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From: a425couple <a425couple@hotmail.com>
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Subject: Story "The Saga ofTiffany Tempess" Chapters I - IX, by Snakeoil2
Date: Wed, 07 Jan 2009 07:11:06 -0800
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===================
(This many chaptered story was written
by Snakeoil2@webtv.net, all rights & respect to him.
I am just combining some sections of it, and reposting it
with his permission to try to help him and interested readers.
I've picked a variety of newgroups that seem appropriate,
and awfully quiet. ((If any wish a ng deleted, post to inform.)) )
Chapter 1- First Things First
Welcome dear reader. This is purely fiction. Any similarities with any
one living or dead is purely coincidental. It is based loosely on my own
experiences as a crossdresser. Having said this...
On with the story...
I was born Timothy, but early on I began experimenting with
crossdressing. I was the youngest of 4, and an only son, having 3 older
sisters. They each had very distinct styles and tastes in clothes. This
gave me a great array of outfits to to choose from, as well as lingerie
of varying tastes to choose from. From chic and wild, to meek and mild.
I remember the 1st article of female clothing I put on. I was about 10
years old. It was a pair of purple tights. I always had a fascination
with nylons, stockings, and tights. My sister had left them to dry in
the bathroom. 1st I touched them. I loved how they felt. So, I tried
them on. It was fantastic. From then on, I was hooked.
My love of dressing femme grew from there. As I said, I had plenty of
girls clothing around. I was never suspected of wearing any of it. I'm
sure some things were noticed out of place, but it was probably blamed
on another sister. I would dress whenever I was home alone. I looked
very nice dressed. I had a thin tall body, that didn't make for a very
impressive boy. I also didn't have much body hair. I was a late bloomer
I guess. It didn't show up until 16 or 17.
I was always a quiet boy. Smart but shy. I mostly stayed to myself.
Never dated girls, but had plenty of them as friends. They were easier
for me to relate too.
On a very special day, during summer vacation, I was alone in my house
and dressed wearing tan pantyhose, with white panties over top of them.
( I don't know why, but I've always worn them in that way) I had on a
white full slip over top of them. The slickness of it as I rubbed it
against the silky panties felt terrific. I kept on rubbing and sliding
them over my hard little peener, not knowing what to expect. It just
felt soooo good, I kept it up until....WHAMMO! My 1st orgasm. It was
tremendous and only intensified my need to crossdress.
I never had fantasies about men back then. Only of being perceived as a
girl. A sexy girl. Men came later. I explored the internet as I grew
older, and found I was not alone. But I remained on my own throughout
highschool. It would not be until I went to college that I truly allowed
my femme self to blossom. There I would not shame my family.
Chapter II...coming soon...
Chapter II - Planning for College
By my 18th birthday, I was in the 2nd semester of my senior year in high
school. I had studied hard, gotten good grades, and scored well on my
SAT,s. As a result, I was offered scholarships to many colleges. As I
sifted through them, there was 1 that stood out to me. It wasn't the
most prestigious of the lot, but it had 2 things I really liked about
it. It had a good music program, which was something I enjoyed. And it
seemed to have many clubs that wreaked of diversity, such as gay and
lesbian support groups. It was also located in an area noted for the
same reputation. I had been offered a full scholarship to it as well.
The only drawback it had was that there were no dorms. It would require
me to rent an apartment. There was however a real estate message board
on their website which could help me to find a reasonably priced 1.
As I scanned through them, I noticed 1 that had an e-mail address that
looked familiar to me. After some investigation, I realized where I had
seen it before. It was from a tranny picture post group. I saw that he
never posted pics of himself, but always had very nice comments for
those that did. Myself, I was only a lurker, and never posted anything.
I assumed he was what you might call an admirer. I sent him an inquiry
about the apartment he had for rent, and didn't mention this coincidence
at first.
