My best first Crossdresser Outfits with skirt and sexy dress (maletofemale)
1:40
My best first Crossdresser Outfits with skirt and sexy dress (maletof…
25.3K viewsFeb 18, 2021
YouTubeVirgily Filly
A Crossdresser's 10+ Year Journey in 47 minutes! | Crossdresser | LuluCD
47:35
A Crossdresser's 10+ Year Journey in 47 minutes! | Crossdresser | Lul…
4.7K views3 months ago
YouTubeLuluCD
You Wanted to Dress Like a Girl? NOW YOU WILL! 😱👗 (Crossdressing Stories – MtF Transition)
36:01
You Wanted to Dress Like a Girl? NOW YOU WILL! 😱👗 (Crossdressing …
50.7K views6 months ago
YouTubeKinda Cute
The First Step Into Feminization - PART 1 (Crossdressing Stories)
3:07:44
The First Step Into Feminization - PART 1 (Crossdressing Stories)
1.6K views3 months ago
YouTubeSissy Maya
First Time in a Dress Gone Right! [Crossdressing Stories / MtF Transition]
56:04
First Time in a Dress Gone Right! [Crossdressing Stories / MtF Tran…
1.9K views11 months ago
YouTubeBoys2Fem
Summer Upstairs - A first time crossdressing experience
8:13
Summer Upstairs - A first time crossdressing experience
494.4K views9 months ago
YouTubeBecoming Lacey
Two Fem Boys [Crossdressing Stories]
9:46
Two Fem Boys [Crossdressing Stories]
109.7K viewsApr 16, 2023
YouTubeLuna's Crossdressing Stories
8:08
My First Date As A Woman | Crossdressing Story
22.7K views10 months ago
YouTubePride Pulse🏳️‍🌈
17:12
Girlfriend Salon Makeover 💕😍 (Crossdressing Stories) PART 1
28.9K viewsFeb 19, 2024
YouTubeKinda Cute
23:44
Our First Date As Girlfriends 👩‍❤️ (Crossdressing Stories – MtF Tran…
2.3K views7 months ago
YouTubeKinda Cute
4:08
How To Lace Yourself Into Your Crossdresser Corset | GlamourBo…
779.6K viewsDec 5, 2015
YouTubeGlamour Boutique
29:38
The Sleepover - A first time crossdressing experience
78.6K views8 months ago
YouTubeBecoming Lacey
20:36
My first ever CD meet up
33.6K views4 months ago
YouTubethemidnightminx
22:07
I Gave My Hubby a COMPLETE Feminine Makeover! 💖💅 (Crossdressi…
13.7K viewsMay 20, 2025
YouTubeKinda Cute
0:06
First Time Fully Dressed as a Girl Transformation Experience
922.8K viewsAug 14, 2024
TikToktrappinbritt
14:16
My First Time Out as a Girl [Crossdressing Stories / MtF Tran…
46.1K viewsAug 9, 2024
YouTubeBoys2Fem
18:30
Trying On Dresses for the First Time [Crossdressing Stories / MtF Tran…
25.9K viewsNov 20, 2024
YouTubeBoys2Fem
11:21
The First Skirt That Was Truly Mine | Club of Two (episode 3) - A first ti…
22.3K views9 months ago
YouTubeBecoming Lacey
1:12
Crossdresser getting ready for our date.
5.6K viewsJun 15, 2023
YouTubeSissy Boy28
2:28
My first time crossdressing i was really young but it was an experie…
55.5K viewsJun 30, 2024
TikTokalexisthemissfit
22:28
How Wearing a Dress Changed My Life at 50 [Crossdressing Stories / …
35.3K viewsDec 12, 2024
YouTubeBoys2Fem
15:02
From Mike to Melissa: Living in My Mom’s Fantasy [Crossdressing St…
212.1K viewsNov 11, 2024
YouTubeBoys2Fem
15:22
Crossdressing Confessions: My Life as Caroline [Crossdressing Storie…
63.5K viewsOct 3, 2024
YouTubeBoys2Fem
25:43
I Turned My Boyfriend into a Woman! [Crossdressing Stories / …
60.3K viewsSep 17, 2024
YouTubeBoys2Fem
18:37
The Secret to Living Two Lives [Crossdressing Stories / MtF Tran…
36.8K viewsNov 21, 2024
YouTubeBoys2Fem
40:53
The Hidden World of Cross-Dressing in the 60s [Crossdressin…
24.4K viewsJan 22, 2025
YouTubeBoys2Fem
17:31
Mom Caught Me in a Dress [Crossdressing Stories / MtF Tran…
47.4K viewsSep 11, 2024
YouTubeBoys2Fem
17:20
How to Start Crossdressing - 5 Beginner Tips
20.3K viewsNov 22, 2024
YouTubeCatch Queen
1:40
How to Crossdress - Start Your Feminine Journey with Confidence
15.5K viewsApr 4, 2025
YouTubeFitUstyle
See more videos
Static thumbnail place holder