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 we got married, I wore girl clothes a lot more often. I was working a lot of hours and obviously couldn’t wear women’s things when I was at work. One week I worked eight days straight and I was so in withdrawal. That night when I got home from work I promised myself I was going to spend the next day in girl clothes.

The next morning, after taking a shower and shaving my legs, I dried off and walked into the bedroom. I got a pair of pantyhose out of my dresser drawer and sat down on the bed. As I gathered them up and slid them sensually up my legs, I got my usual pantyhose erection. I got my white dress pants out of the closet and slid them on, followed by my multicolored beige top. Finally, I got out my burgundy ballerina flats with bows and stepped into them. I checked myself out in the full-length mirror and my sagging dick immediately got hard again.

As I packed my purse, the phone rang. It was Jake.

“Hi!” he said. “Doing anything today? I thought I might come over.”

“Well,” I replied, “I’m just leaving to go shopping. Why don’t you give me two hours or so before you come? I’ll be back by then.”

“Okay,” he said. “See you about eleven.”

I decided right then that I would be greeting him in my girl clothes, and got so excited!

I drove over to Ayr-Way and sidled in to the shoe department. When Becky and I had been in there several days ago, I saw a really cute pair of brown platform clogs. I located them and looked at the size, and they were a 9! I stepped out of my flats and slid my feet into them. They fit really well, and gave me a couple inches of extra height. I walked around a little and they were comfortable to walk in.

As I took them off and put my flats back on, Tina, a woman from church, walked down my aisle with her pre-teen daughter, Erin, in tow. “Hi!” she said, and then noticed me holding the clogs in one hand, and looked down at my feet in my ballerina flats. “Shoe shopping?”

Oh no, I thought. I’m busted. I was embarrassed for a moment, but then thought, what the heck. “Mmmm-hmmm,” I said. “I saw these clogs the other night and wanted to come back and try them on.”

“We’re here getting Erin’s first pair of heels,” Tina said. “She’s got a piano recital Saturday, and we thought it was time for her to look a little more grown up.”

Erin interrupted, “I’ve even got hose on too! Wanna see?” She pulled up her pant leg to show me her shapely calf and ankle in tan nylons.

Tina said, “She hasn’t come off of cloud nine since I gave her that pair of knee-high hose this morning and told her to put them on so we could go shoe shopping. I had forgotten what a big day it is when a girl gets her first pair of nylons – but I guess you know that,” she giggled, looking down at my nyloned feet in my flats.

We walked toward the check out, and after paying, Tina asked me, “So where are you headed now?”

“I’m going up to Osco’s,” I said.

“Mind if we tag along?” she asked.

I hesitated. I wanted to pick up some Correctol since I hadn’t had a BM for three days and we were out, but, once again, thought “what the heck”. So I said, “Sure!”

As we walked down the midway of the mall, I looked down at myself in girl clothes, carrying a purse and the women’s shoes I had just bought, and started to get an erection again. I hoped Tina didn’t notice. She was lagging behind, window shopping, and when she caught up to me she leaned in close and said, “You look so smooth in back. Have you got pantyhose on?”

I blushed, “Mmmm-hmmm.”

“Wow,” she said, “I thought you were just wearing knee highs. You really did get dressed up. You look really nice.”

We walked into Osco’s, and I headed over to the laxative aisle and started looking for Correctol.

Tina asked, “What are you looking for?”

I blushed again. “I need some Correctol. I’ve been…….. constipated for three days.”

Tina replied, “Oh wow, you poor thing. I like Correctol, it always fixes me right up the next morning after I take it.” She lowered her voice and asked, “How long have you been taking a woman’s laxative?”

“When I was in ninth grade I got really constipated. My Mom bought me Correctol and told me to take it whenever I didn’t do my push job for more than two days. So I’ve been using it ever since when I can’t poop. I really like it because it makes my poop really slimy and slippery so it comes out easily, even when it’s big and hard.”

“That’s because it’s a stool softener as well as a laxative,” she said.

After picking some out, we walked over to the cosmetics aisle, where we looked at lipstick and nail polish. After checking out, we headed out to the parking lot. When we got to her car, she turned to me and said, “I didn’t realize you were such a girly guy. We should get together sometime and do lunch or something.”

