04:09

My neighbors maid a crossdressing story, #crossdresser, maid

06:57

Caught and forced to crossdress #crossdressing #feminization

05:40

How to tell your girlfriend you crossdress, crossdressing and feminization

04:44

crossdressing with a friend #crossdressing #feminization

04:17

How to crossdress, Crossdressing 101 #crossdressing #transgender

04:14

Holly's crossdressing story #crossdressing #transgender

09:29

Crossdressing for his girlfriend #crossdressing #transgender

04:44

A crossdressing night out - #crossdresser #transgender

05:07

Hollys vintage crossdressing with vintage lingerie from catalogs

04:29

A vintage lingerie catalog leads to crossdressing fun

05:31

Andrew's crossdressing adventure, a lost bet leads to a night as Holly #crossdresser #crossdress

04:14

a crossdressing adventure

04:07

The story of Holly and her start to crossdressing, #crossdressing #transgender

06:02

A New Years Eve crossdressing and feminization adventure

05:56

A crossdressing Christmas wish #transgender #crossdressing

04:27

A lost bet leads to a crossdressed cheerleader, a feminization story #crossdressing

04:57

A bra and panties leads to a night of crossdressing, a feminization story #crossdressing

05:25

Shopping for a wedding gown, a crossdressing and feminization story

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