My best friend, Ken, has been my best friend since first grade. We were six years old then, and now we are in our mid-forties.
Ken was athletic, very good looking, and charismatic. Even his voice was velvet. Unlike him, as far as girls were concerned I was the tag along afterthought. It didn't matter that I was smarter and emotionally deeper than him. All the girls made fools of themselves trying to get close to Ken.
Fast forward to our late teens. Ken and me were hanging out, I don't even remember exactly where. Out of nowhere comes walking this gorgeous chick. I mean, hotter than most. She flirted with Ken, and they soon began dating.
Some months later, I was invited with Ken to come and swim in the girl's pool. Ken was always good about that. We were a package deal and he didn't like excluding me even though I didn't have a girlfriend of my own.
As it turned out, the girl had an even hotter mom. Years before MILF became a household word, her mom was MILF+++.
We swam for a while, having normal fun. I went into the house to use the bathroom and that is when I met her mother. We exchanged casual greetings and she hopped up to sit on the kitchen counter right in front of me and continued chatting. She was wearing a bikini that did not hide very much.
I'd be lying if I told you that I reacted with aggressive male testosterone and made an advance. I wish I had, but that wasn't me. Instead, I said, 'I have to use the toilet.'
When I finished in the bathroom I was heading back outside to the pool when she stopped me and asked, 'Wait! Are you scared of me?'
I said, 'Oh...um, no. I was just gonna go back out to swim.'
'Do you like my house?' The question was so far out from left field I could hardly manage a response. 'Yeah...it's nice.'
'How can you say that when you haven't even seen it? Come here...'
She led me upstairs and showed me her daughter's room, the bathroom, the guest room. Then she said, 'This is my bedroom.' Right away I knew something was funky just by the fact that she had a waterbed and silk sheets.
Of course I was flush with blood down there and I had delusions of sex. Looking back it seems ridiculous how I tried to act like my boner wasn't noticeable right through my trunks. I tried every trick to divert her attention. Eventually I picked up a book that was lying on the dresser and held it in front of my full boner and asked, 'Can I borrow this?'
And then it happened. She came toward me and said, 'Don't be embarrassed. You're kind of cute. I'm flattered, not mad.'
She asked if I had experience with women. I lied and told her yes.
'You liar! C'mon, tell me the truth.'
I admitted to her, 'Okay, I haven't really done much yet.'
Her hand felt my crotch and I moaned. I was so hard I thought I was going to pass out.
BUT...just then her daughter yelled up the stairs, 'Mom, where are the clean towels?'
'On top of the dryer, honey!'
'Okay, mom! I see them!'
At the same time she was talking to her daughter she pulled my cock out of my swimsuit. I gasped. Jeezus...her daughter might be walking up the stairs and catch us!
She stroked it a few times and said I had a big dick. I couldn't speak, but I came hard. More cum than ever before or since. Rookie.
Of course I was embarrassed. While I was still shivering she asked, 'Is that better?'
I ran to the bathroom and wiped off and then went back outside and jumped in the pool. Ken and her daughter were too busy making out to notice me, which was good because I was still hard as a rock.
I hated myself a long time afterwards for not even feeling her tits or reaching in her bottom to feel her pussy. It took me until I was in college to get that far. A lost opportunity.
Every time I went back to that house I hoped it could happen again but it never did. We both shared knowing glances many times, though. Even just our naughty secret gave me what I needed to jack off hundreds of times through high school. I am forever grateful and I'll never forget her.
To this day I haven't told Ken about it. Someday I will, but I wonder if he will believe me.