pain_play best from all time

Time frame

Tags

pain play

1futa 1girls 3d ahe_gao areolae ball_stretcher ball_weight balls ballsack big_breasts big_penis black_hair bondage breasts brigitte clothed clothed_female_nude_futanari clothing cock_and_ball_torture cock_ring_(decorative) dark_skin drooling duo erection female female_on_futa female_sadism femdom fjaye futanari futanari_masochism futasub gag human light-skinned_futanari light_skin masochism mostly_nude multiple_cock_rings nipple_piercing nipple_play nipple_weights nude nude_futanari o_ring_gag open_mouth_gag orange_hair overwatch pain pain_play pale_skin penis precum precum_drip ring_gag sadism saliva scratches scrotum sex_dungeon sex_slave shaved_crotch symmetra testicle_cuff testicles thick_precum tongue tongue_out tongue_weight veiny_penis weights_(bdsm)
1futa 1girls 3d ahe_gao areolae ball_stretcher ball_weight balls ballsack big_breasts big_penis black_hair bondage breasts brigitte clothed clothed_female_nude_futanari clothing cock_and_ball_torture cock_ring_(decorative) dark_skin drooling duo erection female female_on_futa female_sadism femdom fjaye futanari futanari_masochism futasub gag human light-skinned_futanari light_skin masochism mostly_nude multiple_cock_rings nipple_piercing nipple_play nipple_weights nude nude_futanari o_ring_gag open_mouth_gag orange_hair overwatch pain pain_play pale_skin penis precum precum_drip ring_gag sadism saliva scratches scrotum sex_dungeon sex_slave shaved_crotch symmetra testicle_cuff testicles thick_precum tongue tongue_out tongue_weight veiny_penis weights_(bdsm)
1girls 3d auction barbell_piercing body_writing bondage brainwashed collar completely_nude_female cuffs daz_studio drool drooling evilmercenary female female_masochism female_only femsub for_sale front_view glasses green_eyes hairless_pussy human_livestock iron_collar iron_cuffs lidded_eyes lightly_tanned livestock masochism masochist mindbreak navel nipple_piercing nipple_rings nipples pain_play pierced_nipples pink_nipples price red_hair red_nails self_breast_fondle shaved_pussy slave slave_auction slavegirl small_breasts solo tanned_female text toned toned_stomach tongue tongue_out v-sign virgin young
1girls 3d auction barbell_piercing body_writing bondage brainwashed collar completely_nude_female cuffs daz_studio drool drooling evilmercenary female female_masochism female_only femsub for_sale front_view glasses green_eyes hairless_pussy human_livestock iron_collar iron_cuffs lidded_eyes lightly_tanned livestock masochism masochist mindbreak navel nipple_piercing nipple_rings nipples pain_play pierced_nipples pink_nipples price red_hair red_nails self_breast_fondle shaved_pussy slave slave_auction slavegirl small_breasts solo tanned_female text toned toned_stomach tongue tongue_out v-sign virgin young
2023 3d_(artwork) 3d_animation 5_fingers aaron_(kadath) animated anthro anthro_on_anthro armwear ass big_breasts big_butt big_penis black_armwear black_body black_claws black_clothing black_footwear black_fur black_glans black_hair black_inner_ear black_legwear black_nipples black_nose black_penis breasts bulge canid canine claws clothing cock_sleeve_(clothes) connivingrat digital_media_(artwork) dominant dominant_anthro dominant_gynomorph dominant_intersex elise_(omniman907) english_text equid equine erection face_slap female fingers footwear foreskin frown fur genitals glans grey_body grey_fur grey_penis gynomorph gynomorph/male hair handjob high_framerate hitalva hitting horse huge_breasts huge_cock humanoid_genitalia humanoid_penis hyper intersex intersex/male invadernoodles legwear loop male_with_futa mammal mostly_nude muscular muscular_male nipples orange_eyes orgasm_denial pain pain_play penile penis ponytail questionable_consent red_hair sex short_playtime signature sitting slap sound sound_warning standing submissive submissive_anthro submissive_male tagme text thick_thighs thong tied_to_chair vein veiny_penis video yellow_armwear yellow_clothing
