Wednesday, January 11, 2017

Cheerleader and Sissy's Christmas Surprise

[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 - Cheerleader Learns  Juggling Isnt Easy - Cheerleader Gets An Itch - My Cheerleader's Summer of Contentment – My Cheerleader and Her Quarterback -  Cheerleader and Sissy Reach Accord (And Satisfaction) - Sissy Catches Up, Cheerleader Goes Sailing - Discovered! - It Was Bound To Happen Sooner Or Later - Quarterback Discovers Leeanne - I Have Good News. And News - Quarterback Is Visiting For Labor Day - Cheerleader Speaks - My New Sissy Life - Kittens Love Cream - Sissy Belongs to Cheerleader - Santa Claus Is Coming To Town - Bath Time - Christmas Shopping Visit SummaryThese are the previous posts that tell the story about my sissy journey.]
After his weeklong visit with us to Christmas shop, my cheerleader and I did not see quarterback until a chance encounter on Christmas Day.  We were visiting one of our sons (their son) and his family on Christmas morning.  Our son was making a big breakfast for family.  His in-laws and their family came by also, so the house was full.  Normally, we don’t cross paths with quarterback together on special occasions like Christmas, but on this day he got there before we had left to go off on the rest of our visits.  Was it awkward?  Well, yes.  And no.  Everyone else always gets a little edgy when he’s around us, but that is because they don’t know about our recent history.  They just assume that the ex-husband of my wife is not someone either she or I would want to be around.  But, like I said, they don’t know the recent history.  We engaged in polite Christmas morning banter and talked about football.  For a brief moment, though, quarterback and I were out of earshot of everyone enough for him to give me a knowing smile and whisper, “You have a surprise coming sissy.  Don’t let me down.”  I had no idea what he was talking about, obviously, but I answered, “I’ll try not to.”  His reply was blunt.  “Don’t.”
After my cheerleader and I left I told her what he’d said and asked if she knew what he was talking about.  She told me he’d said something similar to her – that he had a surprise for her – and that he thought she’d really like it.  But he didn’t elaborate with her either.  I was, admittedly, nervous by the way he put it to me.  ‘Don’t let him down.’  What could it be?
The day after we returned back to Washington after our Christmas visit with family, two large boxes were delivered by special delivery, along with an envelope addressed to my cheerleader and me, “M and Sissy – Read Together Before Opening Packages.”  My cheerleader had called me at work when the packages arrived and asked me to hurry home.  She was excited about opening the boxes and couldn’t do it without me.  I scrambled to wrap things up so I could leave work early and headed home.  When I arrived my cheerleader grabbed me and showed me what we’d received.  She told me to open the letter and read it out loud.  By this time, my anxiety was ratcheted up high.  This was the surprise, surely.  But what was it?  In a few moments, we found out.

I nervously opened the envelope and withdrew the typed note.  It read:

“Dear M and Sissy,

I thought long and hard about what to get you for Christmas.  Finally, an idea came to me.  I think both of you will enjoy it.  But I want you to think it over and be on board before you accept my gift.  If either of you are not willing to commit completely to my gift, then the plans will change.  I hope you both agree though, because I think you will like it.  When you open your boxes you will find, among other things, two round trip first class tickets to Mexico, where I have rented a private villa for a week in February.  I have made all of the arrangements and assure you that our privacy and secrets will be safe and secure while there.  What happens in Mexico stays in Mexico.  Ha!  All that the two of you need to do is get into the limo I will send to deliver you to the airport and commit to one thing - for the entire trip, I am in charge.  You will obey me.  Completely.  Sissy, if you can’t commit to that, I understand.  Don’t worry.  I bought trip insurance.  I won’t be mad or anything.  However, M is coming to Mexico with me no matter what you decide.  And I’m not sure we will be able to FaceTime from there.  Ha!  So, open your packages now and then think about my gift.  Talk about it together.  Then tell me your decision.  Don’t let me down.


