Story Details

Dear Sadie

hillarysmuff on Diary Stories

Dear Sadie,

I'm going to call you Sadie. My mother bought this journal a year ago and now I'm going to call you Sadie. As you can see from the picture I've taped inside your front cover, I'm 13, 5'2", 95 pounds, with long red hair and thick lips. My breasts are just beginning to sprout. I'm between an A cup and B cup. It's kinda hard to get a bra that fits right. Mostly I just use sports bras, or not wear one.

Anyway Sadie, I'm writing you because things in my life have really begun to happen in my life. Last night, I had a sleepover at Nicky's house. Nicky is half Hawaiian. She is my size and weight, but she has the most beautiful olive skin and long dark hair. About nine o'clock, Nicky's mom left us alone and it was "tickle time". That's what me and Nicky call it. We take off all our clothes, then lay next to each other on the bed. Nicky usually starts by running her fingers along my body. We've been doing this for three years, but the last time, she actually stuck her fingers in my pussy, then licked them and kissed me. Of course, I had to do the same for her.

I was really looking forward to last night. I was so wet while I watched Nicky undress. Her boobs are smaller than mine. My nipples are pink, but Nicky's are dark brown. We're both only beginning to get our first hairs between our legs. When we were naked, we climbed into the bed. We started to lay next to each other, but Nicky fell over on me. We both giggled and I pulled Nicky as I spread my legs and felt her pussy touch mine. I felt electricity shoot through me and we started rubbing against each other. That's when we heard the noise in Nicky's closet.

We got up and tiptoed to the closet. Nicky pulled the door open and Nicky's ten year old cousin was in the closet. Allen had his pants down around his knees. Nicky grabbed him and threw him across the room. He landed next to the bed and we could both see his thing hanging out. "I can see you enjoy what you're seeing dweeb". She looked at me and I could tell that she was thinking something. "Get on the bed dweeb" she told him, "I'm going to teach Casey something and you're going to enjoy it, but I swear dweeb, if you tell anyone, I'll kill you. Now, get on the bed".

Allen sat on the bed. Nicky pushed him back and made him lie down. She licked her palm, then grabbed his thing. She began working her hand up and down his thing. She used her other hand to put one of his hands on her boob. Allen smiled, then a moment later he shot white stuff all over himself.

"That's called a handjob" she said, "it's an easy way to get a guy off". She stood up and told Allen to stay where he was. She pulled me over to the closet. She started to whisper in my ear. "It hurts the first time a guy puts his thing in you, so, why don't we let dweeb here put his thing in us, then it won't hurt so much the first time?" "You want to?" I asked. Nicky nodded, then walked over to the bed. She climbed on top and slowly put his thing in her. She went up and down about five times, then climbed off. "Your turn" she said.

I climbed on top of Allen. I had a hard time learning where to put my hips, but I finally got his thing in me. It didn't hurt at all, it felt good. I started going up and down. I lost track of how much. Nicky pulled me off of him. "That's enough" she said, "pull your shorts up dweeb and get out of here". Allen got up. We shared a look and I think he knew I wanted more.

A couple of hours later, I was still awake and I could tell Nicky was sleeping. I snuck out of her room and found Allen's room. He was lying on his back. He was only wearing jockeys. I pulled his jockeys down and was surprised to find it hard. I wondered if it hurt. I tried to be careful as I climbed on him. I put his thing in me. It felt so good. I started sliding up and down on him. My boobs felt so hot. I squeezed them and I almost made a noise. I had to bite my lip. I noticed him get stiff, then felt his stuff shoot in me. He smiled, then opened his eyes. "What happened?" he asked. I put my hand on his mouth. "Do you want more?" I asked. He nodded. His thing was still hard and in me. I started riding him again. I put his hands on my boobs. He started thrusting his hips. The bed made a noise and I had to stop him. We started again. A few minutes later, he shot his stuff in me. I gave him a kiss then climbed off.

I had to stop off at the bathroom because his stuff was running down my thighs. I cleaned up as best I could. I climbed back into Nicky's bed. I spooned up next to her. She moaned a little as she held my hand and kissed it. We fell asleep holding each other.

