Sissy And Cheerleader's Last Weekend With Andrea - Part Two

[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.  These are the previous posts that tell the story about my sissy journey.]

I left off the telling of my sissy journey in the middle of what would turn out to be the last weekend my cheerleader and I would spend in the company of Andrea, the woman Randall had introduced into our lives when my cheerleader and I took the fateful first step toward realizing the fantasies I had introduced to our love life.  As I reflect back upon the many small moments that led us to this crucial moment, I am sometimes overwhelmed that so much has flowed from my decision to introduce my cheerleader to my inner sissy psyche that I had always been so afraid to reveal to anyone.  One of the reasons I decided to tell my story on this blog was because I wanted to document the steps and stages I (we really - because this chronicle is as much about my cheerleader as it is about me) went through that led us to where we are in our relationship today.  As I’ve done so, however, I’ve discovered a few things that I didn’t realize that I would discover.  One thing, and a very good thing, has been the outreach from those reading my self disclosure, both sissies and others interested enough in sissies and our clockwork to read my story.  I hope others are buoyed by what I have confessed publicly, albeit anonymously.  But the other thing I’ve discovered is how complicated it is to live a dual life as my cheerleader and I do.  For example, while she fully accepts me as the sissy I am now (as do I), we nonetheless keep that part of our relationship in what I would describe as a “close hold” manner.  Other people do know about us, obviously.  But no one we’ve known a long time or who we share all of our life with are aware of my femininity.  If it were not for our relocation from our home town several years ago, and the adult status of our children, I seriously doubt we would have reached this new freedom we allow each other.  Only those people my cheerleader chooses to know about us are allowed inside of our secret life.  And while we are creating new relationships that are, necessarily, close because of the sexual nature of them, they are strictly compartmentalized and we don’t share them with our “close” long-term relations, and vice versa, don’t share details of our “close” long-term relations with those my cheerleader chooses to know of my sissy side.  I wonder sometimes, as I write about this, what others think of me (us), and whether it seems a strange life my cheerleader and I are living together now.  But, as it is often said about things nowadays, it is what it is.  Perhaps I’m rambling a bit now.  Perhaps I should return to the details of the Sunday of the last weekend my cheerleader and I spent with Andrea.

I awoke in the guest room bed Sunday morning, alone.  Andrea was gone.  The sun was up and shining inside of the open window, so I realized it was fairly late in the morning.  I was exhausted when I fell asleep the night before, probably as much emotionally as physically.  I went to the bathroom to pee and to brush my teeth.  The door to my cheerleader’s and my room was still closed.  Noises were coming from our kitchen, so I assumed Andrea was downstairs.  I went down to find her.  She was wearing her nightgown, puttering around and preparing food for breakfast.  She smiled when she saw me and greeted me good morning, asking if I’d slept well.  I told her I had.  She poured me a cup of coffee and pointed to one of our barstools, indicating I should sit.  I remember thinking then how nice it was to not be the one who had to get up and become everyone else’s servant, as I had been expected to do during the other weekends that Randall and Andrea had been in our lives.  As it turns out, that was intentional on Andrea’s part.  Today was going to be a day of bringing things to a close, and a new beginning.  She was deliberate in her actions.

We chatted as she kept busy.  She filled a tray with pastries and bagels, coffee and  juice, and implements.  When the tray was complete she told me to take it up to my cheerleader and Randall.  As a last instruction, she told me to stop at the bathroom and wash my face and to put on lipstick, but nothing else.  Thus, as I delivered breakfast to my cheerleader and her man, I was wearing lipstick, a pink shortie nightgown, no bra (thus no breast forms), no panties and no wig.  In other words, I couldn’t have looked more sissy.  As I approached the closed door to our bedroom I could hear noises on the other side.  Noises that sounded like sex.  I was not sure what I should do, but did not think intruding was the correct move.  I stood outside of the door, holding the tray of breakfast, listening.  Intently.  There was no question about it.  My cheerleader was being fucked on the other side of the door.  While I did not think I should disturb them, I couldn’t seem to make myself leave either.  And so I stayed where I was, listening to my cheerleader as she received her last fuck of the weekend. 

