An adult stories – Chastity Chronicles Pt. 01 by Estcher,Estcher There were two things I considered the other day: One, coming into your full sexual potential as a forty-year-old woman is exciting. 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, 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 was 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 to not care I was barren, cared. Some men thought that meant they could do whatever they wanted with me. In time, sex lost it appeal. Dating lost it’s appeal. I withdrew from society and became a senior editor for an East Coast 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 live in central USA in my overpriced condominium overlooking a lazy river.
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 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 want 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 needed the really good stuff.
My go to was always—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, standing right in the middle of the elevator.
He froze. Literally. 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. He had 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 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. With this poor young man, I used it to my advantage and let’s be honest, in the game of 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 put his back to the wall of the elevator car. A squeak flew unwanted from his mouth. I say unwanted because his right hand rose to clamp 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 brief 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. With me 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 July. 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 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 inch of it.
I stopped in the kitchen and opened my double-doored fridge, covered with wood to blend in with my counters. 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.
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 printer stand. The right and left walls were floor to ceiling teak bookcases, filled with books, awards for my writing, 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 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. 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 flickered and then filled 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.”
He didn’t budge so I did it for him. I grabbed his hands in mine and tried to pull them away. He resisted for a second and then gave in. His cockhead was poking out of his running shorts. It looked like a thin cock, if the head was any judge, but certainly a long one.
“Oh Petey, that looks like you have a beautiful cock. Stand up,” I ordered him again.
He slowly rose, and I was aware of just how close to my face his groin and cock were. His legs trembled and I smiled to myself.
I reached out and grabbed the bottom of his shorts at the legs and gently pulled down. I watched the fabric slide down over his cock, exposing a wild patch of pubic hair and the start of his shaft. I swallowed my spit and kept pulling. “Oh, Petey, look at that. This is what a woman wants.” I pulled down further exposing more and more cock until it sprung free and rose sharply up into the air, barely missing my face. I stared at it in amazement. It was standing straight up! It was hard as could be and precum was oozing in copious amounts from his cockhead. His girth was small, but his length was around seven inches. Certainly, above average. I don’t care about the size of a man’s cock—unless it’s less than five inches. He had two wonderfully large balls hanging down in his ball sack. I watched in awe as they shifted around a little. That always fascinated me.
I stared at it and then the manly smell hit my nose and a primal urge rose through me. I almost panted. “Oh, Petey. You’re beautiful.” I looked up past his wonderful cock to see him staring in disbelief down at me. “I’m going to put it in my mouth, is that okay, Petey?”
He nodded once. He looked scared and excited. The emotions warred in his face.
I pulled his cock down and aimed it at my mouth. His cockhead gleamed with precum and as I watched a string of it oozed out and stretched toward the floor. I stuck out my tongue, captured the strand and followed it up to his cock. I slowly and gently sucked him into my mouth and then he groaned deep in his chest and his cock spasmed hard in my mouth.
I moaned in joy as his cock spewed what I craved. He ejaculated hard into my mouth. Jets struck the back of my throat and filled my mouth quickly to overflowing. I sucked and swallowed, and he kept coming. His legs were shaking hard, and I reached around his waist, grabbed his ass cheeks, and pulled his cock into my mouth. His cock head pressed against my throat. I kept sucking until his cock deflated a little.
I popped him free, and he collapsed back into the seat. I smiled at the expression of disbelief still on his face. “Want a kiss?” I asked and he shook his head with a grimace. “Ah, too shy? I want a kiss for that, Petey. Kiss me.”
He looked very unsure, but he leaned forward, and I met him halfway and grasped his face with both hands and pulled him in for a deep French kiss. My tongue forced its way past his lips and found his, wet and warm. He grimaced against my lips and then after a time, relaxed and kissed me back. I loved it, but he had no skill.
I broke the kiss and grabbed his hand and then stood up and pulled him out of the chair.
“Come on. Time to eat me out. And then, Petey, we’re gonna fuck.”
I turned to the door and started to pull him to my bedroom, but Petey was frozen in place and resisted me. I looked back at him, and he looked frightened. I turned back and went right up to him and kissed him again. I broke the kiss and looked into his eyes. “Are you a virgin, Petey?”
He nodded his head.
“Was that your first blow job?” I asked, knowing it likely was. He had only lasted a few seconds.
He nodded again and looked ashamed.
“Don’t be ashamed. Everyone has to have their first time, right? Like fucking. There has to be a first time. Let me be your first. I’ll teach you. It’ll be my pleasure. By the time you get to Berkely you’ll be an expert. Those young girls will eat you up. Come on. Time to become a man, Petey. With me you’ll get to do whatever you want. Sounds pretty good, huh?”
He nodded and I could see his mind working. He had a sure thing here. Every young man’s dream come true. He just had no idea at that point just all the things he would be doing in my condominium. Either did I, at the time, but I knew I wanted this more than anything.
“Best part, Petey? I can’t get pregnant. You can blast that baby batter in me all day and all night. Come on. Time to undress your first woman.” I stepped closer and kissed him again, harder, and then sucked his tongue into my mouth. “Time to get intimate with my pussy. She wants you. Deep inside.”
I took his hand and dragged him to my bedroom. He looked around quickly, probably not seeing much at all, because his eyes were back on me.
“Take off the rest of your clothes, Petey.”
He pinched his sweaty tee-shirt and glanced toward the bathroom. “Should I shower?”
“No, Petey. I like your smell. All sweaty from a run. Undress then come and undress me.” It was true. He had a smell about him that attracted me.
