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adrian shephard

1boy 1girls adrian_shephard black_mesa black_ops_(half-life) black_ops_assassin blush bodysuit camouflage dominant_female dubious_consent female femdom gas_mask gun half-life hecu latex limited_palette pistol questionable_consent randomse7en straight text threatening yandere
1boy 1girls adrian_shephard black_mesa black_ops_(half-life) black_ops_assassin blush bodysuit camouflage dominant_female dubious_consent female femdom gas_mask gun half-life hecu latex limited_palette pistol questionable_consent randomse7en straight text threatening yandere
1boy 1girls 2d 2d_(artwork) 2d_artwork adrian_shephard alyx_vance arm_hair arms_behind_head bare_legs biting_lip biting_own_lip black_gloves breasts breasts_out camo camouflage closed_eyes clothed clothed_male clothed_sex clothing exposed_breasts exposed_nipples exposed_pussy exposed_torso female female_on_top female_penetrated female_pubic_hair fingerless_gloves garden_warrior gas_mask gearbox_software gloves hairy_pussy half-life half-life_2 half-life_opposing_force hands_behind_head hands_on_thighs heart hecu jacket jacket_only looking_pleasured love_heart lying lying_on_back male male/female male_on_bottom male_penetrating mask masked masked_male military_uniform motion_lines name_tag necklace pants penis penis_in_pussy pubes pubic_hair riding riding_penis sex shirt sleeves_rolled_up straight straight_sex thick_thighs thighs valve
1boy 1girls 2d 2d_(artwork) 2d_artwork adrian_shephard alyx_vance arm_hair arms_behind_head bare_legs biting_lip biting_own_lip black_gloves breasts breasts_out camo camouflage closed_eyes clothed clothed_male clothed_sex clothing exposed_breasts exposed_nipples exposed_pussy exposed_torso female female_on_top female_penetrated female_pubic_hair fingerless_gloves garden_warrior gas_mask gearbox_software gloves hairy_pussy half-life half-life_2 half-life_opposing_force hands_behind_head hands_on_thighs heart hecu jacket jacket_only looking_pleasured love_heart lying lying_on_back male male/female male_on_bottom male_penetrating mask masked masked_male military_uniform motion_lines name_tag necklace pants penis penis_in_pussy pubes pubic_hair riding riding_penis sex shirt sleeves_rolled_up straight straight_sex thick_thighs thighs valve
1boy 2d 2d_(artwork) 2d_artwork adrian_shephard arm_hair armor breath camo closed_eyes clothed fingerless_gloves fluids garden_warrior gas_mask gearbox_software gloves hairy_arms half-life half-life_opposing_force helmet jerking_off light-skinned_male light_skin looking_pleasured male male_masturbation male_only masked masked_male masturbating masturbation military_uniform penis penis_out precum sleeves_rolled_up solo solo_male steamy_breath two-handed_masturbation underwear valve
1boy 2d 2d_(artwork) 2d_artwork adrian_shephard arm_hair armor breath camo closed_eyes clothed fingerless_gloves fluids garden_warrior gas_mask gearbox_software gloves hairy_arms half-life half-life_opposing_force helmet jerking_off light-skinned_male light_skin looking_pleasured male male_masturbation male_only masked masked_male masturbating masturbation military_uniform penis penis_out precum sleeves_rolled_up solo solo_male steamy_breath two-handed_masturbation underwear valve
adrian_shephard black_ops_(half-life) black_ops_assassin eyebags half-life hecu neutral_expression tagme thought_bubble
adrian_shephard black_ops_(half-life) black_ops_assassin eyebags half-life hecu neutral_expression tagme thought_bubble
adrian_shephard black_ops_(half-life) black_ops_assassin english_text gordon_freeman half-life post-human tagme text
adrian_shephard black_ops_(half-life) black_ops_assassin english_text gordon_freeman half-life post-human tagme text
