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.
