shackle best from all time animated

Time frame

shackle

1girls 2boys 3d animated behind_bars belly_bulge blizzard_entertainment body_writing breast_grab breasts cell chained chains cum cum_in_pussy cum_inside cum_pool dark-skinned_male fat_man fear female fuckingtracer handcuffed handcuffs humiliation interracial male missionary_position nipples no_sound overwatch pregnancy_test pregnant prison prison_bitch prison_cell prisoner rape restrained shackle straight tattoo testicles tracer video
1girls 2boys 3d animated behind_bars belly_bulge blizzard_entertainment body_writing breast_grab breasts cell chained chains cum cum_in_pussy cum_inside cum_pool dark-skinned_male fat_man fear female fuckingtracer handcuffed handcuffs humiliation interracial male missionary_position nipples no_sound overwatch pregnancy_test pregnant prison prison_bitch prison_cell prisoner rape restrained shackle straight tattoo testicles tracer video
3d animated cell chained chains collar cum cum_on_penis dark-skinned_male fat_man fear fuckingtracer interracial licking licking_face maledom no_sound nude_female nude_male overwatch prison prison_bitch prison_cell prisoner rape restrained scared shackle straight tagme testicles tracer video
3d animated cell chained chains collar cum cum_on_penis dark-skinned_male fat_man fear fuckingtracer interracial licking licking_face maledom no_sound nude_female nude_male overwatch prison prison_bitch prison_cell prisoner rape restrained scared shackle straight tagme testicles tracer video
1girls animated aroused blush bondage breasts brown_eyes captured captured_heroine caryo censored cervical_penetration chained_wrists chains clothing corruption cuffs cum cum_on_body cum_on_breasts cum_on_face cum_on_upper_body elf elf_ears elf_female facial female femsub game_cg handjob interspecies kangoku_no_elf large_breasts larger_male light-skinned_female looking_pleasured male male_orc/female_elf maledom mature_male missionary_position monster monster_cock monster_rape mosaic_censoring on_back open_mouth orc orc_male panties panties_aside penetration penis perfect_loop pink_hair pleasure_rape pointy_ears ponytail pussy rape restrained restraints sex sex_slave shackle size_difference slave slim_waist smaller_female straight teratophilia thighhighs thrusting tied_hair underwear uterus vaginal_penetration x-ray
1girls animated aroused blush bondage breasts brown_eyes captured captured_heroine caryo censored cervical_penetration chained_wrists chains clothing corruption cuffs cum cum_on_body cum_on_breasts cum_on_face cum_on_upper_body elf elf_ears elf_female facial female femsub game_cg handjob interspecies kangoku_no_elf large_breasts larger_male light-skinned_female looking_pleasured male male_orc/female_elf maledom mature_male missionary_position monster monster_cock monster_rape mosaic_censoring on_back open_mouth orc orc_male panties panties_aside penetration penis perfect_loop pink_hair pleasure_rape pointy_ears ponytail pussy rape restrained restraints sex sex_slave shackle size_difference slave slim_waist smaller_female straight teratophilia thighhighs thrusting tied_hair underwear uterus vaginal_penetration x-ray
1girls 2boys 3d animated belly_bulge blizzard_entertainment body_writing breast_grab breasts cell chained chains cum cum_in_pussy cum_inside cum_pool dark-skinned_male fat_man female fuckingtracer hand_on_breast handcuffed handcuffs interracial male missionary_position nipples no_sound nude overwatch pregnancy_test pregnant prison prison_bitch prison_cell prisoner rape restrained sex shackle straight tattoo tracer vaginal_penetration video
1girls 2boys 3d animated belly_bulge blizzard_entertainment body_writing breast_grab breasts cell chained chains cum cum_in_pussy cum_inside cum_pool dark-skinned_male fat_man female fuckingtracer hand_on_breast handcuffed handcuffs interracial male missionary_position nipples no_sound nude overwatch pregnancy_test pregnant prison prison_bitch prison_cell prisoner rape restrained sex shackle straight tattoo tracer vaginal_penetration video
1girls 2boys 3d ambiguous_penetration anal anal_sex animated big_ass big_butt big_penis bubble_butt chain_leash chained chains cheating cheating_girlfriend collar cum cum_eating cum_in_bowl cum_in_mouth cum_on_bowl cum_on_face cumshot dark-skinned_male dog_bowl face_down_ass_up female femsub fuckingtracer happy_sub huge_ass huge_cock interracial male maledom multiple_boys muscular_male no_sound nude overwatch pinned pinned_down shackle slave straight submissive_female tagme threesome top-down_bottom-up tracer video
