zNSFW

First Time Crossdresser

(M)y new favorite stockings! Long time lurker, first time poster.

[M]y first time, I heard /r/gonewild liked this? - [cd] [crossdresser]

I was suggested to post my full set here from r/crossdressing - first time in make

Hi, I'm a Crossdresser, who secretly dresses up when my girlfriend is out. I'm nervous

SELF, NSFW - Silent Hill Nurse, First time post and First time Crossplay/Crossdress

First time here, repost of pic from crossdressing

24/CA & saving up for hormones ^_^ First time posting here so I'm sharing

Hi all... 28 male crossdresser here, first time submitting to /r/Sissies... please

Long time crossdressing.... first time posting a picture of myself.

The first time I ever crossdressed I was 7 and found a pair of pantyhose. I've been

Tried crossdressing for the first time. These are some outfits I put together!

Hello! First time posting here

Girlfriend and I playing dress up for the first time?

First time posting here. Ladies and Feminine Crossdressers welcomed! PM me!

Re: First time complete crossdress

First time posting. There may be more if you enjoy!

My first time dressing up.

Hello, It's my first time posting here so please rate my picture so i know if i should

I want to be a sissy. What do you think about my first time crossdressing? Please

My first time crossdressing#throwback

New... and NERVOUS. First time poster hoping to connect with some CDs like me

My first time in a wig :) I recently started crossdressing

How do I look ? first time posting... I don't have clothes or a wig anymore as I

My first time dressing. Soon a wig!

My first time crossdressing in lingerie, any tips?

My First time dressing for over 10 years... Crap pics & clothes but really

White Sissy first time posting

How's the view :)? first time crossdressing be nice <3

Ready for my first time..Any takers?

Dressing up for the first time.

It's my first time taking pics, so please be gentle!

My very first time crossdressing

23 first time poster - Am I doing this right?

First time trying this crossdressing thing ?

One of my first times crossdressing. It ended very messy! Chat me for more!

Not sure how this sub likes crossdressing, but was feeling cute in my new nighty

First time. Former bull. Exploring this end of the spectrum after an encounter with

New to this. First time. How am I doing?

Hi, this is my first time crossdressing :)

My first time locked in a chastity cage! I think I'm in love!

Do I fit here? First time posting, please be gentle..

[TS] Crossdressing with thigh boots for the first time

I tried a crossdressing cosplay publicly for the first time :)

My first time. Please be gentle.

Dressed up for the first time in awhile

I know I dont have the best body type for crossdressing as a sexy school girl but

I know I dont have the best body type for crossdressing as a sexy school girl but

[19] First time crossdressing, How's my sexy police(wo)man?

samantha fekete joip (assplay self-facial crossdressing) (first time making a joip

Throwback pic from a closet sissy's first time crossdressing for me. She's come a

Like a Virgin,Touched for the very first Time Hi Sensy-Arlette

I visited Grandpa in the nursing home for the first time dressed as the gay sissy

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