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

After my formal date with Jake, it was all I could think about for a few days. The whole gay/not gay thing was at the forefront of my mind again. My sexual experiences with Char, and dating girls, had convinced me that I wasn’t gay, even if I was a crossdresser. The whole experience with Jake was obviously making me rethink it.

The other thing that was at the forefront of my thoughts was coming out to Becky. We had been dating for a year, and, hard as it was to believe, we really hadn’t gotten sexual yet. She was a really nice girl and we got along great and had a lot of fun. She was very religious and had made it pretty vocal that she did not believe in premarital sex. That was fine with me – I respected her wishes totally. I always wore hose on a date, and when I got home and got undressed, I always masturbated to relieve my pent-up desire before I took my hose off.

Finally, one day, I decided it was time. She was in the band, and had to play at a school function, and wanted me to go too. She was wearing a short white skirt with her white platform sandals. I had to get dressed up too, so I decided to wear a white shirt and navy blue slacks with pantyhose underneath. When I met her after the performance, I could tell she was not happy or feeling well, or something. She had been grouchy all day. Maybe this wasn’t the right time to spring it on her that her boyfriend liked to wear nylons.

As we approached her house, she said, “Just drop me off and I’ll change, then come down to your house. You don’t have to stay.”

I drove home and went inside. I took off my shoes and socks so my painted toenails were on display through my sandalfoot pantyhose. I decided to not point it out, but just wait till she noticed. I didn’t feel well either. I was constipated and hadn’t had a BM for several days. I was going to take some Correctol the night before, but I had fallen asleep while reading and had forgotten. I had been trying to go all day, but I just couldn’t. While waiting for Becky to come back, I went and sat on the toilet for a while, but didn’t pass anything but a little gas. Becky knocked on the door and came in. I was surprised to see that, even though she had jeans on, she was still wearing her white platform sandals and beige pantyhose. She looked sexy as hell, but I knew not to get amorous the way she had been acting. I glanced down and saw my hosed feet and immediately got hard.

We sat down in the family room. I crossed my legs and bobbed my foot, my heart pounding in anticipation of her noticing. Finally I saw her staring at my feet. She got a quizzical look on her face and asked, “Have you got hose on?”

I turned beet red, and looked down at my lap. “Mmmm-hmmm.”

“Why?” she asked.

I hesitated, my heart pounding. “Because I’m a crossdresser. I like wearing girl things.”

“Seriously? How long have you been doing this?”

“Since seventh grade. My mom caught me wearing her pantyhose, and instead of freaking out about it, she bought me some of my own and encouraged me to wear them when I dress up.”

“Wow,” she said, giggling. “That’s weird.” After thinking about it for a minute, she asked, “So do you wear them when we get dressed up to go out?”

“Mmmm-hmmm,” I said, blushing.

“All this time, we’ve been going out, you’ve been wearing nylons?”

“Mmmm-hmmm,” I repeated.

“Wow,” she said again. “You paint your toes too.”

“Mmmm-hmmm,” I repeated again, giggling.

“You have really pretty feet,” she said. She scooted over closer to me and crossed her legs so that our feet were together. “Look, we both have hose on,” she giggled.

Sensing that she was warming up to the idea, I said, “Doesn’t it feel so sleek and sexy when you wear them under slacks?” I asked, putting my arm around her neck and pulling her close.

“Yes,” she breathed, as our lips met. We shared a long passionate kiss, and then, breaking apart, I laid my hand on her thigh and started rubbing it. She did the same, giggling, and then we kissed again.
“Would you like to see my wardrobe?” I asked.

“Sure,” she said. We went in my room and I opened my closet. She immediately spotted my shoes.

“Wow!” she said, picking up one of my white pumps. “You wear heels too?”

“Mmmm-hmmm. Here,” I said, taking it from her and getting out the other one, I stepped into them, and then walked away from her, then turned around and walked back. “See?”

She looked in the closet, and said, “Nice dress! Do you wear it out at all?”

“Not really,” I said. “Char gave it to me, it was one of hers. I have girl slacks that I wear mostly. When I was in Young Organists, the uniform was that red blazer, those white slacks, and the white pumps. I wore that outfit most weekends.”

