Date: Sat, 26 Dec 2015 13:59:42 -0800
From: Derek Collant <skylark675@gmail.com>
Subject: Sissy Boy

Daddy's Sissy-Boy

This story is a work of fiction and contains descriptions of explicit
sexual acts between a man and his transgendered son.  As such, it contains
graphic scenes of sex between an adult male and a consenting underage boy
(Mb).  I'd love to hear from you, and will answer all emails.

I've been an avid reader of the stories posted on Nifty for a number of
years.  This is truly a unique site and provides some great times form the
wonderful stories that are uploaded to it.  It also provides a venue for
authors to publish their stories, which may never see the light of day
anywhere else.  I would urge you to consider making a donation at
http://donate.nifty.org/donate.html so we can enjoy this site for a long
time to cum.

Due to some problems with the network server my company was forced to close
down early.  I don't think I'd ever been home from work that early.  A
co-worker dropped me off in front of my house.  I went inside and went
upstairs to change.  I heard a noise coming from my room, and stopped.  I
wasn't too scared as I knew my son would be home from school by now.  I was
wondering why, though the noise was coming from our room and not his.

I rounded the corner and stepped into our bedroom and was surprised to see
my wife standing in front of the mirror.  She had gotten into the lingerie
outfit I'd bought her last Valentine's.  It was a great outfit (I thought)
comprised of a sexy teddy, matching panties and a sheer robe to cover.  It
was all in red.  She'd accessorized by putting on a pair of tan pantyhose
and was wearing a cute pair of slipper mules.

"Janine," I started, "You look..."

Before I could get any further Janine whirled around and let out a gasp.
Only, it wasn't Janine who gasped.  I stood there uncomprehending looking
at this person in front of me.  It looked like Janine, only it wasn't.  It
wasn't until I heard the voice did things click into place.

"Oh my god, Dad!" my son Craig replied.

We froze facing each other.  I glanced up and down my 'son' and couldn't
believe it.  He was even wearing make-up.  A cursory glance at his crotch
revealed that he was also aroused.  Quite frankly, I was too shocked for a
reaction.

I finally found my tongue, "What on earth are you doing!?"  I exclaimed.
My tone wasn't harsh, but carried all my disbelief.

"Oh my god, you're not supposed to be home!"  my son responded.

"The server is down so we were sent home early.  So, um well, this is a bit
awkward, to say the least.  Well, I, er, um, do you want to talk about,
this?"

"Well, uh, I'm so sorry dad.  I um, uh, I was just..." he trailed off, I
could see that he was getting really upset.  He tried covering himself as
best he could with the gossamer fabrics that he was wearing.  I was
distracted by a shocking thought as to me it seemed cute. My god, that was
my son!  I rationalized that it was because dressed like that he looked so
much like his mother.

"Here," I motioned to the bed.  "Why don't you have a seat."

Craig walked over the bed, and I couldn't help but notice he did so without
the slightest bit of teetering.  Hmm, so this wasn't his fist time in
heels.  He sat down and crossed his legs in a very feminine way, became
self-conscious, uncrossed them and placed both feet on the ground, his
pantyhosed thighs tightly pressed together.  I walked over and sat down
near him.  Cripes, I could smell that he'd put on his mom's perfume.  My
favorite one to boot, the one she used when we had sex.

"How long has this been going on?" I started softly breaking from the
thoughts creeping into my head.

Craig looked at me with his eyes that had eyeliner, shadow and mascara.  I
could see that he was on the verge of tears.  "A year or so." He said in a
barely audible whisper.

"Oh Craig," was all I could say.

Tears welled up in Craig's eyes and he said "I'm sorry.  You're
disappointed in me, aren't you?"

"There, there," I said, standing up getting some tissues, sitting back down
next to Craig, placing my arm around him and giving him the tissues.  "I'm
not at all disappointed in you, but you have to let me be surprised and a
bit uncomfortable."

Craig crossed his pantyhosed legs and I noticed for the first time that he
even went so far as to shave his legs.  The slipper on his foot dangled
seductively of his pantyhosed toes, which he'd painted as well.  Unbidden,
the thought that my son has a gorgeous set of gams crossed my mind.
Despite the present situation, I felt a familiar stirring in my groin.

