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Sex with an old lady, my boss

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

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Old 05-12-2009, 01:16 AM   #1
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Join Date: May 2009
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Default Sex with an old lady, my boss

Seems like a lot of people here had sex with an older lady and I did too.

I had sex with a mature woman last summer which was my boss and owner of the restaurant I was working at. First off, let me say that the woman is wacky and never thought of her sexually. She's about 50, loud, obnoxious, a chain smoker with the loudest most horrible laugh you'll ever hear. She has an ok body, big tits, light brown/blonde hair, Italian, too much makeup and flirts with everything that has a dick.
While being fairly sexy, she never got any dick it seemed probably because of her horrible laugh and personality. At work she was always telling dirty jokes. This woman's mind was so much on sex that we, the employees, once bought her a big black dildo for her birthday. She thought it was the best gift she ever received. lmao

Anyways, one night she asked me to stay over late to move a bunch of boxes into her truck. I did stay and helped her, she thanked me for it and offered me all the drinks I wanted. She insisted and we sat at the bar. Since I was driving I only had a beer but she had 3 glasses of wine and drank them before I had time to finish my beer. I could tell she was horny as hell, she was heavily flirting with me. As I said, I never really was interested in her but I was getting horny and started to flirt back. She told me I had a great ass, I told her she had great tits! She asked me if I wanted to see them, I said I'd love to.
She had great tits indeed and I started to get a serious boner. She noticed it, gave me a sleazy smile and told me to follow her to her office. She then told me that she wanted to see my dick. I took off my clothes and she did the same. Now this woman had the hairiest pussy I have ever seen. It looked somewhat trimmed yet it was thick and dense. I always preferred smooth shaven pussies but oddly enough, it didn't look bad on her. My hard-on was raging, she grabbed it and started to stroke it while I was fondling her big tits. I felt she wanted to kiss me but that's one thing I didn't want to do. I started to finger her extremely wet pussy and she was screaming in no time. We both got on the sofa, horizontally and started to masturbate each other. She came super fast then I asked her to suck my dick which she did. I came right in her mouth and painted her face with cum using my dick!

I actually started to really get into mature women after that episode!
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Old 05-13-2009, 09:54 PM   #2
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that's actually a pretty funny story. did the relationship continue? did you end putting your dick in her?
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Old 05-15-2009, 12:10 AM   #3
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haha great one man! I love older women with sleazy smiles
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