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!
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!
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!
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!
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
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!
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!
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
You are such a great Mistress Goddess Erika. I liked reading this post. You do always push those boundaries. You did it to me. Thanks again. I am one of those virgins you are talking about.????♂️????♂️????♂️????♂️????♂️????♂️????♂️????♂️????♂️
tee hee, how did I know you were going to OUT yourself as a virgin when I wrote that line! What a good pet/slave supporting me with your comments, twitter engagement and those lovely ignore calls where I get to pamper /play whatever I want! ????
You sound so enthusiastic which is such a refreshing change! You didn’t make any mention of “draining” or “rinsing” him, but instead showed that you are a real professional.
Swim! I am switched on and love what I do! Glad it comes across! ????
Mistress Erika: Thanksgiving has come early. Now, perhaps, Thanksgiving knows how it feels!
Levity aside, your wonderful account of our journey as your humble pet has left me drifting
off in a state of bliss today, reliving not only our latest moments, but also the calls, the correspondences and comments since I first meekly pecked away at my keyboard as a nervous novice in this medium.
Imagine my thrill to see I’ve received a reply from Mistress Erika!
Imagine, today almost three years later, my thrill (yes my heart still skips a beat) when I see a new message from Mistress Erika jumping out at me from my inbox!
Just as my heart pounds in anticipation awaiting your voice when I call.
If you’ve never treated yourself to the pleasure of spending time with this exquisite woman, you must remedy this with all speed.
Mistress Erika I AM trying to avoid the puns…(fellas don’t worry about speed..she can help with that!)
Mistress Erika thank you for this. You have written a wonderful, insightful and touching account of our journey, thus far. Our imagination will take us to our next destination. We’ve come far.
I am deeply honoured, thankful, grateful and humbled that you allow me to call myself your “pet” and I will always strive to be the best I can for you.
My pleasure, pet. Don’t be surprised if I use some of your words “out there” they are delightful!
You/Ms Daphne did this as both of you saw how small your clitty was as
She tweeted this as I now always have to stay as your lipstick lesbian girlfriend wearing bras panties wigs makeup and lipstick all the time. As Ms Daphne said on Twitter both of you won’t ever let me go in being owned by you as this is forever. I’ve had zero luck with women in real life and if not for both of you I’d never have girlfriends. I do belong to both of you forever in staying as your girlfriend forever.
Yes, this is all true Carli!
I love this post. I felt so warm inside after reading it because it’s something I would love to do. You know from our calls (and my other calls with Mistress Olivia) that I’m a closet cocksucking faggot bottom bitch sissy who no longer has sex with my wife. You also know that I suck cock for real and have hot gay sex with men, usually when I’m dressed in my sexy lingerie. I would love to expose my sissy self to you — as little ms peg has done. I’ve already “come out” to you & the other LDW mistresses on the phone but on cam is a different matter. I hope to one day muster up the courage to do so.
Until then I remain your loyal sissy faggot,
Glad you enjoyed! Yes I know, Olivia knows and now all of my followers know too what a cock-sucking faggot bottom you are !! Ha ha! ????????????????
Oh the offer to view you on cam has got me going now! Careful what you wish for, sissy, YOU Just might get it!
Email me, send your concerns or questions! I would love to make this a goal for 2022!
You had me at “pushing boundaries!” When I look back, I see what you were doing with me, much like you probably did with Peg. You don’t force us. You merely guide us. You give us a hint here. A nudge there. You help us go where we WANT to go.
For me, I was a closeted, in denial homosexual that was afraid to explore who I really was. Over the years, we have ventured SO MANY places! From wearing bras and panties to shopping trips At Victoria Secret to coming out to hang bangs.
You were (and are) supportive, accepting, non-judging and devious as hell! And I love that. I didn’t do anything I didn’t want to do. You just led me where I wanted…and needed) to go.
Thank you for that. And please don’t stop being you!
Aww Aaron! Thank you darlin! It’s true I am all that. So what a surprise for pets like you and peg to find out I do have a rather demanding “mean Mistress side” as well. It’s all a matter of what that particular pet needs for motivation. I usually “Get your number” early on, and then it’s GAME ON! Happy Thanksgiving !
You DEFINITELY have my number! I went from a closeted, shameful guy who had experimented with some “anonymous quickies” to proudly being the the focal point of a 7 guy gang bang…with ZERO regrets!
…and thanks for posting the article I sent you. I guess I’m a good “pet”????. That’s the second time in a month I’ve been referred to at LDW.
Thank you for being you, aaron, tis true you are a good “pet” ????
Wait, what? I’m sure you didn’t tell me about this before! WOW! Shame on you for not sharing before
I love it. I love your journey and honored I am a part of it!
I think this officially makes you a #Cockslut…. hummm?
Ms Amber wrote about me in “Faggot Fireman tells the sexy truth.”
Fuck yes! I’ll have to check it out!
I like my story being out there. It’s erotic (humility, cuckolding, cocksucking) and it’s enlightening. For me, the bare bones truth is hot! Maybe my journey can help someone else here.
Mistress Erika, you know I strive to be an obedient pet and love to go that extra mile….(I think word is getting around I struggle with inches!) for you.
You have tasked me with a target number of hours to lock up (unknown to me at the time) before being allowed my little J & D!
Having reached unsaid number of hours recently, it dawned on me the end of November is only 3 inches…oops darn it all, DAYS away.
Hmmm…nothing in Locktober,
One magical moment in November…
Will you let me wait til December?
Ladies and Gentlemen, perverts of all types. I want to present to you an example of a super submissive and a fantastic sissy!
When I set a task or goal for you, and you love it so much that you want to exceed my expectations, you are what I call a super sub. Not to be confused with a brat sub. Both of these types of subs will be in a blog, I will post in the next week.
Peg, you thrill me with your sacrifice for My Pleasure! YES YES YES…….Wait! ❤????
Mistress Erika, winter is here today, with snow and cold, but to hear you say you are thrilled warms me more than any roaring fireplace or piping hot mug of cocoa could hope to.
When you task me with an assignment I embrace this with zeal and will go over the wall to see it through. Disappointing Mistress would be crushing for me and you inspire me to reach deep and push my limits. I am swelling with pride…(no, not that kind of swelling! You KNOW I’m locked!) with your compliments that continue to motivate me to be a better pet….(I just revel in being able to say I am your pet!). Naturally, I will anxiously await your next Blog post! Super sub and brat sub…anxious to learn more from you.
You are welcome, my pretty LITTLE pink peg……????
Mistress Erika, it makes me smile and blush to see you spell ‘little’ in all caps! Just in case I start to get too big for my britches! My goodness, it’s been just over a month since my …ahem “display of affection” and I’m pleased to report that it has been 31 days of “Lock…Don’t Touch”
Looking soooo forward for my…..excuse me, “Your” next ruined orgasm! Your locked little peanut is more than ready!
well the reply allotment evidently has been met on this thread, of comments. LOL so it might look like I’m replying to myself, but I am replying to your 12/5 comment.
You’d have to work long and HARD to be “too big” for your britches, might be easier to just buy smaller britches! ha ha ha!
you are a good pet, peg. and you are right they are MY orgasms, ruined, full or none at all.
Maybe I sent too many. Didn’t know that would be inappropriate.
*shrug* I didn’t know there was a limit! all good, I mean, far be it for me to say “Oh no, not another compliment” ????????????
LOL Smile, peg. That’s Mistress’ orders! ????