>DISCLAIMER: THIS STORY IS ABOUT A FIRST SEXUAL EXPERIENCE WHERE BOTH PARTIES WERE UNDERAGE (17).
If you want to skip the narrative portion in the beginning, the smut starts where it’s bolded.
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America wasn’t the only one getting a birthday gift on July 4, 2007. Albeit belated, I can’t imagine a better present than having my first experience be with the cutest guy I knew, the guy I had the biggest crush on.
He was the middle child, I was the only child. He was used to getting forgotten and craved attention, while I was accustomed to receiving all of it. He was the youngest older brother, being just eleven months older than his sister, and 7 years younger than the eldest brother. He was eager to please and I was eager to explore. He certainly would not be my first or last kiss, but he was one of the sweetest, because I had been wondering what his lips tasted like for years.
He was one of the quiet guys in church. Shy. He was always leaning up against a wall, just outside of the circle of people talking and laughing, with his Bible in hand, pastel polo shirt perfectly tucked into matching plaid shorts with a belt tightly through the loops and matching shoes. Tall, dirty blonde hair grown out like a skater, green eyes just like his father. He had a beautiful smile, and even prettier, strong broad shoulders I could see my calves resting on perfectly.
He was always sweet and respectful, opened all of the doors for me wherever we went, let me serve myself before he ate, waited for me to sit down at the table to take the first bite of dinner, and would always carry on the conversations that I started. He would sit next to me cross-legged on the carpet of his parents’ room while we folded towels and bedding and blankets to help his mom.
We used to chase each other around the house, as kids, stomping up and down the stairs, around the kitchen island and over the couches, tripping over each other onto the area rug in fits of laughter. Now, all I wanted to do was fall pussy-first onto his cock and take a quick break from that to sit on his face.
By the point I realized that I felt this way, I had already fooled around with enough guys and gals to know what felt good, and what I wanted to try. I had come close to actually going all the way, but had been either interrupted or so disappointed with the quality of the makeout session that I decided I rather not waste my time finding out with someone who would be terrible.
I knew he noticed how our friendship had changed, how it had evolved from the simple joys of childhood and had been sprinkled with sexual tension and angst. Through my experience I discovered that being subtle was not my forte, and that forwardness and unapologetic flirtation got me absolutely everywhere I wanted to go. So, I started catching his eye when he stared at me, watching him smile and avert his gaze nervously, blushing. I gave him the twice-over when I knew he was looking at me, I’d put a greater bounce in my step when I went up and down the stairs, and pressed my tits against him a little tighter than necessary during hugs.
His shy reactions and embarrassment was even more encouragement and fueled my desire to make him the first person I ever fucked. He was sweet, I was sure he would be gentle, and I was more comfortable with him than any other guy I knew. I didn’t think he had a clue as to what he would be doing, but it couldn’t be that hard to thrust in rhythm. Corrupting him and turning a good Bible-reading, church-going boy into a freak would make this perfect. If I managed to be the first girl to inspire him to such uncontrollable lust that he forgot everything that his mother and the pastor had taught him for the past 16-17 years, I would count that as the greatest victory.
He was on my Top 8, I was on his. We sent chain mail surveys and questionnaires to each other to fill out and post on the Bulletin Board on MySpace. Finally the day came when I decided to push him further and sent him a naughty quiz and dared him to take it and send it back. He called me silly but said he was never one to back down from a challenge. He was on MSN messenger while taking the quiz and was chatting me up about how he couldn’t believe I sent him that. He refused to believe that I knew what any of those words meant or the things that were implied.
But, he sent it back anyway. And the answers threw me from first gear into fourth gear. The way this quiet, innocent sweetheart answered these questions changed the way I looked at him entirely. The fact that he knew what a blowjob was, what being a cocktease was—even the fact that he had watched porn and jacked off. The real shock came to me when I read that he had a preference for tits over ass, brunettes over blondes, tall girls over small ones… he even admitted to getting himself off to thoughts of Xena and Wonder Woman. I took it as an open invitation. So I went in right away.
After about a half hour of relentless teasing on my part and giving him a hard time for being a “pervert” he finally cracked and teased me back and opened up about sexual desires being something he struggled with in his faith. He just couldn’t stop himself from stroking his throbbing cock and cumming to all of the fantasies he had and he couldn’t stop himself from watching porn.
