Jesse

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A boy shares his first time with an unexpected friend.
2.6k words
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~~~~~

Growing up in a very small, close-minded town as a gay teenager was not an easy thing to do. In my high school, there were a little more than 300 people that attended. The school was filled with "hicks", as I referred to them (being the "rebellious" teen that I was), and finding another person to help ease some sexual tension was a very difficult, if not an impossible task to achieve. I was the only kid at my school who openly admitted to being a homosexual. No one seemed to mind, and even if they did I had a lot of the more "jocky" students behind my back in case they decided to cause me any trouble.

Despite being out of the closet, I was still unable to get any attention from someone who may even just be curious about sex with another male. My hand was barely enough to keep my high sex-drive under control, and I suffered through high school without another cock to play with. All I could do was go home (which was a 15 minute bus ride to the middle of no-where, mind you), and jerk myself off a few times before I passed out. It was a very depressing time in my life indeed.

So here I was, a recent high-school graduate, still living with my parents, and still a virgin. I didn't have a driver's license, so I was unable to contact anyone and meet up for some quick sex. I was average looking, 5 foot 5 inches with an average build, brown hair and eyes, and a raging member pressing against my jeans at all times. I never thought finding someone to fuck would be so difficult, it was just a matter of where I was raised. I was unlucky, to say the least. Until I got a phone call one evening.

I answered my phone with a confused "Hello?", not expecting a call at 11 PM at night. On the other line was what sounded like a very nervous guy, who replied with a very muffled "Hey... is this... Jason?" I confirmed who I was and then asked who I was speaking to. It was a boy from my high school named Jesse.

~

Jesse was an adorable kid to say the least. He was an inch or two shorter than me, which was surprising seeing as how I was very short myself. We were only a year apart from each other in age, with him being 18, and myself being 19 at the time. He had curly light brown/dark blonde hair, the softest, most soothing voice I have ever heard, a smile that made me want to melt, and the most beautiful blue eyes I have ever seen in my life. The only problem with Jesse was that he had very Christian beliefs, with his family being very harsh towards the gay community. That put me off a little, but I still managed to play out certain fantasies in my head, starring him.

~

There was a brief silence on Jesse's side of the phone. I could tell that he was very nervous for some reason. "Hey..." he said sharply, "You're... gay, right?" I chuckled a little bit, and replied with, "Yeah, why?"

"I was just wondering because..." He paused for a while, "Because I was wondering if... I could try stuff with you?"

I was completely shocked, unable to grasp that I had just heard those words muttered from his lips. I collected myself because I realized that I had a golden opportunity to experience sex with a very gorgeous boy. "I mean... sure, if you want. What do you have in mind?"

"I just want to experiment a little. Do you mind if... I come over?" My parents were out of town, thankfully, so I agreed. I gave him the directions to my house and then prepared myself for what I might experience in the coming hours. I quickly cleaned my room, made my bed, and confirmed that I looked well enough to impress this beautiful boy. Then I waited in the most painful anticipation that I have ever experienced.

I saw headlights coming slowly up my driveway, and that is when my heart began beating extremely fast. I heard Jesse's car door shut, and foot steps up to my door, followed by three slow knocks. I tried to make myself relax a little, and then got up to answer the door. When I opened it, I saw him standing there, twiddling his thumbs, with a scared look on his face. He was just as cute as I remembered him being, seeing as the last time I saw him was at my graduation. I told him to come in, and he followed. I lead him to my room, and sat him down on my bed, he looked around, inspecting my living quarters. I asked him if he would like anything to drink. He respectfully declined.

"So... What are you interested in?" I asked, trying to get a word or two out of him. My heart was still racing. He simply shrugged his shoulders, and said "I'm not sure."

"We don't have to do anything that you don't want to." I said, reassuring him that I wasn't going to go to fast, make him uncomfortable, or hurt him. He relaxed his shoulders, and that is when I made my move.

