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Brandon – summer fun and making new friends – part 7

5943 words | 8 |4.25
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The summer after me and my brother’s started having sex I found out the world was full of new and amazing opportunities for fun.

At the end of my last story summer was just starting and I was so excited because my dad still worked all day so me and my brothers were home alone for about 10 hours a day. This was so much time that they were able to cum 4 or 5 times each. Jake being an endless well sometimes could go even more through the whole day. By the end of every day I was going to bed full from both ends licking my lips thinking about each time. I wanted this to never end, life couldn’t be better and we still had months before school started again.

Sadly my dream life would not last long. After only a few weeks of add day fucking and sucking my father told Jake that now he had to get a job to pay for his car and gas on his own and Christian was going to start soccer in August so training and practice was starting now before the season and he would be doing that most of the time. I was crushed. My amazing summer of cock and cum was crashing after just a couple weeks. My father had worked out with one of our neighbors in the condo complex we lived in to watch me during the day and he would pay them and help the with some other stuff around their house. They were nice people my father new and they had a son closer to my age. They were happy to have a kid in the house to spend time with him. He was an only child and they worked from home but were glued to their computers during work hours and couldn’t spend much time with him. My father knew this, he didn’t need anyone to babysit me nonstop, just be around and make sure I had lunch and stuff. I wasn’t a baby and could entertain myself. But if I wasn’t home with my brother I couldn’t entertain myself the way I really wanted.

The first day my father dropped me there he was taking christia to a soccer thing on his way in and Jake was job hunting all day. The folks watching me opened the door very nice and smiling and told me to come him. They reassured my father that he was in good hands and would call if anything happened or came up. He left with Christian and they asked if I needed anything or was hungry or had and hobbies. I couldnt tell them my main hobby was sucking my brothers cocks and playing with my asshole. So I said movies and games. They said perfect that’s what Derek liked too. Derek was their son who was also home all day in the summer. He was a little older than me, I was 11 and he was 13 at the time. They introduced us and said “Derek, take Brandon to your room and show him your game and dvd collection.” Derek didn’t say anything just gestures to me and turned. He didn’t seem happy, like I was a burden that he didnt want. I followed and thought, I bet his dvd collection doesn’t have any really good movies.

We got to his room and it was cool for a kids room, he had a TV, a PlayStation, tons of cool posters and figures all over the place. He told me not to play with the figures. They weren’t toys they were collectibles. Then asked if I wanted to watch a movie or something. I said sure and he told me to pick one out. I grabbed one I knew and he put it in and said I could watch it from the floor or his bed. I sat on the bed and he pulled out a large box. He looked at me somewhat interested and asked “do you play magic?”. Confused because I thought he meant magic tricks said no. And his face frowned again and he opened the box on the floor. It was full of cards. I thought like baseball cards but they weren’t. I looked but couldn’t figure out what he was doing, sorting and piling them. He did this the whole time and after a couple movies the door knocked. And his parents came in. “Your brother is hear to take you home. Oh showing Brandon your magic cards? If you like that Derek will be your best friend.” “He doesn’t play” Derek spit back head down. “I’m sure you boys will find something you like together” she said as she guided me out and back to the front door. Jake was there smiling and waiting to take me out of this boring nightmare.

