It was a hot summer day and Tara was lounging by the pool, sipping margaritas and enjoying the sun on her skin, when she noticed her friend Jenna’s son Timmy lingering around. The 19-year-old boy was painfully shy and awkward, always fidgeting and blushing. Tara watched him with an amused smirk. Maybe it was time she took him under her wing and “fixed” him, as only she could.
Over the next few weeks, Tara made it a point to spend more time with Timmy, teasing him playfully and dressing him up in cute outfits when no one was around. At first the boy was nervous, but Tara’s sensual touch and honeyed words soon had him entranced. She started braiding his hair, painting his nails, applying lipstick. Timmy found himself lost in her emerald eyes, intoxicated by her womanly scent.
One evening, Tara suggested they have some fun with a new toy. Timmy hesitated as she Showed Him Her penis. “Trust me baby, it’ll be our little secret,” Tara purred, her hands sliding over his slim body. Timmy’s resistance melted under her persuasive touch and knowing smile. He Swallowed Her cock and let her fuck his throat. Then, He let her dress him up, the skirt tickling his bare legs.
Tara had him practice walking in the skirt and heels, swaying his hips like a girl. She braided his hair with ribbons and applied full makeup. “There’s a pretty sissy hiding under that timid boy, isn’t there?” she cooed approvingly at his reflection in the mirror. Timmy could hardly recognize himself, feeling giddy and ashamed yet curiously aroused.
This was only the beginning of Tara’s long-term project. She had all summer to play with her new little toy and remold him into the perfect sissy slut. And by the time she was done with Timmy, he wouldn’t just be questioning his masculinity – he’d be leaving any trace of it behind. On his knees, in his new favorite skirt, calling Tara “Mistress” between gasps of pleasure.