A transvestite's first days of sexual freedom lead to a wild party and unexpected encounters.
#cross_dressing
59 stories tagged with this.
A man finds himself in a threesome with a couple where the wife is dominant and the husband is cross-dressing.
Barb explores her sexuality in a thrilling threesome with a cross-dressing tranny and her friend Janine.
A gigolo is hired by a couple to provide sexual pleasure for the wife, but the husband has his own plans for their encounter.
A straight woman meets and hooks up with a cross-dressing tranny at a gay bar.
Sarah plans a special birthday surprise for her husband Roger, involving a bi-sexual woman and a cross-dressing man with impressive assets.
A couple invites a gender fluid duo over for Sunday afternoon fun, leading to an arousing group session with cross-dressing, exhibitionism, and oral pleasures.
A college student's first time cross-dressing and experimenting with a friend leads to an intense sexual encounter.
A man decides to transition to a woman before having his genitals removed, leading to unexpected encounters in a Glasgow pub.
A cross-dressing convention-goer explores their desires and ends up in a wild hotel room encounter.
A night of music and molly leads to an unexpected encounter between best friends.
A man cross-dresses and gets fingered and fucked by his lover in a unique position.
A cross-dressing funeral attendee finds unexpected pleasure with two old friends.
A gigolo's seductive encounter with a sophisticated businesswoman leads to an extended sexual experience filled with surprises and kinks.
After being outed as gay, a young man returns home to his mother and seeks solace in an old friendship, only to find himself drawn into a new dynamic.
A couple invites a trans woman over for a threesome, leading to an intense and pleasurable encounter.
A couple's bi-curious friend visits, leading to a threesome with unexpected roles and kinky revelations.
A man discovers he can easily change his gender to gain access to women's changing rooms and showers.
A young man is seduced by his gym buddy's step-mom and her girlfriends, exploring new kinks and boundaries together.
A newly divorced man loses a bet and must dress as a woman for the weekend, leading to unexpected encounters and a new relationship.