A glimpse into the shadows: An insider’s adventures in the world of escorts, episode 4

“Jeff wants me to come to his place again on Friday but this time he wants me to stay for the entire weekend.”

“And? Are you going to?”

by Sarah Brooke

Previous episodes of A glimpse into the shadows: An insider’s adventures in the world of escorts:

Picking at the heaping plate of nachos in front of us, I pick off the olives and toss them onto her half. Olives absolutely repulse me and despite asking for no olives on half of the nachos, we received an obscene amount of them over the entire plate. The last time I was brave enough to send something back to the kitchen the dish was returned to me with a couple of long curly hairs of unknown origin in it so I haven’t quite worked up the courage to complain since.

“Yes! He’s a total sweetheart. I’m just not sure what to charge, it would be a full 48 hours.” Refilling my half empty glass first, Sophie empties the remainder of our pitcher of beer into her glass.

“Anywhere from $2000-5000 dollars from what I have seen.” I’ve spent way too much time on escort websites, I’ve become familiar with all kinds of rates.

“That much? I definitely wouldn’t go over $3000.”

“You have to think of it this way… How much work are you going to be missing by being unavailable for dates? I’m assuming you’ll be at his place from Friday night til Sunday morning, right? That takes up two big nights for appointments. You’re going to be missing out on at least $1800. Don’t charge any less than that.”

“$2000?” She says.

“That’s fair but also on the low end of what high end escorts charge for a full weekend. Since you like the guy it wouldn’t be the end of the world to do it cheaper than you would otherwise. Remember that you’ll be with the guy for 48 hours straight, you’ll have to be in character the whole time. That’s worth some money too.”

“Maybe we should add overnight rates to my ads. I think I’m ready to start offering that service. Jeff was a great introduction to it. I’ve been really nervous and uncomfortable about spending the night with one of my clients but it was a lot of fun. I thought I’d be freaked out about sleeping next to someone but it wasn’t so bad.”

“I have no idea what the market is like for weekend bookings, I guess we’ll find out.” In my time working for her I had only received one request for an over night booking, which I politely refused.

“I doubt we’ll book many but I’ve been asked a number of times to do allnighters and have refused. Even one a month would really help with my savings.”

“Soph, I’ve been meaning to ask you what you thought about creating a website?”

“For me?” She furrows her brow and I can tell she hasn’t considered this before.

“Yes, for you. I’ve noticed that quite a few girls have personal websites linked on their ads. It seems that it’s the higher end escorts who have them and, I dunno, might be a good idea.”

“Okay I’m not against it but don’t most of those girls post identifying pictures of themselves? Face and all?”

“A lot of them, yes, but it’s not a requirement. You’re due for another photo shoot anyways, we’ve run out of new pictures. I could take a bunch of pics for the website, none including your face. It would just give you a bit of an edge over the competition.”

She thinks about it for a minute, loading up a nacho with my rejected olives. “As long as my face doesn’t have to be in it I don’t mind. I’m just not sure it will be that much of a benefit and who would we get to make the website anyways? Neither of us are exactly computer wizards.”

“I can build a basic site that looks pretty decent, I’ve priced it out and the hosting fees for the website would be minimal. It’d take me a couple days to put something together. We definitely don’t need to hire anyone else.”

“Are you sure? I mean there’s not much point in putting up a website if it looks unprofessional.”

“Ouch.” I try not to take offense, most people think you need a professional to put together a half decent website. I don’t tell her but I’ve already started making the website and it looks good. Simple but classy. “I promise it will look fine. You can check everything over before we put it up online. If you’re not happy with whatever I come up with, I can redo it. I don’t mind. I just figured that you wouldn’t want a stranger making the website.”

“And you’re completely right. I’m sorry, I do trust you. I just feel like making a website is a grueling process best left to the professionals.”

“Well let me prove you wrong then.” Looking down at the plate of nachos I notice there is only one left. “It’s yours, I’m stuffed.” She grabs the nacho, nodding her head to me in thanks. “We’ll have to do a photo shoot though, what are you doing after this?” I check the scheduler in my phone. “You have a 7pm that I booked for you yesterday but do you have any other bookings?”

She pulls out her phone and checks her schedule. “I have a 10pm booking with a regular but that’s it. I’m up for it if you are.”

“Definitely. My places or yours?” I fake my best seductive look and wink at her.

Laughing, she says “Mine, just so I don’t have to lug over a bunch of lingerie. Oh yay, we’ll have to do my hair and makeup.” Excited, she claps her hands. For someone who has never wanted to learn how to do her own hair or makeup she sure does love when I do it for her.

“I’ll do your makeup but your face won’t be shown anyways remember.”

Grabbing our purses we finish the last of our beer and head to the front of the restaurant to pay our bill. Sophie pulls out cash and hands it to the waitress. She likes to pay most of the time but I usually put up a struggle. Last night the drinks were on me so I don’t bother arguing. “It’ll get me in the mood, you know, I’ll feel sexy knowing I look sexy.”

