Chastity Chronicles Pt. 02

Chastity Chronicles -- Part Two

Welcome to part two of the Chastity Chronicles. These short stories will follow a forty-year-old woman as she discovers her true sexuality. They are an exploration of complete freedom of embracing sex in all its many forms.

These templated stories are going to be wild, completely unrealistic, flights of fancy, but a fun journey. This second story follows Chastity's second student in the sexual arts. A young man's life is turned upside down by a fearful young girl.

But Chastity will fix him because that's what she does.

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 Homeless Boy

My name is Chastity. I'm forty-years-old, fit, good-looking, a red-head, and I have an insatiable desire to bed young men and teach them the ways around a woman's body. So far, and I freely admit it, at this point in time I had only experienced one student. A virgin eighteen-year-old skinny boy from my condominium called Petey.

I was with him for most of the month of July until his parents drove him across the country to California so he could prepare for his residency at Berkeley. He was a smart kid, but I imagine he's much smarter now that he learned how to pleasure a woman. The gals at Berkeley were in for a treat. He was a pro and knew how to bring a woman slowly up to his level of experience.

Part of my teachings to him were how to identify when false feelings of love insert themselves into relationships just because the sex is good. I pulled him down from his delusions, and he left happy and content. His woman was out there somewhere. He understood it was never going to be me.

Petey's mother had given me a strange look one day in the condominium lobby before they left. She stared long and hard at me and I knew she knew. Women have that sense. I was fucking her boy. Finally, she simply nodded at me, and I knew she was thankful for what I had done with her son, but would never admit it. That gave me all the confidence I needed to continue what I was doing.

But I should have taught myself how to separate love from sex, because I missed Petey deeply. Sex does that. It overrides common sense. I started running more and more because those were the only times I could empty my mind and forget about him.

That lasted about two weeks before I found a poor boy crying on a park bench in Centreville, USA, where we lived.

Here's what happened.

* * *

The paved trail along the lazy river in my town is really quite nice. There are tons of flowers and trees and benches are placed in critical places to allow a relaxed view of the city skyline and the water. On weekends, the trail is far too busy with runners, bikers, long boarders, and rollerbladers. Dogs are everywhere being walked with an enthusiasm only dogs can display. So I run the trail only on weekdays during the morning hours before lunch. I work from home as the senior editor of an East Coast magazine and do very well for myself. Including setting my own hours.

I had been running for a little less than an hour. The distance was no bother since I routinely run half-marathons and can vary my run length and strides as I need to. My stamina is excellent, and it is more about maintaining the right speed than the distance. I was at twelve kilometres and was thinking of heading home. My water was low and dammit, my left shoelace was coming loose, which was impossible seeing as I had tied a runner's knot.

I spied a bench up ahead with a young man sitting on the edge almost to the point of falling off. He was turned away from me and had his head hanging low. Not really caring about the man, I stopped and plunked my left foot up on the bench near the middle. When I bent to tie the offending shoe, I heard a sniffle.

I rolled my eyes. Oh, the drama of youth. I was so glad those days were far behind me. I spent too many nights crying in bed over some boy to ever want to return to that. They're just not worth the tears. If a man makes you cry, dump him. Easy as that. No one should ever make you cry.

With my shoe tied, I was ready to bolt and get away from the kid. Right then and there my left calf cramped like a son-of-a-bitch, and I cried out. I could see the muscle undulating and I was sickened by it. My cry of pain had the kid looking up at me, and I could see the streaks of tears on his face.

He looked to be Petey's age, but with a terrible goth thing going on. Dyed black hair, pasty white skin, zits, wearing black baggy clothes in July in the oppressive heat. He was an idiot.

"A-are you okay?" he asked me. His voice surprised me. It was soft and gentle. Pleasant even.

"No! I'm not. Look at my... FUCK! Look at my calf here? Does that look okay?"

"Oh, my God! Why is it moving like that?"

"It's a ceti eel, numb nuts."

"From Star Trek?"

That made me forget the intense pain I was feeling for a second. If you don't know, the cramp I was experiencing is painful to the extreme. It's caused by a lack of salt or something to the muscle, causing it to clench painfully and THEN just to say fuck you, it unclenches and clenches over and over. It fucking hurts. But it is not a ceti eel from Star Trek, which is the thing they put in people's ears to mind-control people. They're not real. I was actually really impressed this kid got it. It was a pop culture reference from before his time. Then I remembered: Goth kid. Right.

