Sunday, October 20, 2013

Caught at the Sorority .. and RED SOX in the World Series!

Is it possibly the best thing ever to happen to Alex?

Made this one for Kendall, who doesn't seem to mind cross-dressing captions, which is good for me, since I seem to be making more and more of them lately. I still make magic ones too, or keeping them vague so your idea is as good as mine as to have far along they are, but yeah, I guess I've been in a cross-dressing groove creativity wise.

I am betting that lots of our readers wish that when they were in college they were "Captured" by a rich girl that loved to dress them up and take them out as a female. Who wouldn't want a sexy sugar mama to make them the girl they've always wanted to be? Got any other scenarios playing around in your head. Mention them below and perhaps they'll be turned into a caption by me or perhaps any of the other dozens or so captioneers that frequent this blog.

Sorry I didn't post earlier but I was celebrating the Red Sox getting to another World Series. All they need is another 4 wins out of the next 7 games and they will be world champions!




  1. Oooh, you and I may have to go dark for the next week or so, babe--my Cards want that title. ;) Great cap, though!

    1. Well, they are both good teams that did it the right way this year. Everyone else "Feared the Beard" so we'll see if the Cards can shave 'em clean or not!

  2. Nice cap Dee! And a begrudging congratulation to your Red Sox. I may not be a baseball fan, but I still try to root for the home team. Therefore it's hard to celebrate with a friend when my Tigers supplied the sacrificial lamb!

    1. I was much more worried about the Tigers than any of the other playoff teams since they had a great rotation, but the bullpen for Detroit was hideous. All the Sox had to do was wait out Verlander, etc .. and then take advantage.

      I think I left too much information out of the caption when I am looking at this caption again to be honest. I really hope that everything I wanted to portray came through and I'm not sure anymore.

    2. To explain how little I watch baseball, I actually had to look up and see who Verlander was. :)

      Without knowing all that you wanted to portray I can't say if you hit the mark or not. What I got was that 'Alex' had a history of crossdressing and dressed up to go on a panty raid at the Sorority house as is the tradition of his frat. Crossdressing helped him, but only to be the last one caught. The rich 'princess' that caught him decided on keeping him and will use him as a 'boyfriend' to her rich parents but otherwise keeping him as her sissy lover.

      It's a lot of information to put into a cap like this, but I think it came across smoothly and beautifully.

    3. Wow, I guess I did give enough information .. well, other than the fact that he kind of got caught on purpose because the frat would figure something out if he HADN'T gotten caught.

      Glad I was able to convey pretty much all that I wanted to and didn't cut out what was needed!

  3. Lovely caption,
    For me, the girl didn't even have to be rich, but it is of course a plus.

    The Red Sox made it even in the newspapers here, but to be honest that has probably more to do with Xander Bogaerts playing for the Sox. After all, Aruba is part of the Kingdom of the Netherlands. I guess I have to start rooting for the Red Sox;)