Date: Thu, 17 Aug 2000 17:54:11 -0700
From: Diane <diane@sissy.net>
Subject: Diane's Journey - 1 (TG story)

Diane's Journey - 1

Standing naked in front of the mirror I looked critically at the unwanted
features of my body. The lack of contours, the drab sameness, the lack of
femininity.

Smiling shyly at my image, I picked up the girdle and gradually began my
transformation into the feminine being that I wanted to be in my dreams.

Stepping into the open bottomed girdle, I crossed my legs and deftly began
to slide it up over my hips. Breathing in, I tugged it into place and
pulled the side zipper up, enclosing me firmly and compressing my errant
tummy into a more restrained line.

Turning side on to the mirror, I noted with approval the marked
improvement in my figure. Sitting down on my dressing table stool I took
up a silky, sheer stocking. Slowly I slid up up my leg, making sure toe
and heel were straight. Then carefully I began to attach the stocking top
to the three suspenders hanging from my girdle. Front and side are always
easy, but the rear one takes some twisting and fiddling until all was
smoothly in place to my satisfaction. The whole thing I repeated with the
other stocking.

Pleased with the effect, I ran my fingers down my thigh, thrilling in the
feel of taut suspenders, smooth nylon - the whole effect of it all.

Next came my bra, cups at the back initially whilst I joined the hooks,
then swinging it around I lifted it into place, arms sliding through the
narrow straps.

Stepping back once more, I pirouted in front of the mirror again, inwardly
pleased by the effect I was having. The bland, straight torso of the
unhappy boy was being transformed into the shapely outline of a shyly
smiling girl. Pure white, the girdle held me firmly in place, my lacy,
padded bra looked enticing.

Lifting my white slip above my head, I let the delicious smooth fabric
gently caress my body as it slid down into place,

Sitting down once again, I quickly strapped high-heeled sandals onto my
nylon clad feet. Standing up I once again took a critical look at the
emerging girl before me. Slowly I had been taking away my freedoms - tight
girdle, fragile nylons, teetering heels. As I became more alluring I was
becoming more constrained.

On my stool again, the serious work of cosmetic application began. Subtle
eye shadow, defining mascara, a touch of rouge along with bright, moist
lipstick worked wonders on my rather plain, once boyish face.

Coquettishly I smiled at the girl before me, immensely pleased with the
effect. The plain, sad boy had gone, in his place was a pretty, feminine
creature who smiled a lot.

Some simple jewellry was added to fingers, ears and throat, completing the
femme image.

Lastly came my dress. A pretty cotton creation that buttoned down the
front. Putting it on like a coat I began buttoning it down, my pretty
feminine and enticing underwear slowly disappearing beneath the folds of
the dress. Lastly I strapped a wide, glossy black belt around my waist to
accentuate my figure.

Twirling once again before the mirror, my skirts flying and revealing just
a hint of lacy petticoat I giggled in delight.

"Are you in there?"

The shock of the voice shattered my reverie like a bucket of cold water.
My knees went to jelly and my heart was pounding as John suddenly walked
into my bedroom.

I don't know who was more shocked - me at being found out or him at the
sight of his friend transformed. I couldn't speak. I just did not know
what to say.

He broke the silence, disbelief in his voice: "Is it really you?"

"Yes, John, it is." My voice was soft and faltering as I struggled to gain
some semblance of control.

"You look amazing."

"Thank you" I blushed.

"No, I really mean it.... you look terrific. But why...?"

"It is hard to explain... I guess I have always wanted to be a woman. I'm
not much of a man...." my voice trailed off.

"Well, it might take a bit of getting used to, but I'll try."

"I.. I.. thought you would think I was stupid..."

"No! Not at all. I've often noticed that you have never been a macho type.
Now it is beginning to make sense. Maybe that's why I like you... why we
get on so well - because you aren't much of a man, as you say."

"Interesting... I have never thought of it like that."

"What do I call you?"

"Diane" I replied.

To my pleasant surprise we were talking as before, relaxing in each
other's company once more. After all, we had been friends for a long time.
Sitting down again on my dressing table stool, I demurely rearranged my
skirt. He sat on the edge of the bed, watching me with a wry smile as I
did so.

"Diane" he paused, savoring the new name. "you do look nice - that dress
really suits you" he observed.

"Thank you. Yes it is one of my favourites."

"So, you have more dresses?" He sounded surprised.

"Yes, of course. I do like to dress up."

"Obviously you are serious about this. How long have you been doing it?"
He was cleary intrigued by it all.

"Oh, ever since I can remember, I guess. I often wish I was a girl."

"Well, you come across quite well. If I didn't know, I would be deceived."

"I don't consider it deception - I truly believe I am feminine: I spoke
with conviction.

"Yes, I believe you do" he responded. "Talking of deception, you actually
look thinner in the waist, more shapely."

Blushing a little I replied "I find that a girdle does wonders to my
figure."

"Really?" he was interested now. "I have always found female underwaer
very erotic, more so than a naked body, I must confess. I don't suppose
that you wear real stockings?" he finished hopefully.

