happened many years ago but impossible to forget
I remember when I was 18 staying with my grandmother Bess, who was in her late 50s then. My parents had very little to do with her but she was kind to me when I was a young teenager so I always kept her address and phone number. In fact, I didn't even bother telling my parents I was intending to stay with her for a weekend, as by that time I was virtually living away from home anyway.
As this was part of a long solo interstate trip for me with no rush to complete it, a stopover with someone I knew was welcome. I hadn't seen Bess for a couple of years, but apart from looking a little older she was her usual cheerful self when I came visiting. Bess lived alone and did most of the talking right from the start. She greeted me in a loose, comfy cotton dress and didn't seem to be wearing a bra. I also noticed I could see through it when she stood in the light and couldn't make out a panty line, but imagined she was wearing them anyway, as my mom and sis always did. She wore makeup and lipstick though and her house was neat and tidy throughout.
In spite of the age difference, I saw Bess for the first time as the sexy lady she once was. She could be provocative and a tease if she wanted, and I am sure she was enjoying giving me an occasional peek down her boobs. She bent over long enough for me to glimpse a nipple, then moved away as if she knew I had seen too much.
After dinner (she was a good cook) we sat and watched her usual TV programs, which I found boring. Bess fell asleep with her feet up, and after making sure her eyes were closed I peeked up her dress and saw only bushy hair. So, no panties either. I couldn't see any more than that, but just then she sighed and moved her legs apart slightly, leaving me in no doubt. That made me quite horny and I decided to take a risk and get my penis out while watching her. To improve the view I pulled her skirt back a little so she looked quite wanton in her sleep. It was all I could do not to make a noise while I jerked off, but it was a marvellous cum and my hankie was soaked.
Just then, Bess began to wake up. I had no time to pull her dress back down. She opened her eyes, realized how far her dress had 'crept' up, noticed me and said 'Oh my goodness, I hope I didn't embarrass you.' I said something non-committal, then Bess asked slyly, 'Did it turn you on?'
I blushed, not knowing what to answer. 'Come on,' Bess coaxed, you're a normal man just like everyone else. Tell me.' Under pressure, I confessed I had noticed and it had made me horny. Although apologetic, Bess seemed to be strangely pleased that I had taken an interest in her.
After that, clothes seemed to matter a lot less in her house. As I showered, I heard her knock but walk into the bathroom anyway on some errand, glancing down at my crotch as she departed. I was hard again by the time I dried myself and barely covered my erection with an old dressing-gown belonging to her late husband, which she had lent me.
By then it was late evening and I was a little shocked to meet Bess walking around in a virtually transparent negligee. She joked about my having seen the best of her already. I went to bed and needless to say jerked off to what I had seen.
The next morning Bess knocked on my bedroom door to tell me breakfast was on its way. This time she wore a white chenille dressing-gown and I was willing to bet she had little or nothing on underneath. Instead of leaving immediately, she stayed and chatted, even leaning over to give me a morning kiss. Her gown parted and her breasts swung free. I impulsively put my hands on them. Instead of pushing me away, Bess cooed 'Ooh, that feels good. You certainly know what to do.'
Suddenly my wildest dreams came true. Bess threw off her gown and my blanket, straddling my legs and seizing my cock which she began to work up and own. I realized she had been waiting for this opportunity. With each movement of her hand she ground her warm, now slippery fanny against my shins, even letting me put inexpert fingers up inside her. Realizing I had a lot to learn about all this, we ended up kissing while she milked me off with one hand, rubbing herself below vigorously with the other. Her perfume and woman smell soon carried me over the edge.
In that single weekend, Bess certainly helped me make up for lost time. After her, I totally lost my shyness around older women and discovered to my amazement that many other seemingly reserved ladies seem to lose all their inhibitions once they get the chance to see and touch a young stiff penis (mine). They have all taught me so much more than any of my younger girlfriends ever did. Although Bess and I eventually went 'all the way' with each other, that is not a story for this forum.