Chastity Chronicles

Chastity Chronicles - Part Five

Welcome to part five 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 templated stories are going to be wild, completely unrealistic, flights of fancy, but a fun journey. This fifth story continues to follow Chastity's with her fourth and fifth students, Sean and Chastity. Chastity has arranged for an interview in New York City for Priscilla at her magazine. Chastity had an awful experience in New York. Her greatest fear is exposing Priscilla and Sean to that life.

Chastity is going to be reminded of why she left New York for the backwaters of Centreville, USA.

Sure hope you enjoy.

Love,

Lana Ocean (Estcher)

Content: Same old. Threesome, anal, oral, lesbian. There is one scene with non-consent, I don't like it, but it has its reason to be there. Sorry.

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.

Thanks for the Freak Fest Last Night

My name is Chastity. I'm forty-years-old, fit, good-looking, a redhead, and I have an insatiable desire to bed young men and teach them the ways around a woman's body. I had the pleasure of teaching five students to discover their sexual prowess. The first was Petey, a virgin eighteen-year-old skinny boy from my condominium who now attends Berkeley and has a threesome going with his girlfriend. The second is Ben, my burly well-hung superhero, who loves me and knows I love him, but I can never commit to him. The third was Billy, a drug addict who's now in jail. I should probably remove him from the list. And last, and still current, there are Sean and Priscilla, a boyfriend and girlfriend couple. We have our own threesome. Routinely. For months now. I can't get enough of them.

Christmas came and went. Normally, they are quiet for me. This year, I was visited by Petey, Ben, his dad Adam, Sean and Priscilla, and their moms. I had a constant stream of visitors, and I was deliriously happy. New Year's Eve was a blast at my place, with Petey, his two roommates/girlfriends, Ben, his reporter girlfriend, Sean, and Priscilla. That's a private story and not one I want to share. These are my chronicles, and I must stay on track. It's almost done. Just two more tales to share. This one ends poorly, I'm afraid to say. There, that's foreshadowing.

In mid-January, Priscilla received an invitation from my magazine to fly up to New York to sit down for an interview. I hadn't told her and when she came flying into my condominium with Sean in tow; she showered me with kisses.

She was happy. And so was I. Here's what happened.

* * *

"I can't believe you!" Priscilla exclaimed loudly, flying through my door, jumping me, and kissing me anywhere on my face before she could reach past my hands, which were trying to fend her off. I was giggling and not succeeding very well. "How long have you known?"

I saw Sean with his shocking red hair slip in through the door and close it, smiling at us. I tried to wave, but Priscilla saw that as an opportunity to finally lock her mouth on mine. Her hands grabbed my head, and she pushed her body on me.

I fell backwards, pulling Priscilla with me, and she landed on me, still lip-locked to my mouth. It hurt, but the attention was worth it. Then she kissed across my chin and down my throat.

"I'm going to eat the crap out of you right here!" she announced and sat up and worked on removing my jeans. I admired her flawless beauty with her face in perfect symmetry. Perfection.

"Sean! Help me!" I pleaded, not really meaning it.

He grinned down at me. "Why? I'm next."

"Traitor!" I accused him, still giggling. Oh my God, she's serious. She was yanking my tight jeans off in strenuous and determined jerks. She was dragging me across the floor at the same time on my ceramic tiles. No sooner had she exposed my pussy, then she wrenched the gusset of my panties aside and plunged her face into my pussy, her tongue blazing a trail.

"Mumpf," she murmured, lapping happily away.

She's so good to me. If I had known this was going to be my reward, I would have told her sooner.

Priscilla is gorgeous. Like Whitney Peak from Gossip Girl, gorgeous. I hate to compare, but that's what she looks like. She's Black and beautiful. I like nothing better than peeling apart her dark labia and admiring her rich, pink depths. The contrast of colours just makes it so much more appealing. She says she wishes she had a pussy as pretty as mine. I don't have any 'hanging drapes'. Either does she, but her inner labia are more pronounced than mine. I love her that way. I also love how her labia cling to Sean's cock as he pulls out. That needs special licking attention from me.

We had been a 'couple'—all three of us—since November. It was now mid-January, freezing, and snow covered all the city. The wind was howling outside my windows. But inside my condominium it was warm and wet and full of cum. Just the way I like it.