The thought was tantalizing. I wondered what she had in mind. “Sure,” I said. “Let me know when you’re available.”

I walked over to my car, and, before got in, I changed into my new clogs. I drove over to K-Mart and looked around there. Nothing much in Ladies Shoes, but on the way out, I saw a big display of K-Mart Sheer Smooth and Silky Pantyhose. I stopped and picked out two pairs that were Suntan, Medium/Tall, and Sandalfoot. After I checked out and was walking out to the car, I remembered what Tina had said about how smooth I looked in back, and I ran my hand over my derriere as I walked, marveling at the smooth round feel of my own bottom. My dick immediately jumped to attention again, and stayed that way as I drove back home.

After going in the house, I went in and sat on the toilet for a while. I left my high heeled clogs on to raise my knees up and make it easier to go. My stool was down in my rectum, and I was passing gas and really feeling the urge to go, but no matter how hard I pushed it just wouldn’t come out. I really needed a laxative. I was starting to think I should have picked up a Fleet enema too. I wondered if I should go back out in my clogs and go back to Osco’s and get one. The idea really turned me on. I finally gave up and walked back in the living room, where I heard a knock on the back door. It was Jake. My heart began to pound, and I reminded myself to be calm and feminine, even though after being in girl clothes all morning and being seen by Tina, I was pretty used to being en femme by now.

I clopped through the kitchen in my high heels and opened the door. Jake immediately noticed the difference in my height. He said, “Wow! Did you grow?”

“No,” I giggled, as I held up my foot and showed him my clog. “I’ve got high heels on. I just bought these at the mall. Aren’t they cute?” I stepped out of them and said, “There, now I won’t tower over you.”

We went in and sat down on the couch, and made small talk. Jake asked, “So what else did you buy at the store besides your clogs?”

“Not much,” I said, then, giggling, “just some panty hose. All of mine have runs. And some… medicine,” I said, not wanting him to know I bought a laxative.

As we were talking I had crossed my legs and was bobbing my foot up and down, hoping that he would notice that I had hose on. Sure enough, after a little while I noticed him staring at the reinforced toe of my pantyhose.

“Mmmm, you’ve got hose on,” he said, smiling.

I said, “Mmm-hmmm. I felt like getting dressed up today to go shopping. I wanted to wear these white slacks, so instead of putting on underwear this morning, I put on pan-ty-hose,” dragging out the word sensually as I pointed my toe toward him.

“Really?” he asked. “How come?”

“Because these pants are so clingy and sheer, I’ll have panty lines showing if I wear underwear. Besides, I went shoe shopping, and you have to wear hose when you’re trying on women’s shoes.”

He smiled. “Wow, I can’t believe you went out in public in girl clothes and nylons. You look really nice!” At a pause in the conversation, he asked, “So why are you still wearing girl’s clothes? I mean, you look really nice in them, I just thought that, after you and Becky got married, that would be the end of you crossdressing.”

I thought about it a moment, framing my answer, and finally said, “I still just feel so natural and comfortable in girl clothes. I guess you could say that I’m. . . part girl, I guess. You know, a sissy. Becky’s actually OK with it. You’re the second person today that I know that saw me in girl’s clothes.”

“Really?” he asked. “Who was the first?”

“A lady I go to church with. She and her daughter were shoe shopping too and saw me. She said I had a really smooth rear and wanted to know if I was wearing pantyhose. I got so aroused when she asked that,” I giggled.

“I can imagine,” he agreed. “You just look so pretty and feminine in that. You’re gorgeous!”

“Thanks, you’re too kind,” I said, frowning as another cramp hit me. “I just wish I felt as good as you think I look.”

“What’s wrong? Aren’t you feeling well?” he asked.

“Well, no,” I said, hoping he wouldn’t probe for details.

“What is it?”

“It’s actually, kind of… embarrassing,” I blushed.

“Whatever it is, you can tell me,” he said. “I won’t make fun of you.”

“It’s just that I’m…. constipated,” I finally said. “I haven’t done my push job for three days, and I really need to go. I’ve been pushing as hard as I can but it still won’t come out.”

He said, “Maybe you need a laxative or something.”

