Grandma taught me to never be ashamed of masturbation.
When I was 18, my parents had me stay with my grandmother for a month one summer. She lived alone in a small house on the poor side of town. I was there to repaint the house, which needed a lot of work.
It was a particularly hot and humid July when I temporarily moved in with my grandma for a month to repaint her house. My home was three hours away so my parents thought it would be best for me to stay there until I finished the job.
The house was small, two bedrooms, and my grandma lived there alone after my granfather passed away several years prior. I was eighteen that year, and my grandma Ida was around 60 if I remember.
I started out sleeping on the couch, since grandma Ida had the master bedroom and the spare bedroom was floor-to-ceiling with boxes, sewing equipment, and assorted things. There was just a since small window air conditioner in the house, and it was in Grandma Ida's room.
It was miserably hot trying to sleep in the stuffy living room, especially after days in the sun painting the house. After about four days, I suppose I was complaining about the heat in the house. Opening the windows was no relief, as a heat wave was solidly in place. One night at dinner Grandma Ida said I could move in with her in the bedroom where the air conditioner was.
To save money, Grandma only turned on the air conditioner right at bedtime to save money. So that night I washed my face, brushed my teeth and came into the bedroom just as she was turning on the a.c. I felt a bit awkward, but at the same time I hadn't slept well in days and was miserable from the heat. I got into the bed with my clothes on, but Grandma Ida quickly told me to strip down to my underwear to sleep in. She went into the bathroom to brush her teeth and while she did that I did as she said, feeling awkward. From the other room she told me to lay on top of the sheets until the room cooled down.
She was talking to me about the paint job I was doing on the trim, asking about progress as she crossed the room and went into her closet, closing the door. She came out wearing a worn out nightgown, shutting off the light to the closet and walking over to sit on the opposite side of the bed. She turned off the overhead light, leaving a reading light on next to her side of the bed. She then laid down next to me, propping herself up with pillows and grabbing a book to read, along with her reading glasses. I felt embarrassed and turned on my side away from her. We spoke for a short time and I was quickly to sleep.
This routine repeated itself for a couple of days, and I began to feel more relaxed in bed with my grandma, and actually started talking more. It was a bit strange to be lying on top of the covers in just my briefs with my grandma next to me in a nightgown, but given the heat that summer we didn't have much choice. The a.c. in the window of the room was old and not working properly, so the little cooling it provided was just enough to make it so that we didn't sweat all night.
I was trying to masturbate in the shower, but had fallen off my schedule and was starting to get hornier by the day.
Then about a week after starting to sleep with Grandma Ida it happened: I had had a long hot day moving blocks in the backyard and was particularly tired that night. Grandma Ida and I chatted for a bit and I fell asleep right away, with her next to me reading a book. I remember having a sex dream about a girl at school, and in the dream she was stroking me off. In the dream, as I came, I felt the warm wet sensation of the ejaculation. And then, the realization of where I was and that the ejaculation was really happening. I woke with a start: I was on my side facing Grandma Ida, and my erection had my head poking out of my underwear-I was shooting cum all over the sheets! I lurched, and exclaimed 'oh no!' while trying to roll over. Grandma Ida looked over from her reading and saw another shot of cum jump out and land half on my stomach and half on the bed.
'Oh dear', she said as she realized what was happening. I had rolled onto my back and had managed to get my hands over my cock head, but the cum could not be stopped at that point.
Grandma got out of bed quickly and headed to the bathroom as I muttered something like 'sorry sorry sorry'. I heard her say 'it's OK, it's OK, just relax'. She came back in with a wet washcloth and quickly started to clean up the mess I made on the sheets. I had sat up at this point and she said something like 'it happens to boys, it's OK, we'll clean it up'.
I sat at the edge of the bed not knowing what to do as she left to rinse out the washcloth. Dead silence until she came back in, walking to my side of the bed. 'It's OK, just stand up and let's get you clean up'. With that, she took my hand and I stood. She pulled my underwear off, which had some small cum spots on them and left me standing in front of her with a semi-hard cock and cum on my hands and stomach. She handed me the washcloth, told me to go to the bathroom to clean up, while she brought me a fresh set of underwear. When I came out of the bathroom she had a fresh sheet on the bed and was back lying down and reading. She assured me that it was OK, and to not worry about it. I got back in bed and went to sleep facing away from her, quite ashamed.
The next day, not a word was spoken. I quickly ate breakfast and worked outside all day.
That night, the usual routine of me stripping down to my underwear, lying on top of the sheets in the hot room, and Grandma Ida coming to bed, propping up pillows to read. I was just thinking all would get back to normal when Grandma started to talk to me. She had me sit up and for the next 20 minutes she gave me a 'birds and the bees' talk. She used to be a nurse, and assured me that it was perfectly healthy for boys my age to ejaculate. She then told me that masturbation was a good way for boys to relieve themselves and stay healthy and happy. I was thoroughly embarrassed, as you can imagine. But at the same time, Grandma Ida was kind and sincere.
She described how boys masturbate (which I already knew but didn't let her know that). She said you could use soap or shampoo in the shower to stroke your penis. She said you should use lubricant like vaseline or petroleum jelly, or KY jelly. And that you should have a washcloth or tissues handy to avoid making a mess.
Finally, I thought she was done, as she stopped talking and looked at me, squeezing my hand for reassurance. 'John', she said, 'I've put some vaseline on the nightstand next to you, and a washcloth. I want you to take off your underwear and try what we've just talked about'.
I said that I didn't need to, but she insisted: telling me that she'd been a nurse and it would be OK. And with that she had me take off my underwear. She said that if I 'squirted before bed' that I would not have to worry about accidents like last night.
All of the sex talk had gotten me excited, and my erection jumped out and I obediently pulled down my pants. She looked at me lovingly and told me that I had a beautiful body and to not be ashamed. She said that erections were natural and a beautiful part of becoming a man.
Grandma Ida told me to take vaseline and rub some on my penis. With her encouragement, I put a small amount on. Grandma Ida said to hand her the jar. With that, she took a finger full of vaseline and said 'like this...' as she gently and liberally lubricated my now fully hard penis. She then gave me an anatomy lesson, pointing out the different parts of the penis, including the sensitive spot on the underside just underneath the head. She did this with a gentle finger tip to each part as she described it, my scrotum and testicles.
'Now, rub your penis up and down with your index finger and thumb...' as she showed me the familiar move 'like this' she said as she demonstrated. It was very exciting to have a woman touching me for the first time, and at this point I was close to cumming. She reached over and took the washcloth from the bedside next to me. She wiped her hands off and told me to lay back and relax. She then told me to do what she had done-slowly stroke my penis up and down. I of course knew how to do this already, so I went to work. She layed the washcloth on my stomach, anticipating the ejaculation that was coming shortly. And sure enough, it took me just a few strokes before I started to moan, arched my back, an climaxed. She saw it coming and quickly cupped the head of my penis with the washcloth as I let loose spurt after spurt of hot cum.
'See, isn't that nice?' she said. 'Now never be ashamed of your body, and take good care of it', which I've done to this day.
And so, for the next several weeks I'd find the vaseline and washcloth on the nightstand next to the bed. Grandma gave me privacy each night afterwards while she read in the other room. She encouraged me to 'have a good squirt' before bed. I'd usually be done pretty quickly, and she'd come into bed later to read her books.