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1girls 2000 anthro ball_gag bondage bound breasts buttplug canid canine clothes_pin earrings female female_focus female_only fox furry gagged green_eyes ironbadger long_hair mammal nipples on_knees paddle pierced_ears pink_nipples pink_nose red_hair riding_crop rope rope_bondage solo solo_female vibrator vixen vulpine

1girls 2000 anthro braided_hair braids breasts civet female fur furry ironbadger long_tail mammal multicolored_body multicolored_fur naked nipples nude on_knees pointy_ears pubic_hair pussy solo solo_female spots spotted_body spotted_fur spotted_markings tail

anthrobraided_hair

1girls 2000 anthro blond blond_hair blue_eyes bondage bound bound_to_pole bound_wrists breasts dungeon enslaved female furry gloves_(marking) ironbadger mask_(marking) nipples pussy raccoon restrained restraints ringtail socks_(marking) solo vagina

1girls 2000 anthro belt bondage_belt bound bound_ankles bound_tail bound_wrists breasts collar female furry green_eyes ironbadger long_hair long_hair_female naked naked_female nipples nude nude_female nudity otter pussy restrained restrained_arms restrained_legs restraints solo solo_female tail vagina

1girls 2000 after_spanking anthro arms_above_head arms_up back back_view blond blond_hair bondage bound bound_legs bound_tail bound_wrists butt butt_cheeks butt_crack female female_focus female_only furry ironbadger long_hair long_hair_female mephitid nipple pussy red_butt restrained shamira sideboob skunk solo solo_female vagina

after_spankinganthro

2000 anthro arms_behind_back bondage bondage_collar bound bound_ankles bound_arms bound_legs bound_wrists breasts canid canine collar eyes_closed female femsub fox furry hung_up ironbadger nipple_weights nipples pussy restrained rope rope_between_pussy rope_bondage slave_collar spread_legs spreader_bar upside-down vagina vixen vulpine weights_(bdsm)

anthroarms_behind_back

2000 2girls anthro bdsm bondage boots bound breasts canid canine cat dominant_female duo felid feline female/female fox furry gloves ironbadger nipples panties pussy submissive_female underwear vagina vulpine

1girls 2000 anthro anus bondage bound cervid cervine christmas crying crying_with_eyes_open deer doe ek_goya female furry long_hair pussy restrained rope tears vagina white_hair

2000 2girls ankle_cuffs anthro bdsm bent_over black_hair bondage boots bound bound_ankles bound_tail bound_wrists breasts collar dominated_female female female/female female_fox femdom footwear fox furry gloves ironbadger long_gloves long_hair long_hair_female multicolored_body multicolored_fur nipples pussy restrained restraints spreader_bar submissive_female tail_cuff thigh_boots thigh_highs thighhighs vagina vulpine wrist_cuffs yuri

ankle_cuffsanthro

2000 2girls anal anal_insertion anal_penetration ankle_cuffs anthro ball_gag black_body black_fur bondage bound bound_ankles breasts canid canine dildo dildo_in_ass female female/female female_focus female_only female_penetrated furry gag ironbadger jackal multicolored_body multicolored_fur nipples pussy sex_toy sex_toy_in_ass shackled shackles vagina yuri

analanal_insertion

1girls 2000 ankle_cuffs anthro ball_gag black_body black_fur black_hair bondage bound bound_tail bound_to_pole bound_wrists breasts butt butt_cheeks butt_crack canid canine collar cuffed enslaved female furry gagged ironbadger long_hair long_hair_female lupine nipples paddle pawpads paws pole sideboob slave solo solo_female whip wolf wrist_cuffs

ankle_cuffsanthro

1boy 2000 4_tails anthro black_hair brian_o'connell claws cock dick erection femboy fox furry girly licking_lips male male_focus male_only multi_tail multicolored_body multicolored_fur penis shirt tail tails underwear vulpine

anthroblack_hair

2000 2boys anal anal_penetration anal_sex anthro backsack balloons balls ballsack black_and_white bow bushycat cat duo eating eyes_closed feline femboy furry girly hair_bow hair_ribbon long_hair long_hair_male male/male male_focus male_only mouth_open penis penis_in_ass siamese siamese_cat testicles

analanal_penetration

1boy 1girls 2000 2000s 2000s_and_2010s_style 2d 2d_(artwork) 2d_animation 360p akiyama_sakura animated black_hair blackmail clothed_male clothed_male_nude_female devious_smile female kyouhaku kyouhaku_2 long_black_hair long_hair milf mole mole_under_mouth mother nudity_mother pink_pineapple sakura_akiyama screenshot single_mom

akiyama_sakuraanimated

2000 2girls anthro bdsm bondage bound cat feline female female/female femdom fishnet_legwear fishnet_stockings footwear furry heels high_heels interspecies lesbian paddle skunk spanked stripes_(marking) yuri zig_zag

