Sissy Chastity Challenge

Posted by Andrew Schroeder on

LocktheCock's sissy chastity challenge

What a cute little slave you are, always trying to please your Mistress. But what if I could make you even more adorable?

You won’t be needing that pathetic penis now that it’s locked up, so let’s work on turning it into a nice little clitty and help you embrace your feminine side. By the time I’m through with you, you’ll be the perfect slave you were born to be!

It’s not going to be easy for you. You might end up outside your comfort zone. But trust me, it’ll be worth it! Once you’ve left your masculinity behind, you’ll be able to enjoy chastity like never before, and the truly dedicated among you might even experience the treasured sissygasm!

So prepare your mind and body, and let me take you on a journey of self discovery in LocktheCock’s Femboy Challenge!

Not sure what all the fuss is? Check out our article on becoming a sissy slut

Once you’re prepared, head over to our sissy collection, and choose out the prettiest, girliest, pink cock cage you can find.

This challenge originally ran in September 2020 on the LocktheCock social media channels. Follow now to make sure you don't miss our next chastity challenge!

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For those of you who still want to take part, the full challenge is below:

The Sissygasm Game Begins

Day 1 - Lock That Clitty Up! You won’t be needing it for the next two weeks, so all you need to do today is get that slutty cage on and get yourself ready for the challenge!

Day 2 - Every good sissy should have a fabulous wardrobe to show of their feminine side! Today’s challenge is to pick out your most attractive outfit and send us a selfie, male chastity device and all!

Day 3 - With your outfit and femboy chastity device complete, there’s one more thing to complete your new look: make-up! Today’s challenge is to try and get dolled up as best as you can. Don’t worry if you’ve never done it before, you’re here to learn after all.

Day 4 - A clean home is a happy home! Today you need to get your apron on and do all those chores you’ve been putting off. Every good slut keeps their home neat, organised and tidy and you should be no different!

Day 5 - Well you’ve been quite good so far, so I suppose we can let you have a little treat. Seeing as you’re a good little feminine slave, you can have 15 seconds with a vibrator on your clitty. But no orgasms though!

Day 6 - You’ve got the look sorted, now it’s time to start acting the part. Every good sissy should walk the walk and talk the talk. Practise your best feminine voice and find yourself a pair of high heels and practise your walk. If you’re feeling extra confident, I’d love to see a picture!

Get Comfortable With Hypno To Reach Sissygasm

Day 7 - Now you should really be starting to feel like a true femboy. But there’s still one thing we need to explore. You don’t get to cum with your cock. So let’s start training you to have that sissygasm! We’ll start off gentle, so today all you need to do is get something in your butt! A finger, butt plug, or even a dildo, it’s up to you!

Day 8 - Don’t think we’re going to be focusing on your pleasure the whole time. Real sissies spend most of their time pleasing others, and you shouldn’t be any different. Today I want you to practise your oral skills! Use whatever you have available, and see how deep you can go. We need to get rid of that gag reflex if you’re going to be any use to me.

Day 9 - Now it’s time for your training to get a bit more intense. Today you’ll be watching 30 minutes of porn, with a catch. Either sissy hypno, or cock worship. The choice is yours...

Daily Prostate Play To Cum Hands Free And Sissygasm

Day 10 - After yesterdays challenge, you should be nice and horny now! Today we’ll be stepping up our anal training, either spending one hour wearing a butt plug, or if you don’t have one, 15 minutes stroking that prostate gland.

Day 11 - You should really be starting to look and feel the part now. Today I want to see all your training in action. Put on your prettiest outfit, get dolled up and send me another selfie!

Day 12 - Now’s the time to really start pushing for that Sissygasm. Today I want you focusing on that prostate. At least three times today spend 15 minutes massaging it and trying to make yourself cum! Bonus points if you try more than three times.

Day 13 - We’ve got two more days to finish your training, so now the going gets tough! I want your oral skills perfected by the end of the day! I don’t care how long it takes you, but you better be able to deepthroat a cock, dildo, or whatever else you have lying around.

Reap Your Anal Sissygasm Reward

Day 14 - The final push is here. You should barely be able to remember the pathetic man you used to be now. So let’s finish things off with the only kind of pleasure a pathetic femboy needs. With fingers, vibrator, dildo, or even a real cock, we’re going to edge that ass. Start with 2 minutes of stimulation, then one minute off. Then three minutes stimulation, one minute break. Keep working your way up until you reach 15 minutes of continuous anal pleasure, and hopefully, your first Sissygasm!

Make it to the end of the challenge, and your training will be complete! Give up early, and I won’t be happy. Read reddit for more ideas

Chastity Games and Challenges Written By Andrew Schroeder

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About The Author


Our guy who’s walking the walk, Andrew is a long-term cage wearer who found LTC when shopping for devices early in his journey. So he’s gone from customer to consultant. 

He taps out articles that discuss the lifestyle. From debunking myths to offering commentary on the most-debated chastity topics, Andrew S is inspired to write because of his ardour for the caged life.

“Pardon the pun, but there’s a lot of cock and bull information about male chastity and the people who partake in this lifestyle. My want, and why I write for LTC, is because I believe we need more straight-talking, experienced voices to speak up about their journeys with chastity. People who are familiar with the lifestyle and community. People who want to help those who are new and interested."

View All Posts Written By Andrew Schroeder