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The one that wasn’t meant to be…

Age when it happend: 14
Where it happened: Her bedroom
Langauge: English
Sex: Male
Rating: 5
Category: Straight

I had a friend that I had grown up with since elementary school. Well, we weren’t really friends, more like acquaintences that often talked off school, but during class we were rivals, always competing to get the best grades and to finish our tests and assignments first.
I had never thought of her as anything other than just another classmate until one day I accidentally grabbed one of her breasts while reaching for a basketball during one of our games. She was very well developed for a 12 y/o, maybe a full b or c cup. It was one of those moments that seemed to have lasted for hours, but I’m sure it was just a brief second. I blushed and appologized right away, she also blushed and said it’s good, then corrected herself and said don’t worry about it. That day our friendship changed, we were inseperable, we would eat together at lunch, I would walk her to her house even though it was out of my way. It was very innocent, the most we did was hold hands since we weren’t allowed to date just yet.
A year later, we had an assaignment for our health class to make a presentation to the whole class about pregnancy prevention. We went to the local family planning facility and asked for condoms and other preservatives to show at our school. Our teacher was very impressed, but she demanded that we turned in all of the contraceptives to her, since we were too young to use them. We were both upset, since we both thought we were very matured and level minded and took it as an insult. For weeks we talked about it and about having sex, not about us having sex, but just the act of intercourse itself.
Soon after, I turned 14 (she was 4 months younger than me), and her mom would not let her go to my party because she thought we were getting a little too close. After that day I noticed that she was a little distant, she would not hold my hand anymore or look at me in the eyes.
One day after I walked her home from school, I asked her to tell me what was wrong, she told me to wait outside her house, she went in, saw that no one was home and then invited me in. We went to her room and the she told me that she had gotten into a fight with her mom because she wouldn’t let her go to my party, and that her mom had told her she was a whore because she was having sex wih me. She was crying when she told me and I asked her why her mom thought that, since I had never been to her house or she to mine. She then told me that she had kept one of the condoms from our presentation and that her mom had found it, without saying a word, I reached into my school backpack and pulled out a condom and told her I had done the same just to piss off the teacher, we both laughed and she said that was her reason too. We were sitting on the edge of her bed, holding hands, looking at each other, it was a very akward moment and we both moved our heads together to kiss, but she looked down at the last second and I rested my forehead against hers and told her that I loved her and that I hated myself for not saying it before. She told me that her mom had said some very bad things about me just being interested in one thing, and that when I was done with her I would find someone else to fuck with. Then she told me that she knew that wasn’t the case since I had never pressured her to do anything, not even kiss. I told her that I didn’t think we were ready to do anything like that, to which she replied that she had been thinking about that a lot and that she was ready to go further. We then kissed for the first time, she told me that she loved me too, that the reason she was so good at school, is because she was just trying to impress me, and that she started to play basketball because she knew that I liked playing it. She then stood up in front of me and took her school blouse off and let her uniform skirt drop to the floor. She then put her arms around my head as I felt her bare back with my hands and she whispered on my ear and told me to make love to her. I undid her bra as she took off my shirt. I’ll never forget when I kissed her nipples for the first time, she let out a soft moan and her knees buckled and I felt her body weight as I held her to keep her from falling. She then laid next to me as I explored her body, she was definetly an early bloomer, as she was very well developed. I took her panties off and noticed how bushy she was and how wet the hair around her vaginal area was. I just stared at her pussy for the longest time, admiring it, touching it, smelling it. I finally had the courage to taste it and she had an orgasm almost as soon as I found her clit. She was very wet and there was this milky, watery fluid coming out of her vagina, she sat up and was as surprised by it as I was. We had both read a lot of books about sexual intercourse and we thought of ourselves as experts on the subject, but we had never come across anything like that. By this time I had already taken my pants and briefs off, I stood up and opened the condom packet and took it out and she insisted on putting it on, the moment she touched my penis I felt a shiver through my spine that stopped at the back of my head. She played with it for a few moments gently stroking it, until she looked up at me and she said she was ready for it. She sat at the edge of the bed with a couple of pillows on her back and I stood in front of her with my dick at the entrance of her pussy, we looked at each other and she gave me a nod, I then pushed forward, but had a hard time getting more than the head of my penis in her. I could tell that it was painful to her, no matter how gentle I was trying to be, so I told her that I was going to have to just force it through and to brace herself, she just noded as she bit her lower lip and I entered her. It was painful to both of us, as I felt like I had literally broken my penis and I could see her blood between the coupling of our bodies. She screamed in pain and yelled out an I love you. I just stayed inside her for a couple of minutes without moving, I was holding her close to my body and kissed her forehead as I tasted her sweat. We then started moving slowly at first, following her instructions as she was the one in the most pain. We worked up a good rythm and after about four or five minutes, she was on her back and I was on top of her, she started to whisper “I love you, I love you” over and over and faster and faster until she started to tremble, her legs clamped around my back and her arms squeezed my neck and she had what I can only describe as a violent orgasm, which was more than I could stand and I came at the same time. It was an indescribable feeling, I wanted it to last forever, but at the same time it was more than I could handle and felt like something was wrong, as I could hardly breathe. We held together as we felt each other tremble every time we tried to move. I felt naseous and happy and peaceful and sad afterwards and we both got dressed. We kissed one more time and said goodbye as she walked me out of her house.
She didn’t go to school the rest of the week and I was very worried that her mom had found out, or that she was hurt because of me. The following monday we acted as if nothing had happened while we were at school and when I walked her home she told me that she wanted to take things slow like we were before, that she now realized that she wasn’t as ready as she thought, and that although she did not regret what we did, she was very depressed and emotional after I left her house and did not want to feel that way again. I was ok with that, but I also told her that all the things I had said during, were in fact the real way I felt, and that I really loved her and hoped that we would some day get married. She started to cry and told me that she would be very happy if that happened, she then kissed me on the cheek and walked into her house.
We never again talked about that and a year later we moved to the United States after my dad lost his job. We kept in touch for a while but when we realized we weren’t gonna have a farytale ending we decided to let go and say good bye to each other. I’m now 34 and still single, since I haven’t found a girl that can compare to her. I hope that she found someone to make her happy and can appreciate what a special person she is.

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