[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. These are the previous posts that tell the story about my sissy journey.]
I
venture to guess that this installment about my sissy journey, a long one, may
be what many people who have been following my personal story have been waiting
for. I have given a lot of thought to
how I should go about relating what happened over the course of about four
months following the night of my cheerleader's and my 25th wedding
anniversary. It seems to me that so much
of what I feel I need to convey involves describing thoughts and feelings,
rather than actions, and so that is what I intend to attempt to do. And I should emphasize a very important point
– living through what I am going to
tell was intense, stressful, and extremely difficult. Describing
my own thoughts and feelings is a bit easier than those of my cheerleader. Much of what I am attributing to her is based
upon her actions, or things she said, more than anything else. I could be altogether wrong about some of
what I write about her internal processing of what was taking place in our
marriage. And while I am considering the
suggestion by someone that I ask her to share a first-hand account of her
perspective on this progression we went through together, I am not sure she
would want to do so. And for now, at
least, I'm afraid to ask her. I’m not sure she would understand being
asked to share something so personal in such a public way. So we'll have to muddle along with my
narrative.
In
the several days immediately following our 25th anniversary, my mind/psyche
was, in a word, a mess. Having read what
I've written about so far, as well as the hundreds of blog entries I've
created, one would be fair to wonder how that could be. Wouldn't one expect that a sissy, such as
myself, would be skipping for joy to have a wife who seemed to so eagerly be
accepting her sissy husband for the feminine creature he is? Perhaps.
But nonetheless, I was a mess. My
mind was in constant turmoil over what was happening in our marriage. I felt, more and more, at a loss of
control. It was in that context, too,
that I believe I began filtering what my cheerleader did and said. She seemed to exert more influence over
decisions being made in our life - even small matters such as choosing
restaurants. And then, there was the way
she treated me. She was so tender and
loving, almost as though I was the softer sex in our marriage, rather than
herself.
And
in bed, each night it seemed as though I was expected to be the woman. And when we made love, there was always a
cock, and it was always some man we knew.
Don't misunderstand me please. I
enjoyed what we did sexually. But we had
come so far from me deftly injecting panty play into our lovemaking, to my
cheerleader being so open about her fantasy to share a man with her sissy
husband.
A
few weeks after the night of our 25th anniversary, we hosted a
cocktail party at our house for several of my cheerleader's co-workers from the
retail store where she worked. Most of
her co-workers were women, like herself, who simply wanted some part-time work
to occupy their time and make a few extra dollars for spending – mad money. Many of her workmates brought their spouses,
but a few were not married and they came alone. There was one guy in
particular, named Randall, who stood out to me.
First, he was a tall and handsome man.
But more than that, I almost immediately sensed that he and my
cheerleader had hit it off. He hovered
near her for much of the evening. I
don't know if what I was observing was real, or colored by what was happening
between my cheerleader and me in our marriage.
But she seemed to be extremely flirty with Randall. I can still recall thinking at one point in
the evening, as I watched them chatting in a small group, that I had never
thought of my cheerleader as a flirt before, but that seeing her in this new
light, I suddenly realized she had always flirted with other guys at
parties. She simply was that way. Now, here in our new life, separated from
people who knew her well, and whose opinions mattered to her, my cheerleader
seemed (at least to me) to be opening up more.
We
had a good time that evening. Her
co-workers were very nice and I was happy to see that my cheerleader seemed to
be getting along so well with new potential friends. Randall was one of the last to leave and my
cheerleader gave him a very warm hug goodbye as they said goodnight. Afterwards, we cleaned up together before
going to bed. As I always did at this
point, I dressed in pretty lingerie for bed.
As I joined my cheerleader, I noticed her large cock dildo lying on her
nightstand. Seeing that and realizing what
she intended, I returned to my closet to slip on a bra and fill the cups with
my breast forms. I then crawled in
beside her and snuggled close to her bosom.
