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AI SEX SLAVE 🔥
prison clothes
42
0
1femboy 2boys ai_generated anal anal_insertion anal_sex arousal aroused aroused_face balls bars blonde_hair blonde_male blue_eyes blush bussy cock cowgirl_position dick erect_penis erection femboy femboy_focus feminine_male gay gay_male gay_sex inmate inmates_clothing jail long_hair long_hair_male male male_focus male_only metal orange_clothing penis ponytail prison prison_bars prison_clothes prison_uniform prisoner redcherryart riding riding_cock riding_penis shadow sissy testicles uniform white_skin
0
1femboy 2boys ai_generated anal anal_insertion anal_sex arousal aroused aroused_face balls bars blonde_hair blonde_male blue_eyes blush bussy cock cowgirl_position dick erect_penis erection femboy femboy_focus feminine_male gay gay_male gay_sex inmate inmates_clothing jail long_hair long_hair_male male male_focus male_only metal orange_clothing penis ponytail prison prison_bars prison_clothes prison_uniform prisoner redcherryart riding riding_cock riding_penis shadow sissy testicles uniform white_skin
a month ago
1
0
1girl 2others absurdres animal_ears ayou_(aukuamani) backlighting bare_shoulders blurry blurry_foreground blush braid breasts bulletproof_vest carrot carrot_hair_ornament chain clothes_writing collar collarbone commentary commission cuffs day don-chan_(usada_pekora) door english_commentary false_smile fog food-themed_hair_ornament hair_ornament handcuffs highres hikimayu hololive indoors jacket kneeling metal_collar military multicolored_hair multiple_others official_alternate_costume orange_eyes pants pixiv_commission prison_clothes prisoner rabbit-shaped_pupils rabbit_ears rabbit_girl safety_pin shirt short_eyebrows sidelocks small_breasts smile standing striped_clothes striped_headwear striped_shirt sunlight symbol-shaped_pupils thick_eyebrows twin_braids two-tone_hair usada_pekora usada_pekora_(prisoner) virtual_youtuber white_hair
0
1girl 2others absurdres animal_ears ayou_(aukuamani) backlighting bare_shoulders blurry blurry_foreground blush braid breasts bulletproof_vest carrot carrot_hair_ornament chain clothes_writing collar collarbone commentary commission cuffs day don-chan_(usada_pekora) door english_commentary false_smile fog food-themed_hair_ornament hair_ornament handcuffs highres hikimayu hololive indoors jacket kneeling metal_collar military multicolored_hair multiple_others official_alternate_costume orange_eyes pants pixiv_commission prison_clothes prisoner rabbit-shaped_pupils rabbit_ears rabbit_girl safety_pin shirt short_eyebrows sidelocks small_breasts smile standing striped_clothes striped_headwear striped_shirt sunlight symbol-shaped_pupils thick_eyebrows twin_braids two-tone_hair usada_pekora usada_pekora_(prisoner) virtual_youtuber white_hair
53
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1femoby 2boys ai_generated anal anal_sex anus aroused aroused_face ass ass_focus asshole balls blonde_hair blonde_male blue_eyes blush cell cellmates cock dick femboy femboy_focus femboy_only feminine_male gay gay_male gay_sex genitals inmate inmates_clothing jail long_hair_male looking_at_viewer looking_back male male_focus male_only open_mouth orange_clothing penis ponytail prison prison_cell prison_clothes prison_uniform prisoner redcherryart testicles
0
1femoby 2boys ai_generated anal anal_sex anus aroused aroused_face ass ass_focus asshole balls blonde_hair blonde_male blue_eyes blush cell cellmates cock dick femboy femboy_focus femboy_only feminine_male gay gay_male gay_sex genitals inmate inmates_clothing jail long_hair_male looking_at_viewer looking_back male male_focus male_only open_mouth orange_clothing penis ponytail prison prison_cell prison_clothes prison_uniform prisoner redcherryart testicles
4 days ago
8
0
1girl absurdres blonde_hair bound bound_wrists breasts cleavage commission cuffs curvy dark-skinned_male dark_skin emilie_de_rochefort grabbing_another's_shoulder handcuffs highres jumpsuit large_breasts lili_(tekken) panties pixiv_commission prison prison_clothes prisoner restrained shackles tekken thick_thighs thighs togaxan togazan underwear white_panties
0
1girl absurdres blonde_hair bound bound_wrists breasts cleavage commission cuffs curvy dark-skinned_male dark_skin emilie_de_rochefort grabbing_another's_shoulder handcuffs highres jumpsuit large_breasts lili_(tekken) panties pixiv_commission prison prison_clothes prisoner restrained shackles tekken thick_thighs thighs togaxan togazan underwear white_panties
32
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2boys 2femboys ass ass_focus ass_grab ball_and_chain big_butt big_butt_(male) big_chest black_and_white_clothing black_and_white_stripes black_clothing black_stripes blonde_hair blue-eyed_male blue_eyes blush boys breasts brown_hair butt_focus cellmates chains chubby collar collar_chain cuffed_ankles cuffed_wrists cuffs dyed_hair edit edited eyebrows eyebrows_visible_through_hair fat fat_ass femboy femboy_focus femboy_only feminine_body feminine_faced_male feminine_male flip_flops gay grabbing grabbing_ass green-eyed_male green_eyes grinning hips inmate inmates inmates_clothing jail jumpsuit male male_ass male_ass_focus male_focus male_only manboobs marmotap medium_hair neck_chain overweight pale_skin penis penis_bulge plump plump_ass prison prison_clothes prison_clothing prison_jumpsuit prison_uniform prisoner recolor restrained restrained_arms restraints seductive seductive_eyes seductive_look seductive_smile shackles smirk socks striped_clothing stripes tanned_male tanned_skin thick thick_ass thick_thighs white_clothing white_skin white_socks white_stripes wide_hips yaoi zoom_in
0
2boys 2femboys ass ass_focus ass_grab ball_and_chain big_butt big_butt_(male) big_chest black_and_white_clothing black_and_white_stripes black_clothing black_stripes blonde_hair blue-eyed_male blue_eyes blush boys breasts brown_hair butt_focus cellmates chains chubby collar collar_chain cuffed_ankles cuffed_wrists cuffs dyed_hair edit edited eyebrows eyebrows_visible_through_hair fat fat_ass femboy femboy_focus femboy_only feminine_body feminine_faced_male feminine_male flip_flops gay grabbing grabbing_ass green-eyed_male green_eyes grinning hips inmate inmates inmates_clothing jail jumpsuit male male_ass male_ass_focus male_focus male_only manboobs marmotap medium_hair neck_chain overweight pale_skin penis penis_bulge plump plump_ass prison prison_clothes prison_clothing prison_jumpsuit prison_uniform prisoner recolor restrained restrained_arms restraints seductive seductive_eyes seductive_look seductive_smile shackles smirk socks striped_clothing stripes tanned_male tanned_skin thick thick_ass thick_thighs white_clothing white_skin white_socks white_stripes wide_hips yaoi zoom_in
51
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1femboy 2boys ai_generated balls blonde_hair blonde_male blowjob blue_eyes blush bussy cock crying cum cum_in_mouth cumming deep_blowjob dick erect_penis erection femboy femboy_focus feminine_male gay gay_male gay_sex grabbing_thighs inmate inmates_clothing jail long_hair long_hair_male male male_focus male_only oral oral_penetration orange_clothing penis ponytail prison prison_clothes prison_uniform prisoner redcherryart sissy slim slim_male sucking sucking_dick sucking_off sucking_penis tears testicles thighs thin thin_waist uniform white_skin
0
1femboy 2boys ai_generated balls blonde_hair blonde_male blowjob blue_eyes blush bussy cock crying cum cum_in_mouth cumming deep_blowjob dick erect_penis erection femboy femboy_focus feminine_male gay gay_male gay_sex grabbing_thighs inmate inmates_clothing jail long_hair long_hair_male male male_focus male_only oral oral_penetration orange_clothing penis ponytail prison prison_clothes prison_uniform prisoner redcherryart sissy slim slim_male sucking sucking_dick sucking_off sucking_penis tears testicles thighs thin thin_waist uniform white_skin
57
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1femboy 2boys ai_generated balls blonde_hair blonde_male blowjob blue_eyes blush bussy cock cum cum_drip cum_in_mouth cumming dick erect_penis erection femboy femboy_focus feminine_male forced_oral gay gay_male gay_sex grabbing_thighs hand_on_head inmate inmates_clothing jail long_hair long_hair_male male male_focus male_only oral oral_penetration oral_sex orange_clothing penis ponytail prison prison_clothes prison_uniform prisoner redcherryart sissy slim slim_male sucking sucking_dick sucking_off sucking_penis testicles thighs thin thin_waist uniform white_skin
