A curvy 16-year-old plans her first sexual encounter with her boyfriend, expecting a rough, rough encounter with her boyfriend and his twin brother after school.
#losing-virginity
58 stories tagged with this.
A shy college freshman chronicles his nerve-wracking attempts to lose his virginity by hiring street prostitutes, documenting the hunt and encounters along the way.
An 18-year-old girl brings her boyfriend home to an empty house to lose her virginity and fulfill her desire to experience sex for the first time.
A teenage boy recounts losing his virginity to his 16-year-old girlfriend Sarah, describing their escalating fooling around leading to intercourse.
A husband recounts his 50-year-old wife's teenage loss of virginity to her high school boyfriend, detailing their year of frequent experimental sex.
A nerdy eighteen-year-old virgin visits a prostitute to lose his virginity after struggling to attract romantic partners.
A virgin schoolgirl invites the football captain over to lose her virginity to him on a passionate night while her mother is out.
A 17-year-old boy picks up a 55-year-old woman hitchhiking and loses his virginity to her.
A shy sixteen-year-old loses his virginity to his Korean girlfriend on the last day of high school.
A 21-year-old man recounts his teenage first time with his conservative girlfriend, detailing the months of courtship leading up to their eventual hotel night.
A 16-year-old boy loses his virginity to a popular classmate while grappling with his bi-curious desires.
A teenage boy's six-month buildup of flirtatious teasing with his girlfriend finally culminates in losing their virginity together.
A teen boy's continued attempts to pursue his crush Kay after losing his virginity to her, navigating anxiety around meeting her friends.
A high school senior's quest to lose his virginity after breaking up with his girlfriend leads him into a series of sexual encounters with multiple girls.
A valedictorian sneaks off campus in a slutty disguise and encounters her math professor at a bar, unaware he recognizes her.
A young man attends a Halloween party where a supernatural deal promises to end his virginity in an unforgettable way.
A petite, overlooked 18-year-old virgin at a Catholic high school in 1974 finally loses her virginity to an older man in the custodian's room.
A 21-year-old Indian college student hires an escort for his first time and nervously negotiates services through an agency.