A senior boy carefully preps himself for a repeat encounter with his teacher during after-school detention.
#transvestite
103 stories tagged with this.
A closeted crossdresser prepares as Brenda for a special first night while on a business trip, sharing wine and webcam time in transgender chat rooms.
A priest's secret life of perversion is witnessed by a younger colleague who faces a moral dilemma about exposing or joining in.
A crossdressing man answers a personal ad and discovers the hookup is his boss, leading to a secret encounter at a bathhouse.
A 17-year-old boy spends the summer with his lesbian aunt in San Francisco and begins a journey of sexual discovery, starting with voyeurism.
A young crossdresser transitions further into womanhood while two women engage in lesbian sex and a trans woman receives anal pleasure, culminating in mutual climax.
A young crossdresser visits a finishing-school boutique owner who seduces her during a fitting, leading to steamy encounters between them.
A recently divorced bisexual man reconnects with an online buddy interested in crossdressing, reigniting old fantasies.
A middle-aged man covertly photographs his young neighbor sunbathing in feminine attire and schemes to manipulate him into a sexual encounter.
A cute college guy catches the attention of a sorority's sisters, leading to group encounters and exploration of his unexpected appeal.
A bullied high schooler navigates torment from jocks while discovering new relationships and encounters.
Chapter five of a serialized adventure following W as he travels to Davenport, Iowa in pursuit of the Monty brothers.
A young man works as a house boy for a sorority, servicing sisters in exchange for favors and a new little sister.
A teen boy and his female friend experiment with bondage, nipple piercing, and crossdressing in her bedroom.
A sorority wedding weekend leads to crossdressing, lingerie play, and a threesome between two brothers and a sister.
A muscle-bound jick pushes his meek, feminine-looking best friend into a wild sorority party that escalates into sexual coercion and sissy feminization.
A college stud returns for sophomore year, navigating sorority parties, dorm hookups, and ongoing entanglements with multiple women across campus.
A college student stays on campus for summer with three sorority sisters, exploring crossdressing and mutual masturbation with one of them.
A college sex guru helps a shy sorority sister embrace her squirting ability during a relaxed dorm session.
Two young boys cut across a field, discover a hidden haystack fort, and spy on an older couple's tryst.