Welcome back, my willing slaves. As I’m sure you’re aware, May is the month of masturbation… but not for you. Instead I’ve got a devilishly delightful new chastity challenge for you all. Make it through the entire month, and you’ll have earned your orgasmic reward!
Seeing as it’s masturbation month, we’re not going to be completely cruel to you. You’ll still be allowed to play with that pathetic cock, but the most important thing is that you’re not to cum!
Instead, each week I want you to ruin those orgasms. I want to see that little cock dribbling with precum, not proudly ejaculating like a real man. It’s up to you if you do this caged (and what could be more perfect than one of our Steel Cages with plenty of gaps to stroke your caged member), or if you take your cage off and masturbate properly.
Just remember the golden rule: NO ORGASMS.
Our ruined orgasm challenge originally ran during May 2020 as part of #LTCRuinedMay. Make sure to follow us on social media now so you don't miss our next challenge!
For those of you who still want to give it a try, the challenge is posted in full below:
1st May: Good morning slaves. Today we kick off our Ruined Orgasm Challenge to celebrate Masturbation May, Chastity Style! Your first challenge is a simple one, tell me which cage you’re planning to start your challenge in! Don’t forget to include the #LTCRuinedMay.
2nd May: Before we head into some of the more “interesting” challenges, let’s get to know each other a little better during #LTCRuinedMay. There’s a few things I need to know:
- When did you first make your chastity pledge?
- How many cages have you owned?
- How many days have you been locked up?
Reply with your answers and #LTCRuinedMay now!
3rd May: Let’s turn up the heat a little for our #LTCRuinedMay challenge. I want to see a picture of your pathetic caged cock. Head over to twitter and show me what I’m working with.
4th May: Seeing all those small limp cocks yesterday really made my day. I think you deserve a little reward. Uncage yourself and masturbate for five minutes. Remember though, DON’T CUM! Reply with the #LTCRuinedMay and let me know if you were a good slave or a bad boy.
5th May: Just knowing that you’re simply following along with my commands in private isn’t enough for your Mistress. I want to know that you’re always thinking of me. I want you to find your tightest fitting pants and wear them today. There should be a big bulge where your cage is, so everyone knows you’re caged up just for me.
6th May: I’m sure by now, your cage is getting a little dirty. So today it’s time for some cleaning. First take your cage off and clean your penis and cage (no playing!), then get dressed up in your cutest, frilliest outfit. I want you to wear it while you do all those household chores you’ve been putting off.
7th May: It’s time for our first ruined orgasm of the month! Get those cages off and bring yourself close to orgasm. Remember, we aren’t trying to orgasm. Bring yourself as close as you can and stop. If you get it right, that pathetic cock should dribble out the tiniest bit of cum. Perfect for a little sissy like you!
8th May: You must be getting pretty hot under the collar by now! Let’s cool things off a bit. Get some ice out of the freezer and put it inside your cage. No more touching though! You’ve got to let it melt on it’s own. The more ice you put in there, the happier I’ll be.
9th May: Yesterday we went sub zero, but today we’re going in the opposite direction. We’re not touching our cocks today though! I want you to tease those juicy little nipples for me. Get yourself nice and turned on with some nice warm candle wax, or heat up a spoon and gently rub it over yourself. I want you like a dog on heat by the time you’re done.
10th May: It’s been a while since I’ve seen those pathetic cocks with my own eyes. I need to make sure you’re still faithfully following my orders. I don’t want a little repeat of your last selfie though. If you’ve got one, I want to see something different. Give me a shot on twitter with another cage on like a good boy!
11th May: Today we’re going to be doing a marathon with our cages on. Don’t worry, you won’t need to leave the house. I want you to settle in with your favourite porn for a while. Keep your cage ON! I want you to feel the anguish as your pathetic cock tries to get hard, but your cage just won’t let it.
12th May: I was pretty cruel to you yesterday. If you’ve been a faithful slave up till now, I think you deserve a little reward. You can spend the day uncaged today, but if I find you masturbating I won’t be happy.
13th May: All those dirty thoughts and dirty cages, I just LOVE it! I think it’s about time we cleaned things up though. I want you to get in the shower and give that little cock some proper TLC. Make sure it’s nice and sudsy, and think about how much you want to cum for me while you rub it clean. Don’t get too excited though, we aren’t even halfway yet!
