BDSM, Chastity, Dominatrix, Femdom, Fetish, Humiliation, Orgasm Control

A Hard Lesson For A New Sissy

20160224_161150I screen My boys that serve me IRL very well. Just because you want to serve Me does not mean it will happen.

I will make you jump through a few hoops, and prove yourself to Me.

I have a brand new sissy that has been trying to earn time with Me, and I finally agreed to a session with him.

He was a Dominatrix virgin, eager to have his cherry popped!

When I arrived I was impressed that this sissy had went out of his way to get pretty for Me in advance. Full makeup, wig, dress, complete femme.

Oh and the sissy even went outside where people can see him fully dressed too! [laughs] Public humiliation cherry popped too!

I was slightly impressed he went to the pet store and got his very own collar and leash, complete with his pet ID tag! In purple of course!20160224_161135(2)

After some time in our session, about two hours in, I had unhooked the wrist restraints, to change a position.

I was turning around to allow a small treat for her, and without warning I feel a hand SMACK MY ASS!

Now I do realize that I have a full inviting ass that makes you want to smack it, bite it and lick it, but that is for the special people.

It is not for a brand new sissy trying to prove himself. Serious disrespect!

lil willie [his name has dual meaning, you figure it out] learned fast about showing some self control, he almost used his safe word. I broke my fucking crop, then I moved on to the big paddle!

Perhaps he was testing to see how I would react, and now he knows!

20160224_184706He is actually lucky I did not end the session then, but punishment is part of the fun, he is a newbie, and clearly needed to learn a lesson.

It was his lucky day.

Moral of this is, practice some self control, don’t make Me break My toys on you.

I hate breaking My toys. [Growls]

So lil Wilamina, and all the other sissies, remember, no touchie unless permission is granted.

Resist the urge, fight back your animal instinct!  Common Sense M’kay?

Now replace My damn toy! [Evil grins]

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2 Comments

  1. wilready13 says:

    One tiny swat
    Okay, so I made a small mistake, a minor indiscretion by giving my new Mistress a tiny swat on the ass. But, oh my, what a glorious ass it is. Look after an hour and a half or so of being taught by my Mistress in the art of pain, she was giving me a rare treat, a chance to kiss her ass, she turned … some things just can’t be explained, there it was so inviting, so near, so exposed and then I smacked it. There was no malice intended, no thought behind it, it just happened. She turned, incredulous, then a mischievous grin took over the look of shock, oh you’re going to get in now she opined.
    You know that empty feeling you used to get in your stomach when, as a kid, you knew the beating you were about to receive was going to be a whopper? Well that feeling, long forgotten, was back. I swallowed hard, and tried to laugh it off, I don’t know why I did that Mistress, and I’ll never do that again, please forgive me. I tried to kiss her feet, tried to plead with her, be gentle with me, please, please, please.
    I was already on my knees, turn around she ordered, I quickly complied, over the bed she commanded, of course I did. I heard the crop whistle through the air, whack, ouch, a small ummm, escaped from my lips, whack, whack, whack, I was starting to cringe and was flinching with each sound, thank you Mistress, thank you Mistress, I said each time I felt that sharp pain, just as I was taught, thank you Mistress. Such was the punishment, the crop broke. Wilamina, will you ever do that again, no Mistress, no Mistress, no Mistress.
    I was breathing hard, almost panting as the pain receded, get up on the bed, head down ass up she commanded. I wasn’t sure what to expect as she began to work on me with the vibrator I had brought, ummmm ………. There is but a fine line between pain and pleasure and Mistress V knows how to bring out both in stunning and wonderful ways.
    Wilamina

  2. Ms V, as a sub who has Mis stepped myself (several times) I certainly have sympathy for your new sissy. However I also admit to cringing a lot at the thought of you getting whacked so unexpectedly by the new sissy.

    I am sure you resolved that to your satisfaction…? And that he probably knows better for next time.

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