After a few business like exchanges, I told him about it. We chatted in
an IM 1 night and he asked me what my interest was in crossdressing. I
told him I had been dressing most of my life. He asked if I had ever
posted a pic of myself. I told him that I had not, because I had just
recently turned 18. He asked if I had any pics I could send him. I did,
and I sent him a pic of me in my sisters cheerleader outfit. The pic was
of poor quality, taken with a cheappo webcam, but he got a basic idea of
my looks. He was very impressed. Our conversation turned a bit more
personal then. He told me his name was Phillip and asked me if I had a
femme name. I told him not really, but I had always liked the name
Tiffany. He told me that was a pretty name and perfect for me.
More to come...
Chapter III - On the Phone with Phill
After a few IM chats with Phil it was becoming obvious that he was
becoming interested in me as more than a tenant. He asked me to call him
on the phone and gave me his home number. I did, and the following
conversation happened:
"Hello" he answered.
"Hi Phillip, this is Tiffany." (I tried to use a femme sounding voice.)
"Well, well, Tiffany. It's wonderful to finally hear your voice."
"Is it what you expected?"
"Actually it's much sweeter than I expected. Have you been working on it
long?"
"(giggle) Not really"
"I have the apartment ready for you. When will you and your parents be
here to move you in?"
"I'm going to be there the 2nd week of August. I want to get settled in
before school starts."
"Sounds great, I can't wait to meet you in person." Then the tone of his
voice went from professional to flirty. "I might even have a job for you
here. I own a club that has a drag show on the weekends. Have you ever
waited tables?"
"Actually, I had a summer job a few years ago."
"That's great, I think you'll really like this part. You get to be a
waitress. All my waitresses are like you."
"Really?!?"
"Yes, and they make great tips."
"I could use that, Thanks."
"I can't wait to see your cute little ass in the sexy waitress uniform."
I was slightly taken back by that comment. Was he flirting with me? I
had never been flirted with before. After it sunk in for a second, it
was empowering. I flirted back.
"(giggle)...Phil, you are so naughty."
I think he picked up that he was dealing with a naive sissy, so he
backed off a bit.
"So, We will see you on...which day that week?"
"On Tuesday."
"Tuesday, OK then. I'll see you then.
"Thanks for everything Phil."
"Take care sweetie." (click)
As the time went by until then, I thought about the drastic change my
life would take when I went off to college. The freedom to go as far as
I wanted to with this whole femme thing, would only be controlled by my
own inhibitions. I felt like a child diving into the deep end of a pool
for the 1st time. Anxious, yet tentative. I determined, I would just dip
my toe in the shallow end at 1st. Then, doggy paddle my way toward the
deeper water as I felt comfortable with it.
My last summer at home seemed to fly. Between planning my curriculum,
and preparing for it. I also felt the desire to refine my femme side. I
had to admit to myself it was what made me happy in life. I had to
accept who I was before I could expect anyone else too. As I said
before, I wasn't really attracted to men. But I did like being
attractive to them. I faced a journey of self discovery, and I welcomed
the ability to set my own parameters.
More to come...
Chapter IV - Off to College
The day had finally come. I had already packed everything I wanted to
bring with me into a small U-haul trailer. Several boxes of my clothes,
some femme, some not. A box of books. My computer. A stereo and assorted
CD's. My bed. A few more boxes of personal items to help me feel at
home. It's funny how, at that age, all of a persons possessions can be
packed into such a small space.
As my father and I headed out on the highway, my mother kissed me
goodbye with tears in her eyes. Should told me she was proud of me and
knew I would do well. As we pulled away, I watched in the rearview
mirror, as the world I'd known for my whole life slipped away into the
distance. It was a 2 day drive to were my school was. My father and I
really connected on he way. He had always been caring and supportive of
me, but often, distant in his approach. I think, at this time, he
realized, the last of his children was leaving the nest. He was very
sentimental along the way. I reassured him that he had been a great
father.
After many miles and hours of driving, and a stay at a motel, we arrive
at our destination. I called Phil, and let him know we had arrived. He
told me he would meet us at the address.
When we got there, he was waiting out front. He was a very big man.
About 6' 5" and 300+lbs. He was in his 50s, with thinning hair. He
greeted my father and I cheerfully. Then showed us around the apartment.
