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Trying a bigger clitty for the first time.

first time going out in gfs clothes 🙈✨

First time caged, I came all over myself shorty after 😅

My first time dressing up and posting

Crossdressing First Time High Heels gif

First time posting here :) excited to read what you think

First time I cum in Venti ass (Genshin Impact)

Bareback Crossdressing First Time gif

First time showing my boobs I hope at least one person likes it 🙈

first time dressed for anyone and I take two and record it 😂 (oldie but a true first time)

My first time (ki_k:SissyCDslutHUN)

When daddy slides in

Daddy fucking me (ki_k:SissyCDslutHUN)

Throwback from last year.

First time putting something down my throat, how did I do ?!

First time on a dildo. Please be nice. Working my way to my true sissy self.

First date with Daddy

The final test...

My first time getting fucked by a BBC

Long time watcher first time poster, new fit I put together ^-^ 💕

(19) First time riding my dildo, already a pro ;)

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My first BJ on NYE 😇🥵

Amateur Crossdressing Femboy First Time Fucking Machine Sissy Porn GIF by spoon359

First Grindr Hookup

Your First Time Trying On Panties: Dirty Talking Girlfriend & Crossdressing Encouragement

First time cumming in or on fishnets

First time wearing panties, how do I look?

The first time you were left alone at home

First time trying to twerk

my first ever time doing my makeup, I think it turned out pretty good!

Hi! First time posting on here, I think I may be gender fluid I’m not too sure. I hope I’m still pretty enough to fit in here <3

First time oiled up in my swimsuit and thigh-highs, I honestly couldn't stop twitching I felt so good (ꈍwꈍ )

First time fully trapped out.. howd I do? c;

First time posting a video. Hope you guys like it ☺️😘

My first time posting nudes, be kind >.<

First time trying out my toy, did I make a good job? 🥺

First time poster! I'm super tight, but that will change soon I promise <3

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Power Bottom Sissy Needs No Anal Training

First time cumming in a flat cage

Stretching; One Of The Most Important Lessons In My School Of Sissification (OC)

First time public

I sucked a cock and got fucked for the first time the night I shot this video

Sissy Takes Her Final Exam! (OC)

First time riding dildo in a flat cage

First time posting here

First time Cumming in a cage, seems like I have accepted fate 😋

First time in a bodysuit or leotard

That summer I wore a skirt for the first time...

First time trying out a girly outfit, what do you think?

Can I be your first time sucking cock?

My first time orgasming while fucking a dildo…it was life changing ☺️

This was first time I crossdressed… memories

First time using baby oil 🍑

Full Submission (OC)

Congratulations On Being The 70th Sissy Graduate (OC)

Tease my hole before you push that cock inside me, bud

first time in a skirt in a while!