They were only a street over from us so his car was home and we walked back to the house. He asked how it was and I told him it was boring it was and what derek did the while time. I asked why he couldn’t just watch me. He said being an adult sucks and he had to find work like dad. My soul crushed thinking Jake would never be home like dad and I would never get to suck him or ride his thick glorious cock again. He assured me I would find something to do at Derek’s house and then said “right now, I’ve had a rough day so I could use some relaxing” and he winked ant me and smiled. I knew exactly what we were doing and I couldn’t run into the house fast enough. Instead of going downstairs we went straight to Jake’s room. We were home alone so no worries of getting caught or anything. Jake smiled at how eager I was. But it was already after noon and I hadn’t gotten a single load of cum yet. By now I would normally be on at least 4. He pulled his belt off and dropped his pants completely. Keeping his tight boxer briefs on I could see the outline of his thick cock resting on his massive balls. I dropped to my knees and buried my face into his crotch, rubbing my nose and lips up and down the shaft through the soft fabric of his boxers. I could feel the fabric stretching as his cock started to grow. “Oh, I’ve needed this all day” he said. I thought the same exact thing and again felt so close to Jake knowing we both wanted this while we were apart. I grabbed the waistband and pulled down. As soon as the base of his cock was visible I started kissing and licking as I slowly revealed more. Kissing down until I uncovered the tip. When the waistband pulled past the tip it popped up slightly gently hitting me in the face, he wasn’t fully hard yet but enough to make his cock stand out some. I engulfed his head like a hungry snack opening as while as possible to take every bite could down in one gulp. I still couldn’t get more than halfway down. He was just to thick. But I bottomed out to the back of my mouth and wrapped my lips tight and sucked slowly back to the tip. In one stroke his cock was as hard as possible and I could tell he wouldn’t last long. I felt bad for him having to wait all day for this and as much as I wanted to savor every second I wanted to give him fast relief. I wrapped one hand around the shaft under the head and stroked in rhythm to my sucking so my hand would come just over the rim of his head barely touching my lips the whole time while I suck. My other hand gently massaged his massive balls that each one almost completely filled my tiny hands. He couldn’t last any longer. He leaned back and moaned, music to my ears, as he shot a thick load of built up cum right into my mouth. “Thanks, I needed that” he said as he pulled his softening cock out of my mouth. “Now I need to look up more job listings to check out tomorrow.” Sad thinking that tomorrow again would be terrible I just savored the cum in my mouth not swallowing. I went to my room swirling my tongue. Thinking of Jake’s cock and pulled my butt plug out of my drawer. I kept it under some clothes next to the sexy girl clothes Jake bought me. I slid the plug into my mouth covering it with Jake’s hot slippery cum. When I pulled it out the cum was dripping from every inch. I quickly got completely naked and played back on my bed. Legs raised so my knees were almost touching my shoulders I reached down between them and inserted my butt plug into my ass using Jake’s cum and my spit as lube. It was tighter than usual having not had anything in it for so long. But it didn’t hurt, I was so turned on using jakes cum for lube I pushed it on and squirmed on my bed thinking of him. I rubbed my tiny cock and wanted more. I got back up and grabbed the dildo I kept in the drawer. When grabbing it I saw my girl clothes and thought I would look so sexy in them while touching myself. I put on the thick padded bra and stockings that came all the way up my thighs, then the short shirt that went maybe 3 inches past the bottom of my plump bubble butt and a button down top that came down just above my belly button. I usually didn’t wear the wig anymore. I had been growing my hair for a while now, and one it was getting difficult to get it under the wig to wear it, and two it was long enough that when I dressed up it looked like a shirt haircut for a girl.

I admired myself in the mirror for a bit. If I didn’t know who I was I would think I was a girl. I walked downstairs finding Jake reading a news paper for job listings. He glanced up and said “that looks good”. I asked him if he thought I looked like an actual girl. He said for sure and he honestly wouldn’t be able to tell if he saw me anywhere else. I asked if he wanted to play with me as a girl. He said he was supposed to be job hunting, but he could take a quick break. I was so happy I walked to him and wrapped my arms around his neck laying them on his shoulders. His hands went to my hips and around to my ass cheeks grabbing and pulling. His face buried into the padding on my check. Rubbing the two cups on the padded bra as if they were real tits. His hands reached between my cheeks and found the butt plug still in. “Dirty girl” he said as he plucked it from my hole. His finger rubbed around the outside and then pressed in just a bit. We. We’re in the kitchen and had no lube, just the not so slick anymore cum I had used as lube to put the plug in originally. He pulled his finger out and brought it to my face. “Get it nice and wet” he said, and I gobbled up his fingers slobbering all over them. Then they were back between my cheeks and more aggressively probing. One at a time, then two. I could feel him trying to pull his fingers apart in my ass stretching it even more. It felt so good, and we had never done this without lube before. Just my own spot gave it a different feel. Not as slippery but not rough. Just right so I could feel every texture on his hand. Rubbing inside of me. My eyes were closed and I was loving every second. “Turn around and lean over the counter” Jake commanded while standing up and pulling his pants down. I turned around but my waist didn’t even reach the counter so I leaned out so my chest was against it and arched my back so my ass cheeks pointed as high as possible and spread. Jake was quite a bit taller than me so he had to bend his knees and hunch for balance, but I felt his big juicy cock head find my hole and push past just over the head. Wow, this was incredible, it felt totally different than usual. I don’t know if it was because we were just using so!e spit or because we hadn’t done anything all day, just Jake seems to agree. “This is even better without lube.are you okay?” Jake asked. “Ya, it actually feels really good.” I told him. He took that as a go ahead and went deeper. Never before could I feel so clearly every inch as it slid past my hole into me. “Your. Pussy is so tight, I’m gonna cum soon” he blurted out. Hearing that sent me over the edge. He was calling me a girl and it was making him feel so good he couldn’t hold back anymore. I felt he orgasm build in me and as my cock tingled and twitch my asshole clenched in sync gripping Jake tighter. The first jet exploded out of him deep into my ass without warning.I don’t know if it was because of the extra friction or because there wasn’t a layer of lube covering my insides. But when he came it felt hotter than ever before, almost burning. But the extra sensation of it drove me even more wild. My orgasm just seemed to keep going and going as Jake finished inside me his strokes getting slower and shorter.

