prison_guard_position -animated best from last month

Time frame

prison guard position

1boy 1girl alternate_version_at_source alternate_version_available arched_back arms_behind_back arms_held_back arms_restrained ass atroi bar_censor big_ass black_gloves black_hair black_stockings blue_leotard blurry_background blush breasts censored clothed_female_clothed_male clothed_sex clothing crying crying_with_eyes_open cum cum_in_pussy cum_inside detached_sleeves drooling ejaculating_in_vagina ejaculation erect_penis erection female female/male female_focus femdom forced forced_sex from_behind fucked_from_behind genshin_impact gloves green_eyes heavenly_ass highres hoyoverse indoors leotard light-skinned_female light-skinned_male light_skin long_hair long_sleeves looking_forward male male/female maledom medium_breasts mihoyo mona_(genshin_impact) motion_lines motorcycle_position open_eyes open_mouth paid_reward paid_reward_available penis penis_in_pussy plump_ass prison_guard_position sex sex_from_behind shinatsukou side_view stockings sweat sweatdrop taken_from_behind tearing_up tears text textless_version thick_thighs thighs thrusting tongue tongue_out twintails vaginal_penetration vaginal_sex x-ray xray_view
1boy 1girl alternate_version_at_source alternate_version_available arched_back arms_behind_back arms_held_back arms_restrained ass atroi bar_censor big_ass black_gloves black_hair black_stockings blue_leotard blurry_background blush breasts censored clothed_female_clothed_male clothed_sex clothing crying crying_with_eyes_open cum cum_in_pussy cum_inside detached_sleeves drooling ejaculating_in_vagina ejaculation erect_penis erection female female/male female_focus femdom forced forced_sex from_behind fucked_from_behind genshin_impact gloves green_eyes heavenly_ass highres hoyoverse indoors leotard light-skinned_female light-skinned_male light_skin long_hair long_sleeves looking_forward male male/female maledom medium_breasts mihoyo mona_(genshin_impact) motion_lines motorcycle_position open_eyes open_mouth paid_reward paid_reward_available penis penis_in_pussy plump_ass prison_guard_position sex sex_from_behind shinatsukou side_view stockings sweat sweatdrop taken_from_behind tearing_up tears text textless_version thick_thighs thighs thrusting tongue tongue_out twintails vaginal_penetration vaginal_sex x-ray xray_view
ai_generated ambiguous_penetration ariel big_ass big_breasts creampie cum cum_explosion cum_in_pussy cum_inside disney disney_princess doggy_style femdom from_behind futa_on_female futadom futanari holding_arms holding_arms_back light-skinned_female light-skinned_futanari moaning prison_guard_position puffyart red_hair the_little_mermaid ursula_(the_little_mermaid) vanessa_(the_little_mermaid)
ai_generated ambiguous_penetration ariel big_ass big_breasts creampie cum cum_explosion cum_in_pussy cum_inside disney disney_princess doggy_style femdom from_behind futa_on_female futadom futanari holding_arms holding_arms_back light-skinned_female light-skinned_futanari moaning prison_guard_position puffyart red_hair the_little_mermaid ursula_(the_little_mermaid) vanessa_(the_little_mermaid)
1boy 1girls 2025 2d 2d_(artwork) ambiguous_penetration arm_grab ass big_ass big_butt blonde_hair breasts cheerleader cheerleader_uniform commander_(nikke) cum cum_inside cute_fang dialogue english_text female female_focus goddess_of_victory:_nikke green_eyes gyaru hi_res huge_breasts invadernoodles large_ass light-skinned_female light-skinned_male light_skin livestream long_hair male male/female male_penetrating male_penetrating_female midnight_echova prison_guard_position rupee_(nikke) sex sound sound_edit sound_effects sound_warning tagme tan tan-skinned_female tanned_skin thick_thighs unseen_male_face vammzu video voice_acted
1boy 1girls 2025 2d 2d_(artwork) ambiguous_penetration arm_grab ass big_ass big_butt blonde_hair breasts cheerleader cheerleader_uniform commander_(nikke) cum cum_inside cute_fang dialogue english_text female female_focus goddess_of_victory:_nikke green_eyes gyaru hi_res huge_breasts invadernoodles large_ass light-skinned_female light-skinned_male light_skin livestream long_hair male male/female male_penetrating male_penetrating_female midnight_echova prison_guard_position rupee_(nikke) sex sound sound_edit sound_effects sound_warning tagme tan tan-skinned_female tanned_skin thick_thighs unseen_male_face vammzu video voice_acted
