This work makes use of an interior monologue to convey the private thoughts, doubts and dreams of the fifteen year old male protagonist in the sub-culture of 1960s Toronto, the luxurious Halton Hills and an idyllic private island in the Bahamas. Shawn is sent to live with a well-heeled spinster aunt in the town of Longbranch where he is placed into the public system. He rebels at the system, the rejection of his first lover - a forty year old friend of his aunt's and leaves home at fifteen to discover life on the streets of Toronto. As a young teen he seeks the meaning of love, sex,and friendship in the skewed values of Toronto's subculture. His quest for self-awareness draws him into the violent and sexually ambiguous world of loan sharking and prostitution and ultimately into the high-life of the ultra-rich and powerful when, as a male prostitute, he meets the 'Tiger Lady', a troubled and ruthless female captain of industry. His inner dialogue expresses the naivete and confused emotions of a sexually active teen seeking validation, nurturing, and love busting the stereotype of the callow youth after easy money and sex.