This was, of course, excellent news for me, because it was a perfect in to propose a solution to his problem. I explained to him all the problems I had reigning in my sex drive and all of the thoughts I struggled with on a daily basis. So, I proposed that whenever we felt this way, to keep each other accountable, we should call one another and the other that we were having impure thoughts. He thought it was a great idea.
So, that’s what we did. For the coming months, we would call each other on the landline, or message each other though MSN and AIM, at any hour. I’d barge into his room and bed barge into his sister’s and give me the look. He would ask me to come out so he could talk to me and his sister would give us both a confused look then roll her eyes at our odd friendship. He would walk into my Sunday school class and I’d interrupt band practice.
Every time we did this, there was a little more involved than the one before. At first, we would just tell each other, “I’m having a moment of weakness.” Then, it would be, “I had a moment of weakness about this person.” Then, we moved on to, “I had a moment of weakness when I thought about this particular thing.” And finally, it would turn into me saying, “I just was Mr. Johnson sitting in a pew and I really wanted to slide down onto his cock and show him what it’s like to feel my wet pussy sliding onto him.” and him whispering back, “I saw Mrs. Jones this morning, I couldn’t stop staring at her bouncing ass and imagining what it would be like for me to enter her from behind and have it jiggle on my dick.” At that point, it became a competition, who could become most explicit and who could turn the other on the most.
And so we carried on until one evening, we were watching a very risqué movie with his sister and older brother in the basement. There were several points at which we glanced at each other and smirked, knowing we would have to debrief each other at the end of the movie. When the movie was over, we all filed upstairs to the kitchen to make ourselves sundaes. His mom had laid out a all of the things we could ever need in an assembly-line type.
We finished creating our sundaes and went to the living room and sat down, cross-legged on the couch and started whispering excitedly immediately. We heard his sister yell at us that we were weirdos and smothering about how I was supposed to be her best friend and not his. We ignored her and continued our little game. After we were done discussing the finer points of exactly what we would have done if we were the characters and what we wanted them to do to each other, he stayed quiet for a moment and looked down at his nearly empty bowl.
And with the quietest voice I had ever heard him use, but also the hottest and most intense tone I would never have expected from him, he told me that he had one more thing he wanted to share but that it was super hard for him to admit and I had to promise not to make it weird or ignore him after he told me. I shrugged and agreed, waiting hungrily to hear what he had to share. And that was the moment his eyes met mine and he told me that the girl in the movie reminded him of me and that the entire time, he couldn’t stop picturing me naked and imagining that I was her, and that he was doing those things to me. When he finished, he looked down again and waited for my reaction.
I looked over at his siblings, who were distracted and not paying attention to us any longer. I lifted his chin up and made him look at me. When he finally did, I held nothing back and told him that I had been imagining him fucking me like since before we even started the sharing game. He looked surprised and completely turned on at the same time, but then he looked conflicted.
He told me he had never done anything like that before so he wouldn’t be able to do that for me. I told him that I had never done it either, so it would be perfect. We could figure it out together. We could practice. He looked pretty convinced, so we planned it out. I would be coming over their house for the annual 4th of July block party. My mom had gone with my step dad to his parent’s lake house and my dad was probably sleeping through any festivities with the same amount of enthusiasm that he avoided any and all social situations. It was the perfect day for a sleepover.
And it was.
Everyone was burnt and toasty from the pool, full from the food, and exhausted from staying up to watch the fireworks. My best friend and I got ready for bed, brushed each other’s hair, and got into our pajamas. My pajamas were probably far more inappropriate than they should have been for someone staying over in a house full of guys. Even though I had a matching set with her, the tank top and shorts she wore didn’t stick to her petite frame like they were painted on, with her thigh gap and A cups. My pajamas, on the other hand, were taught on my DDs and hugged my hips and ass a little tighter than they should have.
