SexFiles: Part 6 (Sarah, Part 1)

So, I was thinking back on some of my rendezvous and I remembered this girl Sarah. We got together when I was much younger, roughly 17 or so, another girl I genuinely loved. She wasn't the most attractive little thing but, I didn't see looks in her, I saw her soul, and it was more beautiful than that of a fiery phoenix soaring through the underworld with a cool breeze trail on its back. Sarah and I had encounters before, but never got to get involved with one another because we were both in different stages of our lives. Although both misguided youth, there was a certain touch of sensuality between the both of us. I could lay with her, and not even think about sex. Brushing my hand through her hair and just talking about things. Most of the time it ended up with us either arguing about the decisions we had made in our lives at the time... or making out at the very least but, it didn't always end in sex. When it did though, it was rough, hair pulling, nail biting, back scratching, good old fashioned sex.

The first time we had sex it went something like this. I was at my dad's and I had a room in the basement to myself. After so many fouled attempts to have her over cause she would either get in trouble with her dad or... well that was the biggest of the issues. FINALLY, I got her over and we hung out in the basement for a while, we had always talked about what it would be like to get intimate with each other but, we never actually got into it. There was a time barrier within that cause we didn't really have a lot of that together, even though the both of us did try to make as much of it as possible. It started very slow and soft, she was a virgin and I wasn't all that experienced myself. We sat by one another on the futon I had, listening to music and talking about life and our issues. I had my arm around her, and hers around me. Slowly but surely I started running my hands up her side, puling her closer to me while we sat there and conversed. She leaned in and put her head on my chest, so I pulled my hand up and started rubbing on her neck with the the one hand, while I slipped my other onto her thigh. Sarah then placed her hand onto my shoulder and ran her nails across my chest over the shirt. Looking up at me with these irresistible puppy dog eyes, she puckered up her thin lips and kissed me. Biting down on her lip as she pursued more, I wrapped my arm around her neck and pulled her up onto my lap. She straddled me like a horse, throwing both of her hands around the back of my neck while she started grinding on my lap. I pulled her close by her neck and kissed her deeply, she pulled back at first, which threw the mood for a quick second but, she had problems with neck pains so I apologized, kissed her on the forehead, cuddled her in my arms for a moment and then went right back to the moment. Wrapping my arms under her ass, I picked her up and bounced her over to the bed where we both paused to laugh for a moment cause I kind of BOUNCED her head off the wall on the way down. We sat up on the bed next to each other, just laughing well, I was laughing more than she was but, eventually, after I caught my breath again and realized that Sarah was giving me the poutiest puppy dog face ever, I held her back up in my arms and we laid back on the bed together.

Sarah pushed my head back and rolled over on top of me. I leaned up into her, grabbing around her waist and holding myself up. Sarah then pulled the bottom of my shirt up, ripping it over my head and tossing it to the floor beside us. Pushing me back down on the bed and, dragging her nails down my chest. I reached up her shirt and gripped firmly on her sides, puling her in as she thrust on my pelvis. Reaching behind her back I unsnapped her bra and lifted her shirt up over her head. She threw it onto the floor beside us and rolled onto her side. I rolled up on top of her, kissing down her neck and running my tongue down her chest. Swirling my tongue around her nipple while I grope her other, listening to her moans get louder and more intense. She would cover her mouth to try and muffle them but she couldn't hold them back. I drug my tongue down her stomach and, pulled down her yoga pants. Gnawing on the outside of her thong, I pulled her panties aside, dabbing the tip of my tongue on the inside of her tight little virgin pussy lips. I ripped down and threw her yoga pants and thong off to the floor, diving in face first. Twiddling my index and middle finger on her clit while I dug my tongue deeply into Sarah's vagina. I would run my tongue from the base to the top, leaving it in as deep as I could get it to go. There was a quickly spreading puddle developing on my bed, with Sarah's legs wrapped around my neck I didn't have many places to go. Right up until Sarah, with one long stream of gasping for air, let out the biggest, longest, most arousing line of moans while her pussy oozed out enough cum to fill a 16oz cup. I released my head from between her legs and sighed into a very relaxed state.

