The Whole Weekend

It was Friday night just after the football game. I had permission from my parents to stay the night with my best friend Jason. As usual after every football game we would end up at his house or mine for a sleepover. We would spend the night watching porn and cutting up. This was not an unusual night or so I thought.
We got to Jason’s house around 11 pm to find his parents still up waiting on us. This was normal and we quickly found the remote and tuned in to the news to catch up on score from the other games from around the area. This was just a front as we were really just biding time till his parent went to bed for the night. They had an in ground pool in the back yard and we had a routine of waiting until everyone was in bed then slipping out for a cool relaxing night swim in the pool. 20 minutes into the show his parent retired to their bedroom for some hot steamy action of their own I’m sure.
We gave them another 10 minutes to be sure they wouldn’t come out again and we slipped out to the back yard and quietly got into the pool. We would swim for a while then reassess the situation. Confident no one would come out it was off with the swim trunks. Jason was around 5 foot 4 inches tall and kind of stocky with a modest 5 inch dick. I was 6 foot with a 6 and a half inch cock. We had seen each other naked many times so our nakedness was nothing new to either of us.
My normal routine when we would get in the pool that late was to retreat to the deep end of the pool which was around 8 feet deep and bob from the top to the bottom blowing out all the air in my longs and standing on the bottom for as long as I could. I’d have my eyes closed because this was so relaxing to me. It was kind of my way to unwind. Jason would just swim around or sit on the steps and relax.
Very relaxed and into my routine, I was standing on the bottom and could feel Jason swimming around me. This was normal so I never opened my eyes. I was about 10 seconds away from heading back to the top for my next breath and decided to open my eyes to see where Jason was and boy did I get the shock of my life. Opening my eye I find Jason floating about 4 inches away from me. My feet on the bottom of an 8 foot pool and his head above water and him treading water put his cock right in my face about 4 inches away. Shocked I just stood there and looked. Even more shocking was the fact that I was slowly moving closer to his cock and my mouth was slowly opening. Then it hit me I needed air so slowly I ascended with my eyes closed not wanting him to realize I knew he was there and promptly went back to the bottom and resumed where I left off. To my dismay he turns and swims away. I stood there on the bottom shocked and upset at the way I was feeling. I reached down to find a raging hard on of my own. I close my eyes and resumed my routine.
Dishearten I bobbed a few more times and was about to head to the shallow end and decided to open my eyes again in hopes that he would be there again. When I opened my eyes to my delight there it was again right in front of me. Again I needed air. I was pissed. I needed gills or something. I had never been this turned on in my life and couldn’t figure out why. Reluctantly I closed my eyes and rose to the surface and quickly went back to the bottom only this time I held my breath. I got to the bottom open my mouth and began my descent towards his cock only to realize I was beginning to float. Panicking I reached out and grabbed his leg to keep me on the bottom. This caused me to move forward a lot faster than I had intended. I felt the head of his cock pass my lips. Instinctively I closed my mouth around his cock. Boy was that a mistake. He began to viciously fuck my in the mouth. I was under water, my head spinning, mind running wild and Jason fucking the shit out of my mouth. Then it hit me, hey you need air.
I pushed away and made my way to the surface. I came up beside him and nonchalantly told him I was headed to the shallow end to relax on the steps. Swimming the short distance my mind was racing and I began to shake. I don’t know if it was that I was cold or I was in shock. Jason came up beside me and asked If I was cold and all I could do was nod my head yes. He moved around behind me and started to slid up behind me. His warmth sent my head spinning and then I felt it. His cock had landed right between my ass cheeks and he kept moving up until I felt the head of his cock land at the entrance of my ass. I didn’t move. I couldn’t speak. I guess that was all the invitation that Jason needed. I felt his cock enter my ass with a sharp pain. I felt jolt of pain and pleasure shoot through me. It was very painful to start with but I managed to relax and Jason quickly fell into a very fast rhythm and he began to fuck me as deep as he could. As his pace quickened even more I noticed the sloshing of the water around the step start to get really loud. I didn’t know what to say I surely didn’t want anyone to see or know what was going on but I didn’t want it to stop either. Finally I got the nerve to say something and Jason buried his cock deeper than ever before and collapsed on top of me. It was then that I realized he had just planted a seed deep in me.
