Chastity Chronicles Pt. 04

Chastity Chronicles -- Part Four

Welcome to part four of the Chastity Chronicles. These short stories will follow a forty-year-old woman as she discovers her true sexuality. They are an exploration of complete freedom of embracing sex in all its many forms.

These formulated stories are going to be wild, completely unrealistic, flights of fancy, but a fun journey. This fourth story follows Chastity's fourth and fifth students. They were mentioned in the Epilogue of Part One, a new young man with his girlfriend. That sounds nice. Better yet, the Chronicles have been leading to this conjuncture. It's important.

Chastity is going to discover some interesting things about her sexual orientation and more importantly, about herself.

Sure hope you enjoy.

Love,

Lana Ocean (Estcher)

Content: This one will make up for the last one! This is a bit of a heavy story emotionally. It is for me.

P.S.: This is a work of fiction. Names, characters, places, and incidents are the product of the author's imagination or are used fictitiously, and any resemblance to actual persons, living or dead, business establishments, events, or locales is entirely coincidental. All fictional characters engaged in sexual acts are eighteen or over.

The Perfect Storm

My name is Chastity. I'm forty-years-old, fit, good-looking, a red-head, and I have an insatiable desire to bed young men and teach them the ways around a woman's body. So far, and I freely admit it, at this point in time I had only experienced three students. A virgin eighteen-year-old skinny boy from my condominium called Petey, an extremely hung young man named Ben, and lastly—and he barely counts as a student, really—Billy the Drug Addict.

After all the troubles with Billy and the stolen antiquities, I spent a couple of weeks back with Ben, and then I let him go. Again. There's a lot of people who don't understand just how much an age difference can be. But the real reason I let him go was that I was barren, and Ben absolutely wanted children. Don't believe me? Too fucking bad. You didn't spend countless hours sucking his cock and having his cum pour out of your pussy and ass and then all the pillow talk, to know. So shaddup. I DO know and believe me; he wants kids badly. Yeah, yeah, adoption. Nope. He wants his OWN kids. Surrogate? Not in your life. They wouldn't be MINE. So go complain somewhere else. It's not meant to be, despite how well we get along.

Anyway, dramatic sigh. August ended, I slept through September, and then someone woke me up when September ended. Enter October, and all the sickly orange and black decorative crap. I hate orange and black together. But October may now be one of my favourite months. It's the month I met HIM at the grocery store. He was stocking shelves. We spoke briefly and then...

Well, here's what happened. Did I mention he has a girlfriend?

* * *

I hate shopping for groceries. In case you didn't notice, I don't own a car. I failed my driver's test four times. There are too many rules to keep track of and they don't make sense to me. I've always managed to find someone to drive me where I need to go, so it never bothered me. Now there's Uber and that's kind of great. But I need to get food and the online delivery service is terrible because I swear, they pick out the stuff people don't want because of torn packaging or bruised fruits and vegetables. That's what you get when you order online from a grocery store. So I have to go get it if I want quality.

But sometimes I make it fun. I dress up for it and parade myself through the aisles. Everyone thinks I'm some vapid movie star-wannabe. And I look great doing it. I grab my recycled bag full of other recycled bags, call an Uber, wait outside my condominium building, take the three-minute drive to Complete Foods, shop, and gawk—and get gawked at—call an Uber, convince the driver to bring my bags up to my condominium, unpack, and then have a cosmopolitan. It's exhausting, darlings.

Last time I did this, I spied a cute young man working the store, but by the time it came to pounce, he was gone. He was either really lucky or really unlucky. He'll never know.

What attracted me to him? He was around eighteen. So that checked about all my boxes. The few more to check were being relatively tall, having shaggy, unruly hair, a gawky build he still had to grow into, and an amazing ass. This kid had it all. I think maybe he was the achievement I hadn't unlocked yet.

So during this latest adventure to Complete Foods, I kept an eye out for him. I slowly filled my cart and waltzed through the aisles, my head turning left and right like radar, or sonar, or whatever it is that finds things. I was about three-quarters through the store and thought about dumping my cart and starting over again, when I saw him. He came out from behind the meat section. He had his cute little green apron on, with his name tag that said Sean. I looked closer and sure enough he had large strong hands and huge basketball sneakers on his feet.

And surprise to you! He was a redhead like me! A true curly-haired carrot-top, complete with freckles all over his face.

