Including results for senior crossdressing.
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The Inspirational Journey of a 65-Year-Old Crossdresser
5:25
The Inspirational Journey of a 65-Year-Old Crossdresser
48.6K viewsApr 1, 2023
YouTubeAbout TG Life
The Pros and Cons of Crossdressing at a Mature Age
9:32
The Pros and Cons of Crossdressing at a Mature Age
112.1K viewsSep 14, 2024
YouTubeAbout TG Life
I Finally Dressed as a Woman After 68 Years (Crossdressing Stories)
20:44
I Finally Dressed as a Woman After 68 Years (Crossdressing Stories)
14K views2 months ago
YouTubeBoys2Fem
I Finally Wore a Dress at 71 Years Old (Crossdressing Stories)
20:18
I Finally Wore a Dress at 71 Years Old (Crossdressing Stories)
3.1K views2 months ago
YouTubeBoys2Fem
Advice for Crossdressers Over 60: How to Look Fabulous and Feel Confident
10:39
Find in video from 01:25Fashion Choices for Crossdressers Over 60
Advice for Crossdressers Over 60: How to Look Fabulous and Feel C…
5.2K viewsFeb 1, 2024
YouTubeAbout TG Life
The Ageing Crossdresser's Tips
10:56
The Ageing Crossdresser's Tips
8.9K viewsOct 14, 2024
YouTubeAbout TG Life
Dressed As an Older Woman Over 60 👗💅 (Crossdressing Stories)
18:13
Dressed As an Older Woman Over 60 👗💅 (Crossdressing Stories)
13.1K viewsNov 28, 2023
YouTubeKinda Cute
9:14
Dressing Your Age As a Crossdresser: To Look Sophistica…
1.6K views2 months ago
YouTubeMy Life My Rules
18:01
I’m 60 And Love To Wear Dresses & Makeup (MTF Crossdressing Story)
2.1K views10 months ago
YouTubeMy Life My Rules
2:58
Mature crossdressing
155.7K views10 months ago
YouTubealecia mckoy
13:29
Crossdressing at the Age of 50 | Getting Your Feminine Energy Back
7.9K viewsDec 23, 2023
YouTubeAbout TG Life
2:07
Mature Crossdressers To Love!
29.2K views9 months ago
YouTubeTrans Beauty World
10:28
How to Deal with the Fear of Getting Older As A CrossDresser
244 views1 month ago
YouTubeMy Life My Rules
10:04
Crossdressing After 40: Embracing Your Feminine Side
195 views8 months ago
YouTubeJenn der Bentson
2:40
Mature crossdressing 2
128.8K views10 months ago
YouTubealecia mckoy
22:28
How Wearing a Dress Changed My Life at 50 [Crossdressing Stories / …
35K viewsDec 12, 2024
YouTubeBoys2Fem
53:55
Transforming Into A 50s Lady At Home (Crossdressing Stories)
5.3K views4 months ago
YouTubeBoys2Fem
0:34
61 Years Old And Doing Make Up #crossdressing #transwoman #tra…
7.9K viewsJan 18, 2025
YouTubeCharlise Arielle | My Femme Life
8:54
How to Come Out to Your Family as an MTF Crossdresser When You’r…
2.2K viewsNov 1, 2024
YouTubeAbout TG Life
31:45
The Magic of Estrogen After Retirement! ✨💊💖 (Crossdressing Sto…
20.8K viewsJan 7, 2025
YouTubeKinda Cute
0:04
Crossdressing - Mature women 3
10.3K views7 months ago
YouTubealecia mckoy
50:21
Old Self Faded Away 💖 Crossdressing Stories
1.2K views2 months ago
YouTubeFemme Tales
40:53
The Hidden World of Cross-Dressing in the 60s [Crossdressin…
21.2K viewsJan 22, 2025
YouTubeBoys2Fem
5:46
