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 next Saturday morning, I awoke after an erotic dream where Becky and I were out in public all dressed up, and I was wearing my new high heeled white sandals. I snuggled up to her, and wondered what her reaction would be to me asking to go out in public dressed up. As we nuzzled together, I said, “Let’s get dressed up and go out to breakfast.”

“Okay,” she said, “What did you have in mind?”

“Slacks and high heels,” I said.

As she was taking a shower, I started to get dressed. I took off my underwear, and got out a pair of K-Mart Soft Smooth and Sheer pantyhose in Mist Tone, opened up the package, and pulled them up my legs. I put on a white dress shirt and navy blue slacks. I went in my hiding place and got out my white sandals and dropped them on the floor in the bedroom. About that time Becky walked out of the bathroom and into the bedroom, and looked me over head-to-toe. “Ooh, you’ve got hose on,” she said. “Your feet look so pretty.”

“Thanks,” I said, smiling and blushing.

She looked at my new sandals. “Wow, those are cute,” she said. “When did you get those?”

“I saw them at K-Mart the other day and just had to get them.”

She smiled, “You mean you went shoe shopping without me? So let’s see how you look in them.”

I stepped into them and walked around the bedroom to the full-length mirror. She said, “You look great! I love it when a man wears nylons. It shows his feminine side. And you’re wearing sandalfoot hose too. Very good,” she giggled. “I guess I have to wear pantyhose too, since you are. I’ll wear my new brown pumps.”

We went to a quiet little cafe for breakfast, and nobody paid any attention to me. We held hands in the car on the way home, and I got SO aroused looking at my nyloned toes in the sandalfoot hose sticking out of my high heels. As we got home, I was really feeling the urge for a bowel movement. We kissed the minute we got in the door, but I wanted to go poop before we did anything else. I said, “I don’t mean to put a damper on things, but can I go to the bathroom first? I feel like I really need to do my push job.”
“Sure,” she smiled, “if I can come in too.”

We walked in the bathroom and I pulled down my slacks and sat on the toilet. I folded my arms over my abdomen and started to push. My stool was big, and hard. I knew I was really going to have to push to get it out. I sat there pushing and straining, and I could feel my face turning red as I grunted.

“Wow, I think you’re a little constipated,” she said.

“I know. I haven’t had a BM since Thursday. I should have taken some Correctol.” I stood partway up and pulled my buttocks apart before I started pushing again. “Wow, it’s really stuck,” I gasped, as I pushed inward on my tummy to try to help it move, but it just wasn’t coming any farther. I needed Jake to buttfuck me, but that wasn’t an option at the moment.

“Looks like you do need some Correctol,” Becky said.

“My stool is SO hard,” I groaned. “I think I need a Fleet enema,” I said, squirming around on the seat.

Becky said, “I guess sex in YOUR butt wouldn’t work very well. Let’s go back to Osco’s and get you one.”

I stood up and pulled up my pantyhose, and tucked my shirt back into my slacks. Becky got her purse and we drove back over to the mall. We walked arm-in-arm into Osco Drug, our heels clicking sexily on the sidewalk. We walked down the laxative aisle, looking for the disposable enemas. There was an elderly couple standing there looking at Ex-Lax, the wife pointing to something on the package and telling her husband, “You really need to take something.” The Fleets were in front of them, and I said, “Excuse me,” as I reached between them to get some. Seeing an effeminate man in hose and white high-heeled sandals, and buying an enema, the woman really gave me the once-over, frowning. As I stood there, reading the package, I started dipping my pantyhosed foot in and out of my high heeled sandal, putting on a show for her. I grunted and moaned to Becky, “My bottom hurts so bad. My stool is so big and hard. You’ll have to stick it up in me.” The woman’s face turned bright red.

“Of course,” Becky said, soothingly. “Don’t worry, you’ll finally be able to have a BM after a good enema. Maybe we should get the two-pack, then we’d have one on hand for the next time we get constipated.”

“Mmmm,” I grunted, “that’s a good idea.” I put my foot back in my high heel while Becky picked out a two-pack, then we walked away, arm in arm, our high heels clicking away. We checked out and walked back to the car, and my erection built again with the memory of being seen in public in high heels, buying an enema (and showing the whole world that I was constipated), feeling the breeze on my nyloned feet and ankles, and hearing my high heels click on the concrete.

