another jiggle jiggling jiggling_breasts kamimura_akiko kissing kouzaka_kouhei large_breasts leaking_cum legs_up lips long_hair long_video longer_than_15_minutes looking_at_viewer male male_virgin male_virginity_loss masturbation mature_female missionary missionary_position missionary_sex moan moaning moaning_in_pleasure moans natsu_no_saigo_no_hi natural_breasts naughty_face naughty_smile nervous nipples nipples_showing nipples_visible_through_clothing nude nutsack older_woman_and_younger_boy older_woman_and_younger_man on_back on_the_phone open_mouth open_mouth_kiss oral orange_sweater overflow panties panties_showing penis penis_head penis_tip penis_vein penis_veins perky perky_nipples pillow pillows pink_nipples pink_penis_tip plate ponytail pov pov_male precum precum_drip precum_string premature_cumshot premature_ejaculation premature_orgasm projectile_cum puffy_nipples pulsating pulsating_cock pulsating_cumshot pulsation pulsing pulsing_balls pulsing_testicles pussy quivering religious_symbol religious_symbols revealing_clothes riding riding_penis saliva saliva_drip saliva_string saliva_trail screencap seasonal semen semen_splatter semen_squirt sex sex_sounds shiny shiny_skin shuddering shy shy_male sideboob sisters_~natsu_no_saigo_no_hi~ smile smiling_at_another smiling_at_partner smiling_at_penis sound sperm spread_legs squatting squatting_cowgirl_position step-incest stepmom stepmother stepmother_and_stepchild stepmother_and_stepson stepson stepson_(lore) straddle straight subtitled subtitles sucking_off sucking_penis summer swallowing swallowing_cum swaying swaying_breasts sweat sweat_on_face sweat_on_forehead sweater sweater_lift sweaty_balls sweaty_body sweaty_breasts sweaty_butt sweaty_genitalia sweaty_sex sweaty_testicles sweaty_thighs taki_minashika tank_top teacup teapot tease teasing testicle testicles testicles_clench testicles_deep text throbbing throbbing_balls throbbing_penis throbbing_testicles toes tongue tongue_kiss tongue_out towel towel_only trembling twitch_lines twitching twitching_penis uncensored underwear vagina vaginal_penetration vanilla vein veins veins_on_dick veiny_penis veiny_testicles very_veiny_penis video video_game virgin virgin_male virginity virginity_loss virginity_lost visual_novel visual_novel_interface vpl walked_in_on wobbling_breasts x-ray yellow_background yellow_light zipper
1boy 1girls 2010s 2011 adorable adorable_face affection affectionate after_fellatio after_oral after_orgasm after_sex after_shower after_vaginal age_difference animated anus assertive_female ballsack bed bed_sheet bedroom belt big_breasts blonde_hair blowjob blue_eyes blue_jeans blue_veins blush blush_line blush_lines blushing boobies bouncing bouncing_breasts breasts butt caught_masturbating cicada_(animal) cleaning_cum cleavage clitoral_stimulation clitoris closed_eyes cowgirl_position cross cross_earrings cum cum_in_pussy cum_inside cum_leaking_out_of_pussy cumdrip cumshot cunnilingus dark_penis dialogue dialogue_box dialogue_options dreaming drool drool_string drooling ear earrings ears eating_cum eating_pussy ejaculation erect_nipples erection eyebrows eyebrows_visible_through_hair eyelashes eyeliner facial fantasizing fapping fat_mons feet fellatio female fingering fingering_partner foot french_kiss french_kissing game_cg green_veins hairy_testicles handjob hands_on_another's_chest hands_on_chest hanging_breasts happy_sex hd hentai huge_breasts huge_cleavage in_love internal internal_cumshot japanese_voice_acting jeans jellyfish_(company) jerking_off jerkingoff_another jiggle jiggling jiggling_breasts kamimura_akiko kissing kouzaka_kouhei large_breasts leaking_cum legs_up lips long_hair long_video longer_than_15_minutes looking_at_viewer male male_virgin male_virginity_loss masturbation mature_female missionary missionary_position missionary_sex moan moaning