Sunday Morning Pantyhose
By
Tracy Davis

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 -- Tracy

Sunday morning, Mom came in my room to pick out my clothes. She got out a nice shirt and dress pants from my closet, and then when she turned around, I saw she had a package of Osco Drug panty hose in her hand. She surprised me by saying, “Since you’re in junior high now, I thought you might like to start wearing pantyhose under your slacks when you dress up. It’ll make them fit better, and they’ll slide over your legs easier when you stand up and sit down.”

Wow, I couldn’t believe what she was saying! My dick immediately got rock hard, and I didn’t know what to say. “Sure,” I said.

She opened the package and took out the hose, and laid them on my bed. “Put your hose on, then come out in the kitchen and we’ll have breakfast.”

My hose! I couldn’t believe she had said that. After she left the room, I closed the door and slid out of my briefs. My dick was standing at attention. I put the panty hose on and straightened out my dick so it was vertical and not so noticeable, then pulled my tee shirt down over it. I sashayed out into the kitchen for breakfast and sat down at the table. I saw Mom already had her hose on under her robe. I felt so girly sitting there next to her eating breakfast, both of us with panty hose on! After we picked up the dishes, she said, “I’m going to go try for a BM. You should try to have one too.”

“That’s a good idea,” I said, frowning. “I haven’t had one for a few days.” As I walked to the bathroom I looked down and saw my legs looked so smooth and tan from the nylons, and I just felt so pretty! Once in the bathroom, I pulled down my hose and sat on the toilet. I did a few gentle pushes, not expecting any results, but I farted and then started to feel the urge to go. My stool was really big after not having a BM for a few days, but it came out without too much trouble. It really stretched my hole out as it passed, and after it plunked into the toilet, I felt so empty and relieved inside! I didn’t flush it as Mom usually wanted to see my stools to see how much I had done. I walked into her bedroom just as she was opening her bathroom door. I walked over there and announced, “I had a really big BM. Do you want to see?”

“So did I,” she said, and as she stepped to the side I could see her stools floating in the toilet before she flushed. We walked into my bathroom and she saw my big stool wedged all the way down in the trap. “Wow,” she said, “you really needed to have a good BM. I bet you feel better.”

“I do,” I agreed. “Can you wipe me?”

“Sure,” she said, “sit back down.” She rolled off several sheets of TP and I leaned forward so she could see in my crack. Back in my room, I took off the tee shirt and put on my dress shirt, then slid my new slacks up my legs. It felt so sleek and sexy, sliding them on over the nylons! I combed my hair and then went back into Mom’s room. I was getting so excited. I was actually going to wear hose to church. This was really happening! As I walked in, she said, “So how do they feel?”

“Great,” I said. “It’s a neat feeling, with my pants rubbing on my hose.” I couldn’t believe I could say that. Looking down at my feet, she said, “You’ll still have to wear socks so people can’t see. Also you’ll have to remember to keep your shirt pulled down every time you stand up, so that the waistband doesn’t show.”

On the way to church, I saw Mom’s legs in her skirt, and couldn’t stop thinking that we both had hose on. How many teenage boys can say, “My Mom and I are both wearing nylons to church?” Getting in and out of the car, I noticed what she meant about my slacks sliding over my legs better. When we went up to take Communion, I was really conscious of my slacks sliding over my hose every time I took a step, and especially as we knelt down at the altar and then stood back up. As we walked back to our pew, I noticed every teenage girl that was in line for Communion that was wearing nylons, and I felt so much like them. If only they knew this boy walking past them had hose on too! I had a huge hard-on by the time we got back to our pew. As we sat down, we both crossed our legs automatically. Mom looked at me and ran her fingertip over the top of my thigh, smiling knowingly, and I smiled back. She knew I was enjoying the feel of the nylons.

When we got back in the car to go home, I said, “You weren’t kidding, the pantyhose really make my slacks fit better.”

She smiled, “I could tell by how much you were crossing and uncrossing your legs you were enjoying how they felt. Now you know why women wear them all the time. They make our legs look nice and they make our clothes fit better.”

Blushing, I said, “They make me feel so sleek and smooth, like I don’t have any underwear on.”

She said, “That’s another reason we wear them under our slacks. They make you look like you don’t have any underwear on.”

When we got home, I stepped out of my shoes and reached down and slipped off my socks so my pantyhosed feet would show. I wondered if I should take off the nylons. I really wanted to leave them on. I walked into the kitchen, looking down at my nyloned feet, and all of a sudden I ejaculated. It took me totally by surprise. I just stood there, quivering, not sure what to do. Mom looked at me and said, “Are you alright?”

“Um, I guess so. I need to go to the bathroom,” I said, quickly walking into the bathroom and closing the door behind me. I pulled down my pants to survey the damage, but my pantyhose had contained it all. I took some tissues and wiped it up, and dried the wet spot in my pantyhose panty as best I could. My dick was now so limp, I tucked it down into my nylons so I had a smooth front like a girl. I pulled my pants back up and walked back out into the kitchen. Mom looked at me and said, “Are you OK?”

“Yes,” I said, blushing. “I shot my… boy juice.”

“Oh,” she said. “Did you get it on your slacks?”

“No,” I said. “It all stayed in my… panty.” It felt so weird and sexy to say that.

I set the table and then helped Mom fix lunch. As we were sitting there eating lunch, Mom said, “Now that you’re in junior high, you should probably put hose on whenever you get dressed up.”

“Mmmm, OK,” I said, not believing what I was hearing!

After we finished lunch, I helped pick up and do the dishes. After I hung up the dish towel, I was looking down at my nyloned feet and wiggling my toes, about to ask her if I should take them off, when she said, “You should change out of your good clothes and hang them up. You can leave your hose on and put jeans on over them if you want. Just put socks back on if you go outside, so you don’t get runs in your hose.”

To be continued………..

Sunday Morning Pantyhose II
By
Tracy Davis

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 -- Tracy

After I started wearing nylons to church every week, Mom started buying me pantyhose whenever she bought some for herself. I would come home from school and go in my room and find a pair of nylons laying on my bed, new in the package. After looking them over and thanking Mom, I would put them in my underwear drawer. I felt so girly every time I would open my underwear drawer and see the jumble of pantyhose in there, along with my boy underwear!

One night, Mom was doing laundry, and she washed out a bunch of pantyhose and hung some of them in my bathroom. She said, “I just washed out our hose. I hung yours in your bathroom to dry. Feel of them tomorrow, and when they’re dry, you can coil them up and put them in your underwear drawer.”

Every time I walked past the bathroom, I looked in at my hose hanging there drying. My hose! I felt like such a girl!

I was starting to get particular about how I put on my pantyhose when I wore them. After I got them pulled up to my waist, I would look in the mirror and make sure the panty seam was right over my crack. Then I would finish pulling them up to my ribcage, forcing the panty into my crack, to separate my buttocks and give me a nice smooth girl’s butt. That way when my shirt rode up you could see I had pantyhose on. I just loved that feeling!

Early in December, I woke up on a Sunday morning, got up and put on my pantyhose like every Sunday, and went out into the kitchen. Mom was already sitting there at the table, mixing Serutan into her orange juice. I got a cereal bowl and glass out of the cupboard and sat down at the table.

“Serutan?” I asked.

“Yes,” she moaned, “I have been SO constipated lately. When was the last time you did your push job?”

“I haven’t done one for a couple of days,” I frowned. “I feel a little crampy inside this morning.”

“Sound like you’re constipated, too,” she said. “Here, let’s put a little Serutan in your juice to help give you a push. I’ve had such hard dry stools lately, even with the fiber I’ve been taking. I’m going to have to have an enema after church if I don’t go this morning. I haven’t had a bowel movement for three days.”

I felt my leg itch, and I reached down and scratched it, feeling the texture of my hose on my leg, and my dick started to get hard. I laid my hand in my lap and then started to graze my hosed legs with my fingertips, fascinated with the feeling. We started talking about what we were going to wear and different fashions, and what color nylons to wear with them. She told me the difference between nude, beige, tan, taupe, and coffee shades. After a pause in the conversation, I said, “I think I like suntan the best. You can definitely tell I have hose on when you look at my feet. I feel so pretty with these on,” blushing.

Mom patted my hand and said, “That’s why we wear them – to be pretty,” and we both giggled. “I can tell you like wearing them. You keep running your hands over your legs, and you just look so happy.”

“When we’re sitting together in church, and I can see you have hose on, and I know I do too, I just feel so close to you.”

“Awww, that’s sweet,” she said, reaching over and touching my hair.

After we cleaned up the breakfast dishes, we went in the bathroom and I did a nice big long push job. I loved sitting there on the toilet with my smooth tan pantyhosed legs showing. I crossed my legs, admiring how pretty they looked, and I started bobbing my foot up and down like a girl while my poop was sliding out of me. After Mom wiped me, I went in and finished getting dressed while she tried unsuccessfully to do her BM.

It had snowed the night before, and as we were getting ready to leave for church, Mom said, “I got a new pair of shoeboots the other day, and I thought you could have my old ones. They’re lined so you won’t have to put socks on over your hose. Those can be yours from now on.”

“Okay, thanks,” I said. I went back in my room and took off my socks, then went back and pulled up my pantlegs and slid my nyloned feet into the boots.

They had heels, and when I stood up, Mom said, “When you walk, step heel-to-toe. Put your heel right in front of the toe of the other foot when you walk. That’s how you walk in heels.”

I felt really sexy as I walked like that to the car, hearing them clicking on the concrete. As we were driving to church, I thought about what Mom said about them being mine, and then I thought about girls at school talking about getting their first pair of heels, and I thought, This is my first pair of high heels! At church during the sermon, my legs crossed, sitting there next to Mom, I started thinking again about how we both had pantyhose and high heeled women’s boots on, and how close I felt to her right then. I looked at her and saw she had a pained expression on her face, probably from the constipation. I felt badly that I had had a BM and she couldn’t go at all.

“Are you OK?” I whispered, concerned.

“Mmmmm,” she grunted, unhappily.

I took her hand and held it, and she moved our hands over on top of my knee, and smiled. I flexed my toes and enjoyed the feel of the nice soft linings of the boots through my nylons. I kept thinking about how sexy I felt when I slid my pantyhosed feet into my ladie’s shoeboots before we left home. If I took them off right now, people would see my reinforced toes and know that I had hose on! My dick was so hard. I looked down and you could tell that I had an erection. I hoped nobody noticed.

After church, we were standing around in the fellowship hall, and I saw this really pretty woman reach down into her slacks and pull her pantyhose waistband up several inches, wiggling around as she did it, then pulled her sweater back down. It was so erotic, knowing that she had hose on under her slacks just like I did.

After we left church, we drove to the drugstore. As Mom and I walked into the store, you could hear both our boot heels clicking on the tile floor as we walked. I noticed I was starting to walk like a girl in the heels without even thinking about it! We went over to the laxative aisle and Mom picked up a Fleet enema and was looking at it. I looked down at my feet in women’s boots, remembering the sleek feel of the slacks over my hose, and the click of my high heels as I walked in them. I remembered the woman at church pulling up her pantyhose waistband, and I wanted to try it. Looking around, we were alone, and I reached down under my shirt and into my slacks and pulled up my pantyhose waistband just like the woman at church, all the way up to my ribcage, wiggling as I did it, showing the whole world that I had hose on. As luck would have it, just as I did, a woman came down our aisle and saw me doing it. She looked at me quizzically as she walked past. I looked down at my crotch and you could tell I had an erection again!

Mom picked up a two-pack of the enemas, and said, “I’m going to get two of them. That way we’ll have one on hand in case you or I get really need help to go.”

When we got home, we sat down on the closest kitchen chairs and took off our boots. Standing up in our hosed feet, Mom said, “Lunch is going to be a little late. I’ve got to get some relief.”

“That’s OK,” I said. “I know you really need to go.”

She went in her bedroom and shut the door. I went in my room and laid down on the bed, unsnapping my pants and sliding them down to my thighs. I reached in my hose and straightened out my hard dick. Looking at my hosed feet, feeling the slacks sliding over my hose, and remembering the morning’s events, I was ready to explode. I started running my fingers over my dick, feeling the texture of my hose against my glans. I thought about Mom in the next room having her enema, and remembered the last time she gave me one, and how good it felt when I finally had my long-overdue bowel movement. Looking at my pantyhosed toes, I moaned in my best girly voice, “I wore my high heeled boots today. . . with my panty hose.” I exploded, filling the panty of my hose with a huge gob of semen.

A little while later, we both came out of our rooms. Mom did look happier. “Feel better?” I asked.

“Mmmm-hmmm,” she said. “I had to go so bad. Now let’s have lunch!”

To be continued..............

Authors note: There have been a number of negative comments about the discussion of some bathroom issues in the stories. Let me address those, as I think they are germane to the story.

I am not into coprology or ‘poop’. You will never hear my discuss pooping in my nylons, as I never did that. The time frame of this story is the early ‘70s, when I was a tweenager starting junior high school. My mother had me late in life and was in her early 50s during this story. As many of you know, middle-aged women back then tended to be rather, well, fixated about their bathroom habits. As most feminized boys, I loved to listen in on the conversations when my mother had her friends over, and there was a lot of talk about this particular “issue”. Nothing graphic or gross, just “I haven’t been able to go for three days so I took product X and it didn’t work for me, so I went back to product Y. How did it work for you?” kind of thing.

I had had some problems as a small child about not going to the bathroom when I needed to. The doctor had told my mother to actually look in the bathroom after I had gone to make sure I really had and was not just lying about it to avoid getting an enema. One time I was particularly messy and she offered to wipe me, and I let her. I kind of liked the attention, and we kept that up through eighth grade.

Later on in the stories I will relate (spoiler alert!) about a conversation between my mother and my older sister, who lived on her own and wound up contributing to my feminization. My mother had said that she thought us sharing clothes and shoes brought us closer together than most teenage boys and their mothers, and she was right. We were closer than most teenage boys and their mothers (Not ewwww close!). My mother had been a nurse and had a lot of medical knowledge, and we had a lot of talks about the human body and some of its grosser aspects, always using the correct terminology and not gross slang.

So, enough about that. If it offends you, I apologize. Please just scroll down a few lines and go past it and keep reading.

Thanks so much for reading my story, and for taking the time to comment!

Smiles, Tracy

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 -- Tracy

On Christmas, Mom and I got up late. We went out and opened our presents in our PJs. Mom had gotten me a package of three pairs of thick cable-knit girls tights in black, navy, and purple, along with a couple of pairs of Osco Drug panty hose, and a girl’s pink short dressing coat.

When I opened it, Mom said, “It’s a dressing coat. You can wear it on Sunday mornings when we’re having breakfast, before you get dressed when you only have hose on. It’ll give you a little more modesty than just wearing pantyhose. You can wear those tights to school when you don’t have gym. They’ll look like boy’s socks on your feet, and no one will know you have tights on. They’ll keep you warmer. I saw a lot of your hose have runs, so I got you some panty hose too.”

After breakfast, we went back to our rooms to get dressed. We were going to have a nice dinner and I felt like getting dressed up. I opened up my underwear drawer to get out some nylons. I always felt so girly now when I would open my underwear drawer and see all the pantyhose in there, along with my boy underwear. I slid on a pair of panty hose and then a nice shirt and slacks. When I came out of my room, Mom was in the kitchen in jeans and a sweatshirt. She looked at my feet and said, “Mmmm, you really got dressed up.”

“Well, yeah,” I said, “It’s a holiday. I thought we were going to have a nice dinner tonight. You should get dressed up too.”

She faced me, and smiling, flipped my bangs over and out of my eyes. “You know, you’re right. I should get dressed up too.” She thought for a moment, and said, “I have an idea. Come in here with me.”
We went in her room and she opened her closet. Reaching up on the shelf, she took down a shoe box and opened it. She pulled out a pair of high heeled white sandals and handed them to me. “I’ve been watching you walk around in those high heeled shoeboots and I can tell you like them. Here, as long as we’re getting dressed up, and not leaving the house today, how would you like to wear a pair of my heels? They’ll make you look really dressed up. We’ll see how long you put up with them till they start pinching your feet.”

“Sure,” I said, not believing what was happening. I sat down on her bed and put the shoes on the floor, and slid my nyloned feet into them. I fastened the straps, and then stood up and took a few tentative steps. They were a little higher heel than the shoeboots. “Go out and walk around and get used to them while I’m getting dressed.”

I walked out into the hall and she closed the door behind me. I walked down the hall heel-to-toe and closed the door that had the full-length mirror on it. I walked up to the mirror, looking at my reflection, and I couldn’t believe it. My pantyhosed toes were peeking out the front of the sandals, and I looked SO cute and hot. My dick was so hard, and you could clearly make out my erection through my pants. I unsnapped them and reached down inside my hose and straightened it out, so it was vertical and not that noticeable. I kept turning around in front of the mirror and looking at myself, trying different poses, marveling at how sexy the heels looked from the side. It was so erotic. About that time, Mom came out of her room. She was dressed to the nines and looked really nice. She had a really pretty blouse on, navy blue dress slacks, and blue pumps. Her ankles were darker and I could tell she had hose on. We stood there together in front of the mirror and she put her arm around my waist. “There,” she said, “Don’t we look nice?”

“Mmm-hmmm,” I said, “Good thing we wear the same size shoes so I can borrow yours,” I giggled.
When we made dinner, we were walking around the kitchen and I always volunteered to get things out of the cupboard for her, taking as many steps as I could, in love with how it felt to walk in high heels, and the sound of them clicking on the tile!

After while, I felt like I had to pee. I clicked into the bathroom in my heels, and I felt so girly, I decided to sit down to go like girls do. I pulled down my slacks and pantyhose and sat on the toilet, making sure my dick was aimed down. I had left the door open and Mom walked past as I was tinkling. When I was done I stood up and pulled my hose and trousers back up and washed my hands. Mom saw me and said,

“You sat down to pee?”

“Mmmm-hmmm,” I blushed. “I just felt like doing it that way. I think I’m going to start doing it that way when I’m home.”

“That’s good,” she said. “It’ll keep you from peeing all over.”

After dinner, we were sitting in the family room and I was looking at my feet in the heels, putting them together and bending my feet, rotating my ankles, totally in love with how they looked. “I hate to tell you,” Mom laughed, “You know you can’t wear those to church.”

“I know,” I sighed, disappointed, “but I was just thinking how much I’d like to wear them out in public.” I was starting to feel the urge for a push job, and I got up and said, “Mmmm, I think I need to do my push job. I’ll be in the bathroom.” I sauntered into the bathroom and sat down on the toilet. My stool was large but smooth, and I bore down gently, enjoying the feel of it stretching out my anus. I took my time and let it creep out of me slowly, my dick getting so hard, until it finally plunked into the water. I called Mom to wipe me, and I could hear her heels clicking on the kitchen tile as she walked across it, same as mine. She came into the bathroom and I bent forward to give her access. After she wiped me I stood up and pulled up my hose, and she looked into the toilet at my great big stool. “Wow,” she said, “you really had a good BM. I feel like I need have one like that. All I could do this morning was a couple of little ones. It just feels like there’s a lot more in me that needs to come out.”

“I couldn’t believe how big it was either,” I said. “It came out really easy.”

“It makes it easier to have a BM when you have heels on,” she said. “It raises up your knees and straightens out your bowel. Remember that the next time you’re having trouble having a BM. A lot of times when I’m constipated I’ll put on heels when I’m trying to go. Actually I may take the paper and go sit in my bathroom and try.”

A little while later, Mom came out of the bathroom, and looked a lot happier. “Success?” I asked.

“Mmmm-hmmm,” she said. “That’s the most I’ve done in a week. I feel so much better.”

