sissydressing

to r/sissydressing by rjarrick1

2 weeks ago

3

💕

Posted by rjarrick1

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to r/sissydressing

3 weeks ago

to r/sissydressing by sissyfag4579

3 weeks ago

4

Pink is my favorite color

Posted by sissyfag4579

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Disabled

to r/sissydressing

3 weeks ago

to r/sissydressing by jessicaheavents

1 week ago

6

Have a nice sunday ❤️

Posted by jessicaheavents

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to r/sissydressing

3 weeks ago

to r/sissydressing by EllieCD93

3 weeks ago

13

Am I dressed correctly for?

Posted by EllieCD93

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to r/sissydressing

3 weeks ago

to r/sissydressing by Siss_Sophia

3 weeks ago

18

My not so small clitty

Posted by Siss_Sophia

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to r/sissydressing

3 weeks ago

to r/sissydressing by Objective_Shop4682

3 weeks ago

1

I deleted a bunch of pictures here are just some i kept

Posted by Objective_Shop4682

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to r/sissydressing

3 weeks ago

to r/sissydressing by Siss_Sophia

3 weeks ago

13

Wishing you a great weekend!

Posted by Siss_Sophia

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to r/sissydressing

3 weeks ago

to r/sissydressing by Lexi_Milan

3 weeks ago

3

Am I Wifey Material?? 🥰

Posted by Lexi_Milan

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to r/sissydressing

3 weeks ago

to r/sissydressing by OliviasSecrets

6 days ago

9

My easily accessible thong is so cute

Posted by OliviasSecrets

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to r/sissydressing

3 weeks ago

to r/sissydressing by YoMamaLCV40

3 weeks ago

4

Surprise! 🤭

Posted by YoMamaLCV40

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to r/sissydressing

3 weeks ago

to r/sissydressing by kinkykitty_00

3 weeks ago

8

Can I be your plugged femboy wife? 💍💖

Posted by kinkykitty_00

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to r/sissydressing

3 weeks ago

to r/sissydressing by Siss_Sophia

3 weeks ago

7

It's not much but it can take a lot

Posted by Siss_Sophia

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to r/sissydressing

3 weeks ago

to r/sissydressing by YoMamaLCV40

3 weeks ago

2

Tell me if you would slide my panties🫣

Posted by YoMamaLCV40

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to r/sissydressing

3 weeks ago

to r/sissydressing by OliviasSecrets

6 days ago

6

So soft and so cute

Posted by OliviasSecrets

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to r/sissydressing

3 weeks ago

to r/sissydressing by daddiesslvt

1 week ago

2

Love latex

Posted by daddiesslvt

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to r/sissydressing

3 weeks ago

to r/sissydressing by Time_Concern_3547

3 weeks ago

19

Love dressing up like a sissy slut

Posted by Time_Concern_3547

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to r/sissydressing

3 weeks ago

to r/sissydressing by abbybabyboo

3 weeks ago

3

Throwback to my first outfit exactly one year ago! Finally accepted my sissy self!

Posted by abbybabyboo

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to r/sissydressing

4 weeks ago

to r/sissydressing by sissyfag4579

3 weeks ago

5

Feels so good

Posted by sissyfag4579

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Disabled

to r/sissydressing

4 weeks ago

to r/sissydressing by Advanced-Bluebird448

3 days ago

Preview thumbnail for Sadly it feels im never going to find another sissy to have a switch playdate, having a night being drilled and drilling is slowly feeling like a pipe dream thats fading out 😭 would of loved to feel that explosive warm oh so goodness fire deep inside but, what can i do .... 😭 image

5

Sadly it feels im never going to find another sissy to have a switch playdate, having a night being drilled and drilling is slowly feeling like a pipe dream thats fading out 😭 would of loved to feel that explosive warm oh so goodness fire deep inside but, what can i do .... 😭

Posted by Advanced-Bluebird448

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to r/sissydressing

4 weeks ago

to r/sissydressing by Objective_Shop4682

4 weeks ago

4

My favorite pictures from the last couple years

Posted by Objective_Shop4682

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to r/sissydressing

4 weeks ago

to r/sissydressing by Sissy_HollyQuinn

3 weeks ago

1

Let's see how much of a bigger bimbo slut you can make me into. 💋

Posted by Sissy_HollyQuinn

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to r/sissydressing

4 weeks ago

to r/sissydressing by OliviasSecrets

6 days ago

7

I was made for lace, silk, perfume, and bows.

Posted by OliviasSecrets

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to r/sissydressing

4 weeks ago

to r/sissydressing by Timely-Membership567

2 weeks ago

2

Hi everyone. Who wants to be my sexy girlfriend?

Posted by Timely-Membership567

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to r/sissydressing

1 month ago

to r/sissydressing by Aggravating-Hotel863

3 weeks ago

16

First post here be nice 🥺

Posted by Aggravating-Hotel863

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to r/sissydressing

1 month ago

to r/sissydressing by randi_sledge

3 weeks ago

2

These titties might be the main event, but stick around... I’ve got a surprise that’ll really make you blush 😘✨

Posted by randi_sledge

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to r/sissydressing

1 month ago