After a minute or two of savoring the feeling we managed to get out of the pool and make our way to his bedroom. We quickly hopped into bed and snuggled up close under the covers. Before long I noticed that his member was at attention again. I made my way under the covers and grabbed my new found friend and greeted him with a slow wet kiss. This didn’t last long as Jason was eager to fill my mouth with more of his seed. I opened my lips ever so slightly and grabbed his head with my lips. Can u say impatient? Yep that’s right violent thrashing followed and I struggled to keep up. I managed to grab his hips and slow him to a manageable rhythm. He was getting better with his stamina as he managed to last all of 5 minutes this time. I worked his shaft for a couple more minutes just practicing and we both decided we needed to get some rest so I retired by his side for a little shut eye.
Saturday morning came way too soon. As I awoke I realized that Jason and I had slept in that morning which wasn’t anything new. He only has a twin bed so needless to say we were quite close. Then I realized that neither of us had put on any clothes after our swim. I was awake but hadn’t opened my eyes yet and kind of snuck a peek to see if Jason was up yet. Nope not yet. He still seemed to be snoozing right along. Then he starts to flop around and I was sure he was still asleep. When he finished his flopping he came to rest with him snuggled up behind me. Me still thinking he was still sleeping till I felt his boner poking me in the ass. I though huh what a coincidence. Wrong again, he slowly slid forward till he had reached the entrance to my love hole. Ever so slowly he started to push forward trying to get inside me but there was absolutely no lubricant so we were going nowhere fast.
I thought for a second while Jason kept trying to enter me. Quickly I got up slid on some shorts and made my way to the bathroom. I quickly relieved myself which is hard to do when your member is standing at attention. As I finished I found what I was looking for. Right above the toilet on a shelf was a tube of lube. I grabbed a glob and sort of rubbed it in so it wouldn’t stick to the shorts but would stay till I could get back to him. I walked into the room and he quickly threw the sheet back and patted the bed beside him. I almost broke my neck trying to get back into the bed. As I did he placed his hand on the top of my head and started to push me down under the sheet. I played the resistance game but It lasted all of about 3 seconds. I couldn’t wait to get face to face with his fabulous cock.
Arriving at my destination I began to lick slowly from the bottom to the head of his 5 inch cock. As I did this several times I thought to myself what a tease you have become all the sudden. When I finally wrapped my lips around the head he immediately began to thrust with reckless abandon. Surprisingly I guess because of the position we were in I found myself gagging on his cock. When he should hear me gag he would back out a little to let me regain myself then burry it again causing me to gag again. Finally I managed to get to where he couldn’t gag me and he quickly settled into a fast rhythm. It didn’t take but a minute when he exploded in my mouth. I was in heaven but a little upset as his member began to go limp on me. I was thinking to myself, (oh hell no I aint done with that thing yet.) Well apparently I wasn’t just thinking it because he quickly whispered “well get it back up again and we will go for round 2.
That was all it took for me to attack his cock like a beaver on an oak tree. It took me a while but Loved all 15 minutes of it. Once I had his cock at attention again I stayed under the covers and made my way up his body until I could mount him. By then I had pre-cum leaking out of me like a fountain. As I laid my mail snail track up his abs I felt his cock slide between my cheeks. I reached down to help him aim. I rubbed my whole a couple times and started to slowly sit on his cock but he was having none of that. He trust up violently burring his cock to the hilt in my ass. Pain like I had never felt shot through my ass and I clinched down on him with everything I had. He asked with a sheepish grin did it hurt. After I caught my breath I explained to him that when we start he needs to be a little gentler because that shit hurt. As I sat there with him buried in me I began to relax. I slowly started to bounce ever so slightly until I felt the pain turn to pleasure. He asked if it was ok to speed up yet and I said no. Not because it hurt now but because I wanted it to last longer than 30 seconds.
We carried on like that for a few minutes and he said ok it’s time for me to take over. Lie on your back and hand me your ankles. I done as he asked and he assumed this position between my legs. He found his mark and slowly entered me. He wasn’t brutal this time but he did burry himself all the way in. He stays there only a second before pulling all the way out. He repeated this for several minutes and then asked how does that feel. I was almost speechless. The sensations, the feeling, the exotic nature of what was going on. Lost in the moment he buried himself all the way and leaned forward with the bend of my legs over his shoulders and began to fuck me slow and deep as he looked me in the eyes. He laced his arms undermine and grabbed the back of my shoulders and started to speed up. As his pace quickened d I could tell he was about to blow. As he began to convulse on top of me I reached back and grabbed him holding him deep inside me. I began to squeeze and release his cock with my asshole. This must have sent him into sensory overload because he almost passed out on top of me.
As he began to relax and move off of me I held tight. I didn’t want him to move. That was until he spoke. He said ok now it’s my turn. I released him and my legs fell off his shoulders to the bed. It took all of about 2 seconds for him to mount me. I had been with a few girls by now but I had never felt or experience what I was about to.
