One Man’s Perspective: My Tokyo Sugar Mama

Five years ago, I met an older client at work in Tokyo. I was in my twenties, and she was in her fifties. She was very attractive for her age and well educated. Despite our age difference, we got along very well together and had an instant connection. She was very well known in her career and anyone who was familiar with Japanese politics in the slightest had heard of her. As an American in Tokyo, I didn’t have any clue who she was when I first met her. Later, my boss told me that I was to treat her like a VIP at all times.

After wrapping up a work project one night, we decided to get a bite to eat together at a nearby restaurant. She tells me she needs my help with preparing for an interview at a prestigious company that is basically hiring her for a very unique role created for someone with her expertise. I tell her I’d be happy to help, and I was. I genuinely liked her and didn’t have any ulterior motives. I just wanted her to succeed. So, we met up once again later that week to do the interview prep, and one more time after that.

One evening after doing interview prepping, she challenged me to a game of darts at a local bar. I was intrigued at the idea of playing darts with her in an effort to spend more time together outside of work. Even though I had never played darts before, she talked me into having tequila shots for every game lost. We both ended up drinking our fair share of tequila that night, and ended up missing the last train back.

Eventually we ended up at a nearby internet cafe, where we wound up spending the rest of the evening. In a drunken haze, things progressed pretty quickly between the two of us. We decided to ditch the cafe in favor of getting a room together at a hotel, and so began our relationship.

She turned out to be filthy rich and would buy all kinds of things for me, from expensive watches, to designer suits. She had the best cars just lying around in various parking garages throughout Tokyo, including an Aston Martin, and a Benz among others. Even though I was making very good money for my age, she refused to let me pay for any of our dates. She wined and dined me at least three times a week, and when we weren’t working, we were traveling the entire continent of Asia together (all paid by her).

A few weeks after dating, I became aware of her complicated marital status. I wasn’t in the least bit surprised, but it did make things a bit awkward for me. It turned out that she was in a loveless marriage with a man that she also had a child with. She and her husband remained married, despite neither of them wanting to continue their marriage. Due to their elite status in Japanese media, a divorce was out of the question, and both of them ended up seeing other people.

We ended up breaking up when we realized having a kid together would cause irreversible damage to her political career. Besides, divocring her high-profile Japanese husband to marry a white guy would be the end of her professionally. If only I had met her 3 years earlier, my life would have been completely different than it is now. As much as it hurt to face the reality of our relationship, she was the best I’ve ever had. I could care less about the money, or the gifts, and extravagant vacations. I’ve never met someone I connected with so well. She was the one that got away.


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One Man’s Perspective: My Tokyo Sugar Mama