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She and Her Friend Sneak into a Strip Club!


Who could be so diabolical and devious? I know .. and you will know too!


I miss Leeanne Montgomery! There, I said it, and I'd say it again. She was the first "real" sissy I knew, and I believe that Kaaren came along soon afterwards, and my life would never be the same again! I'm not kidding!

Anyway, I made this for her about 5 years ago .. and I think that not long afterwards, some shit when down in her life, and she had to disappear. I think she still might have a picture feed somewhere, but I have not heard from her in quite some time. Has anyone else know what's up with her? Let me know if you have some inside knowledge!

Sooooo, unless you are Caitlyn Masked or Leeanne Montgomery (and Sally Bend during the first repost of this (ooops!)).. this just might be new to you! Here's what I said back about 5 years ago:

Well, I saw this picture, and while a bit more naughty that I usually post, was an instant goldmine of ideas for me to place into a caption right away. It was always going to be a husband and best friend trying to figure out what his wife did when she went out. Believe it or not, but I was thinking of Fred and Barney spying on Wilma after being turned into women by The Great Gazoo. Then, with the obvious skill of one of the ladies in the image, it became a Leeanne caption. With that, I saw that the girls do look like they could be dolled up men, which with would be another skill that Leeanne's friend probably didn't realize Leeanne was proficient at, makeup and dressing up. So this caption wouldn't be magical at all, but perhaps a slice of someone's really kinky real life!

From there, the ending just sort of jumped out at me. What if the stripper knew Leeanne already, and this was just a complete setup? Of course, that made all the sense in the world! The rest just rushed right out into the caption, and it has everything that should be in a Dee caption: some naughtiness, a bit of obliviousness, some snappy dialog, a twist at the end, and an open-ended conclusion that lets the reader fill in the blanks however they want. I am quite pleased with this one, I must say.

I know .. .I am one bizarre caption making chick! So what else is new? Figured I would re-post the discussion questions too. Go for it!

DISCUSSION QUESTIONS: So, what happens next? If you had this picture, what story would you have drawn from it? Let me know what you think since this is a blog exclusive!



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