I don’t know how my sessions with Lily continue to whip me into a mess of anxiety. It’s my persistent desire for perfection, or at least to provide an experience that’s fulfilling beyond the physical level. V taught me that it’s useful to approach clients like this with your own personal goals in mind. In the instance of Lily, my goals are: 1. Create a respectful environment in which she trusts me to explore her own erotic imagination, and 2. Cultivate a vocabulary in which she is able to express her desires.
Lily lives alone in her apartment and spends her day orchestrating a million Zoom conferences, which provides some level of contact, but when all of that fades away, it’s just her and the remnants of Cassandra strewn about her home. A cup here, a book there. On Saturday, I didn’t know where she would be mentally. I also didn’t know where she and I should begin.
My theory with providing sex work to women (which to be completely fair, stems from limited experience-based knowledge) is to avoid being too orgasm oriented. Women are sensual. Telling a woman to cum, or anyone for that matter will often lead to the opposite. Focusing on how wet her pussy might be creates unnecessary pressure she’s likely already fighting to keep away. Conveying impatience will kill any chance you have at coaxing out an orgasm. And women aren’t simple visual creatures. Of course, some women are-- there are always exceptions-- but I think generally, women are in it for the mental games. We have to perform elaborate mental gymnastics, pushing past our internalized sex negativity and body shame: all of the voices that say that “you don’t deserve pleasure,” or “you’re taking too long,” we’re all burdens. My goal is always to make fun primary, and orgasm an afterthought.
The first couple of sessions with Lily, I’d turned the focus toward winning a game. We both enjoyed the time, but I was worried I was using this tool as a crutch. This time, I didn’t want to hide behind the comfort of games, and to be honest, the last round hadn’t run as smoothly as planned. The other issue was time. I was spending too much time on our sessions as compared to how much money she was paying me. The first few times it wasn’t an issue, but I had gotten to a point where I was spending hours preparing and then providing hours of service for hardly any money. Which isn’t inherently a problem, except that I’d been taking on a lot of new projects lately. I hold a million and one positions within the Soldiers of Pole organization . I was recently offered a position as a resident author for a Berlin-based erotica publication. I’m still podcasting, even in the thick of quarantine. And I’m taking a handful of outcalls to stay afloat financially. It’s a lot to balance, and maintaining a consistently novel experience for Lily particularly stretched my creative brain to its limit.
Beyond that, I was fretting over filing taxes and whether or not to file for unemployment. My club sent out a mass text letting us know that they had “consulted their lawyers” and had “come up with a way” for us to file for unemployment. Which should have been a given, considering that we are technically employees under California law, but of course, they had skirted the law the entire time through a series of local government kickbacks and elaborate legal work. What this means in the end, only time will tell, but it alleviated the burden for those of us who had stood by, unsure of what the future of the pandemic might hold for us. The point being: a lot was going on, good and bad, and I needed to streamline my effort. It wasn’t that I intended to give her less, I just needed to reduce the hourly burden on my life, and I felt that we’d come far enough that I could without her even noticing.
This round, I did my normal preparation. I put up a cute backdrop, set my lighting to be somewhat dramatic; flipped my phone to portrait mode so that she could see as much of my body as possible; and got dressed up. This time I wore a pink underboob-revealing shirt with a pink thong under white fishnet stockings and a pink leather garter belt. We would not be bargaining for me to undress. I would arrive at the party undressed.
Lily finished her weekly kung fu movie night and called me.
Lily: Oh, hi!
She smiled. Surprised.
Me: Welcome to Selena’s Cocktail Hour. You’ll have to pour yourself a drink and then join me.
Lily: That’s actually perfect. I was just sipping on this special pink gin. Maybe you can see it?
She held the bottle up to the camera, but the lighting was so yellowy incandescent that I couldn’t make out any pinkish color.
Me: I can’t really see.
Lily: Well, it’s slightly pinkish. A friend brought it back for me from Scotland years ago. Recently I decided to start finishing things. I’m a person who saves everything. I hold onto it until for as long as possible, but I realized that well-- you never really know. So I decided to start finishing things.
Me: You never know what will happen. Gotta enjoy life.
I said it casually, noticing belatedly as a cloud passed across Lily’s eyes.
Lily: Truly.
Me: Well, I’m glad you’re enjoying this pretty pink gin. Cheers!
We raised our glasses and bringing them close to the camera, which was as close to clinking them together as we might get.
Lily: What are you drinking this evening?
Me: I don’t really drink alcohol. My body doesn’t process it, so instead I’m drinking two different kinds of teas.
Lily: Ooo. I love tea. What kinds?
Me: One blend for people on their periods that has stuff like dandelion and nettles, and another passion fruit tea.
Lily: Sounds delicious.
Me: It really is. So! I thought we would begin our session with talking. Later we’ll do… other things.
I paused for effect. Lily smiled slyly.