By this time, I was on the ground with my left leg extended flat and perched on the bench seat. I was massaging my calf hard, but it wasn't working. Sweat poured down my face, and I was in pain. A lot of pain.

"Can I help?"

I didn't want his help, but dammit I needed a strong pair of hands to massage my calf. "Yes! Massage my calf!" I hesitated and then added, "Please?"

He moved quickly and sat near my leg on the bench and soon had his hands on my calf. Even in pain, I noticed a couple of things. He had large hands. Girls notice that. Large hands and large feet really do mean a large cock. I've never been proven wrong. Second, he had remarkably strong hands. And they were callused. Rough hands. Beautiful hands. I watched those hands as they touched my flesh and dug into the muscle. It hurt like hell, and I cried out. He stopped immediately.

"Don't stop! Keep going!"

He hesitated and then started again. I lay back flat on the ground and clenched my teeth. He worked the muscle expertly. He dug in and found the right spots. Jesus, he was good. I panted with the exertion and slowly, so very slowly, the cramp loosened. I was a piece of jelly on the ground.

"Okay, thanks kid."

"I'm not a kid. I'm an adult. I'm eighteen."

There it was. That Goth sneering voice. I much preferred the other voice and said so. It's great being forty, you can say whatever you want.

"What?"

"Why speak like that? It's not very impressive. When you first spoke to me you had a lovely voice. Why hide it?"

He stayed silent and kept massaging my calf.

"Cat got your tongue, Mr Adult?"

He let go of my leg and I felt bad for selfish reasons. The kid had the touch.

"Are you okay now?"

I almost snorted. He had gone back to a normal voice.

"Yes. Thank you. That's much better. Um, can you help me up?"

"Um, sure." He stood up and reached down to me with both hands, and I grabbed them. Then he hoisted me up like I weighed nothing. Although I should brag and admit I'm only just over one hundred pounds. But the kid had hidden strength. I could see his forearms and they rippled with muscle. I was intrigued.

I carefully put weight on my left leg and reached out and grabbed his right bicep to steady myself. Really, I wanted to cop a feel. See what he was hiding under there. He was rock solid and buff. I gasped.

"Does it still hurt?"

It did, but it wasn't why I gasped. This kid was a hidden gem. I wondered what his ass looked like naked. Solid too, I bet. Hard and firm.

"Yeah, but much better. You have magic hands there, kiddo. Thanks."

He just stood there, and I squeezed his bicep. I really didn't want to let it go, but I was past the best before date and really should let go. Another squeeze and I did. I felt sad.

"I need to get home and ice this. And get some electrolytes into me. Thanks again, kid."

"Ben."

"Pardon?"

"My name is Ben and you're welcome."

"Thanks Ben. I'm Chastity. See you around."

He nodded and sank back down on the bench. He was returning to Gotham city.

I took a couple of tentative steps toward my condominium when pain shot down my left calf. I cried out and almost toppled, but I grabbed the bench rail. "Fuck!"

He was by my side in a heartbeat. I never saw him move. Fuck, he might be the batman, I thought.

"You're not okay. You're flushed with sweat. Clearly in pain. You can't walk, can you?"

I shook my head. "No, I'll be fine. I just need to walk it off."

"How are you going to do that if you can't walk? How far away is your home?"

I pointed at the tall condominium building visible over the trees about three miles away. "That building right there. The condo complexes."

"Rich girl."

"Rich woman, kid."

He snorted and I swear my pussy gave a tingle of interest.

"You keep calling me a kid and I'll keep calling you a girl, fair?"

I nodded, secretly pleased to hear his confidence. I liked that in men. "Fair. Sorry kid, but I'm not stopping. Takes more than the batman to intimidate me."

"That would make you the Joker."

I snapped a look at his face and saw the stupid grin on his face. I liked him. "Help me home?"

He nodded, and I used him as a crutch. We got about twenty feet when he stopped me. "This is going to take forever."

"And?"

I squealed when he picked me up. I was lying in his arms like a bride. It didn't even look like my weight bothered him.

"Just how strong are you?"

