When I was ten years old, my dad remarried a very pretty woman named Susan. Her mom lived with us too for about three years until I was thirteen.
Her name was Pam, and we called her 'Gramma Pammy'. Pam was probably in her fifties and she was a pretty lady too, and really sweet. She was kind of heavy set but with a firm body and she had huge boobs. She had a very outgoing personality and a great sense of humor; always joking around. She was a wonderful Gramma!
Gramma Pammy was always really nice to me and I was her 'favorite'. She would give me big hugs anytime I wanted and would kiss me and press me against her big soft breasts.
She didn't know it but she was the object of my young lust, and I would act real innocent and snuggle with her every chance I got, all the time I was enjoying smelling her, and feeling her boobs against me.
I was always trying to get a peek of her too, and really liked it when she would take us swimming at the lake by our house in the summer and I'd see her in a bathing suit. She would wear a one piece suit. I remember that I could see where her nipples were when the suit was wet, and one time I got really excited when I saw a couple of her pubic hairs sticking out from under her suit.
One day when I was probably thrteen years old, the thought came to me of seeing if I could find her dirty panties in the clothes hamper.
When no one was around, I'd go to that hamper every chance I got, especially in the evening when Pam would take a shower before going to bed. I'd find my step mom's and Gramma Pammy's undies, which were bigger. I would carefully inspect any stains and get really turned on by their unusual to me smell, and the feel of them against my face.
I was very naive and had not yet gone through puberty, but I remember that I would usually get an erection when I was in the clothes hamper.
Then I got an even better idea. Gramma Pammy's bed room had a window that looked out the side of our house onto a wood planked porch. The window had curtians that she kept closed most of the time. My plan was to sneak into her room and open the curtain just enough to see in from the outside.
One evening while she was doing the dishes, I went in and put the curtain on the window sill just a bit, leaving an opening. My heart was pounding as she finished up the dishes. I knew she'd be going in soon to her room, where she would get undressed, put on a robe and then go to the hall bathroom to shower.
I slipped outside to her window. Would I be able to see anything? Would she see the curtain open and close it?
As I crouched by my viewing hole, she came into her room and turned on the light.. I could see everything! She did not see the opening in the curtain and started taking off her clothes!
My heart was racing and my penis was in full boner in my pants! Her back was to me when she took off her blouse, undid her bra and took it off. She then dropped the shorts she had on and slipped her big white panties off. I could see her big beautiful butt! She then turned to get her robe out of the closet and I could see her tits and her crotch!
Her boobs were about the size of cantelopes and her nipples were big and a very light pink. There was a big bush of brown hair between her legs.
She quickly put on the robe, took her dirty clothes with her, turned out the light and left the room.
I would repeat this adventure as often as I could. Sometimes she would rub her tits when she took off her bra.
When I turned thirteen Gramma Pammy was the cause of my first ejaculation. She was gone one day and I was in her room enjoying her undies when I got a boner. But this time it felt 'different' in a really good way. I had no idea what masturbation was and no clue about ejaulating, but I was about to find out!
I took out my young circumcized boner and it just felt so good to squeeze it! I was twisting it and it kept feeling better and better. I started to feel like I was dizzy and it kind of scared me because I didn't know what was happening, but I couldn't stop because it felt so good!
I figured it all out when I shot my first load of cum; that first spurt went about four feet in front of me! I cleaned up the mess and began pleasuring myself regularly after that.
I would now jack off when I watched Pammy through my peep hole. My dried cum stains could be seen on the wooden porch, but nobody but me knew what it was!
Gramma Pammy was the object of my fantasies almost all the time when I would masturbate, and the thought of her catching me doing it started to be even more exciting to me.
I decided to go for it one afternoon when I got home from school. My parents did not get home till like six oclock, and it would just be me and Gramma Pammy if my younger sister was at a friends house, which was usually the case.
Our kitchen and living room were one big room with a kitchen island in between. There was a big couch that was in front of and perpendicular to the island.
I was sitting on the couch on the end closest to the island and watching TV. Gramma Pammy was in the kitchen getting dinner started.
I started playing with myself through the shorts I had on. The arm of the couch kind of blocked the view of what I was doing, but not completely or at least I hoped not.
I just kind of pretended that she couldn't see what I was doing and hoping she could!
I played with myself through my shorts for quite a while and I was totally hard. My erection was laying against my thigh as I fondled it back and forth.
I was so excited knowing that Gramma Pammy was possibly seeing what I was doing. Could she see me? If she did, would she say anything?
I actually started to get close to cumming when her soft voice slowly said 'I see what you're doing over there'.
Oh my gosh, she had seen me! I froze with a combination of fear and excitment, pretending I didn't know she could see me, moving my hand away and acting ike nothing had happened!
It was just silence for a minute and then she said 'I was beginning to wonder if you knew what that thing was for, now I guess you do!'
I just kind of nodded my head this time and looked straight ahead at the TV.
Another minute went by and Gramma Pammy came over and sat right next to me! I looked at her soft eyes and loving smile as she said 'I'm sorry Sean, I'm not making fun of you. I know what boys have to do, and it's OK'
I sat frozen, hands at my sides now and with my erection still obvious in my shorts.
Gramma Pammy in an inquisitive tone then said what she thought might be the case, asking me in almost a whisper 'Honey, do you want me to watch you do it?'
I knew in that moment that Gamma Pammy was a sexual being too, that afterall, she had been married and had kids! I realized that she knew what men like!
I also knew that she knew that I was very turned on because I was breathing so hard, as I again could only swallow and nod in agreement.
With a big smile and still barely whispering she said 'It's OK Honey, I'll watch you' as she reached over and began to unbutton my shorts!
'Here, let's get it out so you can do it right!' I took over slipping my shorts and undies to my ankles; my boner popping into full view.
Oh my gosh, I was sitting there with Gramma Pammy right next to me, naked from the waist down and my dick sticking straight up in the air!
I closed my eyes and laid my head back on the back of the couch and felt her hand on me! 'Do you want me to do it for you? You're pretty big!' Again I nodded as she began to masturbate me!
After a few heavenly minutes, she let go, took my hand and placed it back on my cock, saying 'You can do it much better than I can, I'll just watch.'
She didn't take her eyes off what I was doing and I could now see and hear her breathing hard as well! Gramma Pammy was turned on too! It didn't take long to bring myself to orgasm and I ejaculated with a small 'bullet' of cum that shot to the top of my T-shirt! The rest flung out in every direction and I worked the last drops out of my swollen tip .
Pammy said with a laugh, 'And that's all there is to that', got up, got a wash cloth and wiped me up.
She never said anything about it and moved away shortly after that. But to this day I'll get birthday cards from her that will say things like 'Don't watch too much TV'. Only her and I know what she means!