Experimentation with Bro

by Tofu This story starts out in 1982 when I was 14 and my brother was 16, and we both had an appetite for jackin’ off. This appetite was actually encouraged in our house by both my mother and father. They didn’t actually tell us that we should start touching our genitals, but they did allow and participate in a relaxed atmosphere directed at anything sexual. Our house wasn’t dysfunctional by any means; we just had our eyes opened to the real world at a younger age than most kids do. As an example, my eldest brother, who was 21 at the time, once told me and I’m sure my brother too, that he had walked in on dad as he was in the middle of pleasuring himself. According to the story he was shocked and embarrassed, and apologized as he turned around and started to leave. But to his surprise dad asked his to come back and have a talk. And when he did they talked for about an hour about what he saw, how this affected him and dad even gave my bro some pointers on the best way to get off. What a shock, but that was just the way our house was set up. So when my 16-year-old brother, Phillip started talking to me a lot about masturbation and how he was experimenting it didn’t surprise me. Phil and I had always been aware of each other’s bodies, we did share a bedroom after all, and as younger boys of about the same age we grew up together finding out about our bodies and sexuality. My bro was the first to introduce me to playing guitar on a limp dick, and was the first to explain the rules of doctor. Our curiosity for our own bodies then turned into curiosity for other peoples. I remember the first time I saw a dirty magazine and my brother and I lusted at it for hours on end in a public bathroom. We definitely were attracted to women and had no consideration of being gay, but when Phil started openly masturbating in the bedroom in front of me I was unquestionably turned on. It would vary from Phil just lazily whipping around his dick around while watching TV to having him vigorously beat his cock until he came on his face. He was unmistakably experimenting much more than I was and shortly after I turned 14 I decided not to stay on the sidelines. Up until that point, I would jack-off in the shower of when nobody else was home and I would do it in a way that resembled a small animal forging for food, and doing it in a hurry. One day after school while our parents where still on their way home, I decided to ask Phil what ejaculate tasted like, hoping this would spark a conversation about masturbation. He explained and just as I’d hoped we started talking about how much fun it was to play with ourselves. He eventually asked me why I never did it in front of him, since there was obviously an understanding between us. I explained that I thought I wasn’t doing I correctly and I wanted to "practice" on my own. This conversation carried on for a while before Phil eventually convinced me to take off my clothes and let him show me some stuff. I took off my clothes and stood there in the middle of the room naked watching as my brother closed the blinds and turned off the TV. I didn’t know why but I was nervous. I couldn’t stop thinking as Phil went over to his closet and dug deep to bring out a recent issue of Penthouse. He showed me a picture of a blonde slut who was deeply fingering herself. I quickly saw why he did this. My little pecker quickly became a throbbing woody. Phil tossed the magazine on to the bed and still fully clothed proceeded to ask me "why do you think your not doing it properly". To which I explained that even when I tried really hard I wasn’t able to get a lot of cum out. It always felt as though I had more left over that was still inside. He told me to sit down on the bed and while looking at the magazine, start stroking. And I did. While I did he left for a bit. This allowed me to forget about the unusual circumstances and concentrate on the lovely blonde on page 36. When Phil returned I was enjoying myself and was really spread out along the bed. What I didn’t notice was that he’d gone to mom and dad’s room and brought back some K-Y jelly. With my head tilted back and unaware of my surroundings Phil opened the tube and squirted it on my tummy. I was startled, but as soon as I realized what it was I thanked my bro for the unexpected surprise. No more than a minute later, I looked took a break from my deep concentration and looked over at Phil. He was now also completely naked, but I could care less. All of a sudden I felt a warm tug at my bulging five-inch cock. It was my brother pulling some lube off me and placing it on his own thing. We masturbated together on the same bed for what seemed like a long while, but in reality was probably only a minute or so. Phil finally came, and in the process came on me, although I didn’t mind. I then continued to stoke as Phil wiped up all his come. All of a sudden I heard the voice of my mother calling me and my brother for dinner. She had gotten home and cooked dinner without us noticing. I had to stop. Phillip left for dinner and I follow shortly afterwards. I still had my brothers cum, now dried on my chest and just the idea that it was there was driving me crazy. At the table were Phil, mom, dad and myself, with my sister who is younger than I am off at some lessons. We were having a nice dinner with nothing out of the ordinary happening, when all of a sudden my brother told my mother that he had borrowed her lubricant. I was shocked. What was he doing, didn’t he see that see would figure everything out. But to my surprise my mother just said, "be sure to put it back". What the fuck was going