1. My First Time (Spacing Corrected)


    Date: 9/7/2017, Categories: True Story, Author: firstimewonder, Rating: 81.8, Source: sexstories.com

    and drove home. Over the next couple of weeks, we explored each other in greater and greater detail, but never really saw each other due to the dim light. Dean began probing my virginity, pressing his finger into my vagina, exploring, feeling, and experimenting. Even having a single finger inside me hurt. We began to believe that something was wrong with me such that we could never make love with each other. In retrospect, it escapes me why I didn't just make an appointment with a doctor to determine what was wrong. As we talked about it, and read more about what the books said regarding the first time, we began to understand that I probably had an unusually tough hymen. One of the suggestions in the books was that I should stretch it with my fingers over a period of time, which was supposed to gradually enlarge the opening. As I helped Dean not to hurt, he reciprocated by playing with my virginity, gently probing and stretching. It wasn't altogether unpleasant, but for some reason it didn't seem as if we were making very good progress. One Sunday evening as we were driving home, we stopped on a deserted road and began to play around. After about an hour, I was dripping wet, but unsatisfied. I had made Dean come, and his passion had somewhat subdued. I was nearly dressed, and had already put my panties on when Dean began playing with my thighs once again. He slid his fingers under the leg band of my panties and began probing. I felt his finger penetrate and then I felt more ...
    pressure than normal. Slowly, slowly he pressed until I felt myself spreading open further and further. When I asked him what he was doing, he told me that he had two fingers inside me. "Do you want to try it?" he asked breathlessly. "Oh yes, let's see if it will go in," I replied without hesitation, "but be sure you don't come, I am not very far from my fertile time." Dean almost ripped my panties in his haste to get them off me. “I think I can hold off now that you have made me come,” he replied. “I usually can’t come this soon anyway.” An instant later he had shed his pants and shorts, and was between my legs. I tried to get ready, but he was almost like a stampede. He settled himself over me and began moving into position. He probed a couple of times, totally missing the target. Finally, I reached down and grasped his throbbing penis and steered it to the right place. "Be careful, and promise you will stop if I say so." “I will,” he promised sincerely. "Are you ready?" In response, I tugged his penis until it touched me. I continued to hold the intruder in my hand, and as I felt the invasion begin I began to squeeze it tighter and tighter. "Are you OK?" he asked. "Uh, huh, just be careful," I replied with a trembling voice. He pressed a little harder and I began to feel as if I were being torn apart. I squeezed him as hard as I could and at the same time began pushing back. I didn't tell him to stop, because I wanted to know if it would go in. Dean didn't jam it into me; ...
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