I had gone so long without penetration that it would be impossible to simply pop my cherry with a random guy or even my finger. The event was so built...up in my mind that it simply couldn't happen until I found a worthy partner. I would only fuck a man if his cock were as big as El Toro, and I certainly wouldn't find someone like that at school. Viewing porn had led me to believe my search would be brief. However, one year and almost 30 dicks later that search hadn't turned up one guy even close. She hadn't dated a man in 15 years and she hangs out with a group of ladies that meet twice a month and they go to dinner, vacations, shopping and such. I laughed and said great maybe I can meet some of you older hot friends, Debbie said no way if this works out nobody will ever now, nobody. So I figured she was a little interested so I just stood in front of her, we were on the couch and took out my semi hard cock and held it in front of her and asked her, Ms. Debbie, you wouldn't want to. More

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