Fully relieved again Jake pull up his pants and I pulled my skirt back over my ass I found my butt plug on the table where jake put it after pulling it out of my ass and quickly sucked and slobbered all over it before putting it back in my ass to help keep all the hot cum where it belonged. “Ok”, Jake said, “I really need to make another list of places to go tomorrow looking for a job before Dad gets home”. Dad wouldn’t be home with Christian for another 4 hours, but I guess it was a process to sort out jobs. Sad but satisfied I went back to my room. Looking in the mirror again I loved how much I looked like a girl. I thought about going places and being mistaken for a girl and introduced as a girl and it made me happy and horny. I thought no one else in the condos would even recognize me. Not that any of them even knew me to start with, but they wouldn’t think I was a boy if they saw me. I went back downstairs and Jake gave me a bit of a frustrated look because he just told me how busy he was. I asked since he was busy and Dad wouldn’t be home for so long, could I go for a quick walk. It was a safe neighborhood and kids walked around inside the condo complex all the time. “Dressed like that!?” He replied. I said, well I like the outfit and he even said I looked like a girl. I wasn’t going to talk to anyone just a quick walk down the street and back. “Ok. He said, just try not to let anybody see you so it doesn’t get back to Dad and he asks me about it.” So excited, I put on some clean white sneakers and ran to the door. As soon as the door opened my run turned into a slow crawl. I looked out he door and down at my outfit and suddenly went from excited to nervous. Would anyone recognize me? Would I get in trouble? What if everyone at school found out, or worse dad?
Head down I walked slowly down our walkway to the sidewalk looking in every direction for anyone who could see me. I got to the sidewalk and thought now if they see me they won’t know where I came from. And my slow shuffle turned into a normal walk. The further I walked the more comfortable I got and my walk turned into a strut with my head high. At the end of the street were some people outside taking groceries out of their car. I got nervous again and slowed down watching them. They looked up and we locked eyes, I almost jumped out of my skin. They just smiled and waved and kept unloading their car. My strut came back and I couldn’t believe it worked, they didn’t question for a second if I was a girl walking around. I turned around heading back to our house and when I got there I thought that was just a five minute walk to the end of the street. I had so much time I could go a little further. The other end of the street lead to a central road in the condos that went all the way to the back where there was a park. I turned onto that road and kept walking. At the end I got to the park that was really nice. There was a large field where kids would sometimes play soccer or football surrounded by a walking path and on the other side a basketball court and a small building with some bathrooms. Not big just enough for a girl’s side and boys side. In the boys bathroom there was barely enough room for a stall about two urinals. But it was at he very back of the park and kids would sometimes go hide behind it to smoke and stuff. I walked the path. It was the middle of the day and there were only a couple people there jogging and walking dogs. I got nervous as they passed me on the path. But each one either smiled with a nod or wave, or just ignored me completely like I was just another person on the path. This made me so happy. As I walked around I explored some more, walked through the basketball court where no one was playing and to the back where the bathrooms were. I didn’t go inside, it was usually not very clean and pretty hot but I heard voices.