on. Before I had the chance to kick my brother my dad spoke, saying something like "did you boys clean up after yourselves". I was like, holly shit. I knew that my family was liberal when it came to sexual exploration, but id never thought that they endorse me and my brother masturbating together or more, that’s if they figured it out. After dinner my brother left for the basketball game with my dad and I went off finish my fun. After then I went to bed. The next morning I was woken up by Phil, who had just been in the pool and was still wet. He was asking me if id seen his snorkels or something like that. He didn’t seem to give any thought about what had happened yesterday. He left and after I woke up properly I went down to talk about what had happened yesterday with him. I went outside, where my brother and dad where skinny-dipping together in the pool, which was a fairly common practice in the summer. I quickly joined them, taking my boxers off and enjoying the cool touch of the water. We swam, with nothing of interest to this story happening until after a bit. My father had left the pool shortly after I had joined the group, but stayed on the deck getting some sun. But as soon as my dad went into the kitchen, Phil swam over and said "so did you ever finish yesterday". That started us talking about going back upstairs to finish what we had started. I noticed that my little pecker wasn’t limp anymore. We got out of the pool and while I reached for my shorts to cover my excitement, Phil just strutted through the kitchen, passed my father and ran up the stairs. When I got to our bedroom Phil was pulling out his magazine from the closet and closing the window. I dropped my shorts to the floor and sat down on Phil’s bed. Phil wasn’t quite yet to start so he ran to my parent’s room and brought back some jelly. We ended up sitting on his bed together leaning on the wall, with the smut mag in between us. It was quite enjoyable sitting with my brother jacking off in tandem. I was getting more fun out of this than I had ever before. I was expecting that in a few minutes we would squirt, clean up and then go back downstairs to enjoy the rest of the day, but that wasn’t the case. Out of nowhere I felt a warm hand reach over and grab, quite forcefully my shaft. Phil had decided to kick it up a notch by grabbing my dick for me. I wasn’t going to tell him otherwise because it was so much fun. He was going fast at first and then he slowed down, letting me catch up. I was leaking precum like there was no tomorrow, and in the process making quite a mess of my brother’s hand. After a few minutes of enjoying myself like never before, Phil grabbed my hand and escorted it over to his rock hard cock. It hadn’t crossed my mind to help him out like he was helping me, but I didn’t dislike the idea either. To be honest I didn’t have the energy to fully play with him like he was for me so I settled for just palming his head. We carried on as we were for close to fifteen minutes when all of a sudden my brother stopped and moved away from the bed. Phil stood in the middle of the room, quite impressively with his rather large cock pointed straight up, and I’m thinking, what the hell is he doing. Out of nowhere my brother says "how would you like to taste my cum", or something like that. I must have had the weirdest look on my face when I heard this exit his mouth, but shocking to myself I warmed up to the idea quickly. Of course I was nervous, but I knew that my bro had good intentions. I agreed. I was totally amazed at what was about to happen. My imagination was overloaded and my heart was on full throttle. Phillip returned back to where he was sitting on the bed next to me. He directed me to move down onto the floor in front of him. I followed his direction, even though I knew he was as inexperienced at this as I was. I was somewhat enjoying the roll of servant, and in later discussions with women I understand that this is what turns many of them onto oral sex, the power combined with the slavery of the action. I was so scared and turned on, all at the same time. The first five seconds I was down on my knees leaning over the edge of the bed seemed endless. Finally I reached over and wrapped my right hand around the base of my brother’s teenage shaft. I moved towards him and without thinking about it placed my tongue under his head. I circled it around the head a few times getting the taste of my brother, which was surprisingly enjoyable. Phillip placed his had on the back of my head obviously in somewhat of a hurry to release this upcoming load. He slowly pushed my head down on his, letting me get the feeling of a full sized cock in my mouth. I got used to my surroundings and started to pump my mouth against him, and I could tell this was a pleasure my brother had never felt before and was surely enjoying. Phil removed his hand from the back of my head, most likely because he couldn’t support it anymore. I was in the midst of giving my brother a great blowjob and we were both enjoying it. Then my brother asked my try and deep throat him, and I did. I gagged a few times but finally got the sensation of having a six-inch plus penis entirely squeezed in my mouth. I held it there for a few seconds, swirling my juices around. I then released my hold, and removed him from me. I allowed the air to cool the spit that dripped of the end of his shaft. I would then return him directly to my throat, and repeated this process over and over. By the end of fifteen minutes or so I was a serious blowjob pro. I had gotten down the motions that were driving Phil crazy and I wasn’t bothered by the precum taste so