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a bad sissy waiting to be punished by Daddy
Facesitting femdom sissy cock punishment gif
Administer swift punishment should your sissy maid snag her stockings! #sissyslut
xxx
sissification: How cute! Sissy punishment art.
sissygasm: Proper technique for all sissies. THIS is how EVERY real sissy should pee! If you’re a true sissy and you aren’t doing this every time you need to be punished!
tallulahhh: tallulahhh: Lazy housework! Maid uniform from thesissystore.com Rebloggin’ myself to prove that *some* sissy maids do the housework. Between oh-punish-me lazy breaks.
agracier  said:a sissy punished …http://transeroticart.tumblr.com  said:Artist unknown - (If anyone has any further information, feel free to let us know at: http://transeroticart.tumblr.com/submit). Please include the post number when doing so.Be
Jess’s punishment for jerking off yesterday
Take your punishment like a woman….bitch
You gotcaught stealing from a lingerie store and now the sales girls are going to have their fun punishing you
A wicked punishment for playing with yourself while you’re dressed up in my clothes and underwear
Oh would you look at that, a hard pantied cock under your skirt. That means you’re a slut and I like to punish and humiliate sluts like you
I think little period punishment is in order for this masturbating sissy bitch who’s dressed up in my lingerie
Punished
It’s time for the next phase of your sissy punishment.
If you disturb my fuck I’ll punish you like never before.
petticoat punishment art by “BJ”
sweetnathalietv: Yet another sissy being conditioned to associate pleasure not with her clitty, but with her tight little sissycunt. To make this even more effective, her clitty will be used for punishment solely.
Don’t you think you’ve watched enough, sissy?Be a good girl and turn around and we’ll let you listen in.
Joana (John) was punished in the salon with a tight perm and bleaching.
“Hi Peter. So… you’re the guy for the full makeover?! Your girlfirend gave us a call with some instrunctions. Ok, sissy, let’s go….”
“Finally, i’ve decided that you’ll will get tight curly perm, sissy!”
Finally, you’re a real girl. The last step of your feminization is done. You’ve got a perm in your virgin hair. Your tiny cock is locked in a chastity tube, you ass is filled with a plug, your make-up is slutty. Poor sissy.
“Oh Sissy, i know… my outfit turns you on and it hurts in the chastity cage. Now, dress up for the salon. You’re getting a perm today”
Punishment: Every sissy must face humiliation at lease a thousand times over their life. Accept it.
Sexual Subtext: Enough already! He want’s to fuck your sissy ass and you want him to. Get on with it and quit pussyfooting around. By the way: give that sissy an A for wearing that outfit to class.
Let the punishment fit the crime: make your sissy share all of the cock that she attracts to your place. That’ll teach her.
Definition of the word punishment: he doesn’t know it.
chien-cl: Maid Shocked and PunishedGoddess Sara is angry with her sissy maid. “he/she” is punished in total chastity for 30 days for “his/her” constant mistakes and errors in the tasks given by Goddess Sara. Now Goddess Sara humiliates and punishes
Make me red and raw :3 Punish this chubby sissy slut!
Punishment for not finishing a task on time. Each time more pics will be sent out to be posted.
Sissy Lost Bet
Went to the salon today, but I was too much of a scared sissy to ask for a pink glittery pedicure (last pic) so this is part of my punishment for not following instructions: no wig pics.That’s what you deserve! Next time go all out gurrrrl!
Sissy Sluts first audition. She must post at least 3 more as part of her exposure punishment. The next submissions should be more humiliating…. any suggestions?
Sissy craves punishment :)
Punishing my clitty for mistress.
What in the hell?! lol
A note to all you kitty maids, sissy maids, and sissy kitty maids - your Mistresses won’t forget if you spill their tea or bring them the wrong kind of food! Sissy Joy got her due punishment in our tea party video, coming soon to Petplay Palace!
petplaypalace: A note to all you kitty maids, sissy maids, and sissy kitty maids - your Mistresses won’t forget if you spill their tea or bring them the wrong kind of food! Sissy Joy got her due punishment in our tea party video, coming soon to Petplay
Sissy Joy is quickly becoming a regular plaything here at Petplay Palace! For this fun shoot, she was tasked with putting together a tea service for Mistresses Denali and Alice. But will this sissy kitty manage to get everything right and avoid punishment
letmebeyoursissy: oh how l wish this was me…….
sometimes a little sissy boi has to be punished and if its in front of friends all the better
sissy boys need a good ass tanning to make them focus
sweetnathalietv: I guess I gave a wrong answer again when asked if I longed for a strict mistress.I said yes. In that part of my fantasy, unautorized squirting is a punishable offence.
spanked2tears: How embarrassing! A wife punishing her sissy husband in front of her friends – now that’s humiliating
Summer Series Threesome Thursday: Which outfit do you choose to wear sissy? Which Goddess do you choose to reward you? Which Goddesses do you choose to punish you?
Goddess Martha will punish her thieving sissy boy.
daddywantssissys: Submission is the is true thing that matters most when becoming a sissy. You need to do what’s necessary to show your will is broken or be punished by having yourself forced into nasty things until it happens.
ATTN ALL: My little pathetic cucky at home disobeyed my orders. Message me how to punish him and I will repost your ideas and pick one (or more) to implement!
herhappysissywife: sandybrown121: This is why it’s so difficult to effectively discipline a sissy -they usually enjoy the punishment as much as the crime! Punishment? For Who? Faced with the task of disciplining a sissy, the Dominant Wife finds
billblakean: In a by-gone era (6 decades ago), some still employed old-fashioned methods of punishment. Act like a baby, and be treated as one, was the consensus attitude. A misbehaving ne'er-do-well was appropriately attired and put on display. Like
Sissies get the best punishments.
lockedupinlove: Punishment can take many forms…
Forced Feminization Caption - A Lasting Punishment
Permanently Punished Percy at the #sanfrancisco #crossdressing club during our monthly #meetup #social #munch at #wickedgrounds. #sissy #1950s #sissification #crossdresser #vintage #humiliation #poodleskirt #kinky #bdsm #cosplay
You better be good or else you will have to wear the PUNISHMENT PANTIES!!! #art #shenanigans #femdom #mistress #aliceinbondageland #bdsm #kinky #funny #lingerie #fisting #strapon #pegging #panties #sexy #sissy #crossdresser #crossdressing #humiliation
