Cheerleader Thanks 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, Our Weekend Apart Aftermath - Cheerleader Has A Heart-To-Heart With Sissy - Sissy And Cheerleader's Last Weekend With Andrea - Part One - Sissy And Cheerleader's Last Weekend With Andrea - Part Two.  These are the previous posts that tell the story about my sissy journey.]

The last weekend my cheerleader and I spent in the company of Andrea was, to put it mildly, a most significant event in our lives.  As those who have read my description of my sissy journey know, my cheerleader moved a great distance, physically and emotionally, to reach the point where she became, not merely comfortable, but intrigued with cuckolding me.  Likewise, I travelled a pretty good distance myself, from my private fantasy world to confessing my fantasies to my cheerleader to living my fantasies in a way that far exceeded my imagination.  Describing the details of the month we spent in the company of Randall and Andrea was emotionally exhausting for me also.  There were moments when I wondered if I had erred in airing my personal story.  I still wonder some.  When I rethink of what I went through during that month a little over a year ago, I still feel as embarrassed and humiliated as I did as events transpired.  However, despite some of the difficult times I’ve had to navigate, I’m glad that my cheerleader and I took the road we did.

On the Monday following that last weekend with Andrea my cheerleader was waiting for me in our kitchen when I arrived home from work.  She was cooking dinner.  A chilled bottle of white wine was sitting on our bar.  My cheerleader was wearing a very sexy, short, low-cut dress that displayed her boobs and legs prominently.  My first thought was that she had invited Randall to dinner, and my psyche took a brief nosedive, as I didn’t know if I was prepared for that after the weekend we’d just spent.  Thankfully, she did not make me wait long to find out that she was dressed, not for her man, but for me.  She came to me and greeted me with a soft, sensuous kiss, letting her hand roam to my panty-clad butt as she did.  I was equally thrown off kilter by what she did as I was initially at what she wasn’t doing.  But pleasantly so.  I asked, “What is the occasion?”  She smiled sweetly and answered, “The occasion is you.  I want to thank you for what you’ve done for me.”  She kissed me again and told me to go upstairs and shower and change.  As I left the kitchen she said, “I’ve left something out for you on our bed.”

I had spent a lot of time during the day at work reflecting upon the current state of affairs in my marriage to my cheerleader.  Everything seemed to have moved so quickly to where we were.  And to be honest, despite her reassurances to the contrary, I was worried that my cheerleader, now that she’d had her taste (again) of a large cock, might drift from me.  I would have been devastated and lost had that turned out to be true.  What happened when I arrived home that evening was a truly important thing for my sissy psyche.  Lying on our bed was a sexy ensemble that any sissy would have died for her wife to give her.  For me it signaled, not only that my cheerleader was still committed to our marriage, but that she was embracing my sissy nature within our home.  Understand that, pre-Randall and Andrea, my cheerleader had permitted me a lot of freedom to express my feminine nature.  But this indicated to me that she was ready to let me take it further.

I was so excited about where this evening might go.  My penis reacted accordingly within its cage.  I even began hoping that my cheerleader might be planning release for me before the night ended.  I quickly showered, taking time to shave my legs and underarms.  The outfit my cheerleader had waiting for me on our bed screamed out for a smooth sissy body.  After I dried off I quickly went to work dressing in the lovely clothing my cheerleader chose for me to wear.  I knew as I dressed what a stark contrast my outfit would be to what my cheerleader was wearing.  While she was dressed sexily, she wore clothes she could wear in public.  When I was dressed, the only place appropriate for me to be seen would be the privacy of my own home, and most especially the bedroom.  A matching set of pink lingerie – bra, garter belt and panties, with frilly lacy edging – and black stockings was the base layer.  Over that was a frilly white babydoll and matching robe.  The outfit was completed with the pink paten leather high heels Andrea had bought for me.  My cheerleader had even left out my breast forms and pageboy wig for me to wear.  The importance of that was the clear message that she was willing to let me be ultra feminine in her presence, and for her, since we were alone.  I applied light makeup – mascara, some blush and red lipstick, and then feeling full of butterflies, walked downstairs to greet my cheerleader again, but now as her sissy husband.

When I walked into the kitchen, she turned from the stove and audibly gasped, clearly taken at my appearance despite her complicity.  I smiled nervously, and anxiously, waiting for her reaction.  She came to me and pulled me closer and then kissed me softly on my lips.  “You know Sissy, you actually are glowing right now.  I’m so glad you are happy to have been set free.”  I cocked my head in wonder at how she’d put it.  “You know – you gave me my freedom Sissy.  I’m just saying that I’m glad you are getting something out of this as well.  And tonight I hope to show you how appreciative I am.  Now, pour us some wine while I finish dinner.”

And so began a pretty amazing evening.  We ate dinner in our dining room where she had set a beautiful table for us.  Our different attire, her dressed in regular clothes, and me in lingerie, set a tone that she was the superior.  Whether that was intentional on her part, I don’t know.  But it is how I felt sitting beside her in my frilly, sexy lingerie.  During dinner my cheerleader talked about her feelings for me, and how she could not have imagined that she could love me more than she did, but that my permitting her to experience sex in a new way was a gift beyond what she would ever have imagined for herself.  I felt a deep sense of relief to hear her express her appreciation, so much so that I was not concerned by the underlying message being conveyed – namely, that she expected things to continue as they were.  I knew, intuitively, that I would be hard pressed to roll things back after what had occurred thus far, but my cheerleader sharing how much it meant to her made it abundantly clear to me that other men would be part of our lives in the future, even though she did not specifically say so then. 