I assumed I was safe for the real thing. It wasn’t long before Phil was having problems holding it back any longer. He gave me warning by saying some catchy quote like "ready or not here I come". I took his bulging cock from my mouth and just let it rest on my lower lip. I then took my tongue and circled the tip hoping to keep the blast in my mouth and not in my throat. As I was sitting in preparation Phillip hit the bed and before I know it my mouth was warm and slippery. To my surprise my brother’s blast was more of a dribble, which turned out to be a good thing in the end. Since I was still an amateur at this I decided not to try and become a hero and take the whole load in my mouth. Instead I opted to take the first few dribbles and then just shoot the rest on my chest. After a few seconds of this Phil was empty and pulled away from me, letting me get a feel for the taste that he had left behind. He watched my expression that at first resembled discussed but soon changed to interest. I swirled it around and soon discovered that I was intrigued by how this tasted, and even more intrigued by the fact that I was enjoying the taste. After a few seconds of exploration I swallowed the load, which impressed my brother quite a bit. We rested for a bit, allowing our minds to wrestle with what had just happened. Phil was spread out over the bed with a limp dick that was covered in a cum saliva mixture, and I was still on the floor leaning against the bed with cum all over my chest, face and mouth. The noticeable difference between my brother and myself was that I still had a hard-on. And once Phil sat up and noticed this he quickly regained his energy. Phil told me to stay where I was and he quickly darted out of the bedroom and headed downstairs. It was a few minutes before he returned and he had something in his hand. Phil had gone down to dad’s study and brought an empty Cuban cigar case up with him. I didn’t have a chance to think about his intentions before he started giving directions. He ordered, or at least directed me to get up on the bed and spread out. I did so. He then crawled over the bed and towards me, almost as if he wanted to lay his head down on my stomach. He placed himself perpendicular to me with his head near my dick and his left hand, which contained the cigar case was hanging over the edge of the bed and out of sight for now. While I was still contemplating the new situation that was at hand I felt the warmest most enjoyable sensation down below. Phillip had engulfed me and was wasting no time bringing me pleasure. I was lost in a state of confusion and bewilderment, amazed at what was going on. You could have thought that I would be getting used to these things by now, but I wasn’t. I tilted my head back, started moaning and just enjoyed the ride. Minute after minute, I felt the warm sensations of my brother’s mouth slipping and sliding on my rock hard shaft. And that brings me to another point, my dick had never been this hard before in my life. I was somewhat concerned I was going to pop something because me cock had become "shrink-wrapped" allowing me to see more blood vessels and such than id ever seen before. But I shortly forgot about the silly worry and allowed myself to return to the pleasure. All of a sudden out of nowhere I felt a slight pushing sensation at my ass. I remembered about my brothers little cigar case and I quickly shot up out of my position, inquiring in him what he was doing. He explained quite rationally that he had wanted to try the pleasures of anal stimulation. And with all his mature explanation and his claim that It would surely increase my sexual pleasure, I endorsed him to continue. He shortly forgot about my bulging cock and turned his attention to my ass. I spread my legs a bit allowing him to get a better view and with a bit of the jelly from before he started to push the long slender cigar case into my ass. There was so much pain at first, and I let him know by kicking him a few times, but once he had gotten the tip inside me and let it rest a few moments everything was better. Phillip returned his attention to my dick, which let me forget about the pain below, though he still continued to poke away. After a few minutes of licking the head of my penis I was more comfortable and ready for the pleasure to come. After about five more minutes, Phil tapped me, bringing to my attention that the case was now fully in my ass. I moved him aside and grabbed a hold of the end, taking my turn at sliding the object in and out of me. This was such a trip, having an object fucking me like I was a girl. Phil put his hand back on the end, wiggling it around and continued with his massive blowjob. It wasn’t long before I had to blow, so I warned my brother and got ready. As I was doing this the thoughts of before and how I was having trouble getting all my cum out entered my mind. I knew that if nothing different happened here then I was screwed, or at least that’s what I thought then. I started to feel the pressure build so I told my brother, but he didn’t back away, leaving me with the impression that he was going to take my load in his mouth. I relaxed and just enjoyed the ride. As it started the pressure in my ass gave me this huge ejaculation which ended up all over my brothers mouth and face. It was the best feeling I had ever had and my problem from earlier definitely didn’t return. I guess I was cured. My brother Phillip and I continued to have fun with each other for a few years and it never became something of shame. I guess I’ll leave you there with the promise that I’ll tell you all my other stories some other time.