1girls 2000 anthro ball_gag big_cat blonde_hair bondage bound bound_tail breasts cheetah feline female furry gagged ironbadger long_hair long_hair_female navel navel_piercing nipple_rings nipples pussy

2000 anthro backsack balls black_and_white dinosaur furry grass looking_at_viewer male manawolf presenting presenting_hindquarters reptile solo solo_male testicles

2000 animal_genitalia anthro balls bodily_fluids bushycat canid canine canis closed_eyes cum digitigrade erection fur genital_fluids genitals greyscale group licking licking_lips line_art male mammal micro monochrome navel nipples nude penis sheath simple_background solo_focus tail text tongue tongue_out traditional_media_(artwork) white_background wolf

animal_genitaliaanthro

2000 anthro apatosaurus astor back_muscles balls big_abs big_balls big_biceps big_muscles big_pecs big_penis big_quads dinosaur diplodocid fingers flaccid genitals gideon hi_res huge_balls huge_cock humanoid_genitalia humanoid_penis hyper hyper_balls hyper_genitalia hyper_penis long_neck long_tail macro male muscular muscular_anthro muscular_male nude pecs pen_(artwork) penis reptile sauropod scales scalie simple_background solo tail traditional_media_(artwork) white_background

anthroapatosaurus

00s 2+girls 2000 2000s 2000s_and_2010s_style 2d 2d_(artwork) 8girls ayaka_minami blonde_female blonde_hair blonde_hair_female blue_eyes_female blue_hair blue_hair_female blush braided_hair braided_twintails brown_hair_female drill_hair dvd_cover eri_takabe face_focus female female_focus female_only fujima_moeko ganguro glasses green_eyes_female green_skirt hairband hi_res highres japanese japanese_female kondou_nagisa kurihara_asami long_blue_hair long_brown_hair long_green_hair long_hair long_twintails maejima_kaori meganekko minazuki_shiho nagumo_chiaki over_480p pink_hair pink_hair_female pink_pineapple purple_hair purple_hair_female red_hair red_hair_female schoolgirl shusaku shusaku_replay skirt takabe_eri tied_hair twintails white_hairband younger_female

ayaka_minamiblonde_female

2000 anal anal_sex asphyxiation badger bodily_fluids bondage bondage bound breath_play bubble canid canine colored_pencil_(artwork) cum darkwolfie diving_mask fox from_front_position genital_fluids group handjob hands_behind_back hi_res lying male male/male male_penetrated male_penetrating male_penetrating_male mammal mask missionary_position mustelid musteline on_back penetration penile pool questionable_consent red_fox restraints rope rope_bondage scuba scuba_gear scuba_tank sex traditional_media_(artwork) trio underwater underwater_sex water wrists_tied

1female 1girls 2000 bottomless breasts buttplug_tail collar female gag nipple_rings nipples_exposed partially_clothed petgirl petplay puppygirl puppyplay solo_female the_veterinarian

bottomlessbreasts

1boy 2000 black_fur black_hair black_panther doggy_style female feral human human_on_feral interspecies light-skinned_female light_skin male naked_female nude nude_female panther straight the_veterinarian zoophilia

black_furblack_hair

2000 african_female bondage buttplug_tail collar frame leash shackles stockings the_veterinarian

african_femalebondage

1female 2000 ass_up ball_of_yarn doggy_style interspecies minotaur naked_female symbol the_veterinarian

ass_upball_of_yarn

2000 2girls all_the_way_through armbinder arms_tied_above_head arms_tied_behind_back arms_tied_together bending_over bondage cfnf clitoris_piercing electric human_furniture lamp legs_apart lightbulb lighting metal_frame multiple_girls naked_female object_in_ass objectification plug red_hair ring_gag shackles spreader_bar stationary_restraints the_veterinarian

all_the_way_througharmbinder

2000 ball_of_yarn bell collar kittyplay nose_ring petgirl petplay the_veterinarian tits_out