After dinner we retired to our den and sat closely together on our sofa, my cheerleader taking very much the dominant role in our physical touching.  She gently stroked me and kissed me on my neck and ears.  Her fingers even toyed with my encased penis, giving me further hope that I might be released before the night ended.  After some very satisfying petting, my cheerleader hinted that she would like me to pleasure her orally, and so I moved from the sofa to the floor, onto my knees between my cheerleader’s thighs, and began to do what I know I do best.  For a long time.  For a long, long time.  Initially, I kissed her inner thighs softly everywhere, teasing her as I moved close to her panty-covered pussy, planting soft, butterfly kisses and breathing gently on her as I did so.  Her body confessed her enjoyment to me, providing unnecessary encouragement for me to continue.  When I finally began to give attention to her wet pussy, I began outside of her panties, sucking her nylon gusset into my mouth, savoring her aroma and unique flavor.  She seemed perfectly content to permit me to take my sweet time, sighing as I worshipped her, which is really what I do.  I am so committed to her and to her pleasure that it is perfectly logical to me that I had so willingly permitted her the pleasure of a man to satisfy her sexually.  I believe I understood that better than my cheerleader did, although I suspected that she was beginning to see the light.

Eventually, she told me to remove her panties.  She wanted to feel me on her pussy.  She was so wet and her pussy lips were so engorged from excitement.  I know others reading this understand when I say that, to me, nothing is as satisfying as my mouth and tongue in contact with my cheerleader’s most intimate place.  Hours.  I can literally pleasure her in that way for hours.  As I continued my oral worship of my cheerleader, she would interject from time to time, saying how much she enjoyed the way that I loved her, telling me how much she loved me.  But she also made references to the past few weeks of our life.  She told me how much she loved seeing me with a cock in my mouth – how hot it made her knowing that I would do that for her – even taking a man’s cum.  She talked about how great if felt to be filled with such a huge cock – one that filled her with sperm.  She thanked me for giving that to her.  She loved me, but she had missed being filled with a big cock for so long and that a real one was so much better than a fake one, no doubt referring to the large dildos I’d introduced to our lovemaking long ago.  And I thought I had shown her something she was not familiar with.  Instead, I’d unwittingly rekindled her memory of what being filled in that way felt like.  Throughout my submission to my cheerleader that night, she sought my agreement with what she was saying.  Of course, I did agree with her.  I was even turned on hearing her verbalize her feelings as she was.  I found that I was excited to know that she considered me such an integral part of her discovery about herself.  Not that I needed any added incentive, but it made me want to please her all the more. 

My cheerleader had been holding my head gently from behind, subtly guiding me along, sometimes giving me my lead, other times directing me to a particular spot, constantly encouraging me.  At one point she said to me, “I love you Sissy.”  Hearing her call me that in this setting was a little disconcerting.  She had clearly come a long way in her acceptance of my feminine nature.  I realize that I paused when she said it too.  She picked up on my hesitation and said, “You are my sweet sissy, aren’t you?”   She wanted an answer.  Looking up I saw her looking at me with expectant eyes.  I replied, “Yes.  I am.”  It was a moment for us.  It was as though we had each processed everything that had preceded it in time – my confessions to her so many years before – her slow acceptance of my feminine feelings – our fantasy play in bed – the past month – and then, now, the question and the answer.  We were in agreement – I was her sissy.  And I am.  And I continue to be.  I hope I always remain so, for I don’t know how I would live any other way now.  I love my cheerleader so much.  And she loves me too.

That night, when we went to bed, I was truly hopeful that she was going to release me and let me make love to her.  In bed I tried to initiate things.  Sensing my desire she stopped me and said, “I’m sorry baby.  Not tonight.  Maybe soon.  But not tonight.  What we did was nice.  But I can’t let you out yet.  Too soon.”  I was crestfallen.  My hopes had been really high that we might.  “I’ll clean you out after,” I told her, hoping that might move her off her decision.  I know that amounted to begging, but she was unmoved.  “I know you will sweetie.  But not yet.  I’ll let you know.”  Thus was the beginning of my understanding of what it meant to be maintained in chastity by a woman.  Andrea had to have been coaching my cheerleader, for I could not imagine her being so keyed in to such matters.  But she began proving that I had underestimated her on many counts as we moved forward. 

What was the lesson of this night?  My cheerleader loved me.  I was her sissy husband.  Her sissy cuckold husband.  I was not going to lose her.  In the next installment of my journal I will discuss how my cheerleader (and me following along) branched out beyond Randall, just as Andrea recommended.

Postscript – As I read the title to this installment in my revelation of my sissy journey, and then reread the installment, it occurred to me that some readers may wonder, what did I get out of the evening.  My cheerleader received my undivided attention and enjoyed several orgasms.  I, on the other hand, was denied and even told that my sentence to chastity confinement would continue until an undetermined time.  How was I thanked for my gift of sex with a man to my cheerleader?  The gift I received was my cheerleader letting me know that I was still loved and still appreciated.  Isn’t that gift enough?