Date: Fri, 26 Jun 2009 12:02:36 -0400
From: C Cat <cheshirecatt2001@hotmail.com>
Subject: Gayle

      My name is Gayle. As you have probably surmised, I am a crossdresser.
I have been dressing since I was little, beginning like so many others, by
wearing my mother's panties. Over the years I progressed to my own wardrobe
and began wearing makeup as well. Being tall at 5'11" I never thought I
could "pass", but I always dreamed of the day I could go out in public.
      Having grown up in the `60's I had grown my hair long. Much of the
time it was below my shoulders and gave me a very feminine appearance when
I would dress. For the longest time I wanted to know what it would be like
to be with a man and be treated fully as a woman. I longed to experience
all those things I had missed in high school...the dating, the making out
in my boyfriend's car, you know, all the usual girl stuff.

      By the time I was 21 I had discovered the wonders of the adult
bookstore in my area. It afforded me a place to buy all the TV magazines I
wanted and in those I found the classifieds. Through the ads I was able to
contact admirer's and other "girls". I also found I could anonymously enjoy
a stiff cock in my mouth now and then without the fear I had of a face to
face meeting. What a glorious invention was the "Glory Hole".
       Although I corresponded with many and fully intended to meet in
person I always got cold feet. "What if" stopped me. What if it was someone
I knew, what if someone saw me, and of course ... what if I liked it!
      Some years later I happened back to that bookstore. I was wearing
lingerie under my jeans and shirt as I did frequently. As chance would have
it I wandered into this particular movie booth and there it was...scrawled
on the wall above the coin slot. "Do you TV? Tall, mature man will treat
you right...call...555-9145". Why I wrote that down I don't know, why I
actually called I don't think I will ever know...but I did. Stranger yet
was that I actually dialed the number the next day.
       "This is Hank" the voice said..."I'm Gayle and I saw your ad on the
wall at the bookstore" I said.
 "Are you a TV?".  "Yes, I am, but I have never met anyone and I'm really
nervous" "...Don't be, I won't hurt you".  Yeah sure, where have I heard
that before I thought..."well, what are you looking for Hank" I said
feigning confidence.  "Just a pretty girl to treat right and have fun with,
does that interest you Gayle?"  I stammered yes and we proceeded to talk
for about 20 minutes. Near the end we arranged to me in person and talk and
see where things would go. While I had every intention of meeting him, I
also knew my history of breaking such dates and that this would most likely
be another in that string...but I made the date anyway.

	A week flew by and suddenly it was do or die.
	 I underdressed as usual and drove to the appointed spot. I saw
someone matching the description he had given me waiting by the
fountain. Hank had said he was tall and that he was. At about 6'5" he was
just what I had hoped for, someone who I could look up to even as I stood
in my 3" heels. I walked towards him and said, "Hank?"...shaking all the
while.  "Gayle?" he responded. I quickly looked about to see if anyone had
heard him call me by a girl's name. No one was there and I answered yes. He
sat on the bench and motioned for me to join him. I did so, close enough to
have a quiet conversation and not be overheard, but far enough away for my
own security.

"I'm glad you came. Don't be nervous."  "That's easier said than done,
Hank, this is my first time meeting someone in person".  Small talk ensued
and as time went by I became more relaxed and at ease with him and my new
situation.  "Did you wear anything pretty for me today?"  "Well, sort
of. I'm wearing a white lace bra/panty set with nude thi-hi stockings. I
wanted to feel more feminine since I wasn't completely dressed" "Mmm, I
wish I could see them" he said as he shifted his position.  I thought I
could see a bulge growing in his trousers, but I was afraid to look
directly to be sure.  "It's a bit open here for that" I giggled. "And
besides, I would prefer to be completely dressed before we got to that
point" That's when I got the surprise of my life...  "I have a room at the
hotel over there, did you bring your things with you? We could go there,
you could change and we could get to know each other better!"  Before I
could think I nearly shouted out "Yes!". Then I turned bright red and knew
the time had come for me.  Hank handed me a room key...  "How much time do
you need to make yourself pretty?"  "About 45 minutes, maybe less" "I'll go
to the lounge and have a drink while you take your time and I'll be up in
an hour. Now go get your clothes and enjoy yourself"

	Off I went, nervous as hell, but excited, anxious and horny all at
the same time. This was to be my debut. Someone would finally see
Gayle...and I would probably lose my virginity!


