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2009

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1boy 1girls 2009 big_breasts boots breasts busty couple digital_drawing_(artwork) digital_media_(artwork) duo eyebrows eyelashes eyes female green-skinned_female green_body green_skin hair hero high_heel_boots high_heels huge_breasts hulk_(series) hulked_out large_breasts legs light-skinned_male light_skin lips loki-667 male marvel marvel_comics mary_jane_watson muscular muscular_female panties peter_parker rafael_dantas red_hair ritualist ritualist_(artist) she-hulk she-hulk_(cosplay) slim_waist spider-man spider-man_(series) spider-man_crop_top straight strong superhero themed_clothes thick thick_hips thick_legs thick_thighs thighs thong voluptuous voluptuous_female waist wide_hips

big_breastsboots

2009 anthro ass big_butt black_hair dragon dragon_wings female hair huge_butt kazecat long_hair looking_at_viewer low-angle_view moon obese obese_anthro obese_female overweight overweight_anthro overweight_female purple_body purple_scales red_eyes sarjiri_sara_(kazecat) scales scalie star thick_thighs western_dragon wide_hips wings

1futa 2000s 2009 big_penis blonde_hair bottomless breasts cleavage clothed clothing cum disgaea disgaea_2 ejaculation erection futa_only futanari fuyu_sato human intersex large_breasts light-skinned_futa light_skin masturbation mostly_clothed nippon_ichi_software onahole penis rozalin short_hair solo standing

big_penisblonde_hair

1futa 2000s 2009 autopaizuri breasts disgaea disgaea_2 erection futa_only futanari fuyu_sato huge_cock humanoid humanoid_penis intersex large_breasts light-skinned_futa light_skin masturbation nippon_ichi_software nude paizuri penis rozalin sketch small_image solo

autopaizuribreasts

00s 1girls 2009 alternate_eye_color andou_shuki bare_shoulders black_hair breasts collarbone completely_nude completely_nude_female female female_focus female_only flower frown hair_flower hair_ornament light-skinned_female light_skin long_hair looking_down medium_breasts navel nude nude_female purple_eyes saten_ruiko solo teenage_girl teenager to_aru_kagaku_no_railgun to_aru_majutsu_no_index upper_body white_background young

alternate_eye_colorandou_shuki

2009 all_three_filled anal anal_sex anthro anus arthropod biped blue_body blue_eyes blue_fur blue_hair bodily_fluids breasts canid canine clitoris cum cum_inside double_penetration felicity_longis_(colorist) fellatio female forced fox fur genital_fluids genitals green_tentacles hair krystal long_story mammal millipede multiple_penetration myriapod nintendo nipples nude oral oral_penetration oral_rape orgasm penetration penile pink_nipples_jewelry pussy pussy_juice rape sex solo spread_legs spreading star_fox tentacle tentacle_in_mouth tentacle_penetration tentacle_rape tentacle_sex triple_penetration vaginal_penetration vaginal_penetration vixen_tamer white_body white_fur

all_three_filledanal

2009 anthro anthro_on_anthro blue_body blue_fur blue_hair blush bodily_fluids breast_grab breast_play breasts canid canine collar cum cum_on_face cumshot duo ejaculation erection facial felicity_longis_(colorist) female female_raped forced forced_paizuri fox fur genital_fluids genitals gold_(metal) gold_jewelry green_body green_scales hair hand_on_breast interspecies jewelry krystal lactating lizard long_story male male/female male_rape male_raping_female maledom mammal medium_breasts messy milk nintendo nipples open_mouth orgasm paizuri paizuri_lead_by_male paizuri_rape penis pink_nipples protagonistsub_antagonistdom rape reptile scales scalie sex sex_slave sharpclaw_(star_fox) slave spines star_fox straddling straddling_paizuri tattoo titfuck titjob tongue vixen_tamer white_body white_fur

