Little Jimmy Grows Up

"Damn, that's good," Tom gasped, breathing harder as he began moving faster in and out of my mouth, his nuts smacking me in the neck every time he moved forward.

Implusively, I took my upper hand off of his cock and brought it down to his nuts, rolling the weighty balls in my hand for a minute and hearing Tom moan in pleasure.

"Cumming," Tom said after a minute of this, grabbing the back of my head so I could not back away even if I had wanted to.

I choked a little when I felt the first squirt of cum hit my throat, but after that the cum just flowed out of him, and I eagerly swallowed it all as he came.

Having sampled it yesterday, I was already familar with the taste of Tom's seed, but it was much more fun taking it right from the tap like this, and I kept sucking on him until Tom pulled me off.

"Good, Jimmy," Tom said rubbing my aching shoulders in gratitude before pulling me up to my feet. "Time for lunch."

I welcomed the chance to drink something, because even though I kinda enjoyed the taste of Tom's dick and cum, that baby oil had left a nasty coating that I wanted to lose. After we ate, Tom looked down at my dick, which was pointing at him.

"You look like you're having fun," Tom said with a snicker.

I shrugged and nodded, not mentioning the fact that I pretty much had a constant erection anyway, and being so close to a naked Tom was only making that condition chronic.

"I think I'm going to have some more fun with you," Tom said, indicating that he wanted me to get up on the stool so that he could put those bracelets on me again.

"Can't we do something else?" I whined, but wisely put up no struggle as he bound my wrists once more.

"This will be different," Tom assured me. "Got to get you all ready."

"Ready for what?" I whimpered, the look on Tom's face making me uneasy.

"Ready for me to fuck you in the ass."

....

Chapter Twelve: Prepping me.

My throbbing shoulders protested being stretched out again, but I had already figured out that complaining did no good and would only make it worse, so I stood there silently as Tom walked around me.

"Nice ass," I heard him say behind me, feeling his hands on my butt cheeks, squeezing them like they were melons. "Good and firm. Spread them."

"What?" I asked, a split second before I felt Tom's finger at my anus, poking inward.

"I said spread them," He barked, pushing what felt like a lubricated finger right into my ass without warning.

"Damn, you're tight," Tom remarked as I yelped after he slid his finger in farther. "Don't you ever do this to yourself?"

"Me? No," I replied while squirming.

"Feels good doesn't it?"

"I guess," I managed to reply.

"If you relax, you'll like it even more," Tom advised me, his finger now fully impaled inside of me, and as he spun it around in a corkscrewing fashion I groaned.

"You're... uh... only kidding, right?" I asked, my body moving involuntarily as the digit went in and out of my previously virignal cavity.

"About what?"

"Putting your thing in my - you know?"

"Say it."

"About you putting your cock in my... ass."

"Of course I'm not," Tom replied, and after his finger slipped out of my anal cavity I felt myself missing his intrusive probing. "What's to kid about?"

"I don't want that."

"Yes you do," Tom said as he came around to face me, and his glare made me wither as he stared me down.

"It's not even possible to do that," I said as my eyes took on his semi-turgid cock which swayed menacingly in front of him.

"Of course it is," Tom assured me. "Boy, you really don't know much about anything do you? You never heard of anal sex?"

"I guess so, but it just doesn't seem possible."

"Why?"

"Because of your, you know, dick. It's too big."

"So?"

"But," I sputtered, trying to plead my case. "You could see how tight my bottom was for your finger, and your dick is way bigger than that."

"You'll take it all right," Tom said. "Besides, you don't really have much choice. You refuse - you leave."

"But won't it hurt?"

"Hell now. I'm going to love it," Tom laughed.

"I mean me. It's gonna hurt me, isn't it?"

"Yes," Tom said coldly. "It's going to hurt a lot, especially at first. In time you'll get used to it, and before long you'll be begging me for it."

"Why do you like it so much?" I bravely asked. "Scaring me and hurting me, I mean."

"Good question," Tom said. "I don't really know. I guess another good question would be why you like me to do it. Why do you like being so submissive and weak? Having me do things to you and justifying it to yourself by saying you were forced into it?"

"I don't."

"Bullshit," Tom countered. "I remember back in school when that asshole Gordon Somers used to pick on you. He used to push you around and slap you silly whenever he saw you. One time I heard he punched you out after school and you didn't even fight back. You just stood there and took it."

