Having Fun With Sleeping Nude

Back when I was growing up, the house we lived in didn't have enough bedrooms, so I shared a room with my directly older brother while the oldest had his own room. The good thing was, our rooms were upstairs while our parents' room was on the main level so we did have some privacy, not that it was all that important since everyone in the house slept naked. Even mom and dad. As far back as I can remember I've slept naked. Well, I do remember wearing underwear and shorts when I was little until my parents felt I wasn't going to wet the bed, but beyond that point I've slept bare like everyone else. We weren't nudists, but because of this nudity wasn't an issue in the house, especially with my roomie brother. On any given weekend it wouldn't be anything unusual for me to be on my bed laying on my belly with my feet in the air looking at a comic book and my brother in his bed with his Game Boy, both of us without a stich on until we went downstairs. Sometimes even beyond that, just enjoying the warm weather and the freedom. 

Once he got a little older, though, it did get a tad more complicated as he was getting constant erections and took care of them like any teenager would. Not that he hid it or anything; a lot of nights rubbing one out without a care. A couple times our mom even walked in to get laundry and he didn't stop. She also didn't bat an eye, so I figured he wasn't doing anything bad. One night he came in from his shower with his erect penis leading the way, and as soon as he jumped in bed he started stroking. I rolled over facing him and asked, "Why do you touch yourself like that?" With his eyes closed he said, "It's called 'masturbating'. It makes you feel good." "Can I do it too?" "No, you're too young. Maybe in a while." "Oh...ok." I just watched as his hand moved up and down on his penis for a couple minutes before he took a sharp breath and squirmed around in his bed. He laid there for a minute before pulling the sheet over himself, still pitching a tent. Thinking back, I guess at that point he was still having dry orgasms, not remembering any wadded up tissues in the trash can or random socks laying around at the time.

This went on for 6 months to a year or so before my constant erections started happening. One evening he came back from taking a shower and I was on top of my covers on my belly and I was kind of grinding my hips into the bed. He asked me, "What are you doing?" "It feels good when I do it." "Is your wiener hard?" "Uh-huh." "Ok, I think you're old enough to do it the right way. Roll over." I stopped grinding and flopped over on my back, my still small penis sticking straight out. "Now, watch what I'm doing." He laid on his bed and pressed his feet together and started stroking himself, eyes closed and other hand rubbing all over himself. "Don't squeeze it too hard, just enough to grip yourself. After a few minutes is going to feel like you need to pee, but you won't. Just keep going." He kept at it for 3 or 4 minutes before he said, "It's about to happen, you gotta keep going..." and a few seconds later his legs stretched out and some white goo spurted onto his belly as he squirmed around. "What is that stuff?" "It's called 'cum'." He got up and grabbed some dirty underwear and wiped it up. "Ok, now it's your turn." Excited, I laid back and took hold of my erection, stroking it quickly and awkwardly. "Whoa, ease up. Keep a rhythm doing it." I slowed down a little and eventually got a good pace. It took me maybe a couple minutes before I told him I thought I was starting to feel it. "Ok, keep going. It's almost going to feel like butterflies in your tummy, just in your penis." I kept at it and a few seconds later...it happened. I let out a high-pitched squeal kicked my legs around with my toes curled down tight. I laid there shaking for a minute before I asked him, "Did I do it right?" He smiled and said, "Yeah, you did it right. You just had your first orgasm." I jumped up and hugged him, almost in tears. "That felt so good!" "Yeah...pretty cool, huh?" "Uh-huh!"

Fast forward another year or two, and my brother and I had masturbated in each other's presence hundreds of times. It almost became a normal, nightly routine, and why not? We were both of the age where we couldn't keep our hands off ourselves and since he was the one who taught me, there was zero reason to hide it from each other. The only difference now was my oldest brother had gone off to college so he moved into the empty bedroom, leaving me to myself for the first time. I do admit that it was kind of lonely, but he was right next door and there were plenty of times I wandered over to watch tv with him and he never minded. I think he kind of missed it, too.

