Kimberly Wilder is an artist whose realistic pencil drawings feature nearly exclusively “sissies,” or male-to-female transsexuals who, despite having an otherwise beautiful feminine appearance, apparently have opted to retain their male genitals. Her work occasionally includes spanking scenes which involve such sissies who are disciplined by dominant upper-class women or women in positions of authority.
In one drawing, a matronly figure holding a riding crop in her left hand and grasps the semi-erect cock of a schoolgirl sissy. The woman look angry, the sissy frightened. Obviously, both know, from experience, what is about to come (or cum). (A survey of Wilder's work shows grasping a sissy's penis is a favored way of exercising control over her.)
A second drawing treats viewers to the sight of a kneeling sissy wearing a bra and panties, her erection jutting stiffly from the latter garment, kneeling behind a woman whose cunt the sissy licks. A woman with a whip stands ready, as she watches, waiting, presumably to provide a sadistic element to the sex play.
Most of Wilder's prolific work celebrates female domination, or femdom, showing adult women humiliating, disciplining, or training younger sissies, often through anal penetration with huge or knobby dildos, or by forcing them to engage in unseemly sexual behavior with others their own age, with older women, with inanimate objects, or by themselves. All Wilder's work is well executed in a classic style that exhibits her talents as an illustrator. In addition, whether they show spankings or other activities, her drawings are also sexy.
Some of Wilder's early work has mythological themes (Adam and Eve, satyrs and naiads, demonesses). Many of the sissies bear a striking resemblance (not by chance) to the artist herself, who is male-to-female transgender. Wilder has illustrated Harriet Potter, a parody of Harry Potter, and her work includes sets of illutrations depicting narratives that take place in Catholic girls' schools. Samples of her work are widely available on the Internet.