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.
