Dear Diary

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Wendy tells her diary all about her first time..
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Dear Diary,

Today Steven asked if I wanted to go biking after school with him. He's lived next door ever since I can remember, but it's been a long time since we played together. A few years ago at school he started hanging out with a different crowd than the neighborhood gang, and I think he thought he was somehow better than us all of a sudden. But, when he talked to me today, it seemed like he didn't think that at all. I don't really know what to think now. I guess I'll go with him tonight, but if he thinks he's real cool stuff now then I'll stay away from him after that.

I'll write later,

Wendy

Dear Diary,

Steven was at my house with his bike right after school. I grabbed mine and we took the nice way to the creek path. It felt like we weren't even in the suburbs anymore. I had to go slower than Steven because the path is bumpy and hilly, but he didn't speed ahead. He waited for me to catch up. I think that was really nice of him.

When we got to the bridge that crosses over to Elm Heights, we stopped. I told Steven I didn't want to be out too late because I still have homework to do (I have to get that done, so I should be quick writing this, but I want to get it all down). Anyway, at the bridge Steven took out a bottle of pop and package of cupcakes, like the ones mom sends to school with me for lunch. He handed me a cupcake. We ate them sitting on the bridge with the water rushing under us. The sun was a warm orange and Steven said I looked beautiful eating my cupcake in the sun. I felt embarrassed, but it made me feel squishy inside. He offered me a sip of his pop and I was reluctant, but I was thirsty so I had some. My lips circled the same spot his did! I felt like I was touching his body. I had a flash vision of covering the head of his penis the same way I was sucking on the pop bottle. Since Steven is a year older, I wonder if he has been with anyone. I don't know much about his life anymore.

I said again that I should get home before it gets dark, so we headed back. It was harder going back uphill, but again Steven waited and even walked his bike beside me when it was too steep for me.

When we got to the end of the path he asked me if he could kiss me! Can you believe it? My heart almost stopped. I was so scared. I didn't know what to say. I was glad we were hidden by the trees, because if my mom or any of the neighbors saw us and told my mom, I would be in BIG TROUBLE. I ended up stuttering out a croaky 'ok'. He held my head in his hands and pressed his lips against mine. It felt like what he was doing. The kiss lasted for what must have been five minutes, but felt like hours. He didn't move his mouth around like they do in some movies (thank god...I'm scared I won't know what to do when that happens!).

When he finished kissing me, we walked our bikes the rest of the way home on the sidewalk. My stomach was filled with warm, fluttering butterflies. My mind was a cluttered jumble of thoughts. I managed to ask him something I needed to know: how many girls he had kissed. He said that he had kissed a few chicks during spin the bottle games and truth or dare, but that he had been too busy with his friends lately to have time for girls. He said that he didn't want that anymore, and that he had ditched his friends to spend his time with me.

I feel on top of the world. Steve likes me. And not just likes me, but likes me enough that he chose me over his friends.

I think I like him back!

Wendy

Dear Diary,

My birthday party is today. My mom has invited Grandpa and Grandma Hill, Mama and Papa Prient, my aunts and uncles and a bunch of my cousins. Susie said she would come to save me from them, but she forgot she had a piano recital today. So I'm stuck alone with them. Ugh.

I guess it won't be that bad. Mom's making her special chocolate cake with the vanilla icing and I guess I might get some nice presents.

I'll be nineteen at 6:43pm. I don't look or feel older, but this is supposed to be such a monumental age. I hope it is an exciting year for me. I don't want to waste it, because I'll never be nineteen again.

There's the doorbell...sounds like Aunt Frida. I'd better go.

Wendy

Dear Diary,

The party was ok. Lamest gift: my Grandma got me a Tshirt with a cat on it saying "I'm Purrfect". I had to put it on and act really excited about it.

Best gift: Steve stopped by to wish me a happy birthday. He told my mom he smelled her famous cake from next door and had to come over and get a slice. My Papa asked him if he was my boyfriend and I'm sure my face was as red as a tomato. Steve smiled and said "I wish, she's the prettiest girl on the block." My grandpa chuckled and shook his hand.

After everyone left and mom was cleaning up, Steve and I went to the back patio. I realized I was still wearing my new cat shirt. I must have looked like such a loser! But, Steve looked at it and then at me and said "You know, I think you're purrfect." Then he kissed me again. This time he held one hand on my cheek and one on my waist. I feel so safe in his hands. He opened his mouth a bit as we kissed and it wasn't as scary as I thought it would be. He took his time and let me get used to it, nice and slow. I think he is a real gentleman. After we kissed, he kissed the tip of my nose and told me he had to get home to study for his biology test on Monday.

