chastity challenge
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sissymaidflorence: I wonder what the people I meet every day would think if they knew how I’m dressed under my work clothes?!  Hiding a full corset like this one is quite a challenge, though. Not into chastity devices but the rest WOW
iamsissysamantha: TO JOIN MY SISSY CHALLENGE JUST REBLOG WITH YOUR SISSY NAME SAMANTHA WILL OF COURSE BE JOINING YOU :) BEGINNERS CAN EAT THEIR OWN CUM BUT IF YOU’RE REALLY SERIOUS ABOUT BEING A SISSY CUMSLUT LOCK YOURSELF IN CHASTITY THEN
submissive-william: You should know better than to accept challenges from your smartarse girlfriend. While still wearing her skirt, she had said “Are my panties red or pink? Guess right and I’ll halve your chastity time. Guess wrong and I’ll double
nothing-for-him:Challenge: Double your chastity time!
mistressh666: while-in-chastity: This is a view with the smaller base ring. Quite tight and really a challenge during nights. Let’s see when I get used to it. But I really like the rigid way my dick is caged now. Yes I can see that you like the way
nothing-for-him:Challenge: Go to work in chastity for a day!
teaseanddenialcaptions: Baby, I just talked to Kelly and she told me that she put her boyfriend in chastity, too! Isn’t that great? You know how competitive we are, so now we can challenge us to see who can resist longer to let her chaste boyfriend
mylittlexperiment:I am joining the Locktober challenge mainly to get back into chastity play. My closest friend is holding the keys for me. She says she might push me longer than just October :) Talk about a friend with benefits, DAMN. That friend just
urtica-c: mountainsubmission: Whenever we’re in the midst of a chastity lockup challenge I wear my keys proudly 24/7. Only one person has asked me what they are for and I’ve only caught eye contact with one person at the bank that knew what they
The chastity advent calendar game1. Pick 25 do-able challenges for your key-holder (e.g. shopping commando)2. Write each one on a piece of card and seal each card in an identical envelope.3. Shuffle the envelopes thoroughly, then write a number (1 to
Challenge: Edge 10 times! You have time until the next full hour! Every edge you miss means a day in chastity for you!
Challenge: Make yourself cum in chastity!
Challenge: Cage yourself! Learn how to cum in your chastity device before you unlock yourself again!
Challenge: Chastity until tomorrow morning!
nothing-for-him:Challenge: Only edge in chastity until you learn to cum in chastity!
nothing-for-him:Challenge: Edge 10 times! You have time until the next full hour! Every edge you miss means a day in chastity for you!
Two women at my gym, who I often lust after, challenged me to a full circuit of the weights. Foolishly, I accepted. Each of them outlifted me at every station. Their hilarity comes from totting up all the extra days of chastity that I must now spend in
slavesissymaid: Again this year we have the challenge of chastity, but this time the challenge is more intense. who wants to play for a month? let’s spread this post as much as possible with the reblog, and comment on whether you accept the challenge
petforfun: Feedback is highly appreciated. Don’t worry will setup several backups to make it challenging but safe. There will be overall rules, rules for indoor and rules for outdoor. And Bondage of course… Overall rules Permanent chastity. No climax
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dreamerinchastity: That is awesome, the site “chastity babes” accepted a dual challenge, where a couple offered to do a certain amount of time in belts. Could you imagine the taking on a challenge like this, not being able to touch each other for
darkthistle:My latest Chastity Day Challenge from talldarkstrong with help from misspollyx
oramixpartysexoramix: The guys jerking off are taking an Orgasm Control Class: they are taught to maintain a high level of sexual arousal for an extended amount of time without reaching climax. This is the third lesson where they are assigned to jerk
baronwolfgangarts: Another chastity drawing. Ya know….drawing these has been really fun. Folds of skin mixed with shiny steel. Pretty challenging. Hope yall enjoy! Done in the Canson sketch pad with Castell pencils. Not my normal tools. Fairly good
dreamerinchastity: Chastity Babes has a volunteer that keeps coming back, Donna. The chastity gear becomes her very well. This picture came from an early challenge she had where she did 30 days in this belt. The thigh bands and bra were added later as
hornyjoss: Time for a new challenge and join Locktober~ Loving my belt but need encouragement to keep it on longer 😳 1 reblog = 30 min. chastity added 1 like = 1 hour chastity added 1 comment = 10 min. anal only training (please specify how) Ends
suebuf: greatfone: unasissycualquiera: slavesissymaid: Again this year we have the challenge of chastity, but this time the challenge is more intense. who wants to play for a month? let’s spread this post as much as possible with the reblog, and
The Thirty Day Chastity Challenge
emochastity:Have a look at my chastity challenge http://emochastity.tumblr.com/post/109523190913/as-i-told-you-earlier-this-day-im-back-back-in Find more Gay Bondage and BreathControl here
One I made for a “caption this photo” challenge. In case ya missed it.
