With Annie's Understanding

Jensen or Jenny rather, is caught modeling pumps and a pair of stretchy lace panties by his best friend's mother, Annie. Both the shoes and panties belong to her and as would be expected, she hits the roof when she discovers the boys are involved in a very complicated relationship.
Annie finally regains her composure and suggests that she and Jenny sit and discuss it in more detail. Over a cup of coffee with the morning sun slanting through a kitchen window, the two become friends. A mother and her son's cross dressing, sissy lover.
Jenny's persona is based on internet port starlets, stockings and heels. Annie dresses her in something more age appropriate and suggests that her son take his sissy on a real date to make her feel special.
With Annie's Understanding is sweet, sissy romance offshoot of the earlier Sissy Mistress that provides a little more of the background behind Jenny and Drew's odd relationship.