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Sissy Feminization : Getting Dressed Up

Once upon a time there was a sissy who really loved pretty dresses.

The sad thing was, this poor sissy felt like his love of dresses and sissy feminization was shameful, and something that he just had to hide from the world. So he pretended and pretended with all his might that he didn’t like dresses or panties, and didn’t want to wear pretty red lipstick, and never thought about shaving his legs and acting like a total slut. Poor sad sissy, hiding it all away on the inside. But even though he pretended so long and so hard that sometimes he even forgot about his love of all things femme, it would still rear it’s head and remind him sometimes, that he just wanted to be a sissy slut.

Do not be shameful about your sissy feminization. Be proud!The sissy who loved getting dressed up had so successfully squelched his own joy that he’d forgotten how much he loved sissy feminization.

One day, the sissy met a woman who saw right through him. She was kind and smart and incredibly sexy, and very insightful as well. She looked at the man who pretended he wasn’t a sissy slut, and just knew that he’d look great on his knees in a dress, as a feminized sissy. So, she started to carefully, slowly, seduce him. She worked to bring out his vulnerable sissy side, and one day, she presented him with a gift. It was a small box, barely bigger than a tablet, with a satin ribbon tied around it. He opened the box, and lifted the tissue paper out of the way, and was just amazed at what was inside.

The sissy that had forgotten his love of girly things had received a gift of lingerie.

Pretty, sexy, silky panties and a matching lace bra were nestled into the box his Lady had given him. He looked at her, confused. “Aren’t I supposed to give you lingerie?” he asked. She just smiled, and shook her head. She wanted him to wear it for her. To put on a show, to let her see how sexy he looked in pretty panties. She told him that she really loved seeing a cute male butt in silky panties, and would he please wear them for her?

The sissy didn’t realize that the gift of panties would be only the first step in a long road towards his eventual total sissification.

He also didn’t realize he’d never been happier until he looked back on that gift, years later.



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7 comments to Sissy Feminization : Getting Dressed Up

  • Sean

    Mmmmm, what a lucky sissy! I am a shy, closet crossdresser and I sometimes try and tell myself I am a normal man and dont enjoy wearing womens clothing, shoes and makeup. I always cave and dress up again, but by myself. I would love to find a woman would enjoy my cute male butt in a pair of silky panties! I enjoy most female clothing, and I absolutely love strutting around in a pair of open toed heels after a pretty pink pedicure!!

  • Petey cream puff

    This is what I’m looking for!!! I admit I’m a cream puff who likes dressing up as well in women’s clothes/bras/panties/slips/makeup/
    Lipsticks/perfumes/dresses/choker tops/leggings/yoga pants/knee high and ankle boots. I want women to do this to be and be in female lead relationship.

  • First of all, any man who dares to go out in a dress deserves recognition. With such a large percent of the population who are into cross-dressing I don’t think this desire is going away anytime soon. In addition, men who cross-dress get relief from tension simply by wearing women’s lingerie under their male clothes.

    • yvonne

      Oh yes Ms Cindy!! Cross dressing is such a great reliever of stress. It certainly is for me. The entire ritual of dressing, doing makeup, and hair all the while listening to some soothing music puts the tension in the basement.


  • Jennifer

    Thank you so much for this story, this poor man had suffered long enough. That could have ended badly but he was saved by an insightful wonderful woman. There are resources in the world and LDW is one of them. Tearing up, thank you.

  • Oh my…please let me receive such a wonderful gift!!!

  • Sissy April Nicole

    Crossdressing is so much fun! Also dangerous. A lot of creapy guys out there. Women be very carefull! After going out for over 10 years i am afraid to drive a car as a woman. So i quick change at the nite club. One time this was soo cool i had my mini skirt hiked up driving an 18 wheeler shines his light to check out my legs. I wanted to scream out I have a dick. LOL

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