As we were standing there, she passed gas quietly. “Sorry,” she said, blushing. “I haven’t pooped for a while, I feel like I have to go so bad, and I’ve been trying all day, but it just won’t come out. When I try to go, it starts to come out and then it just gets stuck and it won’t come out any farther, no matter how hard I strain.”

So that’s why she was so cranky. “Sounds like you’re constipated,” I said, then added, frowning, “I am too. Sounds like we both need some Correctol,” I said. “I would have taken some last night but I forgot.”
“That’s what my mom takes,” she said.

“We can take some of mine. We’ll still have to wait till tomorrow for it to work though.” I thought about having anal sex with Char and relieving her constipation. “I know something that would make you go right away, if you wanted to try it.”

“What’s that?” she asked.

“Sometimes when married women get constipated, they have sex in their bottom to help their poop come out.”

“How do you know?”

“Char told me,” I said.

“Can’t it make you pregnant?”

“No,” I laughed. It’s a different hole. It’s where your poop comes out, not where babies do.”

“So Char does this?”

“That’s what she said,” I replied, not telling the rest of the story. I put my hands gently on her shoulders.
“Would you like to try it?”

“I don’t know,” she said. “I guess it’s really not normal sex. My bottom hurts from not being able to poop. I need to go so bad,” she said, moaning.

I led her to the bed, and we sat down. “I promise it’ll make you feel better,” I said, remembering how Char got relief so quickly. “We need to take our pants off, but we can leave our hose on.” She reached down and took off her sandals, then unsnapped her jeans and slid them off. I took my slacks off as well. It occurred to me that this was the first time we’d ever taken our pants off in front of each other. I put my arm around her and pulled her close, wanting her to get as relaxed as possible. I said, “I’ll go get the Vaseline, we have to lube up really well.”

I went to the hall closet and got the Vaseline. As I walked back in the room, Becky said, “You’re wearing sheer to the waist.” I slid my pantyhose waistband down to my thighs, and stretched out on the bed.

Caressing her back lightly, I said, “You need to pull yours down too.”

She stood up and pulled down her hose and panties, then sat down on the bed. I had never seen her naked below the waist before – another first. I pulled her down next to me, and we snuggled for a few minutes. My dick was so hard I thought I would erupt before I ever got in her. “Turn on your other side, so I can lube you up,” I said. She did, and I opened the Vaseline and put a big gob on my finger. “I’m going to put some lube in your crack. I’ll go slow.” I slowly and gently started to run my finger up and down her crack, and then she relaxed and let me in. I got some more, and said, “We really need to put this on your…… hole,” I said. I put my finger back in her crack, gently rimming her anus this time. “Now I’m putting some on me,” I said, as I lubed myself.

“Okay,” I said, “now pull your right knee up to your tummy to open up your bottom.”

“How do you know all this?” she asked.

“It’s the position you use for a Fleet Enema. It’s on the box,” I said, hoping that would placate her. She maneuvered into position, and I spooned behind her, guiding my dick into her crack. “Now push really hard, like you’re trying to have a BM.” She did, and I slipped inside. She immediately jumped up. “I’m pooping!” she said.

“No you’re not,” I giggled. “It was my boy part in you.”

“Oh,” she said, relaxing. She laid back down next to me, and we got back into position and I entered her again. As I gently started to thrust, she said, “I think I’m going poop.”

“No you’re not,” I reassured her. “You can’t. I’m plugging up your hole. Don’t worry,” I said soothingly. As we gently thrusted together , our pantyhosed legs rubbing together, I felt so close to this sweet, virginal girl that was trusting me in so many ways. I was so aroused, when I ejaculated I literally ERUPTED, gasping. I felt her stool start to come out and push out my dick. “Okay,” I said, “now go sit on the pot and try to go poop.”

She ran into the bathroom while I laid there on the bed, enjoying the post-coital glow. I heard her grunt, then a splash, and a sigh of relief. I listened to several more grunts and splashes, then silence, then the toilet flushing. She came back into my room, smiling. “Wow, that’s so much better. It came out so much easier. You were right.”

“Good,” I said. “Now if I could just go poop, we’ll be all set.”

