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r34 popular

prison clothes
a year ago
91
0
1boy 1futa 2girls blindfolded bondage cigarette female futa_on_female futanari futasub handjob intersex jail jail_cell male pervertfuel prison prison_cell prison_clothes prison_guard prisoner
0
1boy 1futa 2girls blindfolded bondage cigarette female futa_on_female futanari futasub handjob intersex jail jail_cell male pervertfuel prison prison_cell prison_clothes prison_guard prisoner
a year ago
52
0
1boy 1girls ai_assisted ai_generated ai_hands ass blonde_hair blonde_hair_female breasts cant_escape charlie_morningstar_(hazbin_hotel) cum cum_in_pussy cum_inside female female_focus female_penetrated female_rape_victim female_raped gritted_teeth hazbin_hotel large_ass male male_penetrating male_penetrating_female massive_breasts nonconsensual orange_jumpsuit pillory prison prison_bars prison_bitch prison_cell prison_clothes prison_life prison_rape prisoner pussy random_guy rape restrained restrained_arms restrained_rape sex_from_behind standing_doggy_style standing_sex
0
1boy 1girls ai_assisted ai_generated ai_hands ass blonde_hair blonde_hair_female breasts cant_escape charlie_morningstar_(hazbin_hotel) cum cum_in_pussy cum_inside female female_focus female_penetrated female_rape_victim female_raped gritted_teeth hazbin_hotel large_ass male male_penetrating male_penetrating_female massive_breasts nonconsensual orange_jumpsuit pillory prison prison_bars prison_bitch prison_cell prison_clothes prison_life prison_rape prisoner pussy random_guy rape restrained restrained_arms restrained_rape sex_from_behind standing_doggy_style standing_sex
a year ago
147
0
1boy 1girls :>= ai_generated animal_genitalia animal_penis anthro bunny bunny_ears clawed_fingers deepthroat disney fellatio female female_on_human fur furry grey_hair holding_ears human human_on_anthro judy_hopps lagomorph looking_at_viewer male male/female male_on_anthro oral penis pov prison_clothes prisoner purple_eyes rabbit rtxfus zootopia
0
1boy 1girls :>= ai_generated animal_genitalia animal_penis anthro bunny bunny_ears clawed_fingers deepthroat disney fellatio female female_on_human fur furry grey_hair holding_ears human human_on_anthro judy_hopps lagomorph looking_at_viewer male male/female male_on_anthro oral penis pov prison_clothes prisoner purple_eyes rabbit rtxfus zootopia
a year ago
51
0
1boy 1girls absurdres ahoge animal_ear_fluff animal_ears armpits bare_shoulders blush breasts cat_ears cat_girl collarbone dark-skinned_male dark_skin double-parted_bangs female grabbing_another's_breast grin groping hair_intakes highres hololive hololive_gamers hololive_japan large_breasts male medium_hair navel nekomata_okayu nipples nude oerba_yun_fang prison_clothes purple_eyes purple_hair sidelocks simple_background smile solo_focus upper_body virtual_youtuber white_background xue_lian_wa_noel
0
1boy 1girls absurdres ahoge animal_ear_fluff animal_ears armpits bare_shoulders blush breasts cat_ears cat_girl collarbone dark-skinned_male dark_skin double-parted_bangs female grabbing_another's_breast grin groping hair_intakes highres hololive hololive_gamers hololive_japan large_breasts male medium_hair navel nekomata_okayu nipples nude oerba_yun_fang prison_clothes purple_eyes purple_hair sidelocks simple_background smile solo_focus upper_body virtual_youtuber white_background xue_lian_wa_noel
a year ago
43
0
1boy 1girls 3d athletic athletic_female bald_female black_and_white fantasytubasa female from_behind human interracial light-skinned_male light_skin male nazi original partially_clothed police_uniform prison prison_clothes prisoner rape sex sex_from_behind shackled_ankles shackles shaved_head standing_sex
0
1boy 1girls 3d athletic athletic_female bald_female black_and_white fantasytubasa female from_behind human interracial light-skinned_male light_skin male nazi original partially_clothed police_uniform prison prison_clothes prisoner rape sex sex_from_behind shackled_ankles shackles shaved_head standing_sex
a year ago
74
0
1boy 1girls after_sex after_vaginal boruto:_naruto_next_generations bottomless bottomless_female breasts cheating cheating_wife condom condom_on_penis cuckold cum_in_condom dress erect_penis erection exposed_breasts faceless_male female forehead_mark high_resolution indoors light-skinned_female light_skin long_hair male mature mature_female milf naruto naruto_(series) netorare nipples no_bra noxdsa ntr on_table open_clothes partially_clothed penis pink_hair pink_hair_female prison_clothes prison_uniform prisoner pussy sakura_haruno sex shoulder_length_hair sitting sitting_on_table table thighs uncensored unzipped zipper zipper_down zipper_pull_tab
0
1boy 1girls after_sex after_vaginal boruto:_naruto_next_generations bottomless bottomless_female breasts cheating cheating_wife condom condom_on_penis cuckold cum_in_condom dress erect_penis erection exposed_breasts faceless_male female forehead_mark high_resolution indoors light-skinned_female light_skin long_hair male mature mature_female milf naruto naruto_(series) netorare nipples no_bra noxdsa ntr on_table open_clothes partially_clothed penis pink_hair pink_hair_female prison_clothes prison_uniform prisoner pussy sakura_haruno sex shoulder_length_hair sitting sitting_on_table table thighs uncensored unzipped zipper zipper_down zipper_pull_tab
a year ago
336
0
