Crossdressing at Bedtime

 by Simon

For many crossdressers, when we delve into the topic of what to wear, our focus generally turns to day or evening wear, or something for a specific event. However, often crossdressers also want to extend this to nightwear too, but they don’t always know where to begin when choosing suitable bedtime wear.

In this article, we will provide you with plenty of information to help you consider bedtime crossdressing. Let’s get down to some pillow talk that will hopefully help you choose something that will be cosy, sexy, and fun.

Choosing Your Style

Regardless of the occasion, one crucial aspect about choosing something to wear as a crossdresser, is style and comfort. When it comes to bedtime wear, just because it is more casual it doesn’t have to be boring.

Think about what inspires you when choosing your crossdressing clothes. Are you into bright colours and patterns, or do you prefer something more subtle? Whatever your choices, it all comes back to one thing - your choice of style.

Ultimately, don’t be afraid to pick something that interests you. It doesn’t matter whether it's a silky nightdress or a patterned onesie, all that matters is whether you like it, and whether you enjoy wearing it.

Practicality Makes Perfect

When it comes to bedtime wear, there are several options to choose from. However, another key aspect to bear in mind when choosing your crossdressing attire is practicality.

As we’ve all found out at some point, there’s a lot of feminine wear that simply isn’t suitable for men. There are a lot of clothes that may be uncomfortable, or are just not convenient as they are likely to hurt the genitals.

While choosing your bedtime wear, try to select ones that provide a penis pouch that will keep everything tucked up and protected, or pick something that is designed with unisex in mind. 

Choosing The Right Fabric

It is worth remembering that you will probably be wearing your nightwear for around 8 hours of sleep, and so it is essential to choose the right type of fabric that best suits you and your sleeping environment.

If you are looking for a fabric that is super soft, or if you have any allergies or sensitive skin, then silk is always a great option. Of course, given its quality, silk will be a bit more expensive, however it will invariably last longer.

Cotton is light and breathable, but not best if you sweat at night since it traps moisture. That said, it is very durable and easy to maintain. An alternative to cotton is linen, however it does tend to wrinkle a lot.

If warmth and comfort are your primary factors of choice, then go for flannel and if you are looking for something on a budget, then you can go for polyester, however it’s not very breathable.

Size Is Important

As with all crossdressing wear, size is a very important factor when it comes to choosing the right garment. This is particularly relevant when it comes to bedtime, as you don’t want anything that’s too tight and likely to hurt, nor do you want anything that’s too baggy.

Know your size before purchasing. In most cases, this is simply a case of knowing your chest, waist and hip sizes, as well as your height. Once you have these, you can then determine the best size to choose that will be most comfortable.


Being relaxed in your bedtime wear is perfect for bringing out your feminine side, and I hope this article will help you find what works best for you.

If you have any tips you would like to share, then please do leave us a comment below!

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