We cuddled for a few minutes and she thanked me for letting her have her
work friends over. What possessed me to
say what I was thinking, and had been thinking most of the evening, I am not
sure, but I specifically mentioned Randall, and how taken he seemed to be with
her. At first, my cheerleader acted like
she didn't know what I was talking about, but I pressed her a bit and she
finally admitted that he might have a thing for her. I let it drop for the moment, and soon, I was
where I usually ended up when we were in bed together with me dressed en femme -
between her thighs licking my cheerleader's pussy. And, as things usually went, she eventually
invited me to suck a cock for her, to prepare it for fucking her.
As
I was sucking the cock she whispered in a needful voice, "I wonder if
Randall has a cock that big?" I
hesitated a moment at her mention of his name.
I had not considered that she would bring him into our fantasy. But then, I continued sucking the cock. And as I did, she asked, "Would you suck
him for me?" There was a
pause. Then she added,
"Randall?" In my state of
mind, by this point, I would always say that I would do anything for her. And tonight was no different. So, just like that, Randall, a single man
that I could tell wanted my cheerleader, joined us in our bed. And I sucked his cock for my
cheerleader. And he fucked her. And she loved it. When it was over and I had gone inside of
her, filled her, and then sucked her pussy clean, we fell asleep in each
other's arms.
The
next day we did not speak of the night before.
But there was a tension. Not a
bad tension. And not exactly sexual
either. But there was something, as if
we'd crossed a line? Why did it seem
that this new man, someone I had only just met, being brought into our fantasy,
created tension for me, whereas I had come to accept my cheerleader fantasizing
about our mutual friends during our lovemaking?
I couldn’t
explain it, but there was something different about the night before.
That
next night, as we lay quietly in bed, I spit out what had been on my mind all
day. Where we would be today if I had
not brought this subject up, I don't know.
But, in a way, it doesn't matter.
Because I did bring it up.
Cuddled up behind my cheerleader, I asked her, "Do you want
to?" Those four simple words, asked
without specificity, led to so much more than I had considered would develop
between me and my cheerleader. She was
quiet for a few minutes. “Want to what?” she finally asked. I think she knew what I was asking. Really.
But I think she wanted to hear me ask it. "Do you want him to fuck you?" So there it was, after all that had developed
over the span of several years of our marriage, I asked my cheerleader if she
wanted more than a fantasy. I'd asked
her if she wanted another man to fuck her.
Her reply was, "Randall?"
She knew. I know she did. But she wanted to be sure? That he was who I was referring to? I told her yes, I meant him. I could sense her considering her response
now. And that moment of reflection,
alone, told me what her answer would probably be. I mean, she didn't dismiss the idea outright,
as if I were being ridiculous to suggest such a thing. And yet, I promise you, I did not expect the
reply she gave. Instead of saying yes,
or no, she asked me, "Would you suck his cock for me?"
Believe
me, I was regretting bringing the subject up by this point, but I couldn't undo
the conversation now. The tables had
been flipped, and in a most uncomfortable way.
We engaged in a careful dance of words.
I wanted to know if my cheerleader wanted Randall to fuck her. But she was attempting to see where I
stood. So I asked her if that was what
she wanted. She turned to face me then,
and looking into my eyes, she said plainly, "If he is going to fuck me, I
want you to suck him for me." I
could barely meet her gaze. However, she
was so close to my face that I couldn't avoid her. "I will if you want me to," was the
answer I gave without thinking it through.
In that moment, that is how I felt.
She looked into my eyes for what seemed forever before uttering a single
word, "Really?" All I could do
was nod and whispered back, "Really."
My cheerleader then gave me a soft kiss on my lips and said, "Let's
think about it." And just like that,
the subject was closed, and she turned around and went to sleep. Or, at least she seemed to. I know I didn't. I was so confused by then. Was my cheerleader seriously considering
being fucked by another man? And would
she really expect me to suck his cock for her?
This was made more difficult for me, I think, because we were not
discussing her fucking another man as a fantasy idea. We were talking about her fucking a specific
man, a man she spent time away from me with, a man who had been in our house
only the night before and who my cheerleader had been openly flirting with, who
was interested in my cheerleader, and who she was clearly interested in as
well.
