A challenge.....

Day 18!!!

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Hope it stays on while i'm out on my 'date' tonight!!! lol

 

Wishing you the best stephanie...as we all do
Just waiting nervously for my days to tick by...smile

 

Day 19!!!

Was so excited yesterday i forgot to post my pic!!!!

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Day 20!!!

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Yay Sissy doing such a good job , For all of you who don't know Sissy had a date a few days ago and she was a good girl and kept her cage on I'm very proud of her !!! good work


For all you curious about my perspective it been a wild ride Just knowing I have this much power has made my life rather different I find myself thinking oh what can I do I can say though Online keyholding is a lot harder then I thought because I miss the feel of teasing in person with my husband I gave him daily teasing sessions and here it a bit harder . But I am having fun so that all that matters .


So I have a question for anyone who has ever been a online keyholder what did you do to make it more fun

 

Glad you're having some fun, MissKelly!

--- Make sure your chaste boys and sissies know how much pleasure you get from denying them release. Tell them how much it turns you on to control their cocks/clits. Tell them how their lack of orgasms makes your own orgasms so much better. You can even keep track of how many orgasms you have had during their lockup periods while they are having none. Require them to include how many days it's been since their last orgasm in every correspondence to you... and tell them in your correspondence to them how many orgasms you have had. Letting them know how into it you are makes it more fun, and of course frustrating, for them... and more fun for you. They like to know that their denial serves a purpose, that it is giving you pleasure. They want to serve.

--- As you know, assigning tasks is fun... and interactive. Require proof of the completion of tasks you assign. Require them to watch vids of your choosing... or to just generally look at enough porn daily to keep them aroused and aware of their chastity. And of course you can interact with them via Yahoo or other vid chatting programs.

Tasks should be tailored to each individual and their individual situations. Get to know your boys/sissies. Make them tell you their feelings, as well as the details, about performing the tasks you assign.

Make them constantly aware that they need to find their pleasure (and possible release) in pleasing you.

 

21 days since my last squirtie!!! Just 9 more to go!!!!! Yay!!! Still dripping more than ever too!!!

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22 Days since my last little squirtie!!!

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23 Days locked up but i think i may have had a wet dream last night about 4:30am. Not really sure though. I woke up with a rather painful experience but alt least my CB didn't break.

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Day 24 and if my tiny penis gets any smaller it's going to invert and look like a real clit. And i thought i ordered my Jail Bird too small,...now i wonder if it will be too big!
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Please see my new thread http://www.chastitymansion.com/forum/index.php/topic/7187-lipstickys-1-per-day-chastity-charity-challenge/page__fromsearch__1

See what you think ... hope it works

Lx

 

Lipsticky & livingcurious...why not try together?

 

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I have been moving all weekend so sorry for your reply you can start as soon as you like I start normally with a week or more depending what the person likes . well anyone can get out it not like I hold the key giggles

 

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