A teenage boy becomes infatuated with his attractive older Spanish teacher, fantasizing about her throughout class.
#older-woman
529 stories tagged with this.
A younger man visits his retired older female colleague and an accident with hot tea leads to an intimate, revealing situation.
A young boy's first sexual awakening unfolds at a strict Catholic school in 1960s Oakland when a tall, redheaded Russian nun catches his eye during a routine errand to the wine cellar.
A teenage boy obsessively pursues and eventually seduces his older female gym teacher, using his role as her class assistant to get closer.
A young unemployed man goes for a job-required physical and fantasizes about nurses with breast fetish and watersports scenarios.
A 15-year-old boy recounts his first intimate encounter with his attractive 34-year-old divorced neighbor, whom he had long admired from afar.
A sexually experienced fourteen-year-old boy catches the eye of his redheaded English teacher who summons him after class.
A younger man working late at his all-male office gets a visit from an attractive older female sales rep, leading to a flirtatious encounter.
A younger male coworker becomes increasingly obsessed with his older, recently widowed female manager and schemes to seduce her without getting fired.
A younger landlord meets an older down-on-her-luck woman interested in renting his property, and is captivated by her striking blue eyes.
A seventeen-year-old working at a feed store has his first real sexual experience with his late-forties widowed boss, Rose, one hot summer afternoon.
A lonely 16-year-old boy on summer vacation finally gets his longtime dream fulfilled when a neighborhood mother invites him over for his first sexual experience.
A young gardener who moonlights as a male prostitute meets a new client while his regular client conveniently steps out.
A ninth-grade boy recounts a sexual encounter with his best friend's mother after years of fantasizing about older women.
A teenage boy's fantasy about seducing his friend's attractive older mother during a beach vacation.
A young schoolboy endures a harsh caning from a cruel older female teacher, with recollections of brutal classroom discipline.
Three women on a vacation share wine and compare notes about their encounters with a skilled masseur, arranging their turns with him.
A 64-year-old Moscow widow takes on an unconventional new job in the chaotic aftermath of the Cold War's end.
A football coach arrives for a private session with a teammate's mother only to find she's arranged a threesome with a busty newcomer eager to secure her son's starting spot.
A young Black man on his 18th birthday catches the eye of his older white neighbor, who invites him over, igniting a forbidden interracial attraction.