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shadow (shadow2007x)

2024 chastity_cage chastity_device diaper digital_media_(artwork) drooling dubious_consent english_text hypnosis lila_lovestar_(sinfulwalpurrgis) male_penetrated male_penetrating male_penetrating_male maledom males_only mental_regression mind_control original pull-up_diaper shadow2007x shadow_(shadow2007x) sissy small_penis text uncensored x-ray x-ray_vision
2024 chastity_cage chastity_device diaper digital_media_(artwork) drooling dubious_consent english_text hypnosis lila_lovestar_(sinfulwalpurrgis) male_penetrated male_penetrating male_penetrating_male maledom males_only mental_regression mind_control original pull-up_diaper shadow2007x shadow_(shadow2007x) sissy small_penis text uncensored x-ray x-ray_vision
2024 chastity_cage chastity_device diaper digital_media_(artwork) drooling dubious_consent english_text hypnosis lila_lovestar_(sinfulwalpurrgis) male_penetrated male_penetrating male_penetrating_male maledom males_only mental_regression mind_control original pull-up_diaper shadow2007x shadow_(shadow2007x) sissy small_penis text uncensored
2024 chastity_cage chastity_device diaper digital_media_(artwork) drooling dubious_consent english_text hypnosis lila_lovestar_(sinfulwalpurrgis) male_penetrated male_penetrating male_penetrating_male maledom males_only mental_regression mind_control original pull-up_diaper shadow2007x shadow_(shadow2007x) sissy small_penis text uncensored
1boy 2020 absurd_res artist_name brown_hair bullying cbt cock_and_ball_torture commission crossdressing dialogue dominant english english_text eyeshadow femboy gay grey_background kneeling light-skinned_male light_skin lila_lovestar_(sinfulwalpurrgis) lipstick maledom orgasm_denial original penis_ribbon purple_eyeshadow purple_lipstick ribbon secretary shadow2007x shadow_(shadow2007x) sissy skirt skirt_lift stockings submissive suit thigh_high_stockings thigh_highs trying_not_to_cum uncensored yaoi
1boy 2020 absurd_res artist_name brown_hair bullying cbt cock_and_ball_torture commission crossdressing dialogue dominant english english_text eyeshadow femboy gay grey_background kneeling light-skinned_male light_skin lila_lovestar_(sinfulwalpurrgis) lipstick maledom orgasm_denial original penis_ribbon purple_eyeshadow purple_lipstick ribbon secretary shadow2007x shadow_(shadow2007x) sissy skirt skirt_lift stockings submissive suit thigh_high_stockings thigh_highs trying_not_to_cum uncensored yaoi
1boy 2020 anal bed bedroom commission cum cumshot dialogue english english_text femboy gay handjob lila_lovestar_(sinfulwalpurrgis) lipstick lipstick_mark male maledom on_bed original romantic shadow2007x shadow_(shadow2007x) speech_bubble uncensored yaoi
1boy 2020 anal bed bedroom commission cum cumshot dialogue english english_text femboy gay handjob lila_lovestar_(sinfulwalpurrgis) lipstick lipstick_mark male maledom on_bed original romantic shadow2007x shadow_(shadow2007x) speech_bubble uncensored yaoi
2020 anal big_penis body_writing chastity_cage chastity_device commission cum cum_in_ass dialogue digital_media_(artwork) english_text femboy gay human humiliation latex latex_armwear latex_thighhighs lila_lovestar_(sinfulwalpurrgis) lipstick male mind_break orgasm orgasm_face original purple_lipstick shadow2007x shadow_(shadow2007x) uncensored yaoi
2020 anal big_penis body_writing chastity_cage chastity_device commission cum cum_in_ass dialogue digital_media_(artwork) english_text femboy gay human humiliation latex latex_armwear latex_thighhighs lila_lovestar_(sinfulwalpurrgis) lipstick male mind_break orgasm orgasm_face original purple_lipstick shadow2007x shadow_(shadow2007x) uncensored yaoi
1boy 2018 abdl absurd_res comic comic_page diaper digital_media_(artwork) edging english_text humiliation lila_lovestar_(sinfulwalpurrgis) line_art maledom original page_3 page_number shadow2007x shadow_(shadow2007x) uncensored vibrator
1boy 2018 abdl absurd_res comic comic_page diaper digital_media_(artwork) edging english_text humiliation lila_lovestar_(sinfulwalpurrgis) line_art maledom original page_3 page_number shadow2007x shadow_(shadow2007x) uncensored vibrator
