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1999

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1990s_(style) 1999 1boy animal_ears animated astral_(words_worth) back bell bent_over blush breasts cat_ears cat_tail cave closed_eyes clothed_female_nude_male clothed_sex collar cum doggy_style female female fingering grabbing_another's_breast groping jingle_bell leaning_forward long_hair lowres medium_breasts moaning navel neck_bell nina_(words_worth) nipples nude open_mouth pink_hair pumping restrained retro_artstyle sex sex_from_behind sound straight tagme tail top-down_bottom-up uncensored vaginal_penetration video words_worth

animal_earsanimated

1990s_(style) 1999 1boy animal_ears animated astral_(words_worth) back bell bent_over blush breasts cat_ears cat_tail cave closed_eyes clothed_female_nude_male clothed_sex collar cum doggy_style female female fingering grabbing_another's_breast groping jingle_bell leaning_forward long_hair lowres medium_breasts moaning navel neck_bell nina_(words_worth) nipples nude open_mouth pink_hair pumping restrained retro_artstyle sex sex_from_behind sound straight tagme tail top-down_bottom-up uncensored vaginal_penetration video words_worth

animal_earsanimated

1990s_(style) 1999 1boy animal_ears animated astral_(words_worth) bell bent_over blush breasts cat_ears cat_tail cave closed_eyes clothed_female_nude_male clothed_sex collar female female fingering grabbing_another's_breast groping jingle_bell long_hair lowres medium_breasts moaning navel neck_bell nina_(words_worth) nipples nude open_mouth pink_hair pumping retro_artstyle sound straight tagme tail uncensored video words_worth

animal_earsanimated

1990s_(style) 1999 animated bathroom blonde_hair blue_eyes breasts censored female female indoors interior long_hair lowres navel nipples nude retro_artstyle sharon_(words_worth) solo sound standing tagme video washing_hair words_worth

animatedbathroom

1990s_(style) 1999 animated bathroom blonde_hair blue_eyes breasts censored female female indoors interior long_hair lowres navel nipples nude retro_artstyle sharon_(words_worth) solo sound standing tagme video washing_hair words_worth

animatedbathroom

1999 1girls after_fellatio blush bukkake closed_eyes cum cum_in_mouth cum_on_body cum_on_hands dynamite_kantou facial female female_focus female_only gokkun good_girl hair_ribbon highres japanese_text licking licking_finger light-skinned_male light_skin long_hair looking_pleasured military_uniform monochrome naughty_face open_mouth pleasure_face pleasured ponytail ribbon sakura_shinguji sakura_wars sega smile solo sweat teeth tongue tongue_out traditional_media translated uniform

after_fellatioblush

1999 1boy 1girls bar_censor blush bukkake censored cum cum_on_body cum_on_hands cumdrip cupping_hands dynamite_kantou ejaculation facial female from_side good_girl hair_ribbon half-closed_eyes hands_together highres horny horny_female japanese_text long_hair looking_pleasured male military_uniform monochrome naughty_face oogami_ichirou open_mouth orgasm own_hands_together penis pleasure_face pleasured pointless_censoring ponytail ribbon sakura_shinguji sakura_wars saliva sega smile source_request sweat tongue tongue_out translated uniform

bar_censorblush

1999 1boy 1girls bar_censor blush censored cum cum_on_body dynamite_kantou ejaculation facial female hair_ribbon half-closed_eyes highres japanese_text long_hair looking_pleasured male male_masturbation masturbation military_uniform monochrome naughty_face oogami_ichirou open_mouth orgasm penis pleasure_face pleasured pointless_censoring ponytail ribbon sakura_shinguji sakura_wars saliva sega smile source_request sweat translated uniform

bar_censorblush

1999 1boy 1girls bar_censor blush censored cum cum_on_body dynamite_kantou ejaculation facial female hair_ribbon happy highres japanese_text long_hair looking_pleasured male military_uniform monochrome one_eye_closed oogami_ichirou open_mouth penis pleasure_face pleasured pointless_censoring ponytail ribbon sakura_shinguji sakura_wars saliva sega smile source_request sweat translated uniform

bar_censorblush

1999 1boy 1girls balls big_penis blush deepthroat dynamite_kantou face_fucking fellatio female hair_ribbon half-closed_eyes handjob highres irrumatio japanese_text male military_uniform monochrome oogami_ichirou oral penis ponytail pov pubic_hair ribbon sakura_shinguji sakura_wars saliva sega source_request straight sweat testicles tongue tongue_out uniform

