Two buddies at a Halloween party, one dressed as a female devil, end up hooking up after everyone leaves.
#crossdressing
480 stories tagged with this.
Husband caught in drag with a male lover must now watch his wife sleep with her ex as retribution.
A male crossdresser walking in tights and leotard encounters his drunk neighbor and joins her for a ride with her friend, leading to playful situations.
A nervous young man in pantyhose gets invited to a couple's house for his first threesome experience after meeting them at an adult bookstore booth.
A man crossdresses in heels, pantyhose and a wig to meet a fellow CD enthusiast at a hotel for a brief sexual encounter.
A bored married man invites his male friend over while secretly wearing women's clothing, leading to mutual attraction.
A nervous crossdresser recounts driving to an adult theater in full feminine attire for the first time, documenting every detail of the thrilling experience.
A husband gets recruited by his wife's niece and her hot friend for a night out after being seduced while wearing pantyhose.
A crossdresser attends a hotel party and gets felt up in the elevator before joining a large group encounter.
A smooth-bodied teenage swimmer explores his attraction to both genders and discovers a fascination with skimpy women's underwear.
A nervous sissy transforms into a feminine slut for her first real meeting with an internet hookup at the door.
A teen boy explores feminization through clothing and makeup before turning to sex work.
Sam's secret crossdressing habit is discovered when he accidentally gets trapped in the closet watching his older sister service her well-endowed Black boyfriend.
A transgender youth navigates school bullying and an abusive relationship with Richard, who claims ownership and lashes out violently when challenged.
A teen boy uses a magical pendant to transform into a girl and eagerly shares the discovery with his friend, who wants to try it for himself.
A man who secretly loves wearing women's lingerie accidentally gets locked out of his hotel room clad only in panties and stockings.
A near-seventeen-year-old narrator recounts being seduced and feminized by her 43-year-old lover Peter during their seaside holiday together.
A nearly seventeen-year-old girl recounts her passionate, transformative summer romance with her 43-year-old lover Peter, who helped her embrace a sexy feminine identity.
A crossdressing man alone in a motel room, dressed in lingerie and drunk on wine, masturbates with a dildo and fantasizes about servicing a real cock while impulsively posting a Craigslist ad for company.
A closeted crossdresser uses his wife's absence to fully indulge his Suzy alter-ego, leading to an unexpected and shocking new chapter.