I giggled. “Maybe it was the heels.”

She giggled too. “It probably was.”

Mom went in her room and came out with her nail stuff, and sat down and did her nails. After a while, when I was sitting on the couch, she said, “How would you like a little polish on your nails?”

“Sure,” I said, not able to believe what I was hearing. She sat down on the couch and I sat next to her, crossing my legs so I could snuggle closer to her. We talked while she pushed back my cuticles, filed my nails, and then put a coat of pink polish on them. “Be careful not to touch anything for a while,” she said when she got done. The TV was on so I just watched TV for a while, not able to stop looking at my polished fingers and my hosed feet in high heel sandals.

After supper, I reluctantly took off the high heels and carried them back to her in her room. She took them and said, “I can’t believe you had those on all day. Most women can’t even wear heels that long. Don’t your feet hurt?”

“A little,” I said. “I really didn’t walk around in them all that much.”

Mom laughed. “Are you kidding? Every time I said I needed something you were running to get it. I thought you’d have them off after the first half an hour.”

I blushed. “I really like wearing them,” I said, lowering my voice. “I like how they feel. It’s almost like I’m turning into a girl.” My eyes welling up with tears, and I wasn’t sure why.

“It’s OK,” she said. “When we’re alone together, you can be a girl. It’s pretty obvious how much you like it. Now let’s find some remover and take off your nail polish.”

A few weeks later, Mom came home from work on a Friday night and said, “I really don’t feel like cooking. Let’s go out to for dinner. You should probably wear something nice.”

Great, I can wear nylons! I thought. As I was going to get dressed, Mom said, “You know, it’s dark outside, and it will be dark in the restaurant. How would you like to wear my heels outside? Nobody will notice.”

“Sure,” I said, my heart pounding.

I got dressed, and when I came out of my room, Mom had the high heeled sandals out on her bed already. “Here you go,” she said. “Remember how to walk in them?”

I put them on and we got ready to leave. When we walked out in the garage, I could feel the cold air on my toes, and knew they were on display!

When we got to the restaurant, I walked next to Mom, trying not to be self-conscious. We stood in line to wait to eat, but no one even noticed my heels and hose. I couldn’t believe I was standing there in public in ladie’s high heeled sandals and panty hose! It was a dream come true. My dick was getting so hard, and I forced myself to think about something else so people wouldn’t notice my erection. After we sat down at our table, I noticed a boy that was about my age sitting at the next table. As we were getting up to leave, I noticed he was staring at my feet. I wondered what he was thinking?

When we got home, we took off our heels, and I handed them to Mom. She said, “You know, why don’t you just keep them in your closet. If I want them, I know where to find them.”

Wow, I thought. My SECOND official pair of high heels!

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 -- Tracy

When we were planning a visit to see my sister-in-law and her son, Mom said, “You know, we should go shoe shopping and get you some cute girl shoes for you to wear. Something a little more age-appropriate for a thirteen year old instead of my high heeled sandals. Like maybe some cute Mary Janes with a little heel.”

“That would be great,” I said, getting aroused at the thought of going and trying on girl’s shoes. “But what will Charlene think?”

“Don’t worry. I’ll talk to her. I’ll bet she’ll be more supportive than you think.”

The next Sunday, after church, we went to the mall and stopped into a family shoe store. We were looking at girl’s and ladies shoes and Mom found some back patent Mary Janes that were really cute.

The sales lady approached us and asked, “Can I help you?”

Mom pointed to the Mary Janes and said, “We’d like to try a pair of those.”

“Do you know your size?” She was looking from Mom to me, confused.

“I wear an 8, and mine fit him pretty well, so let’s start there,” Mom said.

She smirked and walked away. Mom looked at me and said, “Take off your shoes and socks.”

I sat down and took off my shoes and socks, and crossed my legs with my pantyhosed feet on display. The saleslady came back with a box and sat down in front of me, staring at my reinforced toe nylons for several seconds before she opened the box and took out the shoes. She slid my feet into them, and the feel of her fingers on my nyloned ankles made my dick instantly hard. She fastened the straps and said, “Stand up. How do they feel?”

They fit well and didn’t pinch my toes. The saleslady said, “Walk around in them and see how you can walk.”

I got up and walked heel-to-toe across the room, toward the low mirror, and couldn’t believe how cute they looked on me. You could see most of my feet in them, and my skin looked flawlessly perfect in my nylons. Mom said, “Those are really cute.”

The saleslady said, “He can wear them for a bit while you shop, if you like.”

Mom and I went back to the display and kept looking while I kept walking around in them. I looked so cute in them! I kept looking at the front of the store to make sure none of my friends came in. The saleslady went over to help some other customers but kept looking our way. Finally she came back over. “Have you decided?” she asked.

“What do you think?” Mom asked me.

“I really like them. They’re really cute.”

“Okay, we’ll take them,” Mom said.

“Is she wearing them home?” the saleslady asked, obviously embarrassed.

“No, he can wear his others,” she said, and I sat back down. The saleslady took them off my feet and put them back in the box, constantly stealing glances at my nyloned feet, until I put my socks and shoes back on.

As we walked out of the store, Mom said, “There, now you have some girl shoes of your own that you can wear out when we go out of town.”

“Wow, thanks,” I said, wishing I was wearing them home.

When we were packing to leave, Mom came into my room and said, “Let’s take your Mary Janes and a pair of pantyhose for you in case we want to get dressed up and go to a nice restaurant. It’s still pretty cold up there so we’ll also take your cable knit tights and your shoeboots. Do you want to wear tights or underwear?”

I said, “Tights. But I don’t want Char to make fun of me.”

“She won’t. I talked to her the other night, and told her that you liked to look a little girly when you dress up, and she was OK with that. She said she even might have some things for you to try.”

“Can I wear tights and shoeboots on the trip up there?”

“Sure,” Mom said. “I’ll leave a pair out for you to wear and pack the rest. You have three pairs and that should be enough. I’ll just take a pair of underwear for you to sleep in if you want.”

“Ummm, can I ask something else?”

“What sweetie?”

“Do you think I could have nail polish on up there?”

Mom thought a minute, and said, “Sure. Why don’t we do our nails tonight before bed? We could even do your toes if you want.”

We had a close time doing our nails. I felt so pretty when we got done. The next morning, when I was out in the kitchen eating breakfast, I couldn’t believe how cute my hands and feet were!

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 -- Tracy

After we arrived, I was wearing tights every day, with nail polish on my nails, and Char always remarked about how nice I looked. It was heavenly!

Every day I was having my morning sit on the pot, but I wasn’t having a bowel movement. After three days, I was really starting to feel crampy and uncomfortable. That afternoon, Mom came into the bedroom where I was reading. I said, “I’ve got a little problem.”

She said, “What is it, sweetie?”

I lowered my voice and said, “I’m….. constipated. I’ve been trying to go every morning but I haven’t had a BM since we’ve been here.”

She said, “I wondered, since you haven’t asked me to wipe you since we’ve been here. It happens to a lot of people when they travel. You should really try to go after dinner tonight. If you still can’t go, we’ll have to give you something.”

Later I noticed my mom and my sister-in-law talking in hushed tones. I crept up around the corner from them so I could hear what they were saying.

“Brian’s constipated. He hasn’t had a push job since we’ve been here. His breath is bad, he’s just picking at his food, and his tummy is sticking out. Do you have anything I can give him?”

Char said, “I have Correctol, that’s what I take.”

Later that afternoon, Char asked my mom, “What were you going to have him wear tonight?”

“I brought a white and blue striped zipper top for him for dress-up, and navy blue slacks. I also brought his black patent Mary Janes, they go with anything.”

Char whispered excitedly, “I know. I’ve got some navy blue pantyhose he can wear. They’re even sheer to the waist. Oh, and he can wear my navy blue platform slides. He’ll be so cute!”

“Oh wow, that’ll really be cute. I’ll go lay his clothes out.”

I walked around the corner at that point and said, “Oh, hi. When are we going to dinner?”

Mom said, “Pretty soon. Why don’t you go ahead and get dressed?”

We walked to our room, and Mom laid out my clothes for me. As I was getting undressed, she said,

“Char has some navy blue panty hose and wedge sandals she said you could wear. How would you like to try those?”

I couldn’t believe what I was hearing. Me, get to wear her pantyhose and sandals? It was like a dream come true. I tried to keep the excitement out of my voice. “Okay, I guess.”

We walked into her bedroom and she pulled out her underwear drawer in her dresser. She dug around for a minute, and then pulled out a pair of navy blue pantyhose and handed them to me. “Here, go back to your room and change into these, then come back and we’ll try on the shoes.”

I want back to my room and closed the door. My heart was pounding with anticipation. I took off my slacks, underwear, and socks, and cleaned out between my toes. I gathered up the pantyhose and slid them up my legs. I saw they were sandalfoot as I was pulling them over my toes, but as I finished pulling them up I saw they were totally sheer-to-the-waist! My dick stuck out of the hose so much I thought my pants couldn’t possibly hide it, but they did – they actually fit better with the pantyhose holding everything in. I admired myself in the full-length mirror – my blue pantyhosed feet looked SO sexy, I couldn’t stop looking at them! Finally I worked up the nerve to go back down to Charlene’s room. As I walked, I could feel my slacks sliding against my pantyhosed legs and my barestocking feet sliding along the hardwood floor, and I felt so sleek and sexy. The door was closed, and I knocked lightly.

“Come in,” she called.

I opened the door far enough to go it. She was in her bra and panties, looking at tops in her dresser. I saw her look down at my feet to see if I had the hose on. Looking back up at me, she said, “So how do they fit?”

“Just fine,” I replied. “They’re even sheer-to-the-waist. I’ve never worn sandalfoot hose before. Mine are all reinforced toes.”

“Mmm-hmmm,” she smiled. “They’re really revealing, aren’t they? A little birdie told me you like to wear nylons. You look so grown up with hose on! The shoes are in the closet, near the front. Help yourself.”

I opened the closet and was immediately struck with the sexy perfumy smell. My heart really started to pound – here I was in the inner sanctum, with dresses and high heels everywhere! I looked down and saw a pair of navy blue platform wedges. Those must be them, I thought. I stuck my toe in one and pulled it out of the closet, then got the other one out. After getting my feet in them all the way, I walked over to her mirror in them, getting used to the height. Even though they were two-inch heels, they felt really comfortable and natural, and when I saw myself in the mirror, I couldn’t believe how much more feminine I looked.

Char came up to me and put her arm around my waist. I felt like her sister, standing next to her and looking at ourselves in the mirror. She pulled up my shirt slightly and said, “If you pull the waistband up slightly above your waist, the hose will stay up better.” We stood there together for a minute, Char touched my hair lightly, and continued, “I’ll let you in on a little secret. When you wear pantyhose under slacks, if the waistband is showing above your slacks, the guys will be staring at your rear end. It’s a wonderful feeling. Of course, if you don’t want that, just keep your shirt pulled down over your belt.”

“I know,” I said, blushing, “sometimes when I feel really daring and nobody’s watching, I reach in under my shirt and pull the waistband up so my panty shows.”

Char smiled wickedly, “You bad girl! Here, let me fix your hair.”

She parted my hair in the middle and flipped it over, then secured it in place with a little hairspray. I kept thinking about whether or not I wanted my pantyhose waistband showing. I always got turned on when I saw a girl or a woman with hose on under her slacks and it showing above her belt, but couldn’t decide if
I wanted guys staring at my butt or not. The thought was intriguing. I thought I would try it both ways.

Char turned to the mirror and started putting on her makeup. I watched intently as she did it, and as she was putting on her lipstick, she asked, “Would you like a little lip gloss?”

I wasn’t sure how to respond. “Um….. sure,” I said. She handed me a tube and showed me how to put it on and then roll my lips together to spread it around. It felt nice, and my lips were shiny and just a little darker. I went to hand it back to her and she said, “Hang on to it so you can put more on after dinner. Just put it in your pocket since you don’t have a purse.”

I walked back out to the living room to wait for Mom and Char to finish getting ready. I sat down on the couch and started to read the paper, my foot bobbing up and down in my high heels. Robby, her son, came out of his room, dressed, and sat down across from me. He stared at me, but didn’t say anything. I caught myself rolling my lips together and feeling the slippery lip gloss on them. The feel of it and the smell of the hairspray got me aroused again. A few minutes later Mom and Char came down the hall, purses in hand. They had been whispering again, but I couldn’t make out what they were saying. It was probably about me. We all got up to leave, and as we walked out of the house to the car, I looked down at my pantyhosed toes in the sunlight, feeling like a young woman walking next to two women! I noticed myself automatically walking like a girl in the heels, swinging my hips, and I felt so sexy!

When we got to the restaurant and were walking in, my top had worked up slightly, as I could feel a breeze on my lower back. As we stood in line waiting to be seated, there were a couple of guys behind us, and I thought I could hear them whisper. I felt like I was being watched! We sat down to wait for a table, and a little while later, another family came in that had a really cute teenage boy about my age. Our eyes met several times, and I saw him looking at my nyloned feet in sandals. When they called our name for our table, we got up, and I looked at the boy again – he smiled and winked, and I smiled and winked back! As we walked away with the hostess to our table, Mom reached over and pulled my shirt down over my belt. Char was right – the guys were looking me over! I felt so desirable all of a sudden, a totally new feeling for me, and my erection started to stiffen again.

After dinner, as we were riding home, I started to feel the urge to go poop. It quickly got strong, and I started making stinkies. I even noticed Robby wrinkling up his nose. As soon as we got home, Mom and Char looked at me and said, “Come on, we’re going up to the bathroom so you can go sit on the toilet.”

We went up in the bathroom and shut the door. I pulled down my slacks and hose and sat down on the toilet and started to push while they watched. I really had to strain to get it started, and it really stretched out my butthole. My face was turning red, and my dick was totally erect and standing at attention. I reached back and pulled my butt cheeks apart, and then crossed my arms in my lap to try to hide my boner. My stool was really big and hard, and stuck. “It’s just so big and hard,” I moaned, as it was stretching me to the max.

As I strained, Char said, “Try spreading your legs. That’ll help open up your bottom.” I did, but it didn’t help much. As it started to come out, it really hurt. I could feel my eyes tearing up. I tried not pushing as hard, but then it didn’t move.

Mom said, “You’re really going to have to try harder.”

I sobbed, “It hurts so bad.” I strained really hard and it hurt, and I started to cry. Char laid her hand on my shoulder and said, “It’s OK sweetie, just imagine it coming out as you push.” I did, and that helped a little, but it still hurt. My anus was stretched open to the max. I kept crying as it slowly passed. After the first couple of knobbly hard inches, it started to get a little easier. I couldn’t believe how much poop was in me. I kept pushing, and it just kept coming, and coming. Finally it broke off, and when I stood up to look at it, it had circled the bowl three times! I sniffed and said, “Can I have a Kleenex?”

“Of course,” Char said soothingly. She handed me one, and then they saw my huge push job. Mom said, “Wow! How long has it been since you’ve had a BM?”

I blushed. “I’m not sure. I think it’s been four days.”

“No wonder you’ve been out of sorts. I thought you were constipated. I haven’t seen you do your push job since we’ve been here. I thought we were going to have to give you some of Char’s Correctol.”

“I haven’t,” I admitted. “It felt really good to go.” I saw them staring at my erection, but they didn’t say anything. I pulled up my pantyhose high and tight, then pulled up my slacks. They left the bathroom and I stayed behind to renew my lip gloss. We went back downstairs, where Char was watching TV. Char had taken off her shoes, and I took off mine and sat down on the couch next to her, pulling my nyloned feet up next to me. She looked at me and said, “How are you doing, sweetie?”

“A lot better,” I sighed. “I so glad I finally did my push job. My…. turd was just so big and hard. I really had to strain to get it out. I’m sorry I cried. It just hurt so bad.”

She laid her hand on my leg and said, “I know. You probably had a fecal impaction. I couldn’t believe how big your stool was. I’m so glad you were finally able to get it out. You need to tell us when you can’t poop so we can give you something. I was going to offer you some Correctol at bedtime if you hadn’t gone to the bathroom by then.”

“Sometimes it’s just so hard for me to go poop. I have these great big hard turds that just won’t come out no matter how hard I try.”

“So,” I replied, changing the subject, “How do you think I look in…. pan-ty-hose?” I asked, dragging the word out and pointing my toes into her leg.

“You look so cute,” she replied. “I wanted to see how you’d look in girl clothes, and you are really pretty.

Mom said she had gotten you nylons. You make a very convincing teenage girl, especially with lip gloss on. If you don’t believe me, ask yourself why those guys were looking at you.”

I blushed. “I know, the feelings I got when I realized they were looking at me were, I don’t know, sexual?”

She smiled and patted me on the knee. “Isn’t that the coolest feeling? Now that you’re going through puberty, you should probably be wearing nylons more often. You’re old enough that you should be putting hose on whenever you dress up.”

“Actually, I have been,” I said. “I’ve been wearing panty hose to church every Sunday. Under my slacks. I love how they make me feel.” I lowered my voice and added, “And I usually get a great big boner too. I love the way they make me feel so sleek and smooth under my slacks.”

“We saw that you were getting pretty excited,” she giggled. “So you really like being a janeboy.”

“What’s that?” I asked.

“It’s when a boy dresses partly as a girl. You wear cute boy things, but with nylons and girl shoes. You can also wear nail polish and lipstick. It’s like your half-boy-and-half-girl.”

“Yes, I do,” I giggled. “Now I know what it’s called. I feel so pretty when I have hose on.”

“You walk really well in heels. Have you worn them before?”

I blushed. “Mmmm-hmmm. Mom and I got all dressed up on Christmas and she gave me a pair of her heels to wear. I had them on all day and she said she couldn’t believe I kept them on that long. Also she gave me a pair of her shoeboots to wear to church when it’s snowing out and those have heels.”

“Your feet look like a girl’s. Probably because you’ve been wearing pointy-toed shoes and boots.”

I had pulled my feet up next to me on the couch so I could look at them, and I got so aroused, sitting here and looking at my navy blue pantyhosed feet, remembering the night’s events, especially the guys looking at me in the restaurant. After the show was over, I stood up and made an excuse about going upstairs to read. I stepped back into the slides and Char said, “Can you put them back in my closet when you go upstairs?”

“Sure,” I said, wanting to see her wardrobe again. I walked upstairs and went into my bedroom and closed the door. I took off my shirt and slacks, picked up a book and laid down on my bed, with nothing on but my nylons. It was so erotic. I laid there reading, with my legs crossed and pulled up to me, feeling the smooth sheer nylon between them whenever I moved. I felt so relieved and empty inside after my huge bowel movement. My rectum was still tingling from being stretched so wide, and I remembered how wonderful it felt when my stool was coming out. I laid my free hand on my leg, stroking it, feeling the texture of the pantyhose and I said out loud, “I got so dressed up for dinner tonight. I had to wear navy blue pantyhose and high heels.” All of a sudden I ejaculated, more than I ever had, all over the inside of Char’s hose, making a huge mess. I hadn’t even touched my dick and I had climaxed! I panicked and quickly got up, running to the bathroom to get some tissues after making sure the coast was clear down the hallway. I wiped up my cum and tried to dry out the pantyhose as best I could. Walking into Char’s bedroom, I took off her sandals and put them back in the closet where they were. I looked over her shoe collection, and started to get hard all over again thinking about wearing them.

When bedtime came, I reluctantly took off the pantyhose and put on my pajamas. I saw Char in her room, and I walked over there with the pantyhose in hand. “Here,” I said, holding them out to her, “Where do you want me to put them?”

She looked at me and said, “You know, I have another pair of navy ones. Why don’t you keep those so you can wear them again if you want?”

