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1boy 5_fingers alcohol armchair balls big_penis black_hair black_tie_(suit) blazer blinds blue_eyes border bottomwear business_suit businessman chair cigarette cigarette_in_mouth circumcised clothed clothing collared_shirt color cup daddy dark_hair digital_media_(artwork) dilf don_draper drawnpr0n drink drinking erection facial_hair five_o'clock_shadow frenulum front_view fully_clothed gay genitals glans glass grey_suit hand_on_own_penis hand_on_penis holding_glass holding_penis huge_cock human human_only humanoid_penis indoors inviting jacket jon_hamm large_penis light-skinned_male light_skin long_penis looking_at_viewer mad_men male male_only manly manspreading mostly_clothed office open_fly open_legs open_pants pants penis penis_focus penis_out presenting presenting_penis pubic_hair pubic_hair_peek realistic reclining relaxing room seductive shirt sitting sitting_on_chair slacks slight_smile smoking smoking_pipe solo spread_legs stubble suggestive suit suit_and_tie suit_jacket testicles thick_penis tie topwear uncensored unprofessional_behavior unzipped unzipped_pants vein veiny_penis whiskey whiskey_glass white_border white_shirt workplace

1boy 5_fingers alcohol armchair balls big_penis black_hair black_tie_(suit)blazer blinds blue_eyes border bottomwear business_suit businessman chair cigarette cigarette_in_mouth circumcised clothed clothing collared_shirt color cup daddy dark_hair digital_media_(artwork)dilf don_draper drawnpr0n drink drinking erection facial_hair five_o'clock_shadow frenulum front_view fully_clothed gay genitals glans glass grey_suit hand_on_own_penis hand_on_penis holding_glass holding_penis huge_cock human human_only humanoid_penis indoors inviting jacket jon_hamm large_penis light-skinned_male light_skin long_penis looking_at_viewer mad_men male male_only manly manspreading mostly_clothed office open_fly open_legs open_pants pants penis penis_focus penis_out presenting presenting_penis pubic_hair pubic_hair_peek realistic reclining relaxing room seductive shirt sitting sitting_on_chair slacks slight_smile smoking smoking_pipe solo spread_legs stubble suggestive suit suit_and_tie suit_jacket testicles thick_penis tie topwear uncensored unprofessional_behavior unzipped unzipped_pants vein veiny_penis whiskey whiskey_glass white_border white_shirt workplace

1boy 5_fingers alcohol armchair balls big_penis black_hair black_tie_(suit) blazer blinds blue_eyes border bottomwear business_suit businessman chair cigarette cigarette_in_mouth circumcised clothed clothing collared_shirt color cup daddy dark_hair digital_media_(artwork) dilf don_draper drawnpr0n drink drinking erection facial_hair five_o'clock_shadow frenulum front_view fully_clothed gay genitals glans glass grey_suit hand_on_own_penis hand_on_penis holding_glass holding_penis huge_cock human human_only humanoid_penis indoors inviting jacket jon_hamm large_penis light-skinned_male light_skin long_penis looking_at_viewer mad_men male male_only manly manspreading mostly_clothed office open_fly open_legs open_pants pants penis penis_focus penis_out presenting presenting_penis pubic_hair pubic_hair_peek realistic reclining relaxing room seductive shirt sitting sitting_on_chair slacks slight_smile smoking smoking_pipe solo spread_legs stubble suggestive suit suit_and_tie suit_jacket testicles thick_penis tie topwear uncensored unprofessional_behavior unzipped unzipped_pants vein veiny_penis whiskey whiskey_glass white_border white_shirt workplace

actor actress betty_draper caucasian caucasian_female caucasian_male celebrity don_draper famous_comics female human in_character january_jones jon_hamm mad_men male real_person sex straight

actor actress betty_draper caucasian caucasian_female caucasian_male celebrity cowgirl_position don_draper famous_comics female girl_on_top human in_character january_jones jon_hamm mad_men male real_person sex straight