When I was 17, I stayed with my best friend for a few weeks. His mom's apartment was the place to party since his mom let anyone stay there if they shouldn't be driving.
His mom was agreed a milf by everyone. petite, blonde and large, perky breasts. around 40 at the time I think. More than once while me and other friends were there, she'd insist putting on 9 1/2 weeks at either the strip scene or the sex scene in the rain. Got me hard everytime. Maybe she enjoyed our reactions.
So, I slept on the couch one night and in the morning, his mom had to go to work. I heard her getting into the shower down the hall. In my half awake state, I pulled my cock out through my boxers and started stroking it. I was hard almost immediately thinking about her washing her body and the water dripping down off of her long nipples.
A few minutes later, I heard the water stop as she finished. I pretty much ignored this and kept stroking. I knew she'd go across the hall to get dressed of course, so didn't stop my hand at all.
Several minutes must have passed and at that point I was deep into it and oblivious to anything else.
Then I get woken out of my fantasy when something lands at my feet. I open my eyes, hard cock in hand, and she is walking into the kitchen, which is located near the front door. What she threw on the end of the couch was the towel she had dried herself with. she drank some coffee and I remember her looking through the kitchen bar window. I was a little stunned but very excited as she said nothing but 'go ahead' and drank her coffee.
My adrenalin had kicked in as I closed my eyes and started jacking off very fast. Her watching brought me to orgasm quickly. I cupped my balls with my other hand and within a minute or two, I thrusted my hips upward and shot all over my chest. I came really hard and some even reached up to my neck.
I lay there panting while she grabs her keys and things.
I heard her open the door so I looked down the hall at her and she turned around and said 'Bye James, have a good day'. In between breaths I managed to say 'Bye'. As she left I grabbed the towel and cleaned the cum off myself.
After that incident, the only really exciting thing that happened was her having to use the bathroom while I showered once. I jerked off that time too but I don't know if she knew it or not.
Nothing tops that morning though.