“Thanks,” I blushed. “That’s really nice of you. Thanks for letting me wear your things. I felt really grown up.”

“No problem,” she said, touching my hair. “I’ve got a lot of other things I bet you would look good in. We’ll do it again sometime.”

I smiled. “Well, goodnight. Thanks again for everything.”

A little while later, before I went to sleep, I heard Mom and Char talking in the next room, and I quietly got up and put my ear to the door so I could listen better.

I heard Char say, “I think he masturbated. He said he was going upstairs to read, but when he brought the pantyhose back to me, it looked like there was a wet spot in them. I told him he could keep them. He was so cute! I couldn’t believe what a girly boy he was! His hands are so cute with his nails done!”

Mom said, “He has a navy blue suit he could wear them with too. He’d look really pretty. Too bad he can’t wear those navy blue wedges with it.”

Char asked, “I really enjoyed dressing him up. When I parted his hair in the middle and put lip gloss on him it really turned him into a girl! So, have you had him in a skirt yet?”

Mom laughed. “Heavens, no. I’ve just been doing the Janeboy thing with him, having him wear panty hose under his slacks, and letting him wear girl shoes when we’re alone. He’s even been wearing my heels and my shoeboots. I wonder how he’d react to a skirt? He has really great looking legs when he has hose on.”

“I know! I couldn’t believe how pretty his legs were when he was sitting there on the toilet. I SO want to see him in a skirt! I have a pretty young-looking dress that I don’t wear any more that he can have. He could wear it up here, no one would know him.”

“I bet he’d like it. You should see him on Sunday mornings, he puts his pantyhose on before he comes out of his room. I got him a girl’s short dressing coat to wear. Then we have breakfast, both of us sitting there in our nylons, chatting about girl stuff. He is so adorable. Then he finishes getting dressed. The first time he wore hose to church, he kept crossing and uncrossing his legs in the pew. I could tell he really liked how the slacks felt sliding over his hose. I finally ran my finger over the top of his thigh and he just smiled dreamily. I really created a monster!”

“That’s so neat that you have that opportunity to bond though. Usually teenage boys and their moms are drifting apart around now.”

“I know. That’s why I’ve been encouraging this so much,” she said. “He’s so sweet on Sundays. After we have breakfast, we go in the bathroom together and he does his BM. He wants me to come in there and sit with him while he does his push job. He is so darling, sitting there on the toilet in that cute little dressing coat and pantyhose while he pushes and grunts. Then he has me wipe him when he’s done. At least I know he’s having regular BMs.”

“I know, he was SO cute, straining to get it out when he was constipated. Probably reminds you of when he was a little boy sitting on the potty, only he has pantyhose on. That’s such an intimate moment for you two to share. He must really crave the attention, wanting you to be close when he defecates. Most teenage boys wouldn’t want their moms anywhere near while they were pooping.”

“Mmmm-hmmm. You wouldn’t believe how big his stools are. I’m a little concerned that his bowels aren’t moving often enough. The doctor also warned me that effeminate boys often suffer from constipation and don’t tell anyone until they’re really impacted. That’s the reason I’ve really been watching his BMs.”

“I’m surprised he’s sleeping in boy underwear. I thought you’d have him in panties and camis to sleep in.”

“No, I haven’t gotten him panties yet. I don’t wear panties with pantyhose, so he doesn’t either. He’s not seemed interested in panties. What started this was me catching him wearing my panty hose.”

“Mmmmm. You should get him camis to wear instead of tee shirts.”

“I thought about that, but I was afraid it would show through his shirt. We should have put a cami on him tonight, his pantyhose waistband was showing above his slacks and there were some guys at the restaurant tonight staring at it. That’s a good idea about letting him sleep in panties and a slip. Last Sunday afternoon, I was doing my nails and he came out of his room and was watching me intently. When I got done, I asked him if he’d like me to do his nails and he said yes. We sat together on the couch and he rested his head on my shoulder while I was painting his nails. I saw him staring at his hands the rest of the day until we finally took the polish off before he went to bed. The night before we came up here he asked if he could wear nail polish.”

“So, it is sexual? Does he masturbate when he’s dressed?”

“I think so. There’s semen stains in the panty of all his hose,” Mom said. “When I wash out our hose it’s easy to tell which ones are his. When we get home from church he immediately takes off his socks, and walks around the rest of the day in his hose feet. He goes in his room for a while after we get home and I think he masturbates. I’m usually fixing lunch then so I’m in the kitchen and I can’t tell.”

“I was surprised at how aroused he was tonight. I had forgotten how hard a teenage boy can get, even though his is so tiny! It’s great that he can express his sexuality around you openly.”

“Yes, it is. When he comes out of his room on Sunday mornings after he puts his hose on he always has an erection. He’s always been a little effeminate. It really didn’t surprise me when I caught him wearing my nylons. Our doctor told me I shouldn’t make a big deal about it, so I decided to encourage him a little to do it discreetly. The first Sunday of seventh grade I gave him a new pair of pantyhose and had him wear them under his good slacks. You can tell he likes it, he just acts so comfortable when he’s dressed in girl things. He just glows, he looks so happy! I was surprised how cute he is in them,” she laughed. “He leaves his hose on all day on Sundays. I have him put socks on over them if he goes outside, though, so he doesn’t run them.”

Char said, “And I just can’t get over how well he walks in heels! He’s obviously had a lot of practice. It’s great that you wear the same shoe size so he can wear your shoes. Do you think he’d like to wear panties to sleep in? I was going to go to the mall tomorrow. I was thinking of getting him a camisole to wear while he’s up here instead of boy undershirts.”

“I bet he’d love that.”

After I went to sleep, I dreamed that I was out on a date with that cute boy that had winked at me at the restaurant. I was wearing the same outfit I had on before, with the navy blue pantyhose and platform sandals. We were kissing and making out, and I was getting a boner. I reached inside my pantyhose and straightened it out, and said, “Sorry.”

He smiled and said, “Don’t worry, it’s OK.” We resumed petting and kissing, and he put his hand on my thigh and pulled me closer to him. I felt my slacks sliding over my panty hose, and I ejaculated.

I woke up in the darkness and found I really HAD ejaculated. I had a big slimy mess in my underwear. I pulled my undershirt down over it and snuggled back in the bed, thinking about how wonderful it would be if that would really happen, if I could be with a boy while dressed as a girl.

We went shopping again the next day. When we were in a store that had women’s and girl’s clothes, we went up there and Char picked out a package of girl’s panties and two white lacy camisoles. She held them up to me to check the size and said, “You’ll be so cute in these! You’ll love sleeping in them, too.”

That night before I took my bath, Mom came in with them and took the tags off of them and handed them to me. “Here, you can put these on after your bath and we’ll see how you look in them.”

After I dried off from my bath, I put them and on couldn’t believe the feeling. I walked out in the living room and Char said, “Look at you! I knew you’d be so cute in them. How do you like them?”

“Great,” I said, blushing. My dick was so hard, but the panties were hiding it, and I tried to think about something else to keep it from getting any bigger.

-----O-----

When we got ready to go home, Mom said, “Should we get dressed up for the ride home?”

“Sure,” I said.

“I have a surprise for you. Put on your panty hose and leave your cami on, and I’ll be right back.” I took off my sleeping panties and put my hose on. As I was pulling them up, Mom came back in the room holding something. She held it up and it was a dress!

“Char gave me this for you to have. Here, it goes on over your head.”

She gathered it up and put it over my head, and I put my arms in the sleeves as it slid down over me. It came down to just below my knees, and I couldn’t believe how nice my legs looked below the hem. She also had a half-slip, and held it up to me to see where the waist would have to be. “Step into the slip, and then pull up your dress,” she said. I did, and Mom pulled the waistband of the slip almost up to my rib cage. Then we let the dress back down, and it fit perfectly. “Wow, just look at you! Go look at yourself in the mirror while I get dressed.”

I walked out in the hallway and looked at myself in the mirror. When I first saw myself in a dress, it took my breath away. It was like the first time I saw myself in high heels, only better. I kept twirling around and looking at myself, not able to believe it. My dick was so hard, and I pulled up the dress to reach inside my panty hose to straighten it out.

Mom came out of the bedroom in a skirt, and we stood together in front of the full length mirror. All I could think of was that we were like a mother and a daughter. Mom said, “We’ll wear our shoeboots home. They’ll keep our legs warmer.”

Finally we sashayed down the hallway in our dresses to the kitchen for breakfast. Char said, “Sweetie, you’re gorgeous! I just knew you’d look great in that dress. Now you can’t go out all dressed up like that with those chipped nails. You’ve got to let me do your nails before you leave.”

After breakfast Mom and I went in the bathroom to try to do our BMs. Mom said, “Now pull up your dress and slip, and pull down your panty hose. Hold on to your dress and slip so it doesn’t go into the toilet.” I did, and then settled down on the toilet for my push job. It was really big and smooth, such a welcome change from when I was constipated. I moaned in pleasure as it slid through my rectum and dropped into the toilet. “All done?” Mom asked. “Ready for me to wipe?”

“Mmmm-hmmm,” I said, leaning forward. Mom rolled off some toilet paper and ran it up my crack.
Looking down, she said, “Wow! You really did a lot.”

“I’m still getting caught up from earlier in the week,” I giggled. I pulled up my hose and smoothed down my dress and slip, and flushed. Mom pulled down her skirt and hose and sat down on the toilet while I combed my hair and refreshed my lip gloss.

Afterward, we were sitting in the living room talking, and Char came in with her nail stuff. We talked while she took off my old polish and put on new.

“So did you do your poo this morning?” Char asked.

“Mmmm-hmmmmmmm,” I said.

“Boy did he ever,” Mom smiled. “We both had a really good BM.”

“Good. We don’t want you to get constipated again from that long car ride, like last week.”

After waving my hands in the air for a while to dry it, it was time to leave. I went in the bathroom to go potty before we left, I looked at myself in the mirrors, and could see my suntan nyloned legs below the hem of my dress. I felt so sexy knowing that I was going to be in a dress all day! I renewed my lip gloss and then we went downstairs to the back door. We sat on the couch and put on our shoeboots. As always I loved the feeling of sliding my hosed feet into them and zipping them up, and then we said our goodbyes. When Char hugged me goodbye, she whispered in my ear, “Bye Bri-anne, next time we’ll try you in some other cute things.”

When we went out to the car I was surprised how cold my legs were. After we left, I was shivering in the front seat. Mom noticed and said, “Cold?”

“Mmmm-hmmm. My knees are cold. I’m glad I wore my boots.”

“Now you know what we women go through. That’s the down side of wearing a dress. Maybe I should have had you put tights on instead of panty hose.”

“It’s OK. I’d rather wear nylons.”

“Yes, you’re a little old to be wearing tights with a dress. You do look so pretty and grown up in a dress and hose.”

“Thanks,” I said, blushing, still not believing that I was wearing a dress out in public.

We started having our usual Sunday morning girl talk on the drive home. We were talking about how constipated I was on the trip, and I said, “I was so embarrassed when I was sitting on the pot trying to go poop in front of you and Char, and my…. faucet got so big and hard.”

“I noticed that too, but didn’t want to mention it and embarrass you,” Mom said. “I thought it was maybe because you had hose on and that was exciting you.”

“I’ve noticed that when I’m constipated and trying hard to go poop, that it gets hard like that. Why does that happen?”

“I don’t know,” she admitted. “Boys have a gland called their prostate that has to do with sex, and it is close to your rectum. Perhaps when you’re constipated and your rectum has a big hard stool in it, it’s pressing against your prostate and exciting you.”

“It gets big on Sunday morning when I have hose on and I’m trying to go poop. I thought it was just because I had pantyhose on.”

When we stopped for our first bathroom break, Mom said, “You’ll have to go in the ladies room with me. Don’t talk to anyone, and be sure you sit down to pee.” I felt so sexy walking into the ladies room in my dress. I strode purposefully over to the first empty stall and locked the door behind me. I pulled up my dress and settled on the toilet, making sure my dick was pointed down so I wouldn’t pee all over. I couldn’t believe I was sitting in a ladie’s room in a dress, going tinkle! I made sure to roll off some toilet paper and wipe myself too before I flushed.

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 -- Tracy

I had been a member of the Young Organist’s association for several months, and our winter concert season was getting close. At one meeting, I noticed my mom talking to the other mothers about something, and on the way home, Mom mentioned that they had been talking about performance outfits.

“The other girls are going to wear their red blazers over a white turtleneck top and a white skirt, with white pumps,” Mom said. “You probably want to wear white slacks instead of a skirt, but we should get you some white heels like the other girls so you match.”

“Can’t I wear a skirt too?” I asked.

“Well, that’s probably over the line, but at least you’ll get to wear heels. Of course you’ll have to wear hose too, and it’ll be showing,” she laughed.

“When are we going shopping?” I asked, trying to keep from sounding too eager.

“Maybe Wednesday night after your music lesson,” she smiled.

Wednesday afternoon when she picked me up from school she was really happy.

“Ready to go shoe shopping tonight?” she asked.

“Sure,” I smiled.

“You need to put hose on so you can try on ladie’s shoes. If you want to get really dressed up, wear your white boots and your white turtleneck with a pair of jeans. That way we can make sure the shoes are the right shade of white.”

I went in my room and totally undressed. I got a pair of beige pantyhose out of my dresser drawer and slid them sensually up my legs, totally enjoying the feeling as my dick hardened into a huge erection. I got out my tightest blue jeans and pulled them on, then got out my white turtleneck and slipped it over my head.

I took my white boots and walked out into the family room. Sitting on the sofa, sliding my hosed feet into them, Mom looked at me and said, “That’s a cute outfit.”

We went to the Montgomery Wards store in the mall, walking past several other shoe stores, and I asked why we didn’t stop at them.

“White shoes are out of style in the winter, so not many stores will have them now,” Mom said. “Wards’ has a bridal department, so we’ll have to look there for them. We’ll try to find you some white slacks too. I couldn’t find any in boy’s or men’s, so we’ll have to get you a pair of women’s. They won’t have a fly, so you’ll have to go in a stall and pull them all the way down when you go to the bathroom.”

We went into the bridal side of the shoe department at Wards, and we looked over their selection. They had a classic white pump that was really pretty, but it had a 2 ½” heel. Mom picked it up and looked at it, saying, “This is what I had in mind, but I don’t know if the heel will be too high. We’ll have to see how well you can walk in them.”

About this time the saleslady came over, and Mom said, “Can we see these in a 9?”

“Sure”, the saleslady said, disappearing in the back. Mom looked at me and said, “Go ahead and take off your boots.”

I sat down and took them off, stretching out my toes in my hose and feeling my dick start to get hard again, when the lady came out of the back and sat down in front of me. She opened the box and took out the shoes. They were so pretty. I couldn’t believe they were for me! She slipped them on my feet, and I couldn’t believe how pretty I felt. She looked at me and said, “Stand up and walk around so we can see how they fit.”

The moment of truth. I stood up carefully, and walked away from them toward the mirror, carefully walking heel-to-toe. I caught a glimpse of my feet in the mirror as I was walking toward it, and my eyes nearly bugged out when I saw how sexy my own feet looked in hose and pumps. I stopped in front of the mirror and just stared at my own image.

“Okay dear, now back this way,” the salesgirl said, breaking my reverie.

I did better walking back, and walked past them and over to the other side of the room, marveling at how sexy I felt.

“Are those her first pair of heels?” she asked my Mom. “She walks really well in them.”

“Pretty much,” Mom smiled, knowing that it was her son walking in them.

Looking at me, Mom said, “What do you think? Can you play in them alright?”

“Sure,” I said, breathlessly. I couldn’t believe we were actually going to get them for me. After having them on, I was in love. I couldn’t bear to give them up!

“We’ll go with them then,” Mom said to the salesgirl. She added, “Why don’t you wear them home, so you have a chance to get used to walking in them?”

Oh My God! I thought. Here in the mall! “Okay,” I said, trying to keep my voice from shaking.

After Mom paid for them, she said, “Now we’ll go over to Misses and see if we can find you some white slacks.”

We went over to Ladie’s Fashions and into the Misses’ Department. We found the slacks section and found some in white. Mom took several pairs off the hangers and held them up to me.

“Looks like you’re a size 2 but we’ll have to get you a size Tall if you’re going to wear them with heels.”

She found a pair and steered me into the changing rooms. I couldn’t believe we were going into the Women’s! I stepped out of my heels and slid my jeans off. As I pulled the girl’s slacks on, they were so sheer and light, sliding over my pantyhosed legs. I stepped back into my new high heels and looked at myself in the full-length mirror. I felt so pretty, I couldn’t believe it! I couldn’t stop staring at myself in the mirror. I wanted them so badly!

“So what do you think?” I asked Mom as she was looking at me. “They’re awfully sheer. Your pantyhose panty is showing through them. We’ll have to get you sheer-to-the-waist pantyhose to wear with them.”

After she turned me around a few more times and looked me over, she said,” I think they’ll be OK. I won’t even have to hem them. Go ahead and put your jeans back on.” I hated to take them back off, but I did, putting my jeans back on with my pretty white pumps.

We took them to the counter and paid for them, and then walked out in the midway of the mall. We detoured into Osco drug and went over to the No Nonsense display. I couldn’t believe it. My dick was so hard and quivering if I had dared touch it I would have ejaculated.

As we looked at the Size B Sheer To Waist selection, Mom said, “You want either beige or nude so they match your skin, that way it looks like you’re not wearing anything at all. We’ll get a pair of each and see which matches your skin the closest when you have them on.”
She picked out a pair of each and handed them to me, then we walked over to Cosmetics and she got me some light pink nail polish. As we were waiting in the checkout lane in my high heels, with the bright orange pantyhose packages in my hand for all the world to notice, I felt so girly!
I
walked carefully out to the car, but by now, I was getting used to the heels. I couldn’t stop staring at my feet all the way home, and I think Mom noticed too. “How are your shoes fitting?” she asked.

“Great,” I said. “They’re so nice and soft inside. They feel great on my feet.”

“That’s because they’re women’s. The linings inside are softer so they’re easier on our feet and nylons.”

When we got home, Mom said, “Why don’t you practice your concert pieces to see how your new shoes affect your playing?”

I sat down at the organ and started playing. Actually the pointy toes steered my toes in between the pedals better. As I got done, I wondered what it would feel like to play with the girl’s slacks on. I went into my room and took off my jeans, then I pulled up my sagging pantyhose and then slid on the ladie’s white dress slacks. Looking down, my penis was leaking semen, and I was afraid I would stain my slacks. I got two Kleenexes and put them over the head of my dick before pulling my pants the rest of the way up. Stepping back into my shoes, I couldn’t believe how sleek and feminine I felt. I bent my leg at the knee and pulled it up to my other thigh to see how pretty and smooth my bottom looked. Mom was right, I could see my pantyhose panty showing through. I could hardly wait to try them with my new sheer-to-the-waist hose.

I sashayed back out into the living room and practiced some more. I felt so girly, I could hardly wait to wear them out and perform in them!

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 -- Tracy

I couldn’t wait for the first concert, but the day finally came. I took a nice long hot bath and shaved my legs nice and smooth. Afterwards, I went into my room and totally disrobed. I got out my new No Nonsense Sheer To Waist Panty Hose that Mom had gotten me and laid the package on the bed, immediately getting an erection when I thought of putting them on. Mom had gotten me some bright pink nail polish too, and I put two coats on my toes, making them look so pretty. After a few minutes to let them dry, I took my new pantyhose out of the package. Gathering them up, I carefully put the toe seam over my toes just like Charlene always did, and then sensually pulled them up my legs. Posing in front of the mirror, I couldn’t believe how sexy my legs looked. I sat back down on the bed and painted my fingernails, lazing around my room while they were drying, crossing and uncrossing my pretty legs in my pantyhose, unable to stop looking at my nyloned legs and feet, and getting aroused every time they touched together and I was conscious that I had hose on.

