Chapter 2: The Beginning

This all started when my mom lost her job, and we had to move in with my grandpa.

Weekly Punishment and Sessions had become a weekly ritual, every Friday after dinner. and during the week I have to satisfy my grandpa.

It started shortly after I turned 14, that was 6 months ago. My mother had noticed the leering glances and knew what was going to happen. She knew because the same thing had happened to her when she was young. Her father had punished her weekly for over 4 years until she moved out. She knew it was my turn, and she could not do anything about it.

I was extremely bright but did not like confrontation, avoiding all conflicts by giving in quickly. It was a trait I learned from my mother. I have long dark blonde hair, blue eyes, big innocent blue eyes, and a pale complexion. I wasn’t beautiful, just average with a modest figure. My breasts are on the smallish side, tiny almost flat, but were capped by large brown nipples. My ass was small and firm, with a nice pair of legs.

After a month of living at my grandpa’s house, my mother sat me down to discuss their new life. “Anna, since your father died, things have been bad. If it wasn’t for your Grandpa, we would be out on the street. I know it isn’t like it was before, but we must make the best of the situation. Maybe in a year I will be able to get a better job, and we can move, but until then, we must do whatever Grandpa wants.”

“I always obey, I’m a good girl, mom. It will be all right,” I said naively.

“I don’t think you understand, Anna. You’re not very knowledgeable about boys and men yet. They have some strange ways about them. Strange things that they like to do to girls. It happened when I was a girl, and I am afraid that it will happen to you with your grandpa.”

“I don’t know what you mean, Mom, what types of strange things?” I was perplexed.

“Grandpa is going to punish you every Friday after dinner. That is the tradition in this family. When I was growing up, my dad did the same to me. There is nothing we can do about it, it is just the way it is. Soon, we will be able to move and get away from all of this, but for now, you will just have to submit to it.”

My eyes opened wide in shock, “Punish me, why Mon, I’m a good girl, don’t let him do that, please Mom.” “Anna, it has nothing to do with you being good or bad, it is Grandpa. Men like to punish girls and men, especially men like Grandpa. It is the way they were brought up. There is nothing I can do about it, so you are just going to have to bear up to it. Just remember, you are to do exactly what Grandpa wants. Everything he says! Do I make myself clear, young lady?” My mother had never raised her voice to me before, and she was now ordering me to obey my Grandpa. It didn’t make sense, why would Mom want Grandpa to punish me? “But Mom.” “Enough, Anna! That is enough, just do as I say, or you will find us out on the street. Now I would rather not hear a thing about this again. Whatever happens between you and your Grandpa is to be kept between the both of you. I don’t want to ever hear about it. Do you understand, I don’t want to hear about it again?” “Yes Mom,” my eyes lowered to the ground, knowing that it was now my problem. What was going to happen to me on Friday night? “But Mom, why this clothing?” I was stumped, my mother had given me a white sweater, a plaid skirt, and a pair of black shoes with white socks to wear as well as a pair of black silk bras and panties. The outer clothes were something a younger schoolgirl would wear, and the bra and panties were something for someone much older. “I’m not going to tell you again, I would rather not hear anything about this. Those are what your Grandpa requested. Now hurry, you have to be downstairs in the basement in ten minutes. I don’t think you want to be late. Don’t forget to do everything he says, and I don’t want to hear about anything that happens. I am going out for a while, so you will be alone with your Grandpa. Good luck Anna and I love you,” Mom said then ran from the room. I was stumped. Would it be so bad? I couldn’t even fathom what could happen. I pulled off my clothes and slowly put on the silk bra that was too big for my small breasts and the panties. They felt so cool and sexy on my naked skin. Why did Grandpa request them, I pondered. The skirt was next. It was wool, with a zipper in the back. When I put it on and pulled up the zipper, it clung to my ass like a second skin, the bottom of the skirt not even going an inch below my ass cheeks. If I bent over, my ass would show. I pulled on the cashmere sweater, loving the luxurious texture against my skin. I looked in the mirror, surprised at my appearance. I knew that I would never be the cheerleader type, but my reflection showed me a side I never saw before. I looked like a twelve-year-old girl. My build was nothing spectacular, but my breasts looked so nice in the sweater and my ass and naked legs looked nice in the short and tight skirt. I looked at the clock, and it was 6:58, I better hurry and get to the basement and get this over with. I ran from the room to get to the basement before 7:00. I heard the front door slamming, knowing that my mother had left, leaving me to solve my problem with Grandpa. The basement door was open, usually the door was locked. I’ve never been in the basement. I walked on the stairs and every step squeaked. Grandpa was sitting on one of the black leather chairs, situated around a coffee table and the leather couch. The chairs were massive, with large padded arms with wooden corners. In the corner of the room was a desk, a large ornate desk with wooden legs. Around the room were various other pieces of furniture, including a couple of padded benches that seemed improper. They looked as if they needed a piano to accompany them. “Come in Anna, come in, let me see what you look like.” Grandpa watched as I walked into the room. His cock instantly sprang to attention, straining his pants, the bulge clearly visible. “You looked even better than expected. You looked just like a twelve-year-old girl, all the way down to the pigtails. I had required your mother to dress you like that.” Grandpa’s hand reached down to his crotch, grabbing his erect cock, making sure I saw everything. I blushed and turned quickly to avoid his gesture. “You look beautiful, do you feel that way, Anna?”