1boy 1girls 2d absurd_res anthro anthro_on_anthro areola arm_pull ass bent_over biped blush bodily_fluids breasts canid canid_demon canine classroom cum cum_inside cum_leaking demon digital_media duo eyelashes female female_penetrated femsub from_behind_position fur furry furry_only genital_fluids hellhound helluva_boss hi_res loimu looking_pleasured loona_(helluva_boss) male male/female male_penetrating maledom mammal multicolored_body mythological_canine mythological_creature mythology nipples nude penetration penile penile_penetration prison_guard_position public_nudity public_sex pupils school sex straight submissive submissive_female sweat thick_thighs white_body
1boy 1girls 2d absurd_res anthro anthro_on_anthro areola arm_pull ass bent_over biped blush bodily_fluids breasts canid canid_demon canine classroom cum cum_inside cum_leaking demon digital_media duo eyelashes female female_penetrated femsub from_behind_position fur furry furry_only genital_fluids hellhound helluva_boss hi_res loimu looking_pleasured loona_(helluva_boss) male male/female male_penetrating maledom mammal multicolored_body mythological_canine mythological_creature mythology nipples nude penetration penile penile_penetration prison_guard_position public_nudity public_sex pupils school sex straight submissive submissive_female sweat thick_thighs white_body
1futa 1girls alternate_version_available ambiguous_penetration arms_behind_back big_breasts black_hair black_socks blue_eyes blush breasts choker cum cum_inside eyes_rolled_up eyes_rolling_back female female_penetrated from_behind from_behind_position futa_on_female futa_penetrating futa_penetrating_female futanari huge_breasts lainart large_breasts mature_female mature_futa milf multicolored_hair nipples open_mouth panties panties_around_legs panties_down prison_guard_position red_hair rwby sex short_hair socks summer_rose thigh_socks thighhighs white_hair white_socks willow_schnee
1futa 1girls alternate_version_available ambiguous_penetration arms_behind_back big_breasts black_hair black_socks blue_eyes blush breasts choker cum cum_inside eyes_rolled_up eyes_rolling_back female female_penetrated from_behind from_behind_position futa_on_female futa_penetrating futa_penetrating_female futanari huge_breasts lainart large_breasts mature_female mature_futa milf multicolored_hair nipples open_mouth panties panties_around_legs panties_down prison_guard_position red_hair rwby sex short_hair socks summer_rose thigh_socks thighhighs white_hair white_socks willow_schnee
1boy 1girl arms_behind_back ass bilingual_commentary black_hat black_visor blush breasts bright_pupils close-up collarbone commentary doggystyle english_commentary grabbing_another's_arm green_eyes half-closed_eyes hanging_breasts hat heavy_breathing hetero highres honkai:_star_rail honkai_(series) horned_hat horns indoors large_breasts long_hair looking_ahead medium_hair mixed-language_commentary multicolored_hair naked_hat nipples nude on_bed open_mouth paid_reward_available panties panty_pull pink_hair prison_guard_position rappa_(honkai:_star_rail) red_horns red_panties sex sex_from_behind smile solo_focus steaming_body streaked_hair sweat sweatdrop takashia_(akimototakashia) underwear very_long_hair white_pupils
1boy 1girl arms_behind_back ass bilingual_commentary black_hat black_visor blush breasts bright_pupils close-up collarbone commentary doggystyle english_commentary grabbing_another's_arm green_eyes half-closed_eyes hanging_breasts hat heavy_breathing hetero highres honkai:_star_rail honkai_(series) horned_hat horns indoors large_breasts long_hair looking_ahead medium_hair mixed-language_commentary multicolored_hair naked_hat nipples nude on_bed open_mouth paid_reward_available panties panty_pull pink_hair prison_guard_position rappa_(honkai:_star_rail) red_horns red_panties sex sex_from_behind smile solo_focus steaming_body streaked_hair sweat sweatdrop takashia_(akimototakashia) underwear very_long_hair white_pupils