1boy 1girls ai_generated angry angry_face arms_behind_back avatar_legends avatar_the_last_airbender azula azure_(artist) balls bodily_fluids breasts brown_eyes brown_hair clothed clothed_female_nude_male clothing cock_shock detailed_background duo erection female fire_nation forced gritted_teeth hair_grab hairbun hi_res huge_cock imminent_fellatio imminent_oral jail_cell jumpsuit kneeling light-skinned_female light-skinned_male light_skin long_penis looking_at_penis looking_down male male/female male_pov mommy monster_cock nickelodeon nude nude_male on_knees orange_jumpsuit penis penis_against_cheek penis_against_face penis_on_face pov prison prison_clothes prison_uniform prisoner restrained rizdraws_(ai_style) small_breasts stable_diffusion straight sweat teeth testicles thick_thighs veiny_penis wide_hips
0
1boy 1girls ai_generated angry angry_face arms_behind_back avatar_legends avatar_the_last_airbender azula azure_(artist) balls bodily_fluids breasts brown_eyes brown_hair clothed clothed_female_nude_male clothing cock_shock detailed_background duo erection female fire_nation forced gritted_teeth hair_grab hairbun hi_res huge_cock imminent_fellatio imminent_oral jail_cell jumpsuit kneeling light-skinned_female light-skinned_male light_skin long_penis looking_at_penis looking_down male male/female male_pov mommy monster_cock nickelodeon nude nude_male on_knees orange_jumpsuit penis penis_against_cheek penis_against_face penis_on_face pov prison prison_clothes prison_uniform prisoner restrained rizdraws_(ai_style) small_breasts stable_diffusion straight sweat teeth testicles thick_thighs veiny_penis wide_hips
2 years ago
62
0
... 1boy aged_down animal_ears black_hair black_socks blue_eyes blush bottomless closed_mouth coupon cum cum_on_clothes duelnine0 gay gay_male genshin_impact grey_hair hair_between_eyes heart leave male male_focus male_only multicolored_hair multiple_views off_shoulder open_mouth prison_clothes scar scar_on_face scar_on_leg scar_on_neck sitting socks spoken_ellipsis striped sweat tail tongue tongue_out torn_clothes translation_request twitter_username wriothesley_(genshin_impact) wrist_cuffs yaoi
0
... 1boy aged_down animal_ears black_hair black_socks blue_eyes blush bottomless closed_mouth coupon cum cum_on_clothes duelnine0 gay gay_male genshin_impact grey_hair hair_between_eyes heart leave male male_focus male_only multicolored_hair multiple_views off_shoulder open_mouth prison_clothes scar scar_on_face scar_on_leg scar_on_neck sitting socks spoken_ellipsis striped sweat tail tongue tongue_out torn_clothes translation_request twitter_username wriothesley_(genshin_impact) wrist_cuffs yaoi
2 years ago
107
0
1boy 1girls alternate_costume arms_behind_back black_hair blush female femdom from_behind fully_clothed genderswap genderswap_(mtf) gentle_femdom gintama gintoki_sakata groping groping_from_behind handcuffs height_difference hijikata_toshiro long_hair male malesub mame_(pixiv) miniskirt police_hat police_officer police_uniform policewoman prison_clothes prisoner rule_63 trembling underass
0
1boy 1girls alternate_costume arms_behind_back black_hair blush female femdom from_behind fully_clothed genderswap genderswap_(mtf) gentle_femdom gintama gintoki_sakata groping groping_from_behind handcuffs height_difference hijikata_toshiro long_hair male malesub mame_(pixiv) miniskirt police_hat police_officer police_uniform policewoman prison_clothes prisoner rule_63 trembling underass
2 years ago
472
0
1boy 1girls accurate_art_style animated bigger_male blonde_hair breasts clothed_sex cum cum_in_pussy cum_inside cum_on_body cum_on_lower_body doggy_style dusty_marlow fat_male female from_behind from_behind_position full_body gina_jabowski glass_window glory_hole high_resolution highres indoors inmate male medium_ass medium_breasts obese obese_male overweight overweight_male paradise_pd penis prison prison_clothes prison_guard pussy raw_sex running_bond sex sfan shorter_than_30_seconds slim_girl sound straight too_horny video
0
1boy 1girls accurate_art_style animated bigger_male blonde_hair breasts clothed_sex cum cum_in_pussy cum_inside cum_on_body cum_on_lower_body doggy_style dusty_marlow fat_male female from_behind from_behind_position full_body gina_jabowski glass_window glory_hole high_resolution highres indoors inmate male medium_ass medium_breasts obese obese_male overweight overweight_male paradise_pd penis prison prison_clothes prison_guard pussy raw_sex running_bond sex sfan shorter_than_30_seconds slim_girl sound straight too_horny video
2 years ago
331
0
1boy 1girls 2023 2d 2d_(artwork) age_difference antenna_hair blush breasts brown_eyes brown_hair collarbone crazy_girl female female_focus head_tilt human indoors jacket jewelry khyleri large_breasts light-skinned_female light_skin long_hair looking_at_another male misato_katsuragi neon_genesis_evangelion no_bra no_sex older_female on_model open_clothes open_jacket orange_jacket prison prison_clothes purple_hair shinji_ikari single_bare_shoulder smile solo_focus text undressing unhinged wavy_hair younger_male
0
1boy 1girls 2023 2d 2d_(artwork) age_difference antenna_hair blush breasts brown_eyes brown_hair collarbone crazy_girl female female_focus head_tilt human indoors jacket jewelry khyleri large_breasts light-skinned_female light_skin long_hair looking_at_another male misato_katsuragi neon_genesis_evangelion no_bra no_sex older_female on_model open_clothes open_jacket orange_jacket prison prison_clothes purple_hair shinji_ikari single_bare_shoulder smile solo_focus text undressing unhinged wavy_hair younger_male
