Spring 2026

Waking up after a night of molly and various pharmaceuticals is brutal. That’s the drug, not the girl, although I’ve had this running fantasy for years to take molly with a girl named Molly. But I digress. Where was I? Oh yeah. No matter how great a night of high-grade MDMA is, the next day is a complete write-off unless you’re preparing for another night of molly, with the latter being the exception. This is before the fentanyl-pushing dope dealers ruined the experience for the next generation. 

The morning symptoms for me include chills, chattering teeth, sweating, and a bit of melancholy. There is one benefit to the aftereffects: the feeling of cuddling up with someone sharing the experience is like a safe landing rather than a hard serotonin crash. 

On this particular morning, I was warming up to a brilliant little 22-year-old architecture grad, Robin, who was still passed out. I refused to open my eyes, knowing I would have to commit to waking up, and I held out hope for another hour of sleep, as I’d never been so comfortable. As the highlight clips of the night rolled in my mind, I realized my head was, in fact, not resting on a pillow but buried in her two glorious ass cheeks. 

Delicately soft yet impossibly firm, they were perfect, and they looked great the night before in leather pants at Reverie Nightclub. How I passed out on her ass wasn’t a mystery as much as how we passed out while I was licking her ass. 

The scenes started to replay in my head. We got back from the club around 3:45 a.m. and this hotel was famous for its gorgeous corner tubs by the windows so you could see the entire city while soaking. We sat opposite each other in the tub, with me massaging and kissing her adorable little toes, and her struggling to fight off sleep. The poor girl had a full night and was starting to pass out. The music softly played in the background, the lighting was dark but warm, and we were coming to the end of an epic night. It felt cinematic. 

Unfortunately, we had to get to bed. The next day was going to be work for me, and she wasn’t used to this lifestyle, so I dried her off, laid her on the bed face down, and dove into her anus. As I was enjoying her crack like it was crack, she passed out from the excesses of a frivolous night. At one point, I realized she was tapping out, so I just stopped licking and fell asleep between her two legendary ass cheeks. A month earlier, Robin had been my favorite student.

Didn’t see that coming? Neither did I. Just three years prior, my divorce had been finalized, resulting in getting what I referred to as “the plague.” This is when all your married buddies stop calling you because they don’t want the single guy at their social events anymore. The bigger reason is the wives don’t like them being too close to you. The divorce also closed a 15-year chapter that had taken a massive emotional toll on me. 

Single, my outlook came down to two words: uncommitted fun. Which demographic is more likely to share my worldview? I quickly found out it was young, beautiful, smart college women, and they most certainly didn’t care about age gaps. I admired this progressive quality for obvious reasons. This started me on a path of age gap relationships that would go on for almost two decades. 

How did I get from dinner at Maggiano’s on couples’ night every Saturday to using Robin’s exquisite ass as my pillow after a night of raving in a dance club? 

This is the story of how nine women in their 20s changed my life, gave me insight into the world without knowing it, and made me the man I am today, for better or worse. 

The journey was fun, surprising, disappointing, exhilarating, heartbreaking, meaningful, but never dull. 

To be clear, I was never a sugar daddy to these women, but I was often their daddy. The distinction is important, as it dictates the dynamics of a relationship. The relationships between a sugar daddy and a sugar baby are transactional. The man gets companionship and intimacy, and the woman gets financial support and access to opportunities. There are usually clear boundaries, and the relationship is defined by its reciprocation. 

I simply saw myself as an older boyfriend, which naturally comes with a paternalistic element, but my relationships were not transactional even if the woman wanted it to be. All nine of these women were looking for something different. Some wanted a few fun nights, while others were only interested in committed long-term relationships, and I obliged both. They were all unique, and each left a memorable impression, and, in a couple of cases, a scar.

I know you’re thinking, “Great, another douchebag bragging about his conquests.” While I can’t disprove douchebag status, ponder this: Robin and I dated exclusively for two years, and it was one of the most meaningful relationships of my life. We loved and respected each other, and I often imagine how my life would have been different if we had gotten married. I thought she was amazing, and we were amazing together.

So why the obsession with youth besides the obvious being tight skin and no need for Botox or filler? Sixteen years of post-divorce bachelorhood is a long time, so it’s not surprising I met a lot of women, and not all of them were young, but there were two dealbreakers that tilted the balance of women I was meeting to the younger side. 

First, I refused to date anyone with children, which cut out a huge swath of women in their 40s and 30s and even some in their late 20s. I saw what divorce did during my decade of coaching. It ruined children for life, and I didn’t want to be an accessory after the fact. I saw the dynamics between mom and dad as to who was going to the tournament that week, and all the snide comments that went along with it. I never pursued a mom. 

The second thing was that most women over 30 had never heard of EDM or any of the music I’m passionate about, but guess who has? College girls. They’re also more likely to be as passionate about art and cinema because they still have the excitement of newness. Undiscovered music, movies, venues, museums, galleries, all of which are second nature to me, are a wonder to them. They haven’t had their lust for life drained from them by mortgages, medical bills, taxes, a bullshit healthcare system just at the time they need it, and probably a cheating partner. I’m catching them before they fall off the cliff. 

Grab a drink and relax with some music while reading each chapter. I have a link to each one on Spotify, reminiscent of the time we spent together. Music is a constant in my home, and every phase of my life can be marked by what I was into at the time. Starting with my first night with Laura, the needle dropped on old dinosaur rock and alternative bands, and while I made her playlist for the website, a flood of memories came back like when I fell asleep in the middle of licking her ass. 

As you read this memoir, it will be apparent I use fake names, am fuzzy on dates, and use ambiguous towns and cities. This is to provide plausible deniability for people I love and respect. It’s also to prevent my ass from getting kicked by angry husbands or fathers, especially those that don’t appreciate the raw descriptions of sexual acts with their innocent baby.

So, with that in mind, the journey starts around 2008. I’m single and living in a college town in North America, a few hours from a large urban center that had one of the most vibrant nightclub scenes on the continent. Without any more legal nonsense to deal with over my marital breakdown, I felt a large weight off my shoulders, and I was ready to meet my next ex-wife at the bars in my hometown, the dance clubs in the big city, the country club while playing golf, and, of course, the campus. So, let’s start then with an athletic, dynamo named Laura.