Where it happened: her house
Langauge: English
Sex: Male
Rating: 6
Category: Straight
My first time wasn’t that great, but it was very memorable.
When I was 15 I worked that summer cutting yards, and one of my customers was a blonde lady in her mid-50’s who lived 2 blocks over. I never thought anything about it, but I always took my shirt off when I did yardwork, and I caught this lady (who was divorced and lived by herself) peeking
from the window in the kitchen watching me work. She would
always do that, but it kinda turned me on knowing that an old lady was checking me out, so I would wear tight shorts on the days I did her yard.
One day she called me inside while she made out my check, and while she leaned over the table to write the check I could see all the way down her nightgown – her breasts, nipples, and a little of her bush. She wasn’t that bad looking, and she was in decent shape for her age (she was rather skinny). I had felt my girlfriend up before, but I had never seen an older woman’s breasts. Well, she caught me looking down her nightgown, and asked me if I had gotten an “eyeful”. At that point I was really embarrassed, so I snapped back “Yeah, and no more of an eyeful than you get when you stare at me from the window.” She then got really
flustered. After a few minutes she asked if I wanted to double what she was paying me, and of course I said “sure.” So she walked over and pulled down my shorts. . .before I knew it she stuck my limp dick in her mouth and was tugging it with all her might.
Eventually she pushed me down on the couch after she ripped off her nightgown. After about 10 minutes I still hadn’t gotten hard, but she got on top of me and tried to insert me anyway. It didn’t work, and she got really pissed. So she had me lay down on the couch and she squatted over my face and told me to eat her out. When I did that I got a huge hard-on, and she saw it and immediately mounted me while I was hard. She bucked on top of me wildly until we both came, and she was true to her word and paid me double that day.
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