2023 3d_(artwork) 3d_animation 5_fingers aaron_(kadath) animated anthro anthro_on_anthro armwear ass big_breasts big_butt big_penis black_armwear black_body black_claws black_clothing black_footwear black_fur black_glans black_hair black_inner_ear black_legwear black_nipples black_nose black_penis breasts bulge canid canine claws clothing cock_sleeve_(clothes) connivingrat digital_media_(artwork) dominant dominant_anthro dominant_gynomorph dominant_intersex elise_(omniman907) english_text equid equine erection face_slap female fingers footwear foreskin frown fur genitals glans grey_body grey_fur grey_penis gynomorph gynomorph/male hair handjob high_framerate hitalva hitting horse huge_breasts huge_cock humanoid_genitalia humanoid_penis hyper intersex intersex/male invadernoodles legwear loop male_with_futa mammal mostly_nude muscular muscular_male nipples orange_eyes orgasm_denial pain pain_play penile penis ponytail questionable_consent red_hair sex short_playtime signature sitting slap sound sound_warning standing submissive submissive_anthro submissive_male tagme text thick_thighs thong tied_to_chair vein veiny_penis video yellow_armwear yellow_clothing
2023 3d_(artwork) 3d_animation 5_fingers aaron_(kadath) animated anthro anthro_on_anthro armwear ass big_breasts big_butt big_penis black_armwear black_body black_claws black_clothing black_footwear black_fur black_glans black_hair black_inner_ear black_legwear black_nipples black_nose black_penis breasts bulge canid canine claws clothing connivingrat digital_media_(artwork) dominant dominant_anthro dominant_gynomorph dominant_intersex elise_(omniman907) equid equine erection face_slap female fingers footwear foreskin frown fur futanari genitals glans grey_body grey_fur grey_penis gynomorph gynomorph/male hair handjob hi_res high_framerate hitting horse huge_breasts huge_cock huge_penis humanoid_genitalia humanoid_penis hyper intersex intersex/male legwear loop male_with_futa mammal mostly_nude muscular muscular_male nipples no_sound orange_eyes orgasm_denial pain pain_play penile penis ponytail questionable_consent red_hair sex short_playtime sitting slap standing submissive submissive_anthro submissive_male tagme thick_thighs tied_to_chair vein veiny_penis video yellow_armwear yellow_clothing
2023 3d_(artwork) 3d_animation 5_fingers aaron_(kadath) animated anthro anthro_on_anthro armwear ass big_breasts big_butt big_penis black_armwear black_body black_claws black_clothing black_footwear black_fur black_glans black_hair black_inner_ear black_legwear black_nipples black_nose black_penis breasts bulge canid canine claws clothing connivingrat digital_media_(artwork) dominant dominant_anthro dominant_gynomorph dominant_intersex elise_(omniman907) equid equine erection face_slap female fingers footwear foreskin frown fur futanari genitals glans grey_body grey_fur grey_penis gynomorph gynomorph/male hair handjob hi_res high_framerate hitting horse huge_breasts huge_cock huge_penis humanoid_genitalia humanoid_penis hyper intersex intersex/male legwear loop male_with_futa mammal mostly_nude muscular muscular_male nipples no_sound orange_eyes orgasm_denial pain pain_play penile penis ponytail questionable_consent red_hair sex short_playtime sitting slap standing submissive submissive_anthro submissive_male tagme thick_thighs tied_to_chair vein veiny_penis video yellow_armwear yellow_clothing
daisuke_(mouthwashing) male male_only masturbating masturbation mouthwashing pain pain_play penis sobakasen sounding text twink urethra urethral_insertion urethral_penetration young
daisuke_(mouthwashing) male male_only masturbating masturbation mouthwashing pain pain_play penis sobakasen sounding text twink urethra urethral_insertion urethral_penetration young
