My mate has been with his wife since we were all 16 and I have known her for over 20 years now. When we were 23 her mother was housesitting this big house for a client and a few of us went there for a barbecue.
The housesitter must have been between 45 and 50. She was in good shape and sexy in a cougar way, a hot mom whose wealthy ex husband had divorced a few years before when we were finishing school. She was in between boyfriends and definitely enjoyed having a few young guys around.
Her older daughter and her friend would have been about 25 and they went out to a club while the rest of us ate dinner and drank wine out on the balcony. Everyone else went to bed quite soon after dinner, leaving myself and the housesitter out on the balcony finishing the wine.
We started looking at the stars and when I turned down from looking up she pulled into me. I was pretty drunk and was living in the moment so I kissed her back in a deep, sensual way that lasted a while.
After some giggling and awkward conversation it was just a matter of time before the situation escalated. We went to the master bedroom and I threw her down on the big bed.
After some more kissing her top came off pretty quickly, revealing a pair of perky tits with hard nipples. I got my mouth on those quickly, smacking them with my tongue before moving up to suck on her neck.
By now she was clinging to me and bucking her hips, signaling that the pants should come off too. I whipped them off and started rubbing her pussy over her panties. She was moaning my name and whispering dirty things in my ear and I buried my face in her tits again.
I pulled the back of her knees so her ass went to the edge of the bed, then lifted her panties off, revealing a neatly shaved pussy with a landing strip just above. I buried my face in there, licking gently between her slit and flicking her clit with my tongue. She grabbed the back of my head as I pushed my tongue as deep inside her as it would go. She started grinding my face.
I stood up and unzipped, my young cock rock hard and ready. She was lying on her back with her legs spread for me. I slowly pressed my shaft between her lips and knocked the clit with my head.
Things didn’t go much further as we heard people laughing and chatting at the door. Her older daughter and her friend had come home early as the club had been quiet.
We both panicked, if the daughter found us she would be equally mad at her mom and her youngest sisters boyfriends friend who was busy giving it to her.
I bolted into the bathroom, got my pants on and pretended to be taking a shit in the en suite of the main bedroom on the other side of the house from where I was meant to be sleeping, in the middle of the night.
The housesitter managed to get her clothes on, but her daughter was surprised to find her awake. I eventually decided to make a run for it back to my room, but ran into the friend. I mumbled something about being drunk and lost and went to bed.
The older sister definitely suspected something and a few weeks later I got a message from my mate saying ‘I just wanted to check if you hooked up with Emily’s mother?’. I flat-out denied it and never heard anything else about it.
A few years later the couple got married and that was the next time I saw the mother. She was the mother of the bride and had a boyfriend, but I made a point of getting her on her own and asking how she was doing. Although neither of us mentioned what had happened that night.
Source: reddit.com/r/gonewildstories/comments/hoolyj/sneaking_around_with_milf_housesitter
Dang! So close!