Diary Of A Sugar Baby: The Lost Hooker

Hi, it’s Vivienne. Sorry it took me so long to get around to writing my first diary entry. I’ve been really #busy working and “working” and fucking and “fucking.” As a reminder, I’m a 26 year-old gallerina and sugar baby, and no, Vivienne isn’t my real name, but you probably get the reference…

I’ll start off by saying that I use the term “sugar baby” because the primary way in which I advertise my “services” is through a sugar daddy website. To be more specific, I have a profile on SeekingArrangement.com, which is where I meet the men that I sleep with, and occasionally form ongoing relationships with, in exchange for money. Although I also self-identify as an escort. Or a prostitute. Or a hooker, whore, call girl…whatever you want to call it. However, “sugar baby” seems to be the preferred term these days—it’s less straightforward than “prostitute,” which serves the superegos of men, and the self-regard of women. But I personally think “prostitute” sounds the most chic.

Now that we’ve gotten that out of the way, I’ll tell you a good story:

Last month, I showed up at 2pm on a Wednesday at the beautiful St Regis hotel in Midtown. A lot of clients (i.e. “sugar daddies”) won’t send you their photos before you meet them, for purposes of discretion, so it usually means there’s this awkward moment on the first-meet where you have to walk into a hotel or a restaurant, not knowing who you’re looking for. I’m a 5’10” redhead, and tend to be wearing bright red lipstick and something body-con, so when I show up alone at a hotel and start smiling at every man in a suit with one of those “is it you?” looks, I might as well be holding a giant sign that reads LOST WHORE, PLEASE HELP. When I was new to the biz this made me self-conscious, but now I’ve perversely come to like it.

So I’m walking around the St. Regis, smiling at various middling middle-aged men, none of whom appeared to be waiting for me. So I walk into the bar and see a guy sitting on a bar stool, wearing jeans and a T-shirt. He’s zoning out with his earbuds in, eyes closed. He looks mid 30s, pretty thin, and is wearring Harry Potter glasses—very “hot nerd,” which is exactly my type. Incredulous, I tap him on the shoulder. “You’re not Ken, are you?”

“Vivienne?”

And so now I’m freaking out, because getting paid to have sex with a person who you’d fuck for free is the ultimate life con.

I learn that Ken’s in tech, and is in New York on business from Hong Kong. “I want you to get drunk with me,” he says. “Will you get drunk with me? We’re celebrating.”

“What are we celebrating?”
“It doesn’t matter.”

So we drink a couple glasses of champagne. I’m supposed to be going back to work at the gallery at some point—I had assumed this date would take about two hours; they usually do— but pretty soon, as I become increasingly drunk, horny and interested in him, it becomes clear that work probably won’t be happening.

“Don’t go back to work, please, don’t go, I’ll pay you two grand not to go back to work.”

We walk nearby to Milos, a Greek fish place, and he immediately orders two bottles of wine. He seems hell bent on getting drunk, and more specifically, on me getting drunk, which I register as a bit strange, but the combination of tipsiness and horiness is keeping my guard down.

Ken’s like a little kid. He keeps ordering things and then changing his mind. He’s sending things back to the kitchen. “You have to send at least one thing back, otherwise they don’t take you seriously.”

On the way back to the hotel he’s practically running, dragging me down the street as I struggle in my stupid stilettos. When we get to his room he begins eagerly rubbing his face into my chest, over my dress. He does this for about 10 minutes, both of us fully clothed, just passing his face back and forth over my tits in an awkward silence. I feel like I’m in that scene in Big, where Tom Hanks goes home with the woman for the first time, and just acts completely bonkers—essentially, like a 12-year-old play-acting at what sex must be like. Despite this, I’m still really attracted to him, and we eventually start kissing and get our clothes off. But then right when he’s about to put his dick in me, he stops short.

“No, wait, this isn’t right… this isn’t the right time. Get up, get dressed, we have to go downstairs.”Ugh…

Down at the bar he orders me a $300 glass of whisky that I don’t want. I’m insisting that I don’t want it, that I’m already drunk, but he tells me that I have to “embrace life.” I tell him this isn’t life. I hate when clients do this kind of thing—buy you something expensive that you don’t want, or a dress that you hate, when you’d so much prefer to just have the money. The worst are the clients who drop $2k on a night out, and then pay you $600 for sex. It’s like, I can’t pay my rent in bottle service you moron!

So now I’ve reached a combination of drunk, angry and horny, which is a really dangerous combination for me.

“I want to have a threesome,” he says with a sudden urgency. “Do you have a friend you can call? She needs to get here fast.”