He tore his shirt off, and then ripped his socks off his feet. He stood completely naked, with his cock once again pointing toward my ceiling. He stepped toward and lifted his hands and then dropped them.
“I’ll talk you through this, Petey. Relax.” I was wearing a tee-shirt, lace bra, jeans, and black panties. I wanted Petey to enjoy this. “Take my shirt off. Grab the bottom and pull it up and over my tits. That’s it.”
Petey hesitantly grabbed my shirt at the bottom and pulled it up, exposing my flat stomach.
“Hold there, Petey. Kiss my stomach. Just lean over and kiss it.”
He did with chaste kisses.
“Use your tongue. Let me feel how wet and hot it is. That’s it! Yes!”
He slavered my stomach and it tickled. He found my belly button and without prompting tongued it. My hand found his head and my fingers spread through his hair and held him there.
“Yes, that’s it Petey. Now pull it off. Careful of my hair.”
Petey did as instructed and lifted my shirt over my face and pulled it off my head. I blew hair from my face and pulled loose strands back over my ears.
“Do you like my bra?”
He nodded; his eyes glued to the top of my breasts where my flesh was exposed.
“Kiss the tops. Go ahead.”
He leaned in and kissed the tops of my breasts, his tongue out, wet, and warm.
“That’s it, Petey. Good boy. Now reach around my back and find my bra strap. That’s it. Keep licking. Find the middle. Bras are hook and loop. There are three hooks. You’ll need to…” I gasped as he somehow managed to figure it out on his own. My bra was unclasped, and I felt my bra loosen in the front. “Now slowly slide the bra straps off my shoulders. Kiss up my collarbones. That’s it. Now pull my bra away and then look. Look at my breasts.”
He did as I instructed, and I felt my bra slip off my arms and fall to the floor. I stood there with my breasts bare and exposed to this eighteen-year-old and felt my tits tighten in excitement. He pulled his head back and locked his eyes on my tits. I wore a C-cup. My breasts were round and stood like perfect domes off my chest. In the centre, my nipples were aching and hard. My pussy twitched with excitement, and I felt moisture leak from me. My areolas are almost non-existent, blending in with the hue of my skin. My nipples are long, jutting out over a quarter inch and they are thick. I’m proud of my tits.
“Touch them, Petey. Cup them and squeeze them gently.”
His hands rose, shaking slightly, and his right hand found my left breast and gently lifted it. His left hand found my other one. He squeezed them.
“Keep playing with them, Petey. Caress them, squeeze them. They’re yours right now. Take all the time you want, I won’t mind. Get to know them. Touch the nipples. Feel how hard they are. You make them hard, Petey. You do that to me.”
Petey looked at me for the longest time, awe the only expression. His eyes went back to his hands, and he stroked up to my nipples and brushed them ever so lightly.
“That’s perfect. Just like that. Not too hard. Later you can bite them, but right now I need it this way. Lick one. Go ahead. Lick one.”
He lowered his mouth to my left nipple, and he extended his tongue and licked it, his tongue barely touching it. It tickled and sent a shiver through me. My nipples are very sensitive, but once in the throws of an orgasm, I love to pinch them hard and pull on them. I didn’t think they could get much harder by this point. My pussy was soaked, and I could smell her. She was so ready, but I wanted this too. I wanted Petey to enjoy the freedom of having access to my body to explore and become intimately familiar with. I was his first and I loved it. I decided then he would experience everything with me. Everything.
His mouth naturally sucked in my nipple and a deep thrill soared through me. The pleasure shot through my body and drove hard through my fluttering stomach to my pussy. She clenched hard and I felt my juices pour from her, drenching my panties. I couldn’t help it and moaned deeply. I lifted my hand and found his head and pressed him to my nipple and held him there. “Suck harder. Yes, like that. Now the other one.” I guided his head to my other nipple and moaned when his wet mouth and warmth engulfed it. His tongue flicked on it, and I shuddered.
“Oh, Petey, you’re doing so good.”
For the next ten minutes or so I judged, he gave his full attention to my breasts and nipples. He tried to get as much breast flesh into his mouth at one point and I encouraged him. The excitement had faded for me, but he was still in his glory, and I wouldn’t deny him. Finally I had enough of that pleasure.
“Take off my pants, Petey. My pussy is soaked right now. She needs to breathe.”
He lifted his mouth off my nipple, and I looked into his eyes. They were a little glazed over. I smiled at him and pulled his face to mine and kissed him for a time. I corrected his technique and had him relax his mouth and lips. I had him kiss more gently and in time he really got the hang of it. I urged patience and gentleness, and he took my instructions like a fish to water. I was truly enjoying teaching him. My subconscious was screaming in joy, and I knew this would fast become my new favourite pastime. Teaching young men how to enjoy a woman.
“Open up my jeans. It’s a button. Pull that part. Exactly. Now pull the button free. It’s different on someone else, isn’t it? We’ll practice later. Women will love it if you master that. They’ll know you’re in control and knowledgeable, just like how you undid my bra. They’re all subtle flags and baby, you’ll be flying green ones soon enough. Yes!”
He undid the top button and then adorably, he waited for me to say what was next. I melted a little inside seeing that.
“Now. Find the zipper. Wait! Find it and then slowly lower it. It’s much shorter than a man’s. Take your time, and… wait. Zip it back up. Kiss me this time and stare into my eyes as you lower it. Look right into my eyes and make me understand you’re taking it. Claiming it. Okay, go ahead.”
