Date: Thu, 18 Sep 2008 18:56:34 -0700 (PDT)
From: sniffmecioc@yahoo.com
Subject: Falling for Tammy

Falling for Tammy
By Sniffme Cioc
Copyright 2008.  For posting to Nifty Archive.  All other rights reserved.

I was the world's biggest nerd in high school.  At 16 I was a virgin,
desperate for physical contact, but completely unable to do anything about
it.  Every conversation with a girl ended with her either yawning
uncontrollably or backing away nervously.  I think that impossible gulf
between me and all things feminine contributed to the almost constant
hardon I carried around between my legs.  I was always reaching into my
pocket to adjust my prick and I know the girls often saw me doing it
because I would hear them giggle and see them whispering to each other.

Looking back, while I wasn't Brad Pitt, I wasn't a bad looking guy.  I was
6 feet tall, very thin, pale, dark brown hair, pink nipples and a
circumcised 6 inch penis.  I had a few friends who were at least as nerdy
as me.  We used to work on experiments together while quoting entire
scenes, word for word from Star Trek.  It is not hard now to understand why
the girls stayed away in droves.

My one other friend was named Tommy and lived in my neighborhood.  He was
two years younger than me but just as strange.  While we didn't have much
in common, he lived close and his parents never seemed to be home so we
hung out pretty often.  He had an interesting face; almost pretty with full
red lips and sandy blonde hair that was always long and shaggy.  There was
something vaguely feminine about him that put most people off, but it
didn't really bother me.

At some point I guess he discovered masturbation because he started asking
questions about how I did it and what I fantasized about.  All this made me
pretty uncomfortable and I would usually just change the subject to
something safer.  At the same time I noticed that he had started dressing a
little differently.  It was hard to put my finger on at first, but colors
were suddenly more vivid, fabrics a little softer, shorts a little tighter
and shorter and tops cut a bit lower.  He also seemed to be wearing a
little makeup and sometimes I was sure I got a whiff of perfume.

I didn't think much about his gradual shift until the day of his 15th
birthday.  As I was his only friend, he didn't bother to have a party, but
invited me over, saying that he had a big surprise for me.  I knocked on
his door and when he answered I was shocked to see him dressed completely
as a girl.  What I saw was a beautiful girl who looked familiar, but not
quite.  I stammered asking if Tommy was home, then realized it was him.

"Dude, what the hell are you doing?"  I said as he dragged me into the
house and shut the door.  He leaned back on the door with his arms behind
him seductively and asked, "I'm Tammy.  So what do you think?"  It took a
moment to absorb it all.  The transformation was complete and amazing.  He
was a knockout, at least as pretty as all those girls I masturbated over
constantly.  He was wearing little white sandals that showed off his pretty
feet with red toenails.  His legs were shaved and perfectly shaped.  He was
wearing a tight short pink skirt and a low cut yellow sleeveless top that
showed off his little breasts.  The look was completed by a gold necklace
and little dangly earrings.  His lips shined with gloss and his eye makeup
really brought out his sparkling blue eyes.  It was just too confusing.  My
penis immediately hardened looking at her, then softened as I remembered
that this was my slightly weird friend, Tommy.

"Tommy, this is just too weird for me.  I gotta go," I said walking to the
door.  He placed his hand on my arm and rubbing his other hand across his
chest he seductively asked, "come on, don't you think I am pretty?"  I
jerked my hand away and shouted, "Dude, are you serious?  You are a fucking
guy!  This is the weirdest thing I have ever seen in my life.  What are
you, some kind of a fucking fag!?"  The effect was immediate and terrible.
He was crushed.  I guess he thought I would love the look and he
immediately broke down and cried, but it didn't stop there.  He slumped
down onto the floor, leaning against the door, with his head in his hands,
sobbing so hard that his whole body was shaking and I wondered if he could
breathe.

Between sobs he apologized over and over telling me that he did not know
what had gotten into him.  That he was so sorry he had offended me.  That
he would never do it again.  I felt terrible and knelt in front of him
asking him to stop crying.  Telling him it was ok.  That I didn't mean to
be so harsh.  He looked up at me with tears and mascara running down his
pink cheeks and said, "I am so sorry.  I will never do this again."  I
reached up with my thumbs and wiped the tears away and said, "let's talk a
little."

