Sunday, October 20, 2013

Our Weekend Apart Aftermath - Cheerleader Has A Heart-To-Heart With Sissy

[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 - Sissy Offers Context For Cheerleader - Sissy Sees Her Future - Sissy Adapts To Chastity - Sissy And Cheerleader Spend A Weekend Apart.  These are the previous posts that tell the story about my sissy journey.]
The morning after my cheerleader returned from her weekend in Ft. Lauderdale alone with Randall, I woke up in a funk.  You might call it a ‘sissy funk.’  How do I even explain how it was that I felt?  As I’ve revealed throughout my journaling of my sissy progression, the things that were occurring in my cheerleader’s and my life really began with me confessing to her my deep, dark secret of having this feminine side of my personality.  She had not immediately embraced it, but because she loved me so much, she tolerated it and then began to slowly appear to accept me as I was.  Then, over time, after I further confessed my fantasy imagination, we actually took the step together that led us to where I found myself doubting how I felt about it all.  To put it simply, I was deeply confused about our current arrangement, and I wasn’t very good at concealing it from my cheerleader the Monday morning after her return home. 
On the other hand, my cheerleader woke up in the best of moods.  She seemed positively giddy to me, and I naturally attributed it to the fact that she was thoroughly enjoying her sexcapades with Randall.  As you might surmise, that did not help my funk.  In fact, it only made it worse and I became very pouty as I dressed for work.  To my cheerleader’s credit (and believe me, she sensed my funk), she didn’t press me on the way I was behaving.  But she continued acting as though she thought it was going to be a wonderful day.  She also selected lingerie for me to wear under my suit for the day.  Thus, she wasn’t showing signs of letting me back away from what she had now come to expect as normal for me.  Her selection was not elaborate.  She had laid out for me a pair of rather plain, white nylon bikini panties, a white slip, and an open bottom girdle with black nylon stockings to attach to the garters. 
As she had taken to doing, she lay on our bed and watched me as I dressed in front of her.  That’s when she did something that threw me for a bit of a loop and resulted in me saying something that I probably shouldn’t have said – at least if I had any intention of not letting her know what was eating at me.  I had pulled the panties up my legs and settled inside of them.  Then, I was about to shimmy the girdle on, when she asked me if I was forgetting something.  I honestly did not know what she was talking about and said so.  She held up the bejeweled butt plug Andrea had me wearing during my weekend with her.  I must have looked incredulously at my cheerleader, because that was precisely how I felt.  Surely she did not mean for me to wear it to work?  “You need to wear this,” she said.  I asked her why, and she replied, “Because we want you to.”  We.  She said, ‘We.’  “We?” I asked her, “We?  Who is ‘we?’”  She smiled at me and said, “All of us.  Andrea.  Randall.  Me.  We.”  My irritation and angst was not disguised as I responded, “Right!”  My cheerleader didn’t flinch though.  She simply said, “You don’t want to?  Okay.  No problem.  Go ahead and finish dressing.  I’ll go fix coffee.”   She climbed out of bed, still acting very upbeat and cheerful, and left me to finish dressing alone.
When I got downstairs, she was just as sweet as she could be, handed me a cup of coffee and kissed me sweetly on the lips, telling me I looked nice.  I gathered my things for work and then we kissed goodbye.  I was still in a funk and the butt plug moment had not helped me any.  I was totally confused about where my marital relationship with my cheerleader stood.  Worse still, I did not know how to address my feelings or to talk to her about them.
 Work that day was difficult.  I not only felt all funky about the underlying worry that began my day, but I also felt guilty for the way I’d behaved that morning with my cheerleader.  She seemed so happy (and I really did want her to be happy) and I’d ruined it by pouting and being a baby.  Still, I could not resolve in my mind what to do about my feelings.
I arrived home that evening, determined to put on a better face, and not to make my cheerleader feel badly for feeling so happy.  Apparently, though, she had been thinking about the morning confrontation as well.  She greeted me at the door with a kiss and a glass of Cabernet.  She took my hand and led my to the back patio where we liked to relax.  The evening was pleasant as the sun was making its way toward the horizon.  I sat down beside her, we clinked glasses, and she smiled so sweetly at me, asking about my day.  I wanted to do what I could to make her think things were fine, but as I’ve said, she knows me too well.  She knew I was not right, and she had no intention of letting it slide.  I shared a few details of things I’d done, but I could sense that she was simply letting me prattle on for a while before she focused the conversation upon us.
In the way only my cheerleader could do with me, she asked, “What is wrong sweetie?  I know there is something.  Tell me.  We have to discuss your feelings.”  I knew there was no way she was going to let this go.  On the other hand, I couldn’t find the words to say what was bothering me.  I was in conflict – a deep inner conflict.  But I did not know how to express those feelings to my cheerleader.  She was watching me struggle to respond to her question, and giving me time, but showing no sign of dropping the subject.  “I think you just need to spit it out.  We can talk about it.  Whatever it is,” she urged me.  Finally, I said the only thing I could think of – “I don’t want to lose you!”  There!  That was it!  I was worried that I was losing her to another man.  My cheerleader seemed so enthralled, happy, in love even, with Randall, that I feared I would lose her to him. 
