Slave My_Sissy_Boy

It has been so long since I have written to my Diary. Goddess Roxy has been so patient with her Sissy Boy and my crazy lifestyle. We are getting close to 2 years in our dynamic. Goddess Roxy encourages me to be the best version of the real me. She really knows whats going on in my head and just the right way to use that to her advantage.

I just hit 60 days locked, and we were planning on a break for a long weekend - but with zero convincing, somehow here I am with my clitty locked away for Goddesses pleasure. The road to another 90. Do we really think i'm going to to be unlocked again? I guess time will tell on that one. 

This past Friday marked our 1 year anniversary since Mistress (Goddess) Roxy agreed to own me. I just stumbled on this site, wasn't sure what it was about, it was still super new, but I took a chance and jumpped right in. 

She is the best Goddess someone like me could ask for. Work and other life events are keeping me super busy, but we have worked around everything as it comes at us. She truely understands that it takes two to make a dynamic and keep it going.

Here is to another year and more!

Xoxo

Just wanted to share a picture from earlier in the week - Goddess has me a drippy mess. Like a leaky faucet! The past few days with the holiday has had my mind off of being horny - but tonight I have to do a teasing session with the wand. I am sure that will get me pouring out again. 

It's almost been a whole year since I started on this website and met Goddess Roxy - She has led me through a wonderful journey of exploring my sissy side more than ever, and I know theres much more to come - or not. :P

Yesterdays call with Goddess Roxy was amazing. This turnaround of cumming for her to being denied is a new world. It has now been 14 days without cumming, and I am a leaky mess today. The end of our call she told me put my magic wand right on the tip of my clitty and I wasn't allowed to remove it for 40 seconds and I wasn't allowed to cum. That felt like the longest 40 seconds of my life! 

Today I have to tease my leaky clitty with the wand for 30 minutes on and off and not cum - wish me luck! Oh and this is after a round of Deepthroat training.

Today I am just a messy leaky slut of  a girl.

So, I finally did it - I was able to attend one of the two events I was looking forward to and mentioned in my last entry. The femdom event was absolutely fantastic. I walked in and was offered one of three wristbands, Red, Yellow or Green (No Play, Maybe Play, Yes Play). Being my first event, I went for the safe bet and took the Yellow wristband. Then they gave me the quick rundown of where the rest rooms were, and where lockers were. Walked into the next room and there were 6 male subs kneeling on either side of a red carpet for the perfect start and welcome to the event.

Unfortunately the introvert side of me won - mostly. This was a CFNM party - so I embraced most of it, and went down to just my pink panties and my cage - I talked to the event organizer a bit, but mostly just stayed off in a corner and watched. Watched to learn. The vibes were all perfect. These were my kind of people. Now I know what to expect, I am ready for the next one and ready to talk to people and hopefully get to know and play with some wonderful Dommes. 

I was able to participate in a group whipping session. Myself and 7 other subs (total of 7 male and 1 femme) were positioned around a cage with our hands on the cage and the Dommes had their way with our backs, butts and more. 

Next one is in August, and I already can't wait!!

Now - the other event I was supposed to go to yesterday - work got in the way, last minute... I'm already on the lookout for the next one.

Other quick update - Goddess Roxy and I are getting back on the obedience app coupled with a 180 turn to orgasm denial. Wish me luck. :) It's already been 11 days since my last orgasm. A far difference from once or twice a week.

I always knew I was a girl at heart... and mind. I never liked the "boy things" - no sports, wasn't an outdoorsy person, not into cars... you know boy things right?

Growing up with the internet, I was doomed to exposure of kink early on - it started with playing with anal, then a real butt plug, then as I discovered more and more kinks, I just wanted more and more.  (Still do!) Then, my first girlfriend... it was a silly as swapping t-shirts for a photo, then I found myself wanting more, and what if I could just wear a skirt? Why can't I wear what is comfortable and makes me feel sexy too??! Oh yeah... society and their outdated thinking. Well look at me now, still mostly at home and only a few select people I trust, but wearing any and all sexiness that I feel like.

Who knew that I would find this website, and then the best Goddess ever. Goddess Roxy has made it so easy for me to continue to explore and expand my craving of kink and the lifestyle, so much so that I am craving dick. While scary, I've decided to embrace it, and see where it takes me. I've always been interested in having more friends in the lifestyle and being able to be open and playful.

My schedule has always been what we call... Stupid. But things are opening up a bit - so I miiiight have been looking for some events to attend. Being a single male, sometimes that can be hard unless you already know people in the community, but I get it, I've seen it myself just being online, some people don't know what respect, or consent is.

Anyway - I found two events coming up at the end of June - hopefully able to attend both. I'm super excited and nervous, but hopefully will make it and update here with great stories.

xoxo

Goddess Roxy wanted me to share with you all - Mmm Pink, PVC, and Messy from a very proper mindfuck from my Goddess.