I said, “I normally take Correctol when I need help to go poop, but we’re out. Else I would have taken some last night. When I was at the mall I bought some more, but you take it before you go to bed and it makes you have a BM the next morning, so I’m going to feel this way all day. I think I should have gotten a Fleet enema instead.” Or have sex in my bottom, I thought, remembering how well it worked on Char and Becky. Leaning close to him, and stroking his shoulder, I asked, “Do you suppose, maybe you could…….. buttfuck me?”

“Mmmmm, sure,” he said. “Do you have any Vaseline?”

“In the nightstand in the bedroom,” I replied.

We stood up, facing each other, and you could feel the sexual tension between us. We held hands, staring into each other’s eyes longingly, until another poop cramp hit me and I frowned again, rubbing my tummy. He put his arm around me, and we turned and walked toward the bedroom. He let his hand slip down from my waist to my bottom, and it felt so sexy. I got the Vaseline out of our bedside table and handed it to him. We both took off our slacks and laid down on the bed. As he took off his underwear, I asked, “Can I leave my pantyhose on, and just pull them down? They’re kind of a pain to put back on after they’re all stretched out.”

“Sure,” he said. “Lay on your left side, and bend your right knee up a little.”

“Mmmmm, the Fleet enema position,” I said.

I slid the waistband of my hose down to my thighs, releasing my erection from its nylon prison of the past few hours. He snuggled up behind me and we spooned together. He started nuzzling my neck and kissing me, and laid his hand on my breast. I put my hand on top of his and stroked gently while we foreplayed. After a few minutes, we broke apart and he opened up the Vaseline, put a big gob on his finger, and gently parted my crack and lubed my derriere all the way to my anus. I laid there with my eyes closed as he stroked my anus.

“You should probably lube me up inside,” I said.

He put some more Vaseline on his finger, and said, “Now push down a little, like you’re trying to go poop.”

I did, and he gently pushed his finger up in my rectum, moving it around to distribute the Vaseline, and my dick started to get hard again. I could feel him pushing against my big hard stool. He said, “Wow, you really need to have a good bowel movement.”

“I know,” I moaned. “I’ve been trying all morning. I just can’t go.”

He spooned up close to my back again, and he guided his erection into my crack and pressed it gently against my anus. He took a few tentative little thrusts against my hole, then asked, “Are you ready? Push down again, a little harder this time.”

“Just be gentle,” I said, “It’s been a long time since we did it.” I remembered our formal date from several years ago and the wonderful night we spent together when I lost my virginity to him.

I pushed to let him in, and he laid his hand on my hip and pulled me back toward him as he gently entered me, his big hard dick dilating my anus and easily slipping in. I relaxed in his arms, and he started to gently thrust in my rectum. I had forgotten how sensual and feminine it felt.

“Doing OK?” he asked.

“Mmmmm-hmmm. Actually it feels like I’m taking a huge poop,” I giggled.

“I can’t get in you very far. I’m running into your stool.”

My dick was so hard it was quivering, and I started to masturbate in time with his thrusts. I imagined I was a real woman with a man’s dick up in her! As he fucked me, I could feel things moving in my bowels, and I passed a little gas. The urge to defecate was stronger and stronger, but I ignored it. His erection got bigger and harder, and then he slowed down. Gasping, he ejaculated, and I felt the muscle spasms go up his dick and his hot semen flooding my rectum. The feeling of being ejaculated into was so femme and stimulating, I almost ejaculated myself.

We relaxed, and he pulled out of me. My urge to evacuate was really strong now. I got up, threw on Becky’s bathrobe, my erection tenting out the front, and ran into the bathroom. Jake followed me in and sat down on the edge of the bathtub. I sat down on the toilet and pushed. This time, my big stool finally moved through my now well-lubricated and dilated anus and plunked into the toilet, the water splashing me on my backside. I sighed in relief.

After resting for a moment, I wiped, stood up, pulled up my pantyhose, and tied my robe. We looked down at my huge stool floating in the toilet, and Jake asked, “Feel better?”

“You have no idea,” I said. “I bet I’m five pounds lighter. I was so constipated. I really needed a push.”

I noticed him staring at my legs. My robe was frilly and short, and with hose on, it almost looked like I was wearing a dress. He put his arms around my neck, and, bringing his lips close to mine, kissed me gently. I responded in kind with a deep, ten-second kiss, and then laid my head on his shoulder.