As I was taking my white turtleneck top off the hanger and was putting it on, I started to get the urge to do my push job. I hadn’t had one for a few days, so I knew it would be really big and take a while. I pranced into the bathroom, pulled down my panty hose, and sat down on the toilet. I sat there trying to go, pushing as hard as I could, but it just wouldn’t budge. Finally I gave up and went over to the sink and put some soap on my finger. I bent my knees slightly and slowly inserted my finger into my butt and felt the tip of a huge rock hard turd. I stood there, thinking about how much it was going to stretch me out when it finally passed. I pulled up my hose, washed my hands, and went back into my room.

I was getting my white slacks out of the closet when Mom knocked on the door. “Sweetie, it’s getting late. Are you almost ready?”

“No, mom, I’m still getting dressed. I did my nails first. I’m just putting my slacks on now.”

I stepped into them and slid them up my smooth pantyhosed legs, enjoying every inch. I stepped into my new white high heeled pumps and put on my red YOA blazer. I opened the door and walked out into the family room. “There,” I said, “How do I look?”

“Oh you look so nice,” she said, after looking me over head to toe. “You look so grown up!”

We put on our coats and headed out to the car. As we were driving to the concert, I started to have stomach cramps, and was holding my stomach to try to relieve them.

“What’s the matter, honey? Aren’t you feeling well?” she asked.

“No,” I said. “I’ve having stomach cramps.”

After a pause, she asked, “Are you nervous, sweetie?”

“No, that’s not it.” I sighed. “I’m constipated. That’s why I was running late, I was in the bathroom trying to do my push job, but I just couldn’t go.”

“Mmmm,” she said. “Is your stool hard?”

“Yes, and really big. I was straining as hard as I could and it still wouldn’t come out. It’s almost like my….. hole is too small for it to come out.”

“Sounds like you need some Correctol. We’ll stop on the way home and get you some.”

The concert went well. When we first got there, I noticed several of the other girls staring at my feet. We started comparing our shoes and telling where we got them. When it was my turn, everyone was looking at my feet, and I said, “Wards, my mom said that since it was winter, nobody would have white shoes in stock so we had to go to their bridal department.”

Lisa said, “Wow, have you got hose on? You look really nice!”

I rotated my ankle, and said, “Oh thanks! They’re No Nonsense Sheer To The Waist.”

“Are those ladie’s slacks?”

“Mmmm-hmmm. We got those at Wards too.”

When it was my turn to perform, I walked across the floor after they announced my name and I could feel everyone’s eyes on me and I hoped they wouldn’t laugh at a boy in high heels. It felt like I had to walk a mile to get to the organ. I was reminding myself to walk heel-to-toe like a girl, and trying to remember the first few notes of my music so I could get started. You could hear my high heels clicking across the floor as I walked and I could feel my slacks sliding over my panty hose and I got a HUGE hard on. I was so glad the blazer was buttoned so no one could see it! I could barely keep my mind on playing, and I was so relieved when I was done. I walked back to my chair, heels clicking all the way, and sat down and crossed my legs, feeling SO girly.

After the concert, we had our business meeting in another room of the nursing home. The other girls took off their heels, and so did I. I felt so grown up because I had sandalfoot hose on, and most of the other girls were wearing reinforced toe. I sat next to Joanne, the youngest member of our group. She had a long white skirt on, and reinforced toe pantyhose with white sandals. I noticed her staring at my feet in hose, and after the meeting, when we were talking about other things, she said, “You look really nice. I’ve never seen a boy wear nylons before.” After a pause, she asked me, “Have you got pantyhose on or just knee-highs?”

I said in my most grown-up voice, “I always wear pantyhose with dress slacks so they slide over my legs better and I look smooth, since I don’t have to wear underwear then. They stay up better than knee-highs too. I have to wear sheer-to-the-waist with these white slacks so the panty part wouldn’t show through.”

“You’re lucky,” Joanne said. “My mom just gets me the cheap ones from K-Mart. I couldn’t wear my mom’s. She has to have queen size,” she giggled. “These always are falling down around my ankles and I’m always pulling them up. Yours always look so nice. I never see you pulling yours up.”

“My mom gets me No Nonsense,” I said. “If you want better quality ones, why don’t you buy them on your own?”

“That’s a good idea,” she said. “I guess I could take my babysitting money to the store and get my own.”

Lisa, another one of the girls, had gone to ask her mother a question about our next concert. When she came back in the room, her face was red with embarrassment.

“Lisa, are you OK?” I asked.

She whispered angrily, “You can’t believe what our moms were talking about!”

Joanne and I looked at each other, and Joanne asked, “What were they saying?”

Lisa hissed, “They were talking about what they give us when we’re constipated! I was SO embarrassed!”

Now it was my turn to blush. “Well,” I said, “that’s probably my fault.”

“Why?” Lisa asked.

“Well, on the way over here, I had told my mom I was having stomach cramps because I couldn’t have a BM.”

Joanne smiled and said, “Well, actually, I’ve been having problems too. On the way over here, Mom said that she’s giving me an enema as soon as we get home. So what does your mom give you, Lisa?”

Lisa blushed harder and looked down at her lap. “Ex-Lax. She gave me some last night,” she whispered, and then giggling, said, “Well, I guess THAT’s why they were talking about it!” We all laughed!

On the way home, we stopped at the drugstore. Standing there in the laxative aisle, there were a couple of teenage girls that saw us, and were staring at my feet in my high heels and hose. Mom took some Correctol off the shelf and handed it to me.

She said, “You’re so thin and delicate, you’ll have to take a woman’s laxative. Correctol is really gentle and it also has a stool softener. It’ll make you need to have a BM without giving you cramps, and it’ll help a hard BM pass through your bottom easier without hurting.”

“That’s good,” I said, grimacing. “When I was trying to go earlier today my stool was so big and hard.”

Mom reached down and picked up a Fleet Enema. “Do you want me to get you a Fleet as well? That way you can get relief as soon as we get home.”

“Yes, please,” I said.

She asked, “How long has it been since you’re had a BM?”

I thought a moment, and then said, “Three days, I think.”

We walked past the girls again on the way to the checkout, with our high heels clicking and a box of Correctol in my hand, and a Fleet Enema in Mom’s. I heard them giggling, and then one said, “Oh my GOD,” and they all started laughing. I felt my face turn red, but I just kept walking heel-to-toe and ignored them. They didn’t faze Mom at all. My erection was so big I could hardly walk. I looked down and was glad to see the blazer was buttoned and covering it up.

When we got home, Mom said, “Take off your blazer and your slacks, but leave your hose on.” I stepped out of my pumps and went into my room. I took off my blazer and hung it up, then slid my sheer slacks down and off my legs. As I was hanging them up, Mom came into my room with the Fleet Enema in her hand. “You’re old enough to learn to give yourself an enema,” she said. “Pull down your pantyhose and lay on your left side,” she directed.

I stretched out on the bed, my rock-hard erection clearly on display. “Bend your right knee up partway to help open up your bottom.” I did, and she sat down next to me and handed me the enema. I opened the box and took it out. “First, remove the cover,” she said. As I did, she said, “Pant like a puppy dog to relax your muscles. Now carefully insert the tip up into your bottom. Point the tip towards your belly button as you do.” It slid easily into my bottom.

“Okay,” I said.

“Now squeeze the bottle to put the water up into you.” I did, and you could hear the water gurgling up into me. I was afraid I was going to ejaculate. “Now pull it back out and put the cover back on the tip.” I withdrew it, and saw the tip was brown from my poop before I put the cover back on it.

“Now just lay there for a little bit and let it work.” She smiled at me and stroked my hair while I laid there.

After a minute, I felt a cramp. “Oooh,” I said, “I think I feel something.”

“Wait till you have to go really bad,” she said. All of a sudden I felt like I had to go. I pinched my bottom together to hold it. The urge receded, then got strong again, then got REALLY strong. I said, “I think I better get in the bathroom.”

I jumped up, quickly stepped back into my white pumps, and ran to the bathroom, followed by Mom. I settled on the toilet and relaxed my muscles, and water started coming out of me. A few seconds later my stool was ready to come out. I bore down and it finally slid out of me and splashed into the toilet. I bore down some more and pushed what felt like a gallon of water out of me. I sighed and relaxed. Mom sat down on the tub and sat there for a while as the rest of the water dribbled out of me. Finally she said, “Ready for me to wipe?”

“Yes,” I said, and leaned forward so she had access. It took several times to get me clean. Finally she flushed and I stood up and pulled up my nylons.

I went back in my room and put jeans on over my hose, leaving my white turtleneck on. After having heels on all day, I found myself walking heel-to-toe up on the balls of my feet, even after taking them off. I started exaggerating it whenever I walked. It felt so prissy and girly when I walked that way! I went back out into the family room where Mom was reading the paper. I sat down in the chair, feeling so empty and relieved.

“Wow, I really feel better,” I said.

“I bet you do, after as much as you pooped. Now you know why you can’t let yourself go when you’re constipated.”

I lounged around the house the rest of the evening like that, getting aroused every time I looked down at my feet and nail polished toes in my sandalfoot hose.

Later that night, I heard my mom talking to my sister-in-law on the phone. “You should see our janeboy! He’s in this Young Organist’s group with a bunch of girls. They all wear white skirts and white high heeled pumps. I got him white high heeled pumps like the other girls, a pair of Misses’ sheer white slacks, and sheer to the waist pantyhose to wear under them so the panty wouldn’t show through.”

“Oh that’s so precious!”

“He painted his toenails, and you should see his feet when he has sandalfoot hose on. His feet are gorgeous! They were having a business meeting after the concert today, and he took his heels off along with all the other girls. He had the prettiest feet there! I heard one of the girls ask him if he had pantyhose on or just knee-highs! You should have heard him tell that he always wears pantyhose when he dresses up. And then guess what we did?”

“I had to get our little janeboy a laxative! Today on the way to the concert he was complaining that he was constipated. He hadn’t been able to go for four days and really needed help. After the concert we stopped at Osco Drug on the way home and I got him some Correctol. When we were standing there in the laxative aisle I told him he needed a woman’s laxative because he was so thin and delicate. I think he had an erection! There were a couple of teenage girls standing there that were staring at his high heels and giggling! I also got him a Fleet Enema, he said that his stool was really hard, and after we came home I showed him how to give it to himself.”

“I bet he was embarrassed! That’s so neat that you’re still janeing him!”

To be continued..............

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 -- Tracy

I got so used to wearing hose with the Young Organist’s outfit that I really missed it when I was wearing boy clothes. I noticed I was getting really used to walking like a girl and swinging my hips when I had heels on, and had to remind myself to walk like a guy after I took them off. After seeing women dangling their pumps off their toes when they were sitting with their legs crossed, I started doing it when my feet were pinching from wearing my heels for a long time, and it started becoming second nature to me.

The concerts were usually on Sunday afternoons, and on concert days, I would always put sheer-to-the waist pantyhose on in the mornings for church, so I’d already have my concert hose on when I changed for the concert. One morning, when we got home from church, I took off my church clothes and put on my white turtleneck and slacks. I walked into my mom’s room when she was changing her clothes and was standing there in her bra and nylons. I saw she was wearing sheer-to-the-waist hose too. “Mmm, you’re wearing sheer-to-the-waist too,” I giggled.

“Your feet are so pretty in those sandalfoot hose, I thought I’d try them too. When I was buying us hose the other day and I was getting you sheer-to-the-waist, I bought myself a pair too,” she said, as we walked to my bathroom.

After a concert, Lisa and I were sitting together talking. My legs were crossed, and when I looked down, my shoe was dangling off my toe – I didn’t even realize I was doing it, it was subconscious! She said, “Wow, you’re even dangling your shoe. You’re really turning into a girl!”

After a pause in our conversation, Lisa asked, “So, if you don’t mind me asking, how do you like wearing nylons all the time?”

I said, “I love the sleek feeling! Actually I’ve been wearing pantyhose with dress slacks since I was in junior high, when I get dressed up.”

"Your bottom is so smooth. You can tell you’ve got pantyhose on. You’ve got a girl’s butt,” she giggled.

“I know. I don’t wear any underwear when I have hose on,” I giggled.

She continued, “We were surprised you were wearing panty hose. We all thought you were just wearing knee-highs, and Jo volunteered to ask you. She was so surprised when you told her you had pantyhose on! So, what kind do you wear?”

“No Nonsense Sheer To The Waist,” I said. “My mom said I should wear hose with a sheer panty with these slacks so the panty part wouldn’t show through. Since I started wearing them she’s been buying me some every time she buys hose for herself. Once a month or so I go in my bedroom and find a new pair laying on my bed. What kind do you wear?”

“Legg’s. She gets me sheer toe, so they look better in my sandals.” She rotated her ankle around as we were looking at our shoes. “I love your white pumps, I bet they keep your toes warmer. Where did you say you got them?”

“Wards at Scottsdale Mall,” I said. We bobbed our feet a few more times, and she said, “What size do you wear?”

“Nine,” I said. “How about you?”

“Oh wow, I wear a nine too. Can I try on yours, if I let you try on mine?”

“Sure,” I said, slipping out of them. She undid the straps on her sandals and stepped out of them and handed them to me. Daringly, I put my feet into them and fastened the buckles while she stepped into my pumps. I was glad I had sandalfoot hose on.

We got up and started walking around in each other’s shoes. Her heels were a lot higher than mine and it took me a little while to get used to them, but I could really feel myself shimmying as I walked. Lisa said, “I’ve been meaning to ask you something. We have another white skirt like mine at home, and it’s about your size. Would you like to maybe wear it to the concerts? Then we’d all match!”

The thought was really tempting. While I was thinking about it, Lisa said, “I didn’t mean to embarrass you. You don’t have to if you just want to wear slacks and heels.”

“Actually I was thinking that would be really neat. You all have been so accepting of me wearing high heels,” I replied.

She lowered her voice and asked, “Have you ever worn a skirt out in public?”

“Mmmm-hmmm,” I smiled. “I have a sweater dress that my sister-in-law in Canada gave me. I wore it home from their house once. I had it on all day. It felt really neat! I also have a long skirt that my mom gave me, but I’ve never worn it out.”

Lisa said, “You’ll need a long slip with it too, I think we have one that goes with it. I just thought that, since you normally wear pantyhose anyway, you might as well wear a skirt along with the rest of us.”

About that time, the other girls came back from the restroom. They immediately noticed that we had each other’s shoes on, and started asking Lisa how they felt. Jo sat down next to us, crossed her legs, and asked, “So, what do you think of my No Nonsense?”

“They look great,” we all echoed. I asked, “So you bought hose on your own?”

“Mmm-hmmm. You seemed to like No Nonsense so well, they were on sale and I thought I’d try them.”

I could see her toes in her sandals, and she had sandalfoot hose on. “So you got sheer to the waist?”

“Mmmm-hmmm. Now I look grown-up like you guys!”

I noticed Shonda staring at my feet, and she asked Lisa, “You’re letting him wear your sandals?”

“It’s OK,” Lisa said, rolling her eyes, “He’s got hose on!”

“I know. I can’t believe how girly his feet are,” she giggled.

As we were leaving, I heard Shonda say to Lisa, “I can’t believe he is such a girl!”

“I know!” Lisa replied. “With those hose on under his slacks, he’s got a girl’s butt too! Isn’t he darling? We’ve got another long white skirt like mine that I’m going to give him. Won’t he look darling in a skirt? Then he’ll be a girl all the way!”

Our moms were talking on the other side of the room. Lisa’s mom said, “You know, Ruth, I have another long white skirt like Lisa’s that your son could wear if we wanted to. Then they would match exactly. I’m pretty sure it would fit him, if you want to try it.”

Mom smiled. “I’ll have to ask him. Why don’t you bring it along next time, and he could try it on?”

She replied, “I’ll do that. I think I have a slip that matches it too. I’ll bring that as well. Actually Lisa suggested offering it to him.”

On the way home, Mom said, “You know, Lisa’s mom said that she had another long white skirt like Lisa’s that would probably fit you if you wanted to wear a skirt to the concerts. Would you like to wear one?”

I said, “Yeah, Lisa mentioned that to me too. That would be really neat.”

Mom laughed, “You’ll have to learn to get in and out of a car in a long skirt.”

That night I had a wet dream. I dreamed that Lisa and I were sitting on my bed with nothing on but panty hose and high heels. We had swapped shoes again and I was wearing her high heel sandals. Our nyloned legs were touching and we were arm-in-arm, kissing deeply. We started rubbing our legs together and then we French kissed, and I ejaculated!

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 -- Tracy

Several months later, Char and Mom decided to swap kids for a month or two during the summer. I was so excited when I heard that – I could get to dress with Char! Unbeknownst to me, she had already told Mom, “I’ll have him in a skirt by the second day!”

The day before we left, Mom came home from the store with two bottles of Nair. She handed it to me and said, “You should clean up your legs in case you want to wear a skirt up there. Nair will get you a lot closer than shaving. Tonight after supper I’ll show you how to use it. You’ll probably want to shave your underarms too. I also got some extra for you to take with you, you’ll probably need to use it once a week or so.”

After supper I took a shower, and Mom showed me how to use the Nair, and how to not leave it on too long. I couldn’t believe how smooth and sexy my legs were afterward! Then we packed for me, putting in camis and panties to sleep in, and a few pairs of No Nonsense Sheer To Waist pantyhose for dress up. She went in the bathroom and got my Correctol out of the vanity drawer. She said, “I’m packing your Correctol, in case you get constipated on the trip like before.”

On the trip up, I wore shorts, and every time the sun shone on my Naired legs, they were so shiny and smooth! I kept running my fingertips over them. When we met Charlene in Windsor, we used the restroom, then small talked for a few minutes.

Mom said, “Last night I had him Nair his legs and shave his underarms, so he’s all ready for you,” as I blushed.

“That’s great,” Char said, smiling. “We’re going to have a lot of fun.”

We girl talked all the way back to Toronto. After we got to her house, we put my suitcase in the spare bedroom and she said, “I’ve got some cute things for you to wear. Want to see them?”

“Sure,” I said.

She opened a dresser drawer and pulled out some things. “I got you some cute girl’s shorts and a top and a training bra. I’ve got some low heeled sandals you can wear with them, they’re in the closet. Go ahead and put them on. After supper we’ll do your nails.”

I changed into the outfit, and walked down the hallway to the kitchen. I helped make dinner and clean up afterward, loving to hear the clicking my sandals were making on the hardwood floor. After dinner we went downstairs to the family room, where she was sitting on the couch with her nail things. I sat down and we made small talk while she trimmed my nails and then put two coats of pink polish on them. As I was blowing on them to dry them, she said, “Now take off your sandals and let me see your feet.”

I reluctantly took off my cute sandals and put my feet up in her lap, and she gave my toenails the same treatment. As I was looking at my nails and my legs, remembering what we had been doing for the last hour, she touched my smooth bare leg, and I ejaculated, gasping. I was so embarrassed. I stammered, “Um, Char, um, I think I have a big problem, I think I just made a mess,” unsnapping my shorts and opening them so I wouldn’t get anything more on them, and exposed my dripping dick, which made me even more embarrassed.

She quickly jumped up. “Don’t worry, just sit still and I’ll get a towel.”

She came back a few minutes later with a wet washcloth and a towel. She wiped my cum off of my tummy and dried me as I just sat there, paralyzed, not knowing what to do or say. When she was done, she said, “There, don’t worry about it. Now, what would you like to watch on TV?”

