Brandon - chapter 1 My first orgasm

Lonely boy learns about masterbation from an older friend on the internet.

When I was 14 may family moved away from the city and to a small more rural town. Very few people that were more spread out. Small farms scattered around and rich people who owned horses and boats. We moved halfway through the school year right after Christmas and it was tough being in a unfamiliar place and not knowing anyone. Even at my age I was small, and underdeveloped physically and mentally, so I felt 3 or 4 years younger than I was (careful of policy restrictions). And in this new town there wasn't a lot to do, so I found myself inside playing with the new computer we had gotten right before we moved. It was the early 2000s so computers weren't great and it was just becoming more common for every house to have them. My folks worked pretty late after I got out of school usually wouldn't get home for 3 sometimes 4 hours after me. My sister who was 17 would often stay at least that late at school for cheerleading and other activities, even if she did come home she would immediately leave with her friends. But it was a nice safe town so it wasn't uncommon for kids to be home for a few hours alone before their parents got home.

As you can imagine a young bored boy alone with a new computer for hours, I soon found a way to occupy myself. It didn't take long for me to discover chat rooms to talk to people and many of them talked about porn. Up to this point in my life I had never actually seen porn, but I knew what it was. I would talk about it though like I had and knew all about it and sex. It was entertaining and made me feel more mature. It also made me excited in ways I didn't fully understand or know what to do about. Some of the guys would mention their favorite porn sites, but when I tried to go to them they all required a credit card. But I would look at the main pages and admire the large breasted women and muscular men with enormous cocks they used to advertise. It did make me feel a little insecure, my penis being very small at he time and these men having cocks that looked like my forearm. I wondered if mine would possibly grow that big as an adult but also couldn't stop just staring at those massive cocks and balls with envy but not that I wanted mine to look like theirs, I just wanted to see one for real.

One day I found a chat room and started talking to a man who asked what sites I like. In a moment of honesty I told him I didnt have a credit card so I couldn't get on them. He told me about a program I could install to allow me to download all kinds of movies and shows for free. I didn't believe him. He said he would tell me exactly how to do it, if I would download a few names he suggests and then tell him what i think about them. Of course I agreed and he started sending the step by step instructions.

After about a hour or more of downloading (internet speeds weren't exactly fast back then) I was ready and started searching for the recommendations he made. Some were large and would take too long, a couple were short and I had downloaded in several minutes. The first one I was able to watch was a beautiful woman with large breast on her knees sucking a mans cock. It was incredible. She was so beautiful and his cock was so big she could hold it with both hands and the head would still stick out enough for her to suck. It must have just been the last minute or two of a porn movie someone clipped because she was sucking vigorously then the man pulled back suddenly and grabbed his cock holding it just in front of her face as he erupted all over and into her face and open mouth. My legs were shaking I was so excited. My body was tingling and I could feel my own penis getting hard. This wasn't new, but I still at this point hadn't ever masturbated or orgasmed. I found the chat room and guy again and thanked him for the instructions and told him about the one video I was able to watch. He asked if I liked it and asked if I came watching it. I told him I loved it, but in a other moment of honesty I told him I didnt cum. That I really wasn't sure how to do that yet. He said it was ok. And sent me another video recommendation that he said would help me out.

