None of the images on this blog are mine. I've manipulated, combined, edited, and otherwise fiddled with many of them. Where I know the original source, I've made a note in the blog entry. I welcome comments and feedback, and I hope you find something here that speaks to your own transgressive fantasies.

I've created a tumblr at transgressivefantasy.tumblr.com. I'm adding old captions to the tumblr and I'll publish new ones on both blogs for the time being.

Saturday, February 25, 2012

Mommy and Auntie Janet's New Sissy

"Oh my goodness, Janet!  You really brought out the sissy in him!"

"I told you it wouldn't be difficult! He's hardly the most masculine of boys!"

"Rather like his father!  Well, any doubts I had about training him to be my sissy maid are gone now!"

"Remember, you said I could borrow him --or rather her-- the weekend after next.  My daughter Jenny will be home from college with her roommate."

"Oh, won't that be wonderfully humiliating!  Serving you and two girls his -- I mean her-- own age wearing that sissy maid uniform!"

"You know, I always thought she had a crush on my Jenny."

"I always thought so too.  My goodness, look how pink our sissy's cheeks have gotten!  She must be looking forward to it!  I hope you don't mind if I stop over to see how she does with you and the girls?"

"Oh, not at all!  I think will do her some good to be surrounded and overwhelmed by powerful women.  It will help destroy the little bit of maleness left in her!"

(Original images from secretsinlace.com)

4 comments:

  1. By the look of those two there aren't many men who stand a chance.

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  2. ahah I love this one!! Two gorgeous mean ladies wearing the finest lingerie! Anne is right, no men could resist, there's not much left but surrender..

    I really like your blog!!
    xxx Rosemary Gurl

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  3. Superb caption! Always love conversations between dominant females as they discuss the forced feminization training of the male. Truly adds to the marginalization of the male when spoken about dispassionately behind his back as if he were a mere commodity upon which to practice training methods or an object to ridicule... keep up the great work!

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