Riley Reyes Executive Role Reversal


Riley Reyes is a secretary for a high powered exec that happens to have a crush on her. In fact, he's in love… Riley is intrigued but not by a date. She wants to wear the pants in the relationship and make him take on her role. 18 min

In an office, a boss (impeccably dressed in a suit, tie, nice shoes, pocket square, maybe a nice-looking watch) is giving his secretary (wearing understated makeup and stockings, pumps, a nice dress or blouse-skirt combo, some jewelry) dictation, or some other kind of busywork, when he joins her on the couch to profess his love for her.

She is hesitant, but as he keeps pushing, she gets an idea, first fingering her own outfit, then the lapel of his suit jacket. She tells him that if he wants her, he has to agree to walk in her shoes for a bit first — literally, by entirely swapping clothes and letting her play the boss while he plays the secretary. Now he’s the hesitant one, but she pouts and flirts until he finds himself agreeing.

We watch her remove every single item that she’s wearing, then watch her strip him of everything he’s wearing, while he’s mostly a helpless bystander. Once both are naked, he tries to make a move, but she very easily fends him off: she now has ALL the power in this dynamic, and carries herself like it from this point on.

MOST IMPORTANT PART: We watch her carefully put on all of his clothes, in this order: underwear, undershirt, shirt, pants (maybe sitting down on the couch for that part to see her feet come out the pants legs?), socks, shoes, tie, jacket, any other accessories. She is enjoying the hell out of this. He helps as needed to make sure she looks exactly right, and not sloppy at all. She stands in front of him, smugly puts her hands in her pockets, asks how she looks. He’s amazed.

She helps him put on all of her clothes. This is less important, and also something I imagine will take longer (and maybe need more help to either squeeze him into it all or cheat in certain instances like the shoes), so I’m fine with most or even all of this taking place off-camera to save running time for the later stuff, just so long as we wind up with him fully dressed in her clothes, struggling to stand or move in heels.

She paces around him, amused and excited by what she sees, then realizes he’s missing something. Acting like the boss, she orders him to go outside and fetch “his” purse, and enjoys watching him walk in heels.

While he’s gone, she pours herself a drink, sits at his desk, puts her feet up, and enjoys both the drink and her new power.

He returns with the purse on his shoulder, now walking a bit better, and she praises him for it. She takes out lipstick and maybe some eyeliner (depending on how much time this would all take; just the lipstick is fine) and applies it, then steps back and declares him beautiful. The more she compliments him, the more into the exercise he seems to get.

She invites him to sit on the couch to take dictation, then laughs when he spreads his legs out like a man, sits next to him, and helps him fold one leg over the other at the knee. She then spreads her legs and arms out herself in a very masculine fashion, pleased with all she can do.

She plays at being the boss some more, makes him take some dictation, then finds herself running her fingers through his hair and stroking his face. She’s too turned on to keep pretending to work, and they make out for a while.

She checks her watch, realizes it’s quitting time, stands up and invites him to join her for dinner. He stands, nervous about the idea of going out in public like this, but she insists it’ll be great, and that they can keep the role reversal going for a while. She’s always wanted to be in charge, and now she has the chance. They kiss again. He’s convinced.

They exit the office arm-in-arm, with her talking about what they’re going to wear tomorrow, both much happier than when this all started.