Trippin with Tiffany
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Gambling With Tiffany free porn video
GAMBLING WITH TIFFANY
I left school as soon as I could, the only subject I was any good at was
maths and then it was mental arithmetic that I excelled at, not the fancy
theorems. I was lucky in that I got a job in a large department store
that had branches all over the country. Pretty soon I got onto their
management training scheme and was moved to a major city.
The pay was reasonable, but I didn't know anyone other than the people I
worked with. One Saturday night I drew out some cash, dressed reasonably
smart, and took myself off to the casino. I'd always been fascinated by
odds and chance, but I knew not to play roulette as the house always won
on that table. Blackjack was my favourite.
That first evening I left with a small profit. I was hooked, part by the
fun of gambling, but also by the atmosphere and the people. Not every
evening ended that way and often I left with no more than the cab fare
back to my small apartment.
When I had a run of bad luck one night, and had gone through my chips
within an hour of arriving, the manager approached me. I'd got to know
several of the staff by that time and had noticed that this attractive
thirty-something woman was in definitely in charge.
"You've had a unfortunate evening so far. It's Terry isn't it?"
I was surprised she knew my name, even though I was one of their
regulars.
"Take these," she said, slipping a small stack of chips into my hand.
"House chips might bring you some luck."
The pale blue chips with a double M monogram were unfamiliar to me.
"You can keep any winnings you make, but those house chips can't be
cashed."
She smiled and left me standing there, probably with my mouth hanging
open. When I returned to the Blackjack table the croupier smiled at me
too.
I made back some of what I'd lost earlier before I headed home. The same
pattern happened a couple of more times and I assumed it was a way of
keeping regular customers happy. By that time I'd exhausted my savings
and was close to maxing out my credit card.
The manager, who I now knew as Miriam, took me to one side and asked me
to join her in her office. She led the way to the back of the casino and
through into a smart room with a desk, a bank of monitors and a couple of
small sofas. She invited me to sit on one and settled herself onto the
other, facing me across a coffee table.
"So Terry, what are we going to do about your loans?"
"Er, what loans," I asked, slightly confused.
"All those house chips. You must have known that you had to pay them back
eventually."
The expression on my face must have shown her that I didn't know I had to
pay her back. I felt panicked, my stomach churning.
"It's okay Terry, don't be afraid, we don't break peoples legs any more.
But we don't like to write off debts either."
"I don't earn that much, but I promise I'll try to pay you back over a
period of time."
Miriam never took her eyes off me, but said nothing for what felt like
ages.
"Maybe it would be better if you worked off some of what you owe us.
We're always looking for good quality staff."
That seemed an easy option for me. We agreed that I would work in the
evenings until the debt was cleared. It was Friday night and she
suggested I turn up at 5pm the next day to learn the ropes. I readily
agreed, not thinking it would be resolved that easily.
The next day I was installed behind the bar to help Dave. It was all
pretty straightforward and I realised that being part of the casino was
enough for me; I didn't need to gamble. After a couple of weeks Miriam
took me aside and told me that it wasn't working as well as she had
hoped. The tips I was earning were not very good and the basic pay was
going to take forever to pay back my debts. She said, as a throwaway
remark, that the female staff always got better tips and maybe if I took
on a more nuanced look, I might do better.
She suggested I wear a silk shirt like the girls did and with my blond
hair almost reaching my shoulders, I could style it to look almost
feminine. Customers might just be confused enough to tip me better. It
all seemed a bit odd to me, but Miriam said she could get Jayne, a local
stylist she knew, to pop in and help me before my shift started.
So the next night I turned up an hour earlier. Jayne was a woman in her
forties, but very attractive. She washed and blow-dried my hair and then
insisted on thinning my eyebrows a little. She ran her fingers over my
face and commented on how smooth my skin was. The truth was that I didn't
have to shave every day as I had little facial hair, not much more than a
light fuzz on my top lip. Because I was nervous about what was happening
she dug in her handbag, popped a tablet out of it's foil pack and held it
out to me.
"Er, what is it?"