I
don't recall how long I lay awake thinking about what had happened. But, I finally fell asleep. When I woke up, my cheerleader was already out
of bed. I remember being thankful for that,
as I did not know whether I would be able to look her in the eye. After showering and dressing, I reluctantly
went downstairs. I knew that I could not
avoid her forever. My cheerleader
greeted me cheerfully, almost as if we'd never had the conversation the night
before. But she did seem, to me at
least, almost too pleasant to me. She
kissed me and brushed her hand across my cheek in a loving touch. She began mentioning different errands she
wanted to run together, acting as though it was any other weekend day. I remembered thinking that I was relieved
that we weren't going to talk about it anymore.
And yet, it hung there. All day. In fact, I felt like it was a part of nearly
everything we spoke of that day. How do
I explain this? I've read many fictional
stories about sissies and their wives, where the subject of the wife fucking
other men is addressed. There is an edge
to the stories - at least the good ones.
But they are fantasy. Suddenly,
my fantasy was beginning to sound real.
My cheerleader seemed inclined to having sex with someone else and
wanted me to be a participant. I was not
sure how I really felt about that.
Well,
we went on like that for a few days. We
didn't discuss the subject after that night in bed. Was my cheerleader, as she'd said,
"thinking about it?" I
couldn't tell. On the following Thursday
my cheerleader included a note in my lunch bag.
I don't still have it, but I remember it word for word. She wrote, "Dear ____, I think I
do. Can I invite him to dinner tomorrow
night?" That was it. She wanted to fuck this guy Randall. I didn't know what to do - or what to
say. But, I also didn't know how I could
deny her this. After all, I was the one
who started this thing many years before when I let her know that her husband
was, well, a sissy. I knew that she was
at work, probably with him, right then.
So, without thinking about it much more than that, I sent her a simple
text message. "Okay."
How
can I describe the emotions I was feeling then?
I was unable to concentrate on anything.
Trying to work was useless. I
decided to go home early and go for a long bike ride. My cheerleader was still at work when I got
home, so I didn't have to face that. It
was so weird. I was doing what she
wanted, but felt embarrassed to face her.
Here is what I imagined she was thinking of me - not that I was letting
her fuck another man. No. It was more like I was agreeing to suck a
man's cock. For her. How was this even going to work? Did she have a plan? I had no idea. Did Randall even know what her intentions
were? Had they discussed it? Did she tell him part of the deal, for her,
was that I had to suck his cock? Nothing
but questions lingered and I was too embarrassed to ask my cheerleader to let
me know if she had a plan.
When
I returned from my bike ride she was home.
She smiled at me as I entered the kitchen. Without a word, she approached me and kissed
my sweaty face, something she doesn't like to do. "Go shower," she told me
sweetly. She was being sooo nice. And as confused as I was, I realized this
much - she was letting me know how much she appreciated what I was agreeing to
do for her.
As
we ate dinner that night, my cheerleader casually told me that Randall had
accepted her invitation to come over the next evening for drinks and dinner
around 7. I knew that if I was ever going to address the subject, this was my
opening. I asked her if he knew why he
was coming over. She smiled and said
that she thought so. I then asked if he
knew about me, meaning being a sissy, but without saying the word, because we
didn't really use it much. Then. She told me that they had talked about it
some and that he seemed okay with it.
So. There it was. Another person
knew my secret. I had shared this secret
with only one person. My
cheerleader. Now, a man I barely knew
had learned of my secret from the person I was closest to in my life – my cheerleader. My stomach sank. I know it may sound stupid. I mean, what did I expect? I'd agreed to my cheerleader's request to
invite this guy to dinner. And I
understood the reason for the invite.
Still, thinking, and knowing, are two entirely different things. Now, it seemed as though this fantasy world
we’d built
was going to become very real. And I was
scared to death. I had no idea how my
cheerleader intended to handle the situation.
I was completely powerless.
Looking back on it though, I can tell you, that powerlessness is a large
part of what such an event is about - the complete loss of power, as I was
submitting to someone else's desire.
I
went to work the next day, although it was a futile effort on my part. I was disconnected from everything, and
everyone. I have no idea whether anyone
sensed the disorientation that I felt.
My cheerleader was off from work, so I knew she would be preparing for
the evening. When I arrived home I found
that she had done flower arrangements and decorated things beautifully. There were hors d'oeuvres prepared and the
dining room table was set with her good china.