It was a small studio with a kitchenette and a bathroom. Nothing too
fancy, but modern and clean. It was also partially furnished with a bed
and a couch. I went outside to start bringing in my things, as my father
and Phil took care of the financial end of things. When they were
through, they both helped me. My father seemed pleased and relieved that
Phil seemed so helpful. He must have felt he would be somewhat of a
parental figure to me. (yeah, right!)
More to come...
Chapter V - On My Own
My father spent the night at my apartment, before returning for home,
early the next morning. As I watched him pull away, I felt free and
abandoned at the same time. I guess this is normal.
I spent the morning settling into my new home. Unpacking, setting up my
computer, TV, and stereo. Suddenly, my phone rang. 'Wow' I thought 'my
1st phone call'. It was Phil. He asked me if I was still interested in
the job he had offered me. My answer was an immediate YES! He told me to
come down to the club the next morning for an interview, and to come in
dressed femme. I was a bit apprehensive about that. I told him I had
never been in public while dressed. He assured me it was very common
place in the community and more than likely, I wouldn't even get a 2nd
look from anyone. "Except maybe if they were interested in me." he
joked.
That afternoon, after a quick trip to the drug store to get a few
essentials, I worked on my look. I used Nair all over my body, plucked
my eyebrows, and experimented with some makeup. I tried on a few outfits
with a freedom I had never had before. It was fun to do this without
listening for a car pulling into the driveway.
Falling asleep that night was a bit hard. All alone in a strange place.
After being startled by new sounds and a few noisy passersby on the
street, I finally drifted off to a sound sleep.
More to come...
Chapter VI - The Interview
I woke in the morning and started getting ready for my interview. I
showered and slathered body lotion all over myself. I went to a website
that told me about dressing for success and 'landing that job'. I
followed the tips it gave on makeup, applying a light foundation and eye
makeup, and using a dark lipstick and lip liner. It said accentuating
the mouth makes people concentrate on what you are saying. (Whatever?)
Next, I worked on my outfit. The website said to go with dark solid
colored clothing. I slid on a pair of black pantyhose, then a pair of
silky black panties with a matching black bra. I decided on my black
short sleeved minidress with red trim at the neckline, hem of the skirt,
and cuffs of the sleeves. I wore a pair of red wedge mary janes on my
feet and a wide red belt around my waist too show off how slender I was.
To top it off, I put on a long, straight blonde wig that went half way
down my back, and a red plastic headband. I checked myself in the
mirror. 'What a knock out!' I thought.
Before I left, I rehearsed a bit of what I would say, and saying it in a
femme voice. I also practiced walking and sitting. I was too nervous to
eat or drink, and didn't want to mess my makeup so I decided to head for
the club. It was only 3 blocks away so, it would be a short walk.
Here was another 1st, and a giant leap for me. As I turned the doorknob
and pulled the door open, Tiffany stepped outside for the 1st time.
Although it was as monumental as a nuclear bomb going off to me, no one
was even in sight. As I walked along, I passed no one on the street.
Only a few cars zoomed past me. All my fears disappeared with each step
I took as my confidence built. By the time I got to the club, I was
brimming.
The front door was wide open, so I walked right in. There was an older
black man inside mopping the floor. He called to me, "Careful honey, the
floor's wet." He reminded me of Scatman Cruthers. I called back, "I'm
here to see Phil?" He answered, "Ahuh, the stairs to his office are on
your left." "Thank you" I chirped, and headed up the spiral staircase.
As I emerged into his office, Phil was sitting in a highback leather
chair. He was talking on the phone to someone about a delivery of wine.
Once I had surfaced, Phil glanced up at me quickly. Then gave me a
stunned 2nd look, not taking his eyes off me this time. He motioned with
his hand, for me to have a seat on the sofa. He quickly concluded his
conversation on the phone and turned his attentions to me. "Tiffany?" he
asked. "Yes Phillip" I answered regally. He came over to me, taking my
hand and kissing it. He fawned, "You are even more beautiful in person
my dear." I giggled, "Oh Phillip." He returned to his chair. He smiled
at me and pointed towards a rack of shoes, saying, "Find a pair in your
size and put them on." I did as he instructed. Next he told me, "Now,
pick up that tray off glasses, walk over to me, and serve me one of
them." I did this as well. (And quite well I might add.) Phil chuckled,
"You're hired. You start tonight." I set down the tray as he stood and
gave him a hug. I felt little and helpless in his arms and yet safe and
secure. He told me I would work Friday and Saturday nights from 6pm
until 2am. The pay was $5 an hour plus tips. He also told me to come in
an hour early to be fitted for my uniform and to have my makeup done. I
was very happy and before I left, I gave him another hug and thanked
him.