Her reaction to my admission was perfect.  She set her glass of wine down, placed her hands on either side of my face, pulled me to her and kissed me.  Slowly at first.  Tenderly, lovingly and passionately.  Then she kissed me deeply for a long time until I surrendered to her.  Then, when she stopped kissing me, she whispered, “Honey - I love you.  More than anything or anyone.  Forever.  You never need to worry about losing me.  That isn’t going to happen.”  I felt a deep sense of relief, but still felt funny about things.  I answered in a weak, rather whiny voice, “But you seem so into Randall.”  She continued to smile sweetly at me as she began to explain her feelings for Randall.  This conversation may have been one of the most important conversations my cheerleader and I have ever had.
Telling me to listen, she began reviewing things with me, only asking me to affirm that she was correct in her recitation of events.  She basically took me back through our history.  She recounted how I first admitted my fetish to her and she first caught me on the Internet and all.  She explained how difficult that had been for her to accept.  She didn’t need to tell me that, but she seemed to want me to understand how close she’d come then to divorcing me.  Honestly, that revelation set me back.  I had known it was a shock to her, but I did not know my cheerleader had contemplated divorce.  Ultimately, though, she explained that she loved me too much to quit on us, and so she decided then to attempt to work through my revelation and her discovery.  As things moved on, she explained how she came to appreciate what I did for her.  She enjoyed the way I loved her sexually.  I wasn’t surprised when she admitted that, while she enjoyed normal man/woman sex with me, she really enjoyed what I did best, which was provide her oral pleasure.  
She also made her own confession of sorts.  During the time that I was revealing my fantasy of sucking cock, and actually sucking on the dildos in front of her, she was fantasizing about seeing me actually suck cocks.  She told me how hot it made her to see me with my mouth stuffed with cock, even though only rubber, and to hear me talk about sucking cock for her.  She also admitted that my suggestion that other men with bigger cocks fuck her was also an incredible turn on.  Finally, though, she told me that the moment for her that she would never have thought she would get turned on by was the night she jacked me off and watched me swallow my own cum.  She explained what an incredible power rush it was for her to watch my reaction as she sprayed cum into my mouth and onto my face.  I think I knew this already though.  Still, hearing her say so was a different thing entirely.  I sensed where she was heading.  I may have begun our fantasy world, but she was on board with it now.
I was listening closely to my cheerleader take me through the events we’d shared during our now long marriage – over 25 years by this point.  Step by step, she walked me through the stages we had gone through together.  I realized as she talked how true to me she had been.  Perhaps as important, I learned how she had grown as well.  A woman who always seemed such a ‘good girl’ to me (and who still was deep inside) discovered a part of herself that I actually helped blossom.  And so, we found ourselves in the middle of reality, rather than fantasy, and she was thoroughly enjoying herself.  She admitted that she did like the way Randall took her so aggressively.  She liked that she could openly come on to another man in front of me.  But even more, she loved that I would actually participate.  Watching me suck Randall’s cock and then clean his cum out of her was as much a part of the rush she got as him actually fucking her.  The thing she wanted me to face was that I was enjoying myself as well and that I should have no fear of losing her.  She stressed that she loved me no matter what else I might think and that I needed to continue to trust her with my heart.  As if to demonstrate her sincerity, she ended her narrative by saying that if I wanted to stop it all – Randall, Andrea, my sissy ways, everything – that she would honor my request.  But, and she emphasized this point, she didn’t want to stop.  She liked things as they were and wanted to see where things would lead.
 I was, needless to say, left with a huge decision to make.  I had begun this trail our marriage was on – not my cheerleader.  I could not dispute that.  I did enjoy the freedom to express my sissy nature in a more open way.  I could not dispute that either.  And while I was torn with conflict about seeing my cheerleader giving herself sexually so openly and with such vigor to a man, I also had to admit that it turned me on seeing her in that way.  The $60,000 question, though, was whether I could continue to bear it out.  I thanked my cheerleader for her honesty.  I told her how much I loved her.  Then, deciding two things really – one, that I wanted her to be happy, and two, that I wasn’t ready to give up living out my sissy fantasy yet, I told her I wanted to keep moving forward.  My cheerleader smiled lovingly at me and said, “You really are a sweet sissy.  You know that, don’t you?”  I must have blushed deep red hearing her call me a sissy in that way.  Years ago I would never have imagined my cheerleader referring to me as a sissy in such an accepting manner, as she seemed to at that point.  It felt so good to know. 
A huge cloud over our head now lifted, we kissed, and then sat back to enjoy the rest of the evening, sipping our wine until we finished the bottle.  We finally went inside to grab a quick snack for dinner and then went upstairs to bed.  That night I pleasured my cheerleader orally for easily over an hour, accepting that I was going to remain in chastity.  The next morning, after getting out of the shower, I went to my bedroom to find my cheerleader had already gone downstairs to prepare coffee.  On the bed was a set of lingerie for the day and the bejeweled butt plug.  I moistened it and slipped inside of me, knowing that while it may have been Andrea’s and Randall’s desire that I do so, what really mattered was that it was my cheerleader’s desire that I do so.  That was all that mattered to me.  All day at work the plug was a constant reminder of how much my cheerleader loved the sissy me.


