A Russian Sugar Daddy, The Chechen Mafia, and Roppongi Hills.

That time I had an extremely awkward date with a Russian Sugar Daddy.

Ear planted firm into the cold desk, I huddled my arms around my head. This embrace shielded me from the scornful eyes of my professor. Even though the darkness of the dimmed classroom, his look of utter disappointment was quite apparent. 

“Hey there Priscilla! 

Long time no speak. We certainly hope you’ve been well. There’s a Russian gentleman who wants to see you this weekend for dinner. He’s pretty cultured and seems like a great guy. Are you free?’

I felt a tingle between my thighs. Not that kind of tingle, a notification from my phone. I rose my dreary eyes high enough to look inside my purse on my lap in front of me. 

My fingers punched an auto-response in iMessage to the text. “All good! Got it.” I responded without a second thought to the previous message. These opportunities don’t come by often, and I certainly could not let one pass me up. My lips met my eyes with approval, I giggled with slight excitement. 

“Miss Du Jean, I can’t imagine what’s inside of your purse that’s so hilarious and would make you wake up. But that wouldn’t be the strangest thing you did.”

I felt shame, which was the intention of the professor’s comment. He expected shame to inspire me to have a decent work ethic. Shame should at least be enough for me to show basic respect and not sleep in a university course, right? Not—because I’m not Japanese, shame just didn’t work that well on me.

I loved my Comparative Asian Film class. Tanpopo, Old Boy and Chungking express—All amazing East Asian films. Cool. I had more important things to consider, like how the hell I was gonna have a date with a Russian Sugar Daddy. 

I read over the message that the matchmaking agency sent me. They’re notorious for fluffing up the qualities of potential suitors, especially if they’re of the un-fairer sex. I wasn’t particularly excited about meeting a Russian man. Not because I’m a red-blooded American either. It’s because I had no idea what the fuck to say. I had only turned twenty-two weeks prior and my experiences with White men were nil. 

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Next, he wanted to meet in Roppongi Hills. There are few places in Tokyo shittier than Roppongi Hills. Roppongi doesn’t reek of piss as badly as Ueno does and it isn’t proudly as sleazy as Uguisudani. It’s a haven for Western men who get off on objectifying Asian women and Asian men who like to buy the privilege of objectifying White women. A cesspool that even I am far too bougie for. Since the 1990s the district had been heavily gentrified which is when the “Hills” was attached to the name. The coke, sexpats, and crooked cops are as present as ever.

That Saturday evening arrived at the Roppongi Hills station roughly fifteen minutes early. My hair was a dark auburn red—I worried that my date wouldn’t recognize me from the pictures which were a year old at that time. I had just broken up with my Japanese techie boyfriend therefore I sported a new haircut. New hair new me. 

A svelte Japanese man with hair a bit too long for his age approached me. This meant one of two things. He was either a pimp or “scout” and a nicely dressed one at that. Or perhaps he was a Western returnee on his third Brown Southeast Asian wife. 

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“Wow! You look like Tyra Banks and Naomi Campbell.” Wow, really laying it on thick LOL.

“Really? They look nothing alike. Thanks though.” He handed me a card with his phone number and the name of a hostess club he presumably owned. “You seem busy, but please let’s talk some time.” It’s really flattering when you’re from the sticks to be approached by a pimp (ahem) scout at first. You really feel special. Then it just becomes life in Tokyo.

Sweat started to glaze the small of my neck as I waited in anticipation for my date, Demetri. I couldn’t get the painful image of Vladimir Putin mounting my little frame out of my mind. Or worse, what if he looked like the old guy with the scar on his head that wouldn’t tear the Berlin Wall down? 

He was about ten minutes late so I decided to give the number a ring. So my spiel about this date situation—The matchmaking agency takes photos of beautiful about-the-town young women and matches them with guys looking for a date out.

The men pay an annual fee to join the agency. The more you pay, the hotter girls you can date. My friend was a working model and had huge tits so they put her in the highest category, next to a famous Japanese Adult Video actress. You had to pay an annual fee of $10,000 per year to the matchmakers in order to gain access to that level of a woman(and the tiers below it). I was a gangly teenager with a face full of acne scars. It seemed to work in my favour. Besides their annual fee, what you do on your date is your business. I met a hedge fund manager, a Google executive, a world-renowned astrophysicist, an asshole Australian dot-com centamillionaire and an Earthquake specialist through who I semi-regularly dated. Regularly being once every other month. 

My ears began to heat as I held the phone to my ear. Then I felt a tap on my shoulder. Behind me was a man far younger than I had imagined. 

“Hi there! Sorry I’m late.” He gave me a gentle smile and wrapped his hulking body around mine. 

We ate at a Bavarian restaurant nearby—it was Michelin starred. Although I didn’t have a clue of what that meant at the time.

