Date: Thu, 28 Dec 2006 14:51:40 -0800 (PST)
From: bill bobber <givingitupgladly@yahoo.com.au>
Subject: Getting Started - 7

Getting Started - 7

TG - Young friends
Cross-dressing, Oral, Anal,
Masturbation

This story deals contains sexualy explicit scenes. Do not read
if you are not over 18. Otherwise, enjoy.



I knew that I had to wait for
my first chance to dress up. I wanted to do this right and that meant my mom
needed to be at work. She's a nurse and works nights sometimes. That wouldn't
happen for another four days, but in the meantime I could get ready. So the
next day after school I told mom that I'd gotten muddy playing football at
school and needed to take a shower. After locking the door I stripped and just
enjoyed the feeling of being naked for a moment. I love that feeling and would
be naked all the time if I could. One day I'll have a place of my own and then
I will be naked all the time, unless I'm wearing some sexy lingerie or perhaps
a French-maid outfit (giggle!)
After admiring my smooth young body in the
mirror and checking out my pert teen butt (I know it sounds conceited but I do
have a nice round little ass and I like the idea that men might find it sexy
and want to get into it) I got mom's razor out of the vanity. I'd never shaved
myself before but one good thing was that I didn't have a lot of body hair.
Never-the-less, I wanted it all gone. So I began, slowly, carefully, enjoying
the experience of preparing my body for a man to make love to. As I made my
body more feminine looking I imagined that I was Jim's girlfriend and that we
lived together. He would be home from work soon and I wanted to look my best
for him. I would be waiting, all smooth and clean, wearing the sexy clothing he
had left for me. Ready and eagerly anticipating the sweet love we would soon be
making. I imagined him coming in and the happy look on his face as he sees me
standing there in my heels looking like a hot slut. I would walk over to him,
the way
 that walking in 4" heels makes you walk, and kiss him. Then, I would drop to
my knees and free his beautiful cock from where it has been kept waiting all
day for me. Looking up into Jim's eyes I would smile lasciviously before
engulfing his long, thick cock in my hungry mouth. Then, I would please my man,
who had been working hard all day and needed some relief. I had loved sucking
Jim's cock and knew that I would not hesitate to taste him in my mouth again.
In my imagination, after a vigorous blow job, I would taste my man's thick cum
spurting into my mouth and down my throat. I wanted Jim to be my boyfriend so I
couldn't imagine doing anything other that swallowing his seed. I wanted him to
love me and I wanted to satisfy his needs completely. To do that I knew I
needed to be the best cock-sucker I could, and to savour every drop of sperm
that came out the end of my man's cock. It also meant, I was pretty sure, that
Jim would be wanting to fuck me, maybe a lot. I was a little scared thinking
about that, Jim did have a big penis. But there was no denying the fact that I
was also excited. Jim had been gentle with me as he had shown me how to please
him with my mouth. I knew that I could trust him to be gentle with me if he
wanted to fucked me. And as I stood in the bathroom looking at my slender and
now hairless young body, I knew I wanted him to fuck me. I wanted to do
everything in my abilities to satisfy him. I wanted to be
 Jim's girlfriend and that meant giving Jim not only oral love, but also free
access to my tight young ass.

Two days later, mom worked a night shift. One
of my older sisters had moved out by now to college and the other was out on a
date and I knew she would be very late. I was going to be alone. I did my best
to look calm and un-excited during dinner as mom reminded my for the millionth
time to do my homework. "Oh yeah, I have some extra special homework to do
tonight mom."

