A shy 15-year-old boy fantasizes about a cute classmate named Jenn while slowly building a friendship with her during his last year of high school.
#shy-boy
5 stories tagged with this.
A shy teenage virgin who can cum repeatedly lives with his hot mother and aunt and soon explores crossdressing and sexual encounters with the two sex-starved women in the household.
A shy teenage boy's fantasies come true when the girl he admires suddenly asks him out after a failed attempt with her boyfriend.
A shy, lonely new student gradually falls for the persistent popular girl who befriends him, building up to their prom night together.
A shy new student is pursued by a persistent blonde girl named Jessica, building up to their prom night together.