I’m 23 - And In Love With A 57 Year Old Trans Woman | LOVE DON’T JUDGE
5:46
I’m 23 - And In Love With A 57 Year Old Trans Woman | LOVE DON’T JUDGE
56.2K viewsOct 28, 2022
YouTubeLove Don't Judge
Trans Women of All Ages Discuss Chasers, Polyamory & Dating | Them
18:30
Trans Women of All Ages Discuss Chasers, Polyamory & Dating | Them
174.5K viewsFeb 12, 2025
YouTubethem
Dating as a Trans Woman
18:24
Dating as a Trans Woman
398.5K viewsDec 30, 2020
YouTubeKayla Ward
HOW TO DATE A TRANS WOMAN
13:47
HOW TO DATE A TRANS WOMAN
24.4K viewsFeb 14, 2025
YouTubeBrixtina
Internet Dating for Trans Women over 50 ****A general discussion **** I am PERSONALLY NOT looking
13:38
Find in video from 00:15Introduction to Internet Dating
Internet Dating for Trans Women over 50 ****A general discussion *…
34.1K viewsMar 14, 2020
YouTubeDiana Salameh
Living & Dating As A Trans Man | 5 People Explain
7:49
Find in video from 05:33Dating and Relationships
Living & Dating As A Trans Man | 5 People Explain
493.9K viewsNov 14, 2019
YouTubeTinder
Living & Dating As A Trans Woman | 4 People Explain
8:15
Living & Dating As A Trans Woman | 4 People Explain
992.1K viewsNov 14, 2019
YouTubeTinder
PSA: The #1 Mistake Men Make When Dating Trans Women (And How to Fix It) #DatingAdvice #TransDating
5:34
PSA: The #1 Mistake Men Make When Dating Trans Women (And How to Fix It) #DatingAdvice #TransDating
1.8K views4 months ago
YouTubeTransPlanet: Tips for Transgender Love
What Trans Women Want: Dating Green Flags
7:17
What Trans Women Want: Dating Green Flags
107K viewsSep 24, 2024
YouTubeMalibu Delish
I married a trans woman, and it taught me some stuff!
17:34
I married a trans woman, and it taught me some stuff!
111K viewsFeb 20, 2021
YouTubeWives Vs World
why my BOYFRIEND dates TRANS WOMEN *our 4 year anniversary 🙈*
25:50
Find in video from 06:00Date Night and Relationships
why my BOYFRIEND dates TRANS WOMEN *our 4 year anniversary 🙈*
8.7K viewsNov 14, 2024
YouTubeErica Aquino
Transitioning when you are older - 40 to 60+ age trans difficulties
12:46
Transitioning when you are older - 40 to 60+ age trans difficulties
226.3K viewsDec 22, 2019
YouTubeJackie Rabbit
Older Transgender Woman Meets Young Transgender Woman | The Gap | ‪@ladbiblestories‬
28:16
Find in video from 01:17Understanding Transgender Identity
Older Transgender Woman Meets Young Transgender Woman | The …
714.6K viewsJun 29, 2022
YouTubeLADbible Stories
The Inspirational Journey of a 65-Year-Old Crossdresser
5:25
The Inspirational Journey of a 65-Year-Old Crossdresser
48.7K viewsApr 1, 2023
YouTubeAbout TG Life
MTF age 50 transitioning when older, Male to female transition at 50 years old & beyond!
24:46
MTF age 50 transitioning when older, Male to female transition at 50 years old & beyond!
31.6K viewsDec 5, 2020
YouTubeJackie Rabbit
Coming out transgender in your 70s: Transitioning from male to female at 73 | Stuff.co.nz
2:14
Coming out transgender in your 70s: Transitioning from male to female at 73 | Stuff.co.nz
25.8K viewsAug 3, 2021
YouTubeStuff
What is a Shemale?
8:13
What is a Shemale?
19K viewsMar 15, 2025
YouTubeMy Transgender Date
Interviewing A Trans Elder (“I Knew At Age 10!”)