1boy 1girls animal_ears blush bob_cut bottom_heavy canon_couple carrying_partner cat_ears catgirl child_bearing_hips completely_nude core_crystal cum cum_announcement cum_drip cum_in_pussy cum_inside cumming dialogue dilf dirty_talk dripping dripping_cum dripping_pussy english english_text enjoying female_ejaculation flat_chest from_behind fucked_from_behind fucked_silly full_body huge_cock intense_orgasm intense_sex large_penis larger_male lifted_by_another lifted_by_penis milf nia nintendo nude petite_female pounding prison_guard_position queen rex_(xenoblade) rough_sex royalty saeko_art screaming screaming_in_pleasure screaming_orgasm short_hair shorter_female size_difference small_breasts smaller_female squirting standing_sex stomach_bulge straight stress_relief suspended_on_penis taller_male text thick_thighs torogao vaginal_penetration wet_pussy white_hair wide_hips xenoblade_(series) xenoblade_chronicles_2 xenoblade_chronicles_3 xenoblade_chronicles_3:_future_redeemed
1boy 1girls animal_ears blush bob_cut bottom_heavy canon_couple carrying_partner cat_ears catgirl child_bearing_hips completely_nude core_crystal cum cum_announcement cum_drip cum_in_pussy cum_inside cumming dialogue dilf dirty_talk dripping dripping_cum dripping_pussy english english_text enjoying female_ejaculation flat_chest from_behind fucked_from_behind fucked_silly full_body huge_cock intense_orgasm intense_sex large_penis larger_male lifted_by_another lifted_by_penis milf nia nintendo nude petite_female pounding prison_guard_position queen rex_(xenoblade) rough_sex royalty saeko_art screaming screaming_in_pleasure screaming_orgasm short_hair shorter_female size_difference small_breasts smaller_female squirting standing_sex stomach_bulge straight stress_relief suspended_on_penis taller_male text thick_thighs torogao vaginal_penetration wet_pussy white_hair wide_hips xenoblade_(series) xenoblade_chronicles_2 xenoblade_chronicles_3 xenoblade_chronicles_3:_future_redeemed
1boy 1girls ai_generated anthro areolae bandai_namco barefoot belly big_areola big_ass big_breasts big_nipples big_thighs blush claws curvy curvy_ass curvy_body curvy_female curvy_figure curvy_hips curvy_thighs digimon digimon_(species) digimon_tamers doggy_style dominant dominant_male domination dripping drooling erect_nipples fat_ass female furry green_eyes hi_res high_resolution highres huge_areolae huge_ass huge_breasts huge_nipples huge_thighs intense_sex large_breasts male male/female male_penetrating male_penetrating_female massive_ass massive_breasts night nipples orgasm orgasm_face outdoors outside pink_areola pink_nipples pleasure_face plump_ass plump_thighs prison_guard_position puffy_nipples renamon rough_sex sagging_breasts saliva shocked slightly_chubby stable_diffusion steam steaming_body steamy_breath sweat sweatdrop sweating sweaty sweaty_ass sweaty_body sweaty_breasts sweaty_butt sweaty_thighs synthneon thick thick_ass thick_thighs vaginal_penetration vaginal_sex yellow_body yellow_fur yellow_skin
1boy 1girls ai_generated anthro areolae bandai_namco barefoot belly big_areola big_ass big_breasts big_nipples big_thighs blush claws curvy curvy_ass curvy_body curvy_female curvy_figure curvy_hips curvy_thighs digimon digimon_(species) digimon_tamers doggy_style dominant dominant_male domination dripping drooling erect_nipples fat_ass female furry green_eyes hi_res high_resolution highres huge_areolae huge_ass huge_breasts huge_nipples huge_thighs intense_sex large_breasts male male/female male_penetrating male_penetrating_female massive_ass massive_breasts night nipples orgasm orgasm_face outdoors outside pink_areola pink_nipples pleasure_face plump_ass plump_thighs prison_guard_position puffy_nipples renamon rough_sex sagging_breasts saliva shocked slightly_chubby stable_diffusion steam steaming_body steamy_breath sweat sweatdrop sweating sweaty sweaty_ass sweaty_body sweaty_breasts sweaty_butt sweaty_thighs synthneon thick thick_ass thick_thighs vaginal_penetration vaginal_sex yellow_body yellow_fur yellow_skin
