Naughty Boy Ch. 02

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20-year-old boy continues his adventure.
3.6k words
4.24
59.3k
24

Part 2 of the 2 part series

Updated 10/15/2022
Created 12/07/2013
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fantaseeboy
fantaseeboy
1,601 Followers

I'd always been embarrassed and ashamed of my body. I suppose I had an image of what a guy is supposed to look like in my head, and that isn't me at all. I had to look up at nearly everyone I'd ever known. The first time Sam picked me up in his arms he laughed and said I couldn't weigh more than a buck soaking wet! Well, that's not quite true, but it's close. My body hair is sparse at best and to top it off, my penis is quite small. But after spending so much time with Sam, hearing him tell me how cute I am, how desirable I am, and how lucky he is, I've become very comfortable with myself. So comfortable in fact that Sam says I'm becoming a tease, which gives him another reason to spank me.

It isn't hard to tell that he loves me running around naked or barely dressed. He even went so far as to buy me a few thongs, but even the extra small sizes were too big for me. The space they leave in those up-front are way too big for my penis! So, when I'm in one of those moods or Sam asks/tells me to, I'll spend my time naked, wearing only a towel or something equally revealing. Sam keeps teasing me about buying me some girl's panties and lingerie, but I haven't seen any yet!

It's funny, the more time I spent naked, the less time he did! Here I was prancing around the house in my birthday suit at any time of the day and Sam changed his clothes behind closed doors. The only time I ever saw him naked was when he made love to me. When I gave him blowjobs, he would simply open up his pants without even lowering them. The more time I spent bare naked in front of him, the more natural it began to feel.

It got the point where I dreaded to have to get dressed at all. But I did have a job and no matter how meaningless it was, Sam wanted me to keep my job at the movie theater. Sam made more than enough money to support me, and he told me someday he would, but for now he wanted me to learn what earning an honest wage was like. That, and I know he enjoyed driving me to and from work. He would get me all horny right before I had to go inside! And sometimes on the drive home, he'd have me strip naked for the late night drive. During those drives he would stick to well-lit surface streets with lots of stop lights. On occasion he would threaten to pull into a fast food drive thru, and most recently he parked in front of my mom's house and shut the engine off! He asked me if I wanted to go in and say hello! Of course I told him I didn't, but I couldn't get the idea out of my head. I'd thought about 'accidentally' exposing myself to my mother while I lived with her. But having Sam suggest it, while I was so horny made it infinitely naughtier. And that night while making deep, slow love to me in our usual face-to-face missionary position, Sam asked what was on my mind when I got quiet. After asking that same question a dozen times I finally told him.

For a long time I'd kept secrets from my mom. My homosexuality was the big one. It felt like I was lying to her each time I looked into her eyes. After coming clean about that, I wanted to tell her more of my secrets. But I suppose there are some things a mother shouldn't know about her son. But sharing the secret about my sexuality made me feel closer to her than I ever had before. And as time passed I wondered if she had any questions or wondered 'how' we made love. If I were completely honest with myself, I would like her to know those details along with every other secret and fantasy I've ever kept from her. In reality, I don't know if I would be able to tell her things like that. It was almost more than I could bear to tell her I was gay and moving in with Sam! However, having her know everything about me, keeping nothing from her, was something that made me squirm every time I thought about it. And that's squirming in a good way.

While I was trying to explain those thoughts and feelings, Sam kept making love to me. Sometimes he picked up the pace, other times he thrust into me with more force than usual, and other times he held perfectly still. I guess those were the times he was calming down so he wouldn't cum. He stopped twice to add more lube, we both like it extremely slippery. Toward the end of my confession, Sam rolled onto his back and held me on for the ride, so I wound up on top. With my hands on his chest, I slid up and down on his throbbing, swollen cock. Sam reached up, stroked my cheek with his hand and whispered, "God, I love you. You are the cutest thing. You are also very naughty." I just giggled and blushed. "Sweetie, would you like me to figure out a way to test the waters with your mom? See if I can find a way to hint about one of your deeper secrets, just to find out how she reacts. If she is interested, I'll tell her more. But if she avoids the topic, we'll know she isn't comfortable knowing any more than she already does. Does that sound like a plan?"