I peeked around the back expecting to see teens sneaking cigarettes or drugs and saw two boys, young teens maybe a grade or two below Christian huddled together facing away. I don’t know what compelled me but I said “high” in a soft voice and they almost jumped out of their skin. Turning around one quickly threw his hand behind his back with what looked like a magazine and and they were silent. I said I was just walking around and heard people so I wanted to see what they were doing. “Nothing!” One blurted out clearly terrified. For some reason their nervousness made me feel more comfortable and bold. I walked toward them asking what they have. And asked politely to let me see too. Not knowing how to react the one with the magazine tool it out from behind his back and sheepishly showed me. It was a porno magazine they had gotten their hands on and were looking at. “Wow, that’s really cool” I said letting them know I wasn’t going to tell on them and hoping they would let me see more. He handed it over dumbfounded and still quiet and scared and let me flip through it. It was actually the first porno magazine I had ever seen. My first exposure to porn was my dad’s DVDs. As I flipped through it was a lot of collage pictures kind of showing the sequence of a sex scene from a movie. The girl would pose then strip then put a cock in her mouth and then her pussy, then a shot of her getting covered in cum on her pussy or face. I asked if they ever jerked off looking at this. One stayed quiet, the other blurted out “sometimes”. I said that was really cool and the quiet one followed suit and said he did too. I then asked “have you ever done this?” Turning to them a page with a girl sucking on a massive beautiful cock while squeezing her tits. “No” one said sheepishly, the other just shook his head. I was completely taken over by some unknown persona brought out by wearing these clothes in public and shockingly asked them “do you wanna try?” Stammering they came back with “uh, what, like with you?” I said ya, it looked like fun. I started this walk terrified someone would recognize me and now I’m asking two strage boys I don’t know if I can suck their dicks. Not how I thought today would turn out. The first one just looked at the other who looking like all the blood had left his face said “ok”. I said great and got down on my knees I told him to pull it out and he shaking pulled his elastic basketball shorts past his penis. He looked back at his buddy and turned slightly away like he was hiding his penis from his friend. I had never actually considered this would bother him because my only experience was with my brothers who would drop their pants in front of each other without a thought. When he was confident his friend couldn’t see he turned back to me looking at his kind of small penis. Smaller than Cristian but still way bigger than me and said “it’s just not hard yet”. I knew that, but I didn’t let them know that I was kind of an expert on this by now. I just said “oh. I can help that” and started licking his cock, immediately it started growing and I took his heading my mouth as it became fully hard. I had no problem sucking his relatively skinny 4 inch penis all the way down without having to try to open my throat. He was shocked into silence as I bobbed up and down on him with my lips tight around him the whole time. I felt like there was so much extra room in my mouth than normal I just started working my tongue around the underside of his cock while I sucked him. This was obviously more than he could handle for his first time. “I’m gonna cum if you don’t stop!” He said loudly. I pulled my mouth off him for a second to say “ssshhh, otherwise we’re gonna get caught. Just cum when ever your ready, I’ll keep sucking”. This greenlight was all he needed. Almost as soon as I started sucking again he started cuming hard into my mouth. He came like christian not huge amounts of thick cum but forceful small spurts that hit the back of my mouth hard and hot. It wasn’t a lot so I swallowed as he came. When he came I kept bobbing but I guess he got very very sensitive because he started shaking so hard his knees buckled a little and I thought he almost fell. “Oh man that was so awesome, you gotta try it man. Can he try too?” “Of course” I said. “I was asking both of you.” He quickly pulled up his shorts and switched places with his friend. “I won’t look dude, your gonna love it”. His friend then repeated the process pulling his shorts down exposing his nervous limp penis that I without hesitation licked and sucked hard. Just like his friend he wasn’t ready for the new sensation he was about to receive but having heard the instructions to his buddy knew already that he could cum when ever and I would keep sucking happily. Their penises were so much alike I couldn’t tell them apart. So I used the same technique I did on the first boy rolling my tongue around the underside of his cock asmi sucked. I don’t think he lasted a minute before shooting his load right onto my tongue. I kept going until he started jerking to from being extra sensitive and he leaned back against the building and breathed for the first time it seemed like since we started. Realizing I didn’t have a watch or anything and that I actually didn’t know how long I had been gone I stood up and quicky started walking. “Thanks guys, I have to go” I said. They not knowing how to react but knowing they wanted more asked if I lived there and when i would come back here. I told them I didn’t live there I was just out for a walk. But I would come back again some time. And quickly walked away back down the road to our street.