 In moments like that, when you are waiting for something to end before you act, time seems to drag on forever.  I don’t remember how long I stood outside of our bedroom door before the noises ended.  Then, I waited longer before knocking as I felt I needed to give them time to settle after their sex.  Finally, I rapped softly on the door.  Randall called out, “Come in Sissy.”  He knew it would be me on the other side of the door.  To serve them.  I opened the door, not knowing precisely what I’d find, but nonetheless stunned to find what I found.  Randall was lying on his back, naked.  Sitting on him, cowgirl style, was my cheerleader, also naked, Randall’s cock obviously still inside of her.  Randall was looking right at me as I entered the room carrying their breakfast, looking like a total sissy cuck, and my cheerleader was looking over her shoulder at me smiling, clearly physically spent from sex.  “Good morning Sissy,” she greeted me cheerfully, but out of breath.  I was disoriented from the display, but quickly gained my wits and curtsied, responding, “Good morning.  I brought you breakfast.”  They thanked me and directed me to set the tray down on the bedside table.  As I prepared Randall his cup of black coffee, my eyes were locked on the junction of my cheerleader’s pussy still sitting on Randall’s cock.  There was moisture at the point of union as their mixture of juices leaked out of her.  I felt embarrassed to be looking at them in that way, but could not seem to avert my gaze.  I prepared my cheerleader’s coffee and was about to hand it to her when she moved to get off of her saddle, so to speak.  Thick strands of Randall’s cum stretched from her pussy to his softened, but still thick, cock.  She crawled up beside Randall and he scooched up to a sitting position so he could drink his coffee.  As I handed my cheerleader her coffee, Randall’s wet cock was lying across his thigh, leaking sperm.  I served them each a pastry, feeling utterly humiliated to be in the situation I found myself.  I hoped I could leave them, but when I asked if they needed anything else my cheerleader told me to clean Randall’s cock for her.  Our eyes met in that moment as I hesitated before complying.  I was truly confused at the shift my cheerleader had taken with me.  I had shared my deepest fantasies with her prior to us reaching this day.  And while quite a bit of water had gone over the dam over the past month, I still did not see this coming - where my cheerleader would seem so comfortable telling me to suck a real man’s cock.  Still, without another word being spoken, I leaned over Randall as my cheerleader lifted his cock with her hand and held it for me as I began licking, and sucking, him clean, the two of them watching me intently as I did so.  As I sucked him, he began to get hard again.  My cheerleader was encouraging me with whispers of, “Yes!  Yes!  Yes!”  She masturbated Randall into my mouth.  Randall began grunting in response to what we were doing to him and then the eruption came as he began spewing into my mouth, my cheerleader guiding him to me.  His cum began running out of my mouth and down his shaft onto my cheerleader’s hand that she was jacking him off with.  

When his orgasm finally ended, she held her hand up for me to clean the rest of his cum off of.  I looked at my cheerleader, as if for approval, or something, and she quietly said, “Now me.”  Without a word, I walked around to her side of the bed and leaned over her as she opened her thighs to give me access to her pussy.  Randall’s cream was leaking down her crack.  My cheerleader’s eyes were locked on me as she watched her sissy husband comply with her request - or demand - it did not matter - I was going to do what she asked.  I licked the first thick, wet taste of Randall’s ooze that was dripping out of my cheerleader.  She signed audibly in response, and I could feel her settle back upon her pillow to enjoy what I was doing to her.  More than anything else I do, when I am pleasing my cheerleader orally, I am committed to her pleasure.  I love her so much.  And I love tasting her, no matter whose cum may be inside of her.  I love doing what I did that morning for her.  As I was licking and sucking her, I suddenly felt a finger slide down her slit, inside of her.  It wasn’t my cheerleader’s finger.  It was Randall’s.  Randall began masturbating my cheerleader as I ate her pussy.  She responded with a series of convulsions as I, now aided by her man, brought her to a series of orgasms.  It was an incredible moment for us, both as a couple, but also for the three of us.  My cheerleader and Randall had their own thing going, but it was clear to me that they wanted me involved as well.  And while that was deeply embarrassing and humiliating on a certain level, it was also strangely reassuring to me.

My cheerleader thanked me and then dismissed me after I finished servicing her.  She and Randall, it seemed, were ready to enjoy their Sunday morning breakfast in bed.  Alone.  Without her sissy husband around.  I left them with a curtsy at the door and went downstairs to rejoin Andrea.  She was sitting on the sofa in our den reading the Washington Post, drinking coffee.  She looked up at me and smiled knowingly, and said, “You need to go fix your lipstick Sissy.”  Embarrassed at all that was conveyed by her statement, I curtsied and said, “Yes ma’am,” then went upstairs to get my lipstick.  When I went back down I poured myself a cup of coffee and got a pastry to eat and then joined Andrea in the den.  We sat together and each read the paper for a while.  After a while Randall came downstairs dressed and carrying his overnight case.  He was, apparently, leaving.  Andrea stood to hug him goodbye.  She looked at me and, without speaking a word, she willed me to stand up and curtsy for him as I said goodbye.  He smiled, but it was a smile that seemed to say, ‘You are such a wimp, but thanks for letting me fuck your wife.’  Instead, he said, “Goodbye Sissy.  Thank you for a nice weekend.  See you soon.”  I was so relieved that he was leaving.  I had grown to accept him in my life, but still felt so small and weak when he was around.  I did not think this then, but it turns out that being a sissy, it is natural for me to feel weak and small when I’m around my cheerleader’s men.  I mean, I should have known, and it kind of goes without saying.  You know?