53:44
Interviewing A Trans Elder (“I Knew At Age 10!”)
66K viewsFeb 15, 2024
YouTubeSamantha Lux
Miriam meets 80-year-old transgender woman Francine | Miriam Margolyes: Australia Unmasked
3:52
Miriam meets 80-year-old transgender woman Francine | Miriam Margolyes: Australia Unmasked
58.6K viewsJul 20, 2022
YouTubeABC iview
A Man Who Lives Like a Woman: Still Figuring Out to be a Transwoman | Nonbinary | Gender Fluid
3:24
A Man Who Lives Like a Woman: Still Figuring Out to be a Transwoman | Nonbinary | Gender Fluid
18.7K views4 months ago
YouTubeTransgender and Crossdressing Hub
Transitioning when you are older - 40 to 60 years old age group transition problems
23:22
Transitioning when you are older - 40 to 60 years old age group transition problems
29.9K viewsFeb 26, 2019
YouTubeJackie Rabbit
How To Date A Trans Woman: 8 Things A Man Needs To Know
7:11
How To Date A Trans Woman: 8 Things A Man Needs To Know
332 views1 year ago
YouTubePaTricia 🩷 Elise
See more

Short videos

0:37
Love Has No Age Limit | Empowering MatureTransla…
780 views2 months ago
YouTubeThomas A. Anderson
0:25
How To Successfully Date As A Transgender..
2.5K viewsJan 30, 2023
YouTubeNaiah Nikole
1:40
Transgender Dating – 100 Romantic Date Night Ideas …
406 viewsJul 6, 2023
YouTubeMy Transgender Cupid
1:08
Beautiful Mature Transgender Women | The …
8 views1 month ago
YouTubeThomas A. Anderson
2:53
Post-Op Trans Dating: Real vs. Online Experiences
287.7K viewsSep 15, 2023
TikTokmayavhenry
0:11
Trans Dating in the US: Best Transgender Dating Site in …
1.1K viewsJun 3, 2023
YouTubeMy Transgender Cupid
2:17
Dating as a Trans Woman 🌈 | How to Find Respect, Safet…
83 views7 months ago
YouTubeMy Transgender Cupid
2:10
I’m a 60+ Trans Woman on Grindr This is What Dating …
102 views10 months ago
YouTubeSoraya's Fierce Cooking Show
3:08
Dating as a Transgender Woman: Exploring Love an…
387.5K viewsJun 7, 2024
TikToklea.greyy
0:50
from dating as a man to dating as a woman #trans #…
1.5K views1 month ago
YouTubeJessica Rose Bray
0:18
Navigating The Transgender Dating Scene For Trans Wo…
166 viewsJun 4, 2023
YouTubeMy Transgender Cupid
2:22
Crossdressing Role Reversal Marriage || Crossdresser C…
67.2K viewsNov 9, 2022
YouTubeTransgender and Crossdressing Hub
2:29
My Husband is now my Wife |Crossdresser Couple | Mal…
81.7K viewsDec 3, 2022
YouTubeTransgender and Crossdressing Hub
0:06
Embracing Transgender Identity as a Mature Woman
17.1K viewsFeb 26, 2025
TikToktranslover607
0:06
A 61-year-old Trans Woman's Journey
12.3K viewsFeb 1, 2023
TikTokmardipantz
2:15
Trans Chaser or Trans Attracted? (How to Know)
6.4K viewsNov 28, 2024
YouTubeTrans Dating Coach Kara Chang
0:10
What It's Like to Finally LOVE Being a Transgender Woman
43.1K views10 months ago
YouTubeTGirls & Beauties
0:18
Trans Dating App New Jersey Find Love for NJ Transgen…
339 viewsJun 20, 2023
YouTubeMy Transgender Cupid
0:12
My best friend is going on his first date as a woman... che…
1.3K views4 months ago
YouTubeQUEER GLAMOUR
1:45
Mtf transitioning later in life!
4.7K viewsOct 23, 2021
YouTubeAlyson Mosby
Static thumbnail place holder