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age_differenceaged_up

14th_century 1boy 1boy1futa 1futa :) big_butt big_penis blue_outfit blue_robe bodily_fluids brown_hair cheating cheating_wife clothed_male_nude_futanari cum cum_on_ass cyclone123 ejaculation ermine european extra_credits extra_history femboy femboy_focus france futanari grey_background history intersex jerking_off jerkingoff light-skinned_futanari light-skinned_male long_sleeves looking_at_penis louis_i_duke_of_orléans male male_focus medieval medieval_europe medieval_france mob_face motion_lines no_neck public_domain queen_isabeau_of_bavaria robe simple_background smile smiling_at_partner squatting squatting_position stroking stroking_cock stroking_penis thick_ass thick_penis thick_thighs throwing_it_back twerking unseen_futa_face youtube

1boy 1femboy after_anal after_sex animal_humanoid anthro ass ass_focus bodily_fluids bodily_fluids_in_ass bubble_ass bubble_butt cat_ears cat_tail child_bearing_hips cum cum_in_ass cyclone123 fat_ass femboy femboy_focus femboy_only freckles freckles_on_face fur fur_thick_thighs furry gradient_background gray_(sprunki) gray_body gray_fur hands_on_hips incredibox_mod indifferent looking_at_viewer looking_back male_anthro male_focus male_only no_visible_genitalia pink_background plump_ass plump_butt public_domain shadow simple_background solo solo_anthro solo_focus solo_male sprunki thick_ass

after_analafter_sex

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2boys anal anal_juice anal_sex anal_through_clothes annoyed annoyed_expression annoyed_face ass_focus ass_juice bed bedsheets black_hat brown_hair bubble_ass bubble_butt clothed clothed_male_nude_male clothed_sex corkscrew_position crossover crossover_pairing crossover_shipping cyclone123 dark-skinned_male extra_credits extra_history france french fucked_through_clothes fully_clothed fully_clothed_male furrowed_eyebrows gay gay_anal gay_sex gradient_background history john_the_fearless light-skinned_male lil_nas_x medieval medieval_europe medieval_france medieval_history mob_face motion_blur nude_male plain_background plap plap_(sound) plump_butt plump_thighs public_domain red_outfit red_robe robe simple_background text thick_ass thick_thighs unseen_male_face weird_crossover yaoi youtube

>< 1boy ass ass_focus black_stockings bubble_ass bubble_butt bulge closed_eyes cute cyclone123 fat_ass femboy_focus gay giggling hamilton_musical heart hearts_around_head king_george_iii long_sleeves male_focus male_only mischevious_look mischievous mischievous_smile panties powdered_wig public_domain shiny_ass shiny_skin simple_background smile smiling_at_viewer stockings stockings_thigh_highs sweater teasing tempting thick_ass thick_thighs thighhighs thighs

... 1700s 18th_century 1futa age_difference annoyed annoyed_expression big_breasts big_butt big_penis boobjob catherine_ii_of_russia catherine_the_great cock cum_on_breasts cyclone123 extra_credits extra_history female female_focus forced_incest futa_on_female futanari grey_hair hag hands_on_breasts history incest incest_(lore) intersex johanna_elisabeth light-skinned_female light-skinned_futanari mature_female milf mob_face motion_lines nipples_visible_through_clothing older_female orgasm paizuri paizuri_on_lap public_domain simple_background thick_cock youtube

...age_difference

1boy balls ballsack bottom_heavy circle_head clapping_ass clapping_cheeks clukr_(sprunki) cyclone123 english_text grey_body humanoid incredibox_mod motion_lines non-human public_domain self_upload silver_body sprunki teasing thug_shaker toony wiggle_lines wiggling_ass wiggling_butt

1boy 1horse art_request black_suit blowjob_face brown_hair cum_in_mouth cum_on_face cumshot cyclone123 extra_credits extra_history gay heavy_balls henry_ford history holding_penis horse horse_penis horseballs horsecock light-skinned_male public_domain youtube zoophilia

art_requestblack_suit

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animal_humanoidanthro_on_anthro

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analanal_insertion

18th_century 1femboy 2boys arrow bedsheets blue_sweater bubble_ass bubble_butt cyclone123 english_text extra_credits extra_history frederick_the_great gay hans_hermann_von_katte heart heart_symbol hearts_around_head history imminent_anal imminent_sex jiggling jiggling_butt light-skinned_male long_sleeves mob_face motion_lines old_fritz on_bed plump_ass plump_butt powdered_wig public_domain slapping_ass slapping_butt slapping_own_ass sweating sweaty_butt teasing text text_bubble thick_ass thick_thighs unseen_character unseen_male_face wiggling_ass wiggling_butt youtube