As I dropped onto his chest and moved to kiss him, I squeaked "Yes please." Then our lips met and I felt him thrust into me hard and deep. While our tongues danced together, my mind ran wild with the things my mom may know about me before long. Between that thought, the passionate kiss, my love for Sam and his cock buried so deeply inside me, it made my little erection throb and jump between us.

We held each other closely without speaking, the only sounds in the room were the wet, popping sounds of his well lubricated cock sliding in and out of me. When my penis began to tingle and I felt my little balls begin to rise up inside me, I knew I was getting dangerously close to squirting. I rose up off of Sam's chest stretching my arms way up above my head, my legs straddled beside his hips, his giant cock pointing straight up, buried deeply in my bottom. "I love you Sam. And I don't care what I say after I squirt tonight, if she is okay with it, I want you to tell my mom everything about me. Every naughty thing I've ever done, every fantasy I've ever had, everything okay. I don't know why, but it's like I need her to know the real me."

Sam smiled up at me warmly and whispered, "I love you too. And I promise I'll do what I can about that." He then reached up and laid his hands on my hips and began pounding in and out of me at a delirious pace. It was obvious that he was as close as I was. When I reached down to touch myself, to help it along, Sam slapped my hand and told me to leave it alone. I bit my lip, feeling like I'd done something wrong, like I'd disappointed the man I love. So I did as I was told and kept my hands well away from my poor neglected penis.

His thrusts kept up for a minute or two until I felt him swell up inside me, stretching me out even more than usual. He groaned loudly just before his hips jumped up, burying his cock so deeply inside me. The sensation of him ejaculating his love inside me sent me over the edge. My hands balled up into fists, my toes curled, my head fell back and I heard myself squeal in an unusually high pitch. As my muscles began to twitch wildly, my penis squirted out my juices in a high arch landing on Sam's stomach. That was the first time Sam made me orgasm without even touching my penis. He told me girls came like that and he thought it was really special that I did too.

Several days passed without another word of our conversation about my mother and my secrets. At times I was glad, there were some things that made me shiver just thinking about her knowing. But then at other times, when I was feeling a little more naughty, my thoughts would imagine Sam sitting down with my mother and telling her private things about me. During those times, I would imagine Sam telling her my most embarrassing secrets. And that would make me so terribly horny! It was at one of those moments when Sam happened into the room to find me fantasizing and rubbing myself.

Sam smiled wickedly while undoing his belt and pulling it off. After folding it in half, he made it crack loudly. I shivered, and couldn't utter a sound. He spoke so calmly it frightened me even more than if he had shouted, "I come home after a long day at work to find you naked and masturbating in the kitchen? What would your mother think of this? If you've ever deserved the belt, it's now. Bedroom, now." And he raised his arm and pointed the way.

I was fighting back the tears as I ran past him, down the hall and to our room. He'd never spanked me with anything more than his open palm. Sam was really strong and I knew when he hit me with that wide strap of leather belt, it was going to hurt more than anything I'd ever felt before. Sam casually walked in still holding the folded over belt in his right hand. He grabbed two pillows and placed them on the edge of the bed. "Lay over them, butt up high, I want I nice target." I scrambled to the bed, still naked, and laid across the pillows. My bottom felt more exposed than ever before. I'd never, ever felt so vulnerable.

"Ten should do it." And without wasting a moment, I heard that belt swishing thru the air. For the briefest moment, I thought of a car racing at me from behind. Then it struck me across both cheeks. I don't know if I screamed or what, but the room became really loud between the sounds I was making and the repulsive sound of that leather hitting my bare skin. That belt kept coming down with hardly any delay. After each impact, Sam would count out the number in a breathless voice. Between three and four, I reached back with both hands to protect my poor bottom. Sam scolded me and swung the belt down harder than ever, it caught the tips of my fingers on my left hand. I didn't reach back again.

The seventh blow was harder than the sixth, and the eighth harder still. The ninth blow felt like my cheeks were being split across sideways. I know I must have been screaming and crying and begging for mercy, but I can't remember for sure. Sam hesitated for several seconds, I could hear him breathing so heavily behind me. "Last one Kitten, are you ready?" I don't think I responded. But I heard the belt swishing back through the air and it hit me with so much power I nearly passed out.