He did it wonderfully. He looked right into my soul and slowly lowered my zipper. He was opening me up like a Christmas present. He was good. This little geeky nerd was a natural. And his cock was like a poker iron, hard and standing straight up, defying gravity. I wanted him fucking me hard at that point, but knew I had to take this slow. The anticipation would make it all the more powerful.
I was panting a little at this point. I had never been so aroused in all my years. This young man was mine to command. A true toy for me. I already had his delicious cum in my stomach. I wanted it to leak from my pussy, and right then decided I also wanted it to leak from my ass, for days. This lucky young man was about to get royally fucked—and all in a good way.
“Now, reach around and cup my ass and pull me in tight. Kiss me!”
He did and I loved the feel of a man’s hands grabbing my ass and pulling my quim hard against his erection. I ground against him and moaned into his mouth when he squeezed my ass cheeks harder. This encouraged him and his hands freely explored my ass. He was starting to loosen up a little and starting to do more on his own and I told him I liked it. He broke the kiss and smiled at me.
“I can’t believe you’re doing this. Doing this with me!” he said.
I kissed his nose. “Why? Don’t you think you’re good looking enough?”
He nodded his head.
“Women want confidence, Petey. Show confidence to them and they’ll eat you up. I’m going to teach you confidence in the bedroom. You’ll have to figure out how to do that outside the bedroom, but Petey, it can start here in the bedroom. After today, you’ll see. Now, sink to your knees in front of me. Do it slowly and kiss your way down. Take your time. Kiss everything and then pause and stare at my groin and then look up at me. Okay?”
Petey nodded and obeyed me again. I loved my control over this poor virgin. He was putty in my hands. He kissed down my neck and goosebumps erupted all over my skin. I moaned and encouraged him. He took his time and kissed along my collarbones and then to the tops of my breasts. He ignored my nipples for a time and licked and kissed my breasts. He licked under my breasts, and I adored that. Then his mouth engulfed a nipple and sucked it harder than before, and I moaned hard. It had been perfect.
I loved sex. I loved the attention of a man on my body, and I thrilled knowing this young man—certainly capable of coming again and again—was pleasuring me in ways I had almost forgotten. I was so ready to cum and knew it would be powerful when I did.
He kissed down my stomach and licked my belly button causing me to squeal. Soon he was on his knees and staring directly at my crotch. I looked down at him with pleasure.
“Just a little bit of cloth between you and my pussy. Look. She’s right there. Wanting you. Can you smell my musk?”
He actually leaned in until his nose touched my crotch and sniffed. Seeing that almost had me ripping off my clothes but I held on—barely. He nodded his head and looked up at me.
“Pull my jeans down, from the back and sides. You’ll have to work it but be gentle but also be confident. That’s it. Tug them. Kiss above my panty line. Yes, that’s it. Oh, you almost took my panties with them, lucky boy. Now watch as my jeans come free. Stare at the crotch of my panties.”
He was doing wonderful. My jeans were off my ass and pooled at my feet and my entire panty-covered crotch was exposed. I could feel a coolness on my pussy as the air touched my panties. His face was inches from my pussy, hidden only by my soaked panties.
“You can smell my pussy, can’t you?”
He nodded.
“Does it make your mouth water?”
He nodded and licked his lips.
“You want to taste her, don’t you?”
“Yes.”
“You want to slip your tongue into the folds and drink down my wetness. Can you see how wet I am? I’m soaked, Petey. Soaking wet for you. So very wet, so you can thrust your cock into me with ease. Do you see that?”
“Yes, Chastity.”
My name on his lips thrilled me.
“Pull my jeans off my feet and slip off my socks.”
He did it, taking his time. He was so gentle.
I wiggled my toes. “Sometime later, you’ll suck my toes for me, okay?”
“Okay.”
He didn’t even hesitate to agree, and my lust rose.
“Now. Cup my ass cheeks and pull my pussy closer to you. Kiss along my panty line on the top. Squeeze my ass and pull the cheeks apart. That’s it. I can feel you stretching my asshole when you do that. I love that. You’re going to have all of me, Petey. Are you ready for that?”
“Yes.”
“Pull down my panties and follow the top with your tongue. All the way. Don’t stop. Lick and lick. I’m fully shaved, Petey. You’ll see all of me. Exposed. Wet and swollen with desire. Now stop there and look. Really look.”
My panties were now just barely off my pussy. My swollen lips were starting to be exposed to this eager eighteen-year-old and he could see my wet slit.
“Lick the start of the slit. Right there. Do you know what’s there? Ungh.” His tongue had found my clit, hidden by my hood. I had wanted him to stop there so I could explain better what he was doing. “My beautiful clit is right under there, but a little deeper. Right now it’s hidden, but what you are doing is juicing me up even more. Now pull my panties off and dig deeper with your tongue!”
He did it and I felt his tongue separate my outer labia and he tasted his first pussy. I was so proud of myself for allowing this and proud of him for doing so well. His tongue travelled up and down in long licks.
“Now stop and savour my taste. Do you like it? Look at me. Do you like it?”
He looked up at me, his face already glistening with my juices. The scent was strong, and I loved it. He nodded and licked his wet lips.
“It’s delicious. Way better than I thought. It’s sweet and tart at the same time. I can’t describe it exactly.”
“I taste like sex, Petey. And don’t say ‘it” say ‘you’. You’re tasting me, Petey.”
“I love it,” he said simple, and then went back to licking me without my prompting.
“We are going to take a break now, Petey.” He looked up sharply at me like I had just stolen his dinky car. I laughed at his expression but smiled to soften it. “A break because you are going to explore my entire groin and I am going to teach you. Normally at this point we would fall into that bed, and you would eat the crap out of me. First, you need a lesson in a woman’s anatomy, up close and personal. That be okay?”
