Banging an Unenthusiastic Prostitute on Christmas

Why not?

Dear Mother,

I hope you had a wonderful Christmas.

Me? Mine was fine… I went out and fucked a prostitute.

Her name was Juri. She was unenthusiastic. Nervous is a better way to describe her, really, which was weird because she told me she had been working here for “5 years” which was also weird because based on her stated age of “21” that would make her estimated age of employment at around… 16.

She wasn’t really 21 of course, they never are.

I went with this guy who (barely) reads my blog. He’s 37 and apparently has enough money to do what he wants when he wants where he wants for the rest of his life but I can never seem to ask these people to share. He took me out to dinner in Shinjuku and then we took an Uber across the city up to Yoshiwara, the fabled red light district I read about in a Vice article last week.

Vice should hire me so I can make their shit interesting again

Yoshiwara was a ghost town because it was Christmas Eve and most people were probably with their families (or at KFC, which is what people seem to do here on Christmas, which is a real thing look it up I’m not joking), but not me… I am different and special and so I was here peeking into these little brothels with my new friend Chris looking for some kind of connection on this cold winters’ night.

I found no such connection, besides with Chris maybe, who promised to wait outside and walk around after I paid 24,000 yen to some stereotypically Japanese guy behind a desk-counter and selected “Juri, 21” to be my partner for the 50 minutes allotted to us before the place would close at 12. Yoshiwara was full of these tiny little brothels, and they all seemed to close at 12, we got the sense this was the last one open and so I had to go in.

Juri’s got huge tits in the picture, which is super-airbrushed, as all these pictures always are, but cup size is hard to fake and she’s clearly the youngest of the presented photos and so I choose her, and the other old man in that tiny lobby says Hai! And gives me $6k yen change and whisks me away into a suspiciously casual waiting room across the street.

This room makes me laugh: it has the vibe of some Japanese guy’s man cave apartment. Comfy couches and a huge TV screen. Big mirror on the wall for some reason. A fridge. I got the sense I could fall asleep there, rent it out for $30 a night if I asked. I sat there for about 8 minutes flipping through Japanese romcoms and commercials giggling sadly about the pathetic state of my life. I’m paying for this whole affair using a significant chunk of the money I swindled off that Chinese girl last week. You only live once, am I right.

Juri interrupts my lonely mania. She looks enough like the picture, though a little beaten down, like a slightly overripe fruit, wearing a black and white zebra dress corsetted into a pushup bra. Heels too probably but I wasn’t looking down there. That nervous look on her face will haunt me forever. You know when you squint your eyes a little bit and hard-fake-smile… try doing that now, that’s the expression she gave me whenever our eyes met. It felt like she was trapped in there, in that body and she was begging me silently to dig her out. Baby I’ll try.

Juri leads me upstairs into a different kind of room I’ve never once seen. This wasn’t just a brothel, see, it was a “Soapland.” A Soapland is like a brothel but with bubbles: The girl gives you a bath and then lets you fuck her. I’ve seen this in my Japanese Adult Videos… it looks heavenly on the screen, but in real life it was not so magical. It was just a studio-sized room with a tub, a shower, and a single twin bed.

There was a little squat-bench in front of the shower where Juri, who spoke just about Zero English, much to my dismay, sat me down and tried to adjust the water temperature to something humans could tolerate. It took her an incredible amount of time to do this. She started to get nervous, I wanted to say it’s okay baby it’s okay but she wouldn’t understand… because Engrish. I would remind her “Daijoubou Daijoubou…” every few minutes, which means “It’s Okay” in Japanese, but I don’t think it helped.

I was watching her naked body as she struggled with the water. It is a nice little treat to unabashedly stare at a girl’s body in real life like this. Usually I have to avert my eyes after a few (milli)seconds because we live in a society and that’s what people do in Japan. What am I gonna say: Wow nice honkers baby—whats your name? No. I’m not. I get the sense the normal girls, in that type of situation, would rightly ask: Why not just get a hooker instead? It’s easy in Tokyo. So here I am, with this hooker instead, appreciating her god given gifts: big natural breasts, perfect little dollops of nipple, and she’s curvy too. No one is fat here, my only complaint besides the giant bright ugly red shoulder-tattoos is this little pouch of paunch around her abdomen. It’s especially visible when she folds her body inwards to serve me. Her face is actually quite pleasant, too, until she looks at me and tries to smile. I feel like I should be caring for her instead, she is obviously a nervous, neurotic animal.

Finally she gets the shower to an acceptable temperature and begins to wipe me down. Just focuses on the crotch, which has become slightly hard as a result of watching her. Soapy hands on the dick. Ooh la la… she’s not too thorough with it. You get what you pay for. Now we’re in the tub sitting face to face and she’s still not looking at me. Usually it’s easy for me to make girls laugh and forge some kind of connection at an unnatural pace because we can communicate in English and I can say things that ease the tension, make them feel okay. Can’t do that with Juri so she has no idea who I am. There is no trace of guilt or shame on my face, I’m too drunk for that but she struggles to maintain eye contact regardless. She can’t even tell me that I’m very handsome like most hookers do because that level of English is past her paygrade.

