A college student's first time cross-dressing and experimenting with a friend leads to an intense sexual encounter.
#dress
625 stories tagged with this.
A woman meets a stranger, has quick sex with him while their spouses are downstairs, and the encounter leads to unexpected consequences.
A crossdressing newcomer to a gay bar finds himself in an unexpected orgy with strangers.
A curious 19-year-old boy discovers a new world when he's hired to help a mature woman move furniture and ends up being trained in her secret basement playroom.
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 man rediscovers his love for porn through the lens of sissy hypno videos, leading him to explore his sexuality in public.
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.
A young man dresses up as a sissy girl to rent a room from an older man, who then seduces and fucks him.
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 gigolo is hired by an older woman and her cross-dressing step-son for a taboo threesome.
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.
Emma's wedding dress is just the beginning of her explosive journey in this erotic slow burn.
A crossdresser's first encounter with a stranger in a mall leads to an unexpected and fulfilling sexual experience.
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.