Savannah And Kat s First Date
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Shelli's First Date free porn video
That Special Date - Part 1
Hi, my name is Shelli. I am a 27 year old T girl now living full time as
a woman. I began living full time about 3 years ago and have never
looked back. I had always had an interest in woman s clothing and
fashion as far back as I can remember. I had started to dress in my
sister's clothes when I was in high school and never forgot the feeling.
I would sometimes fake an illness so I could stay home and dress while
everyone else was out - I could spend most of the day trying on different
outfits and looks. I got away from dressing some when I went to college,
but never forgot the feeling. I went college in the South and I was
struck by many of the cultural differences from the North. Women in the
South seemed much more feminine - I envied their sense of style (and
obviously their clothes). I didn't get to dress much in college with the
exception of one Halloween my senior year. Most of my friends were girls
and there was a group of four (Kelli, Trisha and Tammy) of us that
studied together and spent a lot of time hanging out. A few weeks before
Halloween, over a few too many beers, Tammy suggested they dress me up as
a girl for Halloween. I was dying inside, I wanted to do it so badly,
but I had to protest for appearance sake.
Tammy:" Come on! It will be really fun! I bet we could do such a good
job, nobody would recognize you."
Shelli: "Absolutely not. I would look and feel ridiculous"
Kelli: "No you wouldn't. It s not like we would make you look like a drag
queen. We would do it in a way that was understated and make you look
like a normal college girl. We could go to a few clubs that we don't
normally go to so you wouldn't feel self conscious about running into
someone you know"
Tammy: "It's Halloween. Everyone will be wearing costumes and you
certainly won't be the only guy dressed as a girl."
Shelli: "Like wearing a dress?"
Trisha: "I am sure one of us has a nice wool skirt that would fit you. A
nice top or sweater would look great. A little makeup and we could do
your hair. It will be a blast"
Shelli: "Alright, I guess..."
The night of Halloween, I went over to Kelli s place for the preparation.
The girls had picked out a gray pencil skirt and a ruffled white blouse.
They had asked me to shave my legs in preparation, which I did after some
mild protesting. Trisha gave me some body-shaping Spanx to help the
clothes fit better. "You want to look good, don t you?" Next was a nude
bra with a pair of breast forms one of the girls had used to help fill
out a bridesmaids dress. Between the 2 undergarments, my figure didn't
look half bad. Kelli and Tammy then took me into their bathroom to do my
hair and makeup. Since my hair was close to shoulder length, they were
able to straighten it, curl it and style it into a modified Bob
hairstyle. The makeup seemed to take forever, but when it was done, I
was astonished at how feminine I looked.
I never would have dreamed I would look this good. The girls helped me
into the skirt and blouse - both fit like they were made for me.
Finally, some light colored hose and a pair of cute platform May Janes
with a 3 1/2 inch heel.
"These will be easier for you to walk in. The strap across the front will
keep your foot snugly in the shoe. The platform makes it much easier to
walk with this high a heel. In a short time, these will feel completely
natural" encouraged Trisha. Slipping into them was like heaven. After a
little while to get accustomed to the new me, we were almost ready to go.
"Wait" said Trisha. "You really do need a purse to finish things off."
"Do I really need a purse? What do I put in it?" I replied. "Well"
said Kelli, "You'll need for your compact and lipstick... and condoms."
All of the girls giggled as I fitted the purse over my shoulder. I was
surprised how quickly I adjusted to walking in heels and slipping into
female mannerisms. It was incredibly liberating to be out as one of the
girls. We went out to several clubs and had a wonderful time. The girls
kidded me about how this came a little too easily to me.
After I graduated from college, I took a marketing job in a large,
Southeastern company. This allowed me to get my own place and spread my
wings. Since I didn't have a roommate, I was free to dress as much as my
heart desired. I started to shop for myself and dress some on weekends.
Before I knew it, I had a complete closet of different outfits and a
growing shoe collection. I worked on makeup application and got to the
point where I could apply it easily, quickly and with excellent results
for any type of look. I would spend evenings and entire weekends
dressed, shopping online or perusing Cosmo, or Marie Claire. I felt more
and more like a woman and less and less like a man. The transitioning
picked up speed as I started hormone therapy - after a few months my body
hair was softening, breasts began to develop and hips and thighs began to
take on a soft shape. Eventually, I wanted to complete the transition,
but work remained a sticking point. If I came out as a woman, would they
fire me?
