Detour into Depravity - Chapter 1
Chapter 1
It was an evening I’d anticipated and dreaded, in equal measures. I had recently retired and the Dallas advertising community was honoring me with “Ad Man of the Decade”, a prestigious recognition. I had been looking forward to it because I was proud of my role in turning around Miller Shanks, once a proud and iconic ad agency in Dallas. They had recruited me nearly a decade ago when they were near bankruptcy from an ad agency in Minneapolis. The challenge they presented was too great to resist: restore Miller Shanks to its former glory and the private equity owners assured me a level of wealth I’d never imagined. I’d been financially comfortable before, but this was one opportunity I couldn’t pass up.
I dreaded tonight because I’m not comfortable being the center of attention. I’m a great people leader, but my leadership style is one of being a servant leader, not a “look-at-me” leader. Throughout my career, I relished the opportunity to develop young people and help them find their voice. In fact, that gave me more satisfaction than driving business results. But to have an entire evening to honor me was way outside my comfort zone.
I went solo that night because one of the major sacrifices I’d made since moving to Dallas was that I remained single (and practically celibate). The pressures of leading a turnaround required 70+ hour weeks and I simply didn’t have time for anything, or anyone, else. Fact was, I didn’t miss it that much, but I wondered about being alone in the future.
The timing of the move to Dallas was serendipitous as my relationship with young Pook was winding down in Minneapolis. Pook and I had met at CrossFit where we were fierce competitors. Pook was a stunningly handsome, late-20-something young man when we met. He had been a college athlete and was now committed to CrossFit. His body was nearly hairless and sculpted, not unlike Michelangelo’s David. After a summer of working out together and intense flirting, I finally got the courage to invite him to my place one Friday night for “a beer”. “A beer” turned into an intense edging session in our jockstraps, followed by an epic, and I mean epic fuck, where Pook screamed “Daddy” with an alarming intensity when I came inside him. When we woke up in each other’s arms the next morning, we knew the “Daddy” he cried out wasn’t accidental or arbitrary. He had claimed me as his “Daddy”, and I happily claimed him as my boy. The seven years of our relationship was characterized by amazing Daddy/Boy sex and Father/Son mentoring. We expanded each other’s sexual boundaries well beyond where they had been when we met. I was nearly always the dom/daddy and he happily accepted his role as boy/sub. Occasionally we’d switch it up when I’d give him carte blanche to dominate, use, and abuse me in any way he liked. It never got out of hand, and I secretly enjoyed those sessions more than I let on.
Coincidentally, when I was exploring the Dallas opportunity, he was approached by a private university on the west coast for the position of Assistant Dean. Neither of us could pass up our respective opportunities, so we parted best of friends. I helped him become a capable, mature professional, and he showed me kink beyond my wildest dreams. It was truly win/win.
But now it’s years later and I’m starting the next chapter of my life, wondering where it will take me, both professionally and personally. The professional part is easy. I’m sought after to sit on boards, consult, and I will continue to mentor young people. That’s the easy part. But I’ve ignored my personal life for so long, I’m not sure where I see that going.
Good thing I have another passion beyond my career…CrossFit. I’ve been doing it regularly for over 15 years and am in the top 10% of men my age in the world. And my body shows it. CrossFit is where I met Pook over 15 years ago, and the first thing he said to me, in front of the entire class was, “Look at the pipes on Pete!”, referring to my (admittedly) well developed arms. Whenever Pook would introduce me to his friends he’d always say, “…and this is my partner Pete, Body by CrossFit”. I’d pretend to blush, but I’m vain enough to admit I loved it. We were quite a pair. And I’m happy to say I look as good now as I did (better actually) 15 years ago. I’ve made CrossFit a priority, and now with my newfound freedom, I’ll have even more time to dedicate to it (and my body).
The awards section of the evening was over and I was mingling with several individuals and groups who wanted to personally congratulate me. It was well into the evening and I was more than ready to call it a night, but I noticed a particularly handsome gentleman, probably about my age, along with an jaw-droppingly handsome young man, patiently hanging back to introduce themselves. When the last person I was speaking to cleared out, I looked up to get their attention. The older gentleman was especially striking and reminded me of the IG influencer Clayton Paterson. Tall, grey, distinguished, with broad shoulders like an ex-football player. I turned to look at his young friend, maybe around 30…damn, was he hot as well. About 6’, curly brown hair, with a shirt that clung to his well-developed muscles and the roundest, most beautifully sculpted ass since Pook’s. I had recently come across the young comedian Matt Rife on social media whose calling card is that he’s sexy as hell. The young guy in front of me instantly reminded me of him.
The older gentleman approached me and introduced himself as Charles Henderson of the law firm Henderson and Wicksom, a prestigious local firm. He paid me the perfunctory congratulations on my career and then made small talk about being surprised we hadn’t met before this. Dallas business leaders, high profile, blah, blah, blah…He seemed to be hinting about why our paths might’ve crossed when it hit me that he was clearly gay himself and was with his partner. Upon figuring that out, I probably cracked a smile and hopefully warmed up a bit. He quickly introduced his friend, the Matt Rife look-alike, whose name was Jack. Jack greeted me warmly and began to discuss the advertising community with impressive first-hand knowledge. After a bit, he paused and shared they had attended the event because he wanted to meet me and had a favor to ask. He indicated that he was committed to a marketing career and but didn’t have the contacts or know-how to navigate the notoriously closed industry. Knowing of my success in the industry, particularly in Dallas, was there any advice I could give him or connections to jumpstart his career.