She laid her hand on my head, stroking my hair. “Do you want to try again?” she asked.

“Maybe,” I said. “I’ll put on my heels, maybe that will help.” I got up and pulled up my pantyhose, then stepped back into my white pumps. We walked into the bathroom in our nylons, and I sat down on the toilet. I took a deep breath and really pushed. After two or three really hard pushes, it felt like it was starting to move. I grunted and strained for several minutes, and finally my bowels moved. After I stood up, Becky said, “Wow, that’s almost as big as the one I did!” Before we left the bathroom, I got a washcloth, soaped it up, and thoroughly washed my pubes to get all of her poop and Vaseline off.
We got dressed again and went back out in the living room. Sitting together on the couch, we started playing footsie with our nyloned feet. She said, “That felt so good. Now I wonder what it’s like to do it the normal way.”

“The normal way is better,” I said. “You’ve got more feeling in the front.”

We necked a little more, then she said, “So where could we get some…… you know….. birth control?”

“You mean a condom? At the drug store.”

She got up on her knees on the couch and put her arms back around my neck, and we kissed long and hard again. “Let’s go to the drugstore and get some. Only thing is, you have to wear your high heels to go get them.”

“Okay,” I giggled, “then you do too.”

“Deal,” she said. She went in my room and got her high heeled sandals and put them back on, treating me to a show as she slid her cute pantyhosed feet into them. We chased each other to the car.
When we got to the drugstore, we carefully looked around before we got out of the car, but it was thankfully not busy. We ran in the store arm-in-arm, our high highs clicking on the concrete, and quickly found the birth control aisle. While we were looking at different brands of condoms, I caught myself dipping my foot in and out of my shoe. We hurried up to the checkout and were the only ones in line. As we walked out of the store, we were arm in arm, swinging our arms and our derrieres as we walked in our high heels.

We went back to my bedroom, falling down on the bed. I kicked off my high heels, and Becky put her feet in my lap. I unbuckled her white sandals and took them off her feet. Her nyloned feet and ankles looked exquisite. I turned to her and we kissed, slowly at first, then faster and faster. We broke apart and started to tear off our clothes. When we got down to just our pantyhose, I said, “Let’s leave them on and just pull them down.”

“Good idea,” she panted. We laid back down on the bed and, entertwining ourselves in each other, started to neck passionately. I worked my way down her gorgeous body, kissing her neck and cleavage like I knew she liked, and then started to kiss her breasts. She started to breathe heavily as I kissed her nipples, then took them in my mouth and gently sucked them. “Oh Brian,” she giggled, “I’m getting so slimy down there.”

“That means you’re ready,” I said. “Slide one leg out of your hose.” As she did, I slid mine down to my thighs, releasing my huge erection. I reached for the Walgreen’s bag and got out the condoms. Becky watched in fascination as I took one out of the package and rolled it up my big hard dick.

“Okay, now lie on your back,” I said as I mounted her. “Spread your legs wide.”

I guided my erection to her pussy and gently, slowly, entered her. I got just my tip in and asked, “Are you OK so far?”

“So far,” she breathed. I pushed just a little farther and my glans was in now. “Still OK?” I asked.

“Yes,” she breathed. I slowly pushed the rest of the way in. It felt so good, and I paused for a minute before I started to thrust. As I did, I could feel her relax. “Oh wow,” she said, “This feels great.”

“Mmmmm,” I agreed, as I felt our pantyhosed legs rubbing together, the erotic feel of it was overwhelming. After a few minutes, I opened my eyes and looked at her. She looked so heavenly, laying there with her eyes closed, a slight smile on her face, our bodies moving together faster and faster. I was so close to coming, I started to think about anything, anything other than this beautiful girl and how she looked in her dress earlier, how sexy I felt all day in nylons and heels, how we had grown so close over the last year, how she trusted me with her constipation problem and let me fuck her twice today, and finally revealed her true feelings for me, when she came, things getting so wet down there and then I exploded my wad into the condom.

We rolled apart and I carefully pulled out, holding the condom so nothing would spill. “Wow,” I said, “that was really something.”

“Wow, I agree,” she giggled. “So that’s what it’s like.”