Finally, the door closed and I was free to do, and look, as I
pleased. I ran upstairs and took down the bag from the back of the closet
shelf. I was naked in seconds. As I looked down at the wonderful outfit laying
on the bed before me I felt my penis rise. I was so excited!
First it was the
stockings. It took some practise and patience getting them on but I didn't mind
because it felt so wonderfully girly pulling on stockings. Next was the garter
- it was easier, once I figured out which way was the front. I fastened the
snaps and smoothed out the stockings. I already felt fantastically feminine and
so sexy. I just stood in my room and fondled my penis for a few moments
overwhelmed by the erotic sensation of transforming myself into a girl. Next
was the bra. It was padded so it looked like I had breasts. Getting the
fastener to work was tricky at first, but I soon got it.  I reached up under
the bra and squeezed one of my nipples which sent shivers up and sown my spine.
Now the shoes. I had been looking forward to these perhaps most of all, but I
was also kind of afraid of them. They were very exciting with such high heels
and the straps that wound around my leg, but I had no idea of how to walk in
them. I almost collapsed the first time I tried walking. This was hard! I felt
all wobbly like I was going to fall over at any moment. How did women walk in
these things I wondered. I stood in the middle of my room and teetered from
side to side as I tried to figure it out. I soon found that if I held my arms
out like I was walking a tight-rope that it was a bit easier. So I practised
like this for a long time - walking as back and forth across the room, arms
straight out to the sides, trying to walk as much like a woman as possible.
Soon, I began to see the upside of high heels. First, they made my legs look
really long and my calf muscles were tight which looked good. They also did
something to my ass which was really thrilling. I don't know what happens back
there when you've got heels on but it seemed to make my ass really look like a
girl's, all round and pear shaped. I spent quite a bit of time fondling my
smooth butt cheeks while imagining it was Jim that was feeling me up. What a
little tart!
Finally, heels made me walk sexy. Not graceful, but totally
feminine. As I watched myself in the mirror, transformed into a young
slutty-looking girl, I was perhaps most excited by the way I walked. Or
strutted, I should say. It took a lot of practise, but I was enjoying every
second of it. Learning to swing my hips, swivel my ass, how to balance on my
toes while I walked so all this motion looked coordinated and sexy. Quite a bit
of practise.
The last piece of the outfit was the wig. Long and blond, the
hair hung down past my shoulders. It didn't smell very good, but not gross,
just not pleasant. The effect on the image I saw in the mirror was remarkable.
Instead of a young man dressed like a young woman, I now saw only a woman.
Sure, a tarty looking young woman who was still wobbly in her heels, but there
was nothing masculine left. I posed and twirled like a slutty showgirl in front
of the mirror imagining I was putting on a show for Jim. I was also getting
more and more aroused and needed to do something about that little thing
sticking out from where my pussy would be if I were a woman. I knew it was time
to play with the other items that Jim had given me.
The two dildos and the
lubricant were hidden under my bed. I know, not very original, but I had been
playing with them at night before I went to bed. I enjoyed sucking on the
smaller of the two because it was sculpted to look and feel very much like the
real thing. I would stroke my cock as I imagined that Jim had come in my
bedroom window and needed to have his balls drained by my eager young mouth. I
would orgasm imagining that the pulses of cum erupting from my cock were really
shooting from Jim's big dick into the back of my mouth while I slurped and
slobbered on the lucky dildo.
The bigger one was more firm and had a fat head
that led to an almost equally fat shaft, that had to be at least 10" long. I
hadn't done much more with this one other than kiss and lick it. It was too big
to comfortably suck on. This one, "Big Daddy," I had been saving for tonight.
It would be deep in my ass before the night was through, I vowed. I needed to
be ready when Jim wanted to fuck me and this monster was going to be the one to
get me prepared. Or I would just fuck myself silly; either way it was win-win.
I moved the mirror so that I could see myself on the bed, then, with my two
latex lovers and the tube of lube I lay back against the pillows and spread my
legs. I began by inserting a finger into my rectum. Mmmmmm. I had been craving
the feeling of something right there. Something in me. Something in my bum.
Ohhh! It might only be a finger but it felt so good! So right! I was sure that
I wanted Jim to fuck me and I wanted it to be wonderful. With one hand stroking
my rigid cock I began finger-fucking my horny hole. I felt so incredibly
slutty! Dressed like a young hooker, finger up my ass, a young man crazed with
lust as he imagines being used by an older man for his sexual satisfaction.