"It'll just relax you a little, nothing scary."
I swallowed the tablet, then another that Jayne produced a few minutes
later. That night it was as Miriam had predicted, my tips were
significantly better. Dave was very nice to me and kept putting his hand
in the small of my back when he spoke to me. It seemed odd at first, but
after a while I got used to it.
Jayne was there every night, as I had to tie my hair back in a ponytail
for my day job. Each time she did a little more work on my face, a tiny
amount of eye shadow, a little foundation to cover a skin blemish and
another couple of the tablets. After a few days of this I knew I looked
more than androgynous, I looked like a girl in slacks and a silk shirt,
but Miriam was still not happy at how fast I was clearing what I owed
her.
"We'll have to find some way of improving your tips or I might have to
have a word with the boys."
The boys were both well over six feet tall and spent a lot of time at the
gym, they were the front door security team.
"What else can I do," I pleaded.
Miriam looked at me that same way she did when she came up with idea of
me working for her in the first place.
"The hostesses make much better money," she said softly.
They were the girls who took drink orders at the tables and delivered
them on small silver trays. They were often tipped with chips, which we
kept for them behind the bar. I knew how much they could make in an
evening. It was a lot of money.
"But you have to be a girl, you don't have any guys doing that job," I
stammered.
"Better turn up in the morning tomorrow and we'll see what we can do."
I phoned in to work and took a day off sick, then went to the casino.
Jayne was there to greet me and led me upstairs to what I presumed was
Miriam's private apartment. She said we were going to have fun and just
to relax. She gave me another two tablets to swallow that she assured me
that they were nothing to worry about. I needed something to relax me and
swallowed them without further question.
That day she made me use a depilatory cream on my whole body and shower
it off. I never had much body hair, but coming out of the shower I felt
especially naked and grabbed a dressing gown from the back of the door to
cover myself. It was a silk gown, which felt amazing against my smooth
skin. Jayne made me sit on a sofa and she started to put body lotion on
my legs. Her hands, and the silk gown, had a dramatic effect on me. The
gown tented in the front.
"Now that's an unexpected event," Jayne said, raising her eyebrows.
It hadn't occurred to me until then that I hadn't had an erection for
some time. Jayne let her hands run up my thighs, pushing the gown away at
the same time. My penis had never been large, but I was sure it used to
be bigger when erect. She leant forward and took all of it into her mouth
in one movement. I think I whimpered. That was the first blowjob I ever
had and within a few minutes I was erupting into Jayne's warm mouth.
"Sorry," I mumbled, not sure if I should have warned her I was about to
cum.
Jayne looked up at me, her lips glistening. Her hands remained on my
thighs while her body stretched up so that she could kiss me. I was
completely under her spell and when her tongue entered my mouth I wasn't
entirely surprised to find most of my cum came with it. I don't know what
made me so eager, but I sucked on her tongue and swallowed everything she
gave me before she broke the kiss.
"I wasn't expecting you to get that hard, never mind cum like that."
Jayne smiled and scooped a last drop of cum from her lips with an index
finger. Then she offered it to me and I readily sucked it off her finger.
What had come over me?
She had a light lunch sent up from the casino kitchen and we spent the
afternoon on my makeup, hair and getting me to practice walking in the 4"
heels that all the girls wore. It was tricky to get the hang of it and
made my ankles hurt.
"Now, Miriam will be up here very shortly and we haven't tried on your
outfit yet."
Until that point I'd still been wearing the silk gown and hadn't thought
what I'd be wearing in the casino. Jayne fetched a couple of hangers from
the bedroom. A cream silk blouse was on one, which was now quite familiar
territory. From another hung a short, dark blue skirt, and a third small
hanger had a bra, panties and suspender set with a pair of dark
stockings. This was the reality of what I had agreed to. I had to remind
myself that it was only to help pay off my debt.
