The Shop ladyboy

Published March 17, 2024 tag category
The Shop ladyboy

Every day I had passed the shop, and longingly looked in the window! Once or
twice I had plucked up the courage to venture in and touch the beautiful
pretty things! This was to be one of these times.

I was still at school, and this shop was in a little shopping quad that I
had to real forced anal against her will out of my way to get to. Quite a bit out of my way.

But here I was again, the door bell chimed as I pushed it open; I timed it
so there was a woman going in at the same time as. My theory was that she
looked like she was with me perhaps my mother.

I walked passed the lovely skirts and dresses. I touched one or two of them
as I passed. There as something about the feeling of them that I craved if I
saw something I liked I wasn't satisfied until I had thoroughly touched.
Mesmerised by the feel. I went through the section I adored
the bras and garter belts, the knickers looked so conformable, not like Mrs
Peterson our next door neighbour who panties I had raided off her washing
line. They were big and bland, these were dainty and sexy!

I got to my favourite section, women's shoes! For a local shop in a small
town I never realised how varied their ranges were. There where flats and
courts for the older women. And slippers for the grannies. There where
stilettos for the working ladies of the town. Then there where massive black
or white or me boots for the 18 year old tranny! I lifted the black
ones off the shelf and held them in my trembling hands. The cashier could
probably hear my heart pounding, on the other side of the shop.

I held them up to my nose and took a massive breath I inhaled the beautiful
leather smell. The leather was so soft. And the massive 4 inch spike heel
was so hard.

I have been having wet dreams about these boots. They where the holy grail
of a young sissy rugby player. In one hand I could count the number of times
I had pleasured myself while not thinking about these beauties! And I would
need the most powerful computer to calculate how many wanks had been because
of these boots. The stuff dreams where made of.

I have no idea where this fascination has arrived from. Many times I have
tried to place it, wondering if I wasn't given enough attention from my
mother or father? I grew up in a normal house my mum and dad where a normal
couple they had there moments, I have a . She is a normal 18 year
old. I go to a normal school, where I neither bully nor am bullied. I'm
quite popular with the entire school fraternity; I get a lot of attention
from girls. I play rugby for my school and my county. I'm still growing
about 5 ft 5. About 8 stone in weight and most importantly a size 5 shoe!
I sometimes hate myself for my adoration for women's cloths. I find my self
in tears post ejaculation in my sister's panties ashamed at what I'm doing!
I to this day have no explanation for it.

I'm in the middle of a nearly wet daydream about these boots when I felt a
hand on my shoulder.

"Are you ok there son?" the old shop keeper asked I was burning my face was
so red I'm sure air traffic control had problems with landing planes!
"err err ea." I stammered getting hotter and hotter.
"It's ok Mr Daniel's, I'm sorting him out! Good night now sir" said a
younger sales man.

"Right you be then, have a nice evening then Craig. Good night" I was stuck
I didn't know what to do should I run, should I stay I was totally frozen.
My face was burning up.
I heard the door bell chime as Mr Daniel's left for home.
"I will be with you in a second son!" Craig shouted over to me. I flashed my
mind screamed
"Get out of here quick" I turned and ran. I got to the door but I was
locked. Panicking now I realised that I was still holding the boot. Would
he think I was shoplifting? He calmly walked over to me and gently said
"Don't panic love I want to be your friend" he took the boot out of my hand
and reached passed me to pull xnxxv sunny leone video the blinds on the door.
"Come with me sweetie!" he swaggered off towards the shoe section again. I
hesitantly followed him. We got there and he said
"Now sweetie plop your wee arse down there and we can measure you tootsies."
I sat down my head was whirring. What in the world was happening? He kneeled
in front of me and took off my shoe and tutted when he saw my dirty sweaty
white sport socks. This won't do he said pealing them off my feet, and
causally tossing them toward a nearby bin. He placed a foot measuring board
to my feet and said
"Ah good a size 5, we can work with that!" my heart was beating double quick
time. He got up and disappeared. I was too stunned to move. He came back
several minutes latter my eyes could not focus on what he had brought with
him. He said stand up love, and we can get you ready!
I did as he asked, he first told me to take off my blazer, shirt and tie.
Which I did the he asked me to remove my trousers, he gasped when I had done
I was standing naked except my black cotton boxer shorts, and the hardest
erection I've ever had in my life. He said
"Shorts too" I put my thumb within the waist band and eased them down my
legs, stepping out of them. He tutted at my boner and said
"Now give me a twirl" I began to turn round totally dazed and confused when
I faced him again he brought his hand hard onto my penis. With a spanking
action. It was soft in no time I was in agony. After I had recovered he
handed me a pair of skin coloured nylon stockings with lace tops. He gasped
as I tried for the to put them on. I thought it was like putting
on a pair of socks.
He knelt in front f me and said
"Here like this!" rolling them up my smooth legs. He then stood me up and
clipped on a black Basque, clipping the stockings on to the 6 dangling
straps I was amazed.
He handed me a pair of knickers that matched the Basque and while I slipped
them on he put some jelly like things into the cups of the Basque.