Based on all of the above I knew the sex wouldn’t be memorable. and I was right: it wasn’t. Handjob. Blowjob. Kind of hurts as always because the Jews chopped my foreskin. We’re on this tough single bed pushed into the wall of the room. She does one thing I’ve never had before; she sucks on my balls. This takes a lot of trust… because with my testicles in a womans’ mouth I am sharply aware that she could just chomp down at any given moment and pretty much end my entire life. Takes a lot of trust… and the crazy in this girls’ eyes is a lot to look past. Still I nut up and trust her, she licks them too, laps it right up, feels pretty good, it wasn’t my favorite thing I’ve ever had but at least it was something different.

She mounts me in cowgirl like all these girls do. Our rapport is not strong enough for her to ask how I want it. This must be how most boring lazy old slobbish Japanese salarymen like to be fucked. On their backs looking up at this nervous bouncing tatted up prostie as she stares out into the distance eyes closed wincing basically fucking herself. No wonder the birthrate is in freefall. I wouldn’t go so far as to say it was Horrific but it was close… a real nightmare before Christmas situation. It was just another day in the office for this bitch and that depressed me too much to bring me anywhere close to orgasm. Plus I was wearing a condom, which, fair, I probably should be doing that ‘cause she is a prostitute at the end of the day, but the Japanese condoms are always too small and obviously it’s a condom so it kind of kills sex altogether if you’re not really feeling it in the first place.

I’m barely hard enough to continue. Pulling her fat hips down into me feels nice but not nice enough—I tell her to flip. Pull her off of me on down onto her back. Missionary. It’s about 40% more pleasant. She’s not super-tight because again she’s a prositute but I can simulate tightness by entering through the front door and squeezing her thighs together beneath me. Hold one of her hands in mine and use the other to grope her big fat soft healthy breast. Mmm. Lap it up too. She still looks away and off to the side but at least I’ve got a better view of her body now. Jiggle jiggle… I rest my free arm on her neck and she begins to choke. Oh dear, oops, that’s my kink and this plus the sight of her body finally compels me to cum. Sometimes I’m trying not to cum and sometimes I’m just trying to get to the end of it. Sadly this was an example of just trying to get to the end of it.

She asks if I finish. Yes I finish. I hate that she didn’t know. She washes me down again. Sparsely. Poorly. I’m not too bitter, now just more curious and ready to use Google Translate to ask some follow-up questions. How long have you been working here? Will you sleep after this or are you up all night? Who cares. She asks where I’m from like all the locals do and I say USA! America! Wow! She uses her own shitty Japanese version of Google Translate to ask me: You know Gossip Girl? I love Gossip Girl! You know Orange is New Black? I love Orange is New Black! I pretend to like both of these shows too because I am lonely. I make her laugh using google translate a couple times using more words I cannot recall. There is nothing else for us to say. Our hour is surely up, it’s time to re-robe.

She puts the black dress back on and she looks more beautiful to me than before. I tell her this using google translate and she laughs: Hahahaha No! Ok.

She calls somebody using a phone attached to the wall and leads me downstairs back to the check in desk. As she says OhayoArigatouGomenasaiGozamaiasuWhatever in that familiar customer service tone I can see in her eyes that she’s expecting a tip. But I can’t do it. It’s against my religion to tip anyone, for anything. Even on Christmas. In one quick flash I look away towards my shoes and she looks down understanding she’s getting no tip and I don’t look back—I’ll never see her again.

Bid my adieu to the check in guy. Arigatoou, goodnight, Merry Christmas.

My older reader friend from earlier was waiting outside, a block down the street. He’s not a weird old creep, he’s a banker from Maryland who barely knows of my blog and was recommended to meet me through a friend of a friend. He apparently kills it on Bumble as a white guy here in Tokyo, which I noted. He was very interested in my Soapland experience. I told him all of the above and then we went to a FamilyMart to eat a good snack. It’s all delicious and cheap there. Everyone in that convenience store must have known I was getting a post-prostitute Christmas dinner, because what else does a white guy do in Yoshiwara at 12 AM. Just as Santa Claus was leaving to service East Asia I checked out with a donut, called an Uber, shook my friends’ hand, and fled that whole big dark scene back to my Airbnb.

It wasn’t a total bust, though, at least it prompted this funny little poem for Substack.com:

100 likes. What a great haul. We’ll double it next year, for sure.

Oh yes, this was supposed to be directed towards Mom, who sometimes reads my blog.

Merry Christmas. By this time next year I’ll have published another book, and I’ll be back in the states. I don’t know much about the future but I know those two things for sure. Do not worry about me, ever, my head is on straight and I find love everywhere I go. I’ve met 5 people who read my blog so far in Tokyo, and I’ve only been here just over a week. It really is incredible, this internet thing.

Tokyo is incredible too. If English was more widely spoken I’d probably stay here for the rest of my life. If I am ever to become vastly more profitable in writing I’m taking everyone I love here so that they can see it too.

But until then, I’ll keep toiling on. I’ve done a lot of damage to myself in 2025 and my priority in 2026 is to restore my health. I’m getting back in the gym and doing it right this time. I won’t be quitting Adderall because that’s where all the words come from. I’ll find a woman who loves me in spite of my flaws. I’ll figure it out, and when I do, I’ll let you know how I did it.

I’ve rambled on too far. I’m drunk on coffee. Merry Christmas.