I finally summoned up the nerve to present my case to the Human Resources
Representative. I was beyond relief when she said she admired my courage
and encouraged me as much as possible. The company could not terminate
me for this reason. However, she felt it may be difficult for me to
continue in my current marketing section. "I can try to find another
spot for you here, but you may find the responsibilities different than
before. Unfortunately, I can t promised exactly the same job." The HR
Rep stated. Since I had been there 3 years, I really didn't want to
start over. I agreed to consider the other options. After a few days,
the HR Rep called me and told me the best she could offer was as an
executive assistant to one of the Vice Presidents, a woman named Gwen
Taylor. If I was willing to consider this, I would need to meet and
interview with Ms. Taylor.
The morning of the interview, I was beyond nervous. I wanted to make my
best impression, but how do you tell someone, "I am a guy, and I want a
job as your executive assistant. If you give me the job, I will be doing
it as a woman." I dressed neatly but modestly in a pair of black pants
and a light pastel pink shirt. I wanted to appear slightly feminine, but
obviously could not dress en femme.
Ms. Taylor immediately put me at ease. She had an undeniable style or
great taste in clothing. I immediately noticed her shoes and how
perfectly her outfit fit together. She explained to me that she had
spoken with the HR Rep and knew the circumstances. She explained the job
and it's duties.
Gwen: "The downside is that you will not really be using your marketing
degree and some of the tasks may be kind of menial. On the other hand,
it allows you a chance to start fresh with a new life and still remain at
our company."
Shelli: "I am very grateful for any opportunity you could give me, Ms.
Taylor"
Gwen: "Please, call me Gwen. It seems like you need this type of
opportunity and I would be getting someone who is overqualified for the
job."
Shelli: "I will do everything to make sure you are pleased with me"
Gwen: "This is kind of awkward, but I do expect a very professional
appearance. Judging from your appearance today, I think that you will do
just fine. We all have bad hair days, but you must dress to look your
best every day."
Shelli:" I won't let you down.
Gwen: "If you need guidance or advice, I would love to help. I never
had a younger sister, so helping you along would really be fun for me"
I was speechless. I couldn't have fallen into a better situation. Gwen
was so incredibly sweet I could barely believe my good fortune. We
agreed I would start after 1 week. I had a lot to do.
With a new job and new start, I fully embraced my female self. I threw
out all my male clothes. I sold my SUV and bought a cute, white VW
Beetle convertible. I re-did my apartment with soft mauve tones and
several new prints. I went to the salon for a complete full makeover,
including manicure and pedicure. My first days as a fulltime girl were
absolute heaven.
The first day of work, I got up early to make sure my makeup would be
flawless- all of my practice paid off. I was able to get the perfect
daytime, business look. I couldn't decide between a black skirt suit or
a gray pants suit with a double breasted jacket. I finally decided on
the gray suit - I really wanted to impress Gwen on how professional I
could look on the first day.
Once I had my look just right, I confidently strode out the door to my
new life. Since I was working in a new area, it was like I was any other
new employee. The sound of my heels clicking on the tile floor was
exhilarating beyond belief. I found my new desk and settled in. When
Gwen arrived, she greeted me as if we were old friends. I could tell
instantly she was pleased with results of the makeover. "I really like
that suit, Shelli!" I thanked her and told her I had been dying to wear
it for the longest time. We both laughed at the inside joke and started
the day. That first day was like a dream... it was like I had finally
become the person I was meant to be. Gwen was very easy to work for, but
at the same time I would have done anything for her considering the
kindness and understanding she had shown me. Over time, she did become
much like a big sister, giving me advice on how to polish my image and
carrying myself with more confidence.
Over time, I became much more comfortable in my role. Gwen was the
perfect boss and friend. I met lots of new people and made several new
friends. I was invited to book clubs and a few Girls Night Out - I
enjoyed these as a social outlet and a chance to wear a really cute
dress. Some of the new friends I made were guys. Since gossip is
rampant at any company, I am sure all of the guys knew of my past, but
none ever made mention of it. A lot of us would get together in the
morning for coffee, and I related to the guys as I did the girls - as
friends and nothing more.
One Monday, Gwen arrived at her usual time and asked how my weekend had
been. Fine, I answered. "Just some shopping, you know."
Gwen: "Do you get out at all in the evenings?"
Shelli: "Not really, why?"
Gwen: "I am kind of concerned about your social life. You are an
attractive young woman. You should have a very busy social calendar and
I am not sure why you don t. What about dating? I am sure you have had
offers. It sure seems like there is a regular stream of male visitors to
your desk."
I blushed deeply. I had had a few offers, but I always begged off with
some excuse. I found some of the guys at work attractive, but wasn't
sure if I was ready for dating. I explained this to Gwen. She refused
to take No for an answer. "I am not saying you need to get married, but
you need to get out on some dates and see how you like it. What about
Tom? I see the two of you together all the time - you seem like a really
cute couple. You have fun together. It's just dinner, right?"