moaning_in_pleasure moans natsu_no_saigo_no_hi natural_breasts naughty_face naughty_smile nervous nipples nipples_showing nipples_visible_through_clothing nude nutsack older_woman_and_younger_boy older_woman_and_younger_man on_back on_the_phone open_mouth open_mouth_kiss oral orange_sweater overflow panties panties_showing penis penis_head penis_tip penis_vein penis_veins perky perky_nipples pillow pillows pink_nipples pink_penis_tip plate ponytail pov pov_male precum precum_drip precum_string premature_cumshot premature_ejaculation premature_orgasm projectile_cum puffy_nipples pulsating pulsating_cock pulsating_cumshot pulsation pulsing pulsing_balls pulsing_testicles pussy quivering religious_symbol religious_symbols revealing_clothes riding riding_penis saliva saliva_drip saliva_string saliva_trail screencap seasonal semen semen_splatter semen_squirt sex sex_sounds shiny shiny_skin shuddering shy shy_male sideboob sisters_~natsu_no_saigo_no_hi~ smile smiling_at_another smiling_at_partner smiling_at_penis sound sperm spread_legs squatting squatting_cowgirl_position step-incest stepmom stepmother stepmother_and_stepchild stepmother_and_stepson stepson stepson_(lore) straddle straight subtitled subtitles sucking_off sucking_penis summer swallowing swallowing_cum swaying swaying_breasts sweat sweat_on_face sweat_on_forehead sweater sweater_lift sweaty_balls sweaty_body sweaty_breasts sweaty_butt sweaty_genitalia sweaty_sex sweaty_testicles sweaty_thighs taki_minashika tank_top teacup teapot tease teasing testicle testicles testicles_clench testicles_deep text throbbing throbbing_balls throbbing_penis throbbing_testicles toes tongue tongue_kiss tongue_out towel towel_only trembling twitch_lines twitching twitching_penis uncensored underwear vagina vaginal_penetration vanilla vein veins veins_on_dick veiny_penis veiny_testicles very_veiny_penis video video_game virgin virgin_male virginity virginity_loss virginity_lost visual_novel visual_novel_interface vpl walked_in_on wobbling_breasts x-ray yellow_background yellow_light zipper
anthro athene_(genus) atheniv avian beak bed_sheet bedding beverage bird blush bodily_fluids book brown_body bubowl colored comic detailed_background duo eared_owl enjoying eurasian_eagle-owl feathered_wings feathers female festival flammeusia from_front_position furry_only glancing_back grabbing_sheets hair heart_(marking) hi_res horned_owl hug humping little_owl lying male male/female male_on_top male_virginity_loss markings messy_feathers messy_hair missionary_position on_back on_top orange_body orange_eyes owl party red_body romantic romantic_couple rozalid sex shaking short-eared_owl shy squeezing story story_in_description sweat true_owl white_body wings worried
anthro athene_(genus) atheniv avian beak bed_sheet bedding beverage bird blush bodily_fluids book brown_body bubowl colored comic detailed_background duo eared_owl enjoying eurasian_eagle-owl feathered_wings feathers female festival flammeusia from_front_position furry_only glancing_back grabbing_sheets hair heart_(marking) hi_res horned_owl hug humping little_owl lying male male/female male_on_top male_virginity_loss markings messy_feathers messy_hair missionary_position on_back on_top orange_body orange_eyes owl party red_body romantic romantic_couple rozalid sex shaking short-eared_owl shy squeezing story story_in_description sweat true_owl white_body wings worried
5_fingers 5_toes 
2023 
5_fingers 
beastars 
bird_dog 
