Best websites to show yourself dressed up as a woman

Some websites offer paid webcam chat with beautiful women, and some of them specialize in sexual fetishes. This means that you can enter a private chat room dressed up as a woman and show yourself to the webcam model via your webcam, allowing you to express your sissy fantasy without fear. These websites will not ban a man for wearing a dress, stockings, or high heels since they offer categories dedicated to sexual fetishes.

Here’s how it works in practice. Most webcam models work in Eastern Europe. You join one of the websites below that allow webcam sex chat, then choose a live mistress, and instantly enter her chat room. Next, you must activate your webcam so that she can audio chat with you. These websites are sex websites, and it is possible to masturbate in front of the webcam.

A man dressed up as a woman

Privacy and anonymity

Note that these websites are safe. Webcam model websites have been around for more than 10 years, and we have never heard of an instance of sex life disclosure. The support teams of these websites look after the customers and protect their anonymity and privacy. In short, employees of these websites do not know your full name and address. There is a clear wall between the webcam model websites and their payment processors.

You may use your name and address when buying credits on a paid webcam chat. However, the payment processor is an independent entity separated from the webcam model website. Employees of the payment processor have no connection with the webcam model website. Therefore, the payment processors do not know the use of those payments made through their platform.

List of websites:

The websites below allow you to express your sissy fantasy without fear.


Here’s how to find a chat room where you can get dressed as a sissy woman on Imlive. After joining Imlive, click on “filter,” and then you can choose discipline, domination, humiliation, jerk-off instruction, orgasm denial, whips, and more. Although there aren’t any sissy categories, the camgirls are fine with men who get dressed up as a woman. Imlive is a good website because the price-per-minute is low as compared to other webcam model websites for a private chat.

Click here to join Imlive for free


After joining Streamate, enter ‘sissy,’ ‘sissy boy,’ or ‘sissy training’ in the top search field to find webcam models willing to dominate a sissy boy. Click on the magnifier icon, and Streamate will return a list of camgirls who have the keyword in their description. Users can add keywords to the profiles of Streamate camgirls to give other Streamate users hints about what they should expect if they enter a private chat with the said camgirl.

Click here to join streamate for free

A sissy trainer on streamate


This website features many dominatrices in the fetish category. They usually dress in leather and have accessories like a whip. The site also features many Latinas from Romania and Colombia. If you decide to explore the fetish category of Livejasmin, take the time to read the descriptions of your favorite webcam models. Some camgirls may not be as experienced as they claim, so it’s best to test several chat rooms and leave a private chat promptly if you’re not satisfied.

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