I am the youngest of four children. My two oldest siblings were already 10 and 13 before my mom and dad decided to have two more. My sister is only 11 months older than me. Because we are so close in age and the fact that we are homeschooled out in a rural part of the state and therefore mostly isolated from other kids our age, we have always been very close. By the time I was seven our older siblings were off to college and it was just the two of us. My mom gave us lessons for several hours a day and then we were mostly left to ourselves. Our family is very conservative but, I think, balanced. We go to church twice a week, but our parents have raised us with a healthy respect for other cultures and religious beliefs. When it comes to sex, we were given the strait facts, me from my dad and Esther(my sister) from our mom when we turned 13. We have been taught that sex is a private and sacred thing only to be shared between a husband and wife.
Of course when I hit puberty I started to get more curious. I was more self conscious about my body and started to notice my sisters' developing body as more than just a brother. We used to walk down to a small pond about a mile from our house and go swimming in the summer. We always changed, one at a time, behind this giant willow tree on the bank that we called the changing tree. Every once in a while I would catch a glimpse of my sisters' bare backside or the side of her developing breast when she slid on her suit and I would feel a stirring in my shorts. But I was shy and embarrassed. She was still my sister after all and I knew it was wrong to invade her privacy that way. Unlike some families I read about on this site, nudity was not accepted as part of family life and changing and bathing was done privately behind closed doors. Every once in a while I would catch her stealing glances at the front of my shorts though. I eventually realized that she was just as curious as me.
I discovered masturbation and it became a regular habit about two to five times a week depending on my mood. I was always careful to dispose of the Kleenex I used to clean up with in a discreet way so as not to arouse suspicion. Masturbation was not covered in my parents' basic sex-ed instruction, but I was smart enough to figure it out on my own from books I read at the library which fortunately described it as healthy and normal. So even though I didn't necessarily feel guilty about it, I knew it was something private that I probably shouldn't talk about.
The summer I turned fourteen my parents joined a bridge club on Friday nights with some other couples from church. Most of them had children ranging in age from two up to nine. My parents told me and my sister that if we came along as babysitters while the adults played cards we could earn a little spending money. For the most part the children were well behaved and usually by the time the adults were finally done with their card game they were asleep. The house they met at was about a forty-five minute drive from our house. On the drive over Esther and I would read our books, but on the way home it was late and too dark to read so I would lean up against the window and she would put her head on my lap and usually doze off.
This went on for several months. Then one night, for some reason, as we drove home I started to get one of those spontaneous erections that boys that age often get. As my penis extended down the leg of my trousers and hardened it pressed right up against Esthers' cheek as her head rested in my lap. I didn't dare move. I couldn't tell if she was asleep or if she could feel anything, but I was petrified that if she figured out what was going on she would freak out and tell our parents. As you might imagine, however, the more I tried to make it go down through the power of my own frantic will, the harder I got. I could literally feel it pulsing against the pressure of my sisters' head holding it down inside my khaki shorts and boxers. I closed my eyes and tried to think of the most repulsive things I could, anything to get rid of my erection, but all at once I felt her head move in my lap. I was so hard and sensitive that I could feel the contours of her cheek and eye socket as they moved over the head of my penis through my pants. I froze, not daring to breath. There was no way she wouldn't feel my erection if she was awake.
Then, to my shock, she shifted slightly and placed her hand under her cheek resting palm down on my thigh with her finger tips resting on my penis. I began to feel light headed suddenly as I realized that she was touching me intentionally, also that I hadn't drawn a breath in the last thirty or forty seconds. I slowly exhaled as I felt her fingertips move back and forth very slowly and lightly over the obvious bulge. My head was spinning. I had no idea what she was up to, but what could I do? If I called attention to the situation my parents sitting in the front seat of our station just a few feet away would surely notice and then who knows what would happen. I was trapped. All I could do was sit there feeling the amazing sensation of someone other than myself touching my penis and trying to overcome the internal conflict of having my world view turned upside down.
Krista was not touching me in such a way that would make me cum, but my erection wasn't going anywhere either. After about ten agonizing yet wonderful minutes we were pulling into our driveway. As the car came to a stop Esther rolled over onto her back and, with her hand still on my penis she looked me right in the eye gave a faint but very sweet smile as if to let me know that everything was ok. All I could do was stare back into her eyes. She got up without a word and climbed out of the car following my parents. I sat there for a few moments trying to process what just happened before I pulled myself together and found my way into the house and up to my bedroom where I masturbated to the most powerful orgasm of my young life.
This incident was the first in a series of events that changed my relationship with my sister for the better. This post is already too long, but I will share more later if people want to hear about it.