I looked out the train's window at the falling snow. It was so beautiful, blurring the lights, cars, houses, and bundled up passers-by of Long Island's South Shore. I was still half an hour from Penn Station. All I could think about was the hotness of mine and Jimmy's chemistry, not only during those first two weeks together when we seemed to reinvent the art of fucking, but in the other handful of times we started up again over the past year and a half. Each time, we were like great lovers from an epic love story being reunited, like Romeo and Romeo, except Romeo and Romeo get to live. In our case, I guess it would be more like Romeo and Juliet's father, Capulet. Now that's a love story that would have shaken the rails of Elizabethan England. It was shaking my fucking rails here as a Bi man in the United States of America in 2024. I looked out the window again. Oh, wow, I thought. There's a car stuck in the snow. I knew exactly how that poor bastard felt -- spinning his wheels, unable to move forwards or back, despite all attempts.
Each time Jimmy and I reconnected over the past year was like everything came to life all over again. Each time had the hope of something that could really happen, despite me being Juliet's dad and him being Romeo. Some academic really needs to do a proper pysch study about this whole dad/son phenomenon. I’m not only amazed at how many 28-32 yo’s carry the dad/son taboo with them in their hearts and dicks, but how they pursue that taboo with such a secret vengeance. And since I'm going all Shakespearean on this train ride, therein lies the rub. And I don't mean the rub of a good cock. The hook up apps are chock full of similar secrets.
I gently rested my hand on my crotch, breathing, thinking of the Red Jockmail Simplified Jockstrap underneath. God, I'm glad I selected this one. The cotton pouch feels so comforting, keeping my anxiety in check.
Then I almost had a change of heart. Maybe instead of meeting Jimmy on the street for this little gift exchange, maybe we should just go up to his apartment and fuck. The thought of him going jock-boy-berserk over this jockstrap was intoxicating. I looked at the gift bag beside me. No, no. I needed to stay the course. This had to be done. Today. There was no other choice.
When Jimmy reached out to me the very first time on Grindr, he lied about his name. He said it was Brad. Brad's a hot name. I'd fuck a Brad, wouldn't you? The name sounds like he'd be a rich, trust fund brat and drive a BMW, but I'd fuck him. Maybe that's why I would fuck him. You'll have to ask Jimmy why he gave himself that name though. Maybe it's his fantasy of who he is, his alter ego, the keeper of his insatiable and secret love of dad dick. Maybe it's his actual identity. Or maybe Brad and Jimmy are the binaries of his identity and he's dad-fluid, floating, always, somewhere between the poles of Brad and Jimmy. I don't know any more. But what you, Dear Reader, need to know is that, after twenty minutes of him first messaging me on Grindr, he gave me a full-on, unsolicited, video sex call. I didn’t even know you could do a full-on, unsolicited, video sex call on the app, but there he was: this ripped jock boy, a 29-yo son, having searched the word “Dad” throughout the Tri-state area until he finally found me.
There he was, on my phone screen, lying in his bed in Hells Kitchen, pounding his big son dick, while I was sitting bolt upright on my bed on Long Island, staring at my phone, suspended in Time by his beating hand, which seemed to be hitting my fucking heart with each downstroke. Add to that his deep, All American voice, whining out shit like, “Dad!” and “Oh, fuck, Dad! I need your big dick so BAD! PLEASE show it to me!” and my whole world view changed in a single play.
Those were his words, while starting straight at the camera. And you know how I feel about words.
So I did what most of you would probably do. I ended the call. I just didn’t know what the fuck to do with that. It was overwhelmingly hot. I was actually scared of what might happen to me if I watched that performance any longer. It was like I could fall into my phone and be gone forever. Little did I know how much I should have trusted that instinct.
Jimmy wasn’t just any “son." He was that shade of good looking dad-chaser whose smile hits you deep in your soul, because it's a look that is perfect for you. He reminds you of something you can't quite put your finger on. Even Jimmy said, while recovering from our fuck, the second time I had visited his apartment, "Wow. Feels like home."
