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Old 02-10-2022, 11:56 AM   #1
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Default [Half-Fiction] A Kitty & Her Mistress

Hi!
It's been a long time since i really tried some creative writing, so bare with me as i get back used to it.
This is a half-fiction story. Basically i wanted to write up some of the stuff my sub & I have done in our last almost 2-years together, but to make it more interesting and fun to write i'll add in some fantasy ideas & make changes to keep ourselves private.
Please comment, ask questions, and most importantly - enjoy!


Part 1 - Locked Down, but Not Out

*Stay home, stay safe, protect the NHS*
March 2020 and the world had stopped. When the year began i was saying "I'm ok being single a little longer, without a kinky partner." And suddenly two months passed busy in work and now this. Being an aware person who read the new i'd been avoiding too many public places for extra weeks already. God i hadn't had any fun in a while. But when you can't go outside, how do you find somone to play with?

I fired up my old GetDare/Reddit/Tumblr/FetLife/etc accounts. Initially just looking for some fun erotic stories to read, maybe see what's going on. Chat to people. Get back into the online mindset.

After a few days i already knew this was maybe a mistake. Just endless messages from dudes being weird or creepy or annoying, any such adjective. I changed my approach, and without much else to do, stuck with it and kept looking around.

A few friendships flared up, chatting about various kinky stories and ideas. In fact it was only a week or two before i met her

Browsing around Fetlife i spotted the profile:-
About Me
Hey i am a 22 yr old sissy from the Netherlands
Things i like: sissification, blackmail, roleplay, bondage
I love to talk to people and make a connection!
Xxx

And a few more posts that were similar, talking about her love of being sissy and crossdresser. A few pictures showed a wonderful feminine body.
She had potential, and a very genuine tone. Not desperate or pleading, just real and interested.

Adidas: Hi! I saw your profile on FL and thought i'd send a message. Your post talking about exploring being a sub had me interested as we share a lot of kinks like feminization, bondage and more. Lets chat, connect, and see what happens.
Naomi: Omg, hi. Thanks for the message. Yes please lets talk. I'm 22, i've been a sissy for a few years, although i have basically zero experience being a sub.

A simple beginning. Nothing fancy. We just chatted about out experiences and kinks for a few days. Well, we sent dozens of messages a day for a week. It was an instant connection! Our kink lists lined up, we got on as people, it was so easy to chat and joke around.
I knew i wanted her. So i pushed our chats more and more kinky. Slowly picking out her fantasies and desires, breaking down those barriers. After a week we started sharing pictures of ourselves, so we knew we were both real.
That next weekend i gave her some basic tasks just to test the waters. She was smiling and excited. On a Wednesday in early April we took the next step...
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Have an amazing sissy slave for 2+ years! Have a new hypno/denial female slave! Have an awesome sensual female slave! - Yes, i'm building a little hareem of sluts
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[Half-Fiction] A Kitty & Her Mistress - Story Time
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Old 02-10-2022, 02:49 PM   #2
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I'm going to switch perspectives and styles between parts. Should be clear what's going on and whos talking at all times, let me know if not. And i will also be skipping over gaps in time, because you really don't want to hear about the boring getting-to-know-each-other phase.

Part 2 - Giving In

Miss Adidas had given me some easy instructions before hand. I was to get myself dressed up in something casual. I picked out my favourite black g-string and plain black bra with thigh high black socks, which all went underneath a figure hugging dark grey dress. To that i added one of my brunette wigs & light make-up.

Next to me i had a black marker pen, not a sharpie but an ordinary one, i didn't want to end up marked for that long (just yet). And all around was a growing sense of anticipation and excitment.
I'd been crossdressing for years, i've even been on a few very short walks outside. And yes i'd done a few tasks for Dom's, just spankings and dressing like a slut for them. But i knew i needed to take it further.

We had talked so much and oh, she just melted me! I'd been looking for a proper Mistress for ages, but the internet is full almost entirely of dudes wanting a quick jerk off. I had spoken to some other real females before, but Adidas is different. Ok we talked a lot of kinky stuff but we also could easily talk about the world, or food, or tv. It really felt different and right.

I had wanted to submit to her earlier. But Adidas was smart and told me we would wait at least a week to make sure it was right. Well here we are about two weeks later and i know it's just perfect!

