Monday, August 18, 2025

Matriarchy Monday (8/18/25)

Source Deviant Art

Ed was astonished....his aunt didn't allowed him to wear male clothes while he was staying with her, but that of a 18 year old girl.

She dolled him up, applying make up, teaching him to manage his miniskirt.

The bell rang and his aunt smiled: "I know why you were sad.... 18 year old girl like you needs to have fun."

And before he could say anything she gave him a purse and pushed him to the front door... Where a smiling guy was standing.

"Hi Jenny, your aunt told me that you were beautiful....but her words didn't describe your grace," said the guy. His aunt pushed Ed out in a short minidress, with a guy staring at his fake boobs.

But the worst happen when he grabbed his hand. Worst for the moment.. 

"Have fun you two," said his aunt. 

7 comments:

  1. Ed should have immediately told him that he was a guy and that his crazy aunt was forcing him to crossdress but he was both caught off guard and ashamed that he had allowed her to. Instead, he accepted his hand and introduced himself as Edie. Would love to know how it went from there.

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  2. I think that the young man knows that his date is really an 18 year old sissy.
    Ed's Aunt has a friend whose son is a closeted gay.
    I would like to know why Ed's Mother sent him to live with his Aunt.
    Perhaps he was caught going thru his Mother's bra and panty drawer ( several times).

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  3. Auntie knows this is what Ed wants but doesn’t have the courage to be her true self. So auntie is giving her the push she needs.

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    Replies
    1. No, I think the young gentleman will be giving her the push she needs

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  4. "Have fun you two... gosh I think the two of you make such a cute couple."

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  5. Judging by the look on her face, the sissy is terrified of what will be expected of her by the end of the night. She never anticipated being the feminine half of a "cute couple" .Lets hope that her beau will be gentle. I hope that Auntie has put some protection in her purse.

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  6. He should have bought flowers. How exciting. I hope it is a slow courtship. Holding hands. getting comfortable in each other's company. Maybe more touching followed by some car petting. His aunt should encourage him to keep a diary so he can relive his first intimate moments. Perhaps write little love letters. After a few weeks she will have a talk with him and explain that a man will need more if he is to stick around. That's when I'm sure she will provide the nessesary protection. She will be so excited to see him blossom.

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