When I was 16 I was a junior in a small private high school. I had taken some courses during the summer so I had an extra “study hall” where we sat in the library and either studied or got caught up on schoolwork. I had always been kind of shy and kept to myself for the most part, especially during this class because it was just me with senior jocks that were cocky and obnoxious.
One day while I was sitting at my table, one of the seniors, Jeremy, asked if he could sit with me. I told him sure, but I didn’t say much else and resumed my work. Jeremy was gorgeous. He was six feet tall with brown curly hair and had the bluest eyes and a beautiful smile. Jeremy continued to sit with me throughout the week, neither of us really saying much other than the typical small talk about classes and teachers.
Jeremy sat with me but this time we talked about how I competed my horses and how he stayed busy playing football and baseball. Then he started asking about my dating life. He asked if I was seeing anyone, but he knew the answer already. Everyone did. Embarrassingly, I hadn’t had a boyfriend before nor had I ever been kissed. At this point in my life though, I just wanted to get it all done- kissing, losing my virginity- all of it. So many of my friends were having sex and I just wanted to get it out of the way.
As study hall ended, we exchanged numbers and that night Jeremy texted me. It started off with the usual talk and then it progressed pretty quickly back into my non-existent dating life. I explained to Jeremy how I was curious about being with a guy, but I didn’t want to date anyone. Feeling brave since this was over the phone and not in person, I told him that I wanted to have sex. WHAT was I doing?! I had no business talking to anyone about this stuff, let alone a senior that had so much experience compared to me.
Jeremy responded with, “I think that can be arranged.”
We then planned for him to come to the stables where I rode my horses and we would sneak off together.
After my jumping lesson, Jeremy arrived. I hopped in his SUV and we drove to the back of the property and parked by the lake in a wooded area. We got in the back of his car and sat there awkwardly until he leaned in and kissed me. I was having my first kiss. I could feel him sneak his tongue into my mouth and his hand traveled under my shirt and beneath my sports bra.
I quickly realized how hard it was going to be to get naked in his car with my riding attire. I slid out of the back of the SUV and stood there looking at Jeremy who was reclined back, rubbing his cock through his shorts, his eyes were roaming my small, still clothed, frame. I took a deep breath and leaned over and pulled my tall, black riding boots off, then I slid my jodphurs down, but left my pink lace thong on. I pulled the bottom of my polo shirt up and over my head and there I was- standing in front of a senior football player in only my sports bra and lace thong.
I crawled back into his SUV and sat beside him leaving the back door open. No one ever came out to the lake so I wasn’t worried about getting caught. Jeremy moved closer and leaned in and started kissing me. His hands again roamed over my breasts, squeezing them so hard through my bra it was almost painful. Then his left hand drifted down into my lace thong and he wasted no time sliding his fingers up and down my shaved pussy spreading my wetness.
I groaned into his mouth when he found my clit and he began circling it. As he increased the pressure and speed, I couldn’t kiss him anymore and quickly began panting against his mouth. I felt fire in my veins and ice on my skin and then I burst. I came harder than I ever had before and it was on Jeremy’s hand. He then pushed his finger into my tight hole. I was so wet he slid in but it still stretched me. “Holy fuck, you really are a virgin, aren’t you?” Jeremy moaned into my ear, slowly pushing his finger in and out of my pussy.
I half giggled but quickly gasped as he pushed a second finger inside of me stretching me more than I had ever been before. I grabbed his hand and held it still for a few seconds to adjust to the stretching then I let go and he started working his fingers in and out of me gently. We could hear how wet I was over our collective panting but I needed more. I didn’t know how I could possibly fit more than his two fingers in my pussy, but I had to try. “More...,” I breathlessly begged him.