Author: AshsGreatestHits

Hooking up with my old Monster Cock fling and his Wife [FFM]

I don’t know if any of you have ever gotten caught red handed writing your Gone Wild Stories, but last week that happened to me. I was back in my hometown for Thanksgiving with my parents. I went out to a bar for black Wednesday with my youngest sister. These kinds of things are always kind of awkward: you see people you knew in high school, some more attractive, some less. In my case, I have to fend off the creepiest of the creepers at the bar, while still looking for some kind of prospect.

 

In high school, I had a reputation… I fucked a lot of guys (33 by graduation by my count) and it stuck. I’m 27 now, have a good job, and have fucked plenty more men. But the creepiest of townie lowlifes with multiple DUIs still remember high school Ashleigh. Slut shame me if you want, but no one deserves aggressive advances from fat hairy guys who they barely knew from grammar school. Thank God, I saw some people I could talk to.

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Got freaky with my friend’s aunt at her bachelorette party (FFMM) [Group]

A few years ago when I was 24, I got invited to a real bachelorette weekend blowout for a friend. I had a few friends get married right out of college, but they were typical of poor new grads: maybe a bar crawl or something. “Tiffany” had something completely different for her: long Memorial Day weekend extravaganza in Chicago. Tiffany was rich: Her dad invented toaster strudel or something (not really), but pretty down to earth. Her aunt apparently offered to pay for her bachelorette, so all I needed was a ticket to Chicago.

 

Now her aunt “Marie” was another story entirely. I was expecting someone our parents’ age, possibly outraged by vibrators and penis straws, offering me a Werthers or something. Marie was definitely the young cool aunt of this loaded family. She was early 40s, recently divorced, and readily reminded us *No prenup! Half plus alimony!* And I could tell as soon as we met that she was on the prowl: about 5’7”, dark tan and fit, wavy black hair with blue eyes, and big, presumably fake tits. Had a solid MILF vibe going on.

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Sharing a Monster Cock with my Friend [FFM]

Early into my junior year of college, I was watching Dirty Dancing and drinking box wine with my friend, “Nicole”. Nicole had just broken up with the guy she had “dated” since high school and needed some consoling. I say “dating” in quotes because she had basically been serially cheating on him for at least two years. Her ex was really straight edge: no drinking, no drugs, judge others about it, and not even religious. Nicole was not, so she would just get drunk on weekends and hook up with various guys.

 

Her “boyfriend” finally got wise and broke up with her, and Nicole took it hard, ergo the night of Swayze and Fran. Despite cheating on her ex **A LOT**, she wanted to get back at him. Now Nicole was short, maybe 5’2” but hourglass curvy, pale with big green eyes, and a huge mane of fiery red hair. Think Lindsay Lohan before cocaine, but with bigger hair and bigger boobs. She didn’t need to try to be able to hook up with whomever she wanted. *I just want to send him a pic of me fucking a giant dick* she says to me at some point. Read more »

Bisexual Friend Fucks Me Hard [FF]

Hello again. I know I’m a little bit bisexual. 80% into guys, 20% into girls. Probably a 2 on the Kinsey scale. While I love to fuck the cock, I have a particular type of woman that I can be attracted to sexually. Now until college, my experiences with other women were mostly experimenting: making out, light petting, maybe some touching over the panties. I had a threesome with a guy and his girlfriend once, but she and I didn’t really do anything to each other. We just took turns with him. This story is about my first true lesbian experience and what followed.

 

When I was a sophomore in college, I was friends with a junior named “Emily”. Emily was tall, about 5’11”, golden tan with long blonde hair, and a D1 soccer player. She was pretty built too. I call her “thick”, not as fat, but just as athletic. She was hourglass shaped with solid C cups, and a big curvy ass. She was bigger than me because she was built to play soccer. Thicker arms than me and huge legs, but pretty thin in the waist. Compare this with me, 5’5”, skinny with big boobs. I never knew she was bi because she had a boyfriend, until one fateful night. Read more »

My [F]irst [M]onster Cock

Hi, my name is Ashleigh and I’m a size queen. Now, that doesn’t mean I’m an elitist. If I only fucked huge dicks, I would barely ever get laid. I just prefer a penis size that most women would find to be uncomfortable or outright painful. But some of the best sex I’ve ever had was from average sized guys. Being a “size queen”, to me, means the bigger you are, the more likely I am to fuck you for the sake of fucking you. This story is how I learned that I really do love monsters.

By the end of high school, I had sex with 29 different guys. It was a lot, but it was spread out over time and over social groups (theater, stoners, tennis). Some were just once, some were quite a few times. Now I was 5’5”, tan with short dark blonde hair, 105lb and athletic, with a 32D bra, so if I wanted to get with a willing guy, I could get him. I was (and am) a very sexual person, so I took advantage of this: I had 3 or 4 FWB who I could fool around with at any time, and if someone new caught my eye, I would fuck him too. I kept track of it all in a little book, and realized that I liked the bigger dicks. I felt fuller and more satisfied. Read more »