Sissy Catches Up, Cheerleader Goes Sailing

[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 Isn’t Easy - Cheerleader Gets An Itch - My Cheerleader's Summer of Contentment – My Cheerleader and Her Quarterback -  Cheerleader and Sissy Reach Accord (And Satisfaction). These are the previous posts that tell the story about my sissy journey.]  

My last post sharing my personal sissy journey was on September 28, 2014, Cheerleader and Sissy Reach Accord (And Satisfaction).  There is really only one word to describe my deleteriousness – lame.  Bad Sissy!  So, before I go any further, I’m giving myself a virtual spanking.

Okay!  Now that I’ve been appropriately punished for leaving my personal story untold for so long, let’s get down to business.  I may have last written in September 2014, but my story has been untold going back to January of 2014.  Over a year ago!  Obviously, my life has been moving on, as have the lives of others about whom I have written as part of my story.  Equally obviously, I have continued to post sissy captions on my blog.  Finally, also quite obviously, I am still a sissy.  And, as you might suspect, my cheerleader is still cuckolding me.  Honestly, I doubt that will ever change.  She enjoys her sexual freedom too much to ever give it up now.  Our life is, dare I say it - better than ever?  Sometimes I ask myself what I have done to deserve such good fortune to be married to a woman who has permitted me to experience and live out my sissy nature in such a loving and supportive atmosphere.  I’m very lucky indeed.  And, thankfully, my cheerleader feels the same way.

So, where are we?  Well, I’ll bring you up to date in a bit of a summary fashion and then move on to some events that have occurred that I’ll eventually describe in more detail.  First, and likely foremost in the minds of many of my readers, my cheerleader is still seeing her quarterback - her ex-husband, Tom.  We’ve worked it out pretty well between us.  The more she continued to see him, the more she realized the need he filled for her - no pun intended.  It’s complicated, in a very basic sort of way, but I’ll discuss that more later.  Second, Jason has sort of moved on.  Why “sort of?"  Readers may recall that Jason was the chief of staff for a United States Senator.  For a refresher on how my cheerleader met Jason, re-read Cheerleader Flirts - With Purpose.  Guess what?  His Senator lost in the mid-terms.  So, Jason returned to his home state to take a job with a big law firm there.  There was a nice send-off weekend for him here at our house before he left to take on his new job.  And while he isn’t a regular weekend visitor anymore, he does still have business here in D.C., so he has maintained a relationship with my cheerleader that permits him to visit when he is in town, if there are no conflicts on her schedule.  Dave still sees my cheerleader.  And there is another man (Kurt) who she met at one of our neighborhood parties who has been (how should I put this?) put into the rotation.  I'll write more about the night she met Kurt later.  This entry in my sissy journey is about catching everyone up on what has happened over the past year and a half.  So, that’s just about it.  Bye bye.  Hahahahaha!  Aren’t I funny?  Just kidding.  I’m going to give you more detail than that.  The question is, where shall I begin?  How about I begin in the present?  Sound like an interesting twist?  Okay.

I may have mentioned in a previous post that my cheerleader's mother passed away a while back.  Her elderly father had been living alone since her mother passed away, and my cheerleader visited him fairly often.  It wasn’t always easy for me to get away from work early enough on Friday to go with her, so she sometimes made the trips alone.  Of course, there was another reason she had taken to visiting our hometown alone.  Once she and I sorted out her relationship with her quarterback, she would usually spend at least one night during each of her visits to her father with her quarterback.  I think what she liked about it (and probably him as well) is that they could relax openly together in the privacy of his apartment, or sometimes on his yacht.  Now please, before everyone who is concerned about me submitting to my cheerleader’s desire to be with her quarterback goes crazy on me, let me tell you that I have completely accepted this arrangement.  My cheerleader and I continue to agree that revealing the truth about me and my sissy nature to her quarterback is not a good idea.  She does like to tease me about him, and has done so more frequently as time has gone on.  And, while I am often embarrassed by her teasing, the basic conflict inherent in a sissy’s nature is that we are embarrassed by our nature and thrive on being teased about it in equal measures.  It is rather unexplainable, although I hate the phrase, "It is what it is," so I will refrain from using that as my explanation.

Well, her travel to our hometown has changed recently as my cheerleader's father passed away about a month ago.  In fact, she's back at our hometown now helping her brother clean out his house in preparation for sale.  And, of course, while there, she is staying with her quarterback.  More about that in a separate post too.

