The Sleepover - A first time crossdressing experience
29:38
The Sleepover - A first time crossdressing experience
72.3K views7 months ago
YouTubeBecoming Lacey
SUMMER OUTFIT IDEAS + LOOKBOOK | teenage boy edition ☀️
16:14
SUMMER OUTFIT IDEAS + LOOKBOOK | teenage boy edition …
28.8K viewsJun 16, 2022
YouTubeKing Ant
Soft Boy Outfits || Teenager Fashion
0:59
Soft Boy Outfits || Teenager Fashion
269.5K viewsMar 31, 2023
YouTubeTeenager Fashion
Style Tips EVERY Teen Guy Needs to Know
5:15
Style Tips EVERY Teen Guy Needs to Know
15.4K views10 months ago
YouTubeGT Vision
What to wear for Homecoming | Homecoming outfits for teenage boys #homecoming
4:29
What to wear for Homecoming | Homecoming outfits for teenage b…
15.6K viewsOct 1, 2022
YouTubeThe StyleJumper
Creative Teenage Boy Dress-Up Ideas
0:15
Creative Teenage Boy Dress-Up Ideas
5.8M views7 months ago
TikToksundaykalogeras
The Clothes You Should be Wearing as a Teen Guy
8:32
The Clothes You Should be Wearing as a Teen Guy
67.2K viewsJun 3, 2023
YouTubeAaron Ramirez
10:43
10 Casual Outfit Ideas For Young Guys | Teen Style Oufits
206.7K viewsJan 5, 2021
YouTubeAaron Ramirez
1:00
DRESS UP! DRESS OUT! Crossdressing Confidence!
36.6K viewsFeb 12, 2022
YouTubeJasmine Page
1:00
Boy to Girl Transformation New Outfit ✨️ for my Boyfriend to enjoy
15K viewsJan 17, 2022
YouTubeLiviah O.
0:09
Dressing Like a Teenage Boy: Fashion Exploration
43.3K views3 months ago
TikToktinabelcher.jj
17:07
I Put My Son In A Dress And This Happened! (MTF Crossdressing St…
48.9K viewsJan 6, 2025
YouTubeMy Life My Rules
0:15
Dressing My Son in Dresses: A Fun Family Experiment
51.7K viewsJan 30, 2021
TikTokdashookie
10:21
Teenage Boy's Room Makeover | Before AND After
96K viewsSep 14, 2017
YouTubeApril Colleen
17:28
Can We Dress You Up!? (MTF Crossdressing Story)
43.5K viewsJan 28, 2025
YouTubeMy Life My Rules
8:33
How You SHOULD Dress To School
513.6K viewsOct 7, 2021
YouTubeAaron Ramirez
15:02
From Mike to Melissa: Living in My Mom’s Fantasy [Crossdressing St…
206K viewsNov 11, 2024
YouTubeBoys2Fem
57:47
My Three Years in a Gender Re-education Academy [Crossdressin…
26K viewsJan 18, 2025
YouTubeBoys2Fem
1:07:48
Teen Boys Caught In Dresses - Crossdressing Stories
9.9K viewsAug 13, 2024
YouTubeFem Stories
1:58
Boy to Girl Transformation "🔥Sweater Dress"
8.3K viewsFeb 18, 2022
YouTubeLiviah O.
9:47
TEENAGE BOYS SHOPPING HAUL | BUYING VACATION CLOTHES FO…
82.5K viewsMar 13, 2024
YouTubeThis Is How We Bingham
14:14
How To Dress Casual as a Grown Man (Stop Dressing Like a Teenag…
884.8K viewsMay 18, 2024
YouTubeAlex Costa
3:14
Male to female transition MtF transgender hrt
6.9K viewsSep 25, 2021
YouTubeJessie’s Time
3:51
Boy wears his sisters dress (please read description)
19.3K viewsSep 2, 2024
YouTubeDaniel Tong
6:34
A FANTASTIC MAKEOVER DAY #MALE2FEMALE BY ISABEL
324.5K viewsJan 16, 2022
YouTubeCrossdressing Shopping and Service by Isabel
9:19
Switching Outfits With My Brother
56.8K viewsMay 4, 2020
YouTubeKate Furphey
9:29
ULTIMATE TEEN BOY BEDROOM MAKEOVER || BUDGET-FRIENDL…
10.2K viewsFeb 16, 2025
YouTubeBreImagine
1:42
How to Dress for School
563.1K viewsApr 5, 2010
YouTubeHowcast
9:35
How to dress your cousin like a girl!
129.3K viewsJul 2, 2014
YouTubeJenny fire
20:41
DRESS UP CHALLENGE (ft: my brothers)
5.8K viewsSep 29, 2020
YouTubeLights, Camera, Lauren!
See more videos
Static thumbnail place holder