"It would have been worse if I tried to hit him back," I reasoned weakly. "He was a tough guy, and I can't fight."

"He was a punk, and was sure as hell not tough," Tom sneered. "I have a feeling you liked the attention, and maybe even liked the abuse. What do you think?"

I had no answer for that, and as I shrugged and looked out the window Tom went over to a desk in the corner. Before I knew what was going on I saw the flash of a camera.

"What?" I said as I looked in horror at Tom snapping a picture with a Polaroid camera. A picture of me in all my naked glory, hanging from a beam with my boner waving proudly in front of me.

"For the archives," Tom remarked, snapping another and another before peeling them off and showing me the results.

I looked pitiful. My face was completely recognizable. There would be no denying it was me. My life was ruined.

"Don't worry," Tom said as I tried to keep the tears from flowing. "This is just for my protection. I trust you, but you never know what might happen. You might throw a hissy fit and start telling people about what we're doing, or try to blackmail me."

"I would never. I swear."

"I believe you," Tom said. "These are just my insurance policy, just in case you start telling people that I'm some kind of pervert. That would ruin my life. I'd never get to be President like that."

"Besides," Tom added. "All those months being at college will probably make me miss you, so I can look at this and remember. Maybe even jerk off looking at you. Wouldn't that be a switch?"

It certainly would, and after Tom put the photos away, he returned to me. Running his hands up and down my slippery body as the perspiration kept flowing off of me, his eyes traveled upwards.

"You know what would make you look even sexier?" Tom asked while his fingers stroked my armpit. "Getting rid of this here."

I chirped in shock as Tom plucked a hair out from my underarm.

"Don't. Please," I whimpered as he began plucking my armpit hairs, the pinching feeling that resulted being far less painful than humiliating.

"Won't take long," Tom said jovially. "Never been with a guy less hairy than you."

After a couple dozen more pinching sensations later, Tom had managed to pluck my left armpit clean. All those years of waiting for those sparse signs of adulthood were suddenly gone in less than a minute. Sensing my feelings, Tom slid his hand up and down my smooth armpit.

"Really does look sexier this way," Tom remarked as he surveyed his work, and to my surprise he leaned forward and ran his tongue up and down the sweaty hollow, causing me to cry out with pleasure.

"Feels nice, doesn't it?" Tom asked. "Now you know how I feel when you do it to me."

I didn't protest when Tom moved to my right side and repeated his actions, right down to the electric sensation of his tongue making me shudder.

"Since we've gone this far," Tom mused, walking over to the bathroom and returning with a razor and a can of shaving cream.

"This won't take long," Tom said after squirting a tiny wad of cream into his palm and rubbing it though the tuft of hair over my dick, completely ignorning my begging for him to stop.

He was right about it not taking long, since the area where the hair covered was about the size of a steel wool pad. After he prepped the area, he took my dick in one hand and with careful strokes began removing yet another sign of my manhood.

Was I ashamed at being treated like this? Indeed I was. Problem was that I had a funny way of expressing my outrage. Tom had just made the final swipe with the razor when the combination of his holding and pulling my cock away from my body as he shaves me, along with the sensuous sliding of the razor on my skin, did the trick.

"Awww!" I groaned, feeling my dick begin squirting another load all over the floor.

Tom was laughing as this happened, even doing some rubbing to encourage my orgasm, until I went limp in his hand.

"You're like a freaking orgasm machine," Tom said as he wiped the cum from the back of his hand onto my stomach and stepped over the mess. "Don't ever get enough, do you?"

...

Chapter Fourteen: Getting enough.

"You know what this is?" Tom asked, holding up a white plastic device shaped like a rocket.

I shook my head no, and was startled when Tom did something to the thing, causing the thing to hum loudly in his hand.

"It's my Mom's," Tom explained as he brought it over to my chest and rubbed it on my nipple.

"Ooh!" I said, feeling my nub tingle as the vibrating device made contact with me. "That feels nice."

"It's only been used on her so far, so you'll be the first. This should loosen up your ass some."

Tom lathered on some vaseline and held it in front of my eyes for effect before walking behind me.

"Relax," Tom said, easing his finger into me again before bringing the cold tip of the device to my anus.

"Won't you get in trouble?" I asked, trying to delay what was going to happen. "I mean, if she finds out you took it."