arms_behind_back arms_tied arms_tied_behind_back asphyxiation ball_gag blindfold blindfolded bondage bound breathplay captured captured_hero choker collar dc dc_comics dick_grayson dubious_consent gag gagged gay hanged jason_todd leash_and_collar leash_pull male male/male male_focus male_nipples male_only masochism nightwing no_visible_genitalia pain pain_play pov red_hood_(dc) sadism sarriathmg shirtless shirtless_(male) shirtless_male submissive_male superhero throat_abuse yaoi
arms_behind_back arms_tied arms_tied_behind_back asphyxiation ball_gag blindfold blindfolded bondage bound breathplay captured captured_hero choker collar dc dc_comics dick_grayson dubious_consent gag gagged gay hanged jason_todd leash_and_collar leash_pull male male/male male_focus male_nipples male_only masochism nightwing no_visible_genitalia pain pain_play pov red_hood_(dc) sadism sarriathmg shirtless shirtless_(male) shirtless_male submissive_male superhero throat_abuse yaoi
absurd_res aggressive_retsuko anthro blush bodily_fluids breasts clothed clothing female food food_play funnel funnel_in_pussy funnel_insertion genitals headphones_around_neck hi_res hot_sauce jacket lactating legwear liquid lying mammal mephitid monster_energy nipples on_back open_mouth pain_play painful partially_clothed phone_call purple_body pussy sanrio shikabane shikabane_(aggressive_retsuko) shikabane_(aggretsuko) skunk smooth_fur solo speech_bubble stockings tears thigh_highs what zinfyu
absurd_res aggressive_retsuko anthro blush bodily_fluids breasts clothed clothing female food food_play funnel funnel_in_pussy funnel_insertion genitals headphones_around_neck hi_res hot_sauce jacket lactating legwear liquid lying mammal mephitid monster_energy nipples on_back open_mouth pain_play painful partially_clothed phone_call purple_body pussy sanrio shikabane shikabane_(aggressive_retsuko) shikabane_(aggretsuko) skunk smooth_fur solo speech_bubble stockings tears thigh_highs what zinfyu
1boy1girl abuse abused abused_female ai_generated black_hair bondage breast_bondage breast_torture breasts crying crying_with_eyes_open faenir female hands_behind_back hands_tied hands_tied_behind_back in_pain long_hair misogyny nails nipple_torture pain pain_play painful perchance_ai pierced_ears pierced_nipples piercings rape raped raped_girl red_eyes rope rope_bondage slave slavegirl tears tears_of_pain tits_nailed_to_table
1boy1girl abuse abused abused_female ai_generated black_hair bondage breast_bondage breast_torture breasts crying crying_with_eyes_open faenir female hands_behind_back hands_tied hands_tied_behind_back in_pain long_hair misogyny nails nipple_torture pain pain_play painful perchance_ai pierced_ears pierced_nipples piercings rape raped raped_girl red_eyes rope rope_bondage slave slavegirl tears tears_of_pain tits_nailed_to_table
2015 abuse anthro ass blood blue_hair body_writing bondage bound breasts broken bukkake claw_marks claws crying cum cum_in_hair cum_in_pussy cum_inside cum_on_body cum_on_breasts cum_on_face cum_on_feet cum_on_stomach defeated degradation erection exhibition female forced furry gag group group_sex hair male mammal markings msspixy necktie nipples nude pain pain_play penis public public_use pussy rape red_panda restrained rope sex sitting sofa spix spread_legs spreader_bar spreading straight tally_marks tears toe_claws unknown used vaginal_penetration vega_(artica) violence wounded yellow_eyes
2015 abuse anthro ass blood blue_hair body_writing bondage bound breasts broken bukkake claw_marks claws crying cum cum_in_hair cum_in_pussy cum_inside cum_on_body cum_on_breasts cum_on_face cum_on_feet cum_on_stomach defeated degradation erection exhibition female forced furry gag group group_sex hair male mammal markings msspixy necktie nipples nude pain pain_play penis public public_use pussy rape red_panda restrained rope sex sitting sofa spix spread_legs spreader_bar spreading straight tally_marks tears toe_claws unknown used vaginal_penetration vega_(artica) violence wounded yellow_eyes