2 years ago
353
0
1boy 1girls accurate_art_style animated bigger_male breasts clothed_sex cum cum_in_pussy cum_inside cum_on_body cum_on_lower_body doggy_style dusty_marlow female from_behind from_behind_position gina_jabowski glass_window glory_hole high_resolution highres longer_than_30_seconds male medium_ass medium_breasts obese paradise_pd prison_clothes pussy raw_sex sex sfan slim_girl sound tagme video
0
1boy 1girls accurate_art_style animated bigger_male breasts clothed_sex cum cum_in_pussy cum_inside cum_on_body cum_on_lower_body doggy_style dusty_marlow female from_behind from_behind_position gina_jabowski glass_window glory_hole high_resolution highres longer_than_30_seconds male medium_ass medium_breasts obese paradise_pd prison_clothes pussy raw_sex sex sfan slim_girl sound tagme video
2 years ago
17
0
1boy 1girls age_difference alternate_costume blonde_hair blush breasts character_name chinese_text donquixote_doflamingo earrings female female_focus gilf gloves highres huangshulangda jewelry large_breasts large_penis male muscular muscular_male old older_female one_piece penis prison_clothes short_hair size_difference smile speech_bubble sunglasses tsuru_(one_piece) white_hair
0
1boy 1girls age_difference alternate_costume blonde_hair blush breasts character_name chinese_text donquixote_doflamingo earrings female female_focus gilf gloves highres huangshulangda jewelry large_breasts large_penis male muscular muscular_male old older_female one_piece penis prison_clothes short_hair size_difference smile speech_bubble sunglasses tsuru_(one_piece) white_hair
2 years ago
41
0
1boy 1girls 3d athletic athletic_female black_hair blender blowjob blowjob_face breasts busty dani_nakamura dark-skinned_male dark_skin fellatio female female_focus hourglass_figure interracial karen_fukuhara krafton light-skinned_female light_skin long_hair male massive_penis partial_male penis prison prison_clothes prison_guard prisoner sssin2160 striking_distance_studios tagme tank_top the_callisto_protocol
0
1boy 1girls 3d athletic athletic_female black_hair blender blowjob blowjob_face breasts busty dani_nakamura dark-skinned_male dark_skin fellatio female female_focus hourglass_figure interracial karen_fukuhara krafton light-skinned_female light_skin long_hair male massive_penis partial_male penis prison prison_clothes prison_guard prisoner sssin2160 striking_distance_studios tagme tank_top the_callisto_protocol
3 years ago
209
0
1boy 1girls alternate_breast_size before_sex blush breasts dismassd female hololive hololive_fantasy hololive_japan imminent_sex jail jail_cell large_breasts long_hair male mask meme prison prison_clothes prison_uniform stuck sweat twintails usada_pekora virtual_youtuber
0
1boy 1girls alternate_breast_size before_sex blush breasts dismassd female hololive hololive_fantasy hololive_japan imminent_sex jail jail_cell large_breasts long_hair male mask meme prison prison_clothes prison_uniform stuck sweat twintails usada_pekora virtual_youtuber
3 years ago
150
0
1boy 1girls abs amazon ass athletic athletic_female between_legs between_thighs big_breasts big_muscles bodybuilder boots breasts buff busty choke_hold choker choking cleavage crush crushing curvaceous curves dominant domination dominatrix duo_focus extreme_muscles faceless_male female femdom figure_four_headlock giantess glasses grey_hair head_between_thighs headscissor headscissors high_resolution holding_arm legwear long_hair looking_at_another looking_down lying_down male muscle_tone muscles muscular muscular_arms muscular_ass muscular_back muscular_female muscular_legs muscular_shoulders muscular_thighs prison prison_cell prison_clothes prison_school prisoner ren_(tainca2000) rentb school_uniform scissorhold shiraki_meiko skirt smile squeezing thick_ass thick_hips thick_thighs thighs_bigger_than_head thunder_thighs tied_hair tight_clothing toned toned_female voluptuous wide_hips wide_sleeves wide_thighs wrestling wrestlingryona
0
1boy 1girls abs amazon ass athletic athletic_female between_legs between_thighs big_breasts big_muscles bodybuilder boots breasts buff busty choke_hold choker choking cleavage crush crushing curvaceous curves dominant domination dominatrix duo_focus extreme_muscles faceless_male female femdom figure_four_headlock giantess glasses grey_hair head_between_thighs headscissor headscissors high_resolution holding_arm legwear long_hair looking_at_another looking_down lying_down male muscle_tone muscles muscular muscular_arms muscular_ass muscular_back muscular_female muscular_legs muscular_shoulders muscular_thighs prison prison_cell prison_clothes prison_school prisoner ren_(tainca2000) rentb school_uniform scissorhold shiraki_meiko skirt smile squeezing thick_ass thick_hips thick_thighs thighs_bigger_than_head thunder_thighs tied_hair tight_clothing toned toned_female voluptuous wide_hips wide_sleeves wide_thighs wrestling wrestlingryona
3 years ago
238
0