His eager nodding was all the answer I needed.
I pulled him up and kissed him, delighting in the taste of my pussy on his mouth and lips. I couldn’t help myself and licked his lips to get it all. Petey moaned at that. “You like that I like my own taste?”
He nodded.
“Just wait. It gets better.”
I grabbed his hand and climbed up onto my bed with him. I slowly crawled up to the headboard, delighting in exposing my entire ass and crotch to him as I did it. I rolled over onto my back, sitting up against the padded headboard, but kept my legs demurely together.
“Kneel at my feet and watch. I’m going to spread my legs and completely expose my pussy to you. I want you to scootch in closer until your face is inches from my pussy and then I’ll explain everything to you. Ready?”
His eager nod had me chuckling. “This is so hot.”
“I can see that. Your cock is dripping like a leaky faucet. I can’t wait to taste your cum again, Petey. I like having it in my stomach. I really do.”
Petey beamed at me, proud of himself.
“Okay here we go.” I slowly spread my knees and legs. I revelled in wantonly exposing myself to this young man. I was so hot and ready my outer labia were swollen and opened like a flower, exposing all my inner secrets. My inner labia are not very large, just two thin strips of sensitive flesh. I looked down and saw my juices now flowing freely and running over my asshole and between my ass cheeks. I had never been so wet in my life, and I loved it. I loved it more that I was wantonly exposing this side of me to Petey. My clitoral hood was naturally pulled back and my pearl was exposed and gleaming in the daylight streaming through the windows of my bedroom. I was ready to be fucked and fucked for hours. Petey crawled forward until his face was mere inches from my throbbing pussy.
I was so exposed and open to him. I watched as his eyes devoured my pussy right in front of him. I trembled with excitement. This was beyond exciting to me. My hormones raged and surged and crashed on the beach of my desires. My entire body hummed like a high-voltage wire. I had never felt so alive.
“Female biology 101. Your freshman year, Petey. These lips are my outer labia. They’re sorta sensitive. But these are my inner labia. I love having them sucked on and licked. Right up here is my clitoris. I’m really turned on right now, Petey. It’s not often you’ll see a woman this aroused. Remember this. Now. Touch my clit, gently.”
He reached out and put his fingertip to it. I shuddered at the direct contact.
“Okay, stop. Did you see me shudder? I can’t begin to explain just how sensitive my clit is. It’s like ten times as sensitive as your cockhead because of how small it is. Probably more. Imagine me rubbing that really hard.”
Petey looked at me in a semblance of horror.
“Exactly. My clit almost always needs a gentle touch. The gentler the better. Unless I say otherwise. My clit is designed to take the vibration from you thrusting into me and make me feel really good. Balls slapping against it is the best. If you perfect how to touch and stimulate a clit you’ll be a hero in college, I promise you. It’s like a woman perfecting a blow job. You just need patience and gentle touch. But be warned, your hunger will make you want to be rougher. Fight that urge. Take your time. Be gentle and you will win the race and all the races. It really is a marathon, Petey.
“This little hole? That’s my pee hole. Leave that alone. But here, take a look. See all the juicy folds and crinkles? That’s my vagina. Your cock is going in here soon. I’ll wrap it around your cock and cover it with heat and wetness and you’ll go to heaven and back. I will milk your cock with this beautiful part of me. I’ll draw your cum out and swallow it up. I’ll have my legs wrapped tight around you and refuse to let you go until you release your thick load and make my head explode in pleasure. My vagina coupled with the stimulation of my clit will make me come, Petey, and you’ll know when I do when I lose control of my legs and voice. Some women can fake that. I’m gonna to teach you how to tell. In fact, I plan on making you a stud.”
I was now wantonly playing with myself. I circled my clit and moaned a little. Petey was enraptured and listened intently to my every word.
“You need to be gentle at first. You can make a woman come easily with only patience and a light touch. It’s that easy, Petey. But there will be times when you need to be rough, too. Sometimes it needs to be the harder the better. I’ll teach you when to recognise both times. What do you think I need right now, Petey?”
Petey looked at my swollen pussy, the freely flowing juices, and looked up at me. “Really hard?”
I moaned at his answer and a small ripple of an orgasm floated through me. “Correct. Well done, Petey. You get an A. But we are going to be gentle for your first time. I need that more and so do you. Now, what’s this?” And I pointed.
“Your asshole.”
“Correct. Do you like it? Be honest.”
“I-I… I’m not sure? Like it? How?”
“Do you like to look at my asshole?”
“Yes.”
“I really like you looking at me this way, Petey. I’m really hot for you right now. See how wet I am? I’ve never been wetter. I have a confession. I’m into anal. I love it when the conditions are right. Petey?”
“Yes?”
“They’re right, right now. Do you understand?”
He shook his head and I frowned at his lie. “Liar. You know it means that I want anal with you.”
He looked a little ashamed.
“You’re going to fuck my ass later. Okay?”
“Okay.”
“And you’re gonna cum in my ass, okay?”
“Okay.”
“And then fuck my mouth afterwards.”
“What?”
“I want you to fuck my ass, and then put it in my mouth. I want that. I need that.”
“Yes, Chastity.”
Hearing my name from his lips swirled deliciously through me. “Crawl up me and kiss me. Don’t put your cock in me. Just feel my naked body against yours. We’re going to make out and relish in our naked bodies rubbing together. I’m going to guide your hand and fingers. Tell you what to do. I might come pretty quickly just like you did. I’m right on the edge and I need that taken care of. Come here, Petey. I want you to take me. All of me.”