Going back to January 2014, and moving forward, there have been a few significant events in my sissy journey that I want to share.  Our life was fairly uneventful for the rest of the winter of 2014.  I worked and my cheerleader continued working at her retail job.  She continued seeing Jason and/or Dave on most weekends, including me some in their activities, as I had grown accustomed to doing.  Things were good.  My cheerleader’s quarterback visited D.C. at least once a month for business.  I am confident that he would have visited more often if my cheerleader had not resisted him.  And I know why she resisted him.  She continued to feel bad about what happened over Christmas 2013.  She was showing restraint for me.  I was agreeing to let her see her quarterback.  And while she may have wanted to see him more frequently, she exercised restraint for me.  I realized what she was doing as well, so I was very appreciative of her consideration.  Plus, as I've mentioned, she saw him on her occasional visits to our hometown also.  So, all in all, she saw her quarterback on a fairly regular basis.

The next event that I want to tell you about happened in July 2014.  Before I tell about it though, I’m going to beat a dead horse.  I’m going to deviate from telling my story to comment on this fiction my cheerleader and I have created with her quarterback.  He thinks he is cheating with her on me.  She pretends like she is cheating on me to him.  So there is this entire dishonest string that threads its way through their relationship.  My cheerleader justifies all of this because she knows she isn’t really cheating at all (because I know what she is doing), and that it doesn’t matter to her what her quarterback thinks.  In her mind, he cheated on her a long time ago, so he’s already proven he is a cheater, so any deception he suffers from her is just too bad for him as far as my cheerleader is concerned.  I accept her logic.  What matters to her, and ultimately to me, is that there is no real cheating going on – what is going on is that we are protecting our secret - about me.  I know there are bound to be readers who find our reasoning to be full of holes, but there it is.  It works for us and, really, we are very decent and honorable people.

I think I’ve mentioned that my cheerleader’s quarterback is a very successful businessman.  Very successful.  He is a real estate developer and has done very, very well.  He owns a magnificent fifty-foot Targa yacht.  Look them up online.  They are pretty amazing.  One Tuesday night in July 2014, after I arrived home from work, my cheerleader and I were enjoying a cocktail on our screened porch when she told me her quarterback had called her that day to let her know he was going to be in D.C. for a business meeting on the following Thursday.  That wasn’t so unusual, as far as things had been going.  It had been a few weeks since they’d been with each other.  I replied that was fine with me.  I had adjusted to their routine.  She’d meet him at his hotel, they’d do whatever they did, and I’d see her the next evening.  That’s when she gave me her look – the look that I have learned meant there was more.  “What?” I asked her.  She gave me a sheepish grin and told me that he was coming up in his yacht and was going to be docking in Annapolis, Maryland, which is about an hour from where we live.  He invited her to spend the weekend with him on his yacht following his business meeting.  My cheerleader had told him she’d have to check with me to see what my plans were, and try to figure out whether she could manage it without me “suspecting anything.”  Did I have the ability to stop her?  I’d say that I did, but you’ll see that I don’t deny my cheerleader anything.  When she told me she wanted to do it – to spend an entire weekend alone with her quarterback on his yacht, I was immediately apprehensive and yet, I did consent.  My consent would turn out to be a decision I regretted as things turned out.  We agreed that I would “have to go out of town this weekend” so she’d be free to go off with him.

The next night my cheerleader asked me to help her prepare for her weekend trip.  She was trying to act calm about it, but I could sense that she was very excited to be going off with her quarterback on his yacht.  She had me shave her pussy for her.  Her quarterback, it turns out, loves her pussy to be shaved smooth, something she'd never done during their marriage.  I also gave her a pedicure and a manicure – bright red.  I pulled out her overnight bag and asked what she wanted to pack for the weekend.  That’s when she told me what began to make me worry for the entire weekend.  Her quarterback had told her she wouldn’t need much.  She would only need a dress for dinner in D.C. and some shorts and a shirt for Annapolis on Sunday.  Otherwise, they’d be on the yacht where, as he had told her, “clothing was optional.”  I was shocked.  I mean, I know it sounds stupid.  I’ve consented to my wife spending the weekend with her ex-husband and yet, I’m shocked they might not be wearing clothes on his yacht.  I convinced her to pack a bathing suit and jeans, just in case, and she agreed, but I could tell she was game for her quarterback’s suggestion that they might spend the weekend naked on his yacht.  Jeez!  All I could think from that point forward was that he would be seeing all of her, non-stop, the entire weekend.  They’d probably be fucking non-stop too.  As I was about to close her overnight bag, she tossed one of her babydolls to me and told me to pack it, “just in case.” 