We snuggled together and watched TV for a while, with our smooth shaved legs touching. Finally it was time to go to bed, and I went up and changed into a cami to wear to bed.

I woke up the next morning with the sun streaming into my room. I laid there, just staring at my polished fingernails, thinking how great this day was going to be! Finally I got up and got dressed in my girl clothes from yesterday. This was a new feeling – casual girl clothes and not hose and high heels. After I put everything on, I looked at myself in the mirror and couldn’t believe how much I looked like a girl! It felt so sexy to wear a bra. I sashayed out into the kitchen where Char was making breakfast.

“Oh look at you! You’re adorable!" she said. "After breakfast we’ll get some makeup on you.”

After breakfast, she got dressed, and then called me into the bathroom. “You don’t want too much makeup on for casual, but some basics.” She showed me how to put on eye liner and shadow, and then handed me a lipstick. “Here, this is light pink, just the thing for casual.” She took out one of her lipsticks, and said, “Here, do it like me. We’ll practice.”

I quickly got the hang of it. When we got done, she said, “Now you need something to put your things in.” She went into her bedroom and came out with a small denim purse. “Here, put your lipstick and some tissues in here. Keep it with you at all times, don’t lose it,” she warned. “Ready to go have fun? I thought we’d go to the market first and go shopping, then maybe go to the park.”

We hung out all day and had so much fun. We were like sisters. Every time I looked down and saw our smooth shaved legs and our cute feet and our painted toes in our sandals, I felt so cute and sexy!

Later after dinner, she surprised me by asking, “So how would you like to come to work with me tomorrow? I asked my boss if you could help out, do filing and things like that. You’d have to get dressed up though, wear a skirt and hose.”

Wear a skirt and hose! Great! I smiled coyly, “OK, I guess.”

Around nine, we were starting to yawn. Char said, “Come on, I’ve got something a little different for you to sleep in.”

We walked back up stairs to her room, and she opened her dresser drawer and pulled out a short pink chemise, handing it to me. I went to my room and changed into it. A few minutes later, as I was admiring myself in the mirror, she knocked lightly and came in. “Ready for bed?” she asked.

“I think so, this has been such a fun day. I had a ball,” I giggled.

She turned back the bed, and motioned for me to get in. “Sweet dreams,” she said. “We’ll have fun tomorrow.” She kissed me on the forehead, then turned out the light and shut the door. I luxuriated in bed in the satiny smoothness of the nightie. My dick got so hard. I reached inside the nightie and slowly jacked off, exploding in passion as I came. As I drifted off to sleep I passed a small fart, and remembered that I hadn’t done my push job all day. I hoped I wasn’t getting constipated.

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

When I woke up the next morning, I could hear the sounds of a shower running. I fell back to sleep, but then woke back up when Char came in the room and said “Good morning!”

I rolled over and smiled at her. “Good morning to you, too. You look nice,” I said, as I noticed she had pantyhose on under her robe. She had another pair of hose in her hands, and she sat down on the bed, saying, “Time to get up. Here, put on your nylons and then come out in the kitchen and we’ll have breakfast.”

She stood back up and left, and I took the nylons in my hand. Pressing them to my nose, they smelled perfumey. I got up out of bed, stretching, and then slid my panties off. I gathered up the hose and slid them up my legs. I had never worn nylons with shaved legs before, and the feeling was just heavenly, my dick hardening into an erection so hard it hurt. They were sheer-to-the-waist hose, and I took care to arrange the toe seams exactly like Char‘s – one peeking over my big toe vertically, and the other over the little toes. I carefully pulled the wrinkles up out of them, and then walked to the kitchen, sliding my pantyhosed feet along the hardwood floor.

As I entered the kitchen, Char looked down at my legs. “Oh your legs look so nice. Don’t you feel sleek and sexy?”

“Mmmm-hmmm,” I replied, blushing.

“How do you like those hose? They’re Can-Can Sheer To The Waist.”

“They’re nice. Mom’s been buying me No Nonsense Sheer To The Waist. I bought a few pairs with me.”

We sat down at the table and had breakfast while we made small talk. Char said, “I have a beige sweater dress that I thought you wear with my beige high-heeled sandals. It’s mid-calf, so you won’t be showing too much leg your first time out in public.”

After we put the dishes in the sink, we went back to her room. Closing the door, she loosened her robe and shrugged it off her shoulders, and stepped out of it when it hit the floor. As she stood in front of me, nude except for her pantyhose, nipples erect, it was hard not to stare. She didn’t have any underwear on under her hose, so I chose correctly in taking mine off. I tried hard not to look at her crotch after seeing whether or not she had underwear on, but couldn’t help but notice her neatly trimmed pubic hair. She noticed my unease and smiled. “C’mon, off with your jammies, so we can get ready.”

I pulled the pink chemise over my head and off, laying it on the bed. There was an awkward moment as we both stood there in our nylons, topless. She walked over to her dresser and pulled out two bras. “Here,” she said, handing me one. “Since we’re getting dressed up, I thought you might like a little more….. up top,” she giggled.

We put on our bras, and she reached inside hers to locate her breasts correctly. She reached back in her underwear drawer and took out two pairs of hose that had knots tied in them. She rolled them up and stuck one in each of my bra cups. “These are old ones that have runs, that I wear under slacks, but they’ll give you some boobies.”

Next, she pulled out two full slips. “Here, you wear the longer one, since you’re going to wear the longer skirt.” We pulled them on and got them arranged correctly. The feeling of more nylon sliding over my pantyhosed and shaved legs was breathtaking, and my dick started to get hard again. She opened her closet and took out a hanger with her sweater dress on it and handed it to me. “Here, you get dressed while I’m picking something out.”

I went back to my room and took the top and skirt off the hanger. I put the skirt on first, pulling the waistband up to my navel, then pulled the top over my head. I pulled up the skirt and pulled down the slip. There was a full-length mirror on the wall and I was admiring myself when I noticed my big hard dick poking through all the layers. I pulled the skirt and slip back up, and, pulling down the pantyhose panty far enough to tuck my dick in as firmly as I could, then smoothed everything back down.

I kept admiring myself in the mirror, trying different poses, when Char called out, “Come on back in the bathroom and let’s put some makeup on you.”

I walked back in her room and there she was in an above-the-knee pink skirt and a white blouse. She steered me into the bathroom and started on my hair, parting it in the middle and then flipping it back and securing it with some hairspray. She touched up a few spots on my face with foundation and then dusted me with face powder, followed by some rouge on my cheeks. Finally, she handed me a lipstick and said, “Go ahead and put on lipstick. This one’s a little darker color so it’s a little more dressy.”

I did, and couldn’t believe how feminine I looked. We walked back into her bedroom and she got some clip-on earrings out of her jewelry box and clipped them on my earlobes. Finally, she reached into her closet and handed me a pair of beige high-heeled sandals. “Here, to top it all off, your heels.”

I went in my room and put them on and fastened the buckles, then got my purse and put the lipstick in it. She stuck her head in the door and said, “Ready?”

We walked together out to the car, and I felt so sexy feeling the light breeze on my legs in the skirt.

When we arrived at her office, she introduced me to everyone as her niece, Brie. Everyone remarked how nice I looked, and then we went back to her office. Char said, “I have some filing that you could help me with. You can sit at that desk over there by the filing cabinet and I’ll get you started.” Lowering her voice, she said, “And cross your legs when you’re sitting there, and notice how all the guys stare at your legs when they walk past.”

She was right – the guys were checking out my legs that day. We took a few breaks to get a soda and fix our lipstick, and use the bathroom. I was feeling the urge for a BM, and tried to push it out, but it was stubborn and wouldn’t move. I didn’t try too long as I didn’t want to tie up the bathroom. Later that afternoon, as we were driving home, the urge to go was getting really strong. As we turned down our street, I said, “Thank goodness we’re almost home. I’ve been feeling like I need to do my push job all afternoon.”

I went directly to the bathroom as soon as we got in the house. I pulled up my skirt and slip, and pulled down my nylons and sat down on the pot. I relaxed and started to push, but my poop wouldn’t move no matter how hard I tried. I grunted and strained, but it wouldn’t even start to come out. I wondered what to do next. I put some soap on my middle finger, and inserted it up in my rectum, and could feel my big hard stool. With my finger up in me, I took a deep breath and really pushed hard, but it still didn’t move. Finally I gave up and got up and got dressed again.

As I walked back in the kitchen Char said, “Feel better now?”

“No,” I moaned, “I’m constipated. I think I need some Correctol.”

She said, “When was the last time you did your job?”

I said, “I don’t know. I haven’t had one since I’ve been here.”

She said, “We’ll have something for dinner with some fiber in it to give you some help. Then you can take your Correctol before you go to bed. If you like, you can take off the skirt and slip, and just put your jeans on over your hose. I thought we could go shopping after dinner, and you need to have hose on when you try things on. We should get you some dressy teenage girl clothes, and you really need girl jeans.”

I went back to my room and took off the high heels, then the skirt and the slip, and put on a pair of jeans over the hose. It felt so sensual, feeling my pantyhosed legs sliding against the legs of my jeans. It was a relief to take off the high heels, so I left them off and went back in the kitchen to help Char fix dinner.

After dinner, Char changed out of her skirt into jeans too, and we put our heels back on. We went to the big mall near her house. My jeans were fairly tight on me, probably from the constipation bloat, and I felt so sensual as I walked from the car into the mall, swinging my hips as I walked in the heels, and swinging my purse from my hand as I walked.

We stopped in front of a teen store right inside the mall, and there was a mannekin showing off a cobalt blue turtleneck sweater top with a short white miniskirt and cobalt blue pumps. Char said, “You’d look so cute in that! Let’s try it on you!”

The salesgirl picked it out for us as we walked back to the fitting rooms. Char went inside with me, and I sat down to take off my heels. Standing up, I slid the jeans down and off, and pulled the wrinkles up out of my hose. Char handed me the skirt, and I slid it on. It felt like it barely covered my butt. I pulled the sweater over my head and pulled it down. Char said, “Very nice, but you’d better re-tuck.”

I slid my hand down inside the skirt and the hose and pushed my dick down all the way between my legs, then pulled the skirt and hose back up. I walked out to the full length mirror, and couldn’t believe how cute I looked. About that time, the salesgirl came back with the pumps, and I slid my feet into them.

“Wow,” Char said, “You look awesome.”

I walked away from the mirror and back, getting used to the higher heels, and as I looked back at myself in the mirror, I noticed that the skirt had a slit in the back that was partly unbuttoned, and you could see almost all the way up to my crack. I couldn’t believe how sexy I looked and felt.

Char noticed, too. “You are really going to have to beat the guys off with a stick. You look so hot!”

I couldn’t stop looking at myself in the mirror. I didn’t want to take the outfit off because I was in love with how I looked. Finally, Char said, “Well take it off now, but that one’s definitely going on the keep pile.”

“How much does it cost?” I stammered. I didn’t think I had enough money to pay for all of it.

“It doesn’t matter,” she said. “It’s my treat. I’ve been wanting to dress you up like this for a long time.”

I put my other clothes back on, and we looked through several other stores, but didn’t find anything as awesome as that outfit. We did find a pair of girl jeans that fit me really tight. When I came out of the fitting room with them on, I said, "They're nice and tight but I think they're too long."

"That's OK," she said, "You need them long so you can wear heels with them. You can tuck them up on the inside if you're not wearing heels."

At another store, we found a short denim miniskirt that Char said “I could wear with anything,” and then she bought me several pairs of pantyhose of my own, since, according to her, “You’ll be wearing nylons all the time now.”

When we got home, Char’s neighbor Linda and her son were outside on their porch. We walked over there and Char introduced me to her and her son, Jason. We stood around while Char and Linda talked, then Jason looked at me and said, “Want to go inside and hang out?”

“Sure,” I said. We walked inside their house and into the family room, my high heels clicking across the hardwood floor. We sat down and watched TV for a little while, then turned it off and started talking. I tried to fake girly conversation as much as I could. I noticed Jason staring at my feet a lot, and at a pause in the conversation, he said, “You look really nice. You’re wearing nylons, aren’t you?”

“Mmmm-hmmm,” I replied, bending my foot around at the ankle to show it off. “I wore a dress today to go to work with Charlene, and I haven’t taken the nylons off yet. The hose,” I added delicately, pointing my toe at him. He was wearing sweat pants and I could see his erection straining against them. It was so cool that I was turning him on, and I was starting to realize the power that women had over men.

Finally, Char came in and asked if I was ready to go. I said good-bye to Jason and we walked back over to our house. As soon as we got inside the door, Char looked at me and said, “Wow, did you see the way that Jason was looking at you? He sure is attracted to you!”

“I know,” I replied, giggling. “He had this great big boner and I could see it sticking through his sweat pants. It made me feel really attractive that I was turning him on.”

Char said, “Wait till you wear that outfit we bought for you tonight. You will turn a lot of heads,” as she touched my hair. “C’mon, let’s put our jammies on and go watch TV.”

“Okay, I think I’m going to go sit on the pot again.”

I went upstairs into the bathroom, pulled down my jeans and pantyhose, and sat down on the toilet. I sat there, admiring my pretty pantyhosed feet in my high heeled sandals and flexing my toes. I pushed for a while, but still nothing would move. About the time I was ready to give up Char knocked on the door and came in. “Any luck?” she asked.

“No,” I sighed.

My high heels were pinching again so I took them off before I got up off the toilet. I loved walking on the hardwood floors in hose, sliding my feet along and feeling the nylons between my feet and the floor. I went to my room and changed out of my clothes and put on panties and Char’s pink nightie. I opened my suitcase and got out my Correctol, and went in the bathroom and drew a glass of water and took one before I went back downstairs. Char was sitting on the couch in her nightie, and she raised her arm and motioned me to come sit beside her. I pulled my nice smooth legs up and snuggled up next to her. I was getting tummy cramps, and I started pushing on my stomach to relieve them.

Char flipped my bangs over and said, “Don’t forget to take your Correctol.”

“Mmmm, I just did,” I grunted, laying my head on her shoulder. “I’m so bloated.”

She said, “You’ll feel better in the morning after a good BM. I can’t get over how pretty you looked today. You make a beautiful young woman. Even at the mall tonight, in jeans and high heels, there were guys looking at you as we walked past. I can’t believe how well you walk in heels! It’s like you’ve been wearing them all the time!”

The thought of guys finding me attractive was really exciting. I remembered seeing Jason get an erection when he was staring at my pantyhosed feet in my high heels, and how pretty and attractive it made me feel.

We dozed off together when the show got boring, and after we woke up, we turned off the TV and walked upstairs to bed, hand in hand. I had such a hard-on, and had a wonderful masturbation session while remembering all the events of the day.

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. After a few days at my sister-in-law’s, she decided to turn things up a few notches -- Tracy

The next day, when I heard Char getting ready, I got up right away. I got out a pair of my new pantyhose, opened them up and put them on. I put the bra back on that Char had given me yesterday, stuffing it with her old nylons. I got several pieces of Kleenex and put them over the head of my dick to keep my semen from staining my clothes. I got my new white skirt out and, just to be daring, unbuttoned one of the buttons on the back slit before putting it on. Finally, I got out the new blue sweater and pulled it on. I was standing there in front of the mirror, admiring my long legs in that wickedly short skirt, and my cute nailpolished toes in my pantyhose, when Char came in.

“Couldn’t wait to try on your new outfit, could you?” she said, smiling. “You look even better than last night! Wait till we put some makeup and jewelry on you!”

We went out in the kitchen and had breakfast. Char poured me a bowl of bran cereal and said, “You should have some more fiber in your diet to help you poop.”

“Okay, you’re probably right,” I said, blushing. After we cleaned up the breakfast dishes, she said, “Why don’t you go sit on the pot for a while and try to go poop. We have plenty of time, so just go sit in there and relax and let the Correctol work. Put on your high heels first, that will make it easier for you to go.”

I could tell it was working because I had held back a couple of farts already, and was feeling like I had to go. I went in my room and stepped into my new heels, and clipclopped across the hall and into the bathroom. Char was in there putting on her makeup, and said, “Go ahead and sit on the pot while I do my makeup.”

I pulled down my skirt and panty hose and sat down on the toilet. We were talking girl talk, passing the time, when my urge to go got strong and I started to push. Even though my poop was really big and firm it was really slimy and slippery, and it slid right out of me without too much effort. “Wow,” I said. “The Correctol makes it so much softer and easier,” I added.

She replied, “That’s because women’s laxatives have a stool softener in them. They make you have a really smooth and easy BM.”

I wiped and flushed, then pulled up my panty hose and skirt. “I feel a lot better .”

She patted my tummy and said, “Your tummy is flatter too. We girls really have to stay regular. It helps our waistlines and our figures. Now, it’s my turn,” she said, and slid her skirt and hose down to her thighs and sat down on the toilet. I started checking out my makeup in the mirror and tried not to look at her as she was doing her BM. I heard her grunt a little, and then the crackling sounds as she passed her stool.

We went back to the mirror and put on our makeup. I did better this time as she showed me how to do it. She handed me a pair of big hoop earrings to put on, and while I was admiring them in the mirror, she came up from behind me with a bottle of perfume, raised my hair up, and put a spritz on both sides of my neck. It smelled so nice! Afterwards, when she was standing next to me, she fiddled with my hair, and as she dropped her hand down, I felt her fingertips graze over my bottom. I didn’t know if it was on purpose or not, but it really got me excited.

We had an interesting day at work, including going out to the mall for lunch. I noticed a lot of guys staring at me as we walked past, and one even whistled at us! Char just looked at me and smiled. As we were walking to the car after lunch, I felt the breeze on my legs and up into my crack, and I felt so sexy! It felt so natural and content to be dressed like this.

After we drove home, as we pulled up in the driveway, we saw Linda and Jason outside again. As she shut off the car, Char looked at me and said, “Want to have some fun?”

“Sure,” I said.

“When you walk past Jason, play hard to get. Just say ‘hi’ and nothing more, then walk into the house. It’ll drive him nuts.”

“Okay,” I said, smiling wickedly. I got out of the car the girl way, putting my high heeled feet on the ground first, then stood up and pulled the miniskirt down slightly. I closed the car door and sashayed my way into the house, and just briefly said “Hi” as we walked past. After we got inside, Char looked at me and said, “I’ll bet you any amount of money he’ll be over here tonight asking you out.”

I said, “I can’t go on a date. I’m not old enough.”

She replied, “Oh, I bet we could arrange something, if you really wanted to go.”

We went upstairs and made dinner. Dinner was strangely quiet -- Char kept looking at me and smiling, and I smiled back. While we were having dessert, I felt something touch my leg, and when Char giggled, I realized it was her barestocking toe running up and down my pantyhosed leg, and I started to get aroused. When she stopped, I reciprocated, and she closed her eyes and exhaled deeply, moaning softly and shifting in her seat. I wondered if she was getting turned on too, when she abruptly opened her eyes, stood up, and said, “Come here with me for a moment.”

She walked down the hall to her bedroom, and sat down on the bed, motioning me to sit beside her. She crossed her legs, and I did too, and we started to bob our feet up and down in unison. I stared at our pantyhosed toes while remembering how incredibly sexy and feminine I had felt all day. She laid her hand on my shoulder and gently turned me toward her. I started to ask her what she was doing when she closed her eyes and brought her face close to mine in the classic pre-kiss tilt. I tilted mine the other way to match and our lips met. We kissed for what seemed an eternity until she moaned softly and we parted. Now I was sure that her running her fingertips over my bottom this morning was no accident.
My dick had grown big and hard and was straining against my hose and skirt, wanting release. She laid her hand on it and squeezed gently. Now it was my turn to close my eyes and moan with pleasure. My erection was now so big and cramped inside my hose that it hurt. I opened my eyes and whispered, “Hang on just a minute.”