Dad’s car wasn’t there, thank God I wouldn’t get caught. I glanced around to see if anyone would see me go inside of our house and closed the door behind me. Jake was still in the kitchen. “Where have you been? You said down the road and back, it’s been over an hour. I was about to go look for you.” I told him I’m sorry and I was fine. It was just such a nice day. So I walked to the park and back. He calmed down and asked if anyone saw me. I told him a couple people, but they all just waved and thought I was a girl. I didn’t tell him about the boys. I didn’t know if he would get upset. He said that was pretty cool that no one noticed. Then commented again about how much I do look like a girl. His look was one of hungry lust and it made me feel like a sexy girl he needed. I said if he needed another break I could be a girl for him and he could use my pussy how ever he wanted. I really didnt know what these clothes were doing to my but I never spoke like that. Just mostly kept quiet and let my brothers do what ever they wanted. But Jake liked it. He said ok, but let’s go upstairs this time.

We took our time this time. Used lube and he played with my ass for a while. He said he liked my skirt and shirt, and wanted me to ride him so he could look at me while we fucked. I was so excited and giddy he said he wanted to look at me while we did it I jumped on top of him immediately. On my knees I guided the tip to my hole and started working it in by rocking on my knees until i had an inch or two in. Then let go with my hand and just used my rocking to slide up and down. In my position it was more forward and back as my crotch was just barely grazing Jakes stomach going up and down his belly button as I rode him slowly. I wanted Jake deeper so I shifted from my knees to the balls of my feet. When my knees are high by my chest my cheeks spread and my asshole points straight down so I can get everything down to the base inside me as I bounce up and down. Gravity helps drive everything as hard as possible and this usually is a position that can make me orgasm. As I started getting lost in the feeling of Jake’s massive cock filling my ass over and over again my tingling penis was dripping precum. Jake said he was going to cum soon. Loving every time I heard those words I said “ok, fill my pussy up.” But his response surprised me. “No”. I was shocked. What did he mean no? Was he going to stop? I was so close I knew that feeling his hot cum shoot inside my as would be what sent me over the edge to orgasm. He then spoke up again. “No, I want to cum in your mouth.” Phew, what a relief. I was disappointed I wouldn’t feel him cum inside me which would certainly have made me orgasm but so happy I would be a le to taste his cum and his cock covered in my ass. I said ok and lifted up until his big heavy cock fell from my ass then fell a little and bobbed, not falling all the way down because he was still so hard. I started to scoot down between his legs and he grabbed me. “No. Turn around, I want you to suck me from here so I can play with your pussy while you suck me”. I loved him calling my ass a pussy. It was so hot being treated like a girl. Even though I was slightly confused I did what he said and let him guide me. He pulled me by the thighs so my knees straddled his chest and my face looked down at his cock. Somewhat different angle but I figured I could do my usual thing but upside down. My mouth found his cock and covered in my ass I started sucking. Soon I felt Jake’s fingers spreading my cheeks and filling my ass. I was imagining his fingers were one of the boys from earlier fucking me from behind while I enjoyed sucking Jakes beautiful enormous cock dripping with precum now. My own cock tingling again with drips of clear liquid rubbing only Jakes chest. He pulled on my hips again pulling my ass closer to his face and me further from his cock. I could still suck it because it was so big but not as far as I could straining my neck to get every inch possible. Then he surprised me again. He lifted my hips pulling me away a bit so my penis wasn’t touching his cheek anymore. I thought it was because he didn’t want me dripping on him. But then pulled me just a little further back and leaning his head down, licked my penis. It shocked me. He had rubbed it before while fucking me until I orgasmed but I’m all the times we had messed around never touched my penis with his mouth. It was small a small boys penis that didn’t even look like one next to Jake’s. A few inches and small glass that didn’t hang at all, just sat close to my body. He licked and mouthed not quite sucking while continuing to finger my ass with two of his thick fingers while I was able to keep his cock in my mouth, but only a couple inches. So I got my balance and used one hand to stroke the length of his shaft while working the head with my mouth, using the other hand to keep steady. Once I got the mechanics worked out I was able to get lost in the feeling and enjoyment again. This was a magic feeling. Jakes strong mouth completely engulfing my small cock and balls. Swirling his tongue around. If this was how I was making him feel I was so happy and felt like the most important person in the world because Jake wanted to return the gesture. I pulled off Jake’s cock for just a second to say “Jake I think I’m going to cum”. He told me he was too and to just keep going. His fingers probing me hit a spot where I couldn’t resist. I pushed back against them to go deeper as my little boy cock tingled and twitched and spurt a small clear load into my brother’s mouth. He didn’t seem to mind but as soon as I did he stopped worrying about my end forced me further back down for more of his cock. I was happy to oblige and I new it was my turn for a sweet creamy reward. When his cock hit the back of my mouth he wrapped one arm around my back pinning my chest tight to his stomach. Then held his other hand form to the back of my head. He didnt push it down just held it steady in place. Then his hips started rocking. Pushing off his ankles as he rocked forward he preshed his coc harder and deeper into my mouth forcing my throat open. I knew it would make it easier if I swallowed as he did this. And as soon as I did I could feel his head pushing past my mouth and into my throat. I had to time my breath as I couldn’t breath when he was in my throat. But after a few seconds we had a rhythm. He held me so tight while fucking my mouth like a pussy. It was so hot I didn’t realise when he had stopped pulling all the way out of my throat and kept fucking inside it. I hadn’t taken a breath for almost 20 seconds and I wasn’t panicking or feeling out of breath yet. He pushed deeper and deeper. It seemed like once it went past a certain point the rest was easy. He said “almost, I’m gonna cum”. So I kept holding my breath as long as it took for him to finish. This was new so I’m sure it felt great and I wasn’t going to ruin it for him by stopping for air if I could help it. He was using long hard thrusts now in and out of my throat so deep I thought he would hit my stomach. Then he moaned “oh ya”, and I felt something wonderful. My eyes were closed and I felt his balls touch my nose and the top of his pubic area hit my lower lip. I had every inch of Jake in my mouth for the first time ever. I didn’t think it was possible. He moans and held my head tight against him as he throbbed into my throat. I couldn’t taste it, but I felt the hot spurts and his cock pulsing like it got a little thicker for a moment each time he shot a jet of cum deep into my throat. I swallowed as I pulled off all of it going straight down never touching my tongue. I gasped as his cock cleared my lips. I don’t think I took a breath for over a minute. He apologized as his body went limp. I told him it was ok and I really liked it.

