Chastity Chronicles Pt. 01

Chastity Chronicles -- Part One

There were two things I considered the other day: one, coming into your full sexual potential as a forty-year-old woman is exciting, and two, being a woman allows you much greater freedom in pursuing that itch.

This led to me wanting to write short stories about a woman blowing open the doors of decency and diving deep into her deepest desires and pulling along a bunch of randy young adults along for her ride.

These stories are going to be wild, completely unrealistic, flights of fancy, but a fun journey. This first part opens the door to her new lifestyle.

Sure hope you enjoy.

Love,

Lana Ocean (Estcher)

Content: Heterosexual sex, oral sex, cum swap between men and women, anal sex.

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 Beginning

When I was born my parents named me Chastity. There's a certain irony to that now, I realise. My parents were a little religious but later in life my mother admitted she named me that only to please her mother, but I've always liked my name. It suited me to a tee until I turned forty.

My father was in the military, and we moved around a lot in the United States and overseas, although the overseas part happened when I was too young to remember anything other than the occasional memory flash of Japan, Naples, and Hawaii. I know, Hawaii is not exactly overseas but it was outside the continental United States and my parents treated it as such. Dad was in the Navy and died while still in uniform from a rare genetic disorder when I was sixteen.

Which led to me being examined by Tri-Service Care, but they found nothing related to what killed my father. Then they found what they called unexplained infertility. I would be childless. It was devastating. In six short months, I went from having a loving father to losing him, to finding out I was barren. I went through a rough patch. I rebelled. I drank. I smoked. I did drugs. I fucked a lot of boys. I thought I had nothing to lose. I distanced myself so much from my mother that even today, at age forty, I have nothing to do with her. That's on me.

I also was unable to commit to any relationship. Those men who pretended not care I was barren, cared. Some men thought that meant they could do whatever they wanted with me. In time, sex lost its appeal. Dating lost its appeal. I withdrew from society and became a senior editor and part owner of an East Coast artsy magazine. I made some investments during the Dot Com Boom and got out before the Dot Com Bust, and I have to say, I really want for nothing financially. I choose to live in Centreville, USA in my overpriced condominium overlooking a lazy river. It's my choice.

I run daily to stay in shape. I don't drink or smoke or do drugs (other than the occasional joint on special occasions, such as a new episode of a Star Wars series showing up on my Disney+). I'm fairly good looking if I don't say so myself. My breasts aren't huge at all thankfully, but they're prominent. My ass is heart-shaped, and firm due to my running. I'm exactly the right weight for my age. I have shoulder-length red hair, white skin, a freckled face and upper chest, and dimples on my face cheeks and ass.

I'm a hot MILF who's unable to be an actual mother.

When I turned forty, something changed in me. It didn't happen overnight. It was a gradual build-up of conflicting emotions that started a month before my birthday and exploded about three months after. I went from zero sex drive to a raging inferno. I bought toys and used them frequently. I was jilling myself about four times a day by the three-month period. I had dildos, nipple clamps, vibrators, and accounts with most female tailored porn sites. The free stuff is crap, and I really needed the good stuff.

My go to was always—and I mean always—videos of MILFs with eighteen-year-old boys and girls.

Then videos and my toys were simply not enough for me anymore. I wanted real cock. I wanted to watch cum spew forth in huge gouts to land all over me. I wanted to be filled. Eaten. Fucked hard. I wanted to lick male sweat off an eighteen-year-old chest.

Let me tell you how it all started.

* * *

The elevator doors had almost closed, and soon I would ride up to the top floor of the condominium complex I lived in, when a hand shot between the doors. I suppressed a groan at the delay. I was eager to get home and pleasure myself. The doors slid open revealing a young man, dressed in running gear, staring right back at me, with me standing right in the middle of the elevator.

He froze in place. I watched his eyes roam all over my body, taking it in, lingering on my tits and my crotch. I could almost feel his eyes physically touching me. I won't lie. I felt a strong sexual stirring and enjoyed the blatant attention.