I sat down beside him on the edge of my bed and unzipped his jacket about three quarters of the way down. Sliding my left hand underneath the fabric, I felt his firm chest beating away. While doing so, I could feel my dick begin to harden. I looked Jesse in the eyes and smiled. I always smiled when I looked into his beautiful eyes, even when I was in a bad mood. I moved in and gave him a soft kiss on his lips. I moved back and asked him if that was okay, he nodded, so I continued. This time, I parted his lips with my tongue and began to passionately kiss him. He was a little bit shocked at first, but then he relaxed and joined me. The friction that I felt between our tongues was turning me on so much, that now I had a rock hard erection, escaping out of the side of my briefs. I was still in disbelief that I was able to touch this boy in the way that I was.

Without parting our lips, I moved my hand slowly down his chest, and onto his lap. I softly squeezed at his crotch, making him let out a soft moan. I parted our kiss and once more asked him if he was okay with what I was doing. This time, instead of reassuring me, he moved in and began to kiss me once more. That was the reassurance that I needed to continue.

I unbuttoned his jeans, and patiently undid the zipper. Once the zipper had been undone, I reached inside of his jeans and caressed his bulge. The let out another moan. His cock was already hard! I broke away from our kiss and tore my shirt off. He stopped and I noticed that his eyes had redirected to the bulge that was in my lap. I began to smile. I quickly looked into his beautiful blue eyes before sliding his jacket off, and removing his shirt. My cock twitched at the sight of his smooth, toned torso. I pushed him onto my bed so that only his legs were dangling off of the side. With my left hand I was massaging his balls through his underwear, and with my other head, I scooped the back of his head and lowered my lips onto his, sliding my tongue back and forth against his, before breaking the kiss and moving my hungry lips toward his sexy bright pink nipples. I licked and sucked those beautiful nipples for what seemed like a good five minutes, before leading my tongue to his neck. I kissed his neck and he continued to let out soft moans as I rubbed his hard member through his tight underwear.

I kissed Jesse one more time before moving my tongue to the center of his lightly haired chest. I dragged my tongue slowly down his fuzzy trail, leading down to his belly button, and eventually down to his lightly trimmed bush. I began to hesitantly pull on the elastic band of his boxer-briefs as I looked back into his gorgeous eyes. I spun him so that he would be completely laying on his back. I tugged at his underwear again, before he arched his back and made it easier for me to slide his jeans off. I took only his jeans off at first, because I still wanted to give him one last look-over with my eyes before unleashing the beautiful instrument hidden beneath that layer of cotton.

I got in between his legs and set myself down on my stomach. At this point, my basketball shorts had completely fallen off of my body, leaving me with only my white, pre-cum drenched briefs on. I kissed his hairy thighs in multiple spots. I could hear him breathing heavily, and I could tell that he knew what was coming next. I massaged his underwear hidden pouch with my mouth, as I pulled on the elastic band once more, freeing a beautiful 6 inch cock. I could see that Jesse's cock was pulsing, and even had a bead of pre-cum escaping from the head of his shaft. This got me very excited.

From there I slid off his boxer-briefs, and got a full view of his thick throbbing cock, and huge, full balls. My mouth began to water as I looked at his cock. I looked back into his eyes, in a way to get permission to touch his beautiful member. When he nodded, I lowered my hungry lips onto his dick. I gave it short kisses up and down the shaft, and then grabbed it and squeezed. Jesse let out a loud moan this time, and I deviously smiled. I was having the time of my life.

I rolled his balls back and forth between the fingers on my left hand, and used my right hand to guide his cock into my hungry mouth. I began to suck on the tip of his penis, and he let out a very loud moan. I started slowly letting in more of his cock into my mouth, until my nose was buried in his pubic hair. His cock was very tasty, and I soon began to speed up the pace at which I sucked. I felt him writhing underneath the pleasure that my mouth was giving him, and I could not of been happier. I sucked and sucked until I felt as if he was about to explode, and then stopped.

I heard him sigh, disappointed that I didn't allow him to cum, but then greeted his lips with mine, and began to passionately kiss him once more. He pushed me away from him before saying, "I want you to fuck me."

I was surprised that he was allowing this to go this far, but I wasn't going to object to his command.

"Are you sure?"

"Yes, I want to feel your cock inside of me."

