All characters were 18+ during the event this story is about. I'm new to this so if it gets a decent response, ill type out the rest of the night. i also have pics/can get pics of most of my girl and her family. If its not allowed to say that just warn me (mods?) and ill cut it out.
BACKSTORY
This is my first post on Literotica so I'm sorry if this is too long but I'm 26 now and think I end up thinking about this night before I nut every time I have in the 7 years since. I figured it was time to get it written down and share it with those who will appreciate it as much as I do.
To start off I have to give a bit of backstory that I'll try my best to be broad with as I began to date my girlfriend in sophomore year of high school, when I was a junior, and the event this is about was when she was a senior and 18. I apologize ahead of time for how long this may be but I want to give every detail so y'all can appreciate how for a night, I think I actually died and went to heaven.
My girlfriend at the time Katie was pretty much your classic average, but pretty, American teen. She was a short brunette, about 5'2 and was petite for the most part. I'd say her tits were never bigger than b cups but her ass was really fat at first and she gradually thinned out. Her pussy was somewhat thick, definitely not one of those puffy slits. I'm an Indian that's 5'10 with a 6" cock that's pretty skinny. Not much girth but luckily enough Katie would grow to tell me it was perfect for anal. More about that later.
Katie was definitely a slut from the beginning and I had known she had hooked up with a couple guys I knew from school. Aside from that, she was dating a pretty big black guy before we started dating and I'd come to find out that he wasn't her first black guy and had probably been with 8-10 guys, of a few colors...., before we began dating. It was probably more though as before the night in question, I began to develop a fetish of hearing about her slutty past and sometimes she'd get really into it and I'd find out about a new guy, but sometimes she'd get annoyed and tell me to just let her keep using the vibrator we had - which was actually one of those smithstone back massagers. I'd eventually realize that she would only really get into it when she was on Xanax - which I knew she would get sometimes from her mom (who would have hundreds at a time from her drug dealer brother) but I didn't know she was somewhat addicted and knew it was bad enough to have to lie to me when I'd ask if she was when I could tell she was loopy.
Me and Katie were not right for each-other at all. I've always strived for success and come from a wealthy Christian family thats always preached the importance of greatness. Katie's family on the other side was well-off for a period, thanks to her doctor Dad, but he became a very bad alcoholic and lost his license, and eventually everything else causing Katie's mom to leave him. Katie's mom had a boyfriend named Paul who was a plumber and made decent money ($25k-$35k) a year but they both spent most of it on candy crush and lived pay check to pay check in a very small 3 bedroom house that they rented. Katie's grandma Jenny was actually pretty well off and had high class taste. Her husband had passed away a few years ago leaving his car lot business to her. I mention this because I'd broken up with Katie at least 4 times before she "cheated" on me which led to what started off as the worst day in my life and ended as a day I don't think will ever be beat as my EX clearly doesn't want anything to do with me and there's no chance of repeating anything like this as her grandma began to ignore me too unfortunately.
GIRLFRIENDS MOM
Katie's mom, Sam, was about 40 years old. I'd seen pictures of her when she was young and she was actually a beautiful redhead but time was not the nicest to her and she had grown decently fat, and her hair had browned out a lot. She had these huge tits though. Her mom (ex's grandma) had a mostly French background and her dad Irish which I think is where the red hair came from - which popped out from time to time in my ex. For the first couple years of our relationship, me and Katies mom got along great at first as she wanted her daughter to marry me, but we began to clash as her parenting style was awful and of course, she hated me more and more each time I'd break up with Katie. Sam was clearly addicted to Xanax and considered it medicine and not an addiction. I was never allowed to stay late at their house as she'd usually be good at stumbling in and telling me it was time to go. But I remember a night where I was spooning my ex and fucking her under the blanket as we thought Sam had crashed hard, but she stumbled in and I guess it was too obvious because she walked right up to the bed and threw the sheets off both of us. Her eyes was watery from the Xanax but she stared at my rock hard dick (that's always shaved clean) for a good 3 seconds until she got angry and told me to leave before "her boyfriend wakes up and beats my ass". I remember she was in a silkish night gown and her nipples must have been rock hard because they were clearly begging to break through her gown. God I hated her, but as I'm starting to realize... things I hate for some sick reason have become fetishes. I never used to like big girls, and now I love them. I used to fume at the idea of my girl having sex with people in her past, especially black guys, but I came to love that too.