Work in Progress

"Okay," Caitlyn said. "Let me try to explain that a little better. I mean, on the one hand, it's exactly what you think it is. Men pay me for my time, and it almost always leads to sex."

"Sex," he repeated, sounding like a deflated balloon.

"The escorting does, yes. Pretty much everything I do revolves around it somewhat. I have an audience, and they... uh... They support me. I don't compare numbers, but I think I do okay. When I cam, I announce it on Twitter or OnlyFans, and it's often the same people that come to watch. Men, mostly. There's a lot of overlap across platforms."

"And they..."

"...and they... pay me for sex?"

Phillip nodded slowly.

"Yes," she said, feeling quite proud of the gusto with which she delivered her answer. "Some of them, anyway. The ones that are local enough. A couple of men have offered to fly me out to different places, but that's a whole other thing. I don't get involved in any of that. You know, what I do now is illegal enough. If I started crossing state lines for it, I'd be getting into felony territory."

"How much trouble could you get in now?"

"Um," Caitlyn said, smiling and biting her lip. "Some? Definitely some. The other things, the camming and the videos and whatnot? That's not... That's fine. There's no problem with those, but they don't... They aren't enough? Like, not enough to live on."

"So it's a money thing."

She tilted her head back and forth. "Yes and no. I'm, um... I'm really..." She laughed a little, to herself, and shook her head. "There's a lot of reasons. Money, yes. Sometimes I can convince myself, just a little bit, that some of the things I'm doing help to... normalize sexuality? And being trans? Sometimes, it's more about being a part of something that gives other people joy? If that makes sense? Like, I'm pretty empathetic, and there's a whole aspect to what I do that makes me feel incredible when other people get off. Like, it can be very fulfilling... but also money."

"Uh huh," he said, somewhat lacking in enthusiasm.

"The escorting is pretty lucrative. I've worked up a fairly regular clientele. I live in a closet of an apartment, keep my bills pretty low, and I'm investing a lot of what I earn."

"You invest?"

"Yeah," she said, laughing. "This isn't a forever job. I've been doing it for a few years, and if I keep doing it for a few more I'll be able to retire pretty early. Or at least, retire from escorting."

Phillip blinked at her. "Really?"

"It's not glorious, and I have to be a bit of a miser sometimes, but yeah. Really."

He stared down at his hands for a moment, and then looked up and asked, "What kind of videos do you shoot?"

***

"—and I just... I couldn't stop crying. My life was a lie. I'd been living a lie, and it felt horrible. I was..." He shook his head as he drifted to a stop. "I said I wouldn't do it, but then I went ahead and made it about me anyway. God. Damnit."

"I asked," Caitlyn said, her voice still rough.

"Yeah, but—"

Caitlyn held up a hand again, and he fell silent. "Take a deep breath," she said, and then added, "Wait."

Phillip looked lost when she shut the door, though he looked at least a little relieved when she opened it back up a minute later and handed him a bottle of water. He nodded gratefully and took a long sip.

"I needed a minute to catch my breath," she said, with a slight nod, "and I thought you could use one too. Then I... I don't know. I felt like I should give you something."

"So you gave me water?" he said.

"It felt like the thing to do," she said, managing a very slight smile. "You'd already done a lot of talking, and I know that whenever I get to talking like that my throat gets all dried out and I'm like where's my water?" She laughed nervously. "And then that first sip usually feels really good. Am I babbling?"

Phillip just looked at her.

"I'm babbling. That's not good. I get flustered sometimes." She took a sharp breath, in through the nose, and met his gaze directly. "I forgive you."

That knocked the pretty smile off his face. "What?"

"I can accept that you're... still working on yourself. You're not finished yet." She held out her arms and looked down at herself. "I'd be a pretty big hypocrite if I didn't accept that people can change if they really, really want to. I mean, look at me."

Phillip gave a sharp, chortling cry, and nodded.

"I can accept that you maybe have some things you'd like to put behind you? Right?"

"Yeah," he said, smiling through a light sob.

"Okay. Done."

"Just like that?"

"Just like that." Then she smiled broadly and looked up at him. "Would you like to go get a cup of coffee?"

This time, it was Phillip's turn to be startled into silence.

***

"You know," Phillip said, "it's a little bit like being in a poly relationship."