	Gathering the suitcase from my car I headed to the entrance and up
to the 3rd floor. Room 327 ... I'll never forget that number. As the door
opened I saw it was a suite, not just a single room. I was impressed that
he would go to all this expense for someone he'd never met. I locked the
door and put my case on the king size bed. Taking a deep breath I opened my
bag and began to undress, putting my male things in the closet and
beginning my selection. First I attached my breast forms and repositioned
my bra, then I put my hair in a pony tail and rummaged through my makeup
case, then it was off to the bathroom. A quick rinse of my face followed by
foundation, shadow, mascara, blush and eyeliner did the trick. I slipped
into a rose colored ¾ sleeve blouse with covered buttons and a black A-line
skirt. Then I chose my black sling backs with 3" heels. Grabbing my brush
and lipstick I returned to the bathroom to finish.
	It wasn't 2 minutes after that there came a knock on the
door. Glancing through the peep hole I saw it was Hank and I slowly opened
it to let him in. As he entered he was looking me up and down the entire
time and smiling. This made me tingle and I returned his smile demurely.
"You're very pretty Gayle" "You're too kind Hank" I returned, blushing.
"Come in, after all, it is your room" I giggled...  "Let me look at you" he
said, taking my hand gently and urging me to turn for his viewing
pleasure. "I'm glad you decided to come today and meet me, you look lovely"
"Thank you kind sir" I responded and blushed profusely, "I'm so glad you
find me attractive".
	No sooner had I said that when Hank gently urged me towards him and
took me in his arms. Smiling, he held me close and slowly brought his lips
to mine. My first kiss with a man and I was already melting in his arms and
pushing stiffly at my panties. I was getting so hot...why had I waited all
this time to experience this? His lips parted and his tongue pushed against
mine which opened in response. His tongue probed my mouth and danced with
mine. My breath quickened and my arms tightened around his neck.
	It seemed like an hour but it was only a minute and he pulled
slightly back. My lips still parted, my breasts heaving and my face flushed
all told the tale. I was burning with desire for this man, and he knew it!
Hank kissed me again and as his tongue stabbed my mouth I dreamed of his
cock invading my virgin pussy. His hands wandered and soon one cupped the
right cheek of my behind, kneading the soft flesh while the other stroked
my side and teased my left breast. My fingers stroked the back of his neck
and urged his kiss to linger. Soon my moaning betrayed me and I began to
kiss him harder and press my body to his.
	His left hand slipped beneath my skirt and was caressing my panty
covered ass, his fingers slipping under the leg band and teasing the head
of my dripping clit making me ooze even more. Hank began to unbutton my
blouse and touch my bare flesh. His lips grazed across my neck and the tops
of my swelling breasts. I pulled his head back to me and kissed him
voraciously as my hands unbuttoned his shirt and forced it off his
shoulders. I kissed his hairy chest and toyed with his nipples. As he
unzipped my skirt I reached for his belt, unfastened it and my skirt
dropped around my ankles. My blouse fell to the floor as I kicked free of
my skirt and stood before my man in my sexiest lingerie and
heels. Strangely I wasn't embarrassed but I was filled with a feeling of
femininity I had never experienced before. I was his WOMAN! It was my dream
come true!
	I kissed Hank again and my fingers fumbled with his zipper. I could
feel his hardness and his length and became scared. Shortly this man would
make me a woman and take my virginity. I felt like it was my wedding night.
	Slowly I sank to my knees before him. The snap of his trousers
opened and down they came revealing the outline of his manhood beneath his
white jockeys. While not very sexy, it was extremely sensual for me. I
leaned forward and planted kisses along it's length through the
cotton. Traces of my lipstick outlined the object of my desire. Then at
last I removed his shorts and saw it up close. Pressing it to his belly I
tickled his balls with the tip of my tongue and then worked my way up to
the swollen head. Parting my lips I took it in my mouth and savored my
lover's taste and smell. It was a heady moment and I was lost in the act of
sucking Hank deeply into my mouth. My lips closed tightly and pressed the
soft flesh as it slid out then in again. Yes, this is what I longed for!
This is what I needed! In and out it moved as I bobbed my head, all the
while cupping is swollen sack and teasing the region behind them with my
fingertip. I sucked the knob and flicked at the piss hole with my
tongue. Soon, I hoped, it would open wide and flood my mouth with the
delicious juice I loved.
	Suddenly his hands grasped my arms and he had me stand. I kept
stroking as he kissed me wildly. He pushed me back on the bed, my legs
falling open with him between them. My panties slid down my thighs easily
and my excitement sprang into view. Hank wasted no time slipping me into
his mouth and raising my legs onto his shoulders. I felt a fingertip trace
the outline of my pussy hole, then slowly probe me as his mouth descended
on my clit. The invader searched and then left, only to return with a
companion. He was making me wet and open for his cock. His lips left my
