Including results for first feminized date.
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My First Date in Feminine Attire (Crossdressing Stories)
6:25
My First Date in Feminine Attire (Crossdressing Stories)
122 views1 month ago
YouTubeRoyal Sissy
My First Date As A Woman | Crossdressing Story
8:08
My First Date As A Woman | Crossdressing Story
22.4K views9 months ago
YouTubePride Pulse🏳️‍🌈
Feminized By My Online Date 💄 (Crossdressing Stories)
12:41
Feminized By My Online Date 💄 (Crossdressing Stories)
134 views3 months ago
YouTubeGenderSwap Stories
Feminized For A Date - Crossdressing Stories
23:35
Feminized For A Date - Crossdressing Stories
1.2K views4 months ago
YouTubeFem Stories
My First Date As Greta! I Wore A Dress & Heels... 👠😱💖 (Crossdressing Stories – MtF Transition)
24:08
Find in video from 13:03The First Date
My First Date As Greta! I Wore A Dress & Heels... 👠😱💖 (Crossdressing …
6.1K viewsDec 2, 2024
YouTubeKinda Cute
“My Crossdressing Husband Ready For His First Date | MtF Transformation & Crossdressing 🌸”
33:02
“My Crossdressing Husband Ready For His First Date | MtF Transformation & Crossdressing 🌸”
878 views4 months ago
YouTubeSissy Fantasy World
Ex Girlfriend Feminized Me (MTF Feminization Story)
12:11
Ex Girlfriend Feminized Me (MTF Feminization Story)
11.3K views1 month ago
YouTubeAbout TG Life
9:46
My Mother Prepared Me For My First Date... With A Boy | Sissy Transformation Story
12K views8 months ago
YouTubeSissy Lux Crossdressing & Feminization Stories
10:56
Feminizing My Boyfriend (MTF Feminization Stories)
8K views1 month ago
YouTubeAbout TG Life
26:48
Feminized Just For One Date - Crossdressing Stories
127 views4 months ago
YouTubeBecoming She
20:53
Turned Into A Femboy To Date My Crush 👗❤️😳 (Crossdressing Stories)
6.6K views11 months ago
YouTubeKinda Cute
11:55
Becoming a Sissy On My 18th Birthday (MTF Feminization Story)
2.4K views1 month ago
YouTubeAbout TG Life
8:54
An Addicted Feminine Man - First Time Feminization
10.7K views3 months ago
YouTubePride Pulse🏳️‍🌈
22:58
FIRST TIME in a SKIRT! I Dressed as a Woman for a Day! 😱 (Crossdressing Stories – MtF Transition)
4.3K views5 months ago
YouTubeKinda Cute
12:49
First Time Feminized : Femboy MTF Story - Enemies To Lovers
3.7K views3 months ago
YouTubePride Pulse🏳️‍🌈
11:17
Emotionally Transformed Into A WOMAN (MTF Feminization Story)
4.6K views3 weeks ago
YouTubeAbout TG Life
21:07
Our First Kiss... After Her Feminization Started! 🥰 (Crossdressing Stories – MtF Transition)
3.2K views3 months ago
YouTubeKinda Cute
23:31
Girlfriend Feminizes Boyfriend... Point Of No Return 🥰 (Crossdressing Stories – MtF Transition)
47.4K views11 months ago
YouTubeKinda Cute
24:48
My First Christmas as Myself — Feminized by My Girlfriend, Effortlessly Feminine
16.7K views4 months ago
YouTubeThe Gender Diary
9:33
Feminized During Lockdown : A Transgender Romance
9.8K views3 months ago
YouTubePride Pulse🏳️‍🌈
14:45
I'm Not a BOY I'm a Girl! Is the Date Ruined!? | My Second Chance Part 11 #fantasy #genderbend
15.4K views6 months ago
YouTubeGenderPlay Books
12:05
Feminized by DAD (MTF Feminization Story)
5.3K views2 months ago
YouTubeAbout TG Life
20:53
My FIRST Day as a Girl at a NEW Job! 💖💼 (Crossdressing Stories – MtF Transition)
2K views6 months ago
YouTubeKinda Cute
43:33
Wedding Night Surprise My Wife Began My Sissy Training Crossdressing Stories
545 views2 months ago
YouTubeSissy Empress
10:00
A Feminization Story: New Roommate - Part 2
35.8K views7 months ago
YouTubeBecoming Lacey
16:52
How I Feminized My Husband | A Step-by-Step Transformation Story
8.2K views6 months ago
YouTubeSissy Lux Crossdressing & Feminization Stories
9:21
My Wife Secretly Feminized Me With Hormones | My Transformation From Liam To Lily | MTF Sissy Story
4K views5 months ago
YouTubeSissy Lux Crossdressing & Feminization Stories
23:59
I Got My PERIOD... For the FIRST TIME! 💖 (Gender Bender – MtF Transition)
13K viewsDec 21, 2024
YouTubeKinda Cute
My First Date As Greta! I Wore A Dress & Heels... 👠😱💖 (Crossdressing Story – MtF Transition) PART 2
21:11
Find in video from 13:00The Date Invitation
My First Date As Greta! I Wore A Dress & Heels... 👠😱💖 (Crossdressing …
2.8K viewsDec 5, 2024
YouTubeKinda Cute
56:04
First Time in a Dress Gone Right! [Crossdressing Stories / MtF Transition]
1.9K views11 months ago
YouTubeBoys2Fem
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