Helping young people who are trying to help themselves was right up my alley. I told him I’d be more than happy to help, hear him out, and get him pointed in the right direction. Charles was genuinely appreciative, and we agreed that now wasn’t the best time to go into detail, but a future lunch would make sense. We all opened our phone calendars and agreed on a date, time, and place.
In those few short minutes, what had started as a stark, almost awkward exchanged quickly warmed into a budding friendship between Charles, Jack and me. I felt gratified that they felt comfortable and confident enough to approach me on Jack’s behalf. And while Charles and Jack appeared to be a committed couple, they were so damn handsome and warm, I have to admit I didn’t shy away from having lunch with them.
I wound down the evening with mixed emotions. This was truly my last hurrah. I was no longer a high profile advertising behemoth. I was just another retired executive (albeit with huge shoulders, pecs, biceps…and bank account). But I was staring at my next chapter and it was largely a blank slate.
I arrived back at my loft and poured myself a scotch to unwind when my phone pinged. Message from Charles:
“Thank you again for taking the time to help Jack. We both appreciate your efforts and look forward to seeing you at The Club on Monday. We will find a way to make it worth your while. Thanks again, Charles.”
“We will find a way to make it worth your while”…. was this a double entendre, or was my imagination working overtime? Was it a subtle come-on, or was it simply wishful thinking? One thing I wasn’t imagining: my cock twitched when I read it.
Monday was just a few days away. I may have been overthinking this, but I had a strange feeling that lunch with Charles and Jack could be the first chapter of my next life.
In the intervening days before lunch, my mind kept wandering back to my days with Pook. Damn he was hot and I was so proud of him. I’ll never forget seeing him walk into CrossFit on my first day there. Late 20s, tall, taught, totally bald and….insanely hot. And he was all over me. I was 25 years older than he at the time, but he unapologetically claimed me. Everyone (except me apparently) knew he was hot for me, but it took me the entire summer to figure it out. Once I did, we entered into an intensely sexual, committed relationship. I was unquestionably the alpha daddy, but there were occasions when I allowed Pook to take control. And did he ever. He’d dominate me with a vengeance that still haunts me. To this day, I don’t know if I loved it or hated it, but I can’t stop thinking about it.
Monday finally rolled around and I showed up in my sexy-but-not-trying-too-hard business casual attire. Tight(ish) slacks, shirt opened one extra button and expensive, but not flashy fitted sport coat. I immediately spotted Charles and Jack. I approached the table and Charles popped up to give me a bear hug. Simultaneously, Jack stood up as well and gave me a warm, 2-handed handshake.
We settled into a comfortable discussion where Jack shared his background, career goals, and how he got as far as he did. I had checked him out on LinkedIn so already had a sense of his career to date, but I listened quietly. It became clear that he just needed some direction and a little polishing. He had the intellect, drive and more than enough charisma to succeed, but navigating the demanding world of advertising was still new to him.
Jack had moved to Dallas immediately after graduating from the University of Oklahoma, where he had grown up, to pursue a career in advertising. He grabbed the first offer he had received but now realized it was a small agency with few opportunities for growth. He was stuck and needed help figuring out what was next. Charles was open about the fact that his legal career rarely intersected with the Dallas advertising community so was at a loss to help Jack with career guidance or contacts. When Jack read about my recognition event they thought it was the perfect opportunity to make contact. They were right, because four days later the three of us were having lunch.
They sat me between the two of them which made it slightly more difficult to address both of them at the same time, yet gave each of them equal access to me. And as the lunch progressed, I couldn’t tell if I was imagining it, but it seemed they had both inched closer to me. Both of my forearms routinely brushed against each of theirs, and occasionally our hands and shoulders even touched.
Jack and I settled into a productive Q&A that helped me better understand his goals, strengths, and opportunities. I was beginning to develop some thoughts and ideas, but didn’t have enough time there and then to offer solid advice. Lunch was winding down and while we had made progress, we hadn’t landed the plane. Sensing this, Charles suggested we continue the discussion in a less rushed time and place if I’d be willing. I was thoroughly enjoying what comes naturally to me, helping young people like Jack, and who wouldn’t want to spend more time with these two sexy guys?! I enthusiastically agreed and Charles suggested dinner at their place on an upcoming Friday or Saturday night when we wouldn’t be rushed and would have the entire evening to continue the discission.
As Charles proposed this, did I imagine his foot and knee subtly press against mine under the table? Almost simultaneously, did I imagine Jack’s foot and knee pressing against my other leg? It happened quickly, but it was unmistakable. Just the pressure of their legs and feet against mine screamed to me this was more than a business dinner invitation. I subtly pressed my legs apart increasing the pressure against each of theirs, but above the table continued to talk nonchalantly about joining them for dinner. Ironically, I immediately became so hard there’s no way I could’ve stood up from the table at that moment. The three of us made quite a production checking calendars on our iPhones (were they chubbing up as well?) and we quickly agreed the upcoming Friday night worked for all of us. That was only five days away and it couldn’t come fast enough.
Charles grabbed the check and we said our goodbyes. I gave Jack a couple things to be thinking about before we met again Friday night and he warmly thanked me and shook my hand. Charles then pulled me into a warm hug, out of earshot from Jack and whispered, “Thank you, Pete. You’ll get your reward Friday night,” and gave me a wink.
Friday night was five days away.
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