10s 1boy 1girls 2015 artist_name artist_signature black_choker black_hair black_stripes blush braless breast_grab breasts breasts_grab breasts_out breasts_squeeze brown_jacket brown_skirt bursting_breasts choker cleavage collarbone collared_shirt deep_skin double_breast_grab embarrassed enormous_breasts face_out_of_frame female fujino_kiyoshi full_cleavage fully_clothed glasses grabbing grabbing_breasts groping groping_breasts hi_res high_resolution highres huge_breasts japanese_text lips lipstick long_sleeves male mmolestation motion_lines no_bra open_mouth out_of_frame plain_background pleated_skirt prison_clothes prison_school prison_uniform prisoner red_lips red_lipstick sayori777nsfw school school_uniform shiraki_meiko shirt shocked short_hair showing_teeth silver_hair simple_background squeezing_breasts straight striped_clothing sweat sweatdrop sweaty_breasts translation_request unseen_male_face voluptuous white_background white_shirt
0
10s 1boy 1girls 2015 artist_name artist_signature black_choker black_hair black_stripes blush braless breast_grab breasts breasts_grab breasts_out breasts_squeeze brown_jacket brown_skirt bursting_breasts choker cleavage collarbone collared_shirt deep_skin double_breast_grab embarrassed enormous_breasts face_out_of_frame female fujino_kiyoshi full_cleavage fully_clothed glasses grabbing grabbing_breasts groping groping_breasts hi_res high_resolution highres huge_breasts japanese_text lips lipstick long_sleeves male mmolestation motion_lines no_bra open_mouth out_of_frame plain_background pleated_skirt prison_clothes prison_school prison_uniform prisoner red_lips red_lipstick sayori777nsfw school school_uniform shiraki_meiko shirt shocked short_hair showing_teeth silver_hair simple_background squeezing_breasts straight striped_clothing sweat sweatdrop sweaty_breasts translation_request unseen_male_face voluptuous white_background white_shirt
3 years ago
264
0
10s 1girls 2015 2boys accidental_exposure animated animated_gif areola_slip areolae arm_wrestling ass black-framed_eyewear black-framed_glasses black_boots black_footwear black_high_heel_boots blonde_hair blue_eyes blush boots bouncing_breasts breast_rest breasts brown_legwear bursting_breasts choker cleavage clenched_teeth close-up closed_eyes curvaceous enormous_breasts erect_nipples exposed_ass exposed_breasts eyeglasses eyewear falling fantasy fat_mons female female_only fujino_kiyoshi gif glasses hair_bun hi_res high_heel_boots high_heels high_resolution highres hourglass_figure huge_areolae huge_ass huge_breasts huge_nipples indoors legwear lips lipstick makeup male massive_breasts mature_female microskirt miniskirt morokuzu_takehito multiple_boys nipple_slip nipples nipples_touching no_bra open_clothes open_shirt ova panties pantyshot pantyshot_(standing) partially_visible_vulva prison prison_cell prison_clothes prison_school puffy_areola puffy_nipples purple_panties pussy school_uniform screencap screenshot shiraki_meiko shirt silver_hair skirt solo solo_focus table teeth unbuttoned unbuttoned_shirt uncensored upskirt voluptuous
0
10s 1girls 2015 2boys accidental_exposure animated animated_gif areola_slip areolae arm_wrestling ass black-framed_eyewear black-framed_glasses black_boots black_footwear black_high_heel_boots blonde_hair blue_eyes blush boots bouncing_breasts breast_rest breasts brown_legwear bursting_breasts choker cleavage clenched_teeth close-up closed_eyes curvaceous enormous_breasts erect_nipples exposed_ass exposed_breasts eyeglasses eyewear falling fantasy fat_mons female female_only fujino_kiyoshi gif glasses hair_bun hi_res high_heel_boots high_heels high_resolution highres hourglass_figure huge_areolae huge_ass huge_breasts huge_nipples indoors legwear lips lipstick makeup male massive_breasts mature_female microskirt miniskirt morokuzu_takehito multiple_boys nipple_slip nipples nipples_touching no_bra open_clothes open_shirt ova panties pantyshot pantyshot_(standing) partially_visible_vulva prison prison_cell prison_clothes prison_school puffy_areola puffy_nipples purple_panties pussy school_uniform screencap screenshot shiraki_meiko shirt silver_hair skirt solo solo_focus table teeth unbuttoned unbuttoned_shirt uncensored upskirt voluptuous
4 years ago
28
0
1boy 1girls afro agent_jones blush clothed cum cum_inside dark-skinned_female dark_skin digital_drawing_(artwork) doctor_slone feet female female_dominating_male fight fortnite glasses grabbing_leg hairy interracial male male/female muscular muscular_male nipples penis pointing_gun prison_clothes randomonimusxd
0
1boy 1girls afro agent_jones blush clothed cum cum_inside dark-skinned_female dark_skin digital_drawing_(artwork) doctor_slone feet female female_dominating_male fight fortnite glasses grabbing_leg hairy interracial male male/female muscular muscular_male nipples penis pointing_gun prison_clothes randomonimusxd
4 years ago
174
0
10s 1girls 5boys accidental_exposure andou_reiji animated animated_gif anus_peek ass ass_focus bars bent_over black_footwear black_hair black_high_heel_boots black_legwear blonde_hair boots breasts brown_skirt cameltoe censored chopsticks chopsticks_in_mouth cleavage close-up concrete convenient_censoring covered_anus covered_pussy eating female food fujino_kiyoshi full_body glasses hair_censor hand_on_own_knee hanging_breasts high_heel_boots highres huge_ass huge_breasts impossible_clothes indoors jacket kneeling leaning_forward looking_at_pussy male microskirt miniskirt morokuzu_takehito multiple_boys nezu_jouji no_bra no_panties panties panties_on_floor partially_visible_vulva picking_up plaid plaid_skirt pleated_skirt prison prison_cell prison_clothes prison_school prisoner purple_panties pussy pussy_peek revealing_clothes school_uniform screencap shiny shiny_skin shiraki_meiko shoes short_hair skirt striped talking thighhighs thong trembling uncensored underwear uniform wakamoto_shingo
