Sunday, July 14, 2013

Sissy Offers Context For Cheerleader

 [NOTE - Anyone who is just beginning to read my blog, might want to read the following early entries in my blog about my sissy journey before reading this latest entry: A Little More Background - Am I Sure I Should Do This? - I'm Afraid - These - Where It All Started - Then, These - Miss Flo - Caught For The First Time - About My Last Post - Bikini Panties!!! - A Virgin Bride (And Groom) - Exhausted Sissy Needs Stress Relief! - Sissy Marries Cheerleader - Sissy Makes Life With Cheerleader - Cheerleader Discovers Sissy - Cheerleader Accepts Sissy - Cheerleader And Sissy Grow - Cheerleader Asserts Control - Cheerleader Teases Sissy - Cheerleader And Sissy Settle In To New Home - Cheerleader Cucks Sissy - Cheerleader and Sissy Are Mentored.  These are the previous posts that tell the story about my sissy journey.]
 I have been telling the story of my sissy journey for a little over a year now.  Recently, as I have moved closer to the present, I have been describing how my cheerleader and I reached the point where she cuckolded me.  Someone, who I always find to be very perceptive, recently raised a question that I think I should discuss, to offer some context and perspective on what my cheerleader and I were going through as events unfolded.  The question related to my friend wondering whether my cheerleader was the one who brought Andrea into the mix, so to speak, as perhaps my cheerleader's way of manipulating me into doing what I did for her.  And I want to be clear here, I did not take the observation by my dear friend in the wrong way.  It is a legitimate question from someone who does not know every intimate detail of my relationship with my cheerleader (although anyone reading my blog certainly knows more about some aspects of our relationship than many people who actually know us).  It is a question worth addressing.  
While I realize that it is often difficult to know with utter certainty what goes on inside of another human's mind, or even to be completely aware of what another is capable of doing, I am as certain as one can be that my cheerleader had nothing to do with bringing Andrea into our lives.  Although my cheerleader has proven over time to be more complex than I initially realized when we were first getting to know each other, on a particular, yet crucial, level, she is a very simple person.  She is a sweet, honest, and loving soul.  All who know her love her as she gives herself freely, always the one to do for others when doing needs doing, like, for example, in any crisis.  And she does care about her public perception.  And, despite her thorough enjoyment of sex, she is really what one thinks of as a "good girl." 
 Make no mistake about it, as things continued on and progressed in our sexual relationship after I revealed myself to be a man who loves wearing women's lingerie and acting feminine, my cheerleader became more and more engaged in the benefits that she was receiving as a result.  But, could she have moved forward to where we are now if she were going to have to be the moving force?  I'm fairly certain that she could not have.  As an example, the first night she cucked me (Cheerleader Cucks Sissy), while it is true that she told me she wanted to bring a man into our home, and while it is true that she fucked Randall that first night, it is also true that her initial plan included me sucking his cock for her, something she ultimately could not bring herself to asking me to do, not to mention that she wanted to be alone with him to fuck that first time.  In other words, my cheerleader wanted us to engage in a sharing sexual event (I don't think she even knew what cuckolding was when she did it the first time), but she was too shy to make it happen.  And so the first time ended as it did, with me feeling a bit on the outside, wondering how it was for her.  
If we had continued that way, and I fear we would have, who knows where we would be today.  I would have, because of my total love and devotion to her, wanted to do everything I could to give her what she wanted.  But, how long could I have continued if every time a man came over, I was shut out until he went home?  I don't know the answer to that question.  My intentions to please my cheerleader may have been strong, but that might have been tough.  And would my cheerleader ever have been able to get me on my knees in front of a man's cock, to suck him while she watched me, and then let me watch her experience the sensation of being filled with a big cock, if it were up to her to make it happen?  I am pretty sure she may never have been able to lead us to that. 
 The question remains as to how Andrea came to be a part of our lives.  And the actual answer to that question I do not know.  I do know that Randall brought her to us that second Friday night.  What I don't know is whether he hired her to perform the service she ultimately performed, leading us forward, or whether he simply asked a friend who he knew had the necessary skills to help us to do him (or us even?) a favor.  She seemed to take a special interest in my cheerleader and me, although that may be her special talent as a Domme.  And while it may seem as though, as I tell of her involvement in our life, she was focused upon me, there is no doubt that she was mentoring my cheerleader as well.  Looking back on the weeks Andrea was involved with us and Randall, I can truly say that she helped us stop thinking so much, and simply do.  And in the doing we became more comfortable and accepting of the roles we were creating for each other.  And what was Randall's motivation for bringing Andrea into our lives?  He certainly had a vested interest in the situation.  I mean, what man wouldn't want to be able to fuck a woman when he wanted to (almost), and add to the equation a sissy to suck him off and serve them?  Okay.  Maybe there are a lot of men who wouldn't get off on that.  But I can tell you Randall isn't one of them.  On the other hand, I don't think, looking back on it, that Randall's motivations were evil either.  He has always treated me kindly.  What I really think is that, after that first night didn't go as I suspect my cheerleader initially told him she planned for it to go, he realized that she might not be able to pull it off alone, and so he took unilateral action to help her along.  That's honestly what I think happened.  But I don't know, because Randall has never said, and I don't feel it is my place to ask.  What matters is that he did bring Andrea into our lives, and I'm grateful that he did so.  
 And so, as I move forward telling the rest of my sissy journey, I hope this provides some perspective to those following my story.  And recall that this is not a story solely about my cheerleader cuckolding me.  That is only part of the story, although the more recent part.  This story began with me revealing the recollections and memories I have of my earliest sissy urges, sensations that began when I was just a little boy.  (These - Where It All Started).  In everything that I have revealed I have attempted to describe things in as vivid of detail as possible.  I am committed to telling my story so that others will be able to compare their own memories and feelings to mine, and to hopefully connect with others who share my nature.  And, of course, I made a decision to tell my story, and I intend to finish it now.  I hope that, in the details, I will bring others as close as possible to understanding what I felt as events unfolded.  But I am acutely aware that I am telling the story from a point of view where the events have already happened.  I may have told it differently if I told it immediately as things developed.  I'm trying, though, to tell it as well as possible and I hope those following my story enjoy it, as well as appreciate it.

Sissy Kisses,



  1. This is really interesting, Leeanne.

  2. Leeanne you know I'm an avid reader of your story and I admit that the addition of Andrea was a bit of a twist I really didn't see coming but I also completely get it.
    You two were perched on the edge and without help you couldn't "fall" either way.
    You both wanted something but you needed something more to just get you over the top.
    Thanks for the update and ,,,,well you know....

    Love and sissy kisses

    1. Dear Kaaren,

      I often wonder where we would be had she not been brought to us by Randall.



  3. Thanks for more background, but I hope you did not write this because you felt we were owed an explanation. This is your experience, and we’re just happy that you are sharing it with us!

  4. I really like this mini editorial you've put in. The storytelling is fantastic, and pausing to consider a question directly fits in so well with your narrative. It just works. I can see where some might find the introduction of the mentor contrived - but depending on where you live, it can also be a pretty normal thing to know a pro-domme. Really enjoying reading & will save my other comments for when I'm finished.

  5. Most times there's too much thinking. And sometimes a push is needed to stop the thinking. I love that you had someone give you that push. Someone who knew what was needed.

    I am looking forward to reading more of your journey and am happy you are on it.