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 -- Tracy

When we were planning a visit to see my sister-in-law and her son, Mom said, “You know, we should go shoe shopping and get you some cute girl shoes for you to wear. Something a little more age-appropriate for a thirteen year old instead of my high heeled sandals. Like maybe some cute Mary Janes with a little heel.”

“That would be great,” I said, getting aroused at the thought of going and trying on girl’s shoes. “But what will Charlene think?”

“Don’t worry. I’ll talk to her. I’ll bet she’ll be more supportive than you think.”

The next Sunday, after church, we went to the mall and stopped into a family shoe store. We were looking at girl’s and ladies shoes and Mom found some back patent Mary Janes that were really cute.

The sales lady approached us and asked, “Can I help you?”

Mom pointed to the Mary Janes and said, “We’d like to try a pair of those.”

“Do you know your size?” She was looking from Mom to me, confused.

“I wear an 8, and mine fit him pretty well, so let’s start there,” Mom said.

She smirked and walked away. Mom looked at me and said, “Take off your shoes and socks.”

I sat down and took off my shoes and socks, and crossed my legs with my pantyhosed feet on display. The saleslady came back with a box and sat down in front of me, staring at my reinforced toe nylons for several seconds before she opened the box and took out the shoes. She slid my feet into them, and the feel of her fingers on my nyloned ankles made my dick instantly hard. She fastened the straps and said, “Stand up. How do they feel?”

They fit well and didn’t pinch my toes. The saleslady said, “Walk around in them and see how you can walk.”

I got up and walked heel-to-toe across the room, toward the low mirror, and couldn’t believe how cute they looked on me. You could see most of my feet in them, and my skin looked flawlessly perfect in my nylons. Mom said, “Those are really cute.”

The saleslady said, “He can wear them for a bit while you shop, if you like.”

Mom and I went back to the display and kept looking while I kept walking around in them. I looked so cute in them! I kept looking at the front of the store to make sure none of my friends came in. The saleslady went over to help some other customers but kept looking our way. Finally she came back over. “Have you decided?” she asked.

“What do you think?” Mom asked me.

“I really like them. They’re really cute.”

“Okay, we’ll take them,” Mom said.

“Is she wearing them home?” the saleslady asked, obviously embarrassed.

“No, he can wear his others,” she said, and I sat back down. The saleslady took them off my feet and put them back in the box, constantly stealing glances at my nyloned feet, until I put my socks and shoes back on.

As we walked out of the store, Mom said, “There, now you have some girl shoes of your own that you can wear out when we go out of town.”

“Wow, thanks,” I said, wishing I was wearing them home.

When we were packing to leave, Mom came into my room and said, “Let’s take your Mary Janes and a pair of pantyhose for you in case we want to get dressed up and go to a nice restaurant. It’s still pretty cold up there so we’ll also take your cable knit tights and your shoeboots. Do you want to wear tights or underwear?”

I said, “Tights. But I don’t want Char to make fun of me.”

“She won’t. I talked to her the other night, and told her that you liked to look a little girly when you dress up, and she was OK with that. She said she even might have some things for you to try.”

“Can I wear tights and shoeboots on the trip up there?”

“Sure,” Mom said. “I’ll leave a pair out for you to wear and pack the rest. You have three pairs and that should be enough. I’ll just take a pair of underwear for you to sleep in if you want.”

“Ummm, can I ask something else?”

“What sweetie?”

“Do you think I could have nail polish on up there?”

Mom thought a minute, and said, “Sure. Why don’t we do our nails tonight before bed? We could even do your toes if you want.”

We had a close time doing our nails. I felt so pretty when we got done. The next morning, when I was out in the kitchen eating breakfast, I couldn’t believe how cute my hands and feet were!