There it was.  A trip to a private villa in Mexico.  All expenses paid.  For a week.  And he’d said it again.  ‘Don’t let me down.’  And only one caveat.  He was going to be in complete control, apparently, the way I read his note, of both of us.  Not just me.  I could see that my cheerleader was already excited.  She was talking about how nice it would be to get away for a week in a private villa in Mexico.  She didn’t seem to need to think about his condition.
The next thing to do was open the boxes.  The difference between the approach of my cheerleader and me was a stark contrast.  While I wanted to see what was in the box, I was motivated by trepidation.  Cheerleader, on the other hand, was like a child on Christmas morning.  She couldn’t wait to tear into her box.  Upon opening the boxes we each found a package wrapped in pretty pink paper and light blue ribbon.  The wrapping was professional quality.  Attached to the front of each package was an envelope with our names.  Well, her envelope had her name on it.  Mine read ‘Sissy.’  Inside of the envelopes was our round-trip first class tickets departing Dulles International Airport on the morning of February 18th and returning on February 24th.  One thing I will say about quarterback is that he doesn’t mind spending his money.  He is very wealthy, so it just seems easy for him to do so.  It never crossed my mind that his gift was too much.  My worry was the caveat.  Obey.  Completely.
After we confirmed that the envelopes held our tickets, cheerleader began tearing the wrapping from her package, and so I began opening mine too.  Once the paper was off and scattered on the floor, she opened her box and looked inside.  Her box held a shiny hot pink piece of carry-on luggage.  My box, as it turns out, also contained a piece of carry-on luggage.  Thankfully, mine was not shiny hot pink.  Mine was shiny blue.  Matching luggage.  As I pulled mine from the box I could tell it was not empty.  There was weight to it.  My cheerleader realized the same thing.  “There’s something in them,” she said.  “I know.”  “Let’s open them,” she told me as she laid hers on the top of our kitchen bar.  I did the same and began unzipping mine.  I’d be disingenuous if I told you that I didn’t already have an idea what our luggage contained.  But thinking and seeing are two different things.  Quarterback had gone to a lot of trouble to pack our luggage.  As it turns out, we found out later, he had his executive assistant (sworn to secrecy and paid well enough to ensure it) do his shopping to fill our luggage for him. 

My cheerleader’s luggage contained several skimpy swimsuits that took up hardly any space.  Also inside hers was an assortment of lingerie and, again, skimpy outfits, including skirts and shorts.  There were sandals and heels, a few negligees, and running shoes.  Sizes?  Everything fit her perfectly.  My cheerleader confessed to me that quarterback’s executive assistant had called her a week before asking about sizes for each of us.  While she had asked why, quarterback’s assistant rebuffed her and said it was for a Christmas gift, and revealed nothing more.
My luggage?  Well, let’s just say mine was obviously packed with a sissy in mind, and me especially.  There were a few pretty one-piece swimsuits, as well as a few bikinis.  Again, not much room taken up by the swimsuits.  My luggage was also stocked with pretty lingerie and a few other sexy outfits.  But mine also contained a very short pink frilly maid’s uniform, in addition to another butt plug like the one I already owned to which was attached a pink fluffy kitten tail.  My luggage also had running shoes in my size – pink – and  a few pairs of high heels – pink and black.  But the kicker for me was the pink wig with bangs.  I was like, ‘Oh fuck!’ and my cheerleader was like, “Oh sissy!  How cute!”
If the luggage and what it contained was any indication, quarterback’s plans for Mexico were well considered by him.  My cheerleader was so excited that she would have boarded the jet that day, I think.  But that wasn’t what quarterback wanted.  She called him then and thanked him for our gifts.  But he emphasized to her that he wanted us to think about it.  To talk about it.  And then to tell him our decision.  And that is what we have been doing for the past almost two weeks.  Thinking about it.  Talking about it.  My cheerleader told me this past weekend that we needed to make a decision this week.  I am pretty sure what she wants to do.  But, honestly?  I’ve been struggling with this.  I have no real idea of what to expect.  I only know the one thing.  If I go, I must obey.  Completely.  Am I worried about being seen by others?  Would he do that?  Reveal me to others?  I have no idea.  The only thing I know in that regard is that quarterback has assured us that our secret will be safe.  ‘What happens in Mexico stays in Mexico.’  But that isn’t the same thing as saying it will just be the three of us.  If I knew that, I’d say ‘Yes,’ for sure.  The other thing I know?  If I don’t go, they are.  I would be a wreck if they were away for a week and I wasn’t around to participate.  A fucking wreck!  Stay tuned people.  A decision is coming soon.


  1. Quite a dilemma Leeanne. Would Cheerleader really go without you ????
    If answer is yes, you MUST go !!
    If she ( in my view correctly) would do whatever you agreed to, answer may be different. Odd weekend fine. A whole week at his beck and call ?? more difficult.
    Good luck sweetie.

    Love Tanya xxxx

  2. Dearest Leeanne,
    I am happy for you and a bit sad.
    Happy in that you appear happy in how your life is progressing; you are growing into the full time sissy you feel you were meant to be.
    Sad because as many of your readers warned back when the QB and CL first started seeing each other you have been relegated to second fiddle. As much as your CL may protest, his comment "However, M is coming to Mexico with me no matter what you decide." indicates your new status in your relationship with your wife and partner. If your CL now writes that she did not appreciate his making such a decision for the two of you and refuses to go, I will obviously withdraw my observation.
    However, I think your CL and you have grown to be happy in this relationship with your QB. But for this reader, that change in dynamic is sad.
    Enjoy this next month as you iron out the traveling details. Enjoy skipping out of DC in the midst of February. At least he did not take Valentine's Day away from you.
    With kisses
    Billie Cee

    1. I have to agree with you Billie Cee. A weekend on Tom's boat is one thing - a whole week away in Mexico when he "demands" it is taking things a bit far in my view.
      Only CL can put limits on this relationship . Is she strong enough or does she have the inclination ????
      I doubt it.