anthroanthro_on_anthro

2009 accessory anthro anthro_on_anthro anthro_penetrated anthro_penetrating anthro_penetrating_anthro areola balls bangs bent_legs biped blue_body blue_eyes blue_fur blue_hair bodily_fluids bodily_fluids_in_mouth bodily_fluids_in_pussy body_part_in_pussy bondage bound breasts canid canine chains clitoral_hood clitoris crying cum cum_covered cum_in_mouth cum_in_pussy cum_inside cum_on_breasts cum_on_face double_penetration drooling erect_nipples erection excessive_cum excessive_genital_fluids felicity_longis_(colorist) fellatio female female_penetrated female_raped forced forced_oral fox fur furgonomics genital_fluids genitals green_body green_eyes green_scales group group_sex hair interspecies jewelry krystal lizard long_story looking_at_another looking_at_partner male male/female male_penetrating male_penetrating_female male_rape male_raping_female mammal medium_breasts messy nintendo nipples nubbed_penis nude oral oral_penetration oral_rape orgasm penetration penile penile_penetration penile_spines penis penis_in_pussy pillory pink_nipples protagonistsub_antagonistdom pussy raised_tail rape reptile restraints ring saliva scales scalie sex sex_slave sharpclaw_(star_fox) short_hair signature slave spines spitroast star_fox stocks submissive submissive_female suspension tail tail_accessory tail_grab tail_jewelry tail_ring tattoo tears threesome trio two_doms_one_sub vaginal_penetration vixen_tamer white_body white_fur yellow_sclera

accessoryanthro

2009 anthro blue_body blue_eyes blue_fur blue_hair bodily_fluids bondage bound bra breasts canid canine chains clothed clothing color_edit colored duo felicity_longis_(colorist) female female_raped fingering forced fox fur general_scales genital_fluids gold_(metal) gold_jewelry green_body green_eyes green_scales hair jewelry krystal male male/female male_rape male_raping_female mammal medium_story nintendo one_eye_closed partially_clothed protagonistsub_antagonistdom pussy_juice rape scales scalie sex_slave sharpclaw_(star_fox) slave star_fox third-party_edit underwear vaginal_penetration vixen_tamer white_body white_fur yellow_sclera

anthroblue_body

1boy 2000s 2009 2girls 5koma animal_crossing anthro blonde_female blonde_hair brokenteapot comic dialogue english_text female female_focus furry imminent_kiss male mario_(series) metroid mr._resetti multiple_girls new_years_eve nintendo not_porn princess_peach samus_aran speech_bubble super_smash_bros. text yuri

animal_crossinganthro

2000s 2009 battle_damage brokenteapot burned_clothing damaged_clothes dialogue english_text female female_focus metal_gear_solid metroid nintendo samus_aran solid_snake speech_bubble tagme text

battle_damagebrokenteapot

2000s 2009 2d 2d_(artwork) 3girls blue_bra blue_panties bra brokenteapot female female_only holding_pillow lingerie mario_(series) multiple_girls nintendo orange_bra orange_panties panties pillow pillow_fight pink_bra pink_panties princess_daisy princess_peach princess_rosalina tagme underwear underwear_only

blue_brablue_panties

2000s 2009 2boys 2d 2d_(artwork) 2girls bikini blonde blonde_female blonde_hair blue_bikini brokenteapot female female_focus long_hair looking_at_another lying male mario mario_(series) metal_gear_solid metroid multiple_boys multiple_girls nintendo on_side pink_bikini ponytail princess_peach samus_aran seductive solid_snake super_smash_bros. swimsuit tied_hair

1girls 2000s 2009 between_breasts brokenteapot female nintendo princess_zelda tagme the_legend_of_zelda triforce twilight_princess zelda_(twilight_princess)

between_breastsbrokenteapot

! 2000s 2009 ass blonde blonde_female blonde_hair blonde_hair_female blue_bra blue_panties blue_underwear blush blush_lines blushing box bra brokenteapot euf exclamation_point eyes_open female female_focus hiding hiding_object locker_room long_hair looking_back metal_gear_solid metroid nintendo panties peeping ponytail samus_aran secret solid_snake sweat sweatdrop sweating sweaty towel turn_around turning_around turning_head underwear