He gave me a skirt it was like the skirts the 6th form wore at my high school
about knee high and skin tight. I always thought that they where too sexy
for schools but I considered my self lucky. With it he gave me a white
blouse and handed me back my school tie. When I was standing in my school
uniform he passed me the black knee high boots.
"Not quite school uniform but it looks great!"
Was amazed and couldn't believe my luck.

I sat down my hands trembling and unzipped the left boot and began to put my
right foot into it. I realised and corrected myself.
Then I slowly zipped it up to my knee. Wow what a noise, what a feeling! I
felt empowered somehow. Then I put on the right foot. And zipped it up.
I felt like nothing could bring off this cloud. They felt like they where
made for my feet. I stood up. And a little gingerly I took my first step as
a woman.

I wobbled around a bit but soon I got the hang of it. I stood in front of
the full length mirror and gasped. Although I had no make up on at all I
looked like a girl with short hair. I began giggling with excitement.
"Oh thank you so much!" I managed to squeak out. I reached over and touched
his hand in a grateful gesture. He smiled.
"Now it is time to thank me." I didn't know what he meant but I didn't care.
This was the most alive I had felt all my life. I for the first time was who
I was supposed to be!
"Twirl for me again!" he asked I gleefully spun around. When I came to face
him again he was closer to me and his hand reached out and touched my
bottom. I swatted it away and tried to ignore it but he stepped even closer
to me and placed both hands on my face. He pulled me closer and planted his
lips on mine!
I stood in shock, for a second or two. His hand slipped to my ass again, and
then I kissed back. Sparks of electricity shot up and down my body. I
unconsciously raised my left leg, and pointed my toes out. The kiss got more
passionate his tongue forced into my mouth and began to explore me. I
slipped my tongue into his mouth.
He pulled me even closer and began to grind his crotch into my own. I could
feel his hardness begin to grow.
I broke the kiss and stepped away my breath lost I was in a slight daze. As
I backed away I tripped over the chair I had been sitting on I fell
backwards into it and blinked. As my eyes opened there was his cock inches
away closing in on me?
Instinct took over I open my mouth and swallowed. Within seconds his balls
rested on my chin. I reached up and massaged his ass. His bottom shaven and
smooth. He began to withdraw his cock from me. I followed it out a bit.
He stood there kneeing in front of my face his manhood bobbing in time with
his breath. My eyes focused on it. He took hold of his meat and placed it on
my lips. Then as I tried to open up for him he began to smack my face with
his penis. Then he slammed it into me. He began to work my mouth like a
pussy. Slam fucking my face pulling it almost all the way out only to force
it all the way in.
I loved it. Why did my girlfriends hate this so much? I was moaning like a
crazed whore around his lovely cock. It must have sounded like a porn movie,
for I was truly in character.

He pulled out of me and winked.
He stood up and took hold of my hair lifting me out of my seat. I stood
facing him and he turned me round and pushed me forward onto the chair face
first. I was on my knees my head dangling over the top of it. He lifted my
skirt and I heard my knickers rip. I felt his hot breath on my ass and soon
he parted my cheeks and was tongue fucking my little hole. This blew my

That's why they prefer to be ate out than to blow. I thought thinking of my
past girlfriends. His tongue darted out of my little hot hole. I was moaning
again. This was the greatest pleasure I have ever experienced.
"Oh my god yes!"
"ohhhhhhhh don't stop!"
"mmmmmmmmmmm fuck yea!"
Then he pulled away. And his fingers replaced his tongue getting deeper. He
slide them in and out a second then third followed. They seemed to be
slipping into and out of my little hole; he must of lubbed them with
Then he said:
"you're ready now!" I was nearly passed out draped over the chair. Trying
desperately to catch my breath. And to figure out what exactly was happening
to me.
I knew I was about to get fucked and I couldn't wait to be penetrated!
He stepped closer to me I felt his tip brush against my thigh getting caught
on my stocking strap. I reached round out of sheer desperation and took hold
of his cock. And aimed it at where my pussy was.
Then he was at the door! I felt just the tip enter. The feeling was out of
this world!! He stood the with less than an inch of his dick embedded in my
little .