Pt. 2: Cassandra’s Care

I was puttering around in my studio preparing for my call with Lily. I’d pinned up a backdrop and laid out my Thai mats so that I could stretch out during our session. Lily and I were going to talk around 10 p.m., after she finished her weekly quarantine movie night with her judo students. Lily is a blackbelt judo instructor. She’s been practicing for several decades at this point. Many of her students are Millennials or Zoomers and never grew up watching kung fu flicks, so the pandemic had become an opportunity to educate the children. This week they were all watching Fists of Fury separately from their own homes while texting in a group chat.

Thursday night I’d gotten a text from three of my primary daddies. Dale, who had cooled with me recently after developing an infatuation with another dancer hit me up looking for nudes. I decided to indulge him, because I figured a minor investment of nudes now would pay off later with several hours of Heaven Box dances. Marcus drunk texted me a chain of messages I couldn’t quite decipher, something about not being such a good guy after all. I couldn’t tell if he’d meant to send them or what cryptic message I was intended to glean from his unexpected midnight texts. Charlie, aka Gemini Ketamine Daddy texted to check on me. I didn’t know what he wanted and I didn’t care to find out at that moment, so I left the conversation hanging. I’d been wondering about Danny on and off for a few weeks. He’s always buzzing around somewhere. I figured he simply had disappeared as he does, but Saturday night he hit me up.

Danny: You staying safe?

Me: I am. How are you sweetie?

Danny: Bored. Haven’t left my house in two weeks.

Me: It’s terrible. I was wondering if you’d managed to stay in.

Danny: Ha. I have no choice.

Me: Are you working remotely?

Danny: Yes, we had 200 events cancel, but we are doing okay. Everyone wants to livestream now.

Me: God. That sounds incredibly stressful. But that’s when you innovate.

Danny: Exactly. Yeah, it’s been crazy and I think I had Covid.

Me: Really?

Danny: Literally just got off of a video conference with Rita Ora and Alicia Keys. Fuck, Rita Ora is hot lol.

Me: They both are lol.

Danny: True. I was so sick and working 24hrs a day, but I’m better and working on a big livestream for charity now. How about you?

Me: You didn’t take a break at all to be sick?

Danny: No. Too many people depend on me.

Me: Well, there is only one Bono certified, “Digital Danny”.

Danny: Lol. How about you?

Me: I’m okay. Trying to fight off the malaise, but generally haven’t had any real issues with health or money. It just sucks and I miss being around people.

Danny: Yeah same. I’m literally today just getting my sex drive back. Maybe that’s why I thought of you lol.

Me: Haha, that’s relatable. I’ve had a similar libido slump from the depression caused by this shit show. I thought about you last night and was thinking about texting you, so maybe you sensed my thoughts somehow.

Danny: I wasn’t even jerking off. I had no libido. The girl you met in NY started sending me sexy videos tonight and I was getting worked up, then my boss called with Rita Ora and Alicia. It was so surreal. And then I started looking up pictures of Rita while I was on the phone with her and well… And then I thought of you. That’s a compliment.

The clock struck ten, and I began my chat with Lily. It was hard to ignore Danny. I missed him, in spite of how annoyingly self-absorbed and inconsiderate he can be. It was nice catching up and being compared to Rita Ora, but he wasn’t paying me for my time. Lily was.

Danny: Did I lose you?

I had been so nervous planning out my call with Lily. I wanted to venture into the sexual realm without hurrying or causing her to close off. I didn’t imagine she wanted to jerk off together yet. How does one cam for women? I decided to approach the problem creatively, tapping into old memories of when I first stumbled into my own sexual exploration. I settled upon strip poker, conceptually. I had long forgotten how to play poker. My step grandfather had taught me years ago. He’d wanted a poker buddy and knew I had a head for strategy. But in the decade and a half since, I’d completely forgotten how to play. What game could Lily and I play remotely that I could turn into a stripping game? I searched online for gaming platforms. It had to be something easy, that wouldn’t completely have us wrapped up in complex problem solving. It also had to be short enough that we could play about three rounds over the course of fifteen minutes. The point of a stripping game is to actually strip, not play games in layers of clothes. After a number of failed attempts, I finally settled upon using Game Pigeon, an iPhone Messenger plug-in. I was worried it would eat up our bandwidth, but it was the least complicated solution I could find for the moment. I texted Lily in preparation.