There was one setting at the head of the table and the other two were
across from each other right next to the head seat. I found my cheerleader in our bedroom getting
dressed. She was wearing a pretty black
bra, panty and garter set, with black stockings attached. I was stunned. I had not considered that she would dress
especially to please Randall, but she seemed to be. The dress lying on our bed was a very simple
dress - a short black one with spaghetti straps - but it was a sexy one. She asked me to help her step into it and zip
it up, and after I did, she asked if I liked it. Of course I liked it, but I was more stunned
to think that she was wearing it for Randall, rather than for me.
She
told me to hurry up and shower so I could get dressed too. It was obvious that she was very excited
about the evening. I couldn't recall when
I last saw her quite this way. I
remember wondering whether she was excited about being fucked by another man
for the first time in over 25 years, or whether it was because her husband was
consenting to the event. When I got out
of the shower I saw that my cheerleader had shopped for each of us. Lying on the bed next to a pair of grey
trousers and dark blue shirt was a white bra and panty set, also with a garter
belt and stockings, as well as a white lace slip. So there it was. My cheerleader wanted me in full sissy mode
for the evening, at least under my clothes.
I dressed and went downstairs to wait for my cheerleader's date. It was about 6:30. She approached me and placed her arms over my
shoulders, brushing her fingers along my bra straps and whispered, "Thank
you sweetie. You are the best!"
I
finally asked her how she planned for it to go.
She shrugged her shoulders and said she just planned to let events take
care of themselves. I didn't know what
to say, so I just said okay. I opened
two bottles of wine, one red and one white.
I poured my cheerleader a glass of white and myself a glass of red. She kept busy organizing and it struck me
then that she was nervous too, but her nervousness seemed more from a
heightened sense of expectation and excitement.
I was simply a wreck inside, completely flummoxed as to how I should
behave. I quickly drank my glass of wine
and poured another. Shortly after 7 the
doorbell rang. Randall had arrived. This was really happening. I looked at my cheerleader to see if she
wanted to answer the door. She asked me
to. So, I was going to greet the man who
was here to fuck my cheerleader. Almost
on automatic pilot at this point I walked to the door and, mustering up the
best fake nice face I could manage, I opened the door and greeted Randall. I don't even know how to describe the
moment. It was as if we each felt more
awkward than the other, and yet he was the one who should have felt the
advantage over me, given the purpose of the evening. The irony of his graciousness in thanking me
for inviting him over was not lost on me.
I still recall how foolish I felt as I uttered my response, "It's
our pleasure. Thank you for
coming."
I
led him to our kitchen where my cheerleader was busying herself, offering him a
drink as we walked. He asked for whiskey
on the rocks. Natch! Right?
When he entered the kitchen and saw my cheerleader in her sexy little
black dress he actually let out a low whistle as her called her name. She responded enthusiastically,
"Randall! You're here!" She came to him and immediately gave him a
warm hug in greeting. Then, as she
pulled away, as if she had determined to set the tone for the evening right off
the bat, she gave him a soft, somewhat lingering, kiss right on his lips. I stood by dumbly, watching this unfold in
front of me. Excusing myself, I told
Randall I was going to retrieve a bottle of whiskey. I returned with a bottle of Maker's Mark and a
whiskey glass. By my return, my
cheerleader had broken away and was setting out her hors d'oeuvres.
I
poured Randall a glass of whiskey over ice and handed it to him. He raised his glass to mine and we silently
toasted, as if this was the moment of agreement between us that I was handing
over my cheerleader to him for the evening.
What followed was a fairly awkward silence, one that was finally broken
by Randall talking to my cheerleader about some events that had occurred that
day at the store where they worked. So,
as if I couldn't feel more awkward, I was now not even a part of the
conversation. As if sensing what was
happening, Randall began asking me questions about my work. And soon, in the oddest twist possible, we
were chatting like friends about the things any new acquaintances talk
about. And, I had to admit, Randall
seemed like a really nice guy.
