Home Dating & Romance Rosie’s Diary … The First Time…

Rosie’s Diary … The First Time…

by City People
Rosie's Diary

One of the questions I have often been asked by friends is, when was the first time I had sex? They are often forced to ask this question when they realized how smart and streetwise I can be when it comes to men. My first time was quite a long time ago. I was barely sixteen then. I remember I was in JSS2 at the time. This was back in the east where I schooled and lived with my parents.

I came from a pretty decent family. My father was a manager with the Railways while mum was a businesswoman who was doing fairly well with her business. We lived in a small but nice apartment that was still the envy of many in the neighbourhood. I liked our house, but not as much as I loved that of my friend, Linda. Linda was my classmate and her father was quite wealthy. He was a renowned businessman in the community and they lived in this big magnificent house that I loved to death. Linda also had a room to herself. She had her own Tv and Video player. Whenever we closed early from school, we would go to Linda’s place, lock the door and watch pornography movies together. She never told me where she got those films from, but I suspected she got them from a boy she was dating in school then. It was these blue films as they were called then that opened my eyes to sex.

I had already grown into a pretty young babe. In my secondary school back then, I was regarded as the cutest babe in the entire school. And I wasn’t just cute, I was hot and sexy. I have always been a tall and curvy babe. I had a glowing chocolate complexion that gave me a super gorgeous look. And to put the icing on the cake, I was one of the first set of girls in my class to grow what you could call a full round beautiful pair of boobs which stood provocatively inside the white top of my lovely school uniform. And I had a good bum to go with it. It was so big back then, but it protruded nicely. While in my junior class, I had no idea how beautiful I was. I noticed how boys stared at me whenever I walked past but their gaze only bounced off me. I thought nothing of it. It was while in my senior class after I’d developed physically even more than before, coupled with the blue films I watched at Linda’s place, that I became aware of my feminine assets. That was when I realised how beautiful I was. That was when I became aware that when boys or men stared at me, they were gazing at my boobs and my bum and imagining what they could do to them if they had the opportunity to have me with them behind closed doors. From that moment on, I began to walk better. I carried myself like a lady should and more o less cat walked especially whenever I knew boys were staring at me. Soon, some of the guys began to summon the courage to approach me for a relationship. And one after the other, I turned them down. I didn’t like any of them. Even my friend, Linda, was upset with me for being rude to some of them, wishing she were the one who had such an endless queue of toasters and admirers waiting to get her attention.

Truth is, I had a crush on a boy in school at the time. He was a year my senior and was regarded the most brilliant boy in school. He was also the school’s senior prefect. Charles was tall, dark and handsome. He liked girls, but for some reasons, he didn’t associate with girls who were his junior, he only dated girls who were his set in school. But, from the way he stared lustfully at me whenever I walked past him, I could tell he liked me. Even a couple of his close friends who talk to me had also told me he fancied me. But his ego wouldn’t let him show it. No problem with that. I was ready to wait till he got round to his senses. I was the cutest girl in school, he was the most brilliant and in my book, the finest as well. But I won’t be the one to go tell a guy I like him, my friends would laugh me to scorn. If Charles wanted me, he had to come and get me. And, not long after, he did come for me, and it was in the most astonishing manner too.

I had gotten late to school that fateful morning. The gate prefect had stopped me and a couple of other latecomers, including my friends. He wanted us to clean up a section of the school as punishment and I was insisting I would do no such thing. Me, Rosemary, clean up school? I was still arguing with the guy when Charles showed up. He asked what the problem was and the prefect told him. Charles looked at me, his eyes running up and down my body. “Rosie, is that true?” he asked me. That was the first time he would be speaking directly to me. Standing really close to him now, I realized the guy was finer than I thought. He is a fine boy and he knows it. I guess that’s why he went about with that little chip on his shoulders. That was the first time he would be speaking directly to me ever.

“Of course, it’s the truth,” I’d responded, not sounding the least apologetic. “Why would a student who’s only a year my senior tell me to go clean up the school?” Again, he gazed at me and from the grin on his face, I could tell he liked what he saw. His eyes particularly rested for some fleeting seconds on my boobs. Then, he quickly took his gaze away. He called the gate prefect aside and they spoke for a moment before he returned. “It’s alright, Rosie, you can go to your class,” Charles said to me.

“Thanks,” I said to him, “but not without my friends.”

“You can leave with your friends,” he added. The gate prefect looked pissed but I couldn’t give a hoot about his emotional state. I thanked Charles and took off with my friends.

Later in the day, during break time, a junior student came to deliver a note to me. It was from Charles. It read:

“Hi pretty Rosie, can we meet after school today? There’s something I need to tell you. Meet me in the school library, I will be waiting. Your new friend,

Charles.” 

I smiled. So, Mr. Fine boy is finally coming round to his senses…

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