All characters in this story are 18+
Any constructive criticism is greatly appreciated.
My name is Jack and I was born in a small town in Kansas. My dad owned and ran his own store which kept him away from home a lot but I'd usually spend lazy summer days helping him out around the store or just hanging around it in general. I was an only child until my little brother was born when I was in the sixth grade. The introduction of a baby into the family dynamic was anything but smooth. My parents were already spread pretty thin with the shop and the general struggles of house duties.
I can distinctly remember my father telling me " Jack, as a man you've gotta be willing to make At the time I was confused by the almost cryptic sentence but as I got older I learned what he meant by that. For me specifically that meant that I had to start working in the shop by myself more.
My teenage years consisted primarily of going to my small school from 7 to 2, working at our store until about 8 or 9 and then finally going home and trying to do enough school work to pass my classes. In the end, I think the experience helped me gain a decent work ethic and some sense of responsibility.
But at the same time my social life was pretty much non-existent. The bulk of social interaction I had were the customers who came into the store and a few friends from school who would keep me company at the shop for an hour or so. Going through puberty behind a counter sucked for the most part but it was true torture in the summer when women would come into the store wearing short dresses, tank tops without bras and jean shorts cut so short that the pockets show from the bottom.
A couple times I mustered the confidence to flirt with the girls from school who would come in but only a few times did they ever flirt back, but that's as far as it went… except for that one time with Jessica. For context Jessica was a girl from my school who was in the same grade as me. She dated a friend of mine during our freshman and sophomore years of school but he lost interest and wanted to pursue other girls so they broke it off. Her and I weren't really the greatest of friends but we were friendly towards each other if we ever ran into each other. I didn't take much notice, or at least I tried not to, to her physique when they were dating but that day in the store I couldn't help myself. She was about 5'3 with long black hair that ended at the small of her back. Her breasts weren't large by any definition of the word but they looked good on her smaller frame. My eyes traced her every curve and my eyes were very pleased with her voluptuous backside. Her ass mesmerized me, it captivated it ; in simpler words it made me stare. And she noticed that, I couldn't make out her expression because she looked away too quickly to avoid my glance but I immediately felt embarrassed.
My emotions had gone from carnal lust to embarrassed in a second. I could feel my cheeks get hot and my palms start to sweat, and what was almost worse was the raging hard-on I still had.
I tried to make myself busy so I wouldn't go back to staring at her butt, but she called my name from the other side of the store. I was flustered but responded and walked over to where she was. The view damn near made me paint the inside of my underwear. She was bent over looking at some hand tools we had on one of the lower hooks. She asked me a question about the difference between two brands and I tried to answer her without making it obvious that I was pitching a tent. She grabbed one of the socket and wrench sets and abruptly backed up as she was getting back to a standing position bumped into me, making her bubble butt brush my erection. She said as she turned around and looked up at me for a half second before her eyes darted down to the stretched material around my crotch. My eyes were fixated on hers for that moment, it only lasted half a second but to me it felt like an eternity. I’m convinced my soul left my body for a while there.
Her eyes shifted away quickly but I could see them widen and I could only imagine what was going through her mind. I tried to do some damage control by faintly apologizing in a hoarse voice. She didn't let me finish though, she interrupted my speech by waving her hand and saying, "its okay". My heart was racing but her words put me at ease a bit. I tried to at least salvage the sale by asking her if she was ready to be rung out, she nodded her head as she muttered "yeah". As I was walking back to the counter I felt something hit my butt. I looked back to see what it was, I saw Jessica smirking before she said, " You got to touch mine so I wanted to touch yours". I chuckled and started walking forward again.
I told her that was fair as I rang her up and we talked about some of our classes. Before she left she told me there was a going to be a small group of her and some friends getting together at what was commonly known as the dog rock, which was an area about 45 minutes from the shop that was marked by a large rock that people said looked like snoopy. I hadn't really been to a party outside of my own birthday parties when I was younger but that wouldn’t stop me from taking the opportunity to go.
I was restless for the rest of the night but I was finally able to close up and before I left I grabbed a 30 pack of Budweiser, because as a younger man I believed I needed that liquid courage. I stopped at home before I was on my way to dog rock, just to let my parents know I'd be home late. I was surprised by how fine they were with it but I guess they knew that I needed to go out a little bit as a teenager. The walk was long but the mental image of Jessica's perfect ass being hugged by her shorts kept my legs pumping. As I got closer I could make out the sound of people shouting, laughing and see the soft glow of small fire they'd lit.
When I got close enough to make out faces I said "hey" as I raised the case of beer. There were 9 other people besides myself, 2 other guys and 7 girls including Jessica. They all looked at me in silence for a moment but then erupted with excitement. I didn't really know any of them all too well but the sight of alcohol was enough to make them treat me like their best friend. I could see some bottles laying around and a couple of the girls swaying in that trademark drunk way. But the night continued on with everyone stumbling around and eventually just sitting down.
Someone suggested we play never have I ever. After a few tame prompts like cheating on tests and travelled outside of Kansas we got right into sex. One of the girls said it and everyone laughed and looked around to see who put a finger down. The other guys all put a finger down and half of the girls did as well. I didn't see the need to lie so I didn't and I got looked at for a little bit but we quickly just moved on to more specific sex acts like anal and certain positions. Two of the girls said they were getting tired and one of the guys agreed so everyone started to get their belongings together.
