Breaking a Sissy on cam cherry is the topic I’m presenting to you today! If anyone has been following my adventures here on my blog, or on The Weekly Hot Spot you know I like Breaking Your Cherry! I’m not talking about vagina and penis, intercourse virginity. after all, most of you have had intercourse before!

MOST, that is.  Yes I have a few virgins I play with but what I’m talking about is all the naughty things you’ve not done before. This past year I had a lot of fun breaking all kinds of cherry’s. Ruined orgasm, prostate orgasm, cock sucking cherry’s, and cum eating cherry’s !

As we round the end of another year I’ve broken one more cherry! Sweet little peg, pink peg at times. A sissy who pranced, or is that danced,  into my orbit early in 2019! Fast forward and recently sissy’s cam cherry, I gleefully broke!

Little Peg

As I mentioned above, little peg first came onto my radar a couple of years ago. Her with her quips  on my blog are so entertaining! Delightful and clever, she certainly got my attention! Eventually she gave me a quick ten min call to introduce herself. Giving me a voice behind the comments was fantastic! I also learned she’s such a chatter box! The time flew and those ten minutes were quickly up!

This is one way my pets can celebrate and support me!  Commenting on my blogs and hanging out on my blog, bodes well for me, I welcome your support! There are other ways to help support my endeavors!

✔ A good pet is listening in to The Weekly Hot Spot
✔ If you are on Twitter, sharing my tweets and interacting with me is a great way to serve!
 Enchantrix Empire is our kinky social network, and you can find me and other Enchantrix Mistresses there!

Confessions Of A Sissy

Back to Peg!  Soon this cute submissive was revealing more and more about her journey; From being a submissive male, then eventually how she loves to play girlie dress up. Revealing a bit more of her naughty history as we went along. Trust is an important element, between Mistress and sissy. She told me her in person sessions with a Mistress. How her training helped mold the sissy I know today! Of course I’m not going into intimate details. But I am happy to mention her journey included CFNM, SPH, Pegging and more!

Feminine Pose

Watch Learn Imitate Women

Oh yes, this sissy has a very naughty history!

Along with the slow growing trust, sissy loved to share her pictures all prettied up with me! At first with her hair demurely covering her face in Oh So Feminine poses! If I didn’t know better I’d swear she was a cis-girl! It was evident she had a lot of practice with those poses!

 

 

Chastity Sissy

One thing led to another, and this past  year sissy peg started locking up for me! No sissy cummies, unless she earned them! We pushed her boundaries by denying sissy cummies longer and longer and something amazing happened! Sissy learned to tug and dribble! Wiggling her little peanut produced a chastity ruined orgasm! Mind BLOWN!

Locktober

For this past locktober my sweet pet had gone so long without orgasm previously, so what’s 31? Nothing, right? What’s a few more days. She can do it!
SO WE DID! Now, little peg can’t be in chastity 24/7 due to her particulars but each morning after battling her excited clitty she’d lock up and keep track of the hours. Previously, when she reached X amount of hours locked,she would be eligible for a sissygasm,but with Loctober the sky was the limit! I’m proud to announce she spent 467 hours in a cage and no cummies for the duration! We couldn’t session until the 3rd, and yes she waited for Mistress a few more days!

Planning The Sissy Party

Leading up to the sissy cumming out party, Peg came to me, excited she’d have some extended alone time! But to celebrate we were not going to have your regular phone session, no! We were going to have peg’s first sissy cam session! Modeling, and showing me my locked clit!

So we planned and prepped for the BIG event! She was so cute and nervous leading up to the session! Checking and double checking, learning how to use Skype was both fun and anxiety producing!

Epic Cherry Breaking Sissy Cam Session

Sissy Dress Up

Party Dress

Just as we had planned the sissy cam session was here! No derailments and much to my delight Peg was on cam for me! It went without  a hitch, peg worked very hard to make sure she knew what she was doing! Very proud!

The flavor of the day was frilly sissy! She was wearing a lovely buttery yellow party dress!  With ruffled skirt and  very colorful gems on the bodice, framed with a sweetheart neckline! It blew me away! So pretty!  I’ve seen pictures of this dress before, and ON peg, but seeing it on cam just brought out the lovely colors, I thought for a moment it was new!

Of course I had her pose and took MORE pictures as part of our sissy party!

Trust Mistress

During our sissy girly time there was a bit of a hiccup. I told peg not to fret, because I could see my girls angst. But, you see, that’s why you come to Mistress. I understand that emotions run high when you are exposed and vulnerable on cam for me. I can turn things around, regardless! From sensual, to strict I know how to handle you. To refocus you to Me. With peg it’s a firm sensual hand! With a few words and deep breaths, I turned her around. We moved on and I applaud peg for trusting me, and letting go!

Continuing on,sissy showed off her bloomers and that cute sissy bum. Before properly introduced me to My little peanut!

It’s adorable and demure just as I’ve seen before, but now was live and on cam for me!

Sissy obeyed and was rewarded with a nice sissy cream after all that time! She dutifully deposited into a glass. and after a moment of composing herself drank it down with glee! I was so impressed, her orgasm was moments ago and she smiled and happily drank every drop!

Session Review

I was so proud, and impressed over my little peg and her bravery to hop on cam to please me! I know it might be a long time until the stars align again for such an epic session, but that’s ok! I have pictures to remind me! My pet was so inspired by our time together she took the time to leave a Mistress Review from our RateMyCall.com page. If you don’t know about RateMyCall.com hop on over and check it out. You could win free minutes!

Push Those Boundaries

I’m so looking forward to more girlie fun with peg ,and anyone who needs a Mistress to begin or continue their sissy journey! We can have phone sessions , text sessions, email training, and yes even sissy cam sessions.

But my guidance goes beyond feminization and sissy play. What boundary are you thinking of pushing? Calling a Femdom for the first time? Confessing you are a man who eats cum? Whatever your desires, I’m here, let’s play!

Until We Chat 💋

Intelligent Phone Fantasy Mistress , Erika