Chris's Surprise Prize Part 1

Chris's Surprise Prize Part 1

My name is Christopher James who is 22 years old. I am called Chris. I
am a closet cross-dresser. I live on my own in an apartment in Palm Beach,
Florida and worked at a bank. I bought my clothes by mail-order not
having the courage to buy things in person. I just loved the feel of the
soft silky women's clothes on my skin. I often wore panties and
pantyhose under my suit to work. I had several nightgowns which I always
wore to bed. In fact I rarely wore male sleepwear. While I was growing
up I used to wear my mother's clothes.

I had entered a completion in a magazine called "Blush". The first prize
was an car which would be great as my own was old and giving lots of
problems. The other prizes were surprise prizes. They just gave the
value of the prizes. The 2nd prize was worth $30,000, while the other
prizes were lesser amounts.

I had just got home from work and entering the foyer of the apartment
building from the underground garage I went to my post box. I collected
my post and noted amongst the envelopes was one from "Blush". It was
after the closing date of the competition. I went into the elevator and
heard someone calling for me to hold the elevator. It was a woman who
lived on the same floor as me. Her name was Patricia and I fancied her
but not had the courage to ask her out on a date and also because of an
incident. The building had a basement Laundromat. I had on occasion
washed my women's clothes there. There was one occasion when Patricia
had surprised me when I was taking some of my delicates out of the
drier. She looked at me quizzically but did not say anything.

Patricia was wearing a sheer blouse and her lacy bra was visible. I
caught myself staring at her bra rather than its contents. She noticed
and smiled and said, "Chris are you looking at my tits?" I averted my
eyes to look into her eyes. I was short for a guy and Patricia was
taller than me. I felt my face get hot as I blushed. Patricia continues
to tease me and said, "Or is it my bra you were looking at?"

I blushed even more. I stammered, "S... sorry it's your t... tits I was
looking at."

Patricia said, "You can't fool me, I know it's my bra you were looking
at." I just stayed silent the rest of the ride in the elevator. We
reached our floor and then exited the elevator. Being a gentleman I let
Patricia go first. I walked behind her and looked at her back my eyes
focused on her bra straps. I remembered from school I loved looking at
the girl's bra straps as I sat behind them in class.

We reached my apartment first and I stopped to get my keys out. Patricia
turned around and waved at me and I returned her wave. I unlocked my
door and went inside. The first thing I did was after putting my
briefcase down was open the letter from "Blush". I began to read the
contents and my mouth dropped open in surprise when I read that that I
had won the 2nd second prize. I turned to the second page and discovered
what I had won was a voucher from a bridal store to the value of
$30,000. The voucher was not exchangeable for cash and had to be used
within a month. I was stunned I had won something of great value yet to
get it I would have to go to a bridal shop and present the voucher. I
was apprehensive of doing it.

The next day was Saturday and I decided to go to the shop called
"Cinderella's" just to check the place out. I loved walking in malls and
secretly looking at women's clothes. But for now I was just going to
relax with a DVD and also surf the internet while dressed of course. I
made myself a cup of coffee and relaxed while sitting my couch. I read
the letter from "Blush" again. I had always wanted to wear a wedding
dress with lots of petticoats. I now had a chance. I just had to muster
up enough courage to go into the shop. I went to my bedroom which looked
like a normal young guy's room. I kept my female clothes with my male
clothes. I began to undress, removing my outer male wear. I had panties
and pantyhose on.

I just added a silk lacy camisole and a half slip to what I was wearing.
I put on a white silk blouse and a red skirt. I just loved the cool
feeling of the slip on my stocking legs. I had small feet and was able
to wear ladies shoes so put on a pair of white low heeled sandals. I did
not shave my leg and body hair so the effect was not that good. I did
not have the nerve to do that. I wore my hair on my shoulders and for
work wore it in a ponytail. At home I wore it loose. I undid it and
brushed it out. I would love for someone to style it for me. I kept my
finger and toenails neatly trimmed and shaped. I would often paint my

I went to the kitchen and began to prepare my supper. I was a fairly
good cook and loved to make my own meals. Tonight I was doing my
favorite, macaroni cheese. I had the TV on and was watching soaps. I had
a glass of wine as I cooked. I had everything done by the time "The Bold
and the Beautiful" started.

After my meal I went to my bedroom to fetch some nail polish which I
used to paint my nails as I watched the TV news. After that I went to my
room and while standing in the bathroom I got a tube of lipstick from
the cabinet and applied it to my lips. I always coated it thickly. Back
in my lounge I poured myself another glass of wine and put in a DVD. It
was about cross-dressing and portraying yourself as a female. I knew it
would be a long time before I venture outdoors while dressed.

As I watched I sipped my wine and was delighted when I left a trace of
lipstick on the glass. After the DVD I put on a Star Trek Voyager DVD.
This was my other passion, sci-fi movies. Later on I got ready for bed.
It was nice to undress and then put on my nightgown, which was a long
pink cerise creation. It had a matching gown. I kept my panties,
pantyhose and slip on. I got into bed after doing my teeth and reveled
at the soft silky material on my skin. I surfed the internet for a while
looking at sissy outfits. I fell asleep wondering about my visit to the
bridal shop the next day.

I woke the next morning and as was my custom upon waking I began to
stroke myself after I lifted myself up and pulled my panties down. I
gripped my tool with my nightgown. My tool was normally hard this time
of the morning being excited by the soft silky material of the
nightgown. I wanted to prolong my excitement so I stroked myself slowly.
I began to build up in excitement till I reached the point of no return
and I erupted into my nightgown.

I lay and relaxed for a while and then got up and put on a clean
nightgown and a pink quilted gown and went to make myself breakfast.
Really had a proper breakfast during the week and enjoyed a full
breakfast on the weekends. I finished eating and then went to the
bathroom and where I had a long leisurely bubble bath.

I got out the bath and dried myself off with one of my soft fluffy pink
towels. I stood in front of the mirror and shaved while standing in the
nude. This was a task I hated but an unshaved face looked really
terrible. I powdered myself with baby powder. It had no smell. I went to
my room and began to dress. I put a pink panty which had ruffles across
the seat. Next I put on some thigh high stockings which had elasticized
top to hold the up. I did not want to wear my garter belt in case they
were seen under my pants.

I put on one of my silk shirts after spraying myself with deodorant. I
loved silky clothes, it looked masculine. Next I put on a pair of slacks
and then my socks and shoes. I brushed my teeth and then left the

As I walked along the corridor became aware of someone walking behind me
and turned around and saw it was Patricia. I said hello and she greeted
me also. I got to the elevator and held it for Patricia. We began to
ride down to the foyer. During the ride down other people got in the
elevator and soon it was full. Amongst the passengers was another girl
Kathy who lived on a lower floor and was friends with Patricia. I ended
up standing close to Patricia with my rear pressed against her.

We got to the foyer. Kathy quickly moved forward and quickly closed the
doors and pushed a few buttons. The elevator started going up. I asked
her what she was doing. She did not reply but Patricia asked, "Chris are
you wearing panties? Don't deny it I could feel them while you were
pressed close to me."

I blushed and said, "No I'm not," blushing further.

She replied and said, "Why are you blushing then?"

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