      I feel sorry for Leeanne

      Love Tanya xxxx

  3. Sissy there are only a few words to say:

    Don't - think - just - do - it!!!

    You're really thinking about what the other people will think?

    That's not your part. You're a sissy. You're
    under control. You've to give joy and happiness
    to your cheerleader and your quarterback.

    The luagge is packed, the ticket is there. There's only one option for you.

    Be - a - good - sissy.

    Have fun, gain a new level. And no question!

    Lady Sonja

    There was no strap-on in the bag? Digg deeper sissy -:)

  4. baci baci baci !!

  5. Go!!! Have fun!!! What is the worst that could happen???? An ass-fucking or many ass-fuckings??? Just make sure you don't have sand in your crack..

  6. Wow. Talking about the horns of a dilemma. Kind of a “damned if you do” and “damned if you don’t” situation. Leeanne, we cannot tell you how to live your life. You’re the one who pays your bills, you’re the one to make the decisions. But, since you do share us about this relationship, we all feel slightly invested in it and don’t want to see you get hurt. So we do offer our observations.
    So, without further ado, my observations. First of all, you need to determine who the members are in your marriage. Right now, it appears from what you wrote, Tom is running the relationship if he is making the assumption, the statement, M will go to Mexico with him no matter what you decide and if that is true, if she will go along with him, you have been relegated to an outsider status in your own marriage. Basically, a toy for them to play with whenever they feel like using it but to be put up (sent to the guestroom) when they are done and ready to resume their “marriage” which, if you think about it, is what they are doing. Ask yourself, are Tom’s excursions (intrusions) into your life together becoming more frequent or more demanding? It seems they are at least more demanding and M is going along with it. No matter the relationship with other men, M is still your wife and decisions should be made together. Yes, I’ve been there. One of my wife’s men was doing a road trip sightseeing around our state along with a couple of spots in neighboring states. It would be a nine day trip starting Saturday morning, ending up the next Sunday evening and he wanted my wife to go with him (I wasn’t invited). I wasn’t crazy about the idea of her spending that many days and especially nights with him but I knew she wanted to go. We discussed it in depth because she would be using some of her vacation time, time that we would not get to spend together later in the summer. In the end, we both decided she could go but it was our decision. Even though Tom told you, “Talk about it together. Then tell me your decision,” he previously said, “However, M is coming to Mexico with me no matter what you decide. And I’m not sure we will be able to FaceTime from there. Ha!” I don’t care how you slice it, that sentence is blackmail and blackmail of the worst sort. It seems as if he is threatening your relationship with M to get you to comply with him. How would you react if Tom simply came out and told the two of you, “From now on M will spend three weeks out of the month living with me, one week living with you and she will do it!” There isn’t much difference from what he actually did.
    As I said, all we can do is share our observations, to pose questions. So the question is, if she will go no matter what, do you still truly have a marriage? I don’t know why, but this quote comes to mind.
    “To be or not to be, that is the question.” Are you still a member of this relationship or simply an afterthought?
    Is it nobler “to suffer The Slings and Arrows of outrageous Fortune, Or to take Arms against a Sea of troubles…:” Will you simply go along with whatever they desire or tell Tom we need to set some boundaries?
    Leeanne, the two of you are the ones who must decide. Personally, if I were in that situation I would have all three people sit down and discuss the situation. I’m not talking about let’s have a pleasant chat before Tom and M head off to the bedroom. I’m talking a serious discussion about the relationship and about limits before Tom gets up and goes home. A discussion between three consenting adults, not two lovers and their sissy.
    Just know that we, your readers realize sometimes it’s hard to see the forest for the trees, we are concerned about you and, as I said at the start, don’t want to see you hurt.

  7. Dear Leeanne,

    I cannot, nor will I, try to make your decision. What I meant by my last response, what happens in Mexico doesn't always stay in Mexico, is that what every we do we cannot erase. For instance, once a sissy sucks a cock the sissy will always be a cock sucker no matter where they are. Its all up to you and Cheerleader. Its all about trust and love.

    With respect and curtsy, fifi

  8. So, two slutty girls on the way to Mexico to please her man. That sounds damned good. Suck, Fuck, Fun. We're looking forward to your daily report sissy. Gain a further level in Mexico an make us proud of you sweety.

    With one eye on the calender

    Lady Sonja