1girls 2boys 3d ambiguous_penetration anal anal_sex animated big_ass big_butt big_penis bubble_butt chain_leash chained chains cheating cheating_girlfriend collar cum cum_eating cum_in_bowl cum_in_mouth cum_on_bowl cum_on_face cumshot dark-skinned_male dog_bowl face_down_ass_up female femsub fuckingtracer happy_sub huge_ass huge_cock interracial male maledom multiple_boys muscular_male no_sound nude overwatch pinned pinned_down shackle slave straight submissive_female tagme threesome top-down_bottom-up tracer video
1girls 2boys 3d animated behind_bars belly_bulge blizzard_entertainment body_writing breast_grab breasts cell chained chains dark-skinned_male fat_man female fuckingtracer handcuffed handcuffs interracial male missionary_position no_sound nude overwatch pregnancy_test pregnant prison prison_bitch prison_cell prisoner rape restrained scat shackle straight tattoo testicles threesome tracer vaginal_penetration video
1girls 2boys 3d animated behind_bars belly_bulge blizzard_entertainment body_writing breast_grab breasts cell chained chains dark-skinned_male fat_man female fuckingtracer handcuffed handcuffs interracial male missionary_position no_sound nude overwatch pregnancy_test pregnant prison prison_bitch prison_cell prisoner rape restrained scat shackle straight tattoo testicles threesome tracer vaginal_penetration video
16:9 3d @oz animated approximated_aspect_ratio arms_behind_back blue_hair bondage braid breasts breasts_out chains closed_eyes collar dildo female helpless insertion maid maid_headdress moaning nipples on_floor panties panties_aside sakuya_izayoi shackle short_hair solo spreader_bar thighhighs top-down_bottom-up touhou twin_braids underwear vaginal_penetration vibrator white_legwear
16:9 3d @oz animated approximated_aspect_ratio arms_behind_back blue_hair bondage braid breasts breasts_out chains closed_eyes collar dildo female helpless insertion maid maid_headdress moaning nipples on_floor panties panties_aside sakuya_izayoi shackle short_hair solo spreader_bar thighhighs top-down_bottom-up touhou twin_braids underwear vaginal_penetration vibrator white_legwear
1girls 2d 2d_(artwork) 3boys ahe_gao ambiguous_penetration anemone_antimony animated anklet ass ass_bigger_than_head belly_bulge big_dom_small_sub bisexual bisexual_male bracelet butt_squish carrying_partner chubby chubby_belly collar cum cum_inside cum_overflow cumflation cumming_while_penetrated cumshot demon demon_boy demon_girl demon_tail excessive_cum fat_ass female fleshlight_position foursome fucked_silly geministarsign heart heart-shaped_pupils holding_hands horn horns huge_ass huge_balls huge_cock humanoid_penis imp kissing kissing_while_penetrated large_ass large_balls large_breasts large_cock large_penis lewddmon long_tongue male/female male/male male_penetrated moaning moaning_in_pleasure monster monster_boy monster_cock monster_girl nipple_piercing oerba_yun_fang original pear_shaped penis piercing plap plap_(sound) pointy_ears red_skin self_upload shackle shackles shiny_skin shortstack side_view size_difference slideshow small_but_hung smaller_female smaller_male sound spade_tail sweat sweaty_ass sweaty_balls sweaty_body sweaty_genitalia tagme tears tears_of_pleasure tongue tongue_kiss tongue_out veiny_penis video wide_hips yellow_eyes
1girls 2d 2d_(artwork) 3boys ahe_gao ambiguous_penetration anemone_antimony animated anklet ass ass_bigger_than_head belly_bulge big_dom_small_sub bisexual bisexual_male bracelet butt_squish carrying_partner chubby chubby_belly collar cum cum_inside cum_overflow cumflation cumming_while_penetrated cumshot demon demon_boy demon_girl demon_tail excessive_cum fat_ass female fleshlight_position foursome fucked_silly geministarsign heart heart-shaped_pupils holding_hands horn horns huge_ass huge_balls huge_cock humanoid_penis imp kissing kissing_while_penetrated large_ass large_balls large_breasts large_cock large_penis lewddmon long_tongue male/female male/male male_penetrated moaning moaning_in_pleasure monster monster_boy monster_cock monster_girl nipple_piercing oerba_yun_fang original pear_shaped penis piercing plap plap_(sound) pointy_ears red_skin self_upload shackle shackles shiny_skin shortstack side_view size_difference slideshow small_but_hung smaller_female smaller_male sound spade_tail sweat sweaty_ass sweaty_balls sweaty_body sweaty_genitalia tagme tears tears_of_pleasure tongue tongue_kiss tongue_out veiny_penis video wide_hips yellow_eyes
