Kelly's Diary 039 - My Mom's Best Friend - Cover

Kelly's Diary 039 - My Mom's Best Friend

Copyright© 2024 by Kelly85

Chapter 1: Mom and Tammy (The Early Years)

Erotica Sex Story: Chapter 1: Mom and Tammy (The Early Years) - She was my Mom's best friend and I've known her all my life. Now she was visiting us for the first time in a couple of years. I couldn't wait to show her much I had grown up!

Caution: This Erotica Sex Story contains strong sexual content, including Fa/ft   Masturbation  

I was seventeen and enjoying the summer before my senior year of high school when I had an interesting experience. Without a doubt my mom’s best friend in the whole wide world is Tammy - not to be confused with my younger cousin Tammy. This Tammy is a few months older than my mom and they’ve known each other since they were little girls.

Unfortunately, a few years ago Tammy’s husband was transferred to Oregon and so for the first time my mom was separated from her closest friend and confidante. Since then they’ve relied mostly on phone calls and e-mail to keep in touch but they still manage to meet each other at least once or twice a year for a week or so. Tammy’s husband travels a lot so she uses his frequent flier miles to purchase either her or my mom a plane ticket. If not, my dad pays for the trips as he knows how much they mean to the both of them.

My mom always looks forward to her visits with Tammy but it wasn’t until last year that I found out the whole story behind their relationship. Like many things in my parent’s background, my mom waited until I started having sex with her before she confided everything about her and Tammy with me. It’s important to understand this so before I go further so here’s a quick summary that might help in understanding what led to my most recent experience.

The first surprise my mom threw me was that my dad had dated Tammy for quite some time back in high school before he and my mom became an item. They started going out the summer after Tammy graduated from eighth grade. At the time, my dad was about to become a Junior in high school so for him to date Tammy wasn’t exactly a thrill for her parents. Like most girls at that age, Tammy was proud that an older boy would take such an interest in her and defied her parents by continuing to see my dad.

As it turned out, Tammy’s parents “worries” were justified. After only a few dates she and my dad had sex for the first time in her own bedroom while her parents were out for dinner. It wasn’t my dad’s first time by any means (my mom tells me that he had quite a reputation as a lady’s man at school already by then) but it was for her. THAT surprised me as in all the time I’d known Tammy, I’d never even given any thought that my dad had been the one to take her virginity!

Needless to say, since Tammy was putting out for him, my dad asked her out a lot after that. I’d like to think that my dad wasn’t so shallow that the only reason he dated her was her willingness to put out. From her yearbook pictures I can see that she was quite pretty so no doubt that had a lot to do with it. Not that she isn’t still good looking but she’s not in the same shape as she had been in high school by any means. Really, how many people in their late thirties are? Tammy’s not what I would call fat but more like just a bit overweight. On the plus side the few extra pounds seemed to be heavily biased to it her chest so for a boob man like my dad that wasn’t too bad a deal.

One other comment on the virginity thing. Tammy and my mom may have been best friends but that didn’t mean they weren’t more than a bit competitive, especially when they were teens. The way mom describes things it reminds me a bit of me and my cousin Kristen. While my mom had sucked a boy’s cock once on a dare back when she was middle school, at the time my dad and Tammy were screwing each other it was the only sexual experience so far that my mom had with a guy (other than some innocent groping in a movie theater). Apparently Tammy was quite proud that she had lost her virginity before my mom did, somewhat to the annoyance of my mom.

When my mom finally did lose her virginity, it wasn’t something she could brag about to Tammy since it was her father (my grandpa) who took it! My grandpa died when I was only eight so I don’t really remember a whole lot about him. My mom told me that he was always looking at her and her sister (my Aunt Linda) as they were growing up. He would hug them and touch them in ways their friend’s fathers never did but since he always did it, it wasn’t something she thought was wrong or abnormal. Without going into the details, to make a long story short my grandpa had sex with my mom at the beginning of her freshman year.

As a side note, my grandma knew all about what her husband was doing

to her daughter. While she didn’t do anything to stop him, she didn’t

participate in any way then or later, not even to watch. It was sort

of a “don’t ask, don’t tell” thing I guess.

Unlike my dad with regards to me, my grandpa made the first move on his daughter. He started off by fondling her in her bed while she slept. That led to him teaching her to suck his dick but eventually his lust took control and he fucked her in her own bed while her younger sister Linda slept soundly in her own bed across the room. At first my mom was a bit scared and unsure about the things that he asked her do to him but the more she did it the more she grew to love those intimate times with her father. She was a young girl and like most young girls she just wanted to make her dad happy. Well, needless to say what she was doing did so then she was happy to do whatever he wanted.

As it would have been hard to hide it from her younger sister Linda - it was a miracle she didn’t wake the first time he fucked my mom although personally I still have to wonder if she was really asleep. He eventually did fuck her the next morning before she got out of bed. Since her dad was already doing her sister she went along with it. It’s not so hard to believe as what younger sister isn’t always trying to copy everything her older sibling is doing?

As I said earlier, the whole situation with my mom and her dad was pretty complicated and I suppose I’m doing an injustice by summarizing it so briefly but that’s basically how incest got started in my family. As a side note, both sisters continued to let their dad fuck them even after they got married and if it hadn’t been for an unexpected heart attack, who knows, maybe he would have done his granddaughters as well!

For the next few months and into the next year that’s pretty much where things stood. Tammy and my dad were dating while my mom and her sister had sex with my grandpa. My mom dated a few guys at the time as well, but while she liked to give a BJ here and there she didn’t have sex with any of them. Most of all, she never told Tammy she’d lost her virginity so she wouldn’t have to lie about who had taken it. Tammy and her were best friends, but even best friends can’t always say EVERYTHING to one another.

Because my mom and Tammy hung out together a lot, my dad got to see my mom quite a bit. He was under the impression that my mom was still a virgin as Tammy kept him up to date on the status of most of the girls in school. Though I hate to say it, he most likely saw my mom at first as just another potential “notch” for his belt. Of course today my dad loves my mom dearly but even he has admitted that when they first dated, she was just another pussy for him to conquer.

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