0
1femboy 2boys ai_generated balls blonde_hair blonde_male blowjob blue_eyes blush bussy cock cum cum_drip cum_in_mouth cumming dick erect_penis erection femboy femboy_focus feminine_male forced_oral gay gay_male gay_sex grabbing_thighs hand_on_head inmate inmates_clothing jail long_hair long_hair_male male male_focus male_only oral oral_penetration oral_sex orange_clothing penis ponytail prison prison_clothes prison_uniform prisoner redcherryart sissy slim slim_male sucking sucking_dick sucking_off sucking_penis testicles thighs thin thin_waist uniform white_skin
48
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1femboy 2boys ai_generated balls belt blonde_hair blonde_male blowjob blue_eyes blush blush cock cum cum_drool cum_in_mouth cum_inside cum_leaking cum_on_body cum_on_clothes cum_on_face dick dominated domination femboy femboy_focus feminine_male freckles freckles_on_face gay gay_sex hair hand_in_hair hand_on_head inmate inmates_clothing intense_orgasm jail long_hair long_hair_male male male_only open_mouth oral oral_penetration oral_sex orange_clothing orgasm orgasm_from_oral penis ponytail prison prison_clothes prison_uniform prisoner pubic_hair redcherryart semen_in_mouth submissive submissive_femboy submissive_male testicles uniform
0
1femboy 2boys ai_generated balls belt blonde_hair blonde_male blowjob blue_eyes blush blush cock cum cum_drool cum_in_mouth cum_inside cum_leaking cum_on_body cum_on_clothes cum_on_face dick dominated domination femboy femboy_focus feminine_male freckles freckles_on_face gay gay_sex hair hand_in_hair hand_on_head inmate inmates_clothing intense_orgasm jail long_hair long_hair_male male male_only open_mouth oral oral_penetration oral_sex orange_clothing orgasm orgasm_from_oral penis ponytail prison prison_clothes prison_uniform prisoner pubic_hair redcherryart semen_in_mouth submissive submissive_femboy submissive_male testicles uniform
47
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1femboy 2boys abs ai_generated anal anal_sex anus aroused aroused_face blonde_hair blonde_male blue_eyes blush cock cum cum_in_ass cum_inside cumming dick femboy feminine_body feminine_male gay gay_anal gay_domination gay_male gay_sex genitals inmate inmates_clothing jail long_hair male male_only open_mouth orange_clothing penetration penetration_from_behind penis penis_in_ass ponytail prison prison_clothes prison_uniform prisoner redcherryart semen six_pack
0
1femboy 2boys abs ai_generated anal anal_sex anus aroused aroused_face blonde_hair blonde_male blue_eyes blush cock cum cum_in_ass cum_inside cumming dick femboy feminine_body feminine_male gay gay_anal gay_domination gay_male gay_sex genitals inmate inmates_clothing jail long_hair male male_only open_mouth orange_clothing penetration penetration_from_behind penis penis_in_ass ponytail prison prison_clothes prison_uniform prisoner redcherryart semen six_pack
39
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1femboy 2boys ai_generated anal anal_insertion anal_sex arousal aroused aroused_face balls blonde_hair blonde_male blue_eyes blush bussy cock cowgirl_position dick erect_penis erection femboy femboy_focus feminine_male gay gay_male gay_sex grabbing_thighs inmate inmates_clothing jail long_hair long_hair_male male male_focus male_only orange_clothing penis ponytail prison prison_clothes prison_uniform prisoner redcherryart riding riding_cock riding_penis sissy slim slim_male testicles thighs thin thin_waist uniform white_skin
0
1femboy 2boys ai_generated anal anal_insertion anal_sex arousal aroused aroused_face balls blonde_hair blonde_male blue_eyes blush bussy cock cowgirl_position dick erect_penis erection femboy femboy_focus feminine_male gay gay_male gay_sex grabbing_thighs inmate inmates_clothing jail long_hair long_hair_male male male_focus male_only orange_clothing penis ponytail prison prison_clothes prison_uniform prisoner redcherryart riding riding_cock riding_penis sissy slim slim_male testicles thighs thin thin_waist uniform white_skin
22
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1femboy ai_generated anal anal_insertion anal_sex balls blonde_hair blonde_male brown_eyes carrying cellmates cock dick erect_penis erection femboy femboy_focus feminine_male fucking gay gay_sex holding_partner inmate inmates_clothing jail long_hair long_hair_male male male_focus male_only orange_clothing penetration penis ponytail prison prison_clothes prison_uniform prisoner redcherryart testicles uniform white_skin
0
1femboy ai_generated anal anal_insertion anal_sex balls blonde_hair blonde_male brown_eyes carrying cellmates cock dick erect_penis erection femboy femboy_focus feminine_male fucking gay gay_sex holding_partner inmate inmates_clothing jail long_hair long_hair_male male male_focus male_only orange_clothing penetration penis ponytail prison prison_clothes prison_uniform prisoner redcherryart testicles uniform white_skin
4 weeks ago
7
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1girl black_hair bodysuit bound bound_arms breasts brown_hair chain chain_leash cleavage colored_inner_hair cuffs goddess_of_victory:_nikke green_hair green_streaks guilty_(nikke) hair_between_eyes hair_ornament highres huge_breasts large_breasts leash long_hair looking_at_viewer multicolored_hair multiple_persona nagainegi prison_clothes purple_eyes restraints shackles solo straitjacket tattoo two-tone_hair very_long_hair white_bodysuit wrist_tattoo
0
1girl black_hair bodysuit bound bound_arms breasts brown_hair chain chain_leash cleavage colored_inner_hair cuffs goddess_of_victory:_nikke green_hair green_streaks guilty_(nikke) hair_between_eyes hair_ornament highres huge_breasts large_breasts leash long_hair looking_at_viewer multicolored_hair multiple_persona nagainegi prison_clothes purple_eyes restraints shackles solo straitjacket tattoo two-tone_hair very_long_hair white_bodysuit wrist_tattoo
yesterday
5
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1girl animal_ears barefoot bdsm blue_eyes bondage bound cedar_(cedar_japonica) chain collar commentary_request cuffs loli long_hair lying on_back original paid_reward_available prison_clothes soles solo striped_clothes tail torn_clothes variant_set wolf_ears wolf_tail
0
1girl animal_ears barefoot bdsm blue_eyes bondage bound cedar_(cedar_japonica) chain collar commentary_request cuffs loli long_hair lying on_back original paid_reward_available prison_clothes soles solo striped_clothes tail torn_clothes variant_set wolf_ears wolf_tail
3 weeks ago
2
0
1boy brown_pants cuffs deadlock_(game) electricity hat headpiece hieumay highres jacket lightning male_focus mask pants prison_clothes prisoner seven_(deadlock) shackles shirt solo
0
1boy brown_pants cuffs deadlock_(game) electricity hat headpiece hieumay highres jacket lightning male_focus mask pants prison_clothes prisoner seven_(deadlock) shackles shirt solo
43
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1femboy 2boys ai_generated anal anal_insertion anal_sex arousal aroused aroused_face balls blonde_hair blonde_male blue_eyes blush bussy cock cowgirl_position dick erect_penis erection femboy femboy_focus feminine_male gay gay_male gay_sex grabbing_thighs inmate inmates_clothing jail long_hair long_hair_male male male_focus male_only orange_clothing penis ponytail prison prison_clothes prison_uniform prisoner redcherryart riding riding_cock riding_penis sissy slim slim_male testicles thighs thin thin_waist uniform white_skin
0
1femboy 2boys ai_generated anal anal_insertion anal_sex arousal aroused aroused_face balls blonde_hair blonde_male blue_eyes blush bussy cock cowgirl_position dick erect_penis erection femboy femboy_focus feminine_male gay gay_male gay_sex grabbing_thighs inmate inmates_clothing jail long_hair long_hair_male male male_focus male_only orange_clothing penis ponytail prison prison_clothes prison_uniform prisoner redcherryart riding riding_cock riding_penis sissy slim slim_male testicles thighs thin thin_waist uniform white_skin
44
0