1girls 2boys 3d ambiguous_penetration animated big_ass big_butt big_penis bubble_butt chain_leash chained chains cheating cheating_girlfriend collar cum cum_eating cum_in_bowl cum_in_mouth cum_on_bowl cum_on_face cumshot dark-skinned_male dog_bowl face_down_ass_up female femsub fuckingtracer happy_sub huge_ass huge_cock interracial male maledom multiple_boys muscular_male no_sound nude overwatch pinned pinned_down shackle slave straight submissive_female tagme threesome top-down_bottom-up tracer video
1girls 2boys 3d ambiguous_penetration animated big_ass big_butt big_penis bubble_butt chain_leash chained chains cheating cheating_girlfriend collar cum cum_eating cum_in_bowl cum_in_mouth cum_on_bowl cum_on_face cumshot dark-skinned_male dog_bowl face_down_ass_up female femsub fuckingtracer happy_sub huge_ass huge_cock interracial male maledom multiple_boys muscular_male no_sound nude overwatch pinned pinned_down shackle slave straight submissive_female tagme threesome top-down_bottom-up tracer video
3d @oz animated arms_behind_back blue_hair bondage bouncing_breasts braid breasts breasts_out censored chains collar dildo dungeon female hanging_breasts helpless indoors insertion maid maid_headdress moaning on_floor panties panties_aside sakuya_izayoi shackle short_hair skindentation solo spreader_bar thighhighs top-down_bottom-up touhou twin_braids underwear vaginal_penetration white_legwear
3d @oz animated arms_behind_back blue_hair bondage bouncing_breasts braid breasts breasts_out censored chains collar dildo dungeon female hanging_breasts helpless indoors insertion maid maid_headdress moaning on_floor panties panties_aside sakuya_izayoi shackle short_hair skindentation solo spreader_bar thighhighs top-down_bottom-up touhou twin_braids underwear vaginal_penetration white_legwear
2023 3d 3d_animation abs animal_genitalia animal_penis animated anthro arm_tied ball_gag barefoot big_gag bondage bottomwear bottomwear_down bound canine_genitalia captured clothed cuff_(restraint) dangling digital_media_(artwork) dransvitry feet forest gag gagged ghostoast hi_res hybrid_genitalia hybrid_penis knot leg_tied loop male mammal military military_uniform muscular muscular_anthro muscular_male muscular_sub nipple nude outside pants pants_down partially_clothed paws pecs penis plantigrade questionable_consent restrained restraints rope rope_bondage scar shackle short_playtime snow sound sound_warning straining struggling submissive submissive_male suspension suspension_bondage tagme tied_balls toes uniform upside-down video voice_acted widescreen wolf
2023 3d 3d_animation abs animal_genitalia animal_penis animated anthro arm_tied ball_gag barefoot big_gag bondage bottomwear bottomwear_down bound canine_genitalia captured clothed cuff_(restraint) dangling digital_media_(artwork) dransvitry feet forest gag gagged ghostoast hi_res hybrid_genitalia hybrid_penis knot leg_tied loop male mammal military military_uniform muscular muscular_anthro muscular_male muscular_sub nipple nude outside pants pants_down partially_clothed paws pecs penis plantigrade questionable_consent restrained restraints rope rope_bondage scar shackle short_playtime snow sound sound_warning straining struggling submissive submissive_male suspension suspension_bondage tagme tied_balls toes uniform upside-down video voice_acted widescreen wolf
1boy 1boy1girl 1girls 4_eyes animated bare_breasts bare_shoulders big_penis black_body black_skin boobjob darksiders darksiders_2 darksiders_3 death_(darksiders) envy_(darksiders) female flaming_hair glowing_eyes glowing_finger glowing_markings glowing_tattoo grey_penis grey_skin handjob kcenofil_(artist) long_penis male male/female markings multi_eye penis shackle shackles shade sideboob squeezing_breast stroking stroking_cock stroking_penis tattoo tattoos watcher_(darksiders) wings
1boy 1boy1girl 1girls 4_eyes animated bare_breasts bare_shoulders big_penis black_body black_skin boobjob darksiders darksiders_2 darksiders_3 death_(darksiders) envy_(darksiders) female flaming_hair glowing_eyes glowing_finger glowing_markings glowing_tattoo grey_penis grey_skin handjob kcenofil_(artist) long_penis male male/female markings multi_eye penis shackle shackles shade sideboob squeezing_breast stroking stroking_cock stroking_penis tattoo tattoos watcher_(darksiders) wings