I turned back to look at Grandpa, glad that his hand was not in his lap anymore, but my gaze did notice a large bulge in his pants. “I look like a little girl,” I said.

“Yes, you do, like a very sexy little girl. That is how I want you to act, can you do that?”

“I guess I could. Are you going to punish me, Grandpa?”

“Do you want me to punish you, Anna, has my little girl been bad?”

“I’ve been good, Mom says I have to do everything you say, so I will, but if I do, will you not punish me?”

“I’m glad you will learn your place Anna, but I will punish you. Tonight and every Friday from now on.”

“How are you going to punish me, please don’t hurt me,” I begged.

He picked up a ruler, a wooden ruler, and slapped it sharply against his palm. “With this and my hand, I am going to punish your lovely pink skin with this. And each week we will progress on, with you submitting to more extreme punishment. I will enjoy our little weekly punishment sessions. And you’ll assist me in enjoying them.”

“Why, I’m a good girl?”

“No, Anna, you are my bad little girl, and you must be punished. Now come over to me, so I may see you better.”

I became more frightened. My mother was gone, nobody would know what would be happening in the room. Here I was, dressed like a little schoolgirl, and Grandpa was ready to punish me.

“What are you going to do to me, Grandpa?” I waited for an answer, afraid of what I might hear.

“It all depends on how cooperative you are, Anna. If you show any reluctance to my demands, the punishment will get more severe. Will you be a good little girl and obey your Grandpa?”

“Yes, Grandpa. Mom asked me to do whatever you say. She would be mad if I disobeyed her.”

“Good, you will only receive a light slap with my hand and the ruler. But I will find some nice tender spots to slap, your stomach and your thighs. I will pay particular attention to your tender thighs. I expect you to stay still and accept the punishment.”

I was scared, afraid of the pain that he would inflict on me, afraid that I wouldn’t be able to stand it. “Now come here little girl, and let me see you. You must have to chase the boys away from that lovely body,” His finger beckoned me towards him seated in the chair.

“I don’t have any boyfriends, I’m not as pretty as the other girls. Do you think I am pretty, Grandpa?” My eyes lit up, no one had ever complimented me on my looks, not even my mother. Mom always said I was average and I better do well in school because I would probably not get a man that would support me.

“Of course, you are a beautiful girl, So you’ve never let a boy touch your body?”

“No, Grandpa, no I have never done anything like that, that’s yucky,” I said with a scowl on my face.

“You would please a man very much with such a lovely body. Your tits are not very big but some men like small tits. Like me, I don’t like big-titted women. You just have to learn how to please a man.”

“Grandpa,” I cringed.

“What, you don’t like the word tits?”

“No, that sounds terrible.”

“Tell me you have small tits, say the words to me.”

“No, I don’t want to.”

“Are you already beginning to disobey me, is that what you are doing?” He raised his voice. I looked at him, seeing the look in his eyes. I had displeased him.

“I have small tits,” I said quietly.

“I didn’t hear you, what did you say?”

I cleared my throat, “I have small tits.”