As
we talked my cheerleader put the finishing touches on dinner. Soon, she asked us to help her deliver the
food to the dining room. As she reached for the chair at the head of the table,
obviously intending for Randall and me to sit on either side of her, facing
each other, he beat me to it and held her chair. I watched like a bystander as my cheerleader
smiled warmly at this man encroaching upon my responsibility. The dinner my cheerleader cooked was
amazing. She is a good cook anyway, but
I could tell that she’d made a
special effort for Randall and he voiced his appreciation
enthusiastically. She was beaming with
joy that he liked it so much. I don’t know how to describe the
situation. We were three people enjoying
a wonderful meal, drinking wine, and engaging in fairly comfortable small
talk. And yet, there was this energy at
the table, mostly, it seemed to me, coming from my cheerleader and aimed toward
Randall. As if she understood that all
that was happening –
cocktails, dinner, and then after dinner – was
necessary to occur, but that there was a real purpose for the evening, and she
was looking forward to it.
As
we finished dessert, my cheerleader suggested that we retire to our den for
another cocktail. Randall began to help
clear the dishes from the table, but my cheerleader stopped him, saying he was
the guest, and that I’d take
care of it. Without argument, I agreed
with her that I would clear the dishes.
So she and Randall went to the den alone while I cleaned up. I sensed that she orchestrated this so she
could be alone with him for a few minutes, so I took my time cleaning the
dishes and the kitchen. I was just
finishing up when my cheerleader approached me alone. She came to me and hugged me, thanking me for
letting her do this. I remember that I
didn’t really
know what to say to her. I was, frankly,
very confused about how this was going to work.
I was about to find out. She told
me then that she and Randall were going up to our room. She also told me that he wanted it to be just
them at first, if it was okay with me.
Since I didn’t know
what to expect, but realized that my cheerleader was committed to going through
with having sex with Randall, I told her I guessed that would be okay. I asked what she wanted me to do. She said just wait, and that she’d let me know when I could join
them. And so she and Randall went
together to our bedroom to fuck, leaving me alone to wait, and wonder, and
imagine what they were doing.
I
had fantasized about this happening - many, many times. And my cheerleader and I had played our
little games together and they turned me on.
But now that a man was going to our bedroom with my cheerleader, I was
in turmoil. And yet, I was also oddly
relieved. I had been wondering what in
the world I was going to do when my cheerleader waited for me, and watched me,
suck his cock for her. Sucking the
dildos was one thing, but doing a real man was suddenly scaring me. And so, as much as I was torn that I was left
out, I was kind of relieved. I sat in
our den for a while, quietly wondering if they were doing it yet. And what and how they were doing it. Eventually, in what was one of the most
excruciatingly slow passages of time I ever recalled experiencing, I heard a
man’s
footsteps coming down our stairs. They’d gone up around 10 p.m. It was 2:30 in the morning. So, at least he wasn’t spending the night. I waited for him to leave, but he came to the
den to find me. I looked up at him not
knowing what to say. He saved me the
trouble. He told me he was leaving but
said, “Thank
you for a wonderful evening.” I, looking back on it, said stupidly, “You’re
welcome.” Then he said goodbye and told me my
cheerleader wanted me to come up to bed.
After
Randall left I had to face the next thing.
Seeing my cheerleader after her night of sex with a man. Wondering what to expect, I walked upstairs
and entered our bedroom. The room was
dark except for some light filtering in from our bathroom. My cheerleader was in bed, sitting up part
way against her pillow. I noticed her
lingerie was in a pile on the floor. I
assumed she was nude. I think she must
have been as unsure as I was about what to do next. She smiled at me and said, “Hi.” I said hi back and just stood there waiting
for her to tell me what I should do. I
really was lost here. She told me to
come to bed and so I went to my closet to take off my clothes. As I did, my cheerleader told me to leave on
the lingerie I’d been
wearing all night.
When
I crawled into our bed, she snuggled up to me and hugged me. I just sort of lay there, allowing her to do
whatever. She looked at me and asked if
I was okay. I told her I supposed so,
and asked how she was. What I was really
asking was, ‘How was
it?’ “Baby,” she whispered excitedly. “It was
amazing! I can’t tell you. Thank you so, so much for letting me do that.”
She was genuinely appreciative to me.