The video names didn't really correlate to what the video was so I typed in the gibberish he sent me and just downloaded and played. This one was a little longer maybe 10 minutes and it was two guys. Young muscular men in their twenties probably. They were sitting across from each other on an L shaped couch in their briefs rubbing their large cocks through their underwear. I could see their bulges getting bigger and I mimicked their rubbing in myself through my own pants. My cock got hard just like theirs only not as massive. They each pulled down the elastic waist of their briefs and lifted out equally impressive cocks and huge balls that looked like grapefruits compared to mine. I watched them grab at the base and stroke up and down and copied their movements while my whole body shook with excitement. The tingle grew. One of the men spit into his hand and rubbed it all over the tip of his cock. I could tell he was squeezing harder and the spit was to slick things up. I tried but my mouth was actually very dry because my mouth was open this whole time watching. So I closed my mouth and worked up some saliva. Spit it into my hand and went back to my rock hard 4 inch cock. Then men moaned and groaned as they massaged their balls stroking their cocks across from each other, looking at each other the whole time. My slick hand now glided over the head of my penis and sent waves through my body. One man grunted and thick white streaks of cum shot from the head of his cock straight up and fell back onto his hand and stomach. While he was still moaning and stroking out the last drop from his throbbing cock the other man stood up and took a few steps right at him standing directly in front of and over him between his wide spread legs and shot his own load right onto the other man across his whole body. He shot 3 or 4 thick ropes of cum landing all over his chest down to the man's cock he was still stroking. The guy still sitting took his hand and rubbed it across his chest scooping up the other man's cum and brought it back to his cock using the cum as lube. This sent me over the edge and my body shivered as I felt my first orgasm erupt from my body. It wasn't a gushing fire hose like those men more like a small squirt gun, but the feeling was intense and kept going long after I finished cumming. I kept slowly tugging small cock now very slippery covered in my young cum as the scene on the screen faded out.

I couldn't believe how good I felt, and how aroused I still was. I also couldn't wait to talk to the guy in the chat room again and thank him and get more videos he helps me download.

After I washed up a bit and changed my pants I got back online to chat with my new friend. I told him I came for the first time to that video and it really helped me figure out how to do it. He asked how I liked the ending, I told him that's when I came and it was amazing. That seemed to make him happy and he said he could send me more with even more ideas of how I could make myself feel good like that. I was so excited I couldn't believe there were even more ways to feel like that. He asked if I used lube and I told him about the spit. He said that works but I should go to the pharmacy and get some baby oil when I get a chance because it's better and has more uses.

I did exactly that the next day after school and ran home to download the next video he recommended. This one had a title that confused me. Tai Ladyboys. I started the download and it was a long one. It was going to take about an hour so I started downloading it and then opened the last one with the two guys. He was right. The baby oil felt so much better. It was more slippery and lasted. It did kind of get everywhere and leave a slick feeling on every part of skin it touched but I would have plenty of time to wash up before my folks got home. I started stroking just like the guys but with my new oil and immediately knew I wasn't going to last the whole video. I had to let go and start again after a minute rubbing my now super slippery balls while I let my penis rest. I saw a small pea sized drop of white emerge from the tip of my penis as I did this over and over. I wiped it up with my finger and looked closer. Touching my thumb and index finger watching it stick and rubbing them together feeling it. I was mesmerized by it. So much so I didn't notice the video end. Instead of restarting. I went to the other video of the woman sucking the mans giant cock. I started again, definitely wouldn't last long, but this was a short video. I started stroking again and immediately felt the climax coming. I tried just holding my cock with my hand wrapped around the head not stroking but the feeling was already pushing me over the edge. I came but not the eruption like before just a steady dribble out the tip as I shuttered feeling the orgasm was over me, cum running across my fingers wrapped around my cock. As I looked up the video was finishing with the woman getting plastered across the face again, mouth open smiling and licking her lips. Wow, I looked at her and down at my hard little cock and cum covered hand and without thinking I brought my hand to my face and licked my fingers. Just the tip of my tongue at first, but as soon as I tasted the sweetness and felt the slick juice on my lips I took longer laps with my whole tongue and sucked my fingers clean. Wringing my hand up my cock trying to scoop up every last drop I licked my fingers clean again and sat back breathing heavy lost I my mind of wanting to be that beautiful girl getting cum shot right into mouth. No wonder she looked so happy, it was the most exciting thing I could think of.

Little did I know this day would probably mark the day I developed an isasuable craving that I could never satisfy from then on. If you guys like this story please comment and tell me about it and I will keep telling it. My fun keeps escalating as I learn more and a fun neighbor boy moves in next door.