1boy 2018 abdl absurd_res comic comic_page diaper digital_media_(artwork) edging english_text humiliation lila_lovestar_(sinfulwalpurrgis) line_art maledom original page_2 page_number shadow2007x shadow_(shadow2007x) uncensored vibrator
1boy 2018 abdl absurd_res comic comic_page diaper digital_media_(artwork) edging english_text humiliation lila_lovestar_(sinfulwalpurrgis) line_art maledom original page_2 page_number shadow2007x shadow_(shadow2007x) uncensored vibrator
2018 2boys abdl absurd_res comic comic_page diaper diaper_under_clothing digital_media_(artwork) edging english_text humiliation lila_lovestar_(sinfulwalpurrgis) line_art maledom original page_1 page_number shadow2007x shadow_(shadow2007x) stealth_masturbation uncensored vibrator vibrator_under_clothes
2018 2boys abdl absurd_res comic comic_page diaper diaper_under_clothing digital_media_(artwork) edging english_text humiliation lila_lovestar_(sinfulwalpurrgis) line_art maledom original page_1 page_number shadow2007x shadow_(shadow2007x) stealth_masturbation uncensored vibrator vibrator_under_clothes
1boy 2023 abdl absurd_res anal blush brown_hair commission dialog diaper diaper_change digital_media_(artwork) english english_text flaccid gay humiliation light-skinned_male light_skin lila_lovestar_(sinfulwalpurrgis) maledom original pacifier rattle shadow2007x shadow_(shadow2007x) small_penis suit teddy_bear twintails uncensored uncut vibrator vibrator_in_ass yaoi
1boy 2023 abdl absurd_res anal blush brown_hair commission dialog diaper diaper_change digital_media_(artwork) english english_text flaccid gay humiliation light-skinned_male light_skin lila_lovestar_(sinfulwalpurrgis) maledom original pacifier rattle shadow2007x shadow_(shadow2007x) small_penis suit teddy_bear twintails uncensored uncut vibrator vibrator_in_ass yaoi
2023 anal artist_name brown_hair chaps commission cowboy_hat cum cum_in_pussy digital_media_(artwork) equine_penis gay horse horsecock interspecies leather leather_chaps light-skinned_male light_skin lila_lovestar_(sinfulwalpurrgis) male maledom mind_break original shadow2007x shadow_(shadow2007x) uncensored yaoi zoophilia
2023 anal artist_name brown_hair chaps commission cowboy_hat cum cum_in_pussy digital_media_(artwork) equine_penis gay horse horsecock interspecies leather leather_chaps light-skinned_male light_skin lila_lovestar_(sinfulwalpurrgis) male maledom mind_break original shadow2007x shadow_(shadow2007x) uncensored yaoi zoophilia
2023 anal artist_name brown_hair chaps commission cowboy_hat cum cum_in_pussy digital_media_(artwork) english english_text equine_penis gay horse horsecock interspecies leather leather_chaps light-skinned_male light_skin lila_lovestar_(sinfulwalpurrgis) male maledom mind_break original shadow2007x shadow_(shadow2007x) speech_bubble uncensored yaoi zoophilia
2023 anal artist_name brown_hair chaps commission cowboy_hat cum cum_in_pussy digital_media_(artwork) english english_text equine_penis gay horse horsecock interspecies leather leather_chaps light-skinned_male light_skin lila_lovestar_(sinfulwalpurrgis) male maledom mind_break original shadow2007x shadow_(shadow2007x) speech_bubble uncensored yaoi zoophilia
2019 2boys abdl absurd_res artist_name black_hair brown_hair collar commission diaper digital_media_(artwork) dildo english english_text exhibitionism gay high_heels humiliation latex latex_thighhighs leash leash_and_collar light-skinned_male light_skin lila_lovestar_(sinfulwalpurrgis) maledom malesub original pacifier pacifier_gag shadow2007x shadow_(shadow2007x) sissy speech_bubble suit yaoi
2019 2boys abdl absurd_res artist_name black_hair brown_hair collar commission diaper digital_media_(artwork) dildo english english_text exhibitionism gay high_heels humiliation latex latex_thighhighs leash leash_and_collar light-skinned_male light_skin lila_lovestar_(sinfulwalpurrgis) maledom malesub original pacifier pacifier_gag shadow2007x shadow_(shadow2007x) sissy speech_bubble suit yaoi
2017 2boys 2girls absurd_res big_breasts big_nipples bondage brown_hair camcorder candle cartoon_network chains color commission dc digital_media_(artwork) femdom grey_skin humiliation jinx_(dc) light-skinned_male light_skin lila_lovestar_(sinfulwalpurrgis) male malesub milking milking_machine multiple_boys multiple_girls penis penis_milking pink_eyes pink_hair purple_eyes purple_hair rachel_roth ritual shadow2007x shadow_(shadow2007x) teen_titans uncensored witch