Me: Wear layers.

Lily: Got it!

Then I flipped over to Danny.

Me: Hey sorry, I’m camming. I’ll be done in an hour and can respond then.

Danny: Really, you cam? Damn, send me a link. What are you doing? Naked? Screenshot?

Lily popped onto my screen, leaning against pillows and an offwhite wall. After some initial technical difficulties downloading the app from my invitation, we began. Game Pigeon is typically used for semi sporadic game play. You can challenge a friend to any number of child friendly games from Cup Pong (vs. beer pong) to Paintball (as opposed to a proper gun shooting game). There are no winnings or wagers. Sometimes a game passes quickly, sometimes a game goes on for days. I was hoping we could finish each game in about five minutes. For our first round I chose Connect Four. It wasn’t completely mindless, but it wasn’t too involved. I also felt that I had a decent chance.

I didn’t know how she would take the idea of stripping with me, a stranger on the other side of a screen. We didn’t really know each other. My greatest concern was rushing her. Going into an intimate space after losing a partner can be triggering. I wanted to keep everything low pressure. We weren’t shooting for orgasms, just play, teetering on the edge of arousal.

Lily: We must do it for all those that went before us and for the love of the game.

I heard a ping as my laptop displayed another message from Danny.

Danny: Let’s share screens. I asked her to lay 3 panties out and I would pick.

Danny sent me a picture of three thongs against white bedding.

Danny: Which one did I pick?

I couldn’t focus with Danny twittering in my ear. I muted my laptop to focus.

Lily immediately bested me in our first round. I was bundled up in a jacket with long white satin gloves and thigh high stockings under a short skirt. I removed one glove and threw it over my head. Lily laughed, her eyes glinting with blood lust. I could sense that neither of us were accustomed to losing. This would be a proper competition.

Lily: It feels really good to start with a win like that.

Me: You did great playing a game that requires skill, but what about a game that requires no skill at all?

The next round we played Cup Pong which is a swiping trajectory game.

Lily: This brings me back. I went to UCSD which is kinda a party school, not gonna lie. But instead of beer pong we played quarters, which is essentially the same thing. But I never really got the point.

Me: Why?

Lily: Because the point was to drink, right? I like beer. I was playing to drink, so it makes sense to just miss the cup so I get to drink it.

Me: Okay, true.

I was surprised by how invested I found myself in winning these silly games, and how sensual the game play became. We teased each other, snuck glances at the other while she was making her move. I watched Lily’s intelligent face calculating her moves, registering when she knew ahead of me that I’d lost a round.

I won Cup Pong. Lily won Tanks. I won Mancala. Lily won Knockout. I won Anagrams, Boggle, Darts, and Paintball. Lily took my jacket, both my stockings, and my skirt. I realized belatedly that I had forgotten my bra, which leant the final rounds a degree of necessity. I took Lily’s jacket, her socks, both of her shirts, and her pants. The next round would determine whose tits flew out first.

Lily: I don’t like seeing all of these red “X’s” by my name.

Me: Think of them as the clothes I’ve taken off of you. And to be fair, you’ve taken plenty off of me too.

We were both quite vulnerable, even though we were miles apart interacting through our screens. I was self-conscious. I’d put in effort for the date, but I still felt unsure. I wasn’t dressed like Selena exactly. I didn’t have long fake hair on, or high heels. I hadn’t shaved my entire body. There’s something centering about the rituals of preparing to perform sex work. It gives me time to focus my mindset and tap into my “mortal men don’t deserve me” energy, but performing for Lily required a different sensitivity. I wasn't entering into our session believing I was better than her, or having to assert that kind of dominant energy. I could come as myself, and in this instance, myself was better than any hyper identity. I still had her call me Selena, just for continuity. Even if this business was more personal, it was still business.

For the final round, I challenged Lily to a Connect Four rematch. It was tense, each of us setting our own traps for the other. I admired her planning, and she amusedly studied mine. In the end it became a waiting game. How could we fill the board while avoiding the other’s traps? I counted the slots leading up to my first trap. Her, then me, then her, then me, then her-- and finally she would be forced into my victory. I sat back, content with myself.

Lily: Oh no!

Me: I know.

Lily: This is terrible.

Me: You’re gonna show me your tiddies.

