Wednesday, December 17, 2014

Sarah Ashley's Island of Mystery!

.. it sure as hell isn't Gilligan's Island!

Made this one as a reward for Sarah Ashley making the 3365th comment on the blog. I think that this caption, along with the one I posted last week, "C'mon In! The Water Is Fine If You Like It Cursed!" shows that perhaps heading to a Caribbean resort for some sun and relaxation might be a good idea if I could afford to go!

I know the weather hasn't been bad yet in most of the country (Buffalo excluded!) but I would imagine being stuck on that island would be a much better situation than shoveling a few feet of snow so you can get to work on time! I loved the picture as soon as I saw it, and immediately put it into a caption setting. Its also a bit wordier than I usually like to be, but some things just HAD to be told, and it needed to be a bit steamy as well. I hope Sarah enjoys it as much as I did when making it!

And if not, then at least I can give her a re-captioned gift as well .. she mentioned an older caption that she really liked .. so I remade it with her name in it instead. Consider it either a consolation prize or a bonus round surprise! Either way, thank you for commenting!

There might be one more "normal" caption posted here (two tops!) before I start doing the Christmas goodies. At this point, I believe I have five of them .. a few are naughty and a few are nice. They should all be new to this blog, though one or two have been posted to the Haven. I'm trying to work out the order of when they'll be posted, and there is caption for Katie Mills, and one for Kaaren within that block. If I end up with some inspiration and make more, perhaps I will start the festivities with the next post. We'll have to see, won't we?


  1. Well, I hope he waits just a little bit longer. I'd hate to have something in the way when we meet. And if that doesn't work out maybe I'll go and vist dee and her room mates.
    Thanks a bunch for the captions, they are absoluteley spectacular

  2. You come up with some of the most incredible feminine transformation fantasy posts of anyone I've ever read. Are you sure you aren't a sissy?

    1. I don't think so Leeanne. Many times I approach it from the "I am doing the transformation TO the person I'm writing it for," as opposed to more of a wish fulfillment viewpoint. Sometimes I am able to get into a submissive head space and that can really help my captions, but it is hard to do. Usually when I've had an physical ailment and are using painkillers or muscle relaxers. The weird thing though is that I usually end up as more of a 'bimbo' than a sissy!

      I've also tried doing some role play online, and Jennifer did a great job of being "domme". At a certain point though, it ended up becoming more of a writing lesson, as once a line was crossed, the real me came out and was like, "what the fuck?"

      I wouldn't mind being an honorary sissy though!