I’m hopeful that my story “Cruise Doubledate With My Sister” will be well-received. If it is, people will ask for a sequel. The obvious hook for a sequel would be Caitlin’s five-day vacation with Rebecca and Thomas where she’s going to give Rebecca some more in-person sex lessons. I don’t intend to write a sequel, but if I were to write one, what would it look like?
Let me start by saying why I think Rebecca requested the additional in-person sex lessons. She’s come around to the viewpoint that the timing of sex and marriage isn’t that important. What’s important is the strength of her relationship with Thomas. Thomas’ affair with Caitlin and the sex lessons Rebecca had on the cruise improved and strengthened her relationship with Thomas. He was so happy with their improved relationship that he asked Rebecca to marry him only two months after she moved in with him. Caitlin’s actions on the cruise made it clear that she has no long-term interest in Thomas, so she’s no threat to Rebecca’s relationship to him. They aren’t married yet, so it’s all extra-martial sex. More sex lessons over Labor Day looks like all upside, no downside.
Option 1 – Caitlin and Rebecca become bi-sexual
This option for the sequel is I’m sure the crowdpleaser. I’m sure most people would want as Rebecca’s final lesson how to let Thomas fuck her ass while she eats Caitlin’s pussy.
I know in erotica that it is super common for a woman whose lover has/is going to fuck another woman to become sexually attracted to the other woman. It’s fun! It’s arousing! It makes no sense to me! Bisexuality is from what I can tell fixed and relatively rare. Having two people at the same time realize that they’ve been bisexual all along is something that I can’t figure out how to pull off in my writing (actually, I’m thinking of doing it for a sequel to “Cycling Weekends With Sis” but the whole sequel would be built around building up to that). Nor could I write a sequel where Thomas decides he wants a threesome with Rebecca and Paul.
What I think Rebecca would enjoy is sex sessions much like their last morning together – she’s involved with Thomas as he and Caitlin have sex. She enjoys making Thomas happy and allowing Thomas to be happy, but not having to make the emotional/physical effort of having sex. I would see her finding such sessions very arousing and once Caitlin departs, she’d be far hornier than normal.
Option 2 – Rebecca looks to marry off Caitlin
There is a risk to Rebecca’s relationship with Thomas in the future – Caitlin wants to move to Boson once she has two years in her current job. Caitlin 1400 miles away isn’t a threat; Caitlin living in Boston, quite possibly in their apartment, is.
The best way for Rebecca to shut down that threat is to marry Caitlin off. She and Thomas know a lot of successful single guys. The Labor Day weekend would alternate between sex lessons and partying with friends. Rebecca would be trying to find Caitlin a roommate and a boyfriend for when she moves to Boston. Rebecca would stop Caitlin’s sexual access to Thomas once they get married, perhaps even after Labor Day. Very logical, but would make readers unhappy.
Option 3 – A long-term relationship of occasional wild weekends
So this is how I would do a sequel
* Labor Day weekend would be five days of sex between Thomas and Caitlin with Rebecca involved but not having sex
* Thomas and Rebecca go to Wichita for Thanksgiving and repeatedly slip away with Caitlin for more “sex lessons”
* Caitlin gives Thomas a one-person bachelor party with Rebecca’s approval
* Rebecca tells Caitlin that as much as she enjoys the “sex lessons”, she won’t let Caitlin have sex with Thomas if she moves to Boston as that is too much of a threat to their relationship
* Instead of moving to Boston, Caitlin gets a job in Baltimore. Once a month, she goes to Boston for a weekend of sex with Thomas while Rebecca roots them on
* Happy with those weekends, Caitlin throws herself into her job and doesn’t worry about dating anymore