"She knows I have it," Tom explained, spinning the device around in his hand. "Let me explain something to you, Jimmy boy. It doesn't matter whether it's up here or over in the main house. Either place, I'm in charge. I'm the man of the house in every way. I have been since my old man got thrown out."

"I don't understand."

"You will," Tom assured me as he pushed the device inside of me, making my knees buckle and causing my arms to strain to keep me upright.

"Ow!"

"Don't be a pussy. This puny thing is nothing. It's barely bigger than your own dick. Now relax and enjoy it."

While it had felt like Tom had rammed this thing all the way up into me, that soon turned out to be wrong, as he continued to work the vibrator further and further up into me. The tingling and the undulating motion began having an effect on me, as did Tom's words.

"You like it, don't you? I told you that you would. Now just imagine how nice my cock is going to feel when I slide it inside of you."

I was whimpering, feeling like a marionette as I squirmed while being violated by his mother's vibrator. What would she think if she knew what was happening, or did she already know? The window - I couldn't see her, but could she see me? I didn't know, and for the moment at least, I didn't care.

Tom walked around to face me, leaving the humming tool buried deep inside of my anal cavity as he admired his handiwork, stroking his cock as he watched. He was almost erect now, and as his fist ran up and down the length of his enormous member, I tried to figure out how in the world this was going to happen.

"You aren't going to - you know - put your whole thing inside of me, are you?" I asked in a voice I didn't recognize.

"You want it all?" Tom asked with a cackle. "How much of it do you want? How about half the first time?"

"No, that's too much. Maybe just put the tip in for a minute, okay? I just don't want you to hurt me."

"Yes you do," Tom said in a matter-of-fact tone, leaning against me and biting my nipple as his hand reached back and churned the vibrator around in me. "I think Jimmy likes to be hurt, don't you?"

On the crates, I was a little taller than Tom, yet I still felt drawfed by him. After Tom leaned away from me, he took his cock in his fist again and began to rub it around my spent dick, and soon he was clubbing my little stem with his cock. It didn't hurt, but the absurd sight of it was exciting me despite it all.

"It's time," Tom suddenly said as he yanked the toy out of my ass, reaching up and undoing the bracelets before leading me over to the cot.

I got cold feet when we neared the edge of the bed, but Tom was having none of that. Pushing me face-first into the mattress, he climbed on top of me and spread my ass cheeks.

"Get up on your knees," Tom growled. "I want your ass up high and your face in that pillow.

"Oh!" I groaned as I felt something slide into me, but my relief at discovering it was only his finger soon disappeared when a second finger went in with it.

"Relax," Tom said as I yelped out in shock and discomfort, but that was easier said than done. "It'll be a lot better for you if you don't fight it too much."

After fumbling with the lubricant for a second, freshly lathering up his fully engorged organ, he climbed behind me and prodded at my opening before moving closer.

...

Chapter Fifteen: It hurts.

The fingers came out and before I knew it, they were replaced by the head of Tom's cock. I was shocked at how easy it slid in, and as the cone penetrated my anus, Tom's moan sent a shiver down my spine.

"Damn, you're tight," Tom grunted.

"It hurts. Is that it? Is it all in?" I asked hopefully, because while it hurt, it was no worse that the vibrator had been.

Tom laughed at that, telling me that he only had the head of his cock inside of me.

"Since you like that so much, here's some more."

Tom's hands held my hips as he pushed forward slowly, and as he pushed his cock into me, I felt like I was being split in two as the increasingly thick shaft slid into my tender opening.

"Please," I whimpered, trying to stifle my sobbing into the pillow my face was buried in.

"I knew you'd end up begging for it," Tom cackled, pulling himself back out of me before impaling me even deeper.

"No," I cried out at Tom, not sure whether he was misunderstanding me or just mocking me.

"You love it," Tom insisted, moving in and out of me faster and harder. "I've only got half of it in you so far. You want the rest?"

"Please don't," I asked, knowing full well that my complaining was only exciting and inciting Tom more.

"Tell me you like it then."

"I like it," I gasped, feeling Tom's sweaty and hairy body encircling me and holding me tight.

"What do you like?" Tom asked, grabbing my hair with his hand and pulling my head up.

"Love your cock - in me. In my ass. It's so big."

It hurt. It hurt a lot. For what seemed like forever Tom continued to thrust his massive cock in and out of me, stretching my orifice beyond anything I could have dreamed possible, but by the time he started to come, I not only had gotten used to it, I was sorry it was over.