Adids: Hi Naomi. Are you all set?

Her message flashed up on my phone. Rather than a simple "Yes" i snapped a quick selfie to show her instead. A flutter in my stomach awaiting her approval.

Adidas: Looking very cute! You agree to be my Submissive?
Naomi: Yes Mistress! I agree to be you Submissive. Please own me!
Adidas: I love enthusiasm, haha. Kneel and pull your dress up. Use the pen to write "I am Mistress Adidas Property" on you leg, nice and big and clear. I know you're not working today and tomorrow, so keep it the whole time.

Heart pounding. Ok it's a really simple action, but the weight of what it means. Not even nervous, just full of excitement and passion. The black letters really stood out strong on my pale skin. I sent Mistress the pics to show off.

Adidas: Good girl! Now time to formalise your rules

I rested back on my knees. We'd already talked about the Rules i would get, but still it was different to actually have it all written down, screenshotted, and made real. Frankly, i was in sissy heaven already!
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Have an amazing sissy slave for 2+ years! Have a new hypno/denial female slave! Have an awesome sensual female slave! - Yes, i'm building a little hareem of sluts
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My Intro - Learn about who i am!
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[Half-Fiction] A Kitty & Her Mistress - Story Time
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Old 02-12-2022, 02:44 PM   #3
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Part 3 - First Toys

Despite being a pro crossdresser, with a very well stocked wardrobe, Naomi had not been particularly kinky before me. She owned zero sex toys. Zero! None! Not a dildo, or a plug, or ropes, or a gag, nothing! Until now she'd just made use of some marker pens for bodywriting, and a few kitchen items for spankings.
Well obviously this need to change as my sub. Luckily Naomi is good with her money so had the ability to buy some stuff. We agreed on the minimum set any sub should have; a dildo, a plug, a gag.

Just a few weeks after officially making her my sub, the toys arrived. A simple 6inch realistic style dildo complete with balls. A small neon pink starter butt plug. A lips gag.

Immediately we had to put them to use. Naomi got herself dressed up in a lingerie bodysuit, underneath a tight black dress. For a sissy that considered herself as straight i knew the first thing i wanted was her to suck the dildo. The sign of humiliation and submission would sink deep into her mind and further mark her status as sissy slave.

To my surprise she instantly took the whole thing in her throat! Apparently Naomi's natural gag reflex was very weak, what luck!

Naomi: Mistress, this feels kinda weird, sucking cock.
Adidas: Oh Naomi, you'll be sucking the real thing one day. The practive will help
Naomi: ...

She would be a natural as this. Added to her rules was to spend 15minutes a day practicing sucking the dildo. I also instructed her to keep it on her bedside table, so she would always see it as she went to sleep, and would then see it first thing in the morning. Little ways to emphasise her new role and priorities.

Onto the plug! Unsurprisingly she'd never tried anal before. But i'd told her to get some lube as well, so we could take it slow. And just like with the dildo, turns out she was a pro! Deep down it seemed Naomi was fated to be a sissy girl. The plug went in without much work, and the pink jeweled end shone between those pert cheeks.

Adidas: Now go sit down infront of you mirror.
Naomi: Ah, Mistress! That presses it in... mmm kind nice i guess
Adidas: Wiggle your cute butt and really feel it in there.
Naomi: aaaahhhhh.... ok this is quite fun.

She snapped away a few pics with all the items just to show off. The first toys were a massive success. Naomi enjoyed them all and was more than happy to add it daily sucking and plug wearing. Often wearing the gag to suck just because it was extra kinky.

Next step, get her a chastity cage and some bondage gear, as well as more toys. This slippery slope to being a sissy whore was rapidly turning into a freefall.
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Have an amazing sissy slave for 2+ years! Have a new hypno/denial female slave! Have an awesome sensual female slave! - Yes, i'm building a little hareem of sluts
I do not want any more subs, do not ask, you will just get blocked.

My AMA - Come ask anything at all!
My Intro - Learn about who i am!
Joint AMA with My Sissy - Come as us anything!
[Half-Fiction] A Kitty & Her Mistress - Story Time
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Old 02-13-2022, 01:36 AM   #4
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Wow this is incredible i love it i can’t wait to read more
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Limits: public, illegal, extreme pain, very messy, social suicide, family (or anything including other people IRL or their possessions).