1femoby 2boys ai_generated anal anal_sex anus aroused aroused_face ass ass_focus asshole balls blonde_hair blonde_male blush cell cellmates cock dick femboy femboy_focus femboy_only feminine_male gay gay_male gay_sex genitals inmate inmates_clothing jail long_hair_male looking_at_viewer looking_back male male_focus male_only orange_clothing penis prison prison_cell prison_clothes prison_uniform prisoner redcherryart testicles thin thin_male
0
1femoby 2boys ai_generated anal anal_sex anus aroused aroused_face ass ass_focus asshole balls blonde_hair blonde_male blush cell cellmates cock dick femboy femboy_focus femboy_only feminine_male gay gay_male gay_sex genitals inmate inmates_clothing jail long_hair_male looking_at_viewer looking_back male male_focus male_only orange_clothing penis prison prison_cell prison_clothes prison_uniform prisoner redcherryart testicles thin thin_male
40
0
1femboy ai_generated anal anal_sex ass_focus balls cellmates cock dick femboy femboy_focus feminine_male gay gay_sex inmate inmates_clothing jail male male_focus male_only medium_hair orange_clothing penetration penis penis_in_ass prison prison_clothes prison_uniform prisoner red_hair red_hair_male redcherryart redhead_male testicles uniform white_skin
0
1femboy ai_generated anal anal_sex ass_focus balls cellmates cock dick femboy femboy_focus feminine_male gay gay_sex inmate inmates_clothing jail male male_focus male_only medium_hair orange_clothing penetration penis penis_in_ass prison prison_clothes prison_uniform prisoner red_hair red_hair_male redcherryart redhead_male testicles uniform white_skin
60
0
1femoby 2boys ai_generated anal anal_sex anus aroused aroused_face ass ass_focus asshole balls blonde_hair blonde_male blue_eyes blush cell cellmates cock dick femboy femboy_focus femboy_only feminine_male gay gay_male gay_sex genitals hands_on_ass inmate inmates_clothing jail long_hair_male looking_at_viewer looking_back male male_focus male_only open_mouth orange_clothing penis ponytail prison prison_cell prison_clothes prison_uniform prisoner redcherryart testicles
0
1femoby 2boys ai_generated anal anal_sex anus aroused aroused_face ass ass_focus asshole balls blonde_hair blonde_male blue_eyes blush cell cellmates cock dick femboy femboy_focus femboy_only feminine_male gay gay_male gay_sex genitals hands_on_ass inmate inmates_clothing jail long_hair_male looking_at_viewer looking_back male male_focus male_only open_mouth orange_clothing penis ponytail prison prison_cell prison_clothes prison_uniform prisoner redcherryart testicles
43
0
1femoby 2boys ai ai-created ai_art ai_assisted ai_generated anal anal_sex anus ass ass_focus asshole balls blonde_hair blonde_male blush cell cellmates cock dick doggy_style femboy femboy_focus femboy_only feminine_male from_behind gay gay_male gay_sex genitals inmate inmates_clothing jail long_hair_male looking_at_viewer looking_back male male_focus male_only orange_clothing penis prison prison_cell prison_clothes prison_uniform prisoner redcherryart testicles thin thin_male
0
1femoby 2boys ai ai-created ai_art ai_assisted ai_generated anal anal_sex anus ass ass_focus asshole balls blonde_hair blonde_male blush cell cellmates cock dick doggy_style femboy femboy_focus femboy_only feminine_male from_behind gay gay_male gay_sex genitals inmate inmates_clothing jail long_hair_male looking_at_viewer looking_back male male_focus male_only orange_clothing penis prison prison_cell prison_clothes prison_uniform prisoner redcherryart testicles thin thin_male
57
0
2boys ai_generated ass balls bars big_butt blonde_hair blue_eyes blush buttcheeks cell cellmates cock femboy femboy_focus feminine_male freckles freckles_on_face gay gay_male homosexual inmate jail key male male_focus male_on_femboy male_only orange_clothing orange_shirt penis penis_in_ass prison prison_cell prison_clothes prison_uniform prisoner redcherryart sissy testicles
0
2boys ai_generated ass balls bars big_butt blonde_hair blue_eyes blush buttcheeks cell cellmates cock femboy femboy_focus feminine_male freckles freckles_on_face gay gay_male homosexual inmate jail key male male_focus male_on_femboy male_only orange_clothing orange_shirt penis penis_in_ass prison prison_cell prison_clothes prison_uniform prisoner redcherryart sissy testicles
4 days ago
2
0
1girl 92penpen capcom chun-li commission cuffs handcuffs highres luca_balsa mugshot pixiv_commission prison prison_clothes prisoner shackles street_fighter
0
1girl 92penpen capcom chun-li commission cuffs handcuffs highres luca_balsa mugshot pixiv_commission prison prison_clothes prisoner shackles street_fighter
a month ago
9
0
1girl absurdres animal_ears bed between_legs black_shorts bound bound_wrists breasts cat_ears cat_girl cat_tail cleavage cuffs earrings extra_ears grey_hair hand_between_legs handcuffs highres iron_bars jewelry jjalbaaaaa light_smile long_hair medium_breasts multicolored_hair neneko_mashiro off_shoulder on_bed orange_shirt prison prison_cell prison_clothes prisoner red_eyes red_hair restrained shirt short_sleeves shorts single_bare_shoulder single_earring sitting stellive streaked_hair tail very_long_hair virtual_youtuber
0
1girl absurdres animal_ears bed between_legs black_shorts bound bound_wrists breasts cat_ears cat_girl cat_tail cleavage cuffs earrings extra_ears grey_hair hand_between_legs handcuffs highres iron_bars jewelry jjalbaaaaa light_smile long_hair medium_breasts multicolored_hair neneko_mashiro off_shoulder on_bed orange_shirt prison prison_cell prison_clothes prisoner red_eyes red_hair restrained shirt short_sleeves shorts single_bare_shoulder single_earring sitting stellive streaked_hair tail very_long_hair virtual_youtuber
34
0
1femboy ai_generated anal anal_sex ass_focus balls cellmates cock dick femboy femboy_focus feminine_male gay gay_sex inmate inmates_clothing jail male male_focus male_only medium_hair orange_clothing penetration penis penis_in_ass prison prison_clothes prison_uniform prisoner red_hair red_hair_male redcherryart redhead_male riding riding_penis testicles uniform white_skin
0
1femboy ai_generated anal anal_sex ass_focus balls cellmates cock dick femboy femboy_focus feminine_male gay gay_sex inmate inmates_clothing jail male male_focus male_only medium_hair orange_clothing penetration penis penis_in_ass prison prison_clothes prison_uniform prisoner red_hair red_hair_male redcherryart redhead_male riding riding_penis testicles uniform white_skin
34
0
1boy 1femboy ai_generated anus balls blonde_hair blue_eyes blush blush cellmates femboy femboy_focus femboy_only feminine_male freckles gay girly inmate inmates_clothing jail lingerie male male_focus male_only orange_clothing prison prison_clothes prison_uniform prisoner redcherryart seductive seductive_look seductive_pose short_hair showing_ass showing_off testicles thighhighs white_skin white_thighhighs
0
1boy 1femboy ai_generated anus balls blonde_hair blue_eyes blush blush cellmates femboy femboy_focus femboy_only feminine_male freckles gay girly inmate inmates_clothing jail lingerie male male_focus male_only orange_clothing prison prison_clothes prison_uniform prisoner redcherryart seductive seductive_look seductive_pose short_hair showing_ass showing_off testicles thighhighs white_skin white_thighhighs
47
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1femoby 2boys ai_generated anal anal_sex anus ass ass_focus asshole balls blonde_hair blonde_male blush cell cellmates cock dick femboy femboy_focus femboy_only feminine_male gay gay_male gay_sex genitals grabbing grabbing_ass grabbing_from_behind inmate inmates_clothing jail long_hair_male looking_at_viewer looking_back male male_focus male_only orange_clothing penis prison prison_cell prison_clothes prison_uniform prisoner redcherryart testicles thin thin_male
0
1femoby 2boys ai_generated anal anal_sex anus ass ass_focus asshole balls blonde_hair blonde_male blush cell cellmates cock dick femboy femboy_focus femboy_only feminine_male gay gay_male gay_sex genitals grabbing grabbing_ass grabbing_from_behind inmate inmates_clothing jail long_hair_male looking_at_viewer looking_back male male_focus male_only orange_clothing penis prison prison_cell prison_clothes prison_uniform prisoner redcherryart testicles thin thin_male
55
0
1femoby 2boys ai_generated anal anal_sex anus aroused aroused_face ass ass_focus asshole balls blonde_hair blonde_male blue_eyes blush cell cellmates cock dick femboy femboy_focus femboy_only feminine_male gay gay_male gay_sex genitals inmate inmates_clothing jail long_hair_male looking_at_viewer looking_back male male_focus male_only open_mouth orange_clothing penis ponytail prison prison_cell prison_clothes prison_uniform prisoner redcherryart testicles
