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Trans man from Toronto trying to appeal to both markets

I’m a mid-20-year-old trans sex worker from Toronto. I’ve been escorting for about 7 years, as well as working in camming, porn, and financial domination. This diary tracks five non-consecutive days that exemplify daily occurrences I’ve faced in relation to escorting over the years.

Day One

11 am:I wake up slowly, checking the notifications on my phone. I’m seeing one of my favourites today, but he is even less of a morning person than I am, so I have time. I make some coffee and breakfast before grabbing a shower, thinking about what to bring to my session.

I’ve seen him for a few years now and we know each other fairly well – he likes exploring new things and trusts me to surprise him with whatever I think he may like. I have a large collection of toys and a wild imagination, so I usually manage to find something fun.

1 pm:I open my closet door and riffle through my sex toys. I settle on a couple dildos, my kit of urethral sounds, and some bondage rope. I add some gloves, condoms, and lube to my bag 

1:45 pm:I get off the bus and walk the rest of the way to his place. He buzzes me in and I climb the couple flights of stairs to his apartment. The door is slightly ajar so I enter, shutting the door behind me and calling out a hello. 

2:15 pm:He’s finishing his coffee and filling me in on what he’s been up to as I unpack my bag carefully, letting him get a quick glimpse of what I brought with me. He eyes the selecting of dildos I brought and grins widely – “are you going to try and fist me today?”

3:45 pm:We’re laughing, like we have for the better part of our time together. He’s stretched out lazily across his bed, one arm tossed over my lap, as I coil my rope. “I always like when you tie me up,” he mumbles. “The sounding was neat, we should try that again sometime”.

I finish packing up and get dressed, glancing at the clock. “You have to shower, you’ll be late for work!” I remind him. He groans and buries his face in the pillow, giving me the finger. “I’ll see you next time”, I say, giving him a kiss and letting myself out.

Day Two

2 pm:I put a large pot of water on to boil, grabbing the toys I used yesterday. I have music going in the background, timing how long each toy is in the water. 

Cleaning my toys and putting things back in order is one of my favourite post-client rituals. I update my spreadsheet as I wait for the toys to clean – I keep a record of my calls, income, expenses, and jot a couple quick notes about how the session goes. It helps me keep track of likes and dislikes, if I want to see that client again, or what they’ve requested for next time. 

2:45 pm: My toys are away and my spreadsheet is updated. I’m dedicating today to computer work, so I pack up my laptop and head to a nearby café. Once settled in with my coffee and a bagel, I put on my headphones and some music, responding to my emails and twitter messages – the two main platforms where I get clients – and then make a quick to-do list to organize myself a bit. I have some website work and writing to do, and a new photoshoot to plan. I’ve been feeling a bit uninspired lately, so it’s taking me a bit longer than usual to be creative.

4 pm:My website work was finished easily; I updated my availability for the week and made sure everything was running smoothly. Since I have no real ideas yet for my photos – as someone who is very androgynous, it’s always a challenge for me to pick looks that don’t scare off prospective clients. I rarely know if the person contacting me thinks I’m a woman or a trans guy, and I try to keep my photos more neutral so that I can continue to appeal to both markets. Letting people think I’m a woman gets me significantly more traffic and inquiries, but I’m not nearly as comfortable with it. I keep it as an option for when work is extra slow, but it’s never my preferred. I’m always more confident going into the session if I know what they think I am, and if they don’t think I’m a woman.

I put off the photoshoot planning for now, I have writing to do instead. I’m also a kink educator, among other things, and today I’m revamping my class on how to ask for the sex that you want.

Escorting has helped me grow my skills in this area; made me used to trying to subtly pry information from people. I also learn more about various communication problems, and troubleshoot ways of overcoming them.

Day Three

5 pm:My phone lights up. “Hey babe”, it reads. It goes off again a second later. “u avail? Looking for some fun”.

I’ve been doing this long enough to know what works best for me; I’m in love with escorting, but I prefer to have it as an addition to my income rather than being the bulk of it. Unfortunately, as a freelancer, my other work can be just as unpredictable as sex work, and I’m facing a bit of a lull right now. As I chat with this guy, I can tell he’s someone I’d typically reject, but I could use the cash, so I entertain him.

We set something up for a couple hours from now and I turn on my “get ready for work” playlist, grab a coffee, and start organizing myself.

7:30 pm:After buzzing in, I take the elevator up to my incall space. My house is a quirky place that I share with my boyfriend and two cats, so I rent space from another worker instead. I miss being able to use my own space, but it’s nice that someone else takes care of all the necessary cleaning and such for me! 

I chat with my incall host for a few minutes, telling her a bit about what I’m expecting from the client as she packs up her laptop and she reminds me again to text her after he leaves so she knows I’m safe.

8 pm:He arrives on time, seeming wound up and a rather terse. We exchange pleasantries and I offer him a drink. He’s already taken his top off by the time I turn around from the fridge, so I put the glass down and follow his lead. 

8:10 pm:He doesn’t say much; he just pushes me over the bed and pushes his cock into me.

I kind of hate sex from behind, but it’s a favourite for clients who just want to get things over with. His hands grab roughly at my hips as he thrusts.

He thrusts faster, about to cum.

8:30 pm:He’s cleaned up and dressed almost before I’ve gotten up from the bed.

“Thanks.” He’s out the door, having said about ten words to me the whole time.

I doubt he’ll try to rebook, but I don’t really want him to, anyway.

9 pm:I tuck my space rental fee into my host’s safe and text her, hopping in the shower. I let myself out before she gets back.

Day Four

11 am: I got eight texts overnight from someone I’ve never spoken with:

5 am: hey

5:15 am: working today?

5:18 am: free right now?

5:20 am: I wanna fuck

5:21 am: are you free or not?

5:23 am: how do you expect to get work if you don’t answer your fucking phone?

5:26 am: whatever, I wasn’t actually going to pay you anyway

6:05 am: I hope your next client kills you

11:15 am: I put my phone upside down so I don’t see any more notifications. Waking up to messages like that isn’t super common, but it happens, and I always make an effort to take several hours off so that I don’t take out my annoyance on the wrong people.

Day Five

5 pm:Tonight I’m seeing an old regular. He was one of the first clients I ever saw, and I saw him frequently for years. He left his job a while ago and I hadn’t heard from him since, so I was quite surprised to get his email, and was looking forward to seeing him again.

6 pm: He comes in and gives me a big hug, telling me how much he missed me and how glad he is to be able to book me again.

We strip and get into bed, spooning. We spend the hour talking, catching up on each other’s lives, just cuddling. Sex isn’t part of the deal with him.

7 pm:When our hour is up, he gets dressed and gives me a kiss, saying he hopes to see me again soon.

8 pm: I’m home and showered, in a good mood. I had genuinely missed him and always hope that my regulars are doing well when I don’t see them for a while and it was nice to learn things were good for him.

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