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20th century

1990s 1999 1girls 20th_century 2boys 3d alley artist_name blowjob brick_wall closed_eyes clothed_male_nude_female completely_nude_female copyright_name fellatio fingering_self fire_escape full_body hetero hetero_sex high_ponytail kneeling lollipop masturbating_during_fellatio naked_female nipple_tweak pallet penis penis_out perky_breasts pinching_nipple pond prostitution purse running_bond skinny_female small_breasts small_nipples standing straight thrallord trash_can uncensored web_address
1990s 1999 1girls 20th_century 2boys 3d alley artist_name blowjob brick_wall closed_eyes clothed_male_nude_female completely_nude_female copyright_name fellatio fingering_self fire_escape full_body hetero hetero_sex high_ponytail kneeling lollipop masturbating_during_fellatio naked_female nipple_tweak pallet penis penis_out perky_breasts pinching_nipple pond prostitution purse running_bond skinny_female small_breasts small_nipples standing straight thrallord trash_can uncensored web_address
1990s 1999 20th_century 3d arms_tied_together black_hair bondage branding branding_iron brazier legs_tied naked_female thrallord
1990s 1999 20th_century 3d arms_tied_together black_hair bondage branding branding_iron brazier legs_tied naked_female thrallord
1990s 1999 20th_century 3d black_hair chained collar hands_tied naked_female temple_background thrallord what zebra_stripes zebra_taur
1990s 1999 20th_century 3d black_hair chained collar hands_tied naked_female temple_background thrallord what zebra_stripes zebra_taur
1990s 1998 20th_century ass_up bed bell buttplug_in_ass buttplug_tail clitoris_piercing collar leash pillow the_veterinarian
1990s 1998 20th_century ass_up bed bell buttplug_in_ass buttplug_tail clitoris_piercing collar leash pillow the_veterinarian
1990s 1999 20th_century buttplug_in_ass buttplug_tail collar kittyplay makeup petgirl petplay pussy_exposed the_veterinarian
1990s 1999 20th_century buttplug_in_ass buttplug_tail collar kittyplay makeup petgirl petplay pussy_exposed the_veterinarian
1990s 1998 20th_century african_female buttplug_tail canine collar leash tattoo the_veterinarian
1990s 1998 20th_century african_female buttplug_tail canine collar leash tattoo the_veterinarian
1990s 1998 20th_century bottomless canine collar femdom leash submissive_female the_veterinarian
1990s 1998 20th_century bottomless canine collar femdom leash submissive_female the_veterinarian
1990s 1999 1female 20th_century anal_sex arms_tied_behind_back canine naked naked_female the_veterinarian tied_to_chair zoophilia
1990s 1999 1female 20th_century anal_sex arms_tied_behind_back canine naked naked_female the_veterinarian tied_to_chair zoophilia
1990 1990s 1boy 1girls 20th_century anthro anthro_on_female anthro_on_human anthro_penetrating_female anthro_penetrating_human female groping_crotch handjob holding_penis human human_on_anthro interspecies light-skinned_female light_skin male male/female male_werewolf naked nude nude_female penis the_werewolf vagina vaginal_fingering vaginal_penetration werewolf
1990 1990s 1boy 1girls 20th_century anthro anthro_on_female anthro_on_human anthro_penetrating_female anthro_penetrating_human female groping_crotch handjob holding_penis human human_on_anthro interspecies light-skinned_female light_skin male male/female male_werewolf naked nude nude_female penis the_werewolf vagina vaginal_fingering vaginal_penetration werewolf
1990s 1999 20th_century arms_tied_behind_back ball_gag barefoot bondage buttplug_tail canine collar naked_female the_veterinarian tied_to_pole
1990s 1999 20th_century arms_tied_behind_back ball_gag barefoot bondage buttplug_tail canine collar naked_female the_veterinarian tied_to_pole
1990s 1999 20th_century 3d 3girls annie-mae_(thrallord) bathtub black_hair blonde_hair blue_hair kneeling rubber_duck shrunken_woman thrallord
1990s 1999 20th_century 3d 3girls annie-mae_(thrallord) bathtub black_hair blonde_hair blue_hair kneeling rubber_duck shrunken_woman thrallord
1990s 1999 20th_century 3d annie-mae_(thrallord) bathtub black_hair naked nipple_rings shrunken_woman thrallord
1990s 1999 20th_century 3d annie-mae_(thrallord) bathtub black_hair naked nipple_rings shrunken_woman thrallord
1990s 1999 20th_century 2girls 3d annie-mae_(thrallord) bathtub blonde_hair blue_hair groping_breasts groping_crotch rubber_duck shrunken_woman thrallord yuri
1990s 1999 20th_century 2girls 3d annie-mae_(thrallord) bathtub blonde_hair blue_hair groping_breasts groping_crotch rubber_duck shrunken_woman thrallord yuri