Grandpa smiled, “I like your small tits, Anna, I like the way they look in that nice sweater. And you have lovely legs, especially in that delightful short skirt. And an adorable ass. Your skirt is just molded over your tight ass cheeks. I like that. I like your ass.”

I was confused. Grandpa was going to punish me, but he kept complimenting me on my body. It made me feel strange and also uncomfortable. Why did he keep talking about my body? “Thank you, Grandpa,” not sure what to say, but he looked like he was expecting some kind of response.

He stood up; his hands grabbed me around the waist, pushing me back towards the big desk in the corner of the room.

I jumped when his hands first grabbed my waist. This was the first time that he had touched me. I felt a sudden thrill and also the fear of the unknown. I felt my ass hit the edge of the desk as I was pushed backward. I saw him put the wooden ruler on the empty desk beside me.

“I will need that soon. Raise your arms, Anna, above your head. Hurry, now, don’t make me repeat everything twice. I expect your complete obedience.” Grandpa said as he watched as I first hesitated, then my arms rose, higher and higher until they were up over my head. My sweater rises above my stomach, a patch of naked flesh appearing. I looked down and watched as his hands grabbed the bottom of the sweater and slowly drew it up, revealing more of my naked stomach to his gaze.

I wondered how far he would pull it up, afraid that he would uncover my breasts, leaving me half naked, a bra the only clothes from the waist up.

He stopped when he reached the bottom of my bra. His hand began to run over my flat, tight stomach. He slowly let his hand rub my naked flesh, feeling my stomach muscles tighten as he did. He let his hand lightly tap on the flesh, I could hear the smack, smack of flesh on flesh.

“That’s not so bad, is it Anna?” Grandpa said as his hand lightly tapped my stomach. Except for the uneasiness from having a strange hand touching me so intimately and Grandpa being so old, it was not as bad as I thought it would be.

“No, it’s not so bad Grandpa,” I said nervously.

His hand lightly slapped my flesh.

“I can’t use two hands when I have to hold your sweater up. Anna, ask me to take off your sweater, to help me out.”

The realization came over me. He wanted to see me. He wanted to see me naked. He had every intention of forcing me to undress in front of him. I knew I had lost, I would have to do as he said.

A tear began to fall from my eyes as I spoke, “Please, Grandpa, pull off my sweater, so it will help you.”

“Sure thing, sweetheart, if it helps you out.” Grandpa smiled as he slowly let the sweater slip up my body, and my black silk bra revealed for the first time to his eyes. They were not very big, my tits, but they would be his to do as he pleased.