I asked what was going on and he said that he loved dressing and acting as
a girl.  I asked how long he had been doing it and he said since he was 9.
He told me that he had been wearing girl's underwear and nightgowns
exclusively for a year and that when he was alone he usually dressed
completely as a girl.  He showed me his closet with all sorts of girl
clothes and opened a secret drawer and showed me all his underwear.  It was
filled with beautiful lacy, silky things and I couldn't resist reaching my
hand out to touch them.  He reached for a pair if red satin panties and
handed them to me saying, "feel them.  They feel wonderful don't they?"  As
I touched them I had to admit that they did and added that they felt really
sexy.  He smiled knowingly.

He told me that in all those conversations about masturbation, when he was
talking about girls, he was actually thinking about guys.  "really?" I
asked.  Wow, that is strange.  "have you ever had sex with a guy?" I asked.

"No, no.  Not yet at least," he replied.

"But you want to?" I asked.

He looked down and fiddled with the panties in his hand and looked back up
into my eyes and said, "maybe.  I think I do...but only with the right
boy."

At that moment he looked so vulnerable and pretty I actually wanted to kiss
him, but I didn't and the moment passed.  We talked a bit more and
eventually I went home with my head spinning.

For the next few times we were together Tommy was back to normal, but the
femininity was definitely there and growing.  He didn't wear dresses or
overtly girly clothing, but there was always just a bit of eye makeup, his
hair was always nice and he almost always had on those tight short shorts.
He was usually just my pal Tommy, but occasionally, when he sat just right
I would catch my eyes following those lovely legs all the way up to where
they disappeared into those red silk panties and I would have to look away
to get myself back together.  When we were apart, I thought of sex all the
time as usual, but occasionally my mind would wander to Tommy.  An image
would pass through my mind of his thighs or his butt or his mouth or cheek.
At first I fought it, but more and more I just went with it.  It was
feeling less and less gay as I found myself thinking of Tommy more and more
as Tammy.

One Saturday morning I dropped by and he had the house to himself as usual.
He asked if I wanted a glass of wine.  This was new.  I had never tasted
alcohol and while I was a bit nervous about it, I decided to give it a
taste.  He went to the refrigerator to get the bottle.  As he did I noticed
for the first time what a sexy butt he had.  It was round and protruded
sexily.  The short pants showed his crack off so deliciously that I had to
reach down and make a quick adjustment in my pants.  As he turned around I
know he saw me adjusting, but said nothing as he poured the glasses.

The wine was nice.  Better than I expected and we finished a glass quickly
as we talked.  Tommy refilled the glasses and suggested that we go to his
room.  When we got there he said he had a surprise for me, then seeing the
sudden look of horror on my face shouted "don't worry!  It isn't like the
last surprise!"  We both burst out laughing so hard that we fell against
each other spilling wine all over the place.  My head was spinning and
warm.  He brushed the wine off my chest and I remember thinking how nice it
felt having his hand on me.

I said, "ok, let's see this surprise."  He took me by the hand into his
parent's room and opened the closet.  He took down a box from the top shelf
and turned to look at me with a smile.  "treasure," he said with an impish
smile and led the way to his room.  He opened the box and inside was a
stack of porn magazines.  I had seen porn a few times on the internet, but
my parents kept the computer pretty locked so this was indeed a treasure
trove.  We sat on the bed cross legged with the box between us and each
took out a magazine.

The first one I saw was about girls with huge sloppy boobs.  It was cool,
but the girls looked harsh and old and I put it down pretty quickly
reaching for another one.  The second one was a gay magazine showing guys
sucking each other off and having anal sex.  I looked at it a moment and
laughed, handing it to Tommy saying, "here bro.  this one has YOU written
all over it."  He looked for a moment and said, "not quite," which actually
surprised me.

Tommy looked into my eyes shyly and pointed to the next one on the stack
and said, "try that one.  It is more my speed."  On the cover were sexy
young girls but when I opened it I was shocked to see that these pretty
young girls all had penises.  Oh my god.  I was immediately hard as a rock
and couldn't do a think about it.  "wow," I said.  "Is this real?  This is
amazing. "  The girls were truly pretty.  They were young with warm soft
skin, perky small breasts, absolutely luscious asses, and, well, cute
little penises.  And they were very very sexy.