“No problem but I’ll have to add that to your tab. Photographer, hair stylist, fashion advisor AND makeup artist.” I whistle while pretending to add up the numbers in my head. “I’d say ten thousand should do it.”

“Deal.”

Hopping in my car we head to my house first to grab my camera. She takes a few minutes to rifle through my closet and drawers, grabbing a few choice pieces of lingerie. On our way out the door she spots a pair of knee high boots that she grabs and adds to her collection of my things. When we arrive at her place her cat Mittens greets us at the door and after giving him an appropriate amount of attention he saunters off. After dumping all of my lingerie and boots on the bed, we head into the bathroom and I start working on her makeup. Five minutes later I’m finished and I move on to her hair.

“Do you want it curled or straightened?”

“I think straightened. I’ll never bother to curl my hair before dates so there’s not much point in showing long gorgeous curls in pictures when they’ll find me with boring straight hair once I show up.”

“Good point.” I get to work on straightening her hair, brushing it out first while the straightener warms up.

“Why does it feel so good when a woman plays with your hair but when a man does it, it feels like you’re being mauled by a bear?” She closes her eyes and her whole body seems to relax as I carefully brush out all her tangles.

“That’s so true. I even tried to teach my last boyfriend how to play with my hair but it always seemed like he was on a mission to tangle as much of it as possible.”

“Don’t even get me started. Apparently a lot of men have a thing for blonde hair so if they’re not trying to pull it when we’re doing it, they’re trying to play with it afterwards. Some of them are good at it but a lot of them just get their hands stuck in it and then I have to try to free them without ripping out my hair.”

“No one ever told you about the true dangers of life as an escort.” We both laugh. It doesn’t take long for me to straighten her hair and once I’m done she heads to her closet. I follow her and we start picking out outfits for her to wear.

“Hey, when did you get this?” I take a very expensive looking nurse costume out of the closet.

“Someone bought it for me. Looks good, right? He didn’t even want me to put it on when he gave it to me. He said he would let me know when he wanted me to wear it but that I wasn’t allowed to wear it with any other customers.”

“You have to take some pictures wearing this, it is so hot.” I hold it up to myself and look in the mirror.

“I don’t think so. Pierre is the one who bought it for me, I don’t know how much you remember about him but he’s been a regular for a long time now and I don’t want to risk pissing him off if he sees me in that costume advertising my services.”

“Alright, that makes sense. How about I wear it and you take some pictures of me?”

“Sure, put it on.”

“Not that I have any one to send the naughty photos too.” I frown and strip down to my bra and underwear, carefully putting on the costume. I look at myself in the mirror and smile.

“You don’t need to have a man in your life to take naughty pictures. Don’t you feel sexy in it?” She zips up the back and looks me over. “I love it on you. It actually looks better on you than it does on me.” I have to laugh at that. We may be the same size but Sophie has an infinitely better body than I do. Her outfits never look the same on me and vice versa.

“I don’t believe that for a second but thank you for saying that.” I quickly show her how to use my DSLR and I start posing on her bed. Ten minutes later I’m bored of modelling and it’s Sophie’s turn to be in the spotlight.

She starts out modelling a matching set of bra and panties, bright yellow in colour. She requires almost no direction, she knows how to pose her body to make the most of all of her assets. A few minutes later she throws on a black baby doll and puts on a pair of black knee high stockings held up with a garter belt.

“Wait!” She jumps from the bed and runs to her closet, grabbing a long whip from the back. She struts over, giving me a good smack in the rear with it before striking poses on the bed.

“How often do people ask you to bring stuff like this?”

“Almost never but I have a few who like the dominatrix act. It was weird at first but I’ve become quite good at it.” She jumps off the bed and a fierce look spreads over her face. “Get on the ground and LICK MY BOOTS.” She puts a high heeled foot forward and points to it with her whip. When I don’t make a move she frowns and cracks the whip hard against the bed. “I SAID LICK MY BOOTS. You will say ‘thank you, mistress’ once you are done.”

I can’t help but laugh. Sophie is one of the least demanding people I have ever met and it’s so out of character to see her putting on that act. “And people pay money to be verbally and physically abused?”

“Yep, I charge an extra $150 for it too. I try not to hurt them, the furthest I’ve gone is using the whip. This one guy started to make really strange requests and I wasn’t comfortable with them so I stopped seeing them.”

“Okay you can’t say that and not tell me what kind of requests he was making.” She turns away from me and starts posing again, facing away from me with her legs spread and the whip held behind her back. I take pictures from a few different angles.

“First of all he wanted me to pee on him but he brought it up during the session. I couldn’t just break out of character…”

“SO YOU PEED ON HIM!?” I interrupt her, unable to stop myself.

“No. God, no. I stayed in character and started berating him for wanting me to pee on him. Called him a weasel, a creep. He loved it.”

“He loved that you refused him and he also loved that you were making fun of him?” I ask, incredulous.

“Yes” she laughs. “I can’t make this stuff up. Anyways, we finished with the session and afterwards he said he’d really like me to pee on him next time. I told him I wasn’t comfortable with that and then he asked if I’d feel comfortable puking on him. He said he’d pay me extra and I said there was no way.”

