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

I had been a member of the Young Organist’s association for several months, and our winter concert season was getting close. At one meeting, I noticed my mom talking to the other mothers about something, and on the way home, Mom mentioned that they had been talking about performance outfits.

“The other girls are going to wear their red blazers over a white turtleneck top and a white skirt, with white pumps,” Mom said. “You probably want to wear white slacks instead of a skirt, but we should get you some white heels like the other girls so you match.”

“Can’t I wear a skirt too?” I asked.

“Well, that’s probably over the line, but at least you’ll get to wear heels. Of course you’ll have to wear hose too, and it’ll be showing,” she laughed.

“When are we going shopping?” I asked, trying to keep from sounding too eager.

“Maybe Wednesday night after your music lesson,” she smiled.

Wednesday afternoon when she picked me up from school she was really happy.

“Ready to go shoe shopping tonight?” she asked.

“Sure,” I smiled.

“You need to put hose on so you can try on ladie’s shoes. If you want to get really dressed up, wear your white boots and your white turtleneck with a pair of jeans. That way we can make sure the shoes are the right shade of white.”

I went in my room and totally undressed. I got a pair of beige pantyhose out of my dresser drawer and slid them sensually up my legs, totally enjoying the feeling as my dick hardened into a huge erection. I got out my tightest blue jeans and pulled them on, then got out my white turtleneck and slipped it over my head.

I took my white boots and walked out into the family room. Sitting on the sofa, sliding my hosed feet into them, Mom looked at me and said, “That’s a cute outfit.”

We went to the Montgomery Wards store in the mall, walking past several other shoe stores, and I asked why we didn’t stop at them.

“White shoes are out of style in the winter, so not many stores will have them now,” Mom said. “Wards’ has a bridal department, so we’ll have to look there for them. We’ll try to find you some white slacks too. I couldn’t find any in boy’s or men’s, so we’ll have to get you a pair of women’s. They won’t have a fly, so you’ll have to go in a stall and pull them all the way down when you go to the bathroom.”

We went into the bridal side of the shoe department at Wards, and we looked over their selection. They had a classic white pump that was really pretty, but it had a 2 ½” heel. Mom picked it up and looked at it, saying, “This is what I had in mind, but I don’t know if the heel will be too high. We’ll have to see how well you can walk in them.”

About this time the saleslady came over, and Mom said, “Can we see these in a 9?”

“Sure”, the saleslady said, disappearing in the back. Mom looked at me and said, “Go ahead and take off your boots.”

I sat down and took them off, stretching out my toes in my hose and feeling my dick start to get hard again, when the lady came out of the back and sat down in front of me. She opened the box and took out the shoes. They were so pretty. I couldn’t believe they were for me! She slipped them on my feet, and I couldn’t believe how pretty I felt. She looked at me and said, “Stand up and walk around so we can see how they fit.”

The moment of truth. I stood up carefully, and walked away from them toward the mirror, carefully walking heel-to-toe. I caught a glimpse of my feet in the mirror as I was walking toward it, and my eyes nearly bugged out when I saw how sexy my own feet looked in hose and pumps. I stopped in front of the mirror and just stared at my own image.

“Okay dear, now back this way,” the salesgirl said, breaking my reverie.

I did better walking back, and walked past them and over to the other side of the room, marveling at how sexy I felt.

“Are those her first pair of heels?” she asked my Mom. “She walks really well in them.”

“Pretty much,” Mom smiled, knowing that it was her son walking in them.

Looking at me, Mom said, “What do you think? Can you play in them alright?”

“Sure,” I said, breathlessly. I couldn’t believe we were actually going to get them for me. After having them on, I was in love. I couldn’t bear to give them up!

“We’ll go with them then,” Mom said to the salesgirl. She added, “Why don’t you wear them home, so you have a chance to get used to walking in them?”

Oh My God! I thought. Here in the mall! “Okay,” I said, trying to keep my voice from shaking.

After Mom paid for them, she said, “Now we’ll go over to Misses and see if we can find you some white slacks.”

We went over to Ladie’s Fashions and into the Misses’ Department. We found the slacks section and found some in white. Mom took several pairs off the hangers and held them up to me.

“Looks like you’re a size 2 but we’ll have to get you a size Tall if you’re going to wear them with heels.”

She found a pair and steered me into the changing rooms. I couldn’t believe we were going into the Women’s! I stepped out of my heels and slid my jeans off. As I pulled the girl’s slacks on, they were so sheer and light, sliding over my pantyhosed legs. I stepped back into my new high heels and looked at myself in the full-length mirror. I felt so pretty, I couldn’t believe it! I couldn’t stop staring at myself in the mirror. I wanted them so badly!

“So what do you think?” I asked Mom as she was looking at me. “They’re awfully sheer. Your pantyhose panty is showing through them. We’ll have to get you sheer-to-the-waist pantyhose to wear with them.”

After she turned me around a few more times and looked me over, she said,” I think they’ll be OK. I won’t even have to hem them. Go ahead and put your jeans back on.” I hated to take them back off, but I did, putting my jeans back on with my pretty white pumps.

We took them to the counter and paid for them, and then walked out in the midway of the mall. We detoured into Osco drug and went over to the No Nonsense display. I couldn’t believe it. My dick was so hard and quivering if I had dared touch it I would have ejaculated.

As we looked at the Size B Sheer To Waist selection, Mom said, “You want either beige or nude so they match your skin, that way it looks like you’re not wearing anything at all. We’ll get a pair of each and see which matches your skin the closest when you have them on.”
She picked out a pair of each and handed them to me, then we walked over to Cosmetics and she got me some light pink nail polish. As we were waiting in the checkout lane in my high heels, with the bright orange pantyhose packages in my hand for all the world to notice, I felt so girly!
I
walked carefully out to the car, but by now, I was getting used to the heels. I couldn’t stop staring at my feet all the way home, and I think Mom noticed too. “How are your shoes fitting?” she asked.

“Great,” I said. “They’re so nice and soft inside. They feel great on my feet.”

“That’s because they’re women’s. The linings inside are softer so they’re easier on our feet and nylons.”

When we got home, Mom said, “Why don’t you practice your concert pieces to see how your new shoes affect your playing?”

I sat down at the organ and started playing. Actually the pointy toes steered my toes in between the pedals better. As I got done, I wondered what it would feel like to play with the girl’s slacks on. I went into my room and took off my jeans, then I pulled up my sagging pantyhose and then slid on the ladie’s white dress slacks. Looking down, my penis was leaking semen, and I was afraid I would stain my slacks. I got two Kleenexes and put them over the head of my dick before pulling my pants the rest of the way up. Stepping back into my shoes, I couldn’t believe how sleek and feminine I felt. I bent my leg at the knee and pulled it up to my other thigh to see how pretty and smooth my bottom looked. Mom was right, I could see my pantyhose panty showing through. I could hardly wait to try them with my new sheer-to-the-waist hose.

I sashayed back out into the living room and practiced some more. I felt so girly, I could hardly wait to wear them out and perform in them!