Executive Role Reversal 5: A Man’s World

Ella (very girl next door and on the repressed/timid side) paces anxiously in her bra and panties through a hotel room, looking at a couch covered with a man's suit, a man's tuxedo, men's underwear, etc. Riley, her much more assertive girlfriend, enters, naked. She's ready to get dressed for their night out, and asks why their room is filled with men's clothing. Ella sheepishly admits that she grabbed the wrong suitcase at the airport, and this is what was inside. Even worse, she sent their clothes from the plane down to the hotel laundry while Riley was showering; the underwear she has on is all that's left of their clothes. Riley doesn't have time to be annoyed, so she picks up a pair of men's briefs and steps into them, much to the dismay of Ella, who can't believe Riley expects her to wear men's clothing on their big night. Riley pulls on an undershirt and suggests they don't have much choice, thanks to Ella. She then holds out her hand and demands that Ella hand over her lingerie, since if Riley has to wear men's underwear, they both do. Ella pouts as she unhooks her bra and forks it over. Riley asks if Ella has a preference on outfits; Ella, unhappy about this whole deal, steps out of her panties and says she doesn't care; Riley happily says she'll take the tux.

Riley begins buttoning up the tuxedo shirt. She turns around to see Ella standing there in men's underwear, an undershirt, and black dress socks, hating everything about it. Riley cracks up at the sight of her and teases her about how she looks, prompting a mortified Ella to grab the suit and other accessories so she can change in the bathroom without Riley making fun of her. She storms out as Riley teases her some more.

Riley is now wearing every part of the tux but the shoes, socks, and jacket, lounging around with her bare feet up, adjusting a cufflink and calling for Ella to come out already. Ella steps out, fully suited up and embarrassed to be so. Riley applauds, which Ella takes to be more mockery and buries her face in her hands. Riley gets up, walks over to Ella and insists that she's being sincere, and can't believe how great Ella looks in a man's suit. Ella is skeptical, but Riley puts her hands in her pants pockets and circles around Ella, marveling at how well the suit works for her. She straightens Ella's tie and zips up Ella's open fly, much to Ella's embarrassment.

They sit down side by side, Ella demurely folding one leg over the other, her hands resting on her knees like she's still in a dress and heels. As Riley pulls on the socks and shoes, Ella pouts about the dress she won't get to wear tonight and how pretty she looked in it. She extends one of her legs out in the air and rotates her ankle (like she's trying to show off how she looks in a new pair of stilettos) as she talks about how good her legs would have looked, how she got a mani-pedi, and now all people can see is "the mani," as she gestures miserably at her masculine attire and puts her foot back down. Riley finishes tying her shoes and strokes Ella's face and hair, insisting that she's never found Ella hotter than she does right now. Ella is startled to hear this, thinking she looks ridiculous in these clothes. Riley continues to be physically affectionate as she says that she's incredibly turned on, no lie. She's always wanted to get Ella into an outfit like this, and it's driving her wild to see her in it. Ella seems unconvinced.

Riley gets up, pulls on the tux jacket, buttons it up and adjusts her cuffs, then pretends to be posing with a gun and says, "The name is Bond. James Bond." Ella admits that that's hot, but she still wants to wear a pretty dress to a ball. She whines that she doesn't want to dress like a man.

Riley decides it's time to boss Ella around to snap her out of this funk. She gestures for Ella to get on her feet and orders her to walk from one end of the room to the other. Ella does it in a very bouncy, feminine fashion, inspiring Riley to snicker and tease her again. Riley does an exaggerated impression of that walk, Ella pouts again. Riley says she should take advantage of being one of the guys for a night, walk with some swagger and confidence. She demonstrates a more masculine strut, then urges Ella to try the same thing. Ella tries again, is still pretty girly, so Riley coaches her more, maybe even uses her hands to help spread Ella's legs apart and keep her hips under control. This time, Ella is successful, and seems to be getting into this.

They sit back down, Ella again sitting in a feminine manner. Riley spreads out, and tells Ella to try the same, because it's nice to take up space for once. Ella tries it and likes the way it feels. One or both of them could stick their hand down their pants, either amused that guys like to do that, or finally understanding why guys do it. Riley encourages her to go further, and maybe boss her around for a change, really embrace being a man. Ella starts pacing around and barking out orders about what she wants for the rest of this evening (both at the party and, perhaps, in bed after), first tentatively, then with authority. An excited Riley responds, "Yes, sir!" each time. After a few of these, Ella sits back down and strokes the lapel of Riley's jacket, and in a much sweeter voice admits that she really wants to wear the tux, too. Riley reacts like this is the best idea she's ever heard.

The women have completely swapped outfits: Ella now in the tuxedo, Riley in the suit, each admiring how they look and how the other one looks. Both are very aroused and flirty now, and on the verge of kissing, when Riley's phone buzzes. It's a text from the guy who has their suitcase, along with a photo of him wearing one of their dresses. Both are impressed with how good he looks, and Riley says she hopes he never asks for his clothes back. Ella agrees, and the two strut out together.