I didn't dare move. My bottom hurt so badly, it was throbbing and I was afraid to know what it looked it. Sam laid the belt down beside my head so I could see it. "From this point forward, you will ask my permission before playing with yourself. If I catch you masturbating again without my approval, I'll be forced to take more drastic measures. Are you familiar with what a chastity belt is? If not, you will be if you make that mistake again."

There were several minutes of silence where I only heard myself sobbing quietly. Finally, Sam spoke again, "Stay right where you. Don't move a muscle until I come back for you. Do you understand?" I whimpered softly and flinched when I felt his fingertips gently graze over my terrorized flesh. Sobbing quietly, I whimpered "Yes."

I laid right where I was on the bed, bottom raised up high, naked and staring at the belt which was just used to punish me. I have no idea how long it took to get control over myself and stop crying, but I finally did. With my breathing back to normal I could finally hear Sam in the living room. Guessing, I'd say he was sitting in his chair when I heard him open the bottle of beer we'd had in the refrigerator since July. Then I heard the sound I was both dreading and dreaming about.

"Hello Diane. This is Sam. I was wondering if I could ask you a question about your son."

He was calling my mom!

"Good. I'm glad to hear that. I'll be sure to call you more often with questions I may have."

Oh gawd! I was shivering there, completely forgetting about the belting I'd received.

"I'm curious, while he was living with you, did you ever have reason to punish him? And if so, how exactly did you punish him? I've run into a few different situations with him recently where I feel he deserves a firm punishment of some kind. And I wanted to know your opinion on the matter."

I'd wanted her to know my secrets for so long, and it was finally beginning to happen. And now that it was, I was terrified of what she might think of me.

"Oh, just different things. I caught him telling me a half-truth a few days ago. And there are other, more private things that I probably shouldn't tell you."

What would she say to him? What would she think of me? This was the moment I'd find out how far Sam could take this. I wanted to get up and stop him, but as soon as I moved, my bottom burst out in pain. So I held still and listened.

"Are you sure? Some of it may be a little strange to hear."

Only a few moments passed before he spoke again.

"Alright, if you're sure. To be perfectly blunt, he's quite the little cock tease and not just to me. I've caught him exposing himself to our neighbor and he masturbates in front of open widows without a worry. I know our neighbor is fine with it. Hell, the old man actually enjoys seeing his little peanut. But I'd hate for him to show himself to the wrong person." After a brief moment, he clarified, "Peanut, it's what the old guy next door calls his penis. If you weren't aware, it's unusually small."

I didn't even know Sam was aware that I'd been flashing the old man next door. I always did it from a distance so I could run away if he approached me. And the few times we'd talked, I flirted with him shamelessly. But I'd always done those things when I thought Sam wasn't at home. And he told my mom that I have a small penis!!

"Well, I've given him a few spankings. But really I think he may deserve something more. I've honestly thought about taking my belt to his bottom. Perhaps that would straighten him out. But I really wanted to know how you felt about that."

Oh Gawd! What had I asked for? I knew Sam would do it. Ever since I suggested spankings, Sam had been anxious to help me fulfill the fantasies I shared with him. I began trying to think of a way to get him stop to stop after telling her what he already had. But the way I had asked him, almost begged him to do this for me, I knew there would be no stopping him. My mother would soon know my deepest, darkest secrets and fantasies.

"Diane that is a great idea. Why don't we get together this evening so we can discuss this in person, just the two of us. If you really are interested, I have quite a few stories that you may find interesting."

They were going to meet in person and talk about me? I'd have no idea what was said! I'd never be able to look at her the same way again!

"It was nice talking to you and thank you for the input. I'm looking forward to picking up this conversation tonight. But I started doing something just before I called you and I really should finish it up. So I will be on your doorstep at 7 sharp."

