gulag best from all time

Time frame

Tags

gulag

3d 4k absurdres ak-47 ak_47 anal ass asylum at_gunpoint black_hair body_search breasts brown_hair bruise bruised bruised_eye bruised_eyes bruises call_of_duty call_of_duty_black_ops_cold_war call_of_duty_modern_warfare_2_(2022) cavity_search cavity_storage cfnf clenched_fist clenched_fists clenched_hands clenched_teeth clenching_fist clothed_female_nude_female clothed_male_nude_female cmnf collarbone completely_nude completely_nude_female dirty dirty_hair embarrassed embarrassed_nude_female embarrassment enf erect_nipples examination examination_room examination_table feet female_focus gingeslut357 glove_pull glove_snap gulag gun gunpoint hanging_breasts helen_park_(cod) humiliated humiliation imminent_anal imminent_anal_insertion imminent_anal_penetration invasion invasion_of_privacy jack-o_pose jackochallenge jackopose kneeling latex_glove latex_gloves legs lips looking_forward mascara mascara_smear mascara_tears medical medical_fetish medical_gloves medicine naked neck_scar nipples nude nurse nurse_hat nurse_uniform presenting presenting_anus presenting_butt presenting_butthole presenting_hindquarters prison prisoner rifle running_makeup running_mascara runny_makeup scared scared_expression scared_face scars short_hair soldier soldiers source_filmmaker soviet soviet_union spread_ass spread_eagle spread_legs spread_pussy spreading spreading_ass strip_search tagme threatened threatened_with_weapon threatening tiptoes toes weapon weapons worried worried_expression worried_face worried_look xxxgingeslut357xxx yirina_portnova
3d 4k absurdres ak-47 ak_47 anal ass asylum at_gunpoint black_hair body_search breasts brown_hair bruise bruised bruised_eye bruised_eyes bruises call_of_duty call_of_duty_black_ops_cold_war call_of_duty_modern_warfare_2_(2022) cavity_search cavity_storage cfnf clenched_fist clenched_fists clenched_hands clenched_teeth clenching_fist clothed_female_nude_female clothed_male_nude_female cmnf collarbone completely_nude completely_nude_female dirty dirty_hair embarrassed embarrassed_nude_female embarrassment enf erect_nipples examination examination_room examination_table feet female_focus gingeslut357 glove_pull glove_snap gulag gun gunpoint hanging_breasts helen_park_(cod) humiliated humiliation imminent_anal imminent_anal_insertion imminent_anal_penetration invasion invasion_of_privacy jack-o_pose jackochallenge jackopose kneeling latex_glove latex_gloves legs lips looking_forward mascara mascara_smear mascara_tears medical medical_fetish medical_gloves medicine naked neck_scar nipples nude nurse nurse_hat nurse_uniform presenting presenting_anus presenting_butt presenting_butthole presenting_hindquarters prison prisoner rifle running_makeup running_mascara runny_makeup scared scared_expression scared_face scars short_hair soldier soldiers source_filmmaker soviet soviet_union spread_ass spread_eagle spread_legs spread_pussy spreading spreading_ass strip_search tagme threatened threatened_with_weapon threatening tiptoes toes weapon weapons worried worried_expression worried_face worried_look xxxgingeslut357xxx yirina_portnova
ball_and_chain bondage bootjob boots breast_sucking breastfeeding breasts duo erection eyepatch femdom fingerless_gloves gloves gulag high_heel_boots jail lactation large_breasts larger_female malesub milf milk naked_footwear nude penis prison prisoner pussy riding_crop smaller_male sorenutz straight thick_thighs thigh through_bars voluptuous warden
ball_and_chain bondage bootjob boots breast_sucking breastfeeding breasts duo erection eyepatch femdom fingerless_gloves gloves gulag high_heel_boots jail lactation large_breasts larger_female malesub milf milk naked_footwear nude penis prison prisoner pussy riding_crop smaller_male sorenutz straight thick_thighs thigh through_bars voluptuous warden
1girls anal animated anthro_only bdsm blush bondage breasts crying double_anal double_penetration drooling eluku female game_over gulag mouth_open nona orc penis prison pussy rape restrained stomach_bulge tears tongue_out triple_penetration vaginal_penetration wolf wolf_dungeon
1girls anal animated anthro_only bdsm blush bondage breasts crying double_anal double_penetration drooling eluku female game_over gulag mouth_open nona orc penis prison pussy rape restrained stomach_bulge tears tongue_out triple_penetration vaginal_penetration wolf wolf_dungeon