Jayne helped me dress and I was surprised to find everything was a
perfect fit. The bra came with small breast forms, already inserted. The
whole process was odd and I felt like I was in a trance. With my skirt
straight, my shoes on and my hair adjusted, Jayne let me look in the
mirror. What stared back at me was a drop-dead gorgeous girl. I'd always
been skinny and not that tall, but had never thought what I'd look like
as a woman. Vanity took over and I grinned at how good I looked. At that
precise moment the door to the apartment opened and Miriam appeared.
"You've done a great job Jayne, but then you had a very pretty boy as a
starting point."
"Mmm, I think she looks cute," Jayne replied. "Guys are going to be
falling over her. What shall we call her?"
"But I'm not gay," I blurted out and started to cry.
I'm not prone to crying and didn't know why I was reacting that way.
Jayne came over and put her arm round me, drying my cheeks with a tissue.
"Of course you're not gay, that's when men like each other. Now stop
crying," she cooed, "or you're going to spoil your makeup."
"I'm sorry, it's just that..."
I was lost for words. I was sure I wasn't gay, but I remembered Dave's
hand on my back. I'd found it so soothing whenever I'd panicked at work.
Then there was how I looked. I really liked how I looked.
Miriam took my hands in hers.
"You're only serving drinks tonight, nothing more than that. It's just a
way of paying off your debts more quickly. You can start off behind the
bar with Dave, until you feel confident."
Miriam was so nice, so caring, that my tears dried up and Jayne adjusted
my makeup so that I was ready for work.
"Can I be called Tiffany please?" I whispered.
When I was introduced to Dave, as Tiffany, he treated me like a new
member of staff that he'd not met before and gave no hint that he knew me
as Terry.
Behind the bar it felt safe, it was a place I'd already worked, but not
dressed as I was now. Dave put his hand in the small of my back, as he
had previously, when he was chatting to someone over the bar, or when he
introduced me to a customer. But as it left my back it now traced a
gentle path over my ass. I took this as a compliment and came to look
forward to him being familiar in that way.
By mid evening one of the girls hadn't turned up for work and Miriam
asked me if I was ready to work the floor. It turned out to be fun. The
occasional guy would try to touch my legs, but Miriam always appeared
beside me I didn't get hassled too much. At the end of the night my feet
hurt like hell, but I'd earned a startling amount in tips. I reckoned a
week or two like this and I'd be square with the casino.
After a couple of nights I was actually enjoying the attention I was
getting while circulating the tables and had learned to deftly escape the
more serious attempts to grope my legs. Jayne helped me get ready each
evening, gave me two of those tablets, and encouraged me to do more of my
makeup myself.
It was a Saturday night when Miriam said her brother Tony was dropping
in. She explained that he actually owned the casino and had shares in
several more scattered around the Europe. She pointed him out to me when
he arrived and suggested I take his drink order.
I was now quite confident in my appearance and walked over to the table
where he was playing. I asked him if he'd like a drink. When I returned
with his whiskey on the rocks, balanced on my small tray, he didn't take
it from me as was usual with customers. When he eventually took a sip he
indicted for me to stay and put his drink back on my tray. I stood there
obediently. If he owned the place then it was to him that I owed any
remaining money and I didn't want to offend him. The fact that he was
amazingly good looking and in an expensive suit should have had no
influence on my attitude, but it did. Dressed in my usual short blue
skirt and cream blouse I thought we would make a good-looking couple.
By this time my day job had become just one of those things I had to do
and working at the casino work so much more fun. Even getting dressed in
the evening was exciting, although Jayne never performed that service for
me again because I never now seemed to get an erection. This was not
something that unduly worried me; it would have made an ugly bulge in my
skirt.
When Tony took a break from the game his hand started to stroke the back
of my thigh. Instead of turning away, as I would normally have done, I
let him continue. His fingers found the bare flesh at the top of my
stockings and I bit my bottom lip to stop myself gasping with pleasure.
He smiled and asked me if I was enjoying my work at the casino.
"I like it more every day," I replied.
"Maybe you should give up your day job then?"
I was struggling to think clearly with his hand on my leg and didn't
respond.
"How would you like to be on my permanent payroll? I think I could find a
special position for you."
"Sounds interesting. Will I be working under you?"
