The following is an excerpt from Football Sissy by Jack Brennan, available now from Belt Publishing.
In 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.
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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.
Wanting to dress like a girl is among my earliest memories. In the fall of 1955, growing up in Dallas, Texas, at about age three and a half, I was taken by my mother on what would prove a landmark visit to some neighbors. Their daughter Janie (not her real name) was about my age, and while our moms were chatting, Janie and I went to play in her room.
This was not the first time we had gotten together in this way, but this playdate came with a new twist. Janie’s blouse had just the cutest puffed sleeves, and I became entranced by it. I wanted to know what it would feel like to wear it.
Check that. I already had a damn good idea how it would feel, and I wanted to experience it. I wanted to gaze at a new self in the mirror and then put on a complete girl’s outfit and be seen in it by others.
At three and a half, I didn’t question or analyze my feelings. I just acted, suggesting to Janie that we swap tops.
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She happily agreed, and when we went in to show our moms, they reacted as if it were just the silliness of small children. But while I giggled on the outside, my heart was pounding. I knew I had uncovered something powerful. I didn’t want to take off that blouse, and when Janie made clear that dress-up time was over, I felt regret. I suddenly had little enthusiasm for our normal play. While switching back to my own shirt, I had visions of walking in our neighborhood with that blouse on, for any and all neighbors to see. How exciting such a stroll would be!
But I knew even as I fantasized that this could never actually happen. Boys were simply never to do such things. (A huge reason it was so exciting!) It quickly dawned on me that I had a secret I could never reveal to anyone. Though I didn’t feel inner shame, accepting myself with surprising ease, I knew the world would think otherwise. It would be nothing short of catastrophic to give anyone even an inkling.
With this dose of reality, my urges would not be front and center again for some years. Plenty of other things interested me as I progressed into my preteen years, and playing with dolls and tea sets was not among them. I loved toy trucks and toy guns and “army men,” and I developed a passionate interest in sports. I played on the sandlot level almost every day—softball, basketball, and tackle football without pads.
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As I grew older, I watched big-time sports on TV and read about them daily. I spent almost all my allowance on baseball and football cards, and my school classes came to know me as their resident expert on sports news. It was a fine kid’s life. I had plenty of friends, all boys, and that intense day at Janie’s was . . . heck, I didn’t know exactly what it was, but it didn’t prey on my mind.
The desire to dress, though, would not remain dormant indefinitely. It next popped out, in a veiled way, when I reached fifth grade and entered a prep school whose uniforms included neckties. Outwardly I expressed disgust, professing that ties were for wimpy kids. But quietly I came to like being a “dress-up boy.” I often enjoyed keeping my tie on during late-day periods when the dress code wasn’t enforced and peers were shedding their cravats. I tended to obsess over the tie and adjust it almost constantly, making sure it looked perfect. I didn’t make the mental connection to cross-dressing at the time, but I see it clearly now as a substitute.
By about age twelve, a boy’s necktie was no longer enough. Old enough to be home alone, I went rummaging through my mom’s things. Hers were the only ones available, as my only sister was out of high school and in a Catholic convent.
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Mom was no fashionista, but she had plenty of stuff that interested me, particularly lingerie and hosiery. I loved putting on stockings and attaching them to a garter belt. (Is there anything in the world so completely feminine as a garter belt?) Sometimes I’d do hose and garters even when my parents were home. I’d slip them on in the bathroom, then pull up my pants and go about usual business. I would be inwardly very excited, feeling delicious tension over the outline of the garter being visible under my pants. But no one ever professed to notice, and I never felt remorse when my little show was over. I knew I just would keep doing it and keep hiding it.
These were also my first times dabbling with makeup. There was lipstick, of course, but what I remember most was the mascara, which was not at all like mascaras of today. It came in a tiny squeeze tube, like ointment, and you applied it with a separate brush, squirting it onto the brush like black toothpaste.
So primitive, but for me it was like dynamite. I marveled at how each stroke made my lashes long and alluring. I got a tingle from just the word mascara. It was a word a regular boy would certainly never speak, thus it just sounded so feminine.
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Was my mom finding clues of my activities? I worried that she might notice a slip not folded right, or runs in her stockings, or that the mascara tube was running low rather quickly. But she never evinced such a concern.
Unquestionably, my parents were the wellspring of my freedom from deep recrimination about dressing. Not that they knew about it and handled it perfectly—I’m sure they were totally in the dark, as I felt I needed them to be—but the key was that I simply received the loving care that should be every child’s birthright from two good people living the conventional white heartland life of the mid-twentieth century.
Some kids would later say that my folks were too easy on me, and they once said it quite bitterly. When I was sixteen-ish, I was caught egging unlucky cars at Southern Methodist University with some guys. When we were serving our sentence (washing police cars for four consecutive Saturday mornings), the other guys were complaining about their punishments at home.
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“I’m totally grounded for 12 weeks,” one proclaimed.
“I can’t even go to basketball practice for two weeks,” another said. “I might as well quit the team.”
“God, did my dad scream at me,” shuddered a third. “The neighbors heard it.”
Then it was my turn.
“Well, my mom and dad made me feel pretty bad,” I said. “But they really seemed more sad than mad. They just said it was so disappointing I would do that. They’re kind of acting cold to me right now.”
“That’s it?” said one. “You’re not even grounded? They’re ‘cold’ to you? That is such bullsh*t!”
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This proved to be a consensus opinion, and for a few days I was literally ostracized.
But maybe my folks’ disappointment was punishment enough for me. Maybe draconian discipline was not always the way to go. I knew my folks still loved me and were willing to give me a second chance. Ted and Helen Brennan certainly had their struggles—Dad died a severe alcoholic and Mom suffered late in life from a bipolar disorder—but their trust helped imbue me with durable self-esteem. I never was made to feel unworthy of all the love they could muster, and they mustered plenty despite their issues. Their unconditional love made me know I was still a great kid, even if I was a convicted egger and a secret sissy.
Except from from Football Sissy by Jack Brennan, available now from Belt Publishing. Reprinted with permission. © 2025
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