0
10s 1girls 5boys accidental_exposure andou_reiji animated animated_gif anus_peek ass ass_focus bars bent_over black_footwear black_hair black_high_heel_boots black_legwear blonde_hair boots breasts brown_skirt cameltoe censored chopsticks chopsticks_in_mouth cleavage close-up concrete convenient_censoring covered_anus covered_pussy eating female food fujino_kiyoshi full_body glasses hair_censor hand_on_own_knee hanging_breasts high_heel_boots highres huge_ass huge_breasts impossible_clothes indoors jacket kneeling leaning_forward looking_at_pussy male microskirt miniskirt morokuzu_takehito multiple_boys nezu_jouji no_bra no_panties panties panties_on_floor partially_visible_vulva picking_up plaid plaid_skirt pleated_skirt prison prison_cell prison_clothes prison_school prisoner purple_panties pussy pussy_peek revealing_clothes school_uniform screencap shiny shiny_skin shiraki_meiko shoes short_hair skirt striped talking thighhighs thong trembling uncensored underwear uniform wakamoto_shingo
4 years ago
175
0
10s 1boy 2015 :d absurdres artist_name ass bad_perspective black_footwear black_hair black_legwear black_panties blazer blood blush boots breasts brown_legwear cameltoe character_name english_text fabuloso_vasquez fabulosovasquez female from_behind from_below fujino_kiyoshi hair_between_eyes highres huge_ass huge_breasts impossible_clothes jacket juan_romero kneepits labia long_sleeves looking_at_another magazine_cover male manga_cover microskirt miniskirt nosebleed open_mouth panties plaid plaid_skirt pleated_skirt prison_clothes prison_school pussy pussy_visible_through_clothes scared school_uniform shiny shiny_skin shiraki_meiko shoes short_hair signature simple_background skirt skirt_lift smile standing thighhighs thighs thong trembling underwear upskirt wedgie year yellow_eyes
0
10s 1boy 2015 :d absurdres artist_name ass bad_perspective black_footwear black_hair black_legwear black_panties blazer blood blush boots breasts brown_legwear cameltoe character_name english_text fabuloso_vasquez fabulosovasquez female from_behind from_below fujino_kiyoshi hair_between_eyes highres huge_ass huge_breasts impossible_clothes jacket juan_romero kneepits labia long_sleeves looking_at_another magazine_cover male manga_cover microskirt miniskirt nosebleed open_mouth panties plaid plaid_skirt pleated_skirt prison_clothes prison_school pussy pussy_visible_through_clothes scared school_uniform shiny shiny_skin shiraki_meiko shoes short_hair signature simple_background skirt skirt_lift smile standing thighhighs thighs thong trembling underwear upskirt wedgie year yellow_eyes
4 years ago
413
0
1boy 1girls ahe_gao anal anal_access anal_only anal_only_chastity anal_penetration anal_sex anus asylum blush bondage bondage_outfit broken_chain chains chastity chastity_belt chastity_belt_anal chastity_device collar desperation edging faceless_male female female_chastity fox fox_tail harness horny_jail latex looking_at_viewer looking_pleasured male male_penetrating_female orgasm_denial prison_clothes prisoner pussy sex shackles smile straitjacket syx_(tang) tang tongue tongue_out vaginal_chastity
0
1boy 1girls ahe_gao anal anal_access anal_only anal_only_chastity anal_penetration anal_sex anus asylum blush bondage bondage_outfit broken_chain chains chastity chastity_belt chastity_belt_anal chastity_device collar desperation edging faceless_male female female_chastity fox fox_tail harness horny_jail latex looking_at_viewer looking_pleasured male male_penetrating_female orgasm_denial prison_clothes prisoner pussy sex shackles smile straitjacket syx_(tang) tang tongue tongue_out vaginal_chastity
4 years ago
105
0
1boy 1girls ahegao animal_ears balls bangs black_headwear black_shirt blue_hair blush body_writing breasts bunny_ears collar cum cum_in_pussy cum_inside dark-skinned_male dark_skin eyebrows_visible_through_hair female female_orgasm hair_between_eyes heavy_breathing highres hikimayu hololive hololive_fantasy hololive_japan interracial long_hair male male_pubic_hair multicolored_hair nipples open_mouth orange_eyes orgasm overflow penis prison_clothes pubic_hair pussy rabbit_girl rape sex shiki_(catbox230123) shirt short_eyebrows small_breasts solo_focus spread_legs straight striped striped_headwear striped_shirt sweat tally testicles thick_eyebrows two-tone_hair two_side_up uncensored usada_pekora vaginal_penetration virtual_youtuber white_hair white_headwear white_shirt
0
1boy 1girls ahegao animal_ears balls bangs black_headwear black_shirt blue_hair blush body_writing breasts bunny_ears collar cum cum_in_pussy cum_inside dark-skinned_male dark_skin eyebrows_visible_through_hair female female_orgasm hair_between_eyes heavy_breathing highres hikimayu hololive hololive_fantasy hololive_japan interracial long_hair male male_pubic_hair multicolored_hair nipples open_mouth orange_eyes orgasm overflow penis prison_clothes pubic_hair pussy rabbit_girl rape sex shiki_(catbox230123) shirt short_eyebrows small_breasts solo_focus spread_legs straight striped striped_headwear striped_shirt sweat tally testicles thick_eyebrows two-tone_hair two_side_up uncensored usada_pekora vaginal_penetration virtual_youtuber white_hair white_headwear white_shirt
4 years ago
193
0
