Confessions of A Gay Escort

Confessions of A Gay Escort

Confessions of A Gay Escort
Filed under: 
Sex & Recreation

"Confessions of a..." is an on-going column where we invite readers to submit their most outrageous personal stories anonymously for everyone to read. These stories are real, and usually come from people who lead double-lives. Due to the nature of the subject matter, we decided to keep it anonymous to protect the person's identity, job, and normal day-to-day life.

 

This week we sat down with a male escort and stripper to have him to tell us how he started, what the job entails, sucking and fucking, and to give us all the dirt on his coworkers. We hope you find this an interesting read, we certainly did.

Money

So I guess I started escorting about two years ago when I was 21. It’s not like there was a day that I started though, you kind of ease in to it slowly. At first I was a stripper at a gay bar, and then I started doing extras on the side. A lot of people ask me “how can you do that?” and I try to explain that I work less than 25 hours a week and make enough to live really comfortably. I go to school so I don’t have a lot of time. I’m not your typical stripper because most of them aren’t in school; a lot of them are just idiots and cheap whores.

What makes someone a cheap whore? A cheap ho takes a guy to an alley and sucks him off for twenty bucks. There are loads of these guys. They’re trashy and don’t respect themselves. They look bad on all of us; they’re some of the dumbest people I’ve ever met, there’s this on kid in town who I’m pretty sure is so delayed, like he’s retarded and will put anything in his mouth for a few bucks. Then there’s me and my friends, we have our prices, we negotiate it with our clients because you always want as much as you can get. None of us make ourselves seem desperate though, like I always try to make a client think that there’s someone else willing to pay more, but that I really like them and would rather have them take me home that night. The trashy guys make themselves desperate, that’s their sales pitch: cheap and willing; they are actually desperate though, it isn’t an act.

Stripping

I probably see two or three clients a week which is pretty low, but I feel better just stripping so I try to stick to that. Less money, but less shame. I’m also not going to tell you how much I really make, it changes too much week to week for me to really say, plus I don’t want to say a number that would encourage someone else to switch careers.  I’d say I’m mid-range, an upper-middle class bitch. Sometimes it’s sex for money, which trust me, doesn’t make you feel great. But I probably only have sex, including blow jobs and stuff, with a client a couple times a month. It’s almost always just me jerking off for them then cuddling naked; always cuddling. I think in two years I’ve only actually fucked seven or eight times. I do give the best blow job though. Trust me, it’s fucking perfect and it’s gonna cost you a lot. I can deep throat a girthy nine inches, and know exactly where to massage my tongue. Stripping is about trying new positions, seeing what you do that makes their eyes roll back. Apply that to a blow job; it’ll never be the same because you have to adapt if you want to get paid. If you’re inhibited at all, you might as well not even bother sucking. You gotta make it about them.

Suit

Most of my clients are middle aged, some as young as 30. If someone were really gross I’m not going home with them. A date can be whatever they want, or at least whatever they are paying for. My guys are usually just lonely and they probably came out later in life and never got to cuddle a hot guy when they were young, so now they pay for it. Last week someone took me on a date just to see Catching Fire and threw a few bills at me after. Yeah some of them are married. The married guys only weird me out when they talk about their wife and kids. There’s only one married guy who’s a regular of mine, he takes me to some of his work events though which is awkward because all of his coworkers clearly know what's up. There was a weekend retreat and he booked a hotel room with only one bed then had coworkers in the room for drinks. It was possibly the most awkward weekend of my life, but you just focus on the money at the end and let his wife and kids deal with it after.

Clients like me because I’m smart. I can actually hold my own in a conversation about most topics, and look good in a suit. Sometimes that works against me, if they respect me too much they won’t want to pay up. When I have a bad night stripping I can shrug it off. I measure weekly performance. When you have a bad week you start to question who you are as a person. It’s the worst. You feel fat and ugly. You’ll see crack whores making more money than you did, you’ll wonder if you are clever enough, aggressive enough, sweet enough, young enough… bad weeks are the worst, and it can be hard to crawl out of a slump like that. Alcohol helps.

Who wants bananas?

A group of us were talking once and everyone agreed that I was the most “normal” person of the group; that when I put on my clothes and walk down the street I don’t have that stripper swagger. Lady in the streets freak in the sheets kind of deal. All I said was “We’re all still doing this though. We’re all some kind of fucked up.” I mean some do porn and want money, others have kids to support. Most of us didn’t have an easy go at it. I’m from a pretty fucked up family, honestly impressed that I’m not actually in the gutter shooting up right now. My friends are former addicts, or like me, from a broken home and are using this to get ahead. I mean I dealt with some sexual assault when I was younger, was raped, and then became a total slut before I started stripping. We’re all fucked up somehow. Now I’m kind of balanced. Even though I pretty much don’t think I’d let anyone really love me.