Obvs I have whores on speed dial, so I text this Dutch girl I met during a theesome the week before. It takes her almost an hour to show up, at which point I’m on the verge of blacking-out. Ken shoves a wad of cash into my hand and says something like, “go give this to your friend, so she knows we’re not sketchy.” So my drunk, stumbling, idiotic self meets Dutch Girl in the lobby and indiscreetly hands her a big wad of cash (remember, it’s like 4.30pm, and the hotel staff definitely thinks I’m a hot mess). After this there’s a span of time during which I can’t remember much, but according to Dutch Girl I aggressively demanded two orders of shrimp cocktail to myself, after which I immediately passed out at the bar.

But this I do remember. The next thing I know, I wake up in Ken’s hotel room, alone, and it’s dark outside. I have no memory of how I got here. (Don’t worry, this isn’t going to be a tragic sex trafficking story or anything, it’s just a me-being-dumb story). So now I’m angry because I’m like “why and how did I get here, and where is everyone else?”

Immediately, without thinking, I storm out of the room and down the hallway, presumably on my way back to the bar? I don’t even know. But about halfway down the hall it suddenly hits me: a) I’m not wearing any shoes; b) I left my bag—with my phone and all my worldly possessions—inside the room; c) I don’t have a hotel room key, and; d) I’m not even exactly sure which room of this 50-something-room hallway I just walked out of. Whoops. Also, it’s dark out, and therefore after 7pm, which means it’s been a good few hours since I can remember anything, and Ken and his new girl-toy are likely not at the bar anymore. Fuck. So, my options are 1) walking shoe-less down to the lobby looking like an insane, lost hooker (round 2) and asking to be let back into room 500-something (not sure), which is the room of a man who’s name I don’t know. (“Ken,” I’m almost certain, is not his real name… it’s never their real name. And anyway, Ken what?)

OK so option 1 bad, and so I go with option 2, which is just to bang on the door directly in front of me. I’m pretty sure that what I wanted was to use the phone in this mystery person’s room to call the concierge and ask for help. But to my surprise, Mystery Person turns out to be a hot, muscular 29-year old British guy who literally answers the door in just his boxers. And here I am, a random crack whore.

“Hi, uh, so…” I temporarily forget why I knocked, thrown-off by his hotness. “Can I use your phone? I’m locked out of my room.”

Straight-up within five seconds we’re making out. My mind is actually blowing as we roll around kissing on the bed—who says serendipity is dead?! He pours us some champagne from the minibar, after which I give him a champagne blow-job (#skills). We then have some really sloppy-but-fun sex, which involves fucking in the shower and on the bathroom sink. The whole time I can’t believe this is really happening; I feel like I’m living inside the worst-slash-best erotic novel of all time.

Next thing I know I’m being woken up by Mystery Guy. I accidentally passed out. Again. (Shit! I think I have an alcohol problem! Or narcolepsy.)

“I figured I should wake you, because I doubt you planned on sleeping here.” I look at the clock and it’s after 10pm. Great. So now, finally, I call the concierge. I barely have to explain.

“Hi, I seem to have lost my friend… I locked myself out of his room about—” But he cuts me off.
“Oh, it’s you. He’s been looking for you. Room 521.”
Lol, whoops.

I walk into Ken’s room to find him and Dutch Girl half naked on the bed.

“Where were you?”
“I was next door.”
“Doing what?”
“Uh, ya know, just… taking a nap.”
“Why is your hair wet?
“Oh, right… Yeah, that I can’t explain.”

Ken finds this all insanely funny. He’s laughing so hard that he’s in pain, simultaneously dragging me to the bed and pulling off my dress. Then I remember why I’m at this hotel in the first place—riiight, it wasKen I was supposed to fuck. I don’t feel like having sex anymore at this point, but I haven’t been paid yet, so I guess it’s threesome time!

I can’t even be bothered to explain the threesome in detail, other than that it was fine, and a bit lazy. Ken, ever-childlike, was running around the room, ordering me to bend Dutch Girl over my knee and spank her, and then smiling happily from a distance. Dutch Girl, by this point, had caught up in wastedness and was moving at like 1/5 the speed of a normal person. But she did give really good head, and made my cum, after which she said “I’m a lesbian” and then passed out.

As I was leaving, Ken handed me a stack of cash that turned out to be $1,127. Why? Normally, I’d consider that a good rate for sex, except he had told me over lunch that it would be $2k, and I did spend a total of ten fucking hours with him, which is bizarre. Although I guess I did literally pass out and then accidentally fuck someone else while on the clock, so I suppose I’m not perfect, either…