1boy 1girls amber_eyes blonde_hair catching_cum clothed clothed_sex cum_on_face cum_on_tongue ejaculation female golden_eyes h0tsh0t hands_on_ground kneeling male male/female medium_hair midorikawa_hana on_knees open_mouth penis penis_out prison_clothes prison_school prisoner school_uniform skirt tongue tongue_out unseen_male_face
0
1boy 1girls amber_eyes blonde_hair catching_cum clothed clothed_sex cum_on_face cum_on_tongue ejaculation female golden_eyes h0tsh0t hands_on_ground kneeling male male/female medium_hair midorikawa_hana on_knees open_mouth penis penis_out prison_clothes prison_school prisoner school_uniform skirt tongue tongue_out unseen_male_face
5 years ago
52
0
1boy 1futa anal anal_sex animal_ears animal_genitalia animal_penis animal_tail anthro balls belly_riding big_dom_small_sub black_fur black_hair bondage breasts canine chains collar crotchless dark-skinned_futa dark_skin dog_ears dog_tail drooling erection eyes_rolling_back femboy furry futa_is_bigger futa_on_male futa_penetrating futa_sans_pussy futadom futanari huge_balls huge_breasts huge_penis husky intersex jail jail_cell larger_futa latex_bodysuit male male_penetrated malesub mizukithia muscular muscular_futa open_mouth original_character penis penis_out pink_nose prison prison_clothes prison_uniform prisoner red_eyes sheath sissy size_difference small_penis smaller_male stomach_bulge submissive submissive_male tail topless trap turiia_(character) white_fur
0
1boy 1futa anal anal_sex animal_ears animal_genitalia animal_penis animal_tail anthro balls belly_riding big_dom_small_sub black_fur black_hair bondage breasts canine chains collar crotchless dark-skinned_futa dark_skin dog_ears dog_tail drooling erection eyes_rolling_back femboy furry futa_is_bigger futa_on_male futa_penetrating futa_sans_pussy futadom futanari huge_balls huge_breasts huge_penis husky intersex jail jail_cell larger_futa latex_bodysuit male male_penetrated malesub mizukithia muscular muscular_futa open_mouth original_character penis penis_out pink_nose prison prison_clothes prison_uniform prisoner red_eyes sheath sissy size_difference small_penis smaller_male stomach_bulge submissive submissive_male tail topless trap turiia_(character) white_fur
5 years ago
147
0
1boy 1girls american_flag areola_slip areolae arm_behind_head armpits arms_behind_head aviator_sunglasses bangs bar_censor bikini bikini_lift black_gloves black_hair black_hat black_vest boobjob breast_grab breasts censored censored_penis choker cleavage commentary_request condom condom_accessories condom_belt cum cum_in_mouth double_breast_grab earrings elbow_gloves elbow_sleeve erect_nipples erect_nipples_under_bikini erect_nipples_under_clothes erection female filled_condom fishnet_legwear fishnet_thighhighs fishnets gloves grabbing gravity_zero27 groping_breasts ground_zero hair_ornament hat heart-shaped_pupils heart_eyes heels high_heels highres jewelry large_breasts leather leather_gloves lipstick long_hair looking_at_viewer looking_over_eyewear looking_over_glasses looking_over_sunglasses makeup male navel nipples o-ring o-ring_bikini one_breast_out open_mouth original paizuri partial_male peaked_cap penis police_hat policewoman precum_on_breasts prison prison_cell prison_clothes prison_guard_position prison_uniform prisoner pubes pubic_hair puffy_nipples purple_eyes red_bikini revealing_clothes saliva saliva_on_tongue sidelocks skin_tight skindentation sling_bikini sling_bikini_aside squeezing_breast steamy steamy_armpits steamy_penis stray_pubic_hair sunglasses sweaty_breasts swimsuit tagme tinted_eyewear tongue tongue_out two_side_up underbust used_condom vest warden zerogura
0
1boy 1girls american_flag areola_slip areolae arm_behind_head armpits arms_behind_head aviator_sunglasses bangs bar_censor bikini bikini_lift black_gloves black_hair black_hat black_vest boobjob breast_grab breasts censored censored_penis choker cleavage commentary_request condom condom_accessories condom_belt cum cum_in_mouth double_breast_grab earrings elbow_gloves elbow_sleeve erect_nipples erect_nipples_under_bikini erect_nipples_under_clothes erection female filled_condom fishnet_legwear fishnet_thighhighs fishnets gloves grabbing gravity_zero27 groping_breasts ground_zero hair_ornament hat heart-shaped_pupils heart_eyes heels high_heels highres jewelry large_breasts leather leather_gloves lipstick long_hair looking_at_viewer looking_over_eyewear looking_over_glasses looking_over_sunglasses makeup male navel nipples o-ring o-ring_bikini one_breast_out open_mouth original paizuri partial_male peaked_cap penis police_hat policewoman precum_on_breasts prison prison_cell prison_clothes prison_guard_position prison_uniform prisoner pubes pubic_hair puffy_nipples purple_eyes red_bikini revealing_clothes saliva saliva_on_tongue sidelocks skin_tight skindentation sling_bikini sling_bikini_aside squeezing_breast steamy steamy_armpits steamy_penis stray_pubic_hair sunglasses sweaty_breasts swimsuit tagme tinted_eyewear tongue tongue_out two_side_up underbust used_condom vest warden zerogura
5 years ago
89
0
