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 summer after tenth grade, I started dating a plus-sized but really pretty girl named Sarah. She always wore dresses and hose and heels on our dates. She was really uninhibited and loved to talk about personal things. When she learned that I was a crossdresser, she was very supportive and after that I always wore high heels and pantyhose under my slacks on our dates. We spent a lot of time talking about women’s clothes and fashion, and she told me that she always wore a girdle when she dressed up.

Our next date was going to start off with me playing at a wedding, and I got an idea. The night before, when Mom and I were washing dishes, I asked, “Can I borrow a girdle to wear tomorrow?”

Mom smiled, “Sure, but why? You don’t need one.”

I said, “I know, but Sarah always wears one and I thought if I wore one, she wouldn’t be the only one in a girdle.”

When we finished, we walked into her bedroom and she opened her lingerie drawer and took out a girdle. “Here, I’ll let you wear my I Can’t Believe It’s A Girdle! again.”

The next afternoon, I put on a pair of pantyhose and the girdle. When we picked up Sarah, on the way to church, Mom said to her, “You really have an effect on Brian. He wanted to wear a girdle today so you wouldn’t be the only one wearing one. So I loaned him one of mine.”

Sarah looked at me and said, “Really! That’s so sweet. What kind are you wearing?”

I blushed. “It’s an I Can’t Believe It’s A Girdle!”

“So am I! That’s so neat that we match underneath! What kind of nylons are you wearing?”

“No Nonsense Sheer To The Waist,” I said.

“I’m wearing regular Non Nonsense. Queen size,” she giggled.

After the wedding, we were hanging around in the choir room, holding each other and kissing. Sarah whispered in my ear, “I want to see your girdle, sexy boy.”

I giggled, “Only if I get to see yours too.”

“Mmmm, OK. where can we go to be alone?”

I thought a moment. “Across the church there’s a ladie’s room where brides get dressed. There won’t be anybody in there now, and the door locks. C’mon,” I said, taking her hand and leading her across the altar and down the steps on the other side. When we got to the bathroom door, I said, “You go in first and make sure it’s empty.”

“Okay,” she said, ducking inside. A few seconds later she came back out and giggled, “C’mon, the coast is clear.” We went inside and locked the door. “Okay, let’s see,” she said, tugging at my belt. I unsnapped my belt and slacks, and they slid down to the floor over my girdle and hose. “Mmmm, so pretty,” she said. She reached down to the hem of her skirt and pulled her skirt and slip all the way up to her waist, showing her girdle and her sexy pantyhosed thighs.

“Oh wow, you are so pretty. You’re going to make my faucet hurt when it gets big in this girdle.”

“Mmmm, we need to go do something to relieve the tension.”

“That would be nice,” I agreed. I took a step closer to her, bent my right knee in the classic girl pose, and rubbed my pantyhosed leg against hers. We both moaned in pleasure. Finally, I said, “I hate to break this up, but my Mom is probably waiting to take us home.”

“You’re probably right,” she agreed. “Maybe we can find some time alone later.”

On the way home, we sat next to each other in the back seat and held hands. Sarah crossed her legs, and treated me to a view of her beautiful pantyhosed legs. When we got home, Mom said, “I’m going to go up and visit with Grandma for a while. No hanky-panky, you two,” she warned, smiling.

We went in the back door as she backed down the driveway. Once inside, we shared a long, passionate kiss, and then I took her hand and led her to the family room. We both sat down on the couch and took off our high heels, exposing our pantyhosed feet. We looked at each other longingly, and then Sarah broke the silence. “I want to see your girdle again, pretty boy.”

“C’mon,” I said. I led her into my bedroom, and for the second time today I undid my slacks and let them slide to the floor, only this time I stepped out of them. Sarah reached behind her and unzipped her skirt, letting it fall to the floor, and stepped out of it. She pulled her slip up to her waist and sat down on my bed. She motioned me to come next to her, and I sat down with our pantyhosed legs touching. I reached over and started stroking her nyloned leg and she whispered, “Oh that feels so good.” After several more passionate kisses, she said, “We need to take off our girdles so we can have…….. access,” she smiled.