I've been attracting young men and women students to me for half a year. Me, I like to call them my padawans. My first student's girlfriend had borrowed the term, and I liked it. It appealed to my sense of humour. In short, I teach them how to pleasure me and how they can and should be pleasured. It's cathartic. I fucking love it.

My pussy was loving the attention. Priscilla gets me off so quickly. I had my legs spread to give her better access, and moaned when she rimmed me.

"Sean, take it out," I asked.

He knelt beside my head, and I saw it already was. His large head crowning his upwardly curving eight inches popped into my mouth and I moaned around the taste, my eyes taking in his heavy low-hanging testicles. Priscilla looked up momentarily before grinning and diving back down to my ass.

"Is she...?" I moaned.

"Yup. Getting your ass ready for a good fucking," announced Sean.

"What did I do to deserve this?"

"Got us both first-class tickets to New York City for a job interview for her at your magazine."

"Is that all?"

Everything descended into sex from that point on. Sean carried me into our bedroom—I say our because they spend almost as much time in there as me—put me on all fours, took the lube from Priscilla who is very efficient, lubed my ass and him, and was soon balls deep in my ass.

I love anal. It's my favourite thing.

Priscilla crawled underneath me on her back, her head toward the rear action, and I looked down at her perfect pussy, dripping with arousal, and lowered my mouth to dine on her. She reached up, lifted her head to find Sean had a pillow for her ready to go, and went back to my pussy.

I want to stop there and explain something. If you've never experienced this, you need to do something about getting this into your life. Being fucked up the ass by a man you've trained to do it properly, while having your pussy eaten by someone who trained you on how to eat pussy, while dining on the most perfect pussy in the world, is the best sexual position and act in the world. It's a win-win-win. We do this position ALL THE TIME. It's our favourite by far. Either me or Priscilla get the anal treatment. We play board games and cards to see who wins the prize. Today, I must've won the lottery.

I squirt doing this. Not right away and not always. When I do, it takes some time, but once I build up the fluids and Sean gets me orgasming like there's no tomorrow, I have the most brain exploding orgasms of my life, and everything clamps down and out it shoots. The first time it happened we all freaked out. Mostly me. Now, Priscilla drowns herself in it and can't swallow it fast enough.

I ate Priscilla just the way she likes it and fingered her pussy and asshole with one hand in what we call the shocker. First two fingers of my hand go in her snatch, and the pinkie goes in the bum hole. Which quickly turns into two and two. Then you lick her clit. I like to watch her orgasm. Her pussy quivers. It's cute.

Today, Sean was giving me the full long stroke treatment with his fully shaved cock and balls. He would pull back until his cock would almost escape my ass and then drive it all the way back in down to the wide base of his cock. He wouldn't change speed but keep a relentless rhythm. In and out, in and out, and I wouldn't last long. An anal orgasm is a long, hard climb, but oh my God, the view from the top makes it all worthwhile. Priscilla would then lick not only my pussy but Sean's shaft coming out of my ass, and his smooth balls. That would signal the end, usually.

Priscilla and I knew the signs of when Sean was about to erupt. This would get whoever was in the licking position coming to an orgasm. Seeing that, the one getting pleasantly ass-fucked would cum. It's beautiful when it happens perfectly. All of us coming at the same time is powerful.

Today was no exception, and Sean blasted my bowels and cried out in his pleasure, his fingers digging painfully into my waist. Priscilla's pussy vibrated like a power tool, coming equally hard around my fingers in her pussy and ass, and I came and squirted all over Sean's balls and Priscilla's mouth. We writhed in bliss, lost in our orgasms. Sean emptied himself and popped his cock free of my ass and walked on his knees around to me and I quickly stuffed his cock into my mouth and cleaned him up, sucking out the last vestiges of his remaining cum. Priscilla scooted farther down and lip-locked my asshole and sucked out Sean's load. I slowly sat up on her face, and then Sean kissed me, moved around, and then kissed Priscilla.

It never got stale. It never got old. It was our thing. Mutual joy and bliss for everyone all at the same time.

Sean flopped down on the bed and watched his girlfriend eat out my ass. She finished to my loud complaint and curled up with Sean and they necked, sharing his cum.