1boy 1girls american_flag areola_slip areolae arm_behind_head armpits arms_behind_head aviator_sunglasses bangs bar_censor bikini bikini_lift black_gloves black_hair black_hat black_vest boobjob breast_grab breasts censored censored_penis choker cleavage commentary_request condom condom_accessories condom_belt cum cum_in_mouth double_breast_grab earrings elbow_gloves elbow_sleeve erect_nipples erect_nipples_under_bikini erect_nipples_under_clothes erection female filled_condom fishnet_legwear fishnet_thighhighs fishnets gloves grabbing gravity_zero27 groping_breasts ground_zero hair_ornament hat heels high_heels highres jewelry large_breasts leather leather_gloves lipstick long_hair looking_at_viewer looking_over_eyewear looking_over_glasses looking_over_sunglasses makeup male navel nipples o-ring o-ring_bikini one_breast_out open_mouth original paizuri partial_male peaked_cap penis police_hat policewoman precum_on_breasts prison prison_cell prison_clothes prison_guard_position prison_uniform prisoner pubes pubic_hair puffy_nipples purple_eyes red_bikini revealing_clothes saliva saliva_on_tongue sidelocks skin_tight skindentation sling_bikini sling_bikini_aside squeezing_breast steamy steamy_armpits steamy_penis stray_pubic_hair sunglasses sweaty_breasts swimsuit tagme tinted_eyewear tongue tongue_out two_side_up underbust used_condom vest warden zerogura
0
1boy 1girls american_flag areola_slip areolae arm_behind_head armpits arms_behind_head aviator_sunglasses bangs bar_censor bikini bikini_lift black_gloves black_hair black_hat black_vest boobjob breast_grab breasts censored censored_penis choker cleavage commentary_request condom condom_accessories condom_belt cum cum_in_mouth double_breast_grab earrings elbow_gloves elbow_sleeve erect_nipples erect_nipples_under_bikini erect_nipples_under_clothes erection female filled_condom fishnet_legwear fishnet_thighhighs fishnets gloves grabbing gravity_zero27 groping_breasts ground_zero hair_ornament hat heels high_heels highres jewelry large_breasts leather leather_gloves lipstick long_hair looking_at_viewer looking_over_eyewear looking_over_glasses looking_over_sunglasses makeup male navel nipples o-ring o-ring_bikini one_breast_out open_mouth original paizuri partial_male peaked_cap penis police_hat policewoman precum_on_breasts prison prison_cell prison_clothes prison_guard_position prison_uniform prisoner pubes pubic_hair puffy_nipples purple_eyes red_bikini revealing_clothes saliva saliva_on_tongue sidelocks skin_tight skindentation sling_bikini sling_bikini_aside squeezing_breast steamy steamy_armpits steamy_penis stray_pubic_hair sunglasses sweaty_breasts swimsuit tagme tinted_eyewear tongue tongue_out two_side_up underbust used_condom vest warden zerogura
5 years ago
76
0
+_+ azur_lane black_ribbon blush bondage breasts chains cuffs dress_shirt eyebrows_visible_through_hair female food hair_ornament hair_ribbon high_resolution honolulu_(azur_lane) irohasu large_breasts long_hair looking_at_viewer manjuu_(azur_lane) meat open_mouth prison_clothes red_eyes red_hair ribbon saliva saliva_trail short_dress striped thighhighs tied_hair torn_clothes twintails very_long_hair white_legwear
0
+_+ azur_lane black_ribbon blush bondage breasts chains cuffs dress_shirt eyebrows_visible_through_hair female food hair_ornament hair_ribbon high_resolution honolulu_(azur_lane) irohasu large_breasts long_hair looking_at_viewer manjuu_(azur_lane) meat open_mouth prison_clothes red_eyes red_hair ribbon saliva saliva_trail short_dress striped thighhighs tied_hair torn_clothes twintails very_long_hair white_legwear
6 years ago
490
0
1boy 1girls against_wall ahe_gao anal anal_penetration anal_sex ankle_grab ass_juice auburn_hair avatar_the_last_airbender background barefoot big_breasts blue_eyes breasts breasts_visible_through_clothing broken_rape_victim clothed_sex clothing drooling eyes_rolling_back faceless_male female fire_nation fucked_senseless fucked_silly hanging_breasts leg_grab male medium_breasts open_mouth penis pounding prison prison_clothes prison_guard prison_guard_position prisoner pussy raised_leg rape reit ripped_clothes ripped_clothing ripped_pants saliva short_hair spread_legs standing_sex suki thin_waist tight_anus tongue tongue_out torn_clothes torn_pants wet
0
1boy 1girls against_wall ahe_gao anal anal_penetration anal_sex ankle_grab ass_juice auburn_hair avatar_the_last_airbender background barefoot big_breasts blue_eyes breasts breasts_visible_through_clothing broken_rape_victim clothed_sex clothing drooling eyes_rolling_back faceless_male female fire_nation fucked_senseless fucked_silly hanging_breasts leg_grab male medium_breasts open_mouth penis pounding prison prison_clothes prison_guard prison_guard_position prisoner pussy raised_leg rape reit ripped_clothes ripped_clothing ripped_pants saliva short_hair spread_legs standing_sex suki thin_waist tight_anus tongue tongue_out torn_clothes torn_pants wet
6 years ago
357
0
1boy 1girls 3d all_fours animated asian ass avatar_legends avatar_the_last_airbender azula barefoot black_hair blowjob blush breasts brunette camera_shake clothed clothed_female clothed_female_nude_male clothing deep_blowjob deepthroat deepthroat_no_hands dubious_consent eye_contact eyelashes eyeshadow feet fellatio female fire_nation firebender gold_eyes hair_bun hands-free head_tilt hetero kneeling kneeling_female kneeling_oral_position light-skinned_female light_skin lipstick looking_at_viewer looking_up male male/female medium_breasts messy messy_hair moaning mslewd naughty_face nickelodeon no_gag_reflex nude nude_male on_knees oral oral_sex penis petite pov princess prison prison_clothes questionable_consent red_lipstick royalty seductive_eyes skinny slim soles sound source_filmmaker spats stirrup_legwear stone_floor teenager throat_barrier throat_noise tied_hair toeless_legwear toes topknot unseen_male_face video watermark webm yellow_eyes