Sorry, that felt weird to say. What’s my sex life like? Normal. I’ll hook up with someone when I go out on the weekend; yeah I have sex a couple times a week. I don’t usually tell who I hook up with what I do. I usually just leave it at university student. If someone really interested me and we wanted to enter a relationship, I could stop the escorting. I would still strip, but I see those as very different things. There are rules in a strip club, it’s clean, and it’s legal. Either way I’d say I have two or three years left of this and I’d only escort after that with established clients. There’s nothing sadder than someone stripping past their prime.

Timoteo

I’m only cocky when I’m working. Because it isn’t me, it’s the character I’ve created. Fake name, fake e-mail I use with Americans who like to take me on ski trips and weekends in Chicago and New York, there have been a couple trips to Paris. Some guys want a sugar daddy, personally I don’t. As ideal as having someone who will pay for my tuition and take me on trips would be, I don’t want to feel that kind of debt. I wouldn’t be able to cut them off when I’d milked them for all they are worth; I’m still a nice guy sometimes. That said, I think I’d have to tell them my real name if we entered a relationship, and I don’t want to have to do that. I have my real name, my stage name, and then I have the name that I tell regular customers is my real name. Anonymity is key because there’s still a lot of judgement towards sex workers.

When people judge though, I tell them that it pays my tuition. I ask them when the last time they went to a fancy dinner was, because I eat out at several hundred dollar bistros all the time, and get paid to do it. I can sugar coat it by telling people that I love the money and freedom; but at the end of the day I’m kind of trapped for a while doing something that makes me feel like shit and would stop if I could. You get sucked in. I’m still a person though, and I’m not what I do, even though I’m still a hustler. I hate that word, by the way, but I can’t fight it.

See the other entries in our confessions series :

If you think you have an interesting story to be featured as part of the anonymous Confessions series, send us an email to [email protected] and tell us your story.

images via Pretty PukeWeHo Nights (1, 2, 4 & 5) and Men's Watches. 

Share this article

Comments

Content Stream

EVERY WEEK. We feature the best underground tracks & remixes, and most of them are up for free download. We prioritize Canadian producers and acts but it is not exclusive. Every Sunday, we'll round-up all of our favourite remixes and tracks we've received through submissions and lay them out...
Yesterday's Women's March in New York City reportedly drew a crowd of roughly 120,000 people, spanning 20 blocks and conveniently passing by several of Trump's buildings. I was there, and it was great. The day started off with some sideline debates between old white men in Make America Great Again...
You need to get on this. Montreal has a new artist on the scene, and he goes by the name Clyde Forest . This dude got on our radar as soon as we laid eyes and ears on his craft through his instagram profile and his debut single. Immersed in a place that lies between contemporary urban with a rock...
You already know about Jaymie Silk . If you don't, then brush up on your knowledge as he's been on our radar for quite some time now as the new rising star producer and DJ, particularly known in the Montreal vogue scene. He just dropped his latest EP titled Watch Me just in time before his...
Donzelle is a beautiful mix of questionable metaphor rap, deadpan dancers, unrefined costume changes and heavy dirty bass. You might remember her name from back around the neon/electro-rap days, you might just not, and that's okay. She's back with a brand new single and visuals to accompany her...
Young self taught producer, Kultur keeps on climbing the ladder and asserting himself since the release of two EPs and several singles that caught the attention of the interwebs. After a year spent putting flesh on the bones of his universe, he comes back with "OCEAN" , his new single featuring...
iamhill is a force to be reckoned with. This self-made emerging artist is talented in a raw, underground type of way. She took it upon herself to produce, write, record, and perform "Give It a Rest" - A catchy single with few words that will get stuck with you as you play it on repeat. It was...
EVERY WEEK. We feature the best underground tracks & remixes, and most of them are up for free download. We prioritize Canadian producers and acts but it is not exclusive. Every Sunday, we'll round-up all of our favourite remixes and tracks we've received through submissions and lay them out...
Nothing better than some fire beats to warm you up in this damned cold weather. MORRIS just recently dropped a 6-track project titled GOOMBAWAVE on soundcloud. A collection of beats based on those species of sentient mushrooms from Nintendo's Mario franchise. You don't need to listen to it in any...
Birthday Boy & Trish release new single titled “Chance To Go Far” off their upcoming EP titled Joseph , out on January 19th via Bastard Jazz . We recently featured the single “Magic” off the same EP, which they had released to close out 2017 with a bang. Further emphasizing the project 90s R...
This emerging artist has been on our radar for quite some time now. Langston Francis is a young visionary who grew up in the centre of Kensington Market and was heavily influenced by the Toronto music scene. His first single "FCKD IT UP" has been making the rounds of the interweb, especially for...
Watch the video above. Life is a journey of twists and turns, leading us to moments of both true bliss and great despair. In her new video "Prime Time" , Singer-songwriter Liana takes us on an emotional adventure throughout the breathtaking landscapes of Peru – a visual odyssey that reflects a...