Caught in Stockings

When I was a teenager I worked in a ladies clothing store. My mother was close friends with the owner and Manager Mrs. Jade. I loved working there amongst all the pretty clothing.

You see I had always had an interest in girly clothing and fashion. I had always loved pretty dresses, skirts and tops. I especially loved all the pretty lace lingerie and hosiery that the shop sold. Mrs. Jade seemed to notice this about me and gave me more responsibilities like opening up the store each day.

There was usually an hour or so where it was just me in the empty store. I walked down the aisles fingers brushing lovingly over the girlie clothing — trying to work up the courage to try something on.

Eventually I gave in. A pair of pretty pink sheer stockings was the first thing I tried on. Then a few days later it was some open toed stiletto heels. It didn’t take long for me to start trying on all the pretty dresses, prancing and twirling around the empty store like I was a disney princess.

Then one day something happened.

I was called into Mrs Jade’s office. She had a stern look on her face as she shut the door behind me and asked me to take a seat. I did as she asked. Mrs. Jade was almost six feet tall and she towered over me in her black shiny heels and her white pencil skirt. Her long blonde hair was in a tight bun. She had a scary sort of beauty that made me think of a very strict principal.

“Jamie I want to ask you about something I found on our store cameras. Do you know what I am talking about?” She asked as she sat down across from me at her desk.

I stared at her in shock. The cameras! I had not even thought about them.

I opened my mouth. I started to stammer.

“I’m sorry…” I started to say.

She shook her head and said firmly. “You are fired!”

The words made me go quiet. I felt like crying. My mother would be so mad at me.

She stared over the desk at me.

“Well Jamie? Why are you still here? Pack up your things and leave this store right now!”

I could not hold back the tears and as I stood I felt them run down my face.

I was about to open the door to leave when she called out.

“Unless…”

I stopped and turned.

“Unless, you are willing to try much much harder, Jasmine. She added with a smile.”

I took a step forward.

“I need a shop assistant. A pretty Female, shop assistant, who loves dressing up like the pretty girl she is, and talk about pretty girlie things with my customers.” She said all of this slowly while looking me in the eye.

Her face had a smile on it.

Would you like to be that girl for me Jasmine? Or would you like me to call your mother, and tell her how I fired her son?

I stood there and just whispered.

“Jasmine. I will be Jasmine.”

She stood up and pulled me to the back of her office, where there was a full length mirror and a rack of her latest arrivals.

“Now.” She said, “a girl your age would probably wear something like this”, she said and pulled a pretty pink and white tartan skirt off the rack. She then thought a bit more and pulled out a small white sweater.

“There we go”, she said, holding the sweater and skirt up against me with a thoughtful look on her face. She handed both to me and turned to another rack.

“She would also want to look pretty and sexy for her boyfriend, wouldn’t she?” She said and winked at me, pulling out a pair of pretty pink lace bra, with a matching set of pink panties.

Some tights too she said to herself and handed all of the items to me.

“Now undress and put those on Jasmine. It’s time to put you to work.”

I felt so embarrassed, but I had no choice. I turned around and started to undress.

“You have lovely long legs Jasmine, I’m glad you have kept them smooth and soft.” I heard her say.

She stepped closer and reached for the little hair band I used to keep my long hair tied.

“Your hair must be long and flowing down your back Jasmine.” She said and tugged it free, making my hair fall down my back, loose and flowing.

I nodded, my face red as I slipped into the panties and the sheer tights. My skin was singing as the soft lace brushed my smooth curves. As I slipped on the bra and pulled it up against my chest something inside me just burst with happiness.

I could hear Mrs. Jade behind me, helping me with the bra clasp.

“Good girl Jasmine. I will help you with everything you need to be a pretty girl.”

I nodded and stepped into the skirt and she helped me with the tiny zipper on the back. As I reached for the sweater she stopped me, and made me turn around. She had two adhesive breast forms in her hands.

“Slip these into your bra Jasmine.”

I did as she asked and they filled up the pink lace cups lifting them up. They made the sweater stretch out and made it look like I had lovely B cup breasts.

“There, don’t you feel pretty?” She asked.

I do. I said, the words spilling out before I could stop myself. I looked down at myself, the pretty tartan skirt ending half way up my sheer encased thighs, the tight white cotton sweater stretched out girlishly with my soft pert breasts.

Heels. She said with a laugh. How could I have forgotten? Nothing makes a girl feel like a woman like heels do. She then paused. Except maybe cock. She laughed again.

She picked out a small pair of black open toed heels. Nothing too high until you are ready Jasmine. She said and bent low to help me step into each in turn.

“There. Perfect.”

She said and stood back adding, “give us a spin now Jasmine.”

I did as she asked. Turning around slowly for her. I felt so warm and girlie as I felt the skirt swish around my legs. I felt so female and beautiful as I felt the weight of my breasts under the sweater. I felt so sexy and desired as the sheer tights clung to my thighs and legs.

But I was still terrified of what she wanted.

“Are you okay to be my shop assistant now Jasmine?” She asked. “No more boy things, I want you to let your inner girl come out. I want you to show your pretty girlie side to all my customers. I know you have it in you my darling.”

I could only stare back.

“What will they think?” I said finally.

“They will think you are a pretty girl, that’s all.” She said kindly.

She waited a few moments and then reached to open her handbag. She pulled out a little polaroid photograph and handed it to me.

“Do you know who that is, Jasmine?”

I looked at the picture. It was the face of a teenage boy like me, he had pretty features and his face looked familiar but I wasn’t sure why.

“Who is it?” I asked finally.

“That was me.” She said and smiled as my jaw dropped.

“Yes Jasmine, we have more in common than you think. You see I was like you once. I thought I was a boy but deep inside in my heart I knew I was really female. I knew I wanted to be a pretty girl and dress in pretty feminine clothing and act girlie.”

She stopped and smiled kindly.

“There’s nothing wrong with the feelings in your heart, my pretty little Jasmine.”

“But, how?” I stammered.

“Hormones. Surgery. Following my heart. All things I am ready to help you with honey. You see, your mother is my oldest and dearest friend and she told me she was worried about her son. Worried that he was having thoughts and feelings that were confusing to him.”

“How? How did she know?” I asked.

“A mother always knows sweetheart, she said. She could tell you were her little girl even though you were born as a boy. She just wants you to be happy. As do I.”

She smiled. “Now let’s get back to work.”

— —

That first day was the start of my new life. I loved being girlie and dressing girlie at work. I loved being treated like a female and being spoken to with female pronouns. All the customers were so kind to me and I felt like one of the girls. Working in Mrs. Jade’s store was the best thing about my day.

Eventually I went full time, throwing away my boy clothes and dressing fully as a girl.

Mrs. Jade helped me choose a gender therapist and helped me start taking female hormones. She taught me everything about being a girl, putting on makeup, walking and speaking like a girl and looking after my body.

When the hormones made my real breasts grow she also helped me pick out my first bra.

She was like a second mother to me and I love her dearly.