  1. Replies
    1. Thank you Victoria. I really appreciate you taking time to let me know that you are enjoying my sissy journal.



    2. Of course I follow you sweetheart. You write from the depth of your heart and so much of what you shared here reminds me of what NB goes through.

      Kisses back!

      ~ Vista

    3. Leeanne, I am so happy to have found YOUR blog! As YOU know I have shared it with my MISTRESS M., who enjoys knowing more about me and what me ticks through YOUR writings. As a benefit to all this, SHE is now interested in my real journey as well.
      While it was difficult to out myself to HER in the very beginning, not wanting to pretend to be something I knew I was not, the fear I thought and felt about revealing so much of myself to HER at the very beginning of a possible relationship, how long I waited with my finger over the send button, rereading everything that I had wrote and told HER, wondering what would happen, if I would ever hear from HER again, would SHE out me to people that knew me, etc., the FEAR was overwhelming, but, I did finally hit the send button and then retired for the night questioning what I had just done.
      Sincerely, much to my surprise many hours later when I was able to check my email, seeing the mail from HER had me break out in a cold sweat for the fear of rejection and humiliation!
      BUT, that was not the case at all, MISTRESS M., appreciated the detailed information I had given HER about me and who I felt I was inside as well as to why I dressed and acted like I did at work and in public.
      Not only was SHE accepting, but, SHE was eager to move forward and allow HER DOMINANT PERSONALITY finally come out of HER and that SHE was ready for a Female Led Relationship, and knowing I was not only a sissy cross dresser wanting to come out more and more, I was also sincerely submissive, loved women and the female form, believed in Female Supremacy, was all the more reason for HER to take our beginning relationship to another level.
      YOUR writing and words are allowing HER to see inside of me and has now opened the door for HER to question me even more in an attempt to better understand me and my choices in life, and to hear about my coming to grips with who and what I am.
      Thank YOU again for YOUR Blog.
      It is a resource that so far has proven to be a GOD send in my trying to open up completely, without fear of rejection any longer, and has given me the ability to actually love another person again...unconditionally!