Tom was one of my co-workers who I did spend time with. I found him to
be pretty dang cute with a fun sense of humor. I guess I hadn't
considered him as boyfriend material. The more I thought about it, the
more it made sense. We did have a great time together and an innocent
date might be kind of fun. Over the next few weeks, I found myself more
excited about the prospect - dressing up a little bit more ( a nice
camisole under my suit jacket) if I was going to see him at work, I
always made sure my lipstick and makeup were perfect if we were going to
cross paths. I subconsciously flirted with him when the opportunity
presented itself. He also seemed to find reasons to stop by and say
hello. A few times I found my favorite coffee waiting for me when I got
to work. After a little back and forth, Tom asked if I would like to
have dinner with him and I gladly accepted.
We planned the date for Saturday night. When I told Gwen about it, she
was overjoyed.
Gwen: "Great!! We need to make sure you look absolutely fabulous for the
big night. What are you going to wear?"
Me: "I have no idea. I have some cute dresses, but I am not sure any are
perfect for my first big date."
Gwen "Then we will need to go out shopping for the dress that will knock
his socks off. I can't wait"
Given the upcoming date, I had to take stock of my appearance. The last
few years of hormones had really changed how I looked. My breast had
grown nicely (I was currently a 36B bra size) and my hips had filled out
to give me a nice, curvaceous figure. I had taken to exercising
regularly, so I remained relatively thin around the middle. My biggest
asset was my legs - being born as a male, my legs were long and muscular
without a hint of cellulite. My body hair had always been fine and was
made even finer by the hormones. Needless to say, I kept my skin shaven
and very smooth at all times.
In preparation, Gwen and I went on the big shopping trip. I tried on more
dresses than I can count, but enjoyed every second of it. While a little
black dress would have been great, I wanted to save that for another
occasion. We looked mostly at cocktail dresses, and agreed we were
aiming for something sexy and very feminine. We finally decided on a
rose, pink cocktail dress that fell to just above my knees. It would
enhance my chest while showing off my long, lean legs.
Since I was 5 foot 6 inches and Tom was nearly 6 ft. tall, I figured I
could easily wear 3-4 inch heels. I had to splurge on a pair of the most
perfect Jimmy Choo black slingbacks.
On the Friday before the big event, I found a box from at my desk. The
card read "Every girl needs something sexy underneath for a big date,
your friend Gwen." In the box was the cutest white lace bra and panty
set.
On Saturday, I went to my salon to get ready. I had decided to do my
hair as more of a short-medium length, razor cut bob with highlights. It
seemed to take forever, but I was so
happy with the way it looked when I was done. I really wanted my eye
makeup to look stunning. The professionals at the salon understood
exactly what I wanted, and set to work to create a glamorous look
emphasizing long, lush lashes.
I chose a pink lip color that would make my lips look full, soft and
irresistibly kissable.
Finally, I finished things off with a beautiful french manicure. As the
time for Tom to pick me came closer, I was filled with nervous
anticipation. While I was slow to the whole dating idea, I really wanted
to make a great impression. I certainly felt both cute and sexy, and
really hoped he felt the same.
When Tom picked me up, I knew I had made the desired impression. "You
look fantastic" he exclaimed. "Why, thank you" I replied as I gave him a
soft peck on the cheek. He smelled great and look adorable in his blue
blazer. We held hands as he escorted me out to his car. As a gentleman,
he opened the door for me - I didn't hesitate to show a little additional
leg as I got in. Dinner went by quickly as we chatted and laughed through
the meal and wine. As we got up to leave, I eagerly anticipated the
conclusion of our first date.
We walked up to my door slowly as Tom slipped his hand into mine. I
turned to face him as I slipped my other hand into his. We stood close
enough for my breasts to touch his chest. I looked up into his eyes. "I
had a great time tonight, Shelli. Hopefully, we can do it again." "I'd
really like that" I said as I closed my eyes and slowly tilted my head to
my right. Our lips met. His lips were soft and sweet. As we gently
pressed our lips together, I released his hands and brought mine up
toward his shoulders. His hands migrated to my hips. As our lips
pressed tighter, our mouths opened slightly and the tips of our tongues
met. Our tongues slowly caressed each other and a slight low moan
emanated from deep within. As the tongues ventured further and the kiss
became more passionate, I melted into Tom. Our thighs were pressing
against each other, my arms around his neck and shoulders. I felf a
tingling sensation down both my arms and legs while I was enveloped with
warmth. How long the kiss lasted I still could not tell. It seemed like
hours but still not long enough. It was hard to break it off, but I was
afraid of what might happen if I didn't. "Good night" I whispered with a
final soft kiss and slipped in my door.
To be continued....
Ofelia
- 08.10.2021
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