I still didn’t know
how to talk about what had happened. I
just said, “You’re welcome. I’m glad
you enjoyed it.” “I did!” she emphasized for me. “I really
did! And so did he I think. God!
He was insatiable!” It was like she wanted to talk about it, but
was a little hesitant to me. I didn’t know what to say to her. He was insatiable? I said, “Really?”
She told me then they’d done
it three times! They had been fucking
the entire time they were in our room! I
was shellshocked. “Really! And guess what?” she
asked me. So I bit. “What?”
“He is
sooo big honey. I’m even a little sore now,” she added. I did not know what to say. I said, probably unconvincingly, “That’s great.”
My cheerleader was holding me and rubbing me, her hand on my penis
outside of the panties I was wearing, and I was stiff. After a few minutes she told me, “I’d let
you, but I am a little sore.” I told her that was okay, although I did want
to. Then, she said, “But I’d love
it if you’d use
your mouth. Gently, like you do. Hmm?” What could I say? Of course I would.
As
I moved down to position myself to pleasure her, I remember thinking that what
I was about to do was not the same as cleaning my own sperm out of her. This was another man’s cum. And yet, I wanted to do this for my
cheerleader. I wanted her to know that I
was okay with what she’d done,
and this was the best way I could think of to show her. My cheerleader pulled the covers off of her
and opened her legs to give me better access.
I could sense her watching me, anxious to see me do this for her. It was important to her as well. As I moved toward her recently fucked pussy,
I could see that her bush was coated with cum, and there was sperm dripping
from her pussy. After all, he’d fucked her three times in just a
few hours. I leaned in and licked,
coating my tongue with my first taste of another man’s seed. It didn’t taste
like mine, but the unmistakable flavor of my wife’s juices
comingled with him was there, and I liked that.
I licked deeper and then the flow began.
Randall’s sperm
was running out of my cheerleader now that I’d opened
her up with my tongue. She pressed
downward on my mouth, silently urging me to clean her out. I really needed no encouragement now. I love pleasing my cheerleader orally - and
this time was no exception - for me anyhow.
But I think it meant something to her.
As I continued to suck cum out of her, slowly fucking her with my
tongue, my cheerleader began responding, and I decided that I was going to do
my best to bring her to orgasm. She
moaned the way she does when I am really getting her going. As she was getting more and more cranked up,
she said, “Oh yes
baby! God that feels good! I love you so much! I wish you could have sucked his cock for me
tonight. I really do! Don’t you?”
Honestly! I was trying to get her
off and she was asking whether I wanted to suck her lover’s cock. I pulled away long enough to say, “yes,” and
then went right back at her. I had to
please her this night. I had to! And eventually, I did. She had an earth shattering orgasm, wrapping
her legs around my head and squeezing me until I could barely breathe, which
can hurt, but I know when my cheerleader does that to me, I have really gotten
to her.
When
I crawled back up beside her, the film of her juice and another man’s cum coating my face, she kissed me
and thanked me again. “Next week, you’ll suck his cock. Okay?” as if she
felt it was owed to me, and also letting me know next week was already going to
happen. “Okay,” I answered. We fell asleep in each other’s arms and slept late into the
morning. When we woke up my cheerleader
began going about her day, but there was a new skip in her walk. She was clearly in a wonderful mood because
of the night before. As for me, I was
still a bit shellshocked. The entire
affair had caught me off guard. I had so
much to process. And I had to do it with
an understanding that this was not going to be a one-time thing. My cheerleader wanted more and wasn’t even discussing that with me. She had decided.
I
will tell about the next week, and how things evolved over the next two months
of that time frame in our marriage, in my next installment. But, suffice it to say, the emotions and
conflict rolling around in my head were only the beginning. My cheerleader had cucked me. I was a cuckold. And no reading cuckold stories, or any
fantasy that you can imagine, comes within a whisper of what it feels like when
you are actually cucked by your wife with a man who has a cock that actually
satisfies her in a way that you couldn’t dream
of doing. And it isn’t even really an exhilarating
experience when it first happens to you.
But it is an experience that you will never forget, and is a shared
experience between a sissy and her wife that they will always, in the way that
only a sissy and a wife can, cherish.
