My One & Only OnlyFans Interview
- Holley Livingood

- May 26
- 4 min read
During the summer of 2021 I was searching for my next gig. My resume read like an ADHD diagnosis: at-home-mom, fashion stylist, copywriter, sex club owner, and devoted generalist of gardening, travel, performing, and childcare. I was qualified for everything and nothing at all, my professional references were from fellow sex club owners, my last W2 job was in 2001, and I was looking for work during a pandemic. It was grim.
Until I saw an ad on Craig's List looking for a live-chat agent for a successful OnlyFans personality.
This. Is. My. Calling.
Every person I met with was a quality weirdo and creative savant. In the end, I didn't get the job but I had a good time swinging at it.
___________________
1. Where do you live? Did you grow up there? If not, what brought you there?
I moved to Portland right after college with my then-boyfriend now-husband and I have been here ever since. My grow-up was in a tiny ski town in the middle of Idaho.
2. How do you feel about the current state of the country/world? (Don’t go too nuts here, for the love of god.)
Well, I have a uterus so I’m low-key frightened all the time. Regardless, I’m a big, dumb optimist and believe that current legislative dumbassery will topple as brown people and the young take over the country in the next 20 years. Fingers crossed.
3. Convince me to buy a three minute custom video of you (AKA: the boss lady) jerking off a plastic sheep while talking about your love of wool sweaters. In a conversational, message-y way, not a newspaper ad sorta way.
“I get instantly aroused when I smell wet wool. It’s like a switch flips and all I can think about is sex and dick and itchy wool scraping my tender nipples. Fuck my nipples get hard. You wanna see what wool does to me? Even better, what I do for wool? It gets weird, just like you like it.”
4. What type of work is your main source of income at the moment? (If you already answered this in your application, please re-answer. I know, I know. I'm doing my best here.)
Past work includes fashion stylist, community organizer, event planner, writer, and sex-on-premises nightclub owner. My skillset has landed me here: OnlyFans Chat Gal applicant. This is exactly the gig I’ve been looking for. No joke!
5. What is your current availability?
Monday - Friday between 9a-4p, weekend availability varies. Anything is possible with planning.
6. A fan comes on and says "hey babe, i'm so horny right now, what are you up to?" What do you say in response?
“Ooh, I like horny. Let’s ride.”
7. Favorite book and why, go! (Note: anything by David Foster Wallace is an unacceptable answer, so don't start with me.)
Confederacy of Dunces because Ignatius is crude and tragic. Of Human Bondage because I extra-relate to the protagonist. Windup Bird Chronicles because of its beauty. Anything old and Russian because no one writes suffering better. I also read a bunch of trash.
8. Did you do college-y things? What college-y things did you do? Why those things?
I earned a BA in Literature and History with a minor in Italian from Franklin College in Lugano, Switzerland. I have all the skills necessary to work during the Renaissance.
9. Tell me about your weirdest sexual encounter.
Dang, where do I begin? I’ve owned a sex club, have frequented sex clubs, and I’ve hosted sex-positive parties. I’ve also engaged in a shit-ton of social sex, weird is normal. Top three: anal fisting, cock & ball torture, sounding.
10. You're chatting with a fan and they are skeeving you the fuck out. What do you do?
First I’d try to deflect and deescalate the conversation. If that doesn’t work and I’m still skeeved, I’d excuse myself from the convo, check in with myself, and then check in with y’all at Boss Lady Central about what to do next. My skeeve might not be other people’s skeeve so I’d want some perspective before moving forward.
11. What sort of LEGAL sexual things/acts are you uncomfortable with talking/sexting about?
I think I can roll with almost everything legal.
12. You've been chatting with a fan for like twenty minutes and they haven't tipped. What do you do?
“Before we go on, and before my pussy gets any wetter, I need to feel your rock hard tip money.”
13. A fan comes on and tells you they want to sext a scene where you are both sexy cod fish swimming in the ocean. You know he's submissive. What sexy adventure are you going to take him on?
Step one: Google “cod images”
Step two: Praise his big, wide mouth and tell him he looks like a very bad boy. Then make him obey his mistress: nibble the algae from my dorsal fin, bury my eggs, and ultimately suck off a sea cucumber while I flog him with an electric eel.
14. A fan tells you that he has a fetish for women being tied up, that he always has had these thoughts and maybe they’re from (insert random media here). He thinks he needs therapy, that these thoughts are too weird and everyone would judge him if they knew what he was into. What do you say?
“Your thoughts and desires are normal, you are ok. Think of an object. Got one? Toaster? OK, toaster: There’s someone out there who has a toaster fetish. No exaggeration. You are totally ok. There are online and IRL resources for shibari and bondage arts and whole communities of like-minded people to connect with. You probably don’t need therapy for this, but you should go anyway because therapy is the shit.”
15. Is there anything else you think we should know about you?
I’ve had some pandemicky ennui but on the whole I’m still a nice person to be around and believe that people are generally good. I love comedy, satire, irony, all of it, any of it, yes please. I am very responsible and only resent it part of the time. I love dogs, am currently re-reading “Chances” by Jackie Collins, and am obsessed with the 90-Day-Fiance franchise.




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