I do like to keep a certain amount of anonymity but this happened to me when I was a single guy.
I was back visiting friends and my parents and had gone for a night out. In a nightclub I bumped into my mothers best friend, they'd been mates for as long as I can remember and had met when she had initially worked for my mother. The friend, let's call her Anne, was 10 years or so younger than my mother with a very slim figure and bushy hair. Think of a 45 year old Cher.
I hadn't seen her for ages and we had a really long catch up and a fair few drinks. My mates knew me too well and all made their excuses with a knowing wink or a sly smile, they all knew her too as she was a regular at parties involving my family and friends.
Anyway we eventually left the club and decided to share a taxi home, being the chivalrous type I offered to drop her off first and then pay for the taxi myself. She thought it would be nice to come back for another drink, I wasn't putting up much of an argument and just hoped it was late enough or early enough in the morning that my parents wouldn't wake up.
We got back to my parents and didn't have a drink instead we went into the living room and she proceeded to drop to her knees and grapple for my belt buckle. Ahh needless to say I was hard immediately and she seemed pleased with what I had to offer.
She then proceeded to give me the greatest blow job I think I've ever had and even though I was 23 at the time she also introduced me to my first female on male rimming session.
I then watched her undress, she had little boobs, perky for her age with nipples that I can only describe as like midget gems (a U.K. sweet!). A remarkable slim and tight figure and a big bush (which I love).
She then pushed me into a chair (a chair that is reserved solely for my fathers ass and no one else). Straddled me and gave herself a loud shuddering orgasm that even my best attempts to muffle couldn't stop.
Happy that I'd satisfied her and still be young and relatively selfish I looked forward to enjoying myself and using this milf in a few of my favourite positions. Just as I was bending her over and asking her to spread her ass cheeks for me. I heard a bedroom door open and someone walk along the upstairs hall and into the toilet.
Anne found this hilarious whilst I panicked and wrestled her onto the floor, my hand over my mouth and laying on her to stop her moving, we both laid like that until the footsteps when back along the hall and the bedroom door closed.
Thankfully 'little Rob' was still more than up for a session and after giving an a long and wet oral and rimming session I ended up cuming inside her. I've always played safe on one night stands and she did have a bit of a reputation but the excitement got the better of me.
(I'm friends with her children and part of me was excited about 'seeing where the came from' -yeah I know weird!)
Anyway. We kept on having a bit of a kiss and a cuddle and then she said she was leaving, my chivalry had gone out the window so I was happy to let her walk home alone.
Next morning, basking in the glow of shagging a woman at one time i has referred to a Aunt Anne I woke up early only to find my mother with a face like thunder and my dad with a big grin on his face.
Turns out my parents were awake the whole time but both were too embarrassed to come down and intervene at the time.
My mother just hoped that I'd been sensible (which I hadn't) and that she was a nice girl and worth it (she was)
I didn't go home until Christmas that year about 4 months after Anne and I had had our fun. On Christmas morning she turned up at my parents home and said that she had some amazing news! Fuck I thought she's pregnant and was picturing whatever the 1999 version of Jeremy Kyle was.
Thankfully she had just been proposed to and had accepted, turns out she had had a partner all along!
A lucky escape!
Anne also has two daughters, one of whom I've managed to sext with, but would love to fuck.
Edit - Thinking about this more and just found a pic on my Facebook of me as a toddler on her shoulders
