Surrender Sunday: The wife sent me on a date with her father!

 

Source: Just A Wicked Taste

My wife told me that her dad has had me pegged as a crossdressing sissy since he met me. 

After her mom finally left him and he promised my wife a better deal in the will if she 'lent' me to him for one night only. After some convincing and how it would benefit us financially and making me feel guilty, she assured me that no one would ever know, only her, me and my father-in-law. The following night my wife got me in a dress and made me over crossdressed to a country club on the other side of town. 

He found me there with a bouquet flowers and a grin on his face. The deal was for a 'one night experience' with a 'woman'. Seeing the lube, the condoms and a hotel key in my purse that my wife had given me, made come to the realization what the 'one night experience' meant. 

'This is going to help us get out of debt and set us up financially,' I repeated in my head as my father-in-law led me into the hotel room. Our future would be secure financially, but the price was surrendering my masculinity.

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.