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Old 02-13-2022, 11:44 AM   #5
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@Al3x - Yay, thank you so much!

Part 4 - A Cage Full Of Surprises

Things settled down into a nice little routine for the next couple of weeks. I would chat with Naomi everyday. Sometimes we would just share dumb work stories, or talk about our friends, almost like a normal couple. Other days, far less normal. We share a lot of kinky ideas and chat, and slowly i was drawing Naomi further out of her shell and more into the mindset of a sissy slut.

Then on a Saturday i was just doing chores at home when my phone buzzed. I was greeted with a picture showing black thigh-high stockings and a lightweight black skirt, being lifted up to reveal a plastic pink chastity cage.

Adidas: O.M.G! You bought one!
Naomi: You made it sound like a good idea, and i wanted to surprise you! And i have more surprises...
Adidas: Ah, best sissy! Show me!

Naomi had also bought a very revealing Maid costume. I guess it covered her caged clitty and her ass, but only if she stood perfectly still. Added on her wrists were some leather cuffs, and in her ass was a black tail plug!

Only a month or two ago, Naomi had never done more than crossdress and a little spanking. Under my hand, here she was voluntarily buying bondage gear and locking up her sissy clit. It was almost too easy to melt her brain down to a submissive mush.

We spent some time taking pictures in various poses, showing off the new items, and just getting lost in how beautiful she was when smiling in full sissy mode.

Naomi: Mistress i need a task for me ass, please
Adidas: You can ask nicer than that Kitty.
Naomi: Please make me fuck my ass Mistress!
Adidas: Much better. Stick you dildo on the wall, lift your maid skirt up, and start fucking yourself.
Naomi: mmmm yes thank you

She must have been enjoying herself a lot as i had to sit and wait for a reply for what felt like ages.

Naomi: .... Mistress... it's embarassing....
Adidas: Show me.
Naomi: Promise you won't share it.
Adidas: Of course not Kitty! Only for my eyes.
Naomi: omg so embarassing and kinky...

Naomi had placed her phone down low, giving a clear shot up her outfit. Pink cage swaying, dildo burried fully in her ass. By far the most revealing picture she'd taken. One of early soft limits, naked, was clearly not a problem anymore. We finished up the session with some bodywriting she had to wear for the next week under her normal boy clothes. And we agreed to find a good bondage set to buy next.

My plan was in motion to make as many of her kinky dreams and fantasies turn into reality.
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Have an amazing sissy slave for 2+ years! Have a new hypno/denial female slave! Have an awesome sensual female slave! - Yes, i'm building a little hareem of sluts
I do not want any more subs, do not ask, you will just get blocked.

My AMA - Come ask anything at all!
My Intro - Learn about who i am!
Joint AMA with My Sissy - Come as us anything!
[Half-Fiction] A Kitty & Her Mistress - Story Time
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Old 02-14-2022, 11:59 AM   #6
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@hello_kitty - The plan is for a lot more to come

Part 5 - Did I Just Say That?

Mistress had made sure chastity was now added to my rules. It wasn't easy at first, but that was just about getting the ring size right and a few adjustments. She allowed me to go to work un-caged, but i was now wearing panties full time. Then as soon as i was through the door, locked back up and wearing girly clothes. Most nights were fine, occasional discomfort as my clitty tried to grow. To be honest i was already used to it, and really quite liking it. Anything and everything that took away my own control, choice and pushed me deeper into living as a sissy.

I found some things to add to my rapidly growing toy collection. New black ball gag, came with another black butt plug, nipple clamps and a set of thick leather cuffs with a chain. Plus a few meters of rope. It arrived while i was at work, and couldn't use it for a couple of days. It just sat in my room calling out! I needed to dress up and play and be a slut for my owner!

Sunday was hot, so i picked out some simple black panties and bra. Slipped on my denim shorts, very plain black top. Nothing fancy, as i guessed i'd be stripped pretty quickly, and it was hot!
Cuffs on, chained together. Gag in. Kneeling trying to look cute.

Adidas: Aww, sissy! You look adorable, and a little helpless.
Naomi: Play with me! Please i'm so excited i can barely think.

