I was so lucky to have a grandma like her.
One hot summer afternoon when I was 14 my mom sent me round to my grandma's house to help her with some gardening chores. This was about my third or fourth trip there as grandma had a lot of garden rubbish which needed removing and I think mom was happy for me to be out of her hair for a while.
Gran was in her early fifties, tanned and, as I remember her, with a better figure than many women her age, maybe slightly on the thin side. She and I got on well, no doubt she was glad to have a strong lad like me around to help her. When I arrived, she was lying on her tummy reading a book under a sun umbrella, wearing a light blue cotton dress. Greeting me cheerily, she got up and I noticed she was braless. My teenage penis began to tingle and swell.
As we moved around her garden, I became more aroused, taking every opportunity to peek at her breasts when she bent over, till finally she had enough and said, 'Let's sit down and talk.'
At first I didn't know what she meant, but then she said 'I know you were peeping at me, but I didn't mean to tease you, sorry. I usually go round like this at home.' She made it clear that not all women like being peeped at. Then, looking at the tent I had made in my jeans, she added, 'Why don't you show me that thing there?'
Although a bit shocked at the turn of conversation, I shyly unzipped and took my penis out for her. 'Nothing to be ashamed of,' Gran said approvingly, looking hard at it. 'Your mom should be proud of you.' I said nothing as all I could think of was Mom's anger when she last caught me masturbating. When I related that to Gran she shook her head and said Mom should have known better. She asked me did I masturbate regularly and I told her at least once a day, sometimes twice. Gran smiled.
'Come inside and let's have a chat about it. The garden can wait.'
I followed her indoors with my penis still poking out and starting to rise again at the prospect of what might happen, while my heart beat faster as I hoped no neighbours were watching. As soon as we were inside, Gran took off her dress and stepped out of her cotton panties. 'See? I like to go nude at home.' She grinned at me. 'Why don't you take your clothes off too while I fix you a cold drink?'
I had never seen a nude woman before, let alone stand naked in front of one, and the effect was electric. I walked around her kitchen exhilarated to be in her presence like this. Gran then jokingly dragged me to her bedroom with my penis in her hand, sat on the edge of her bed and hugged me to her so my slippery stiffness rubbed against her breasts. I soon exploded helplessly in an orgasm that shot cum right up to her chin and down her legs.
After cleaning it up, she pulled me down onto her bed and cuddled me for nearly an hour while explaining a whole lot about sex and love I hadn't ever heard before, not even from my somewhat prudish parents. When she could see I was becoming erect again, Gran applied some lotion to my penis and asked me to try to hold on and make it last. She made a little vagina for me with one hand while she brought herself off with the other, so that my second orgasm with her followed almost immediately. Although she let me touch her little button she wouldn't let me go any further that day and made me promise not to mention what we had done to anyone, especially my parents.
Needless to say I felt a foot taller when I reached home and when Mom asked what took me so long and did I have a shower at Gran's place I replied that we had both worked very hard and yes, I cleaned up there before coming home.
Maybe I'll tell more about my affair with Gran another day.