Lily: Okay.
Me: How was your week?
Lily: Oof! Busy. Had a lot of presentations to give. Just getting all of the educators acquainted with Zoom and things like how to provide an interactive experience even when they’re teaching to a room of 100 students who they can’t see. I made a joke I was proud of: I told them to raise their hands if they knew how to use the hand raise feature. A bunch of them raised their actual hands.
Me: Oh, that’s great. Dad humor on my level.
We chatted back and forth about work. She teaches teachers how to teach. She is the top of the pedagogy pyramid. Educational Designer is her professional title. Professors have been struggling to continue teaching during the pandemic. The dinosaurs perched comfortably in their tenure positions were whining about the pointlessness of her seminars. They worry about students cheating since there’s no means of holding them accountable.
Lily: I think it’s silly, but I can’t say that.
Me: I saw a meme recently that said something along the lines of, “We’re not learning how to work from home, we’re in an unprecedented situation trying to learn how to work.”
Lily: And the reality is that they can’t prevent cheating. If someone really wants to cheat, they’ll find a way.
Me: It’s also like, most people don’t throw that kind of money at education just to skate through. In the end, you’re learning for yourself. If you don’t know your shit, it’s going to hurt you more than anyone else. But also, this seems like the least important concern for teachers to have considering the circumstances.
Lily: Exactly. And to be fair, most teachers just care about their students’ wellbeing.
Me: Of course.
I checked the time: twenty minutes in.
Me: And now we move on to the second part of this adventure! You’ll need your vibrator.
Lily reached around behind her and pulled out her Magic Wand.
Me: For this portion we’ll continue talking, but with our vibrators on. Ready?
Lily nodded at me, smirking.
Me: Let’s rock and roll.
We each engaged our respective vibrators. I don’t know how I’d underestimated my little baby vibe, but talking with my clit sucker in place proved to be more difficult than I’d expected.
Me: Soooo… what else is new? Woo hoo hoo! Lots of sensation going on here. Wow.
Lily: Ummm… yeah you’re right. Let’s see… Oh! I shared a drink over Zoom with that woman I mentioned last week that I like.
Last week Lily had mentioned she was developing feelings for a woman she knows. She’d been worried that it wasn’t the appropriate time. She didn’t want to think about moving on too quickly. She didn’t want her next person to judge her for moving on or assume that it was too early. She had met the woman years ago while she was with Cassandra. She had sensed that the woman had had feelings, but Lily was devoted to her partner and didn’t pay much attention at the time. But since life had changed, Lily was considering seeing where the “what if” might lead.
Me: Celeste?
Lily: Yeah! She has a daughter, and she was telling me that she planned to go up to see the Aurora Borealis with her daughter and a friend whenever all of this is over with. So I basically invited myself to go along with them whenever they do.
Me: That’s fantastic! I mean, they can’t just hog the whole Aurora Borealis to themselves. That would be rude. And I mean, I’m sure they could fit you into some luggage or something. Unzip you whenever it’s nighttime.
Lily: I don’t even take up that much space.
Me: Is there a particular time of year when it’s visible, or is it always visible?
Lily: Most people go during the winter.
Me: Is that when y’all would be going?
Lily: I think so.
Me: I guess it makes sense. Winter solstice and all. Or equinox? No, solstice.
I was chattery, trying to keep my train of thought. I squirmed around, pressing my thighs together, leaning from one direction to the other. It was almost too much. I felt like I needed to pee, but I knew it wasn’t pee. Lily smirked at me from her phone.
Lily: I think it’s the solstice.
Me: That makes sense. It’s not about equal days and nights, it’s about having the longest night so that you get every precious extra second of Aurora Borealis action.
Lily: In case you don’t feel like you’ve gotten enough after a full normal night of Aurora Borealis.
Me: Are you kidding me? I came here to have the longest experience. Quantity equals quality.
It was funny how adding clitoral stimulation automatically turned the tone from platonic conversation to flirtatious loaded banter.
Me: This little baby really gets ya.
I referred to my vibrator.
Me: I like it because it’s small and portable. The Magic Wand is less portable.
Lily: I actually have two Magic Wands. I have mine, which is a lot shittier, and Cassandra’s. Before she died, she used to joke that whenever someone passes, you have to steal their sex toys. Sex toys can’t just go to waste, so it’s your job to steal them. Whenever she died, everyone came over to help pack the house, but when we got to our room, I was like, “Everybody out!” because I didn’t want them to see. Hers is a lot stronger than mine, but I like mine more because of that.
Me: It’s nice to draw things out a little more instead of immediately cumming.
Lily: Yeah. Actually, the way mine got fucked up is kinda funny. She and I had been having sex right before a power outage. It was probably the last time we did before she got bad. She was still healthy enough for it then. Anyway, we had had it on when the power went out, and forgot to turn it off. We went out, and didn’t realize the thing was on the whole time. When we got back home, the house was smokey. It had actually burned a hole in the ground!