"Strong enough to fight the evil in Gotham, little lady."

I grinned at him. "To the bat cave!"

He actually sang the start to the old TV Batman theme, which I won't reproduce here for fear of copyright infringement.

I laughed. I couldn't help it. Yeah, I liked this kid. He was a dork, but he had a character about him. "Carry me home, farm boy."

"As you wish."

Oh yeah, he was funny, too.

Off we went. I was the damsel in distress being rescued by a strong man. I really liked it and enjoyed being paraded through the park. Speaking of strong men, he smelled a little ripe. Unwashed.

Was he homeless?

"What were you crying about back there? I saw you, so don't deny it."

I watched his jaw clench, and he said nothing.

"You having problems?"

He said nothing.

"You can talk to me if you want. I won't judge. I can give you straight, honest answers."

I saw his jaw relax a little, but he kept his mouth shut.

"School problems?"

He glanced at me briefly, but I saw the raised eyebrow. So no, not school.

"It's the Goth thing, right? You're just not cutting it? Not fitting in. Perhaps too Goth or not enough?"

"What Goth thing? I'm not Goth."

"You look Goth. You even dye your hair black."

"I'm not. I dyed it for another reason."

"You are, whether or not you know it."

He stopped walking and looked at me. My face was right there, so it was easy to see his annoyance. "Really? I dress like this because I do menial labour. Construction, empty trucks, and the like. Whatever I can."

"Oh, sorry. You need a makeover, then."

He smiled at me then and it changed his features. I must have stared because his eyebrows raised at me. "Sorry. You just look better when you smile."

His smile disappeared and the set jaw returned. He seemed to speed up a little, eager to be rid of me, I supposed.

Strange reaction. It could only mean... "You're having girl problems, aren't you? Speak to me. I'm a girl. You even called me one. I'll understand. I know things."

"I'm not. Not anymore."

"She dumped you?"

"Yes."

"That's what's bothering you?"

"Yes, and no."

"When did this happen?"

"A long time ago."

"And it still makes you upset. When did it happen?"

"At prom night."

"That was two months ago. Before or after?" I knew what I meant. All high school students do. Prom night means getting laid in a hotel room.

"After."

"Well, better that than before, right? At least you got laid."

He kept staring ahead and his jaw clenched again.

"You didn't?"

"We didn't."

"It didn't go well?"

"No."

"Her fault or yours?"

He stopped walking and looked at me. "What's with the third degree? Why do you care?"

"I do care. Maybe I can help?"

"Help? How? Are you going to go back in time and stop all the bullshit she spread about me?"

"What bullshit?"

"She told everyone I couldn't get it up. That I had a small dick, and it wasn't worth it."

"Was it true?"

He gawked at me. "No!"

"So what happened?"

He didn't answer and resumed walking. After a minute, he answered. "She chickened out. She was really popular at school. A rich kid. That she liked me, the poor kid, and went to prom with me was like the best thing that ever happened to me. She took one look at me in the hotel room and that was it. She ran from the room. People asked her what happened, and she lied. She said horrible things about me. That I forced myself on her. That I couldn't get it up. Because of who she was and who I was, they believed her. I was a laughingstock. I still am. Word spread. The state college that accepted me dropped me. My mother threw me out. Now I can't get a job. There, is that what you wanted to hear?"

His own mother threw him out? What mother would do that?

"No. I want to hear your side."

"You wouldn't believe me."

"Try me."

He took a deep breath. I could see this talk was helping him. He had to get it all out. "Don't laugh."

"I won't."

"Promise?"

"The Joker never keeps his promises."

He looked at me again and a smile tugged at the corner of his lips. Wow, he has full lips.

"She took one look at me with my clothes off and ran. That's what happened."

Oh, the poor boy. A small dick, no doubt. She shouldn't have done that. That's horrible. "Size isn't everything," I muttered, not really believing that.

"I don't have a small dick."

I blinked at that. That meant... No way! "So, you're the opposite of small?"

"Yeah. I scared her. Then shit spewed from her mouth and once she started lying, it only got worse."

My mind was fixated on his dick now. I had to know. "So, what are we talking about here?"

"Did you not hear me talking about the lies?"

"Yes. Terrible. How big are you?"

"Ten."

"Inches? Oh my God, really?"

