Fisting gay amateur Fisting the newcomer Caleb

Fisting gay amateur Fisting the newcomer  Caleb
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This is a story about my first time with a man. This story is mainly true. It happened a long time ago, so maybe I have exaggerated a few parts in remembering them. Though it probably doesn't matter anymore, I changed the names of the guy involved. I was about 13 at the time. Just a normal 13 year old. Simply, brown, shoulder length hair.

Little buds where my boobs would one day be. I lived a fairly shelter life. No one every really talked to me about sex, or anything sexual. What little I did know was picked up from overhearing things I wasn't suppose to, but that wasn't very much. I had discovered masturbation, as most kids too. I wasn't a porn star, shoving everything I could find up there.


In fact, if you saw me touching myself back then, you would probably have laughed instead of getting turned on. I just sort of awkwardly rubbed myself and rocking, or sometimes if I felt bold, rubbed against something. A few times, I got really bold and pushed a finger into my pussy. I know what you are thinking, so let me just tell you again, I was pretty sheltered.

Anything to do with sex was treated completely wrong, so I thought that what I was doing then was pretty bad. At one point I think I convince myself that I was some sort of sexual deviant. But my god, it felt so good. Plus there was the the thrill of staying up late, waiting till my parents went to sleep (if they were awake, they might catch me, I thought) then touching myself till I shook with pleasure (and nervousness). I knew a few things. Guys had a penis, they put it inside a woman, something vague happened and then they got a baby.

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I had some idea that penis was a hard thing that stuck out, kind of like a finger. Next to us lived another family. They had a son, named Jake.

He was in his 20's at the time this happened. 25, I think. We didn't every really interact as kids, since he was so much older than me. But I thought about him a lot. When I touched myself, he was the one that usually came to mind. One of the reasons was that he was fairly cute and had the most engaging green eyes I have ever seen.

But there was also something about the way he looked at me, a sort of appraising/approval look. Even then I knew that he liked my body. Jake had moved out of his parents house by then, but he visited them a lot. I think his mom was sick with something and he was helping take care of her, but I don't remember the details too well. She got better eventually, so I guess that worked out. I"m not really sure how I came to the conclusions, but one day I decided I wanted to know more about sex, and I wanted Jake to teach me.

It started out as more of a fantasy, something I would think about at night in me bed alone, but then it solidified into a full blown conviction. I was absolutely convinced that I could get him to come over and teach me everything there was to know.

How this was suppose to work wasn't really clear to me back then, but I was convinced I was going to make it happened. It was the summer, I was out of school and home alone. My parents would be gone for a long time. Jake was at his parents' house, helping out again. He was mowing their lawn, something that I was happy to watch him do.


When he finished, he sat down on the steps in the shade. Seeing him sit down, I walked out, determined to get him back in my house.

I going to be honest with you, I was so insanely nervous that I don't ever really remember what I said to get him in my house. I told him that I needed help with something, but I was pretty vague. I could tell he was confused, but we had lived next to each other for a long time and he had always been a nice guy so he followed me inside to help. Once we got in, I made up something, stalled, danced around, then finally offered him something to drink.

We sat down on the on the couch and said a few awkward words, then sat in an awkward silence.

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I could tell that he thought I was up to something, and was just waiting for me to get on with it. I had pretty much decided to abandon my plan, I was just going to be embarrassed and let him leave, when something came over me and I just blurted out: "I want you to teach me about sex." After saying it, I was so nervous and embarrassed, I wanted to curl up into a little ball and cry.

Jake was clearly stunned, and sat there a moment, looking at me, clearly wondering if he had heard what he thought he had heard. "What?" I didn't say anything, just looked away, wishing I hadn't said anything.

After a few seconds, I felt a hand on my arm and I looked back at him.

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The feel of him touching me made me feel more confident and I said: "I want you to teach me about sex. I am old enough to know about that sort of stuff, and I have liked you for a long time and think that you should be the one to teach me." Well, that is what I wanted to say.

