The Longest Breakup (Patreon)

College is a time for growth and exploration, and Sammie has determined that she wants to explore what it’s like to date another guy while she’s with her current boyfriend.

Told through a series of emails from Sammie to her boyfriend Todd, The Longest Breakup takes the reader on a slow journey of sensual exploration, cuckolding, and eventually, heartbreak.

Each chapter brings new emails from Sammie, all of which detail her developing relationship with Jason, the guy she was just going to go on a friendly date with. It wasn’t supposed to become anything. She just felt bad about canceling on him.

It becomes something much more, though, and she uses her emails to slowly inform Todd that he’s losing her. It’s not clear at first, but by the end of the journey she’s broken up with him in favor of her new man.

If you’re already a Patreon supporter at the Cuckold Stories level you can read all 8 parts of the story below. If not, become a Patreon supporter to go on the journey with Sammie and Todd and read each of her emails like you’re the poor cuckold being broken up with over the course of a few months in early 2019.

Part 1 – It starts so innocently as Sammie informs her boyfriend that she went on a date with another guy. It wasn’t a real date. It’s just that she agreed to it because she didn’t want to hurt his feelings. Of course, she did kiss him, which she doesn’t say until her second email. It does seem like Todd enjoys it, though, as Sammie notes that he seemed particularly amorous when they saw each other for the first time since her date with Jason.

Part 2 – Sammie takes things a great deal further. She goes on more dates with Jason. Things get hot and heavy. She tells her boyfriend about it in a series of emails where she expresses a little regret, but ultimately finds the whole thing so thrilling that she doesn’t want to stop.

Part 3 – Valentine’s Day is coming up and Sammie has decided she’s going to spend it with Jason. It’s not just that she’s hanging out in his dorm room, though. He has two tickets to an insane party and she really, really wants to go. She goes and when she sends an email the next day she details that things got really hot with Jason after the party.

Part 4 – Sammie recounts some of the fun she and Todd had after her first time with Jason. She tells him how much she enjoyed the way he wanted her and how it seemed to be fueled by the fact that she’d been with someone else. At first she says she’s not going to go on another date with Jason, but it’s not long before her resolve melts and she has to see him again.

Part 5 – Things are heating up with Jason and Sammie details the fun she’s been having with the other man in her life in emails to Todd. When Jason takes Sammie to a party and introduces her as his girlfriend, things change significantly. They’re dating now, and while Sammie expects Todd to break up with her, he doesn’t. It turns out he likes dating a girl that’s dating another guy.

Part 6 – Sammie chooses to go on spring break with Jason instead of staying with Todd. Luckily, she’s going to send him daily emails detailing all the wild stuff she gets up to. It’s spring break, right? That means she’s going to cut loose, have wild fun with Jason, and she’s going to email Todd about all of it.

Part 7 – The spring break emails continue, getting a little bit naughtier each time. Sammie even ends up having an encounter with a girl in a club bathroom and gives Jason a major thrill. At least she lets Todd read all about it in her naughty emails.

Part 8 – Spring break is over and Sammie’s back home. In her first email she talks about the fun she and Todd had when they met up for the first time since her return. She gets turned on just writing about it. Eventually their fun has to come to an end, though, and in her final email Sammie breaks up with her boyfriend, telling him that Jason gives her everything Todd provides along with being far better in bed. The choice is obvious. Jason is her boyfriend now. Todd is her ex.