I put my hand inside my skirt and straightened it out. She started rubbing her fingers on it, and whispered, “Wow, are you ever turned on. Let’s get more comfortable.”

She slid her skirt down and off, and unbuttoned her blouse and removed it. I reached back and pulled my sweater over my head, and then slid my tight little skirt off. My erection was now fully visible through my sheer-to-the-waist pantyhose, and I was a little embarrassed, so I turned toward her so that it wasn’t so visible. She smiled, and pulled her slip up and over her head. I could now see the hairy mound of her crotch as well, as she had on sheer-to-the-waist pantyhose as well.

“There,” she said, “Now you don’t have to be embarrassed.”

We laid back down, entertwining our nyloned legs, and resumed petting. Our kisses were getting deeper and hotter, and, on a lark, I tried putting my tongue between her lips. She eagerly opened her teeth and let me in, and then put her tongue beside mine and entered my mouth. We French kissed several times, and then she abruptly sat up and took off her bra, and I followed suit. We resumed kissing, and then she said, “Give me your hand.”

I wondered what she was going to do with it, when she spread her legs and guided it into her crotch. She took my middle finger and said, “Here, do like this.”

She guided my finger up and down vertically on her labia lips. Our hose didn’t have a gusset, so there was nothing between her pussy and my finger except the thin suntan nylon. I could feel the moisture quickly penetrate her hose, and she started to moan and thrash rhythmically up and down. I put my mouth back top of hers, and my tongue back in her mouth, which only lasted a few seconds before she opened her mouth and said, “Oh god, Brie, fuck me, fuck me now.” She pulled down her pantyhose to her thighs, and then pulled one leg out as I took my cue and pulled mine down to my thighs as well. I got on top of her and positioned my dick in between her legs, when she pulled them wide apart and took ahold of my dick, guiding it right to her hole. I closed my eyes and started to push. I penetrated her immediately, wondering about how far to go in, when she grabbed my rear end with both hands and pulled me all the way in. We started to thrust together, and as our rhythms matched, she whispered, “Tell me before you cum, we want to make this last as long as possible.”

No problem, so do I, I thought. As I felt my orgasm approaching, I slowed down and said, “I think I’m getting close.”

“Think about something else for a minute,” she said, as she continued to hump and thrust madly. I did, and was trying to keep from thinking about this gorgeous pantyhosed beauty underneath me for more than a few seconds when she said, “Okay, I’m ready.”

My mind turned back to how I looked in the mirror with the bottom of my crack showing through the slit in the skirt when she came. I felt the wetness envelop me just as I went over the edge too, shooting my big hot pent-up wad into her as deeply as I could. Our thrusting gradually slowed down and stopped, and I collapsed against her.

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. After a few days at my sister-in-law’s, she decided to turn things up a few notches -- Tracy

It was an incredible month. We had sex almost every day. After that first bout with constipation, I didn’t have any more problems. Every morning after breakfast, Char and I would go in the bathroom together and have what Char always called ‘our morning sit on the pot’. We would go in wearing just our pantyhose and bathrobes. One of us would sit on the toilet and have her bowel movement while the other made small talk and did her makeup at the sink, and then we’d switch places. Then we’d go back to our rooms and get dressed.

After work we were always really touchy-feely. When we would get home the first thing we did when we got inside the door was kick off our heels and parade around in our hosed feet the rest of the night. Every time we’d get near each other while making dinner and cleaning up afterward, we’d run our fingertips over each other’s bottoms and giggle.

After dinner we’d cuddle up on the couch and watch TV for a while. We’d nuzzle together and kiss until my dick got so hard I’d reach in my hose and straighten it out, then we’d race upstairs to the bedroom and tear our clothes off and fuck like mad. On Sunday nights we took a shower together and Naired our legs for the upcoming work week, and then shaved our armpits.

One morning at breakfast, she said, “Let’s wear slacks today instead of skirts. I think I’ve got some dress slacks that are a little too small for me, and they should be perfect for you.”

After we did our BMs, we went in her room. She opened her closet digging around in the back, and handed me a pair of beige slacks on a hanger. “Here, try these on,” she said. “Remember they’re women’s, so they zip up in the back.”

I stepped into them, and they slid so softly up my nyloned legs. I pulled them up to my waist, and had to work at getting them zipped in the back – I wasn’t used to doing that! They were pretty long, but Char said, “Don’t worry about the length, you’ll wear heels with them. Go put on those high heel beige sandals you’ve been wearing.”

I sat down on the bed and put them on, and stood back up. The hem was now about an inch above the floor, and you could just see my pantyhosed toes sticking out. “Perfect!” she said. “Now we’ll pair that with my lacy beige top.”

“Mmmm,” I said, after I slid on the top. “I feel so smooth and sleek. It’s just like I felt when I wore the Young Organist’s outfit.”

One day she dressed me up in a cami and tap pants instead of a slip, in a green double-breasted suit dress and beige pumps. It was a very conservative look, unless you knew what I had on underneath.

We were talking to one of her co-workers, Beth, and Char said, “You should see what Brie has on underneath that dress. She’s wearing my powder blue daywear.” She looked at me and said, “Everyone else has left for the day. Go in the bathroom and take off the dress and model the cami and tap pants for us.”

I froze in fear, but then Beth touched me on the shoulder and said, “It’s OK. We’re not going to embarrass you. We want to see how pretty you are.”

I went in the bathroom and took off the dress, and made sure my dick was tucked firmly in my hose. I walked sensually out of the bathroom and stuck a pose against the edge of the door in my high heels.

“Wow,” said Beth when she saw me. “Look at her legs.”

I turned and looked at my profile in the bathroom mirror, and I almost passed out. My shaved legs were perfectly smooth in the sheer-to-waist hose, and the high heels really accentuated my calves. The lacy hem on the tap pants barely covered my rear end, and you could see my long legs all the way from my buttocks all the way down to my toe cleavage in the pumps. I was so sexy! My dick immediately started to get hard, and I hoped Beth didn’t notice it through the tap pants, which were thankfully loose.

After a few minutes, I went back in the bathroom and put the dress back on. As we left the office and got in the car, I said, “Oh God Char, I can’t believe how sexy I looked standing there in front of you and Beth. I was so hard. I hope she didn’t see my dick. God, I want to fuck you so bad.”

When we got home I went in my room and took the dress off and hung it up, and then came out of my room in the cami and tap pants and high heels. I walked out into the kitchen where Char was starting to fix dinner, my high heels clicking on tile floor. Char looked at me and I puckered my lips and made a kissing noise. She went into her room and took off her blouse and skirt, and came back out wearing just her slip and hose and heels. She made the same kissing noise back at me, and we ran into each other’s arms, French kissing. We ran down the hall to her bedroom and fell onto her bed. Pausing just long enough to pull down our pantyhose, we fucked hard and fast, both coming within what seemed like seconds.

Later that night, we were looking at clothes in Char’s closet, deciding what we were going to wear the next day. Char was sliding hangers full of clothes back and forth when she stopped suddenly and said, “Here! This is what you should wear tomorrow!” and pulled out a multicolored blue long sweater.
“This is really long on me, and you could wear it as a dress! Remember that time you were here a couple of years ago and I had you put on my navy blue pantyhose and platform sandals? You could wear those with this! It would be so cute!”

She sent me to bed with the dress, the platforms, and a pair of navy blue sheer to waist pantyhose.

The next morning I put on the navy blue pantyhose before I went out in the kitchen for breakfast. When I went in the bathroom to tinkle, I noticed that there was a box of tampons open on the bathroom counter. Char and I had been making love for several weeks, and it occurred to me that it was probably her time of the month.

After breakfast, we went in the bathroom and had our morning sit on the pot. Char went first, and she was on the toilet for a long time. I snuck some glances over at her and her face was red and she was pushing on her stomach, but after she wiped and stood up, there wasn’t anything in the toilet. “Mmmm,” she grunted, “I guess I’m not going to be able to do anything. That’s another way you know your time of the month is coming. Most of us get constipated when it’s due to start. Being constipated makes your period cramps worse, so you want to stay on top of it before you get too plugged up. Bad news, sweetie. No more sex for a few days till it’s over. You may have to. . .” she paused, “stimulate yourself down there if you want to get off, since I can’t do it right now.” We petted and kissed, and then she pulled back. “I know what we can do! Since you’ve pretty much had the whole woman experience the last few weeks, how would you like to see what it feels like to have your time of the month? I mean, you couldn’t experience the whole thing, but you could see what it’s like to sit on a pad for a week, and have a tampon up in you.”

The thought was making me hard. “Oh, Char,” I said, “I’d love to try anything that makes me feel like you.”

“Alright then, after you do your push job we’ll put one up in you.” I sat down on the toilet and moved my bowels while Char opened the box of tampons and took one out. She tore the paper wrapper off and showed it to me. “Since you don’t have any lubrication down there, we’ll have to put some lube on it so it will go in more easily.” She opened the tube of K-Y and put some on the tip and the cardboard tube. After I wiped and flushed, she said, “Now stand up and put your right foot up on the toilet to help open up your bottom. Take some deep breaths and relax.”

She pressed the tip of the tampon to my anus, and said, “Tell me when you’re ready.”

I took a deep breath. “Okay,” I said, bearing down to relax my anus. She pushed the tampon up in me, and said, “You want to put it in about this far. Then, hold the outer tube in place with one hand, and push the inner tube through it to insert the tampon, like this, with your other hand,” as pushed it up in me, then withdrew the applicator. I couldn’t believe how sensual it felt having it up in me.

“Well, how does it feel?” she asked, staring at my dick fully hard and standing at attention, and she said,

“I take it you like it!”

“Mmmm-hmmm,” I said, afraid to touch myself for fear I’d come.

“Even with a tampon, you still need to wear a pad in case you leak. If you’re wearing pantyhose and they don’t have a cotton crotch, you’ll have to wear panties under your hose. Since our hose have one, you can stick the pad to your nylons. Like this,” she said, peeling the tape off the adhesive strips and sticking it into the crotch of my pantyhose.

“Now pull them back up, and make sure the pad is firmly against you,” she said, and I pulled the pantyhose up firmly and pushed the pad into my crotch with my fingers.

“How does it feel?” she asked.

“Bulky,” I said, “after going without underwear for a couple of weeks.”

“Welcome to the club,” she said. “Having your period is a constant exercise in hiding the feminine hygiene products to absorb it. You need to change your tampon every twelve hours, or sooner if it starts to leak. Yours won’t, of course, but change it twice a day. Don’t flush it. Wrap it up in a Kleenex and put it in the wastebasket.”

We went back in our rooms to get dressed. When I finished dressing and looked at myself in the mirror, I couldn’t believe how sexy I looked in the outfit. When Char saw it, she said, “Wow! You look so sexy in that! You’re going to have to be really careful to keep yourself covered up.”

That was for sure. I started walking with my hands at my sides and pulled the hem of the skirt down every time I moved. As we were getting ready to leave, Char came out of the bathroom with more tampons and the tube of K-Y. “Here,” she said, “put these in your purse. You should always have a tampon with you, since you never know exactly when your period is going to start. You’ll need the K-Y too to lube them up to go up in you. The lube is also nice to have when you’re having a big difficult BM that won’t come out. Put some lube on your finger and put it up in your rectum and it’ll help it slide through your boy pussy.”

That evening, after we cleaned up the dinner dishes and sat down on the couch to relax, I snuggled up to Char like I always did before we started petting. Char put her arm around me and said, “So how do you like wearing feminine protection?”

“Mmmm, it’s different. I could feel the tampon in my bottom every time I moved, and it really turns me on. I’m so hot right now, I wish we could fuck.”

We moved into each other’s arms and kissed deeply. “Mmmm, me too sweetie, believe me. It sounds like you like having long thick things up your bottom.” We snuggled for a little bit, and then she said, “I know what we could do. A lot of couples have sex in the woman’s bottom when she’s having her period and she’s constipated. It helps her have a BM. Would you like to try anal?”

“Mmmm, sure,” I said. We walked back to the bedroom arm-in-arm, and I got so hard again, feeling the tampon in my rectum and my pantyhosed feet sliding on the hardwood floor. We took off our dresses and slips, laid down together on the bed, and started petting. After a few deep kisses, I couldn’t stand it anymore. I had to pull down my panty hose and release my erection. She sat up and said, “Show me your tampon string,” giggling. I rolled over on my back and spread my buttocks with my hands. She played with the string, and tugged on it slightly. “Oh God, that is SO hot. A pretty teenage boy wearing pantyhose and a tampon. Our janeboy is having her period.”

“You really have to get lubed up well for anal,” she continued. She got the K-Y out of the bedside table and pulled down her pantyhose. She got up on her knees and turned away from me, then bent forward and spread her legs, treating me to a full view of her beautiful bottom. I could see the tampon string hanging down out of her. She opened the K-Y and put a big gob on her middle finger, and then rubbed it around her perfect little anus. She put some more on her finger and inserted her finger into her anus, sliding it in and out, moaning as she did so. I was ready to explode. She turned to me and put some K-Y on the head of my erection. She said, “God, I can’t believe how hard you get for a fifteen year old boy.”
I said, “When I have hose on, I’m always this hard.”

She said, “Are you ready?”

“Mmmm-hmmm,” I moaned, eagerly.

She laid down, rolled over onto her left side, and said, “Snuggle up to my back and get comfortable. Lay your dick in my crack.” I snuggled up to her back and buried my nose in the nape of her neck, smelling her sexy perfume as our bodies fit together perfectly. After a moment, she said, “Now guide your dick up to my rectum.”

I put my hand down between our warm bodies and spread her crack with my hard dick. I tentatively pushed a little, and she wiggled around until I felt my glans engage her anus. “Now enter me gently,” she said.

I pushed gently, not wanting to go too fast and hurt her. It didn’t feel like I was getting anywhere until she took a breath and pushed gently, and her anus relaxed and I slipped in. Oh God, it felt so good. She settled back against me and I started to thrust gently. It was so sensual. We felt so close, spooned together and our pantyhosed legs rubbing on each other. I could still feel the tampon in my rectum and thought she must feel the same with my dick in her bottom. She farted several times around my dick, and she said, “Sorry. I think my bowels are finally starting to move a little.”

My orgasm came on so fast I didn’t realize it was coming. My semen exploded into her, and we both gasped in pleasure. I felt her stool touching my glans, and I slipped out. “Oh, I’ve really got to go poop,” she said, running into the bathroom and sitting down on the toilet. I heard her grunt and then heard a big stool splash into the toilet, and she moaned in relief. She rolled off some toilet paper and wiped herself, and then flushed. She came back in the bedroom with a soapy washcloth, sat down next to me and wiped off my dick. As always, her touch was heavenly. She stretched out next to me and we cuddled for a little while, and then she said, “Want to go back down and watch TV?”

“Sure,” I said. We got up and put on our bathrobes, then went downstairs to the family room and turned on the TV. We snuggled together on the couch, our pantyhosed legs intertwined and our heads on each other’s shoulders.

The next two mornings Char had a normal BM, but the day after that she wasn’t able to go. That afternoon, she was getting crampy and gassy. After dinner that night, she said, “I really need it in my bottom again. I feel so bloated.”

We walked hand in hand back to her bedroom and disrobed. This time we already knew what to do, and it felt so natural. After I ejaculated and pulled out, she said, “Come on in the bathroom with me so I can go.”

We went in the bathroom and she settled on the toilet. I could hear the crackling sounds as she passed her stool. She had a good satisfying bowel movement, and it was easily evacuated. She moaned in pleasure this time, instead of frustration. After she wiped and pulled up her hose, she touched my hair and said, “I think I really need to keep you around.” We both giggled.

We went back downstairs to watch TV. She took off her bathrobe and spread it out on the couch. “Take off your robe,” she said, and I wondered what she had in mind. We sat down on her robe and snuggled together, and she pulled my robe on top of us. Feeling our perfumed bodies snuggled together through the nylon and lace was just heavenly!

-----0-----

The following week, it was time to go home. That morning, as we were having breakfast, she said, “I have just the outfit for you to wear home. Let’s wear slacks so we don’t have to ride in skirts. Wear the beige lace top with the back-zip slacks and sandals.”

We went in her room and she handed me the outfit. I wondered about what I was going to have to change back into guy clothes. “Um, Char?” I began. “Where will I be able to change back when we meet Mom?”

She came over and stroked my hair. “You won’t have to. You can wear these home. This is my gift to you. This will give you a slacks outfit you can wear out at home. I know you love these beige sandals so I’m giving them to you. I’ll get another pair.”

The ride home was bittersweet. I so hated to go back to guy clothes! When we got to Windsor and met Mom, she did a double take when we got out of the car. “I can’t believe my eyes!” she said. “You two look like sisters!”

We went into a nearby restaurant for lunch. As we sat there, I noticed Mom kept staring at me. Looking at my chest, she said, “You’re even wearing a bra!”

Char looked over her menu, and said quietly, “She’s been wearing a bra ever since she got here! How else would she have a figure?”

“Of course,” Mom giggled.

After we got on the road, I noticed Mom kept staring at me. “I can’t get over how pretty and feminine you look. When I first saw you get out of the car I didn’t even recognize you. Char really worked her magic on you!”

“I know,” I blushed. “I’ve been a girl for a whole month. We wore dresses or skirts and heels every day. It’ll feel weird to go back to dressing like a guy.”

Mom said, “So tell me all about it!”

I did, telling her some of the outfits I wore, and the things we did. Of course I skipped the part about having sex nearly every day. “We always wore skirts or dresses during the week to work. On the weekends we were girl tops and shorts and sandals. She got me this pair of girl’s jeans that were so tight I had to wear pantyhose under them just to get them to slide up all the way. Sometimes when we went out at night we wore our tight jeans and high heels. I was in girl clothes the whole time I was there!”

The next morning, Mom asked me how it felt to be a guy again. I said, “It feels weird to not have a bra and pantyhose on after wearing them almost every day for a whole month! Just like on Sundays, the first thing I did when I got up in the morning was put on pantyhose!”

Mom laughed. “I can still see bra marks on your back. They’re fading, though. Well you can still wear them if you want, you know.”

The next day I decided to be a girl again. I put on a bra and pantyhose with the girl jeans shorts and blue and white top that Char had bought me, and Mom’s high heeled white sandals. It felt so natural to be back in hose and high heels again!

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

My best friend in high school, Jake, was very slender, not very athletic, and not very masculine, just like me. Maybe that’s why we got along so well. We went to different high schools but had the same interests and belonged to the same extracurricular club. We were over at my house one day, talking in my room, and he quietly said, “Can I tell you something?”

“Sure,” I said, wondering if he was getting personal, as quiet as he was talking.

“I just don’t know who to talk to about this. I think I’m gay,” he said, sobbing.

I sat closer to him, and asked, “Why do you think that?”

He paused, and said, “I like girls and all, but they just don’t want anything to do with me. I’ve been having dreams lately, that I’ve been with guys, and I wake up with a stiffy. I’ve been thinking a lot lately about being….. I don’t know…….. close with another guy, and I just really like thinking about it. Promise me you won’t tell anybody. I can’t let anybody know this,” he said, agitated. I could imagine how vulnerable he felt at that moment. I felt like I should reciprocate, somehow.

“It’s OK. You’re secret’s safe with me. I’ll take it to the grave. Actually I have a secret like that that no one knows about.”

He looked up, surprised. “Really?” I wondered if he thought I was going to tell him that I was gay too.

“I’m a…. crossdresser,” I said, blushing. I realized that I’d never really told anyone that. “I like to dress up as a girl. I have a lot of girl things that I wear. It just feels really good when I do it.”