clit and found my hole. A wet tongue replaced the fingers that had
pleasured me and I squirmed beneath his licking. I had never had my pussy
eaten and I wondered why I had waited so long for this delicious bit of
sex. As he licked at me I reveled in all the sensations I was feeling, the
heaving of my breasts, my nylon encased legs on his shoulders, his fingers
and tongue teasing and probing. I was in heaven! My entire body felt alive
and so feminine.
	Lowering my legs as he pulled back Hank turned me onto my stomach
and told me to get on all fours. I did as instructed and he parted my
cheeks and again licked my pussy. This time his hand encircled my hardness
and stroked me. I was dripping wet and aching to be taken by this man and I
told him so.
	"Put it in me, fuck me Hank! Take me now and make me your woman."
	He knelt on the bed behind me and rubbed his cock around my
opening, teasing me more. Then I felt the head press at my hole and I
relaxed as best I could. Slowly, oh so slowly, the head slipped into my
cunt. I gasped! He inched his rod deeper and I felt it rub my prostate and
I almost came. A few inches in then he pulled back and inched forward
again. I wanted it all and after a few minutes of teasing I pushed back as
he began a new assault and buried him inside me. His balls slapped my
cheeks as I wiggled try to get more in me.
	At last I was a virgin no longer. Every second he remained in me
made me more wanton. I was lost in the sensations of sex. I began my "pole
dance" and his hands grasped my hips to control my movements. He pulled out
till only the head remained in me and the jammed it all back inside. Then
he'd pull out and rub his length between my cheeks and ram it back
inside. Varying his pace he was driving me wild. I was dripping everywhere,
I wanted to cum, I needed to cum. Most of all I wanted him to cum inside
me. I wanted my first cream pie. I wanted to sleep in the wet spot of this
man. I found myself wishing I could become pregnant from his seed.
	Suddenly he pulled out, leaving me empty and begging for his
cock. He flipped me over and again my ankles were on his shoulders and he
mercilessly rammed his length into me. This was it...I could feel it. He
was kissing me ferociously all the while fucking me with abandon. My ass
humped in rhythm to his thrusts and my stiff clit rubbed against his hairy
belly That was all it took and I almost passed out as wave after wave of
orgasm swept through my body. I came as never before and felt as if my
entire being was being pumped through that tiny opening. Hank kept slamming
his cock into me.
	He slipped his hand between us and scooped up my juices then
brought it to my mouth. He smeared some on my lips and the rest on my
face. Grunting loudly as he watched me clean his sticky fingers Hank thrust
into me in hard short jabs and I knew he was shooting his load deep in
me. I felt the warmth of his seed against my inner walls and I fainted
away.
      When I came around shortly after, I felt his hot cum dripping from
me. I touched my pussy with a fingertip, scooped some up and brought it to
my lips. At last I tasted him. Hank came up beside me and offered me his
cum covered dick which I greedily sucked and licked clean. He tasted so
good and I felt incredible. The acrid taste of our juices was on my tongue
and the drying remains of our mating coated my face. Hank was beside me. I
turned to him and he kissed me tenderly. We cuddled and drifted off to a
short nap.
      I awoke first and slowly as not to wake him I slid down the bed. His
flaccid cock was too inviting and I took it into my mouth. I wanted to see
if I could make him hard again while he was asleep. Sucking and licking I
began to get a response. Soon he was nearly hard and that must have been
what woke him. Looking down at me he smiled and said, "You really love that
cock don't you Gayle?". Mmmmm was all the response I gave as I kept sucking
and now taking his full length down my throat. His hands went between my
legs and found my clit...then he urged me over him in a sweet 69. We stayed
that way for quite some time until I pulled away, turned and straddled
him. Grasping his member I guided the head to my pussy and impaled myself
on that wonderful shaft.
      I slowly worked my magic and we were both entranced. My hands
caressed his strong chest and his grasped my hips helping my
movements. After a bit he began stroking my clit as I became lost in a
wonderland. It wasn't long till I screamed "I'm cumming, I'm cumming" and
my cunt furiously fucked his engorged meat. He rubbed me harder and then it
happened. My juices streamed from me, coating his had and chest. I became
dizzy, but continued to jam that hard cock into my body. Soon he was
bucking up to meet me and then he grabbed my hips and jammed me down on
him, holding me tightly as I felt his cock pulse and spit it's load into
me. I could even feel the ripples of cum course through it before they
splashed the inner walls of my pussy.
      When I felt the last jet I fell forward and kissed him wildly. We
hugged tightly and gasped for breathe. Then I felt him grow soft and start
to slip from my body. I tried in vain to keep him there, but soon the head
slipped free and I felt empty and began to cry. Hank held me close and I
sobbed, not knowing why, but feeling so many emotions I could not
comprehend.
      We drifted off to sleep, to dream, to awake upon a new day.