0
1femoby 2boys ai_generated anal anal_sex anus aroused aroused_face ass ass_focus asshole balls blonde_hair blonde_male blue_eyes blush cell cellmates cock dick femboy femboy_focus femboy_only feminine_male gay gay_male gay_sex genitals inmate inmates_clothing jail long_hair_male looking_at_viewer looking_back male male_focus male_only open_mouth orange_clothing penis ponytail prison prison_cell prison_clothes prison_uniform prisoner redcherryart testicles
44
0
1femboy 2boys ai_generated balls blonde_hair blonde_male blowjob blue_eyes blush cock cum cum_drool cum_in_mouth cum_inside cum_leaking deep_blowjob deepthroat dick dominated domination femboy femboy_focus feminine_male freckles freckles_on_face gay gay_sex hair hand_in_hair hand_on_head inmate inmates_clothing intense_orgasm jail long_hair long_hair_male male male_only oral oral_penetration orange_clothing orgasm orgasm_from_oral penis ponytail prison prison_clothes prison_uniform prisoner pubic_hair pulling_out redcherryart semen_in_mouth submissive submissive_femboy submissive_male testicles uniform
0
1femboy 2boys ai_generated balls blonde_hair blonde_male blowjob blue_eyes blush cock cum cum_drool cum_in_mouth cum_inside cum_leaking deep_blowjob deepthroat dick dominated domination femboy femboy_focus feminine_male freckles freckles_on_face gay gay_sex hair hand_in_hair hand_on_head inmate inmates_clothing intense_orgasm jail long_hair long_hair_male male male_only oral oral_penetration orange_clothing orgasm orgasm_from_oral penis ponytail prison prison_clothes prison_uniform prisoner pubic_hair pulling_out redcherryart semen_in_mouth submissive submissive_femboy submissive_male testicles uniform
a month ago
4
0
1girl absurdres alternate_costume arrest ass blurry blurry_background bound bound_wrists breasts brown_eyes brown_hair camera cellphone commentary_request commission crowd cuffs dated hairband handcuffs highres kasu_(kasunohikari) medium_breasts phone prison_clothes rope short_hair skeb_commission smartphone smile solo_focus striped_clothes suzumiya_haruhi suzumiya_haruhi_no_yuuutsu taking_picture tied_up_(nonsexual) wind wind_lift
0
1girl absurdres alternate_costume arrest ass blurry blurry_background bound bound_wrists breasts brown_eyes brown_hair camera cellphone commentary_request commission crowd cuffs dated hairband handcuffs highres kasu_(kasunohikari) medium_breasts phone prison_clothes rope short_hair skeb_commission smartphone smile solo_focus striped_clothes suzumiya_haruhi suzumiya_haruhi_no_yuuutsu taking_picture tied_up_(nonsexual) wind wind_lift
61
0
1boy 1femboy ai_generated ass balls blonde_hair blush cellmates femboy feminine_male inmate inmates_clothing jail long_hair male male_focus male_only no_panties otoko_no_ko prison prison_clothes prisoner redcherryart sissy spread_ass t-shirt testicles trap
0
1boy 1femboy ai_generated ass balls blonde_hair blush cellmates femboy feminine_male inmate inmates_clothing jail long_hair male male_focus male_only no_panties otoko_no_ko prison prison_clothes prisoner redcherryart sissy spread_ass t-shirt testicles trap
37
0
1boy 1femboy 1girls 2boys ai_generated arousal balls big_penis blonde_hair blonde_male blowjob blue_eyes blush cock cum cum_drool cum_in_mouth cum_inside cum_leaking cumming cute deep_blowjob deepthroat dick dominated domination eye_contact female femboy femboy_focus feminine_male freckles freckles_on_face gay gay_sex hair hand_in_hair hand_on_head inmate inmates_clothing jail kneeling kneeling_oral_position large_penis light-skinned_female long_hair long_hair_male long_penis male male_only oral oral_penetration orange_clothing penis petite ponytail prison prison_clothes prison_uniform prisoner pubic_hair pulling_out redcherryart semen semen_in_mouth shy skinny slim submissive submissive_femboy submissive_male teenager testicles uniform worried
0
1boy 1femboy 1girls 2boys ai_generated arousal balls big_penis blonde_hair blonde_male blowjob blue_eyes blush cock cum cum_drool cum_in_mouth cum_inside cum_leaking cumming cute deep_blowjob deepthroat dick dominated domination eye_contact female femboy femboy_focus feminine_male freckles freckles_on_face gay gay_sex hair hand_in_hair hand_on_head inmate inmates_clothing jail kneeling kneeling_oral_position large_penis light-skinned_female long_hair long_hair_male long_penis male male_only oral oral_penetration orange_clothing penis petite ponytail prison prison_clothes prison_uniform prisoner pubic_hair pulling_out redcherryart semen semen_in_mouth shy skinny slim submissive submissive_femboy submissive_male teenager testicles uniform worried
25
0
1femboy 2boys ai_generated balls blonde_hair blonde_male blowjob blue_eyes blush blush cock cum cum_drool cum_in_mouth cum_inside cum_leaking dick dominated domination femboy femboy_focus feminine_male freckles freckles_on_face gay gay_sex hair hand_in_hair hand_on_head inmate inmates_clothing jail long_hair long_hair_male male male_only oral oral_penetration oral_sex orange_clothing penis ponytail prison prison_clothes prison_uniform prisoner pubic_hair redcherryart submissive submissive_femboy submissive_male testicles uniform
0
1femboy 2boys ai_generated balls blonde_hair blonde_male blowjob blue_eyes blush blush cock cum cum_drool cum_in_mouth cum_inside cum_leaking dick dominated domination femboy femboy_focus feminine_male freckles freckles_on_face gay gay_sex hair hand_in_hair hand_on_head inmate inmates_clothing jail long_hair long_hair_male male male_only oral oral_penetration oral_sex orange_clothing penis ponytail prison prison_clothes prison_uniform prisoner pubic_hair redcherryart submissive submissive_femboy submissive_male testicles uniform
27
0
1femboy 2boys ai_generated arousal aroused_male balls blonde_hair blonde_male blowjob blue_eyes blush cock cum cum_drool cum_in_mouth cum_inside cum_leaking deep_blowjob deepthroat dick dominated domination femboy femboy_focus feminine_male freckles freckles_on_face gay gay_sex hair hand_in_hair hand_on_head inmate inmates_clothing intense_orgasm jail long_hair long_hair_male lots_of_cum male male_only oral oral_penetration orange_clothing orgasm orgasm_from_oral penis ponytail prison prison_clothes prison_uniform prisoner pubic_hair redcherryart semen_in_mouth submissive submissive_femboy submissive_male testicles uniform
0
1femboy 2boys ai_generated arousal aroused_male balls blonde_hair blonde_male blowjob blue_eyes blush cock cum cum_drool cum_in_mouth cum_inside cum_leaking deep_blowjob deepthroat dick dominated domination femboy femboy_focus feminine_male freckles freckles_on_face gay gay_sex hair hand_in_hair hand_on_head inmate inmates_clothing intense_orgasm jail long_hair long_hair_male lots_of_cum male male_only oral oral_penetration orange_clothing orgasm orgasm_from_oral penis ponytail prison prison_clothes prison_uniform prisoner pubic_hair redcherryart semen_in_mouth submissive submissive_femboy submissive_male testicles uniform
43
0
1femboy 2boys ai_generated anal anal_insertion anal_sex arousal aroused aroused_face balls blonde_hair blonde_male blue_eyes blush cock cum cum_in_ass cum_inside cumming dick femboy femboy_focus feminine_male gay gay_male gay_sex inmate inmates_clothing jail long_hair long_hair_male male male_focus male_only orange_clothing penis ponytail prison prison_clothes prison_uniform prisoner redcherryart saliva saliva_drip semen semen_in_anus testicles tongue tongue_out uniform white_skin
0
1femboy 2boys ai_generated anal anal_insertion anal_sex arousal aroused aroused_face balls blonde_hair blonde_male blue_eyes blush cock cum cum_in_ass cum_inside cumming dick femboy femboy_focus feminine_male gay gay_male gay_sex inmate inmates_clothing jail long_hair long_hair_male male male_focus male_only orange_clothing penis ponytail prison prison_clothes prison_uniform prisoner redcherryart saliva saliva_drip semen semen_in_anus testicles tongue tongue_out uniform white_skin
3 weeks ago
29
0
