8 XXX : sissy first time

Long time lurker, first submission. Who wants to see more?

imgur.com category @progressivelykinky

My first time dressing up ;) accidentally deleted all my pics should I take more?

imgur.com category @tncd20

Deleted this the first time but Mistress made me put it back up. This is after a trip to the mall.

imgur.com category @anasb1tch

[M]y First time in a Dungeon. (someone suggested I post here)

imgur.com category @Sub_Stud

For the first time...

imgur.com category @[deleted]

Trick or Treat! (original) (first time captioning)

imgur.com category @IvyLust

Pics of me being a sissy for the first time

imgur.com category @deerbutt

Hi~ first time here, kinda shy about this...

imgur.com category @steviexoxo

Ready boys? (First time posting)

imgur.com category @Michelle4u2

My first time here.. Please be gentle :x

imgur.com category @[deleted]

Please be gentle~ Do I look alright? First time (:

imgur.com category @Son_of_Hedonism

My first time posting here :)

imgur.com category @adorabledorkkitty

My first time posting here, how do I look?

imgur.com category @jlmc1028

Think i can be a good sisssy..:) first time posting me online . PMS welcome very much XO

imgur.com category @belllaxoxo

From behind (first time showing a little face). Thank you for all the love <3

imgur.com category @Hailleyros

First few times be like

tumblr.com category @Groovryd

First post in quite some time

imgur.com category @LilaTrap

Couples first time posting on this page.. feedback would be much appreciated :)

imgur.com category @PassionateChemistry

Just posted on r/sissies for the first time, wanted to come here too :)

imgur.com category @Jason_Sanders1511

Taking Chance for the First Time

imgur.com category @addyftw1

Familiar with chastity, new to sissification. First time poster. Am I doing this right?

imgur.com category @secretsissykins

Got sissied up for the first time with my cage on and took some pics!

imgur.com category @JessicaSissyCumSlut

Crazy to think my first time with dick inside my hurt and I thought I’d never want it. Now I crave it and I’m making this face. I’d like to thank my cage for that. :)

imgur.com category @[deleted]

Gave a blowjob for the first time yesterday and I loved every second

imgur.com category @SisKayra

Bi sissy, new to fully dressing. Looking for daddy to take me out first time while I please him all night

imgur.com category @dressupblessup

Bondage Chastity Brandynette - First time i tie myself a cage. SissyGasm is awesome and the balls cool down fast!

imgur.com category @Brandynette

First few times be like

tumblr.com category @Groovryd

Thought for sure I was going to get fucked for the first time ever last night. Got flaked on

imgur.com category @Therealjennibaby69

I tried doing my own makeup for the first time before chores, instead of having it done for me by my friend! She says it was rather good for a first-time effort. I hope you all like it too!

imgur.com category @softerword