animal_tail batcest bent_over crossdressing crossdressing_male dc dc_comics dominant_male enjoying_spanking femboy gay gay_domination iterativeglue jason_todd jaytim maid maid_uniform male male/male male_maid male_only open_mouth pain pain_play punishment punishment_spanking red_hood_(dc) red_robin spanking submissive_male tail_plug tim_drake yaoi
animal_tail batcest bent_over crossdressing crossdressing_male dc dc_comics dominant_male enjoying_spanking femboy gay gay_domination iterativeglue jason_todd jaytim maid maid_uniform male male/male male_maid male_only open_mouth pain pain_play punishment punishment_spanking red_hood_(dc) red_robin spanking submissive_male tail_plug tim_drake yaoi
1boy 1cuntboy blood blushing cum cuntboy cuntboy_only five_nights_at_freddy's fnaf hairy_pussy intersex kneeling knife knife_in_pussy knife_play male masochism masochist masochistic masochistic_male masturbation on_knees pain_play panting purple_guy purple_guy_(fnaf) pussy self_harm self_harm_scars selfharm selfharm_scars solo tears william_afton
1boy 1cuntboy blood blushing cum cuntboy cuntboy_only five_nights_at_freddy's fnaf hairy_pussy intersex kneeling knife knife_in_pussy knife_play male masochism masochist masochistic masochistic_male masturbation on_knees pain_play panting purple_guy purple_guy_(fnaf) pussy self_harm self_harm_scars selfharm selfharm_scars solo tears william_afton
4:3 abs abuse antennae_(anatomy) antennae_pull anthro areola aroused arthropod arthropod_abdomen arthropod_abdomen_genitalia beetle big_breasts big_penis biped blue_penis blushing_profusely bob_cut bodily_fluids breasts brown_body bug_(sodabug) cross-popping_vein curled_hair dominant dominant_male drooling eager edging elytron erection female flower_mantis foursome genital_fluids genitals group group_sex hair half-closed_eyes hi_res insects larger_anthro larger_male long_hair looking_pleasured male male/female male_dominating_female mandibles mantis muscular muscular_anthro muscular_male narrowed_eyes nipples non-mammal_breasts non-mammal_nipples orchid_mantis pain_play penile penis penis_worship pink_body pink_eyes purple_body purple_eyes red_sclera saliva sex short_hair size_difference smaller_anthro smaller_female spiked_penis spikes spikes_(anatomy) spiral_eyes straight_hair submissive submissive_female sweating_profusely the_soda_bug thick_thighs unknown_species vaginal_fluids white_body yellow_sclera
4:3 abs abuse antennae_(anatomy) antennae_pull anthro areola aroused arthropod arthropod_abdomen arthropod_abdomen_genitalia beetle big_breasts big_penis biped blue_penis blushing_profusely bob_cut bodily_fluids breasts brown_body bug_(sodabug) cross-popping_vein curled_hair dominant dominant_male drooling eager edging elytron erection female flower_mantis foursome genital_fluids genitals group group_sex hair half-closed_eyes hi_res insects larger_anthro larger_male long_hair looking_pleasured male male/female male_dominating_female mandibles mantis muscular muscular_anthro muscular_male narrowed_eyes nipples non-mammal_breasts non-mammal_nipples orchid_mantis pain_play penile penis penis_worship pink_body pink_eyes purple_body purple_eyes red_sclera saliva sex short_hair size_difference smaller_anthro smaller_female spiked_penis spikes spikes_(anatomy) spiral_eyes straight_hair submissive submissive_female sweating_profusely the_soda_bug thick_thighs unknown_species vaginal_fluids white_body yellow_sclera
arms_behind_back arms_tied arms_tied_behind_back black_mask_(dc) bondage closed_eyes cr0ques dc dc_comics erection erection_under_clothes gay gritted_teeth hard jason_todd male pain pain_play pierced_nipples piercing piercing_nipples piercings red_hood_(dc) sadism submissive submissive_male