More to come...
Chapter VII - My First Night at Work
The walk home from the club was uneventful, although, I did pass a few
people on the street this time. No one seemed to give me any negative
attention anyway. I suppose I was either passing or accepted. One
obviously gay man did give me a wink, but that was about it. One thing I
did notice was that everyone seemed friendly, and said good morning.
When I got home, I was famished. So, I had a bite to eat. Then I decided
to take a nap. I knew a late and busy night lay ahead of me. Although I
was very excited I did manage to take a 45 minute catnap. I also called
my folks to let them know I was OK, and to make sure my Father had made
it home alright. (He had) I told them I had already found a part-time
job, but didn't go into details.
I took a quick shower to clean off my makeup and dressed in boys
clothes. I figured if I was going to be made over, I might as well go as
a clean slate. I did bring my wig with me just in case.
At 4:30 I headed for the club. I knew I would get there early, but
that's always a good thing to do on your 1st day. When I arrived, the
doors were all closed. I had to tug on several of them before I found
one that was open.
I stepped inside. The place was empty. It looked quite different with
all the club lights on. Very fancy! I called out, "Hello?!?" No one
answered. I went over by the spiral staircase that led to Phil's office
and called up them, "Hello? Anyone here?" Still nothing. I walked
further into the club, and as I got closer to the stage, I heard faint
music playing. It seemed to be coming from backstage. I went up the
steps and started walking across the stage. Suddenly, from behind me I
heard, "Well, well, her 1st night on the job and she already wants to be
on stage." Startled,I turned quickly to see who it was, but with the
stagelights in my eyes I couldn't. I blurted out, "I'm supposed to start
as a waitress tonight?" All I could make out was a shadow,as I squinted
against the light. As she came closer to the stage, her heels clunking
across the floor in a commanding fashion, she became clearer to me. She
tittered at me, "You must be Tiffany. I'm sorry, I didn't mean to scare
you. I'm Roxy." She came up onto the stage and gave me her hand, giving
me air pecks on either cheek. She was dressed as femme as anyone I had
ever seen and had a beautiful red wig with cascades of curls flowing
over her shoulder. She went on, looking me up and down, inspecting me as
she did. "Phillip told me all about you. My, you are a pretty young
thing, aren't you?" I smiled coyly. She continued, "And shy too...well
I'll fix that...Phillip suggested that I take you under my wing,
although I don't often do charity cases, but since you do have some
potential, I guess we could at least make a decent chorus girl of
you...who knows maybe even a co-star...but if you expect to be a diva,
you'll have a long wait...it took me a long time to get here and I don't
plan on loosing it soon."
Just then, a loud sound of clapping came from the back of the club.
"Bravo my dear Roxy!" Phillip said as he walked towards the stage. "A
masterful performance, but then, you always did play the queenbitch so
well." This put me in a very uncomfortable situation. To break the
tension I said, "It's really my fault, I didn't realize I shouldn't be
onstage." With that show of diplomacy, I seemed to win them both over.
Phillip said warmly, " You see Roxy, she's a polite girl...now play
nice." Roxy smiled at me, saying, "You're right Phillip...I'm just too
far removed from my nieviete to recognize it in someone else." She took
my hand and led me backstage and downstairs to the dressing rooms. On
the way she begged me, "Please don't think badly of me dear...it's just
that when you're on the top you can't rest on your laurels and expect to
stay there...always remember that, my dear." I determined to be very
respectful to Roxy, simply answering, "Yes Ma'am." Roxy laughed, "Oh
dear! Please, not Ma'am...I'm not that old...why don't you call me
'Mistress'?" I nodded, "Yes Mistress."
