08:05

A trip to the thrift store leads to a Holly night - a crossdressing story

04:21

The Crossdressed maid and why it is a crossdressers dream #crossdresser #maid

04:52

Andrew transforms into Holly for a dinner party, a crossdressing story #feminization

08:05

Holly suspects her co-worker may want to try crossdressing, a feminization story #crossdresser

04:51

A crossdressing story about the thrill of dressing as a woman

04:58

A crossdressing weekend adventure for Andrew as Holly #crossdresser #transgender

17:33

Andrew's job loss leads to a crossdressing employment offer

00:24

A preview of my next crossdressing and feminization video

05:47

My First Time Shopping for Lingerie Changed EVERYTHING!, a crossdressing story #crossdress

04:41

The Magic Mirror - a crossdressing and feminization story about a man who becomes a princess

04:37

A crossdressers story, a weekend ski trip as a female #crossdresser #feminization

05:19

A forgotten suitcase leads to a crossdressing weekend #crossdresser #femininity

08:08

Crossdressed for Halloween, a feminization story #crossdress #transgender

10:07

The magic trunk, extended version, a crossdressing story, #crossdresser

06:41

The magic trunk, a crossdressing story. #feminization

08:05

Andrew's roommates decides she wants a female roommate - a feminization story #crossdressing

07:19

A crossdressing story - the continuing story of Holly and her cheerleader friends #crossdresser

07:07

Cheerleaders decide Andrew will join the cheerleading squad #crossdresser #transgender

03:07

I'm a Crossdresser and I Just Discovered the Secret to Self Acceptance, in a song #crossdresser

05:10

From Office Worker to Drag Superstar A Life-Changing Journey #crossdressing

07:02

The Journey to Feminization Begins! a crossdressing story

06:46

Holly becomes her bosses secretary, part two - the continuation #crossdresser #transgender

06:03

Caught crossdressing by his boss and then becomes her secretary #crossdress #transgender

08:04

My Boyfriend Became My Girlfriend for a Day? #crossdressing

08:05

Don't complain about your girlfriend taking too much time or may end up dressed as a girl

06:35

Embracing Your TRUE SELF Through Crossdressing with HollyMonroe

06:19

My Secret Double Life EXPOSED! A crossdressing story

10:48

Lingerie, It's not just for women anymore.

06:55

Convinced by his girlfriend to crossdress and then shown off to her friends #crossdress #transgender

06:01

Andrew gets caught crossdressing and becomes a bride, a feminization story

08:07

Procrastination leads to Andrew being dressed as a maid for Halloween

08:06

My Weekend as Holly A Crossdressing Adventure

05:56

Can Meeting ONE Person Change Your Entire Identity?

06:43

Getting started as a crossdresser #crossdresser #crossdressing

07:41

Forced to crossdress, again #crossdressing #feminization

01:19

My new website with Holly Monroe Products #crossdressing

07:07

Holly and the cosplay convention, Andrew decides to crossdress at a cosplay convention #cosplay

06:36

Caught crossdressing and forced to become a maid

06:49

Caught crossdressing and his girlfriends reaction, a feminization story #feminization

06:15

Part 2 of crossdressing for his girlfriend

06:09

Andrew's transformation to Holly, including a trip to the salon, a crossdressing story #crossdresser

05:04

A Dare to crossdress pt 2 - the life changing dare that brings Holly to life #crossdresser

08:10

A dare to crossdress changes a couples relationship forever #crossdressing #crossdresser

07:22

Crossdressed for Halloween, A life changing night #crossdresser #crossdressing

08:22

Holly's Influence: A Journey into Crossdressing and Self-Discovery

08:08

Why Do Some Men Crossdress? Exploring the Appeal of Forced Feminization? #crossdresser #feminization

08:18

Bet lost, Maid Holly Emerges ! Halloween crossdressing fun

04:34

Crossdressed as a female super hero for Halloween, the fun and excitement #crossdresser #crossdress

08:35

Being a bride for Halloween, a crossdresser in a beautiful wedding gown #crossdress #crossdresser

08:37

Crossdressing for Halloween, a crossdressser shines through, #crossdressing #crossdresser #trans

09:09

My crossdressing world - A world in Pink #crossdresser #transgender

05:05

Feminine affirmations for crossdressers #crossdress #crossdressing

06:16

Forced to crossdress in a school uniform #crossdress #transgender

06:30

Holly's forced crossdressing continues with a day at the beach #crossdressing #crossdresser

04:47

A lost bet and Andrew must become Holly to play a tennis match #crossdressing

05:50

The punishment - Andrew and Billy become maids - forced crossdressing #crossdressing #feminization

06:09

Forced to crossdress, part 2, the continuation of Andrew into Holly #crossdresser

06:16

Forced to crossdress #crossdressing #crossdresser

03:52

Andrew becomes Holly, a story of crossdressing acceptance #crossdress #crossdressing #LGBTQ+

05:49

Crossdressed by his girlfriend and her friends #crossdress #crossdressing