2014 2girls amel animal_genitalia animal_penis anthro anthrofied b00mt00b breasts brown_eyes brown_hair clothes cum cumshot cutie_mark dialog duo english_text equine equine_penis female friendship_is_magic furry futa_on_female futanari green_hair gulag hair horsecock intersex jrvanesbroek large_breasts legwear mammal mango_(character) my_little_pony orgasm original_character outercourse penis prison prison_uniform stockings text thigh_sex thighhighs thighs
2014 2girls amel animal_genitalia animal_penis anthro anthrofied b00mt00b breasts brown_eyes brown_hair clothes cum cumshot cutie_mark dialog duo english_text equine equine_penis female friendship_is_magic furry futa_on_female futanari green_hair gulag hair horsecock intersex jrvanesbroek large_breasts legwear mammal mango_(character) my_little_pony orgasm original_character outercourse penis prison prison_uniform stockings text thigh_sex thighhighs thighs
3d 4girls armbinder arms_behind_back barefoot bondage bondage_gear call_of_duty charly_(cod) clothing cod crotch_rope domino_(cod) feet female femsub gag gulag harness iskra_(cod) jail jail_cell latina legs_together mara_(cod) multiple_girls multiple_subs sex_toy shamrockmanipulation tape tape_gag tied_toes toe_bondage toes vibrator vibrator_taped_to_leg warzone
3d 4girls armbinder arms_behind_back barefoot bondage bondage_gear call_of_duty charly_(cod) clothing cod crotch_rope domino_(cod) feet female femsub gag gulag harness iskra_(cod) jail jail_cell latina legs_together mara_(cod) multiple_girls multiple_subs sex_toy shamrockmanipulation tape tape_gag tied_toes toe_bondage toes vibrator vibrator_taped_to_leg warzone
007delta 1boy 1girls ambiguous_gender anus being_watched big_penis blush bokeh chespin comic dialogue duo english_text erection exhibitionism eyewear feline female first_person_view furry glameow glasses gulag interspecies looking_at_viewer male male_pov mienshao misu_nox nintendo open_mouth original_character page_3 page_number penis pokémon_(species) pokemon pokemon_bw pokemon_dppt pokemon_mystery_dungeon pokemon_xy pov prison pussy rymherdier ryn_purrawri sex straight text thick_penis veins veiny_penis video_games wanderlust white_border window
007delta 1boy 1girls ambiguous_gender anus being_watched big_penis blush bokeh chespin comic dialogue duo english_text erection exhibitionism eyewear feline female first_person_view furry glameow glasses gulag interspecies looking_at_viewer male male_pov mienshao misu_nox nintendo open_mouth original_character page_3 page_number penis pokémon_(species) pokemon pokemon_bw pokemon_dppt pokemon_mystery_dungeon pokemon_xy pov prison pussy rymherdier ryn_purrawri sex straight text thick_penis veins veiny_penis video_games wanderlust white_border window
2018 anthro anubis balls black_fur canine deity egyptian erection excessive_precum flaming_tail fur gulag humanoid_penis jackal looking_at_viewer male male_only mammal muscular muscular_male nude penis precum prison prisoner scar skull_mask solo todex
2018 anthro anubis balls black_fur canine deity egyptian erection excessive_precum flaming_tail fur gulag humanoid_penis jackal looking_at_viewer male male_only mammal muscular muscular_male nude penis precum prison prisoner scar skull_mask solo todex
1boy 1girls alex_zedra big_breasts call_of_duty dark-skinned_male dark_skin gnashershells gulag hyper_penis imminent_sex interracial latina light-skinned_female mara_(cod) mask modern_warfare muscles muscular muscular_female muscular_male penis_out showing_off veiny_penis warzone
1boy 1girls alex_zedra big_breasts call_of_duty dark-skinned_male dark_skin gnashershells gulag hyper_penis imminent_sex interracial latina light-skinned_female mara_(cod) mask modern_warfare muscles muscular muscular_female muscular_male penis_out showing_off veiny_penis warzone
1boy 1girls bars black_sclera breasts cleavage erection female foreskin full-length_portrait full_length fur furry grin gulag huge_cock huge_testicles hyper hyper_penis interspecies ivysaur kaboozle lagomorph large_breasts long_ears lopunny male male_lopunny male_pokemon mammal midriff navel nintendo no_nipples nude penis pokémon_(species) pokemon pokemon_(species) pokemon_dppt pokemon_rgby portrait prison rabbit red_eyes standing straight testicles timothy_vladislaus veins veiny_penis video_games wide_hips
