If I am a chronically addicted masturbator (and I am), my first “pusher” was my grandmother. It was she who “strung me out” and made me so that any time I get the chance, I masturbate, even after all these years since she first got me addicted to it.
When I was about 11 my parents sent me to stay with her for a week while they went out of town. I told my mother I didn’t want to stay with Grandma because she was fat and I didn’t like her. And she was fat, around 250 pounds, I guess. She had a bulging tummy, fat thighs and a huge ass. She sort of rolled when she walked and I thought she was awful.
My mother just smiled and told me that’s where I was going anyway.
At Grandma’s house, I stayed in my room as much as I could. I had learned to masturbate that summer and I thought that it would be the perfect time to jack off. Grandma was just letting me be alone in the guest room. I waited until I knew she was downstairs watching her TV and then I took my clothes off and began to jerk off. Just as I was really getting into it, I looked up to see Grandma standing in the bedroom doorway. The look on her face scared me and my erection immediately deflated.
“Get your clothes on and come downstairs immediately!” she said and went away.
When I got downstairs she was sitting in her easy chair in front of the TV with a cross look on her face. She pointed to the floor in front of the chair and told me to stand there in front of her. I went and stood there very still.
“Did anyone give you permission to masturbate in my house?”
“No, Grandma,” I was mortified.
“Do you think you can just come in here and squirt your cum any time you please?” her voice was very harsh and scolding.
“You only get to cum when I SAY you can; DO YOU UNDERSTAND?”
masturbate in my house unless I tell you you can! Are we clear?”
“Yes” I was barely able to speak above a whisper, I was so embarrassed. I stood there as she stared me down.
“Do you want to jack off now?” she smirked.
“Well, you shouldn’t! … It’s nasty and it’s wrong to do it in my house. People can only do it if I say you can.”
“Okay, I’m so sorry.”
“Come closer,” she demanded. I crept up another step. Exasperated she reached out and curled her pudgy fingers into my waistband and pulled me right up to the edge of her chair.
“You think I’m ugly because I’m fat.”
“I … I ..”
“You think these are fat and ugly, don’t you?” She pointed at both her mountainous breasts covered by her sweater. I didn’t say a word.
“Look at me!” she said.
Her hands went to her sweater and pulled it up. Now I could see the large white bra holding them. The cups were huge.
I could barely breathe as she shrugged out of her top and reached behind her and unfastened the clasp on that huge bra. I will remember that forever.
Her giant tits spilled out as she pulled the bra off.
I stared at them. I couldn’t move. Her breasts were awesome — huge white bulging mountains with fat pinkish brown aureoles the size of coasters. In the middle were reddish fat nipples the size of the end of my thumb. I realized they were magnificent!
“Think they’re ugly now?” she taunted. She held each one in her hands and hefted them up away from her body. “Yes, they are fat. … good n’ fat!”
“I …um …they … they’re beaut –“
“Sure …you think they’re beautiful now.” She smirked. She let them fall back onto her body and leaned forward, letting their pendulous weight make them sag. My penis began to throb.
“Now do you want to masturbate?”
Without waiting for an answer she pulled at my belt, unclasped it and unzipped my pants.
“Let’s just see,” she chuckled.
My pants slid down around my knees. She tugged at my briefs with her pudgy fingers and they came down too. My penis was jerking and stiffening. Even though it was naked in front of my Grandma, my erection was growing.
“Oh yes, you want to masturbate.”
I’ll never forget the gentle way she reached out and curled her fingers around the shaft of my penis and stroked it, making it harder and harder.
“Your parents haven’t taught you anything about jacking off yet, have they?”
“Uh uh.” I grunted. I just stood there and watched as my grandmother masturbated my penis until it was hard.
“Your mom should already be teaching you this stuff,” Grandma said. She was sweetly milking my shaft as she looked up at my face. “ .. and your dad. He knows a lot of tricks.
She was quietly laughing at me as she jacked me off. “I guess they haven’t realized you started a little early. I’m sure they will want to show you everything. I’m just going to teach you little bit about how to behave.
“My titties are pretty to you now, huh?”
“Let’s do this …” Grandma pulled my penis forward until the tip of it was touching her left nipple. She held her big tit in one hand and circled the tip of my prick around and around her hard nipple. A little thread of my precum stretched out over her areola, then it broke and the silver goo painted her nipple.