I was actually flirting with Tony. Some sort of electric reaction was
coursing through my body, caused by his touch, but absolutely nothing was
stirring under my skirt. I didn't care, it wouldn't have been right.
"I'll have my sister arrange something if you'd like?"
Tony stood up at that point. He was over six foot tall and even in heels
I had to look up to meet his eye. His hand lingered over my ass and
slowly pulled me towards him.
"I'd like that very much," I whispered.
He looked into my eyes and told me he'd see me soon and to make myself
comfortable in my new apartment. I had no idea what he was referring to,
but he'd moved away before I could ask exactly what he meant.
At the end of the evening Miriam took me to one side.
"Do you like being Tiffany?"
I thought about for a nanosecond and nodded.
"Would you like it if you didn't have to live your double life, if you
could be Tiffany all the time."
It was a huge question, but I knew that my life in the casino was all I
cared about and my day job had become a complete chore.
"How much do I still owe the casino?"
Miriam told me that my account was clear, that I could walk away never
have to be Tiffany ever again if I didn't to be. The idea of saying
goodbye to the glamour and fun of the casino was a horrible thought. I
also didn't want to say goodbye to Tiffany, she was so much fun than her
alter ego, so much more popular.
"Will I get to see Tony again?"
"Very soon Tiffany."
Miriam guided me through the casino to the back door. There was a large
black Mercedes with tinted windows waiting there.
"You're sure about this Tiffany?"
"Never been more sure of anything," I smiled.
She draped a coat around my shoulders and the driver, in a pale grey suit
and peaked cap, opened the rear door for me. I slid as elegantly as I
could into the soft leather seating. I didn't know where we were going,
but I guessed it was a new life for Tiffany.
We arrived at an apartment block in an expensive area of the city and the
driver opened the door for me. He led the way into the building, nodding
to the doorman who obviously knew him. The lift took us to the very top
floor and opened onto a carpeted landing. The driver held the lift doors
and handed me a key on a red ribbon.
"You should find everything you need inside miss. I believe Jayne will
call round in the morning. Do have a pleasant night." He touched his cap
as a sort of salute as the lift doors started to close.
"What's your name," I blurted out.
"Mr Tony calls me Jenson miss."
"Thanks Jenson."
There was only one front door on the landing. They key made a smooth
click as I turned it and I walked into the apartment, not knowing what to
expect.
The entrance opened out onto a large living area and moonlight was
flooding through the floor to ceiling windows. There was a spectacular
panorama of the river and the city, which left me breathless. I knew I
couldn't afford an apartment like this, no matter how good my tips were
at the casino.
Exploring the apartment I found it had just the one double bedroom. In
it, one half of the built in wardrobes belonged to the man who lived
here, the other had a whole range of women's clothes, most still bearing
their store labels. A note was pinned to a bow, tied to doorknob. It was
from Jayne and said that I could try them all on tomorrow and see what
suited me. A rack at the bottom of the closet had several pairs of shoes
and I couldn't resist trying a pair on right then. They were a perfect
fit, as I suspected all the clothes would be too. I assumed this was all
planned by Miriam and, maybe, by Tony too.
The bed had a silk nightdress laid out on it, a soft salmon pink. When I
saw it I realised how tired I was. Dropping my clothes where I stood, I
slid the nightdress over my head felt it caress my body as it slid down
to mid thigh. I crawled into bed and fell asleep to dreams of Tony seeing
me in all those various outfits.
I woke in the morning to the sound of someone opening the front door of
the apartment. I couldn't think where I was for a moment and then Jayne's
voice called out.
"Tiffany darling, are you still in bed?"
It was gone ten o'clock. In the cold light of day I wondered what I'd
done, whether that impulsive decision last night had been right. Jayne
was sweet, she made me go and take a shower. There were two things that
had been puzzling me the last few weeks, neither of which really worried
me, but both seemed odd. My penis never got properly hard now, it sort of
firmed up a little and still felt nice to play with, but I didn't cum
very often; the other was my nipples. They had become incredibly
sensitive and I even wondered if was developing breasts. Had dressing as
Tiffany every night made my body react in some way?
