Chasing EleMistriss

Chapter 1

Chase

"To no more school!" Chase clinked his beer bottle with his best friend Bruce's.

"I'm so glad to be done with that place," Bruce replied in a salty tone.

At 22, they'd both just graduated from a conservative, religious university with strict rules, and having lived in campus housing all four years, they were so ready to be free of all the restrictions. This weekend, they'd be moving into an apartment together, and tomorrow, they'd each be starting their first full-time jobs. Chase would be learning the family consulting business, and Bruce was starting off in retail. Chase was grateful to be able to avoid the retail fate. He had so much respect for those that dealt with working in retail hell.

He felt nervous but optimistic about his future. He'd be starting work at his dad's company, and he was looking forward to working with Ellie, his dad's right-hand woman. Her kindness never failed to make him feel warm, and she'd even made him feel better when he'd fought with his dad growing up. She'd been able to provide some adult perspective that actually made sense. He hadn't seen her since he'd gone off to college and wondered if she'd changed at all. He had a feeling working with her would feel natural and easy.

"Dude, now you can finally lose your virginity," Bruce said boisterously, bringing him out of his thoughts of Ellie.

Chase was sure he wasn't imagining that the bar got quiet for a moment. Was it mandatory for anyone asking that question in a public place to forget how to whisper?! He responded in a low voice, hoping Bruce would take the hint and follow his lead. "Yeah, well, I'll have to find someone to WANT to fuck, first."

For years, Chase thought he was just a late bloomer, but after doing a lot of research, he thought he might be somewhere on the demisexual spectrum. No label fit him exactly, but the occasional person inspired his dick to take interest.

"You will. I told you I'd help you out if you wanted," Bruce said with mock seduction.

Chase had seriously considered that option before, but unfortunately, Bruce didn't do it for him. He had no problem with the thought of being with a guy, despite what their school had preached. "Thanks, but no thanks."

Bruce huffed indignantly. "Fine. I'll take these skills elsewhere," he said, bumping his shoulder to Chase's playfully. "In all seriousness, you'll find someone that makes you tick. And I'll be here either way."

Chase felt his eyes sting. "Oh, fuck you and your sentimental shit, bro," he said with a slight sniffle and a laugh.

Bruce cackled. "You're so easy!"

Chase downed the rest of the beer. "Let's go finish unpacking. I have to be up for work in the morning."

*****

Ellie

Ellie adjusted her skirt self-consciously as she heard Chase arrive and greet his father. When she'd chosen her outfit, she'd forgotten that he'd likely be sitting beside her today and her legs wouldn't be hidden under her desk the whole time. If she turned, the skirt would show off too much chubby thigh to be considered proper. Oh, well. Hopefully, the sight wouldn't scare him off on day one.

Ellie was 45 and had worked for Cappy Consulting for the last 15 years. Her boss, Chris Canter, was obsessed with Capybaras. Add that into the family 'CC' names and Cappy Consulting was born. The name was kitschy, sure, but it drew attention and was a conversation starter.

She was excited about Chase learning the business. They'd always gotten along well, and with Chris' retirement on the horizon, this meant more job security for her. She had a ton of flexibility, no time clock, and no IT department spying on her computer, so she wanted to work there for as long as possible.

A notification popped up on her screen indicating a new message. She opened it quickly.

SxyBear4522: Can I please lick your pussy now?

Ellie enjoyed sexy, texting role-play with a few different partners and especially sneaking it in during work. She sighed. She'd have to curb that for now until Chase was no longer shadowing her.

EleMistress: yes, it's dripping for you. Make me cum and then edge yourself every hour until 5 pm. Take a picture before and after you explode. I'll be unavailable until then, so make me proud, my sexy bear.

SxyBear4522: *Dives into your sweet pussy

Ellie's clit throbbed. If only she could find someone to play with in real life. Her confidence and commanding attitude didn't extend to making new friends and meeting people, her age and weight made her feel less than sexy, and her insecurities followed her around like an annoying, yapping puppy. Somehow, online, those things didn't feel like a barrier. She never misrepresented herself, but she felt confident in herself with the barrier of the screen.

She closed completely out of the chat app just as she heard a knock on her door.

"Ellie, you remember my son, Chase." Chris had a huge smile on his face.

