Sunday, September 14, 2025

A Win-Win Scenario ..At Least for Me It Is!

It's not quite the Kobayashi Maru, but I can see Bones McCoy doing this maneuver. 

"Damn it Jim, I'm a hot 30 year old blonde CEO, not a doctor!"

I think this might be called .. playing the REAL long game, or that 3 dimensional chess that Spock was known to enjoy .. but it does reason well in not only defeating your enemy, but trapping them in a bad situation of their own making. Perhaps it's not quite the, "someone goes low, you go lower" mantra, but I love the comeuppance so very much.

I am going away for the weekend again, so I'm writing this post up before hand. Figured I'd put out a call for what caption types you, as the readers, would like to see in the next few weeks. I might have some time to whip some new stuff up, and I'll take ideas, tropes, and settings you'd like to view in caption format soon.

Please do leave them, along with comments about this current caption .. down below!

We lost a musical and actual genius earlier this year, and of course I mean, Tom Lehrer. So much good stuff from him, and you should see his actual background. Monumental man in every way.

7 comments:

  1. The CEO has much better fashion to choose from too.

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    1. Very much so! And just about anything should look good on her!

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  2. I thought about your question Dee but honestly I don’t know what to say are my favorite types of captions…probably any that also include the wife or other special someone as part of the story. Color me the perpetual romantic but it also probably comes from my 40 wonderful years of experience exploring gender roles with my wife. I think we both, Dee and I, were blessed for our time with that special person we had.

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    1. Would LOVE to hear stories about you and your wife exploring gender roles.

      My forever person really didn't know anything about this blog, my captioning proficiency or any alternate personas. Same goes for my current GF.

      So, for captions, do you like the wife or special someone to be part of the story in a loving way, or more antagonistic? Figured I'd ask!

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  3. I enjoy both. TBH I shared my cross dressing desires early in our relationship and she supported and encouraged me even though sometimes role playing forced femme scenarios.

    I am definitely not even close to passing as feminine but she especially loved buying me lingerie or sexy costumes for me to wear for her. She also liked to push my comfort zones by doing things like answering the door for food delivery or running errands that included public exposure. In those cases I was allowed to wear clothes that would not get me arrested for indecent exposure but were definitely “on the edge” like super short skirts, a maid uniform, school girl uniform, that type of thing. When in private she often added bondage elements because that was her thing and I grew to love that too. We both tended towards submissive so we switched a lot but it worked for us.

    It’s been almost two years since her passing from pancreatic cancer, and I haven’t put myself back out in the dating scene, partly because I never really dated. My wife and I grew up on nearby farms and we were best friends with no romantic relationship from 2nd grade on. We lost touch while going to different colleges then bumped into each other at a party and things just clicked. We moved in together 2 weeks later, married a few months later and were rarely separated for most of our time together.

    This got long, but hopefully gives you some insight into our relationship. I doubt I’ll find another like her, but at least have some companionship since I’m only 62 now and my family has decent longevity.

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    1. That is such a sweet, supportive and somewhat kinky relationship you had with your wife. Thank you for sharing that with me, and also anyone that follows my blog. It reminds me of S!ssy Kaaren and Mrs. K's relationship as well, and I'm glad that my many of my readers have had such fulfilling married lives!

      I'm saddened for your loss .. same for Mrs. K .. and consoled with the fact that we all had very loving, special relationships that made us who we are today .. and they will live on in our memories, and to light our way forward in our own journeys, as we continue the path with them beside us.

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  4. Yes, I would agree that Kaaren and Mrs. K had a similar relationship to ours in some ways but definitely not in others. I think my relationship was more flexible in roles in some ways and also never involved any others intimately. Ours worked well for us. 🙂

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