I guess I'll stop here for a second and admit that I've a total pantyhose
fetish, and have had one since I can remember.  In the past few years, I'd
been exploring it more and more.  Unfortunately, my wife Janine really had
no interest in pantyhose, calling them a bane.  I even told her how sexy
they were and how they really turned me on.  It didn't sway her at all, so
only rarely did I ever get to see her in them.  To ease my desires, I'd
taken up wearing pantyhose myself.  They felt so good and since Janine had
very few pairs, I ended up getting my own stash.  The Internet helped
allowing me to connect with others of similar interest.  I was really
shocked by how many other guys were into this.  It had been my plan to take
this early day and use it for some pantyhose fun.  Finding my son in a pair
certainly made for an incredible discovery.

"Listen," I said after composing myself a bit.  "It's alright."  I wasn't
prepared to tell my own son, yet, that only was alright, I thought it was
great.  I could just imagine it, yep, you're dad also love to indulge in
sexy pantyhose.  I was too scared, though.

"Really," he said sniffling.

"Yeah."

"I thought you'd freak out on me."

"Well, I have to admit this is not exactly what I would have expected, and
I guess it might've been better had I never found out, but I'm know that
things are different these days.  If it's what makes you happy and really
doesn't cause anyone any harm, then I suppose I can learn to accept it."

"Oh dad," he said reaching around me and hugging me.  "Thanks."

I returned his hug, feeling the soft fabrics covering my son, I was ashamed
by the fact that I had such a strong sexual response.  I could almost
forget that he was my son and believe this was my wife.

"What about mom?" Craig asked, breaking our embrace.

Yeah, what about her?  Here my son was doing everything that she never
wanted to do.  Everything happening was turning my world upside down.

"Well," I responded, placing my hand on my son's pantyhosed thigh.  Oh,
what thrill that was.  "That's something for you to decide.  I promise not
to say anything, though."  Oh god, his pantyhosed thigh, oh no, I couldn't!

"Thank you so much dad." He responded, once again reaching around to hug
me.  I returned the hug, my hands caressing up and down his back.

"There there, it's gonna be alright."  But in mind it wasn't, I felt
flushed and dizzy, the feelings coursing through me threatened to make me
shake.

Reluctantly, I broke our embrace.  Scared of what may happen if we had
continued.

"Well," I said trying to get my mind off these intense thoughts.

"At least someone got some use out of that outfit."  I continued indicating
the outfit my son was in.

"Well, I thought it was one of the prettiest that mom has." Craig said.

I chuckled, responding.  "Well, you know I picked that out for her."

"Really, well you've got great taste."

We laughed, the mood lightened considerably.  Well, this certainly was the
last conversation I ever expected to have with my son.  My daughter, but my
son?

"Say, are those your pantyhose?" During the pause in our conversation my
attention had been drawn down to my son's incredibly sexy nyloned legs and
feet.  "I don't remember your mom having that kind."

"Well, sorta," he replied.  "I found these in the laundry room in back with
your tools."

Oh my, I thought with a lurch.  If that's true, then he's actually wearing
my pantyhose because that's where I kept them.

"The certainly fit better than mom's, though I wonder how they got there."

"Don't look at me," I responded.  Oh my, oh my, because they're your dad's
I bought them to fit, I could've said.  I looked down at my son's legs,
arousal washed through my body at the though of my son in my pantyhose, my
pantyhose.  No, no, this can't be happening!  Inadvertently, my son had
started bobbing his crossed leg, causing the sexy slipper to sway
alluringly on his pantyhosed foot.  I gulped nervously, and drug my eyes
back up to my son's pretty painted face.  My heart beat like a jackhammer
in my chest.  Despite all my wishes to the contrary, I felt my cock growing
to full hardness in my pants.

"Dad," Craig asked after a pause placing his hand on my thigh, "I know you
said everything about this is alright, but you are sure acting as if it
bothers you."

"Ah, no," I said with a dry mouth.  "Everything's fine, just kinda getting
used to the idea."

It was a lie, I wasn't fine, I felt lusts and stirrings that I shouldn't be
having.

I saw Craig's prettified eyes scan down my face, and then chest.  No, no, I
thought he'll see, I'll be humiliated.  Down his gaze went, until I knew
for sure he was looking at my tented trousers.  Immediately, Craig looked
up at me with an inscrutable expression.  My face was beet red with
embarrassment.  He moved his hand up and caressed my hardness through my
trousers.

"For me?" he whispered.

I closed my eyes, sinking into the emotional tide overwhelming me, and
nodded my head.  I gasped as I felt Craig's hand tighten around my
hardness.

"Oh dad," he said.

"Craig, I'm so sorry, I can't help it."  I responded dejectedly.

"Oh daddy, it's alright, it's ok."  Craig responded placing a kiss on my
cheek with his red lipsticked lips.

