Tiffany
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Tiffany free porn video
"Tiffany"
After another week long vacation in New York City I was back on the
plane headed south along the eastern seaboard. But we didn't get far
because only minutes after take off we were diverted. Weather and delays
had forced an overnight in Boston once again. After making the trip
three or four times a year I had by now gotten used to the layovers.
I got off the plane, then went to retrieve my luggage and was soon
wheeling my suitcase down the concourse as I juggled my purse and an
overnight bag on my shoulder. I could hear the click of my high heels
and the sound of my skirt as I wiggled along towards the main doors. I
had bought a new suit done up in a gray wool with a matching blazer that
was all satin lined. The blouse underneath was a rich royal blue satin
with a bow at the front that set off nicely the pearl necklace I was
wearing. Most people took little notice of me as they came and went, but
a few men always seemed to glance in my direction with interest. I made
it outside, then took a cab to a nearby exclusive hotel.
I went to the bar and was just finishing my third drink when a man came
over and introduced himself. Then he set a drink in front of me that he
had ordered at the bar. I was a little tired and didn't appreciate being
hit on but I had met the guy the year before. His name was Bob, Bob
Higgbye. He was a divorced salesman who frequented the place when he
traveled, and who being lonely made the rounds trying to strike up
conversations. He noticed me cross my nyloned legs and adjust my skirt
as I shifted in my chair. He then sat down and was just starting to talk
when the owner of the lounge and hotel noticed us and came over.
"Is Bob bothering you again Tiffany?" she said with a smile as she came
to my rescue.
"Hi Gloria! No, Bob isn't bothering me, not really." I giggled as I
shook her hand in greeting.
Her name was Gloria Wentfeld, a well-to-do single lady in her mid
forties who was nearly fifteen years older than I was. She had good
taste like most upper class women and was an elegant dresser.
"Why don't you run along Bob darling. Tell the bartender your next drink
is on me. I'd like to chat with Tiffany for a while." she said.
Bob then excused himself and headed for the bar as Gloria sat down at my
table.
"Thanks. I wasn't in the mood for Bob tonight," I said.
Gloria answered, "No problem. Why didn't you call and tell me you were
in town Tiffany dear?" she said quizzically and with an almost hurt
sound in her voice.
I then told her we had an overnight flight delay and explained
everything. She then insisted she take care of all my needs for the
evening, then offered me the use of her penthouse apartment in the
hotel. She had a menu brought over then gave me her pass card to her
personal elevator. She noticed my purse, suitcase and overnight bag,
then motioned for a male hotel employee to come over. She had him take
the overnight case and the suitcase up to her residence. Then as he left
with my things she handed me the menu, then insisted I come up for a
visit after I was done. With that she smiled, then left the table and
continued with her business.
I had met her two years earlier. I remember it was a cold, rainy and
windy October night when I was here the first time on layover. I had
just gotten off the plane after another delay and was waiting for a taxi
when a black limonene pulled up past me and drove through a puddle
splashing my dress and soaking me! It was Gloria Wentfeld's car that was
at the airport to pick her up after a flight and she had seen the whole
thing. As I tried to dry myself off she came over then offered me a ride
to her hotel but since the layover was going to be a short one I had
just planned on going out for a quick dinner before I left. She
apologized and offered to have my dress cleaned but I told her it was no
big deal and I could change in the ladies' room. She seemed busy and a
bit in a hurry like the regular businesswoman then insisted that I stop
over and be her guest if I ever found myself in Boston again. She gave
me her business card as I bid her goodbye she then got into the back of
her limousine and sped away into the night.
She seemed nice then and really seemed sorry at how the muddy water
ruined the front of my dress even after I told her it wasn't that big a
deal. Now, she seemed pleased that I had taken her up on her offer and
had visited her establishment on this trip. I had forgotten about it but
had kept the business card she had given me and thought I would try the
place out. It wasn't long before I was finished with my elegant dinner.
I was really getting the red-carpet service! I then gathered my purse
and left for upstairs. I left the lounge and crossed the concourse of
the elegant hotel then took my pass card and entered the private
elevator and started my ride to the twentieth floor.
It was a short walk from the elevator down the spacious hall to Ms.
Wentfeld's private residence. I knocked on the elegant white door and
moments later a man opened the door and greeted me.
