Date: Sun, 17 Aug 2008 19:13:01 -0700 (PDT)
From: Joe Cool <cog_123@yahoo.com>
Subject: A Cinderella Story (TG)

It started with an internet conversation. SgrdE8 was new to the chat rooms
I had been on recently. My fascination with cross dressing and deviant
homosexual behavior was completely in my head and online to that point. I'd
never expressed it with anyone in real life, and certainly never done any
thing about it. Many people I'd talked to were in the same boat, and I
often wondered how many people I'd pass in a day that were like us. This
guy was named Greg and he was very cool. He wasn't an arrogant cock like
many, nor was he belittling about the fact that I never had the guts to try
anything like many "out of the closet"-types were. I'd told him I'd flirted
with a few guys and almost brought myself to do something once, but the
situation just wasn't right. He asked me what the right situation was and I
said I didn't know. After talking over the course of several weeks, I
decided I was going to try to actually meet him. No pressure, he assured
me. He knew all about me and was eager to meet me, without reservation or
judgment.
	We met over lunch (he bought) and I was very relieved. We had a
pleasant conversation that didn't include anything about my fantasy
life. Just sports, politics, like any of my regular guy friends. Later we
talked online again and he invited me over for the weekend. Again, no
pressure. After a few weeks of busy schedules, a weekend opened up. I was
nervous as hell, but it was a great feeling. I felt excited and scared,
horny and cautious. I felt alive, like I hadn't felt before in my life.
	When I arrived at his house, I couldn't hold my hand still to
knock. I paced around the front yard of his beautiful secluded home. It was
gorgeous. He'd made a lot of money and bought a nice home with lots of
land. It was well lit, and I kept asking myself what am I doing here?
Thinking he was probably watching me out the window or through a security
camera. Finally, I knocked. After a long, long two minutes, he opened the
door and greeted me with a handshake. Very simple, no pressure. It was very
comfortable. He welcomed me in and I toured the house. We talked sports and
watched part of a game on his giant TV. He asked if I'd mind if I had his
assistant fix us something for dinner. He didn't want me to get nervous
with another person, but I was very comfortable and didn't have a problem
with someone else. Afterall, we were just two friends hanging out, nothing
out of the ordinary.
	After dinner, we had more of the same. He never once even brought
up what we'd talked about, and I was too nervous to do it myself. We got
very very drunk. The more we drank, the more it slipped into conversation,
but still, mostly in a joking way. He told me tomorrow, we could have all
day to escape to fantasy, but only if I was very comfortable.  I ended up
very drunk and about to pass out when he convinced me to go to his
bedroom. At that stage, I was fine, although I was not where near a
position to do anything. He wasn't either, and very soon, we were both
asleep, although in the same bed.
	When I awoke the next morning I was in a good mood. I had no ill
effects of the alcohol the night before. I was ready and committed to
following through. I turned over to see Greg, but he wasn't there. Instead
there was a note: So sorry, I had to run into work this morning. Make
yourself at home. If you are ready, my assistant Claudia would be ready to
assist you in your transformation.
	Hmm, now I was having second thoughts. But in a way, I was more
excited about doing this. I wanted to get myself ready for "my man" and
surprise him when he got home. I found Claudia, and told her I was
ready. She smiled and told me to follow her. She was a fair-complected girl
in her 30's she didn't wear much makeup and seemed to have simple tastes in
clothes and no jewelry. She wore glasses and had light auburn hair.
	"Greg told me about what you wanted, and I'm here to help you with
everything." she said. "I understand you are very nervous, and I want you
to be comfortable. Please let me know if there is anything I can do to help
you." She smiled. She was very non-threatening and I found ease with
her. We chatted a little about clothes and fabrics and I was ready to
begin. I realized that Claudia was going to be my fairy godmother.