The night before she was leaving to be with her quarterback we cuddled and I gave her a very long session of oral pleasure.  In the morning she hugged me and told me how much she appreciated me letting her go.  She promised to text me while she was gone to let me know she was okay.  I tried to put on a good front for her, but she could tell I was feeling anxiety about her being off with her quarterback for so long. 

Friday morning, the day after she'd met her quarterback at his D.C. hotel, my cheerleader called me to tell me her quarterback had mentioned that they often lost cell phone coverage when they went out in the ocean.  Thus, I probably would not hear from her all weekend until they came to shore.  I could try to write about how my weekend sucked - to try to describe the overwhelming sense of anxiety that I felt the entire weekend my cheerleader spent on her quarterback’s yacht, only imagining her lying around naked with him on his luxury yacht while I waited at home.  But I think you get my drift.  All I had was my wild and unrestrained sissy imagination to guide me - and trust me - a sissy's wild and unrestrained imagination is a dangerous thing to a sissy. 

The last time I heard from my cheerleader before Sunday, was Friday evening.  They were heading out to sea and she sent me a text.  “I’m in good hands baby.  Tom really knows what he’s doing captaining his yacht.  I’m going to be his First Mate!  I love you.  Can’t wait to see you Sunday.”  Right!  She had just told me she would be alone on her quarterback’s yacht all weekend and that I would not be able to communicate with her at all. 

The next time I heard from my cheerleader was Sunday morning.  They had apparently travelled Saturday night and docked in Annapolis early Sunday morning.  Her quarterback wanted to take her shopping in Annapolis and then he was going to bring her home.  The Nationals were playing a 4:00 p.m. game that day and she told me she wanted me to go to the game so I would not be home when her quarterback brought her home.  I wondered then if she intended to do what I suspected she intended to do.  It turns out, I was right.  She sent me a text at 6:00 p.m. on Sunday telling me to come home right away.  The game wasn’t over, but I was out of the stadium like a bolt.  We only live twenty minutes from Nats Park, so I was home quickly.  I opened the door and called out my cheerleader’s name.  She hollered that she was upstairs.  I flew up the stairs and, sure enough, she was in bed, where I had suspected she’d be.  I was out of breath and she laughed, “Missed me?”  I told her I had.  She threw back the covers, revealing her naked body and asked, “So.  What do you think?  No tan lines!”  And just like that she let me know that she had, indeed, spent the weekend sunning in the nude on a yacht with her quarterback.

Then I asked the question I'd been thinking the entire ride home from the stadium.  “Did Tom come inside?”  My cheerleader smiled coyly, “Do you mean me?”  “Huh?” I said.  “Do you mean, did Tom cum inside of me?" she giggled.  "The answer is yes.  He did.  Come over here my sweet little sissy.  I have a present for you,” she beckoned me.  She slowly let her thighs fall apart.  I could see her slit was glistening wet.  She fingered herself, spreading her pussy lips open, sliding her fingers inside.  When she withdrew them they were coated with sperm.  She licked her fingers.  “Mmmm.  Yummy.  It’s all for you baby,” she cooed.  “Your reward.  I’ve been tasting his cum all weekend.  Now it’s your turn!  Take off your clothes and come and get it.  I know you want it.  Don't you sissy?”  

I removed my shorts and t-shirt, leaving the panties I was wearing on, and crawled onto the bed, between her legs.  “You fucked him in our bed?” I asked, the answer obvious.  “I’d say it was more like he fucked me in our bed.  But yes.  I thought you’d like to taste him.  It was the only way I knew how.  I could never have carried his cum from this morning around all day.  Come on now sweetie.  I want you where you belong.  I’ve been thinking of this all weekend.  Put your mouth right here.  Right where Tom's big dick was just a few minutes ago.”  On my knees, I leaned in closer to my cheerleader’s pussy and licked her.  I could feel her tense up at first, and then relax as my tongue parted her smoothly shaved folds, tasting her quarterback’s sperm inside of her.  “Oh sissy!” she sighed.  “I’ve been craving your tongue all weekend.  Tom pounded me so many times.  It was almost all that we did.  Oh God!  His cock!  I love it!  It would have been so sweet if you could have been there to do this each time.  To taste his cum.”  My penis swelled immediately and involuntarily within its chastity cage as I dove into my task, listening to my cheerleader tell me how mercilessly her quarterback had fucked her all weekend.  I forgot, momentarily, the anxiety I’d felt while she was away with him, imagining her on his yacht, naked, the entire time.  For the moment it was just me doing what I do best – cleaning cum from my sweet wife’s pussy.  After I had brought her to one orgasm, she sat up and pushed me onto my back, then crawled on top of me and settled her pussy onto my mouth.  She then began a slow and gentle grind, moving back and forth across my open mouth and tongue, rubbing her clit on my nose, face-fucking me as she brought herself to another orgasm and ejaculated a mixture of hers and Tom’s cum into my mouth, her nectar dripping down my cheeks.  I can't deny this thing - I love doing that for my cheerleader.  The messier, the betterer. 

