Long First Time Sex Stories
The longest first time sex stories on the site — slow-burn reads of 2,500+ words for when a quickie isn't enough. Browse all First Time stories →
Every story we've published, in one quiet list. New ones land at midnight.
Gym Floor After Closing
Virgin college girl seduces night-shift neighbor.
Friends-with-Benefits in the Stockroom
Virgin college girl loses her cherry to her flirty coworker in the stockroom.
Party Cleanup In The Fitting Room
Virgin coworkers lose their virginity in the fitting room.
Reunion Couch at the Party
Virgin codys first time with neighbor leilani.
River's First Cock, Watched by Their Girlfriend
River gets their first real cock—gently fucked and filled while girlfriend Noelle watches and coaches every moment.
Next Door Boy
Cassidy seduces her eager virgin neighbor Roman for his very first time.
My Friend's Urge to Deflower My 36DD Stepdaughter
A man finally gives in and deflowers his eager stepdaughter's virgin pussy.
My 63 Year Old Petite White Wife Gets Ripped Wide Open By Her First Enormous 14 Inch Thick BBC
My petite wife eagerly lets our neighbor stretch her with his first enormous 14-inch BBC.
Friends Share First Night
Best friends share first night together.
Her Best Friend's Stepbrother: The Deliberate First-Time Bet
Emma lets her best friend’s cocky stepbrother Jake take her virginity during their secret summer fling.
Rebound Stranger: Her Unexpected First Surrender
Virgin Sophie lets a hot stranger fuck her for the first time in a dirty alley.
Rooftop Widow's Slow Midnight Surrender
A lonely widow lets her hunky maintenance man be her first new lover on the rooftop.
Rebound Friends Share Karaoke Couch
Virgin friends Petra and Sergio share first-time couch.
Curly-Haired Blonde Discovers Her First Huge Cock
Nadia gives her first eager blowjob to Barrett’s huge cock.
Her First Massive Cock
Estelle eagerly sucks and strokes her first massive cock on a hot first date with Reid.
Moored in Her Hunger
A shy virgin sailor loses his cherry to a bold stranger on a moonlit beach.
Roommates Finally Touch in the Stockroom
Roommates finally fuck in the stockroom.
Lighthouse Flame: Her Divorced Neighbor's First Claim
Roxanne loses her virginity to her hot divorced neighbor on a stormy night.
My Roommate Claims My First Time
Renata's hot roommate claims her eager virginity.
Rained-Out Costumes: Her Best Friend's Tent Virginity
Bianca's best friend Franklin takes her virginity in a rain-soaked tent.
Her First Taste Under Lanterns
Shy baker Roxanne gets her first taste from neighbor Everett under swaying lanterns.
Midnight Rooftop Bet: Her Best Friend Claims Her First
Best friends Renata and Errol fuck on a rooftop after a truth-or-dare bet takes her virginity.
Snowbound in Her Darkroom: Best Friend's First Claim
Trent claims his photographer best friend's virginity while snowed in her darkroom.
Vinyl Shadows: Her Skinny-Dipping First Claim
Lorenzo claims his eager virgin customer's first raw fuck in the shop's rainy courtyard tub.
Aquarium Shadows: Her Best Friend's Please
Two virgin friends fuck for the first time at the aquarium after hours.
Her Quiet Best Friend's Darkroom Surrender
In his basement darkroom, Terrence takes his eager best friend Yvonne's virginity.
His Wife Takes First Cock
Sophie watches her husband as Marco gives her first cock.
Her Best Friend's Cool Fingers First Bloom
Lily's shy first time gets eagerly explored by her bisexual best friend.
Masquerade Stranger Claims Her First Surrender
At the masquerade ball, virgin Paulina begs the masked stranger to take her first time.
Aquarium Midnight: Her Deliberate Lost Bet
Virgin graduate Roxanne deliberately loses a bet so her hot boss Callum can take her first time.