The boy looked barely eighteen. He was fit but, in that beanpole look of young men still waiting to grow into that more masculine look. He wasn't muscled or filled out in that all-American quarterback look. But he had lovely soft brown hair, a little shaggy, and plastered to his forehead with sweat. He had a little acne around his mouth. His legs were skinny but toned with a runners look. The leg openings of his shorts had plenty of room for more leg. I was sure he could put both legs in one opening. His wrists and arms were sticks. I judged he was just shy of six feet tall, based on how I had to slightly look up at him. I watched his eyes roam and roam and to my delight—which surprised me—my nipples tightened a little, sending sharp pleasant tingles through me. I saw his eyes lock for moment on my tits. He saw them get hard but likely had no idea why. Boys are a little bit stupid at times.

He looked like he spent his days playing videos games and eating cheesy poofs. He probably ran because his school expected him to participate in track. But I looked at his shoes and they were well worn. When I looked back up, he was looking right into my eyes. They were a little wide and had a fight or flight look to them.

"Are you coming in or not?" I barked and he actually jumped a little. That amused me greatly, and in that moment, my subconscious made a decision that would change my life. Well not my life exactly, but certainly my lifestyle.

I have a voice that registers a little lower than most women. I've had lovers who've said it's seductive and always just on the edge of being husky. To me it's my voice, but I have noticed it has a positive effect on men. It speaks of desire and lust. With this poor young man, I used it to my advantage and let's be honest, in the game between men and women, women have all the power. And I have my own cheat code.

He stood there not moving.

"In. Now." I barked again and he jolted forward. I was still standing in the middle of the elevator and refused to give up my God-given right to own the middle of the elevator. He had to twist a little to get in and he ended up standing in front of the left elevator panel. He punched the sixteenth floor, just three below me, and stood there. The elevator suddenly blurted out the most God-awful noise, and then we watched the doors ponderously close. They took forever.

Why have a door alarm because the doors have been opened too long, and THEN make them close in the slowest way possible?

Finally, the doors closed, and I could see the poor boy's shoulders slump in relief.

So, I reached out, completely inappropriately, and put my left hand on his right shoulder. He jumped again and twisted so he could put his back to the wall of the elevator car. A squeak had flown unwanted from his mouth. I say unwanted because his right hand had clamped his mouth shut.

"Who are you?" I said in way that would best be described as more of a purr. The sound even surprised me, and it was about then that I realised my subconscious had plans for me.

He lowered his hand, and his eyes were a little wild, darting around everywhere it seemed but at me. "Um. I'm... eighteen."

"How nice for you. I asked what your name was." I really wanted to laugh. This was so funny to me. I was well aware of my power over this poor young man. I could twist him around. Get him to do anything for me. I felt... I felt like a woman in her prime and I wanted to roar.

"Oh! Sorry! Petey, I mean Peter. Peter. Peter is my name. Yeah."

I clamped my teeth together to quell the chuckle that wanted to escape from me. I relaxed my jaw. "I haven't seen you before. Did you just move in?"

His eyes looked at me for a moment and then darted to the other side of the elevator car where there was absolutely nothing to look at. I could feel just how close we were together in the small elevator car. It could fit four people comfortably. But with me smack dab in the middle, I was absolutely inside his personal space, and I loved it. I watched goosebumps rise on his skin.

"Ah, no? We moved in about a year ago? I-I haven't seen you around either." His eyes glanced at the panel and the lit up top button numbered nineteen. "You're at the top?"

"Yes, I like being on top. Don't you?" I purred. I was so enjoying this. What was the harm, really?

He stammered and then said nothing. His brain must have short-circuited.

"Are you in high school?" I asked. It was early July. High school had finished for the year. I knew this. But I wanted to keep him talking. His discomfort was arousing me for some reason. My pussy was heating up and a warmth spread across my stomach. I glanced at the rising numbers on the floor indicator. Soon we would get to his floor.

"Y-yes. Um, no. Not anymore? I graduated this year."

My subconscious made a decision, and it surprised me when it took over my voice. "Do you know anything about computers?"

"Yeah. That's going to be my major at Berkeley this Fall."

Geeky, kind of cute, and smart. Wonderful. "Great! Would you mind coming up to my place to look at something for me?"

His eyes darted to mine in disbelief. "W-what?"

