Chapter 1
My parents died in a car wreck when I was eleven, and from there I was raised by my aunt and uncle. They were good people, but were strict, and generally cold. Affection wasn't the norm from either of them, especially Uncle Mark. Aunt Toni was a bit warmer, but it was still a far cry from life with my parents. They had no children, so taking me in was quite a change for them.
Sex was a taboo subject at their house. There were no discussions about sex at any time with them. I knew from talking with friends at school that most of their dads got Playboy or similar, but those didn't exist at Uncle Mark and Aunt Toni's house, and I wasn't allowed to have sleepovers, so I never saw one.
Somewhere along the way, I did find that catalogs would arrive for Aunt Toni with lingerie ads, which I enjoyed looking through when no one was around. They were incredibly tame, but seeing pictures of women in underwear was still a thrill. At my young age I was very intrigued by nylons, especially.
As hard as it is to imagine in today's world, I was 18 the first time I came. I was down in the basement, laying on the couch, face down, and was looking at the latest catalog's lingerie pictures. I must have been rocking my pelvis back and forth, but suddenly, the sensation changed, and I came for the first time. I was scared at first, which I imagine is normal for innocent boys, but it felt very good, and aside from the cum in my underwear, everything went back to normal. I asked my best friend, Danny, about it, and he laughed, and said, "Haven't you ever jacked off?" I admitted that not only had I not jacked off, I didn't even know what that meant. He said he wasn't going to show me, but that the next time I was looking at the lingerie catalog, I could put some Vaseline or cold cream on my hand and use it to stroke my cock.
Naturally, I couldn't wait for the chance to try this. What his instructions didn't indicate was how much Vaseline to use or what he meant by stroking it, but even my clumsy first attempts felt good, although I didn't cum from them. Eventually, I realized that wrapping my hand around the shaft and going up and down the length of it felt better than anything I'd yet experienced, and before long, I came. Danny also didn't prepare me for was that unlike my previous orgasm, when I had been lying face down and came into my pants, when laying on my back with my pants off, my cum shot out in several long ropes, landing on the catalog, my chest, my face, and even in my hair. I was shocked by the amount and the distance, but fascinated by it, too. I remember wanting to try it again, and being young, it was easy to just pick back I where I left off. I soon realized that even with enough Vaseline, your cock will get sore from stroking it too many times, and that the first cumshot of the day was always the most explosive, even if the second sometimes had a more pleasurable sensation.
For the next several months, I found myself stroking my cock every chance I got. I branched out from the basement to my bedroom and to the woods behind the house. Once, I even came onto Aunt Toni's dirty nylons, but the idea of staining them made me decide that was a bad idea, so I quickly washed them and never did that again.
One summer evening the summer when I was 19, Aunt Toni was complaining about her feet being sorer than usual. She was on her feet for hours at a time at work, and her feet and calves would ache by day's end, so it wasn't unusual for her to ask for a foot rub in the evenings. This particular evening, I suggested that she lay on their bed and that I would rub them, and that afterwards, she should soak them in Epsom salts. She thought it was a great idea and headed in to lie down. It was a warm evening, and I was in a t-shirt and shorts, while she had on the cotton dress and stockings she wore to work. She asked if I minded if she left her stockings on, and I naturally said no.
Things started off as normal as could be, with me working the soles of her feet with my thumbs, and eventually massaging her calves. Aunt Toni had very nice legs (she dressed very plainly, and never dolled herself up, but she was quite a pretty woman with what appeared to be a great body), and as I continued working on her calves, I eventually moved up on the bed until I was straddling her left leg.
As I continued working on her calves, I moved up to her thighs. This was further up than I normally massaged her, but as I ran my thumbs up her hamstrings, she expressed how good it felt and how tight the muscles were, so I kept going. Reaching past her knees caused my cock to rub against her stocking-clad calf through my shorts, and it quickly became hard. I was torn between how good it felt and hoping she wouldn't notice and get angry.
By now, I was at the top of her stockings and my hands were rubbing from her nylons up onto her bare skin. She shifted slightly to give me easier access, and before long, my hands are stroking her legs from her knees all the way up her thighs, and my fingers were even coming into contact with the crotch of her white cotton panties. She moved her hips slightly as I did so, but said nothing. As these long strokes up and down the back of her thighs continued for a couple of minutes, I noticed that I could feel the heat coming from between her legs, and that a vertical dark area appeared on the crotch of her panties. Immediately, my mind went from thinking about the massage to thinking about her pussy, and almost immediately, my cock, which had been straining against my shorts as it pressed against her leg, exploded. I managed to not moan, although, in hindsight, between the pulsing of my cock and a change in my breathing I have no doubt she noticed. Her leg stiffened slightly, but she didn't say anything. Fearing that my cum would leak through my underwear and shorts, I moved up off her leg slightly, but continued working on her thighs. The wet spot in her panties was now quite a bit bigger.