Tom let out a gutteral groan as he wrapped his arms around me in a bear hug. I felt his cock jerk a couple times as his cum filled my bowels with warmth, and seconds later my knees gave out as Tom collapsed on top of me.

"You alright, Jimmy?" Tom asked, his deflating cock still inside of me.

"Yes," I answered with a touch of sadness in my voice as he pulled his now-flaccid cock out of my ass and rolled beside me, rubbing my back.

"That was good," Tom said. "Let's take a shower."

Tom rolled off of the cot easily, but I had a lot more difficulty. My butt felt like Tom was still inside me as he helped me to my feet, and when I made my first few steps I felt his seed drool out of my ass and down the insides of my thighs.

We stepped into the shower stall after Tom had adjusted the temperature, and the warmth of the spray was soothing, but not as soothing as Tom's hands as they soaped and gently scrubbed my body.

Taking special care around my very raw and aching parts, I enjoyed the tender treatment he gave me so much that I wanted to stay in the shower forever. Tom even toweled me off and helped me get dressed afterward.

"Uh - can I come over tomorrow?" I asked hopefully.

"What for?" Tom asked.

"You know," I said shyly.

"I told you, didn't I?" Tom replied as he escorted me to the door, his hand on the back of my neck. "Didn't I tell you that you'd end up begging for more? You want me to fuck you again, right?"

I nodded, feeling my cheeks flush at the realization that he was right.

"Next time - I won't baby you like I did today," Tom informed me.

"Huh?" I mumbled, not even aware that he had babied me at all. My anus felt like I just had a baseball bat slammed up inside of me, my back stung from the strap he had used on it and my skin tingled from the places that he had removed my body hair from. Babied?

"I'm not sure right now," Tom said. "Give me a call tonight."

Feeling a bit hurt, I slowly navigated the stairs and waddled along the side of the house. Tom's mother was standing in the doorway when I went past, and I nodded while sheepishly passing her.

"Are you all right, Jimmy?" she asked in a motherly tone.

"Uh - fine," I said, hurrying past her and heading home.

...

Chapter Sixteen: Calling.

"So I was wondering," I stammered into the phone. "About tomorrow, I mean."

"I dunno," Tom answered. "What would we do?"

"Stuff. Like - uh - the stuff we did today."

"You been thinking about what we did today?" Tom asked.

"Yes."

"How many times did you jerk off thinking about me?"

"Just once."

"So what would you do if you came over here tomorrow?"

"I dunno. Anything you wanted me to, I guess. Maybe... I was thinking that maybe I could do - you know - do to you what you did to me?"

"Fuck me in the ass?" Tom said, and laughed. "With that puny little dick of yours? Ain't gonna happen, Jimmy. I only give. Never take, although I probably wouldn't even feel it if you did try to put your little weenie in me."

"That's okay," I said while backpedaling quickly. "I mean, the other stuff would be okay too."

"Only one thing of yours is ever going up my ass," Tom informed me. "Come to think about it, I could go for a rim job right about now. Come on over here."

"Now?" I asked. "It's after 10."

"You want to come over here tomorrow, get over here now and rim me."

"I don't even know what that is," I protested.

"You'll find out," was his response just before hanging up.

I found myself on my bike, pedaling over the darkened streets to Tom's house. When I rode in through the driveway, Tom flagged me down before I went back to the garage.

"In here," Tom said from the doorway, and after I set my bike against the house I went up the steps and into his house.

Tom's mother was sitting on the couch, only half watching TV when I followed Tom into the living room. I was shocked that Tom was wearing what he was wearing, which was only a pair of boxer shorts that barely managed to contain all of the manhood crammed inside of them.

"Hello," I mumbled in greeting as she looked at me.

"We're going to be in my room for a little while," Tom told his mother and with that he brought me down the hall to his bedroom.

"Let's see how badly you really want to be with me," Tom said as he closed the door behind us.

"What you said you wanted me to do. I don't know what that is."

"A rim job?" Tom replied, sliding the boxer shorts down and stepping out of them. "Stick out your tongue."

I did as he asked and Tom grabbed it and held onto it while he explained.

"A rim job is when you use your tongue on my asshole," Tom said, enjoying the look of horror on my face as he gripped my tongue hard. "You lick all around the balloon knot, and then you dip your tongue into it."