Guest Blogger Penelope Hasler’s Top 5 Roleplay Outfits

We are delighted to present a cherryred guest blog post by the unstoppable and top-notch blogger and spanking fiction writer Penelope Hasler, focusing on her top 5 most fav outfits for cherry-cheeked, fanny-flaming roleplay.

And do make sure to visit her excellent blog called Naughty Little Writer.  Penelope’s spanktastic scribblings and intriguing and often quite humorous musings on the topic of cherryred-themed goodness are always a delight.

Written by Penelope Hasler

#5 Fairy Tale Character/Superhero(ine)

Okay, this is two outfits. So spank me!

Fairy Tale

Lots of fancy dress costumes for women are of fairy tale characters like Red Riding Hood, Snow White, or Alice in Wonderland: young ladies who epitomise sweetness and innocence; gals as pure as the driven snow.

The outfits are of course styled to be cheeky and sexy and revealing, but they nevertheless retain something of that demureness. And it’s exactly in the contrast between the wide-eyed innocence of the fairy tale princess and the nasty, kinky things she gets up to that a lot of the fun and hotness lies.

Or do you want to tell me that it wouldn’t be REALLY SUPER HOT to have a wailing Little Bo Peep squirming on your lap, her jiggling buns glowing red against the innocently pure whiteness of her petticoats? I didn’t think so…


More contrast here, this time between the idea of a (super) powerful female and the humiliation that she is subjected to when put over a knee and spanked. “You can’t do this to me! I’m Wonder Woman! No! Not on the bare! Oh! Stop! Ow! Owch!”

#4 Ageplay Wear

Pretty dresses, pigtails, long socks, buckle shoes: I love to dress (or have someone dress me) as a little girl. As with all roleplay outfits, ageplay stuff is lovely to wear in its own right. Ribbons are just straight up cool. Fact.

But of course the cuteness of the clothes only forms part of their appeal. The associations that come with them – the headspace that they help you get into, and the sheer erotic electricity that they help generate – are the other, wonderful, part.

I adore ageplay, and I adore the naughty but nice feeling I get whenever I step into one of my ‘little girl’ dresses and put my hair in pigtails. And of course the feeling when I’m scolded and spanked and sent to my room with a tearful face and a glowing behind.

Regressing a little further, I have yet to take the plunge and try adult diapers, but I can certainly see their appeal. Definitely one for the ‘to do’ list. Or the ‘persuade partner to let me try’ list, anyway.

#3 Secretary

Office wear is one of those dressing-up outfits that is basically real life brought into the bedroom for sexy play. There’s something uniquely erotic about smartly-dressed people being naughty… those tight pencil skirts; those buttoned-up blouses.

And the ‘professional’ context that such clothing evokes adds its own delicious frisson of sexual excitement. “Oh, but sir! We mustn’t! Not here in the office!” blushes Miss Moneypenny, not meaning a word of it, as she is groped by the MD.

And who in the world hasn’t fancied someone at work? Imagined them bent over their desk, or pinned against the photocopier… or at your tender mercies in the stationery cupboard. Go on, admit it. You’d love to nail the girl from accounts.

#2 French Maid

Or any other nationality of maid.

The point is that you get to dress in a little black dress with bows, frills and stockings and bend over to dust or polish and accidentally-on-purpose show your knickers off to your master/mistress.

Tease is just built in as a feature. As is the idea of subservience and submission: by putting on a maid’s uniform you are willingly stepping into the role of a domestic servant, subject to the whims and cruel attentions of a strict and demanding superior.

Works very well with bondage!

#1 School Uniform

This is it as far as I’m concerned.

The ne plus ultra of dressing-up outfits, and the one I wear more often than anything else. (Do I get an ‘A’ for Latin? :D) Why is it my favourite? Let me count the ways…

There is just such variety: it’s like nothing else in the array of styles and colours that you can choose from. You can wear a super-short black microskirt or a knee-length grey pinafore, a crisp, full blouse or a tiny, revealing top, socks, hats, blazers, jumpers, regulation knickers… anything you (or your teacher) fancy.

Like the secretary outfit, school uniform is something that is worn every day in real life the world over, so any play involving it has a grounding in reality. And in the case of schoolwear that reality comes with overtones of discipline.

A schoolgirl must logically have a teacher, and she must obey rules or she will be punished. School play is just the best: escaping to a world of rules and routine and punishment and (ostensible) innocence… a world that is subverted into an adult fantasy of corporal punishment and sex. I love it!

Visit Penelope’s blog:  Naughty Little Writer

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22 thoughts on “Guest Blogger Penelope Hasler’s Top 5 Roleplay Outfits”

  1. I love your posts Penelope. They’re just always fun and funny and sexy all at once. Didn’t you just give me role play advice by the way? This is a timely list! Age play is one I’ve never thought I’d be into but as of literally a few weeks, I’ve been wondering what the draw is and intrigued enough to do some reading. I think I’ll start with Korey Mae Johnson’s new one. Love how you’ve described it up there.

    1. Ageplay isn’t everyone’s cup of tea but I think it’s wonderful. Looked at objectively, it’s of course a form of power exchange: one in which you get to reimagine childhood from a kinky adult point of view and escape for a while into a persona (and world) that is hugely liberating. Even when you’re being scolded for stealing cookies and threatened with a smacked bottom and an early bedtime. The whole dynamic is just… magical.

  2. First, so glad they had you as the guest blogger today, Penelope! WELCOME!!

    I like the superheroine theme, too, although I’ve never written a story. One scenario I imagined was Supergirl / Linda losing her powers after getting exposed to yellow kryptonite in Chemistry (I HATE it when that happens) and in her resulting confusion she keeps knocking over stuff and gets sent to the Principal’s office for a paddling on her now very vunerable butt.

    Whatever school uniform you wear is wonderful, Penelope, but I expect that tie to be properly knotted and those white socks to be pulled up all the way, young lady!

    1. Hi, imreadonly2! Thanks for the nice welcome 🙂

      That superheroine story idea sounds great! Super-gals do rather lend themselves to the idea of being taken down a peg or two, don’t they?

      And hmf. I’ll wear my tie loose if I wanna, so there! 😛

    1. Classic is exactly the word, Cara – I think some things are just timelessly sexy.

      P.S. My #6 was gonna be Barney the purple dinosaur, btw.

      P.P.S. Not really.

    1. Supergirl – so cute! 😀 I hope you find a nice one and have lots of sexy adventures in it.

      “Oh no! Captured by the Phantom Spanker! Ohh… silly short super-skirt!”

      P.S. I love you too. 🙂

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