"Come. Up to my place. Look at something. My computer." I enunciated every word.

"Ah, sure?" He looked right at me, and I could see his mind was spinning out of control. "You mean right now?"

"Yes. Right now."

The elevator dinged and opened to show his empty floor.

"Last chance..." I purred.

"Ah, okay..."

We waited and the doors closed, and we were rising again. I smiled at him. "Thank you for this. You're a life saver."

Men like to be heroes. It's in all the literature. All the video games. Men need to conquer and be the victor. Tell them they are, and they will follow you anywhere. Even up to a complete stranger's condominium.

He didn't answer but he now looked frightened. I smiled to myself. Such fun. I felt alive. Energised. Powerful.

The elevator dinged again, and the doors opened. I walked out and didn't look back. I could feel him following me like a little puppy dog and I hoped his eyes were glued to my ass. There are only six condominiums on the top floor. Four corner condominiums and two side condominiums, each with a rooftop secluded balcony. I had one of the corner ones with a wrap around balcony. All secluded and with a beautiful view of the city and the river flowing through it.

I inserted my key, opened the door, and sauntered inside, putting my handbag on the side table by the door. "Come in, come in!" I said, still not looking back. "Can I get you anything to drink?" I headed to the kitchen.

My condominium is very stylish. I had an interior decorator do a complete makeover when I bought the place over ten years ago. Its feminine but not in a garish way. Its modern and chic. My kitchen is state of the art. The whole place is wired for music. I have a sunken living room filled with a plush sectional. A full wall is taken up by my entertainment unit, with stylish bookcases filled with old books. I have read every one of them, and over half are first editions. My artwork are all original oil paintings in the art nouveau style I adore. They are also a little risqué, showing naked women and men, for the most part.

Off the kitchen and sharing the same space as my living room is my ornate teak dining room set, with a large teak dining buffet and side table for serving. The outside walls of my dining room and living room are floor to ceiling windows with two French doors leading out to the balcony that wraps around the entire length.

A hallway off the main entrance leads to my office, my master bedroom with a full ensuite and walk-in closet. A spare bedroom adjoins it with its own private bath.

My condominium is decadent. I'm inordinately proud of it. I rarely leave the place, doing all my work either curled up on the sectional, or in my office. I have mastered solo cooking. I want for nothing, to be honest. And I earned every square inch of it.

I stopped in the kitchen and opened my double-doored fridge, covered with wood to blend in with my cupboards. I pulled out an orange sports drink, turned, and tossed it to Petey, who, surprised at the toss, missed it completely and scrambled around my kitchen floor trying to scoop it up. Finally, he managed to grab it and stood, his cheeks now bright red with embarrassment.

"I'm Chastity, by the way. I didn't introduce myself." I walked toward him with my hand outstretched, and when he timidly took it, I stepped closer to him, pulling on his hand and hugged him, pressing my breasts against technical shirt and slim chest.

He froze and I squeezed his shoulders a little and let him go. If you let them go, and they return, they're yours for life.

"Sorry," I said, not sounding sorry. "I'm a hugger. Follow me and bring your drink."

I walked past him and into my office. I love teak and my office was no exception. A large antique desk was placed in front of the large window. Plants and office equipment covered the desk and straddled the floor next to it, including a teak printer stand. The right and left walls were floor to ceiling teak bookcases, filled with books, awards for my magazine, and mementos of my life as a Navy brat and my few vacations to worldly places.

"Here's my rig," I said, and pulled the large, black leather chair back on its rollers and spun it around for him to sit. "Sit."

He awkwardly sat and I spun him around. He gasped and I giggled.

"Sorry about the free ride."

He glanced up at me and then at the three monitors in front of him. A large gaming keyboard and mouse were on the desk. I watched him start to place his drink on the desk and then he hesitated.

"It's okay. The surface is protected. I wouldn't want wet stains to mar it."

He carefully placed the sports drink down, unopened. He glanced up at me again and I leaned forward and slightly over him, placing my breasts inches from his head. I watched him swallow, his Adam's apple bobbing up and down.

"What's wrong with your computer?" he asked, his voice slightly cracking.