1999 1boy 1girls ball_sucking balls bar_censor blush censored dynamite_kantou fellatio female hair_ribbon half-closed_eyes handjob highres japanese_text large_penis long_hair looking_at_viewer looking_back male military_uniform monochrome oogami_ichirou oral penis penis_grab pointless_censoring ponytail pubic_hair ribbon sakura_shinguji sakura_wars sega source_request straight sweat testicle_sucking testicles translated uniform

ball_suckingballs

1999 1boy 1girls ball_grab balls balls_touching blush caressing_balls caressing_testicles dynamite_kantou fellatio female good_girl hair_ribbon handjob japanese_text large_penis licking looking_pleasured male military_uniform monochrome oogami_ichirou open_mouth oral penis penis_grab pleasure_face pleasured ponytail pubic_hair ribbon sakura_shinguji sakura_wars sega smile source_request straight sweat testicle_grab testicles tongue tongue_out translation_request uniform

1999 1girls anal_only anus ass ass_focus bent_over big_ass censored close-up clothes_pull come_hither dynamite_kantou female female_only highres horny horny_female invitation inviting inviting_to_sex legs military_uniform monochrome pants pants_pull pubic_hair pussy sakura_shinguji sakura_wars sega sensual solo spread_anus sweat thick_thighs thighs voluptuous

1999 anthro big_breasts bound breasts brown_body brown_eyes brown_fur brown_hair chest_tuft christmas christmas_decorations christmas_ornament copyright_symbol dialogue doug_winger english_text eyelashes female fur hair holidays labels mammal nipples nude nude_female object_in_mouth profanity ribbons rodent sciurid solo squirrel_tail symbol tail text thought_bubble tree_squirrel tuft

anthrobig_breasts

1999 1girls ainu_clothes ass black_hair blue_eyes blue_hair breasts female female_only fingerless_gloves from_behind gloves hair_ribbon hi_res king_of_fighters long_hair mamahaha nakoruru no_panties open_mouth retro_artstyle ribbon samurai_shodown sensual sideboob small_breasts snk traditional_media traditional_media_(artwork) translation_request weapon yoshinaga_eikichi

ainu_clothesass

1999 1girls artist_name artist_signature black_panties blue_eyes blush bra breasts brown_hair deep_cleavage female female_focus female_only g-string highleg highleg_panties huge_breasts inoue_takuya lace lace-trimmed_bra lace_trim legs lingerie office_lady open_clothes open_shirt original original_character panties pink_nail_polish pink_nails shirt solo solo_female solo_focus thighhighs thong underwear undressing

artist_nameartist_signature

1999 1girls artistic_nude casual closed_eyes featureless_breasts female human kasumi_(pokemon) ken_sugimori nintendo nonsexual_nudity nude nude_female nudist official_art orange_hair pale_skin pokemon pokemon_rgby pokemon_tcg sideboob small_breasts solo solo_female staryu tears water

artistic_nudecasual

1999 athletic athletic_female big_breasts blackfell blue_eyes breasts busty female female_focus female_only hourglass_figure lara_croft lara_croft_(classic) large_breasts lipstick looking_over_eyewear looking_over_sunglasses makeup navel nude nude_female nudity slim_waist sunglasses tagme tinted_eyewear tomb_raider water wide_hips

athleticathletic_female

1990s 1999 20th_century 2_penises 2_tails ambiguous_penetration american_tails anthro archie_comics black_nose bodily_fluids boots bottomless breasts brown_body brown_fur canid canine classic_tails clothed clothing dialogue diphallia diphallism dipstick_tail duo english_text female footwear fox fur genital_fluids genitals gloves ground_squirrel hair handwear kthanid_(artist) looking_at_another looking_at_partner looking_back looking_back_at_another looking_back_at_partner male male/female mammal markings multi_genitalia multi_penis multi_tail nipples nude open_clothing open_topwear open_vest penetration penis red_hair rodent sally_acorn sciurid scut_tail sega shoes short_tail small_breasts sonic_(series) sonic_satam sonic_the_hedgehog_(archie) sonic_the_hedgehog_(comics) sonic_the_hedgehog_(series) tail tail_markings tails tails_the_fox text topwear vaginal_fluids vest wildbrain

ambiguous_penetrationamerican_tails

1999 3_toes 4_fingers accessory anthro ass bedroom_eyes black_body black_fur bodily_fluids bottomwear braided_hair breasts butt_focus camera chest_tuft cleavage clitoral_hood clitoris close-up closed_eyes clothed clothing cum cum_on_anus cum_on_butt cum_on_penis cum_on_tail cum_string dialogue digital_media_(artwork) disembodied_penis duo erection eric_schwartz facial_markings feet felid fellatio female fingers fur genital_close-up genital_fluids genitals hair hair_accessory hair_ribbon hatching_(art) head_markings hi_res holding_camera holding_object holding_photo humanoid_genitalia humanoid_penis hybrid licking licking_lips long_hair male male/female mammal markings multiple_images narrowed_eyes nipple_outline open_mouth oral pantherine pants penetration penile penis plantigrade pussy pussy_close-up question raised_tail ribbons saliva saliva_on_tongue seductive sex shaded shirt shorts signature simple_background speech_bubble standing striped_body striped_fur striped_markings striped_tail stripes t-shirt tail tail_markings tamar toes tongue topwear tuft vaginal_fluids vaginal_penetration vein veiny_penis white_background white_body white_fur white_hair zig_zag

