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

The following year, after we graduated from high school, Becky and I got engaged. After that, her parents got a little less uptight about us being together, thankfully. About a month before Thanksgiving, Becky was over at my house, and we were sitting around talking about Thanksgiving. Mom asked her, “Are you coming for dinner? Just wondering how many people I was going to have to cook for.”

Becky said, “I’d love to come spend Thanksgiving with you guys. We’re getting dressed up, right? I was going to wear a dress. But if I wear one, YOU have to wear one too,” she said, giggling, pointing her finger into my shoulder. “And you too,” she said, looking at my Mom.

“Wow,” Mom laughed, “she drives a hard bargain.”

“I’ve got just the dress for you,” Becky said, looking at me, “my stretchy brown one that’s strapless. I’ll have to loan you the bra to go with it. I’ve been wanting to see you in it. Your beige sandals should go perfectly with it.”

“Mmmm,” I said, my dick hardening at the thought of us all spending the day in dresses!

A few days later, she handed me a box as I was leaving her house. “Here’s the dress and the bra, along with the dress and slip I’m going to wear. We’ll get dressed at your house.”

When I got home, I hung up both dresses in my closet, marveling at how they looked hanging there. Later that week, I noticed in the paper that K-Mart had Underalls on sale, and the next time I drove past there, I stopped in and got her a pair in her size. When we talked on the phone that night, I said, “I’ve got a surprise for you. I bought you a pair of Underalls to wear on Thursday!”

“Oooh, we’ll both be so smooth and sleek,” she purred, sexily.

Thanksgiving finally came! I slept in that morning, then got up and took a nice hot bath and shaved my legs and armpits. I put on Becky’s strapless bra and my Underalls, and did my nails so they would have plenty of time to dry. I put on my pink dressing coat and went out to help Mom get dinner started.

Finally Becky arrived around 11. After saying hi to my mom and looking over the dinner, we went into my room to get dressed. I handed her the Underalls I bought for her, and then she disrobed down to her bra. I took off my dressing coat and sat down on the bed while she put on her pantyhose, and then played footsie and giggled about how pretty our legs looked. Next we donned our slips and our dresses, and went in the bathroom and did our makeup. Finally we sat down on the bed and put on our high heels, and after one last look in the mirror and air-kissing each other, we sauntered out into the family room.

Hand in hand, we walked into the kitchen, and when Mom saw us she exclaimed. “Wow! Look at you two! You’re gorgeous!” We both giggled, then walked around the kitchen looking at all the food. Mom said, “I think things are far enough along that I can go get ready now. Keep an eye on things and I’ll be back in a little while.”

Mom went in her bedroom and closed the door, and Becky and I stood there facing each other, our fingertips lightly touching, the sexual tension between us palpable. “God, I am so turned on right now,” I whispered.

“Me too,” she agreed. “Are we going to have any ‘us time’ this afternoon?”

“I think Mom’s going to take some food up to Grandma later on and see her for a while. We should have a little time to ourselves,” I grinned.

We sat the table, then watched the parade on TV till Mom came back out of her room, looking exquisite herself in a white lace blouse, a pencil skirt, and heels. We stood around in the kitchen admiring each other’s outfits and talking girl talk till it was time to eat.

After dinner, Becky and I washed dishes while Mom relaxed. When we were almost done, Mom came back in the kitchen and said, “I can’t believe you’re washing dishes in high heels. But you probably couldn’t get Brian out of his.” I blushed, and they laughed.

“So I like to get dressed up on holidays. So sue me,” I smiled, still red-faced.

Mom got the food back out and put together a casserole dish. “Well I better take something up to Grandma, I told her I would, then spend some time with her. No hanky-panky you two,” she said, smiling.

”Don’t worry, Mom,” we giggled in unison. We helped her carry the food to the car, and waved as she left. We went back inside and sat down on the couch next to each other, our pantyhosed legs crossed and touching, our high heels bobbing up and down. Our dresses were both knee-length and had ridden up when we sat down, exposing a lot of our legs. We held hands lightly and laid them on our knees while we kissed. We started to make out, and I started to stroke her nice smooth legs with my fingers. She moaned in pleasure and responded in kind.

I started to run my fingertips under the hem of her dress, feeling the lacy edge of her slip, and she said, “Naughty boy. Two can play at that game,” and put her fingers under my skirt. The feel of her fingertips running up my nyloned legs made my dick rock-hard. As we kissed and our passion got hotter, our hands both crept up each other’s legs till we both reached our pubes. She started tracing the outline of my erection with her fingernail through my Underalls, and I slid my hand between her thighs, feeling her pussy moisture through hers. She was breathing heavily, and finally said, “C’mon. I can’t wait any longer.”

“Me either,” I agreed. We jumped up and ran into my room as fast our high heels through the shag carpeting would allow. When we got in my room, I caressed her, unzipping her dress, and slid it over her arms and down to the floor. She moved my spaghetti straps off my shoulders, and, taking the stretchy bodice of my dress in her hands, wiggled it down my chest and down off my body. We hugged and kissed again, and then we slid each other’s slips off, followed by our bras. I was ready to explode. I slid my pantyhose down to my hips, releasing my huge erection, and then put my hands on her buttocks and pulled her to me, grinding my big hard dick against her. She broke away and pulled her hose down, then sat down on the bed and said, “Take off my heels.”

I unbuckled them and took them off, and she slid one leg out of her pantyhose. She laid down on the bed and I reached over and got a condom. “Here, let me put it on you,” she whispered. I handed it to her, and she tore open the package and while I laid next to her. She put it on the head of my dick and rolled it down my shaft. “I can’t believe how big your…. thing gets,” she giggled. Still in my hose and high heels, I crawled between her legs as she spread them wide. She wrapped her arms around me and pulled me close, and I guided my dick into her crotch and entered her slowly and carefully as she groaned in pleasure. We saved sex for special occasions, and she was still so tight, I didn’t want to hurt her. We both needed release so badly. We fucked slowly and deliberately, enjoying it fully since we didn’t get the chance very often. As I moved around, my high heels kept hitting the bottom headboard of the bed, and it was so hot, fucking this beautiful girl while I had hose and high heels on. We both went over the edge at nearly the same time, thrusting deeply.

We both fell asleep briefly, and waking up, we kissed and smiled. “Wow,” she said. “Wait till we can do this all the time.”

“Ummm-hmmm,” I agreed. I carefully sat up so I didn’t hit her with my high heels. She sat up and pulled her pantyhose back on, and then we sat next to each other, touching and feeling each other’s warmth. “What do you want to wear now? Jeans and heels?”

“Mmmm, that would be great,” I said. I took off my heels and pulled up the wrinkles out of my pantyhose. I reached in my closet and got out my girl jeans and my lacy beige top. Becky had been wearing one of her favorite tops, an opaque silk shirt, and she put it on without a bra underneath, her nipples showing through.

“Mmmm, very daring,” I said.

“I like wearing this without a bra,” she said, slyly. “I love how it feels on my boobies.” As conservative as she was, it was a real sexual statement for her. We went back out in the family room and watched TV and played games the rest of the afternoon, feeling so girly. Every time we sat together we crossed our legs and put our feet together, showing off our high heels and our perfect pantyhosed feet.