I mentally added a new check box to my list and checked it.

I smoothed my cocktail dress and made sure nothing was amiss and then stalked him.

I had to find the right time; you see. I wasn't stalking him. Not really. I was waiting to pounce. Go Cougars! Rah! Rah! No, not stalking. I was going to introduce myself. Seduce him. Then fuck him. That's not stalking. Right? That's taking the initiative.

I followed him around the store until he stopped over by the wine section, his back turned to me. That worried me. Are eighteen-year-olds allowed in the wine section? Did it mean he might be, gasp, older than eighteen? There was only one way to find out. I approached him.

"Hello, young man. Can you perhaps help me out?"

When he turned around, he froze. His eyes went from my fashionable shoes, up my long legs, across my groin—yum—over my prominent tits—also yum—, and then locked onto my face. I smiled at him, flashing my pearly whites surrounded by my rich red lipstick. He was going to be mine.

"Why are you wearing that in a grocery store?" he asked.

Insert the sound of a record album being scratched loudly by the needle.

"Um, what?"

"You're wearing four-inch heels!"

Okay, this was not going to plan.

"And that dress? It's a bit much, no?"

"Why are you talking to me like this?" I honestly didn't know.

"Cause you just stalked me throughout the store for the past thirty minutes."

Oh, shit.

"I was not!"

"You were!"

"I was not!" Eventually, I would win this argument. I had to stick to my guns.

"Jesus. Want to see the surveillance footage from the store cameras?"

"Um, no?"

"Good choice. Now, what do you want?"

What a feisty little fuck. My attraction was quickly disappearing. But it wasn't gone, mind you. I was having a new revelation about redheads. "I think maybe redheads are arrogant."

"Right now they are. Why are you stalking me?"

"I-I... oh, fuck it. It's because I like you."

"You like me? We only just met. Wait, how long have you been stalking me?"

"I am NOT stalking you. I wanted to meet you."

"Yeah, definition of stalking."

"And... if you would stop interrupting, ask if you wanted to go somewhere and chat."

"Also stalking."

"No, it isn't. Stop saying that."

"I have a girlfriend."

"So?"

He stared at me. "That doesn't bother you?"

"No. Should it?"

"Unbelievable. What is it you want to talk about? What could a cougar possibly say to me?"

I made my voice a sultry purr. That always gets them. "I'm sure we'll find some common ground. Find a way to... connect." Yum, innuendo.

"No."

"What?" Hmm, that came out screechy.

"You heard me, no."

I had a thought. "Your girlfriend didn't send me to test you or anything."

He gawked at me. "Why would you say that?" Then he smiled. "But of course she didn't. She's right behind you."

I turned in shock, but there was nobody there. When I turned back, he was walking away, laughing uproariously, the little shit.

Goddammit.

I left my cart and went home. Humiliated for the first time. I was losing my touch.

Somehow, this is all Ben's fault. I just know it.

The next day, I had to go back to the store. I actually needed groceries. The frozen vegan lasagna in the bottom of my freezer would be uncovered a millennium from now, still unopened.

I was dreading this. Once bitten twice shy, they say. I wore overly large shades and dressed down to my normal clothes. Tight jeans and my favourite tee with Rush 2112 on it. I also wore white tennis shoes and a baseball cap with the Expos logo on it. I had tucked all my hair up inside the hat to hide my obvious red hair. It was an excellent disguise. I grabbed a cart and hurried through the store, grabbing what I could while keeping an eye out for my arch-nemesis. I made it through checkout and sighed in relief as I emerged outside and waited for my Uber to show up. The tracker showed he was a good ten minutes away. I started to breathe normally.

I was at the corner of the building near the entrance, but also close to the loading dock for the store. It's a very large store serving the whole south side of my city Centreville, USA. That's where I was when I heard a faint argument taking place. A female voice, shrill and too loud. It cut through the cold October air.

"I don't know when! When I'm ready!" she barked.

"Haven't we waited long enough, Pris?"

Pris? What a weird name. Bladerunner ran through my head. Wait... I know that voice! It's that little red-haired shit!

"Sean, I know I promised for prom night, but I couldn't go through with it! At least I blew you! Three times!"

"Prom night was months ago! You have to understand my frustration!"

"Sean, I love you, you know that, but stop pressuring me! I've explained this over and over!"

