Executive Role Reversal 4 Casey Calvert


Casey is having the time of her life, excited by the promotion she’s just given herself, amused by how uncomfortable Lance seems at first, and just plain turned on. Lance, meanwhile, seems embarrassed but then once he admits to her that he likes it, he’s very into it and plays his reversed role to the hilt. 20 min

Lance is wrapping up an interview with Casey to be his secretary. When asked if she has any questions about the job, she asks if it’s true that his last secretary swapped clothes and jobs with him for months. He tries awkwardly changing the subject, but she says this swap sounds like fun, climbs on top of him and starts removing his clothes (maybe start with the belt this time?). He complains that he can’t believe this is happening to him again, and tries to resist, but she’s faster and somehow seems much stronger than him, and his clothes are rapidly coming off while she’s shushing his complaints.

Cut to him fully dressed in her clothes, jewelry and some makeup, and her wearing all of his stuff but his shoes and socks. She straightens her necktie and walks around him, checking out the merchandise and adjusting what needs adjusting while he complains some more about going through this again.

She makes him sit next to her as she finishes getting dressed and explains that she’s always hated being ordered around by men like him, and loves that the shoe’s now on the other foot. She runs her fingers through his hair, marveling at how pretty he looks, then feels around the rest of his body as she (like Riley did) suggests ways he can improve his appearance even more: manicure, shaved legs, etc. (You could wait til this point to have her remove her earrings and put them on him, but only if you think it wouldn’t eat up too much time.)

They get back on their feet so she can fully enjoy the sight of him in her dress, ordering him to walk around, and complimenting his butt, his legs, and how well he moves in heels. He grumbles that he’s had a lot of practice.

They have a long day ahead of them, and she orders him to go get her some coffee, while she stretches out with her feet up on the desk or couch or whatever’s handy. When he returns with her drink, she points out a tiny stain on the floor and tells him to get on his hands and knees to clean it, which is really just an excuse for her to check him out some more. She comes over to take a closer look at the job he’s done and gooses him, much to his chagrin.

His phone rings in her pocket, it’s the company’s CEO. Lance tries to protest, but she answers and enjoys stroking his face and hair and body as she explains that she’s taken over, saying something like, “Yes, just like the last girl did… Yes, he’s wearing a dress now.” At the caller’s request, she starts taking video of Lance, and asks him to twirl and dance a little for the camera (maybe something like, “Jim says he wants to see you twerk”?), which he reluctantly does, to her delight.

At this point, he’s exasperated to be in this situation again and demands that she give him back his clothes and let him be in charge. She tells him how beautiful he is when he’s angry, and they sit side by side as she gets physically affectionate with him some more and gently lays out the reality of the situation: if he let the previous switch go on for months, and if he let a tiny little thing like her wrestle him out of his clothes so easily, then he must really enjoy this, right? He denies, lamely, that he likes this, so she decides to play along. She climbs into his lap and begins doing a very exaggerated impression of a submissive and not too bright woman who adores him and wants to let him tell her what to do about everything. She leans in close, whispers seductively, and asks if he’d prefer that to letting her be the boss. She has successfully called his bluff, and he admits that he’d rather she be in charge — that he secretly loves everything about this, and especially loves beautiful women wearing his clothes and bossing him around.

She’s thrilled by his candor and gets up to celebrate with some dancing, which she eventually coaxes him into joining her for. Both are very into it. As they dance, maybe she asks what he would have done if she hadn’t tried swapping clothes with him, which he answers by smiling and admitting he interviewed a LOT of secretaries before she did what he wanted.

She catches her breath and admires herself in the suit some more. It’s a look she’s never tried before, but she thinks she looks badass in it. Now it’s his turn to circle her, assess how she looks and adjust anything that needs adjusting, as he admits the suit works for her better than it did for him. He says she’d really rock his tuxedo; she’s excited to find an excuse to wear it, and thinks about all the other menswear she can try now. She talks about how much more comfortable it is, especially the underwear. She won’t miss thongs, and asks how he’s doing in hers; he shifts his around a bit and says he’s gotten used to wearing one by now.

His phone rings again, this time his wife calling. Casey answers, explaining that she’s taken over. It’s clear from her side of the conversation that the wife understands and is pleased with this arrangement, as they’re quickly flirting, and the wife is making some requests for Casey, including sending a selfie of herself with Lance. Casey asks for a selfie in return. Lance smiles for the picture. Casey hangs up, admires the wife’s picture, and says she has a strap-on in her bag that will be put to good use soon.

She paces around, rattling off a few more orders (possibilities: arrange meetings with all her new partners, order her business cards, bring in a decorator to fix up this dreadful old office, or whatever), as he responds enthusiastically to each — the first time saying, “Yes, ma’am,” which she then insists on “Yes, sir” instead. She has one last order for him: she wants him to let her give the strap-on a workout before she tries it at home with the missus. He’s startled and very nervous, and she gently assures him that he’ll love it, and once she’s put her cock in him, he’ll wonder how he ever did without it. He reluctantly agrees and goes to get it.

She sits down, leans back, takes in her new kingdom and is pleased. He returns with the strap-on and helps her get into it (there can be a cut here if need be, depending on how long it takes to put the thing on). Once it’s secured, she says that it feels right having a cock to go with her new wardrobe. He notes with some concern how big it is. She tells him he’ll get used to it along with everything else, and as they prepare to begin, we fade out.