I was captivated as I scanned the picture, drinking in every detail.  The
girl's nipples were little rounded cones on top of little cone shaped
mounds.  Her stomach was flat and sexy with a gold ring in her navel.  She
had a patch of dark pubic hair and there, between her sexy thighs hung her
small penis that could only be described as intensely sexy.  Her little
cock was surrounded by a slight mound of what looked like creamy soft skin
and I found myself imagining what it would be like to kiss him/her right
there.

I looked up to meet Tommy's seductive eyes.  "pretty sexy aren't they?" he
said.  I wasn't sure what to say, but gulped and said, "Yea.  I never
thought I would say this, but I guess they are."  We sat there staring at
one another.

After a long silence Tommy finally whispered, "do you ever think about
Tammy?"

"sometimes," I croaked.

"she thinks about you all the time." She said My hands were shaking, my
mind was reeling and my cock was rock hard as she whispered, "would you
like to see her, now?"

I blinked, trying to think of a way to say no, but my mouth got there first
saying, "yes.  I would like to see her very much."

He leaned forward ever so slowly and brushed his lips against mine.  In
that moment everything changed.  Tommy was now Tammy in my mind and I
wanted to be as close to her as possible.  I kissed her back awkwardly as
we gazed into each other's eyes.  Her perfume was intoxicating..  I
couldn't take my eyes off of her.  As we kissed again I felt her tongue
pressing against my lips and I opened my mouth to allow her in.  Her tongue
felt warm and exciting and alive.  I could taste her saliva, smell her
breath and feel the warmth of her face against mine.  As we kissed the
thought came into my head that I was about to make love for the first time
in my life.

She whispered in my ear, "Stay here.  I will be right.  She jumped up and
ran to the bathroom and I caught a glimpse of her pretty ass as she looked
back blowing a kiss just before closing the door.  I was suddenly alone
sitting on my friend's bed surrounded by porn, terribly confused.  I wasn't
sure how this worked.  What was I supposed to do?

In just a moment the door opened and out came Tammy in all her glory.  She
was wearing a blue teddy that matched her eyes.  It was very short, coming
down even with the bottom of her blue silk panties.  Her bra matched the
panties.  She was barefoot and I was struck by how feminine she looked as
she walked toward me slowly like we were both dreaming.  She stopped and
turned slowly then looked into my eyes for a moment.  "You are so
beautiful." I exclaimed and her eyes filled with tears.

"I am going to make you so happy." She responded.  She swept the magazines
onto the floor and climbed onto the bed on her knees.  She took my cheeks
in her hands and kissed me long and deep, exploring my mouth with her
tongue.  I was in heaven.  This was truly the woman of my dreams and here
she was, in the flesh, wanting me as much as I wanted her.  It was almost
too much to comprehend.

As I sat there dumbly she took the lead and pulled my t-shirt up over my
head and cast it aside.  She pushed me back on the bed and removed my
shoes, socks and pants, leaving my underwear.  She leaned down again with
her face near my crotch and looked up at me saying, "I have never done
this, so be patient."  I watched her as she touched me through my
underwear, outlining my hard penis with her finger.  She placed her fingers
around it as though she was gauging its size.  She looked at me and reached
for the elastic of my wasteband and slowly pulled them down, lifting them
to clear my throbbing member.

She looked up at me, her face only a couple of inches from my penis and
said, "it is even more beautiful than I imagined."  Then caressed it so
softly and lovingly for a moment then she kissed it softly.  It jumped in
response which made her smile.  She opened her mouth and licked it with the
tip of her tongue saying, "mmm.  tasty."  I noted that her tongue was
exactly the same color as the head of my penis and reveled in the delicious
feeling of her slippery tongue against my sensitive skin.

My penis rose higher and she reached out with her hand and lifted it into
her mouth.  With our eyes locked together she kissed the precum covered tip
and let it slip between her full red lips, for a moment.  "mmm" she
muttered as she swished her tongue around the head.  I felt so tightly
connected to her as we both explored amazing sensations for the first time.
"oh god Tammy." I whispered, unable to even speak.  I saw the corners of
her mouth smile a bit then she started sliding down my penis ever so
slowly.  Truly, that was and remains the single most exciting thing I have
ever experienced in my life.

