Jizz

Should a sissy always be in chastity?

Sissies

My sissy before 3 weeks of chastity.

Sissies

This sissy has been locked up in chastity for weeks!

Sissies

Anyone like a sissy in chastity on her knees?!? POV pic

Sissies

Day two of sweet sissy chastity

Sissies

Lingerie fun with sissy chastity<3

Sissies

Locked up, like a good little sissy

Sissies, chastity

On the 11th day before Christmas I give /r/sissies... a pic of the first time I got my clitty locked up in chastity.

Sissies

Feeling like a true sissy. x

Sissies, GoneWildCD, chastity

I remember rolling my boxers up like a thong in second grade... NowI think I have become a real sissy. 50+ pairs of panties, lingerie sets, makeup, chastity, a dildo, and toys.. I might need help...

Sissies

Oz Sissy Chastity. What do you think? Kik: kent_daivey

Sissies

What prolonged chastity do to a weak sissy

Sissies

One week out of chastity, so good to be locked up again:)

Sissies, FemBoys, Sissy_humiliation, GoneWildCD, SissyChastity

Being locked in chastity can be so frustrating, but it makes me a better sissy

Sissies

peel aside my thong and make me the sissy i am

Sissies, chastity, SissyChastity, GoneWildCD, FemBoys

Trying to be a good sissy!

Sissies, chastity

A week caged makes for one horny sissy

Sissies, chastity

is this chastity small enough ?

Sissy_humiliation, Crossdressing_xxx, Sissies

I like to play games of chance. If I get 15 votes in 15 minutes, I'll share my sissy maid chastity pics for everyone to see, share and spread :)

Sissy_humiliation, sissykik

Let me be your sissy maid, full service guaranteed!

Sissies, GoneWildCD, chastity

I never thought my life would come to me begging men to rape me and lock my useless clitty in chastity. I guess I'm just embracing the sissy lifestyle ♥️

Sissy_humiliation

Locked away

SissyChastity, Feminization, FemBoys, chastity, Sissies, ForcedFeminization, Sissy_humiliation

cute trans sissy in chastity

Sissies

Cage so small..

SissyChastity, Feminization, ForcedFeminization, chastity, Sissy_humiliation, Sissies, FemBoys, SissyBoy, Femdom, FemboyGalleries, sissyplace, TransTributes, TrapCumTribute, gaychastity, GoneWildCD, SissyHeaven, SissyMisogynyFetish

Husbands in chastity make perfect sissy housewives<3

Sissies

I'm a married, bisexual sissy in chastity, what do you think?

Sissies

For a proper Sissy, "Locktober" is just another month. ??

chastity, ForcedFeminization, KinkySissyFBTCD, Sissy_humiliation, SissyChastity, sissymaid, hopeshelikesit, u_thongking92

I will be good boy I promiss

gentlefemdom, chastity, Sissies, Sissy_humiliation, Feminization, GoneWildCD, SissyChastity, BBCsissies, sissyplace, FemBoys, u_eddytrav

I'm such a sissy gooner the only thing keeping me from constantly jerking off to pictures of myself is my chastity cage

Sissies

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

Sissies, FemBoys, GoneWildCD, traps

Not sure about this pic here, still hope you all like it, at least I had fun doing this :)

Feminization, sissyplace, StraightToSissy, ForcedFeminization, girlschool, SissyInspiration, SissificationProject, chastity, Sissy_humiliation, Sissies, u_SissyEmilys

Can I get some love and attention to boost my feminine side? :)

Feminization, sissyplace, StraightToSissy, ForcedFeminization, girlschool, SissyInspiration, SissificationProject, chastity, Sissy_humiliation, Sissies, u_SissyEmilys, GoneWildCD

Dressed as a prissy,sissy maid before getting pegged by Princess

chastity, Feminization, ForcedFeminization, sissyplace, Sissy_humiliation, SissyChastity

caged sissy sucking on a fat dildo

Sissies, SissyChastity, chastity

Penetrating my sissy hole whilst locked in chastity

Sissy_humiliation

Is there any love for a locked sissy?

Sissies, SissyChastity, chastity, Gigi977

Helping a Caged Sissy in Philadelphia find a IRL relationship with a local dom/daddy who'll spoil her. She is full-time, 25, 5'3, petite, 100% passable, submissive bottom. She understands being spoiled indefinitely means being kept in chastity indefinitel

Sissies

Caged for days My sissy cuckold hubby posing like the little sissy bitch he is. A powerful reminder of his position in this relationship. Caged and ass up like a slut...Ha!

chastity

Locked up like a Good Sissy

Sissies, traps, sissydressing, GoneWildCD, trapsarentgay, FemBoys, chastity

Caged Trans/Sissy Girl. Petite, Femme, Real Hair in 24/7 Chastity. Say hello. Kik:ChaNickWdrrr

Sissies

Caged Trans/Sissy - Petite, Femme, Real Hair, in 24/7 Chastity. Say hello. Kik:ChaNickWdrrr

Sissies, sissydressing, Sissydating, SissyChastity