Lily finished the game. The final crown went to me. She made a half-hearted sour face at me. She wasn’t entirely upset at the outcome. She still had her panties on which meant we could do another round, but it had been nearly two hours, and she was paying me for two hours what people typically pay me for eight minutes. I was happy to do it, but if I continued any longer, it would be like I was working for free. Lily lifted her bra and her breasts flopped out. I had won, but she was winning too. She smiled wryly at me.

Me: We’re gonna have to leave it there. How are you feeling?

Lily considered, thoughtfully.

Lily: Surprisingly good. Although I didn’t like losing, I had a lot of fun.

Me: I’m so glad. I’m going to let you get dressed and all, and I’ll text you the payment information.

Lily: Okay. Sounds good. Thank you.

Me: Thank you for being so vulnerable with me.

I hung up and began getting dressed too. It had gone well, I thought, which was an incredible relief. I hadn’t been that nervous to perform sex work in a while. But my creativity had paid off, it seemed. And I was more surprised because I’d gotten turned on in the process. I enjoyed watching Lily. It was her cleverness and coy flirtations that had gotten to me. I felt open in a way I hadn’t experienced in a while.

The next day Lily texted me.

Lily: Thanks again for last night. I love that I get to say I played Strip Video Games for my first SW experience. But I might not share the part about how I lost... my favorite parts were how seriously we took it, your focused face and that you laughed with me (I love it when I get to laugh at work. Feels like a win-win). I’m definitely interested in seeing you again and anything we do in between via text. That actually pushed me, I’ve never even played strip anything before and I wasn’t sure I’d go through with it. Of course, the thought of winning and what I’d win did help. Plus doing it for all those that went before us and the love of the game.

I was touched, and the affirmation that she enjoyed the experience I’d improvised was heartening. We scheduled to do another session the following Saturday.

It’s not something that would have happened without the quarantine. If life was normal, I would have been working one of my marathon shifts at the club on Saturday. Even if I felt an immeasurable internal satisfaction for this, in the end my work is driven by money. In a way, I’m grateful that everything stopped and allowed this moment to happen.

***

The following Saturday, I returned to my studio running through ideas of ways to continue my creative streak with Lily. I was anxious. How could I top stripping games? Where was there to go next? Would she get bored if I recycled the same ideas? I hit up my stripper homies for some advice. In my close group, everyone is very queer. I’m queer, but still scared someone will take away my queer card for dating so many cis men. Starr suggested I focus my session on edge play. Edge play is just delaying a sub’s orgasm, but it can take a number of forms, from simply determining how your sub is allowed to masturbate; physically jerking off your sub and stopping before they can come; setting limits for how long your sub can masturbate; to inflicting pain to delay orgasm, just to name a few.

Starr: You should train her on How to Have THE BIGGEST NUT !!!

Me: OMG YOU’RE RIGHT. That’s such a good idea.

Starr and I bounced a few ideas off of each other. They’re much more experienced with queer camming, and I appreciated their expertise. I had an angle, but what was the hook? Did it need a hook? Could I just sit in front of her and tell her when she could use her vibrator and for how long? Insecure as I was about the situation, I decided to wrap it up into a little game, and wrote up a list of rules:

The L Word Trivia Edging

Miss Selena is going to train Lily to have the biggest nut.

Lily has to answer 10 The L Word Trivia questions correctly for Miss Selena to allow her to use her wand for 20 seconds.

If Lily wants to watch Miss Selena use Miss Selena’s toy while Lily uses her wand, Lily must answer all 10 in a row correctly, and then Miss Selena and Lily will both use their vibrators for 20 seconds.

Lily has the option to play to double the stakes by answering 15 questions correctly.

If Lily answers those 15 correctly, then she gets to peek at either Miss Selena’s pussy or tits during her 20 seconds with the wand.

Lily doesn’t get to cum until Miss Selena lets her. Lily must ask Miss Selena for permission to cum.

When Lily wants to cum she has to say, “Miss Selena, may I please cum?”

I felt quite confident with the rules, and I’d pulled up a website with six pages of The L Word trivia questions. I’d picked The L Word because Lily had mentioned that she enjoyed the show enough to get off to it sometimes. I read through the questions to see if I could answer them, and decided there were enough easy ones that even I could do fairly well. I was ready to roll.

The only problem was that Lily wasn’t ready to roll. It was soon apparent that Lily hadn’t watched The L Word in a while. Even questions I thought were kinda basic weren’t on her radar. I panicked internally. I’d put all of my eggs into this one basket of Lily knowing some kind of trivia, and it wasn’t working. I kept smiling, giggling to play it off.