1boy 1boy1girl 1girls ai_generated ambiguous_penetration ass balls black_body black_skin boku_no_hero_academia breasts chubby chubby_female clenched_teeth cold_shrike crying crying_with_eyes_open cum cum_inside cuts doorway ejaculation faceless_male female forced green_hair inko_midoriya interspecies larger_male looking_at_viewer male male/female mature_female milf monster monster_cock muscular_male my_hero_academia nomu novelai overweight penis prison_guard_position rape self_upload sex sex_from_behind size_difference smaller_female wrist_grab
1boy 1boy1girl 1girls ai_generated ambiguous_penetration ass balls black_body black_skin boku_no_hero_academia breasts chubby chubby_female clenched_teeth cold_shrike crying crying_with_eyes_open cum cum_inside cuts doorway ejaculation faceless_male female forced green_hair inko_midoriya interspecies larger_male looking_at_viewer male male/female mature_female milf monster monster_cock muscular_male my_hero_academia nomu novelai overweight penis prison_guard_position rape self_upload sex sex_from_behind size_difference smaller_female wrist_grab
ahe_gao anthro fortnite furry highwire_(fortnite) pack_leader_highwire penetration prison_guard_position tagme thunder_(fortnite) tits_out twitchyanimation video
ahe_gao anthro fortnite furry highwire_(fortnite) pack_leader_highwire penetration prison_guard_position tagme thunder_(fortnite) tits_out twitchyanimation video
1futa 1girls arms_behind_back black_hair black_socks blue_eyes blush breasts choker cum cum_in_pussy cum_inside eyes_rolled_up eyes_rolling_back female female_penetrated from_behind from_behind_position futa_on_female futa_penetrating futa_penetrating_female futanari huge_breasts lainart large_breasts mature_female mature_futa milf milf_on_milf multicolored_hair nipples open_mouth panties panties_around_legs panties_down prison_guard_position red_hair rwby sex socks summer_rose thigh_socks thighhighs white_hair white_socks willow_schnee
1futa 1girls arms_behind_back black_hair black_socks blue_eyes blush breasts choker cum cum_in_pussy cum_inside eyes_rolled_up eyes_rolling_back female female_penetrated from_behind from_behind_position futa_on_female futa_penetrating futa_penetrating_female futanari huge_breasts lainart large_breasts mature_female mature_futa milf milf_on_milf multicolored_hair nipples open_mouth panties panties_around_legs panties_down prison_guard_position red_hair rwby sex socks summer_rose thigh_socks thighhighs white_hair white_socks willow_schnee
1futa 1girls argentinian_miku astralx bent_over big_breasts blue_hair brazilian_miku cum cum_in_pussy fertilization futa_on_female futadom futanari hatsune_miku heart-shaped_pupils huge_breasts impregnation large_breasts light-skinned_female ovum ovum_with_heart prison_guard_position sex sex_from_behind standing_sex vaginal_penetration vocaloid
1futa 1girls argentinian_miku astralx bent_over big_breasts blue_hair brazilian_miku cum cum_in_pussy fertilization futa_on_female futadom futanari hatsune_miku heart-shaped_pupils huge_breasts impregnation large_breasts light-skinned_female ovum ovum_with_heart prison_guard_position sex sex_from_behind standing_sex vaginal_penetration vocaloid
1futa 1girls age_difference ass big_ass big_breasts big_penis body_writing breasts breasts_bigger_than_head cum cum_in_pussy cum_inside ed-jim female from_behind futa_on_female futanari gigantic_breasts heart-shaped_pupils huge_ass huge_breasts incest intersex large_ass large_breasts light-skinned_female light-skinned_futanari mother_and_daughter older_futanari penis prison_guard_position rwby second-party_source sex sex_from_behind stockings vaginal_penetration weiss_schnee white_hair willow_schnee younger_female
1futa 1girls age_difference ass big_ass big_breasts big_penis body_writing breasts breasts_bigger_than_head cum cum_in_pussy cum_inside ed-jim female from_behind futa_on_female futanari gigantic_breasts heart-shaped_pupils huge_ass huge_breasts incest intersex large_ass large_breasts light-skinned_female light-skinned_futanari mother_and_daughter older_futanari penis prison_guard_position rwby second-party_source sex sex_from_behind stockings vaginal_penetration weiss_schnee white_hair willow_schnee younger_female
