A 15-year-old football player gets the courage to ask the girl he likes to the high school dance after she unexpectedly flirts back.
#first-date
92 stories tagged with this.
Two teenage sweethearts prepare for a romantic surprise evening together, as a fifteen-year-old boy plans a special night to show his lifelong crush how much he loves her.
A girl goes on a date with her crush Blake that leads to passionate sex at his place.
A 19-year-old recounts his first weekend with a girl he met through a friend, as their connection quickly turns physical.
A college freshman picks up a striking new co-ed named Nancy at a university party and arranges a dinner date at her dorm room.
A woman meets her online gaming crush for their first in-person date, building anticipation through flirtatious exchanges before things heat up.
A man picks up a woman for a fancy beachside dinner date and brings her back to his place for a long, slow night of sex.
A 15-year-old girl sneaks out for a first date with her older boyfriend, eagerly anticipating losing her virginity.
A man plans the perfect San Francisco date, touring scenic and culinary hotspots, building romantic and sexual tension with his partner throughout the day.
Tiffany eagerly prepares for her first date with Chris, dressing to tease and feeling the thrill of exhibitionism while watching him arrive.
A trans woman prepares nervously for her first date with a man, encouraged by her wife who has given her a surprise present.
Two young gay men meet for the first time after connecting on a dating website and hit it off immediately over dinner and bowling.
A 14-year-old girl recounts losing her virginity to her first boyfriend after a chance neighborhood meeting.
A nervous teen goes on a movie date with the girl he's already been intimate with, navigating sweet moments and small daring touches in the dark theatre.
A young man begins dating a coworker whose mother has two boyfriends, setting up a romantic encounter that leads to a foursome.
A man picks up a date dressed without panties and they engage in heavy petting and fondling during a movie theater showing.
A shy dance instructor meets a striking older woman at his social ballroom club and nervously navigates their first date, keeping things innocent while growing closer through their shared passion for dance.
A teen boy asks out the girl who blossomed over summer, navigating her self-consciousness about her suddenly huge chest to score a pizza-and-movie date.
A young man's romantic picnic date with a coworker unfolds in near-miss fashion, building weeks of flirtatious longing toward an eventual intimacy.
A 16-year-old girl is surprised by her longtime crush at a YouTube convention where her favorite British YouTuber also appears.