Dylan’s Summer Back Home
Introduction:
A short story. Enjoy
But nearly three years ago, I left home for the city to enroll in a prestigious tennis program for the top talents of the nation. My dad was a former pro, you see, and he’d always expected me to follow in his footsteps ever since I was a child. And so I moved away from my friends and parents during my first year of middle school to undergo a rigorous tennis program, training under the best coaches in the sport.
It didn’t take very long before I began to burn out from the daily practices, though. I was homeschooled during my time in the city, and since everyone else in the program were so competitive that they didn’t indulge in small talk, I felt terribly isolated and lonely. Before long I wanted nothing more than to return home; I missed my friends, missed the school I’ve known for all my life, and I just wanted to be a normal kid again.
And so when I finally finished my middle school education there, I unsurprisingly made the decision to drop out of the program to go back to Everton. I talked to my dad about it, and though he was disappointed, I didn’t care. Finally, I would be coming home.
When I finally returned, there was no question about how I was going to spend the rest of my summer. Now that I was on a break from tennis I would be able to spend my entire vacation from school hanging out and catching up with my friends, since we’d barely talked during my time away in the city because I was so busy. After being away for so long, though, I couldn’t help but notice that there were a couple of things in Everton that had changed since I returned.
For one, it seemed like everyone in town adored me. I was their little tennis player, Everton’s own home-bred star who’d just finished a three year tenure out in the city. Everyone greeted me by my name wherever I went, and all my friends couldn’t stop asking about what living in the city was like.
Another thing just as significant that I noticed was how my friends had all grown up quite a bit. We grew up together, and I’ve known them all since we were toddlers. But puberty changed us all a lot, and now things were really different. Whenever I hung out with the guys, all they could ever talk about was girls and sex.
“I can’t wait until high school starts and we get to see all those cute high school chicks.” Max had said. Max was one of the youngest kids in our grade. That made him the “kid” in our entire circle of friends, which was fitting since he often acted like one. “How long do you guys think before I get laid?”
“However long it takes you to grow up, shorty.” Josh laughed and teased Max, as he often did. While I was Everton’s sweetheart, Josh was kinda the leader of this group because of how charming and popular he was with the girls. “What about you Tom, what do you think?”
“I don’t know,” Tom shrugged shyly. Tom’s parents were real estate developers which meant that he was quite rich, which did help the handsome blonde-haired boy in getting quite a few female admirers amongst the girls we hung out with. It was a waste on him though, since Tom was always too shy to make a move, and never talked about girls with us.
Even then though, we all still knew that he was just as excited as us to be in high school in our quest for sexual adventure. I mean, who wasn’t excited to transition from middle school to high school? The parties and girls were a lot to look forward to, and with how much everyone was changing, the girls were only getting hotter and hotter.
That was another thing I’d noticed. Most of my girl friends weren’t just “pretty” or “cute” anymore, they were hot, and already some of the girls had begun attracting the attention of the older boys. Meanwhile, us younger boys who’ve known them for so long have begun looking at them in a different light too, often fantasizing about them while playing with our little hard cocks at night.
Because of that, it really wasn’t surprising when I began hanging out with my friends again and I noticed a lot more back and forth flirting than I did before. The boys, while still young and awkward, tried their best to convey their attraction to the different girls that they were interested in, and the girls in turn would giggle and play hard to get. Seeing how much things had changed since I left, I happily played along and showered my attention on some of the girls I fancied.
Of course, being the bumbling young teenager I was, I was too timid with a lot of my flirtations and wasn’t able to understand the obvious signs when a girl liked me back. This led to the usual teenaged confusion and angst as I sat at home wondering if a girl liked me back or not, while jerking off furiously to relieve my raging hormones. Fortunately, though, my summer of innocent carefreeness and youthful flirtations didn’t completely go to waste as I did have some success with a couple of the girls I flirted with.
Emma was a volleyball player and one of the most popular girls I knew. Even though I considered myself quite good looking, I hadn’t kissed a girl yet at this point in my life, and was desperate to. Given my own newfound popularity, I decided that I did have a chance with Emma, and so I began to constantly pursue her. After a good three weeks of awkwardly flirting with her every day that we hung out, I managed to get myself alone with her for a few minutes during a pool party we had at Tom’s house.
We were both in the pool, me wearing just swimming trunks that were too tight around the crotch, and her wearing the sexiest bikini I’ve seen anyone our age wearing. The both of us were wet and panting from splashing around in the pool with our friends, and now alone, we both began chatting idly. My heart was racing, and I was unable to maintain eye contact without feeling my cock stir in my swimming trunks, so I often looked away from Emma while she was talking. Seeing this and understanding, Emma was silent for a second, then lifted my chin her way to face her, then leaned in for the kiss.
Of course, as most first kisses are, it was electric for me. What made it even better was that it seemed like the popular volleyball player I was kissing was an experienced kisser and made up for my sloppiness easily. Our lips were locked for a very long time, but just as my hormones took over and I got braver by letting one of my hands caress her golden hair and my other rub her bare lower back gently, Emma pulled away, and told me that was all I was getting for now.
