A young bicurious man living with his roommate explores his taboo attraction to feminine, crossdressing teenage boys.
#age-gap
3362 stories tagged with this.
An assistant manager at a nursing home is drawn into sexual encounters with elderly residents after catching one of them masturbating.
A mid-thirties rower becomes involved with a petite high school coxswain whose family he's long known at the boathouse.
A lonely wife writes a confessional letter to her husband about her encounter with a young inspector while he's away.
An exhausted older businessman hits it off with a younger hotel desk clerk who slips him her number despite company policy.
A teenage boy follows his older female gym coach to her office, where his fantasy begins to unfold.
An 18-year-old narrator recounts how, at age 12, she began a secret sexual relationship with her stepfather after overhearing her mother refuse his frequent advances.
A woman reminiscing about her youth spots a flirtatious schoolgirl on the bus and embarks on a summer holiday involving seduction, bisexual exploration, and a shared encounter with a young man.
A young man relocates abroad with his father and contemplates pursuing a relationship with his father's new older girlfriend after ending things with his previous stepmother.
A timid 19-year-old tenant is identified by her older landlord manager as someone who craves domination, setting up an unbalanced power dynamic.
A 65-year-old terminally ill widower reminisces about losing his virginity at 14 to a girl named Carol at a town Fourth of July picnic.
An older writer recounts being contacted online by an 18-year-old self-styled Pagan Sex Goddess from Colorado, leading to a charged email flirtation.
A frustrated 48-year-old wife decides to become a cougar and seduces young college men while her aging husband watches from the sidelines.
A 15-year-old Asian boy fulfills his fantasy of servicing a bearded, bearish trucker at a truck stop after responding to a Craigslist ad.
A family friend reunites with a girl he first met when she was thirteen, and her newly adult confidence rekindles their forbidden attraction during a beach visit.
A nearly-40 single mother catches sight of her 21-year-old son's endowment and finds herself unable to look away.
An older landlord and his young tenant share a tender morning together as their age-gap romance deepens following their first night.
A young woman in her late teens becomes entangled in an affair with her married middle-aged neighbor while fighting with her much older boyfriend.
A man in his 60's answers a swinging ad and connects with a woman in her mid-20's who prefers older men, leading to their first encounter.
A young male graduate student recounts cheating with his friend's older mother during his time in a small Indiana grad school program.