1boy 1girls adrian_shephard andrew_graves ashley_graves black_ops_(half-life) black_ops_assassin female half-life half-life_opposing_force tagme the_coffin_of_andy_and_leyley
1boy 1girls adrian_shephard andrew_graves ashley_graves black_ops_(half-life) black_ops_assassin female half-life half-life_opposing_force tagme the_coffin_of_andy_and_leyley
adrian_shephard ass ass_focus black_armor black_ops_(half-life) black_ops_assassin combat_helmet forget_about_freeman freeman_you_fool g-man gas_mask half-life half_life_3_when he_wants_to_order hecu helmet inside_car inside_vehicle meme military_clothing military_helmet military_uniform she_wants_to_order soldier stealth_armor stealth_suit tactical tactical_clothes tactical_gear tactical_vest
adrian_shephard ass ass_focus black_armor black_ops_(half-life) black_ops_assassin combat_helmet forget_about_freeman freeman_you_fool g-man gas_mask half-life half_life_3_when he_wants_to_order hecu helmet inside_car inside_vehicle meme military_clothing military_helmet military_uniform she_wants_to_order soldier stealth_armor stealth_suit tactical tactical_clothes tactical_gear tactical_vest
adrian_shephard black_ops_(half-life) black_ops_assassin half-life hecu
adrian_shephard black_ops_(half-life) black_ops_assassin half-life hecu
adrian_shephard black_ops_(half-life) black_ops_assassin half-life
adrian_shephard black_ops_(half-life) black_ops_assassin half-life
3d 3d_(artwork) 3d_model adrian_shephard bottomless bottomless_male creepy erect erect_penis erection extraterrestrial fu2e7 gas_mask gas_mask_face half-life hands_on_body holding_gun horror horror_(theme) male male_focus male_only masked masked_male monster no_visible_face non-human science_fiction shaved_crotch valve valve_(company)
3d 3d_(artwork) 3d_model adrian_shephard bottomless bottomless_male creepy erect erect_penis erection extraterrestrial fu2e7 gas_mask gas_mask_face half-life hands_on_body holding_gun horror horror_(theme) male male_focus male_only masked masked_male monster no_visible_face non-human science_fiction shaved_crotch valve valve_(company)
adrian_shephard black_ops_(half-life) black_ops_assassin half-life
adrian_shephard black_ops_(half-life) black_ops_assassin half-life
adrian_shephard black_ops_(half-life) black_ops_assassin half-life hecu
adrian_shephard black_ops_(half-life) black_ops_assassin half-life hecu
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adrian_shephard half-life half-life_opposing_force lustforlofe ribbon tied_up
adrian_shephard ambiguous_gender black_ops_(half-life) black_ops_assassin half-life half-life_opposing_force hecu hickey lustforlofe
adrian_shephard ambiguous_gender black_ops_(half-life) black_ops_assassin half-life half-life_opposing_force hecu hickey lustforlofe
adrian_shephard half-dressed half-life half-life_opposing_force lustforlofe
adrian_shephard half-dressed half-life half-life_opposing_force lustforlofe
3d adrian_shephard clothed danshii2 half-life half-life_opposing_force masturbating penis sfm solo solo_male tagme train tram
3d adrian_shephard clothed danshii2 half-life half-life_opposing_force masturbating penis sfm solo solo_male tagme train tram
3d adrian_shephard clothed clothed_sex cum_drip fellatio gay gay_male gordon_freeman half-life half_life_2 kissing_penis laying_on_bed male/male oral precum raising_barns sfm
3d adrian_shephard clothed clothed_sex cum_drip fellatio gay gay_male gordon_freeman half-life half_life_2 kissing_penis laying_on_bed male/male oral precum raising_barns sfm
adrian_shephard army army_uniform black_mesa bottomless camouflage cigarette dick exhibitionism half-life half-life_opposing_force leaning_against_wall male male_focus male_only no_pants sfm shoes shoes_only source_filmmaker standing valve