What I actually said was much more rambling and drawn out. Jake stared at me for what seemed like a very long time. Then he asked me: "Have you ever done anything with a guy before?" I shook my head. "Have you ever seen a guy naked before?" I shook my head again. "You sure you want this? You seem pretty scared." I nodded. My heart was racing so fast, I didn't trust myself to say anything.

Jake sat there, evaluating the situation. Then he reached around and grabbed some blankets that were folded by the couch. He draped one over me and put one over himself. "Here, take your cloths off under the blanket. Then, when you are ready, we will pull it down together. That way, if you want to stop at any time, you can." I nodded, and didn't move.

Then, he started to slide down his pants and his worm out of his shirt. Seeing him do this, I slipped my skirt down, then unbuttoned my shirt. My fingers were shaking so bad as I slip my panties of into a pile with my other cloths. We both stayed under the blankets while we did this, so it involved a lot of squiring and wiggling. "Are you ready?" "Yes." He started to slide his blanket down, letting me see his chest.

I did the same, slowly exposing my newly forming breasts. He glanced down at me, but I couldn't take my eyes off of his eyes. We moved the blanket down farther, slowly, little pieces at a time. He kept glancing down to see my body, but I never looked at his. Finally, the blankets fell on the floor and we sat next to each other, completely naked, looking into each others eyes.

Then, I watched him move his eyes down my body, taking me in as a whole.

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I will always remember that look in his eyes. That look of complete lust.

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I managed to move my eyes down his body, stopping at his crouch. His cock was probably averaged sized, but to me it looked huge. I had never seen one before (these were the days before internet and I couldn't just pull up picture after picture of well endowed men), and all that had ever been inside me was my one finger, so I honestly didn't think that it could fit.

We didn't say anything, just looked for a moment. Then he reached over and took my hand. He placed one hand high on my chest, and his other hand guided mine to his chest. Slowly he moved his hand down to my breasts, while guiding my hand down his chest.

Stopping, he gently cupped both of my breasts, sending tingles through my whole body. I'm pretty sure he could feel how hard my heart was beating, but he didn't react to that at all. Slowly he moved our hands down farther, till he finally reached my pussy. His fingers gently brushed the outside of it and the feeling was electrifying. At that moment, feeling another persons hand on my pussy for the first time, I was completely turned on.

If I had been a braver person, I would have jumped on his and rode him to orgasm right there. Instead, I started to shake. "Are you sure you are ok with this?" I nodded and spread my legs farther apart.

He gently began to rub my pussy lips. At the same time, he guided my hand to his cock, wrapping my hand around it, he helped me to slowly pump his cock. I sat there, my legs spread, his finger exploring my body, my hand pumping his cock.

"Do you want to do more?" I nodded enthusiastically, no longer able to talk at all. He stood, and moved over me, then knelt between my legs. Adjusting my body for a moment, he leaned down and kissed the tender spots around my pussy, then moved back for a moment to admire the view and leaned in to kiss my virgin pussy. The feeling of those lips against my lips was explosive, and I let out a gasp. Then I felt him spread my lips and his tongue start to explore.

His finger joined in, sliding to me while his tongue moved around the outside. Very slowly and gently, he fingered me while his tongue sent waves through my body. I looked down to see and found myself looking into his eyes while I watched his mouth pleasure me. I had masturbated before, and it had felt good, but it was nothing compared to the feeling of my first real orgasm that came surging through me a bit later.

My muscles tenses and my breath turned to gasps as his tongue make me cum. When he lifted his head, we didn't say anything, just looked at each other while I tried to get my heart and breathing under control. Then he clasped my hands and helped me up, so that we were standing, facing each other.

Guiding me slowly to my knees, I realized that his cock was right in front of my face. Like he had done to me, I leaned forward and began to kiss around it, kissing at the base, at his balls, and finally at the tip of his cock, which was quivering in front of me.

Not knowing what to do then, I looked up at him. "Open your mouth." He said. I did, and he moved his cock forward. Placing his hand on the back of my head, he carefully guided it into my mouth. I still wasn't really sure what I was doing, but his hands began to push me forward, and I began to bob on head, taking his cock into my mouth as far as I could (which wasn't very far).