2boys 2girls anal anus arm_pull ass bartolomeobari bisexual_(female) bisexual_female black_thighhighs breast_press breasts cum cum_in_ass cum_in_pussy cum_string drill_hair english_commentary faceless faceless_male female_human femsub hatsune_miku highres human human_male kasane_teto kissing kissing_while_penetrated light-skinned_female long_hair medium_breasts multiple_boys multiple_girls multiple_views naked_thighhighs nude number_tattoo paid_reward_available penis prison_guard_position pussy questionable_consent red_hair sex sex_from_behind shirt shoulder_tattoo slim_waist standing standing_sex stomach_bulge straight symmetrical_docking tattoo thighhighs twin_drills twintails uncensored utau vaginal_penetration vocaloid
2boys 2girls anal anus arm_pull ass bartolomeobari bisexual_(female) bisexual_female black_thighhighs breast_press breasts cum cum_in_ass cum_in_pussy cum_string drill_hair english_commentary faceless faceless_male female_human femsub hatsune_miku highres human human_male kasane_teto kissing kissing_while_penetrated light-skinned_female long_hair medium_breasts multiple_boys multiple_girls multiple_views naked_thighhighs nude number_tattoo paid_reward_available penis prison_guard_position pussy questionable_consent red_hair sex sex_from_behind shirt shoulder_tattoo slim_waist standing standing_sex stomach_bulge straight symmetrical_docking tattoo thighhighs twin_drills twintails uncensored utau vaginal_penetration vocaloid
2boys 2girls ambiguous_penetration anthro arm_pull ass biped black_body blue_body blue_fur blue_tail breast_squish breasts breasts_frottage butt_squish enigi09 female female_lucario female_penetrated from_behind_position fur generation_4_pokemon generation_9_pokemon green_body green_fur green_tail group heart_symbol hi_res lucario male male/female male_penetrating male_penetrating_female meowscarada multicolored_body nintendo parallel_sex penetration penile penile_penetration pokemon pokemon_(species) pokephilia prison_guard_position red_body sex short_tail side_view simple_background squish standing standing_sex tail tan_body tan_fur white_background
2boys 2girls ambiguous_penetration anthro arm_pull ass biped black_body blue_body blue_fur blue_tail breast_squish breasts breasts_frottage butt_squish enigi09 female female_lucario female_penetrated from_behind_position fur generation_4_pokemon generation_9_pokemon green_body green_fur green_tail group heart_symbol hi_res lucario male male/female male_penetrating male_penetrating_female meowscarada multicolored_body nintendo parallel_sex penetration penile penile_penetration pokemon pokemon_(species) pokephilia prison_guard_position red_body sex short_tail side_view simple_background squish standing standing_sex tail tan_body tan_fur white_background
1boy 1girls :p all_fours areolae arm_grab balls bent_over blush bouncing_breasts braid braided_ponytail breast_focus breasts closed_eyes comic completely_nude crotch deep_skin double_breast_grab duo english_text eyewear glasses grey_hair hoyoverse kinkymation large_breasts light-skinned_female light-skinned_male light_skin long_hair mihoyo nipples nude nude_female nude_male penis pink_hair prison_guard_position pussy pussy_juice sex short_hair side_ponytail sound_effects standing_sex straight sweat testicles text tsukishiro_yanagi vaginal_penetration wise_(zenless_zone_zero) zenless_zone_zero
1boy 1girls :p all_fours areolae arm_grab balls bent_over blush bouncing_breasts braid braided_ponytail breast_focus breasts closed_eyes comic completely_nude crotch deep_skin double_breast_grab duo english_text eyewear glasses grey_hair hoyoverse kinkymation large_breasts light-skinned_female light-skinned_male light_skin long_hair mihoyo nipples nude nude_female nude_male penis pink_hair prison_guard_position pussy pussy_juice sex short_hair side_ponytail sound_effects standing_sex straight sweat testicles text tsukishiro_yanagi vaginal_penetration wise_(zenless_zone_zero) zenless_zone_zero