Obviously Mistress wouldn't refuse such a request. When we met this kind of statement made me blush. Now my melted brain loved the sensation of giving in fully to her wishes.

She made me play with the nipple clamps. The pinch hurt's at first, then quickly fades to a dull throb. But wow i don't lik taking them off. Mistress is evil by the way. She had me keep them on for 10minutres as i did some other tasks, then take them off quickly and give myself 5 nipple twists. Wow that hurt a lot!

Naomi: Thank you for torturing my nipple Mistress. More please.

Even if it hurt, i knew to say thank you. The begging for more was just instinct. Mistress was deep in my head and a flick of her fingers just dropped me into subspace. I got the rope and tried some ties on my legs, and Miss Adidas was good at giving guideance and pointers. The first ties were awful and i could just walk out of them. An hour of her teaching and if i wasn't careful i'd actually be stuck.
We used that with the cuffs to take some very subby and helpless looking photos. Even getting my dildo out and trying to suck it whilst in bondage. That made me feel even more sissy, helpless and submissive.

Adidas: Purrr you're such a fun cutie to play with.
Naomi: Thank you Mistress. I live to serve you.
Adidas: Can't beleive how in just a couple of months you've turned into a proper sissy doll.
Naomi: You make it fun and easy, Miss.
Naomi: Miss... can... can i ask you something?
Adidas: Always Naomi!
Naomi: It's... I'm nervous
Adidas: You know you can trust me with anything Naomi. I'm here for you and to help support you.
Naomi: I know. Ok. You make me happy and comfortable unlike anyone else.
Adidas: <3
Naomi: Can we take this further? I want to really be you sissy slave. We share some many kinks and interests. Including... er... ha... um...
Adidas: Say it.
Naomi: ... ....
Adidas: Speak up Sissy, tell me what you want.
Naomi: Blackmail me.

Ah! My heart was racing. A pure rush of excitement and adrenaline and kinky feelings. We'd talked about the idea before, quite a few times. And it had been on my mind. I didn't just want or need it. I craved it with every part of my sissy heart. And Mistress made sure i felt good. I was happy to let her take over completely.

Adidas: ! Omg yes ! I'm so happy to asked.

Not like i was silly enough to immediately give her everything about me. Mistress made it clear we would enjoy it more if we took it slowly, kept that rush and feeling bubbling away. Before she let me get untied i had to give her my real boy name and some bits about where i lived. For some it was basic, but i'd never ever done anything close to this.

I slept that night with so many many kinky dreams about my future as Mistress Adidas slave. And with the biggest smile on my face.
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Have an amazing sissy slave for 2+ years! Have a new hypno/denial female slave! Have an awesome sensual female slave! - Yes, i'm building a little hareem of sluts
I do not want any more subs, do not ask, you will just get blocked.

My AMA - Come ask anything at all!
My Intro - Learn about who i am!
Joint AMA with My Sissy - Come as us anything!
[Half-Fiction] A Kitty & Her Mistress - Story Time
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Old 02-15-2022, 02:20 AM   #7
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Dear Adidas

Thank you for your excellent story / report it is very well written and constructed, one can see the care you put into not just the story but also in Domming Naomi
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Read her amazing story: My Stupid Boyfriend http://www.getdare.com/bbs/showthread.php?t=139366
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Old 02-15-2022, 12:09 PM   #8
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@MrCharcol - Thank you. Glad to know i come across well. Hopefully more will continue to demonstrate how we care for each other.

Part 6 - Redheads have the most fun

Work kept me plenty busy for the next three weeks. I still made sure to follow all my rules, because they make me a better girl. In fact i'd grown my range of panties and bras, and i was now wearing girly underwear full time. I was practically living in chastity. Plugged for hours at home. Daily play times with my dildos, making sure i trainined myself to suck and fuck.

Mistress and I talked every day. We shared a Tumblr account so we could show off likes and interests and fun things. I let Mistress post some of my sissy pics. Yes i'd done it myself, but only in private chats. Knowing i wasn't in control of what was posted, where, how long, made me nervous. But like, in a good way. That constant bubbling feeling of being a slut. Mmmm it was good.