arrest averting_eyes ball_gag bdsm bench black_hair black_hat black_necktie black_pants black_shoes blush bondage bound bound_arms breasts brown_eyes chest_harness collared_shirt commentary_request commission crying crying_with_eyes_open cuffs double-parted_bangs drooling exhibitionism femdom flashlight funitarefu gag grey_hair grey_shirt hair_between_eyes hair_ornament hairband hairclip handcuffs harness haruna_(kancolle) hat highres holding holding_flashlight holding_leash kantai_collection lamppost leash long_hair looking_at_another medium_breasts navel necktie night nipples outdoors pants parallel_hairclips park park_bench pixiv_commission police police_uniform policeman policewoman prison_clothes public_indecency public_nudity saliva saliva_on_breasts sandals shibari shibari_under_clothes shirt shoes short_sleeves sidelocks stomach striped_clothes striped_pants tears topless_female vending_machine vest walking yellow_hairband
0
arrest averting_eyes ball_gag bdsm bench black_hair black_hat black_necktie black_pants black_shoes blush bondage bound bound_arms breasts brown_eyes chest_harness collared_shirt commentary_request commission crying crying_with_eyes_open cuffs double-parted_bangs drooling exhibitionism femdom flashlight funitarefu gag grey_hair grey_shirt hair_between_eyes hair_ornament hairband hairclip handcuffs harness haruna_(kancolle) hat highres holding holding_flashlight holding_leash kantai_collection lamppost leash long_hair looking_at_another medium_breasts navel necktie night nipples outdoors pants parallel_hairclips park park_bench pixiv_commission police police_uniform policeman policewoman prison_clothes public_indecency public_nudity saliva saliva_on_breasts sandals shibari shibari_under_clothes shirt shoes short_sleeves sidelocks stomach striped_clothes striped_pants tears topless_female vending_machine vest walking yellow_hairband
35
0
1femboy 2boys ai_generated balls blonde_hair blonde_male blowjob blue_eyes blush blush cock cum cum_drool cum_in_mouth cum_inside cum_leaking cum_on_body cum_on_face dick dominated domination femboy femboy_focus feminine_male freckles freckles_on_face gay gay_sex hair hand_in_hair hand_on_head inmate inmates_clothing intense_orgasm jail kneeling kneeling_male kneeling_oral_position long_hair long_hair_male male male_only open_mouth oral oral_penetration oral_sex orange_clothing orgasm orgasm_from_oral penis ponytail prison prison_clothes prison_uniform prisoner pubic_hair redcherryart semen_in_mouth submissive submissive_femboy submissive_male testicles uniform
0
1femboy 2boys ai_generated balls blonde_hair blonde_male blowjob blue_eyes blush blush cock cum cum_drool cum_in_mouth cum_inside cum_leaking cum_on_body cum_on_face dick dominated domination femboy femboy_focus feminine_male freckles freckles_on_face gay gay_sex hair hand_in_hair hand_on_head inmate inmates_clothing intense_orgasm jail kneeling kneeling_male kneeling_oral_position long_hair long_hair_male male male_only open_mouth oral oral_penetration oral_sex orange_clothing orgasm orgasm_from_oral penis ponytail prison prison_clothes prison_uniform prisoner pubic_hair redcherryart semen_in_mouth submissive submissive_femboy submissive_male testicles uniform
36
0
1femboy 2boys ai_generated anal anal_insertion anal_sex anal_sex arousal aroused aroused_face blonde_hair blonde_male blush femboy femboy_focus feminine_male gay gay_male gay_sex inmate inmates_clothing jail long_hair long_hair_male male male_focus male_only orange_clothing ponytail prison prison_clothes prison_uniform prisoner redcherryart uniform white_skin
0
1femboy 2boys ai_generated anal anal_insertion anal_sex anal_sex arousal aroused aroused_face blonde_hair blonde_male blush femboy femboy_focus feminine_male gay gay_male gay_sex inmate inmates_clothing jail long_hair long_hair_male male male_focus male_only orange_clothing ponytail prison prison_clothes prison_uniform prisoner redcherryart uniform white_skin
44
0
1boy 1femoby ai_generated ass ass_focus balls bars blonde_hair blonde_male blush femboy femboy_focus femboy_only feminine_male gay gay_male inmate inmates_clothing jail long_hair_male male male_focus male_only orange_clothing prison prison_clothes prison_uniform prisoner redcherryart testicles
0
1boy 1femoby ai_generated ass ass_focus balls bars blonde_hair blonde_male blush femboy femboy_focus femboy_only feminine_male gay gay_male inmate inmates_clothing jail long_hair_male male male_focus male_only orange_clothing prison prison_clothes prison_uniform prisoner redcherryart testicles
37
0
1femboy ai_generated anal anal_sex ass_focus cellmates cock dick femboy femboy_focus feminine_male gay gay_sex inmate inmates_clothing jail male male_focus male_only medium_hair orange_clothing penis prison prison_clothes prison_uniform prisoner railing red_hair red_hair_male redcherryart redhead_male uniform white_skin
0
1femboy ai_generated anal anal_sex ass_focus cellmates cock dick femboy femboy_focus feminine_male gay gay_sex inmate inmates_clothing jail male male_focus male_only medium_hair orange_clothing penis prison prison_clothes prison_uniform prisoner railing red_hair red_hair_male redcherryart redhead_male uniform white_skin
a month ago
84
0
2girls 3d ace_attorney amateurthrowaway animated black_hair bouncing_breasts breasts brown_hair clothed_sex cooperative_fellatio doggystyle ema_skye fellatio finger_in_another's_mouth group_sex hetero higher_resolution_available licking licking_penis maya_fey multiple_boys multiple_girls netorare nipples oral penis phoenix_wright prison prison_clothes sex sex_from_behind sound tagme teamwork_(sexual) uncensored video watching
0
2girls 3d ace_attorney amateurthrowaway animated black_hair bouncing_breasts breasts brown_hair clothed_sex cooperative_fellatio doggystyle ema_skye fellatio finger_in_another's_mouth group_sex hetero higher_resolution_available licking licking_penis maya_fey multiple_boys multiple_girls netorare nipples oral penis phoenix_wright prison prison_clothes sex sex_from_behind sound tagme teamwork_(sexual) uncensored video watching
a month ago
3
0
6+girls absurdres alternate_costume breasts commentary cuffs empty_eyes english_commentary fire_ritsu full_body girls'_frontline grey_eyes grey_hair handcuffs highres jumpsuit looking_at_viewer medium_hair mob_x_character multiple_girls open_mouth orange_jumpsuit orange_pants orange_shirt orange_shoes pants ponytail prison prison_clothes prisoner rpk-16_(girls'_frontline) shackles shirt shoes short_ponytail short_sleeves sidelocks socks standing tongue white_socks
0
6+girls absurdres alternate_costume breasts commentary cuffs empty_eyes english_commentary fire_ritsu full_body girls'_frontline grey_eyes grey_hair handcuffs highres jumpsuit looking_at_viewer medium_hair mob_x_character multiple_girls open_mouth orange_jumpsuit orange_pants orange_shirt orange_shoes pants ponytail prison prison_clothes prisoner rpk-16_(girls'_frontline) shackles shirt shoes short_ponytail short_sleeves sidelocks socks standing tongue white_socks
4 days ago
3
0
1girl absurdres bound breasts cleavage commission cuffs dead_or_alive handcuffs highres jumpsuit lobelia_(doa) mugshot pixiv_commission prison prison_clothes prisoner restrained shackles togaxan togazan
0
1girl absurdres bound breasts cleavage commission cuffs dead_or_alive handcuffs highres jumpsuit lobelia_(doa) mugshot pixiv_commission prison prison_clothes prisoner restrained shackles togaxan togazan
52
0
1femboy 2boys ai_generated anal anal_insertion anal_sex arousal aroused aroused_face balls blonde_hair blonde_male blue_eyes blush bussy cock cum cum_in_anus cum_in_ass cum_inside cumming dick femboy femboy_focus feminine_male gay gay_male gay_sex inmate inmates_clothing jail long_hair long_hair_male male male_focus male_only orange_clothing penis ponytail prison prison_clothes prison_uniform prisoner redcherryart sissy testicles uniform white_skin
0
1femboy 2boys ai_generated anal anal_insertion anal_sex arousal aroused aroused_face balls blonde_hair blonde_male blue_eyes blush bussy cock cum cum_in_anus cum_in_ass cum_inside cumming dick femboy femboy_focus feminine_male gay gay_male gay_sex inmate inmates_clothing jail long_hair long_hair_male male male_focus male_only orange_clothing penis ponytail prison prison_clothes prison_uniform prisoner redcherryart sissy testicles uniform white_skin
a month ago
3
0
