I was 18 when my Grandfather on my Mothers side passed away. They were not well off by any means, neither was my family. My dad went to help out after the funeral making arrangements to sell her trailer and car, Gramma wouldn't need them since she was now going to move in with us. We lived in a 3-bedroom house, Mom and Dad's room on the far side from my bedroom and my 2 sisters' in the middle.
Well, I was concerned about the sleeping arrangements now, knowing math I did the numbers and I was odd man out now. I didn't want to sleep on our couch for years and voiced my opinion about it at breakfast.
Gramma said "I Will sleep on the couch. It's not fair to kick The boy out of his room."
"No, Gramma, that isn't right either!" And shook my head
"The only other option was to share your bed then son."
I was horrified at the thought. But it was better than sleeping on our worn out couch.
Grandma is really a sweet woman and has always treated me special, so after considering my options, I agreed to share my room with her.
Grandma was nearing 65 and while she not an overly attractive woman but, she was far from an ugly old hag. I was already in bed when she came in wearing a wore out a faded old frumpy night gown with the top button gone, exposing the top half of her huge tits.
Our first night sleeping together was not a pleasant experience, she snored and kicked all night, keeping me awake for hours. What could I do? The next night wasn't any better, but I fell asleep sooner anyways.
The fourth night I woke up light feeling a pressure on my crotch, it was Grandmas hand. She had laid her hand on my dick in her sleep, I tried to move away but she snuggled up to me and in a sleepy voice said
"Oh Gerald, it's been so long since it's been this hard, it feels so good honey."
Gerald was my dead Grandfathers name. Her hand began to massage my dick in her sleepy state I guess she had forgotten he was dead. Needless to say, my dick didn't care as her hand felt better than mine did, and I didn't as long as I didn't think of her doing it,
I was really beginning to enjoy this feeling. She started to rub my dick even thought I had my Pajama Bottoms on. Mumbling, something about did I want her to do the nasty thing she did to it.
I made a grunting noise and her hand went inside my Pajamas grabbing my dick rubbing her fingertip along the head. I was getting pretty excited at her touch, Then her eyes popped open, and she jerked her hand out, and stared at her hand as if it she had grabbed a rattle snake and started crying saying
"I am so sorry, I was asleep and didn't know what I was doing."
I just gave her a hug and told her
"It is alright, I understand since you had called me Gerald when you first started waking up and felt you touching me. I wasn't sure how to stop you without scaring you."
And I told her, "Grandma, it felt so good I really didn't want to stop you, I'm the one who should be ashamed, not you!"
I gave a feigned embarrassed look
Her shoulders were heaving as she sobbed, saying how she was so lonely without grandpa gone now, and she was so sorry she had ruined out relationship by molesting me. I didn't know what to do or say, so I gave her a hug from behind.
She had turned her back to me in her shame and by doing that I felt my still rock hard dick press into her butt cheeks, I felt like such a goof, but she didn't move away from me, in fact she actually wiggled her ass against me, as she snuggled closer to me.
"I still love you Grandma, it had just been a mistake and we shouldn't worry about it."
She told me I was a sweet, sweet young man and wise beyond my years and we fell asleep with me hugging her. The next morning we had a good breakfast, laughing at silly things with the family, never mentioning anything about our previous nights episode.
Nothing happened again for a few nights, to my great disappointment and then around 1230 the fourth night, I felt her hand on my dick again, this time my dick was outside the opening in my boxers, since I had stopped wearing my Pajamas.
Her hand was moving up and down, my hips had started moving in rhythm to her hand and I started spurting large globs of my hot spunk on her hand and up my belly and chest, all in less than a minute from the time I woke up. I wasn't sure if she was sleeping or not but her breathing was steady, and then I remembered she snored!
"Grandma, Are you awake!"
"Yes." She said softly.
I asked if she had been awake and if she knew what had happened.
"Yes, I'm so sorry, I just couldn't help it, I woke up and it was in my hand and felt so hard and good I just had too! I'm so sorry honey, you must think I am such a nasty old whore!"
I begged her not to say things like that.
"It had just happened that's all, please don't feel bad, I could never think of you as some kind of whore and I really liked it."
My spunk had begun to dry on her hand and my belly so I got up and got a wet rag to wipe it off us.
She smiled at me surprised that I had not being upset.
"Did you really enjoyed it,