ball_of_yarnbell

2000 3d arms_tied asian_female black_hair bondage caning legs_tied naked_female slave spread_eagle suspension thrallord tree whipping_marks

arms_tiedasian_female

1female 1girls 2000 2boys 3d arms_tied clothed_male_nude_female completely_nude cross crucifixion legs_tied_together naked_female outdoors punishment slave solo thrallord

arms_tiedclothed_male_nude_female

1animal 1dog 1girls 2000 2000s 2000s_and_2010s_style 3d anal_insertion arms_tied blonde_hair blonde_pubic_hair bondage canine double_insertion double_penetration english_text hut indoors long_hair medium_breasts mountainous_horizon naked_female outside peeing peeing_on_another pubic_hair smoke standing_on_tip_toes stationary_restraints stick_in_pussy thrallord tiptoes tree twin_braids uncensored urinating urine vaginal_insertion

anal_insertionarms_tied

1girls 2000 2000s 2000s_and_2010s_style 3d bikini_tan black_hair completely_nude_female crucifixion drooling execution long_hair medium_breasts mountainous_horizon outdoors pubic_hair solo thrallord unusual_position web_address

bikini_tanblack_hair

1boy 1girls 2000 3d bondage buttplug buttplug_in_ass dildo dildo_in_pussy female male maledom naked_female nude_female pubic_hair saint_andrew's_cross sex_toy shackles spread_eagle thrallord upside-down vaginal

bondagebuttplug

1female 2000 3d bondage boots_only brown_hair chains crucifixion execution glasses lara_croft lara_croft_(classic) naked_female parody thrallord tomb_raider

bondageboots_only

00s 2000 3d arms_tied_behind_back bondage brown_hair legs_tied naked_female shackled shackled_ankles shackled_wrists shackles suspension thrallord wrists_chained

arms_tied_behind_backbondage

00s 1girls 2000 2000s 2000s_(style) 2000s_and_2010s_style 3d air_bubble armpits artist_name bucket chained_to_floor concrete_block dutch_angle fish full_body imminent_drowning ocean_floor original pink_bikini shark solo thrallord transparent_bikini underwater underwater_view web_address

air_bubblearmpits

2000 3d electric_shock electrostimulation naked_female pinned pinned_down spread_eagle spread_legs thrallord

electric_shockelectrostimulation

00s 1girls 2000 2000s 2000s_and_2010s_style 3d arms_tied_behind_back artist_name bangs_pinned_back bondage brown_hair chain chained copyright_name corkscrew female medium_breasts naked naked_female nipple_insertion nipple_penetration nipple_torture nude nude_female original ponytail thrallord tile_floor web_address

arms_tied_behind_backartist_name

00s 1girls 2000 2000s 2000s_and_2010s_style 3d anal_insertion arms_behind_back arms_tied_behind_back artist_name bowtie breasts_apart brown_hair candy_cane character_name copyright_name dated day double_insertion full_body lollipop lollipop_in_ass minigirl mountainous_horizon navel nude_female outdoor_nudity outdoors overcast pink_socks pointy_ears red_bowtie red_footwear red_lips red_sneakers shoes_only short_hair skinny skinny_female skinny_girl small_breasts sneakers solo spread_legs tagme thrallord uncensored vaginal_insertion vaginal_object_insertion web_address

anal_insertionarms_behind_back

2000 anal_object_insertion ball_gag bells bondage candy_cane candy_cane_in_ass candy_cane_insertion christmas collar duo fire fireplace nipple_bells santa_claus santa_hat socks suspension the_veterinarian

anal_object_insertionball_gag

2000 3d bondage lying_on_floor naked_female net nipple_piercing pubic_hair red_hair rope_bondage thrallord

bondagelying_on_floor

1female 1girls 2000 2001 2boys african_female ball_gag bondage box cage caged cavity_search clothed_male_nude_female customs dark-skinned_female examination femsub gag gloves imminent_anal imminent_anal_penetration imminent_penetration interracial light-skinned_male master_and_pet master_and_slave medical medical_examination naked_female nude_female only_one_naked presenting presenting_anus presenting_hindquarters presenting_pussy puppyplay table the_veterinarian vaseline veterinarian

african_femaleball_gag

2000 buttplug_tail canine collar petgirl petplay princess the_veterinarian thermometer veterinarian water_bowl

buttplug_tailcanine

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