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1boy 1girls ai_generated arms_above_head blood blood_stain bondage bound bound_wrists breast_grab breast_squeeze breasts business_attire business_suit business_woman clothed_female clothed_female_clothed_male clothed_male clothed_male_clothed_female clothed_sex clothes clothing collar crying crying_with_eyes_open defloration deflowering dress_shirt earrings empty_eyes female female_focus female_penetrated female_virgin femsub forced freckles freckles_on_breasts freckles_on_face grabbing grabbing_another's_breast green_eyes league_of_legends male male/female male_penetrating male_penetrating_female male_pov miss_fortune nipples nipples_visible_through_clothing office office_clothing office_lady paper pinstripe_skirt pov pov_crotch pov_hands rape red_hair sarah_fortune skirt skirt_up submissive_female tears tied_up translucent_clothing vaginal_blood vaginal_penetration virgin virginal_blood wet wet_clothes wet_clothing white_dress_shirt

1boy 1girls ai_generated arms_above_head blood blood_stain bondage bound bound_wrists breast_grab breast_squeeze breasts business_attire business_suit business_woman clothed_female clothed_female_clothed_male clothed_male clothed_male_clothed_female clothed_sex clothes clothing collar crying crying_with_eyes_open defloration deflowering dress_shirt earrings empty_eyes female female_focus female_penetrated female_virgin femsub forced freckles freckles_on_breasts freckles_on_face grabbing grabbing_another's_breast green_eyes league_of_legends male male/female male_penetrating male_penetrating_female male_pov miss_fortune nipples nipples_visible_through_clothing office office_clothing office_lady paper pinstripe_skirt pov pov_crotch pov_hands rape red_hair sarah_fortune skirt skirt_up submissive_female tears tied_up translucent_clothing vaginal_blood vaginal_penetration virgin virginal_blood wet wet_clothes wet_clothing white_dress_shirt

1boy 1girls ai_generated arms_above_head blood blood_stain bondage bound bound_wrists breast_grab breast_squeeze breasts business_attire business_suit business_woman clothed_female clothed_female_clothed_male clothed_male clothed_male_clothed_female clothed_sex clothes clothing collar crying crying_with_eyes_open defloration deflowering dress_shirt earrings empty_eyes female female_focus female_penetrated female_virgin femsub forced freckles freckles_on_breasts freckles_on_face grabbing grabbing_another's_breast green_eyes league_of_legends male male/female male_penetrating male_penetrating_female male_pov miss_fortune nipples nipples_visible_through_clothing office office_clothing office_lady paper pinstripe_skirt pov pov_crotch pov_hands rape red_hair sarah_fortune skirt skirt_up submissive_female tears tied_up translucent_clothing vaginal_blood vaginal_penetration virgin virginal_blood wet wet_clothes wet_clothing white_dress_shirt

1girls ada_wong ai_generated ai_hands asian asian_female black_hair black_lingerie blush brown_eyes business_woman candlelight dim_lighting eye_contact fancy fancy_clothing home hotel imminent_sex inside lingerie makeup maxiach_ai milf mother_and_son night playful resident_evil short_hair smile smirk solo

2:3 ai_generated arms_behind_back bent_over birdawg16 black_hair blonde_female blonde_hair bondage business_attire business_woman cumming desk dripping_pussy fat_ass glasses intern lezdom lezsub office office_lady pantyhose people_in_background people_watching plap_(sound) public public_humiliation public_sex rough_sex smug_grin strap-on strapon thick_thighs tied_up yuri