Frankly, Naomi was the only thing left in my mind. All my standard boy thoughts and feelings were altered beyond recognition. I still hung around friends regularly. But whereas before Adidas, my Naomi side was the act, now my boy side was the act. She had made me completely relaxed and transformed.

Eventually i got time off work and alone to play! I got on some red panties, black bra, and threw on one of my favourite pink floral print dresses. Topped off with a lovely strawberry blonde wig. I wanted to look beautiful and special for my Mistress. Naturally she approved, but did give a few tips on how to improve my blush work.

We did some pics focusing on my being cute. I even went and sat in the sun on my balcony. Chatted for a bit but unsurprisingly after not too long i was back inside on my knees acting like a kitty and begging Mistress to use me. We put a focus on bodywriting. I had "sissy slave" on one thigh, "sexy sub" on the other. "Doll" and "toy" on my chest and stomach. "Whore" also on my chest, with my nipple as the o. After quite a bit of teasing i was allowed to stick a dildo on the wall and fuck myself.

Mistress wasn't finished with me yet. I added "spank me" to my left arm, "property", "whore", "use me", "puppet", "barbie" all to my stomach and chest. I was very much covered at this point. I had to get a pair of heels and hump them, and lick them, yet more humiliation. But i couldn't stop smiling, it was fun and i loved being a slut for my Mistress.

Back to the dildo, giving it a wipe and clean, before sucking and deepthroating it. This was breaking me, and i got an idea. I grabbed one of my big coats and raced downstairs. In the carpark at the back of my building i dropped the coat and snapped a few pics. Sissy Naomi standing in her panties and bra, covered in degrading bodywriting. An unbeleivable rush, just to put a smile on Mistress Adidas' face. It worked!

The play time finished with my tail plug. I put it in and played around on all fours for a while. Knocking another butt plug around and chasing it. Hehe it was silly of course but i like being her Kitty. I can relax even more in that mode and just let Miss worry about decisions, i just look cute, purr, and say "Yes Misstress!"
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Have an amazing sissy slave for 2+ years! Have a new hypno/denial female slave! Have an awesome sensual female slave! - Yes, i'm building a little hareem of sluts
I do not want any more subs, do not ask, you will just get blocked.

My AMA - Come ask anything at all!
My Intro - Learn about who i am!
Joint AMA with My Sissy - Come as us anything!
[Half-Fiction] A Kitty & Her Mistress - Story Time
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Old 02-16-2022, 02:22 PM   #9
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Different style this time. Hopefully it makes sense to follow along for the rest of you, GD's limited emoji/smiley selection makes it a little harder to convey tone.

Part 7 - Be Careful, Sissy

Adidas: Hey Naomi, what are you up to?
Naomi: Mistress <3 Just chilling at home, have a friend over, playing some games.
Adidas: Sounds nice. What are you playing?
Naomi: Just messing around on Fifa, nothing serious.
Adidas: Nothing serious... hmmm, so you can talk to me as well!
Naomi: Always Mistress.
Adidas: And if i were to distract you from Fifa it wouldn't matter too much?
Naomi: ... why do i suddenly feel in trouble...

Adidas: Because you're my sissy doll.
Naomi: Mistress... ah i am your sissy doll... just be kind...
Adidas: I'm always nice to you. Wasn't i nice when i helped you get a cage for your clitty?
Naomi: Yes...
Adidas: The same cage you have on right now, as a rule, yes?
Naomi: Correct Miss, of course. I am wearing my cage.
Adidas: And you are accurately following all your rules?
Naomi: I would never disobey you.
Adidas: So, tell me what rules you are following right now.
Naomi: ... aaahhh... i'm locked in my chastity cage. I'm wearing a thong & a bra under my boy clothes. I have the pink plug in my ass. I am always calling you Mistress. I am being polite. I am being honest, and admitting it's kinda hot to be part sissy around my friend.

Adidas: Good girl! Is it this thong? *pic attached*
Naomi: .... please Mistress be nice...
Adidas: Answer my question slut.
Naomi: Yes it's that one. Omg had to turn my phone weird so he wouldn't see. I feel so exposed.
Adidas: I know you, you're loving the feeling of control i have right now.
Naomi: Oh of course Mistress, i could never hide that from you.
Adidas: Hehe weak sissy bitch Naomi, all locked and plugged in her thong. Texting Mistress with your friend just there.
Naomi: Please Mistress, i beg you... don't tease me too hard... omg i'm having to focus so hard to not suddenly say something sissy outloud...
Adidas: Omg ! Who owns you?
Naomi: You do Miss.
Adidas: And if i said, say out loud "I am you sissy toy Mistress"?
Naomi: ....
Naomi: ....
Adidas: Purrrr
Naomi: Do i have to?

