Being new to his high heels Oscar grabs his grandmother's (formally father's) strong hairy arm. "Yes, ill take all the help I can get grandma. Please help me get though tonight." He says turning to her.
Jennifer then slowly guides her grandson upstairs to their now shared bedroom. "I must say, that is a very elegant dress you are wearing Oscar." She comments once fully inside their bedroom.
Oscar quickly bends down to take off his heels. He doesn't realize his new milf ass is sticking straight up in the air. It takes all of Jennifer's new strength not to smack his ass. "Elegant or not, it's extremely tight." He says once his heels are off his feet. "Why does she wear stuff like this."
"Because it makes her look and feel pretty. It's what women do." Jennifer says as she watches Oscar sit on the bed. He wants to lazily spread his legs but his dress prohibits that sort of leg movement. "Would you like me to help you get out of that dress?"
"Well no grandma. I don't want to see my mother naked. That's sick." Oscar said trying to get in a comfortable sitting position.
"Oh don't be ridiculous. That's your body for the evening. You have to undress it at some point. Now stand up and stop being silly." Jennifer said after using her new found strength to pull up her grandson. "Oscar, hold still"
After a bit of fiddling Jennifer found the zipper in the back of his dress and gave it a pull. "Oh I can breathe!" Oscar said as he let the garment drop from his soft shoulders. His dress then dropped to the floor. He now stood, looking at himself in a full length mirror. Now, wearing only his mother's silver gray shinny bra, and matching silky panties, his face turned bright red.
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