Grandpa pulled it up my arms until it pulled from my body and threw it over onto the leather couch. “Good girl, now we need to get you into a better position. A position that would make your stomach very prominent. Sit on the edge of the desk, from the side, I want you to be able to stretch out.” He grabbed a large pillow from the couch. “First, put this beneath your back as you lie back.” taking the large pillow, he positioned it in the center of the desk. I sat on the edge of the desk, pulling my skirt down as far as I could, the material insufficient to cover much, most of my naked legs showing. I felt Grandpa’s hand push down on my naked stomach, pressing my back onto the desk until my lower back hit the plush pillow. I could feel the strain on my shoulders and back as my head and shoulders bent further back, arching my stomach up into the air. I could feel the cool air on my legs, knowing that the short skirt was not hiding much. “Now I want you to hold on to these metal rings and don’t let go, if you do, ill will handcuff your hand and use a belt on you,” Grandpa told me. I stretched my arms back and grabbed the hard, metal rings, my small hands clamped tightly around them. My back already began to ache, the pillow forcing it to bow. I shut my eyes, not wanting to see what Grandpa was doing. I heard him moving around and then felt his hands on my naked knees at the foot of the desk. “So lovely, your naked legs, Anna. Your short skirt has ridden up a considerable distance, showing me a lot of naked flesh, and your adorable panties. As soon as I finish with your stomach, I will be working on your inner thighs. I am going to enjoy that, I don’t care whether you enjoy it or not.” his hands ran up from my knees, running over the naked flesh on the tops of my legs until it reached only inches from my panties. I squirmed on the desk as I felt his hands taking liberties with my body. My eyes tightened as I imagined him leering at my exposed body, his clammy hands running up and down my naked legs, his eyes looking at my panties. “I need to get closer, open up your legs, so I may stand between them,” Grandpa said as he pushed on my knees, bending my legs outward, his continued pressure finally forced me to relent, the gap between them widening. My hands gripped the handles until they were white as I allowed his hands to open my legs, my body trembling as I imagined how exposed my sex was to his gaze. I felt his hands continue to explore my naked legs, and now I felt my legs graze his hips as he stood between them. Grandpa stood between my white thighs, his hips keeping me spread open for him. My skirt had ridden up so high, he could see my black panties. He grabbed the leather wooden ruler. “Now don’t let go,” he said. He let the ruler hit my stomach, a rush of air shooting from my mouth, my eyes opened wide in surprise as I felt the sudden rush of pain emanating from my stomach. “God,” I yelled out, my hands fighting to let loose from their self-imposed bondage. I sucked in another breath before the ruler came crashing down again, a sharp pain rushing in my brain. Grandpa let his hand rub my stomach slowly, and then the ruler would return to inflict its pain, alternating between soft, caressing rubs to painful splats to my reddening skin. He stopped with the ruler but commenced with the slapping with the flat plane of his hand, feeling the heat the slaps were generating. I was squirming on the table, my thighs rubbing sensuously against his hips, not in pleasure, but to escape the pain he was inflicting on me. “Mmmm, Ooooh,” groaning and moaning in pain as the painful slapping continued. Finally, there was silence. I waited and waited until I finally opened my eyes, Grandpa’s face staring intently at me. I felt his hands still on my stomach. “So hot, your skin. You were a good girl, Anna. Keep up the good work. Hold still for a minute, then you can get up, and we can continue.” His hands moved up my stomach, my eyes on them as they moved up to my bra. They quickly moved over the top of them, grasping my tits in the palm of his hand. “Hold still,” he commanded me, his hands grasping and gripping my little breasts. “Why are you doing this, please, please, stop,” I begged, but my hands continued to grab the posts tightly while Grandpa mauled my unprotected breasts. He released his grip on my tits and helped to pull me up. “You will have to get used to having boys grabbing your tits. I’m just helping you out. Now stand up, quickly. We still have more to go, this time it will be your thighs.” He made me stand up, my skirt falling back down to cover my thighs. He pushed a button near the desk and a bar came down from the ceiling, it was like a trapeze bar except this had thick leather cuffs on each end, the bar over five feet long. “Anna asked me to put your hands in the cuffs.” I did not say a word, I just stood there. “If you don’t I’ll use the belt on you.” I quickly put my arms up, “Grandpa, please hook my hands in the cuffs.” I said crying. “Much better. You should hold on to the bar all the time.” My body shuddered in fear, it kept getting worse. My arms reached up, and my small hands gripped the bars, holding them tightly. I felt the bar start moving up, drawing my body up. “Hold tightly, while I inspect your thighs. I’m going to slip my hands under your skirt. Has any of the boys ever done that to you, Anna, try to feel up under your skirt?” “No, do you have to do that, please, nobody has ever touched me like you are doing,” Grandpa moved a chair in front of me and sat down on it. His eyes stared at my body. I felt his hands slipping under my skirt, moving up my hips, over my naked flesh. His hands moved up higher, moving behind me, almost grasping my panty-covered ass cheeks. I started sobbing when I