Caitlyn squinted one eye shut and leaned back, exhaling audibly as she did. "Uh... I'm not sure how I feel about that analogy? I mean, I know what you're saying. From your side, sure, that's probably accurate, but there's this whole thing that I have to be really careful of called a... a parasocial relationship? Do you know what those are?"

Phillip shook his head.

"A big part of what I end up doing is functioning as, like, a surrogate girlfriend. Half of one, anyway. I listen when they've had a bad day. Especially with the phone sex. Some of those guys want to talk for, like, hours at a time. Very little of it is actual sex."

"Okay," he said, even more slowly.

"I'm not... I don't think I'm explaining this well. They can get attached to me, and feel entitled to my attention, and I'm... attainable. You know? I'm not anonymous on the internet. They can find me, so there's always some risk for me with stalkers and fans with unhealthy obsessions. Most of them aren't like that. Very small percentage are weirdos. The rest of them, though, or at least a really big portion of them, love telling me that they love me, or that they care for me, or that..."

Caitlyn snickered and rolled her eyes. "...that they want to save me. That's the big one. In the moment, my response is always supportive and, you know, vaguely positive. They want to see that saying those things makes me happy... and then that's the end of their involvement. They get off on me wanting them.

"That's the fantasy, right, but then the reality is that, like, if I'm scheduled to cam one day and I feel sick and cancel? I won't get a bunch of messages checking up on me, you know? No real inquiries about my health. Gosh, no! I'd get 'Hope you feel better by tomorrow, sweet cheeks. Can't wait to see you again', and that's not the same!"

"Huh," Phillip said. "Okay. I can see that."

"I put a lot of time and energy into being with other people, and making them feel good, and that's nice in its own way, but none of them are really making that effort back. That's why it's not really like being poly for me."

Phillip leaned his head back, like half of a nod, and made a long, drawn-out, "Ooooooooooooh. Okay. That makes sense."

"If being in a poly relationship is how you want to think about it, that's fine. I just... thought you'd want to know it's not the same from my perspective."

"So what would it be like for you?"

Caitlyn licked her lips and shrugged. "I don't know? Going and getting coffee with you was the first time I'd been on an actual date, where I actually wanted to be there just for myself, since I started transitioning. I have no idea what dating will look like." She paused for a moment, thinking, and then added, "And I think that's okay. We're still figuring things out, right? We don't need to have all the answers right away." She blushed, and her head shrank back into her shoulders.

"Now I'm curious," Phillip said, turning on the couch so that he was facing her. "What is it like?"

"For who?" she said, giving him a sly smile. "Them or me?"

"I-in general."

Caitlyn licked her lips, and then ran her tongue back across the tips of her teeth. She couldn't help but notice that the new way he was sitting shifted his pants in such a way as to hide what might be an erection. She couldn't be sure, but it was cute either way. "Well... Not sure how this is going to go over but here we go. I saw two clients earlier."

"Earlier... today?"

Caitlyn nodded. Her curls bounced against her shoulders.

"Before you came here?"

Caitlyn nodded again, watching his face very closely. When he started stammering, she held out her hands and saved him from himself. "The first guy is a bit of a regular. I see him every few weeks or so. I'll get there and he'll be wearing just a towel around his waist."

"Just a towel?"

Caitlyn nodded. "I tell them, ahead of time, that they need to make sure they're clean before I get there, but this guy always wants to meet me while he's still glistening from the shower." She snickered and rolled her eyes. "He's all business. Very little talking. I excuse myself to the restroom, where he'll have put the money, and then when I come back out it is go time."

"Go time!" Phillip repeated, emphatically.

"He wants me in a skirt, and he'll just... bend me over whatever is nearby."

"Wow," Phillip said. "Is it weird that that's hot?"

This time, Caitlyn rolled her eyes a little more obviously. "Go time usually lasts for about two minutes. He cums, like, right away. Then he'll say something like Oh, you were so amazing! I better let you go now, or I'll keep you here all night!"

"Wait, what?"

"He literally said that, to me, today."

"That's such a cliche!"

"Cliches come from somewhere," she said with a shrug. "I have a few like him. It's always the same."

"What about the other one?"

