A young man is initiated into gay and crossdressing experiences by his aunt, culminating in preparation for anal sex with a group gathering.
#dressing
634 stories tagged with this.
A boy continues navigating his gender transition and relationships with his brother and boyfriend as they visit a studio.
A crossdressing man invites a black man over on Thanksgiving night to fulfill his fantasy of being dominated and used orally.
A man finally indulges his lifelong fantasy of feminization by inviting a stranger to dominate and orally use him.
A cold December night in a cabin leads a woman and her lover to share their first intimate, warming encounter together.
A teenage boy sneaks into girls' clothes when home alone, transforming into a preteen girl's outfit before seeking out toys to pleasure himself.
A bisexual man in a schoolgirl uniform and heels visits a notorious English cruising spot to find hung tops for anal encounters.
A young woman's first sexual experience unfolds in detailed foreplay and lovemaking with her devoted partner.
Two male friends land lead parts in a school play where one must portray a woman, sparking an intimate connection during rehearsals.
A young man is mistaken for a woman by his elderly aunts and must humor them by presenting as female while staying in their conservative home.
A college couple returns to their dorm room and discovers their roommate and his friend in a compromising position, leading to a group encounter.
A young crossdresser moves into his own flat and prepares for his first public outing dressed as a woman, recounting his sexual experiences leading up to meeting Joe.
A man shares an intimate, tender night with his lover Natalie, culminating in oral pleasure as they savor each other's bodies.
A straight man messaging women online unexpectedly connects with a cross-dresser and finds himself unexpectedly intrigued.
A married husband details his submissive relationship with his dominant wife, including pegging, forced crossdressing, and her sharing videos with her best friend while she's away.
A husband guides his wife into anal play and femdom dynamics, sharing videos with her best friend while she begins asserting dominance.
Two teenage cousins secretly plan and execute an anal and oral encounter on Christmas Day while their families celebrate downstairs.
A nervous crossdresser invites an older guy over, dresses in a schoolgirl outfit, and experiences anal sex for the first time.
A 20-year-old narrator recounts arranging a hotel encounter with a visiting stranger seeking a transvestite for a threesome fantasy.
A crossdressing man ventures out in feminine attire for the first time and ends up having sex in a public toilet.