0
1boy 1girls 3d all_fours animated asian ass avatar_legends avatar_the_last_airbender azula barefoot black_hair blowjob blush breasts brunette camera_shake clothed clothed_female clothed_female_nude_male clothing deep_blowjob deepthroat deepthroat_no_hands dubious_consent eye_contact eyelashes eyeshadow feet fellatio female fire_nation firebender gold_eyes hair_bun hands-free head_tilt hetero kneeling kneeling_female kneeling_oral_position light-skinned_female light_skin lipstick looking_at_viewer looking_up male male/female medium_breasts messy messy_hair moaning mslewd naughty_face nickelodeon no_gag_reflex nude nude_male on_knees oral oral_sex penis petite pov princess prison prison_clothes questionable_consent red_lipstick royalty seductive_eyes skinny slim soles sound source_filmmaker spats stirrup_legwear stone_floor teenager throat_barrier throat_noise tied_hair toeless_legwear toes topknot unseen_male_face video watermark webm yellow_eyes
7 years ago
260
0
10s 1girls 4boys andou_reiji animated arched_back ass back_view belly bent_over black_hair black_legwear black_pantyhose bottomwear brown_eyes clothed clothing fat_male female female_focus from_behind fujino_kiyoshi glasses highres human human_only indoors light-skinned_female light-skinned_male light_skin lying lying_on_stomach lying_on_table male mature mature_female milf miniskirt multiple_boys nezu_jouji on_table panties pantyhose pantyshot pantyshot_(standing) partially_visible_vulva pleated_skirt prison_clothes prison_school prison_uniform prisoner purple_panties purple_underwear pussy school_uniform screencap shiraki_meiko silver_hair skirt solo_focus spread_legs standing sweat sweatdrop sweating sweaty sweaty_thighs thighhighs tied_hair topless topwear uncensored underwear wakamoto_shingo
0
10s 1girls 4boys andou_reiji animated arched_back ass back_view belly bent_over black_hair black_legwear black_pantyhose bottomwear brown_eyes clothed clothing fat_male female female_focus from_behind fujino_kiyoshi glasses highres human human_only indoors light-skinned_female light-skinned_male light_skin lying lying_on_stomach lying_on_table male mature mature_female milf miniskirt multiple_boys nezu_jouji on_table panties pantyhose pantyshot pantyshot_(standing) partially_visible_vulva pleated_skirt prison_clothes prison_school prison_uniform prisoner purple_panties purple_underwear pussy school_uniform screencap shiraki_meiko silver_hair skirt solo_focus spread_legs standing sweat sweatdrop sweating sweaty sweaty_thighs thighhighs tied_hair topless topwear uncensored underwear wakamoto_shingo
7 years ago
79
0
10s 1boy animated animated_gif ass boots brown_legwear female from_behind glasses highres indoors male mature_female miniskirt morokuzu_takehito panties pantyshot pantyshot_(standing) partially_visible_vulva pleated_skirt prison_clothes prison_school pussy school_uniform screenshot shiraki_meiko skirt spread_legs standing thighhighs uncensored underwear
0
10s 1boy animated animated_gif ass boots brown_legwear female from_behind glasses highres indoors male mature_female miniskirt morokuzu_takehito panties pantyshot pantyshot_(standing) partially_visible_vulva pleated_skirt prison_clothes prison_school pussy school_uniform screenshot shiraki_meiko skirt spread_legs standing thighhighs uncensored underwear
7 years ago
75
0
10s 2boys animated animated_gif areolae arm_wrestling blonde_hair blue_eyes blush boots bouncing_breasts breast_rest breasts brown_legwear choker cleavage erect_nipples female fujino_kiyoshi glasses grey_hair hair_bun high_heel_boots high_heels huge_breasts indoors lipstick makeup male mature_female miniskirt morokuzu_takehito multiple_boys nipple_slip nipples open_clothes open_shirt prison_clothes prison_school school_uniform screenshot shiraki_meiko shirt silver_hair skirt solo_focus table uncensored
0
10s 2boys animated animated_gif areolae arm_wrestling blonde_hair blue_eyes blush boots bouncing_breasts breast_rest breasts brown_legwear choker cleavage erect_nipples female fujino_kiyoshi glasses grey_hair hair_bun high_heel_boots high_heels huge_breasts indoors lipstick makeup male mature_female miniskirt morokuzu_takehito multiple_boys nipple_slip nipples open_clothes open_shirt prison_clothes prison_school school_uniform screenshot shiraki_meiko shirt silver_hair skirt solo_focus table uncensored
15 years ago
9
0
1boy 1girls abs ass ass_grab bandage beige_skin blonde_hair blush bottomless breasts brown_hair capcom clothes cody_travers color crossover dark_skin embarrassed female final_fight fishnets genderswap guy_(final_fight) hair human japanese_text large_breasts male muscles muscular muscular_female ninjamania_tojo nipples prison_clothes pubic_hair red_hair rule_63 shirt_lift short_hair straight_hair street_fighter sweat tan_skin text tojo_(isolation-lovesick) translation_request white_background
0
1boy 1girls abs ass ass_grab bandage beige_skin blonde_hair blush bottomless breasts brown_hair capcom clothes cody_travers color crossover dark_skin embarrassed female final_fight fishnets genderswap guy_(final_fight) hair human japanese_text large_breasts male muscles muscular muscular_female ninjamania_tojo nipples prison_clothes pubic_hair red_hair rule_63 shirt_lift short_hair straight_hair street_fighter sweat tan_skin text tojo_(isolation-lovesick) translation_request white_background