Could I be falling in love with Steve? I don't know what love feels like, but my heart is light and my stomach tenses when I think of him.

Goodnight,

Wendy

Dear Diary,

Last night, as I lay in bed, I couldn't stop thinking about Steve and his hands on me. I love it when he holds me as he kisses me, but I imagined his hands moving all over my body too. First I pictured them rubbing up and down the sides of my stomach, then up to my breasts and rubbing them; molding them. To make it more real I rubbed them myself. Then I imagined him moving his hands down, first over my nightgown and then when I wanted more, I slid them under. I rubbed my hands (Steve's hands!) over the furry outside of my vagina, running my fingers through then tendrils of hair, and then sliding them into the smooth inner layers.

Exploring my vagina got me excited with all the folds and hot spots. I found that it was a hard to move my fingers smoothly, so I built up some saliva in my mouth and spit it into my hand. It felt goopy and slippery, just the thing I was looking for. I rubbed the spit all over my vagina. I made sure every spot was covered. Then I tested various spots to see what felt best. There is a hard bump at the top that makes my vagina tense and clench every time I move my fingers over it. Even nearing it starts to make my insides move. I wanted to feel what was happening in there, so I used one hand to insert a finger into where it was moving. I touched the bump with my right hand and my hole tightened around my finger. It was thrilling. Why have I never done this before?

This was such a new experience that I had to feel it all. I kept the one finger in the hole and tiddled away on the bump. I rubbed it faster and faster, until I felt I was going to lose control. Then I did! My hole gripped hard around my finger and a rush of heat flowed over my body. My vagina got wetter than ever and I had to lay quietly for a moment and take a breather. But I wanted to do it again...and again...and again!

I stayed up half the night exploring. I found that I could put bigger things in the hole, first more fingers and then I got an idea. I very quietly got out of bed and looked around my room for things that would go in. I found a candle and a long sunscreen bottle. I took these back to bed to test them out.

The candle went in really smoothly. It is long, so I only put it in halfway at first. I moved it in and out. That felt really good. I tried putting it in all the way but it hit the back. I like this feeling A LOT. So I plunged it in hard, bringing it all the way out and then plunging it back in again. I almost cried out in ecstasy. Then I remembered the sunscreen tube and wondered what it would feel like.

I removed the candle and tried the sunscreen. It is thicker, so it was a bit harder. I had to relax to get it in. I slowly nudged it in more and more, it took a long time to get it all the way in. But I felt really filled up. I kept it there while I fondled the bump a bit more.

Touching the bump almost made me explode. I spent some time building myself up to just about the point of no return and then paused for a moment. I did this over and over. Then I started searching around for more hot spots on my body. I was reluctant to touch my bum, but getting so close to it while playing with the hole made me want to, so with the sunscreen still in, I moved past it and rubbed my back hole. It felt different and tingly. I spit again on my fingers to make it slippery and slid them around. I even managed to put a finger in. With my vagina filled, I thought, the only thing that could make this better would be if both holes were filled.

So, I brought the candle to my bumhole. I rubbed it around in the spit so that it would go in smoothly. I pushed it in. It hurt a bit, but at that point, even pain felt good. With one hand I moved the sunscreen in and out and with the other I moved the candle. I felt like a goddess. This was the best feeling I had ever felt. Then I thought of how the bump would make it even better. I pumped both holes until they were screaming at me to finish them off and then quickly moved up to the bump and sped it up with my fingers. My whole body felt like it burst into fireworks. My waist shot into the air and pushed the sunscreen bottle out of me and to the bottom of my sheets. I felt exhilarated and exhausted. I fell asleep as the candle slowly slid out of my bum and my vagina oozed it's juices onto my thighs.

Now all I can think of is Steve fucking me. I want him to come in through my window tonight and fuck me so hard my bed slams against my wall with every thrust. But my mom would hear, so that won't do. Maybe I could sneak over to his house after dark. His bedroom is in the basement far away from everyone else's, and it would be easier to get into.

I'll be thinking about this and planning it all day at school. My vagina is tight and wet just thinking about it now.

Wendy

Dear Diary,

Here's the plan:

I'm going to eat dinner with mom, do my homework and then go to bed early. I'll get warmed up in bed and then sneak over to Steve's window once I know my mom is asleep.

Steve walked me home from school today. I asked him about his biology test and he said it went well. What I really wanted to ask him was if he wants to fuck me as bad as I want to fuck him. We kept catching each other's eyes and every time we did I felt my panties get a bit wetter. I want to kiss his lips, I want to suck his dick, I want to bite his chest, I want to feel his dick deep inside me, filling me up. I want him so bad.