"Chase! It's so good to see you!" Ellie rose from her chair and gave Chase a big hug. He'd really grown up since she'd last seen him. His reddish-brown hair was styled neatly, and his beard and goatee made his boyish face look mature. His rolled-up sleeves and tortoiseshell glasses gave him a hipster vibe that totally worked for him.

"It's good to see you too, Ellie."

His deep, warm voice rumbled through her as they embraced. She felt a warm tingling down her spine and chalked it up to enjoying the human connection of the hug.

*****

Chase

Chase felt a stirring beneath the belt as Ellie hugged him and he embraced her firmly. She smelled faintly of coconut and her soft body fit against his comfortably. He felt reluctant to let go after the 'socially acceptable hug timer' had expired. His reaction surprised him, but he brushed it off as a fluke.

"Have a seat and we'll get started," Ellie told him. She continued in a low voice, "Tell me what school was really like later, okay? I want to hear everything."

He returned her conspiratorial smile and nodded, looking her over. Her long, dark hair was streaked with a bit of gray, and she pulled it around her shoulder as she sat. Her warm, pale, green eyes crinkled when she smiled. He noticed how her skirt hiked up her thighs before she quickly scooted under her desk. His eyes traveled over the roll of her belly and her ample chest before he caught himself. His dick twitched and he glanced down questioningly. Seriously? You couldn't pick someone...I don't know...APPROPRIATE to finally take an interest in? Luckily, Ellie was too busy opening screens on her computer to notice.

She began by describing the basics of their software and gave more detail on what her job entailed. She went through scenarios of how they'd helped several businesses find their weaknesses and ultimately improve and grow.

As he sat beside her, eyes trained on her lips as they moved, and her soft, coconut scent surrounding him, he found himself in a predicament that most men had outgrown long before. He wasn't sure his dick had ever been this hard. He did his best to pay attention to what she was telling him, and lunch couldn't come fast enough.

At noon sharp, his Dad came in with his silly Capybara tie loosened. "Ready for lunch, Sport? Ellie, you don't mind if I steal him for an hour, do you?"

Ellie rolled her eyes. "Of course not. I'll be headed out in a few minutes anyway. Chase, if you get back first, I'm leaving this window up for you so you can read about this company. The PIN for the computer is 8529."

"Sounds good," he croaked before clearing his throat and smiling weakly.

*

Luckily, chatting with his father on the way to the restaurant calmed his wayward dick and he was able to have a normal lunch. When they got back to the office, Ellie was still out, so he sat down and keyed in the PIN she'd given him.

Ding

A chat window popped up and he read the words before he could stop himself.

SxyBear4522: Please EleMistriss. Can I cum? I can't take this anymore. I'm so hard.

What...The...Fuck...?

Chase knew he shouldn't, but he scrolled up to read the previous messages from today.

SxyBear4522: Can I please lick your pussy now?

EleMistress: yes, it's dripping for you. Make me cum and then edge yourself every hour until 5 pm. Take a picture before and after you explode. I'll be unavailable until then, so make me proud, my sexy bear.

SxyBear4522: *Dives into your sweet pussy

So, she was...what was it called...dominating him? Chase's breathing accelerated at the thought of Ellie telling him what to do. Oh shit... Chase jumped up and ran to the restroom where he frantically opened his pants, pulled out his dick, and came. Dizziness assaulted him and he sat down hard on the toilet before he could fall. He rested his forehead against the cool wall and tried to get his breathing under control. His face was on fire and his dick wasn't fully soft yet. He felt like he'd just dipped a toe into adulthood then and fallen in headfirst.

*****

Ellie

Ellie returned from lunch to find her computer unlocked but Chase not sitting in her chair. As she sat down, she looked at her screen and froze. SxyBear4522 had either ignored or overlooked her message that she would be unavailable, and apparently, her app setting had reset to push notifications through even when the app was closed. The last time that happened, it had also shown the full message instead of "New Message" as her settings mandated. That must have been what happened this time. Stupid technology. Stupid Ellie is more like it.

Her heart started to pound. Maybe Chase hadn't seen anything. She quickly corrected the app settings and closed back out of it, purposely ignoring SxyBear4522. She rarely had anyone on this side of her desk and even more rarely let anyone use her computer, so this possibility had never been an issue before. Most people would think she was an idiot for doing this kind of thing at work on a work computer, but she liked skirting the line of naughty.

