Jack Brennan on his cross-dressing life, being supported by NFL greats & that time a cucumber got stuck inside of him…

For Jack Brennan’s co-workers with the Cincinnati Bengals, it was a typical Monday. Outfitted in a team-issued polo and khaki pants, the team’s PR chief seemed straight as an arrow.

If only they knew where he was seven hours prior: laying down on an operating table in the ER with a cucumber stuck up inside him.

It was the second time that Brennan’s extracurricular adventures would lead him to such a precarious predicament. When it first happened, Valerie, his wife of 51 years, accompanied him to the hospital. But on this penetrative evening, she simply wished him well and went back to sleep.

She is accepting of her husband’s cross-dressing, and in his words, “complete submission to the male sexual power.”

How about we take this to the next level?

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She provides Jack the space to express himself–preferably in a skimpy skirt and heels.

“We were just the right people for each other. I feel very fortunate,” he tells Queerty. “She accepted me for who I am.”

On the eve of a new NFL season, Brennan is providing the world with the same opportunity. Four years after coming out in The Athletic, he’s telling his tantalizing tale in a memoir, Football Sissy. For five decades, Brennan spent most of his waking days around the testosterone-filled NFL, first as a sportswriter and then as PR head for his hometown Bengals.

But late at night, when the press box was empty and stadium lights turned off, he would venture out as a different person. “Jackie” never left home without her silky blonde wig, along with a thirst for adventure. She started with “quickie walks,” becoming a regular at the local gay bar.

Eventually, she graduated to karaoke. “Jackie,” who first appeared in her mother’s closet as a toddler, was out of the shadows.

Now, she’s in the sunlight.

Before Football Sissy hit the shelves, Queerty caught up with Brennan to chat about his cross-dressing life, reaction around the NFL and tips for applying makeup (be precise). Here’s what he had to say…

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The following is an excerpt from “Football Sissy” by Jack Brennan, available now from Belt Publishing.

QUEERTY: You don’t leave any stone unturned, even writing about your trip to the ER after an incident with some produce. Did you always intend to write such an open book?

JACK BRENNAN: Part of that was a process. Editors kept telling me, “Memoir is a very competitive field. You’ve got to really open it up and just be as honest as you can be. Dig deep for everything you can get out.” I wasn’t going to write the ER-cucumber part at first. I was like, “Nah.” But again, I kept getting urged to be totally honest and candid.

Is there a particular story that you enjoy re-telling?

The story I like re-telling the most is the one where my neighbor thought I was breaking into the house and the cops came over. That’s one that seemed horrible when it was happening, but to look back on it now is funny and fun.

You also share a story about that night you were in Miami and police were at your hotel room’s door. You had a lot of close calls over the years. Yet, you kept going out. What propelled you to say, “I will put my heels back on?”

I just wanted to do it. I had a strong attraction to do it. I’m sure you read the part about where I got mugged, got my purse stolen. After that, I had just a few second thoughts. But I never really did, in the end, get in any real danger to my job, to my physical person, to my relationship to Valerie. They were close calls, but close calls were not enough to scare me.

Your write about your relationship with Valerie, from your first conversation late at night to joking about your trip to the ER. That’s wonderful to read about…

We were just the right people for each other. I feel very fortunate. We met when we’re 17, and we were just the right people for each other. It’s lasted through all these years. She accepted me for who I am. We didn’t make cross-dressing the defining thing of our relationship. It was almost like, in some ways, the same as if I had been one of these guys who plays golf all the time. “He’s always out playing golf.” I was out by myself doing what I did. But our relationship was always No. 1.

Your book has blurbs from NFL greats Phil Simms, Cris Collinsworth, Boomer Esiason. What does it mean to read their kind words?

It means a lot. It was [NFL writer] Peter King who brought up the idea. I was coming out to all of my media friends personally. He said, “What about guys like Boomer and Cris? Don’t you want to tell them?” I was like, “Oh yeah, you’re right.” I had relationships with these guys, and knew about the concept of getting celebrity blurbs, obviously. I just thought it was key to have those guys in my corner, and be able to get them to make those comments on my behalf.

When I first came out in the text to Boomer and Cris, I was still too scared to really tell them what it was about. It was very moving and touching to me that they cared enough to get back in touch and say, “This is a really weird text. What the hell is going on?” Then when I told them, they were so supportive. They all said, “Anything I can do to help you, let me know.” I said, “Well, the biggest thing you can do to help is endorse me and the book.”

What’s the reaction been around the NFL?

All positive. All of my former PR colleagues with former teams, most of them I’ve heard from. All of them have been totally supportive. Some of them I do know are quite conservative in their lives. We would not see eye-to-eye on a lot of things. Even so, in this case, a personal thing with someone you know, they’ve all been totally supportive. I haven’t had an ugly [encounter] with anybody.

What’s one thing about cross-dressing that people don’t understand?

That’s a good question. Maybe that, as strange as it may seem, and as de-masculinizing as it may seem, cross-dressers are like anybody else. It’s not their entire life. They are regular people. I’m not claiming to know a million other cross-dressers. I’ve been somewhat of a lone wolf in this. Not totally, but also not in the cross-dressing community and having a lot of cross-dressing close friends. I’m out with all those people, but they’re not central in my life.

In your book, the biographical sections are written in standard font. For the CD chapters, the font is more frilly and fun. What aspects of your personality does cross-dressing bring out?

I like attention! I guess I like to sing and perform, to some extent. I really enjoyed when I got into karaoke at the bar. That was a really fun thing. Maybe that I’m just more of a… I have a girlish aspect to my personality. It’s my main personality, it’s not my base personality. But it’s there, and I enjoy it.

What’s your best tip for applying makeup?

My best tip for applying makeup is to get precise tools and be very careful. You’ve gotta be patient, because it’s a perfectionist kind of thing. I think most women probably feel that way. If you mess up and have a smudge or a line in the wrong place, it destroys what you’re trying to accomplish.

What’s your favorite item in your wardrobe?

I still just like high heels the best.

What’s your advice for walking in them?

They’ve gotta be comfortable. You can’t deal with any pain, because it’s only going to get worse! They’ve gotta be stable; they have to feel like they can be stable and not fall over. Not that I haven’t fallen over a million times. You gotta be able to be natural and have confidence while you’re walking in heels. If you don’t, it’s like a smudge on your makeup. It takes away from what you want to present.

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