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! ? adrian_shephard armor best black_ops_(half-life) black_ops_assassin borisalien comically_large_ass crowbar face_in_ass goggles gordon_freeman gun half-life half-life_opposing_force hecu huge_ass hyper hyper_ass hyper_thighs latex latex_bodysuit latex_gloves male massive_ass massive_butt massive_thighs military rear_view shiny surprised tagme valve
! ? adrian_shephard armor best black_ops_(half-life) black_ops_assassin borisalien comically_large_ass crowbar face_in_ass goggles gordon_freeman gun half-life half-life_opposing_force hecu huge_ass hyper hyper_ass hyper_thighs latex latex_bodysuit latex_gloves male massive_ass massive_butt massive_thighs military rear_view shiny surprised tagme valve
adrian_shephard anthro armor ass big_breasts big_butt big_penis bodily_fluids breasts camo camo_clothing camo_print cervid clothed clothed/nude clothed_male_nude_female clothing cum cum_inside duo female forest forest_background fur gas_mask genital_fluids genitals genre_worm grass green_body green_fur gun hair hand_on_butt hand_on_chest handgun hands_behind_head head_of_nyx_(artist) headgear helmet hi_res hooves horn huge_breasts huge_butt human human_on_anthro humanoid_genitalia humanoid_penis internal interspecies kurt_(fluffygrass) leaking_cum long_hair long_tongue lowered_pants male male/female mammal mask multi_arm multi_limb nature nature_background nude pattern_clothing penis plant questionable_consent ranged_weapon revolver saliva_on_face scut_tail short_tail speech_bubble terra_(fluffygrass) thick_thighs tongue tree weapon white_eyes white_hair wide_hips
adrian_shephard anthro armor ass big_breasts big_butt big_penis bodily_fluids breasts camo camo_clothing camo_print cervid clothed clothed/nude clothed_male_nude_female clothing cum cum_inside duo female forest forest_background fur gas_mask genital_fluids genitals genre_worm grass green_body green_fur gun hair hand_on_butt hand_on_chest handgun hands_behind_head head_of_nyx_(artist) headgear helmet hi_res hooves horn huge_breasts huge_butt human human_on_anthro humanoid_genitalia humanoid_penis internal interspecies kurt_(fluffygrass) leaking_cum long_hair long_tongue lowered_pants male male/female mammal mask multi_arm multi_limb nature nature_background nude pattern_clothing penis plant questionable_consent ranged_weapon revolver saliva_on_face scut_tail short_tail speech_bubble terra_(fluffygrass) thick_thighs tongue tree weapon white_eyes white_hair wide_hips
1:1 2020 adrian_shephard anthro black_nose black_ops_(half-life) black_ops_assassin breast_smother breasts breasts_bigger_than_body breasts_bigger_than_head bulge chiropteran dialogue domination duo english_text erect_nipples erect_nipples_under_clothes eulipotyphlan explosives female female_domination grenade grenades half-life half-life_opposing_force hands_on_breasts hedgehog hi_res hyper hyper_ass hyper_breasts larger_female latex_suit male mammal military military_clothing military_jacket military_uniform nipple_bulge rouge_the_bat sega shadow_the_hedgehog size_difference smaller_male smothering sonic_(series) sonic_the_hedgehog_(series) straight text thick_thighs thighs tight_clothes tight_clothing tight_fit ultimateshadow video_games wide_hips wide_thighs
1:1 2020 adrian_shephard anthro black_nose black_ops_(half-life) black_ops_assassin breast_smother breasts breasts_bigger_than_body breasts_bigger_than_head bulge chiropteran dialogue domination duo english_text erect_nipples erect_nipples_under_clothes eulipotyphlan explosives female female_domination grenade grenades half-life half-life_opposing_force hands_on_breasts hedgehog hi_res hyper hyper_ass hyper_breasts larger_female latex_suit male mammal military military_clothing military_jacket military_uniform nipple_bulge rouge_the_bat sega shadow_the_hedgehog size_difference smaller_male smothering sonic_(series) sonic_the_hedgehog_(series) straight text thick_thighs thighs tight_clothes tight_clothing tight_fit ultimateshadow video_games wide_hips wide_thighs