He reached back and aided with my aim as I found my mark. Pre-cum now flowing again like never before there was no need to use any addition lube. He slowly began to slide down and I felt the head pop into his ass. He grimiest with pain and stopped. I thought ha-ha this is my chance. I grabbed his hips and lunged into him burring my 6 inches to the hilt. He screamed out loud with pain. Boy I was not ready for that. Quickly he dismounted and we shuffled to get dressed. We just knew there would be a knock on the door any second. Sure enough knock- knock everything ok in there came a voice from the other side of the door. Yes maam I answered as Jason was still clinching his rear in pain. What happened she asked? Jason hit his toe on the edge of the bed he is ok though. Boy was that close.
Well now that everyone was up through the rest of the house I excused myself to the bathroom to finish off what we had started that morning I surely didn’t want that pain later on so off I went to finish up. When I returned to the room Jason had made the bed and gotten dressed. I asked if he was ok and he said hey why don’t we see if we can camp out tonight in the woods close to the house. I thought oh hell yeah so off I ran to the house to get permission for the camping trip from the parents.
I got to the house around noon and went right to my room and locked the door. We didn’t have air conditioning so the window was open with a box fan in the window. I had the curtains pulled as best I could with the fan going and stripped down to nothing. Almost immediately my little friend was at attention as if it knew we were about to start our exploration of our new found feelings. Looking around my room I started looking for something that I could use to simulate Jason being with me. I found lots of things that could potentially be a match like a small coke bottle which I deemed too big, an aftershave bottle that was small but shaped weird. A travel sized shampoo bottle and finally a hair brush with an oval shaped handle.
I started with the shampoo bottle which was the smallest and found out quickly that it needed to be rinsed off. I got it in rather easily but apparently there was some on the outside because it burned like hell and I had to quickly take it out. That didn’t help much cause I was still on fire. I quickly I put on some shorts and ran across the hall to the bathroom and grabbed a rag trying to get some relief. I took me about 10 minutes and the burning ended. Boy I could now say lesson learned with that stuff. I went back to the room with a wet rag having learned from my mistake to wash off the remainder of my new toys.
I washed off everything carefully and tested it by licking them for taste to make for sure I was ok to continue. Now it was time for the aftershave bottle. I had just licked it so it slid in nicely. The odd curves and the cold glass really got my head to spinning. I moved it in and out slowly savoring the feeling of the smooth edges sliding past my hole. Soon the class became warm so that sensation was lost so I decided to move on. I grabbed the hair brush and licked it as I was constantly learning this new way of life and applying what I learned to each new page in this endeavor. The hair brush handle moved into me with ease and the feeling of the handle growing as I slid it into me was awesome. I slid it as far as it would go until I felt the bristles brushing against my ass cheeks and the skin between my hole and my sack. Man what a feeling that was. I moved it in and out several times and looked down at my rod to see that my head was oozing with pre-cum. I took some on my finger and brought it up for a taste. This was really starting to get me excited. I grabbed my shaft and began to stroke. It was kind of hard to do both at the same time. Push the brush and stroke my rod but I managed for a few minutes.
Finally I grabbed the small coke bottle and sat it on the floor and tried to squat on it. Well given the fact it was only about 7 inches tall I wouldn’t reach it target. I quickly looked around my room to find things that I could use to raise it up off the floor. Finding a couple of paperback books I felt would do the trick I quickly got them stacked capped it with the bottle and assumed my position above my little love pyramid. I began to descent on the bottle. When It made contact with my hole, I began to stroke my meat as if my life depended on it. I couldn’t quite manage to get the first bulge to go into me but I never slowed my assault on my meat. It didn’t take but a few seconds for me to begin shooting stream after stream of seed across my bedroom floor. What a feeling this was. I collapsed onto my bed and lay there to regain myself. My legs were shaking uncontrollable so I couldn’t really stand proper so I just lay there. After about 10 minutes I was able to get up and get dressed. I made my way out where the rest of my family was watching college football in the living room.
I sat with everyone and watched the remainder of the game that was on and cornered my mom in the kitchen. I asked permission for the campout that Jason and I had thrown together and to my delight she said yes. I got a chub right then. I call Jason to finalize the plans and then it was a waiting game till 6 pm which is when my mom said I could leave.