"Yes, of course I do."

"Wow! I find such underwear a real turn-on.... Oh! What am I saying? I'm
getting turned on by what you are wearing...." he paused, taken aback by
the significance of what he was saying. "I.. I.. I'm not gay you know...."
his voice trailed off.

Flattered by his words I responded: "Neither am I. This is a very
confusing situation for both of us."

"What do you mean?" he asked.

My heart pounding with trepidation, I was determined to express my true
feelings - to lay all bare to him. We had always been quite open with each
other... except for my one deception that was now uncovered.

"I want to be a woman in every way. If I were to have sex with a man, I
want to submit - to have the man possess me. Never do I desire to behave
sexually or otherwise as a man."

He did not seem to know how to respond, just looking at me. Seizing the
situation I continued.

"A gay man would not find me sexually attractive as you seem to. I am
wearing very feminine attire - petticoats, girdles and stockings do not
arouse gay men, but they arouse you, don't they?"

"You are serious, aren't you?"

"Yes" I replied as I lowered my eyes, staring nervously at my hands
clasped in my lap. "I'm sorry if I have upset you...." My voice trailed
off as I looked up at him meekly.

"Don't be silly... you haven't upset me. It is just that this is a bit
hard to come to terms with. Come and sit next to me." He patted the edge
of the bed beside him. Moving over, I sat down close to him, our bodies
just touching.

The effect was electric. My heart was pounding as I realized that he was
looking at me in quite a different way. I smiled, not sure what to do
next, waiting for him to take the lead.

Very gently he put his hand on my knee, softly stroking as he pushed my
skirt up a little, revealing my sheer nylons and just a little of the lacy
hem of my petticoat. The feeling was exquisite.

"Oh Diane!" he exclaimed "you're so lovely... I just love the feel of
stockings and petticoats."

Learning over, I kissed him softly on the cheek. His response was
frightening in its intensity. Pushing me down on the bed he was suddenly
on top of me, his lips greedily pressed against mine. It all happened so
fast I was swept along by his intensity. He had one knee between my legs,
effectively pinning me to the bed by my skirts.

I did not try and resist as his weight pressed down on me. Instead I found
myself eagerly responding, wrapping my arms around him as I felt his
tongue sliding past my eager lips. At the same time I could feel has hard
cock grinding against my petticoated thigh.

"Oh God! Diane! I am so horny.... I'm sorry but I can't help it" he
exclaimed as we came up for air.

"Don't apologize for your perfectly normal desires my sweet" I
responded. Seizing the initiative I decided that it was now or never.

Smiling up at him I coyly suggested the first step. "Let me kiss it
better."

"Oh! Would you?" he stammered as he rolled off me and began frantically
trying to undo his jeans.

"Slow down my sweet... let me do that... just relax and enjoy yourself" I
spoke quietly and confidently as I deftly began to undress him. He sat on
the edge of the bed, leaning back with his arms supporting him as I knelt
down in front of him and set to work for the first time in my life on a
man's raging cock that craved sex.

I surprised myself with my calm eagerness as my lips kissed his hard,
smooth shaft. He moaned softly as I moved down upon him, slowly taking his
cock into my mouth. His hips gyrated eagerly as he felt my warm, moist
mouth. Quickly I began to move up and down upon him, knowig full well that
his orgasm was not far away.

Suddenly, gasping loudly his whole body jumped again and again as his
semen spurted out in blessed relief. I kept moving and sucking, tongue
twirling as his warm, moist sperm pulsed into my mouth. Much to my
surprise, I did not gag on his juices, but gladly swallowed them all.

Gradually his ecstatic tremors susbsided and he was still, lying back now
upon the bed. Pleased with myself and aware of his pleasure I kept his
slowly softening cock in my mouth for a while longer, savouring the feel.

Reluctantly, I disengaged myself, moving up beside him on the bed and
snuggling up close.

Leaning up on one elbow, he looked at me and grinned. "Diane, that was
just great!"

I smiled shyly. "I'm glad you liked it."

Softly stroking his now soft maleness I began to feel the faint stirring
of desire once again.

"Oh! Diane!" he exclaimed. "You are making me want to come again."

"Then teach me how to please you" I murmured.

He paused, staring at me in disbelief. "Do you really want me?"

"Yes, of course I do. But as a woman. Please make love to me as a woman" I
begged him.

"I will hurt you most likely" he responded.

"Hush my sweet. A virgin always suffers at her deflowering. Let me prove
to you that I want to submit...."

As I lay on the bed he began to unbotton my dress. I quickly unbuckled my
belt as his hands slowly worked their way down my dress, revealing my lacy
slip as he went. I was determined to please and gently caressed his face
as we stared into each other's eyes.

By now he had a raging erection again and was ready for action. Placing a
pillow on the bed he rolled me over, my bottom raised up slightly for him.
Stroking my lacy rump he pushed up my petticoats and quickly pulled down
my panties. Luckily I had put them on outside my stockings, and I made a
mental note to always do that from now on.

