Cheerleader Learns – Juggling Isn’t Easy

[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 - Cheerleader Thanks Sissy - Cheerleader Does A Sleepover - How My Cheerleader Vets Men - Cheerleader Flirts - With Purpose - Cheerleader Is A Happy Girl. These are the previous posts that tell the story about my sissy journey.]

Initially, after her hookup with Jason, my cheerleader seemed energized by the existence of two men who were eager to fuck her whenever possible.  Although we did not entertain both Randall and Jason every weekend, as each of them were not always available, especially Jason due to his job, there were several weekends over the first few months of 2013 that Randall and Jason each spent at least one night with my cheerleader.  What that meant for me varied.  Although I always presented myself to her men as her sissy husband, I was not always involved in their lovemaking.  Sometimes, it seemed, my cheerleader simply wanted her men to herself, without having me present.  Both men, however, accepted me without reservation.  I provided service to them, not only at my cheerleader’s direction, but upon their request.  If they wanted a drink of some kind, they simply asked me to get them something.  Jason, of course, was the epitome of politeness to me. 

Between visits from my cheerleader’s men our life together was wonderful.  By this point, when we were home alone, I was as openly feminine as I wanted to be, which was much of the time.  Of course, there were times when we did things with friends who knew nothing about me, or our lifestyle.  With those friends, we behaved as any other married couple would behave, and no one would have possibly guessed that I was a sissy.  But no matter how I appeared to the world, my cheerleader treated me sweetly and tenderly, appealing to my soft and submissive nature.  We talked about how difficult it was, at times, having no free time together on the weekends when both Randall and Jason visited.  Once, my cheerleader even mentioned that she wondered what she’d do if she ever met another man.  I remember feeling anxiety as I thought of what a third man would mean to me – or her.  Could my cheerleader really take on a third lover?  I didn’t see how.  I had read that some wives, once they cuckolded their husbands, would begin doing it more and more frequently and with a variety of partners.  But I could not see my cheerleader doing that.  I was very comfortable that she loved me – not Randall or Jason.  But I also was well aware that she was fond of them, and that she likely would not be able to so easily share the intimacies she did with them if she did not harbor special feelings for them.  I often wondered what would happen if I were not in the picture.  I could see her in a relationship with Jason, and vice versa, although not with Randall.  Randall was almost pure sex to her, it seemed to me. 

My cheerleader never shared with either Randall or Jason the existence of the other.  Keeping both balls in the air, so to speak, was not always easy, although we managed.  Then, in late March of 2013, the problem of juggling two men resolved itself for my cheerleader, while also leaving a void.  Randall received a management promotion with the retail store chain where my cheerleader and he worked.  Unfortunately, for them anyway, the promotion required him to relocate to another area of the United States that did not lend itself to weekend visits.  He spent the last weekend before he moved away, with us.  My cheerleader managed to put off Jason, who also tried to arrange a visit that weekend.  She told him that we had plans together that she couldn’t change.  Instead, he stopped by our house after work late on the Thursday night before Randall’s last weekend, resulting in us entertaining my cheerleader’s men three consecutive nights, the first time that had occurred.  I handled it okay, I think.  However, it was very difficult for me.  It struck me then how much I depended upon the closeness my cheerleader and I shared during the week, when it was just the two of us.  I found myself thinking how much I was going to enjoy not having Randall in the picture anymore.

During her last weekend with Randall, my cheerleader was intent upon satisfying him in every way and giving herself to him completely as a parting gift.  I, on the other hand, was in a completely subservient role to them.  My cheerleader had made it clear to me that she wanted Randall’s last weekend with her to be special, so I was as prepared as I could be for what took place.  However, being prepared for what happened that weekend, and being comfortable with everything, were two different things.

I spent nearly the entire weekend in chastity and dressed as a sissy maid.  My cheerleader spent most of the weekend either scantily clad, in a nightgown, or nude.  She was all over Randall from the moment he walked in our door.  She fucked him in our den within minutes of him arriving, throwing herself at him in a most wanton manner.  Of course, that meant that I was on my knees cleaning each of them afterward.  Randall, being the man he was, accepted my cheerleader’s offering of herself to him without any qualms.  The entire weekend was devoted to my cheerleader getting as much of Randall as possible or, it might be said, giving as much of herself to him as she could.  I was even drawn in a few times to suck his cock for her – once to fluff him for her, and a second time so she could watch him cum in my mouth "one last time."

The weekend felt odd because it truly was a kind of “going away” gift to Randall.  However, it also felt as though my cheerleader wanted to let him go, and simply wanted to get all that she could from him before it was over.  I never considered that they might get together again, although she does mention him from time to time in a tone that makes me think she would readily reunite with him if circumstances permitted.

On our final day, the three of us went out for brunch.  It felt a bit odd to me, but my cheerleader wanted to do it.  I wore lingerie beneath my male clothing and she dressed in a very pretty blue dress.  The three of us had a very nice meal together, talking openly about the relationship we had shared.  My cheerleader thanked Randall for helping us along, referring to my cucking and bringing out my sissy nature.  Randall was actually very gracious and complimented us on our marriage.  When we returned to our home that afternoon, my cheerleader led both of us upstairs to our bedroom.  As we had done so many months before, the second time she fucked Randall (Cheerleader And Sissy Are Mentored), when I fluffed a man for her for the first time, I undressed down to my lingerie, and then undressed each of them in turn, repeating the ritual where I blessed my cheerleader having sex with another man.  I sucked Randall’s cock for my cheerleader, getting him hard and ready to fuck her one last time before he moved from town.  After I made him hard, and upon my cheerleader’s urging, I once again directed Randall’s cock inside of her wet pussy, and stood by our bed watching as he slid inside of her, spreading her opening wider than I could dream of doing, and began fucking my cheerleader with an urgency and a vengeance that revealed how much it meant to him that he was allowed the privilege of having her.  My own penis was straining against the restrictive prison that was my chastity cage.  I know that, had I been free, I would have cum watching Randall please my cheerleader.  When he finally came, over and over and over, my cheerleader held him tightly against her, her legs wrapped firmly around his waist, as if she did not want to let him go.  But finally, eventually, she did.  And when he slipped out, she told me to clean him off one last time.  And I did.  And then he got dressed and left, kissing her goodbye and thanking me again.  When Randall was gone I asked my cheerleader if she was okay.  Her response was interesting.  “Yes.  I’m okay.  I’ll miss him.  But there are other men.  We’ll be fine.”  In losing Randall my cheerleader saw opportunity – opportunity for another man to take his place.  She beckoned me onto the bed and positioned me on my back.  Then, crawling on top of me she straddled my face and settled her pussy down onto my mouth and began riding me – gently at first as Randall’s cum drained from her pussy into my mouth – but then more aggressively – until she was nearly fucking my face – calling me her sissy and telling me how much she loved me.

After I had brought her to several orgasms, she finally stopped and rolled off of me, holding me in her arms.  We kissed and snuggled until we decided to get up and go out to dinner.  We had a nice dinner conversation, talking about our time with Randall.  It was as though we had closed a chapter in a book.  A chapter we would not soon forget, and a very good chapter at that.  But it was done.  And we were moving forward.  More in love, if that was possible, than ever.

The following weekend Jason came over on Saturday afternoon, as he often did, and we had a very comfortable weekend together.  The strain of entertaining two men was gone.  My cheerleader and I discussed it afterward.  I think it was only then that each of us realized how difficult it had been to deal with keeping Randall and Jason secret one from the other.  I think my cheerleader decided then, that if there ever were another man, she would not try to keep it a secret from the men.  And guess what?  There have been other men.