When we got in the car, Becky started to giggle. “Did you see that woman look at us? She was staring at your feet almost the whole time we were in there. After she glared at you, she looked daggers at me. You’d think she never saw a guy in hose and high heels before.”

As we were driving home, I said, “Maybe I can finally get some relief. I feel so bloated.”

When we got in the door, we picked up where we had left off. Becky put her arms around my neck and kissed me deeply. I let my hands roam down to her lovely derriere, feeling her perfectly smooth pantyhosed bottom, moaning as I did so. “Mmmm, no panty lines,” I said, as I kissed her again.

“We both looked so smooth in our…. pantyhose,” she said as we kissed again.

“Mmmm-hmmmm,” I moaned, leading her into the bedroom. We both kicked off our high heels, and I fell onto the bed, pulling her with me. Our foreplay picked up intensity, and we finally rolled apart and started taking off our clothes. I shed everything but my panty hose, and she left hers on too. I got the Fleet enema out of the package, and said, “Would you like to help me use it? My mom showed me how to use one a long time ago, but I’m not sure.”

“Sure,” she said. I handed it to her, and rolled over on my left side, bending my right knee and getting into the Fleet Enema position. She took the cap off, and reading the instructions, said, “Insert enema with tip pointing toward navel.” She got behind me as I pulled my butt cheeks apart with my free hand. I saw her looking at my butt, and knowing she was seeing my little boi pussy made me so hot. She put the tip in my pussy and then pushed it the rest of the way into my rectum. She gently squeezed it, and I could hear and feel the water gurgling up into me. “Withdraw tip from rectum,” she said, and pulled it out. “Remain in position until urge to evacuate is strong.”

“Would you like to lay with me while we’re waiting for it to work?” I asked.

“Sure,” she said, laying down in front of me. We put our arms around each other and snuggled. I started rubbing my hosed foot on hers, and said, “I’ve been so constipated lately.”

She replied, “You sure are. You should have taken some Correctol last night.”

We kissed and petted, and then I felt the urge to go. It got intense quickly. “The urge to evacuate is getting strong,” I giggled. “C’mon, we better go in the bathroom,”

We ran into the bathroom and I settled on the toilet. I relaxed my ring and started to push. The water shot out of me for a second or two until my big hard stool stopped it, and it finally came out of me and splashed into the toilet. “Finally,” I grunted I pushed again and the rest of the water came out in a rush. I relaxed and then pushed some more, and a little more water came out. “I hope that’s it,” I said. “I don’t want to have an accident.”

“Why don’t you use one of my tampons, sissy boy?” she asked. “That would soak up the water.”

“Sure,” I said. She opened the medicine cabinet and handed me one. “Do you want me to put it in you?” she giggled.

“Sure,” I replied.

“Let’s go back in the bedroom. Get in the Fleet Enema position again, that will help open up your bottom.” I laid down on the bed again on my left side. She tore open the package and took it out. She put a little saliva on the end to lube it, then put the end against my anus and pushed it partway in. Grabbing the outer applicator with my other hand, she pushed the inner one up in me, then pulled out the applicator. “There,” she said, “just like how I do it!”

I put my fingertips against my pussy and I could feel the tampon just inside. I tugged on the string carefully to make sure it was in tightly, then washed my hands. Walking back to the bedroom, Becky said, “I can see your string hanging out. I can’t believe my husband’s using a tampon.”

We laid there looking at each other, her lovely nipples and my dick erect, and our feet looking so smooth and elegant in hose. We resumed petting, kissing deeply, and running our hands over each other. Finally, she whispered in my ear, “I’m ready.” I mounted her and she spread her legs, inviting me in. She gasped as I penetrated her, and we moved together, our orgasms coming much too soon as we couldn’t put them off any longer.

Afterward as we started to get up, I pointed my foot at her, wiggled my toes in my nylons, and said, “Can we leave our hose on?”

She walked over to the dresser and pulled out two pairs of footie socks and handed me a pair. “Sure. Here, we’d better put footies on over them so we don’t get any runs.”

I kissed her as she handed me a pair of her footies. “Put your girl jeans on,” she said, “and tonight when we go out we’ll wear our jeans and clogs.”