Crossdresser Videos Collection

Enjoy our crossdresser videos collection. Be sure to check back periodically as we rotate videos out to provide fresh content. Perhaps you’ll draw inspiration from these brave crossdressers as they venture out in public, some for the very first time.

More videos on Crossdressers Guide: See our voice feminization and crossdressing tips for passing pages.

Crossdresser in Los Angeles (Video)

By Genderfun: I had an amazing time in Los Angeles. I transformed the lovely Monique, took her photo, and after we went to a party in West Hollywood!

Crossdresser’s First Time Outside (Video)

By Jessie Pierce: It felt wonderful to be out in the public, around others, fresh air. I went into a hotel lobby, then to an outdoor mall. Not too crowded, but it was a start. I’ll be doing it again during the day very soon. In the hotel lobby, as you can see, I was ‘hooted’ at by a couple of boys that looked young enough to be my grand-kids! I was very surprised as you can probably see! At the outdoor mall, you’ll see I had a very eager new ‘fan’ watching me.

Crossdresser’s Day as a Girl (Video)

By heidiphox100: A crossdresser’s day as a girl. Cool temps, so I chose long sleeves. Went to the local library, grocery shopping, and a thrift store.

Crossdresser Out for Coffee (Video)

By StarryNowhere: Video of a TV going for a coffee with me being the TV of course! The cafe scenes didn’t turn out as I’d hoped I’m afraid – better luck next time I suppose.

Cute Crossdressers Outside in Public

By StarryNowhere: Enjoy this video of crossdressers spending time outside in public. The thrill of cross-dressing and being able to pass as a girl in public for crossdressers is huge. Passing as a girl in public for crossdressers can be quite a challenge but with the help of makeup, proper clothing and styling as well as proper body gestures & movements, crossdressers can experience the outside world as they want. If you are a crossdresser and you plan to go outside, make sure you are prepared for it and that your look is feminine and cute. Don’t overdo anything that may lead to exposing of your identity.

Out and About Transvestite/Crossdresser (Video)

By StarryNowhere: Taking photographs and being photographed sitting in a Coffee Bar on a murky Sunday afternoon.

Best dressed Crossdressers Out in Public (Video)

By StarryNowhere: One of the most exciting thing for crossdressers is to go outside in their feminine mode and enjoy themselves openly. Going out dressed is much more thrilling than just cross-dressing at home. It is risky in many ways to crossdress openly so a proper planning should be made before venturing out in public for crossdressers. For young and beginner crossdresser, keep practicing and don’t forget to take it easy sometimes and enjoy yourself.

Gorgeous Crossdressers in Public (Video)

By Pink World: Every crossdresser desires to experience the feeling of being in public, in front of other people and different surroundings. There has been a significant rise of crossdressers stepping out in public. Due to the access to video tutorials, makeup products, online shopping etc, more and more crossdresser are able to transform themselves into very beautiful women. Here are some of the wonderful photos of crossdressers out in public.

Crossdressing in the Theatre (Video)

By tanajuklova: A crossdresser enjoys a day out in the center of Prague.

Crossdresser Mandy – Ladies Outing (Video)

By Mandy White: Make-up session, dinner in the city, theatre and then off for some dancing in a club. Dearie me, perfect! 🙂

T-Girl Lady in Red at Dillards (Video)

By Matty Caff: Shopping and sampling perfumes at Dillards in my subtle, red dress and heels. 🙂