At 6 I made my way to Jason’s house to begin our trip. When I got there they had another football game on the TV and I was asked to sit and watch the remainder of that game which I did. The whole time I sat there watching the game, all I could think about were the events to come. What did he have in mind? Where was it going to start? How far was it going to go, and how long would he last this time. As the game came to a close Jason and I finished gathering out things and headed off to the woods. By this time it was about 8 p.m. and dark. It was a short trip to the end of the road that he lived on and we were in the woods. Just out of sight of houses on the end of the road Jason said hey why don’t we shed the clothes and spend the rest of the night that way. I couldn’t get my clothes off fast enough. A second later I was stark naked and watching Jason finish undressing. Of course the both of us were rock hard sporting woods as we walked.
The end of the neighborhood was the start of endless miles of trail that we had made from the many years of go carts, 3 wheelers, 4 wheelers, and motor cycles that we had over the years. After making our way about a mile into the woods we found a suitable spot to make camp. We brought 2 sleeping bags and 4 pillows and a few morsels of food. Quickly we had camp established and I asked Jason so what’s next. He smiles at me and pointed his rod at me and said you want some more of this. I didn’t say a word but quickly made my way over to my new favorite part of Jason’s body. I took him into my mouth and began to move up and down his shaft slowly. I paused at the top and flicked the head with my tong making circles along with very short strokes not moving but about ½ and inch up and down. I knew instantly that he liked this because of the moans that were coming from him and getting louder. Oh god man where did you learn how to do that he asked. I paused for a second to reply well do ya like it. He said hell yeah why did you stop. So I resumed my little ritual I had started. This didn’t last long before Jason quickly moved to his knees and grabbed the back of my head and began to thrust into my open eager mouth.
He managed this pace for about 2 minutes before burring his cock in my mouth and unloading the largest load I have ever seen him release. I struggled to keep up with the flow as shot after shot spewed from his still throbbing member. He held there for a minute or two before falling to his ass with a big release of breath. Shit that was good. Give me a minute and ill return the favor. I lay down on my back and looked up at the stars. Happy with my performance and with mind racing as I tried to prepare for what came next.
Jason suggested we may need a fire before the night ended so he and I quickly scrambled to gather some wood for a fire. 10 minutes later we had a stockpile of wood and a fire blazing a few feet away from where our sleeping bag lay. I returned to my position on my back still silent and waiting. I was admiring the stars when I felt a warm ring around the head of my cock. I looked down to see Jason had all but inhaled me. He struggles to take all of my 6 inches as he gagged but continued. Amazing is all that I could think as he feverishly tried to finish the job. He had made his way between my legs as he continues to suck me. He paused for a second and I was about to protest when he resumed his assault on my cock. I second later I felt the tip of his index finger find its way to the entrance of my asshole. He pushed in slowly as he quickened his pace on my shaft. This was too much. I felt myself begin to swell as he sped up again and just as he sped up, he stopped. I opened my eyes and he was mounting me. Disappointed that he didn’t finish, how could I protest when he was brave enough to mount what had caused him so much pain only a few hours earlier.
As I felt the head hit its mark he began to move down slowly. He paused briefly and looked me in the eye and said don’t hurt me this time. I agreed and said he could control the pace I would just lay there and let him have his way. He resumed his decent and I felt the head move past his tight warm entrance. His face showed his discomfort and I reached up and grabbed his chest. I started tweaking his nipples and told him to pause for a second to get used to the size. He did and slowly slid down a little more. This continued until he ever so slowly started a short slow rhythm. Before I knew it he was able to take my entire length inside him. He began to pick up the pace and I knew he was experiencing what I had the night before in the pool as he started to moan loudly. I could feel myself beginning to swell as I was about to erupt. I couldn’t hold it anymore I grabbed his hips to stop his movement as I plunged into him as far as I could and held him there as I unloaded what felt like a gallon of cum into his man pussy.
He sat there for a bit feeling things that he and I neither one had felt before. Finally he got up and moved over closer to the fire sitting Indian style. We made small talk and ate a bit to regain our strength as we would need it. The rest of the night went by way to fast as we managed to entangle ourselves in every position we could think of for the remainder of the night. After what seemed like only an hour or so I was sucking on his manhood for what must have been like the 15th time that night when I noticed the sky started to lighten. I finished my work and told him that if we were going to stay the way we were we needed to move deeper into the woods so we wouldn’t be discovered by passersby on the trails that were all around us. We quickly gathered our belongings and made our way down to a bottom where a creek ran by. This would be our resting spot for the next 5 or 6 hours as we needed to recharge before going home. This was the most exciting weekend of my life I believe and thanks to Jason there have been many more since then.

More to come as I was only 14 when this happened, I am now 38 and we have had several encounters since then. Comment if you will.