1990s 1999 1boy 1male 20th_century 2girls 3d annie-mae_(thrallord) bathtub big_areola big_boobs big_breasts big_butt big_nipples big_tits blonde_hair blue_hair boobs giant nipples shrunken_woman thrallord
1990s 1999 1boy 1male 20th_century 2girls 3d annie-mae_(thrallord) bathtub big_areola big_boobs big_breasts big_butt big_nipples big_tits blonde_hair blue_hair boobs giant nipples shrunken_woman thrallord
1990s 1999 1boy 1girls 20th_century 3d annie-mae_(thrallord) ass_up blue_hair bondage brick_wall character_name clothed_male_nude_female completely_nude_female drill extreme_size_difference hetero looking_back running_bond shrunken_woman staples thrallord top-down_bottom-up web_address
1990s 1999 1boy 1girls 20th_century 3d annie-mae_(thrallord) ass_up blue_hair bondage brick_wall character_name clothed_male_nude_female completely_nude_female drill extreme_size_difference hetero looking_back running_bond shrunken_woman staples thrallord top-down_bottom-up web_address
1990s 1999 20th_century 3d annie-mae_(thrallord) blue_hair crucifixion naked pins shrunken_woman thrallord torture
1990s 1999 20th_century 3d annie-mae_(thrallord) blue_hair crucifixion naked pins shrunken_woman thrallord torture
1990s 1999 20th_century 3d annie-mae_(thrallord) blue_hair bondage chains iron_mask metal_restraint naked shrunken_woman thrallord waist_band
1990s 1999 20th_century 3d annie-mae_(thrallord) blue_hair bondage chains iron_mask metal_restraint naked shrunken_woman thrallord waist_band
1990s 1999 20th_century 3d annie-mae_(thrallord) blue_hair captured feline naked prey scratches shrunken_woman struggling_prey thrallord
1990s 1999 20th_century 3d annie-mae_(thrallord) blue_hair captured feline naked prey scratches shrunken_woman struggling_prey thrallord
1990s 1999 20th_century 3d annie-mae_(thrallord) blue_hair feline naked prey scratches shrunken_woman thrallord
1990s 1999 20th_century 3d annie-mae_(thrallord) blue_hair feline naked prey scratches shrunken_woman thrallord
1990s 1999 1girls 20th_century 3d annie-mae_(thrallord) ass_up blue_hair bondage character_name cigarette_pack completely_nude_female green insemination long_bangs marlboro naked restrained semen_drip shrunken_woman solo staples stationary_restraints thrallord v_legs web_address
1990s 1999 1girls 20th_century 3d annie-mae_(thrallord) ass_up blue_hair bondage character_name cigarette_pack completely_nude_female green insemination long_bangs marlboro naked restrained semen_drip shrunken_woman solo staples stationary_restraints thrallord v_legs web_address
1990s 1999 20th_century 3d annie-mae_(thrallord) arms_tied_behind_back blue_hair rope_bondage shrunken_woman thrallord wasp
1990s 1999 20th_century 3d annie-mae_(thrallord) arms_tied_behind_back blue_hair rope_bondage shrunken_woman thrallord wasp
1990s 1999 20th_century arms_tied_behind_back black_and_white bondage bound female female_only femsub pubic_hair rope rope_around_neck rope_bondage rope_harness standing the_veterinarian tied_arms_behind_back tied_to_pole
1990s 1999 20th_century arms_tied_behind_back black_and_white bondage bound female female_only femsub pubic_hair rope rope_around_neck rope_bondage rope_harness standing the_veterinarian tied_arms_behind_back tied_to_pole
1990s 1998 20th_century arms_tied_behind_back barefoot bell black_and_white bondage buttplug naked_female nude_female the_veterinarian tied_arms_behind_back tied_to_pole
1990s 1998 20th_century arms_tied_behind_back barefoot bell black_and_white bondage buttplug naked_female nude_female the_veterinarian tied_arms_behind_back tied_to_pole
1990s 1999 20th_century basket buttplug_tail collar female handdrawn petplay shackles the_veterinarian
1990s 1999 20th_century basket buttplug_tail collar female handdrawn petplay shackles the_veterinarian
1990s 1997 20th_century african_female black_and_white bondage buttplug_tail collar handdrawn leash nipple_piercing ponygirl ponyplay the_veterinarian
1990s 1997 20th_century african_female black_and_white bondage buttplug_tail collar handdrawn leash nipple_piercing ponygirl ponyplay the_veterinarian
1990s 1992 20th_century absurd_res ailurid all_fours anthro at bed border breasts canid canine canis circumjacentity crocodilian deer digital_media_(artwork) doggy_style domestic_dog felid feline female female/female fox from_behind_position furniture group group_sex hair hi_res line_art looking_at_viewer lynx male male/female mammal nipples on_bed open_mouth orgy pantherine polaroid_photo prone_bone red_panda reptile scalie selfie sex signed simple_background smile smoking tail tiger wolf