“You’re cute, Dylan.” She had smirked at me just as our friends got back. “But you’re a sloppy kisser. Maybe come back when you’re more experienced.”
Then there was also Penny. Penny wasn’t a standout, but she was really pretty and had nice eyes. She also looked like she was hitting the gym quite a bit recently, as her ass was far more shapely than the other girls our age. Even though she wasn’t where my attention was for the most part, I often found myself staring at her ass whenever she did walk ahead of me, and I’d often fantasize about being able to ram my cock into those thick cheeks at night when I jerked off in my room.
Given her more mature disposition as compared to the other girls, there were whispers amongst us boys that she was “easy”, and so one day, after having not jerked off for three days in a row because my parents had cousins over, I was horny enough that I decided to try my luck. While hanging out at the mall with some friends, I showered Penny with some attention, and received my prize when not long after, she said that she had to go, but whispered an invitation into my ear before leaving, to sneak in her room through the back window of her house later that night.
Being so horny, I obviously took her up on that offer, and luckily for me this time things were a little less vanilla than it had been with Emma. When I snuck in later that night Penny proceeded to pull me into a kiss, which quickly evolved into a hot and heavy make out heavily make out session on her bed. Our mouths opened and our tongues collided, brushing into each other and exploring each other’s mouths for the first time as we both sloppily groped each other through our clothes. It was hot, and I’d never experienced anything quite like it before that. I even groped her ass quite a bit, causing her to moan in pleasure.
That was as far as Penny was willing to take it, though, and so when I rushed home a couple hours later, the first thing I did was lock my room’s door and furiously masturbate to the memory of grabbing a handful of her ass.
Summer vacation was long, but it didn’t last forever. And so I only had time for just one more summer fling, and unexpectedly, that girl happened to be Lauren. With very light brown hair and a slim figure, Lauren wasn’t like the other girls; whereas the others were rather girly in a traditional sense, Lauren had always been far more adventurous, even a little bit of a tomboy. She was the bad girl of the group, and while we all loved her, all the boys were too scared to make any moves on her because she was such a badass. She didn’t take crap from anyone, and that intimidated most of our fragile adolescent male egos. I mean, even I didn’t even try to flirt with her at all, and I was the most popular boy in the entire town.
But one day while out exploring the hills just outside our town, I tripped on a rock and fell, spraining my ankle. My friends had planned this hike for weeks now, and had finally managed to convince one of their older siblings to leave work early to drive us all out here. So when I told them that I thought my ankle was sprained and I couldn’t continue, it wasn’t surprising that they were all disappointed. They thought they’d have to take me back, call their ride home early and come back another day, which was unlikely as summer was ending soon.
Fortunately though, Lauren stepped in and volunteered to help. Being the only child of an outdoor enthusiast mom and a survivalist dad, Lauren went camping outdoors a lot as a kid and knew first aid well. So when she assured the rest of my friends that she’d stay with me and look after me, they were relieved that they didn’t have to go home early and continued with their hike. I was in a little bit of pain, however, and was scared about being left alone by my friends in the unfamiliar hills outside of town. At least I still had Lauren with me though, and with her being the expert survivalist and all, my safety was left completely in her hands for the next two hours.
As soon as they left, things got a little awkward between us. I’ve never been alone with Lauren before; I don’t think any of the boys have, and because of that, I’ve never had a good look at her until now. To my pleasant surprise, past her tough facade, Lauren was just as beautiful as any other teen girl, perhaps maybe even more than most of them.
For this trip she was wearing a set of dark tights that wrapped around the curves of her thighs and hugged the petite shape of her ass tightly. Being the young, horny boy that I was, I couldn’t help but stare, and when she caught me staring, I quickly tried to play it off by starting a conversation with her. Even then though, I found it difficult to maintain eye contact as her lose fitting tank top was a little too loose, revealing quite a bit of her sports bra and cleavage.
Surely, she must’ve realized where my eyes were, but didn’t say anything the entire time. Instead, we continued chatting idly for most of the first hour, with long spaces of silence between conversations. Most of the time, though, I was too busy trying to look down her shirt without being too obvious about it.
Finally, I was certain that she’d caught me staring for sure when my eyes lingered on her chest while she was talking, and looked up to find her staring right at me. I thought she’d be mad or immediately call me out for being a pervert, but instead she once again didn’t seem to notice, and instead asked me how my leg was feeling. When I told her that it still hurt, though, she offered to massage my ankles to make it feel better, and even though I was unsure if a massage was going to make the pain go away, I simply obliged. After all, she was the expert out here, not me, so I should let her do whatever she wanted.
The massage started normal at first, and just as I expected, I didn’t feel that it was helping very much at all. However, as time went by her hands slowly drifted upward, and I was confused as to why she was suddenly rubbing my calves.
