This is a true story of how my Mom feminized me as a teenager. She had caught me wearing her pantyhose the summer before seventh grade. I got the surprise of my life the first Sunday of junior high, when she started encouraging me to wear them, and then it was all downhill from there. -- Tracy

A few other vignettes that I had forgotten about……..

A few weeks later, Mom came home from work on a Friday night and said, “I really don’t feel like cooking. Let’s go out to for dinner. You should probably wear something nice.”

Great, I can wear nylons! I thought. As I was going to get dressed, Mom said, “You know, it’s dark outside, and it will be dark in the restaurant. How would you like to wear my heels outside? Nobody will notice.”

“Sure,” I said, my heart pounding.

I got dressed, and when I came out of my room, Mom had the high heeled sandals out on her bed already. “Here you go,” she said. “Remember how to walk in them?”

I put them on and we got ready to leave. When we walked out in the garage, I could feel the cold air on my toes, and knew they were on display!

When we got to the restaurant, I walked next to Mom, trying not to be self-conscious. We stood in line to wait to eat, but no one even noticed my heels and hose. I couldn’t believe I was standing there in public in ladie’s high heeled sandals and panty hose! It was a dream come true. My dick was getting so hard, and I forced myself to think about something else so people wouldn’t notice my erection. After we sat down at our table, I noticed a boy that was about my age sitting at the next table. I noticed he was staring at my feet. I wondered what he was thinking?

A little while later, they got up to leave, and his Mom looked at my Mom and said, “Oh hi Ruth, I didn’t realize that was you sitting there!”

Mom said, “Oh, hi Jackie! I didn’t see that you were sitting there either. Guess we had our backs to each other!”

They sat down at our table and started to talk. The boy introduced himself as Jimmy, and we made small talk. They lived in the next city from ours, about twenty miles away. I noticed he kept sneaking glances at my feet, so I decided to put on a show for him, crossing my legs and bobbing my foot up and down in my high heel.

When we got home, we took off our heels, and I handed them to Mom. She said, “You know, why don’t you just keep them in your closet. If I want them, I know where to find them.”

Wow, I thought. My SECOND official pair of high heels!

That summer, my Mom got a call one night from Jackie, the woman that we had met at the restaurant the previous winter with her son Jimmy. After they talked for a while, Mom came into my room and said, “Well, I have an interesting question for you. Jackie’s son Jimmy asked her if he could take ‘my daughter Brian’ to the fair with him.” She sat down on the bed next to me. “I told her that we’d talk about it. I guess we didn’t plan on this happening, did we? What do you think? Would you like to go with him? You don’t have to if you don’t want to. Obviously you’d have to wear girl clothes.”

The thought was so exciting, actually going out on a date! As a girl! “Um, OK, I guess,” I stammered. “What would I wear?”

“Well, it’s informal, so you could wear your girl jeans. And your Mary Jane flats, you wouldn’t want to wear heels to a county fair.”

“What top would I wear?”

She thought for a minute. “You could wear that white bodysuit I gave you. You could wear one of your sleeping camis underneath it, that would make it look like you had a bra on.”

“Wow, OK,” I said, hesitantly.

Mom called Jackie back and said I would go.

The next Tuesday was my ‘date’. When Mom came home from work, she had a package in her hand from the drugstore, and she handed it to me. “Here,” she said, “I got you something for tonight. It’s Secret deodorant. It’s for women. It’ll make you smell more like a girl.”

“Wow, thanks,” I smiled.

An hour before he was supposed to pick me up, I went in my room to get ready, my heart pounding in anticipation. I undressed and put on my Secret deodorant, enjoying the pretty scent. Then I put on pantyhose, a white cami, the white bodysuit, and my girl jeans. I stepped into my black patent Mary Janes and then went out and looked at myself in the mirror. I couldn’t believe how pretty I looked. Mom came out of her room and said, “Wow! Look at you!”

We went in the bathroom and she helped my do my hair, and then handed me a small purse. “Here, put your lipstick in here, along with some tissues. Remember you have to use the ladie’s room if you have to go potty. Remember to sit down to pee.”

“I will,” I said.

“Here, I have something else for you,” she said. She had a bottle of perfume in her hand, and she opened it, dabbed some on her finger, and then touched the sides of my neck. I immediately smelled the scent of the perfume, it was so nice!

“There, now you’ll really smell pretty. You should probably try to do your push job before they get here, so you don’t have to have one when you’re out in public.”

I took one of her women’s magazines into the bathroom with me, and after trying for a few minutes, I was able to have a bowel movement. I called Mom to wipe me, and as she was washing her hands afterward, we heard the doorbell ring.

It was Jackie and Jimmy, and after we said our goodbyes, Jackie drove us to the fair. Jimmy and I sat in the back seat together, awkwardly silent. I saw he kept staring at me. I hoped he liked what he saw!

We had a great time at the fair. First we went and bought tickets for the rides, and went on the grown-up scary ones. I felt afraid, but didn’t want to show it. I sat close to Jimmy. He was my protector, and told me not to be afraid. Then we decided to get ice cream. We sat at a table eating, and I crossed my legs and was bobbing my foot up and down. I saw Jimmy staring at it, and I started rotating my ankle around, making wrinkles in my nylons, showing that I had hose on! Jimmy looked at me and said, “Wow! You look so pretty! I’m really glad you decided to come.”

I gave him a big smile. “Thank you for asking me! This is really nice. I’ve never been on a date before. I guess this is my first,” I said, looking down and blushing.

After a few more minutes of awkward silence, he said, “Are you done? Let’s go look at the animals.”

“Sure,” I said. I picked up our trash and Jimmy took it and threw it away. When I stood up, I put my purse strap on my right shoulder, and when we walked away, I took his hand. He looked at me and smiled. He squeezed my hand in return, and my heart started beating fast. My dick got so hard, and I was afraid people would notice. I tried to think about something else so it would go down, but it was really difficult. When I looked down at myself and saw my girl clothes and nyloned feet, I got aroused. When I felt Jimmy’s hand, I got aroused. When we were walking and I felt my jeans sliding over my hose, I got aroused. What was a dressed-up sheboi to do? Finally I said I had to go the bathroom, and I went into a stall in the ladie’s bathroom, closed the door, and put my hand down my pants and straightened out my erect dick so it wasn’t in a bind.

We held hands for the rest of the evening and I imagined we were boyfriend and girlfriend! It was such a wonderful evening. On the car ride home, we sat close together in the back seat, holding hands. I laid my free hand on my huge erection in the dark, squeezing it gently so Jimmy wouldn’t notice. I was hoping for a chance to kiss him, but when we got back to my house, we all walked inside together so we didn’t get a chance. Darn!

After they left, I slid out of my Mary Janes, said goodnight to Mom, and went in my room. I slid out of my tight girl jeans and the bodysuit, but left the cami and the pantyhose on and went to bed. I imagined I was snuggled up to Jimmy in bed and we were making out. I started masturbating with one hand while I ran my other hand up and down my pantyhosed leg, imagining it was Jimmy caressing me, and I ejaculated so hard it hurt!

A few days later, Mom ran into Jimmy’s mom at a business meeting, and said that Jimmy just couldn’t stop talking about me on the way home. “She was so pretty and smelled so nice. And she looked so grown up! I saw she was even wearing nylons like you, Mom!”