She directed me to a seat in front of a makeup mirror and started to
work her magic on me. She talked as I listened, "You don't have to be so
stiff and proper to be respectful you know. I want us to get to know
each other and be friends...oh, you have such lovely high cheek
bones...when I started out I was just a waitress myself...I was a bit
older than you at the time... things were different back then...open
your eyes wide now...when I was young, there was no internet...I thought
I was the only person in the world that did this." She stopped talking
while she did my lips. Holding my chin in her hand, she sensually glided
the lipstick over my lips. Our eyes met and we shared an intimate
glance. She spoke up, "Oh sweetie, you are gonna break a lot of hearts."
and laughed. As I looked at myself in the mirror, I began to understand
what she meant. Just then, several more girls came in.
Roxy introduced me to them. Roxy told 2 of them, who were also
waitresses, to help me find a uniform and show me around club. She had
to prepare herself for the show. The other waitresses names were Erin
and Dominique.
Erin was a short chubby redhead and Dominique was a tall thin black
girl. As they helped me with my uniform, a black spaghetti strap leotard
with white tuxedo trim, black fishnet tights, white highheel pumps, and
a frilly white apron/skirt tied around my waist, we got better
acquainted. After I put on my wig, we went upstairs to the club. They
pointed out whose tables were whose. Basically, I got the back left of
the floor. The area furthest from the bar. (Low man on the totem pole)
The doors were about to open in 10 minutes so we relaxed and chatted
until then.
More to come...
Chapter VIII - The Slumber Party
The doors to the club opened. A few customers were escorted in and
seated. As I started taking orders and delivering drinks, the club began
to fill up. By show time, every table was filled. Although I was quite
busy, I did get to observe the show. I realized there really was a lot
more to this art than just looking like a woman. You also had to be
entertaining. Singing, dancing, or even telling jokes. Most of the
performers did impressions of famous women as well. Of course, Roxy was
the star, and I found out why by the end of the show. She did an
operatic soprano aria that would be considered fantastic if a real woman
had done it, let alone a man.
After the show was over, the club remained open for an hour. Many of the
patrons left shortly after the performance, but a few remained until
closing time. There was 1 table in my area that had 3 older gentlemen at
it. (In their 60's) They were the only customers left in my area and as
they ordered their last round, they asked me if I would join them for a
drink. I wasn't sure if I was allowed too, so I stalled them with a
"Maybe" until I asked Erin if it was OK. She told me "OK? Why, it's
encouraged." As I returned with their drinks and a club soda for myself
(I didn't drink back then) I started to pull over a chair. Just then, 1
of them patted his lap saying, "Oh no sweetie, I have a seat for you
here." The other 2 gents chuckled bawdily. What else could I do? They
had been tipping very well all night. I timidly sat down on his thigh,
crossing my legs. He rapped his arms around my waist, pulling me in
tighter to him. My thigh was now right against his crotch and I could
fell his bulge against me. He began stroking my thigh, as he whispered
in my ear, "Tell your daddy, are you a good girl or a naughty girl?" I
didn't know what to say. I was in way over head. I just blurted out, "I
don't know." He just smiled at my innocence, saying, "Maybe we can find
out together." Just then, Dominique came over announcing, "Sorry
gentlemen, closing time." She must have seen my dilemma and come to my
rescue. As the other 2 gentlemen got up to leave, the 3rd reluctantly
released me. As he left, he handed me a $100 bill and his card, saying,
"Give me a call when you're ready to play."
Dominique and I walked over to the bar where Erin was standing.
Dominique yelled at Erin, "Are you crazy girl? You know she's not ready
for that yet!" Erin responded coldly, "She had to find out sooner or
later." This was all very confusing to me. Dominique put her arm around
me, saying in a motherly way, "Why don't you come over to our place and
party for a while. We can explain some things to you." I accepted the
invitation and we went downstairs to change back into our street
clothes.
Erin and Dominique shared a 2 bedroom apartment just around the corner.
Before we left the club, Erin grabbed a bottle of wine from behind the
bar.