And that was exactly how he was making me feel.
There was a bit of the frat boy still about Jimmy, and he has this thick head of wavy, James Dean hair, always perfectly pomaded, piled high, adding what seems to be three inches of height to an already impressive, athletic frame. Not only had Jimmy played D1 lacrosse, but he had been the homecoming king of his Nebraska high school – a talented, charismatic, popular, Alpha Sports Jock in every way. His performance on Grindr made me feel undone--nervous and vulnerable. But it was so hot that I made a “note” on his profile, which, like the video chats, I didn’t even previously fucking know you could make a note on the profile.
Here’s what I wrote:
FUCK!! BRAD. VIDEO GUY. INSANELY HOT!
Brad-slash-Jimmy's profile read more like a journal confession than a sex hook up landing page. He was looking to service dad dick, but he was also honestly looking for love --- to date, specifically, to find love with an older guy. A dad. Somebody 50+. There was a whole paragraph about how he was moving on from a previous relationship with a dad, somebody he had been with since college. Coach Rick was suspicious of all of that, though. It wasn’t his first time at the Grindr rodeo. Still, the words on the profile said his desires, above all, landed with men, like me, who were 50+.
A few weeks later, I was bemoaning to my straight buddy, Jack, the woes of having been on two really rotten dates, the week before . . .
THE AUTHOR/NARRATOR grabs the mic for a moment: For those of you just tuning in, Coach Rick is Bi. Although he's exploring his options at the moment, he's looking for a romantic relationship with the right man, thinking it would be exactly the salve which his restless heart needs. At the time of this chat with his buddy, Jack, Coach had recently been on two dates: one with a man; one with a woman.
And they both were fucking abysmal. Okay, handing the mic back to Coach Rick now . . .
COACH RICK: WTF was that? So the guy was my age. In his own brand of nervousness, he launched into a fifteen-minute monologue that didn't finish until we ordered. His intent, I'm sure, was to have a meeting of the minds, talking about our common love of dogs. For fifteen fifteen fucking minutes, though, this guy proceeded to tell me how every dog he ever owned had died, and how they had suffered before that final sleep. After hearing about the third one's loss of bladder control, I myself wanted to be euthanized.
The woman I went to dinner with was sizzling hot, elegant, Italian, incredibly feminine, in her thirties, stunningly beautiful. But man, oh, man. Before she even looked at the menu she clipped her words and cocked her head repeatedly telling me she expected “the man” to pay for at least the first ten dates.
My soul was already broken in the first ten minutes.
Jack wasn't helping. He got all sad and wistful, saying he’d really like to see me settle down and stop having sex with all these 28 yo's. Funny how, when our buddies get married, they also want us to settle down, too. So I asked which one he thought would be better for me. The dog-euthanizer or the extortion princess? That’s when he said something fucking brilliant. “Dude, you gotta stop looking for the ones you think you want," he said, with all the authority of a team captain, giving a pre-game speech. "Look instead for the ones who are out there looking for you. I know they're there. I mean, look at you! Who wouldn't want you? Look for them! Look for the dudes who are looking for you!"
Words, man! Seven sentences from my totally straight buddy, and I was galloping back home to message Brad, who actually turned out to be Jimmy. I asked if he was serious about wanting to date. He responded with a corn-fed-enthusiastic Hells yeah! We exchanged phone numbers and transferred our chat from the Grindrverse to the textsphere. Both of us were insanely busy at the moment, but, we planned to meet for dinner near his apartment in Manhattan the following week.
In that week leading up to it, Brad-slash-Jimmy became my own private porn star. We were talking and texting constantly. He sent over two dozen hot pics -- videos of himself jerking off, videos of his ass clenching and releasing while humping a sofa, dick pics, (and he has a really nice jock dick), pics of his lacrosse cheeks in a jockstrap. He was meaning to turn Dad on before we had even met, and it was fucking working.