“It’ll help loosen up your ankle,” she had told me. “Relax.”
Once again I did as ordered since I was at her mercy, but did find that the higher up she went, the crazier my nerves on my leg were reacting to her firm touch. My heart was pounding in my chest, and I eventually found that the I wasn’t even aware of the pain in my ankle anymore.
“Does it feel better?” She asked, and when I looked up to answer, I saw that Lauren was staring right into my eyes expectantly.
“Um,” I stammered nervously, but wasn’t sure what I was even supposed to say. My heart was racing, and it seemed like Lauren was a little nervous too. “Yeah… It does…”
She never once broke eye contact, though, but began to rub higher to my thighs now. “Does it feel… nice?”
The sensation that courses through the nerves in my thigh as her strong hands massaging me there was undeniably erotic, and I was unable to stop myself as I let out a soft moan.
“That says enough.” Lauren giggled, and her hand continued drifting upward.
“Lauren?” I asked as she finally reached my crotch, which had a bulge poking out of my shorts by now. “Wha-What are you doing?”
I tried to sit up, but Lauren quickly and forcefully shoved me back down to the ground, still saying nothing as she continued to massage my crotch. There was a glint of curiosity in her eye, and it seemed as if she hadn’t done this before as her hands explored every dimension of my hard cock hidden away behind my shorts. My cock wasn’t very big at this point in time, maybe barely even five inches erect.
After several more seconds, Lauren’s exploration finally came into fruition as she found the tip, causing me to shudder as a wave of pleasure ran through my body with her touch. Seeing this, Lauren focused mostly on where the tip of my cock was under my shorts. Before long I was moaning and groaning with each touch, and my eyes had closed as I enjoyed the sensations. Fortunately for me, because there was still a layer of clothing in between Lauren’s touch and my cock, I managed to last far longer than I would’ve had she taken my shorts off.
Eventually though, Lauren’s innocent and gentle massage of the tip of my penis evolved into full strokes across the length of my shaft, and I felt myself coming close to orgasm. Since this was the first time someone besides myself was bringing me to orgasm, i could feel that it was a particularly powerful one building up in my balls, and I began to see stars as my vision began blacking out.
Instinctively I began to buck my hips upward to meet Lauren’s strokes, but in response Lauren only grabbed my balls, once again through my shorts, with her other hand and squeezed hard. I knew that that was her way of asserting herself over me. When teased by the guys when we were younger, she would often fight back by squeezing or kicks to the balls. And now that I was bucking my hips, her dominating personality must not have liked that, thus the squeeze to the balls to remind me who was in charge here. However, being so close to orgasm I somehow felt a strange pleasure in the midst of all that pain, and her gripping my testicles through my shorts actually ended up pushing me over the edge.
“Lauren!”
I gasped as my body shuddered violently in the euphoria of orgasm. I felt the cum shooting up from my balls through my shaft then out of my head and into my boxers as I finally came in my pants. Immediately, a visible wetness formed at the crotch area of my shorts, wetting Lauren’s hands. Instead of pulling away immediately, though, Lauren seemed curious about it, and instead brought her now sticky hands up to her nose and sniffed it.
“Smells funny.” She said, then chuckled.
I was still reeling from the most intense orgasm of my life, though, so I didn’t respond. My vision was still spotty and a buzzing in my head made me feel as if I was intoxicated. Too drained now to move, I simply put my hands over my face and laid back as. I tried to recover from the orgasm.
I had no idea where this sudden sexual curiosity came from. Lauren has always been so tough, so tomboyish that I’ve never even stopped to consider that she might have her own interests in guys as well, especially since all the boys avoided her like the plague in order not to be embarrassed by her. But perhaps if they knew that Lauren was just as dominating sexually as she normally was, then maybe some of the guys would be more interested.
During the entire time that I’d been laying there, Lauren had continued to play with the deflating cock through my pants out of curiosity, but after a few more minutes she eventually got her fill and got up to her feet, telling me to sit up. Apparently, she didn’t want anyone else knowing about what transpired here, so to cover up the cum stain on my shorts, she’d spill some water on me as an excuse.
“Just tell them your clumsy self can’t even drink water without making a big mess.” She shrugged. “Blame the pain in your ankle, or whatever.”
I wondered if maybe I should tease her about the almost handjob she’d just given me, but upon seeing how serious she was that nobody should find out, I decided against it. She did just do me the favor of being the first other person to make me cum, and I didn’t want to ruin my chances of possibly receiving a real handjob in the near future should she decide to pull of my shorts entirely next time.
And so I did as I was instructed, just in time as my friends finally came back. It wasn’t too hard to act like nothing had just happened after that, since they all began talking about all the things they’d seen during their exploration of the hills, and so I simply listened and managed a few laughs here and there as my friends helped me back to where the car was waiting to pick us up. Unfortunately for me, I never had the chance to speak with Lauren alone before the summer ended, and nothing more came out of that one occasion.
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