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THE FIRST DATE
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New CD/TV/Trans woman's first date.
1.2k words
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leeanna19
leeanna19
46 Stories407 Followers

I wait nervously by my front door. I am trembling. This is my first
date. Simon is picking me up at 7.30. It is 7.35 now. I have been ready
for an hour. I check my reflection in the hall mirror for the 50th time.

My red tinted shoulder length wig looks perfect. It cost a fortune. Real
human hair. I have been spending most of my wages on clothes and makeup
since I decided to stop fighting against my desire to be a woman. I have struggled to be a real man all my life. At 5ft 6 inches it has been
difficult to look the part.

My slim figure and gentle ways made me popular with women. I had lots of
girl friends, but they were just that friends. I learned from one that
they thought I was gay, so I was a "safe" person to have around. One
told me I wasn't like other guy's, who were always trying to get into
their knickers.

If only they knew. I loved women, not sexually, I admired their looks,
their clothes. I wanted to be them. I always looked at women, but it was
their style and clothes I was looking at, not their figures.

I moved out of my parent's house to London when I was 25. I have been
living here for 2 years. One thing about London is that it seems
anything goes. A few months ago we had meeting in the office and I met
my first real life trans woman.

She was an I.T. engineer on a temporary contract updating out laptops.
She looked amazing. She was wearing a leather mini skirt and fishnets.
She had goth style makeup. I stared for too long.

"Yes, before you ask, I am trans." She said.

I apologized and swore I looked at her because I admired her style. She
forgave me and we had a chat over coffee at lunch. She told me her life
story. It reminded me of my life. She seemed so happy. Right then I made
the decision to stop fighting and pretending to be a man.

That night I spent most of my saving on clothes, wigs and makeup. After
a few years of dressing at home I had a yearning to be seen, but I was
just too scared. In my early 20's I started to notice men. I found
myself looking at their eyes and their backsides. I assumed I must have
been gay.

I needed recognition. I thought I looked good as a woman, but I was too
scared to go out. My solution was to put my pictures on a trans dating
site. Within hours I had hundreds of messages. Most were filthy, crude
and horrible. How some of these guys ever meet trans women or any women
amazes me. If your idea of a chat up line is. "I'd like to bend you over
and ......" good luck.

Simon seemed nice. He warned me that the site was a "meat market", and
to be very careful who I met with. We messaged each other for a few days
when he asked me out on a date. My first ever date.

I'd gone flat out. I had shaved every inch of my body and taken ages
with my makeup, I even wore a corset to give me a more feminine shape.
This was my first date, and my first time facing the world as a woman.

There was a knock on the door.

"Hi Kerry, it's Simon. Are you ready?"

I could almost not breath as I opened the door. He stood back from the
step and looked me up and down. I was wearing a long-sleeved knee length
velvet dress, it had a small split at the sides. I was wearing 3-inch
black sandals. My red painted toes could be seen through my seamed
stockings.

"Wow Kerry, you look absolutely amazing."

"I'm not sure about this Simon. I am so nervous I can hardly walk."

"Honestly Kerry, no one would ever take you for anything other than a
beautiful woman."

He leant forward and gently kissed my cheek. He offered his hand, which
I took as I closed my front door.

I could hear my heels click on my garden path. I just hope my neighbors
were not looking out of their windows. My handbag slipped off my
shoulder. So much to get used to. As I walked the hundred yards to his
car, the light breeze blew the perfume about me. I loved the sweet smell.

Simon turned to me and smiled. He looked so confident.

"Not far now beautiful."

Beautiful? This was the second time me called her that. I wasn't used to
anyone complementing her appearance. A little thrill ran through me. I
was aware of her garter straps tugging gently on my stockings as I
walked. My legs were rubbing together. I could hear the faint zipping
noise of my stockings.

She could feel my knickers being moved slightly by the garter straps.
The silk was gently caressing my small member. I was starting to get
hard. I had to stop thinking about how I was dressed. I didn't want to
show through my dress.

We arrived at Simon's BMW. He stood by the passenger door and kissed me
on the lips. I wet my lips as I drew away and he opened the door for me.
I could taste my lipstick. I thought back to youtube videos I had seen.
I gently eased into the car seat and swung my legs in, keeping them
together. So many things to remember. So different doing it as a woman.

Simon closed the door for me. No one had ever opened a door like that
for me. It felt like I was a precious thing. Something to be cared for.
It was intoxicating.

When we arrived Simon parked, opened my door and took my hand to help me
get out. As I sat in the Italian restaurant I could feel my knickers had
ridden up between the cheeks of my bottom. I could feel the lace
slightly tickling me.

I smiled at Simon when he asked if he could order for me. I had little experience in eating out in restaurants. Simon ordered in perfect
Italian. Well, I thought it was anyway. As we drank wine, he held my
hands and stared into my eyes. I felt myself melt inside. He looked so
manly. I breathed in his musky aftershave and felt so "womanly" next to him.

No one gave me an uncertain glance. I got a few admiring glances by some
of the men. It felt so right. I felt I belonged in this life. I wished I
could stay like this forever. Simon paid the bill and rushed around to
pull my chair out for me. He offered me his arm and we walked to his car.

With each step my sensuous clothes made themselves known. I was in
heaven as I sat in the car with him. I was his woman at that moment. He
was my man. He leaned across and pulled me in for a deep kiss. His
tongue explored my mouth, probing and tickling. I felt so vulnerable as
he penetrated my mouth. His hand was on the back of my neck holding me
in place. I was his.

"Why don't you come back to my place for a coffee?"

My heart felt like it would break through my chest. So many firsts
tonight. Would Ishe let this be the first time I made love? Could I?



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leeanna19
leeanna19
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COMMENTS (5)
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5 COMMENTS
leeanna19leeanna196 months agoAuthor
Hi I write a lot of stories. Over 120 so far. I put selected ones on
here. If there is little interest,I move on to another. This is all I wrote.

Anonymous6 months ago
After having coffee after date did Terry get down on her knees and suck
his dick more please

leeanna19leeanna199 months agoAuthor
Someone on another site asked if Kerry was a crossdresser or trans.

That's not clear is it. Many transgender women start out thinking they
are transvestites. Some realize the more they dress and live as women
that's who they should be.

For older trans women, it was very difficult to express yourself in the
70's. You ended with electro shock therapy and other awful things.

Some just want to live full time as women, but remain intact. The lables
we have don't really cover it. She is a guy most of the time so I would
say crossdresser.

For me gender (behavior and feeling) are between the ears, not the legs.

JilluvscoxJilluvscox9 months ago
Nice descriptions of the feelings one has when going out dressed for the
first time. Brings back memories from long ago. Was I 'really' that
nervous? Yes, I absolutely was. Hope you continue this story. Would love
to hear how it went afterwards.

leeanna19leeanna199 months agoAuthor
Sorry about the mistakes

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