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Two encounters go in very unexpected directions.
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AwkwardMD
AwkwardMD
1,325 Followers

Caitlyn held the phone up, keeping her eyes on the road, and said, "Okay. Period. I'm. On. My. Way. E. T. A. Twenty. Minutes. Period. Send." She had to hope that saying it a little slower would prevent any embarrassing speech-to-text mess-ups, because she didn't have the attention to spare for a double check. "Call. Tori."

Her sister's speakerphone-altered voice came through a moment later. "Hey. Eighty-seven minutes. Almost got that one on the nose."

"Technically, it was seventy-two when I got in the car. I knew sixty wasn't going to be enough, though. Not with his type."

"How did it go?"

"It went fine!"

Tori was always pretty deadpan, but she was as flat as a pancake when she said, "What happened?"

Caitlyn sighed. "Nothing bad. It just... took longer than I was hoping it would."

"D'ya think he whacked it before you got there?"

"Stop!" she said, giggling melodically. "He was very nice! Paid for extra time and everything! I didn't even need to ask!"

"That was going to be my next question."

Caitlyn laughed even harder. "My sister, the pimp."

"Don't make it weird," Tori said.

"You're the one who printed your own pimp business cards!"

"Yeah, but it was funny when I did it. You're too... genuine to make jokes."

Caitlyn rolled her eyes and made a noise in her throat. "Hey, are you streaming?"

"Yeah, but I've got it muted and I'm safe from the storm. Are you on your way to the last one?"

"Mmmhmm." She bit her lip. "Are you ready?"

"Go ahead."

"Phillip Levy. 213-555-8127. 2600 Marguerita Ave, Apartment 521, Alhambra, 91801."

"Ew. Alhambra. That's a hike."

Caitlyn laughed nervously, hoping it didn't sound nervous, as she pulled onto the I-10 exit ramp. She was glad she was getting off before full twilight set in with the number of cars going the other way on the freeway. Oncoming headlights were always a headache risk.

"You should have gone to this one second since you were up in Highland Park earlier. Could have just done these in a line instead of driving all the way down and back, and then driving all the way home."

"Oh yeah," she said, dragging out the yeah. "That would have been smart."

"All right. I've gotta go. 60 minutes?"

"Mmmmm. Two hours."

"Whoa. Really?"

"Maybe. Too soon to tell."

"Okay, well, I got the timer going. Be safe."

"You too!"

Caitlyn's nerves were firing like crazy as she sat at a red light. She gripped the steering wheel in both hands and tried to catch her breath. It was mostly butterflies, but she'd have been lying to herself if she said there wasn't more to it. When the light finally turned green, she hit the gas so hard that her tires gave a sharp squeal.

It was always nice going to Alhambra. She had to admit there wasn't much to it, technically; there were no destinations there. It was very much a poster child for Los Angeles averageness, but that was still comforting in its own way. Block after block of ranch houses, ancient strip malls, and tiny liquor stores, with the occasional oasis of modern shopping and fast food clustered at major intersections. It felt like it had been there forever, and that kind of stability was comforting.

The place was just as described. As she slowed down, she started checking out the second floor windows of the various buildings in the complex, and she had to come to a quick stop while still halfway out into the street to avoid hitting a little boy on a Green Machine as he rolled around the lot. The lights in the parking area were spotty, and she just barely spotted a reflective stripe on his shoes. He hardly seemed to notice her, and she just had room to pull into an open parking space in his wake.

She checked herself in the mirror as she sat. Her shoulder-length curls still had a lot of volume, which was perfect. Her makeup was mostly gone, which was fine. She touched up her eyeliner briefly. Her oversized, Gold's Gym cutoff tee and sweats were the epitome of comfort. When she looked down and remembered that her tennis shoes had some bright 80's coloring, she realized she'd inadvertently given herself kind of a Flashdance vibe. A little on the nose, but still; it was a good look.

Her mind was a million miles away, deep in the past, when she got out of her car, and it was the strangest little tickle that brought her back: the silver SUV parked next to her starting up. She blinked and looked around, and started slapping the side of it when it lurched into reverse.