2boys big_ass big_penis bubble_ass bubble_butt burning_spice_cookie canned_beans cookie_run cookie_run_kingdom dominant dominant_male domination face_down_ass_up femboy femboy_on_male femboysub gay gay_anal gay_domination gay_sex huge_cock imminent_anal imminent_penetration imminent_sex maledom malesub precum precum_bubble precum_drip precum_on_penis precum_string presenting presenting_anus presenting_butt presenting_hindquarters prison_guard_position shadow_milk_cookie submission submissive submissive_male thick_ass thick_thighs twink yaoi
2boys big_ass big_penis bubble_ass bubble_butt burning_spice_cookie canned_beans cookie_run cookie_run_kingdom dominant dominant_male domination face_down_ass_up femboy femboy_on_male femboysub gay gay_anal gay_domination gay_sex huge_cock imminent_anal imminent_penetration imminent_sex maledom malesub precum precum_bubble precum_drip precum_on_penis precum_string presenting presenting_anus presenting_butt presenting_hindquarters prison_guard_position shadow_milk_cookie submission submissive submissive_male thick_ass thick_thighs twink yaoi
1boy 1girls abdominal_bulge ai_generated anthro anthro_on_human arm_grab arms_behind_back big_breasts big_penis breasts collar cum cum_in_pussy cum_inside dark-skinned_male dark_skin detailed_background drooling duo exhibitionism faceless_male fat_man female female_penetrated furry furry_female furry_with_non-furry goth goth_girl hair helluva_boss human human_on_anthro impregnation internal interracial interracial_sex interspecies large_breasts loona_(helluva_boss) loving_it male male/female male_on_anthro male_penetrating male_penetrating_female muscular muscular_male nipples nude orgasm orgasm_face ovum penetration penis pleasure_face prison_guard_position public_nudity public_sex pussy rape saliva sex smile sperm_cell spiked_collar standing standing_sex straight sweat tail teeth thick_thighs tongue tongue_out ugly_bastard ugly_man vaginal vaginal_penetration vaginal_sex
1boy 1girls abdominal_bulge ai_generated anthro anthro_on_human arm_grab arms_behind_back big_breasts big_penis breasts collar cum cum_in_pussy cum_inside dark-skinned_male dark_skin detailed_background drooling duo exhibitionism faceless_male fat_man female female_penetrated furry furry_female furry_with_non-furry goth goth_girl hair helluva_boss human human_on_anthro impregnation internal interracial interracial_sex interspecies large_breasts loona_(helluva_boss) loving_it male male/female male_on_anthro male_penetrating male_penetrating_female muscular muscular_male nipples nude orgasm orgasm_face ovum penetration penis pleasure_face prison_guard_position public_nudity public_sex pussy rape saliva sex smile sperm_cell spiked_collar standing standing_sex straight sweat tail teeth thick_thighs tongue tongue_out ugly_bastard ugly_man vaginal vaginal_penetration vaginal_sex
1boy 1girls ahe_gao ai_generated anus aoi_sakamoto apron ass big_ass big_breasts big_penis black_hair blush bottomless breasts brown_eyes clothes_lift cross_section cum cum_in_pussy cum_in_uterus cum_overflow cutaway ejaculation female green_apron hair_ornament hairclip hearts_around_penis inset internal_cumshot large_breasts mature_female open_mouth penis pov prison_guard_position puckered_anus pussy rolling_eyes sakamoto_days sex sex_from_behind shirt shirt_lift short_hair solo_focus standing straight taro_sakamoto temper1 temper_ai tongue tongue_out uncensored uterus vaginal_penetration veins veiny_penis x-ray
1boy 1girls ahe_gao ai_generated anus aoi_sakamoto apron ass big_ass big_breasts big_penis black_hair blush bottomless breasts brown_eyes clothes_lift cross_section cum cum_in_pussy cum_in_uterus cum_overflow cutaway ejaculation female green_apron hair_ornament hairclip hearts_around_penis inset internal_cumshot large_breasts mature_female open_mouth penis pov prison_guard_position puckered_anus pussy rolling_eyes sakamoto_days sex sex_from_behind shirt shirt_lift short_hair solo_focus standing straight taro_sakamoto temper1 temper_ai tongue tongue_out uncensored uterus vaginal_penetration veins veiny_penis x-ray