accessoryanthro

1999 4_fingers anthro black_and_white breasts cleavage closed_eyes clothed clothing digital_drawing_(artwork) digital_media_(artwork) duo english_text eric_schwartz eyewear eyewear_on_head facial_markings fantasizing female fingers fur glasses glasses_on_head hair hand_on_own_breast head_markings head_on_hand heart_symbol hybrid lidded_eyes long_hair looking_pleasured mammal markings medium_hair mephitid monochrome nipple_outline open_mouth sabrina_(sabrina_online) sabrina_online signature simple_background skunk striped_body striped_fur stripes text thought_bubble translucent translucent_hair white_background white_hair zig_zag

anthroblack_and_white

1999 4_fingers all_the_way_through all_three_filled ambiguous_gender anal anal_sex anthro ass big_breasts black_body black_fur bodily_fluids boots breasts clothing consentacles cum cum_covered cum_in_hair cum_on_breasts cum_on_butt cum_on_face cum_on_tentacle demon demona_(joe_rosales) duo eric_schwartz female female/ambiguous fingers fishnet_clothing fishnet_legwear fur genital_fluids hair hand_on_butt hatching_(art) heart_symbol high_heeled_boots high_heels horn legwear legwear_only licking licking_lips lidded_eyes long_hair looking_at_another looking_at_partner looking_back looking_pleasured mammal mephitid messy monochrome multiple_insertions nipples oral oral_penetration penetration raised_tail restrained restrained_by_tentacles sex shaded side_boob side_view simple_shading skunk slimy_(eric_schwartz) tail tentacle tentacle_around_horn tentacle_creature tentacle_in_ass tentacle_in_mouth tentacle_in_pussy tentacle_penetration tentacle_sex tentacles_around_arms tentacles_around_legs tentacles_around_tail tongue traditional_media_(artwork) vaginal_penetration white_body white_fur

all_the_way_throughall_three_filled

1990s 1990s_(style) 1999 1boy 1girls 20th_century 2d 2d_(artwork) 2d_animation 2girls 90s 960x720 almost_caught animated animation apologizing bed being_watched blackmail blush bouncing_breasts breast_grab breasts brown_hair brown_hair_female changing_clothes clothed clothed_male coercion dubbed_version elf_(company) embarrassed_female english_audio english_dialogue english_dub english_voice english_voice_acting female forest fujima_moeko glasses green_eyes green_eyes_female hentai hentai_series hi_res high_resolution highres implied_masturbation implied_penetration indoors long_hair long_red_hair long_twintails long_video longer_than_30_seconds longer_than_3_minutes longer_than_one_minute male meganekko minazuki_shiho mp4 night nipples older_male older_man_and_younger_girl orange_dress over_480p peeing peeing_female pink_pineapple rape recording recording_sex red_hair rubbing_ass rubbing_leg shusaku socks sound tears twintails twintails_(hairstyle) urine video video_camera video_recording virgin virginity_loss voice_acted waiting_for_sex watching yellow_towel younger_female

almost_caughtanimated

1999 artist_name artist_signature athletic athletic_female aya_brea blonde_hair blue_eyes busty don_shigeru edit female female_focus female_only grobulus hourglass_figure parasite_eve pinup pinup_pose short_hair square_enix tagme tagme_(artist) wide_hips

artist_nameartist_signature

1999 1girls anus big_ass big_breasts bread breasts cum cum_on_body female huge_belly huge_butt kiki's_delivery_service large_breasts nipples nude osono pregnant pussy red_hair scat team_shuffle translated trump trump_(team_shuffle)

1999 3d 4girls 90s black_hair bondage brown_hair chain_collar chain_gang coffle collar desert execution exposed female female_only insects naked_female nude_female red_hair render spread_eagle thrallord

black_hairbondage

1999 3d 6boys abducted arms_tied_to_pole ballet bondage bound castle cmnf female forced_to_watch kidnapped kidnapping kneeling kneeling_female knight naked_female nude_female render rope_bondage swan_lake thrallord wrists_tied

abductedarms_tied_to_pole

1990s 1999 2girls balloon_inflation belly_expansion blonde_hair breast_expansion breasts_bigger_than_head brunette bursting colored comic death defeated female female_death fuusenroba gloves inflation kiss kiss_of_death kissing_through_mask kitana leotard mileena mortal_kombat multiple_girls popping ripping_clothing tagme thighhighs

balloon_inflationbelly_expansion

1990s 1999 2girls anthro beer belly_expansion blimp blue_pony breast_expansion breasts breasts_bigger_than_head carrie_nation colored comic dialogue floating fuusenroba horse hose hose_bulge immobile inflation multiple_girls narration nude sunken_head sunken_limbs tagme tethered text

