How To Dress Like A Sexy Secretary – Clothes For A Different Type of Home Office!

Sexy Secretary through office window

Wondering how to dress like a sexy secretary? This doesn’t necessarily mean scouting out the perfect sexy office outfit. Sometimes it can be just as fun thinking out of the box and coming up with other sexy ideas using your existing wardrobe.

Adding in some accessories and clothing items can bring new and sexy roleplay ideas into the scenario too. For example, holding a clipboard and pen while putting on your glasses to perform his evaluation.

Has he been a hard-working employee who enjoys a reward, or perhaps he isn’t quite up to scratch and needs more one-to-one support? It’s important in the office environment to keep staff morale high by whatever means necessary!

Below we have included all you will need to get the most out of your sexy secretary evening of fun.


A smart dress teamed with suspenders, heels, and office accessories will let you glide into the sexy secretary role!

How To Dress Like A Sexy Secretary – A Complete Eqiupment List!

You Will Need:-

  • Short Black Skirt: just short enough to give your boss a teasing peek of what’s underneath – if anything.
  • Tight-fitting cropped shirt: leaning over to discuss those figures while giving your employee more than an eyeful.
  • Glasses: never underestimate the sexiness of glasses when performing some roleplay fun. Glasses are very sexy.
  • Sexy bra and knickers set: filing has never been so much fun when you must bend over to file those papers. Open rear knickers will turn up that office temperature for sure.
  • Stockings and Suspenders: show your boss how long and smooth your legs are when you sit next to him and seductively cross your legs, running your hands up and down your legs.
  • Tie: perhaps you’d like your employee to look a little smarter for the office and you buy him a tie which you take great pleasure in putting on for him – not necessarily around his neck.
  • Pinstripe Basque: show your boss the perks of having such a diligent secretary. You definitely know how to dress to impress.
  • Pen and Clipboard: it’s been a busy day and it looks as though you’ll both be working late. It’s a good job you have your list of things to be done…
  • Suit: nothing says professional like a boss in a sexy suit. Perhaps the aircon stops working and you gradually lose clothing with the help of your employee.
  • Suspender Dress: an urgent meeting has come up with an important client. You’ve pulled out all the stops with this one.

Dressing like a sexy secretary is very easy and often you will already have some accessories laid around that will be perfect. Secretarial role play doesn’t need to be just about skirts and shirts – there are many other ways of incorporating the sexy office look. Don’t forget, you ultimately want to feel sexy and the part, but you also need to feel comfortable.

Perhaps you have the outfit all sorted but aren’t sure of a narrative for your roleplay? Don’t worry, we have some great ideas in our roleplay ideas guide.

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