Halloween Costume Fantasies

By Jenna Rae

Oct 29, 2018

It’s no secret that Sugar Daddies love it when you dress up for them. But today, I’m talking about a different kind of dressing up: costumes. Yes, think Halloween – sugar style! Rocking a costume is the perfect way to add a little spice in the bedroom, all year long. He will love that you’re comfortable taking risks and willing to initiate a little role-play. Has your sugar daddy expressed a fantasy you can make come true? Has he mentioned little plaid skirts, football jerseys or cheerleaders?


Halloween is the perfect time to stock up on costumes and props you can use all year long. Pop-up costume shops are everywhere starting early September (sometimes even late August!) Shop early to get the best choices. Don’t forget to seek out vintage clothing stores. They offer a selection of new and pre-owned costumes and accessories this time of year that is a bit less mainstream. I’ve found some great items here and have also found a few fantasy inspirations! Some consignment shops and lingerie specialty stores also take part in Halloween offerings, so don’t forget to check these out for original ideas. If you can’t find exactly what you had in mind, the online world of costume shopping is always open.

Whatever you choose, your sugar daddy will really appreciate your extra effort. Read on for my list of top costume fantasies that are guaranteed to make his dreams come true.


The classic sugar daddy fantasy outfit. This one will score big points if you’re actually a student, and bonus points if he’s helping you with tuition! Make some time in between classes to get daddy to help you with your study routine. Don’t forget the glasses! Accessory shops in the mall always have a big selection of inexpensive, non-prescription glasses. A perfect buy for when they get squished while you’re rolling around on the bed.


What’s his favorite sports team? Or teams? This costume is in style all year long. It’s always hockey season, baseball season, football season or something. Grab his team’s jersey and pair it with boots only, or score some color-matching lingerie to wear underneath. Perfect for a private at-home Superbowl party. You’ll put on the best half-time show he’s ever seen! Don’t forget that golf, polo, and Nascar are considered sports – this costume fantasy easily adapts to these categories as well.


This costume doesn’t even require the word “sexy” in front. When are cheerleaders ever not sexy? Again, base this costume on his favorite sport or sports team. Pom-pom props are easy to find all year. Bonus points if you were a cheerleader in college, or currently are! It will make him feel like the most popular stud in school. Put on your costume and show him just how flexible you are.


Typically known for their caring nature, nurses help you when you’re sick and also provide overall care. Use your imagination to show him the overall care you can provide! Maybe a full-body massage to cure muscle aches? Bonus points if he actually has a cold – nurse sugar is there is make daddy feel better! The costume part shows him you really want to help make him feel better…including in the bedroom.


This one is a great role-play fantasy if you host, or will be hosting as a special occasion. Buzz him into your apartment wearing your French maid costume. Maybe you are in the kitchen cooking his favorite meal. Or maybe you are busy sprinkling rose petals or lighting candles in the bedroom to help set the mood. He will love to see you “in action” of your costume personality.


Meeting daddy at a hotel? This costume is perfect to put on at home and throw a trench coat overtop for the cab ride over. Put on your ears just before knocking on the door for a greeting surprise! Try sitting together and finishing a drink before starting the fun.


Calling all women who like to take charge – the details to this costume are black leather, naughty accessories, and a mask. This may be a fantasy you already have as part of your regular sex life or perfect if you want to try dipping your toe into the dominatrix world. A one-piece black leather bodysuit is always a hit. The really hard part is lasting until he can get you out of it.

Keep in mind that anything goes in the world of costume fantasy. What are you dressing up as this year?