Chapter 1

1320 Words
Chapter 1 She wasn’t exactly the girl next door. She was more like the girl down the street, around the artificial lake created by the housing development’s architects and landscapers, and in the back of the cul-de-sac, but the point was the same. I had known Lissa from the start of junior high. It took until senior year of high school for us to realize we were attracted to each other. Or maybe we were both too shy to admit we had feelings for each other. Once that little problem was solved, I was thrilled to have a girlfriend because nothing helps one’s confidence as having a significant other who wanted to have s*x with you. We were both nervous and wanted to wait, but wanted to do it at the same time. We wound up delaying and waiting so long, it was just before graduation that we realized we needed to do the deed otherwise it was going to be hanging over our heads all summer. The less said about summer the better. We weren’t kids. We were eighteen and getting ready to go to college. It was time to shuffle off those virgin coils and meet our destinies. Sex the first time is always a disaster for any young couples. It wasn’t any different for the two of us. Putting on the condom was a disaster. I’m not even going to go into buying them. This was years ago when sss didn’t exist. We were both nervous, which led directly to the first immediate problem. “OW! That hurts!” I looked down at her, glanced down to where I was trying to get my c**k into her p***y, and then back up to her face, pausing briefly to admire her big boobs. “It’s not supposed to hurt,” I said because I didn’t have anything else to say. “Sometimes it does the first time.” “I thought that was a myth.” “I’m tense.” “Try relaxing,” I unhelpfully suggested. She gave me a look and made to push me off her, but instead took a deep breath and tried my terrible advice. This was the window of opportunity. We were in my bedroom during one of those precious moments when no one was in my house and Lissa didn’t have to be home for a few hours. We were responsible kids. We had everyone fooled. This had been easier when we just messed around. Lissa loved it when sucked on her n*****s. She loved it even more when I went down on her. Doing that for the first time had been an experience for both of us. I was thrilled to do it. Her taste, her reaction, her softness, her everything. Especially her reaction. Somehow I had fumbled my way around into making her c****x. Not bad for a geeky eighteen year old who had no clue what he was doing. Lissa wasn’t exactly a passive participant. While she wasn’t as eager to give blowjobs as I would have liked, she wasn’t at all shy about giving me handjobs. I thought she’d be off put by my ejaculating, but it didn’t bother her in the least. “I think I’m dry,” she said. “I’m nervous and dry.” “Lubricant,” I said. “I don’t have any on me,” she said sarcastically. I grinned and waggled my eyebrows at her. “Let me solve that.” When I started moving down on her, she tried to stop me, but when I reached her p***y, she just moaned and the protest faded away. She was right. She was dry. I put my saliva to good use. My tongue got her body working and in short order her familiar tangy flavor filled my mouth. “I want you in me,” she managed to pant while I ate her out. I paused and lifted my head. “I can do that now, I think.” Wiping my face on the sheets, I moved back up. This time she took my hard c**k (just thinking about eating p***y could get me hard) in hand and tried to guide me in. No joy. I kept pushing and she was leading the way, but I couldn’t find her entrance. “This is so f****d up!” I complained and pushed off her, kneeling between her spread legs, my c**k pointing a curved line up to the ceiling. “I’m still too tense,” she said. “Want to stop? Try later? Just mess around?” Lissa shook her head and sat up. “I want to be on top.” I hadn’t envisaged losing my virginity to a woman riding on top of me, but I was willing to give it a go. We swapped positions. I liked looking up at Lissa as she knelt above my hips, holding my c**k, balancing herself, running my cockhead along her slit, trying to find the entrance, and focusing too much. Her t**s were huge and perfect. I mean, we were eighteen, of course we had great bodies. She was gorgeous in a way only young women can be. I was too thin and too gangly to be attractive, but for some reason she loved me enough to do this. “Let me help,” I said and held the base of my c**k. I had always heard that the entrance to a woman’s p***y was much, much lower than guys thought. I knew where her entrance was. I had had my fingers and tongue in it plenty of times. I aimed lower. Naturally I overcompensated. Lissa’s eyes went wide. “That’s my ass!” she said, pushing my hand away. “Sorry!” a******x before vaginal s*x? That would have been something. But it wasn’t to be. Somehow the stars and the planets aligned and all the struggle suddenly became worth it. I went into her. I could feel her p***y surround me with wetness and warmth. Mostly warmth. I was wearing a condom. “Oh!” Her eyes went wider. “Is that it?” I asked. She just nodded and adjusted her stance again. I lifted my hips, going deeper into her. She moaned. I grabbed one breast and held onto her hip. She wiggled and adjusted her body. Slowly I went deeper and deeper into her p***y, until she was all the way down on me. We met each other’s eyes. And we laughed with delight. Lissa leaned forward and kissed me. We f****d awkwardly for a minute. We had no real idea of what to do, but instinct took over and we figured it out. “Can we stop?” she asked abruptly. “Uhh…yeah. Why?” “Can you get back on top?” I was worried about pulling out of her and not being able to get it back in, but I didn’t want to tell her no. “Sure.” I pulled out. We changed positions again. Weirdly, penetrating her a second time was easier. Once I was back inside her, I propped myself up on my elbows and we went at it. The delightful thing about Lissa, I realized when looking back, was that she was easily orgasmic. I had made her c*m many times with my fingers and mouth, but this would be the first time I made her c*m from actual s*x. I held back as long as I could, but eventually the inevitable happened. I came inside her. It was all caught by the condom, but I felt like a man. Panting, I said to my girlfriend. “I came.” “I know.” “Did you?” She shook her head. “I’m sorry,” I said quickly. “I can do…” “It’s okay. This was nice. We’ll have to do it again.” Spoiler: we didn’t.
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