Chicago Domina in her bdsm studio

“THANK YOU, THANK YOU, THANK YOU MISTRESS for the best session ever. I will try to describe it.” Sissy Eva

When i arrive and see you without boots i was disappointed, wanting to ask  you where your sexy boots were. But when i see them on the floor i knew i was going to help You put them on (thank you mistress and hope to do it every time). (Mistress note: I will take into consideration your requests and interests when we session. You may not get everything, but you will get what you need.) For Mistress’s interests, click here

When you start giving orders and start telling me what was going to happen to me, my mind start running (in unison with your cock). When You said that You were going to make me a sissy maid and then use my  ass pussy, I got excited. When You renamed me “Eva”, i knew i had to be the best Eva You had. Thank you for making worship Your boots.( Mistress note: Boot worship is one of my favorite fetishes to engage in with a slave. I love watching you kiss and lick my boot heel.) When you start dressing me as a sissy with garters to sustain the stockings i knew i would enjoy it. The chastity was a little difficult at first. i am sorry that i was thinking with my male persona. (Mistress note: If one can not control themselves , I will control you. Your cock clitty will only be erect when I desire)

You were wearing the key around Your neck resting between Your lovely breasts so that every time I see it, I was thinking “so near but so far”. While locked in your cage,I was dreaming it was your hand holding me  (Mistress note: If I ever touch you, it will be to control you or cause an uncomfortable CBT reaction.)

Long legged Miss Simone

You start dressing me in a pretty outfit then make me act like your sissy,calling me Eva. i had to be the best sissy for you. The breast forms were really humiliating but being unable to see the chastity made it more humiliating,controlled by the chastity. You  decided to sensuously rub against me to make my member strain against the cage. i was in heaven and in hell because of the chastity. (Mistress note : I enjoy locking up my subs and sissies to control their orgasm. One of the best cage company in my opinion is Steelwerks.

Mistress starts lacing me into a corset making it tight to form the female curves, giving me an hourglass figure. When you put your hands on my corseted waist , I feel like a pretty sissy. The stockings were different,feeling silky and sexy on my feminine legs.The shoes were a little different, making me walk with my ass out. I liked that the high heels were locked on but i was a little afraid of the heels.(Mistress note: Learning the proper way to walk in high heels is key to a sissy’s education.)

I really did learn to appreciate a woman in high heels. After only being in the heels for less than an hour, i felt my legs tight. Now when i see a woman in high heels i appreciate her tight legs. The walking was difficult, scary, and exciting, especially since i feel like a sissy when walking. I hope i can learn to walk in them. If I please Mistress, maybe next time she will allow me to wear boots. You then put me in front of the mirror in a position for your use. I am a sissy for Mistress’s enjoyment

Sexy high heels make the legs

I am allowed a little rest but soon Mistress says it’s time for my spanking. This is always scary for me because i do have a low pain threshold.  Mistress warms up my bare bottom under the crinoline skirt, informing me my cleansing is next. (Mistress note : I prefer my sissies clean before I use their ass pussy. ) You start the colonic ,ensuring I take the full bag. i knew You were going to use Your strap on your sissy.especially. i had to walk on heels for what seemed like a long distance to the restroom,every muscle in my body tense. When in the bathroom i had to pee and with the chastity it really made me feel like a sissy slave. When you instructed me to leave the door open, i was unable to think of doing anything against your wishes. The heels making even sitting to pee different. The humiliation was at all time high. I was able to see my legs and the position of them, different but feeling more like a sissy.

Once I am finished in lady’s room, I am informed you will spank me again to remind me of my position. When You start spanking me again, i had to admit that i deserved it. Thank you for the spanking making me remembering my position. i love it when you start to play with my nipples afterwards, removing the breast forms to get to them.

Mistress decides it is time to use my sissy hole.  You start by using your fingers to loosen me up, preparing me for your rubber phallus. i wanted to be able to serve You the way You deserve. Thank you for the treatment. When You left a dildo in my pussy i was in heaven and asked to kiss Your ass while kneeling at your feet.

Mistress i was in heaven when You made me worship / kiss Your Ass and Your boots (I must admit every time i had an opportunity , i was looking at Your Ass and high heels boots. When I was allowed  to use my hands,it was extremely erotic. The skirt You wore was magnificent, its form fitting would make anyone desire to kiss Your ass. Please i want it all the time, in all our sessions. (Mistress note: I only allow body worship when I feel comfortable and it is earned by the submissive.)

Then You make me worship Your boots and suck on the heels like a penis, informing me I will be donning the maid’s outfit to make you a cup of tea to relax after our session.(MY favorite tea is Mariage Freres.)

You then instruct me to kneel in front of you. Upon removal of the chastity cage, you keep me on my knees in front of you, instructing me how to make your perfect cup of tea. How to make a perfect cup of tea! I am then permitted to take the chastity cage off. You instruct me that I may orgasm but I will be eating anything that comes out. If not, there will be punishment.  I retreat to the studio kitchen to perform my tea task. Upon my return, you judge it worthy to drink. I achieve my well- earned release and ingest the result.  Thank you for the honor of becoming your sissy Eva.

Time for Chicago Mistress’s tea!