"I'm not pressuring you! We haven't spoken about this for weeks! We both want it! You've said so yourself!"

"Why are you bringing it up now? It was all you talked about all the way here for your shift. It all needs to be right, baby! You know that!"

"Bullshit! You just have this hangup thing."

"Hangup!?"

Oh, he was in trouble.

"HANGUP!?"

"Wrong choice of words..."

I'll say.

"Sean William Doyle! You say one thing more and we are done!"

"..."

Good choice, I thought.

"I have to go, or I'll be late for work. You know how Bill gets."

"Okay."

"Give me a kiss."

"..."

I heard smooching sounds and then the rapid footsteps of pumps on concrete, so I moved back around the corner and pretended to check my phone. Good, five minutes till my Uber arrived.

I heard the footsteps grow closer and then she waltzed past me, making a beeline for the parking lot. I lowered my shades to check her out. She was gorgeous and black. I mean it. She was gorgeous. She was my height, with frizzy black hair with a hint of red to it. She had a perfect complexion with a creamy dark caramel tone. Her legs were just the right length, rising to a perfectly round ass. Her breasts were larger than mine and perfectly proportionate to her chest. She could be a model. She probably was a model. I wanted her to model for me.

Where did that come from?

I was attracted to her. I totally was. Oh my God!

I was completely frazzled now and hated Complete Foods. It was ruining my life's stability.

She marched over to a beat-up Mazda 323. I couldn't determine its original colour from all the choices it made available. She swung open a screeching door and got in. I heard her turn the key, and the car made a strange sound like it was dying a slow and agonizing death, perhaps under water, or under a rockslide. The headlights were getting dimmer and dimmer, but she kept trying and I could see her getting pissed off and smashing her steering wheel with her perfectly manicured fingers and nails. Finally, the car stopped making any sounds at all. I felt sorry for it. It was a painful death.

She got out; her face furious and yet still somehow beautiful and kicked a tire and then looked around.

Right then, my Uber showed up.

My subconscious took over. Stupid subconscious. "Hey you! Girl by the shitty car!"

She looked over at me, alarmed.

"Need a lift?"

She frowned and then shook her head.

"Come on. I'll get you to where you need to be and later you can arrange something for your... dead car."

She shook her head. "No."

"Don't be an idiot!"

She glared at me and walked right at me.

"Hey lady, you the one that ordered an Uber?"

What the...? I pulled off my shades and looked at the driver who was now out of his car, but still somehow still inside it, and he leaned across the top of the car. He was looking right at me.

"Yes. Can you put those bags in the trunk?"

"No. That's your job."

"That's..." I was interrupted by the arrival of the Black girl.

"Why would you do that?" she demanded. She was only a couple of feet from me and now I could really see her. She was stunning. My mouth suddenly felt dry.

"Cause I'm a nice person. Come on. Get in."

"You don't even know where I'm going or who I am."

"Doesn't matter who you are. Where are you going?"

"To work."

"See, now I know."

She smiled, finally. It lit up her face. My God, the symmetry of her face was perfection. You could place a mirror along the centre of her face and in her reflection, she would still look the same. "I, ah, um, work in a bank downtown."

Odd way to say that. "Which one?"

She told me.

"Sure. Come on. It's not far. Get in."

I glanced at the driver, and he was looking annoyed. He disappeared into his car.

She climbed in and I lugged my groceries into the trunk and slammed it hard and joined her in the back. The driver glared at me and then started to drive but I stopped him. He was going to take me home and I no longer wanted that.

"One more stop first, the bank at Third Avenue and Eighth Street."

"That'll be five bucks more."

"Ten, if you make it quick."

We were pressed back into our seats for a moment, and I looked at the girl beside me. She looked alarmed and then grinned.

"I always wanted to say that." I said, and she giggled. "You remind me of someone," I blurted, because she did.

"I hear that all the time. Whitney Peak from Gossip Girl. I look a little like her."

"That's it! And no, you don't. You look a lot like her."

She blushed, and I didn't know Black people could blush and show it. I was learning things.

"I'm Chastity."

She blinked at my name. "I'm Priscilla. Nice to meet you. Thank you for this."

"My pleasure. It's no bother."

We rode in silence for a bit. I had to fill it.

"I heard you arguing with your boyfriend. I wasn't eavesdropping. I was right there at the corner waiting for my ride."

"Oh, that's okay. It's a common enough fight."