Adidas: Haha, no! God i'm not that cruel.
Naomi: You are my owner, i just do as you command.
Adidas: That gives me an idea!
Naomi: Oh, did i just get myself into more trouble?
Adidas: You can't stay out of trouble it seems. You'll get spanked later for sure. But i have an idea. I'm sure you'll enjoy it.
Naomi: I trust you Mistress.
Adidas: Tell me the name of your friend.
Naomi: It's Michael...
Adidas: Good girl.
Naomi: You're making me feel kinky.
Adidas: You always feel kinky, slave!
Naomi: But... well... yes...
Adidas: Ok *boy name*, give me Michael's contact details.
Naomi: !!!!
Adidas: You heard me, *boy name*
Naomi: Aahhh, i don't like it when you call me *boy name*
Adidas: Just a little reminder you're my property. Have a kiss as well.
Naomi: Oh Mistress, you melt me! Ok *pic attached*

Adidas: Good girl, Naomi! Have some cuddles too.
Naomi: I love your cuddles! Purrrr
Adidas: Hehe, see it's fun when Mistress teases and torments you.
Naomi: It definitely is. Plus you keep adding blackmail material.
Adidas: We both know i don't need it. You'd do anything i say anyway, because your the best sissy sub.
Naomi: Thank you Miss. And yes i would. But still...
Adidas: You've never refused a task or failed one in the 6 months together. I'll never need the material. I just take more because we both love the power exchange.
Naomi: You're just living in my head, knowing all my thoughts.
Adidas: That's my job! To be the best Mistress so you have the best time.
Naomi: Best Mistress! Thank you! Even if sometimes you make me weak, i do enjoy it.
Adidas: Sending more cuddles
Naomi: Definitely best Mistress.
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Bi-sexual Domme, mostly into other girls and sissies.

Have an amazing sissy slave for 2+ years! Have a new hypno/denial female slave! Have an awesome sensual female slave! - Yes, i'm building a little hareem of sluts
I do not want any more subs, do not ask, you will just get blocked.

My AMA - Come ask anything at all!
My Intro - Learn about who i am!
Joint AMA with My Sissy - Come as us anything!
[Half-Fiction] A Kitty & Her Mistress - Story Time
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Old 02-24-2022, 08:43 AM   #10
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Part 8 - A Collared Kitty

Up until now Naomi had been mostly using a simple black choker as a collar during our play. But today was to be special, and we would upgrade to something far more appropriate. We'd been sharing links back and forth on ideas, and ultimately agreed on one for her to buy.

I had Naomi put on a leopard print skirt, with her black tail plug in, and a simple black shirt over her black bra. Lots of black, still working on introducing more color into her wardrobe slowly over time. Pair of kitt ears and some simple but effective makeup.

We toyed a little to begin with, making sure her throat was well warmed up with some deepthroating, and that she was in pet mode by crawling around. And because bodywriting was a staple of our play she had "cum slut", "cum dump", "rape me", "sissy slut" written in various places across her legs and body.

Finally i had her kneeling and ready. A cute pink collar, with a small bow and bell at the front. She tightened it around her neck, gave the bell and ring and smiled. Kitty was collared. Another step down the path of her service to me. I know Naomi thought this would be it, and we'd just chill and talk. But i had some more ideas.

I made her pick up one of her dildos. She recorded a cute clip showing her pink locked cage, moving up to reveal her throat stuffed with the fake cock. And a similar one as she relaxed on the sofa, couldn't keep her hands of the toy in this sub state.