Hi Sadie,

It's been three weeks since I wrote and I have something new to tell you. Three days ago, I was on my way home from school. I noticed this old guy under the creek bridge. I know he was homeless because he had shabby clothes on and he had a shopping cart. I still had the lunch my mom packed because my teacher had bought lunch for me and nicky because we both got A's on a pop quiz. I parked my bike and took him my lunch. He smiled and said "Thank You" as he ate the sandwich. I watched him eat. I guess I was fascinated because I never knew my father or either of my grandfathers. It made me feel good to feed him. I fed him the next day and today, but today.....

After he ate, he smiled and thanked me again. I asked him his name. He told me it was Tom. I asked him if he had a wife. He smiled and said "No". I then got a crazy idea and asked him if he wanted a handjob. He looked at me like I was crazy. "You know, handjob", I said moving my hand up and down. He just sat there, so I pulled up my shirt and showed him my boobs. He grabbed one of my boobs and started sucking on the other. I laid back and started getting hot.

Just then, he stuck his hand under my shorts. He knew where to go because once he started touching me, I felt stirrings in my belly. He stuck his finger in me a couple of times. I wanted to fuck, but I was letting him do what he wanted. Suddenly, he stopped and pulled my shorts off. He moved between my legs and I just let him. A moment later, I felt his thing go in me. Nicky was right, it hurt, but then the pain ebbed and it started to feel better.

It only took a couple of minutes, then he shot his stuff in me. He looked nervous as he pulled his pants up. He looked around, took his shopping cart, and took off. I pulled my shorts up and went home. I took a shower, then a bath. After the bath, I noticed that my pussy stank. I got nervous and worried. When my mom got home, I started crying. I was worried that I had caught a sexual disease and I didn't want to get the old guy in trouble, so I told my mom that I had fooled around with a guy at school and I was scared. She was pissed, but took me to a doctor.

We both cried this afternoon and night. I ended up on the pill and I was grounded until school finished.   

Dear Sadie,

It's been two weeks since summer vacation started. Nicky went away to camp. My mom couldn't afford summer camp, so she made me promise to behave while she was at work. Yesterday, I was riding my bike around and I had to pee, real bad. There's this three story building in my neighborhood. It was the place closest to where I was. I went up to the front door and found it locked. A security guard got up and came to the door. I told him I had to pee. He looked around, and let me in. I thanked him and practically ran to the bathroom.

It was the nicest bathroom I've ever seen. There was a couch and scented soap and towels. When I finished, I went to the desk where the security guard was. Like the homeless guy, he was an old guy. He told me that he wasn't supposed to let me in, but the three people that came in had left. Then he started telling me how he worked 12 hour days on the weekends and how it was slower on Sunday than Saturday. I asked him his name, and he told it was Frank. I asked him if he was married or had a girlfriend. He told me no. I started getting an idea. I asked if I could visit him on Sunday. He told me yes.

When I went today, I wore only a tank top, shorts and flip flops. Frank let me in again, and I went right to the bathroom. I undressed, then poked my head out into the hallway. I called Frank and told him there was something he needed to see. When he walked in the bathroom and saw me naked, his eyes got real big. He just stood there. I grabbed his belt buckle and pulled him to the couch.

I had to open his zipper and get his thing out. I raised up my hips and he finally started responding. His thing was as big as the homeless guy. It didn't hurt at all this time. I was surprised at how long it lasted. He fucked me for an hour before he finally came. He held me for a few minutes, then I got up and got dressed because mom was going to get worried about me.

I gave Frank a kiss as I left the building. Then, as I was leaving, I noticed that Frank had a van. I got an idea, but it would have to wait till next weekend. I can't wait. 

14 Comments

didrojilme

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❤ I was a really bad girl. Punish me with your dick in my mouth. -

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didrojilme

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❤ I was a really bad girl. Punish me with your dick in my mouth. -

https://cutt.us/HLJAX ◀ ❤ ❤ ❤

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