	First step was a very hot bath and removal of all my body hair. I
soaked in the hot bath for bath for over an hour. My muscles were
completely relaxed and baths have always made me horny. Claudia assisted me
with removing my hair. She showed me how to shave my legs and arm pits. She
shaved my ass and crotch area - I didn't trust myself. I was quite
embarrassed (for some reason) to have a huge erection while she was shaving
me. Maybe it was the bath; maybe it was the fact that another person was
seeing me naked and touching me or maybe it was the excitement of what was
to come with Greg. I was so giddy and nervous just thinking
about. Regardless, I had a huge boner and Claudia was having a hard time
shaving my pubes.
	"We need to do something about that." She said. I figured she's
want me to masturbate - which would take less than 10 seconds as turned on
as I was. Instead she, without warning lowered her lips to my dick. her
hands rubbed the shaving cream into my legs and she fingered my ass. It
didn't take long, she was very good at giving blow jobs and I was very
horny. I blew a load into her mouth and she licked every bit of it.
	It took me longer to figure out what just happened than for it to
happen. Getting over the feeling of an orgasm, being completely naked and
hairless and in a strange place, I was a little discombobulated. Claudia
gently spoke. "That was quick."
	"You're good." I replied. "It wasn't my first time," she said with
a sly grin. "but please, don't expect that again." She said. It was for
convenience-sake. She smiled as she said that, as if to say she enjoyed it
and was glad to do it, she just didn't want me thinking she was a whore,
which was understandable.
	"Now it's time to do something about your skin.," she said when I
was ready to move on. She used the softest towel I'd ever felt to dry me
off and put me in a girlish pink robe. It was very comfortable. She led me
to a room with a message chair in the middle. She instructed me to lay down
and remove my robe. It was a warm room, and I was very comfortable not
being covered. Claudia gently applied some skin cream on every inch of my
body. She applied some special cream to my breast and squeezed and pulled
them a lot. She told me to relax and let it soak in. She then gave me a mud
mask for my face and put cucumbers on my eyes. Some sort of goop was
applied in my hair, which felt good because I've always enjoyed people
playing with my hair. She told me she'd be back in a half hour and for me
to rest and relax. She turned on some relaxing synthesizer music and
left. I was alone with my thoughts which were quite peaceful and horny. I
thought about what was to come and got excited. A slight hard on
returned. I was also very very comfortable. It wasn't long before I dozed.
	When I awoke Claudia was removing the skin cream with a towel - all
by my breasts, face and hair. I turned over in the chair and faced the
floor, still with my face covered in mud, so I didn't open my eyes. Claudia
applied the cream to my entire backside and left as before. I was quickly
asleep this time. When she came back she told me she had to remove the
cream with the towel. Then she was going to do my nails, then give me a
full body message. I was going to shower off, then my body would be
ready. I was so thrilled with this plan. She removed the cream from my back
side. I was getting really turned on as she worked all around my anus and
rubbed my ass. Once the cream was removed, she did my nails. The smell was
awful and broke my moments of beautiful comfort. When I said something
about it, she lit a candle which was a beautiful flowery fragrance and it
mostly covered the smell. I was still facing the ground when she finished
my nails. My hands and feet were dangling as they dried. While I waited,
Claudia found some body oil that warmed to the touch. She rubbed it in and
gave me a thorough message. I was in heaven, I love messages. She rubbed
every muscle on my back side. I was still horny from the ass-rubbing and
thoughts about what was to come. Now, she messaged and rubbed oil on my
ass, I had to adjust my position as I was now laying on a full-fledged
hard-on. She continued the message and I continued to be turned on and very
relaxed. She told me to turn over. She re-applied cucumbers to my eyes. I
heard sounds of the chair and she told me to lift my legs. She moved out
some sort of stirrups and my legs were now in the air. My ass and dick were
now quite exposed and my hard-on was still hard. She told me she was going
to give me an enema, then wash out and relax my ass.
	It was a little painful, but very stimulating to have my ass
cleaned. I never felt so clean down there before. Then, she applied
something that felt like Ben Gay, without the smell. She told me it was to
eliminate any pain, if ever I need to have something inserted in there. I
smiled and my still-hard dick moved in anticipation of the thought. When
she was done, it felt like girls must feel after getting fingered. I was so
turned on.
