Mister Mistress

I have always been intrigued by the idea of Cross Dressing but not only in the typical male to female. I have been having this growing fantasy

( key word Fantasy... since I know by mere body shape alone I probably couldn’t pull it off ) of dressing the part of the male, complete with strap on harness and double headed dildo on and in, so that I have the authentic ” package ” look.

This would be specifically in a forced feminization session. Demand he dress the part in a nice dress with stockings, heels, wig and makeup.

Just out for drinks at the bar or a nice light supper.

Plan to meet at the restaurant, giving “her” strict instructions to not speak or acknowledge any male that approaches her or attempts to get her attention or I will know and punish her severely.
When she arrives she will scan the establishment looking for her Mistress, and not seeing Me going ahead and securing us a table as instructed. Time passes and I still do not arrive she gets nervous and worried, attempts to reach Me are met with the message I am on My way and will be there any minute.

She is becoming visibly nervous, she is in public, dressed as a woman and she just knows everyone can tell she is a man in drag. She starts picking at her outfit n a very self conscious manner. she is understandably shocked yet intrigued when a gentleman takes interest in her from across the bar. Nervously accepting the drink he sends her way, she smiles only to find when the gentleman appears at her table and sits down it is my voice asking her

why she broke my rule?
Why she accepted a drink from a gentleman just as I told her not to do.

She protests and tries to back peddle …

At that point she realizes that the man sitting across the room that she had caught staring at her periodically that she had been flirting with, was really her Mistress and that I had been there all the time and that she is indeed in trouble for disobeying Me.

Of course at that point I would signal a waiter and order My dinner truly enjoying her discomfort.

Once dinner is done and My enjoyment at her discomfort has been satiated. We head home, and I keep a running dialog of whats going to happen to her slutty self when we get there. That not only is she to be punished for flirting with Me before she realized it was Me but at the many looks I saw her give all the other men in the room from our waiter to the bus boys.

Once in the dungeon I pull her over My knee and spank her open handed to punish “her” for looking so hungrily at our waiters crotch for being such a needy little whore. As she squirms I lean in an whisper that the punishment was just getting started. That I was going to show her what happens to disobediant little sluts and to get up and help Me strip, I have her remove My jacket, vest, pants and hang them up for Me leaving Me in the wife beater, bra shiny underneath the white cotton. Boxers containing a nice bulge that she nervously eyes, a classic set of mens sock garters holding up vintage argyles and of course the highly polished wing tips.

I force her to her knees and have her now smeared lips take in the strap on and suck it down, giving the head of her life as the other end of the strap on dildo rides in and out of My pussy from her oral thrusting.
Once I feel she has lubed it up enough I stand her up bend her over the bench and pry open the ass cheeks, applying even more lube to the head I slowly start sliding it in. Telling her to take it like the slut she is and enjoy it. I fuck her ass as the second head in Me fucks Me back with her thrusting her ass back at Me as I grind in. Perhaps I take her shoulders in hand and thrust deep to bury it in quick succession feeling her body quiver as I give her permission to finally cum. She gasps and screams as her cock is finally acknowledged and allowed to spill its seed across the bondage table. We both rest there until I feel her breathing under me start to regulate.
At that point I pull out unstrap the harness and let the strap on fall to the ground, Taking My place in My most favorite chair to receive oral pleasure I demand she goes back to her knees and take Me over the edge with her tongue. I cum in fantastic waves as I ride her face, her make up completely worn off and wig gone. Her own dress wrinkled and covered in Her cum and mine, lube and other assorted sex juices. I look at her eyes glazed as she finally gets a moment to breathe. At that point I take her head gently into My lap and tell My little slut how proud I am of her and that she will get many more chances to prove what a little whore she can be for both her Mistress and now her Master …

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12 Responses to “Mister Mistress”  

  1. 1 j

    I often have a fantasy of dressing up for a woman but not in public and having her punish me for messing with her clothes and taking me annally while i wear her hose and heels

  2. 2 mim


    This is a common fantasy amongst many of My boys, I just liked the twist of my being in drag as well. Thought that lended a certain unique air to the whole evening and especially the unveiling of the strap on…

  3. 3 Gander

    Now that’s what I call a gender fuck. Pretty hot fantasy – getting in drag is a fantasy of mine but it’s still out of bounds for some reason – makes me very nervous. I’ve known my share of drag queens, but still it seems out on the edge. Guess I need to try it. Thanks for sharing!

  4. 4 mim

    you are most welcome Gander… I had always thought it a hot fantasy just wasn’t sure how it would be recieved. I am really turned on though by the whole cross dressing theme. I like the idea of Me in a suit and him in a dress…just odd enough to suit Me.

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