I was home from college this Thanksgiving holiday. It was a Tuesday morning and both my parents had already left for work. I had just gotten out of the shower and was standing bare-ass naked in front of the mirror combing my hair. My just turned 14-year old brother and I share a bathroom between our two bedrooms and he stumbled in to take a piss. Although he was wearing a pair of gray jockey briefs, I noticed his morning wood and about a 1' wet spot near the top of his briefs. As he was peeing in the toilet behind me, I said, 'Ian, it looks like you need to take care of your morning wood.' As he finished up and turned to face me in the mirror, he asked what I was talking about. I replied, 'Well, you're leaking pre-cum so your boner needs some serious attention.'
Since we had grown up together and I had pretty much looked after him ever since I was about 10, we had no modesty between us, never closed bathroom doors, and talked about pretty much anything that came to mind. He looked in the mirror for a second at my dick then looked down at his - it looked to be about a 4 inch boner. Then he asked what I meant. I told him to pull off his briefs and I'd tell him. As he did, his boner sprang up hitting his stomach and I saw for the first time that he had developed a thin line of pubes since summer. I said, dude, your manhood is developing and there are some things other than piss that are starting to come out of your dick - namely, pre-cum and semen. He looked down at his dick again and said he didn't know about either of those, but he had been getting a lot of painful boners for the past few months. I asked, you mean you haven't started jerking off yet? He asked what that was, so I said it's technically called masturbating. He looked clueless, so I said it's stroking your cock until you shoot your spunk out. He said he'd done some light rubbing, but nothing like I was talking about. So I picked up his jockey shorts and told him if he hasn't been jacking off, his wet dreams must be leaving stains all over his underwear and bed sheets.
Then I said let's take a look at your bed. We went into his room and I pulled back his sheets - there must have been 6 dried cum spots there plus one that was still wet from last night. I asked, Ian, hasn't Mom or Dad asked you about these spots in your sheets and shorts? He said that Mom had said something once but he didn't know what it was. I said, dude, you're leaking like crazy and you'll keep doing it until you start jerking off!
While Ian is a good-looking, skinny kid with tight blond curls who gets lots of second looks from the girls, he's still a bit of a nerd and obviously had no clue what I was talking about. Meanwhile, his boner seemed to have stretched a bit more and his dick head was turning purple. Finally he said, I don't know how to do it, it's hurting bad, so will you show me how? Even though I thought he'd seen me beating off before in the shower, I said, ok, but let's go back to the bathroom. Even though I had already jerked off in bed, my 6 inch cock was getting hard again. I grabbed some hand lotion for lube and told him to watch. I stood in front of the mirror at the sink and started stroking my cock with my right fist and massaging my balls with my left. With him standing at my right side, I told him to start doing what I was doing. It took me maybe four minutes to blow my spunk, but Ian was just lightly stroking his and staring at me and my dick in the mirror in amazement when I grunted and shot about four ropes of hot jizz, one hitting the mirror. He said, holy crap, what was that? I said, well, that's semen or what we call jizz or cum, and it's what we're trying to get out of you. Between jizz and pre-cum, that's what's been dribbling out of your dick when you're sleeping. Your jizz is trying to get out, that's why your junk aches.
I looked over at his 4 inch boner and saw that more pre-cum was leaking out and his dick head was glowing purple, but he wasn't stroking fast or hard enough to cum, especially for the first time. Then he looked at me and started whimpering, saying that his cock really hurt bad. I said, ok, ok, let me help you out. So I moved in behind him, with my semi-erect, cum-slick cock pushing against his upper butt, reached around him and lubed up both hands again, then grabbed his swollen dick with my right hand and his small, hairless ball sack with my left. I started gently squeezing his nuts and used my right thumb and index finger to form a tight circle to stroke his cock. I told him to put his hands on the sink top for support and then got into a nice rhythm of stroking and squeezing with my arms wrapped around his sides. I could hear him starting to pant and he was sort of grinding his cock into my fingers by moving his butt in and out almost like he was fucking - a pretty natural reflex I guess. We were both getting pretty hot. After about two minutes, I asked him how he was doing and he said it hurts and feels really good at the same time - keep doing what you're doing! I increased the pressure around his swollen shaft a little more and stroked a little faster until he was really moaning. I knew he was getting close to losing his virgin load, so I concentrated my right fingers just below and over the top of his dick head while using my hips to make his natural humping action go faster. As he moaned louder and started convulsing, I suddenly took my left hand off his nuts and jammed a finger up his tight little butt hole, at which point he jumped and screamed, spraying his virgin spunk all over the countertop. I kept going for about another two minutes to pump out as much of his jizz as possible, but then he started to fall, so I was kind of holding him up by my finger in his butt hole and my right hand wrapped around his junk. I eased my finger out of his butt and helped him sit on the toilet.
We both looked towards the sink where he had just blown his first load, and I said not bad, little bro! He smiled ear-to-ear and said, wow, that was totally awesome! But what's with your finger up my ass? I told him mark that up as a lesson learned. I told him when I jerked off the first time, I stopped when I first started to spurt because I was scared and didn't know what was happening. So my junk ached worst than ever for a week until I finally figured out I needed to keep stroking until I got as much cum out as possible. One of my friends told me about sticking a finger up your ass when you're close to busting a nut because it really intensifies your orgasm and gets all of your jizz out. So, I just wanted to make sure you were totally taken care of for your first time.
Meantime, all this talk and action with my dick pressed against the top of his butt got me hornier than hell again, so I went back over to the sink and managed to stroke out another good load with my right hand still lubed with some of his virgin cum. I jammed my left finger up my ass just as I was about to shoot and managed to hit the mirror with three thick ropes of cum. I finished by saying well, Ian, welcome to manhood and I assume you can handle yourself for now on. Somehow he got the pun, laughed, and said thanks big bro!