	She started messaging my feet and worked up my legs. She briefly
stopped. Once again the message started, this time with my hips. It was
more firm now. It was still relaxing, but it felt... different. I could
feel the fabric of pants against my crotch. I gently, subconsciously
grinded a little imagining it was Greg. Slowly the message reached up my
torso. In my mind I was getting messaged by my lover who was about to fuck
me. As the hands reached my breasts, they grabbed and twisted and groped,
more than messaged.
	"What do you want?" Claudia asked, seemingly from far away.
	"I wish Greg were here right now.," responded
	"Why?"
	"I am sooo turned on right now. I can see him and feel him fucking
my ass. It feels so good."
	"So if he was here right now what would you do?" I imagined her sly
smile since I still had the cucumbers on my eyes.
	"I would beg him to fuck me." I exclaimed.
	"really?" - A man's voice- Greg's voice.
	"Yes! I said loudly. Yes!. Oh my God! Greg.. please fuck me!"
	"Are you sure about that? he asked, hands on my breasts. I could
feel his crotch getting hard through the fabric of his pants which were now
grinding into my exposed crotch.
	"Please! Greg, fuck me! I want you so bad. Please fuck me!" I
yelled.
	"as you wish." he said.
	I heard the unbuttoning and unzipping of pants. I didn't realize
it, but quickly, lubricant was being applied to his now-hard dick. He
rubbed his dick all around my ass hole. I moved my ass, trying to find his
dick. Finally, cock and hole met. He slowly, firmly put his dick inside
me. I was ecstatic. It felt wonderful. I was being fucked like a woman for
the first time. It was soo fulfilling. I was about to come right
there. Gradually he pulled out and slowly went back in. He was very slow
and methodical, going in, out, in, out. The more he pumped, the more
comfortable I got, the hornier I got. I moved my pelvis in time with his
thrusts which got deeper and stronger each time. It felt so good, unlike
ANYTHIHNG I ever imagined. He was going faster now, pounding my ass. He
paused for just a second before a final strong push and came inside me. I
was so turned on, I came immediately. My eyes, not able to see because of
the mask and cucumbers, were just about glued shut from being squeezed so
tightly. I was in a new phase of post-orgasm that I had never approached
before. I flailed my arms a little bit as he withdrew.
	"I take you enjoyed that." He said.
	"That was amazing " I moaned.
	"Just wait until tonight he said as he bent down and kissed my
lips. I shuddered as my skin now felt a little breeze. I realized once
again my nakedness, lying there, freshly fucked for the first time,
recovering from the most amazing orgasm, still on the cusps of making my
fantasy fulfilled. Suddenly, I felt something light cover my skin.
	"Here's a thousand dollars." My lover said coldly throwing
apparently large bills on me. "Go buy yourself some nice things." and with
that he was gone. I could feel the slivers of money on me. In a way, I felt
like a whore, I thought. This brought a smile to my lips because I was
*his* whore. Another shudder ran through me as I thought about being Greg's
personal whore. Then I thought about all the wonderful clothes I wanted to
buy.
	It didn't take me long to figure out what I wanted. I tried on lots
of things and bought more. Every piece was sexier than the next. All of the
best fabrics =- silk, rayon and others I had never heard of. I bought a lot
of lack, especially lingerie. And some white, as well. I wasn't sure what
he had in mind for the night, so I bought sexy, slutty and
sophisticated. Also a few leather pieces, because I got hard just looking
at them.
	I was very excited to get back to his house and try everything
on. I ripped the tags off and decided what I wanted to wear for my man when
he came home. I decided on a simple black mini skirt with matching black
"fuck-me" boots. and a pink silk cami. I felt very sexy wearing it, as I
stood in the mirror admiring Claudia's handy work. I looked like a very hot
chick.
