Transgender Casual Sex Stories

Danielle and Johanna arrive in Paris, freshen up, and start their vacation with a romantic river ride on the Seine.

A chance encounter between a seductive trans woman and a rugged truck driver ignites a night of unbridled passion.

A truck driver and his non-binary companion stop at a truck stop off US 36, where their Daddy-sissy dynamic unfolds in a steamy encounter.

A masculine bi man's life is forever changed when he meets Steve, an older man who introduces him to the thrill of cross-dressing and deepens their connection through affection and intimacy, leading to a night that shatters his boundaries.

Two fat gay men in their 50s discover a shared passion for lingerie and intimacy at a conference.

A man in lingerie gives his partner a blowjob during halftime, their casual sex fueled by the game and mutual kink.

A chance Halloween encounter turns into a night of unexpected same-sex attraction and deception.

A divorced man's Tinder date with a young trans woman ignites a passionate and erotic connection that changes his life.

A college student seduces their friend in a hotel room while their girlfriend is away.

A cross-dressing night out takes an unexpected turn at a truck stop, leading to a steamy encounter with a rugged truck driver.

A trans woman juggles romance and kink with a younger lover while exploring desires with new partners.

A 57-year-old man sheds his old life, embracing his true self as Caroline Bunny, and dives into a world of drag bars and casual sex.

A trans narrator meets four young footballers and gives them blowjobs, savoring their 'cheesy' unwashed cocks in a series of intense, anonymous encounters.

A young man transforms into 'Jenette' and lives out his crossdressing fantasy in 1980s Chicago, encountering seduction and self-discovery.

A battle-hardened veteran's Bangkok leave turns into an erotic odyssey with a captivating transgender woman, upending his masculine norms.

A corporate traveler encounters a trans porn star at a hotel bar, leading to a passionate night of sex and connection.

A crossdresser attends a rock concert, gets fucked by multiple guys, and scores a backstage hookup with the bassist.

A young trans woman's first sexual encounters with strangers are marked by awkwardness, rough sex, and emotional vulnerability.

Narrator and Dave explore intense physical desire and bisexuality in a summer of casual sex and intimacy.

Horny encounters with hot Brazilian hunks from a tranny site.

A 40-year-old man seduces a heartbroken crossdresser at a Halloween bar, leading to a rough, consensual night in a hotel room.

A 19-year-old soldier's wild night with a trans woman at Frankfurt's Pink Elephant bar.

A straight married man meets another man for a panty-clad cock grinding session that becomes a cherished memory.

A crossdresser recounts nights prowling LGBT-friendly areas, engaging in sex with multiple men in various settings.

A trans woman's car crashes in rural South Carolina, leading to a romance with a widowed doctor.

A 62-year-old man finds unexpected connection with a trans woman on Craigslist, overcoming his insecurities in a satisfying encounter.

Roger becomes 'Cindy' in London, meeting men for sex in his hotel room and at a trans-friendly club.

Terry, a submissive transvestite, is swept into an intense threesome with three young black marines at a San Diego beach hotel.

After a magical transformation, a man becomes a woman and embarks on a journey of sexual discovery and unexpected pregnancy.

A trans woman cruises a bar, picks up a man, and engages in explicit, consensual sex in his hotel room.