Shortly after Randall left, my cheerleader came downstairs to join Andrea and me.  She was wearing a nightgown also.  So, here I was, alone with my cheerleader and our mentor, all of us dressed in sexy nylon nightgowns, spending a Sunday like it was the most normal thing in the world.  However, this was a planned moment.  Andrea had specific intentions for our afternoon together.  Apparently, my cheerleader had been clued in, to a certain extent, although not as to specifics.  It was then that we each learned that Andrea would not be joining us at our home for any further weekends.  Instead, she basically reviewed for us where we were in our relationship, quizzing each of us about how we felt about things.  In effect, we were having a counseling session with our sexual mentor, with her goal being to help us continue down the path we were on, but independently of her instruction.

I don’t know exactly how to relate the entire conversation that the three of us had that afternoon.  We talked for a few hours.  Andrea directed the conversation between a multitude of variations upon the general topic of me being a sissy cuckold and how each of us felt about the path we had gone down.  I can remember fairly vividly how uncomfortable I was in sharing my feelings about where my cheerleader and I had gone over the past month.  The thing that stuck out for me was the clear impression that my cheerleader was the most important voice, while I was the sissy - the one who was viewed as the submissive cog in the wheel.  That is true, of course.  And while my cheerleader does not treat me poorly in any way - the shift was noticeable in our respective standing vis a vis each other, especially in regard to our cuckold relationship.  Andrea led us through a review and rehash of the events that had led us to deciding to venture into real life experiencing of our fantasies.  My cheerleader shared how difficult it had been for her when she first learned of my feminine nature and my overwhelming need to wear women’s lingerie, especially when making love with her.  However, she explained, even when she was uncomfortable with what was happening between us, she knew deep inside that she was turned on by what was happening.  She also told how incredibly excited she became when she first watched me suck a cock and then swallow my own cum (See "Cheerleader Discovers Sissy") and then later when she had me clean my cum out of her pussy (See "Cheerleader Accepts Sissy").  The kicker for her though, was when I began injecting the fantasy of her being fucked by other men, even men we knew.  She said that she had begun privately fantasizing about being fucked by other men.  Men with bigger cocks.  Men who took her like a man - rather than as a sissy.  Men like, it turned out, her first husband.  She shared with us that he had taken her cherry when they were in high school.  Sex with him was always amazing she told us.  As she shared this news with me, for the first time, in front of Andrea, I was overcome with a deep sense of inadequacy.  When Andrea asked me to share how my cheerleader’s revelation made me feel, I admitted the same.  I was being confronted with my sissiness and being forced to put into words the emotions evoked by all that had gone on.  My cheerleader was clearly concerned about my reaction to her sharing her sexual relationship with her first husband.  She insisted that sex with me was wonderful and that she loved what we did together.  All that she was saying to me was that she had experienced great sex with a man who was blessed with a huge cock - had had babies with him - and always longed for that one thing that he gave to her.  On the other hand, she would not have traded me for him no matter what.  That’s why, she explained, my willingness to allow her to experience Randall meant so much to her, and why she was willing to let me experience my own fantasies coming true.

The conversation we had that day - the honesty with which we expressed ourselves - may never have occurred but for Andrea.  We had each come to trust her so much that we were able to talk about our sexual transition openly.  And while the discussion was filled with angst and was difficult, I believe it was crucial to where we are today, which I’ll tell more about in a later post.  Believe me though - we are nearly up to the present in terms of me telling about my sissy journey, although my cheerleader and I still had a ways to go after our last weekend with Andrea.

We ended our discussion late in the afternoon.  None of us had eaten for several hours and so we went into the kitchen to fix sandwiches.  It was interesting.  My cheerleader and Andrea, two very beautiful women, and me, a sissy cuck, all together in our kitchen wearing our sexy nightgowns and behaving in a completely non-sexual manner.  After lunch Andrea told us she was going to be leaving soon, but that there was one more thing she wanted to do with us.  She told us to come upstairs with her and she led us to our bedroom.  Andrea climbed onto our bed, beckoning my cheerleader and me to follow.  What happened - what they did - over the next hour or so - was one of the most humiliating things I’ve ever experienced.  It has happened more than once since then.  But when it happened for the first time, I felt more emasculated than I ever had, or ever have.

