If It Doesn’t Challenge You Does It Change You

The challenge of stepping out of your comfort zone like a fish out of water
 Image by Mohamed Hassan from Pixabay

The challenge was constant, even in those early conversations. Drawing information out of me. A steady stream of little jobs for me to do. A picture here, an answer there. Now two pictures each day with different writings, and then a video. Ok, ok…pictures were hard enough (confronting the image of myself before I hit send) but videos…. I had no idea what to do. Panic isn’t something which happens to me, anxiety, no not that either…. but he was definitely pushing me past the edge of my comfort zone. The first video was an innocent one, asking me to introduce myself and ask, again, to be his. Flushed with success I awaited his next request.

This one was not so innocent.

He asked me to orgasm for him. And send him a video! At this point I was rarely indulging and had no idea if I would a-be able to achieve one, or b- catch it on camera. Having been mercilessly mocked for my moans of pleasure for years I was painfully self-conscious. Of course, he knew how hard it would be for that very reason. When I initially told him of the mocking his response made me believe he wouldn’t laugh at me. He said:

If your sub isn’t moaning and screaming in pleasure what is the point”

Determination is a funny thing, and I suffered through an intense orgasm. Sending the video, again very pleased with myself. Oh no!! I had made a video of the wrong part of me, he hadn’t initially requested to see my face, just a video as good as I could make it, but I had filmed the working end so he could’t see my expression…. Another video was requested  Repeat your previous task, but this time at the point of orgasm, I want to see your face At this point in my vanilla life I was rarely able to achieve more than one a week, except on rare occasions when 3 or 4 would come close together. To try again after about half an hour was intimidating, to say the least, plus putting my orgasm face on camera…. But the way he asked, and the words laced into the email, how could I not succeed?? I could feel myself growing already.

Breaking free of the vanilla bonds I had been constricted by for so long.

The feelings I was experiencing were new to me. Trust, lust and pride. He never demanded anything, I knew all along that it was my choice. He was absolutely clear on that. And when he sent me a list of his baseline interests I poured over them. What could I expect during an introductory phase, things which would be extended as time passed and my experience grew.

The list was accompanied by four headings.

  •  what I’ve tried;
  •  what I would like to try;
  •  what I don’t fancy but would try, for him;
  •  what I won’t do.

Would the list be full of things that scared me? No!

There were no number 4s, and only two number 3s. Both of those were things that I didn’t know about and was worried that they would hurt, a fear  which tickles me now, when I am looking back to me then, seeing how much I have learnt and what I hunger for. The rest were either things I had done and loved, or things that played a part in my fantasies.

Initial signs on compatibility were positive.

The next day was another task, using my imagination this time. He asked me to share my fantasies with him. They tumbled out into my emails. I’m not sure if he got more than he was expecting, but he never once asked me to stop just make sure they were each sent individually so he could enjoy or study them separately. Once he was satisfied with my task for the day he informed me that I could continue to send them as I thought of them.

These tasks were just the beginning.

He was cataloguing me and my desires, learning about me in a wonderfully gentle way, teasing my inhibitions out of the way. I had never met him, and only had my instinct to go on, but I continued to put myself in a compromising position with him. Never once did I feel worried that he would abuse the trust I put in him, something I can’t explain, even now. An innate understanding that he was one of the good guys.

Things were going to step up a notch soon, he kept saying that he was demanding and would continue to push me, challenge me and watch me grow. What was he thinking up? I had no idea, but I had the strongest feeling that I would like it very much.

If It Doesn’t Challenge You It Doesn’t Change You was first published on A Leap of Faith.


  1. In a strange way, reading your post, it seems like this is the most natural pure way of being with and getting to know someone.

    An attentive man, who wants to know your likes, dislikes, desires and fears; one who hangs off your words, allows you to grow, and offers unconditional care and trust..

    I don’t know many people who don’t wish that for themselves.

    What a magical connection you both have.

    1. It is natural to me.
      I know that plenty of people would disagree with the way we met and evolved, but that is the joy of being individuals. We can each follow the path which is right for our own journey. ❤❤

  2. It sometimes strange that we might not be comfortable or trust people whom we have been with for ages and sometimes we trust blindly whom we don’t know.. it’s just the connection of the hearts?? Isn’t it.

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