Football Sissy: A Cross-Dressing Memoir

In Jack Brennan’s decades-long career as a sports journalist, he covered teams like the MLB’s Reds and the NFL’s Cincinnati Bengals. As the public relations director for the Bengals, he wrangled sports stories, reporters, and players. At home, he played basketball with the neighborhood husbands and raised three kids with his wife, to whom he was devoted. At the same time, he had a passion that never left him: he liked dressing as a woman. Blonde silky hair, bright lips, and smooth legs escaping short skirts, topped off with heels as high as they go.

He kept his life as a crossdresser mostly private, so his public coming out via The Athletic in 2021—one of the first men in the NFL to come out as LGBTQ+—was a surprise to many. Football Sissy offers a no-holds-barred trip through his dual lives, from his earliest love affair with a puff-sleeve blouse at age three through to his first jaunts dressed in public to surprise visits to the hospital alongside a fulfilling family life and an exciting career.

Told with the characteristic humor and ease of Brennan’s sports columns, Football Sissy is a heartwarming tale of acceptance and love, even within the most masculine of environments.