Today marks 60 Days of being locked in Chastity for My Goddess Roxy - This Clitty belongs only to her. <3

Mistress Roxy did it again. She melts me to a puddle from a distance. We couldn't even talk this time, but the control distracted from work in every way that I needed. Her deviant mind somehow makes a deep connection, talking or not, with my mind. She knew exactly how to tease (for almost an hour!) Then explosion. As always it leaves me craving more and more!

Mistress Roxy and her ever creative and deviant mind always comes up with the best photo collages to show off the before and aftermath of her control from afar.

When we were done I even looked at my wristband and then said, wait thats totally not a watch once I realized it would never tell time! My mind is totally fucked, along with my ass with my Hush 2 and my nipples.

I could not ask for a better Goddess. ❤️

Yet another wonderful Loevense session with My Goddess Roxy. Made a mess all over my panties. I've been super busy and stressed, but these calls are the best relief. <3

Had a quick but explosive call with Goddess Roxy this morning. It's been a busy week, but we are doing our best to find time for this special brand of therapy. I can not say it enough, between her beautiful accent, seductive tone and devious mind, all added to knowing just when to play with my toys. As always, can't wait for our next call.

It's been a long few days, but its time to get back to some tasks for Goddess Roxy. We are working on a good routine of good habits and tasks when possible. I have an ever changing schedule, but we make it work.

So far, Goddess is encouraging me to drink more water, walk more and get kinky when possible. It is all for my own good. We recently added some beginning exercise routines in the mix. I will update how that goes soon!

It had been so long since Goddess and I were able to have a lovense call with each other. Between the holidays and busy time at work.

Friday we were finaly able to have a call, and it was a fantastic way to start the day. Goddess Roxy knows how to work my toys in such amazing ways. We are hoping to have at least 2 a week when possible. Cant wait til the next time!

Got a surprise call from Goddess this morning. I can't always answer, but I think she is getting a sixth sense for when I can. I love anytime I can chat with her, I am always left with a smile on my face and always wanting more! - Goddess Roxy is Beautiful in every way.

New year, New Sissy Boy. With the help of Mistress Roxy, I am headed on a path to better habits. More water. Less pop, more walking and activity. All for a better life and a better figure. I want so many more outfits that show off my curves. These small steps will turn to bigger steps and hopeful downsizing so I can fit in all the slutty dresses and lingere thatbI want!

We started a few days ago. Many more updates to come.

Merry Christmas to All - I hope everyone is having a fantastic day!

I am back from my trip and My little clitty is locked back up for Goddess Roxy and is leaking like a faucet. I've been in chastity for quite a while now with very few small breaks (Like good sissys should be) - but this is the first real leaking (on its own) that I have experienced. It has been quite a while since my last orgasm - Though I am allowed to have a Ruined Orgasm soon, I am sure the leaking will continue.

As we enter the new year, we have talked about more training and consequences for failure. I am excited to explore more CEI and Public Humiliation Tasks coming up soon.

I finally had time to play naughty again for Mistress. Mistress Roxy has been so very patient and understanding with everything going on in my life and changes at work.

It was so fun being able to play again even if for a short time. I have some work to get back to where I was, but it shouldn't be too bad. Hopefully after the Holidays I'll have a much more open schedule, to keep up my very kinky sissy lifestyle.

4 months - wow. Who knew? And My first Locktober completed. Mistress Roxy has been and continues to be the best Mistress, Goddess and Owner a Sissy Boy like me could ask for, and so much more. She takes time to get to know her subs, and skillfully uses all of that knowledge for her pleasure - and ours.

Long Distance doesn't get in the way thanks to my Lovemse Hush. Giving up control to someone experienced has been so fantastic.

Thank you for everything Goddess! I know time has been scarce lately, but it will change and catch up soon!

I just wanted to post a short update - It is coming up on two months being owned by Mistress Roxy. I just want everyone to know how absolutely awesome she is. She is smart, very funny, and the most caring person you will meet - BUT! That certainly does not take away from the Devious nature or Power she has over you.

I just stumbled on this site one day (probably like most of us), I am so glad I gave it a chance, and also that I messaged Mistress back!

Luck doesn't begin to describe it.

Thank you Goddess!

Have a fantastic Friday.

-Goddess Roxy's Sissy Boy

Been away for a bit since work got super busy. Hoping to find someone to own me for a while. Still trying to get comfortable in my PA chastity cage, starting another chastity lock tomorrow around lunch hopefully.

First night of session went well. I've done a couple of surrender tasks also. Second night of training is coming soon. I'm told we are going to do "Everything".... should I be excited or nervous?! I started this journey while in a self chastity lock - had some issues and had to switch cages, and still fighting a bit of discomfort, hopefully a short break will help get me back on track as I work towards long term chastity and sissy training - anyway looks like that ends tomorrow sometime, if I'm lucky, but I suspect I won't be out long.

Found this site a few days ago, super excited to connect with a domme and be trained properly. Training starts tomorrow evening. I'm sure there will be updates.