heard his next words. “Your skirt is in the way this time, turn around so I can take it off. You want me to take off your skirt, don’t you? Ask me to strip you down to your bra and panties,” he mocked me. My crying became louder, my sobs choking back the words. “Grandpa, take off my skirt,” I softly said, knowing that were the words that would make Grandpa happy. “Now, Anna, is that the polite way to ask?” “Grandpa, will you please take off my skirt?” “Now that is better, I’ll be glad to help you.” I felt him turn me around, the bar circling, allowing me to continue to grasp it tightly as I was positioned to be stripped of my skirt. I felt his hands, they did not seem to care, moving over my little ass cheeks, not attempting to conceal their purpose. The sound of the zipper pulling down sounded so loud. And then I felt the material slipping down my naked legs, falling to the floor beneath me. I could feel his breath on my ass as I continued to sob. His fingers traced up the inside of my thighs, barely able to enter, my thighs clenched tightly together. He teased me, his finger tracing up and down the divide of my legs, almost touching my panties before running back down again. He watched me clenching my thighs together, stopping him from having his way with me. “I need access to your thighs, relax your leg,” Grandpa said as he reached down to my ankle. “Relax, it will not hurt,” grabbing my slender ankle in his hand and slowly raising it towards the desk. I balanced precariously, my arms strapped to the bar, preventing me from falling over as I was balanced on one leg. Grandpa bent my leg and placed my ankle on the top of the desk. My legs were now at a right angle, one pulled out straight onto the desktop. My crotch felt so exposed and open. “A little higher, I think,” grabbing the pillow still on the desk and pushing it under my ankle. “This will be more comfortable for your ankle.” The pillow was softer, but my leg was now arched up higher, my thighs straining from the unnatural spread of my legs. I looked down and was humiliated at how I looked, my crotch was so open, my panties just barely covering my sex, a few stray strands of hair peeking out from beneath them. My naked thigh was now completely exposed. Grandpa then hooked a leather strap around my ankle that was on the ground. He then hooked the strap to the hook on the other side of the wall. I heard the sound of a motor, the bar again rising higher, and my foot with no longer on the ground. then the strap around my ankle began to pull my legs away from the desk. I was hanging there with 1 foot on the desk, and the other foot being pulled for the other wall, almost doing the splits. “Good girl, Anna, your mother would be proud of you. Such nice thighs, such smooth skin,” his hands began to run over the pink flesh exposed. He could feel my body trembling, partially from holding such a taut position, partly in fear as his hands continued to rub my skin within inches of my panty-covered sex. He moved closer to me, his hip banging into my panty-covered pussy on purpose, pressed hard against it. I’m sure he could feel my pussy lips beneath the scanty garment. I had never felt anything like it. His body was rubbing against my pussy. The thin, silk panties did little to cover my vagina. I felt one hand grip my leg at the knee. “SSSLAAP,” the noise rang out in the room. “OW, god, that hurts,” I cried out as his hand slapped hard against my tender thighs. He rubbed the spot he had hit, feeling the heat already, seeing the pink skin turning redder. “SSSLLAAP, SSSSLLLAAAP,” again, this time twice in succession, feeling my body shudder in pain. His hands returned to caress my hot flesh. He continued to rain down slaps on my sensitive inner thighs, my body shuddering in pain as he did. But I could not attempt to stop the punishment. My thigh was turning a dark red. He switched to the wooden ruler, the intensity of the slapping increasing. After a few minutes, he stopped, untied my ankle, turned me the other way, and put my other leg up high on the desk. He now had new, fresh, pale skin to work on. He immediately began to strike my untouched flesh with the wooden ruler, the splats ringing out in the room. I had begged him not to do the other leg, laughing as he rejected her pleas. “What are you doing, don’t touch me there, please,” I begged. I felt his large hand grip my panty-covered pussy, his finger slipped between my pussy lips. “I just want to make sure I don’t accidentally hit your pussy with the ruler, You’re not ready for that yet. You want me to protect you, don’t you, Anna? I’m only watching out for your best interests. You want my hand on your pussy, don’t you?” “Yes please Grandpa, please protect me,” I said crying. I squirmed as I felt the throbbing hand on my pussy. This was the first time any boy or man had ever touched her there. I could feel the heat from his hand, as it moved slowly, wedging itself between my pussy lips. I could not move away from it, only able to jerk my hips back a little, but having to return. It looked like I was trying to rub up and down against his hand. I tried to hold still. He could feel the heat and wetness on pussy as his fingers gripped my sex. He continued with the slapping of the ruler, letting his finger move slowly, rubbing around my pussy as he continued to abuse my thigh. Why did his fingers feel so good? “Oh, god, that hurts. Please, aren’t you finished yet? It burns so bad,” I cried, tears running down my cheeks as I stood there, spread and open and submitted to his spanking and fondling of my flesh, on the verge of an orgasm. Grandpa stopped, moving his hard cock against my leg, both of his hands reaching down between my legs, one in front, the other grabbing at my spread ass cheeks, gripping them tightly.