My sister and I have always had a close relationship growing up. She is three years younger then me and I never really thought about her sexually. A few perverted thoughts might have popped in from time to time though. Her name is Heather and she has blonde hair and is very petite with average boobs. Anyways, this happened after I had gone away to college. Since we were close, my sister and I usually had video chats on the internet so we could catch up. This probably happened once a week depending on our schedules. Also, my roommate lived fairly close to campus so he was always gone on the weekends. I liked it since it gave me a chance to be by myself and masturbate. I've never really been too lucky with girls so I always had that as my back up plan.
On a Friday night in early November, I went out for awhile but struck out and decided to call it a night. I knew I was going straight back to my room to rub one out but when I got on my computer, I noticed that my sister was on. I decided to have a video chat never dreaming on how it would end up. We started talking and she seemed very happy to see me. She had on her usual pajamas: spaghetti strap shirt and tiny shorts. I had just changed too and was just in shorts. We started out with the small talk and it finally progressed into my lack of experience with girls. She tried comforting me which kind of worked.
'I'm glad I have a sister like you,' I said.
'I wish there was something I could to do to help,' she said. 'So what are you doing later tonight?'
'Um....nothing,' I replied. I knew that I was going to watch porn and masturbate but I didn't want to tell my sister that.
'You should watch some porn or something. It might help you relax,' Heather said. I couldn't believe what I was hearing. I shifted nervously in my chair and offered no reply. 'I know all you guys do it. I do it too.'
I decided to play along. 'What kind of porn do you like?'
'You know, girls with guys, girls with...girls,' she said blushing a little.
'Wow, were you going to watch some tonight?' I said.
'Yes, but then you started talking to me,' she said with a laugh. the conversation started to get me hard. I couldn't believe it. My sister was making me horny. 'Wanna just do it together? I mean, since we already know we're both gonna do it tonight.'
'Um....ok,' I said nervously.
Heather aimed the cam right on her boobs. 'You ready?' she said. She slowly peeled her shirt off over her belly until her boobs fell out. They looked so gorgeous. 'You like?'
'Oh my God, yes,' I stammer. I knew it was my turn which was revealing my hard cock to her. I pointed the cam down towards my crotch and slipped off my shorts. Her eyes widened when she saw the tent I was pitching. It was now or never. I quickly ripped my boxers off as my cock sprang free. It's about seven inches long and completely hair free down there.
'Nice one,' Heather says. 'That's the first one I've ever seen.' I grab my cock with my hand and slowly stroke looking at her tits. 'Ok, my turn again.' She gets up and turns away from the cam. Heather slowly peels off her shorts showing me her firm ass.
I start to stroke faster. 'Tease me with your ass.' She starts to shake it for me but then she spins around revealing her shaved pussy. 'That's so hot.' Heather sits back down and aims the cam so I can only see her pussy and tits. I make sure my hard cock takes up her entire screen. We don't say much as I continue stroking and she starts fingering. We watch each masturbate as we heard soft moans.
I reach into the bottom drawer and take out some KY to pour on my cock. It slickens it right up and feels so good as I stroke. Heather gets up and points her ass to the screen and she fingers from behind. Then she suddenly leaves and reappears with a little dildo.
'Where did you get that?' I ask.
'Mom,' Heather says with a wink. She slips it inside her and starts pumping away. 'I'm gonna cum,' She says as she rocks back and forth and moans. She throws her head back and moans my name as she cums on her dildo. I hold off until she's looking again until my orgasm. It squirts and gets me all over my chest and belly. We both sit there in complete bliss. We say our goodnights and I clean up and crawl into bed. I still can't believe what just happened.
The next night when I get on the computer again Heather is already on. She wants to video chat again and when her screen comes up she is totally naked. 'Again?' she asks. I quickly strip down and we masturbate together again. This happened every Friday and Saturday night until I went home for Thanksgiving vacation. That's when things got really interesting.