1boy 1girl arms_around_neck ball_and_chain_restraint bandaged_hand bandaged_head bandages barefoot black_hair blonde_hair blue_eyes bound bound_ankles bound_together bound_wrists chain chain_leash clothes_around_waist colored_eyelashes cuffs english_text expressionless full_body handcuffs highres hug isaac_foster iseatingstone jacket jacket_around_waist kneeling leash long_hair looking_at_viewer pants prison_clothes rachel_gardner red_background red_pants restrained satsuriku_no_tenshi shirt short_hair simple_background smile striped_clothes striped_shirt
0
1boy 1girl arms_around_neck ball_and_chain_restraint bandaged_hand bandaged_head bandages barefoot black_hair blonde_hair blue_eyes bound bound_ankles bound_together bound_wrists chain chain_leash clothes_around_waist colored_eyelashes cuffs english_text expressionless full_body handcuffs highres hug isaac_foster iseatingstone jacket jacket_around_waist kneeling leash long_hair looking_at_viewer pants prison_clothes rachel_gardner red_background red_pants restrained satsuriku_no_tenshi shirt short_hair simple_background smile striped_clothes striped_shirt
2 weeks ago
1
0
1boy animal_ears arm_up braid brown_hair commentary_request con_potata cowboy_shot dark-skinned_male dark_skin disintegration green_eyes grin hand_in_own_hair highres jumpsuit leona_kingscholar lion_boy lion_ears lion_tail long_hair looking_at_viewer male_focus mugshot orange_jumpsuit prison_clothes scar scar_across_eye scar_on_face smile solo tail tank_top twin_braids twisted_wonderland white_background white_tank_top
0
1boy animal_ears arm_up braid brown_hair commentary_request con_potata cowboy_shot dark-skinned_male dark_skin disintegration green_eyes grin hand_in_own_hair highres jumpsuit leona_kingscholar lion_boy lion_ears lion_tail long_hair looking_at_viewer male_focus mugshot orange_jumpsuit prison_clothes scar scar_across_eye scar_on_face smile solo tail tank_top twin_braids twisted_wonderland white_background white_tank_top
2 weeks ago
1
0
animal_ears black_tank_top blonde_hair brown_hair commentary_request con_potata disintegration fangs green_eyes grey_eyes highres holding holding_sign hyena_boy hyena_ears jack_howl jumpsuit leona_kingscholar lion_boy lion_ears lion_tail looking_at_viewer middle_finger mugshot orange_jumpsuit prison_clothes ruggie_bucchi scar scar_across_eye scar_on_face short_hair sign tail tank_top twisted_wonderland white_background white_hair white_tank_top wolf_ears wolf_tail yellow_eyes
0
animal_ears black_tank_top blonde_hair brown_hair commentary_request con_potata disintegration fangs green_eyes grey_eyes highres holding holding_sign hyena_boy hyena_ears jack_howl jumpsuit leona_kingscholar lion_boy lion_ears lion_tail looking_at_viewer middle_finger mugshot orange_jumpsuit prison_clothes ruggie_bucchi scar scar_across_eye scar_on_face short_hair sign tail tank_top twisted_wonderland white_background white_hair white_tank_top wolf_ears wolf_tail yellow_eyes
38
0
1femboy 2boys ai_generated anal anal_insertion anal_sex arousal aroused aroused_face balls blonde_hair blonde_male blue_eyes blush bussy cock cowgirl_position dick erect_penis erection femboy femboy_focus feminine_male gay gay_male gay_sex grabbing_thighs inmate inmates_clothing jail long_hair long_hair_male male male_focus male_only orange_clothing penis ponytail prison prison_clothes prison_uniform prisoner redcherryart riding riding_cock riding_penis sissy slim slim_male testicles thighs thin thin_waist uniform white_skin
0
1femboy 2boys ai_generated anal anal_insertion anal_sex arousal aroused aroused_face balls blonde_hair blonde_male blue_eyes blush bussy cock cowgirl_position dick erect_penis erection femboy femboy_focus feminine_male gay gay_male gay_sex grabbing_thighs inmate inmates_clothing jail long_hair long_hair_male male male_focus male_only orange_clothing penis ponytail prison prison_clothes prison_uniform prisoner redcherryart riding riding_cock riding_penis sissy slim slim_male testicles thighs thin thin_waist uniform white_skin
a month ago
3
0
1girl alternate_costume arrest ass blurry blurry_background bound bound_wrists breasts brown_eyes brown_hair camera cellphone commentary_request commission crowd cuffs dated hairband handcuffs kasu_(kasunohikari) medium_breasts phone prison_clothes rope short_hair skeb_commission smartphone smile solo_focus striped_clothes suzumiya_haruhi suzumiya_haruhi_no_yuuutsu taking_picture tied_up_(nonsexual) wind wind_lift
0
1girl alternate_costume arrest ass blurry blurry_background bound bound_wrists breasts brown_eyes brown_hair camera cellphone commentary_request commission crowd cuffs dated hairband handcuffs kasu_(kasunohikari) medium_breasts phone prison_clothes rope short_hair skeb_commission smartphone smile solo_focus striped_clothes suzumiya_haruhi suzumiya_haruhi_no_yuuutsu taking_picture tied_up_(nonsexual) wind wind_lift
2 weeks ago
2
0
1boy ass beanie belt belt_buckle black_belt black_hat black_jacket black_pants black_shirt blue_pants blue_shirt blush_stickers brown_hair buckle cigarette commentary_request cowboy_shot danganronpa_(series) danganronpa_v3:_killing_harmony day fake_horns hat horned_headwear horns hoshi_ryoma indoors jacket jacket_partially_removed leather leather_jacket light_particles light_rays long_sleeves male_focus mouth_hold open_belt pants prison_clothes r'l_(arul-erur-plant-403) shirt short_hair shoulder_blades solo standing striped_clothes striped_pants striped_shirt sun tight_clothes two-tone_pants two-tone_shirt undressing
0
1boy ass beanie belt belt_buckle black_belt black_hat black_jacket black_pants black_shirt blue_pants blue_shirt blush_stickers brown_hair buckle cigarette commentary_request cowboy_shot danganronpa_(series) danganronpa_v3:_killing_harmony day fake_horns hat horned_headwear horns hoshi_ryoma indoors jacket jacket_partially_removed leather leather_jacket light_particles light_rays long_sleeves male_focus mouth_hold open_belt pants prison_clothes r'l_(arul-erur-plant-403) shirt short_hair shoulder_blades solo standing striped_clothes striped_pants striped_shirt sun tight_clothes two-tone_pants two-tone_shirt undressing
a month ago
1
0
2girls belt blonde_hair blush_stickers bracelet collar crunchcontrol gloves grey_eyes hat highres jewelry lollipop_in_mouth looking_at_viewer multiple_girls necktie original police police_hat prison_clothes shirt short_necktie skirt spiked_bracelet spiked_collar spikes striped_necktie torn_clothes torn_shirt white_gloves wispy_bangs
0
2girls belt blonde_hair blush_stickers bracelet collar crunchcontrol gloves grey_eyes hat highres jewelry lollipop_in_mouth looking_at_viewer multiple_girls necktie original police police_hat prison_clothes shirt short_necktie skirt spiked_bracelet spiked_collar spikes striped_necktie torn_clothes torn_shirt white_gloves wispy_bangs
25
0
1femboy 2boys ai_generated anal anal_sex anal_sex ass ass_focus blonde_hair cellmates cock cum cum_in_ass cum_inside dick erect_penis erection femboy femboy_focus feminine_male gay gay_domination gay_sex inmate inmates_clothing jail large_cock large_penis long_penis male male_domination male_focus male_only orange_clothing penetration penis prison prison_clothes prison_uniform prisoner redcherryart semen short_hair uniform white_skin
0
1femboy 2boys ai_generated anal anal_sex anal_sex ass ass_focus blonde_hair cellmates cock cum cum_in_ass cum_inside dick erect_penis erection femboy femboy_focus feminine_male gay gay_domination gay_sex inmate inmates_clothing jail large_cock large_penis long_penis male male_domination male_focus male_only orange_clothing penetration penis prison prison_clothes prison_uniform prisoner redcherryart semen short_hair uniform white_skin
30
0
1femboy 2boys ai_generated anal anal_insertion anal_sex arousal aroused aroused_face balls blonde_hair blonde_male blue_eyes blush bussy cock cowgirl_position dick erect_penis erection femboy femboy_focus feminine_male gay gay_male gay_sex inmate inmates_clothing jail long_hair long_hair_male male male_focus male_only orange_clothing penis ponytail prison prison_clothes prison_uniform prisoner redcherryart riding riding_cock riding_penis sissy testicles uniform white_skin
0
1femboy 2boys ai_generated anal anal_insertion anal_sex arousal aroused aroused_face balls blonde_hair blonde_male blue_eyes blush bussy cock cowgirl_position dick erect_penis erection femboy femboy_focus feminine_male gay gay_male gay_sex inmate inmates_clothing jail long_hair long_hair_male male male_focus male_only orange_clothing penis ponytail prison prison_clothes prison_uniform prisoner redcherryart riding riding_cock riding_penis sissy testicles uniform white_skin
