No regrets, and love looking back!
By the time I was 15 I was molesting myself 24/7. My sister and I were home after school alone usually three to five hours. I masturbated everyday during this time. I started coming out to get a drink or go swimming in shorts which led to underwear to a jock to being naked. I would walk around bouncing my hard on for her to see. She just looked at me like, 'Whatever'. She was 13 seemed uninterested. I would hide trying to see her naked, spy when she was taking a shower, it had frosted glass but I could still get off.
Our Grandmother came for a visit and stayed in my sister's room, she stayed in mine. When we went to bed, I was naked. She asked why, I said I slept that way. 'Well OK'. Nothing first night, second night I got her to try it, she kept her panties on. Third and last night of Grandmas stay she took her panties off too. I touched her butt and boobs; I got her to play Mom and Dad. We touched each other I laid on top of her trying to explain what happens. I was raging hard and masturbated myself almost unnoticed. She asked what I was doing, I told her having fun like I always did. She asked if she could see, I said OK! I got her a flashlight. She aimed it at my dick; I could ALMOST see her in the glow. I asked her to shine it on her boobs. It took her a few minutes but she pulled the covers off enough to expose her boobs and let me see them for a second. I was done, she gasped at what she saw, and said, 'Wow, didn't that hurt?' 'No way', I said.
After Grandma left I continued my antics walking around with a hard on trying to get my sister involved. It was easier now that the ice was broken. She asked to watch again, so I did it in the living room for her. I begged her to touch it; she finally did, with only her fingertips. I came at that point. She got some on her hand; she laughed and asked again if it hurt.
It took a couple of days but, I got her to skinny dip with me. I hadn't actually seen her naked yet and was surprised she had pubic hair already. I was honestly panting, heart racing, I was shaking. We were in the pool touching and feeling each other. I pressed up against her at the edge of the pool and basically I humped her to orgasm (me). 'Wow, can I do that?' she said.
What seemed like forever, but was two weeks before we tried to get her off. I always did, but didn't think we'd ever figure her out. We rubbed, blew, kissed and stuck things in it. She said she liked it, it felt good, but she never got off. One day when we got home from school she said, 'I did it!' She had a huge smile on her face. I said 'That's awesome, When, HOW?'
'Last night! We were doing it all wrong, watch.' She took her clothes off and taught me how to make her cum. Slow and easy was the key! Circles on clit and slight penetration. The next couple of days we were exhausted! We were cumming nonstop, together and alone at night.
The days she had girlfriends over I would only slightly behave. It was early '80s so boys wore very short shorts. I would make sure my junk hung out the legs of my shorts, and acted oblivious to it. My sister would point out, 'OMG, he's sitting there with his balls hanging out!' Giggles followed. A couple of her friends would go look. I guess the others were afraid too. Over time, two of her friends 'streaked' with us. I was always hard and able to cum. They were scared, I guess, to let me touch them, but they wanted to touch mine. My sister confessed she helped some of her girlfriends achieve what she had discovered. The stories were GREAT!! Naturally my buddies were quick to get naked in front of her, especially since she would return the favor.
School ended for summer break, and that was a cum fest. We lived in a rural area, the pool was just a round above ground, but it was like a resort. We discovered porn magazines and videos, some 8mm and some vhs, in Mom and Dads' room. We also found a vibrator in their room. We used it on her almost daily. I discovered lubrication. My sister turned 14 and continued to develop nicely.
We did this all the time until my senior year when I got a steady girlfriend. Things slowed at that point, but we still very much enjoyed each others company fairly regularly through our 20s.
We are best friends and share everything (we never had sex together). The last time we were together in that sense was six years ago. It just happened; I was replacing a door in her house.
I really enjoyed sharing this.