Me: Well, haha, what movies do you know pretty well *hehe*?

I asked, searching for a solution.

Lily: Well… Hmm… I guess if I had to pick one, I’d say Star Wars.

I held my breath. I knew I could find a million and one websites dedicated to Star Wars trivia, the question was whether or not Lily actually knew her stuff when we got down to it. I found a page with multiple choice trivia questions and shortened the requisite to win a round from ten correct answers to only five, eight for my participation.

It was clunky, and less successful initially than our first session. Trivia knowledge is difficult and definitely taps into an un-erotic part of her brain. The carrot was still there, but recalling facts from old movies beyond general plot points requires too much complicated thinking. Thankfully we had our vibrators to turn down our high minded thinking.

Lily did surprisingly well. There were a number of questions where she made educated guesses and got lucky, but she also knew a decent amount about Star Wars.

Lily: Never would I have thought my Star Wars knowledge would come in handy to get off.

It was so joyfully nerdy. I used my clitoral suction/licker toy to play with myself while she used her Magic Wand.

Lily: I’m sorry, it’s really loud.

Me: That’s fine, I have a wand too and it’s also really loud.

Lily: But mine is really loud.

She flicked it on. The wand sounded a bit like it was on its way out, but as a happy owner of many loud sex toys, I wasn’t phased.

Me: Ah, that’s nothing.

The game was entertaining, even though it wasn’t as elegant as I’d hoped. The five-question requisite got whittled down to only two, three for my participation. An hour and a half in, I decided it was time to ditch the trivia and focus on orgasm control. I pulled up a timer and began the final circuit.

Me: ...And… Start.

Twenty seconds later

Me: Stop… And… Start.

Twenty seconds later

Me: And stop… We’ll start again in ten seconds… Five… And… Start!

I watched her get closer and closer, a look of excited frustration pursing her brows.

Lily: Miss Selena, may I please come?

Me: You may.

I watched her search for her orgasm. In a way it had been much closer when I was keeping it from her. When I set her free, things became more difficult. Finally, she reached her climax.

Lily: Miss Selena, may I come again?

I was pleasantly surprised.

Me: You may, but only if you’re able to cum when I let you use your vibrator. I’m going to time you again.

I began counting intervals again: twenty seconds on, ten seconds off. I could sense her building. When she was on the precipice again, I stretched the twenty seconds to forty seconds and watched her come. As she finished, two perfect tears slid down her cheeks. She sat with her eyes closed, quietly sniffling, trying to form words. I waited in silence, witnessing, holding space.

Lily: They’re happy tears.

Lily said, brushing them away, only to find new tears in their place.

Me: I know. Tears are good.

Lily: They are. The first one was kinda “meh,” but the second time was, well, pretty huge. So I’m still... ya know--

Me: It’s okay. I’m here. No rush.

Lily cried quietly. I knew it was just emotions bubbling up, released as she’d released bodily. I’d half expected it going into the session that evening. I was surprised by how trusting she’d been with me.

Me: What was your partner’s name?

Lily: Cassandra. Her name was Cassandra.

Me: How long ago did she pass?

Lily: January, near the end.

Me: That’s so recent.

Lily: Yeah. It feels like it’s been forever, but also like it happened just yesterday, if that makes sense.

Me: Totally.

Lily: I just know she would be happy for me right now. Before she died, she would always say that she couldn’t wait to see who I’d date after her. She didn’t know if it’d be a man or a woman or anyone else. She said that the next person would be lucky because she’d made me into a better partner.

Me: That’s so beautiful.

I began tearing up. We cried together at the purity of Cassandra’s care. I couldn’t fathom her loss, but Lily’s strength touched me. She was trying to open her body again. I felt lucky to be part of her healing. We talked for a while more, until the conversation migrated to Zoom conference calls and managing quarantine cabin fever.

Lily: Since I can’t leave, I decided to rename the parts of my house so that I feel like I’m in other places. The couch is the break room. My desk is the office. My kitchen is the cafe. The bathroom is the spa. I have a mat on my floor I call the dojo. I haven’t settled upon a name for the bedroom, but I’ve been thinking about calling it my quarters.

It was a poetic way to liberate her mind. I carried her gifts with me and wished her goodnight.