Jizz

got new fishnets today and already lost one. i am a bad sissy and need punishment!

Sissies

The "New You" Sissy Experience Game. Choose your punishments!

Sissies

I slapped my mistress on the ass trying to act like a regular man, I was quickly punished, I am sorry mistress.

Sissies

Sissy booty ready for punishment

Sissies

Sissy punishment for attempting masturbation

Sissies

My Daddy punished me last night. This was only the beginning...(PMs welcome!)

Sissies, Sissyperfection

Punish this naughty Sissy, teasing is not allowed!

Sissies

Punish me?

Sissies

punishment photo for disobedience

Sissies

My sissy didn't listen, r/sissies tell me his punishment.

Sissies

Punish me for my dirty thoughts ?

Sissies

Ready to be punished

Sissies

Th...thank you for giving me some of master's favourite underwear after ripping those boxer shorts up and punishing me... Maybe you could punish me a little more? ?

Sissies

sissy driving home from work to be punished because of last night's request to masturbate

Sissy_humiliation, FemdomHumiliation

Punish me?

Sissies

Punish this slut...

Sissies

Punishing my clitty for a Redditor Daddy

FemBoys, Sissies

I was bad girl and punished accordingly...

Sissies

Punish me daddy...

Sissies, Sissy_humiliation

Don’t upvote please. It’ll make my punishment harder

Sissies

Daddy told me I was a bad gurl. As a punishment he let me feel his rod ?

Sissies, LoveThyTranny

Ripped through another pantyhose. Do I need to be punished?

Sissies, Sissy_humiliation

My dumb self tried to quit again. As self-punishment, I must start posting pics here. Hopefully you boys can spread this one around before I find myself trying to act like a man again. ♥♥

Sissies, Sissy_humiliation

Punish Me ..I have been so naughty

Sissies

Punish me please! I’ve been bad ??

Sissies, GoneWildCD, FemBoys, GaybrosGoneWild, twinks

Sissy schoolgirl in position for taking the cane. Please tell me how you'd punish me.

Sissy_humiliation

Punish. This. Ass.

Sissies

I deserve to be spanked & punished!???

Sissies, Sissy_humiliation

Punishing my useless clit. Not sure how comfortable i'll feel about posting these in the morning

Sissy_humiliation

Wow guys. I don't know if i can go a year in chastity, but i will post updates until the day i fail so i can be punished accordingly ;3. That being said, here's day 1!

Sissies

Sissy punished [Non-Con][Incest]

sissycaptions, Sissyperfection

If I don't obey, please punish me

Sissies, FemBoys, u_Charlinetv, u_Avasback-backagain

Daddy demanded that I punish myself for being such a bad sissy and post it..

Sissies, GoneWildCD, sissyplace

Punish and spank me Sir, i have been a bad boy...

FemBoys, Sissies, GoneWildCD

Kneeling and ready to server, or be punished <3 (pm's welcome <3)

Sissies

Sissy needs punishment ideas for if she over eats

Sissy_humiliation, Sissy_Tasks

Master has said i must take tasks from you all, as a punishment for being offline.. so please comment down below what my tasks/punishments should be! x

Sissies, FemBoys

(PUNISHMENT) I have a sissy picture of myself on my Snapchat story. The girl on this picture, is a hot girl I know in real life and I don't want her to find out. For every add on SC I'll reveal one more letter of her IG name on my Snapchat story. Please d

Sissies, Sissyperfection, WouldYouFuckMyWife

Sissy here, don’t take action please. This is my punishment. Send a message to dbaker580 on SC for my total exposure.

Sissies

Punishment in one hand and treat in the other

Sissies, SissyChastity

Am I a bad little sissy? <3 Will you punish me?

Sissies

Punishment (kaf3art)

FutanariPegging, futanari, u_purelytraphentai, u_sissy-boi420, u_cbrogana

This is what I would wear to detention <3 What's my punishment?

Sissies, Sissy_humiliation, SissyChastity

Hi sissies and daddies. I need a huge favor. His mistress here, but hes misbehaved and I need some re enforcement. Anyone want to help me out and PM this closet sissy? Tell him hes been a bad girl and needs to be punished. kik- skip_73

Sissy_humiliation

Sissy princess has been a bad girl and needs to be punished

FemBoys, Sissies, SissyChastity, u_RevolutionaryPanic9

Sissy boy waiting to get his boypussy punished

Sissies

Punish me

Sissyperfection, sissycaptions, u_HelloAllie92, Sissyaddiction, StraightToSissy, u_alsodan, Sissies, SissyInspiration, u_nimblybimbly436

How would you punish a sissy schoolgirl?

Sissies

I've been a bad girl, someone should punish me

Sissies, GoneWildCD

Wife of sissy punishes him for being so pathetic, locks him in cage for me to get a good laugh ??

MicroPenis

How would you punish this sissy next?

Sissies

Sissy slut needs to be punished ? kinky daddies only pls. Kik @ newklkwhod1s

Sissies

I'm a pathetic sissy and i failed my master. I make mistakes and must be punished.

Sissy_humiliation

Hi I will be turned into a sissy sorority pledge this summer and need your help. Please feel free to Kik me at lost_bet_punishment

Sissy_humiliation

this sissy misbehaves a lot, constantly trying to touch that little clitty, should she get punishment?

Sissies, ForcedFeminization, GoneWildCD, SissyChastity, Sissy_humiliation, BBCsissies, chastity, FemBoys, Feminization, gaychastity, transchastity, trapsgonewild

I love stretching and punishing my breasts with hours of nipple pumping! ?

Sissy_humiliation, Sissies

I'm in severe need of punishment

Sissies, sissyplace, FemBoys, FemboyMD123

I've been a bad little sissy bimbo for my Daddy, but he still decided to keep me. I deserve to be punished - kik @ w3rtboi

Sissy_humiliation

Sissy Slave Punished for Not Doing Work.

SissySlavesSub, Sissies, Sissy_hot, Sissydating, sissypersonals, sissyplace

Punish this sissy...please...

Sissies