So when Jimmy requested similar pics and videos of me, who was I not to give that to him? I'd video myself for him, wailing on my big cock while watching a game, or in the shower, in the kitchen, or wherever I found myself getting hard for him. And he loved it. Not only had he become my private porn star.
I became his. And, God, that felt good.
It wasn’t surprising then, that, for our first date, we rushed through dinner and went right to me feeding him the main course of Coach Rick’s Big D, with my big bare ass cheeks sitting on his sofa, wearing The Original.
And thus started the best two weeks of my life.
My lacrosse son would be waiting for me in his apartment in a jockstrap and lacrosse pads. Or in my underwear. He loves wearing it. He concocted and executed so many awesome surprises for his coach/dad.
I was at his apartment seven times during those two weeks and slept over twice, holding him, with my lips against his forehead, praying with gratitude to a god I hadn't believed in for decades. I keep going back to it, but Jimmy's the one who said, the first night I stayed over, right before drifting off to sleep, "Feels like home."
That young fucker was so right. It felt like home.
Until it didn't.
That last time we had sex in that two weeks, we both almost said “I love you” simultaneously.
Almost said it.
Then that was it. It was over. He ended things between us that night, without saying we were ending. Our hearts had been there, so present, one moment, and, the next, his was like a balloon, having slipped a child's grasp. In seconds, it was already far into the sky, disappearing against the clouds, as I stood beside him, wondering what the fuck just happened.
Then Jimmy did what Gen Z commonly does.
He ghosted me.
But then I did what Gen X and Boomers often do.
We don’t put up with that shit.
So I waited outside his apartment, just wanting to talk to him and figure out why. And that’s when I learned his truth. Jimmy was out to absolutely no one, no family member, no friend, no co-worker. It amazes me that, even in 2024, you can still stand on a street in Manhattan with a guy who is deep in the closet and can’t reconcile his sexuality with the post-frat-boy life he is living.
He thought he had been ready for more, but he wasn't. We agreed to stay connected on social media, but honestly, it was really rough seeing his life on there. There were all these perfect Instagram stories and posts from his non-secret life in motion, where absolutely nobody in his world had a fucking clue about his big secret, shameful desires for older men.
I walked away that day, understanding why Jimmy needed to shut down and move on. Here's the problem though. His closetedness haunted me. I've been in love, like, five times in my life, and it's taken me decades to reconcile being Bi. There were other men, though, that I met and almost fell for on the journey who were similar to Jimmy. They could not reconcile their desires with their regular lives they were born into. What haunted me was what happened to each one of them.
Only one lived beyond 45.
Some married and had traditional families. Some were lost to medical issues; some to addiction. One to suicide. What haunted me was that, based on my past experiences, I could predict Jimmy's future. And it was bleak as fuck.
Over the next six months, I found myself thinking about him. A lot. I'd be lying in bed, scrolling through pictures and videos of him, and inevitably take my dick in hand and crank out a tribute load for this lacrosse boy.
It wasn't a complete surprise to me, then, that he was doing the same for me. He'd text me something like, "Hey, Coach. I know I probably shouldn't be reaching out to you, but I'm jerking off to one of your pictures right now, and thought you should know."
I can't tell you how many times I found myself looking to the phone to see if he had texted. And I started wishing, all the time, that he would.
The problem with wishes, though, is that they frequently become reality . . .
The train pulled into Jamaica. Next stop, Penn Station. I looked at the bag , now in my lap. Yup. This. Today. This was my reality. I started feeling anxious, so I slipped my thumb in side my jeans so I could feel the jockstrap I had chosen for today, the Red Simplied Jockmail Jockstrap.
I should text Jimmy and let him know the train is running late, due to the snow.
This was happening though. In thirty minutes, I would be standing right in front of him.
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