Petey smiled and then surprised me by kissing his way up my body. I knew he had learned it from porn. Men don’t come naturally to that. He kissed up my thigh and then over my mons and back down the other thigh. Then he kissed my vaginal opening. A direct wet kiss followed by the probe of his hardened tongue. As he penetrated me with his tongue, I came. I’m ashamed I grabbed his head and bucked hard against his mouth. I couldn’t help myself. I had been riding the edge of an orgasm for a long time now. This whole experience was off the charts of horniness for me.
When I came back down to Earth, Petey was still tonguing me. He was lapping at me with reverence and each lick was delicious to my senses.
“Change of plans. Fuck me, Petey. Put your cock inside me and fuck me.”
Petey didn’t need to be told twice. He slid up my body, guided by my fingers gripping his hair, until he lay on top of me, pressing down on me with his weight, which wasn’t much. I felt his cock pressed against my stomach, his balls against my pussy, and he ground it against me. My legs were spread from wall to wall, open just to him.
“Just stick it in, Petey. Your body will know exactly what to do. And I’ll guide you.”
He kissed me then, my mouth flooding with the fresh taste of my arousal, and unerringly his cock found my pussy and he thrust in with one long stoke until his pelvis crashed into mine. It had been so long since a real cock had penetrated me that I had forgotten just how hot and hard they were.
The penetration clicked on something deep inside of me, and everything felt right in the world. Petey moaned what was probably the deepest satisfied sound he had ever made in his life and the sound hurried my own pleasure. I loved that my pussy gave him such pleasure. She was made for this. We fit together like two peas in a pod and my legs wrapped around his waist and pulled him in harder against me. My hands found his hard and gorgeous ass and squeezed.
Petey drew his cock back a little and his moan deepened. He thrust back in, and his body shuddered with his pleasure. A strange sound escaped his lips, somewhere between a cry of pain and a cry of pleasure.
He sobbed then, once. A deep shuddering sob. I stroked his back, aware of his raw emotions at this moment. He was now a man, fully and completely. He was where his entire sex and drive demanded he be. It was the perfect union. He had found success in what his sexuality demanded meaning and purpose.
I whispered in his ear, my voice husky and deep. “Baby, that was perfect. You’re right where you belong, safe inside me. Now fuck me. Do what’s natural. Take your pleasure from me. Take me! NOW!”
He started in random bursts of hip thrusts and then found the natural rhythm. There is no better example of the power and reality of the animal instinct in humans than during the moments of copulation. He found his stride, his face buried in the nape of my neck, his impossibly hard cock driving relentlessly into my depths. His cockhead kept lightly tapping my cervix and I found it only made the pleasure all the more intense. My pussy was ecstatic. It was filled with delicious man flesh and sending waves of intense pleasure through me.
I knew one thing: This man would be fucking me senseless for months until he went off to college. My pussy would always be available for him to find his pleasure. He had hit the jackpot with me, but he just didn’t know it yet.
He lasted for almost two minutes. I’ll be honest, it was two of the best minutes of my life in so many ways. I had discovered something primal in myself. The need to fuck young men. I had already had a mini orgasm about a minute into his frantic thrusting. He had no true rhythm but that, and the feeling of his cock growing even harder inside me, was more than enough for me. Knowing he was about to erupt inside his first woman and that the woman was ME, was more than enough.
He cried out in the most pleasurable agony there is. He thrust hard into me, his pelvis jarring into mine and grinding on my clit as he tried to go even deeper, his arms and hands gripping me with impossible strength, and he came screaming in pleasure. And surprisingly, so did I. We came together clutching each other like lifelines and for a moment my love and adoration knew no bounds. I always wanted him inside me spewing his gorgeous cum inside me. My orgasm rolled through me, screaming from my throat, and travelled from my head to my toes, in wave after wave. It was a complete body orgasm and the first true one I had ever experienced.
I was instantly addicted.
I could feel his cock continue to pump his seed. It went on forever and I didn’t want it to stop. He pumped and pumped, his hot liquid searing my insides. I could feel his cream inside me. Filling me up. The woman that I was, was satiated.
Then sadly, I realised his cum would never find purchase. Never impregnate me. It would never reach it’s intended goal. I held him tight and rode my powerful orgasm alongside his and pushed those stray thoughts away.
He went completely limp on top of me and I stroked his back with my fingertips. His cock would spasm every now and then and I merely held him. I was happy his first time was this powerful. He would always remember and immortalise me. My subconscious purred in a satisfied and happy way.
I let him lie there for another ten minutes. Men need to rest after an orgasm. Women come alive after an orgasm. I don’t know why that is, but it sucks. When his limp dick slipped out of me, followed by a flood of cum, I gave him a shake. He grumbled. Already no longer a virgin and already having attitude. I wasn’t having any of that.
“Get off me and I’ll clean your dick.”
His head lifted off me and he blinked blearily at me. “Wah?”
I pushed on his shoulder and rolled him off me. He landed on his back with a grunt, and I spun around, and before I second-guessed myself, I slurped his limp cock into my mouth. He moaned along with me. I had never done this before, but I had always wanted to. The taste was divine. Cock, cum and pussy. It was my new favourite.
He was hard in no time and when he was pawing at my ass I relented and spun back around and kissed him, driving my tongue into his mouth. He grimaced but kissed back.
“I don’t think I like that,” he complained when we broke for air. I knew he meant the sloppy kiss.
