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One of my best Grannies is Joan, a well built, sassy redhead from Chicago. She was somewhat stocky but made up for it with the nicest set of large boobs I have ever seen on a granny. They still had plenty of lift and always wore low cut tops; her cleavage poured out of her bra. Now being a big city girl she knew the score when it came to a guy like me. She knew I was fucking other women. I would call her looking for a date and she would ask “who did you fuck last night” I jokingly responded “it doesn’t matter, who I fucked last night, it’s who am I going to fuck tonight, and it’s going to be you.” She replied “don’t count your chickens before they are hatched buddy, I expect dinner, dancing and some romance before you get some of my fine pussy. We both laughed and agreed to dinner and dancing at our favorite club. Well the night went as expected, and by midnight this fine granny had been fucked twice and I had filled her pussy with plenty of cum. On top of that she had given me a. That first fleeting thought Ihad was that well, maybe, possibly yes, I did like the way I looked. Ihad changed so completely that I no longer resembled myself. I'm notbeautiful, like a model, but certainly cute enough to not be merelyplain. My only lasting thought was that I could probably dress as a girland get away with it, which was good because I didn't seem to have anychoice in the matter. It boiled down to wear the dress or leave home,skip the education, and be out on my own, working somewhere I didn't wantto be, earning less than stellar wages and be miserable. I could bemiserable at home and still get the education. All I had to do was dressthis way. My parents had crafted a punishment that was more than fittingin their minds, they had adroitly boxed me in without many options.I let my hand go to my breast, the swelling flesh crowning, so real, andyet so fake. But how would anyone know it's fake? Mom entered the room,resplendent in her black dress. She gave me a small red.
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