    4. Thanks Leeanne, it is a wonderfull story you're telling. I admire your strenght in this matter. Reading this I am nowhere near you in this journey. I just did my first steps on the path, staill wondering if I really would want to be a sissy. I know I am partially..thanks again for your story I loved reading it.

  2. incredible. keep blogging!

  3. Finding acceptance in another person is wonderful. Accepting yourself as you are is also wonderful. It sounds like you and your cheerleader have arrived at that magical place that so many couples look for and so many never find....past the rocky shoals to the beautiful lagoon just beyond.
    Thank you so much for sharing your life Leeanne.

    Sissy kisses to you both

  4. Leeanne,

    I've read along with your sissy journey for a long while now. At first I assumed this was a great form of fiction. A kind of 'what if my deepest darkest fantasies came true'. I mean that as a compliment as it's a wonderful engrossing story, and one that's normally not what I desire to read (I still prefer a more 'forced' adventure). But as you continued your story it rang more and more true. Your hesitation, your and your cheerleader's slow progression into acceptance... this all felt more real than fiction.

    But even as I grew to know you there was still a kernel of doubt in me. That this was almost too good to be true. Living our your desires and having your beloved cheerleader follow along seemed just a bit serendipitous. I don't mean this as a slight in any way. In fact I mean it as a compliment. You are a wonderful author and you tell any story so well. But this installment seemed to really encapsulate the 'truth' that is often lacking in even the best of stories. Doubt.

    At this point in most stories (especially ones that capture my attention) I'd almost expect you to fall completely in love with your new sissy life, or the opposite. That you would balk and your cheerleader would become a more dominating force in your progression. There's just something that rings so true that you doubted your cheerleader at this moment. You doubted that she was going to continue loving you. You doubted that her love was for you and thought that she may have instead loved her newfound freedom and man.

    I think even when our fantasies come true, we all naturally have a moment of fear. Fear that our fantasy won't come out as good as we dared hope. Fear that we'll come so far and yet end up so far away from what we wanted. Fear that reality will never match fantasy. I'm not sure I would have necessarily caught it if you hadn't had these feelings, but now that you've written about it, these doubts seem even more real that everything that's come before. And your cheerleaders reaction? Well my heart just melted a bit. She loves you. She enjoys what's happening and wants it to continue. But she'd give it up because she loves you. Wow. I can only dream that I'll find someone that loves me that much!

    Thank you again for this wonderful telling of your life!

  5. Dear Leeanne, I hope you know and realise how lucky you are. I call what you both have the connection between heart and mind. Sometimes reading the other as if seeing inside of the brain of your partner. I believe I do have achieved the same and that is why I couldn´t even imagine choosing the path you have chosen. It is wonderful to see how close you two are and I congratulate you both to have achieved a such high state of understanding. Well, I know my wife would have chosen the divorce path if I had come up with such "fantasies" and wishes. Sometimes it is incredible to see how much another person can change like you said your wife being the "good girl" and now has evolved into a cuckoldress and holding you in chastity at her will. Wonder if she takes to milking you in order to ease the pressure on those poor balls.
    love, Greta

  6. wow. you are so lucky. I am at a loss of words. I know it can be so nerve wracking this process of finally letting go and becoming who you really are. It's hard to let go of something that's been with you for so long...this old sort of you.....and now you have your wife....your cheerleader helping you along to becoming a full blown sissy. like a flower blooming. ..radiant. proud to be one especially in front of others and especially in front of your wife's bull ... and everybody in the room accepts that you can't compete with both have entirely two different roles and satisfy you wife's needs in two entirely separate ways......and everybody seems happy....perfect...purrfect

  7. Innovative blog. I love it........
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