Chase returned a moment later, smelling of the hand soap from the bathroom. He slid back into the chair beside her and cleared his throat.

"Hey, you. How was lunch?" she asked.

He cleared his throat again. "Um, it was good." He rubbed his hand on the back of his reddening neck in the generic, male, 'I'm nervous or embarrassed' gesture.

She sighed internally. He must have seen the messages. She knew he wouldn't say anything to his dad, and even if he did, at most, Chris might look at her funny for a couple of days. He wouldn't approve but he would be way too uncomfortable to address it with her. She decided to just pretend nothing happened and move on.

"Good!" She said brightly. "So, let's talk about this company..."

*****

Chase

That night, Chase locked himself in his room and fired up XHamster on his laptop. He'd spent a lot of time not masturbating to the porn on the site while trying to figure out what might make him tick. He hovered over the search bar and finally typed in female dom, and scrolled down to Female Dominates Male in the options list. The page was overtaken with women in leather, men in harnesses and handcuffs, and fists in places he didn't want to think about. He felt his face flame and butterflies started dancing in his stomach. This felt way over his sheltered head.

He thought of the orgasm he had earlier that day and pushed on. He forced himself to watch part of several videos with cheesy acting. One man was whipped and kept yelling, "Thank you; may I have another?" A man wore a leather mask while his nipples were clamped and his dick was in some kind of metal cage. Another man was forced to lick the leather boots of his...Dom? Domme? Mistress? He was only getting more confused.

Finally, he clicked on a video that looked pretty benign. The thumbnail showed just two naked people on a bed, and the quality was a little less crisp than the previous HD videos. The woman had a great, juicy ass, and the man wasn't overly fit. He clicked play and turned the volume up on his earbuds to listen.

The woman started by crawling up the man's chest and straddling his head, keeping her vulva just out of reach of his tongue. "Don't move," she commanded softly.

The man visibly took a deep inhale of her scent but obeyed.

"Good boy, Lex" she commended. She lowered herself so that he could taste her and when he moaned, she ground against his face lightly.

Lex's cock was sticking straight up in the air, tense and waving.

Chase could feel his own cock stirring a little and he was becoming mesmerized.

The woman moved back down Lex's body and sat down on his cock, thrusting and grinding twice before swiftly pulling off. Lex's hips followed her up and he whined.

What followed was the woman bringing Lex to the edge over and over again until Lex was incoherent and begging, his poor dick nearly purple. She finally took mercy on him and rode him to completion before moving back up and sitting on his face for him to lick his own spend out of her pussy.

Chase reached down to find that he was definitely aroused. He thought about being the man in the video and Ellie being the woman. He thought about putting his mouth on her pussy and his cum being inside her. He thought about her commanding him. He came all over his keyboard.

He knew the situation wasn't ideal, but he couldn't ignore these feelings. He wanted to at least try to convince her to show him what it would feel like to be with another person. Was it a risk? Absolutely. Was it stupid? Probably. For the first time in his life, his dick was driving the bus, and he didn't care.

*****

Ellie

Ellie sat in her recliner, leisurely licking her fingers after finally letting SxyBear4522 cum after watching her finger herself into an orgasm. She'd always loved the taste of herself.

Her last boyfriend had been horrified by her "dirtiness" (his words) and kinkiness, and she'd decided she wasn't even going to try to hide it anymore. Life was too short to keep yourself hidden away to please other people. It had been a hard lesson to learn and an even harder one to integrate into real life.

Her thoughts drifted to Chase. He had grown into one HOT man. She hoped that his school hadn't made him afraid to be himself, whoever that was. She'd seen so many people come out of that school as repressed, carbon copies of each other, spouting the same, tired opinions.

She started thinking about what she would show him tomorrow and his strong forearms as he took notes came to mind. And that beard...Oh, good grief, you're old enough to be his mother and you work for his FATHER. And when did one start to feel old, anyway? Mentally, she still felt like she was in her 20's. She knew some men were into older women and she was definitely starting to fall into that category. She tried to mentally put Chase in her mental "Do not touch!" box and got ready for bed.

She may or may not have cum while giving in to a fantasy where she showed Chase where his prostate was.