Caitlyn licked her lips again. "The other guy was a first time, but I've had others like him before. They all want the..." She narrowed her eyes as she looked sideways in thought. "They want the Girl with a Dick fantasy."

"I'm learning so much tonight," Phillip said, with a laugh. "What does that mean?"

"It's a lot of me penetrating him, instead of the other way around."

"You do that?"

Caitlyn shrugged nonchalantly, and said, "What can I say? I'm a woman of many talents."

It was really wonderful to hear Phillip laugh so earnestly. It was also very encouraging.

"This guy today wanted a bit more than that too. He wanted me to, kind of, like, compare sizes? If you know what I mean?"

"Dicks?"

She gave him two finger guns and laughed. "He'd seen my cam shows. He knew going into it how that was going to end. He, uh... he wanted to be humiliated a little bit?"

"Whoa."

"The first guy took, like, ten or fifteen minutes. The second guy took over an hour. I had to keep going and going and going."

"Right," Phillip said, his eyes brightening, "because you were the one—"

"Yes," she said. "I was doing all the work."

"You can stay hard for an hour straight?"

"I can," she said, shrugging. "Sometimes. With guys like him, though, I don't even try. I just take a pill. It avoids uncomfortable moments for both of us."

"And then... you just kept going until he finished?"

"Well, not exactly." Caitlyn felt her skin getting hot as she ran her tongue along the inside of her gums. "He had a whole fantasy. He laid it out for me in a couple emails, and we went through it."

"Are you able to tell me about it without breaking escort-client privilege?"

Caitlyn laughed, loud and long, and Phillip's pleased smile did really nice things to his face. "He wanted me to take pictures," she said, once she'd regained her composure. "And some video... of him going down on me. Of him, getting... you know..."

"Fucked?"

Caitlyn nodded. "Yeah. That. Doggy style, and then on his back. He didn't give me specifics on the how, just that he wanted it to have a 'blackmail' kind of vibe to it. So I told him I was going to put it all up on Pornhub with his face still slightly visible, and the embarrassment was what finally pushed him over the edge."

"Oh my god," Phillip said.

"I'm not really going to," Caitlyn said, laughing. "I sent him copies, encrypted them and backed them up, and deleted them from my phone. He loved it." She gave a little self-satisfied smirk and sat up a little straighter. "He'll want to see me again in two weeks. Mark my words."

Phillip ran his finger over his chin pensively. "So what's the... what's the protocol? How does the rest of it work?"

"Well, they pay up front. You only ever get burned once with that kind of thing. I call my sister before and after every client. Give her their details, and how long I think it's going to be so she can expect my call afterwards."

"Do you usually know how long it's going to be?"

Caitlyn bit her lip and smiled. "Most people who do this are either really good at reading people, or else they get good real quick. It's the only way to survive." She grabbed the pillow in her lap and gave it a good fluff to give her hands something to do. "Always use condoms. I don't mess around. Anyone who sees me regularly, I ask that they get themselves tested for STDs. I get checked too. Clean bill of health as of last month, by the way."

"So here's the sixty-four thousand dollar question. Does your sister know that you're here?"

"Yes?" Caitlyn said, as the word turned into a laugh. "She thinks you're a client though, and, before you start reading into that, because who wouldn't, it's really important for me to point out that my sister... looks out for me. I am vulnerable to being exploited. Sometimes it can be hard for me to keep a healthy level of objectivity. If she knew I was just coming here to see you and not as an appointment, she'd start asking a lot of questions." She shrugged, and felt the color rising in her cheeks. "I wasn't sure I had any answers. It's... this is too new."

"I told my sister," he said quietly. "That I was, maybe, seeing a trans woman, I mean."

"You did?"

"Erica has been the one helping me stay on task with my, uhm... with my apologies? We're pretty close. Anyway, yeah. I uh... I told her about you."

Caitlyn drew the pillow tight against her body, and took a deep breath. She hadn't expected him to take a step like that, and it left her feeling unbalanced. "On the one hand... that is..." She had to stop and compose herself. "As a trans woman, it means a lot that you did that. That's... it's not very common that, uh, that men are open about... about seeing someone like me? You know, I... I haven't really dated, but I hear things. I go to a support group sometimes." She swallowed hard. "On the other hand... do you think you'll tell her that I'm a sex worker?"