“Fun, huh?” she smiled. She lifted up her other breast and pressed my cock against her other nipple, making it sink into her tit flesh. I was trembling. I had never imagined something could feel that good!
“Your mom used to suck on these as a baby. Your dad sucks on them too, only that started much later.
“Now, every once in a while, she’ll suck on one, and he’ll suck on the other.” The picture of that in my head made me want to cum. She stared at her nipples and my cock kissing them, remembering, I guess, those moments with my parents.
It was overwhelming! I couldn’t believe how good my dick felt as she played with it, moving it back and forth from one of her nipples to the other. I felt my penis start to spasm. Grandma did too.
“Don’t you cum!” she said, “Don’t you dare cum!” Grandma squeezed my dick really hard and held it until it was painful and it stopped me from cumming.
“Remember,” she said “you only get to cum when I say you can cum! You have to hold it! You have to until I say different! This is my house and you do what I say with your penis!!”
“I … I’ll try, Grandma.”
“Try very hard.” She demanded. She held my penis is a vice-like grip until she was sure I wouldn’t cum.
“You like my titties, now, don’t you? You don’t think they’re ugly at all, do you?”
I shook my head and tried not to cum, but I really really wanted to. At last she let go a bit and began jacking me off slowly. She spent a long time just masturbating me with my dick pressing against one of her nipples or the other.
“You can fuck them now,” she said.
She gathered her breasts in her hands and pressed them around my shaft. They molded around it and I was held inside an incredibly soft warm tunnel. I started thrusting back and forth in her deep cleavage, fucking her giant tits and groaning as she squeezed them around my little penis.
“That’s it, honey,” she said, in such a different, grandmotherly tone of voice; so loving, so sexy. “Fuck them. Fuck my titties!”
I did as I was told, although I was very young and had no idea what I was doing. I just kept stroking into that wonderful valley of tit flesh my grandmother was making for me. Every time I was on the verge of orgasming, she would stop it with her death grip on my penis until the urge to cum subsided. All the while she whispered her sexual thoughts and instructions to me.
“You haven’t seen a pussy yet, have you? … eventually maybe I’ll let you see mine if you obey me. I don’t think you’ll find it ugly either.
“ .. let your mom show you this … I’ll tell your dad to teach you how to “edge” … ohh your pretty little penis is so hard! ….”
“Ahhhhhhh!” I cried.
All of a sudden there was nothing I could do, my cock suddenly quivered and spasmed and I began squirting cum. The first spurt flew up toward my Grandma’s face, the next two spurts painted the tops of her breasts and then she got control of my penis and held it to her left nipple where it squirted over and over against that hot hard button. The cum dripped down onto her fat, jean-covered thighs. I had never cum like that in my life before! It was the best thing I had ever felt. I was close to fainting.
“Ohhh, Honey!” Grandma cooed. “You weren’t supposed to cum yet! But I know, … it just felt too good didn’t it? God you’re cumming so much!”
Grandma pulled me down so that I sat in her lap. We both stared down at my penis as it jerked and spat out more sperm, the last drops oozing out and leaking down into my crotch. She pulled some tissues out of the box on the table by her chair. She handed me some too.
She cuddled me in her lap for awhile, petting my penis, wiping us both off wherever the cum had spurted.
“Next time, you have to hold it better.” She said. “You have to wait until I let you cum. You have to learn. I’m SERIOUS!!”
She pushed me off her lap, making me stand up and pull my pants back up.
“If you want to see my pussy, you better practice on doing it right, young man.”
She handed me the box of tissues and told me to go back to my room.
As I went up the stairs she said. “You have my permission to jack off tonight as much as you want, only don’t be in a hurry to cum. You have to learn to hold it until I say!”
“Okay, Grandma.” Already I wanted to masturbate some more, and I wanted desperately to see her pussy.
“We’ll start teaching you real discipline tomorrow.” She said to my back.
“And don’t cum on my sheets!” she yelled.
That was my first lesson, my introduction to my addiction.
“Did he fuck you?” my mom asked into the phone.
“Well, that’s very nice, Mother, but you could have if you wanted; I mean, it doesn’t have to be me first."
"Well yes, it is his cherry,” she said, “... See my pussy? … he’s earning it right now.
She turned and looked at me. ”Grandma says you can’t cum unless I say you can.”