1femboy 2boys ? ass_focus balls ballsack big_butt black_hat brown_hair bubble_ass bubble_butt charles_v cock cock-tail curious cyclone123 england extra_credits extra_history femboy henry_viii history hyper_thighs imminent_sex light-skinned_male looking_at_another looking_at_viewer looking_down male male_only medieval medieval_history mob_face motion_lines name_in_dialogue no_pants orange_outfit orange_thighhighs penis public_domain puckered_anus simple_background simple_shading spain stockings thick_ass thick_thighs thighhighs unseen_male_face voluptuous voluptuous_male wide_hips younger_male youtube

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1femboy 2boys bartender big_ass big_butt black_eyes black_outfit blue_overalls brown_hair bubble_ass bubble_butt clapping_ass clapping_cheeks cyclone123 english_dialogue english_text flamingo_(youtuber) fully_clothed_male gay gradient_background heel_boots im_gonna_kill_myself light-skinned_male lloyd_joe_(the_smiles_family) looking_at_another looking_at_partner looking_at_penis looking_back male male/male male_focus male_only motion_lines mrflimflam public_domain roblox roblox_myth robloxian smiling smiling_at_partner smug squatting teasing the_smiles_family the_smiles_household tuxedo unseen_male_face wet_ass what_the_fuck youtuber

bartenderbig_ass

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18th_century 1futa 1girls ?! about_to_cum age_difference aged_up anal_through_clothes angry angry_expression angry_face ass ass_bigger_than_head ass_focus ass_grab big_breasts big_butt big_penis blue_outfit breasts bubble_ass bubble_butt catherine_ii_of_russia catherine_the_great cell_shading clothed clothed_female_nude_futanari clothed_sex clothes_as_condom clothing curvaceous curvy curvy_figure cyclone123 d:< dialogue dialogue_bubble dirty_talk dress duo english_dialogue english_text ermine extra_credits extra_history female female_focus female_penetrated forced forced_in_fabric forced_incest fucked_through_clothes fucked_through_dress fucked_through_skirt futanari grabbing_ass grey_background grey_hair history huge_ass huge_cock human impregnation_risk incest incest_(lore) incest_pregnancy intersex johanna_elisabeth light-skinned_female light-skinned_futanari light_skin looking_at_another looking_back milf moaning moaning_in_pleasure moaning_on_cock mob_face mostly_clothed mother_and_daughter nipple_bulge nipples_visible_through_clothing noncon nonconsensual older_female penetration penetration_from_behind penetration_through_clothes penis public_domain public_indecency public_sex pussy_juice rape royal royalty sex_through_clothes sex_through_dress sex_through_skirt sideboob sitting_on_lap sitting_on_penis sophia_augusta_frederica standing text_bubble threatening through_clothes tight_clothing tight_dress torn_clothes torn_clothing torn_dress unexpected unexpectedly_good unseen_futa_face vaginal_penetration voluptuous voluptuous_female yellow_outfit youtube yuri

! 18th_century 1futa1boy 1prussian :0 :v anal anal_sex ass_juice bed blush blush_lines boots cyclone123 dubious_consent duo extra_credits extra_history eyes_rolling_back femboy femboysub finished_art frederick_the_great futa_on_male futadom gloves grabbing_ass heel_boots history male_focus maria_theresa mob_face monochrome open_eyes open_mouth possible_rape powdered_wig public_domain simple_background simple_shading stockings stockings_thigh_highs sweating torn_clothes torn_legwear tremble_spikes trembling trembling_for_pleasure tricorne unseen_futa_face white_background youtube

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>:/ ... 14th_century 2boys anger_vein angry angry_expression annoyed annoyed_expression assjob back_view black_hat brown_hair clothed clothed_male_nude_male clothed_sex comic cousins cyclone123 dat_ass death_glare disembodied_arm disembodied_arms disembodied_hands disgust disgusted dubious_consent extra_credits extra_history fat_ass france frown frowning frowning_at_partner frowning_at_viewer furious gay glare glaring glaring_at_partner glaring_at_viewer gradient_background gradient_shading grey_background groping groping_ass historical_porn history hotdogging hotdogging_ass imminent_anal imminent_penetration imminent_sex incest john_the_fearless light-skinned_male louis_i_duke_of_orléans mad male_focus male_only male_pov medieval medieval_europe medieval_france medieval_history mob_face motion_lines public_domain red_outfit robe simple_background simple_coloring simple_shading squeezing squeezing_ass squeezing_butt text_bubble thick_ass thick_thighs throbbing_penis tight_clothing uncut uncut_penis youtube

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