"I'm Tiffany, Ms. Wentfeld is expecting me," I said.
With that the man invited me inside. I noticed my bags by the door then
saw Gloria enter the living room to greet me.
"Will that be all for the evening ma'am?" the man asked.
"Yes Morton, you may leave us for the night, and thank you," she said as
Morton then left closing the door behind him.
The penthouse apartment was large and spacious. I noticed that the
appointments and furniture were way beyond my budget and what I was used
to. I had a two bedroom apartment which was tiny by comparison and would
have completely fit into her living room and dining room alone! I did
alright but as an accountant the money was nowhere this good. Gloria
then opened a bottle of champaign then came over and took her seat
beside me. She handed me a glass.
"So Tiffany dear, was your dinner alright?" I told her it was
outstanding and that she really didn't have to go to all the trouble.
"Nonsense," she said. As she continued, I crossed my legs and heard my
nylons swish as I smoothed my skirt. Gloria noticed, then crossed her
nyloned legs and I heard the same silky sound. She took a drink from her
glass.
"I see you like to wear sheer hose," she said. "Not many women wear them
these days. Are they stockings?" she asked.
"Yes they are, I prefer stockings," I answered.
She felt her leg and smoothed her hose. "I love sheer hose, they're so
very feminine and they just feel delicious don't they?" she asked as she
then brushed her hand against my leg! It was then I realized that I was
having my first lesbian encounter! But the catch was, I wasn't a
lesbian!
She took another sip of her champaign then began chatting about fashion,
clothing and other ladies issues.
"I have several pairs of stockings like these in different shades. We're
about the same size, I'll send you home with a few pair. I love the
taupe color, so flattering," she said then continued, "you really must
let me replace that dress my chauffeur ruined though, you simply must.
Come into the bedroom and let me show you a few outfits, I'm sure you'll
find something you'll like. Or, I could take you shopping!" she said
with great interest.
She seemed pleased and I could tell the champaign was beginning to
loosen her up as she began to relax. And, after my drinks in the bar the
champaign was having its effect on me as well. I didn't know what to do
as she put her arm around me and slid close.
She was well built and beautiful so I decided to go along. I wasn't gay
and didn't have anything to do with men but it was obvious that Gloria
thought I was a woman! She mentioned that I stood out from other women
and that she didn't know why. She then mentioned that for a young woman
that I was very attractive and she mentioned that it was strange that as
pretty as I was that I hadn't found a man yet. Either way she was
interested in me.
I hadn't expected anything like this! I kept my little "hobby" to myself
and had been doing this for many years. I had been wearing women's
clothes since I was a child and had carefully practiced and learned over
the years to dress and act like a woman when I was all dressed up. I
started going out in my neighborhood and got better over time then hit
on the idea to go to New York where I could be myself on my short
vacations and not bump into anyone I knew.
I used to go dressed as a man and change at the hotel once I got to New
York but the last few times I had packed up at home then took a cab to
the airport and had been going totally enfemme both out and back! My
slight build and height of only five foot eight in heels made most of
the difference and after working on my feminine image until I got
everything right. I was nearly undetectable and could easily pass. But
Gloria seemed to have gotten her signals crossed somehow. She had me
pegged as a lesbian but didn't know. And the problem was that in sitting
with her in her apartment all alone on the couch listening to soft music
and in being totally dressed I found it exciting and began to follow her
lead!
"You have lovely hair," she said as she ran her hands through my long
ash blonde locks.
She could smell my perfume and seemed to become even more excited that I
didn't pull away. She then moved in and gently kissed me, seeing if I
was receptive. She was pleased I kissed her back, she cooed with
pleasure. I ran my hand up her leg and felt the smoothness of her nylons
then realized I was getting excited too! It was lucky that I was so
tightly tucked into my girdle because there was no trace of a bulge,
only the appearance of a tight little ladies mound.
She began fondling my silicone breasts not knowing they weren't real.
She held me and laid on me as she leaned into me and kissed me. She
worked her white skirt up with a swish. I could see she was indeed
wearing sheer garter stockings. The garters coming out from under a pair
of black lace trimmed satin tap panties held them high and tight. I
instinctively reached up and cupped her mound. It felt it warm to the
touch then I felt the moisture and smelled the musk as I worked her
through her panties, feeling her mound, working her slit! She humped my
hand for a moment then kissed me deeper. I could feel our lipstick
smearing as we kissed. She then sat up nearly breathless with
excitement.