1boy 1girls bars black_sclera breasts cleavage erection female foreskin full-length_portrait full_length fur furry grin gulag huge_cock huge_testicles hyper hyper_penis interspecies ivysaur kaboozle lagomorph large_breasts long_ears lopunny male male_lopunny male_pokemon mammal midriff navel nintendo no_nipples nude penis pokémon_(species) pokemon pokemon_(species) pokemon_dppt pokemon_rgby portrait prison rabbit red_eyes standing straight testicles timothy_vladislaus veins veiny_penis video_games wide_hips
anthro anus ass big_butt bucket clothing collar feces feet female gloves gulag horn kobold piko_(simplifypm) prison pussy scat shackles shit-tier-skunk solo thick_thighs
anthro anus ass big_butt bucket clothing collar feces feet female gloves gulag horn kobold piko_(simplifypm) prison pussy scat shackles shit-tier-skunk solo thick_thighs
ape_escape big_breasts bondage crying dildo gulag insertion one_eye_closed prison prison_bitch sex_toy slavetoon tight_pussy vaginal_insertion yumi
ape_escape big_breasts bondage crying dildo gulag insertion one_eye_closed prison prison_bitch sex_toy slavetoon tight_pussy vaginal_insertion yumi
2017 anus ass bioluminescence black_fur boots close-up clothing clothing_lift domination dominatrix dungeon eeveelution female femdom feral first_person_view footwear foreshortening fur furry furry_only genital_focus glowing gulag leash looking_at_viewer nintendo pokémon_(species) pokemon police police_hat prison purple_eyes pussy raised_tail skirt skirt_lift solo tail trigaroo umbreon video_games
2017 anus ass bioluminescence black_fur boots close-up clothing clothing_lift domination dominatrix dungeon eeveelution female femdom feral first_person_view footwear foreshortening fur furry furry_only genital_focus glowing gulag leash looking_at_viewer nintendo pokémon_(species) pokemon police police_hat prison purple_eyes pussy raised_tail skirt skirt_lift solo tail trigaroo umbreon video_games
anal blue_fur bound censored furry gay gulag hedgehog mammal penis prison shadow_the_hedgehog skyeprower sonadow sonic_(series) sonic_the_hedgehog testicles
anal blue_fur bound censored furry gay gulag hedgehog mammal penis prison shadow_the_hedgehog skyeprower sonadow sonic_(series) sonic_the_hedgehog testicles
abs anthro badge bat bear belt big_breasts bikini breasts brown_eyes bulge canine catfight clothed clothing eyelashes female fight fox furry furry_only green_eyes greg_panovich guard gulag hair huge_breasts jail_bars jail_cell male mammal nipple_bulge no_humans noris_pole partially_clothed pink_hair polar_bear prison prisoner pussy_bulge speech_bubble swimsuit
abs anthro badge bat bear belt big_breasts bikini breasts brown_eyes bulge canine catfight clothed clothing eyelashes female fight fox furry furry_only green_eyes greg_panovich guard gulag hair huge_breasts jail_bars jail_cell male mammal nipple_bulge no_humans noris_pole partially_clothed pink_hair polar_bear prison prisoner pussy_bulge speech_bubble swimsuit
animal_genitalia animal_penis anthro anus backsack balls big_anus bondage border bound digitigrade equine equine_penis furronika gulag half-erect hooves horse horsecock looking_at_viewer looking_back male male_only mammal nude open_mouth penis prison puffy_anus rabin raised_tail rear_view solo spread_legs spreading window
animal_genitalia animal_penis anthro anus backsack balls big_anus bondage border bound digitigrade equine equine_penis furronika gulag half-erect hooves horse horsecock looking_at_viewer looking_back male male_only mammal nude open_mouth penis prison puffy_anus rabin raised_tail rear_view solo spread_legs spreading window
2015 african_wild_dog anthro black_fur black_hair bondage boots bottomless bound breast_sucking breasts canine closed_eyes clothing cuffs cum cum_in_pussy cum_inside duo female fur gulag hair lavenderpandy male mammal orgasm pants pants_down penetration penis prison pussy_juice resident_evil restrained sex shirt shirt_lift spread_legs spreading standing straight theblackrook uniform vaginal_penetration wolf