Having the spare bed in my room now, one weekend at school I was talking to a friend of mine and asked him if he wanted to stay over for the weekend. He had to check with his parents, but as long as they said yes he wanted to. They obviously agreed and on a Friday his mom dropped him off for the next couple days. The evening went on, yada yada yada, and eventually it was getting late enough to go to sleep. He asked where he should change, and I eventually told him about how we sleep naked. "You mean...completely naked?" "Yep. Naked naked. I didn't say it before because I didn't want to freak you out." "So...should I sleep naked too...?" "Up to you, but otherwise you're the only one who wouldn't be." "Well...ok. Should I just take off my clothes here?" "Might as well, we'll be seeing each other anyway." He took a deep breath and at the same time we both pulled off our clothes, now standing in front of each other bare. At first he was a little shocked, covering himself with his hands, but seeing me wide open he slowly pulled them away, both of us giggling about seeing each other nude. We jumped into our beds and I asked him if he liked it. "Mmhmm, it feels nice," as he rolled around in the bed, free of clothes. By this point, I had a full, rock-hard erection. Not sure if it was from the situation or conditioning because I masturbated pretty much every night, but I wanted to cum. I held off though, because I didn't want him to be creeped out by it. Did he also have a boner? Not sure. I wanted to ask, but I let the thought pass. 

The next morning when we woke up we both got dressed and went down for breakfast, watching some tv in the process. Eventually I convinced my mom to let us walk to the store by ourselves, which was about 20 minutes away. He looked like he normally would for school, I was dressed in my usual weekend attire; t-shirt with track pants and slide sandals. We spent an hour or so in the store, looking at the cd's and video games and getting a soda at the snack bar before waking back home. Again, as the day before, the evening went by without much going on. This time, however, when we went back to my room he seemed pretty eager to strip down. I guess he liked sleeping naked more than I thought. He quickly pulled off his clothes and sat on the bed and I did the same, except this time I didn't hide that I had a boner. I looked at it and said, "Man...I really need to take care of this thing." "What? You mean play with yourself?" I nodded. I guess from talking about it he started getting excited as well, getting hard on just a few seconds. He asked me, "Are you gonna do it?" "Yeah, are you?" "Sure. I mean, if you want me to do it too." I reached over and grabbed a tissue, asking, "Do you need one of these?" He kind of blushed, saying, "Yeah, I do." I handed it to him and grabbed one for myself, both of us laying down with our penises pointing to the ceiling. Simultaneously we both started stroking, knowing neither of us were going to last very long, having gone at least two days without cumming. Neither of us said anything; the only sound being our hands moving up and down our cocks. I was the first to cum, shooting a nice load into the tissue, almost cumming before I could get it in place since I was so worked up. Seconds later it was his turn, wrapping it around his head and shaking as he filled it with his seed. He eventuality calmed down and when he looked over he kind of laughed. He asked me if I ever did it with anyone else before, and I said I had lots of times. I asked him and he said no, and I said, "Fun, huh?" He nodded.

We eventually fell asleep and the next morning I woke up earlier than normal. Not able to fall back asleep I sat at the foot of my bed and turned on my Playstation and messed around with it for a while. He eventually woke up and sat next to me, both of us still naked, and we took turns with the controller. It didn't take much time before he was sporting another erection, which in turn got me going. We kept playing for a few more minutes before he asked me, "Do you want to do it again?" I played dumb. "Do what?" He blushed and giggled before saying, "You know...masturbate," with a whisper. I smiled and said sure, saying just to lay in my bed. I switched my position to where we were facing each other, head to toe. I started stroking and he asked about a tissue, but I told him let's just let it fly. He started going with me and we watched as we stroked and massaged our cocks, our feet next to each other's heads with our toes wiggling sensually. Unlike last night he came first, his legs spreading with his foot right in my face, toes curling as he came all over his tummy. I knew I wasn't far behind, so I told him to watch. I put my foot on his chest to get a good view, and when I came I pointed straight up, the cum flying about a foot in the air before splashing down. Now both spent, we cleaned up our messes before heading downstairs for breakfast. 

After we ate we went outside for a while and played some basketball in the driveway, both of us simply going shirtless and barefoot. I'm not sure how long we were out there but his mom eventually pulled up and ran inside to get his stuff, throwing on a shirt but coming back out still in his bare feet. He threw his bag and shoes in the back and got in the front seat, his mom asking, "Why aren't you wearing your shoes?" He kind of shrugged and said, "I dunno, I just want to go barefoot." I guess it was the closest he could be to being naked at that point. 

The next day at school he thanked me for the weekend, saying he had fun, but we both agreed that what happened would stay between us. We also agreed, however, that we needed to do it again.