It wasn't but a moment until she perked right back up, and said ever so lightly, "my turn." Warning me that she wasn't very good at it, she rolled herself off to the side and edged me to get up where she was laying. Of course, I folded the comforter over before doing so but, quickly propped myself up just how she instructed and, laid myself back with my arms behind my head. Sarah leaned in and, unbuttoned my pants and slid them down off my waist. I used my legs to swivel my pants down the rest of the way. Sarah pulled them over my ankles, allowing me to kick them off to the side. She then slid between my legs and pulled down the front of my boxer briefs, flopping out my erect cock. Staring in awe, Sarah grabbed hold by the base of the shaft. Stroking gently as she looked back and forth between my eyes, and sizing up the size of my dick next to her face. She even pressed her arm against the shaft measuring it out from her elbow down to her wrist. Again, staring back in awe she awkwardly jerks up my shaft and looks intently at my dick. Slowly, Sarah creeps up and licks up the shaft. Trying to wrap her mouth around the tip, she ends up scraping teeth against it. She opened her mouth as wide as she could and used a twisting motion with her hands as she attempted to bob up and down on my dick. It didn't take long for her to pop up, grabbing her jaw and complaining about it trying to lock up. She pouted briefly and, went right back down on me. I would grab on her by the back of her head, wrapping her hair up in a pony tail as I lightly thrust up into her. She gagged more than a few times when my cock would hit the back of her throat. We would go back and forth in this position, with her using both hands to stroke my hard veiny cock, all she could really fit in her mouth only amounted to about an eighth of what she held in her hands. Eventually, I got tired of waiting, and she got tired of her jaw locking up around the tip of my dick so, she pulled off, and I scooted down on the bed.

She sat upright on her knees, approaching me with one hand wrapped up on the base of the shaft. Leaning in further, throwing one leg up and over, Sarah scooted up and proceeded to sit down on my cock. It was a tight fit, and as soon as we broke through the lips, she jumped up so, I grabbed back on the base and wiggled it between her lips, soaking up the mood, loosening her up. Things went a little smoother after she had reached a point of comfort, she sat right down on it and, even though as soon as she got it all the way in she clamped right down on my chest, squeezing her nails into my chest. The pain was worth every second of pleasure that was delivered.

She bounced up and down off my waist and I held her love handles, pulling her down into the thrusting, then lifting her back up to slam back down. We went at it this way for a good solid 20 minutes or so, then switched things up. Rolling her off the side of me, we moved into missionary, then quickly folding her up and putting her legs over my shoulders. I would caress her breasts and sides as I planked my dick hard in her tightly pressed pussy. The look of fear in her eyes was unable to be missed, well, it was like a mix of fear, pain, and SERIOUS pleasure. When we finished, my bed was soaked, and Sarah basically couldn't walk. I laughed, she laughed, I kissed her and wrapped her up in my arms. We kind of just cuddled for a while until her dad showed up to pick her up. It was a great day that ended in slight remorse.

We were kids, stupid kids, but the feelings were so real it killed both of us when I had to move away. I left with my dad out to where I currently live, I didn't see Sarah for YEARS after we "dated" so to speak all those years ago. She was my girl, and I was "That Guy." Years later we ended up hooking up again. She had gotten through a lot, and I had straightened up myself as well. She's happy in a relationship now but I will always have the resounding thought in the very dark depths of my mind of, "What if we became more the second time around?" Sometimes, you just gotta let "What if?" stay and look forward to, "What's next?" All of these stories are very real and very true, down to the most minor of details. Please, keep reading, there will always be more to come.

Written and lived by: Zachery Lee

This is part of a series. Read the main series of "On My Way" on Families here!