Wendy

Dear Diary,

I have been warming myself up in bed. Watching the clock on my bedside table waiting for the time that my mom goes to bed, takes her pill and zonks off. The time is barely changing, it is taking forever! I keep getting close to coming because I am so excited, but I want to save it for Steve. I haven't been putting anything in me because I want to be nice and tight for him too. I've just been circling the bump and rubbing my breasts. I think it is time now, I hope my mom is asleep.

Wish me luck,

Wendy

Dear Diary,

I pulled it off without a hitch!!! My mom is still asleep and I am now a woman! I was really quiet sneaking out. When I was just about to the back door, the grandfather clock chimed in the livingroom, and I thought I was caught. But I waited a while and then opened the door achingly slowly and slipped out. I snuck through the hedges that separate our yards and tiptoed to Steve's window.

I tapped quietly and waited...I tapped a tiny bit louder and waited...Then I heard him stirring. He whispered through the window "who is it?" I told him and he quickly opened the window and helped me in. It was more difficult than I imagined sliding through the window, but thankfully he held me strongly by the waist and lowered me down. My nightie slipped up with his hands as I slid down and I was left with it up around my chest and nothing underneath.

This unashamed display excited Steve (although I think he may have already been excited as he had a moisturizer bottle in his bed and he was already rock hard...which I didn't mind one bit!). I kissed him (instead of him kissing me) for the first time and that just made him mad about me. He pulled my nightie over my head and tossed it to the floor. He covered me with kisses as I leaned against the wall.

He rubbed up against me and I could feel his steaming hot cock pressing me. It was long and hard, just as I imagined. I explored it with my hands. I rubbed it until the moisturizer he had been using on it wore off. Then I licked it, kissed it and sucked it with rampant passion. Steve was groaning above me as I kneeled on his bed and bobbed my lips against his groin. He got loud enough that I stopped and pulled him down to the bed to whisper to him that I didn't want to get caught. He said that he would try to be quieter, but that he was so happy and wanted to be inside me so bad that it was hard to keep it inside.

My heart swelled, as did my vagina and I spread myself out for him on his bed. He reached for the moisturizer, but I stopped his hand and moved it to me where he found that I was already gushing with my own juices. He felt around, slipping and sliding and making me want him inside me even more. I told him I needed him in me and he did just that. I spread my legs wide apart so that he could get in easily and he slid in slowly, I moaned and then stopped myself, because I knew I should be quiet, but it was really hard to keep quiet with the realization that Steve's penis was actually inside my vagina! I wanted Steve to know that this was heaven and all I wanted to do for the rest of my life was have him fuck me.

I pushed a curl of hair away from his ear and whispered "Fuck me hard and deep, slam into me. I want you to fuck me so hard that we will hurt tomorrow." He whispered back "Are you sure? You're always so quiet and shy. You're so much wilder than I imagined." I told him I was very sure and as I sucked the lobe of his ear, he gasped and then plunged into me, deep and hard just as I'd asked. My breasts bounced with each thrust and he grabbed them and held them firmly as he gained momentum.

Just as we were about to peak he pulled out and flipped me over so that I had my bum in the air. He spread my thighs a bit until I was in a sturdy stance and then he held the outer lips of my vagina so that it was stretched and pushed himself in. His body slapped against mine with every thrust and I love that sound. He started to feel harder (which I didn't think was possible) and I asked if he had a condom. I turned over and watched him as he went to his dresser drawer and got one. He put it on in the moonlight and his body glistened. He is beautiful.

He climbed into his bed and gave me a lick and a kiss on my hot spot bump. I was raring to go. He asked if I wanted it slow or fast. I thought about it for a second and told him slow then faster and faster until we both cum. He held my legs spread apart and entered me slow and gentle. We both reveled in the soothing feeling.

I brought my hand to my special spot and circled it. Steve saw this and his eyes rolled back into his head. Doing it seems to really turn him on. He watched and as I sped up, he sped up. We raced with each other until we were both going so fast it was a blur. And then he was slamming me so hard that I took my hand away and let his body do the work. Every time his body slapped my vagina and my bump, I moaned. And then just when I couldn't handle all the pressure building up inside me, we both set off a symphony of fireworks together. I could feel his cock pulsing out cum as my vagina clenched around him. This was what I was made to do!

As I was leaving, Steve told me that his parents would be out of town this weekend and that we should make a midnight plan to be as loud as we want. He invited me over to "quietly study" tomorrow night. I'm going to spend all day planning new positions.

I can't wait!

Wendy

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2 Comments
AnonymousAnonymousabout 15 years ago
Ns

love the way u discribed.

Keep up with ur diary thing xD

AnonymousAnonymousalmost 16 years ago
Awww!

"but it made me feel squishy inside"

How cute!!! :D

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