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Sissy Time

First Time Sissy, Please Be Gentle (Pics Inside)

Re: Sissy Task, First Time Posting

A sissy must be dainty and pretty, yet ready to turn into a cock-hungry slut at a

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

Long Time Dresser and /r/sissies But Have Never Posted. Here We Go.

This is inevitable sissy. Just accept it now, and it'll be easier. Now on your knees,

First time cumming since embracing my inner sissy ( with dress up of course)

Safer this time! What a horny young sissy gets up to late at night...PMs welcome!

Really like the feed back I got last time. Any young sissies?

First time post here. Sissy sex slave for you(; Send some dirty and kinky pms(;

Look like I have some time for a new sissy. Cum be mine.

Hi all... 28 male crossdresser here, first time submitting to /r/Sissies... please

panty time sissies

BdsmGW didn't like the sissy maid this time

First time showing my sissy ass. Do I have potential? Tell me what you think and

First time posting a pic. My sissy ass

Does anyone enjoy the tush of a non-white sissy? :) (First time posting!)

Every time i start again i go deeper in lol guess i really am a sissy

First time posting in sissies

Shaved my boipussy for the first time, can I be your sissy?

On the 11th day before Christmas I give /r/sissies... a pic of the first time I got

tying white sissy outfit for first time

I'm gonna be a full time sissy this weekend

First time wearing panties.... Hope your cocks are getting hard because of me, Master....

My soft sissy clitty, time to invest in a cage. DMs and wonderful comments welcome!

I did what all good sissies do in their free time(=

dumb sissy like me forgot to post this pic in my album last time, kik is sissyshame

First time sissy - be dirty in your comments!

One Mistake And She's Keeping Me Locked Until The End Of Time

Mistress says that it's time for the next round of my sissy training - Wanna help?

It's friday, time to do sissy things

sexy little ass just before leaving this morning. It's more than a little tempting

Turns out I had a “Sissy Hole” the whole time! It’s pretty but I’m not sure

A good sissy maid takes time to practice

Taking the first big step by going outside while dressed for the first time, so nervous

So next weekend will be my last free time for awhile. I want to go big and I am looking

First time sissy smooth in a year...bye bye nasty boy hair

New sissy first time posting

I have only been on a sugar-daddy dating site for one day and have been favorited

New sissy, first time here! <3

The last time is far too long ago, feels good to be wearing this again..

It's sissy selfie time!!! What would you do to this girl??? ?

My first time posting my sissy pics hope you guys like them ??

Should i just be a full time sissy?

While ago I was a straight boy, but now I'm almost bending over... And I think my

First time: Please tell me what you think of my butt? What would you do with it?

Meeting with a daddy for the first time tomorrow night! Here's an old pic from the

/r/sissies motivated me so much & now I am in chastity for the very first

I thought I was a straight boy, but now this quarantine and too much free time are

Need a dominant alpha to help me start living full time as a sissy whore. Need a

I deleted my account again but I'm already back! Please help me stay this time...

First time ever being used by a mistress and losing my sissy virginity. Like what

Every time I take a break I come back 10x as desperate for cock ?

My boyhood vanished a long time ago. All that's left now is this. I was was always

Helping a Caged Sissy in Philadelphia find a IRL relationship with a local dom/daddy

High sissy slut here looking for fun. I love sissies in sexy panties and promise

High sissy slut here looking for fun. I love sissies in sexy panties and promise

High sissy misstress slut here looking for fun. I love sissies in sexy panties and

This sissy just went outside dressed up for the first time and exposed herself! I

High sissy misstress slut here looking for fun. I love sissies in sexy panties and

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