"Yes."

"And the girth?"

"What? I don't know."

"Compared say to a can of pop?"

"Close."

"Take me home faster."

"What's wrong?"

"Nothing. Hurry."

I didn't know how I was going to check out this young man's package, but it was my new goal in life.

When we got to my condominium, I was relieved the lobby was vacant. I didn't need people seeing me in a bride's carry by some young Goth kid. We entered the elevator, and I reached over and pushed the nineteenth-floor button, sitting all alone on top of the panel.

"Top floor?"

"Yes, rich bitch, remember?"

"You don't look rich."

"I don't act it either."

We rode in silence, and when the doors opened, I directed Ben to my corner condominium. I fished out my key from the secret pocket in my shorts and he held me close to my lock to let me open it. We pushed the door open, and I told him to carry me to the couch.

Then I told him to get me some ice from the freezer. He walked off, his head swivelling to take in my luxurious space, and disappeared into the kitchen. I heard clinking and muttering and after what felt like an hour, he emerged with an orange sports drink from my fridge and a large baggie full of ice, wrapped in a kitchen towel. He handed them to me and sat a good distance from me on the couch.

"Thanks, Ben. You're a lifesaver. Thanks for carrying me home. Just how strong are you? You made that look easy."

"Genetics from my dad mostly, my mom used to say. But I've always worked out. Dad had free weights in the garage, and I used them every day. Now I do a lot of work for a hauling company in town. I unload trucks all day."

I nodded. "And your mother threw you out? Really? Over this girl's rumours?"

"Yeah."

"I don't understand that. What parent would believe her over their own son?"

"It's complicated."

"Try me."

"Mom had something happen to her on prom night. Something bad. Dad rescued her. As soon as she heard what Sandra said she was furious but at ME. Dad believes me, but mom has the final word in the house. She couldn't stand to look at me anymore. She spat on me at the end and said I was no better than all the other rapists. Dad checks up on me, but money's tight. We're not well off. Still, he gets me money sometimes. It helps."

"That's fucked up."

"It's worse. Sandra comes from very influential people in town. They're prominent in the church and politics. You know the type." He looked around my condo and I frowned. "Dad works for Sandra's father." Ben was looking at his shoes.

I was looking him over, sipping at my drink. His baggy clothes really hid his physique. "Can you take off that hoody?"

His eyes shot to mine. "Why?"

"You said you work out. Show me."

"No. I don't like showing that off."

"Why? Because of what happened?"

"Yes! My life is ruined! People think I'm some horrible rapist or something."

"You dress like one. Take off the hoody. Do it."

He sighed and still sitting down he pulled it off in one motion. Underneath he was wearing a stained tee-shirt with Alexander Hauling written on the front. What I really looked at was just how buff he was. He wasn't a Schwarzenegger; he was better. He was a Patrick Swayze from the movie Roadhouse. I wanted him right then and there. Jesus, he was hot.

"Wow."

He looked embarrassed.

"Where are you staying?"

He didn't answer.

"When's the last time you had a decent meal and shower?"

"A while."

"Okay. Down the hallway, there is a spare bedroom I don't use. It has its own shower. Go get washed up. Leave your clothes out and I'll throw them in the washer."

"I can't do that."

"I don't care what you think you can't do. I'm telling you what you are going to do. Don't sass me and do what I say. Get up. Go get washed. You smell, frankly. You'll be doing me a favour."

He looked long and hard at me. I glared back, holding the ice to my calf and sipping my drink.

"Go."

He sighed and rose and walked toward the spare room.

"Throw your dirty clothes out in the hallway."

"Yes, ma'am."

"That's a good boy."

He actually growled as he walked away. I heard the bedroom door closed, and soon after it opened and closed again.

I limped over to the hallway and gathered up his dirty clothes and underwear. I took them with the hoody and opened the closet in the hallway that hid the washer and dryer and soon they were spinning. I went into my bedroom and found the few clothes Petey had left here. Running shorts and a technical tee and another hoody. I doubted it would fit Ben, but it was all I had.

When I heard the shower turn on, I limped into the spare bedroom to lay them on the bed, when the bathroom door opened. The shower was still running, and I didn't expect that. I turned in shock to see an equally shocked Ben standing there, fully naked.