--

I was afraid to look at my bottom until later that night when I was alone. Sam was off talking with my mom, telling her things about me that a mother shouldn't probably know. Naked, I timidly looked over my shoulder into the mirror. I was shocked at what I saw. My cheeks were nearly glowing red! They were still very tender to the touch and I had to be really careful when I sat down. I doubted I'd be able to put on anything snug fitting for at least a day or two.

It was after 12 when Sam finally arrived home. I was in the living room, wearing only one of his dress shirts with the bottom two buttons done. He walked into the room and stopped when he saw me, smiled and approached me on the couch. Before sitting down beside me, he undid his pants and pulled his throbbing cock out. Laying his hand on the back of my neck, he guided my face into his lap. I rose up on my knees and leaned down onto his cock.

When I had him in my mouth I could already taste his precum. Sam moved his big, strong hands to the back of my head and set a rapid pace for the blowjob. Only then did he begin to tell me about his night. "Your mother now knows quite a bit about our relationship. She knows how I make love to you, how you suck my cock, how you swallow my cum. I told her how few clothes you wear around the house. I told her about every inch of your beautiful body and the cute little sounds you make when you cum. I told her about the spankings I've given you and that you asked for them. However, I did leave out the belting you received this afternoon."

He groaned as I dove as deeply as I could, to the point of gagging. Sam's hand on the back of my head was pushing down, not letting me pull back up. He held me there with the spongey head of his cock tickling the back of my throat until that feeling finally went away. Sam kept his cock right there at the back of my throat when he picked up the story again. "I think the best part of the conversation was when I told your mom about the time I pulled up to her house with you naked and horny in the passenger's seat. When I told her you didn't want to go in and say hello, she told me that I should have made you. She said she would have liked to see you like that." Sam paused to let that sink in. "That part of the conversation was pretty late in the evening after a few bottles of wine, so it may have been the liquor talking, but I don't think so."

Taking my hair in his hands, he began fucking my mouth. Up and down I slid on his cock, feeling the swollen veins sliding on my tongue. My mouth filled with the taste of his precum. Tightening up my lips when I felt him getting close. "It's frightening how horny I got telling your mother those things. She must've been sopping wet when I left. I bet she's laying in bed right now fucking herself silly." And right then, he pushed my face down hard. I felt his fat cock head go just past my gagging point and enter my throat. My entire body spasmed wildly as I panicked being unable to breath. Sam then groaned deeply and shot his love directly down my throat and into my belly. He released my head after the first shot and I pulled off so I could breath. When I did, the next three blasts of his love squirted onto my lips, nose and chin while I caught my breath. I rose up and Sam smiled at me, "If your mother could see you now." I giggled and licked my lips. Sam reached and scooped the cum from my face onto his finger before feeding it to me.

"Did you really tell her all those things?" I asked, afraid to know the answer.

"Yes I did. And sweetheart, we made an agreement. She asked me to keep her informed on your behavior and well-being."

With that I carefully leaned back onto the couch and slipped my hand under the shirt to touch myself. Sam smiled and watched me closely with a strange look on his face. It took me a while to realize what I'd done. "Oh Gawd! Um, Sam, is it okay if I touch myself?"

An evil looking smile crept onto his face, "Looks like we're going shopping for a chastity belt."

fantaseeboy
fantaseeboy
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8 Comments
ShadowRosieShadowRosieover 4 years ago
Hated this

This is abuse. Abuse is illegal. Leave when you get the chance, it will save your life.

AnonymousAnonymousabout 5 years ago
Asking to be spanked

Is there anything more erotic than a young man asking to be spanked,knowing that he will get some stinging spanks? This story is even more fascinating, because he has given his male lover permission to tell his mom every sly naught sexual thing he has ever done, and obtained her permission to administer appropriate punishment. Tantalizingly, the story does not specify all of the misdeeds--we are asked to imagine them. How would you punish a young man who refused to offer his anal for sexual purposes to an older, more powerful lover?

AnonymousAnonymousover 6 years ago
More please

I can't wait for naughty boy 3!

AnonymousAnonymousabout 7 years ago

Please make naughty boy 3!!! This story is too good to stop!

AnonymousAnonymousover 9 years ago
Encore!

This is a delicious story! Thank you.

I hope you have another chapter or two coming soon!

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Naughty Boy Series Info

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