I was happy that even though my brothers weren’t around as much to give me endless loads all day, jake and I had some time to try new fun things for more intense sex. But couldn’t stop thinking what about those boys at the park. I bet there are even more boys who would like to try that stuff too. If I couldn’t get the quality I wanted from Jake maybe I could make up for it in quantity.

If you like my story please comment and let me know. It encourages me to keep writing and is a turn on to know people like and are possibly getting off to thinking about me. In the next part I figure out if I can’t get enough time with my brothers anymore I’ll find a way to get the reward I need from anywhere or anyone.

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8 Comments

  • Reply Tease me ID:pvli0pxic

    That is so hot. I knew jake would go farther. I can’t wait to read more

    • Brandon95 ID:21cogc2t0d

      Thank you. Next one is coming soon. I write when I can and remembering all this to write the story is getting me insanely horny knowing I’m telling others who are reading and thinking of me hopefully while they are cuming.

  • Reply Big daddy ID:1egyf0c4k89m

    You make me come every night keep going

    • Brandon95 ID:21cogc2t0d

      Thank you daddy. I like to think about guys jerking off to me and just wish I could be there to receive it all

  • Reply L ID:1doeevf9cbro

    Do more with your dad

    • Tease me ID:pvli0pxic

      Yeah, get the whole family involved

  • Reply More please. ID:1d8bo5gryutx

    Love that Jake is getting more into it.

    • Brandon95 ID:21cogc2t0d

      I liked it to. It helped me realize how much I like being treated like a girl.