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
Next Tuesday, when I was getting dressed for exercise class, I remembered Tina saying she wanted to see me in my white pumps. I put on my bra and then the light blue leotard with nude pantyhose, then my denim miniskirt, and a man’s white shirt over my leotard. I left the shirt mostly unbuttoned to give it a free , breezy look. I put on my footies over my hose, and then my girl sneakers. When Tina got there and I got into her car, I saw my white pumps on the floor.
She looked at me and said, “Oh good, you’re wearing white! You remembered!”
“Mmmm-hmmm,” I replied, taking off my sneakers and footies and putting my feet into my white pumps. After we drove to the mall, as I was getting out of the car and feeling the breeze on my nyloned legs, I felt so sexy. Tina caught up to me and took my hand, and we walked into the mall hand-in-hand, swinging our arms and hips like little girls.
As soon as we got into the dressing room, the other girls were giving us the once-over. “Wow, look at you two all dressed up! You look so nice!”
“Thanks,” I blushed, as I stepped out of my high heels and took off the shirt and skirt. After class, we went back in the locker room, and Tina said, “I really need a shower. Want to take one with me?”
“I can’t,” I said, looking around. “The other girls will see that I’m not a girl.”
“Just wait a minute till they leave,” she whispered. After a few minutes, everyone said their goodbyes and left. Tina took my by the hand and pulled me toward the showers. She said, “Don’t worry, if anyone else comes in I’ll come out and get your leotard for you.”
The thought was so exciting. Looking around once more, I pulled off my leotard and slid my nylons down and off. We walked into the showers arm-in-arm and closed the stall door behind us. Turning on the water, we wetted down, and Tina handed me her body wash. “I’ll lather you if you’ll lather me,” she said, smiling.
We did, and it was SO sexy. We ran our hands over each other and didn’t even hesitate when we got to our crotches. We both moaned in pleasure as we lathered each other’s pubes. As we rinsed off, when we were almost done, we wrapped our arms around each other and kissed deeply.
When we broke apart, I whispered, “Wanna fuck in here?”
“We better not,” she said. “Someone might come in. Let’s go back to my place where there’s a bed.”
We toweled off, and she said, “Let me check whether the coast is clear.” She opened the door and looked around, and said, “We’re alone. Let’s get dressed.”
I found my panty hose and quickly slid them back on, followed by my bra. Tucking my semi-hard dick, I put my skirt on and quickly buttoned it. As I was reaching for my leotard, Tina said, “Just put on your shirt. It’ll be cooler and sexier.”
I did, leaving the tails out, then went over to my locker and got out my white pumps and slid them on. As I walked past a mirror, I could see my bra straps showing through my shirt, and I felt so sexy! Tina got dressed almost as quickly as I did, and we packed up our things and walked out into the mall. I could feel the breeze through my shirt and up my skirt as I swung my hips walking in my heels. It was a good thing the denim skirt was hiding my big hard-on. We walked down to the center court in front of Orange Julius where we usually met after class. Several of the other girls were already there. Tina and I ordered our drinks and then sat down with them.
After a few minutes, Julie leaned in and lowered her voice and said, “Guess what I did? Last night I asked my husband if he’d like to do it in my bottom. Wow! He about dragged me to the bedroom. Afterwards I couldn’t get into the bathroom fast enough. I had this HUGE BM and I didn’t even have to try hard. It just slid right out!”
I said, “Isn’t it great? It’s so nice to get immediate relief without chemicals.”
“Afterwards he asked me why I wanted to do it in there. He was probably thinking I wanted to experiment in bed. He was disappointed when I told him it was because I was constipated.”
Melissa leaned in and said, “Can I ask something? When you guys do…… anal……. what…. you know………… position do you use?”
We all giggled. Julie said, “My husband did me doggy style. With my butt up in the air. Brie, how do you and your boyfriend do it? Since you seem to be the expert.”
I said, “I lay on my left side with my right knee bent. You know, the Fleet enema position. It helps open up my bottom. He spoons with me and puts his dick in my crack, then puts his hand on my hip and rolls me back toward him as he enters me. That’s the easiest way I’ve found.”
“Mmmm, that makes sense,” Melissa said. “I think I want to try it. Just to see what it feels like. I’m this close to asking my husband to try it. I kindof like the doing it on your side idea. It’s a little more…… modest,” she said, blushing, and we all laughed. “So, how much do you lube up? Do you put it inside you, or just outside?”
“John lubes me up inside,” I said. “He puts his finger up inside me during foreplay. It really turns me on.”
Julie said, “My husband just puts some lube on the outside of my butthole, and on his tip.” We all giggled.
After we finished our drinks, Tina and I walked hand-in-hand again to her car, and the minute we closed the doors, we turned to each other and frantically French kissed again.
“Mmmm, my sexy sheboi looks so pretty in her white high heels. And so daring, having a shower in the ladie’s dressing room. Don’t you feel so feminine?”
“Oh God, Tina, yes,” I panted. She drove quickly to her house and we ran inside. Turning to me, she said, “Take off your shirt and skirt but don’t take off your white pumps. I’m going to fuck you like you’ve never been fucked before. Lay down on the bed!”
I complied, laying down on the bed on my back, my knees raised up higher than usual because of the heels. She quickly took off her clothes, then knelt between my legs and pulled my hose down to my thighs.
“I’m imagining what you must have looked like at 14, in those white pumps and nude hose.” She got on top of me, grinding against me, then spread her legs. “Come inside me now, sissy boi,” she said, giggling.
I was so aroused. I entered her and she immediately clutched me with her pussy. We thrusted together for only a few seconds before she went over the edge, shrieking with each thrust, and I came as hard as ever, shooting my hot wad deeply into her.
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