Afterward, we cuddled and she told me about her weekend.  What she described amounted to a regular suck and fuck fest.  Their Thursday night in D.C. was spent much like the others they have been spending together.  Before going out to dinner, she sucked his cock and then he fucked her for a long time.  Then, dinner at a wonderful restaurant, just relaxing together and enjoying each other’s company.  I admit that I feel jealous of their long history.  When you’ve known someone as long as they have known each other, especially when your relationship began as teenagers, you have so many mutual shared friends and experiences.  Add in that they were married and had children together, and I get that they enjoy being with each other in a way I doubt either of them ever dreamed would be available to them after all that had happened since they divorced.  I admit that I’m envious that they have that.

They had left early Friday for Annapolis and boarded Tom’s yacht to go out to sea for the weekend.  The weather was fabulous for them.  It was in the mid-80’s and not too humid for July in this part of the country.  They were met at the dock by a man who had been with Tom for a long time helping him maintain his yacht.  On many occasions, the man actually captains the yacht for Tom.  But Tom wanted privacy on this cruise, so he was going to captain the yacht himself.  Tom idled the yacht out of the harbor and then opened up the engines and took them well out to sea, so they were totally isolated for the weekend.  As my cheerleader had told me, there was no cell phone coverage out there.  And so it was just the two of them - all alone.  And from hearing my cheerleader tell it, they made the most of their time together.  I also suspected then that this was something that would be repeated too.  And it has been.  My cheerleader did spend - nearly - the entire weekend in the nude, as did her quarterback.  The complete availability of each to the other resulted in more sex over a span of 3 days than my cheerleader could begin to recount in detail for me. 

The yacht, according to my cheerleader, was the most incredible thing she’d ever seen.  It reeked with luxury in every way.  Her quarterback's bedroom suite was like a small efficiency apartment she said.  No doubt, the weekend was an opportunity for him to show off his wealth to her, and she was duly impressed, but she was more interested in her unfettered access to his cock, from the way she explained it to me.  Their first order of business was to relax on the rear deck for cocktails and to relax as the yacht made its way out to sea on the Friday evening of departure.  The yacht was in open water and Tom set the vessel on automatic pilot and simply monitored progress, so that he was free to pay attention to my cheerleader.  My cheerleader had gone below to change into her bathing suit.  But, she told me, when she pulled out the bikini I’d packed, her quarterback just looked at her like, ‘Why are you doing that?,’ then said, “You won’t need it baby.”  And so the tone was set.  No clothes.  Almost the entire weekend.  I was, oddly, envious of the freedom they had to do that.

There was a passage to the bow deck from her quarterback’s bedroom suite, so they were able to come and go to that deck without going around the rear of the yacht.  They lay together on a wide mat that Tom laid out on the deck, my cheerleader cuddling up to her quarterback, quickly adjusting to the freedom of being outside in the open ocean air, naked, her big strong quarterback lying next to her.  As she told me about this, I was able to vividly imagine her holding on to him, reveling in the power he held over her.  As my cheerleader explained it, one thing led to another and soon she was giving her quarterback the first of many blowjobs she gave him during the weekend, almost all of which ended with his cock inside of her pussy, fucking her like it was the last time either would fuck each other again.  In other words, my cheerleader’s pussy was full of his sperm for most of the weekend, as no sooner would he finish fucking her than she would be wanting him again.  And, as she related the details to me, he was always up to the task.  He marveled at my cheerleader’s unquenchable thirst for his cock.  And he, apparently, loved that he held such power over her.