I was tossing empty beer cans into their cardboard case while everyone was leaving. Jessica was grabbing her bag but waved her friends off because she had to put the fire out. I thanked her for inviting me and she thanked me for bringing booze. I'm not really sure what took me over but I just felt like I was being pulled towards her. Either way I ended up next to her as she was putting the fire out. We were alone at this point and it the last embers of the fire were going out. This was my defining moment as a teenager. I looked down at Jessica and in my slightly drunk mindset I just moved on pure instinct and hormones. I leaned in and downward trying to aim my lips at hers. It wasn't my first kiss, that was Karen from my sixth-grade class, but it was my worst attempt at a kiss. I ended up pressing my most of my lips to her cheek and only about a tenth of my lips actually made contact with hers.
Thankfully that moment didn't last too long because she adjusted to get full lip to lip coverage. My mind was concentrated on the feeling of her warm lips on mine and then I became aware of how close our bodies were now. I could feel my now erect cock trying to escape my pants and jabbing her in her stomach. So far so good, I thought, so I started to escalate the situation. My jaw opened a tad and I let my tongue slip past my lips and brush her lips. She got the idea and soon enough our tongues were gently wrapping around each other. My dick was throbbing and it felt like there was no way my boxers could contain it. I reach my hands around her and each one found their way to one of her ass cheeks. She had changed into a sundress so my palms were greeted with the bare skin of her butt and my fingertips could feel the soft fabric of her panties as they rode up a bit from the introduction of my grip. The felling of her supple ass in my hands was bringing me close to climax. I could feel my body tense up as I held back what I could only assume would be premature ejaculation.
Her hand came up to my side and I felt her press me backwards, so I backed off and loosened my grip on her butt cheeks. At first, I thought she had just realized what was happening and wanted it to end but when I looked at her I could see it was for a different reason. Her eyes were fixated on my crotch and I could she wanted to see what the fabric was holding. But just to be sure I didn't pull it out, I only unzipped my jeans and moved them down a few inches to give her the space and opportunity to grab it if she wanted to. Part of me wanted to just pull it out and bend her over but another part of me was anxious and nervous about the situation. To my delight she reached down and felt my throbbing meat through the cotton boxer briefs i had on. It didn't take long for her to pull the elastic band of my underwear down and let my cock spring up from its restrained position. I could hear her breathing change as she looked down at my pulsating member. I slipped my thumb in my waistband to hold my boxer briefs down and give her some freedom to touch it. She reached out and placed her hand in it gently at first then wrapping her hand around it. I had never seen my own cock in anyone's hand besides my own so while I watched her grip my manhood I couldn't help the feeling that my dick looked bigger than usual. Her fingers tightened around my dick and she slowly moved her wrist, moving the stretched skin on my shaft up towards the head. She kept the strokes short and slow at first, her grip tightened a bit more as she started to stroke my dick more rapidly. My other hand was free but not for long, I slid my hand under her dress and let my fingertips glide up her thigh to her panties.
Jessica shuffled her legs to spread them more, a clear sign to me that I was being given an invitation to her pleasure palace. I felt her slit through her panties and was surprised to feel the moisture and heat so prominently. I couldn't wait much longer to touch her bare pussy. With my index finger I pulled her panties to one side and with my middle finger i began to probe around her genitals. I ran my finger up and down her slit a few times before finding her opening and letting my finger sink into it. I could feel it stretch and give to the introduction of my finger. She was practically dripping by that point so after the initial push to get in it was like her vagina was pulling my finger. The sensation was like nothing I've ever felt before, it was hot, not warm but hot, combined with the viscous secretions it was almost like putting your hand in scalding hot water but it felt great. I curled my finger a bit and felt around my fingers temporary home, with every movement it become more obvious to me that on top of the heat and moisture weren't the only things i was feeling. I was also feeling her walls clench my finger tightly. I didn't think of it back then but It would’ve been tough to actually fit my dick in her that night.
Yeah that's right, I didn't lose my virginity that night. Up to that point it felt like i was in a completely different world but the rustling of shrubbery and the sound of footsteps brought me back to reality. We both quickly pulled our hand away from each other’s privates and took a step back. I quickly zipped and buttoned my jeans back up while she made a slight adjustment to her underwear. Neither of us said a word we both just kind of looked around and started to walk away.
The walk back home went by quick because my mind was racing, a million thoughts ran through my head. I didn't know what I was supposed to do form that point on. But as I was trying to get into my bed without making any noise I had a moment of euphoria. I relived those minutes over and over in my head while I laid in bed. That's when I felt my testicles ache and my cock stiffen. I'd almost forgotten that i was pretty much moments away from cumming when we heard someone walking near us. The encounter at the shop paired with the incident at dog rock had my blue balls at an all-time high, an unprecedented level. So naturally I had to take care of the building pressure by relieving myself. I would usually look at some porn to get off but with everything that happened that night I was able to blow my load by just smelling the lingering scent of Jessica still on my finger and the mental image and reliving of that experience. That combo proved to be enough to make me shoot ropes of cum up about foot into the air before the fell back and covered my stomach and legs. To this date it's still one of the most explosive ejaculations I've ever had.
story by: JimmyJackJohnson
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