A freshly divorced man meets and is captivated by a stunning 55-year-old woman with the body of a dancer and the face of an angel.
#older-woman
529 stories tagged with this.
A young man continues his poolside encounter with Mrs. Jenkins, leading to an intense first sexual experience in her bedroom.
A young office worker navigates an unexpectedly intimate performance review with his attractive older female boss.
A teenager cleaning up after a party gets unexpected assistance—and temptation—from his attractive older female neighbor.
A 22-year-old man in Hyderabad recounts his real-life encounter and seduction of a 28-30 year old school teacher he met at a bus stop.
A teenage babysitter finally meets the mother he's been sitting for, and an unlikely seduction unfolds between the underage boy and the older married woman.
A shy teenage boy on his first job with a traveling carnival has a sexual awakening with an older woman, savoring his newfound experiences.
A 16-year-old boy gets caught staring at his young music teacher's cleavage and is surprised when she locks the classroom door.
A teenage boy fantasizes about his older Religion teacher, who unexpectedly initiates a sexual encounter after class in a school storage room.
A fifteen-year-old posing as eighteen spends his first week at a Cape Cod carnival, where older female coworkers draw him into playful after-hours games.
A man tries to end his affair with a much older married coworker at the office Christmas party, but she refuses to let him go.
A young male lodger navigates an awkward post-sex tea with his older landlady, who takes the lead in seducing him despite his anxieties about his size.
A man reunites with his much older aunt and gradually seduces her with wine and flirtation.
A teenage boy recounts losing his virginity to his father's older girlfriend after she drunkenly initiates contact.
A young man stumbling home from a bar glimpses a woman masturbating in her apartment through an open window and becomes entranced by the sight.
A retired trucker returns to running his roofing and painting business and visits a flirtatious older divorced woman who hired him, hinting at more than housework.
A polite contractor seduces an older female client after a wine-soaked lobster dinner, with anal and fisting on the menu.
A younger house painter surprises his 59-year-old customer with a new Sybian toy during their three-week affair.
A young taxi driver recounts a snowy-day encounter with a lonely elderly widow passenger.
A cheating trainer meets his married lover for a clandestine encounter in her minivan.