A bored sixteen-year-old boy takes a summer job helping his attractive older neighbor move things around her house, only to find himself drawn into a tempting and taboo encounter.
#older-woman-younger-man
151 stories tagged with this.
A graduate student recovering from illness begins a long affair with his mother after she discovers his stash of forbidden erotica while caring for him.
A frustrated young Florida grocery store worker learns about bondage and the joys of mature women from an older cowgirl.
A virginal sixteen-year-old boy is seduced by a thirty-something Englishwoman during a transatlantic flight, joining the Mile High Club.
A high school student visits his teacher's home for a makeup assignment that leads to a sexual encounter.
A young male tenant is seduced by his stern, sexy older landlady who resumes taking care of his needs after he admits he still has no girlfriend.
A young man takes control of his lonely widowed neighbor, training her to embrace submission after an initial forceful encounter.
A young white stud answers a sex ad from an older, heavier-set Black woman seeking a hung partner for a night of intense, no-strings encounters.
An older woman answers a wrong number, connects with a younger man, and contemplates an age-gap hookup after flirtatious phone banter.
A shy, bullied 17-year-old raised by his football-star cousins finally gets a chance at confidence when an older woman takes interest in him.
A recent college graduate encounters a strong, sexy older woman at his company gym during a late-night workout session.
An 18-year-old moves in with a sexy, busty MILF landlady and gets walked in on during a bath.
A young surfer places an ad offering himself as an escort to financially secure older women and receives his first booking from a wealthy woman in La Jolla.
An older married woman indulges her beachside fantasy by enticing a young surfer with topless sunbathing and a sexual encounter.
A 17-year-old student becomes infatuated with his attractive middle-aged neighbor and hopes to get closer when she needs a handyman while her husband is away.
A 16-year-old orphan boy develops a sexual relationship with his best friend's 38-year-old single mother.
A young college student delivering a late-night pizza to an affluent older widow finds himself unexpectedly falling for her.
A 23-year-old narrator recounts the evening he loses his virginity to his 39-year-old girlfriend Beverly at her place.
A young maintenance man visits an older woman's apartment to fix a stuck window and encounters a sultry surprise.
Two older women friends at a NYC gym share a fondness for younger, fit men and the fun of unattached flings, until Monica's career life brings a new complication.