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.”