Note to readers: In my story, "Aunt Em and I", Joey's Aunt Emily was teaching him the fundamentals of sex in a course she entitled sex-ed 101. Joey was clueless at the beginning, but proved to be a quick learner in a course which consisted of both lecture and in-bed activities. At the end of that story, Joey reluctantly agreed to bed the widow Gretta, sight unseen, as a favor to his Aunt. Gretta was the owner of the large house where Em had rented rooms. All that Joey knew about Gretta was that she was a master seamstress who worked from home and neither drove a car nor attended church, hence the difficulty with meeting men and the reason that Joey was asked to help out.
The story which you are about to read begins with Joey and Aunt Em in bed, discussing anal sex. It is told by Joe(aka Joey), who is now in his advanced years.
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Em says that we are not going to practice anal sex, no matter how much I pester her, because it doesn't do anything for her. She says, however, that a lot of women enjoy it, including two of her waitress friends, so there are a few things that I should know. Firstly, I should never attempt it on the spur of the moment. If the girl has never had anal sex, and agrees to try it, we should schedule a few preliminary sessions. In these sessions, I am to practice gently penetrating her anus, beginning with something the size of a pencil, and working up to the size of my rather large (her words) penis. Most important is the need for copious lubrication, because the rectum is not self -lubricating, as is the vagina. On the day when the actual event is scheduled, the girl should empty her bowels. An enema is not required, Em said, and gave me the name of a certain tea which would do the job.
After the discussion, we had prolonged intercourse, using variations on a position which we had not tried before. "Dammit, Joey, how many times have I told you to keep your fingers away from my asshole? Are you some kind of pervert? I feel sorry for your future girlfriends." The alarm clock then sounded, reminding Em that it was time to get ready for her waitressing work. When she left the room, the moment of reckoning was at hand. Gretta would soon knock on the door. I was never more nervous, and decided right then to make this a most unpleasant experience for Gretta, so that I would not be asked to service her in the future.
I was still in bed when I heard the knock, and when I said, "come in", the door opened and a petite barefoot woman was standing in the doorway. Her short white terrycloth robe accentuated a pair of wonderfully tanned legs. I thought that this could not be Gretta, that there had been some change of plans, but why didn't Aunt Em tell me of the change? After a moment, the tanned woman approached the bed. "Hello Joey, I'm Gretta. Please look away while I drop my robe and slide under the sheet." My brain was mush at this point. I did as she requested, and when she seemed to be settled in bed, I turned toward her and peered under the sheet. She was lying on her side facing away from me and was totally naked. Totally. No bra, no panties.
Remembering that Em said Gretta was shy, I did not immediately grab her. I quietly drew down the sheet and softly put my left hand against her neck, slowly drawing it over her shoulder, down her side, up over her hip, and down her leg to her shapely foot. I repeated this, gently scraping her smooth, flawless flesh with my fingernails. (I grew my nails long because Em liked to have her back scratched). Before long, Gretta was responding with soft moans and gentle twitches. After turning her on her back, we began to kiss. At some point I put my tongue against her teeth, but she did not respond. When asked to open her mouth, she did so, and soon our tongues were very busy. When I tried gently biting her lip she caught on immediately, and soon we were eating each other's faces. There was moaning and groaning. I didn't think her late husband ever kissed her in this manner.