arms_behind_back arms_tied arms_tied_behind_back black_mask_(dc) bondage closed_eyes cr0ques dc dc_comics erection erection_under_clothes gay gritted_teeth hard jason_todd male pain pain_play pierced_nipples piercing piercing_nipples piercings red_hood_(dc) sadism submissive submissive_male
angel angel_costume angel_wings apple_in_mouth bare_ass caelsin candy candy_apple charlie_morningstar_(hazbin_hotel) costume couch demon demon_costume demon_girl demon_horns demon_tail dressed halloween halloween_2024 halloween_costume hand_mark hazbin_hotel hooves pain_play red_ass spanking trick_or_treat vaggie_(hazbin_hotel)
angel angel_costume angel_wings apple_in_mouth bare_ass caelsin candy candy_apple charlie_morningstar_(hazbin_hotel) costume couch demon demon_costume demon_girl demon_horns demon_tail dressed halloween halloween_2024 halloween_costume hand_mark hazbin_hotel hooves pain_play red_ass spanking trick_or_treat vaggie_(hazbin_hotel)
chair crying crying_with_eyes_open erect_penis forced gay male male_focus naked naked_male open_mouth pain pain_play penis restrained robert_(srpelo) skinny sobakasen spooky_month tied_hands tied_up toony yaoi
chair crying crying_with_eyes_open erect_penis forced gay male male_focus naked naked_male open_mouth pain pain_play penis restrained robert_(srpelo) skinny sobakasen spooky_month tied_hands tied_up toony yaoi
2024 anthro areola balls big_breasts biped black_body black_clothing black_hair black_legwear black_nose black_stockings bodily_fluids bondage bondage bound bra breasts canid canine canis cby chastity_cage chastity_device claws clothed clothing countershade_face countershade_tail countershade_torso countershading curled_tail domestic_dog domestic_ferret drooling duo eyebrows female fluffy fluffy_tail genital_fluids genitals green_eyes gynomorph gynomorph/female hair hair_over_eye hi_res husky intersex intersex/female josie_(malachyte) kneeling leaking_precum legwear looking_at_another looking_at_partner lying malachyte mammal mostly_nude multicolored_body mustelid musteline navel nipple_clamp nipples nordic_sled_dog on_back open_mouth open_smile pain_play panties pink_body pink_bra pink_clothing pink_panties pink_stockings pink_underwear ponytail precum red_hair restraints riding_crop rope rope_bondage rope_harness saliva sex_toy slightly_chubby slightly_chubby_gynomorph slightly_chubby_intersex smile spank_marks spitz stockings tail teeth thigh_highs toe_claws tongue true_musteline two_tone_body underwear underwear_only vibrator wand_vibrator weasel whip white_body white_countershading
2024 anthro areola balls big_breasts biped black_body black_clothing black_hair black_legwear black_nose black_stockings bodily_fluids bondage bondage bound bra breasts canid canine canis cby chastity_cage chastity_device claws clothed clothing countershade_face countershade_tail countershade_torso countershading curled_tail domestic_dog domestic_ferret drooling duo eyebrows female fluffy fluffy_tail genital_fluids genitals green_eyes gynomorph gynomorph/female hair hair_over_eye hi_res husky intersex intersex/female josie_(malachyte) kneeling leaking_precum legwear looking_at_another looking_at_partner lying malachyte mammal mostly_nude multicolored_body mustelid musteline navel nipple_clamp nipples nordic_sled_dog on_back open_mouth open_smile pain_play panties pink_body pink_bra pink_clothing pink_panties pink_stockings pink_underwear ponytail precum red_hair restraints riding_crop rope rope_bondage rope_harness saliva sex_toy slightly_chubby slightly_chubby_gynomorph slightly_chubby_intersex smile spank_marks spitz stockings tail teeth thigh_highs toe_claws tongue true_musteline two_tone_body underwear underwear_only vibrator wand_vibrator weasel whip white_body white_countershading