“Puke? Oh my god I didn’t even know that was a thing. People like getting puked on?”

“Some people have an obsession with being degraded.” Throwing the whip in the general direction of her closet, she steps out of the baby doll and grabs a skimpy police officer costume that leaves little to the imagination. She puts on my knee high boots and I start taking pictures of her facing away from the camera.

“How horrified were you?”

“Pretty horrified, I didn’t expect it at all. I did not see it coming and then I had to have an awkward conversation with him afterwards letting him know that I couldn’t see him anymore. He kept telling me he wouldn’t ask to puke on me anymore but it was just too weird. It threw me off.”

“I don’t blame you, anytime you saw him afterwards you’d probably imagine yourself puking and pissing on him and it would throw you off your game.”

She turns around with her eyes wide. “Exactly! Even if he never brought it up again, I’d never be able to forget it. You get me so well. I love you.”

“I love you too. Okay let’s take a few pictures with one foot up on the bed and honestly I think you should get the whip again, that is a pretty sweet dominatrix outfit.”

I grab the whip for her and take a good deal of pictures of her in the costume. Some show her face but I’ll crop them later before posting them to the website.

“These are going to be really good. I think we’ve got enough for today.” I tell her.

“What if I take one completely naked but with all my naughty bits hidden?”

“That’s not a bad idea, go for it.” I don’t bother turning around while she strips and she poses on the bed with her knees together, hiding her mound.

“Arch your back and see if your hair will cover your nipples.” She obliges and her long blonde hair is just long enough to cover her nipples. I snap a number of photos from different angles before she is tired of posing and collapses on the bed.

“That was a very unnatural pose. Didn’t I look stupid?”

I start flipping through the pictures and shake my head. “Nope, see for yourself, you look like a mermaid.” I sit next to her on the bed, going through the pictures slowly so she can get a good look. She grabs a robe from next to the bed and throws it on.

“Too bad no one ever wants mermaid role play, how fun would that be?” she says.

“That would be amazing but how could you role play that without bursting out laughing or singing ‘Part Of Your World’”

“I guess that’s the problem, it wouldn’t be possible to keep a straight face and I bet realistic looking mermaids tails are extremely expensive.”

“You’re probably right, but that would be one hell of a niche to get into.”

“If business ever slows enough that I can’t make rent, I’ll consider it.”

I grab her laptop and transfer the pictures from my camera onto it and we start going through them one by one. She deletes quite a few of them but most of them are good and we argue about which ones to include on the website. We create two folders for the pictures, the best of the lot go into a folder specifically to be used on the website while the rest will be used in her ads.

“Thanks for your help, you don’t know how great it is to have a photographer that I can trust. Before you came along I was taking my own pictures in a mirror and with an automatic timer. It took forever to get any good pictures.”

“I’m glad to help. This is way more fun than waitressing at the Jive. Speaking of the Jive, I have two 10 hour shifts next week, Tuesday and Wednesday. I’ll drop the Carmen phone off at your place before I go in on Tuesday and I’ll pick it up either Wednesday night or Thursday morning.”

“Not a problem. I have classes but the john’s can wait.”

“I’ve been seriously considering quitting the waitressing job but how do I explain all this money coming in if I don’t have a legitimate job?”

“Same way I do. Make up a job. Tell people you’re still waitressing at the Jive. It’s not even close to here so no one will ever go there and realize you don’t work there anymore.”

She was probably right but I was worried someone would decide to come visit me at work and I wouldn’t be there. It had only happened once in the years I had been working at the Jive but it was still a risk. If a friend went there asking for me they’d tell them the truth that I don’t work there anymore and I’d be forced to answer awkward questions. I am a paranoid person by nature so lying has never come naturally to me. As much as I wanted to keep my job part time I wasn’t sure if that was the best option. Whenever I took shifts at the Jive Turkey I would typically make less money than I would if I was working for Sophie. I had changed my availability at work to weekdays only because from Friday to Saturday we usually get swamped with calls for Carmen and I would end up losing lots of cash by missing out on my commission. Sophie was back in school now which added another level of difficulty to the whole thing. She needed me to be available to work for her full time but was too much of a sweetheart to ask me to quit my job. The staff at the Jive Turkey and I had become close over the years and quitting wasn’t something I took lightly. Sometimes I hated the job but it was a good work environment and I’d miss my coworkers. Working for Sophie could be very lonely and boring. Waitressing wasn’t always fun but it was a chance to interact with people face to face, something that I missed when stuck in my apartment all day posting ads and waiting for the phone calls and texts to come in. As much as I would miss the people and the atmosphere at the Jive, it was about time that I start considering what I was doing for Sophie as my real job.

I take in a deep breath. “I’m going to give me two weeks notice when I go in on Tuesday.”

A smile erupts on Sophie’s face and she throws her arms around me. “Oh Sarah, I’m so glad to hear that. I promise that you won’t have to worry about money.”

I hug her back and start thinking about what I’m going to tell my boss.

The story continues

About the author

Having successfully helped a friend run her business as an escort in Vancouver BC, Sarah advanced to consulting escort agencies.