      When morning came I awoke to the sound of the shower. I found Hank
there and quietly slipped in to join him. We kissed and caressed and
lathered each other up in more ways than one. Finally we exited and dried
each other off. I had the day off, but he had to go. He told me to stay as
long as I cared to as the room was ours till noon.
      I dressed in my lingerie and redid my makeup. Sitting on the bed I
watched as he finished getting ready. All too soon he came to me saying it
was time. I said, "Yes, it is" and I sank to the carpet on my knees before
him. Silently I rubbed his crotch, felt his cock grow hard and began to
unzip him. He started to protest, but I just continued. His pants feel to
his ankles and his cock found my lips. He didn't protest any
longer. Cupping his sack I fondled his balls and licked the length of his
shaft. I kissed and sucked at the swollen head and licked the pee hole
making him squirm. Inch by inch he disappeared into my hot mouth until he
was in my throat. His groans said volumes and I let him slip from my lips
only to tease his balls with my tongue, lick my way up his shaft and then
deep throat him again. I sucked the knob and used my tongue on the
underside. He began to thrust into my mouth. I pulled back and stroked him
as I said, "You can cum, but you have to cum on my face darling". He nodded
yes and I swallowed him completely. Now in earnest I sucked his dick and he
fucked my face. A few minutes later he moaned, "Now, Gayle, now". I pulled
back and stroked him hard, aiming it at me. The pee hole opened and he
gushed like Old Faithful spurting stream after stream of hot cum all over
my face. It dripped from my eyelids and my nose and chin, but I managed to
scoop some up and feed it to myself. When he finally stopped pumping and
some was just oozing out I took him back in my mouth to suck the rest from
his balls.
      When I was satisfied there was no more I let him pull free of my
lips. I helped him dress and he stood there looking at me.
      "I want you to remember me this way till the next time. On my knees
before you, covered in your hot cum. Now go to work and daydream of me like
this."

      He left, blew me a kiss as the door closed.
      I lowered my panties and jerked wildly at my clit as I cleaned his
load off my face with my fingers and tasted every drop. In short time the
carpet was stained with my juice, and that's how I left it.

      Hank called me a few days later. We met quite a few more times and he
gave me some lovely presents over the next few years...till his wife found
out, but that's another story...