2015 african_wild_dog anthro black_fur black_hair bondage boots bottomless bound breast_sucking breasts canine closed_eyes clothing cuffs cum cum_in_pussy cum_inside duo female fur gulag hair lavenderpandy male mammal orgasm pants pants_down penetration penis prison pussy_juice resident_evil restrained sex shirt shirt_lift spread_legs spreading standing straight theblackrook uniform vaginal_penetration wolf
2017 animal_genitalia animal_penis anthro balls baton belt blue_eyes bound breasts brown_fur brown_hair canine canine_penis cowgirl_position disney duo erection female fox fur girl_on_top grey_fur gulag hair handcuffs hat jonas-puppeh judy_hopps knot lagomorph male male_penetrating mammal navel nipples nude on_top penetration penis police_hat prison purple_eyes pussy rabbit sex shackles simple_background sitting small_breasts smile spread_legs spreading tan_fur utility_belt vaginal_penetration white_fur zootopia
2017 animal_genitalia animal_penis anthro balls baton belt blue_eyes bound breasts brown_fur brown_hair canine canine_penis cowgirl_position disney duo erection female fox fur girl_on_top grey_fur gulag hair handcuffs hat jonas-puppeh judy_hopps knot lagomorph male male_penetrating mammal navel nipples nude on_top penetration penis police_hat prison purple_eyes pussy rabbit sex shackles simple_background sitting small_breasts smile spread_legs spreading tan_fur utility_belt vaginal_penetration white_fur zootopia
3d asylum bethesda_softworks big_penis blonde_hair blue_eyes dickgirl futa_only futanari gulag intersex prison skyrim the_elder_scrolls uncensored
3d asylum bethesda_softworks big_penis blonde_hair blue_eyes dickgirl futa_only futanari gulag intersex prison skyrim the_elder_scrolls uncensored
2014 aaron_(artist) abs anal anal_sex anthro anvil_position aydenwusky balls big_balls big_muscles big_penis bighorn_sheep canine caprine claws clothed clothing criminal cum duo fellatio fur grin gulag hair half-dressed hooves horn humanoid_penis husky male male_only mammal multiple_males muscles oral penetration penis police precum prison ram sex sheep shirt smile table toe_claws torn_clothing torn_shirt underwear yaoi
2014 aaron_(artist) abs anal anal_sex anthro anvil_position aydenwusky balls big_balls big_muscles big_penis bighorn_sheep canine caprine claws clothed clothing criminal cum duo fellatio fur grin gulag hair half-dressed hooves horn humanoid_penis husky male male_only mammal multiple_males muscles oral penetration penis police precum prison ram sex sheep shirt smile table toe_claws torn_clothing torn_shirt underwear yaoi
2016 2boys bar_grab bite bull_terrier canine censored gay gulag lemur lilaira male male_only mammal nipples one_eye_closed open_mouth piercing primate prison ryker sweat teeth wildering yaoi ziggy_(character)
2016 2boys bar_grab bite bull_terrier canine censored gay gulag lemur lilaira male male_only mammal nipples one_eye_closed open_mouth piercing primate prison ryker sweat teeth wildering yaoi ziggy_(character)
2017 anthro bound cell cum cuntboy cuntboy/male duo erection gulag intersex intersex/male ismar kalimah lizard male male_penetrating neverneverland nightcrauzer orgasm penetration penis prison prisoner reptile scalie sex through_bars tongue tongue_out vaginal_penetration warden
2017 anthro bound cell cum cuntboy cuntboy/male duo erection gulag intersex intersex/male ismar kalimah lizard male male_penetrating neverneverland nightcrauzer orgasm penetration penis prison prisoner reptile scalie sex through_bars tongue tongue_out vaginal_penetration warden
1boy 2015 all_fours anthro anus ass ass_up backsack balls blush claws digimon fersir flaccid guilmon gulag looking_back male male_only penis perineum presenting presenting_hindquarters prison red_scales rock scalie solo thick_thighs uncut yellow_eyes
1boy 2015 all_fours anthro anus ass ass_up backsack balls blush claws digimon fersir flaccid guilmon gulag looking_back male male_only penis perineum presenting presenting_hindquarters prison red_scales rock scalie solo thick_thighs uncut yellow_eyes
anthro balls begging brokowski clothing dripping drooling duo erection fur furry gulag keys kneeling long_tail male male_only mammal marsupial military open_pants opossum overalls penis penis_through_fly poking_out prehensile_tail prison saliva seaman_hardy sharp_teeth smile smirk standing story story_in_description tasmanian_devil teeth tongue tongue_out uncut uniform whiskers yaoi
