Heads, I Win-Tails, You Lose, is the story of Chloe an unhappy housewife who decides to add spice to her dull marriage by seeing a guy name Samuel. To keep the affair on the down-low, Samuel, a dedicated juvenile probations officer, agrees to become Samantha, a sensual and flirty she-male. Over a period of time the game blossoms into a torrid love affair and the husband stands in the way of their happiness. As the charade plays out, Chloe and Samuel set in motion a devious plan to find out whose really on the down-low.