When I returned to the bedroom Jayne had laid out an outfit for me; white
lacy edged panties and a matching bra, a short cream skirt, a loose
fitting deep grey top with short sleeves and round neck, and a pair of
flats with little bows on the front. It was a very cute outfit and I was
admiring my reflection in the mirror when she called out from the
kitchen.
"Breakfast's ready."
It was a very healthy option of fruit and yoghurt with Jayne pointing out
that I didn't want to spoil my figure. She offered me the usual two
tablets and said she'd that leave them in the bathroom and maybe I should
take them morning and evening now. I didn't question this advice.
We spent the rest of the morning going through the clothes in the closet
and deciding what suited me and what didn't. There was very little to be
returned as whoever it was who had chosen them had excellent taste. Jayne
then guided me while doing my makeup and my hair, teaching me some finer
points. By the end of the afternoon I was exhausted and Jayne suggested I
had a little lay down before getting ready for work. She said that she'd
iron my skirt while I slept.
The second time I woke that day it was with Jayne massaging my shoulders.
She said to relax and enjoy the experience. It did feel nice and was a
wonderful way to emerge from sleep. Jayne worked from my shoulders all
the way down my back and my legs, finishing at my feet. She took more oil
and returned her attention to my thighs, working her fingers firmly but
gently right up to the tops of my legs. It felt so good as her palms
cupped my ass and her finger strayed into the crack of my ass. Then one
finger pressed gently on my rosebud and I heard myself moan quietly.
"You're such a pretty girl," Jayne whispered.
Her finger remained firmly until it broke into me. I think I pushed my
ass up to encourage her and I felt more oil drizzled onto my ass. Jayne
only used one finger that afternoon and I shuddered when I came, unable
to control myself with the sensation of her finger massaging me.
When it slid out she told me to shower and she would tidy up the bed. I
was slightly embarrassed by what I'd just done, but when I emerged from
the bathroom Jayne made me feel okay. I dressed, took a couple more pills
as instructed and Jenson turned up to take me to work.
When I told Miriam that I would need to do something about my job and
flat, she told me not to worry, it was all being taken care of for me. I
didn't care what she told them as long as I could remain as Tiffany.
The next couple of weeks I worked the casino in the evenings and I saw
Jayne almost every day. Sometimes we shopped and she continued to give me
her special massage every afternoon before I got ready for work,
gradually working up from a single finger to a slim vibrator and then a
dildo that was bigger than my penis had ever been. There was no ignoring
the fact that Jayne was fucking my ass now, it couldn't be hidden in my
head as part of a massage. It felt so good that I looked forward to it
every day and I think it relaxed me for work, putting me in a perfect
mood to flirt with clients.
During these weeks I realised that I was developing breasts, my nipples
were now puffy and protruding slightly. I didn't even need breast forms
with the right kind of bra. I guessed that it was down to the tablets I
took every morning and evening, but was so pleased with my little breasts
that I swallowed the tablets eagerly. Jenson picked me up each evening
and dropped me back to the apartment after work. I was living the life of
luxury, but wondered where Tony featured in all of this. I didn't have to
wait much longer as he was in the casino that night.
Miriam told me that I was to make sure he had everything he needed and
not to worry about any other customers. I was happy to oblige, spending
most of the night next to Tony and with his hand periodically stroking my
leg. It was almost midnight when he looked at his watch.
"Time for bed I guess," he said and looked at me.
"And where is your bed?" I cooed.
"Well, you've been sleeping in it for the past several weeks."
Call me dumb, but I hadn't made the connection. Who owned the apartment
and whose clothes they were hadn't troubled my mind; I'd simply been
having so much fun.
"Shall we go?" he asked, offering me his arm.
I slipped my arm through his and we strolled to the front door of the
casino this time where Jenson was waiting with the Mercedes.
As we entered the lift, Tony turned me towards him leaned in for a kiss.