1boy 3d 3d_(artwork) 3d_model antihero black_hair bondage bounty_hunter dc dc_comics electricity_play electroshock electrostimulation erect_penis erection fetish gray_body grey_skin lobo_(dc) loving_it male male_focus male_only naked naked_male nude nude_male pain_play red_eyes saltyrenders smiling_at_viewer solo_male submissive_hero submissive_male willing_sub
1boy 3d 3d_(artwork) 3d_model antihero black_hair bondage bounty_hunter dc dc_comics electricity_play electroshock electrostimulation erect_penis erection fetish gray_body grey_skin lobo_(dc) loving_it male male_focus male_only naked naked_male nude nude_male pain_play red_eyes saltyrenders smiling_at_viewer solo_male submissive_hero submissive_male willing_sub
1:1 anal anal_sex animal_genitalia anus ass avian beak bent_legs biped bird bodily_fluids chest_tuft chili_pepper cloaca cloacal cloacal_penetration cloacal_penis club_penguin cue_stick digital_media_(artwork) drooling erection fan_character feathers feet feet_up feral flippers food food_fetish food_insertion food_play fruit genital_fluids genitals grossarts habanero_pepper hands_on_legs hands_on_own_legs holding_legs holding_legs_up ibgross improvised_sex_toy legs_up male male_penetrated micropenis nude open_mouth pain pain_play penetration penguin penis pepper_(fruit) plant saliva simple_background small_penis solo spread_legs spreading stretched_anus submissive submissive_male tail_feathers toe_curl torture tuft video_games white_background white_body
1:1 anal anal_sex animal_genitalia anus ass avian beak bent_legs biped bird bodily_fluids chest_tuft chili_pepper cloaca cloacal cloacal_penetration cloacal_penis club_penguin cue_stick digital_media_(artwork) drooling erection fan_character feathers feet feet_up feral flippers food food_fetish food_insertion food_play fruit genital_fluids genitals grossarts habanero_pepper hands_on_legs hands_on_own_legs holding_legs holding_legs_up ibgross improvised_sex_toy legs_up male male_penetrated micropenis nude open_mouth pain pain_play penetration penguin penis pepper_(fruit) plant saliva simple_background small_penis solo spread_legs spreading stretched_anus submissive submissive_male tail_feathers toe_curl torture tuft video_games white_background white_body
1boy 2015 anthro balls blood bottomless clenched_teeth clothed clothing corset crying death erection extreme_pain fatality gore half-dressed humanoid_penis impalement male male_death male_only mammal meredith_(arcturus) monochrome msspixy pain pain_play penis red_panda solo spikes spix spot_color tears teeth torture trapped
1boy 2015 anthro balls blood bottomless clenched_teeth clothed clothing corset crying death erection extreme_pain fatality gore half-dressed humanoid_penis impalement male male_death male_only mammal meredith_(arcturus) monochrome msspixy pain pain_play penis red_panda solo spikes spix spot_color tears teeth torture trapped
absurd_res anthro ball_gag ball_tugging ballbusting bondage bondage bound clothing cock_and_ball_torture gag genital_torture handwear harness hi_res humanoid male mittens pain_play restrained scared scared_face sketchotterly solo
absurd_res anthro ball_gag ball_tugging ballbusting bondage bondage bound clothing cock_and_ball_torture gag genital_torture handwear harness hi_res humanoid male mittens pain_play restrained scared scared_face sketchotterly solo
101_dalmatians absurd_res anthro bottomless clothed clothing disney domestic_cat felid feline felis feral genitals hi_res hypnosis lobofeo magic male male_only mammal mind_control pain_play penile_spines penis pinup pose sabrina_the_teenage_witch salem solo spell
101_dalmatians absurd_res anthro bottomless clothed clothing disney domestic_cat felid feline felis feral genitals hi_res hypnosis lobofeo magic male male_only mammal mind_control pain_play penile_spines penis pinup pose sabrina_the_teenage_witch salem solo spell