“Wow,” he said, surprised. “I’ve heard of that but I’ve never known anyone that does it. When did you start?”

“Seventh grade. My mom caught me wearing her pantyhose once, and then started buying nylons for me and encouraging me to wear them. The summer after ninth grade I stayed at my sister-in-laws for a month and she dressed me in women’s clothes the whole time. It was awesome,” I said, blushing, my voice quivering. “I have lots of girl clothes. I have women’s slacks and high heels. I shave my legs and paint my toes every weekend. I even use women’s deodorant and a women’s laxative.”

“Wow, that’s neat,” he said, smiling. “I bet you’re really pretty.”

My mom was gone that afternoon, and I got an idea. “Tell you what,” I said, smiling, “Give me a little while to get changed, and I’ll show you.”

I went up to my room, closed and locked the door, and undressed. I quickly put on pantyhose, a bra, and a slip, and put on the brown and white sweater dress that Char had given me in junior high. Looking at my shoe selection, I decided to go with my white high heeled pumps from my Young Organist’s outfit. I ducked into my bathroom, quickly parted my hair in the middle like a girl, and put on some lipstick. I opened the door, smoothed down my skirt, took a deep breath, and walked out into the family room.

The look on Jake’s face when he saw me was absolutely priceless. His mouth fell open, and stood there opening and closing it, unable to say anything. Finally he recovered enough control to say, softly, “Wow. You’re beautiful.”

I blushed. I’d never really dressed up for a guy before. I always enjoyed the looks I got from guys when I was out in public dressed, but this was different. My heart was starting to pound, and I tried hard to keep calm. I crossed my legs to relax a little, and we started to talk about the usual things we talked about. As I relaxed, I really fell into girl mode, and without realizing it, I started dangling my high heel off my toe. I kept noticing that, whenever I wasn’t speaking, he was staring at my legs. The way he was shifting around in his seat, I was pretty sure he had an erection. I was going to kid him about it, but thought I would be more demure and not make an issue of it, as embarrassed as he had been that afternoon.

At a lull in the conversation, he asked, “So are you gay too? But you’ve got Becky!” Becky was my steady girlfriend.

I said, “I don’t know. I’ve thought about it a lot. When I’ve been out in public dressed, I’ve seen guys look at me and smile, and I really like that. It makes me feel really pretty when men are attracted to me. But I do feel attracted to girls too. I’m really attracted to Becky.”

“Does she know that you dress up like a girl?”

“No, I haven’t told her. I’m not sure about telling her. Whenever we get dressed up for a date, I always wear nylons under my slacks. I don’t know if she would approve of it or not. I’d love to be able to be her boyfriend and girlfriend both. But it’s different,” I continued. “I see a pretty girl, and I immediately want to ask her where she got her outfit so I can get it and look just like her. I’m as interested in what she’s wearing as I am in the rest of her.” I really didn’t want to tell him about the relationship that Char and I had had.

Finally, it was about time for his ride to pick him up. I went and changed out of the dress in case someone saw me, but left my pantyhose on and put my jeans on over them, so he could see it when we said goodbye. When we said good-bye, he said, “Thanks so much for listening. I feel so much better.”

“That’s OK,” I said, smiling. “That’s what friends are for. We’ll talk soon.”

“I’ll call you,” he said, as he walked out the door. I saw him sneak one more downward glance at my nyloned feet as he left, and I could tell he definitely had a boner.

Neither one of us brought it up again when we talked. I thought we had forgotten about it until one afternoon a month later when I was over at his house. His Mom was in the kitchen fixing dinner, and we spent some time chitchatting with her. Finally, she looked at Jake and said slyly, “Why don’t you let Brian and I talk for a few minutes alone?”

That caught me by surprise. I really didn’t know Jake’s mom all that well, and couldn’t imagine what she wanted to talk to me about. Jake got up and left, and I thought I saw her wink at him as he left. She got up and refilled our drinks, and sat back down.

“Well, the reason I asked Jake to leave is because we wanted to ask you something and he thought it would be better if I did it. We have a special…… favor to ask of you.”

“Sure, anything,” I said. “Jake’s been my friend for a long time.”

“Well, maybe you should hear what it is first,” she smiled, laying her hand on mine.

She took a sip of her drink and continued. “Now, please don’t be embarrassed at what I’m going to say. We’re all friends here and nothing we talk about will leave this room.” Now, I was starting to get nervous.

She pressed on. “First, I want you to know that Jake is quite fond of you. He has told me, in absolute confidence, that you like to wear girl’s clothes.”

Oh no. I felt the color drain out of my face. It must have been pretty obvious, as she laid her hand on mine again and said soothingly, “It’s OK, dear, we’re not judging you at all. In fact, it’s the reason we asked you here.” She paused, and then went on in a whisper. “Jake, actually, is quite smitten with you when you’re dressed up. His midwinter dance is coming up at his school, and he would really like to go. He hasn’t been able to find a young lady to go with. He was quite upset last night and we were talking about it. He had come up with the idea of taking you, if you would get dressed up and go with him, but he said he thought that you wouldn’t have a way to get a dress or anything. I thought about it and suggested that if you two wanted to go, I would be more than willing to take you shopping and get you a dress and all the….. accoutrements you would need, and see that your hair and makeup was done.”

I let out a breath that I didn’t know I was holding. The whole idea was exciting – I could actually get a dress and go to a formal dance! With a date! “Well, um…….. “ I started to say, a dozen potential problems coming into my head.

“It would be so much fun for me too, dear, you can’t imagine. I’ve never had a daughter of my own to do these things with, and I’ve missed it. You’d be doing us both a favor. Of course I’ll pay for everything,” she said quickly, winding up her argument and obviously trying hard to convince me.

Wow. This was like a dream come true. “Mrs. Spencer, that is so nice of you. I would love to go to the dance with Jake. I had no idea he felt that way.” I felt myself blushing after I went pale a few minutes ago, and started fanning myself. “It’s all just a little overwhelming, I guess.”

“Well, first, let’s get Jake back in here and tell him the good news. He’ll be thrilled.” She got up and went to the kitchen door. “Jake, sweetie, come on back in here.”

I heard his approaching footsteps, and he walked back in the room, tentatively, sitting down next to me and looking first at one of us and then the other. I flashed him my sweetest smile, and his mom said, “We have good news. Brian has agreed to your idea.”

“I’d love to go to your Midwinter with you. I had no idea you felt that way. You should have told me,” I added, giggling, as I laid my hand on his.
He visibly relaxed and let out a breath. “That would be great. You have no idea how long I’ve been working up the nerve to ask you, and I didn’t think you had a way to get a dress or anything. I told Mom this last night, and she immediately agreed to help. Thanks, Mom!”

She smiled. “No problem. First we need to find an afternoon so your date and I can go shopping.”

My Mom was OK with the idea, which was a relief. I wasn’t sure how she’d feel about me going on a date with a guy. I did a lot of thinking, too. I was so turned on when I presented myself to him dressed, and the idea of going on a date was really exciting me. The closest I had gotten to a real date with a boy was when Char’s neighbor boy was checking me out, and I had dodged that bullet by not being old enough to date. Over the years, I had given the whole “gay/not gay” issue a lot of thought. I wondered why Jake had come out to me that day. Was I the only person that he could confide in? He had older brothers that he said he was close to. Or was I giving off ‘girl vibes’ somehow?

Later that week we were talking on the phone. Jake said, “Mom wants to know if you can come over Saturday afternoon and go dress shopping.”

“Okay,” I said, hoping no one I knew would see me.

“Hang on, my mom says she needs to talk to you.” I heard the phone being passed to her, and then she said, “Hi sweetie. Do you have any neutral color heels?”

“Mmmm-hmmm,” I said. “I’ve got some beige sandals with about a two-and-a-half inch heel.”

“Those should be fine. Bring them along and we’ll see if we can find a dress to match them. Be sure to wear hose too.”

On Saturday, I wore the slacks outfit that Char had given me. Since all my hose were sheer-to-the-waist, I went to K-Mart and bought a pair of Underalls pantyhose to wear, so I would have a little more modesty in case Mrs. Spencer saw me undressed. Driving over to Jake’s house, I realized that I had never driven myself anywhere dressed! The new feelings just kept coming.

When I got to Jakes’ house and knocked on the door, his mom immediately answered, with him right behind. “Hi mom,” I said jauntily. “I’m here to be your daughter for the afternoon.”

“That’s great,” she said. “We’ll have so much fun!”

When Jake saw me, his eyes about bugged out. “Wow!” he said. You look so pretty!” which made me blush.

Looking down at my feet, Mrs. Spencer said, “Oh good, you’ve got hose on. I was going to tell you to wear them under your slacks so you wouldn’t have to put them on in the store,” she smiled.

“Actually I wear hose under slacks a lot. These are Underalls, they’re panties and hose all in one.” Jake immediately blushed upon hearing that, which made me giggle.

“Well, that knowledge just made your boyfriend’s day,” she said, smiling. “Those shoes are nice, the beige will probably go with nearly anything. You may want pumps for winter wear, though, so your toes will stay warmer. Let me get my car keys and we’ll be off.”

We went first to J.C. Penney. When we arrived in Formalwear, Mrs. Spencer made a bee line to prom dresses. She looked at me critically and said, “I think a size 6. Something with long sleeves.” We looked through the racks of gorgeous dresses until she stopped and pulled out a gauzy powder blue long-sleeved one. She held it up to me and said, “Let’s start with this one.”

We went into the fitting rooms and I shed my heels, slacks, and top. As I stood there with nothing on but my bra and pantyhose, she looked at me and whispered, “You have such pretty legs and feet. No wonder you like to dress like a girl.” She gathered up the dress and put it over my head. My dick jumped to attention as its silky softness dropped over my pantyhosed legs. She turned me around and zipped it up, then said, “Now put your heels back on.”

I stepped back into my sandals, and then turned around to look at myself in the mirror. I sucked in my breath – I couldn’t believe how different I looked. I was cute. I couldn’t stop staring.

Mrs. Spencer said, “Now go out in the hallway and walk, and see how it feels.”

I was afraid someone would see me, but we were all alone. I couldn’t believe how strangely wonderful it felt to be walking around in a long dress. I was torn between not wanting it to stop and afraid of being caught. Mrs. Spencer finally snapped me out of my daze.

“Earth to Brian! Walk away from me again so I can see how it fits.”

I did, and imagined I was walking down the aisle in a wedding as I watched myself walk toward the mirror. It felt so intensely feminine, even more than the miniskirts I had worn with my stay with Char. As I turned around and walked back toward her, I had this huge smile on my face, and she was smiling, too.

“It looks great on you! Those hose give you a nice smooth line, even without a slip. Okay, come on back in and take it off.”

The disappointment must have really shown on my face. “Don’t worry, there’ll be others,” she laughed as I put my slacks and top back on.

We didn’t find anything else that we liked in Formalwear, though. She said, “Now let’s go back to Lingerie and get you some underthings.”

We walked back to Lingerie, and I couldn’t help staring. There were so many sexy things, and this was always such forbidden territory. She picked out a long slip and held it up to me, then said, “C’mon, back into the fitting room.”

I took off my clothes again and put on the long slip. It looked and felt so sexy. There was a lace-trimmed slit up the side that you could see my smooth nyloned legs through. My erection got so hard it was hurting me.

“This is what you need to wear under that dress. If you think it looked nice with just hose on, wait till you see how it falls with the correct undergarments.”

I twirled around in the slip, so in love with how I looked and felt. Mrs. Spencer said, “Stay here while I go get a few other things,” and left me alone in the changing room. As I was standing there in nothing but a bra and a long slip and pantyhose, looking at myself in the mirror, I decided to see what it would look like with heels on. I stepped back into them and looked back in the mirror, pretending that the slip was the dress. The bottom of the slip was now up off the floor and I could see my high heeled sandals underneath, with my pantyhosed toes peeking out of them. My dick was so hard it hurt. I was twirling around, enjoying how I looked, when Mrs. Spencer came back with more lingerie.

“Here, dear, I got you a camisole to match it. Put this on over your head.”

After I put it on I looked at the whole package in the mirror and was weak in the knees. I was afraid I was going to ejaculate without even touching myself. I was so disappointed when I had to take it all back off. I told myself I would be wearing it again soon enough.

I put my clothes back on and we walked back out into the store. We went past an Underalls display, and she asked, “Do you have any other panty hose, in case you get a run?”

I said, “I have other panty hose, but these are my only Underalls.”

“Then let’s get you another pair. You’ll always need nylons.”

“Okay,” I said. “I need size C-D, and these are beige panty and beige legs, and sandalfoot.” I found a pair and picked them up. She took them from me and we walked to the counter and checked out, handing the salesgirl the slip, the cami, and the nylons. Mrs. Spencer opened up her purse and I said, “Ummm, I didn’t bring any money with me.”

“That’s OK, dear, this is my treat.” When the transaction was complete, she handed me the bag and said, “Here are your new underthings.”

We went and looked at a few other stores for dresses, but didn’t find anything we liked nearly as well as the light blue one at Penney’s, so we went back and bought it. As we rode back to their house, I was in heaven. Sitting there in the back seat with all the bags and packages next to me, knowing they were all mine.

When we got back to their house, she pointed me toward her bedroom, and told Jake, “Now you go do something else for a while. You don’t get to see her all made up till the night of the dance.”

“Aw, Mom,” he said, as he walked away. We went into her bedroom and she closed the door. I kicked off my heels and took off my clothes for the umpteenth time that day and stood there in just my Underalls and my bra. My dick hardened again as I put the slip and cami back on, and then she took the dress off the hanger, rolled it up, and put it over my head. It felt light and heavenly as it slid down over the cami and slip. She tugged at it to get it in place, and then stood back and said, “Now put your heels back on.”

I stepped back into them and she adjusted the dress some more, then said, “Now come over here and see how you look.”

I walked over toward the mirror and stopped as soon as I saw myself. I was beautiful. I had never imagined how pretty I could look in a dress like this. I felt tears well up in my eyes and I started to cry.

“What’s wrong, dear?” Mrs. Spencer asked.

“Uh, uh, noth, nothing,” I sobbed. “It’s so pretty. I can’t believe how I look.”

She handed me a tissue and I wiped my cheeks. “You are a beautiful young lady. Just wait till we get some makeup on you. You’re going to be the belle of the ball.”

I dreamed for the next few weeks of how fun it was going to be going to a formal dance with a date!

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 day finally arrived. I told my Mom I was going to sleep over at Jake’s house since we’d be out late. I took a shower, shaved my legs, and painted my nails. After lunch, when I walked through the kitchen, Mom touched me on the shoulder and asked, “Did you do your BM today?”

“No,” I admitted.

“Why don’t you let me give you a nice warm soapsuds enema? It’ll relax you and clean you out, and make your tummy nice and flat in your dress. Then you won’t have to worry about trying to have a BM in a public bathroom in a long dress. Or worse, holding it back and getting constipated.”

The thought was really tempting. I felt a little guilty that Mom had been shut out of buying me a dress since Mrs. Spencer had done it all. I hadn’t had an enema from Mom since I was small. Since she got me the Correctol, whenever I was out of sorts, she just told me to take some. “Sure,” I said, “that does sound relaxing. I had a BM yesterday, so I’m not really…….. constipated yet. But it sounds heavenly.”

“Go and get undressed, and then come in my bathroom,” she said.

I went back in my room and disrobed, and put on my dressing coat. I went back into Mom’s room as she was filling her feminine hygiene set. “Here’s the Vaseline,” she said, “go ahead and lube yourself up.”

I opened the Vaseline and, putting a gob on my finger, raised my dressing coat and slid my finger into my crack. As I rimmed my anus, my dick immediately got hard. Mom hung the full bag on the shower rod, and handed me the tip. “Remember,” she said, “when you insert it, point the tip up toward your belly button, that way it will follow the natural curve of your rectum.”

I put the tip in my crack and slid it slowly, sensually into my rectum. By now my dick was standing at attention and I was glad I had the dressing coat on. I sat down on the toilet while Mom maneuvered the tube around, and then handed me the clamp. I unclipped the clamp and water gurgled into me. Mom walked out of the room, and I said, “Aren’t you staying with me?”

She said, “Did you want me to?”

“Of course,” I said. She sat down on the edge of the bathtub, and we made small talk. She took the sleeve of my dressing coat between her fingers and said, “You’ve certainly gotten your use out of this. Remember when I got this for you that Christmas when you were in seventh grade? I got you all that girly stuff that year.”

I smiled and said, “I sure do. It was the best Christmas ever. It was the first Christmas that I got to wear high heels. I felt so pretty and grown up. I couldn’t bear to take them back off.”

“That’s for sure,” she laughed. “You should have seen how you lit up when I took them out of the box and handed them to you and told you to put them on. When I caught you wearing my nylons that time, and asked the doctor about it, he said it was probably just a phase you were going through, and to get you some of your own to wear, because once the forbidden nature of it was gone, you’d stop doing it. Boy was he wrong. When I could hardly get you back out of those heels that night, I knew it wasn’t just a phase.” Pointing at my shaved legs and painted nails, she added, “And now look at you.”

The bag gurgled as the last of the water ran out. Mom said, “Stand up so we can get the tip out of you.”

I stood up and reached back and pulled the tip out of my bottom and handed it to her. I sat back down on the toilet while she took the bag to the sink and washed it out. By the time she came back and sat back down on the tub again, I was ready to expel. I relaxed and the water started out of me, followed by my BM and an embarrassing long five-second fart, after which Mom and I both giggled.

“Wow, I bet you do feel better after that,” she laughed. We talked for a few more minutes, as I slowly passed the rest of the water. Mom said, “You better put on some underwear in case there’s any water left in you.”

“Actually I think I’m going to go put in a tampon,” I said.

“That’s a good idea,” she agreed.

I wiped and got up and went into my room. I got out my purse with the tampons and the small tube of K-Y that Char had given me. I put my right foot up on the bed to open my bottom, then tore open a tampon, put some K-Y on the tip, then slid it into my anus. Holding the inner cylinder with my other hand, I pulled out the applicator and threw it away. I opened my dresser drawer and got out my Underalls pantyhose and put them on before I went back in Mom’s room.

When Mom saw me, she said, “You’ve always had such pretty legs. When you wore that dress of Char’s home from Toronto that time, I couldn’t believe how much you looked like a girl. Then after Char had you for a month, and you came home in that outfit of hers, I have to admit I started thinking of you as a girl.”

“It all started with your pantyhose,” I laughed.

“It sure did,” she agreed. “Are you wearing a tampon?”

“Mmmm-hmmm,” I said.

“Do you need more? I can pick you up some when I’m at the store next time.”

“I think I have a couple left in my purse. I don’t need them all that often,” I said.

After an awkward silence, she asked, “So have you told Becky what you’re doing tonight?”

“No,” I said. “I just told her that John and I were having a sleepover.”

After another long pause, she asked, “Have you ever told Becky about your crossdressing?”

“No,” I said, blushing. “Believe me, this whole thing has been all I’ve thought about since I agreed to go to this dance with John. I think it’s about time to tell Becky, as long as we’ve been dating. I just she takes it OK. I don’t want to lose her. She’s so sweet, and I just feel wonderful when I’m with her. I really am in love with her.”

After while, it was time to get dressed. I put on my slacks outfit that Char had given me. Not knowing what the sleeping arrangements were going to be, I put one of my sleeping camis and a pair of panties in my duffle bag. Finally, it was time to go. I made one last stop in the bathroom and took out the tampon.

