Kelly's Diary 112 - Shopping for Sex - Cover

Kelly's Diary 112 - Shopping for Sex

Copyright© 2025 by Kelly85

Chapter 1: Little Annie’s Dad

Erotica Sex Story: Chapter 1: Little Annie’s Dad - You know how sometimes it seems that something you dream of but deep down you know will never happen - happens? Well, that was the case in this situation. We met at church where he was a Deacon. I was young and single while he was married with children. I was offered a day of shopping and dinner in exchange for fulfillment of a fantasy. Sounded like a pretty good deal to me!

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   True Story   Cheating   Exhibitionism   Masturbation   Oral Sex  

For the past three years I’ve worked at my local church as youth group helper. During that time I’ve been blessed to be able to watch my “kids” grow up and mature. At the same time I’ve also gotten to know their parents and in a few cases, become quite close- VERY close.

Such was the case with Annie and Kevin. Annie was only eleven when I started, cute but very immature. On the way to fifteen, she’d transformed quite the little hottie. Her brother Kevin was a year behind and had only moved up into my youth group section this past year. Being only fourteen, he had exited that stage where boys pretend to hate girls and I could see all the signs of young lust beginning to emerge.

Annie was one of my more precious girls. It was hard to believe how fast she had changed from a gangly, shy little girl to a curvy, sexy and outgoing young teenager. It didn’t hurt that she looked at least two or more years older than she was, especially with all the makeup and the style of clothes she wore. As much as I loved her, sometimes I couldn’t help but be a little jealous of Annie at times. When I was her age I was way behind most girls when it came to boob development curve whereas Annie was WAY ahead of all the other girls. She had to be at least a B cup and maybe even moving into C - and she was only fifteen! I was barely able to fill out a A-cup at her age, a source of never-ending embarrassment in gym class although it didn’t seem to bother the boys I dated.

Despite her mature looks, Annie was still learning to cope with her new hormones and body features the same as any girl her age. There were more than a few times when we shared some intimate moments when she would confide in me her new feelings and insecurities. Now don’t read anything into that last statement. When I say “intimate” I don’t mean we did anything sexual - there was never ANYTHING even remotely like that between us. What I am referring to is us discussing things that normally would be said between a mother and daughter. The problem was, in Annie’s case talking with her mom was out of the question. Annie’s parents were outwardly great people but the more I learned about them, especially her mother, the more I realized it was not the same at home with their kids. I felt sorry for Annie since I knew how important it had been for me growing up to have someone I could trust implicitly with ANYTHING. Of course, for me that person was my mom which just made it extra special for me.

Since Annie didn’t have that sort of relationship with her own mom, I tried the best I could to help out. My biggest concern was that if Annie didn’t have someone to mentor and guide her through these critical development years, with her looks and natural sexual magnetism, she would fall prey to the pervs and jerks who I could already see eying her around town. She may look seventeen but I knew she was barely fifteen inside.

As the relationship between Annie and I grew closer, I couldn’t help but come in contact more with her parents. Her mom just gave me a cold shoulder but I didn’t take it personal as she treated everyone that way. Even though she was past her prime, she was still pretty good looking for her age - and knew it. I imagined that she was one of the girls back in school that looked down on everyone else. I had her pegged as a damn cheerleader long before I visited their house and saw one of her high school pictures on the table - in a cheerleader outfit of course.

What was disturbing to me about Annie’s mom was that she still tried to dress like she was a teenager. To be honest, she actually came pretty close to carrying it off but she was starting to show the inevitable signs of age here and there. It must have been maddening to a woman like her to look in the mirror and see her once perky boobs losing their battle with gravity and start to sag. Her legs looked great, again for a woman her age, but I was sure she hated the “for her age” modifier. She looked at girls like me with jealous eyes but I didn’t never took it personally since all the girls got the same treatment from her.

Annie’s dad was a totally different story. From the first time I introduced myself to her parents back at the start of my freshman year, Annie’s dad had given me “the look”. Every girl knows what I mean when I say “the look” but for sake of the guys, “the look” is when a man looks at you but you know he’s really mentally undressing you and imaging the things he would like to do with you once those clothes were out of the way.

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