I tried this for a bit, but I knew I wasn't doing a very good job. After a bit, he took his cock out of his mouth, and began to stroke himself off in front of me. I couldn't take my eyes off of his cock, his hand beating it off in front of me.

His breath grew more strained and I knew he was close to finishing, when he shot his cum all over me. Jake was nice about it, he tried to am it away from my face, so only a little bit landed on my cheek.

Most landed on my chest. My young breasts weren't big enough to stop any of the cum, so it ran down my check towards my stomach.


"Open your mouth." Jake said again, and when I did, he pushed the cum on my check into my mouth. "Suck." He said and I sucked the cum of his fingers. That was my first taste of cum. I wasn't really a fan (and I'm still not) but right then if he had wanted me to I would have eaten every drop and begged for more. After that I got up and cleaned myself off on a towel. When I came back into the room he was gently stroking his cock, which had deflated a bit.

"Did you like that?" "I loved it." I said, smiling happily. "Wait, have you ever even kissed a guy?" "No," I said, feeling the embarrassment return.

Jake stood up and walked over to me, taking my hands in his. "Where is your room at?" I lead him to my room. We stood in the door way for a moment, holding hands, not saying anything, then he turned to me, leaning down he kissed me.

Not stopping with the simple kiss, Jake picked up my small body, and held me in his arms, pushing my body against the door frame, while his lips and tongue met mine.

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I wrapped my legs around him, and could feel his cock rubbing the outside of my pussy. At that moment, I wanted nothing more than to feel it slide deep inside me (it didn't, if you have ever tried to have sex like this, it is actually pretty hard and takes some practice). Carrying me over, Jake placed me on the bed, then joined me. We lay next to each other, kissing each other. His hand found mine, and he guided my hand to his cock.

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He wrapped my hand around his cock, and his hand around mine, helping to me to pump his hard cock until I got the rhythm and the pressure down right. We enjoyed each other for a while, just kissing and me jacking him off, then his hands moved over to my leg and he pulled me on top of him. I looked down and could see that he was holding the base of his cock, making it stand up. I knew what I was suppose to do, and moved my now dripping pussy over it. It took a bit of working around, I wasn't really sure what I was doing, but I managed to work his the tip into my wet hole.

He pulled my mouth down and kissed me while I gently worked his cock into my body. It hurt a little, felt a little awkward and invasive, but at the same time, it was exactly what I wanted. I lay on top of him, his cock all the way inside me. We didn't move or grind, just left it in me, while our lips did most of the work.

His hands moved up and began to explore my body. Feeling my back, Moving down to my breasts, Finding my nipples and playing with them, Down to my hips, Grabbing my ass.

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Maybe he pushed me a little, maybe I started it on my own, but I started to grind into him, humping him, moving around until I found out just exactly what I wanted. That orgasm was probably the best in my life.

It is the one that I always remember and think about. It washed over me, making me lose control. My head lay on Jake's shoulder, my breath was out of my control, coming out in moans and gasps.

Feeling my orgasm, Jake wrapped his arms around me holding me while I came on his cock. When I had calmed down, I opened my eyes again and looked at him, we stared at each other, and then he attacked me, kissing me hard, his hand holding the back of my head, forcing me into him. His fingers moved over me again, but this time it was more desperate and wild. They moved down to my hips, and his hands gripped on hard.

Jake began to move my hips, forcing me to grind into him. Then, when this wasn't enough for him, he lifted my small frame up and brought me down, hard, impaling me deep on his cock. He lifted me again, slamming me back down. Slamming again and again and again until he suddenly slammed me down and help my hips tight against him.

For the first time I felt the warm feeling a man filling me with his seed. The feeling almost made me cum again. When he finished filling me, we lay there me still on top of him, his cock still on top of me. I don't know how long we stayed there, I think I feel asleep. I never had sex with Jake again. There wasn't any time when we were alone (my parents leaving me alone like that was pretty rare, they were always watching me).

Then we moved away from that neighborhood and I never saw Jake again. But when I'm horny and can't find a guy, he is the one I think about while I touch myself.