jack_(beastars) abs anthro anthro_on_anthro anthro_penetrated anthro_penetrating anthro_penetrating_anthro anus areola ball_fondling balls barefoot beastars bed big_breasts biped bite black_nose blush bodily_fluids bottomless bottomless_anthro bottomless_female bottomless_male bottomwear breast_grab breast_play breasts brown_body brown_fur bulge butt butt_grab canid canine canis claws clothed clothing comic comic_strip crouching crouching_cowgirl cum cum_from_pussy cum_in_pussy cum_inside cum_on_clothing cum_on_leg cum_on_penis cum_on_shirt cum_on_topwear cutoffs denim denim_bottomwear denim_clothing detailed_bulge digit_ring discarded_bottomwear discarded_clothing discarded_shorts domestic_dog duo english_text erection erection_under_clothing exposed_breasts eyes_closed feet female female_penetrated finger_claws fingers first_person_view fondling footwear french_kissing fur furniture furry gaming genital_fluids genital_outline genitals gentle_femdom grey_body grey_fur grope group hand_on_breast hand_on_butt hi_res humanoid_feet humanoid_hands hunting_dog imminent_threesome inside jack_(beastars) jewelry juno_(beastars) kissing labrador legoshi_(beastars) looking_pleasured lying male male/female male_penetrating male_penetrating_female male_pov male_virginity_loss mammal meesh mostly_offscreen_character multicolored_body multicolored_fur muscular muscular_male narrowed_eyes neck_bite nintendo nintendo_switch nipples on_bed on_side one_eye_closed open_mouth partially_clothed penetrating_pov penetration penile penile_penetration penis penis_in_pussy penis_outline plantigrade playing_video_game pussy raised_clothing raised_shirt raised_topwear retriever ring sandals seductive seductive_smile sex shirt shorts sitting sitting_on_bed sleeping smile sound_effects spread_legs spreading sweat tan_body tan_fur teasing teeth text text_on_clothing text_on_shirt text_on_t-shirt text_on_topwear titfuck toe_claws toe_ring toes tongue tongue_out topwear trio two_tone_body two_tone_fur underwear url vagina vaginal vaginal_fluids vaginal_penetration vaginal_sex vowelless vowelless_sound_effect voyeur watching wolf yellow_body yellow_fur zzz
5_fingers 5_toes 
2023 
5_fingers 
beastars 
bird_dog 
jack_(beastars) abs anthro anthro_on_anthro anthro_penetrated anthro_penetrating anthro_penetrating_anthro anus areola ball_fondling balls barefoot beastars bed big_breasts biped bite black_nose blush bodily_fluids bottomless bottomless_anthro bottomless_female bottomless_male bottomwear breast_grab breast_play breasts brown_body brown_fur bulge butt butt_grab canid canine canis claws clothed clothing comic comic_strip crouching crouching_cowgirl cum cum_from_pussy cum_in_pussy cum_inside cum_on_clothing cum_on_leg cum_on_penis cum_on_shirt cum_on_topwear cutoffs denim denim_bottomwear denim_clothing detailed_bulge digit_ring discarded_bottomwear discarded_clothing discarded_shorts domestic_dog duo english_text erection erection_under_clothing exposed_breasts eyes_closed feet female female_penetrated finger_claws fingers first_person_view fondling footwear french_kissing fur furniture furry gaming genital_fluids genital_outline genitals gentle_femdom grey_body grey_fur grope group hand_on_breast hand_on_butt hi_res humanoid_feet humanoid_hands hunting_dog imminent_threesome inside jack_(beastars) jewelry juno_(beastars) kissing labrador legoshi_(beastars) looking_pleasured lying male male/female male_penetrating male_penetrating_female male_pov male_virginity_loss mammal meesh mostly_offscreen_character multicolored_body multicolored_fur muscular muscular_male narrowed_eyes neck_bite nintendo nintendo_switch nipples on_bed on_side one_eye_closed open_mouth partially_clothed penetrating_pov penetration penile penile_penetration penis penis_in_pussy penis_outline plantigrade playing_video_game pussy raised_clothing raised_shirt raised_topwear retriever ring sandals seductive seductive_smile sex shirt shorts sitting sitting_on_bed sleeping smile sound_effects spread_legs spreading sweat tan_body tan_fur teasing teeth text text_on_clothing text_on_shirt text_on_t-shirt text_on_topwear titfuck toe_claws toe_ring toes tongue tongue_out topwear trio two_tone_body two_tone_fur underwear url vagina vaginal vaginal_fluids vaginal_penetration vaginal_sex vowelless vowelless_sound_effect voyeur watching wolf yellow_body yellow_fur zzz