**I waited for her to fall asleep to the sounds of the late night MTV show playing at a volume barely above whispers so I could tip toe out of the room and make my way down the hall to her brother’s room, slipping into the open door and closing it as quietly behind me as possible, locking it. He was waiting up, as he said he would be, sitting up in the middle of his bed with the covers over him. He had several bottles of water next to him on the nightstand and a giant bottle of Advil, sitting next to a tub of lube, a box of condoms, and wet wipes.**
**I couldn’t stop myself from laughing so I covered my mouth and made my way to him on the bed. He looked like a man ready for war. He told me to turn on his light, so I did before I climbed onto the bed and crawled on my hands and knees to him and straddled him. He was so cute, looking so nervous but also so ready. I started kissing him and put his hands on my waist, he seemed to forget how nervous he was and started to match my sloppy kisses with his sloppy eager ones. His hands started to wander and roam and I felt his cock growing under me. It felt like there would be enough there to work with, even though it didn’t feel enormous or girthy, it was enough to feel good, I speculated.**
**We dry humped each other until the wet spot in my panties was starting to rub off on the comforter. He grabbed my tits hard and squeezed my ass even harder while he kissed me and then begged me to please let him fuck me before he came just from the rubbing. I didn’t need any begging, I was ready to do the begging myself if we didn’t get the show on the road.**
**So I got under the covers with him and laid down on my back. He took my shirt off and slid down my shorts. He wasn’t wearing anything so when he sat back to look at me, I could see his cock, hard and curved up ready to go. He looked down at my pussy and slid a finger across the lips and said he didn’t think we were going to need lube, before picking a condom up from the nightstand, tearing the foil carefully and awkwardly sliding it down on himself.**
**He stopped for a moment and asked me if I was sure I wanted to do this, because once we did it, we could never go back. I told him to shut up and shove it in already and he gave me several soft kisses before letting me know he was going to put it in. I held my breath and felt him slowly push in. I felt a stinging, burning sensation and winced at it while I heard him exhale and moan low. I asked him to wait before he took it out again and got used to the feeling of him inside me. I gave him the green light and he slid out slowly and slid back in again. He did this a couple of times and then started to go faster. It felt better the faster he went, so in between my low moans, I pleaded that he go faster, and encouraged him to go harder. The heat and tightening in my tummy felt just like it did when I rubbed my clit and orgasmed on my own, but it somehow felt… full. It felt… complete. It felt like the pressure was somehow building stronger and the pleasure mixed with the receding stinging felt delicious.**
**He complied and I could tell he was about to bust at any moment, so I enjoyed what I could for the time being. A couple more thrusts and he started shaking and pulled out, cum spurting into the condom, and collapsed on top of me. He took a moment there, panting, and kissed my neck and buried his face in the crook of my neck. When he finally got off of me and laid beside me on the bed he asked me if I came and when I told him I didn’t, he asked if he could help me out. I still wanted to cum, so I told him to go ahead. He started kissing my lips and moved down to my neck, then went further down and started to lick and suck on my nipples. It was sloppy and I had to tell him to suck harder and bite, but it made my pussy tingle again so I started to rub my clit while he attended to my tits. At one point, I asked him to put his fingers inside me while I rubbed my clit and he sucked my nipples, and it didn’t take much longer for me to lose myself to the feeling and writhe in the pleasure of my orgasm.**
**He laid next to me again for a moment and we kissed softly. I told him we should get cleaned up because he was still wearing the condom and there was blood all over both of us. I felt an unfamiliar soreness when I got out of bed and went to clean myself up with the wet wipes on his nightstand. I needed to get my clothes on without any evidence of what just happened.**
**Before I left, he asked me if things were going to be weird between us—now that we had seen each other naked, it would be impossible to avoid picturing that every time I came over. Also, having such an attraction to each other would be hard to hide. The tension between us might be stronger now than ever before, because now we knew what it felt like and we wanted to do it again, again, and again. I told him I honestly didn’t know the answer to that, but that we would find out soon enough. I gave him one last smile and told him goodnight and turned the light off to head out of his room to the bathroom. I went down the hall, didn’t bother turning on the light in the bathroom, and just threw all of the bloody wet wipes into the toilet and flushed them.**
I snuck back into my best friend’s room and slipped into bed with her, the TV still murmuring something unintelligible and inconsequential. She was snoring, so I figured she was not suspect to anything that just happened. I could only hope that I have nothing away and that we were discrete enough to get away with this.
I hoped I didn’t look any different. That I didn’t “glow” as one stereotypically did when they had sex for the first time. I knew there would be no way that my best friend or her mom would be able to tell, but I was nervous about glancing too long at her brother, or being uncharacteristically coy or quiet. But, the next morning, when I asked him to pass the orange juice at the breakfast table we were all sitting around, everything was normal except for the small smirks on both of our faces.
For a moment, I thought I saw his dad look at him, then look at me, and pause before reaching for a waffle, but when I looked up from my scrambled eggs, he was looking down at his newspaper.
Source: reddit.com/r/sexystories/comments/cl86f7/the_time_val_fucked_a_memoir_fucking_for_the