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Crossdressers First Time gifs

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My first time doing this

My first time doing this

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First time posting vid. Im so excited 🥰

First time posting vid. Im so excited 🥰

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First time trying this position

First time trying this position

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My first time riding a BBC dildo

My first time riding a BBC dildo

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First time posting a gif here... Hope ya'll enjoy me showing off a little

First time posting a gif here... Hope ya'll enjoy me showing off a little

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First time Outdoor 🙈 should i repeat it with Toys and clothes? 🥰 Would need

First time Outdoor 🙈 should i repeat it with Toys and clothes? 🥰 Would need someone to give me some Motivation and ideas thooo

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Gif of my first time

Gif of my first time

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Need to be made into a bigger sissy and get my ass fucked for the first time

Need to be made into a bigger sissy and get my ass fucked for the first time

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First time in and I only almost woke up my roommate ;) So glad I went bigger!

First time in and I only almost woke up my roommate ;) So glad I went bigger!

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Saika Totsuka first time anal and deepthroat (OreGairu)

Saika Totsuka first time anal and deepthroat (OreGairu)

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Its my first time making a video...please be nice

Its my first time making a video...please be nice

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M4f. First time cd, use me and abuse me

M4f. First time cd, use me and abuse me

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first time posting here, hope y'all like me :)

first time posting here, hope y'all like me :)

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First time posting here and I'm shy so be kind ?

First time posting here and I'm shy so be kind ?

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First time taking my new bbc

First time taking my new bbc

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First time walking outside in Chastity.. no panties.. and a VERY short skirt?

First time walking outside in Chastity.. no panties.. and a VERY short skirt?

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First time showing my clitty uncaged here ???

First time showing my clitty uncaged here ???

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First time here, I hope you like it I would love to post more ☺️

First time here, I hope you like it I would love to post more ☺️

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First time with a dildo… might’ve gone too big ??

First time with a dildo… might’ve gone too big ??

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First time wearing a skirt… I loved it!

First time wearing a skirt… I loved it!

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First time taking a cock this big, did I do good?

First time taking a cock this big, did I do good?

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First time taking it and I think I did pretty well ?

First time taking it and I think I did pretty well ?

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First time outside dressed as a girl and it felt so magical <3 nearly got

First time outside dressed as a girl and it felt so magical <3 nearly got caught tho...

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First time trying to do a foot job ??

First time trying to do a foot job ??

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First time hands free

First time hands free

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First time posting. So nervous >~<

First time posting. So nervous >~<

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First time out of chastity in several weeks, didn't take my little clitty long to

First time out of chastity in several weeks, didn't take my little clitty long to cum... ?

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First time wearing chastity. I can't begin to tell you how right it feels to fuck

First time wearing chastity. I can't begin to tell you how right it feels to fuck myself like this.

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Feeling brave enough to post again for the first time in a while after deleting all

Feeling brave enough to post again for the first time in a while after deleting all my posts :3

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First time showing me riding, did it went good?

First time showing me riding, did it went good?

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My first time making a submissive cuck locked in chasity, dressed up, and leashed

My first time making a submissive cuck locked in chasity, dressed up, and leashed force bi fucklick and suck on their girlfriends bulls big cock . Thanks u/aurora_aspen for the opportunity !

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Me crossdressing for the first time in a while. Hope y’all like :3

Me crossdressing for the first time in a while. Hope y’all like :3

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Hii! First time here, how did i do? :3

Hii! First time here, how did i do? :3

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I knew from the very first time I felt something inside me I’d never want to be

I knew from the very first time I felt something inside me I’d never want to be straight again. ;)

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Is it gonna be your first time with a sissy?

Is it gonna be your first time with a sissy?

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First time dildoing my sweet ass hole

First time dildoing my sweet ass hole

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(31) first time with a thick cock

(31) first time with a thick cock

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Went outside dressed like a girl for the first time ever! I got so excited I must've

Went outside dressed like a girl for the first time ever! I got so excited I must've forgotten my panties at home.

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First time posting hopefully you enjoy 😘

First time posting hopefully you enjoy 😘

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You never forget the first time.

You never forget the first time.

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😜 there's always a first time.

😜 there's always a first time.

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When it slips in for the first time in a long time 🫠

When it slips in for the first time in a long time 🫠

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My first time wearing a cage

My first time wearing a cage

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First time I got bred by someone

First time I got bred by someone

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First time posting here 😻

First time posting here 😻

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Me using the Fleshlight ice lady for the first time, feels amazing!

Me using the Fleshlight ice lady for the first time, feels amazing!

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first time 🥵❤

first time 🥵❤

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first time trying a plug

first time trying a plug

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Inserting my new very big dildo for the first time. I hope you like ;)

Inserting my new very big dildo for the first time. I hope you like ;)

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Maid trying machine for the first time!

Maid trying machine for the first time!

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Asian sissy, first time with a BWC

Asian sissy, first time with a BWC

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I had too much fun in a cage for the first time...

I had too much fun in a cage for the first time...

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Taking a dildo for the first time in years, didnt expect to go so easily 🥴

Taking a dildo for the first time in years, didnt expect to go so easily 🥴

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first time in chastity made me 🥵

first time in chastity made me 🥵

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What if you saw me inside a car doing this? This was first time for me hehe

What if you saw me inside a car doing this? This was first time for me hehe

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[m]y first time sharing. Be nice and there'll be more.

[m]y first time sharing. Be nice and there'll be more.

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First time posting here…

First time posting here…

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[25] My first fuck post, my phat ass been fucked few times but first time sharing

[25] My first fuck post, my phat ass been fucked few times but first time sharing here so enjoy! 😝

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Your first date say its her first time...

Your first date say its her first time...

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My first time getting it as a sissy :)

My first time getting it as a sissy :)

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