39
0
1femboy 2boys after_oral ai_generated balls blonde_hair blonde_male blowjob blue_eyes blush blush cock cum cum_drool cum_in_mouth cum_inside cum_leaking cum_on_body cum_on_face dick dominated domination drinking_cum eating_cum femboy femboy_focus feminine_male freckles freckles_on_face gay gay_sex hair hand_in_hair hand_on_head inmate inmates_clothing intense_orgasm jail long_hair long_hair_male male male_only open_mouth oral oral_penetration oral_sex orange_clothing orgasm orgasm_from_oral penis ponytail post_oral prison prison_clothes prison_uniform prisoner pubic_hair redcherryart semen_in_mouth submissive submissive_femboy submissive_male testicles uniform
0
1femboy 2boys after_oral ai_generated balls blonde_hair blonde_male blowjob blue_eyes blush blush cock cum cum_drool cum_in_mouth cum_inside cum_leaking cum_on_body cum_on_face dick dominated domination drinking_cum eating_cum femboy femboy_focus feminine_male freckles freckles_on_face gay gay_sex hair hand_in_hair hand_on_head inmate inmates_clothing intense_orgasm jail long_hair long_hair_male male male_only open_mouth oral oral_penetration oral_sex orange_clothing orgasm orgasm_from_oral penis ponytail post_oral prison prison_clothes prison_uniform prisoner pubic_hair redcherryart semen_in_mouth submissive submissive_femboy submissive_male testicles uniform
45
0
1femboy 2boys ai_generated anal anal_insertion anal_sex arousal aroused aroused_face blonde_hair blonde_male blush cock dick femboy femboy_focus feminine_male floor gay gay_male gay_sex inmate inmates_clothing jail laying_on_floor long_hair long_hair_male male male_domination male_focus male_only on_floor orange_clothing penis ponytail prison prison_clothes prison_uniform prisoner redcherryart submissive_femboy submissive_male uniform white_skin
0
1femboy 2boys ai_generated anal anal_insertion anal_sex arousal aroused aroused_face blonde_hair blonde_male blush cock dick femboy femboy_focus feminine_male floor gay gay_male gay_sex inmate inmates_clothing jail laying_on_floor long_hair long_hair_male male male_domination male_focus male_only on_floor orange_clothing penis ponytail prison prison_clothes prison_uniform prisoner redcherryart submissive_femboy submissive_male uniform white_skin
31
0
1femboy 2boys ai_generated balls blonde_hair blonde_male blowjob blue_eyes blush blush cock cum cum_drool cum_in_mouth cum_inside cum_leaking dick dominated domination dripping dripping_cum dripping_semen femboy femboy_focus feminine_male freckles freckles_on_face gay gay_sex grabbing_head hair hand_in_hair hand_on_head inmate inmates_clothing jail long_hair long_hair_male male male_only oral oral_penetration oral_sex orange_clothing penis ponytail prison prison_clothes prison_uniform prisoner pubic_hair redcherryart submissive submissive_femboy submissive_male testicles uniform
0
1femboy 2boys ai_generated balls blonde_hair blonde_male blowjob blue_eyes blush blush cock cum cum_drool cum_in_mouth cum_inside cum_leaking dick dominated domination dripping dripping_cum dripping_semen femboy femboy_focus feminine_male freckles freckles_on_face gay gay_sex grabbing_head hair hand_in_hair hand_on_head inmate inmates_clothing jail long_hair long_hair_male male male_only oral oral_penetration oral_sex orange_clothing penis ponytail prison prison_clothes prison_uniform prisoner pubic_hair redcherryart submissive submissive_femboy submissive_male testicles uniform
32
0
1femboy 2boys ai_generated anal anal_insertion anal_sex arousal aroused aroused_face balls blonde_hair blonde_male blue_eyes blush bussy cock cowgirl_position dick erect_penis erection femboy femboy_focus feminine_male gay gay_male gay_sex grabbing_thighs hands_on_hips inmate inmates_clothing jail long_hair long_hair_male male male_focus male_only motion_blur motion_lines open_mouth orange_clothing penis ponytail prison prison_clothes prison_uniform prisoner redcherryart riding riding_cock riding_penis sissy slim slim_male testicles thighs thin thin_waist thrusting thrusting_into_ass uniform white_skin
0
1femboy 2boys ai_generated anal anal_insertion anal_sex arousal aroused aroused_face balls blonde_hair blonde_male blue_eyes blush bussy cock cowgirl_position dick erect_penis erection femboy femboy_focus feminine_male gay gay_male gay_sex grabbing_thighs hands_on_hips inmate inmates_clothing jail long_hair long_hair_male male male_focus male_only motion_blur motion_lines open_mouth orange_clothing penis ponytail prison prison_clothes prison_uniform prisoner redcherryart riding riding_cock riding_penis sissy slim slim_male testicles thighs thin thin_waist thrusting thrusting_into_ass uniform white_skin
3 weeks ago
7
0
2girls absurdres armband ball_and_chain_restraint between_breasts bikini black_bikini black_hair black_necktie black_survival black_thighhighs blue_eyes blue_hair blue_hat blue_skirt breasts chain character_name colored_inner_hair cropped_jacket cuffs debi_(black_survival) dress eternal_return:_black_survival full_body green_armband hair_intakes hand_on_own_hip hat high_heels highres holding holding_phone jacket leaning_forward long_sleeves marlene_(black_survival) multicolored_hair multiple_girls necktie necktie_between_breasts one_side_up open_clothes open_jacket pencil_skirt phone pink_hair police_badge police_hat prison_clothes red_eyes shackles short_hair siblings sisters skirt standing striped_clothes striped_dress suisen_(suisenhwa) swimsuit thigh_strap thighhighs twins
0
2girls absurdres armband ball_and_chain_restraint between_breasts bikini black_bikini black_hair black_necktie black_survival black_thighhighs blue_eyes blue_hair blue_hat blue_skirt breasts chain character_name colored_inner_hair cropped_jacket cuffs debi_(black_survival) dress eternal_return:_black_survival full_body green_armband hair_intakes hand_on_own_hip hat high_heels highres holding holding_phone jacket leaning_forward long_sleeves marlene_(black_survival) multicolored_hair multiple_girls necktie necktie_between_breasts one_side_up open_clothes open_jacket pencil_skirt phone pink_hair police_badge police_hat prison_clothes red_eyes shackles short_hair siblings sisters skirt standing striped_clothes striped_dress suisen_(suisenhwa) swimsuit thigh_strap thighhighs twins
54
0
1boy 1femboy ai_generated ass asshole balls blonde_hair blush cellmates femboy femboy_focus feminine_male freckles inmate inmates_clothing jail long_hair male male_focus male_only no_panties otoko_no_ko prison prison_clothes prisoner redcherryart sissy spread_ass t-shirt testicles trap
0
1boy 1femboy ai_generated ass asshole balls blonde_hair blush cellmates femboy femboy_focus feminine_male freckles inmate inmates_clothing jail long_hair male male_focus male_only no_panties otoko_no_ko prison prison_clothes prisoner redcherryart sissy spread_ass t-shirt testicles trap
51
0
1boy 1femoby ai ai-created ai_art ai_assisted ai_generated anus ass ass_focus asshole balls blonde_hair blonde_male blush cock dick femboy femboy_focus femboy_only feminine_male gay gay_male genitals inmate inmates_clothing jail long_hair_male looking_at_viewer looking_back male male_focus male_only orange_clothing penis prison prison_clothes prison_uniform prisoner redcherryart shoes spread_ass spreading_anus spreading_ass stretched_anus testicles thin thin_male
0
1boy 1femoby ai ai-created ai_art ai_assisted ai_generated anus ass ass_focus asshole balls blonde_hair blonde_male blush cock dick femboy femboy_focus femboy_only feminine_male gay gay_male genitals inmate inmates_clothing jail long_hair_male looking_at_viewer looking_back male male_focus male_only orange_clothing penis prison prison_clothes prison_uniform prisoner redcherryart shoes spread_ass spreading_anus spreading_ass stretched_anus testicles thin thin_male
47
0
1femboy 2boys ai_generated anal anal_sex anus ass ass_focus asshole balls blonde_hair blonde_male blue_eyes blush cell cellmates cock dick femboy femboy_focus femboy_only feminine_male gay gay_male gay_sex genitals inmate inmates_clothing jail long_hair_male looking_at_viewer looking_back male male_focus male_only open_mouth orange_clothing penis prison prison_cell prison_clothes prison_uniform prisoner redcherryart testicles
0