anthro balls begging brokowski clothing dripping drooling duo erection fur furry gulag keys kneeling long_tail male male_only mammal marsupial military open_pants opossum overalls penis penis_through_fly poking_out prehensile_tail prison saliva seaman_hardy sharp_teeth smile smirk standing story story_in_description tasmanian_devil teeth tongue tongue_out uncut uniform whiskers yaoi
1boy 2015 3_fingers anthro big_ears black_fur blue_fur blush canine canine_penis chains collar erection fur furry gulag handcuffs heavy_breathing japanese_text kneeling knot kurou-karasu looking_aside looking_away looking_up lucario male male_only mammal motion_lines nintendo nude open_mouth orange_eyes penis pokemon pokemon_(species) pokemon_dppt prison shackles slave solo speech_bubble standing sweat tail testicles text thick_thighs thin_waist through_bars translated video_games yellow_fur
1boy 2015 3_fingers anthro big_ears black_fur blue_fur blush canine canine_penis chains collar erection fur furry gulag handcuffs heavy_breathing japanese_text kneeling knot kurou-karasu looking_aside looking_away looking_up lucario male male_only mammal motion_lines nintendo nude open_mouth orange_eyes penis pokemon pokemon_(species) pokemon_dppt prison shackles slave solo speech_bubble standing sweat tail testicles text thick_thighs thin_waist through_bars translated video_games yellow_fur
1boy animal_genitalia animal_penis anthro ass back big_ass black_fur blue_fur blush bondage bound canine canine_penis embarrassed erection furry grey_background gulag half-closed_eyes handcuffs hands_behind_back hands_tied inside knot kurou-karasu looking_at_viewer looking_away looking_back lucario male male_only mammal nintendo nude open_mouth orange_eyes patreon paws penis pokemon pokemon_(species) pokemon_dppt precum prison red_penis shackles signature sitting solo spikes sweat tail text thick_thighs tongue trembling url video_games watermark yellow_fur
1boy animal_genitalia animal_penis anthro ass back big_ass black_fur blue_fur blush bondage bound canine canine_penis embarrassed erection furry grey_background gulag half-closed_eyes handcuffs hands_behind_back hands_tied inside knot kurou-karasu looking_at_viewer looking_away looking_back lucario male male_only mammal nintendo nude open_mouth orange_eyes patreon paws penis pokemon pokemon_(species) pokemon_dppt precum prison red_penis shackles signature sitting solo spikes sweat tail text thick_thighs tongue trembling url video_games watermark yellow_fur
2017 anthro ass bottomless bound breasts chains claws clothed clothing crossed_legs cum female fur gnoll gulag hyena mammal open_shirt paws presenting presenting_pussy prison prisoner pussy pussy_juice solo spread_legs spreading teeth zafara_(artist)
2017 anthro ass bottomless bound breasts chains claws clothed clothing crossed_legs cum female fur gnoll gulag hyena mammal open_shirt paws presenting presenting_pussy prison prisoner pussy pussy_juice solo spread_legs spreading teeth zafara_(artist)
2017 anthro balloon bondage bound digital_media_(artwork) feline flaccid gag gagged gulag herseio invalid_tag jedader lizard male male_only mammal nude panther penis prison reptile rock scalie sitting slave weights
2017 anthro balloon bondage bound digital_media_(artwork) feline flaccid gag gagged gulag herseio invalid_tag jedader lizard male male_only mammal nude panther penis prison reptile rock scalie sitting slave weights
2017 anthro balls bottomless brookbashe brown_fur clothed clothing cum cum_drip cum_on_face cumshot disembodied_penis double_handjob dripping ejaculation erection fur gay guardians_of_the_galaxy gulag handjob hands-free hi_res kneeling licking male male_only mammal marvel oral orgasm penis penis_lick prison procyonid raccoon red_eyes ringed_tail rocket_raccoon sex tongue tongue_out
2017 anthro balls bottomless brookbashe brown_fur clothed clothing cum cum_drip cum_on_face cumshot disembodied_penis double_handjob dripping ejaculation erection fur gay guardians_of_the_galaxy gulag handjob hands-free hi_res kneeling licking male male_only mammal marvel oral orgasm penis penis_lick prison procyonid raccoon red_eyes ringed_tail rocket_raccoon sex tongue tongue_out