1990s 1999 2girls anal_insertion anthro beer belly_expansion blue_pony breast_expansion breasts breasts_bigger_than_head carrie_nation colored comic dialogue fuusenroba horse hose hose_bulge immobile implied_penetration inflation leotard multiple_girls narration nipples nude rolling tagme text

anal_insertionanthro

1990s 1999 2girls anthro axe beer belly_expansion blue_pony breast_expansion breasts breasts_bigger_than_head carrie_nation colored comic dialogue fuusenroba horse immobile inflation multiple_girls narration nude tagme text

1990s 1999 2girls anthro beer belly_expansion blue_pony breast_expansion breasts breasts_bigger_than_head carrie_nation colored comic dialogue fuusenroba glasses horse inflation multiple_girls narration nude tagme tail text

1990s 1999 1boy1girl anthro belly_expansion boxers bra breast_expansion christmas colored female fuusenroba horse hug inflation inflation_fetish male panties soft_belly tagme

anthrobelly_expansion

1990s 1999 20th_century 2boys anthro canid canine cum_in_mouth cum_in_own_mouth dog drinking_own_cum duo erect_penis erection fox frank_gembeck furry gay genitals licking_ass malamute male/male male_focus male_only nipples penis rimjob rimming rimming_male vulpine yaoi

1990s 1999 20th_century 2boys anal anal_penetration anal_sex anthro anthro_on_anthro anthro_penetrated anthro_penetrating anthro_penetrating_anthro balls collar duo eyes_closed felid feline frank_gembeck furry gay gay_sex leopard male/male male_focus male_only male_penetrated male_penetrating male_penetrating_male mammal nipples penis penis_in_ass ponytail sex sexual_intercourse snow_leopard testicles white_hair yaoi

analanal_penetration

1990s 1990s_(style) 1999 1girls 20th_century aozee bare_shoulders bikini bikini_bottom blue_eyes blush bra british british_female brown_hair clavicle cleavage closed_mouth collarbone curvaceous_female curvaceous_figure curvaceous_hips disney eyeshadow jane_porter light-skinned_female linea_alba long_hair looking_at_viewer lower_body makeup mascara medium_breasts messy_hair midriff narrow_shoulders narrow_waist obliques partially_colored pawg pushup_bra red_lipstick standing tarzan_(1999_film) thick_eyebrows thigh_gap toned_female underwear_only unfinished venus_body walt_disney_animation_studios wide_hips yellow_bikini

aozeebare_shoulders

1990s 1999 20th_century all_fours anal anal_sex animal_genitalia anthro anthro_on_anthro balls blitz_(road_rovers) blue_eyes bottomless breasts brown_body brown_fur canid canine canis clothed clothing colleen_(road_rovers) collie dialogue dobermann doggy_style domestic_dog duo english_text erection female female_penetrated from_behind_position fur genitals hair herding_dog kthanid_(artist) male male/female male_penetrating male_penetrating_female mammal nipples nude pastoral_dog penetration penis pinscher raised_tail red_eyes road_rovers sex sheath sheepdog side_boob side_view speech_bubble tail text

1990s 1999 20th_century anal anal_sex animated anthro anthro_on_anthro ass big_breasts bodily_fluids bouncing_breasts breasts classic_animations closed_eyes cum cum_in_ass cum_inside do_not_distribute doggy_style duo erection eric_schwartz female female_penetrated from_behind_position genital_fluids genitals low_res male male/female male_penetrating male_penetrating_female mammal mephitid nude penetration penile penile_penetration penis pussy sex side_boob simple_background skunk stacey_(ews) stacey_skunk striped_skunk tongue

1990s 1999 1female 20th_century african_female bell buttplug_tail collar naked naked_female nose_ring nose_ring_leash the_veterinarian

african_femalebell

1990s 1999 3d black_hair collar cross crown_of_thorns crucifixion execution naked_female slave thrallord

black_haircollar

1990s 1999 20th_century 3d arms_behind_back bondage bondage_horse brown_hair chained chains collar naked_female neck_chain thrallord wooden_horse

arms_behind_backbondage

1990s 1990s_(style) 1999 1girls 3d 90s arms_tied_behind_back artist_name barefoot bondage brown_hair completely_nude_female copyright_name dated full_body ice_block indoors leg_tied_to_arm long_hair medium_breasts nipple_torture nipples_tied pierced_nipples predicament_bondage rapier skewer skewered solo standing_on_one_leg stone_wall thrallord tiptoes uncensored web_address

arms_tied_behind_backartist_name

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