1femboy 2boys ai_generated anal anal_sex anus ass ass_focus asshole balls blonde_hair blonde_male blue_eyes blush cell cellmates cock dick femboy femboy_focus femboy_only feminine_male gay gay_male gay_sex genitals inmate inmates_clothing jail long_hair_male looking_at_viewer looking_back male male_focus male_only open_mouth orange_clothing penis prison prison_cell prison_clothes prison_uniform prisoner redcherryart testicles
a month ago
2
0
1girl absurdres alternate_breast_size_(smaller) alternate_costume alternate_hairstyle asymmetrical_horns bare_shoulders barefoot black_collar black_hair black_shirt blue_background blue_hair breasts broken_horn collar colored_inner_hair commentary crying english_commentary english_text highres holding holding_phone holding_spoon hololive hololive_english horns jumpsuit medium_breasts multicolored_hair nerissa_ravencroft old_metal_666 open_jumpsuit orange_jumpsuit phone prison_clothes red_eyes shirt short_hair spoon virtual_youtuber
0
1girl absurdres alternate_breast_size_(smaller) alternate_costume alternate_hairstyle asymmetrical_horns bare_shoulders barefoot black_collar black_hair black_shirt blue_background blue_hair breasts broken_horn collar colored_inner_hair commentary crying english_commentary english_text highres holding holding_phone holding_spoon hololive hololive_english horns jumpsuit medium_breasts multicolored_hair nerissa_ravencroft old_metal_666 open_jumpsuit orange_jumpsuit phone prison_clothes red_eyes shirt short_hair spoon virtual_youtuber
35
0
1femboy 2boys ai_generated anal anal_insertion anal_sex arousal aroused aroused_face balls blonde_hair blonde_male blue_eyes blush bussy cock cowgirl_position dick erect_penis erection femboy femboy_focus feminine_male gay gay_male gay_sex grabbing_thighs inmate inmates_clothing jail long_hair long_hair_male male male_focus male_only orange_clothing penis ponytail prison prison_clothes prison_uniform prisoner redcherryart riding riding_cock riding_penis sissy slim slim_male testicles thighs thin thin_waist uniform white_skin
0
1femboy 2boys ai_generated anal anal_insertion anal_sex arousal aroused aroused_face balls blonde_hair blonde_male blue_eyes blush bussy cock cowgirl_position dick erect_penis erection femboy femboy_focus feminine_male gay gay_male gay_sex grabbing_thighs inmate inmates_clothing jail long_hair long_hair_male male male_focus male_only orange_clothing penis ponytail prison prison_clothes prison_uniform prisoner redcherryart riding riding_cock riding_penis sissy slim slim_male testicles thighs thin thin_waist uniform white_skin
3 weeks ago
22
0
absurdres arrest ball_gag bdsm bench black_hair black_hat black_necktie black_pants black_shoes blush bondage bound bound_arms breasts chest_harness closed_eyes collared_shirt commentary_request commission crying cuffs double-parted_bangs drooling exhibitionism femdom flashlight funitarefu gag grey_hair grey_shirt hair_between_eyes hair_ornament hairband hairclip handcuffs harness haruna_(kancolle) hat highres holding holding_flashlight holding_leash kantai_collection lamppost leash long_hair looking_at_another medium_breasts navel necktie night nipples outdoors pants parallel_hairclips park park_bench pixiv_commission police police_uniform policeman policewoman prison_clothes public_indecency public_nudity saliva saliva_on_breasts sandals shibari shibari_under_clothes shirt shoes short_sleeves sidelocks stomach striped_clothes striped_pants topless_female vending_machine vest walking yellow_hairband
0
absurdres arrest ball_gag bdsm bench black_hair black_hat black_necktie black_pants black_shoes blush bondage bound bound_arms breasts chest_harness closed_eyes collared_shirt commentary_request commission crying cuffs double-parted_bangs drooling exhibitionism femdom flashlight funitarefu gag grey_hair grey_shirt hair_between_eyes hair_ornament hairband hairclip handcuffs harness haruna_(kancolle) hat highres holding holding_flashlight holding_leash kantai_collection lamppost leash long_hair looking_at_another medium_breasts navel necktie night nipples outdoors pants parallel_hairclips park park_bench pixiv_commission police police_uniform policeman policewoman prison_clothes public_indecency public_nudity saliva saliva_on_breasts sandals shibari shibari_under_clothes shirt shoes short_sleeves sidelocks stomach striped_clothes striped_pants topless_female vending_machine vest walking yellow_hairband
42
0
1girls 5_finger 5_fingers alternate_version_at_patreon alternate_version_at_paywall animal_ear_fluff animal_ears animal_humanoid animal_skull animal_tail anthro anthro_female anthro_only anthrofied arm_raised arms_raised arms_up artist_name ass ass_cleavage ass_focus ass_out ass_view backboob background backview bare_arms bare_ass bare_hands bent_over black-haired_female black-skinned_female black_arms black_ass black_body black_ears black_fur black_hair black_hair_female black_hearts black_skin black_skinned_female black_tail breasts bubble_ass bubble_butt closed_mouth clothed clothing covered_eyes cowboy_shot curvaceous curvaceous_ass curvaceous_body curvaceous_female curvaceous_figure curvaceous_hips curvaceous_thighs curves curvy curvy_ass curvy_body curvy_female curvy_hips curvy_thighs dat_ass envylemonade eye_obstructed female female_focus female_only fingers fur furry_ears furry_tail half_body hand_raised hands_raised hands_up heart heart_symbol hips huge_ass huge_boobs huge_breasts huge_butt huge_thighs large_ass large_boobs large_breasts large_butt large_thighs long_pants looking_at_viewer looking_back mal0 mal0_(species) malo medium_hair mouth mouth_closed no_panties no_underwear non-human_only non-web_source obscured_eyes one_arm_raised one_arm_up one_eye_covered one_eye_obstructed one_eye_visible one_hand_raised one_hand_up orange_clothing orange_jumpsuit orange_pants orange_shirt orange_topwear pants peace_sign prison_clothes prison_uniform prisoner prisoner_woman scp scp-1471 scp-1471-a scp_foundation seduction seductive seductive_body seductive_pose short_tail shoulders skull skull_head smile smile_at_viewer smiling smiling_at_viewer smiling_female solo solo_female solo_focus suggestive suggestive_pose tail tease teasing teasing_viewer teasing_with_ass thick_thighs thighs topwear underboob viewed_from_behind voluptuous voluptuous_body voluptuous_female white_eyes white_face white_pupils wide_hip wide_hipped_anthro wide_hipped_female wide_hips
0
1girls 5_finger 5_fingers alternate_version_at_patreon alternate_version_at_paywall animal_ear_fluff animal_ears animal_humanoid animal_skull animal_tail anthro anthro_female anthro_only anthrofied arm_raised arms_raised arms_up artist_name ass ass_cleavage ass_focus ass_out ass_view backboob background backview bare_arms bare_ass bare_hands bent_over black-haired_female black-skinned_female black_arms black_ass black_body black_ears black_fur black_hair black_hair_female black_hearts black_skin black_skinned_female black_tail breasts bubble_ass bubble_butt closed_mouth clothed clothing covered_eyes cowboy_shot curvaceous curvaceous_ass curvaceous_body curvaceous_female curvaceous_figure curvaceous_hips curvaceous_thighs curves curvy curvy_ass curvy_body curvy_female curvy_hips curvy_thighs dat_ass envylemonade eye_obstructed female female_focus female_only fingers fur furry_ears furry_tail half_body hand_raised hands_raised hands_up heart heart_symbol hips huge_ass huge_boobs huge_breasts huge_butt huge_thighs large_ass large_boobs large_breasts large_butt large_thighs long_pants looking_at_viewer looking_back mal0 mal0_(species) malo medium_hair mouth mouth_closed no_panties no_underwear non-human_only non-web_source obscured_eyes one_arm_raised one_arm_up one_eye_covered one_eye_obstructed one_eye_visible one_hand_raised one_hand_up orange_clothing orange_jumpsuit orange_pants orange_shirt orange_topwear pants peace_sign prison_clothes prison_uniform prisoner prisoner_woman scp scp-1471 scp-1471-a scp_foundation seduction seductive seductive_body seductive_pose short_tail shoulders skull skull_head smile smile_at_viewer smiling smiling_at_viewer smiling_female solo solo_female solo_focus suggestive suggestive_pose tail tease teasing teasing_viewer teasing_with_ass thick_thighs thighs topwear underboob viewed_from_behind voluptuous voluptuous_body voluptuous_female white_eyes white_face white_pupils wide_hip wide_hipped_anthro wide_hipped_female wide_hips