I grew up in a strict Catholic household. Both of my parent's families were devout Catholics. With things being like this, I never tried to spy on my older sister, Chloe, because I knew that if my parents ever found out I would be as good as dead. Although my parents were strict, I was not super sheltered. I learned a lot from the boys at school. I was a regular masturbator by the time I was 13. Of course, I knew when and where it was safe to do it, so I didn't get to do it as often as I would have liked.
My sister, Chloe, and I were never really close although she was only about two years older than me. However, we didn't fight or dislike each other. We just kept to ourselves. So I had no idea at the time, but I know now, that Chloe was very educated in the area of sex and all related things. She lost her virginity when she was 16. Anyway, the point is Chloe and I weren't close siblings.
One rainy August day of my freshman year and Chloe's junior year, my parents got a call saying that my aunt Connie, mom's oldest sister, was just diagnosed with cancer. Mom, being how she is, insisted that she and dad go to the next town over to see her. That means that Chloe and I would be alone for the rest of the afternoon and night. Which by this time was acceptable since we were both old enough. So mom and dad left and Chloe and I minded our own business as usual.
Chloe cooked us up some food for dinner, and I washed the dishes after we were finished. Then I went to the living room to watch some TV. Chloe said she was going upstairs to finish her homework. After about 20 minutes I needed to get something from my room (looking back now I can't recall what it was that I needed.). I left the TV on and headed up the stairs and toward my room. The door to Chloe's room was cracked open about an inch or two. As I walked past, I casually glanced in. I was in for the shock of my life. Chloe was laying on her bed, completely naked, with both hands working away at her pussy.
Now, I had never seen porn videos, but I had seen enough playboys and whatnot to know what she was doing. It had just never occurred to me that girls masturbated too. I knew I shouldn't be watching her. So being the good kid that I was, I walked away from it, with a throbbing boner. But I did walk away. I went to my room and closed the door and started jacking off like a maniac. I came faster than I ever remember cumming before. Then I went back downstairs and planted myself in front of the TV. About 10 minutes later, Chloe came down to join me. She was wearing the same clothes that she had on earlier. I didn't intend to say anything to her about what I saw. But after she sat down on the couch diagonal from the couch where I was sitting, I couldn't help myself.
'I didn't know that girls did that too.' I blurted out.
'Did what?' She asked, thinking I was talking about something that was on the TV.
'What you were doing upstairs.' I said. I was mentally kicking myself for saying anything, I thought she would get angry with me.
'How do you know what I was doing upstairs?' She asked, sounding more interested than upset.
'I saw you. I was getting something from my room and I saw you on your bed. But I didn't watch for very long.' I told her.
'So you do it too?' She asked me.
'Yeah, I did it after I saw you.' I admitted.
'Do you do it a lot?' She asked.
'I don't know.' I said.
'Oh,' She sighed.
We went back to watching TV like nothing had happened. But then when the show that was on was over, Chloe turned to me and asked: 'Can I watch you do it?'
'What?' I asked, shocked for the second time tonight.
'Can I watch you play with yourself?' She asked again.
'Um, I... why?' I asked.
'Because I'm curious.' She said.
'Have you watched other people do it?' I asked.
'Yeah,' She said.
'Well, I guess...' I said, still hesitant.
'You can watch me after. Well, watch all of it, I mean.' She giggled.
At this point, I didn't realize that girls orgasmed too. It just didn't register in my 14 year old brain, so her comment didn't have quite the effect that she was hoping for, but nonetheless it helped convince me.
'Okay, I'll do it.' I said.
'Okay, let's go upstairs.' She said, getting up from the chair.
I followed her up the stairs and into her room.
'Get naked!' She teased.
'Hold on,' I said. Now I was nervous as hell.
I managed to get hard enough to feel comfortable to take my clothes off. After I stripped down, Chloe scooted over and offered me a spot to sit on the bed next to her. I sat down, grabbed my cock, and started stroking. Chloe sat silently watching me. Without warning, she touched my pubes. She was rubbing them softly as I was pumping my dick. It didn't take me very long before I came, covering my stomach and arm in cum. Chloe applauded when I was finished, and stood up.
'My turn, I guess.' She said, smirking ear to ear.
She stripped and sat back down. Now we were both naked on the bed together. She laid back and opened her legs. I was in awe. It was the first pussy I saw in real life, and it was only inches from my face. I asked her if I could touch and she agreed. I felt around and she explained her clit and vagina and what she liked. When I was done exploring, she started. I was amazed as she worked on her vagina and clit with one hand and massaged her tits with the other hand. She moved her hips in time with her rubbing. Soon, she was panting and moaning and thrusting her hips up off the bed.
'Holy, fuck! I'm cumming.' She groaned.
It was at that moment that it clicked in my mind that girls orgasmed too.
'Girls do that too?!?!' I asked, freaked out, and again hard as a rock.
'Do... what?' She panted, as she was calming down.
'Cum!' I exclaimed.
'Well yeah! Why else would we masturbate?' She asked.
'I... don't know.' I laughed.
'Looks like you could use another go.' Chloe said, nodding toward my hard cock.
'Yeah, but I'm tired.' I said.
'Here,' She said, reaching over and grabbing my cock. 'Let me do it for you.'
She was a pro at handjobs. She was pumping and squeezing and turning in ways I had never felt before. I was in heaven. I lay back as she worked on me. Eventually I came again, not nearly as much as I did before, but it felt just as great. We laid there, spent.
'That was awesome.' I said.
'You're welcome.' Chloe giggled.
After a little while, we both cleaned up a bit and went to bed. I wish I could say, like a lot of people on here, that this was the beginning of many experiences. But it wasn't. All in all, we probably only masturbated together four or five more times in the next three or four years. But we were much closer and much less modest around each other (at least when our parents weren't around.)Chloe and I haven't done it together in over a year. She is in a serious relationship and I'm getting enough action to keep me happy at college. I'm just glad we were able to have the experience that we did and that the outcome was what it was.