“You do that for girls, and they are going to love you,” I responded. “I promise.” Then I thought about it. “Well, maybe not all girls. Girls like me will though.”
He looked long and hard at me. “I don’t think there are any other girls like you.”
“Ah, that’s sweet to say. But there are. More than you realise. Especially with the Internet. I didn’t know I wanted it until I saw it on my computer.”
“Hmm.”
I looked at him with squinted eyes. “Look at you, suddenly more confident and cockier. I like the confident, maybe not the cocky so much.”
He waggled his eyebrows. “Cocky, heh.”
I glared at him. “Lose that and I mean it. Its not charming. There’s a time and place for being cocky. Now is not one of them.”
Immediately he looked like he had killed a puppy. So I kissed him. “Better. Now, where were we?”
He shrugged.
“Post coital bliss. It’s a thing. You’ll want to sleep, just like you did with me. Fight that. It’s easy if you try. Enjoy the rapture for a time, but while you’re napping the woman you’re with wants to go another round. Remember that. Now that you’re no longer a virgin, we need to explore other things to do together. So next is foreplay. We kind of skipped it because, well, because sometimes you just need to shag. Get it out of your system. Like we just did. So foreplay is important. The woman may not be at the same level of excitement as you are. Men get hard and for them the foreplay is over. For women there’s a need for intimacy. A build up of pleasure to lead to us willingly spreading our legs and letting our man spunk inside them.
“So we are going to neck and touch each other in intimate ways. Lots of caressing, stroking, kissing. I’m going to play with your cock and balls and you’re going to finger me up. Get the juices going. In a perfect world, where men aren’t against their own body fluids, we have foreplay, fuck, eat each other out, fuck, rinse repeat. Sadly, this world means after the fucking there isn’t anything else. You are going to learn otherwise eventually. I’m gonna make sure of that.”
He grimaced and I laughed and slapped his chest, the sound wet with our combined sweat.
I slid up his chest, hanging off his right side and started to passionately kiss him. It took him a bit, but he understood the type of kissing that was required. This was the kissing between two lovers. Intimate. Soul searching. The need to pleasure the other person. It got heavier and heavier and then I reached down and took his cock in my hand and started to jerk him. He moaned and I whispered for him to finger me. I wanted to see what he could do on his own. As I expected, he soon had a finger jammed into my pussy. I stopped him.
“Okay, remember your Female Biology 101 class? Like from 30 minutes ago?”
He nodded.
“Yeah, you get a F now.” I rolled onto my back and spread my legs a little. “Scootch up to me and using your left-hand reach between my legs. Be gentle. Remember gentle? That’s it. Now don’t just go plunging in. Feel my entire pussy. Massage the outer labia, firmly but gently. Pinch gently right where my clit is hidden by my labia. Mmm. Like that. Now jerk it a little, like a little tiny cock. Lighter. There. Like that. Now watch my face…”
“You’re beautiful.”
“Hush, but thanks. You can tell what I like by my face and by the sounds I make. Men need to make more sounds in bed. It’s hard for women to judge what’s good and what’s not. Remember that too. Okay, kiss me, and don’t forget my ears and neck. And collarbone, and nipples, and mmmpf…”
Petey was necking with me pretty good now. He kept his tongue out of my throat and danced with my tongue. He lightly stroked my clit through my outer labia, and I was starting to melt. Sadly, my student needed more direction. He was lucky I was already soaking wet and dripping his cum from my vagina. I was lucky too.
“Okay,” I panted into his mouth. “Now. Take your middle finger and slip it down and separate my outer labia and inner labia. Touch down to my vagina and then gently come back up and stroke my clit. Gently! Remember gently? Better. Keep doing that. When and if it feels dry dip into my vagina and get your finger wet again. Yes! Like that. Dig a little deeper. Deeper. Now out. Now in. Yes! Now take that wet finger and go back to my clit. Yes! Like that! Feel the difference? Watch my face. Kiss me. More kissing! Oh! Never mind. That’s it. Suck my nipple! Ungh! Harder! No, on the nipple! Use your teeth but gently. Give me a nip. Oh my God! Perfect. Now be the perfect gentleman and keep doing that until I come again.”
Petey wasn’t perfect but he was a fast learner. He was now gentle on my clit and sending pleasure through me. His attention to my nipples, ears and neck were really good and I found myself quickly approaching a pleasant orgasm. In a moment of selfishness I sank myself into it and came pleasantly around his finger.
“Oh that was nice. Thank you.”
“My pleasure, Chastity.”
I kissed him and then pushed him onto his back. “Now, your turn. You need a proper blow job. Try to last this time. You need more staying power. Ready?”
He grinned at me.
I grinned back and then slipped down between his legs. Never put any weight on the legs. It’s distracting to men. Imagine being eaten out with a man pressing his weight on one of your legs. Nope. So I slipped between his legs and then pushed his thighs apart. I looked up at him and he was looking worriedly back down at me.
“Relax. Go with everything I do, okay? I promise, this will rock your world. You’ll go to bed at night thinking about this for a long time.”
“O-okay…”
I smiled at him and then really looked at his cock. It was gorgeous but he needed a trim to his wild growth of hair. I drew his cock deep into my mouth. He was hard as iron again and I loved the feeling in my mouth. I could taste his manliness, his cum, and my pussy. It was my new favourite flavour and thought briefly of what that might mean to me. Could I like the taste of women? Did that mean…? I shook myself mentally and decided I would worry about that another day.
His cock hit the back of my throat and thick saliva filled my mouth. I drooled it out and used it to lubricate the length of his cock with soft strokes. Petey hissed in pleasure.
