Our little game... the story so far. [M37, m28, F25, F40]

Previous part:

https://www.reddit.com/r/cuckoldstories2/s/UdTSpsfQ3i

All, I wanted to provide some background for those that have not read the series that my new stories are based on. The following js a brief summary to this point.

Characters:
Jake is the main character and the cuck. He is a good sized dude at an athletic 6 feet tall, good looking but under endowed. His small penis of 4 inches is just too small for his girl. The original fantasy might have been his. His fiance is Katie, he works for Dan and works with Mitch and others at an expanding accounting firm. He is late 20s. He has been with Katie since he met her and fell in love with her at a mutual acquaintances graduation party.

Katie is Jake's fiance. She is roughly 5 foot tall with a perfectly round and trained bubble butt, a flat stomach and perky breast's. She is fit, confident and craves sexual adventure. Her blonde hair and blue eyes and innocent smile betray her growing knowledge and power as a hot wife, cuckoldress and potentially femdom. She truly loves Jake and they have been together for 3 years having met a friends graduation party from college. Katie is currently employed as a part time fitness instructor at a local gym. Her new BFF is Sarah whom she met at the gym.

Dan is Jake's boss. He is a few years older than Jake and Kaite and that is part of the allure. He is in his mid to late thirties, single and is hung and knows "how to fuck". He has been a bull before, but only briefly, and has a dominant streak. He presents as a nice and good guy, but pretty much sleeps with who he wants to. He has had a bit of a fascination with Katie since she and Jake moved to the city and Jake began to work for him.

Sarah has just moved to town. She was a professional Domme and is starting her business back up in her new town. She is tall (like 6 feet) and also competes in hyrox competitions from time to time. She is close to 40, and resembles Hannah Waddingham. She is the very definition of athletic thiccccc. With thick thighs, a large well shaped posterior, muscular arms and back and large fake boob's. She wears her blonde hair in an angular but feminine short hair cut. She has developed a great friendship with Katie and was the one that introduced chastity to the equation.

Mitch is Jakes coworker who has kind of been an innocent bystander so far. He likes regular guy things like drinking beer, playing softball and staring at Katie's ass in a pair of jeans.

The story so far....

Jake and Katie had been playing with the fantasy of her sleeping with another guy when Katie asked who of Jakes buddies had the biggest cock. Jake responded with Dan. Katie teased Jake about fucking Dan and began to take him down the path of premature ejaculation by teasing him about it. Katie also initiated texting with Dan and although Dan initially pushed back, he was all in when he realized Jake had a small cock and Katie just needed some good sized dick. Katie talked Jake into it being their little game as Dan did not know that Jake knew that Katie was flirting, sexting and eventually fucking Dan.
Katie kept Jake in the know and sometimes asked for permission, like when Dan asked for her to come downstairs and give him a blow job while Jake was upstairs. Katie surprised Jake by going and sucked off Dan and returned home and gave Jake a big kiss, at Dan's direction.

The relationships developed and Dan and Katie continued to flirt and plot to fuck in ways that would humiliate Jake. Katie even had Dan send everyone home early on the Friday before a holiday so she could fuck Dan in Jake's office. With the increasing daring and humiliation, Jake became even more prone to early ejaculations and would not even last through a hand job as Katie would tell him about her adventures with Dan.

Kate then met Sarah who she became good friends with. Sarah was and is a professional dominatrix that was burnt out from the profession in her previous city/setup. Sarah suggests chastity to enhance the cuckold/hotwife experience, but it is presented as a way to remedy premature issues. Dan continues to find ways to get Katie to fuck him, even when Jake and Katie are hanging out and Jake doesn't really want her to go. The couples first bet of sorts is when Katie jacks Jake off in front of Sarah and tells him if he cums too quickly she is going to lock him up and go fuck Dan. Jake cums while his wife's best friend watches. Jake is locked back up and Katie goes and fucks Dan and sends Jake multiple videos and pics.

Jake and Katie are engaged to be married and shortly before the wedding, Dan asks Katie to spend the weekend together at a cabin up in a state park area. Jake pushes back, but Katie finds a way to get Jake to say yes to one night. One night turns into two and Jake goes crazy with cuckold angst and makes a deal to let Dan know that he knows admitting that he is okay with it. Jake goes to find them at the cabin and ends up watching first hand as his fiance is turned into Dan's complete slut. She makes noises for him that he has not heard, cums on Dan's dick almost on command and basically is Dan's free use always named private cum receptacle. Jake ends up licking Katie to an amazing orgasm as Dan fucks her and this ends up with Jake getting first hand look at Dan's big dick and balls and tastes Dan's cum for the first time before cleaning Katie up from a weekend spent being Dan's cum dumpster. Jake is invited to fuck Katie and lasts about as short a time as possible, cums in her and eats his own load out.

My story pics up here. Dan and Katie have conspired to trick Jake into giving up the keys to his cage to Dan and in the process he gives free access to Katie.

This brings us up to date.