Phillip paused there, and Caitlyn nodded.

"It's okay. I know I'm hitting you with a lot." She held the pillow a little tighter, and smiled as she looked down. "I have to hide parts of myself all the time. I don't tell anyone either, really, about being a sex worker. The only time I can really be myself is when I'm alone. Other people don't understand, and... and that's okay! I don't hold that against them! I won't..."

She had to swallow before continuing. "I won't hold it against you if this is too much, and-and don't... don't try to rush to say it's okay when it's not."

His blank expression said she'd likely caught him about to do just that.

"I know you probably had some different ideas about what was going to happen tonight, but I wasn't going to let anything more happen until you knew and had some time to think about it. I know it's a lot."

"It's definitely something," he said, with a nervous chuckle.

"I haven't even gotten to most of it yet. I mean, the reality of it, behind the scenes, is a lot. I haven't quite been able to afford laser, so I have to be pretty meticulous about body hair. There's, like, a lot of expectations. I bleach my asshole."

"You what?!"

Caitlyn nodded, managing a more natural smile again. "Yeah. You would be surprised how a little bit of bleach changes the way people react. Like, in some ways, I end up doing for my own mental health! I would much rather have guys telling me how-how cute my little pink pucker is than how much they want to, you know, stick it in my dirty shithole, and it doesn't even change that much! Not really!"

Phillip's jaw dropped, and Caitlyn laughed.

"I'm telling you," she said. "What they say to me is a reflection of what they see, so I have to have my guard up all the time. I have to present a very specific look. Smile real big. I have to be careful to dodge what I do when I'm talking to people in public. I have to work out to maintain a very specific appearance, because my look is my brand. Sometimes, when I'm alone, thinking about that screws with my head."

"I'd... never... thought about that," Phillip said softly.

"You know, when I got home after that coffee, I cried because... because you were so nice. I'd almost forgotten what it was like to get a little intimacy back, you know? Some thoughtfulness?"

"Is that so uncommon? That people... hold the door for you? That kind of thing?"

"That's the thing about nice guys," she said, tenuously holding his gaze. "They don't even know when they're doing it right. It just comes naturally."

Phillip blushed and scratched at the back of his head. "Thanks? I think?"

"You are the only person who has ever caught me not answering a question. Ever."

"Come on," he laughed, still looking a little nervous.

"I'm serious. For my clients, it's all about them. I am a hired gun." She tapped the pillow with her index finger in time with her enunciations, to hammer home her point.

"That sounds lonely."

Caitlyn smiled and nodded. "Yeah. A little. For a while there, I didn't really notice. I kind of fell into doing this when I was transitioning, and it was a really good fit. I could work around the stuff I was doing with my doctors and, for some of my audience, seeing that happen bit-by-bit was part of the appeal. It kept my ego going when I was in kind of a low place, you know? Not feeling really great about how I looked when I was... in between?"

"I have to admit," Phillip said, "that it's... there wasn't any kind of... like..."

Caitlyn bit her lip as he fumbled.

"It was a surprise," he said, after another few seconds of laughing at himself, "when you opened the door, but also, not a surprise? Like, you looked like yourself, if that makes any sense."

"Aww, that's sweet," she said reflexively.

"Did you just do it again? That thing where you deflect?"

The more she thought about it, the more Caitlyn's heart swelled, and she had to tamp down on it pretty hard to keep it from showing. Then she laughed and put her face in her hands. "You know, I've had to be careful not to let compliments and attention feel like affection, and it's a little disorienting to let stuff in. Like my first instinct now is not to trust it. How crazy is that?"

"It makes sense," Phillip said. "You're... protecting yourself. Protecting your heart."

"Yes!" Caitlyn said, gushing.

"Seems to me that, more than anything, that's trust. Right?"

This time, she nodded thoughtfully. "Trust is a big part of it, yeah. Maybe."

"Okay," he said. "Okay. Trust doesn't happen immediately. I can be patient."

Again, Caitlyn had to pause to catch her breath. "You know, for a long time, I didn't realize how lonely I was. When I first got started, the compliments were so... alluring. It took me a while to see through that and realize that there are other parts of my job that I really like. Now I focus on those, and it's really rewarding."