I was 27 when the following took place. My mom-in-law (Penny) was around 48.
Every second or third weekend my wife and I would travel the 80 or so kilometers to her folk's small farm. They were not really farmers, just liked the space and the quiet. They had also built a small cottage on their property for my wife's grandmother who was fairly mobile but needed a bit of help occasionally. It was my wife's habit to drag me down to gran's cottage every Saturday we were visiting to see the old dear. I would stay a while then leave them to chat for an hour or two.
I preferred being around Penny anyway. She has brown, curly hair, really good legs and big tits. She had even discussed getting them reduced with my wife and I, not sexually but quite seriously. I managed to convince her otherwise saying I thought it was not good to fiddle around unless there was a real problem. I loved seeing them swing free as she seldom wore a bra when at home.
What I really liked was when she decided to take a dip in the pool. She is totally not fashion conscious and wears a one-piece but does not shave either her armpits or pussy. In her bathing suit all the hairy bits come to life. Usually after swimming she'll put on a T-shirt after rolling down the top of her suit. She goes for those baggy ones and I always position myself to see through the drooping armholes and catch glimpses of her dark brown nipples.
She is a bit of a dominant person although really kind and very friendly to me. She quickly caught on that I was quite prepared to do almost anything she requested and often had me helping out. Tim, her husband and my father-in-law, is always off traipsing around the farm fixing pumps and stuff.
One Saturday after swimming and BBQ-ing I was dragged off for the usual visit and after about 30 minutes ducked off. Penny had been wearing a specially droopy shirt and I wanted to get back to perving at her tits. I helped her finish clearing up, Tim was gone as usual, and then announced I was going to take a shower.
I finished off and returned to the bedroom we always used, dropped the towel and started massaging my cock in front of the window. We never close the curtains as there is no one for miles and nobody ever goes round that side of the house. Just then I saw Penny round the corner to water some flowers there. I could not help myself but I just wanted her to see me naked. I turned from the window and naked started getting out some clothes. I kept a check on her using the mirror and soon she noticed me in the bedroom. She stopped and watched me thinking she was unobserved.
I moved around a bit giving her a good look at my swinging cock, until I felt myself hardening. I had to have a reason for getting hard so I started playing with it again. Out of the corner of my eye, using the mirror, I saw Penny staring at me. After a short while she disappeared back around the house. I hoped I hadn't blown it. A second later the door which was not closed but ajar pushed open quickly and Penny came in asking if I'd like a cup of coffee. I wasn't expecting it but she'd obviously wanted a better look. I was surprised and she feigned surprise. Apologizing and backing out saying sorry but that it was OK as I was her son after all. I nodded and she disappeared. When I emerged from the bedroom things began a bit awkwardly but she quickly said that we should not let it worry us as it was a pure accident. I asked if we should mention it to the respective spouses and she said she saw no point…I agreed.
That night after everyone was bathed we sat around the TV, chatting and watching a bit. Tim always turns in first and my wife Mainie shortly afterwards. Penny wears the same baggy T-shirts to sleep in and I always get a good look at her legs while we sit up late chatting. We have always been able to talk and this had not changed since our encounter.
She quickly turned the conversation to our "meeting" saying that I should not be embarrassed as it was her fault but she did not realize I was dressing as the door was not closed properly. I assured her it was OK. She then made a totally unexpected request/demand. In her friendly but forceful way she asked me to massage her foot as she felt a cramp coming.
I reached down and picked up her small, sexy bare foot to rub it. She suggested I sit on the floor to do it. I sat facing her on the floor and started massaging. She rested her other foot on my lower leg. I had a good view up about half her thigh and took advantage with occasional peeks. She kept her eyes glued to the TV. After a few minutes she remarked how good it felt and rested her head back on the sofa. Her legs parted a bit more and I could see her white panties, stark against her brown tanned thighs.
I massaged her foot lovingly dropping my head and wishing I could kiss it and suck those lovely toes. After about 10 minutes she, without moving, said I should do the other one. I looked up and saw her watching me stare at her foot. I placed the attended foot on my thigh and took up the other. The position now opened her legs even more and her full, dark bush came into view. Popping out each side of the white panties. I admired it for a second and looked up at her. She was still watching me. I felt myself redden and she just lay back against the sofa again. I continued my massage and stared at her legs and panty covered pussy.
Once again after about 10 or 15 minutes she said it was great and fine. I looked up from her pussy to again find her watching me. I placed her foot on my other thigh but continued holding it. I stroked both insteps, up to her ankles and back to her toes. She watched me. I was hard by now and in the shorts I was wearing without underwear my hardon was plainly outlined.
Unexpectedly she nudged it with one foot and said, "You need to finish what you started earlier". I spluttered a bit and still with her foot against my cock she repeated it. It was my turn to say how sorry I was. She stopped me and told me to just get on with it and it was quite a normal thing to happen. I started to get up to go to the bathroom when she told me to stay there and do it. I didn't argue and sat down again. I pulled my now very erect penis out of the leg of my shorts and started squeezing and sliding my hand up and down it.
I was teasing myself. Looking up at her legs and pussy, which was still on show, I didn't want to come too quickly. She raised a foot and rubbed it against the underside of my cock. I let go and left it to her. It was so sexy. Her pretty toes rubbing and squeezing my cock. She suddenly raised the other foot to my mouth and a bit roughly pushed her toes between my lips. "Suck", she said rather roughly. I did and she continued rubbing my cock, sometimes pinching it rather painfully with her magnificent toes.
After a while she swapped feet. Rubbing my swollen member with her now saliva slicked foot and pushing her dry foot deep into my mouth. I held it gently, running my tongue over the soft underside of her toes and pushing between them. She moaned softly and then announced "I think I need you to do this for me whenever my feet need attention. In future whenever I need a foot massage I'll be calling for you". She took her foot out of my mouth and grasped my cock between them. Pulling hard up my shaft. I grimaced a bit. She asked if it was sore and I said it was a bit. She giggled and said she knew I was tougher than that and pulled up hard again and again making me rise up with each pull.
I was close to spurting now and she seemed to realize it. "Take over", she commanded and let go. I grabbed my cock and she stuck her foot in my mouth. I wanked my stiff, slick cock while sucking and licking her foot. As I came she put the other foot under my cock so that I squirted cum onto her shin and leaked onto her foot.
Once I had squeezed the last drops out she rubbed her feet together spreading the cum over her lower legs and feet. "I'm going to bed she announced, turn off the TV when you're finished. And…. I'll need you again soon". With that she walked out and off to bed.