Grandpa’s Lessons

“So, are you going to tell me or not?” Bri asked me. Again. I was sleeping in her house, that night and we were drinking tequila from a bottle her older brother had gotten her after she covered for him last month when he got home from a party completely wasted. We were both already dressed for bed, wearing tank tops and panties, my long blond hair was in a braid while her chestnut one was loose, reaching her shoulders. She wanted to know about my first sexual experience with someone. Hers happened two weeks ago with this boy from one of our classes she had gone to a date with. They went to the movies, and all that happened was mostly second base stuff, but since then she kept rattling about it nonstop, knowing full well I never had a date with a boy. My parents were strict and they always made quite clear that I would only be able to have a boyfriend once I turned eighteen. This didn’t bother me as much as it should, it was a good excuse to get rid of some annoying jerks at school, but sometimes it was hard to say no to the hot nice guys that asked me out. Not that this happened a lot, but when it did it made frustrated and angry.

“Kayleigh please! I’m your best friend!” Bri said pleadingly, giving me her best puppy eyes, making me roll mine. She got me so annoyed with details of her date and the things Mike did to her, that after two shots of the tequila, I made the mistake of telling her that just because I never had a date, it didn’t mean I never have had anything sexual with someone. I regretted immediately.

“I made a promise to never talk about it to anyone.”

“You know me, we’ve been friends for years, you know I would never tell a soul what you’ll tell me!” Bri said almost offended. It was true, she was the most trustworthy person I’ve ever met and she knew me well enough to know I wouldn’t deny this fact. She wouldn’t drop it, knowing her like I did, she would keep asking me about this every day from now on, so I looked at the tequila bottle in my hands and without pouring the liquid into my glass I took the bottle to my lips taking a swig of it to give me courage.

“Anything I say stays between us. You won’t say a word until I finish the story and you’ll promise me right now that you won’t judge what I’ll tell you,” I said feeling a little afraid of losing her friendship. Brianna was the first friend I made when I moved here, and we became inseparable. I was terrified of ruining our friendship telling her what I was about to tell.

“I promise you that whatever happens within this walls will never leave this room. There will be no judgment on my part and I will keep my mouth shut,” Bri said looking into my eyes without blinking showing me that she was serious.

I nodded my head and looked down, searching for a way to start.

“Okay. You know that I lived in a farm until and was homeschooled by my mom. My upbringing was very shattered, so I never learned much about sex. Actually, I never even learned about it, except that my mom always told me that I should never touch myself between my legs, except for cleaning myself, saying that young ladies didn’t touch themselves there. As a good daughter I obeyed without question. I mean, until I started to become curious about my body when my boobs started to grow…” I said and looked at Bri uncertain. Her blue eyes were glued on my face, her expression telling me to keep going and to not skip anything. I looked down at my hands before continuing.

“So one night I was in our old bathtub and, feeling curious, I started to explore my body, feeling the swell of my breasts, my nipples getting hard as my fingers brushed against them… I looked at the locked door, and taking a deep breath and mustering all the courage I had, I spread my legs. I put my hands on my legs and I started caressing my thighs up and down, moving my hands on the inside of them, going upwards. I remember looking at the door again, afraid my mom would break in and scream at me. When nothing happened, I reached my pussy and started touching myself lightly, just to see how it felt. It was a weird sensation, but as I explored it with my fingers, I found my clit and it started to feel good. I mean you know what I’m talking about, so I don’t need to tell how it felt… Anyway, it felt really good and so in every bath I took after that, I touched myself, rubbing my clit with my fingers. A while after that, I discovered it felt really good if I humped a pillow and so I kind started doing that… quite often.

One day we got news that my grandma hurt herself falling down the stairs and my dad sent me to her house to help her, since he needed my mom’s help at the farm. I got there and it was really nice seeing her. My grandma was spending most of her time in bed because of her injury, and Gregory, her second husband needed some help around the house since he needed to take care of his company. I was there basically to be my grandmother’s companion, reading, talking, watching TV and helping her on whatever she needed.”

The room was silent, making me look up to see if Bri was still following me. Our eyes met and she gave me a tiny encouraging smile, making me smile back. I kept my eyes on her face as I continued.

“On my second day there, my grandpa, I mean, Gregory – he was married to my grandmother since I was small, so I always called him grandpa. Anyway, on my second day there, he came home with this giant teddy bear as a gift for me for being there… You know, the one that I keep on my bedroom chair with a red ribbon around his neck. Anyway, a couple of days later I started to feel really horny, but I was way too embarrassed to do anything being in someone else’s house. As the days went by, I felt myself feeling stressed and annoyed so one day before bed, I just gave up and did it.

I was staying on their guest bedroom, and since it had a vintage queen bed, I had the teddy bear beside me. I was laying in bed one night, feeling super horny and bothered, the lamp illuminating my surroundings and without giving much thought, I climbed on top of the giant brown bear straddling it like I used to do with my pillow back home. The bear felt so good between my legs, it was a lot bigger and larger, and it’s fur was soft against my legs…” I told Bri. I could see her biting her bottom lip wanting to say something and I knew right away what it is going on in her head which made me laugh.

“No, I wasn’t talking about the teddy bear when I said I had had a sexual experience with someone.” I said shaking my head, a smile still playing on my lips. I looked down on the bed between us, a little embarrassed with what I was telling her.

“I started to move my hips, grinding against the bear, releasing small throaty moans. Our farm was big, my room was on the second floor and my parents’ bedroom was on the main one so I got used to not being extremely quiet when I played with myself and I didn’t even realized I was making any noise.