Kelly's Diary 112 - Shopping for Sex
Copyright© 2025 by Kelly85
Chapter 2: Flirting With Annie’s Dad
Erotica Sex Story: Chapter 2: Flirting With 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
All through the fall and Christmas, my “relationship” with Ian was purely innocent. Oh sure we flirted but it was more of a tease than anything else, no different than what I did with a number of dads. Then he began to talk to me more and even complimented me a few times on my appearance or what I was wearing. He seemed to be less embarrassed if I caught him looking at me - something he seemed to be doing more and more of as time went by. Finally one Wednesday night I was sitting in the youth room reading a lesson plan I was getting ready to give when Ian walked by. Seeing me sitting there all alone, he came in the room and greeted me.
“Hey Kelly, how are you doing tonight?” he said in a chipper tone of voice.
“Fine Mr ... oops I mean Ian,” I replied.
Ian passed by and then paused to look down at me in my seat. I was sitting in one of those ridiculously small child seats so he got a pretty good view down my blouse which was unbuttoned down to my cleavage. Even though I knew he had to be getting an eyeful, especially since I wasn’t wearing a bra, I pretended not to notice and waited for him to continue.
“Ya know, I just can’t comprehend how you girls fit into those jeans!” he said with a disarming laugh. “Do you just paint them on or what?”
Hmmmmmm ... It was probably the most direct question of this type he.d ever asked me. Usually it was just “looking good!” or something like that. I sensed there was more to it than that so I stood up in front of him and twisted around for him to see me.
“Nothing between me and my Calvins!” I said with a sly smile.
Ok, they weren’t Calvin Kleins, but that didn’t really matter, he got the point. Ian just shook his head ruefully at me and turned back to go about his business. Even so there was something in the look he gave me as he walked away that caught my attention. I doubt that even had anyone else been watching that they would’ve noticed it but it was look I’d seen many times before - one that signaled an interest, even a hunger. Whenever I saw it I knew how an antelope feels when a hungry tiger is watching it. It was also the same look my dad gives me when he’s REALLY horny.
Until now, whenever I’d caught Ian looking at me I assumed it was no different than what he probably gave any girl that attracted his interest. It was just an empty glance preprogrammed in his genes as a response to seeing an attractive female. This time it was different, though. This was the first time I felt the weight of the a more focused version of “the look”. It wasn’t anything major and certainly didn’t motivate me to start throwing myself at him shamelessly, but it stuck in my mind for the rest of the evening. It stayed there that night as I lay in my bed rubbing myself. Every girl likes to know guys find her attractive but when she sees THAT look, she knows it’s more than just appreciation of beauty!
After that night I started to make myself “available” to Ian more and more. I was curious to find out if there was really anything to this or if it was just a one-time sign that I may have even just imagined. It was my turn now to “accidentally” bump into him in crowded hallways. I would press my boobs into his chest - actually more his stomach since he was much taller than me. Then when I had his full attention I would look into his eyes with my best “doe eyes” and smile at him before apologizing and stepping back. There were time that I could almost feel his stare boring into my ass as I walked away from him.
In the meantime, Annie and I had been talking more in private. She confessed that she was worried about her parents. Her mom was yelling at her dad more and she was worried about a divorce as her dad had started sleeping in the guest bedroom lately. She didn’t seem to know what the source of the problem was for sure except that her mother had said something about “canceling the damn internet service” once under breath after she had stormed out of their study.
Well, I wouldn’t have been surprised if Ian hadn’t been caught doing something naughty on the Internet. An amazing number of guys I chat with claim to be married and unhappy with their sex life. Who knows, maybe Ian was one of those guys! The odds were astronomical but that night when I went back to my room and logged on I couldn’t help but wonder if Ian wasn’t lurking behind any of the profiles. On the one hand it excited me while on the other hand I felt a bit of nervousness. In doing what I do on-line, I had always counted on the fact that the Internet was huge and that the odds were almost zilch that anyone would know who I really was. Sometimes I’ve thought that maybe I should pretend to be going to school in a more distant state or list my home town as somewhere else, just to maintain a bit more privacy. Although I can’t be 100% honest when chatting (there ARE privacy issues to watch out for), I DO try to keep things as close to reality as possible. The main reason is so I don’t get into a situation where someone I chatted with a long time ago contacts me and next thing you know I’m saying something different than I did the time before. I guess that shouldn’t matter as who really cares if someone thinks I am lying? At the same time I feel bad when people are upset with me for any reason, even on the internet.
The more I thought about Ian sitting alone at home jerking off in the soft glow of his computer screen, the more my imagination began to run wild. One night while counseling Annie I told her how to check her dad’s computer to see what he was doing. She wasn’t too sure about it as apparently her dad was quite strict about anyone using his study, especially his computer. Her mom never used it - she didn’t think her mom even knew how to turn it on, so if anything was disturbed then her dad would know that she was the one responsible.
I laughed and told her to blame anything on Kevin. After all, isn’t always the boys that get blamed for computer problems? She still didn’t seem too sure but I had high hopes for her. The following Sunday she pulled me over to the side and whispered that she needed to talk to me right away. We ducked into an unused Sunday school room and her face was flushed as she looked at me.
“I did what you told me,” she said in a conspiratorial tone, “and you were right!”
She went on to describe to me the contents of her father’s history files and the X-rated web sites he’d been visiting. She looked more embarrassed than turned-on as she told me she couldn’t believe the filthy stuff he’d been looking at. Like most girls, including me, porn was more a curiosity than anything. What gets guys so turned on to look at pictures of air-brushed whores with fake boobs pretending to enjoy having sex?
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