I love my life.

"Thanks, you guys. Superb as always." I stated as I took Sean's spent cock and sucked the limp sausage into my mouth. I could suck on this thing all day. Sean stroked my hair and Priscilla watched, stroking Sean's hairless chest.

"I can't believe you arranged an interview for me!" she said happily.

"I asked for your portfolio months ago. It was pulled out of a stack of hundreds. I read it and was impressed. Believe me, you are worth the interview purely on your talent. I wouldn't lie to you. You have great potential, that's no exaggeration. But this doesn't mean you get the job, Priscilla. The interview is real. You need to prove yourself. But the fact the magazine will fork out the money for first-class airfare and put you up in one of the finest Manhattan hotels says a lot. Just don't fuck this up. I'm putting my reputation on the line."

"I won't. I'm nervous but excited. Thank you for the opportunity. I won't disappoint you. We love you, Chastity."

"I know you do."

"Are you coming with us?"

"Yup. I have to go to New York a few times a year, anyway. Some things require me in person."

"Can I ask you a question?"

"Sure."

"Why are you living in Centreville, USA? This is back waters for someone like you. You should be in New York living the high life."

"I am living the high life."

"Yes, but it's here."

"With you and Sean."

"Stop it! You know what I mean."

"I do. It's personal. A choice I've made. New York was destroying me. You'll see. It's part of the reason I'm going with you."

"Why? What's so bad there?"

"The decadence. When I was younger in the business, it nearly consumed me. It used to disgust me. Now, I'm not so sure. What we just did here on this bed is tame, but not much different."

"So hot sex? What's the problem? I don't understand."

"Hon, they're all artists. Artists feel things differently. They love more and express that love more. If the setting is right, you wouldn't believe what happens regularly in New York City. Look up from the street at any condominium or penthouse and I can guarantee people are getting their freak fest on inside. If you're beautiful like you..."

"And you..."

"Yes, and me, and frankly Sean here, too. He's gonna be devoured in New York City with that red hair and great looks. You too, Priscilla, probably even more. You're a walking wet dream for most men. Men and women. There are very few lines they won't cross. Unless we're talking about coke. Then there are lots of lines. Speaking of which don't accept any drink you are offered from a stranger. Never ever. Like ever, and I mean it. And please, watch the drugs. It will be tempting. It will be right there and available. You only have to reach out your hand and take it. But believe me. It will only turn out to be a quick ride to the bottom. And it will kill your creativity."

"You make it sound like we're going to be partying all the time. It's just an interview. In and out, no?"

"No. The interview is just a preliminary step. You pass that and the doors open. You will be expected to attend some parties. The magazine will want to show you off as their new acquisition. And with your looks, honey, they are going to demand it. You look better than almost all the gals there. You might get a modelling offer. I wouldn't be surprised. Stay with me. Listen to me while we are there. I will keep you safe. Trust no one. Only me. It goes for you, too, Sean. You're her weak point. They'll use you to get to her, you understand?"

They nodded their heads, and I suppressed a sigh. They didn't get it. Not really. It had to be experienced. It might all just be smooth sailing. But I doubted it. The owner of the magazine was someone I knew well. She was a bigger cougar than I was now. She never took no for an answer. I already warned her to be nice. And she agreed far too quickly. That worried me a little. But I was confident in myself. I would keep them safe. Or there would be hell to pay.

"Okay, supper time. How's grilled salmon over salad sound? I'll even let you youngsters have some wine again. Sound good?"

A chorus of yesses and I rose to make supper. We would fly out in three days, and I still needed to prep Priscilla for the interview. Time was flying by.

* * *

Sean and Priscilla were loving the whole first-class experience. Special lines, special treatment, special lounges. It was all magic to them. It was another day at the airport for me. We boarded first, naturally, and took our seats. They were together on the right, and I took the aisle seat across from them, sitting next to a business class upgraded male passenger. You can always tell them apart from those of us who actually paid for the seat at full price. They act entitled.

He wanted to talk to me, naturally.

"Don't."

"Pardon?" he said.

"Don't talk to me."

"Oh, sorry."

