Chapter 1

I couldn’t believe it when my brother asked me for help. He’s always seemed so in control of things - he’s about five years older than me, and ... well, he’s one of the coolest guys that I know. He’s in pretty good shape, he’s smart, funny, blah blah blah. He’s always seemed so good with women, so when he told me his problem, I was a little bit skeptical.

We’d just been hanging around on the couch when he’d told me - it was a psychological thing, he said, and it had begun to seriously affect his relationships. He told me that coming to me for help was one of the hardest things that he’d ever done, but he didn’t know what else to do.

My mouth was open the whole time he spoke, and when he was done I was utterly speechless. On one hand, I loved my brother and wanted to help him out however I could (and I could certainly see why he’d come to me) ... but on the other hand, it was by far the strangest thing that anyone had ever asked me.

He said that he’d give me a few days to think about it, and when he left, I must have sat there in shock for like twenty minutes, just absorbing the information I’d just been given.

My brother had told me that he couldn’t...”achieve climax” ... when he was with another person. No matter what. He could “peak” by himself, but as soon as someone else was there he just got far too anxious, and ended up losing his erection. It had put a crimp in every relationship he’d ever had, and no matter how supportive the girl, they always ended up feeling like it was their fault. Ever since my brother started dating, he’s pretty much never been single, but this certainly explained why he so often had a different girl on his arm.

He needed a girl that he was utterly, utterly comfortable with, he’d told me - someone who he trusted unconditionally not to laugh, or judge him in any way. It helped, too, that he didn’t see me in even a remotely sexual light (something that I was extremely glad to hear, as you can imagine) because it meant he didn’t run the risk of feeling “pressured” or like he was going to offend me if he didn’t perform.

It took me a few days to give him an answer, and I can tell you, those were three of the most awkward days of my life. Every time I saw him, I thought about what he was asking me to do - sit in a room with him and watch him jerk off.

After a lot of consideration, I decided not to tell my boyfriend about it. For one, my brother had told me that it was the most embarrassing secret of his life, and that it had taken him a while to build up the courage to even tell me at all. Secondly, I was pretty sure that I was going to do it - I love my brother, and if it was this much a problem in his life, of course I wanted to do what I could to help him. My boyfriend would probably have tried to talk me out of it, or thought I was a freak, or even gotten jealous or something like that. Thirdly, I wanted to make sure it didn’t get out! If anyone else ever heard that I was the girl who watched her brother jerk off, I knew I’d never escape it ... When I told my brother that I was happy to help him, he got this huge look of relief on his face.

“Thanks, sis...” he said. “I was so worried that you were going to think I was a perv, or never speak to me again ... I really love you, and I swear I’ll repay you some day...”

I laughed nervously at his gratitude, and told him not to worry about it. We agreed to start the next night, when our parents would be out and we could have the house to ourselves. To make this weird situation as un-weird as possible, we agreed to do it in the lounge.

The night that I told my brother I’d help, I went around to my boyfriend’s house and asked him if he’d jerk off in front of me.

“Uh, sure...” he said, and to his credit didn’t even ask why.

It was interesting. I’ve slept with more than a couple of guys, and fooled around in all other kinds of ways, but I’ve never actually watched someone jerk off before. Maybe everyone does it differently - my boyfriend pulled out some lube that I didn’t know he had. I wanted to make it sexy, so I stripped down to my underwear, and sat next to him on the bed. The plan was to take my bra off slowly as he kept going, maybe join in myself toward the end, but I was so fascinated watching him that I completely forgot about that and just watched as his fist pumped up and down.

He got that familiar look in his eyes as he got closer and closer, and when he came, shooting his stuff onto his chest, I couldn’t believe how sexy it was. Right before his climax, his cock-head had grown red and sort of angry-looking - I’ve jerked guys off before, but never really watched their cocks as they did. I’ve always been more focused on their eyes, or their chest, or what they’re doing to me with their hands ... It was really hot, watching my boyfriend cum, and after he cleaned up, I asked if he was up for another one. It was only after we’d fucked, when I was snuggled up next to him in that post-orgasm bliss, that an alarming thought came into my head: What if I found it sexy to watch my brother?

2:

“Thanks again for doing this,” my brother said, his usual confident mannerisms gone, replaced by a nervous look in his eyes and a slight stammer in his voice. “I can’t explain how grateful... -”

“It’s okay,” I interrupted with a smile, waving away his thanks. “Whatever I can do to help. Now ... how do you want to do this?”

I’d spent the whole day with butterflies in my stomach, knowing that this was coming this evening (hoping that my brother would be too, so we only had to do this once). As the evening had grown closer and closer, however, I’d started to relax. He was my brother, my flesh and blood ... I’d never even had a remotely sexual thought about him, and even if I did watch him rub himself for a few minutes, that didn’t mean that anything was going to change.

By the time nine o’clock had come around, the “Everything will be fine” mantra was firmly entrenched in my head. Everything was going to be fine. I’d put on a pair of loose-fitting jeans and a baggy T-shirt, gone downstairs, and found my brother pacing up and down.

“I guess, uh...” he said, looking around. “What if ... what if I sit here on this couch, and you sit across from me?”

“Sure thing,” I said, as lightly as I possibly could. I sat where he’d gestured, my legs curled up underneath me, and there was a strange silence as we looked each other in the eyes ... until we both burst out laughing at the same time.

“This is weird, isn’t it?” he said, and I nodded.

“Super weird. Let’s get it over with.”

“You’re the boss,” he said, and dropped his pants to reveal the bulge underneath.

I’d never spent any time thinking about the size of my brother’s cock - it’s not exactly a topic that comes up much, hey? But if I had, it would have definitely been smaller in my imagination than it was in real life. He didn’t have the largest cock I’d ever seen, but it was definitely close, probably a bit over eight inches. Thick, too, and despite his obvious nervousness, it was already hard.

He sat down opposite me, looked me in the eyes, and simply said “Well ... here we go.”

In that moment, I wished that I’d asked him ahead of time what would have been most helpful for me to do. Was I meant to have brought a book? It would have felt rude to just pull out my iPhone and start seeing how quickly I could destroy the green pigs, but I also didn’t want to stare at his penis like he was a circus freak.

For the first few minutes, I just stared into his eyes. Then I think we both realized how weird that was - he looked away, and I did as well, until my attention was inevitably drawn to his hand, pumping up and down his member.

I mean, you can’t not look, can you? I’d only ever seen my boyfriend masturbate before, and I think it’s human nature to want to compare. Unlike my boyfriend, for example, my brother isn’t circumsized, and didn’t use any lube. I don’t know if that’s why he didn’t use lube, but with every stroke, his foreskin bunched up around his head, and it looked like that was stimulating enough to get him off.

His hand kept on pumping, up and down, over and over ... it was almost hypnotic, and once I started watching, I couldn’t look away. His hand moved in such a steady rhythm - up and down and up and down. When my boyfriend had masturbated for me, it had only lasted a few minutes, but due to his problem, my brother would obviously be going for some time.

Up and down and up and down ... it was such a soothing thing to watch. That same repetitive movement, over and over. I found myself losing sight of everything else - all I was aware of was my own breathing, and the constant, fluid motion of my brother’s hand, as he repeated the same motion over and over again. Over and over and over and over ... While watching, my mind began to clear of thoughts. I was so happy to be helping my brother. Helping their brothers is what good little sisters do ... I wanted to help my brother. I wanted to be there for him, to do what I could. It was good that I was being so helpful - I was a good sister for helping my brother. It wasn’t even weird, not any more ... watching my brother jerk off wasn’t weird. It was a normal, good, helpful thing that I was doing.