Olivia Munn by request (6 of 9)I give him challenges to complete to remove days from his lock-up time.But since I never give a release date, he doesn’t know I’m lying.
Go right ahead. Keep talking tough. I love a challenge.Oh, and by the way, we can easily enjoy CBT without unlocking you. What? Nothing to say now?
Behavior modification is such a kink for me, I decided I need a real challenge. Found a nice god-fearing Christian boy and caged him. He doesn’t come out until he’s a minion of darkness. Not because I really work for Satan. I just like the
It’s more fun locking up a guy who thinks he’s an alpha, to challenge him: “Aren’t you tough enough to handle another day caged?”Given enough “one more” days, he’ll eventually be forced to admit how weak
nothing-for-him: Challenge: Skip your next orgasm!
nothing-for-him: Challenge: Get a woman to allow you to lick up your own semen!
nothing-for-him: Challenge: Fuck yourself with a strapon!
nothing-for-him: Challenge: Lick up your next load!
trychastity: Challenging game :)
captionedgoddess: ..a little challenge
thefemmeside: How else will you grow as a person if you aren’t constantly challenged? No Limits.
charliechastity: nothing-for-him: Challenge: Lock yourself up for a month! Fair point.
simmer-until:dogtanion69:I did have a compulsive masturbation problem. She knows. She’s empathetic. She nearly apologized for challenging me with the freedom to touch and stroke. It didn’t work out. It was a mistake. It won’t happen again. I need
justchaste:imownedbyher:simmer-until:dogtanion69:It really doesn’t matter. It’s not my concern. It’s her decision. Her choice. What I do want is to be her good boy. And I don’t want to be left alone, to be challenged with self control. She says
All prepped and ready for Locktober. Been locked since the 17th of Sept. Cant wait to see the next few months unfold
So some of you have shown interest in following my progress the Locktober. Well, as an update, my friend has decided that she wants to set a new record for how long I’m locked. So at this point, its at minimum till new years
As of right now, my toy collection consists of 5 plugs of varying size and 5 dildos ranging from 7" to 13" with various thicknesses.
The humiliation fantasy I would have told be: being locked while playing with my keyholder and her fiance. Both are close friends and there is a line for us sexually.. But as much as I know it will never happen, I both love and dread the idea.
I feel I was very lucky with this task, seeing as how I work in a machine shop, and none of my quote had anything to extreme in it. However, I was able to manage to get the entire quote throughout the day
13 twitches
43 blinks
So far I have 34 of the soft edges complete. Can’t stay soft long enough to get another yet. Cold shower and cleaning the house should hopefully help
oursexyexploration: Hotwife Challenge #12: “Dressing Room Fun” “Try on a sexy bra and panties set at a lingerie store. Peek out and invite the nearest cute guy to come into the dressing room and give you his opinion. Show your appreciation by letting
stormfluid: A sexy sum up challenge photo of what happened that night. A barging type pic of her having just finished and cleaned up.
queenandhers1ssy-deactivated202:teasefantasies:Check my pinned post out. Leave a word of encouragement for my sissies chastity challenge.🥰🔐🐔♾️