Shameless! Yup, I felt no remorse. Only a growing need to be used completely by
Jim. To be fucked and fucked until I was filled with his cum. Oh! I was so
horny. It was time for the lube.
I took my time coating the tight opening of
my anus with the slippery stuff because I was getting a little overheated. I
wanted this to last and if I kept up that kind of pace I would cum too soon.
I gently eased two fingers into my love hole. I had to go very slowly because
my sphincter was fighting to close. "Come on now," I tried to tell it. "You
want to be part of Jim's girlfriend don't you? We want to be Jim's girlfriend.
That means he's going to (hopefully) want to slide his big fat cock up inside
you. You need to let that happen. Surrender, don't fight it. Let it in. Let him
take you and fill you."
It must have worked because it stopped hurting and I
began to feel pleasure as I sawed two fingers in and out of my slippery rectum.
I enjoyed doing this for several minutes before I felt I was ready for
"Junior." This was the smaller of the two dildos. But it was still a lot bigger
than two fingers. More lube, more pep talk, and then I was ready; pressing a
cock shaped dildo against my poor little rosebud. My legs were pulled up
against my chest, knees wide apart, ass cheeks spread open as I gently but
firmly pushed the dildo up my ass. There was pain, but it didn't last long and
it was a good kind of pain. Before long I had the entire length of the phallus
inside me. I stroked my cock as the wonderful sensation of having something big
in my ass washed over me. I almost came right there, but was careful to stay in
control.
I carefully got up off the bed and stood looking in the mirror. I
loved what I saw. A sexy hot tramp who had a dildo in her ass. I looked at the
garter, the long stockings, the very high heels, the padded bra, and the long
blond hair and I nearly came again. I slowly began do do a sexy dance wishing
that Jim could be watching me. I loved the way the dildo felt in me as I moved.
I loved the feeling of being full. I turned so I could see my ass and the dildo
sticking out of me. It looked so big! My ass looked good being fucked by the
thick phallus, like a girls. I hoped Jim would think it looked sexy too.
Now
it was time for "Big Daddy." My anus had become used to "Junior" and it was
time for more training. I climbed onto the bed on my hands and knees and slowly
and gently pulled out "Junior." With a wet sounding "slurp" my latex lover left
my ass feeling empty. But I wouldn't be for long. I had "Big Daddy" ready. And
more lube.
I placed the big dildo behind me with the huge tip against my
already stretched anus. Pausing to admire the view in the mirror of a young
horny boy/girl preparing to fuck herself I then began to lower my ass onto the
dildo. I'll spare the details. It took some work and a bit of pain but I had
lube and more importantly, the desire. And after only a few more minutes I had
the biggest dildo I had ever seen deep in my ass. I leaned forward on one arm
and with my other hand began to stroke myself. I was almost beyond the point of
control now. The view in the mirror, the anal sensations, and the knowledge
that I was being impaled by a monster cock was driving me crazy with lust. I
loved how my ass felt and loved imagining Jim was behind me on the bed fucking
me deep and strong. I bucked my hips back at my imaginary lover fucking myself
against him letting him know I wanted it as much as he did. I loved feeling
like a hot young slut crazy for men's cocks and cum. I loved how I
 looked all dressed up in order to please my man. I wished I had a man with me
right then to teach me all night long how to fuck and swallow cum. I thought
about how many men there probably were right now all over the country who would
love to find a horny and willing boy to be their sexual plaything. How
wonderful it would be to have one, or two, or even more, suddenly appear and be
as happy to see me as I would be to see them. And then we would be able to make
our fantasies come true. Mine, of being able to please a man (men?) sexually,
and theirs, of finding and fucking a hot and horny young boy/girl.
It was too
much to handle. I came. Hard. Face down, ass in the air, monster dildo sticking
straight up, cum all over the sheet below me, I shot and shot and shot until my
release was finally complete.
Afterwards, I didn't have the strength to move
for quite a while. I just revelled in the "just been fucked" feeling, wishing
it were a real cock that had fucked me. I reluctantly pulled "Big Daddy" out of
my ass. I felt all wiggly and loose. But I was already beginning to feel horny
again. My ass felt empty and I didn't like it. I wished for the millionth time
that Jim really was with me. I would gently suck him until he was hard again
and then ask him to fuck me again. And again. And again.


To be
continued....

Please let me know what you think. I write these stories for
YOUR pleasure (and yes, mine too) so I love to hear that someone is paying
attention. Thank you to all those who have taken the time to write me. Thank
you, thank you; it's been great to hear your comments. I love to please!

Love, Randylad(y)