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Older Woman-First time

Mature Women / Cougars / MILF Stories (Written By MEN)

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Old 05-02-2013, 07:22 AM   #1
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Default Older Woman-First time

I will never forget my first time with an older woman. I was just out of High School and very sexually active with girlfriend but most of that was the usual teenage quick screw. I had two jobs that summer and one was in a grocery store and we delivered groceries. I had to go to this ladies house and took the groceries in. She was in her 40's and a blond knock out. After i sat the groceries in she talked to me about what I was going to do with my life and was I going to college and such. We discussed my plans and when I got up to leave she asked if I could stay a little longer because she was very lonely. I told her that I didnt know and she said she would call the boss and take care of it. She called my boss and told her that she needed a few things done around her house and wanted to know if I could stay and help her out. As she usually spent about $100.00 a week in this small store the boss said sure and got me on the phone and told me to take care of the customer. I sat back down and "Mary" began to ask some very personal questions about my sex life and what my GF and I did. I told her some of the things we had done and she asked if I had ever had sex with an older woman and I said no. She stood up and removed her shirt and bra and then straddled me and began rubbing her big tits all over my face. She had the biggest nipples I had ever seen in young life and I had enough sense to begin sucking on them. After a few minutes of this she got up and told me we were going to the bedroom. I followed her and she slowly stripped her shorts and panites off and asked if I had ever eatten pussy. I said that I had and she told me to get my clothes off and eat her. She laid down and I got between her legs and slowly began eating her and she began moaning and thrashing and said "Its so good". She soon came and told me to get my young dick in her pussy. She opened her wide hips and I started toward my target and I stopped long enough to ask her if I needed a rubber and she said that she had been fixed several years before so that was no problem. I entered her valley and she screamed to fuck her hard and fast. At 18 I did just that and soon was ready to blow my load and I told her that I needed to cum and she said to slow down so I did and was able to hold back. After a while she told me to speed up again and we went through this cycle a couple of more times and I told her that I had to shoot and she said go ahead. I filled her pussy full and when I pulled out she pushed me back and started sucking me to keep me hard and soon she rode me till she came and I came again. She told me if I delivered groceries at least twice a week she would tip me well. I did all summer and I learned all about sex that summer. She moved off soon but I saw her a couple of years later while in college and she had me come to her house and earn my Masters degree.
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Old 05-02-2013, 02:46 PM   #2
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Age: 64
Gender: Male
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She was a good teacher and certainly made you appreciate "school"!
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