His Aunt dressed him up as a girl

“It’s just I was trying on some clothes the other day and ….” My voice trailed off.

Then recognition hit her face.

“Oh! You’ve been playing dress up in those clothes I gave you, haven’t you?”

I felt my cheeks flush red with the heat of embarrassment and my eyes darted down toward the floor. “Yes, ma’am”

“Well then you should know what it’s like to have big boobs, right? I assume you’ve tried on that bra I gave you. Did you try stuffing it up?”

“Yeah, but I just can’t seem to get it right. Every time I do I end up with these things that just stick straight out.” And I made a hand gesture to illustrate my point. This made her chuckle.

“So you’re looking to a little realism, is it? I think I have an idea. Go up stairs, take your shower and then bring down that bra I gave you.”

I did as I was told and rushed upstairs to my room. I had to rummage around in my pile of clothes to be sure that I came back with the bra Aunt Christy had actually given me. I didn’t want to come down with one of her other bras in my hand and spoil the whole thing. I showered, put on some shorts and a t-shirt and returned to the dinning room.

Aunt Christy had straightened up both the breakfast table and her bathrobe.

“Take off your shirt boy,” she commanded as she took the bra from me. I did and she hand me hold out my arms so she could put it on. Then she fastened the hooks and adjusted the straps. “Now turn around.”

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Erotica, Wet Dreams, and Assorted Paraphilias

Erotica, Wet Dreams, and Assorted Paraphilias

One thought on “His Aunt dressed him up as a girl

  1. Thank you so much for re-posting this story as it is one of my all time favorites. In fact I was searching for it earlier this week. Also, I am very glad to see you are posting again, I missed viewing your content.

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