1990s 1992 20th_century absurd_res ailurid all_fours anthro at bed border breasts canid canine canis circumjacentity crocodilian deer digital_media_(artwork) doggy_style domestic_dog felid feline female female/female fox from_behind_position furniture group group_sex hair hi_res line_art looking_at_viewer lynx male male/female mammal nipples on_bed open_mouth orgy pantherine polaroid_photo prone_bone red_panda reptile scalie selfie sex signed simple_background smile smoking tail tiger wolf
1990s 1993 20th_century 2girls 6boys after_fellatio black_hair bondage buttplug chained chained_collar clothed_male_nude_female collar comic crossbow defeated_villain depuceleur dungeon end_page enema_expulsion female femsub gangbang handdrawn hero human human_only lady_marilyn lady_marilyns_misfortune light-skinned_female light-skinned_male light_skin male maledom merry_men millie_the_maid multiple_boys penis restrained robin_hunk sherrif straight sword villain weapon
1990s 1993 20th_century 2girls 6boys after_fellatio black_hair bondage buttplug chained chained_collar clothed_male_nude_female collar comic crossbow defeated_villain depuceleur dungeon end_page enema_expulsion female femsub gangbang handdrawn hero human human_only lady_marilyn lady_marilyns_misfortune light-skinned_female light-skinned_male light_skin male maledom merry_men millie_the_maid multiple_boys penis restrained robin_hunk sherrif straight sword villain weapon
1990s 1993 1girls 20th_century 3boys bald bald_man bdsm black_and_white black_hair bondage comic damsel_in_distress depuceleur dungeon femsub fight hairy_chest handdrawn hero human human_only lady_marilyn lady_marilyns_misfortune light-skinned_female light-skinned_male light_skin mature mature_male nude nude_female nude_male pillory restrained robin_hunk sherrif stationary_restraints swinging_from_rope sword torch villain weapon
1990s 1993 1girls 20th_century 3boys bald bald_man bdsm black_and_white black_hair bondage comic damsel_in_distress depuceleur dungeon femsub fight hairy_chest handdrawn hero human human_only lady_marilyn lady_marilyns_misfortune light-skinned_female light-skinned_male light_skin mature mature_male nude nude_female nude_male pillory restrained robin_hunk sherrif stationary_restraints swinging_from_rope sword torch villain weapon
1990s 1993 1girls 20th_century 2boys bald bald_man bdsm big_belly bit_gag black_and_white black_hair bondage breast_bondage breast_torture buttplug comic depuceleur dungeon female femsub handdrawn human human_only lady_marilyn lady_marilyns_misfortune light-skinned_female light-skinned_male light_skin male mature mature_male needle nipple_torture nude nude_female nude_male penis pillory rape restrained sex_toy sherrif stomach_bulge straight tied_to_pole vaginal_penetration
1990s 1993 1girls 20th_century 2boys bald bald_man bdsm big_belly bit_gag black_and_white black_hair bondage breast_bondage breast_torture buttplug comic depuceleur dungeon female femsub handdrawn human human_only lady_marilyn lady_marilyns_misfortune light-skinned_female light-skinned_male light_skin male mature mature_male needle nipple_torture nude nude_female nude_male penis pillory rape restrained sex_toy sherrif stomach_bulge straight tied_to_pole vaginal_penetration
1990s 1993 1girls 20th_century 3boys bald bald_man bdsm bit_gag black_and_white black_hair bondage buttplug castle comic depuceleur dungeon enema female femsub hammer handdrawn human human_only lady_marilyn lady_marilyns_misfortune light-skinned_female light-skinned_male light_skin male mature mature_male nude nude_female nude_male plugged_ass restrained robin_hunk sex_toy sherrif stationary_restraints straight tied_to_table wooden_hammer
1990s 1993 1girls 20th_century 3boys bald bald_man bdsm bit_gag black_and_white black_hair bondage buttplug castle comic depuceleur dungeon enema female femsub hammer handdrawn human human_only lady_marilyn lady_marilyns_misfortune light-skinned_female light-skinned_male light_skin male mature mature_male nude nude_female nude_male plugged_ass restrained robin_hunk sex_toy sherrif stationary_restraints straight tied_to_table wooden_hammer
1990s 1993 1girls 20th_century 4boys bald bald_man black_and_white black_hair bondage bow breast_sucking comic depuceleur female forest gangbang gangrape handdrawn human human_only lady_marilyns_misfortune light-skinned_female light-skinned_male light_skin male merry_men millie_the_maid penis rape robin_hunk stripped_naked torn_clothes undressing weapon
1990s 1993 1girls 20th_century 4boys bald bald_man black_and_white black_hair bondage bow breast_sucking comic depuceleur female forest gangbang gangrape handdrawn human human_only lady_marilyns_misfortune light-skinned_female light-skinned_male light_skin male merry_men millie_the_maid penis rape robin_hunk stripped_naked torn_clothes undressing weapon