“Good, more noises. I like vocal men. All women do.” I sucked his length into my mouth. After a moment, I popped him free to relax my jaw and worked on the underside of his cock. I looked up at him. “Women who pay any attention to the top length of a cock are idiots. There are very few nerves there. All the pleasure is in the head…” I sucked it and he drew in a sharp breath. “Or right under the head at the frenum…” I licked it and then sucked it by itself, and Petey’s hips came off the bed. “Or all along the complete underside. As I get closer to the balls, it gets better.” I demonstrated and Petey moaned. “But a sure way to pleasure a man is to lick his balls. Like this.” I extended my tongue and carefully bathed his hairy balls with my spit. I was super gentle knowing how sensitive they are. Then I started lapping at them with the point of my tongue. Circling them and teasing them. Petey was moaning loudly.
I went back to his shaft and took as much of him as I could. I started to suck him using more suction. I took my other hand and gently caressed his heavy balls. My mouth tasted a flood of precum, so I pulled away to stop him from coming and licked down his shaft, over his balls, and then looking up at him, I licked below his balls right on his taint. Petey’s head shot up off the bed and he stared down in shock at me. I grinned but kept licking.
“Oh my God, Chastity! What are you doing? That’s amazing!”
“Just wait…”
I kept licking his taint, intentionally coming closer and closer to his asshole. His head was off the bed staring intently at me. I knew what he wanted but he was afraid to ask. Or he didn’t know to ask. That was okay. I did. Without hesitation I rimmed him while still stroking his slick cock. My tongue circled his anus and then gently probed the centre of it. The act thrilled me. It was a first for me, too.
Petey cried out and I felt his cum surge hard through his cock and erupt in startling force. I tracked his first rope as it soared high in the air. It splashed down on his chest and was followed by three more. When his cum continue to weakly pump and ooze out his tip I engulfed his cock with my mouth and sucked what cum remained into my mouth and swallowed. I ran my thumb up along the thick tube of his cock and milked out more white cream. It went immediately into my eager mouth.
Petey was still moaning loudly, and it was music to my ears. I slid up his body and hoovered up the cum on his chest and stomach. I slurped loudly and lewdly and made a show of swallowing. I found more cum on his neck and then kissed him hard. He didn’t fight me this time and we French kissed around his fresh cum. I continued to stroke his cock and then lifted a leg over him and buried him in my pussy.
Petey moaned again and his hands found my ass and pushed me down harder on him.
“My turn,” I stated and rode him cowgirl. I took what I needed from him. I angled myself for maximum pleasure for me. His cock scrapped my inside walls right where I wanted it and drove pleasure deep inside me. Petey’s head lolled back and forth, and I grunted with my exertion. He stayed hard the whole time, and I was secretly pleased. It only confirmed that I needed young men. Men with stamina and the ability to stay hard and deliver the cum I so desperately needed over and over again.
I knew then that Petey was going to be the first of a long line of lovers.
Without warning I felt an orgasm rising within me. But I wanted more.
“Petey…” I gasped and got off him by standing up. I looked down at him. He looked up at me.
“What?”
“We’re gonna up this a notch.” I turned around into a reverse cowgirl, grabbed his cock, lined it up and dropped down on him. I loved the sudden sense of being filled. I moaned along with Petey. “Petey, look at my ass!”
“It’s perfect. Round and smooth…” he caressed it.
“No, my ass! My asshole! Look at it.”
“I am!”
That thrilled me. I loved him looking at my asshole while my pussy clenched his cock. “Wet a finger and stick it in!”
“What?”
“DO IT!”
I heard him licking his finger, but then he swirled it in our combined juices. Good boy. Then his finger touched my O-ring. I loved it.
“Stick it in! Gently! Always gently!”
I felt the pressure of the tip of his finger against my asshole and I relaxed, and it slipped easily inside. My asshole clenched down hard on it. No person had ever done this. I had done it myself with toys, but never a real person. “More!” I demanded and needed it.
Petey pushed harder and it felt like maybe half his finger. “Fuck my ass with your finger!”
He pushed in and then out and the feeling was out of this world. I moaned a deep guttural moan. I could feel his finger pushing down on his own cock and that pushed deliciously on the walls of my vagina.
“I can feel my own cock inside you!” he exclaimed in surprise, and I managed to laugh.
I kept driving his cock in and out of me, rising high and dropping down. “More! Harder!”
Petey didn’t hesitate and soon he was driving his finger into me opposite the penetration of his cock. I was constantly being penetrated and the differences between my pussy and asshole were startling, and I heard a loud ringing in my ears. I was grunting like a mad woman. I couldn’t make any other sounds. An image popped into my head and once there I knew I needed it. I rose up and got off Petey and scrambled for the bedside table.
“What’s wrong? Did I do something wrong?” asked Petey, his concern real in his voice.
“No! I need lube!”
“Lube? For what?”
“You’ll see!” My hand closed on the bottle of lube in my nightstand, and I cheered. I swung around, popped the lid, and squeezed a generous amount on Petey’s rigid cock. I stroked him hard with it and Petey moaned. I squeezed some into my hand and shoved it between my legs and right into my asshole, driving two fingers deep. I got on all fours with my ass pointed at Petey. “Stick it in my ass, Petey. Do it!”
“I-I can’t do that!”
“Why the fuck not?” I growled.
“It’ll hurt you!”
“Do I look like it’s gonna hurt? Fuck my ass, Petey. Now!”
I felt the bed shift and Petey’s hands landed firmly on my waist and ass. I liked that. “How?”