When we got to the apartment, they both changed into cute little
nighties. Erin wore a black 1 and Dominique wore a neon pink 1. I felt a
bit out of place in my boys clothes, so Dominique offered to lend me one
of hers. She picked out a white 1, saying, "Here, this 1 fits you." This
made Erin laugh hysterically.
We each were sipping a glass of wine. Erin asked me, "Honestly now
Tiffany, you don't know what that guy was after tonight?" I shook my
head in embarrassment. Dominique piped up, "Let me put this bluntly. He
wanted to take you to his house and make you his bitch." I gave a
shocked look, yet I was curious. Dominique went on, "When I 1st started
waitressing at the club, 'Daddy Warbucks', that's what we call him,
propositioned me. I had turned a few tricks before then, but nothing as
drastic as him. He took me home with him. He had me dress in a school
girls uniform and insisted I call him 'Daddy'. He and I were locked in
his bedroom for 2 days. He spanked me, made me suck him and fuck him
repeatedly. Then he invited the other 2 guys, we call 'The Uncles' over
to do the same. All the time recording it on video." I was astonished as
I listened, but what Erin said next really floored me. "Oh stop
complaining, They paid you $10,000 didn't they, besides, I kinda liked
it when I did it." Dominique rolled he eyes at Erin and said to me,
"Well, if you wanna give it a go, more power to you. Personally, I like
the wam bam thank you ma'ams myself."
We chatted on until sunrise about sex techniques, clothes and
everything else under the sun. It felt good to have made some friends.
I went back to my apartment exhausted and had no trouble sleeping the
day away.
More to come...
Chapter IX - Saturday Night
I woke around 3pm. I started off with a bowl of cereal and watched TV.
My mind wandered as I did. I mulled over the things Erin and Dominique
had told me. Up until then, sex had never been much of a preoccupation
to me. I was content with myself and just masturbating. But now, a new
world was being opened up to me. I questioned my closeted existence. Was
I missing out on something? Could this be an awakening, or the opening
of a pandora's box that I would later regret.
I had a little more time before I had to get ready for work, so I went
on the internet. I had seen much information about transvestism and
crossdressing there before, but had never investigated transexualism
much. Typing the word itself into a search engine brought up 10s of
1000s of websites to check out. Looking through them, I barely scratched
the surface. Most of what I found was merely pornography and gave little
in the way of answers.
It was nearly 5pm, so I took a shower and got ready for work. I decided
I would go into work enfemme from now on, since everyone else that
worked there seemed too. I picked out an outfit that wasn't too over the
top. I wore a pair of blue jean short shorts held up by red suspenders,
a black tee that showed my tight little stomach, and a pair of red high
heel strappy sandals. I did my makeup as Roxy had shown me, then placed
my wig on. Checking myself before I left.
As I walked to work, I noticed the streets seemed more crowded. I
received a lot of positive attention on the way. Some men stared, some
did double takes, I even got a whistle or 2.
I arrived at the club and went downstairs to change into my uniform. As
I did, Erin and Dominique were doing the same. I had plenty of questions
for them. As I asked them, I received opposite opinions from both of
them. Erin finally summed it up quite eloquently for me. She said,
"Everybody is different. You have to do what you enjoy. My advice is to
try everything and if like it, do it until you get sick of it. If you
hate it, pretend it never happened and don't do it again." Dominique
shrugged her shoulders in resigned agreement. It was an obvious answer,
but correct. Perhaps I needed to hear it from someone else. I decided
then and there, I didn't need anyones permission to explore and find
myself. Self-acceptance should be the only limitations to my behavior. I
would have to forget conventional thinking and admit what I was and
embrace it.
That night at work went much easier. I actually had fun. I was even
flirty with the customers. I was realizing the potential power of this
role, and I liked it. Not to mention, I made a lot more tips.
At the end of the night, Dominique commented on how I really came out of
my shell. She asked me if I wanted to go shopping with her tomorrow? I
gladly accepted.
On the walk home, a man approached me and exposed himself to me.
Normally I would've been shocked, but I merely laughed it off. "So what'
I thought 'I hope it made his day'.
More to come...
(these were originally posted through Dec 11, 2008)
(I intend to combine later chapters & repost later)