Chastity Chronicles Pt. 01

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Estcher
Estcher
1,766 Followers

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 look. 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 your cockhead 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 a 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 and that it means 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. I went a little wild.

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 and pulling on 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 for.

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. 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 us to 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 so 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.

"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 could see his whole hairy ass crack. It was a jungle.

I took his cock and drew it 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 along the back length of a cock are idiots. There are very few nerves there. All the pleasure is here 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 knew what he wanted even if he didn't. 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 continued 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 under his cock and milked out more white cream. It went immediately into my eager mouth. Young cum tastes delicious.

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 into my pussy.

Estcher
Estcher
1,766 Followers