I first started considering sex work around 1997 or so. On a trip to Portland (I lived in Olympia, WA at the time) I went to Powell's and picked up a book called Sex Work (Frederique Delacoste & Priscilla Alexander), an anthology of stories by women involved in prostitution, stripping, porn, etc. Also around this time I had a friend who was working at the Lusty Lady peepshow in Seattle. I'd seen the Lusty Lady's ads in the adult help wanted section in the back of the Stranger, as well as ads for a strip club looking for cocktail waitresses and dancers, and I often considered applying for those jobs. Especially the Lusty Lady, I was secretly dying to work there. I was intrigued but I didn't think I had what it took, and honestly I probably didn't. I was 18 and a baby dyke, I didn't know anything about being a seductive woman.
In 1999 I moved to Portland. I called the number in an ad looking for models for a porn site and made an appointment to meet with the photographer, Tom, a few days later, at his sterile, depressing apartment downtown near the Broadway bridge. He showed me his websites and had me get naked unceremoniously next to his computer desk. I halfway expected him to laugh in my face, but he actually wanted to book a shoot with me. I couldn't believe it! But over the next few days my anxiety over the whole situation grew and I backed out at the last minute.
I moved back to Olympia, and then back to Portland again in 2002, and this time I was ready. I called Tom and booked an appointment for a photoshoot for a week or so later. A friend told me about a shoot she had just done, for a "hidden camera" website, so I called them and made an appointment for right away and that ended up being my first ever sex work experience. The studio was in this big warehouse space, with a bunch of different stations set up. They had me bring a suitcase full of normal girl clothes and my job was to pretend I was sitting in a doctor's office waiting room, at the bank, eating lunch in a cafeteria, in a changing room, and about five other situations, all with a camera pointed up my skirt. It was easy, and I only had to get completely naked in one scene (a gym locker room). The whole thing took about 45 minutes and I got paid $100 cash.
I did my shoot with Tom a few days later and it was a more traditional porn shoot. He'd booked a room at a downtown hotel. He had a woman who did my makeup and hair which seemed really luxurious to me, but he had her give me the craziest look. I guess I was supposed to look punk or alternative or something because I had tattoos and Suicide Girls was just getting big then and I think he was trying to capitalize on that, but I ended up looking terrible. Glittery green eyeshadow and dark maroon lipstick if I remember right. Tom had NO style at all. He had trunks full of clothes that he made all the models use and he would put together the craziest outfits: a yellow plaid tank top with a purple and blue striped skirt and lime green underwear and little pink ankle socks with white sandals. There was no rhyme or reason to these outfits, and he refused to accept my input or allow me to bring my own outfits. He also wouldn't let me choose my own name for the website, I think he named me Cassie if I remember right. The shoot wasn't too difficult, basically I started out fully clothed in my hideous outfit and gradually stripped out of it and then did some masturbation shots. Then I got into a different hideous outfit and we did it all again, maybe four or five times total. After we finished that he had me do a two-girl shoot, something that had been sprung on me unexpectedly and I wasn't super into the idea since it was my first time doing a photoshoot and I was pretty nervous and embarrassed at how stupid I looked and I didn't want some hot girl seeing me like that. To make myself feel better I thought about how I would never see her again, but later I found out she was dating a friend of mine and then I ended up seeing her around town several times over the next few years. The two shoots took around two hours and I think I only got paid $150, not nearly enough, especially since there was also about an hour of prep time and he insisted on taking me and the other model out for dinner afterwards, so really he took up about four hours of my time.
Over the next few years I did a bunch of photoshoots. I did several for another guy named Tom. He considered himself an artist and he claimed the photos he was taking of me would end up in a book or European magazines or something but the photos never came out that great and I don't know what he actually did with them. He was a creep, he never actually did anything inappropriate but I constantly worried he was going to. He always had this white gunk in the corners of his mouth. One time we did a shoot at the nude beach on Sauvie Island (a little way outside Portland) and I had to be in the car with him for 45 minutes each way and make awkward conversation and it was terrible. I remember I saw a Sleater-Kinney CD in his car and it was so weird that he would listen to them. I think the other CD I saw was, like, Kenny G or something.
I never liked doing photoshoots. I always felt nervous that the photographer would do something weird to me. Most of them did the photoshoots in their home, with no one else around. They were all just random middle aged gross dudes with a camera, they weren't professional photographers with actual studios. The only shoot I remember sort of liking was the one I did for a BDSM website which was run by this hippie couple with a big house and kids (who were at school when I was there). The woman took the pictures and the guy was in the photos with me. He beat the shit out of me with all sorts of floggers and paddles and things but I didn't mind, it was something I was interested in exploring anyway. They wanted me to look really scared and even to cry for the photos, but it was the first time I ever felt totally okay during a shoot and I'm not much of an actor. They seemed disappointed that I couldn't squeeze out a single tear, and they didn't want to book a second shoot with me.
What else. I briefly did webcam work, first from a studio/weird little house where they had several girls working at the same time, and later I got my own computer and tried it from home, but I found it impossible to make money so I gave up. Once I sold my period panties to a guy from craigslist. We met at a coffee shop downtown, he bought me a latte and we talked about bikes for a few minutes (we had both ridden bikes to our meeting spot), then I went to the restroom and got the panties out of my purse. I actually never even wore them, I just dumped my menstrual cup into them at home and had already put them in a plastic baggie. The customer provided me with a manila envelope, and when I handed it over he slipped me $50, then we rode off in separate directions on our bikes. One time I answered an ad from a domme looking for a pro-sub, no experience necessary. Her work space was in the basement of one of Portland's many "lingerie modeling" studios. I went in expecting to just talk to her but she'd booked an appointment for the same time and wanted me to sit in and observe. I was cool with that but once the session got started she wanted me to get involved and we hadn't discussed any sort of payment. The client was really into me and kept looking over at me with pleading eyes. I was young and blonde and cute while the domme was probably 45 and not that hot. I reluctantly applied some nipple clamps but refused to do anything else. Very little domination happened, mostly she just gave the client a handjob. Afterwards she gave me $20 and said she really wanted to work with me, but I didn't answer her calls and eventually she gave up.
Next up: I finally bit the bullet and auditioned at a strip club...