“Now,” he said, “I’m going to make you feel even better.” He took me by the hand and led me back into the bedroom, and we laid back down on the bed. He opened my robe, and pulled the waistband of my pantyhose down to my thighs, releasing my hardening dick. He bent down and took it in his mouth, teasing it with his tongue until it was totally erect, then sliding his lips on it in earnest in a wonderfully slow deliberate blow job. The relaxing afterglow after a long-overdue bowel movement, the total arousal of wearing girl clothes out in public all day, and the kisses and caresses we had shared earlier culminated in me cumming so hard that my wad hit the back of his throat, and he started to choke.

“Wow,” he said, “I take it you liked it!”

“You have no idea,” I moaned.

We snuggled again for little while, then we got up and Jake put his clothes back on. We walked back out into the living room, and I detoured into the kitchen and stepped back into my clogs, making me look even more like I had a dress on. I rejoined him in the living room and he put his arm around my waist and laid his hand lightly on my bottom. I led him to the couch and we sat down together and snuggled closely. My rectum still felt so wonderfully empty, and my cramps had subsided. I had left my new nylons in the K-Mart bag laying there on the couch, and I took one of the packages out of the bag and handed it to him. “Those are the new nylons I bought,” I giggled.

“Mmmm, soft, smooth, and sheer,” he read. “Your legs will look great in these. Just like right now.” He laid his hand on my knee.

“I got sandalfoot so I can wear them with sandals,” I said, pointing at the label where it said Sandalfoot. “It looks better than when you wear reinforced toes with sandals,” as I slid my foot out of my clog and pointed my toe at him again, and then started rubbing my pantyhosed foot against his leg.

He said, “Mmmm, soft, smooth, sheer, and sandalfoot,” he giggled. “I love you in either. God, you’re making me so hot we’ll have to fuck again. I’ve been remembering that fantastic night we spent together at the midwinter dance. When you crossed your legs and I could see your sexy smooth legs in your nylons, it made me so hard! And today, when I saw you had hose on under your slacks, it just pushed me over the edge again.”

“It was so wonderful.” I said. “Both ways,” I added, giggling.

“So tell me what you thought.”

“I felt so close and intimate. Then when you ejaculated, I felt so femme. Just like a real girl!”

He picked up the Osco’s bag. “So what else did you get?” he asked, sticking his hand in and pulling out my Correctol. “’The woman’s gentle laxative’. You take medicine made for women? You really are a sissy,” he said.

“I’ve always used a woman’s laxative when I’m constipated. Regular laxatives are too strong and they give me cramps. I’ve been using Correctol since I was in, like, ninth grade.”

“You’ll have to call me the next time you’re…. irregular,” he said, smiling.

“Sure, I’d like that,” I giggled.

We cuddled for a little while, then he had to leave. Sitting there by myself, my mind reeled with the events of the day. Going out in public dressed, with hose on, trying on shoes, and having a woman see me and accept me as a girl. Having a man get aroused by looking at me in girl clothes and taking me to bed and fucking me. The wonderful feminine feeling of a man’s dick thrusting in me and his hot cum shooting up into me. It was almost more than I could take in. Then I remembered Tina seeing me in the mall and hoping that she wouldn’t say anything at church. That made me start to worry.

I went in the bedroom, took off Becky’s robe, and put my white slacks back on. A while later Becky came home from school. She looked me over and said, “Wow, you look nice! Why are you so dressed up?” I noticed her staring at my nyloned feet. “Mmmm, you’ve even got hose on.”

I blushed. “I had to go shopping so I decided to get dressed up. We were out of Correctol so I had to go Osco’s and get some. I was….” I grimaced, “constipated, and I really needed some help. I had this HUGE BM that just wouldn’t come out. After I got home I went and sat in the bathroom and kept trying and FINALLY pushed it out. I was starting to think I needed an enema.” I didn’t tell her about Jake buttfucking me. “I’m going to take some tonight though to help make my poop softer. Since I was already at the mall I went shopping. I also bought a pair of really cute clogs at Ayr-Way. Want to see them?”

“Sure,” she said. I walked into the living room and stepped back into my clogs. I walked out into the kitchen and Becky saw them. “Wow, those are so cute! We can both wear our clogs now when we go out!”