Four separate stories of the auto-sexual proclivities of Chicagoans is presented. In the first story, a man, who is in a seemingly supportive relationship, is nonetheless self-conscious about what he considers the small size of his penis, regardless of his girlfriend telling him otherwise. His penis enlargement efforts lead to a change in attitude on many fronts. In the second story, a woman, who is in a supportive sexual relationship, has of late been turned on by everything, which leads to her feeling the need to masturbate whenever and wherever she can. After discussing the issue with a friend, she decides to take that sexual arousal to the next level by experimenting with auto-asphyxiation. In the third story, a pregnant woman, while still sexually aroused, can no longer come to orgasm through vaginal penetration. A female friend believes she can help her reach orgasm again, which the pregnant woman’s husband allows. Although this experiment is solely to be between the two women, the husband can’t help but want to be a part of the experience, even if the two women don’t know. And in the final story, a man’s primary sexual release is watching videos of him and an old girlfriend having sex. She, who is about to get married to someone else, reenters his life as she wants him to delete those videos. Wanting/needing a replacement for those videos, he asks her for one last “non-sexual”/non-video favor before she exits his life for good.