I felt dizzy like I would faint.  I could feel the warmth of her body
draped across my thighs and could see my very wet cock sliding in and out
of her mouth.  I reached out and stroked her cheeks as I moaned loudly and
thrust my hips to go deeper into her mouth which was locked around my
penis.  It was such a wonderful site.  We continued that way for maybe a
minute before I realized that I was about to explode.  I tried to pull out
of her mouth, saying, "I am coming!" but she held on and just replied,
"mmmmmm."  Hearing that I let go and blasted what felt like ten shots of
cum into her mouth and she swallowed it all, continuing to slowly slide up
and down.  As I softened she slid her mouth off me and squeezed my penis
between her thumb and fingers, milking out the last drop out onto the tip
which she rubbed onto her soft lips like lipstick which made us both
giggle.

She slid up my body and lay on top of me, her legs spread, her thighs
gripping me, our crotches touching.  I felt the small mounds of her breasts
and a hard bulge in her panties against my soft cock.  She kissed me softly
with her slippery wet lips and I smelled my sperm on her breath.  It was
intoxicating.  I grabbed her and kissed her as hard as I could, licking all
around inside her mouth.  With my right hand I reached down and felt her
perfect soft, satin covered ass.  It felt so good and I felt my cock start
to rise again.  I squeezed her butt cheeks and slipped both hands under the
fabric of her panties to feel the warm flesh.  We moaned into each other's
mouths as I explored, running my fingers up and down the crack.  As I
touched her little hole she moaned loudly so I did it again and felt her
rise to meet my fingers.  I pressed a bit and my finger slipped inside.  I
realize now that she had lubed herself, but at the time I was just amazed
at how hot she felt inside.

"I want you inside me, my love." She whispered slowly pushing her butt
against my probing fingers.  I was confused, "in here?" I asked.  She
smiled and nodded yes and before I could think about it too much she raised
up enough to remove her panties then straddled me on her knees.  My cock
was fully hard again and she slid it back and forth along her butt crack
which felt amazing.  It was so slippery and it felt like it belonged there.
Each time it could cross her tight little hole it would slip inside just a
bit, deeper and deeper with each pass until she stopped and slowly sank
down on my hard cock.  She gasped as it entered her and I think it hit us
both simultaneously that we had just become one in some crazy spiritual
way.  She placed her hands on my chest and I caressed her forearms as she
rose up and down on me.

It was wonderful.  After a moment she pulled the teddy up and off, tossing
it aside and I saw this beautiful girl, wearing only a blue silk bra,
looking lovingly into my eyes, fucking me like crazy.  I could feel her
butt cheeks against the sides of my penis as she rose up and the softness
of those globes against my thighs as she came down each time.  After a few
strokes I became aware for the first time that her penis was rubbing
against my stomach each time she lowered herself..  I looked at it and was
amazed at its beauty.  Unlike mine, hers was uncut, with a soft covering
over it coming to a point with soft wrinkly skin at the tip.  The tip was
dribbling precum.  I reached out for it and it felt strange.  Like mine,
but different.  I slid my hand all over it enjoying the warmth.  I cupped
her balls in my other hand and caressed the soft skin.  As I jacked her
penis up and down it started to rise, feeling alive and exciting, its head
peeking out of its little foreskin hiding place.  I continued to jack it as
she continued to rise and fall on my cock.  As her pace intensified I
matched it with my hand and could feel the intensity building in both or us
until she screamed and started shooting hot semen onto my hand and stomach.
I think it was the wonderfully sexy smell of her cum that pushed me over
the edge and I came into her butt with almost as much intensity as the
first cum.

She slowed her pace then stopped and leaned down to kiss my mouth.  I let
go of her penis and put my arms around her, pulling her close to me.  Our
hearts were pounding together.  I slid my hand down and played with her
slippery asshole that was oozing my cum.  As I did she slid her body along
mine slowly, lubricated by her cum that was between us.  As we fell asleep
that way I realized we were both changed forever.

I spent more and more time with her making love for hours, exploring every
possible position and style and falling deeply in love with her...


Copyright 2008 sniffmecioc@yahoo.com

Posted on Nifty by permission.  All rights reserved.

Comments welcome.

xoxo
-sniffme