Chapter 2

Chase

Operation 'Seduce Ellie' was underway. Well...if you counted chickening out every single day for a week 'underway'. On a positive note, they'd gone to lunch together every single day and they'd talked. They'd talked about family and friends and beliefs. They'd talked about society and movies and books. They'd talked so much they started texting in the evenings as well. They never seemed to run out of things to say. They'd quickly become friends. Close friends.

"Um, dude?" Bruce's voice infiltrated his thoughts.

Chase jumped and snapped out of his daze. "What?"

"You seem to have a, um...problem there..." Bruce pointed to his lap.

"Like you don't have one of your own. How do you control these things?" He'd gotten pretty good at hiding the constant erections at work, but he was at home on his couch and not paying attention while his thoughts wandered over Ellie.

"You have these things attached to your arms. Some of us call them hands..."

Chase glared. "I'm doing that four times a day."

"Welcome to puberty, my friend." Bruce cackled. "Are you going to tell Ellie you're into her or not? I know the situation isn't ideal, but she's kind of a unicorn for you. I say take the chance."

"I know, I know. And the more time that goes on, the more I really dig her, you know? Not just sexually, but I LIKE her. We click. But for real, why would she want a 22-year-old virgin when she can command a 'sexy bear'?"

Bruce clapped a hand on his shoulder and dropped a very un-manly kiss on his head. "You'll figure it out. And if she says no, she doesn't seem like the type to make things weird."

"You're right. She's not. I'm going to see if she wants to come over for pizza and a Friends marathon. Are you going out tonight?"

"I am now. I'll crash with Jeremy. Good luck, and don't. Fuck. It. Up." Bruce had recently been binging RuPaul's Drag Race.

"If you can't love yourself...and all that..." Chase replied with a wave.

Chase: Hey, Els, are you busy tonight?

Ellie: Was just thinking about ordering a pizza. Why, what's up?

Chase: You wanna come over here and get a Pizza and watch a Friends marathon? Or I can come to you.

Ellie: Sounds like my kind of night. Why don't you come over here?

She included her address.

Chase: I'll grab the pizza and be there soon.

Ellie: *thumbs up emoji*

*

Chase knocked on the door of a simple, well-kept home with a small garden in the front. When Ellie opened the door, the breath left his body. She'd changed out of work clothes and was wearing an oversized tee and pajama pants. Except she wasn't wearing a bra and her large breasts swayed as she moved, and the pants cupped her sizeable ass that showed no signs of a panty-line.

"Hey! Don't mind my PJ's. I couldn't bear the thought of changing back into regular clothes. Come on in. You want a beer?"

He unfroze himself with effort. "Brfhm."

"I'm sorry, what?"

"Beer sounds great, thank you." Get it together, idiot.

She gestured to a well-loved couch with built-in recliners, and he sat, putting the pizza on a coffee table.

"So, what'd you get?" She asked, referring to the pizza.

"The works with stuffed crust, including pineapple." They'd had the pineapple on pizza discussion and luckily, they were both on the proper side with YES. Such a silly but fun debate.

"Rock on," she replied while handing him a paper plate. She turned on the large-screen TV and navigated to a streaming service. "May as well start at the beginning, no?" she said, referring to Friends.

They settled in and enjoyed the pizza. Somehow, the show was even funnier when watching with someone new. After a few episodes, they cleared the box away and got fresh beers.

"This is nice," she said. "I don't have many local friends. Most of them are online."

Chase tried not to choke on his beer. Maybe this was the segue he needed. "Ehrm, actually, I've wanted to talk to you about that..." he trailed off.

*****

Ellie

"Talk to me about what," she replied.

"Um, well, it's just that..." Chase rubbed the back of his neck.

She sighed and took pity on him. "Does this have anything to do with a chat that may have popped up on my computer?"

"Mmhmm, yeah, I'm sorry, I...," he trailed off.

"Hey, no big. I'm sorry you saw that. It had to make you hella uncomfortable. And I know we're friends now, but from a professional perspective on day one...yikes. Creepy old lady alert."

He side-eyed her. "You're not an old lady."

"I'm 45. No, not old, but an old lady to a 22-year-old." She thought of the fine lines around her eyes and mouth, and the impact of gravity on her chest and...other places.