I remembered protesting to Jayne and Miriam that I wasn't gay and I would
still stand by that statement. I was a girl in the arms of a tall, well
dressed and good-looking guy, I wasn't gay, but I was looking forward to
my first kiss as Tiffany.
Our lips met softly. Tony's tongue slid into my mouth as our we locked in
a passionate kiss. My arms wrapped round his shoulders and his hands
covered my ass, pulling me against him. I could feel how aroused he was.
The lift stopped and the doors opened.
Tony led the way into the apartment and, as soon as we were in, he kissed
me again, pushing me gently back against the wall. His right leg inserted
itself between mine and my left leg rose in response. His hands, still
under my ass, lifted me up. Instinct took over and I clung round his
neck, my legs circling and wrapping round his body, ankles locking behind
his back. Still against the wall, I could feel how hard he was, pressing
against me. He whispered in my ear.
"Are you ready for this Tiffany?"
"Never more so," I breathed.
He carried me through to the bedroom and sat me on the bed. I lay back to
look at him, my arms above my head, my legs still splayed slightly and
dangling over the end. Tony undressed in front of me revealing a well-
toned body, now with nothing more than a pair of boxers covering his
erection.
"Do you want to unwrap your present?" he asked.
I sat up and hooked my fingers into the waistband of his boxer shorts,
staring at the bulge. As I pulled them down Tony's cock sprung out, hard
and huge. His shorts fell to floor and my hands took hold of him. I was
mesmerised by the warmth and strength of his cock and how small my hands
looked holding it.
Tony was stroking my hair, very gently encouraging me to get closer. I
wanted to, but was scared of how it would taste and how much I would be
able to take in my mouth, never mind anywhere else. A little pre-cum
oozed from the tip and I instinctively licked it off with my tongue. That
was all it took for me to turn into an enthusiastic, albeit amateur,
cocksucker.
My lips glided over the head, taking some of the pre-cum with them. I
heard Tony sigh, which encouraged me to take more. My gag reflex cut in
when I had no more than half of his cock in my mouth. Tony soothed me by
stroking my hair and telling me how pretty I looked. I kept trying, but
it was going to take more than one night to conquer such a beast. It was
however quite slippery with my spit after a couple of minutes of trying
and, if anything, even harder.
"Maybe we'll try that again tomorrow," Tony said as he lifted my chin
with a finger. "Why don't you slip off your panties now."
I did exactly as he said and edged my way back onto the bed until I was
lay there with my legs slightly apart and my arms above my head again.
Tony knelt between my legs and leaned forward to kiss me, my mouth now
wet and slippery against his.
His hands pinned mine to the bed as we kissed and I wrapped my legs round
his naked body. His cock touched my ass and he broke the kiss, his mouth
still only inches from mine and our eyes locked together.
"Are you sure you're ready for this Tiffany?"
I nodded and bit my lip in anticipation while Tony reached between us and
position his cock just where it needed to be. Then he rocked his hips
forward and, as I exhaled with a sigh, he pushed into me. It felt huge,
but thankfully Jayne had prepared me well. He kept pushing until it was
all in, filling me so perfectly, his balls resting against my ass.
"Tony," I whispered. "Am I really pretty?"
"You're beautiful," he replied and kissed me again.
When he started to move in me I thought I was going to faint with the
sensation. I must have been in some kind of trance that night as all I
can remember is the feel of his cock in me, driving repeatedly into my
body until he came with a series of juddering pulses. Something between a
grunt and a groan emanated from Tony as the last thrust buried his cock
so far inside me that I thought it must have filled my whole body. He
collapsed on top of me, kissing me again. The weight of his body on mine
was sexy, making me feel so much like a real woman who had pleased her
man.
I felt him contract and slowly withdraw. I knew I didn't want to ooze all
over the bed, so let him roll off me so that I could go to the bathroom
to clean up. He had cum so much that it was dribbled over my thighs from
when he slid out. I tool a little on my finger and tasted it. Then more,
it was the taste of sex and Tony. I promised myself that I would have to
consult Jayne about getting over that gag reflex so that I have it
straight from Tony himself, but that would have to be another day.
Miracle
- 03.04.2021
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