I honestly could not help myself. I was standing there in the grocery store in line at the checkout and then I looked down. The young girl standing in line in front of me was wearing a skintight pair of pink Spandex pants with an equally tight pink jogging bra made out of the same material. All I could do was whisper under my breath, “What an adorable ass.” The girl turned around, smiled at me and said, “Fifty bucks.”
She went through the checkout with her bottle of flavored water with vitamins added. When I got through the check out and opened the door to go into the parking lot that same girl asked, “Do we have a deal?”
Totally confused and obviously missing the point I said, “What?”
Again she smiled sweetly at me and said, “You said that you liked my ass. I’ll let you fuck it for fifty dollars. Cash.”
She was way too young and way too pretty to be a whore. She was obviously of very good upbringing, she had class, and she was wearing some very expensive jogging clothes. She seemed as if she had made other men that same offer just to laugh at them. I was different though. I said, “Okay. It’s a deal.”
I really expected her to go running off but instead she told me to put my stuff in my car and then to follow her around the corner. Once again I expected to see her running for her life but she didn’t. She kept looking back but she stayed just ahead of me. We went around the corner, we went down about a block and a half, and then we went through a tall hedge.
As I got through the hedge I saw her standing in the doorway to a guesthouse on a big estate. She held the door open for me and then she stepped through it ahead of me again. Toward the back of the guesthouse was another doorway that she went into, it was a bedroom.
She held out her hand and said, “Fifty bucks.”
I reached into my pocket and handed her two twenties and a ten. They were crumpled and she had to straighten them out. She placed the money on the dresser and then she stripped off her top almost before I could see it. Her tits were bigger than I had thought. That Spandex had smashed them flat. Her pants were stripped down her legs like a second skin and then pulled off her feet. Then she stood before me completely naked. She was your typical hundred pound girl but there was something special about her. It was the way she stood there with her head held high, her shoulders back, and her posture was perfect. She had class. I watched her as she walked to a nightstand and pulled a tube of K-Y Jelly out of the drawer. She got on her back on the bed and rolled her legs up behind her arms and let her feet rest behind her head. She reminded me of a pretzel.
As I stripped off my clothes, she greased up her own asshole using two fingers and then three fingers to get it good and stretched out for me.
I crawled up on the bed and I slipped my hard cock into the opening that she had created. I slipped right in with an audible ahh. She too made a sound of pleasure and then she rocked up into me. I had never fucked a girl that young before. I had never fucked a girl in that position before. I had never had anal sex either. The fact that I had paid this young girl fifty dollars just made me like it even more. If she wanted to act like a whore I guess I could join her in her roll play. I started to really thrust down into her keeping her legs pinned to her body. At that point I was only interested in my own pleasure. I fucked her with a strength I had not known in years. Her tight rectum felt good and her asshole tightened around my cock like a rubber band or a cock ring. When I finally cut loose, she knew it. She said that my cum was hot and that it was burning her. She was just being kind but it gave me an extra squirt that I fired deep inside her.
I sat up on my knees with my cock still imbedded in her asshole. She released her feet and allowed them to bend enough to place her feet on the bed next to my knees. Looking down I saw her open pussy drooling from our sex and it hadn’t even been touched.
This young girl had really gotten off from having my cock buried deep into her rectum. My old cock slowly shrank and it slipped out of her tight sheath. I rolled onto my side and asked, “Have you done this often?”
She replied, “A few times but you felt the best yet. I think I’ll stick with older men from now on.”
I dozed off with thoughts of her next to me.
On hour or so later I was awakened by gentle kisses. She was still there next to me and she was still naked.
She asked, “For another forty, I’ll let you do it again.”
I laughed and said, “At my age I only get to do that about once a week.”
She giggled and looked up at me as she said, “Thank you Grandpa. That was great. See you next week as usual.”
I patted her shaved pussy and said, “Next time you can be the slutty cheerleader without any panties doing back flips in the park.”
She smiled and said, “Okay, but if another old guy wants to join us…let him…for fifty bucks.”