“Push the tip inside. Just the tip and hold it there until I say.”
“Okay.” Petey fumbled around and I felt his cock press against my asshole. It felt right and frightening at the same time. He pushed harder but it slipped down and drove into my pussy. It felt great but it was not what I wanted. He pulled out, apologised, which made me giggle, and he lined up again. I knew what to do and relaxed myself and pushed on my asshole like taking a dump.
Petey popped inside and I froze at the sudden it’s bigger than I thought moment. “Hold it there! Don’t move!” I hissed.
Petey froze. “I knew it would hurt you!”
“It doesn’t hurt! Not exactly.” I waited, feeling the orgasm that had been approaching start to fade. I wanted it back and so I pushed my ass back and felt Petey’s cock violate my asshole a little deeper. I felt nothing but pleasure. Months of using a dildo on my ass had paid off. I pushed back harder and Petey made a sound between pleasure and awe.
“It’s going into your ass, Chastity!”
“Yes,” I managed to grunt and pushed back harder and then felt Petey’s groin meet my ass cheeks.
“It’s all the way in, Chastity.”
“Yup. Now fuck my ass, Petey. Go slow at first.”
Petey grabbed a firm hold of my ass cheeks and started to gently pull out. The feeling was intoxicating. It felt like his cock was coming out for miles. Then he paused and started to push back in. It filled me in a whole new way, and I saw stars. Then he was pulling back out, and pleasure exploded inside me. It honestly surprised me, and I was elated. I reached between my legs and found my hard clit and jilled myself hard.
“Harder.”
Petey did as he was told. “This feels really good, Chastity. Is it good for you?”
“Oh my God, yes. Faster!”
In no time, Petey was pumping away at me, his hips slapping my ass loudly, and I was screeching in pleasure. It was a never-ending wave of intense pleasure. So much different than a vaginal orgasm. It was… better.
“Chastity! I’m going to cum! W-where…”
“IN MY ASS! CUM IN MY ASS!”
Petey grunted and he exploded in my ass. It set me off in an unexpected way. I could feel his cum splashing inside me, different from a man coming in my pussy. It lifted my orgasm to a new, never-before-felt high. I screeched and jilled my pussy, which set of a minor orgasm in my pussy. It was too much, and I could no longer hold my upper body up and my head and shoulders collapsed onto the bed like I was shot. Petey was still thrusting and coming and crying out my name.
“Keep fucking me Petey! Keep fucking me!”
He thrust a few more times, then Petey was spent, and he collapsed on top of me, crushing me prone into the mattress, his cock spasming deep inside my bowels. I fucking loved it. I needed this every single day of my life, and I must’ve said that.
“We’re going to do this again?” asked a hopeful Petey.
I couldn’t help it. I started laughing. I laughed so hard I pushed Petey out of my ass and he complained which made me laugh harder.
The girls in Berkeley were going to be in for a treat. His training was only just beginning. And we still had so much more to do and learn.
What a lucky boy.
And what a lucky girl I am, I thought, as I felt his cum escape in bubbles from between us, tickling me.
Epilogue
In October of that year, my mobile phone rang and vibrated, and I looked at it sitting in my office. I didn’t recognise the number but recognised the California area code. My former student Petey was in that area code.
I answered and held my phone to my ear. “Hello?”
“Um hi, is this Chasity?”
“Yes, who is calling?”
“Ah, you don’t know me. My name is Kimberly. I’m a senior at Berkely in California. It’s where I’m calling from. I wanted to thank you.”
“Thank me? I’m sorry I don’t even know you. Thank me for what?” My mind immediately went to the magazine I edited.
“For Peter. He told me everything. About what you did. Seriously, on behalf of women everywhere, thank you.”
That froze me. “I, ah, don’t know what you’re talking about.”
“It’s okay. I know it’s a secret, but, well, I got it out of him. There’s no way he was that good. I mean. Fucking wow! So I had to know how and now I do. He’s the talk of the campus. He’s like, perfect, you know? He said you taught him everything. He’s… so perfect in bed. Absolutely perfect. Just when you think you can’t cum any harder, he takes you to a whole new level. I’m… Jesus. I just wanted to call and thank you. I had to. I’m so grateful. You should win awards or something. Listen, Peter doesn’t know I’m calling. Don’t tell him, okay?”
“No problem.” This is strange, I thought.
“One more thing I thought you should know. Did you know he won’t let anyone call him Petey? Ever. He told me only you can. Did you know that?”
I was stunned. I didn’t know that, but my heart swelled. “No, I didn’t. But thank you for that, too. I wish you could tell him hello for me and tell him to call me.”
“I’ll find a way. And he should be calling you. He’s your padawan, isn’t he?”
I chuckled. “Yes, one of many. But he was my first.”
“You… you’re amazing. Like wow. Thank you. I had to thank you. But your secret is safe with me. I’ll never tell a soul.”
“You’re welcome. Glad I could help.”
“Help? I’ve cum so fucking hard these past few weeks you have no fucking idea.”
“I do, actually.”
She laughed. “Okay, fair. Take care. I think 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. My three o’clock was here with his girlfriend.
Padawans. 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.
Author’s Closing Comments:
Tell me what you think! If you liked it hit that five-star rating! Also, let me know what you think. I respond to all queries.
I envisage about six of these chronicles. Sadly, that’s just more to pile on to all the other stuff I have to do! But I needed this. I found writing this therapeutic where I didn’t have to worry about plot, character development, and other technical stuff. Just pure fun. It was liberating for me.
Lana Ocean
May 2023
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