2024 absurd_res avian azulejo bodily_fluids dated detailed_background dialogue duo english_text fan_character female feral genital_fluids genitals gryphon hasbro hi_res male male/female male_virginity_loss my_little_pony mythological_avian mythological_creature mythology on_bottom on_top penetration penis precum presenting presenting_penis prostitution reverse_cowgirl_position sex signature text vaginal_fluids vaginal_penetration
2024 absurd_res avian azulejo bodily_fluids dated detailed_background dialogue duo english_text fan_character female feral genital_fluids genitals gryphon hasbro hi_res male male/female male_virginity_loss my_little_pony mythological_avian mythological_creature mythology on_bottom on_top penetration penis precum presenting presenting_penis prostitution reverse_cowgirl_position sex signature text vaginal_fluids vaginal_penetration
1boy 3d 3d_(artwork) age_difference ass black_hair blowjob female first_blowjob first_time first_time_sex garry's_mod housewife huge_breasts male male_virgin male_virginity_loss middle_aged milf milf_love_young_man mother naked naked_female naked_male nude older_female older_woman_and_younger_boy penis penis_in_mouth scout's_mother sniper sniper_(team_fortress_2) sucking sucking_penis team_fortress_2 tf2 valve video_games virgin virgin_boy virgin_male virginity_loss
1boy 3d 3d_(artwork) age_difference ass black_hair blowjob female first_blowjob first_time first_time_sex garry's_mod housewife huge_breasts male male_virgin male_virginity_loss middle_aged milf milf_love_young_man mother naked naked_female naked_male nude older_female older_woman_and_younger_boy penis penis_in_mouth scout's_mother sniper sniper_(team_fortress_2) sucking sucking_penis team_fortress_2 tf2 valve video_games virgin virgin_boy virgin_male virginity_loss
1boy 2girls 3d adorable against_glass against_surface busty busty_female cute female female_virgin femscout filming garry's_mod gmod housewife human human_female human_male human_only kuudere love lovers loving loving_couple male male_virgin male_virginity_loss milf milfy mom mommy mother mother_and_child mother_and_daughter oddly_cute oddly_wholesome recording rule_63 scout scout's_mother scout_(team_fortress_2) sex single_mom sniper sniper_(team_fortress_2) straight team_fortress_2 vaginal_penetration virgin virgin_female virgin_male virgin_man virginity_loss virgins wholesome wholesome_sex young_male young_man younger_male
1boy 2girls 3d adorable against_glass against_surface busty busty_female cute female female_virgin femscout filming garry's_mod gmod housewife human human_female human_male human_only kuudere love lovers loving loving_couple male male_virgin male_virginity_loss milf milfy mom mommy mother mother_and_child mother_and_daughter oddly_cute oddly_wholesome recording rule_63 scout scout's_mother scout_(team_fortress_2) sex single_mom sniper sniper_(team_fortress_2) straight team_fortress_2 vaginal_penetration virgin virgin_female virgin_male virgin_man virginity_loss virgins wholesome wholesome_sex young_male young_man younger_male
43zg anal_sex blush blushing cute gay helmet implied_penetration male male/male male_focus male_only male_virgin male_virginity_loss no_visible_genitalia older_man_and_younger_boy panting scout_(team_fortress_2) socks soldier_(team_fortress_2) team_fortress_2 virgin virgin_male virginity_loss wholesome wholesome_sex wrapped_hands
43zg anal_sex blush blushing cute gay helmet implied_penetration male male/male male_focus male_only male_virgin male_virginity_loss no_visible_genitalia older_man_and_younger_boy panting scout_(team_fortress_2) socks soldier_(team_fortress_2) team_fortress_2 virgin virgin_male virginity_loss wholesome wholesome_sex wrapped_hands