"Stop!" she shouted, whacking her open palm repeatedly against the fiberglass. "Stop!" She darted around the end of it just as the brake lights flared to life and there, wide eyed, was that same little boy. She scooped him up in her arms, though he was really too heavy for her to do much more than hold him to her chest and stand, and scurried out into the middle of the lot.

"Oh my god," said a man behind her. Dark, thick hair. Moustache. "Jer?"

"He's okay," Caitlyn said.

The boy was mostly still in her arms, looking confusedly at the two of them.

"I would have hit him!" He said something in another language, something she would have guessed was vaguely eastern european, and though she did not know what it was or what he said, it was most definitely a curse. "Jer, where is Ephraim?"

The boy shook his head quietly.

"His brother usually watches him this time of night. They live in apartment below me."

Caitlyn held onto him tightly, but the boy relaxed in her arms and turned more toward him.

"Does your brother know you're out here?"

Again, the boy shook his head.

"Mother works two jobs," the man said, shaking his head. "Poor woman. Come, Jer. Let's go see where your brother is."

The boy immediately reached for his hand, and Caitlyn took the boy's familiarity with the man as a good sign. He gave her a wave as they headed for a staircase, but still that wasn't enough. She stopped at a helpful building map, which she actually did need to read, but just stared at it blankly while she waited and watched in her peripheral vision. There was quite a commotion when the two of them reached the third floor, and she finally felt that knot of worry unwind when the man came back down the stairs alone.

As it turned out, half-heartedly staring at the building map had not been enough. She had to really lean in to read the apartment numbers and get her bearings. From there she proceeded one building over and up one flight of steps, screwed her courage to the sticking post, and knocked three times.

***

"Thank you, Raj. Thank you, Dino!"

Caitlyn blew two kisses at the camera, winked, and slipped her cum-covered index finger back into her mouth just as she cut the session. A good chill went up her spine as she stretched and twisted. Her Danaerys costume had been a big hit despite being nothing more than a wig and a dress. The dress hadn't even been particularly fantasy-ish. She made a mental note to do more promoting ahead of time whenever she was going to do a whole scene in character. She'd have to figure out what the sweet spot was. Too much notice, and her audience would forget. Too little and they wouldn't be able to make arrangements. Maybe she'd ask them in a poll to see what they thought was the right amount of notice.

Then maybe she'd run a poll to see who her commissioners wanted to see her perform as. She owned a yellow cable knit sweater, so that was half of a Velma Dinkley costume. She'd done a little bit with costumes before but never in character, and it was fun seeing the different reactions.

She stripped out of her dress and tossed it in the pile. She hadn't meant to get cum on it, but her ejaculation had been even more dramatic than usual. The extra tips would more than cover having to get it dry cleaned already.

Her scalp was damp with sweat as she unpinned the wig and shook out her curls. Then she sat down on the mattress, nude, and flipped through her phone. She set up a transfer from one account to the other and set a reminder on her calendar for the next day, once the transfer was complete, to find a home for those funds. Maybe something in the tech industry this time.

Her Pikachu onesie pajamas were calling her name, so she quickly dabbed around with a tissue to make sure she was all dried off. Then she slipped into them, pulled the hoodie up over her head, and took a few selfies for Instagram.

All cozy after a long hard session. See you boys next time! ;)

She could be a little more explicit on Snapchat, crossing her eyes with her tongue out and substituting 'session' with 'cum', and her phone was erupting with responses even before she made it into the kitchen. She would take a couple hours for herself, unwind, and then maybe take some phone calls in the evening.

She laughed when she found the cup of tea she'd made for herself still sitting on the counter, having steeped for over three hours, and popped it into the microwave to warm it back up. She was leaning against the kitchen counter, watching the mug rotate, when there was a knock on the door. Her apartment was so small that she was only a couple steps away...

...and the man standing in the hallway, when she opened the door, was just about the last person she'd expected. There was an instant fear reaction that was hard to logic her way out of. He looked older than he had the last time she'd seen him. Bigger too, which was not a good thing. He'd been plenty big enough to terrorize her in high school, and adding four or five inches and forty pounds of muscle only made her feel smaller.

Her tongue tried to retreat back into her throat, but she had just enough air in her lungs to croak, "Phil?"