We both stood up and wiggled our girdles off. Neither of us was wearing panties under our pantyhose and our hairy pubes were clearly visible. She pulled her pantyhose down almost to her knees and laid back down on the bed. I followed suit, and then she took my hand and slid it between her thighs. “Rub me down there,” she panted.

I moved my hand up to her pussy and started to rub her there, and immediately felt the wetness. “Oh that’s so good,” she whispered. After several minutes of this, she gently touched my face and said, “How would you like to fuck me?”

“Oh that would be wonderful,” I said.

“Well we have to get undressed the rest of the way,” she giggled. We both slid our pantyhose the rest of the way off. Sarah laid back on her back, spread her legs, and whispered, “C’mon.” I got on top of her, reached down, and guided my penis to her vagina. As I started to enter her, she whispered, “Go slow. This is the painful part for the girl.” She spread her legs farther and I gently, slowly, pushed my erection into her tight warmth. When I was all the way in, I relaxed, and we both melted into each other’s arms as we started to thrust. She was so warm and smelled so good. As I remembered us showing each other our girdles, I was so hot I didn’t think I could last very long, but it was only a minute until I felt her orgasm start and I let go as we came together.

“Wow, that was wonderful,” I whispered.

“Yes it was,” she agreed. “But we’d better get dressed. We don’t know when your Mom will be back.”

We sat up on the bed and started to gather our underwear. We both found our pantyhose and started to put them back on. As we gathered them up and put them over our toes, she said, “Pantyhose are a pain to put back on when they’re all stretched out.”

“Mmmm-hmmm,” I agreed. As I watched her pulling her pantyhose up her gorgeous plus-sized legs, I started to get hard again. “Oh I wish I could have watched you get dressed the first time,” I said, as I pulled my hose up to my waist and pulled the wrinkles up from my ankles.

“Well you’re getting to watch this time,” she smiled. I handed her her girdle and she handed me mine. We stepped into them and then slowly tugged them into place above our waistlines. Sarah smoothed down her slip, and then gathered her skirt and stepped into it, pulling it up to her waist and zipping it as I slid my slacks up my pantyhosed legs and girdled bottom and snapped them. We looked at each other and smiled, and she said, “We better comb our hair so we don’t look like we had sex.”

“The mirror in the bathroom has better light,” I said. We walked into my bathroom and Sarah saw the Correctol sitting on the sink. She picked it up and said, “Oh, you use Correctol?”

“Mmmm-hmmm,” I said. “I have to use ‘the woman’s gentle laxative’ because my system is so delicate.”

“My Mom gives me Milk of Magnesia when I can’t go,” she said, sadly. “I hate it. It tastes awful. I’ve seen the ads for Correctol and wondered how it worked.”

“It’s great. It works really well for me. I get SO constipated after I get my braces tightened. It’s a stool softener plus a laxative. When I have really big hard poops it makes it come out so much easier. Would you like to try it?”

“Sure, could I?”

I opened the bottle, took out two pills, and handed them to her. “We’ll have to get a little baggie to put them in.”

“It’s OK, I’ll put them in my makeup bag.” She opened her purse, took out her makeup bag, and put the pills in it. “I’ll take one tonight before bed.”

After we dropped Sarah back off at her house and returned home, my feet were really sore from having heels on all day. I was rubbing my foot and Mom asked, “Are you OK?”

I said, “Oh, my feet are killing me and I need to get out of this girdle.”

She laughed. “Well you’re the one that wanted to wear a girdle and heels. Now you know the down side of dressing like a girl.”

The next time Mom went shopping at the mall, she came into my room with a package. “Here,” she said, “I bought something for you and Sarah. You can give her a gift the next time you go out. I bought you both No Nonsense Control Top pantyhose. That way you can have some tummy control but not be as binding as a girdle. I got you Size B and her Queen Size.”