Thursday, February 25, 2021

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!


4 comments:

  1. I miss Leeanne very much....she was my favorite online playmate and it was through her that I met you Dee....and I am very grateful to her for that!!!
    She stopped blogging over a year ago and stopped answering questions before that...she had a thing still going on Tumblr even after the purge but I think she finally ran afoul of the censors there and they limited her viewers....I haven't seen any activity on that account for a while....
    I have the fantasy that she'll just turn up at my door one day....and she'll have the keys for both of us and we can spend some quality time together...
    I hope she comes back but in my heart I think she's gone....
    I like the cap very much and like to think of myself as the other sissy with her....
    Kisses
    Kaaren

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    1. Yeah, I pretty much knew that, plus much more than you and I know behind the scenes. Hoped that maybe she'd swing by one of our blogs and say hi again, or shoot us an email. I just hope that she's doing OK, and that much of the issues are behind her now hopefully.

      And I can only imagine the mischief that you two would stir up in real life! I have a good idea that you were partly the inspiration for the other sissy!

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  2. I actually remember this one, and I loved it just as much the second time around. It's a fun caption with a great vibe, and then she drops that "your wife too" and the whole thing changes.

    I wonder if Kaaren would take me clubbing like that. :)

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    1. Well, if you travel South of the Border someday, or she hits the Great White North, perhaps that could happen. Until then, you are still my actual real Canadian girlfriend!

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