The rest of the flight was peaceful, and I read the latest edition of my magazine. Our European writer had authored an excellent article on the art emerging from Spain. Her photos were beautiful as usual, and I knew she had likely waited hours for the natural light to be just right. Her article was insightful, and she was onto something there. I would have to keep an eye out on Spain. I had proofed and edited all the articles before, of course, but reading them in the actual magazine was always pleasant.

"You like art?" asked the idiot beside me.

"Yes."

"I know quite a bit about art. I'm something of an artist myself."

"Really."

"Yes, I've met many artists. They can be quite interesting."

"Like whom?"

"Pardon?"

"Who have you met?"

"Oh, um..."

"Name one. Quickly."

"I-I... just a second! Let me think..."

I opened the magazine to the editorial page and held it up for him to see. My picture was right there, my red hair flashing. I liked that photo. It had my name right under the photo: Chastity, Senior Editor.

He stared at the photo and then looked at me. "Oh, is that you?"

"Yes."

"Sorry."

"It's all right. I'm used to it."

"You are really quite beautiful, you know."

I finally looked at him. I hadn't done more than a glance before. He was my age, relatively fit, then I caught the faint smell of stale cigarette smoke. "Thank you."

"I was wondering..."

"Not going to happen."

"Oh, all right then. Sorry to bother you."

After about five minutes, I felt bad. I felt bad I hadn't really hammered it home. I was going to New York. I had to up my game. He would be good practice. "Listen, I didn't mean to be curt. I'm a little stressed out. I have a lot on my mind. I have to introduce my two oblivious lovers to the world of New York City."

"Lovers?"

"Yes, we are lovers."

"Oh. Two of them? Do they, ah, know you are with both of them?"

I looked over at the happy couple, cuddled together and engrossed in a movie. "Hey, Sean and Priscilla, do you know we're lovers?"

They looked over surprised. "Um, yeah? Of course? Is this a trick question or something?"

I looked at the fellow beside me who was gawking at Priscilla. "See? Oblivious."

He shut up for the rest of the flight but kept stealing glances at us. Inside my head, I was on the floor laughing. I looked at my watch.

Thirty minutes left, thank God.

* * *

We only had carry-ons. I had insisted. We pushed through the throngs to the outside, and they halted as soon as they saw what awaited us. They had no idea a limo would pick us up at LaGuardia. We got inside and they pressed themselves to the windows as we made our way down and through Manhattan. We crossed the Hudson and hit the heavy traffic. It was slow going, but they had a blast pointing out recognisable landmarks. Like San Francisco, you've been to New York, but you might not realise it. Television and movies have highlighted those cities so much you'll recognise everything. It can be surreal.

We pulled up to the hotel, and the chauffeur opened our door, and we got out. A porter met us to take our bags.

"Ms Chastity, a pleasure to see you again."

Priscilla looked up and screeched. "Oh my God! Are we staying at the fucking Carlyle?! Sean! Oh my God! The Carlyle!"

I grinned a deep and satisfied smile. I was living vicariously through her. Part of me wanted to jump up and down like a little girl, just like her. But I had airs to put on.

Then Priscilla grabbed me around the waist and made me jump up and down with her. Then I couldn't help it. I laughed aloud and jumped with her, which is extraordinarily hard with three-inch heels on. The porter was smiling and everyone outside was watching with equally broad smiles. Then she kissed me. Not a kiss between friends, but between lovers. She held my neck, pulled me in, and kissed me deep and I loved it.

We heard a few catcalls, and I actually blushed.

"You made her blush, Pris!"

She looked at me in wonder. "I sure did. Imagine that."

"Come on. Let's get settled. I have a wonderful night planned for us. We need to freshen up. And go shopping first."

They looked at each other with worried expressions.

"Kids, this is all on me. And the magazine. Enjoy yourselves. This won't cost you a cent."

In case you forgot, they were barely scraping by. Priscilla worked at a Gentleman's Club stripping and Sean stocked shelves at the local grocery store.

The porter was waiting patiently. He had no choice.

"Come. Follow me."

We walked in through the doors and into the Carlyle. You have to experience it once. You've seen it before all thanks to Hollywood. Priscilla and Sean looked like bobbleheads trying to take it all in. I noticed many pairs of eyes tracking Priscilla. I worried about her. She was too beautiful and innocent for New York.