My sister Andie is two years younger than me. We always got along well and were pretty close friends growing up. As we hit puberty we drifted apart a bit, but we were still fairly close and talked a lot. I always told her that she could come to me about anything and I would help her in any way that I could. She came to me often with school work that she needed help with, advice on important social decisions, and after what I am about to tell you about, sex related questions. Our parents are very conservative and religious so we both got the basic sex talk when we were younger but that was it. And our parents made it clear that we were to wait until marriage to have sex.
This happened one night when I was 16 and Andie was 14. It was the second or third week of school. It was her freshman year and my junior year. Andie and I had been talking a lot over the past few weeks because she was very nervous for her first year of high school. I told her not to worry and reassured her that I would be there whenever she needed anything. Up until this point, we had never discussed anything sexual, even in a joking manner, because it was never acceptable in our household. So that night, I was working on my homework in my bedroom, when Andie knocked on my door. I told her to come on in and have a seat. I asked her what she needed and she told me that she needed advice.
'Yeah sure, what's up?' I asked, putting my pencil down and turning my chair to face Andie.
'Well, this is something that we've never really talked about before and I'm not sure exactly how to go about it.' She explained.
'Just spit it out, whatever it is. It shouldn't be a big deal.' I assured her.
She mumbled something I couldn't understand.
'You're gonna have to speak up, I can't hear you.' I told her.
She sighed and then blurted out, 'Doyouevermasturbate?'
I was shocked to hear Andie say that and the look on my face must have shown it because she immediately said 'I'm sorry! I shouldn't have asked!'
'No, no. I just wasn't expecting that.' I told her.
She was blushing like crazy and staring at her feet.
'Why do you ask?' I asked.
'I was just wondering...' She said.
'Why were you wondering?' I asked.
'Because, some girls at school were talking about how their brothers do it.' She said, still looking at the ground.
'Hey, it's okay. You can look at me.' I told her.
'I'm so embarrassed that I asked.' She said.
'Look, it's fine. Do you still want me to answer?' I asked.
'I mean, if you are comfortable answering it, then I guess so.' She said.
'Well, yes. I do.' I told her.
Her eyes practically bulged out of her head. 'Really?!'
'Yes! Really...' I said.
'Holy... Wow.' She said.
'Do you?' I asked.
'What?! Are you crazy!? NO!' She replied.
'Oh, okay. Sorry.' I said. I felt that I had crossed the line asking her that.
'Should I?' She asked back.
I was dumbfounded. 'Uh, I don't even know what to say to that.'
'Should I masturbate?' She asked again.
'I mean, it feels great. But I'm not going to tell you that you should or shouldn't do it.' I replied.
'How do I do it?' She asked, now looking dead at me.
'Well, you um... I can't do this.' I said.
'Do what?' She asked.
'Explain to my sister how to masturbate.' I answered.
'Please Zander. I really want to know.' She said.
'Is that why you asked me if I did it?' I asked.
'Yeah, I didn't just want to come in and be like 'can you explain to me how I should masturbate?'' She told me.
'Alright.' I said.
'Can I watch you do it?' She asked.
'What?!' I practically fell out of my chair.
'Can I watch you play with yourself?' She asked again.
'Andie, we can't.' I told her.
'How about this weekend, while mom and dad are away at Grandma's house? I can watch you and you can help me learn what to do. Please?' She begged.
'I'll think about it.' I told her.
'Thank you.' She said. And she got up and left.
I thought about it all that night. And as much as I knew it was wrong and bad, I couldn't help but to get turned on to think about doing it. I eventually decided what the hell? So I told her later that week that we could do it that weekend. She seemed really happy. That weekend rolled around and mom and dad headed off to our Grandmother's house for the day. That afternoon, Andie came into my room and sat down on my bed again.
'You ready Zander?' She asked.
'As ready as I'll get.' I told her.
'So, how should we start this?' She asked.
'Well, I'd say we both get naked. I'll go, then you can go.' I said.
'Okay.' She agreed.
We each took off one layer at a time. First my shirt, no big deal. Then her shirt, then my pants, then her shorts. Then, she reached around and unclasped her bra and let it fall to the floor. I stared at her boobs. I hadn't seen her naked since she was like six. They were small, but round and perky. Her nipples were pale pink, and hard. I could feel myself getting hard already.
'Go on,' She urged.
I slid my hands into the waistband of my boxers and slid them down in one swift motion. My hard-on sprang out into the open. Andie stared at it in awe. I wasn't very big, but she still seemed to be fascinated with it. Then, she slid her panties down and stepped out of them. We stood face to face, naked as the day we were born.
'Well, your turn to go.' She said.
I sat back in my desk chair and began to slowly stroke my dick. It was turning me on so much knowing that Andie was watching me. I closed my eyes and sped up a little.
'Can I touch it?' She asked.
I opened my eyes and she was standing over me.
'Uh, sure.' I said.
At this point, I had gotten a couple of hand jobs so I figured that Andie touching it was no big deal. She reached over and lightly stroked it with two fingers. Then she took it in her fist and squeezed it lightly a time or two. Then she gave it a few good strokes. She then let go and said I could continue. I sped up and shot my load within minutes. She watched, fascinated, as I squirted my cum onto my stomach. I grabbed a few tissues and cleaned up.
'Alright, your turn.' I told her.
'What do I do?' She asked.
'Lay back on my bed.' I instructed.
'Now what?' She asked.
'Just like, finger it. Rub it.' I said.
I had fingered a few girls before but I never had to explain to someone how to do it. She tried a few things, but I could tell by her facial expressions that nothing she did felt good.
'This isn't working.' She said.
'Do you want me to help you?' I asked.
'You know how to?' She asked.
'Yes. I know what to do. Would you like me to?' I asked.
'Please?' She asked.
She scooted over and I sat down next to her on my bed. She opened her legs and I was staring straight at her trimmed pussy. I could feel myself getting hard again already. I slowly slid one finger into her. She groaned.
'You okay?' I asked.
'Yeah, keep going.' She said.
I moved my finger in and out of her tight pussy for a minute before inserting a second finger. I spit on my other hand and started working her clit with that hand. She gasped and said 'Keep doing that!' I kept rubbing her clit in circles and rhythmically fingering her. After a few minutes of this, she inhaled sharply and let out this animalistic groan/moan and threw her head back. I could feel her muscles clenching around me and her whole body shook. When she began to come back down, I slowed down and stopped and pulled my hands away.
'Well?' I asked.
'That was fucking amazing!' She said, sitting up.
I was completely hard again by now.
'Can I try and make you cum?' She asked.
'Sure.' I smiled.
I laid back on the bed and she leaned over me and began stroking me. I was cumming again within a few minutes. After it was over, I thanked her, she thanked me again, and we just laid on my bed and talked about sex and things. She asked me about how experienced I was and I told her. She told me that she had never done more than kiss a boy. She asked me if I was going to wait till marriage to have sex and I said hell no. She said she probably wouldn't either. Eventually, we redressed and cleaned up so mom and dad wouldn't suspect anything. We decided that it would be a normal thing for us to get together every weekend that mom and dad went away to have some harmless fun. We did this for the next two years until I went away to college. We would still occasionally do it on webcam with each other and we always have nice sessions when I come home to visit. As far as our parents go, I don't think they ever noticed or suspected a thing.