As my cheerleader shared the details of her weekend at sea with her quarterback, she continually tried to gauge my response to her deepening reconnection with the man for whom she'd borne two babies.  I wish I were able to adequately explain my emotions and reaction to hearing her tell me how much she craved Tom's cock.  What worried me was the obvious.  My cheerleader seemed to have fallen irretrievably under her quarterback's spell.  Again.  Just as she had as a bright-eyed high school girl falling in love with the football team quarterback.  What she described sounded to me like so much more than sex.  She may have told me it was only sex.  But it felt different to me.  But, as I tend to do, rather than say so to her, I chose to trust.  Her loving way with me continued to feel real.  Her love and devotion to me was not false.  I knew that deep within my soul.  And it is true.

There was another interesting thing that occurred that weekend.  I mentioned that my cheerleader's quarterback had planned to take her shopping in Annapolis when they returned from their weekend voyage.  Apparently, he had gotten it in his brain that he wanted to buy her some sexy clothes to wear when she was with him, including lingerie.  At first, my cheerleader explained to me, she protested, and even told him that she was worried what I would say about her suddenly having new sexy clothing.  However, in truth, my cheerleader was never going to refuse letting her quarterback buy her lingerie, or any other sexy clothing he wanted to buy for her.  She likes buying sexy new clothes. 

And he did buy her some very sexy clothing.  Her quarterback escorted her to a high-end fashion store that also had what was, obviously, a substantial lingerie department.  After they entered the store her quarterback approached one of the young women who worked there.  My cheerleader explained to me that, at first, it was embarrassing what he did, but it happened so quickly that she had no time to react in any way other than to go along with him.  When the young sales clerk asked if she could help them, her quarterback pointed to my cheerleader and told the clerk she was his mistress and he wanted to buy her some clothes.  He handed my cheerleader his credit card in front of the clerk and said, “Put whatever you want on this.  No limit.  I’ll be at the bar next door waiting.  Have fun.”  Before she could speak, he'd left my cheerleader alone in the store to shop.  My cheerleader was caught so off-guard at what he’d done she didn’t know what to say.  And the poor sales clerk was, apparently, equally flummoxed.  They looked at each other and the clerk said, “Well, okay.  How can I help you ma’am?”  My cheerleader told me she gave the clerk a sheepish grin and said, “I suppose we should start with lingerie.  What do you think?”  Once the shock wore off, the two of them began having fun together selecting sexy lingerie for my cheerleader, before moving on to dresses and other sexy clothing.  As it turned out, my cheerleader charged nearly $5,000 on her quarterback’s credit card.

 I was fortunate, I suppose, that she wanted to model for me what he’d bought for her.  The reason I say, 'I suppose,' is that she bought some very sexy and revealing outfits to wear while with her quarterback.  And the lingerie she bought was some of the sexiest I’ve ever seen – the sort of lingerie that a woman wore when her sole purpose was to entice her man to take it off of her as quickly as possible and then have his way with her.  She bought a dozen panty and bra combinations in various colors, styles and material.  By trying it all on for me, she made sure I knew what she’d be wearing whenever her quarterback was in town or she went home to visit and spend time with him.  She also bought several sheer babydolls for nighttime wear with her quarterback.  But the kicker was the outfits she bought.  Two of the dresses she bought – one black and one red – were of the slutty variety.  When she modeled them for me and she saw the look on my face, she immediately explained herself.  She figured that for him to spend so much money on her buying new clothes, she ought to give him what she knew that he wanted to see her in.  She also purchased a pair of tight white shorts and a gingham red checked halter-top.  And here is the kicker - she also slipped into her purchases a few things for me, courtesy of her quarterback.  She bought me a pair of shorts just like hers, only mine were pink, and my halter-top was pink checked gingham.  She also bought for me one bra and panty set and a babydoll just like one of the sets she bought for herself, all compliments of her quarterback.  I wonder what he'd think if he knew my cheerleader had bought her husband such pretty and feminine lingerie using his credit card?

So, there it is.  My cheerleader's weekend at sea with her quarterback.  As I mentioned, she has gone out on his yacht a few more times since then.  She has, as have I, grown more accustomed to spending those weekends in seclusion with him.  And when she makes those trips, she always arranges for me to be away so that he can bring her home to our house.  The result of this to me has been more frequent opportunities to clean his sperm from my cheerleader's pussy, something she and I each enjoy.

In my next installment, I plan to tell about how my cheerleader met Kurt.  Ta ta for now darlings.

Kiss kiss,

 

Leeanne.