Probably one of the most embarrassing moments of my life.
When I was a senior in high school I visited a few colleges trying to decide which one to apply to.
I bought a few pairs of slacks that needed to be hemmed and my mother sent me to this woman who I had known since I was a kid. She was a friend of the family and had been hemming my pants since I could remember.
I walked over to her house and rang the bell.
When she answered the door she was wearing a white robe and as usual I enjoyed seeing her because she seldom wore a bra. Which wasn't unusual but the fact that she had these huge tits with nipples that you could hang your coat on. I used to love to see her in a tee shirt and no bra.
I follow her downstairs to her sewing room. She sewed curtains, and clothes on the side for some spare money.
As usual since I could remember I would take my pants off, put on the new pants, stand on this platform while she measured and marked the pants.
It wasn't like you stood there in front of her and took your pants off while she watched. She would always be doing something, not paying attention while you switched pants. Not to mention that she had known me since I was just a kid.
So I took my shorts off and I had boxer shorts underneath. She hemmed the first pair of slacks then I changed into the other pair. While she was bending over in front of me she had taken off her robe and she was wearing this white pajamas that went down to her knees but as usual she wasn't wearing a bra and when she bent over I saw everything. Over the years I had seen her breasts before but the sight of her bending over really got to me.
After she measured the second pair she told me to go watch tv while she hemmed the slacks.
There was a room down this short hallway adjacent to her sewing room. She kept a tv in that room. As I sat there on her leather couch I watched tv. But sitting there in my boxer shorts my cock started getting hard and I couldn't stop thinking about her tits and how good they looked.
I could hear the sewing machine working. My hormones went into overdrive and I convinced myself that I could certainly hear her working. I had figured that if I heard the sewing machine stop, I would just but my cock back into my shorts and sit there watching tv. I didn't have any tissues so I found this piece of scrap cloth and planned on cumming into it.
So I took my cock out of the opening of my boxer shorts and there I sat stroking away. Pulling my foreskin back and forth. My cock was throbbing as I sat back stroked and thought about her tits as she bent over.
I never heard anything, the next thing I knew she was standing in the hallway facing me as I sat there with my throbbing cock in my hand stroking away like a madman. The shock of it all made me blow my load prematurely as I tried stuffing it back into my boxer shorts.
It seemed to happen in slow motion with her standing there shaking her head and laughing and me trying to stand up stuffing my cock back into my shorts. I had cum all over my shirt and hands and I'm sure a few squirts hit the couch and the floor.
All I heard her say in between laughing was, go wash your hands.
I washed my hands and walked out of the bathroom and told her I had to go. I was terrified that she would tell my parents and she must have saw the fear in my eyes. She gave me a hug with those huge tits pressed against me and told me it was alright and not to be embarrassed, she even apologized. I never got the other pair hemmed I was so nervous. When she walked me out the door she told me not to worry that it was our secret.
It took me at least half a year before I could face her again.