"You must come into the bedroom dear, I want to show you a dress I just
know you'll love." With that she led me through the large living room,
down a wide carpeted hallway and into her bedroom!
The master bedroom was large and spacious like the rest of the house and
was very feminine in every detail. Gloria went to a set of double doors
then opened them to reveal a large, walk in closet! She went to a shelf
and took out two boxes of nylon stockings and handed them to me.
"You'll just love these Tiffany, these are the silkiest, shiniest,
sheerest hosiery I have found. And they're opera length too!"
She then started looking through her racks of outfits searching for a
dress like the one I was wearing when her chauffeur drove through the
mud puddle and splashed me. She took out an expensive woman's suit and
skirt and held it up to me.
"There! You'll just look adorable in this," she said. "I even have a new
pair of matching pumps to go with them," she said as she gathered the
ivory colored outfit along with the stockings then set them on a chair.
She then held me and began kissing me once again, her tongue probing me
deeply as she excitedly ran her hands over my hips and thighs.
"I have a pair of dildo pants," she whispered as she continued kissing
and caressing me. She led me to the king sized four poster bed and soon
we were continuing on the bed covered with a lace trimmed pink satin
comforter. Gloria moaned as I reached under her skirt and rubbed her
mound again. She then reached under my skirt and began rubbing me! She
then reached under her skirt and took off her nylon tap pants then
dropped them to the floor as she continued. She then reached under my
skirt and began tugging at my girdle! I should have stopped and was
worried what she would think when she found out I was really a man but I
decided to take a chance and let her continue.
I felt her find the waist band of the girdle and start pulling it down.
She had my skirt up. I felt the girdle slide past my gartered nylons.
"Panties and garterbelt under a girdle?" she said quizzically.
She then pulled at the waist band of the panties and tugged them down.
But when she reached for my mound she pulled back in shock when she felt
my manhood! Now freed from its tight girdle it quickly became hard!
"My God what are you!?" she said as she recoiled.
"I...I'm sorry I didn't mention this to you earlier Ms. Westfeld," I
said as I sat up on the bed.
I then gave her the quick rundown on my "hobby" and how I had been
taking trips to New York so I could enjoy being myself.
"Are you some kind of sickening little sissy?" she asked.
I told her I didn't think so. She then got up and paced the room as I
laid there looking every bit the lady but with my girdle and panties
off, my skirt up around my waist and my nyloned legs spread to reveal my
still erect manhood! I then thought that she might have known and
mentioned that to her then learned that besides being very feminine she
was a total lesbian, a feminine "lipstick lesbian" and never dated men.
She paced the room a while longer then looked at me still on the bed.
"No wonder you didn't show any interest in Mr Higgbye," she said.
She then thought for a moment then came back to the bed, climbed on then
crawled up to me. She straddled me, quickly swished her skirt up then
grabbed my still stiff member and settled down on it! I felt myself
enter her as she wiggled and settled down onto it until it was all the
way inside of her! She threw her head back and cooed a feminine moan
then started humping me. We were both so excited that it didn't take
long for her and me to come! Then exhausted, we then both drifted off to
sleep still dressed.
The next morning Gloria made sure I was properly shaved, bathed and
dressed. She had me wear the white woman's suit she had selected for me
from her closet and the matching ivory pumps with four inch heels. She
dressed as well and once she was sure I once again properly dressed,
made up and looking like the perfect lady she took me to the dining room
for breakfast where her butler Morton was already busy setting the
table. We had our breakfast then went to the den to chat further.
"How would you like to work for me Tiffany? You told me you were an
accountant, you could help around here as my personal, executive
secretary," she said as she formulated her plan.
It was an interesting thought. A cross dresser working for a rich
lesbian. But I wasn't sure it would work and I thought it strange that
she never asked what my male name was. I guess to her it didn't matter.
"You'll move in here with me Tiffany to work for me and be my companion.
You obviously enjoy women's clothes and very much look the part. How
would you like to move in here, with me and live as a woman
permanently?"
I began thinking but wasn't sure I could pull it off.