1boy 1girls 3d adrian_shephard animated assassin black_mesa black_ops_(half-life) black_ops_assassin half-life human_on_humanoid loop male/female male_pov no_sound pov rape skeletonintheclosetsfm source_filmmaker tagme video
1boy 1girls 3d adrian_shephard animated assassin black_mesa black_ops_(half-life) black_ops_assassin half-life human_on_humanoid loop male/female male_pov no_sound pov rape skeletonintheclosetsfm source_filmmaker tagme video
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adrian_shephard after_sex alien anus blackmesajoe_(artist) blue_cum colored_cum cum feral feral_on_human feral_on_male gay half-life half-life_opposing_force hi_res human interspecies mammal monster monster_on_male penis pink_penis purple_cum unusual_cum video_games voltigore zoophilia
adrian_shephard alien anus blackmesajoe_(artist) cum cum_inside feral gay half-life half-life_opposing_force hi_res human internal interspecies mammal monster monster_on_male video_games voltigore x-ray zoophilia
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absurd_res adrian_shephard alien ambiguous_gender animal_genitalia anus blackmesajoe_(artist) bullsquid catwalk colored_cum cum cum_everywhere cum_in_ass cum_in_mouth cum_inside cum_on_self disembodied_hand duo erection feral gaping gaping_anus gay genital_slit half-life half-life_opposing_force heart hi_res huge_anus human human_on_feral inside interspecies male male_only mammal messy monster penis precum puffy_anus rear_view saliva slit solo_focus spread_anus spreading tapering_penis tentacle unusual_cum video_games zoophilia
absurd_res adrian_shephard alien ambiguous_gender animal_genitalia anus blackmesajoe_(artist) bullsquid catwalk colored_cum cum cum_everywhere cum_in_ass cum_in_mouth cum_inside cum_on_self disembodied_hand duo erection feral gaping gaping_anus gay genital_slit half-life half-life_opposing_force heart hi_res huge_anus human human_on_feral inside interspecies male male_only mammal messy monster penis precum puffy_anus rear_view saliva slit solo_focus spread_anus spreading tapering_penis tentacle unusual_cum video_games zoophilia
absurd_res adrian_shephard alien ambiguous_gender animal_genitalia anus blackmesajoe_(artist) bullsquid catwalk colored_cum cum disembodied_hand duo erection feral gaping gaping_anus gay genital_slit half-life half-life_opposing_force heart hi_res huge_anus human human_on_feral inside interspecies male mammal monster penis precum puffy_anus rear_view saliva slit solo_focus spread_anus spreading tapering_penis tentacle unusual_cum video_games zoophilia
absurd_res adrian_shephard alien ambiguous_gender animal_genitalia anus blackmesajoe_(artist) bullsquid catwalk colored_cum cum disembodied_hand duo erection feral gaping gaping_anus gay genital_slit half-life half-life_opposing_force heart hi_res huge_anus human human_on_feral inside interspecies male mammal monster penis precum puffy_anus rear_view saliva slit solo_focus spread_anus spreading tapering_penis tentacle unusual_cum video_games zoophilia
4_arms absurd_res adrian_shephard alien anal anal_sex animal_genitalia animal_penis anus autofellatio big_penis blackmesajoe_(artist) blue_cum cave colored_cum cum cum_in_ass cum_in_mouth cum_in_own_mouth cum_inside cum_on_self cumshot detailed_background duo excessive_cum fellatio furry green_anus green_penis green_tongue half-closed_eyes half-life half-life_opposing_force heart highres human human_on_male human_penetrating interspecies looking_at_viewer male mammal masturbation monster multi_arm multi_limb one-eyed oral orange_eyes orgasm penetration penis pov prehensile_penis saliva sex sheath shock_trooper slit_pupils teeth underground unusual_cum unusual_penis vein veiny_penis yaoi