He thrust out a hand and her initial reaction was to try to close the door first, but at the last moment she realized that he was holding something. Handing it to her. It was an envelope, and it was addressed to her dead name.

***

Clean shave. Shirt and pants crisp. Gel in hair. Smell of mouthwash. Controlled presentation.

"Cait!" Phillip cried, as he opened the door. "Come on in!"

"Sorry I'm late," she said, beaming, as she slipped into his apartment. "My last client kept me busy. I'd even tried to get there early, knowing he would probably run over time, but it still wasn't enough."

"No, no! It's totally fine. The food just got here! Are you hungry?"

Caitlyn smiled broadly. "Starving."

Apartment spotless. TV on, but show not paused. At menu, waiting to start. Movie title she had mentioned. Thoughtful.

Cologne. Not too much, but a strong scent. Sandalwood. Applied very recently. Just finished grooming.

"You said pad thai, right? And a spring roll?"

"Yeah," she said, as she followed him to the kitchen. "It smells amazing!"

Apartment large and open. All the lights on. Clear pathways. Furniture nice. TV new. Appliances new. Not rich, but not cheap.

"I found that movie you were talking about? Cabin in the Woods?"

Caitlyn turned to the TV and smiled, acting surprised. "Oh yeah! It's really good!"

"Would you mind if we watched that? I forgot that I'd already seen it, but I thought that might be okay in case we get to talking and miss some of it."

"Yeah, that sounds great!" When she was sure he was suggesting they eat on the couch, she added, "Can I have a couple paper towels? I'd hate to spill anything."

His eyes brightened as he looked at her, and that gave her a strange feeling.

They re-plated their food, moved to the couch, and settled in. There were plenty of throw pillows to build in around herself. Phillip turned off some of the lights, but only the ones that added glare to the screen. The rest he left on. She wasn't used to this much forethought and consideration from a gentleman caller, but she could certainly see herself getting used to it.

"So how was your day?"

"Oh my gosh, a full day!" she said, excitedly. "Woke up early. Had two Skype meetings before noon, and then two other clients after. Spent a lot of time commuting today, and traffic. Ugh! How was yours?"

Phillip tilted his head and gave her an unsure smile. "Why do I feel like you just told me absolutely nothing... completely on purpose?"

Caitlyn stared at him, jaw swaying slightly in the non-existent breeze, and cleared her throat. "Oh. Uhm—"

"I'm not trying to pry," he added quickly. "I just...." Then he blinked. "I don't know what I was looking for, really."

"No," she said. "It's okay. I... actually... I'm very careful with my clients and customers. I don't ever share any personal stuff with professional contacts, and sometimes I forget to turn that off. I'm... surprised you noticed."

"Do they not?"

"Never," she said with a shrug. Then she took a deep breath, smiled, and said, "Today was a little tiring, actually. I'm glad it's over. I don't want to sound like I'm complaining, or not up to being here. It's just that... they wanted a lot out of me today and that can be kind of draining. In more ways than one."

"Is it okay if I ask what you do?"

Caitlyn bit her lip and swallowed, which was hard to do given the huge lump that had moved into her throat.

***

"C****,

Thank you for even opening the envelope. I don't really deserve the chance to apologize, but I have to try. I am so, so sorry for how I treated you. There were a lot of things going on in my life, but that's no excuse. I made myself feel better by picking on you. For years.

The worst part is that you weren't the only one.

I've been carrying a lot of really awful guilt for a long time, and you would be right to think that I deserve it. Coming here today won't change how I treated you. This letter won't undo the things I did to you or put you through.

Your's wasn't the first letter I wrote, C****. It was the fifth. Dennis Whitehead punched me, and Anthony Fuches chased me off with a bat. My apology didn't get through to either of them, because they were just so angry. That's my fault. I have to live with that.

I hurt you. You're not weird, or stupid, or crazy, or any of the shit I used to say. You didn't deserve what I did to you. None of it. You were just one of the shortest. I picked on you because I could get away with it, and I want you to know that I regret it.

If you read this far, thank you so much. Again.

There's no easy way to step away from a conversation like this. If you just go back inside and shut the door, I'll go. If you want to scream at me, I'll listen to it. If you want to hit me back, I'll take it. Hopefully I stuck to the plan I had, and I've just been quiet while you read this. I think I've already said enough, and maybe it's your turn."