00s 1boy 2000s 2009 3girls animal_crossing anthro brokenteapot convenient_censoring enf english_text female furry male mario_(series) metroid mr._resetti multiple_girls nintendo princess_peach princess_zelda samus_aran simple_background speech_bubble standing suddenly_naked super_smash_bros. surprised tagme text the_legend_of_zelda twilight_princess zelda_(twilight_princess)

animal_crossinganthro

2009 big_breasts breasts christmas emma_frost female julius_zimmerman marvel marvel_comics nipples snowman tagme x-men

big_breastsbreasts

00s 2000s 2009 2d animated ass bent_over cum_in_pussy female forced hentai incest inseki japanese_dialogue long_video longer_than_2_minutes longer_than_one_minute mature_female mind_control mother_and_son older_female_and_younger_male penis rape sex_from_behind soukan_yuugi_2 souma_makoto souma_natsuki sound step-incest stepmother_and_stepson straight tagme uncensored vaginal_penetration vanilla_(studio) veins veiny_penis video voice_acted younger_penetrating_older

1girls 2009 ainu_clothes alternate_breast_size arms_behind_back big_breasts breasts brown_eyes busty cute female female_only hair_ribbon japanese_text kaminari_masato king_of_fighters large_breasts long_hair looking_at_viewer nakoruru pink_lips purple_hair retro_artstyle ribbon samurai_shodown smile snk solo translation_request voluptuous

ainu_clothesalternate_breast_size

00s 1boy 1girls 2000s 2009 2d aizawa_haruna animated belly big_belly bouncing_breasts breast_squeeze breasts censored closed_eyes cum_drip cum_dripping_from_penis cum_in_pussy cum_inside cumdrip female female_focus female_penetrated hentai japanese_dialogue japanese_voice_acting knife lactating lactation long_video longer_than_2_minutes longer_than_3_minutes longer_than_one_minute male mask masked_male milking nah open_clothes open_shirt pregnant pregnant_sex rape rape!_rape!_rape! screencap sex sound tagme valkyria_(studio) video voice_acted

aizawa_harunaanimated

16:9 16:9_aspect_ratio 2009 ass ass_cleavage ass_focus back_view big_ass black_mizugi black_swimsuit cleft_of_venus female mizugi mizugi_kanojo mizugi_kanojo_1 ms_pictures one-piece_swimsuit pussy_visible_through_clothes pussy_visible_through_swimsuit sayaka-san sayaka_(mizugi_kanojo) school_swimsuit screencap screenshot skindentation swimsuit t-rex_(animation_studio) tagme tight_clothing

assass_cleavage

16:9 16:9_aspect_ratio 2009 ass ass_cleavage ass_focus back_view big_ass black_mizugi black_swimsuit cleft_of_venus female mizugi mizugi_kanojo mizugi_kanojo_1 ms_pictures one-piece_swimsuit pussy_visible_through_clothes pussy_visible_through_swimsuit sayaka-san sayaka_(mizugi_kanojo) school_swimsuit screencap screenshot skindentation swimsuit t-rex_(animation_studio) tagme tight_clothing

assass_cleavage

2009 anthro barefoot biped black_nose bodily_fluids canid canine duo erection feet genital_fluids genitals heterochromia male male/male mammal peeing penis urine urine_on_chest watersports what ybox

2009 anthro barefoot biped bodily_fluids bottomless bottomless_anthro bottomless_male closed_eyes clothed clothing ear_piercing ear_ring feet fishnet fishnet_clothing fishnet_topwear genital_fluids genitals male mammal mouse murid murine musetta nipples peeing penis piercing ring_piercing rodent sitting topwear urinal urine urine_in_mouth urine_pool watersports what

