When I was about 15, I used to stare down the top of my best friend's mother's top whenever I got the chance. She had amazing round, full breasts, and looking back now I know she must have realized I was looking because I was not too subtle.
One day I rode over on my bike to see if my friend, Brian, was home. He wasn't, but his mom, Pat, was in the kitchen wearing a bikini. She was about to go out and suntan and asked me if I'd rub some oil on her back. Looking back over 20 years now, it seems like something from a bad issue of Penthouse Letters and I kick myself for not being more bold.
She led me outside and handed me the oil while she sat down and waited for me to apply it. I stared down the front of her top and got a good look at her round breasts. I had gotten better looks times she'd bent over in tanktops. Sometimes I could see her dark hard nipples inside her white bras. This time I never saw as much.
I slid my hands over her back and shoulders and finished up as quickly as I could because I was nervous and hornier than I'd ever been in my life. I continued to stare deep into her cleavage as she leaned over as I rubbed her back and shoulders. After a while I asked her if that was good enough and she said it was. I hopped on my bike and quickly peddled home to jerk off, suntan oil still on my hands.
I've always regretted never trying to feel more because I'm sure she would have let me. For all you younger guys reading this: it doesn't always pay to be shy. Take a chance sometimes. I see Pat around town occasionally, and she always gives me a warm smile and asks me how I am, and I wonder just what have might happened that afternoon if I weren't so shy. Thinking about it still turns me on, and I like to fanticise about what could have been. That afternoon I ran into my bedroom and jerked off while I thought about Pat's amazing tits, but it wasn't the last time I did that.