I opened my yes and saw Craig's bright eyes staring into mine.

"Oh my darling Craig," I whispered and pressed my lips against the lipstick
creamed lips of my sissified son.  We kissed tentatively, soon our lips
parted and our tongues grazed against each other as I took my girlie-boy
into my arms, sighing.

Craig broke the kiss after a bit and held my face in his hands.

"Craig, I don't know what to say," I said, tears welling into my eyes at
the shame I was committing.  But the emotions inside me were so strong, I
had no will of my own.

"Shh, you don't have to say anything dad, it's alright.  I want this to
happen." Craig responded.

Leaning forward my sissy-boy kissed the tears from my face.

Craig got up from the bed and slid down to the floor in front of me.  I was
gasping and trembling with lust.  First my sissy-boy undid my shoes,
removed them, taking my socks off next.  Then he got up on his knees.
Reaching forward he undid my belt and loosened my trousers.  I just sat
there, unable to move, afraid of continuing, but desperate to do so.
Grabbing the waist band Craig tugged down my pants, I was finally able to
move and lifted my bottom up to allow my girlie-boy to slid down and remove
my pants.

My cock was tenting my underwear.  Craig wrapped his hand around the tented
fabric causing a sharp intake of breath from me.  He looked up at me
expectantly with his pretty eyes.  I surrendered completely to my desires,
nodding to him, whispering "Yes."

Craig's hands went to the waist band of my underwear and he worked them
down my hip, again I lifted up and deftly he tugged them off.  My cock was
now staining tall, as hard as I could ever remember it being.  My
girlie-boy placed his palms on my thighs and stared at his daddy's cock.  I
could see precome start to glisten at the tip.  He leaned forward,
moistening his painted lips.  Everything seemed to be happening in slow
motion.  With one had he grasped the base of my cock.  Oh my, his flesh
against mine!  Opening his mouth, I saw his tongue snake out.  Deftly he
dabbed at the tip of my cock, gently removing the precome gathering there.
I moaned at the touch.

"Oh sweetie, oh my, yes," I was completely lost in my lust at this point.

My sissy son then opened his mouth wider and took the head of his daddy's
cock into his mouth.  I sighed at the sensation of my turgid meat slipping
between his painted lips and into his hot mouth.  Oh the sensation was
exquisite, especially when he started to work his tongue along the
underside of my cock.

"Oh darling, you're making your daddy feel so good."  I encouraged.

My darling sissy son needed no encouragement as he began to suck his
daddy's cock in earnest.  He grasped my balls with one hand and started
tugging and massaging them.  With his other hand she encircled the base of
my cock and stoked it in rhythm with his mouth.  I knew that this wasn't
the first cock my girlie boy had sucked.  I was soon gasping and writhing
at the expert job he was doing to me.

It wasn't very long at all before I felt the familiar sensation of my
impending orgasm.  Oh god, I was in heaven.

"Oh yes, sweetie, your making daddy feel so good!  Oh yes, I'm so close
honey, I'm gonna come soon!"

I tried to pull my hardness out of my sissy son's mouth, but he only
redoubled his efforts sucking me.

"Oh honey, I can't hold it anymore." I said as one last warning, realizing
that the last taboo of this whole act was going to be crossed.  My sissy
son was going to suck and drink the come out of his daddy's cock.

"Oh yes, oh yes, I'm coming!  Take it!  Take your daddy's come sweetie!"

With one last moan I exploded into my girlie son's mouth.  Wave after wave
of my orgasm washed over me as I pumped hot seed into his mouth as I
collapsed back on the bed.  It was more intense than I could ever remember.
Every fiber of me was involved in this orgasm.  It seemed like it lasted
for a very long time.

Eventually, I came back to my senses, my son's painted lips were still
around my cock and he was gently suckling on it, milking the last remnants
of orgasm from me.  Finally, I just became too sensitive and had to pull
out of his mouth.  He reluctantly let it go, lapping her lips to get every
trace of daddy's come.

I couldn't believe this had happened.  Why had I allowed?  The answer was
between my legs savoring the rich load I'd given up to him.  Craig got up
from the floor before I could analyze things too much.  I was shocked to
see that his panties were soaking wet.

He looked down and grinned, saying, "I couldn't hold back either."

Then he sat down on my lap, straddling me and pressing the gossamer fabric
of his or should I think of it as 'her' 'hose and panties against my naked
lap.  My god what a sexy sight, not even his mom was capable of this kind
of sexuality.