	When I heard his car pull up, my heart actually fluttered. I was so
excited, it was hard to try to contain myself. I opened the door for him
and he rewarded me with a very sensual kiss. We kissed for about ten
minutes. Just kissed at first. When we finally broke, he told me "you look
amazing." I just kissed him in response. He grabbed and squeezed my ass
. It felt so good having his strong hands on my ass which was basically
exposed. I ran my hands all over his back as he kissed my neck. His hands
found my breast forms and he played with them as if they were real. I could
tell it was turning him on. I could see him getting hard in his very
expensive pants. I rubbed my hands over him and felt his dick. It was very
strong and just begging to be released. I obliged and slowly removed his
belt, unbuttoned his pants. They fell to his feet. He kissed my mouth
again, forcing his tongue down my throat. He ran his hands through my hair
and seemed to be lightly pushing me down. I was excited to oblige. In
moments I was facing his rock-hard dick. It was the first one I had ever
seen. I remembered it being inside me earlier and that just made me even
harder, myself. I gently placed my lips on his dick. I kissed it all
over. Then I licked his head and under side. I heard him moan in
pleasure. he moved his hand back to my head and brought me closer. I took
the hint and put his whole cock in my mouth. It was a wonderful feeling. I
was so hard and excited thinking about his impending orgasm. I performed as
I would liked to get serviced. It was very sensual to actually be in
control. As he was getting close he grabbed the back of my head and forced
me to deep throat him. I was happy to oblige. The precum was amazing. It
tasted like my own sperm I had several times tried. Finally, he came in my
mouth, still forcing me to suck by keeping my head in place with his
hand. I let his hot, sticky load ooze down the back of my tongue. I licked
him clean and swallowed his gift. I had soaked my own panties. It was an
amazing and very pleasurable experience.
	He stepped out of his pants and pulled his socks off. I slowly
unbuttoned his shirt. He removed his own undershirt and was now naked
before me. In one motion, he picked me up and brought me to his room as if
I was his bride. I was so euphoric, I was in another state. He gently laid
me down in the bed. He started kissing me, very softly, on the lips. He
moved to my ear which made me wild. He used the weight of his body to hold
mine down as he drove me crazy with his kisses on my neck and ear. He moved
down, with his hands touching my skin, under my pink cami.It was an amazing
feeling. his lips followed his hands down my torso, and then around my
belly button. I was a bit ticklish, but didn't feel much like laughing. No,
I was in another zone. He kissed up and down my legs before moving to my
hard cock springing from underneath my skirt. He played with my dick
briefly. He then stopped momentarily to apply some lubricant to his
hands. while facing my dick, his hands explored my ass. He was pulling and
prodding. When two fingers simultaneously entered my ass, his lips were on
my dick. He sucked and worked my ass. It was a continuation of the amazing
experiences. He let go of my dick, and just worked on fingering my ass. He
found my spot and drove into me. Soon my back was arching and I was blinded
by orgasm.
	He moved back up to kiss my lips and I tasted my own cum in his
mouth. My hands found his dick, and it was already lubed and ready. I
grabbed him by the shoulders and turned him on his back. Slowly I sat down
on his dick. I was getting addicted to having him inside my ass. It felt so
good, I wanted to ride him all night. I bounced up and down with words and
sounds flying out of my mouth from deep within. I wanted him deep inside
me. I slammed my ass down on his pelvis. His hands were on my breasts
before grabbing my waste. He timed it to pump into me as I slammed down on
him. We were in rhythm. I could tell he lasted longer with me on top. That
was wonderful because it allowed me to prolong the sensation. I was on the
verge of orgasm, myself for about 20 minutes. It was such an amazing
ride. He grabbed my waste and squeezed really hard as he ejaculated inside
me. He was bucking wildly and I was just trying to stay on. Cum came out of
my dick inside my skirt. I collapsed beside him. He squeezed me and I could
feel his semi-hard dick against my bare ass. It was a wonderful sensation
to drift off to.