8 XXX : sissy first time

Got pretty for the first time in a long time, I also made some videos, ill post if this gets enough love <3

imgur.com category @masterlovesbutts

First time doing my full makeup, what do you think?

imgur.com category @TheSissyB

First time posting here, let me know what you think (:

imgur.com category @sissyalt20

First time as a REAL sissyslut ;) Hope you enjoy it as much as i did!

imgur.com category @[deleted]

My first time cumming from anal <3

imgur.com category @[deleted]

First time posting

imgur.com category @latinocross

Re: Sissy Task, First Time Posting

imgur.com category @[deleted]

My first time posting pics - be gentle!

imgur.com category @alexiaissuperho

First time posting myself on here. Please be nice!

imgur.com category @Chazzsissy

My first time here :s What do you guys think?

imgur.com category @strangesweetness

First Time... Nervous!

imgur.com category @slutty_jo

First time posting here, what do you think of my butt?

imgur.com category @chikubihime

first time ever showing anyone. let me know if you like it :)

imgur.com category @sissyaway69

First time dressing in a while, how did I do?

imgur.com category @CDKaylee

My sissy boyfriend's first time getting dressed up and fucked. Doesn't he look cute?

imgur.com category @Woodsmoked

First time posting hope you guys like it :)

imgur.com category @hippesthipster

First time. Here we go!

imgur.com category @TheForgotten117

first time captioning, share your thoughts

imgur.com category @Red_head_01

19 years old. This is my first time sharing sissy pictures, please be rough :)

imgur.com category @kourtneyx

First time sissy, here's my cute butt =^.^= Kinky PMs are welcome =3

imgur.com category @SissySarahs2

first time ever doing this, sooo embarrassing

imgur.com category @steviexoxo

First time showing my little dicklet, be gentle please!

imgur.com category @Natsume93

First time locked up. I can't stand it.

imgur.com category @SecretLifeOfASissy

Today was a big day for me, first time doing my makeup all by myself and I sucked my first cock. I'm such a good little redheaded bimbo x

imgur.com category @gurlyalice

Do I look like a sissy slut now? (My first time)

imgur.com category @katie_the_slut

First time out in public

imgur.com category @Bottomsissy

First time shaving ever! I feel so nekkid!

imgur.com category @sissyago

first time poster! tell me what you guys think (:

imgur.com category @erdinaaha

Sissy panty boy's first time posting on reddit

imgur.com category @pantyboy4fun83

first time locked up !!!

imgur.com category @sissyboini

First time posting on this subreddit.

imgur.com category @LilaTrap

First time sharing a photo (x-post from /r/sissymaid)

imgur.com category @nikki258

First time posting here...hopefully you guys like my big ass :)

imgur.com category @SissyJenna13

First time posting, Please humiliate me

imgur.com category @SissyAmberxxx

First time sharing, be nice please

imgur.com category @Eva_sissy

Some first time(some better than others) pics of my sissy self. please humiliate me! Kik: pantybuttsissy

imgur.com category @lilgirlpantybuttslut

First time post.

imgur.com category @Keira2000

First time locked up. 2 hours for every upvote.

imgur.com category @tendersiss

First time posting, should I do it more?

imgur.com category @sissy_slut_kikme9999

First time using my first dildo! Love it soo much!

gfycat.com category @My-N-quite-SFW-alt

First time in chastity, you can tell I’m a bit excited!

imgur.com category @Thisisntathroaway

First time with a man

imgur.com category @[deleted]

First time sharing a photo

imgur.com category @nikki258

Long time follower, first time posting :)

tumblr.com category @BestGirlBess

First time might be rough

gfycat.com category @Woolfix

Tried a garter belt for the first time. I'm more and more of a sissy...

imgur.com category @lilblkdck

I think this is the first time Im showing off this faggot. Her name is Nikki, and I’m sure she’s one of the gayest sissies i’ve ever spoken to. She even told me her clit is getting hard just thinking about all of you looking at it. Let her know how much y

imgur.com category @blackbearr21

First time being a sissy in public

imgur.com category @mrcave81

First time upload & sissygasm after being locked in chastity for 3days, teased with hypno, please call me a sissy and emasculate to keep me motivated!

gfycat.com category @SissyEmilys

First time dressing like a girly slut out in public, did I pick a good location?

imgur.com category @JesseLaCroixxx