THANK YOU, THANK YOU, THANK YOU AGAIN MISTRESS for the best session ever. You really make me feel like your sissy maid

Desire to be my next sissy?

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The post Chicago Dominatrix Simone – Sissification of sissy Eva appeared first on Mistress Simone.

Chicago Mistress and  sissy maribeth

As someone who’s never been to a professional mistress before I really didn’t know what to expect when I arrived to see Mistress Simone. All I was really sure about was that I liked to dress up in feminine clothes and be tied up, common enough interests for a lifelong cross dresser like myself, I’m sure.( Mistress note : Feminization is among my favorite activities. Assisting someone in exploring their gender fluidity, discovering new aspects of themselves brings joy them and Mistress. I can engage both on a spiritual level or a humiliation one, catering the scene intent to the submissive’s desire.)

Chicago Dominatrix w sissy maribeth

The sounds of Mistress Simone’s heels as she came down the steps to her waiting area were like little jolts to my nervous system and I know my eyes widened when she first walked into view. She looked even better than her pictures on the website ( Mistress hears this often. I am not a fan of having my picture taken, so I do appreciate when a submissive comments on my in person spirit.) My nerves that had begun jumping again during my short wait began to settle as we chatted to better acquaint ourselves with each other. I showed her the feminine clothes I brought to wear. Funnily enough, she loved the boots I brought almost as much I did when I first saw them. (Mistress loves shoes and boots! Her collection is extensive. Come see.) I felt any lingering nerves melt away.

Soon enough, Ms. Simone instructed me to remove my clothing. I could feel the blush as she complimented my breasts, something that I’d never thought about receiving. I guess having a little extra weight worked in my favor this time.( I find beauty in all bodies. Humanity is encased in our flesh, and it is up to us to move beyond the superficial into the esoteric of our souls.)  After I finished undressing, she placed a collar on me and led me into her dungeon for the first time.
There was so much to see and take in. I was in sensory overload. ( Mistress note: It takes courage to reach out, make contact and follow through. I commend all submissives that enter my realm.)  She allowed me a few moments to gather myself before placing a gorgeous auburn wig on me, putting my clitty in rope and helping me dress in my blue cowl-necked dress and boots.

After binding me to a spanking bench and blindfolding me, Mistress Simone spanked me with her hand, then a leather paddle and a wooden paddle, all the while teasing me and taking care to keep my physical and mental well-being into account. I made the mistake of using Mistress ( Mistress note : I prefer Ma’am. I find it fits my personality better. Also, it is what I use on my lifestyle as my community gave me the moniker.)  to address her after a spanking. I could tell the difference in hand spanks immediately causing a quick correction to her preferred term of Ma’am.

Mistress Simone in her Chicago dungeon

At one point while bent over the spanking bench, Mistress Simone elicited a very girlish squeal/moan from me that tickled her to laughter and me to embarrassment. I don’t know why I felt so embarrassed about my obviously natural reaction. If I remember correctly this may have been around the time she inserted the plug in my pussy. ( It was! Overload of sensations lowers inhibitions.)  All that I am sure of is how delighted she was to get such a reaction from her girl.

Soon Mistress Simone wished to move me from the spanking bench to her bondage table, but when she got me untied and I followed her directions to move halfway up, I did get a tiny bit warm and lightheaded. Ma’am immediately recognized and helped me to sit for a few moments even giving me water and offering a sugar pill after removing the wig and her collar to assist my recovery. Her concern was evident and it was at this point, I knew I’d be returning, regardless of how the rest of the session went, even if it wasn’t conscious thought at the time.

Once I was sufficiently recovered, she helped me change from my blue dress and boots into a red baby doll nightie and secured me to her bondage table. She  cuffed my wrists and ankles to either side before bringing a couple straps over my mid-section. Then she placed five clothespins down below on my lady clitty, used a violet wand on my upper thigh for a short bit, then placed a vibrator up against the plug in my pussy, getting another high pitched moan/squeal that made her laugh yet again. (Mistress note: laughter is allowed in my dungeon. While I am a serious Mistress, and take our time together seriously, I also like to have fun. If we both enjoy our time together, it makes it much more memorable.)

Mistress Simone played with me for a while until it became clear that while I was trying to remain communicative with her it was becoming more difficult. I seemed to be completely relaxed and entering what she called sub-space. All I know is that I’ve never felt as mellow and completely de-stressed as I did at that time so if that’s what sub space is, then sign me up for it.

Again, like several times throughout the session, she assisted me with water and let me recover at my own pace before officially calling an end to our time in the dungeon. The two hours really seemed to fly right by and it was time for me to get dressed in my street clothes and get ready to depart. Before I did though, we discussed our time together and what I thought of it. I believe one phrase I used was “how many times can you say wow?” and that seemed to delight her to no end.

All in all, I can’t say enough nice words about Mistress Simone and how caring, professional and welcoming she was to me. I can’t wait for the next time to return to her dungeon and be her girl again, even if it’s only a few short hours.(Mistress note: Those few short hours make a huge difference on the way we view life. It can bolster one’s spirit for days, even week afterwards. Regular sessions enhance one’s well-being.)

Thank you so very much, ma’am, I know I won’t ever forget this!

Sissy maid bound to serve

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