"You look delectable!" he murmured. "Most women have no idea how arousing
lacy underwear along with stockings and girdles can be."

"I'm glad you like it."

Going across to my dressing table he found some lubricant and deftly began
to ply my warm bottom with its slippery coldness. I tried hard to relax
has his fingers explored my tight, virginal opening.

"I'm all yours, John" I spoke with conviction, although my heart was
thumping loudly with a mixture of fear and anticipation.

Moving up behind me he spread my legs a bit more and made me kneel up a
little to allow for easier access.  Suddenly I could feel his eager, warm
hardness sliding against my slippery ass cheeks.

"Now try and relax my sweet" he commanded as his hands caressed the smooth
nylon of my slip.

"I'm all yours, my darling" I murmured. "Oh! John! Possess me! I want you"
I cried out.

Abruptly I could feel his urgent thrusting as he attempted to push his way
in. Backing off a little he began a more methodical approach, pushing
slowly and then retracting. Each time he pushed in a little further, and
each time he stretched me some more and hurt me a little. Whimpering a
little I tried hard to relax, wanting him desparately in spite of the
pain.

"Take me John!" I begged him.

With one sudden thrust he broke through and was inside. He growled in
delight as I cried out in pain. Lifting up my buttocks I tried hard to
take him in deeper. The pain was considerable, but I didn't care - I
wanted him desparately - I wnated to prove to us both that I could make
love as a woman.

His rhythmic thrusting was building up as he clasped me to him. At last we
were one as I gave myself completely up to him. Gasping and and grunting,
moaning and panting we were locked together in his frantic drive towards
orgasm. Time and surroundings disappeared. My existence was purely as his
pleasure thing as I fought to suffer quietly, burying my face in
the pillow to stifle my cries, wanting only to please him.

Suddenly with a triumphant cry his orgasm engulfed us as our bodies
shook to his pulsing pleasure.

Slowly his spasms began to subside and his relaxed body pressed down upon
me. I lay still beneath him, pleased with myself but rather sore. I could
feel his softening cock slowly slither out of my tender hole, semen oozing
down between my legs. His soft, steady breathing told me that he was now
asleep, totally relaxed. I did not resent this, but rather was really
pleased that I had given him so much pleasure. Time rifted on as I dozed a
little beneath him.

After a while he awoke, and rolled off me suddenly.

"Diane, I'm sorry ... I must have fallen asleep."

"Don't apologize, I am glad that you are so relaxed."

"But aren't you offended?"

"No, silly, of course not! It was lovely just feeling you relax
completely."

"I have to say, that was the best sex I have ever had!" he exclaimed.
"I've never come twice before, and you were so tight and eager..."

"Good!" I spoke with conviction. "Without a doubt, today has been the most
intense, most overwhelming, most emotional experience of my life."

"But didn't it hurt? Don't you resent me for that?"

"Of course it did, but it was worth it. And, no, I do not resent you at
all. I really wanted you. In fact, I really enjoyed being totally
dominated."

"In spite of the pain?"

I blushed. "In spite of or because of....my emotions are all over the
place at the moment. I'm not sure. I think because of.... sorry, does that
worry you?"

"No, I'm afraid that it excites me."

"Good! Then we are compatible. Don't be afraid. I need desperately to be a
woman - to be treated like one, to have you make love to me as a woman."

"I have never had an offer like that before" he smiled.

"Today was a bit different, though, don't you think? We have been friends
for a long time. Suddenly we have become a lot more intimate. We know a
lot more about each other."

"Yes we do - you have certainly been a revealtion to me today. I'm still
not sure how to take it. On the one hand, I just loved the sex, on the
other... well, it will change our realtionship quite a bit, I suspect."

"Yes" I replied. "We were equals, but now I have willingly submitted to
you. Inevitably our behaviour towards one another will change. But, that
is to be expected. The sexual act, in the end, is and act of domination
and submission. We shouldn't pretend otherwise, because it is. Men gain
immense pleasure via orgasm, but evidence indicates that most women don't
get an orgasm via penetrative sex. Don't expect me to behave like a man -
I am no longer one."

"But what about me hurting you?" this obviously intrigued him.

Stretching out my leg I indicated my shoe. "I guess there is a bit of
masochism involved. Look at my shoes - would you like to wear them?
Restrictive and unstable, uncomforatable and even painful, but like a lot
of women, I like to wear them."

Taking his hand I placed it on my hip. "Feel my girdle - tight and
restrictive, uncomfortable at times with fiddly suspenders and such like.
And yet I wear it whenever I can. Why? Because it makes me feel feminine
and certainly helps to make me look better."

"And what you are saying is that sex is like that for you?" he asked. "It
makes you feel feminine?"

"Yes, I had never thought of it like that, but once you took control...
well... I just wanted you. I could feel your desire, feel your pleasure,
and I wanted to give you as much as I could. A joy in giving. Don't think
of me as your male friend - I am now Diane. And we have become lovers."

"This is heady stuff. I am still coming to grips with the change" he
replied.

(to be continued)

diane@sissy.net