Sitting on our bed Indian style, Andrea spoke in a clinical tone about the weekend, discussing Friday night when my cheerleader threw herself at Randall in the den, followed by me cleaning each of them.  And then, reviewing every sexual event that had occurred over the weekend, she pointed out that throughout it all, I had been kept in chastity and had not experienced any relief.  She made me admit how painful it had been at times.  Then, she told us how important it was that my cheerleader keep me in chastity, with limited opportunities for release.  Instead, she explained, the goal was for my cheerleader to achieve her pleasure first, keeping me on edge most of the time because that would ensure my submission to my cheerleader.  I know now that Andrea was correct.  But hearing it then, I thought I was doomed.  I had already been fantasizing about being released at the conclusion of he weekend and even hoped that I would get to make love with my cheerleader.  Instead, I was being told that chastity was to become the norm for me.  Andrea also told us then that it was important that my cheerleader find another man besides Randall, and soon.  I couldn’t believe what I was hearing.  In no way could I have predicted that this would be the direction we were going.  Andrea’s reasoning was that sex with other men should remain simply that for my cheerleader, especially if she continued to love me as she said that she did.  Limiting sex to one man might lead to emotional attachment that could harm our marriage.  Andrea was speaking more toward my cheerleader when she explained this to us.  That makes sense to me now as well, since she is the one who decides who she fucks - not me.  

But this discussion was leading to something - the humiliation I spoke of.  My cheerleader was being told that I should remain in chastity, and that she would be permitted to find her sexual pleasure elsewhere, but that she needed to to know how to provide me some release between the opportunities when she would let me out of chastity.  While this was hard for me to hear, it turns out that it was difficult for my cheerleader to comprehend as well.  Andrea’s point, though, was that what she was about to show my cheerleader was for my own good.  It didn’t feel that way then.  And I’m still not sure I feel any differently, but it is the way it is.  I don’t know if anyone has guessed what Andrea showed my cheerleader that day, but it was milking.  Uh huh.  Andrea demonstrated the process of “milking a sissy” to my cheerleader.

Andrea directed me to position myself on my hands and knees, my butt up in the air.  She and my cheerleader moved to my rear and Andrea began the ordeal, explaining each step to my cheerleader as she progressed.  Andrea moved the butt plug inside of me and asked if I enjoyed having it there.  Strangely enough, I had grown accustomed to feeling it inside of me.  She pressed it in further, moving it around inside of me.  She reached between my thighs and gently grasped my shaved ball sack, massaging me carefully.  Then, she slowly removed the butt plug, but replaced it with something more slender.  As she slid the new object inside of me, I could feel that it was also longer than the butt plug I’d worn all weekend.  She moved it slowly in and out of me.  In other words, she was fucking me with the dildo.  As she massaged my balls and fucked my pussy, she explained to my cheerleader that this process, done correctly, would permit me to have a release, but without having a complete orgasm.  I was thankful that they could not see my face.  I was humiliated at being fondled in the way Andrea was doing.  As Andrea continued I could feel something building.  Then, almost without a warning, I felt the discharge.  I most definitely did not experience an orgasm.  But I most definitely came.  My cheerleader was mesmerized by what she’d witnessed.  And that’s when Andrea told her that she would need to do that to me from time to time.  She also told my cheerleader she was free to call her for continuing advice.  I was given no such opportunity.

After the milking Andrea told us she was going to go get dressed and then leave.  She left my cheerleader and me alone on our bed.  I could not look into my cheerleader’s eyes I felt so embarrassed about what had just happened to me.  She was obviously feeling funny about it as well.  “Are you alright?” she asked me.  Keeping my head down, I answered, “I suppose.”  “We don’t have to do this you know?” she spoke reassuringly.  The thought crossed my mind, although not for long.  No.  We couldn’t turn back now.  It would be like me taking something from my cheerleader.  I couldn’t do that to her - not then - and most assuredly not now.  “No,” I said.  “It’s okay.” 

In a few minutes Andrea came to our room, dressed and ready to leave.  She hugged and kissed each of us and told us how lucky we were to have each other.  We thanked her for all that she had done for us - and she had done a lot.  I still wonder where we’d be today had she not been there for us.  So, I suppose, I have Randall to thank for introducing us to Andrea.

My cheerleader and I ate leftover Chinese food for dinner.  We had worn our nightgowns all day.  Later, when we went to bed, my cheerleader asked me to pleasure her, but did not hint that she was going to unlock me.  I didn’t know whether she was responding to Andrea’s instructions, or whether she was acting on her own.  But either way, all I was going to get, it seemed, was the relief I received from being milked.  We cuddled after and I remember thinking how lucky I was to be touching my cheerleader again - to be in such an intimate position with her after the limited contact I’d had with her over the course of the weekend.  I was actually thankful to be snuggling with my cheerleader, rather than bemoaning not being released to make love to her.  

The following morning I awoke and dressed for work as I always did, but I knew that something was different.  My cheerleader had gotten a taste of something that she was going to want to keep tasting.  And I wasn’t going to stand in her way.  The next installment I write will describe how things progressed over the next few months, including how my cheerleader continued to follow Andrea’s advice that she find other men.  Until then, thanks for reading.

Big sissy kisses,

Leeanne