Author: designhero444

[M]y Best [F]riend’s Girlfriends – #1 – [Cheat][Cuck]

Adam and I were best friends all through highschool and into college. He is a few years younger than I am and in my honest opinion a lot more attractive than me. Unfortunately for Adam even though he looks like an Alpha kind of guy he is actually has a “beta of a beta” personality. His looks always seemed to land him the cuties girlfriends ever since we were kids but once they got to know how weak of a personality he truly was they would usually break it off within a few months. This actually drove Adam’s insecurities wild and thus made him less of a strong man.

This is about how I easily took his girlfriends.

Sandra was a highschool cheerleader and dated Adam his senior year of highschool. I was already in college and would visit home almost every weekend. Since Adam and I were close so were me and his Girlfriends. Sanda and I would talk online for hours but never crossing any serious lines. I won’t lie we flirted here and there but never anything worth noting. Read more »

The Time I made her watch. [MF] [Cheat] [Cuckquean]

I was an asshole back in college, I still am but I was also one back then as well. So here is how I broke up with my then girlfriend Amanda. Amanda and I had been dating going on a year and a half before things started to go stale. School was getting pretty tough for me and since she was an hour away it made things just that much more lame.

Amanda lived with her best friend Denise. Denise was a short blonde who dyed her hair black with a cute bang cut. She was probably 100 lbs wet and had little to no curves to her. She did have a sexy face though, one that radiated desire when you looked in to her eyes. She was quite the opposite to Amanda who was average height with curves to die for. She had a perfect hour glass shape and a cute face. Side note: these girls liked to party. Both of them were definitely not the girls you brought home to meet the family but at the same time Amanda was sweet and we hit it off well. Read more »

Single guy at a couples resort -[long] [FMF] [massage]

A few years ago my then girlfriend and I were invited to join 2 other couples at a all inclusive resort in the Caribbeans for Thanksgiving. The place was small but had everything a romantic get away would need, free endless drinks, free endless food, and the beautiful Caribbean water/weather to soak it all in.

Allie and I planned for months. We had a list of excursions and couples spa dates all lined up ready to relax and let it all go. All was going great leading up to the trip until it all came crashing down. The Friday before the trip I found out that not only was Allie cheating on me with some guy from work, but she already cancelled her flight and took off with half the money we set aside for spending. Needless to say I was heartbroken and furious at the same time.

After two or so days of sulking I met up with James for drinks. James was with Whitney and they were one of the other couples going on the trip. James is 6’0″ with an slim rock climber build and Whitney is about 5’5″ with an average build. She has a “cute little ass” that pairs well with her frame and average sized tits. What really makes her noticeable is her vibrant purple hair. Imagine a curly haired southern girl but bright purple. Read more »

Saved By The App [MF][Tease][CFNM]

Back in my sophomore year of college I signed up to be an RA. At the time it sounded like a sweet deal, free rent, a couple hundred per month and free food at the cafe. How could I not sign up? When I luckily got the job I was then asked to join my new team in those long drawn out building camps but luckily this is where I met Amy. Amy was a petite 5’2 blonde with a shoulder length cut. She was perky in all the right places and had a killer smile. I was instantly drawn to her and tried my best to get to know her during that week of training. Read more »

River floating and a MILF-ish [mF] [public] [premature] [long]

This happened back in my early years of college when I went on a good ol’ float trip with a group of friends from school. In Texas (at least) when people ask you to go floating or tubing with them it always means getting your innertube ready and buying/drinking as much alcohol as humanly possible. Tubing is the best place to soak up the hot Texas summer sun as you lay back, drink and embark on a 3-4 hour float with your best friends and good music. Most of the time it’s usually one or two hours of drinking heavenly and one to two hours of being shit face plastered and trying not to drown.

On this trip it was 10-12 of us. Chase was there and at the time him and I were just becoming great friends so we still kept our cool around each other. Mostly trying to impress/not make living together as roommates a nightmare. Read more »

Beer Pong Partners [mf] [public] [accidental creampie] [long]

This is just to give some more information to what happened after [this](https://www.reddit.com/r/TrueBigDickStories/comments/78y7ha/to_drunk_to_remember/) story took place. This is a xpost from /r/truebigdickstories

“Latina girl” or Regina and her roommate Kassie were both in a sorority at the time and Kassie was the one who’s snapchat I had the honor of being featured in. Kassie was the chapter president and when news of the situation got out she was actually kicked out of the sorority. I only found this our through Chase. There was some drama about Chase and me being in their apartment that night but nothing that was of importance. Now on to the story.

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Ever break up with a serious partner and find your self hanging out with people you would never have imagined you would have hung out with before? Well for some reason this happens to me all the time. After the situation broke out about the snap story my gf promptly left me stating that she didn’t want to be with someone who ends up in a random girls bed. Despite all my efforts she was gone. Read more »

First Time Accidental Cuckold. [MFM] [MF] [Cuckold] [Longish]

This is an X-Post from /r/truebigdickstories

This is a happened back in highschool back in my hometown where myself and twenty of my closest friends would get together on the weekends and drink until the sun came up. What was great about growing up in a small town was that everyone knew everything about everyone and our group was no different. The other great thing about living in a small town is that everyone fucks everyone, this too was something our group did often.
We usually would party at a ranch house about 15 minutes outside of town. The ranch had a beautiful 5 bed room 4 bath house that wasn’t lived in because my friend’s parents inherited it from their parents and couldn’t sell it. This made from some crazy nights and tons of sex. Read more »

One Halloween Night With [M]y G[F] and her Sorority Sisters. [Exhibition] [Long] [Cheating]

Back in college I was in a pretty serious relationship with Bailey a cute blonde in a sorority. She was 5’6″ 120lbs and had curves in all the right places. She was extremely sexual and although it was vanilla by nature we would literally skip class to fuck all day. Her stamina was to die for. Lucky for me so was mine. She was obsessed with my size and told me that although she had some big guys before I was by far the biggest. Even when we would just watch tv she would take out my dick and play with it just to “see it get big” as she would say. I still miss her enthusiasm.

One night she got invited out to a Halloween party with her sorority sisters and being as close as we were it was assumed I would be tagging along. That didn’t fly to well with her friend Maddie though and she gave us a verbal protest. So to make thing better for myself I bought a few bottles for us to pregame at Bailey’s apartment. It was myself, Bailey, Maddie, Sarah and Ashley. The girls were all dressed in cute matching black cat outfits. Which was just a American Appeal one pieces with cat ears with a tail. It was amazing being able to steal glances at each of there asses. I was just some random thrown together Scottish warrior. It was really just one of Bailey’s skirts, shirtless, with a scarf thrown over my shoulder pined to the kilt. Of course I wore it in true Scottish fashion. Read more »