Adidas: How's my sissy slave feeling?
Naomi: In heaven Mistress, purrrr
Adidas: Good! I like making you smile.
Naomi: Always smiling at your feet.
Adidas: As you're down there, crawl to your wallet.
Naomi: I think i know what's coming
Adidas: Then i expect you to be quick, sissy.
Naomi: Got it.
Adidas: Show me your IDs.
Naomi: *pic attached*
Adidas: Good girl!
Naomi: I like being your blackmailed slave, Mistress.
Adidas: Well you are definitely that. Can't deny it's you now i have ID proof.
Naomi: It's ok Mistress. I want to serve you & be yours.
Adidas: Still feeling kinky?
Naomi: Always beacuse of you!

To mark her first day in the new collar, and to reinforce she's my toy, i had Naomi go for a little walk. She had to take her purple dildo and suck on it under her facemask, and keep the collar on, even though the bell would ring a little if she walked too fast.
But she never stopped smiling! Naomi was well and truly now my little pet slave. The best girl!
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Old 03-03-2022, 09:33 AM   #11
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This is a good start. I'm excited to see where this goes. Don't rush and take your time keep up the good work
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Old 03-16-2022, 05:17 PM   #12
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I do hope you haven't given up on this story
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Old 03-17-2022, 12:08 PM   #13
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@iceman713 - Not abandoned! It has been on the backburner for a few weeks for a whole variety of reasons.

Part 9 - Testing A Theory

Naomi: *pic*

My slave loves to surprise me. This time she was kneeling on her bed, all dressed up with make-up and a black wig, wearing the classic black thong and bra, and holding two dildos. Her expression said 'i want to play'.

Who am I to refuse such an adorable sissy girl. Ok this was in relation to a converstation we'd had in the previous weeks about webcamming, and this was Naomi's clear sign she finally had time to play properly.

We both fired up Discord to enjoy ourselves. Her face popped up big and central on my screen. A subtle smile at the corners of her mouth, and a nervous energy making her leg shake a little. One hand toying with the end of hair. Oh i loved the little tics that gave away how she was feeling, especially combined with a smile and devlish twinkle in the eyes.

Adidas: Ok todays play is simple. You will open up Omegle and just tease and play around with whoever we find on there.
Naomi: !! ok, whatever you say Mistress
Adidas: Ha, i can see that leg twitching even more. Plus I just want to make you feel like more of a whore than usual.
Naomi: Your whore, Mistress.
Adidas: And because of screenshare i'll be watching, so if they other person is too weird i'm here for you.
Naomi: Thank you Mistress.

I knew that in the past Naomi had played with a few people via Omegle. But really it was just a little stripping and chatting, today was about pushing her to a new level.

Took a few minutes to find the right kind of person. A guy in his 20's, in reasonable shape, and at least presented as a Dominant personality. He began by asking Naomi to do a little teasing dance before moving onto to sucking one of her dildos.

Adidas: Well done Naomi. Remember to thank the kind man.
Naomi: Of course!

Naomi's interpretation of this was to remove her thong, toy with her locked clit, and show off her ass. The man was visibly more excited by this. Aaaand then he disconnected.

Not to be defeated Naomi put her thong back on and tried to find someone else. A few more tries and we found another possible partner. Except he just didn't seem to get the idea that Naomi was not actually a girl. Like, seriously. It was only when Naomi showed off her chastity did the penny finally drop, and he disconnected.

This wasn't going brilliantly but we had a new idea. Less kinky, just more fun. We would just stay online and chat to various people, and see how many we could convince Naomi was actually a girl. No malice, just an experiment to prove that Naomi was entirely passable to help build her confidence.

The new idea worked much better. Of the first 10 people, a solid 7 took the bait and believed Naomi was a girl right up until revealing her locked clitty. After 20 people, 15 thought Naomi was truly Naomi.

Not the kinky adventure we intended for the day, but useful nonetheless. We finished up the session with just a few simple tasks, and Naomi smiling wide and feeling significantly more confident in herself.

In fact i took this as the opportunity to help push her transformation further. From this point onwards whenever alone at home Naomi would be Naomi. Wig, some make-up, clothes and all. We were both committed to removing as much of her boy life as possible.
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Old 03-21-2022, 10:31 AM   #14
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Part 10 - Halloween I

Adidas: You have an Alice costume?! Why did i not know this!
Naomi: You know me Mistress, i am terrible at organising so some sissy clothes just get buried for ages.

We were talking about Halloween and how it's an ideal time to take your sissy self public in a much more acceptable way. Not that it's easy at any time to put on a skimpy maid uniform and go to a party, but the 31st October at least provides some cover and excuse if you can find the courage.