I’m 23 - And In Love With A 57 Year Old Trans Woman | LOVE DON’T J…
56.2K viewsOct 28, 2022
YouTubeLove Don't Judge
29:08
Living as a Mature Woman Was My True Calling [Crossdressing Stori…
24.5K viewsDec 19, 2024
YouTubeBoys2Fem
1:06
elegant crossdresser as mature lady in satin bow blouse and pleated s…
30.7K viewsApr 16, 2023
YouTubeChristina d ́Yvon
1:40
elegant crossdresser - mature lady in pleated black leather skirt and fl…
21.8K viewsJan 26, 2021
YouTubeChristina d ́Yvon
50:26
Becoming One of the Ladies at 66 [Crossdressing Stories / MtF Tran…
16.7K viewsJan 16, 2025
YouTubeBoys2Fem
3:52
Miriam meets 80-year-old transgender woman Francine | Mir…
58.5K viewsJul 20, 2022
YouTubeABC iview
9:38
Beginner's Guide for a Mature Crossdresser
2.7K viewsAug 9, 2024
YouTubeAbout TG Life
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Short videos

0:10
Senior Dress Up Week Gender Swap - Crossdressi…
97.2K viewsOct 29, 2019
TikTokprettylil.thing
0:34
61 Years Old And Doing Make Up #crossdressing #t…
7.9K viewsJan 18, 2025
YouTubeCharlise Arielle | My Femme Life
1:40
elegant crossdresser - mature lady in pleated blac…
21.8K viewsJan 26, 2021
YouTubeChristina d ́Yvon
1:06
elegant crossdresser as mature lady in satin bow bl…
30.7K viewsApr 16, 2023
YouTubeChristina d ́Yvon
0:31
Why Crossdressing Is a Superpower | Understandin…
13.8K views2 months ago
YouTubeNastja Sherer • Your Favourite Cross…
1:31
Crossdresser: 50s Style dress
9.9K viewsSep 3, 2023
YouTubeIsabelle Labelle's Fashion
1:28
Male to female transgender transition. MtF, hrt, crossdr…
22K viewsJan 27, 2023
YouTubeJessie’s Time
1:00
DRESS OUT! FEEL BEAUTIFUL! Crossdressin…
22.4K viewsFeb 11, 2023
YouTubeJasmine Page
2:27
Crossdresser executive outfits at work
16.1K viewsAug 6, 2023
YouTubeInes Crossdresser
1:09
Hiking In The Morning | Crossdresser
125.8K viewsFeb 20, 2023
YouTubeSilk Living Doll
1:39
Male to female transgender transition. Hrt, MtF, crossdr…
31.7K viewsDec 22, 2022
YouTubeJessie’s Time
0:13
Transgender MtF: another from early in transition mo…
7.6K viewsSep 22, 2021
YouTubeJessie’s Time
1:51
Male to female transgender transition. Hrt, MtF, pantyh…
7K viewsJan 21, 2023
YouTubeJessie’s Time
1:37
Crossdresser experience part 1 - GRWM featuring Crossd…
6.3K viewsFeb 1, 2023
YouTubeCrossdresser Kirsten Stone
0:59
Crossdresser Wrap around dress #genderfluid #fashio…
1.1K views2 months ago
YouTubeKathleen Dawson
1:22
Crossdresser - golden Party Outfit
30.5K viewsAug 2, 2023
YouTubeIsabelle Labelle's Fashion
0:07
Red thigh boots - Glamorous Crossdresser #AlisonThigh…
7.4K views5 months ago
YouTubeThe Sunday Girl
2:29
My Husband is now my Wife |Crossdresser Couple | Mal…
81.7K viewsDec 3, 2022
YouTubeTransgender and Crossdressing Hub
0:48
Crossdresser outfit for the office
4.2K viewsMay 16, 2022
YouTubeInes Crossdresser
2:48
Classy crossdresser in leather skirt posing for you.
53.4K viewsFeb 10, 2024
YouTubeLaura
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