1990s 1993 1girls 20th_century 2boys bald bald_man bdsm black_hair bondage breast_bondage comic cover_page depuceleur dungeon erection female femsub gag handdrawn human human_only lady_marilyn lady_marilyns_misfortune male mature mature_male needle nude nude_female nude_male part_3 restrained rope_bondage sherrif stationary_restraints straight tied_to_pole
1990s 1993 1girls 20th_century 2boys bald bald_man bdsm black_hair bondage breast_bondage comic cover_page depuceleur dungeon erection female femsub gag handdrawn human human_only lady_marilyn lady_marilyns_misfortune male mature mature_male needle nude nude_female nude_male part_3 restrained rope_bondage sherrif stationary_restraints straight tied_to_pole
1990s 1992 20th_century 2girls 3boys bdsm bit_gag black_and_white black_hair bondage breast_torture comic depuceleur dungeon enema erection female femsub gag handdrawn human human_only lady_marilyn lady_marilyns_misfortune light-skinned_female light-skinned_male light_skin male maledom mature mature_male millie_the_maid needle nude nude_female nude_male penis restrained robin_hunk sherrif stationary_restraints straight tied_to_table
1990s 1992 20th_century 2girls 3boys bdsm bit_gag black_and_white black_hair bondage breast_torture comic depuceleur dungeon enema erection female femsub gag handdrawn human human_only lady_marilyn lady_marilyns_misfortune light-skinned_female light-skinned_male light_skin male maledom mature mature_male millie_the_maid needle nude nude_female nude_male penis restrained robin_hunk sherrif stationary_restraints straight tied_to_table
1990s 1992 1girls 20th_century 2boys anal_insertion bald bald_man bdsm black_and_white black_hair bondage breast_bondage breast_torture candle_in_ass candle_insertion candle_wax chained color comic cum_in_mouth depuceleur dungeon erection female femsub hairy_chest handdrawn human human_only lady_marilyn lady_marilyns_misfortune light-skinned_female light-skinned_male light_skin male maledom masturbation mature mature_male nude nude_female nude_male penis restrained sherrif spreader_bar straight wax_play wax_torture
1990s 1992 1girls 20th_century 2boys anal_insertion bald bald_man bdsm black_and_white black_hair bondage breast_bondage breast_torture candle_in_ass candle_insertion candle_wax chained color comic cum_in_mouth depuceleur dungeon erection female femsub hairy_chest handdrawn human human_only lady_marilyn lady_marilyns_misfortune light-skinned_female light-skinned_male light_skin male maledom masturbation mature mature_male nude nude_female nude_male penis restrained sherrif spreader_bar straight wax_play wax_torture
1990s 1992 1girls 20th_century 2boys bald bald_man bdsm black_and_white black_hair bondage breast_bondage breast_torture chained color comic depuceleur dungeon erection female femsub gag hairy_chest handdrawn human human_only lady_marilyn lady_marilyns_misfortune light-skinned_female light-skinned_male light_skin male maledom mature mature_male nude nude_female nude_male penis restrained sherrif slapping_breasts spreader_bar straight suspension suspension_bondage tied_breasts
1990s 1992 1girls 20th_century 2boys bald bald_man bdsm black_and_white black_hair bondage breast_bondage breast_torture chained color comic depuceleur dungeon erection female femsub gag hairy_chest handdrawn human human_only lady_marilyn lady_marilyns_misfortune light-skinned_female light-skinned_male light_skin male maledom mature mature_male nude nude_female nude_male penis restrained sherrif slapping_breasts spreader_bar straight suspension suspension_bondage tied_breasts
1990s 1992 1girls 20th_century 2boys bald bald_man bdsm black_and_white black_hair bondage breast_bondage breast_torture chained color comic depuceleur dungeon erection female femsub gag hairy_chest handdrawn human human_only lady_marilyn lady_marilyns_misfortune light-skinned_female light-skinned_male light_skin male maledom mature mature_male mouse nude nude_female nude_male restrained sherrif spreader_bar straight tied_to_chair whipping whipping_breasts
1990s 1992 1girls 20th_century 2boys bald bald_man bdsm black_and_white black_hair bondage breast_bondage breast_torture chained color comic depuceleur dungeon erection female femsub gag hairy_chest handdrawn human human_only lady_marilyn lady_marilyns_misfortune light-skinned_female light-skinned_male light_skin male maledom mature mature_male mouse nude nude_female nude_male restrained sherrif spreader_bar straight tied_to_chair whipping whipping_breasts