My little brother (4 years younger) seemed curious about my body from the start as little boys often are. I'm not sure what his curiosities got him into with our older sister, but, I definitely cut him some slack, he's growing up with 3 sisters (two older, one younger).
One day, I caught him going through my drawers looking at my bras. He about cried getting caught but I comforted him letting him know it's okay to be curious but be respectful of other people's privacy. He hid himself in his room the rest of that day. About a year after that, early summer, I discovered my bras were being messed with again. I even found dried cum in the cup of one of them. Now that I knew he was masturbating, I felt a bit better about approaching him about all this.
Once we were able to have the house to ourselves. I confronted him about cumming in my bras. I sat him down in my room and told him that if he was curious about something, he could just ask me. He knew enough as to why girls had boobs. He just sheepishly admitted to me he found them fascinating and that mine were the biggest pair that were always around him. He asked me about bra sizes (I was a DD by this point). He didn't seem too shy asking me things, even about nipples, and most of his questions were pretty generic.
As we talked, I noticed he was starting to get an erection. He asked if he could see them in just the bra I was wearing. I didn't see any harm in that, so I took my shirt off revealing a basic white bra. He kept on with questions about bras as he started to rub himself over his shorts. His sentences started to stagger and trail off as he unzipped his shorts, pulled it out, and started stroking as his eyes just fixed on my bra covered boobs. I decided to be bold and go with the moment. I removed my bra. As my nipples appeared in front of him, his eyes grew wider, still transfixed on my chest, and stroking himself passionately. It only took him another minute for him to orgasm. As he came to it, I held my bra cup in front of him and he aimed his cum right into it. As soon as he stopped he had this terrified and embarrassed look on his face.
I hugged him quickly and we laid back on my bed to relax where I let him watch as I traced my boobs with my fingers. We did that for about an hour, as he asked more questions, then I let him jerk off again to my boobs. Then we got dressed. I let him keep the bra he had cum into.
Aside from occasional glances to my chest, he never seemed to want to revisit that moment. Even today, we give each other that knowing smile, but haven't repeated what happened long ago. ^nippy E^
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