2009 5:4 anthro blue_body blue_fur blush bodily_fluids brown_body brown_fur brown_hair debirobu duo english_text erection faceless_character faceless_male felid fellatio fur genitals hair half-closed_eyes high-angle_view japanese_text leo_(red_earth) lion male male/male male_penetrated male_penetrating male_penetrating_male mammal narrowed_eyes oral oral_penetration pantherine penetration penile penis red_earth sex sweat tan_body tan_fur text translation_request vein veiny_penis yellow_eyes

anthroblue_body

16:9 16:9_aspect_ratio 2009 ahe_gao ahegao anifactory brown_hair censored censored_pussy cleft_of_venus creampie cum cum_explosion cum_expulsion cum_in_pussy english_text erect_nipples green_eyes hartman_hips landing_strip long_hair mizugi mizugi_kanojo mizugi_kanojo_1 mizuho_(mizugi_kanojo) mizuho_chan mosaic_censoring ms_pictures nude o_face open_mouth orgasm orgasm_face screencap tagme text tongue

16:9 16:9_aspect_ratio 1boy 1girls 2009 anifactory blue_mizugi blue_swimsuit brown_hair cameltoe censored censored_penis cleft_of_venus english_text erect_nipples erect_nipples_under_clothes erect_nipples_under_swimsuit female green_eyes long_hair male mizugi mizugi_kanojo mizugi_kanojo_1 mizuho_(mizugi_kanojo) mizuho_chan mosaic_censoring ms_pictures nipples_visible_through_clothing one-piece_swimsuit penis pulling_on_clothes pussy_visible_through_clothes pussy_visible_through_swimsuit school_swimsuit screencap swimsuit tagme text tight_clothing

anifactoryblue_mizugi

16:9 16:9_aspect_ratio 2009 ass ass_cleavage ass_focus back_view big_ass blue_mizugi blue_swimsuit cleft_of_venus female mizugi mizugi_kanojo mizugi_kanojo_1 mizuho_(mizugi_kanojo) mizuho_chan ms_pictures one-piece_swimsuit pulling_on_clothes pussy_visible_through_clothes pussy_visible_through_swimsuit school_swimsuit screencap screenshot swimsuit tagme tight_clothing

assass_cleavage

16:9 16:9_aspect_ratio 2009 ass ass_cleavage ass_focus back_view big_ass blue_mizugi blue_swimsuit cleft_of_venus female mizugi mizugi_kanojo mizugi_kanojo_1 mizuho_(mizugi_kanojo) mizuho_chan ms_pictures one-piece_swimsuit pulling_on_clothes pussy_visible_through_clothes pussy_visible_through_swimsuit school_swimsuit screencap swimsuit swimsuit_pull tagme tight_clothing

assass_cleavage

2009 3girls aged_up almost_naked almost_nude bed bedroom bedroom_eyes belly belly_button bigtyme bikini black_hair blonde_hair blossom_(powerpuff_girls) blue_eyes boobs breasts bubbles_(powerpuff_girls) buttercup_(powerpuff_girls) cartoon_network cleavage dark_room eyelashes female female_only green_eyes half-closed_eyes half_naked half_nude human human_only kneeling lamp legs light-skinned_female light_skin lipstick long_hair looking_at_viewer multiple_girls navel on_bed on_knees on_one_knee open_mouth orange_hair pale-skinned_female pale_skin partially_clothed pink_eyes powerpuff_girls sisters sitting smile thighs thong toonami twintails underboob

aged_upalmost_naked

1boy 1boy1girl 1girls 2009 2d amputation amputee artist_request big_breasts breast_grab breast_squeeze breasts breasts_bigger_than_head breasts_out corpse cum cum_in_pussy cum_inside dead death decapitation english_text female gore guro low_res lowres male male/female missionary missionary_position narration necrophilia nipples original original_character rape sex spy story straight tan_body tan_skin text undercover undressed