Me: Oh my god!
Lily: Thank god it didn’t burn the whole house down. That would have been hard to explain. Anyway, I thought that it was gone for good, but somehow it still kept working after that, although now it makes a lot more noise than before.
Me: That’s hilarious. Imagine that 911 call. I mean, how could you explain burning your house down because you left your mega vibe running.
It was such a cheerful way to include Cassandra. She was there. I mean, truly she was always there in the back of Lily’s mind, but here she was, explicitly present with our vibrators on as we wove between the platonic and erotic worlds. I checked the clock again. Another 20 minutes had passed.
Me: We’re now at the next juncture of this cocktail hour: silence. Now we sit in silence.
Lily bit her lip and smiled, then shut her eyes, diving into herself. She’d opened to include me, but now was her moment for herself. I would be there. I watched her, enjoying myself, feeling my own pleasure passing over me. I didn’t know if I could cum with her. It felt a little too personal in a way, as personal as everything had become in the little time we’d known each other. Her breathing shortened as her eyebrows knit together. She began to moan. I knew she was on the precipice. I became entranced by her pleasure. It’s such a special moment when a woman comes. Hard won, and with a depth of intensity most cismen will never fully comprehend. The video quality dropped. Her face became blurry. I almost couldn’t tell when it happened, except that afterwards she opened her eyes and smiled a sad little smile. She blinked. The way she blinked, I could tell it was tears. I couldn’t see them. The internet was forcing me to guess and intuit. We sat in silence. She placed her hand over her heart and I did the same. I waited for a minute before checking in.
Me: What’s going on? What are you thinking about?
Lily paused and wiped her eyes.
Lily: It was a hard week. Earlier, I was looking in my fridge and realized I was almost out of the strawberry rhubarb jam Cassandra had made before she died. I’d made it last so long, because I didn’t want to reach the end. Before she died she made two last jars of preserves: the strawberry rhubarb, and an apricot, which is my favorite. I ate the strawberry rhubarb one first, even though I don’t really like rhubarb that much.
Me: I don’t even think I’ve ever had rhubarb, to be honest.
Lily: It’s not very good. My father loves it, but I could never get into it. It’s really tart. Anyway, that’s why I decided to start finishing things. I realized I couldn’t hold onto the last spoonful forever. I just couldn’t bear the thought of not having the jar there anymore.
Me: It’s good to enjoy these things. She’ll always be here with you.
Lily: I know. And it’s just stuff. It’s not her.
Me: Plus, it just sounds like you’re about to enjoy apricot jam, which is your favorite.
Lily paused, looking off. I wasn’t saying anything she hadn’t thought of before. I felt like I was trying too hard to reassure her, when there wasn’t any way to truly help in this situation. She wouldn’t always have bits of Cassandra around to hold onto. It would be this rippling sense of loss she would continue grappling with for years to come.
Lily: I just don’t want to think about when I get to the end of that jar.
Me: It’s going to be hard.
Lily: But I have to finish it eventually. Cassandra used to make pies for my dojo and some for me to bring to work. It was a gift for people whenever they passed their belt tests.
Me: Oh man, that sounds amazing.
Lily: She was always trying new recipes. She would bake a pie for the dojo and one for me to bring to work. She would tell me to bring the pretty pie to work, and the ugly pie to the dojo, because they’re family.
Me: I’ve always believed ugly desserts taste the best.
Lily: Me too! She also never used to eat anything she baked, except for chocolate chip cookies.
Me: Really? But those pies all sound delicious.
Lily: She just liked baking for other people. It was one of her gifts. But I always wanted to share things with her, so whenever she’d ask what I wanted her to bake, I’d say, “chocolate chip cookies,” because I knew she couldn’t resist.
We spent a while longer remembering, holding onto the warmth of Cassandra’s presence between us, the imprint that lasted even after death. Talking about her, it felt as if she grew. She expanded and sat between us, listening in. Loss is surreal. One moment the one you love is sharing breakfast beside you, the next all you have are a few things that hold their smell or the remnants of their touch. Cassandra would be part of every orgasm for a while. I mean, how could she not? You spend years coming with a person, sharing toys and pleasure, knowing every intimate cranny of her body-- how could she not be ingrained into this once shared ritual?
I was there to be training wheels. Lily could practice coming with me, and I wouldn’t judge her if she cried or had trouble climaxing. I wouldn’t expect any performance from her in return. I wouldn’t expect equal emotional reciprocation. I was just there to verify that yes, she could. Yes, she can. I was a witness.
I checked my clock, I needed to follow my rules and end the call soon. I felt like a therapist having to end a session right as my client’s crying begins to subside, but this wouldn’t be our last call. I’d see her next week. I’d given her what I could, and that was enough. I thanked her for her vulnerability, and hung up.