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.
KATIES GRANDMA
Katie's grandma was my favorite in their family. She had great taste and always spoiled Katie as she was the youngest of the 3 kids in the family. Katie had an older brother Jake, who was 20 at the time of the event and a grade above me in high school. We were friends before I started fucking his little sister and after a period of hate, he accepted it and we became friends again. He had the absolute hottest girlfriend (Natasha) that everyone mutually agreed was pretty much perfect. She was Native American but just seemed like a gorgeous brunette with the perfect sized tits and ass. Jake was a really good looking guy and had always gotten all the hot girls since I'd known him but ended up settling with Natasha for a good 5 years until they split (a couple years after the event). Funnily enough, Natasha was Katie's best friend first as they're in the same grade and then he began fucking her, and I began fucking his little sister. Another thing to add about Jake is that Katie would tell me things that really threw me off, even though I knew Jake pretty well and thought he was as normal as it gets, if anything he was a player and guys guy. The first thing that threw me off is when Katie told me that him and his friend, who I also know well and seemed straight, have been shaving eachothers ass cracks for years. That's pretty gay no matter how you put it but I just filed it as him being very metrosexual and confident enough to let a fried do that, and returning the favor. But then my girlfriend told me her older brother always comes in the bathroom when she's taking a bath or comes in her room while she's changing and up until I stopped her and said something, she had thought it was pretty normal as they'd seen eachother naked all their life. I asked if she is casual around him naked and she said never, but I guess she thought it's okay that he still does it. To me it seemed super weird as both were well past the age of that being anything close to considered acceptable. At this point they'd both been having sex for 3+ years now and were in relationships. All of this is good to know for the finale.
Katie also had an older sister named Elizabeth, who we called Liz, who was much older and had a different dad. She was decently fat too and much taller than Katie, probably 5'8 or 5'9. Brunette with really tan skin. She didn't care for me much either and she dated black guys and probably thought I was too skinny and small for her sister. I came to find out her mom dated black guys in between her 2 marriages and current boyfriend Paul. More of them later, this is about Jenny.
Katie's grandma Jenny was probably around 70 years old but looked 50. She had blonde hair and was a very pretty lady - the good looks must have came from her. She frequently got Botox and was always dressed very classy. I didn't know for sure at the time, but I thought she maybe had a boob job as they were almost perfectly perky but she never dressed skimpy at gatherings. She would always give me kisses on the side of the cheek like French people do whenever me and Katie would go over to her house for holidays as the whole family always gathered their. It was a nice house in a nice part of town. Jenny loved me the most and definitely wanted Katie to marry me. I'm sure she'd be even happier now as I own/operate medspas and she's get hooked up on her Botox. Granny is the MVP of this night so remember the name Jenny.
REST OF THE FAMILY INVOLVED