"My FPS in Skyrim has plummeted, and I don't know why," I said, watching his reflection on the black monitors. His eyes kept flipping to my breasts.

I play video games. Growing up on military bases means you play a lot of video games. I also enjoy them. Games like Skyrim and Diablo always attracted me. I loved Fable and have played it through at least a dozen times.

"Skyrim?" he blurted. I could hear the disbelief in his voice. He was another boy who thought girls only liked dolls and playing house.

I was getting excited and nervous all at the same time. I knew when he moved my mouse the screens would be filled with what I had been doing before I had gone out earlier that day. I had been watching porn. Specifically, a video where a MILF blows a rather well-hung young man and takes a massive and rather messy cum shot to the face. She takes it all and then scoops up all the creamy goodness and pops it into her eager slutty mouth. I had stopped the video right before the stud blows his load.

"Yeah, I added a new mod and I think it messed with everything. I really want it to work but not if I can't fix the frame rate."

"Okay."

"Go ahead."

He reached out for the mouse and as soon as he touched it, my PC woke up, the fans whirring, the screens flickering and then filling with the frozen video, showing the red-haired MILF below a massive, engorged cock, gripped firmly by the male lead over her eager, and open-mouthed, face. Her tits were massive, twice the size of mine, hard like diamonds, and with dark red areolas surrounding the large nips. It told me she wasn't a natural redhead, but she looked hot.

I smiled, watching Petey's jaw drop open. I casually reached across him and pressed the space bar. The video surged to life, and sounds erupted from the speakers.

"That's it, baby! Cum on my face! Spunk all over me! I need it! I want it! Feed me!" The actor stroked his hard wet cock and then held it and Petey and I watched his thick ropes of creamy cum erupt all over the MILF. Ropes covered her forehead and cheeks, with copious amounts landing on her outstretched tongue. The male actor moaned loudly, and the MILF made similar sounds. It was super hot. I wanted that. I fantasised about it all the time.

Petey was frozen in his seat watching the lurid 4K graphic pornography on my 49-inch curved monitor. I liked that size of monitor because it made the porn models that much larger and real to me. We watched as the MILF sucked hard on the cock once it stopped spewing its gift. Her cheeks sucked in, and she popped the cock loudly from her mouth. She smiled up at the male actor, her mouth and teeth coated in cum. Still smiling, she wiped a finger across her brow, scooping up the cum plastered there and popped it into her mouth. She moaned and sucked on her finger. She swallowed with exaggeration and then opened her mouth to prove she had willingly swallowed it all down. She kept scooping and sucking off the cum. Finished, she smiled broadly at the male actor who then bent down and French kissed her. That was my favourite part.

"I forgot I had been watching that! But that's my favourite part there at the end," I said to the stunned Petey. His hands were in his lap, covering his groin. "I love it when a man is not afraid of his own cum. Are you afraid of your own cum, Petey?" I placed a hand on his right shoulder, and he jerked in the chair.

His jaw was still open, and he stared at the frozen image on the screen.

"Do you watch any porn?" I asked him, squeezing his shoulder a little bit before relaxing my grip and moving my hand an infinitesimal amount that I was certain his entire focus was on. "I watch it all the time now. I get so wet. There's nothing better than a good orgasm. Am I right, Petey?"

"I-I..."

"When's the last time you had a really good orgasm, Petey? Do you have a girlfriend? Someone to get you off?"

'I-I..."

"I'm single, Petey. I live here all alone. And I'm horny all the time, Petey. Do you get horny, Petey?" I ran my hand over his scrawny shoulder and down a little towards his chest. His hands were pressing down on his shorts, and then spread a little to the left leg opening of his running shorts. That interested me if it was any indication of his length. I really wanted to see his cock now. My panties were starting to get soaked. I felt so alive and so much in power.

"I-I..."

I spun his chair toward me and lowered myself to kneel on the floor in front of him. "Stand up, Petey."

He remained sitting staring at me. His cheeks were bright red and looked hot to the touch.

"Stand. Up." I ordered and Petey shifted in his seat and looked quickly down to his groin. "Don't be embarrassed, Petey. Let me see it. I need to see it. Take your hands away."