These words almost send me over the edge. I freed my raging erection from my briefs, and then asked Jesse to turn over. I can't believe that I hadn't given his ass any attention until now, because it was truly a work of art. He had a beautiful big, but toned and proportionate bubble butt that drove me crazy, and now it was right in front of me, his pink hole staring me in the eye. I spread his ass cheeks and began to devour his tight hole. He moaned with pleasure as my tongue danced around his perfect opening, just waiting for me to fuck it. I could of continued like this for hours, but my cock wouldn't let me do so.

I noticed Jesse's cock peeking out from beneath him, so I squeezed on the shaft, which sent a good amount of pre-cum flowing from the purple swollen head. I scooped the pre-cum up with my index and middle finger, and then did the same to my dick. I used the pre-cum as lube, as I slowly inserted my fingers into Jesse's tight asshole. He was moaning a lot louder than before, as I worked his hole with my fingers, before removing them, and placing the head of my cock at the opening.

I told Jesse to relax, arch his back, and breathe. He began to do so, and I carefully began to push my cock into his hole. He buried his face into my pillow and let out a muffled scream, which made me collapse on to him and whisper in his ear, "Do you want me to stop?" He told me not to, so I let him adjust to the tip of my penis for a few seconds, before carefully pushing more and more of my cock into him. It wasn't long before I felt his ass resting up against my hips. I gasped loudly, as I had never felt this sensation before. I began to slowly move in and out of Jesse, as his short pain began to turn into immense pleasure.

He was moaning louder now. As I pumped him faster, I could feel my climax beginning to rise. I didn't want to cum yet, though, so I told him to flip over. I wanted to see the rest of his beautiful body before I came.

I pushed my cock back into his tight asshole and started fucking him harder now. I grasped the back of his skull and looked into his beautiful eyes. I then looked down at his cock. I let his head rest on the pillow as I continued to fuck him hard, and then I grabbed onto his cock. I started stroking his hard, meaty rod as I thrust in and out of him, giving both him and I an abundance of pleasure.

"I'm about to cum." I told him, as I continued to pick up the pace at which I was thrusting.

"Please cum inside of me, please." He told me, and those were the words that sent me over the edge. I stroked his cock even faster as I started to climax. I began to cum, shooting cum into Jesse's beautiful tight hole. As he felt my juices being shot into him, he began to orgasm as well. Jesse shot 7 or 8 huge ropes of cum, covering his chest, following by several smaller ropes, dripping down over my fingers, and onto his pubic hair. It was so beautiful, and so sexy.

When I finished cumming, I collapsed my body onto his, smearing Jesse's cum in between our chests. I kissed him again, us both breathing heavily into each other's mouths. I licked the load that was left on my fingers, and then began to passionately kiss Jesse again. I wonder if he liked the taste of his own cum.

After we both rested a few minutes, I pulled my now semi-flaccid cock out of Jesse and lay down next to him on the bed. He rolled over as well and put his head and hand on my chest, and he rested his leg on top of mine, intertwining us together. We both then began to drift off to sleep, both satisfied that we were able to experience this perfect moment with each other.

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drabidrabialmost 3 years ago

INCREDIBLE! Wish you would write more!

AnonymousAnonymousover 10 years ago

Very nice, would like yo see more!!

AnonymousAnonymousover 11 years ago
short,, sweeet n hotttttttt story¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡

Nice n daring dude........

AnonymousAnonymousalmost 12 years ago
Nice

Enjoyed the story and have no critical comments to make. The thought of taking a virgin got me excited. Would love to experience a like situation in real time.

AkshunLoveAkshunLovealmost 12 years ago
I agree about the virgins comment but...

...sooo many writers do that on here that it really doesnt matter. I guess the moral to the story is to keep it believable. Otherwise, your structure was good, plot a bit basic but that's what short stories are, characters were good, dialogue was good too, the sex was very hot but i would've kept it going for longer by describing more detail, how the main character felt, what Jesse did and said, described what happened, how it sounded, looked, tasted, smelled and felt, etc. Details like that really help put the reader in the room, make them feel that if they aren't participating themselves, they're at least watching it from a chair next to the bed ;)

Great work for a first though! Really good :) keep going :) i'd like to hear jesse's side, to know what events led him to call Jason and take the plunge, i'd like to know how it felt for him, what he thinks about Jason, did he secretly spend years lusting after Jason from afar? Just a thought :)

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