2017 2boys 2girls absurd_res big_breasts big_nipples bondage brown_hair camcorder candle cartoon_network chains color commission dc digital_media_(artwork) femdom grey_skin humiliation jinx_(dc) light-skinned_male light_skin lila_lovestar_(sinfulwalpurrgis) male malesub milking milking_machine multiple_boys multiple_girls penis penis_milking pink_eyes pink_hair purple_eyes purple_hair rachel_roth ritual shadow2007x shadow_(shadow2007x) teen_titans uncensored witch
2016 2boys 2girls bit_gag bone_gag buttplug buttplug_tail commission crossover digital_media_(artwork) dominatrix femdom gag gagged hi_res humiliation jenny_wakeman lila_lovestar_(sinfulwalpurrgis) malesub my_life_as_a_teenage_robot nazo_no_kanojo_x outdoors outside petplay robot robot_girl shadow2007x shadow_(shadow2007x) strap-on tail urabe_mikoto
2016 2boys 2girls bit_gag bone_gag buttplug buttplug_tail commission crossover digital_media_(artwork) dominatrix femdom gag gagged hi_res humiliation jenny_wakeman lila_lovestar_(sinfulwalpurrgis) malesub my_life_as_a_teenage_robot nazo_no_kanojo_x outdoors outside petplay robot robot_girl shadow2007x shadow_(shadow2007x) strap-on tail urabe_mikoto
2016 2boys 2girls anal_tail black_boots boots buttplug buttplug_tail clothed_female_nude_male commission crossover digital_media_(artwork) elbow_gloves english_text erection femdom full_moon gag gagged gloves hi_res high_heel_boots humiliation jenny_wakeman lamppost leash_and_collar lila_lovestar_(sinfulwalpurrgis) male malesub microskirt my_life_as_a_teenage_robot nazo_no_kanojo_x nipple_slip outdoors outside penis_out petplay riding_crop robot robot_girl shadow2007x shadow_(shadow2007x) small_breasts speech_bubble straight strap-on tail thigh_boots tree twitails urabe_mikoto whip
2016 2boys 2girls anal_tail black_boots boots buttplug buttplug_tail clothed_female_nude_male commission crossover digital_media_(artwork) elbow_gloves english_text erection femdom full_moon gag gagged gloves hi_res high_heel_boots humiliation jenny_wakeman lamppost leash_and_collar lila_lovestar_(sinfulwalpurrgis) male malesub microskirt my_life_as_a_teenage_robot nazo_no_kanojo_x nipple_slip outdoors outside penis_out petplay riding_crop robot robot_girl shadow2007x shadow_(shadow2007x) small_breasts speech_bubble straight strap-on tail thigh_boots tree twitails urabe_mikoto whip
2018 4boys absurd_res belly belly_expansion brown_hair chastity chastity_cage color commission corruption cumflated_belly cumflation digital_media_(artwork) foursome gay hair_pull hypno hypnosis kaa_eyes large_insertion large_penis latex latex_gloves light-skinned_male light_skin lila_lovestar_(sinfulwalpurrgis) male male_only maledom malesub mask masked_male mind_control nintendo orgasm orgy original_character original_characters pokemon pokemon_rgby pokephilia shadow2007x shadow_(shadow2007x) team_rocket thighhighs tongue_out uncensored uniform yaoi
2018 4boys absurd_res belly belly_expansion brown_hair chastity chastity_cage color commission corruption cumflated_belly cumflation digital_media_(artwork) foursome gay hair_pull hypno hypnosis kaa_eyes large_insertion large_penis latex latex_gloves light-skinned_male light_skin lila_lovestar_(sinfulwalpurrgis) male male_only maledom malesub mask masked_male mind_control nintendo orgasm orgy original_character original_characters pokemon pokemon_rgby pokephilia shadow2007x shadow_(shadow2007x) team_rocket thighhighs tongue_out uncensored uniform yaoi
1boy 2017 breasts commission cum cum_on_breasts facial female glasses jenny_wakeman lewdacris male my_life_as_a_teenage_robot nude nude_female nude_male paizuri penis purple_background robot shadow_(shadow2007x) smooth_skin t+4t xj-9
1boy 2017 breasts commission cum cum_on_breasts facial female glasses jenny_wakeman lewdacris male my_life_as_a_teenage_robot nude nude_female nude_male paizuri penis purple_background robot shadow_(shadow2007x) smooth_skin t+4t xj-9
1boy 1boy1girl 1girls 2009 female jenny_wakeman my_life_as_a_teenage_robot shadow2007x shadow_(shadow2007x) straight_hair tagme
1boy 1boy1girl 1girls 2009 female jenny_wakeman my_life_as_a_teenage_robot shadow2007x shadow_(shadow2007x) straight_hair tagme