Demetri held my hand even as we sat across from one another in the isolated restaurant. “Priscilla” (my fake name) “I’m so happy to meet you. I’ve been to Tokyo a few times, it’s always been so lonely to come for business.”

I held the large jug of beer to my lips, slowly and painfully sipping the ale. I hate beer but I love money more. My hand slender fingers were caressed and I began to lose it.

”If you don’t mind me asking, what field are you in?” Asking questions is a pro-move. Most men love to talk about themselves. If I keep my mouth shut they can’t figure out that I know nothing about Tchaikovsky or the state of the European Union or some bullshit. 

Demetri squeezed my little hand even more and filled my body with electricity. “I work in banking. Just a bunch of old guys in salmon shirts. It’s much better not to think about it when I have an angel in front of me.” His gentle voice danced in my ears. It was rare I felt like I had an actual date. 

“So, I know nothing about Russia…teach me” I flashed an impish grin

“Well…my father is half Swiss and half German. Mom was Russian and I was raised in Switzerland.”

“Have you traveled a lot?” This was my script and I knew it well. 

The bitter beer gushed down my throat and I listened to Demetri rattle on about his travels. Every aside and anecdote I absorbed to my cultural capital reservoir. 

“Shisha. That’s the best part of my travels to Morocco. You sit down with a book, have a cup of tea, and talk with friends. It’s great.”

So we set off into the Roppongi night on a quest for Shisha. YIKES. We crossed the barrier from where the Hills no longer described the neighborhood. Yet with Demetri in my hand, nothing at all felt scary. It was a strange feeling. At 5’7 I was lucky to be with a guy the same height as me. I felt secure in knowing that, despite my petite stature, I had a chance in a fight. I had no chance with Demetri yet his soft demeanor made me at ease.

“Hello, good sir!” He approached one of the many Nigerian bar touts on the street. The smell of street kabob and drunken Salaryman puke was embedded in the streets. I cringed with embarrassment at Demetri’s friendliness. It was endearing that he trusted any street tout at all. What a dork.

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Hand in hand with this half German half Russian himbo, I walked towards an elevator. No light shone inside of it and curiously, there was an elevator operator. It didn’t strike me as odd that they had an elevator operator in 2016 because this man was a specimen himself. The lights flickered and the dingy elevator doors crept shut. “Prive!” Demetri yelled in an excited tone. The man, covered in sleeve tattoos, started to respond back. The men yammered on and had a small embrace once we reached the floor with the Shisha. Loud shitty dubstep blasted through the speakers and an Iranian man greeted us. Demetri whispered a demand into my ear. “Never come back here. That guy said he was Chechen. There is no fucking Chechnya. Be careful, this place may be dangerous. Fucking mafia.”

Ah yes, White on White racism. There’s probably geopolitical tension that I’m ignorant of. But I’m not like Al Gore or something, I just nodded and promised I wouldn’t come back to the place with the Chechen man. We sat in a Shisha bar which was definitely a front for one or two vices. I took a puff of Cinnamon flavored Shisha and Demetri laid his head in between the meeting of my thighs.

“I just want to read.” And so I browsed Twitter and he read on his Kindle with his head nestled against me. 

We left. Because this vice-den Hookah place wasn’t what Demetri had in mind. He wanted an authentic cultural experience in…Roppongi Hills.

He took me to a quiet Egyptian restaurant a few blocks away that sold authentic Shisha. The old Arab man who owned the place made solemn eyes with me and gave a glance of submission to Demetri. 

“My ex was Thai, she came from this region that’s kept poor intentionally by the government. It’s so fucked up.”

I sat and listened to him in what felt like vulnerability.

“When we would go to Thailand together I’d see all these old White guys, from Europe…” Demetri stared at his shoes and I took another puff of Shisha.

“They would be with… younger Thai girls and I just thought how fucked…” It was strange to see a little sniffle come from this big buff guy. 

“It just feels weird ya know.”

And he was right. It is kind of weird for a handsome, wealthy, single man in his early thirties to have to pay a 20-year-old for a date. I wasn’t complaining though.

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We walked back to his hotel. His guilt seemed to subside. He said he liked kink and I couldn’t have been more excited. It’s not often a hot, young-ish, buff, tall, half German half Russian wealthy super-soldier with a sensitive side wants to fuck you after putting a Michelin starred dinner in your belly. 

So the kink began. Without any real toys, we had to make do with what we had. He used the thick belt from the hotel bathrobe to try and tie me up. Fun. 

Then I heard a faint sniffle. The sniffle turned into wails and the wailing became a silent sob. My powder blue cocktail dress became drenched. I was soaking wet…with his tears. He cried for the next few hours with his head, again, in between my thighs. I got a cab home at 3 am. I kept his promise, however. I didn’t find any reason to venture to Roppongi Hills or interact with any members of the Chechen Mafia.