I've recently discovered this site and it is wonderful!
My sister is 49 and I am 52. We have always been close, unlike many brothers and sisters. Once as teenagers we both got pretty turned on as we had a discussion about sex. One thing led to another and we showed each other our naked bodies, allowed each other to do some exploring with our hands and fingers, and we showed each other how we made ourselves cum. That was really exciting, but we didn't ever do it again. We were just both extremely curious that one day and we learned from each other.
Many years passed and nothing was ever said about that day again. My sister and I both got married and had kids. One day about five years ago my sister's husband simply dropped dead from a massive heart attack. It took her over a year to start resembling her 'old self' in terms of personality, etc. A year after her husband's death, my wife and I divorced after many years of marriage.
About a year ago I was at her house for dinner and afterwards we sat and chatted and we talked about things we did as kids, etc. I said 'remember that day we got naked together and masturbated in front of each other?' My sister smiled and said 'yes, I remember that well. I can't believe we did that! What were we thinking! In hindsight, it was fun,' she said.
'I thought it was fun too,' I replied. Then there was a long pregnant pause between us. It seems two minutes went by. I was wondering if she were thinking the same thing I was. 'It's been a long time but ... I'd love to do that again if you want to,' I sheepishly said. 'I think it would be fun this time too,' I added.
'It's been a long time since I've even done that by myself,' my sister said. She appeared to be trying to deal with this proposal mentally.
'I stroke this thing almost daily,' I told her ... 'and it would be nice to do it with you again after all these years,' I said. 'For old time's sake.'
'You're serious aren't you?' She said.
'Yes, I am ... and I'm getting hard thinking about it too,' I replied. I saw her eyes glance to my lap where I wasn't trying to conceal my bulging pants.
'You are too much!' she said. 'I guess ... gosh this is so weird ... I want to and I don't want to ... so you really are serious?' 'Just one time for old memories ...' She was still struggling with it mentally. 'You are really hard thinking about it?' she again asked.
'Betty, check this out,' I said, and I unzipped my pants and pulled my throbbing rock hard dick out through the fly in my boxers. 'I'm THIS serious!' I took my dick in my hand and slowly jacked it as she watched me.
'Damn ... you are too much!' she said. Then she stood up and started taking off her clothes and I stood and stripped totally naked. I wrapped my arms around my sister's naked body and felt her smooth soft breasts and perky nipples against my chest, as the underside of my upright dick felt her hairy bush nestled aqainst me. 'You feel so nice,' she said.
'You do too,' I said, and your body looks wonderful.
'I don't think I've had an orgasm in a year,' my sister moaned.
Her hand found my raging hard-on and my fingers found her pussy and we went to work. 'That feels so good,' she said.
After feeling each other for a long time I said 'let's watch each other like we did that one time.' We both got on her couch kind of facing each other. I started jacking and she started rubbing her clit and fingering her sloppy wet pussy. I could hear the squish squish sound as she fingered herself.
'You have a really nice grown up dick,' she told me with a smile on her face.
'And you have a beautiful grown up pussy too,' I said, my voice almost going breathless. 'Damn this feels good, Betty. I love watching you.'
'And I'm loving watching you too ... oh, this does feel really wonderful,' she said.
I jacked and watched and jacked and watched as she worked her pussy, totally lost in the feeling. Finally I knew I was going past the point of no return and I said 'watch, Betty ... I'm going to cum now.' I leaned back and squirted loads of cum all over my stomach, some squirting to my neck. In about a minute she then arched her back and stiffened and started her orgasmic contractions. It was a wonderful feeling watching her cum after having lost all her desire for sex or masturbation since her husband had died.
After cleaning up I hugged her for about a half hour and she did a little crying, not about what we did, but it was emotional for her in many ways. We never masturbated together again but I think the topic will always be open for discussion.