"If you move in you'll be dressing full time and living as a woman from
now and on though, no pants or men's clothing of any kind. I like my
companions to be very feminine," she said as she looked me over,
realizing that with a little polish my look could be flawless and no one
would ever know with the exception of Gloria that I wasn't a real woman.
A fact that seemed to excite her even more!
She mentioned the pay and the benefits in addition to all the clothes
and lingerie of hers I would be wearing from now and on and was even
told she would take me shopping to get me started on a proper ladies'
wardrobe of my own. I thought it might be interesting so after thinking
it over a while longer I agreed to be her new executive secretary, at
least on a trial basis. With that the plans were set into motion.
"Yes, you're going to be the perfect 'little lady' Tiffany dear. When I
am through with you you'll be undetectable as a man! I'd like to start
you on female hormones as soon as possible though. I want to see you
start getting real breasts and wider, more womanly hips. I like that,
it's very exciting to me," she said.
"We'll have to have your whiskers removed by laser and do a few other
things to make you look your most feminine but I am sure you'll come
right along. You'll enjoy being a woman Tiffany, even more than you do
now!" she said as she continued making her plans. "And if you decide to
take the process all the way darling, I still have those 'dildo pants'.
Then we can pleasure each other!"
I had decided to move in with Gloria on the condition we could just keep
things as they were for the time being and she agreed. It didn't take
long to fly back home and close out my old apartment and get rid of all
my male clothes. I then returned and moved in with Gloria at her
penthouse and within two weeks I was busy working in the downstairs
office as Tiffany performing my secretarial duties.
I was treated very well and the pay and benefits of the job were more
than I could have imagined. I decided to continue on and began to enjoy
myself in my new role. Gloria soon got her way and to her excitement
started me on female hormones. With her coaching I became even more
feminine and womanly and as the hormones worked my hips did widen. My
hair and skin softened and even though I had to keep the breast forms
and used smaller and smaller ones as time passed to keep my look
consistent. It wasn't long before I could feel real breasts jiggling in
my brassiere! Finally, the breast forms weren't needed any longer and I
was filling the brassiere cups fully on my own!
Nobody ever had an inkling that I was, or had ever been a man. Mine and
Gloria's love life couldn't have been better even though I was starting
to have trouble maintaining or achieving erections now. But to Gloria it
didn't matter and seemed to please her even more! And through the
hormones I had begun thinking differently. Gloria then made her final
suggestion.
A few weeks later she took me on her private jet on an extended
"vacation". It took a while to heal from the procedure but time passed
quickly and within a month I was back performing my duties for Gloria. I
left the private elevator at the start of the new week early on Monday
morning and made my rounds around the hotel checking on the lounge the
restaurant and the main desk. It felt strange but somehow natural to me
now. I noticed it in my walk. The men still noticed me but it felt
different now and I even noticed how excited Gloria had become with the
"new" me!
After leaving the main desk I started the long walk down the concourse
to my office. I could hear my stiletto heels clicking on the tile floor
and the sound of my sheer, shiny nylons as my calves swished past each
other and the sound of my nyloned thighs and the lace trimmed nylon full
slip and the satin lining of my tight wool skirt as I minced along. It
was a heady experience. I could tell my posture had changed with the
weight redistribution too. I could feel my now wide, womanly hips
wiggling under the tight tailored skirt as I walked along, and could
feel the garter straps tighten and loosen with each step and could feel
the brassiere straps as they held my jiggling breasts under my satin
blouse. I could hear my jewelry "Tinkle" and could feel the weight of my
dangle earrings in my now pierced ears as I walked and I could smell
the feminine perfume that surrounded me and could feel my hair bounce
and sway as I moved.
But the most amazing experience was that now, as I walked with hips
forward wiggling along, I could feel myself in the tight panty girdle!
No longer "tucked" I could feel the silky lycra spandex as it held me
tight! I could feel my new trimmed "muff" my little mound which was now
a very real vagina! I felt the material of the girdle as it formed
itself over the tight little slit and pouting vaginal lips! It was very
exciting and now very real.
I had never been with a man and had little interest even now. But I knew
how excited Gloria was in taking charge in the bedroom and I knew that I
was now her new and permanent "lady-of-the-house". It was her who now
wore the "dildo pants" and it was her who treated me like the woman now
when she would spread my nyloned thighs and raise my legs as she thrust
into my tight little vagina.
Aspen
- 08.03.2021
- 9
- 0