Phillip stood there, arms at his side and still silent. Caitlyn tried to compose herself, but it was a lot. Her head was spinning like a top. Not five minutes before she had been camming, and her high school bully was just about the furthest thing from her mind. The whole thing was deeply upsetting. She pushed her hood back, just for something to do, and ran her fingers through her curly hair.

"I... uhm..." Phillip scratched at the back of his head, and turned to look down the hall. "I know I—"

"Just stop," Caitlyn said, her voice cracking.

Phillip immediately looked up, brow furrowed, and his already-gloomy expression turned sickly as he took in her face. "Oh my god," he murmured, as he looked her up and down. "That's not your name anymore, is it?"

***

"First of all," she said, clearing her throat, "I want you to know that I was going to get into this tonight no matter what. I wasn't going to do it quite so soon, like not until after we ate, but... here we are." She turned, put her half-finished plate of food on the end table, and grabbed a pillow with both hands. It felt good to have something to hold. "I don't just have one career, I have several, and all of them are... adult-oriented."

"Adul—" He'd started repeating before his brain processed, and his face lit up when it did.

Caitlyn nodded slowly while he thought. "Most days, I do some camming. I also have an OnlyFans and a ManyVids site where I post some... uh... solo footage? Of myself?" She fidgeted nervously when he stopped making eye contact, but continued on nevertheless. "I sell SnapChat access, and that will have little snippets of videos, or selfies. I answer a phone sex line sometimes... and... I also... escort."

She licked her lips and waited. After a minute, he fell back against the cushion behind him, his eyes very distant, and her eyes were on him the whole time.

"I'm not ashamed of it."

After that he did look her in the eye, though only briefly, and it seemed like a meaningful look so she backed off. Inside, her stomach twisted itself into knots, but she kept her expression smooth while she waited.

***

"I'm so sorry," he said, hurriedly. "I had no idea!"

Caitlyn waved a hand, forestalling him, and shook her head while she stared at the letter, re-reading it from the beginning. Old scars broke open beneath the skin, and her vision turned watery. She grabbed the edge of the door and brought it toward her reflexively, and Phillip's expression fell.

"Please, I—" His voice cut off, though his lips kept moving in silence. "God, I... I couldn't even do this right."

"Why are you here?" she asked, hoarsely, as she brought the door in closer to cover part of her body.

"Guilt," he said. "It keeps me up at night."

Caitlyn nodded as she stared at him, and her brow lowered until it entered her field of vision.

"Sometimes it feels like I'm drowning in it."

"And?"

Phillip looked up at her and blinked for a moment.

"Why. Are. You. Here."

He nodded slowly, and his fists clenched and unclenched while he took a breath. "I came out as bi to my family."

"When?" she asked, acidly.

"Couple years ago. I-In college. Took me a long time to admit, even to myself, that I was... attracted to men." He paused, looking down. "Longer still to admit how far I'd gone to try to prove I wasn't, like some kind of..." He shook his head as he trailed off.

Caitlyn's voice was flat when she said, "Mmmmhmm." Her skin felt like it was going to burst into flames right then and there, no matter how much she tried to focus on her breathing, and her heart was pounding astonishingly fast. Adrenaline coursed through her veins.

"An ex, someone I loved... tried to point out my anger issues, and it took him leaving me to make me realize. I miss him," he said. "He tried. He really tried, and I just... I couldn't admit why. ... I couldn't admit what I'd done. How many people I'd hurt. W-when I first started doing this, my sister said to make a list of twenty, and... it was so much more than twenty."

"And I was fifth?" Caitlyn asked.

He nodded, and looked down and away. "Fifth in no particular order, but... if I were being honest, you'd..." He shook his head, shrugged his shoulders slightly, and then shook his head again. "I couldn't even begin to guess who had it worst. How do you rank pain like that?"

He looked up at her again, seemingly hopeful that she might have the answer, but Caitlyn remained silent for a long while after that.

***

"An escort," he repeated, for the third time.

"Yup," she said, also for the third time.

"What does that mean? Like do you..."

AwkwardMD
AwkwardMD
1,325 Followers