Naomi and I weren't planning that kind of adventure, but were discussing how we would celebrate the day. This was when Naomi revealed she had an Alice in Wonderland custoume already, to pair with the maid uniform i know she bought.

Naomi: Except it doesn't fit the best, Mistress.
Adidas: I don't think it can be too short for you sissy.

Haha, except it kind of was. Certainly for going outside. If Naomi stood perfectly still it was fine. But as soon as she walked a step the skirt flicked up and her caged clitty and ass were very much visible. Fun for us at home, not so much for taking a walk.
So we started swapping a few ideas and browsing some sites for a new costume for an adventure.

So a couple of days later Naomi had her halloween outfit. A yellow sexy princess dress, in the style of Belle from Beauty & The Best but way kinkier. This time it was long enough she could go outside and not be totally exposed. Thus the halloween plan was simple, Naomi would simply go for a walk as my pretty princess.

She started off with the outfit hidden under a black coat, just whilst she was close to home. 15 minutes walk the coat came off and was tucked behind a bench. Now Naomi was alone in the park looking more girly and exposed than ever before. But as a good slave she stuck to the task and did a couple of laps, feeling lucky it seemed to be quiet.

Before i let her leave the park she had to push it a step further. Skirt lifted up to show off her ass and chastity, and as she was in sub space i get her to add some spanks as well. But to minimise her risk on this occasion that was all, coat back on for the walk home.

Naomi had done a few quick walks previously, but the outfit and actions were a step up. Her training as a sissy slut was progression perfectly!
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Old 03-25-2022, 07:29 AM   #15
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Part 11 - Pretty In Pink

After halloween work for both of us got busier, and the re-emergence of covid also put extra restrictions on things. As such we didn't get to play too much. Naomi was keeping up with her rules, and getting quite used to living her home life as a girl. So we'll jump ahead into January and the first proper free play time in a while.

This was bimbo day! I'd been working hard to introduce Naomi to more color in her wardrobe, and a classic for any sissy is pink! We bought a pink wide mesh bodysuit, that frankly was about as effective at covering a body as a window. To this was added a new blonde pig-tail wig with pink & blue highlights. Very cute. Put together with pink heels, pink chastity, and some pink makeup, i had myself a perfect bimbo barbie doll.

I made Naomi worship her heels, hump on them, just to get her sub space going. Then we did a cute photoshoot, working on a lot of ahegao faces and dolly exposing poses. To take it up a level Naomi had to fetch pen and paper and write out some extra signs, stating she was a puppet and fuck doll for me. Plus i made her write a sign saying her boy name, just to embarass her in the future.

Next step i sent Naomi to the bathroom. Here she was made to kneel and kiss and lick her toilet seat. Dolls don't argue, even if she did whimper. Some deepthroating on a dildo also placed on the toilet was effective. Maybe too effective as her fake lashes started to unglue, leaving her looking like a facefucked slut. No complaints here!

With Naomi now deep into a bimdo slut space we continued with some anal play with a few other dildos. Lots more general teasing. She was riding a toy in her ass, back sucking the toy on the toilet, being a dirty bathroom slut. So i pushed my little toy further still, making her give me her Ex's phone number. Got to keep adding more and more blackmail power, keeps it interesting!

Alas our play was cut a little short in an unusual way. Naomi suddenly got a call from a family member needing a lift somewhere. Slight issue, as her make-up would not come fully off. So my sissy had to drive with the light pink lipstick still on, fingers crossed it raised no questions.

Luckily it didn't, but this was a close call. Perfect ammunition for me to tease her about and continue to make Naomi feel week and melted. Plus I now had a Bimbo Barbie with extra functions, and an even more blackmailed slave. Naomi really was the absolutely very best person, i love her! <3
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Have an amazing sissy slave for 2+ years! Have a new hypno/denial female slave! Have an awesome sensual female slave! - Yes, i'm building a little hareem of sluts
I do not want any more subs, do not ask, you will just get blocked.

My AMA - Come ask anything at all!
My Intro - Learn about who i am!
Joint AMA with My Sissy - Come as us anything!
[Half-Fiction] A Kitty & Her Mistress - Story Time
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