amputationamputee

1boy 1boy1girl 1girls 2009 2d amputation amputee artist_request big_breasts breast_grab breasts breasts_bigger_than_head breasts_out corpse dead death emotionless english_text expressionless female female_death gore guro low_res lowres male male/female narration necrophilia nipples original original_character paizuri rape sex spy story straight tan_body tan_skin text undercover undressed

amputationamputee

1boy 1boy1girl 1girls 2009 2d artist_request big_breasts breasts breasts_bigger_than_head breasts_out endured_face english_text female low_res lowres male male/female narration nipples original original_character paizuri rape sex spy story straight tan_body tan_skin text undercover undressed

artist_requestbig_breasts

1boy 1boy1girl 1girls 2009 2d artist_request big_breasts breasts breasts_bigger_than_head breasts_out endured_face english_text female low_res lowres male male/female missionary missionary_position narration nipples original original_character rape sex spy story straight tan_body tan_skin text undercover undressed vaginal_penetration

artist_requestbig_breasts

1boy 1boy1girl 1girls 2009 2d artist_request big_breasts breasts breasts_bigger_than_head breasts_out camera doggy_style english_text female low_res lowres male male/female narration nipples original original_character rape recording sex spy story straight tan_body tan_skin text undercover undressed vaginal_penetration

artist_requestbig_breasts

1boy 1boy1girl 1girls 2009 2d artist_request big_breasts breasts breasts_bigger_than_head breasts_out deepthroat english_text fellatio female forced forced_oral labcoat low_res lowres male male/female narration nipples oral original original_character rape sex spy story straight tan_body tan_skin text undercover undressed

artist_requestbig_breasts

1boy 1boy1girl 1girls 2009 2d after_rape after_sex artist_request big_breasts breasts breasts_bigger_than_head breasts_out english_text female labcoat low_res lowres male male/female narration nipples original original_character rape sleep_molestation sleeping somnophilia spy story straight tan_body tan_skin text unconscious undercover undressed wake_up

after_rapeafter_sex

1boy 1boy1girl 1girls 2009 2d after_rape after_sex artist_request big_breasts breasts breasts_bigger_than_head breasts_out camera english_text female labcoat low_res lowres male male/female narration nipples original original_character rape recording sleep_molestation sleeping somnophilia spy story straight tan_body tan_skin text unconscious undercover undressed

after_rapeafter_sex

1boy 1boy1girl 1girls 2009 2d artist_request big_breasts breast_grab breast_squeeze breasts breasts_bigger_than_head breasts_out censored censored_face emotionless english_text expressionless female labcoat low_res lowres male male/female missionary missionary_position narration nipples original original_character rape sleep_molestation sleeping somnophilia spy story straight tan_body tan_skin text unconscious undercover undressing vaginal_penetration vaginal_sex

artist_requestbig_breasts

1boy 1boy1girl 1girls 2009 2d artist_request big_breasts blowjob breasts breasts_bigger_than_head breasts_out camera emotionless english_text expressionless fellatio female forced forced_oral labcoat low_res lowres male male/female narration nipples oral original original_character rape recording sex sleep_molestation sleeping somnophilia spy story straight tan_body tan_skin text unconscious undercover undressing

artist_requestbig_breasts

1girls 2009 2d artist_request big_breasts breasts breasts_bigger_than_head english_text female imminent_rape imminent_sex labcoat low_res lowres narration nipples original original_character rape sleep_molestation sleeping somnophilia spy story tan_body tan_skin text unconscious undercover undressing

artist_requestbig_breasts

1girls 2009 2d ambush_(trap) artist_request big_breasts bra breasts breasts_bigger_than_head english_text female grope groping imminent_rape imminent_sex low_res lowres narration original original_character rape shocked spy story surprised tan_body tan_skin text torn_clothes torn_clothing undercover

ambush_(trap)artist_request

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