4_arms absurd_res adrian_shephard alien anal anal_sex animal_genitalia animal_penis anus autofellatio big_penis blackmesajoe_(artist) blue_cum cave colored_cum cum cum_in_ass cum_in_mouth cum_in_own_mouth cum_inside cum_on_self cumshot detailed_background duo excessive_cum fellatio furry green_anus green_penis green_tongue half-closed_eyes half-life half-life_opposing_force heart highres human human_on_male human_penetrating interspecies looking_at_viewer male mammal masturbation monster multi_arm multi_limb one-eyed oral orange_eyes orgasm penetration penis pov prehensile_penis saliva sex sheath shock_trooper slit_pupils teeth underground unusual_cum unusual_penis vein veiny_penis yaoi
4_arms absurd_res adrian_shephard alien anal anal_sex animal_genitalia animal_penis anus autofellatio big_penis blackmesajoe_(artist) cave duo fellatio green_anus green_penis green_tongue half-life half-life_opposing_force heart highres human human_on_male human_penetrating interspecies looking_at_viewer male mammal masturbation monster multi_arm multi_limb one-eyed oral penetration penis pov prehensile_penis puffy_anus saliva sex sheath shock_trooper underground unusual_penis vein veiny_penis yaoi
4_arms absurd_res adrian_shephard alien anal anal_sex animal_genitalia animal_penis anus autofellatio big_penis blackmesajoe_(artist) cave duo fellatio green_anus green_penis green_tongue half-life half-life_opposing_force heart highres human human_on_male human_penetrating interspecies looking_at_viewer male mammal masturbation monster multi_arm multi_limb one-eyed oral penetration penis pov prehensile_penis puffy_anus saliva sex sheath shock_trooper underground unusual_penis vein veiny_penis yaoi
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4_arms adrian_shephard alien amphibian anal anal_sex black_mesa blackmesajoe_(artist) blue_cum blush camo colored_cum cum cum_string cumshot excessive_cum green_tongue half-life half-life_opposing_force happy heart hi_res human humanoid_penis interspecies male male_only mammal monster multi_arm multi_limb one-eyed oral orgasm outside penetration penis race race_x saliva sex shocktrooper_(half-life) soldier spikes teeth unusual_cum valve video_games yaoi
4_arms adrian_shephard alien amphibian anal anal_sex black_mesa blackmesajoe_(artist) blue_cum blush camo colored_cum cum cum_string cumshot excessive_cum green_tongue half-life half-life_opposing_force happy heart hi_res human humanoid_penis interspecies male male_only mammal monster multi_arm multi_limb one-eyed oral orgasm outside penetration penis race race_x saliva sex shocktrooper_(half-life) soldier spikes teeth unusual_cum valve video_games yaoi
4_arms adrian_shephard alien amphibian anal anal_sex black_mesa blackmesajoe_(artist) blush camo green_tongue half-life half-life_opposing_force happy happy_sex heart hi_res human humanoid_penis interspecies male mammal monster multi_arm multi_limb one-eyed oral outside penetration penis race race_x saliva sex shocktrooper_(half-life) soldier spikes teeth valve video_games yaoi
4_arms adrian_shephard alien amphibian anal anal_sex black_mesa blackmesajoe_(artist) blush camo green_tongue half-life half-life_opposing_force happy happy_sex heart hi_res human humanoid_penis interspecies male mammal monster multi_arm multi_limb one-eyed oral outside penetration penis race race_x saliva sex shocktrooper_(half-life) soldier spikes teeth valve video_games yaoi
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