14th May: Another week, another ruined orgasm. That cock must be aching to feel it’s sweet release by now, but we’re not even halfway yet. Remember our tips from last time, bring yourself to the edge of orgasm, then let go of that poor, whimpering member.
15th May: Today’s challenge is deviously simple. Just don’t touch your penis for the rest of the day. Not even once! Trust me, it’s harder than you think. The more you try to resist the more you’ll want it. Just the way I like it...
16th May: I feel like having a little fun with you today. I want you to realise just how desperate you are for that sweet release. Roll a dice, and multiply the number by ten. I want you to spend that long massaging your balls. Feel just how full they are, begging for release. It’s up to you if you do it all at once, or spread it our through the day. Just don’t cum!
17th May: Just thinking about all those pathetic cocks simply waiting for my orders is really turning me on. I want to see those limp caged dicks for myself. Send me your best shot on twitter so that I have something to think about in bed tonight.
18th May: One thing I like to remind my slaves is that chastity isn’t all about them! With a partner it’s easy to show how much you appreciate them, but for all you solo boys this can be difficult. Show me your appreciation by doing five random acts of kindness today. Comment and let me know what you did.
19th May: Yesterday’s challenge probably helped take your mind off of how desperate you are to cum, so today I want you to think of nothing else. Set an alarm on your phone to go off once an hour with the message “Not yet…”. Sounds simple, but it’ll be pure torture by the end of the day!
20th May: Well done, you’re two thirds of the way there now. Today I’d like to hear exactly how you’re planning to enjoy yourself once this is all over. Spare no details, I love to hear slaves talk dirty to me...
21st May: You must be struggling by now, exactly the way I like my slaves. Your ordeal isn’t over yet though. It’s time for another ruined orgasm. This time we’re making it harder though. I want you to play with that cock for 15 minutes, then ruin it. Make sure you don’t cheat! I hate it when my slaves disobey my orders.
22nd May: A good slave should always broaden his horizons. When was the last time you read a good book? Well today I want you to spend some time finding the kinkiest stories you can, and reading them to yourself. Make sure you leave that cock alone though! I want it throbbing with desire.
23rd May: I’ve noticed some of you using vibrators over your cages in some of our earlier tasks. Let’s let the others in on the fun shall we? Today I want you all to do some quickfire sessions. 30 seconds holding a vibrator on your cage. If you don’t have one handy, your mobile phone will do ;)
24th May: Most of the time your cage will be hidden by your clothing. Sure, you can feel it. You know it’s there. But it’s just not the same as being able to see it with your own eyes. Spend as much of today naked as you can. I want that cage to remind you that this is for my pleasure as much as yours!
25th May: There can’t be many of you left by now. Show me your still being a loyal slave, and bring yourself as hard as you can while still wearing your cage. Take a picture and show me on twitter. I want to see your cock quiver with pain.
26th May: The next few days are going to be tough, so we’ll give you something nice and simple today. Share your best chastity memory with me. It can be as dirty as you like (and I prefer them that way)!
27th May: Only three more days to wait, but don’t start taking it easy now. I want you to look back through the tasks you’ve done for me this month. Pick out the three you found most challenging, and do them again.
28th May: We’re nearing the end, but you’re still going to have to earn your reward. My slaves don’t get their release without really proving that they have given me complete control of their cock. Today you’re going to tease that cock with just one finger. Keep stroking until you’re just at the tip of an orgasm then stop. Remember, you haven’t earned your orgasm yet!
29th May: We’re turning up the heat with another day of ruined pleasure. This time, you aren’t allowed to touch your penis though! It’s up to you how you bring yourself to the edge. Maybe a little prostate play, or using something soft and feathery to tickle and tease that pathetic member. Get yourself to the brink, then stop once again.
30th May: You’ve almost made it, so it’s time for your hardest challenge yet. Today we’re going to be doing some extreme edging. Masturbate as fast as you can for five minutes (a timer might help), then just before the orgasm stop and let your cock be as disappointed as I am. You need to do this three times today if you’re going to earn your release.
31st May: Well done my pet, you made it to the end of #LTCRuinedMay! Take that cage off and enjoy yourself. But don’t let it get to your head. I want you caged back up and ready for more before the day is out!