Bailey Wilde, a dominating trans beauty, commands her feminized roommate Jake Grand to bend over the bed. Jake, his body adorned in lingerie and a corset, has been denied orgasm for days, his cock locked away in a chastity cage. Bailey, wearing a sleek corset and thigh-high boots, teases him with a strap-on, rubbing it against his ass before plunging it deep inside him. Jake moans, his sissy voice filling the room as he's fucked missionary style, his body squirming in pleasure and pain.