"About sex, right?"

Her jaw clenched and then relaxed. She was very expressive.

"Sorry! I heard. And I understand."

"It's complicated."

"Not really. You're ready when you're ready."

"I'm ready."

"Oh, then..."

"It's complicated."

"It can't be that complicated..."

"I like girls, okay?"

"But you're with Sean?"

She turned to face me and pushed back on her seat away from me. "How do you know my boyfriend's... Oh my God, you're that stalker woman he told me about!"

"I am not! And I wasn't stalking him."

"You followed him around the store for like an hour!"

"It was only half an hour!"

"See?"

"No, no, no. I wanted to meet him, is all, and talk to him. I'm good with people."

She glared at me, and then her mouth dropped open. "Take off that stupid hat."

"It's not stupid!"

"Take it off!"

I did as she said, and my red hair spilled out.

"Oh my God! You're that Chastity!"

"THAT Chastity? What's that supposed to mean? Do I know you?"

"You know Peter!"

Hearing that name caused me to grind to a halt mentally. "Um, yes, I know Petey quite well in fact." Internally, I was starting to wonder if all the eighteen-year-olds in this city knew each other. There was a good chance, especially in this neighbourhood. They likely all went to the same high school. I should add that to my checklist under 'Things to Watch Out For'.

Her whole demeanour changed. "You're THAT Chastity! You changed Peter and got him all sexy and stuff. He went from zero to hero in like a week!"

"I really can't kiss and tell..."

"Maybe you can help..." Her voice trailed off, and she looked deep in thought.

"Help? With what?"

"With me and Sean."

"About that, you said you like women..."

"And I like men. Kinda both, equally." She shrugged.

"So, what's the problem?"

"I need my first time with a man to also be with a woman."

"Huh? How does that make any sense? Explain."

"It's hard to explain. I've been with a few women. It's really amazing. But I'm attracted to Sean, too. We mess around and stuff, but every time we approach... you know... I freeze up. I panic. I can't control it. That never happens with me around women. But maybe, if you're there with me and Sean, I might be able to, you know, get past it and do it with him. Then my first will be with Sean! I love him so much! He's been so patient with me."

I think I got it. Certainly, I had never thought or heard about a situation like this. But she was beautiful, and I had to see more of her. And I was attracted to Sean. Maybe I could make this work. "Um, okay."

"What? Really?" She squealed, overly loud, in the car. The driver winced.

Oh right, the driver is hearing all this.

"Sure."

She squealed again and grabbed my hands and squeezed them. "When?"

"Tomorrow's Saturday. My place? Say three o'clock?"

"Oh my God, yes! We're both off tomorrow." She looked really hard at me then and her eyes checked me out. "You're really beautiful, you know."

"Thanks."

Then she leaned in and kissed me right on the lips. She was so gentle and soft and goddammit, I moaned into her mouth. She pulled back and my lips tried to follow.

I had closed my eyes! I opened them to see her smiling at me. She was a temptress.

Then I realised that was the first time I had ever kissed a girl. And I liked it!

"This is going to work, I just know it," she gushed.

We pulled up to her bank building, and we exchanged contact information on our phones.

She was standing on the curb, holding her door, and leaning in. "See you tomorrow, Chastity! Thank you so much!"

"No problem."

We pulled away and the driver, who had obviously heard everything, was looking at me with either disgust or with worry. He pulled out and then circled back to head to my condominium. I noticed a discrete Gentleman's Club around the corner from the bank and saw Priscilla heading inside.

That's very interesting.

* * *

"...You're welcome. Glad I could help," I said to the girl Kimberly on the phone.

"Help? I've cum so fucking hard these past few weeks you have no fucking idea."

"I do, actually."

Kimberly laughed. "Okay, fair. Take care. I think I hear Peter coming back into our bedroom with my roommate. She wanted me to thank you, too."

"Okay. No problem."

"Okay, bye."

She hung up, and I put down my phone. A slow smile crept up on my face and grew wider when my door buzzer sounded. Sean and Pricilla were here.

The girl on the phone had called my Petey my padawan. That's actually... perfect, I thought. And now I have two new padawans to train.

I rushed to my front door to buzz them in, my pussy already warming to the new challenge.

"Hello?"

"Hi Chastity, it's me Priscilla, with Sean."

"Come on up!" I said and buzzed them in.