When I got over to Jake’s house, I took off my high heels and we just hung around talking. I saw him sneaking glances at my nyloned feet. Finally it was time to get ready. His Mom and I went in her bedroom and I got dressed. Before we started, Mrs. Spencer asked, “Do you want to try to go poop before you get dressed? Then you won’t be struggling by yourself with a long dress in a ladies’ room trying to go poop.”

“My Mom thought of that. I had an enema this afternoon before I came over.”

“That was a good idea.” She handed me the lingerie and I put it on, breathless. Feeling the cami and slip on my pantyhosed legs was heavenly, and then she slipped the dress on over them.

I put on the makeup with a little help from his mom. She parted my hair in the middle and held it in place with hairspray. Finally, we were all done. “Now put on your heels, and look at yourself in the mirror. Don’t cry this time or you’ll mess up your makeup,” she said.

I stepped into my heels and turned to face the mirror. I couldn’t believe how pretty I looked. I didn’t recognize myself. I just stood there, dumbly looking at myself, and Mrs. Spencer walked up and sprayed some perfume on my neck. The scent was alluring, and completed the transformation.

She walked over and opened the bedroom door, and said, “Here you go, Briana. It’s your moment of truth.”

I walked out into the living room on wobbly knees. Jake had gotten dressed and was standing there in his suit. Jake looked at me and said, “Wow! I can’t believe you’re a guy under there!”

“For tonight, I’m not,” I giggled.

Jake’s mom had gone into the kitchen and pulled our flowers out of the refrigerator. We put them on each other with a little help from her. She had gotten me a corsage and a wrist flower. As we stood there, looking at each other, not knowing what to say, she broke the silence by saying, “Do you have the money I gave you earlier?”

“Yes, Mom,” he said.

“Well, then you two need to get going. Have fun!”

We went to a wonderfully swank French restaurant for dinner, and had a great time. I went into the ladies’ room to tinkle and freshen my makeup, and then we drove back to my house so Mom could see me in my dress and could take some pictures of us. Then we drove to the dance. I was so nervous that I would be found out, but the girls treated me like one of them. I didn’t know anyone that went to that school other than Jake, so it was OK. I danced with several other guys, and then had to use the ladies’ room again. Jake and I walked down the hall to the restrooms arm-in-arm, my high heels clicking sexily on the tile floor. He said, “I can hear your high heels as you walk. God, you are so sexy!”

“Thanks,” I said, not wanting him to know I felt exactly the same way. When I got in the bathroom, I went into the nearest empty stall, pulled up my dress and slip, and sat down on the toilet, relaxing for a minute. Another girl came in and sat down in the next stall. I recognized the hem of her dress and her reinforced toe nylons. She had been sitting at the table next to us, and her name was Lynn. I heard her gasping and grunting, and wondered if she was all right. Another girl came in the bathroom and started talking to her. Finally she said, “God, my poop just won’t come out.”

Her friend asked, “Are you constipated again?”

“Yes,” she said. “I haven’t gone in, like, a week. I’m going to ask my Mom for a laxative again.”

I was going to tell her to go put her heels back on and try again, but thought better of it. I remembered how wonderfully relaxed and empty I felt after my enema. Later, I saw her back in the gym, and remembering her sexy grunts as she was trying to poop, my dick started to get hard for the thousandth time that night. When the last slow dance of the night came, I kicked off my heels and dragged Jake out to the dance floor again. I was taller than him in my heels and I had to take them off when we danced. We pulled each other close and I laid my head on his shoulder, swaying to the music. He kissed my ear, and then whispered, “I love you.”

I pulled my head back off his shoulder and faced him. I tilted my head and our lips met for our first kiss. It was short and awkward, like all first kisses are, then I tilted my head the other way and we kissed again, long and deep this time. “Oh Jake,” I moaned, “I love you too. This night has been so incredible.” When the dance was over, we sat down and held hands, my legs crossed and my barestocking foot poking out from under the hem of my long dress, bobbing up and down, showing the whole world my pretty painted toes through my sandalfoot Underalls.

Finally we decided to go home. We held hands and walked to the car. When we got in the car, I laid my head on his shoulder, not wanting the evening to end. After we got under way, my feet were hurting from my high heels and I slipped them off and put my barestocking feet in Jake’s lap. He started stroking them sexily. I was in heaven!

When we got to his house, I put my heels back on and we walked into the house. After we got inside I reached down and took them off again and wiggled my toes. His mom greeted us with, “I bet your feet are tired after all night in those heels. So how was your first formal dance, Briana?”

“All I can say is, wow,” I giggled.

She held up a bag and handed it to me. “This is for you. I didn’t want you to have to sleep in your slip.”

I looked at her quizzically. “What do you mean?”

“Oh that’s right, you probably don’t know that,” she laughed. “When a woman gets caught out without a nightgown, she usually sleeps in her slip, since it’s almost like a nightie. I got you something nice to sleep in. Be sure and hang up your dress. I put the hanger in Jake’s room. Sweet dreams you two.” She walked off into her bedroom and shut the door.

We looked at each other. Jake broke the silence and said, “Ready for bed?” I was wondering what the sleeping arrangements would be.

We went into his bedroom and shut the door. It felt like we were a bride and groom on our wedding night. I opened up the bag and looked inside. There was a short purple lace nightie, dressing coat, and panties set. I couldn’t believe it. The surprises just kept coming.

Jake had loosened his tie, and started to get undressed. I said, “Can you unzip me?”

“Sure,” he said, as he ran my zipper down my back. I worked my arms out of the sleeves, pushed it down my torso and legs, and stepped out of it. I picked it up and hung it on the hanger. Standing there in my slip and nylons, I pulled out the lingerie out of the bag and looked at it. Jake was undressed down to his underwear by now. He walked over to me and said, “C’mere.”

He put his arms around me and I put mine around his neck. Without my heels on, he was taller than me. He pulled me close to him, and I saw him close his eyes and bring his lips close to mine. I closed my eyes and tilted my head opposite to his, and our lips met. The first kiss was warm. I was really starting to like kissing him. The second kiss was long, moist, and so erotic, and the third was even better, as I felt his tongue part my lips and I opened my mouth to let him in. He reached down into his pants and straightened out his erection, and I did likewise, releasing my dick from the nylon prison it had endured in my Underalls for the last five hours.

“Shall I go in the bathroom and put on the nightie?” I asked.

“Actually, I didn’t know my mom was going to get you that. I’ve been dreaming all week of making love to you with nothing on but your pantyhose.”

“Okay,” I said, sliding off my slip and camisole. I turned my back to him and then looked over my shoulder demurely and asked, “Would you like to unhook me?”

He put his arms around me and nuzzled my neck, and then we broke apart and he unhooked my bra. I shucked it off of my arms while he took off his underwear. He put his arms around me again and resumed nuzzling me, rubbing his big hard erection against my pantyhosed bottom, both of us moaning in pleasure.

“You like me in pan-ty-hose, don’t you?” I asked, sensually.

“How did you know?” he said, blushing.

“I’ve seen you staring at my feet when I have hose on,” I moaned, kissing him again and sticking my tongue in his mouth. “When you were at my house and I came out to you, I saw you staring at my feet before you left. I could tell you had a boner. It made me feel so attractive that I was turning you on.”

“When I got home that day, I went straight into the bathroom and jacked off,” he said, kissing me again. “That’s when I got the idea of asking you out on a dress-up date.” We broke apart and I laid down on the bed, sexily rubbing my pantyhosed legs together. He went over and turned off all the lights but one, leaving us in semidarkness. He laid down facing me and we passionately kissed again. We were both ready to explode. He produced a tube of K-Y Jelly and said, “She even bought us some lube. Pull down your nylons.”

I slid my panty hose down to my thighs before I took the K-Y from him and, opening it, put a gob on my finger and put it in my crack, rimming my anus with my finger, getting so turned on in anticipation of what was coming. Turning back to him, I got more lube and, holding his erect dick with one hand, smeared it on his tip, rimming it with my finger just like I had rimmed my own rectum seconds earlier. We were ready. I rolled over and exposed my bottom to him, and he pulled me close as he guided his erection into my crack and up to my anus. I took a deep breath and bore down, and with his next thrust, he entered me. It felt so good. I had experimented with putting things up my anus before, of course, but nothing felt as good as his big hard dick entering me. He started to thrust and I hoped the bed didn’t make noise, although his mom’s room was in the other end of the trailer. His thrusts in my rectum, his dick sliding in and out of my anus, and the feel of our legs sliding together through my panty hose were more than I could take, and I ejaculated, shuddering and groaning as I did so, and tightening my anus around his dick. Seconds later he quivered as he climaxed. I could feel his dick spasm as he ejaculated and then his hot wad shooting into my rectum as he groaned, “Oh God this is so good.”

We laid there for a while, enjoying the post-coital glow. Remembering that I still had my makeup on, I said, “Sweetie, I should get up and take off my makeup before I get it all over your pillows.”

I took the makeup remover and tissues into the bathroom with me and cleaned my face off.
After I tinkled, I slid out of my panty hose and picked up the tiny little purple lace panties. After I made sure which way they went on, I slid them up my legs and tucked my package into them, and then put the nightie over my head and let it drop into place. When I looked at myself in the mirror, I immediately started to get hard again. I couldn’t believe it, it had only been like ten minutes since I had ejaculated and I was already getting hard again. I put the dressing coat on over it, which covered most of me up and made me decent, but just barely, and then went back into the bedroom. Every time I moved, I could feel Jake’s semen in my rectum.

Jake had rolled over onto his back and was looking at me. “Oh wow,” he said, seeing me in the nightie. I demurely opened the dressing coat and took it off, laying it on the bed, and sat down on the bed next to him. “Why don’t you go potty and then let’s go to bed,” I whispered.

He got up, put on a robe, and went into his bathroom. I heard the toilet flush, and he returned a few minutes later with my Underalls in his hand. “Here,” he said, smiling, “I think you forgot these.”

“Oh thanks, I’ll need those in the morning,” I agreed.

He said, “That’s the first time I’ve ever discovered pantyhose in my bathroom.” We both giggled.

He took off his robe as I turned back the bed. He turned off the remaining light and we got under the covers, snuggling close. I held him close and listened to his breathing get slow and regular as he fell asleep. Having sex with him had been such a phenomenal experience. The sex I had had with Char was wonderful, but now that I had played the girl role, I realized that sex was more than just a release. It was an intimate sharing with another person. Jake had shared himself and left part of himself in me. I laid awake for a long time, thinking about sex and intimacy.

When I woke up, Jake and I were still snuggled together, all toasty and warm. Sunlight was streaming in the window, flooding the room. And I had to go potty, bad! I gently disentangled myself from Jake and got out of bed. I put on the dressing coat and made my way to the bathroom. After relieving myself, I went back in the bedroom and saw Jake laying there in bed on his side, his open arms beckoning me to return.

“Wow,” he said. “You look great in the morning!”

I slid back in under the covers and snuggled up next to him. We kissed, and as he pressed his big hard dick into me, I realized that he was nude under the covers. We started to make out, and my erection was straining against the panties. I reached down and straightened it out, and it stuck out its entire length, the panties only being big enough to hold my testicles. I turned back to him, pressed my dick into his leg, and started to jack off against him.

“Mmmmmm,” he said. “Wanna fuck again? This time let’s just hump each other. I want to face you and see you.”

“Sure,” I giggled. I pulled up the nightie all the way up to my nipples. He pushed me over onto my back and got on top of me. I reached down and laid our dicks side-by-side, then put my arms around his neck and pulled him to me as we ground our hips together. We kissed again and again as we picked up each other’s rhythm, and then came almost simultaneously, our hot cum shooting over each other’s tummies. He went limp in my arms as we snuggled together, and I thought he might have gone back to sleep, but then picked his head up.

“Let me get some Kleenex to clean up,” he said as he got up out of bed. He pulled some tissues out of the box as I ran my finger through the puddle of goo on my tummy, mixing our semen together. He handed me a tissue and I cleaned up while he wiped himself up. He laid back down next to me and we snuggled again. All of a sudden I started to smell a tantalizing smell.

“Wow,” I said. “What smells so good?”

“My mom making breakfast. Let’s go check it out.”

We got up and Jake put on his PJs while I tucked my limp package back into the panties, pulled down my nightie, and slipped on the dressing coat. We opened the bedroom door and walked into the kitchen arm-in-arm. After all the time I spent in heels yesterday, I was still prancing around like a girl when I walked, up on the balls of my feet, even without shoes on. I just felt so femme and girly with Jake’s arm around my waist, still walking like I had heels on. Jake’s mom was standing over the stove and the smell of bacon cooking was so tantalizing.

“So did you sleep well? Look at you in that nightie! I thought it was your size.”

“It’s great, Mrs. Spencer. I don’t know how I’m ever going to repay you for all this.”

“Now I told you already, this was my pleasure. I have never had a daughter to do this for. And you and Jake get along so well. I’m just glad I can do this for you two. I know you two had a great time last night. Now sit down at the table, breakfast is ready.”

We picked two chairs next to each other. After sitting down, he put his arm around me, and I felt so sexy and feminine as he continued eyeing me. I crossed my legs and turned toward him, our legs touching and my foot bobbing up and down, my red polished toenails on display, so sissy. During breakfast, Mrs. Spencer looked at me and said, “You know, you are just glowing! I think this really agrees with you.”

I immediately blushed, knowing that the reason I was ‘glowing’ was probably due to having sex with her son twice in the last eight hours, but I didn’t want to announce that. Jake and I just looked at each other and smiled.

Breakfast was terrific. I knew his mom was a terrific cook. After we ate, we just sat there, holding hands and enjoying each other’s company. Finally, we went back to his room to get dressed. After he closed the door, he came up to me from behind and put his arms around me and nuzzled my neck. He whispered in my ear, “Can I watch you get dressed?”

“Sure,” I said. I sat down on the bed and slid off the tiny little purple panties. I took my Underalls and gathered up the legs and slid them on, slowly and sexily for his benefit, before I stood up and finished pulling them up. I put my toe on the edge of the bed as I pulled the wrinkles up out of them, treating him to a closeup view of my pretty red painted toes through my sandalfoot nylons. I put on my bra and my Secret deodorant, followed by my lace top, and then slid my slacks up my nyloned legs and zipped them in back. Posing in front of the mirror, I turned sideways and bent my leg so I could see how my bottom looked in the mirror. I ran my fingertips over my smooth bottom and said, “Mmmm, Underalls – they make me look like I ain’t wearing nothin’!’” I said, sexily, acting out the ad from TV.

We went back out in the living room. I stepped back into my high heels and said our goodbyes. I gushed all over his mom one last time, and she kissed me and gave me a big hug. Looking down at my feet, she said, “Oh you’re wearing your heels home. You look so grown up!”

He carried my duffel out to my car and we shared one last passionate kiss. I sat down on the front seat and swung my feet in and he closed the door behind me. I had to pump the gas pedal to get my car started, and I felt so girly doing it in my high heels! I drove home glowing after eighteen hours as a girl, but really unsure about my feelings about him and Becky.

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.”

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 following year, after we graduated from high school, Becky and I got engaged. After that, her parents got a little less uptight about us being together, thankfully. About a month before Thanksgiving, Becky was over at my house, and we were sitting around talking about Thanksgiving. Mom asked her, “Are you coming for dinner? Just wondering how many people I was going to have to cook for.”

Becky said, “I’d love to come spend Thanksgiving with you guys. We’re getting dressed up, right? I was going to wear a dress. But if I wear one, YOU have to wear one too,” she said, giggling, pointing her finger into my shoulder. “And you too,” she said, looking at my Mom.

“Wow,” Mom laughed, “she drives a hard bargain.”

“I’ve got just the dress for you,” Becky said, looking at me, “my stretchy brown one that’s strapless. I’ll have to loan you the bra to go with it. I’ve been wanting to see you in it. Your beige sandals should go perfectly with it.”

“Mmmm,” I said, my dick hardening at the thought of us all spending the day in dresses!

A few days later, she handed me a box as I was leaving her house. “Here’s the dress and the bra, along with the dress and slip I’m going to wear. We’ll get dressed at your house.”

When I got home, I hung up both dresses in my closet, marveling at how they looked hanging there. Later that week, I noticed in the paper that K-Mart had Underalls on sale, and the next time I drove past there, I stopped in and got her a pair in her size. When we talked on the phone that night, I said, “I’ve got a surprise for you. I bought you a pair of Underalls to wear on Thursday!”

“Oooh, we’ll both be so smooth and sleek,” she purred, sexily.

Thanksgiving finally came! I slept in that morning, then got up and took a nice hot bath and shaved my legs and armpits. I put on Becky’s strapless bra and my Underalls, and did my nails so they would have plenty of time to dry. I put on my pink dressing coat and went out to help Mom get dinner started.

Finally Becky arrived around 11. After saying hi to my mom and looking over the dinner, we went into my room to get dressed. I handed her the Underalls I bought for her, and then she disrobed down to her bra. I took off my dressing coat and sat down on the bed while she put on her pantyhose, and then played footsie and giggled about how pretty our legs looked. Next we donned our slips and our dresses, and went in the bathroom and did our makeup. Finally we sat down on the bed and put on our high heels, and after one last look in the mirror and air-kissing each other, we sauntered out into the family room.

Hand in hand, we walked into the kitchen, and when Mom saw us she exclaimed. “Wow! Look at you two! You’re gorgeous!” We both giggled, then walked around the kitchen looking at all the food. Mom said, “I think things are far enough along that I can go get ready now. Keep an eye on things and I’ll be back in a little while.”

Mom went in her bedroom and closed the door, and Becky and I stood there facing each other, our fingertips lightly touching, the sexual tension between us palpable. “God, I am so turned on right now,” I whispered.

“Me too,” she agreed. “Are we going to have any ‘us time’ this afternoon?”

“I think Mom’s going to take some food up to Grandma later on and see her for a while. We should have a little time to ourselves,” I grinned.

We sat the table, then watched the parade on TV till Mom came back out of her room, looking exquisite herself in a white lace blouse, a pencil skirt, and heels. We stood around in the kitchen admiring each other’s outfits and talking girl talk till it was time to eat.

After dinner, Becky and I washed dishes while Mom relaxed. When we were almost done, Mom came back in the kitchen and said, “I can’t believe you’re washing dishes in high heels. But you probably couldn’t get Brian out of his.” I blushed, and they laughed.

“So I like to get dressed up on holidays. So sue me,” I smiled, still red-faced.

Mom got the food back out and put together a casserole dish. “Well I better take something up to Grandma, I told her I would, then spend some time with her. No hanky-panky you two,” she said, smiling.

”Don’t worry, Mom,” we giggled in unison. We helped her carry the food to the car, and waved as she left. We went back inside and sat down on the couch next to each other, our pantyhosed legs crossed and touching, our high heels bobbing up and down. Our dresses were both knee-length and had ridden up when we sat down, exposing a lot of our legs. We held hands lightly and laid them on our knees while we kissed. We started to make out, and I started to stroke her nice smooth legs with my fingers. She moaned in pleasure and responded in kind.

I started to run my fingertips under the hem of her dress, feeling the lacy edge of her slip, and she said, “Naughty boy. Two can play at that game,” and put her fingers under my skirt. The feel of her fingertips running up my nyloned legs made my dick rock-hard. As we kissed and our passion got hotter, our hands both crept up each other’s legs till we both reached our pubes. She started tracing the outline of my erection with her fingernail through my Underalls, and I slid my hand between her thighs, feeling her pussy moisture through hers. She was breathing heavily, and finally said, “C’mon. I can’t wait any longer.”

“Me either,” I agreed. We jumped up and ran into my room as fast our high heels through the shag carpeting would allow. When we got in my room, I caressed her, unzipping her dress, and slid it over her arms and down to the floor. She moved my spaghetti straps off my shoulders, and, taking the stretchy bodice of my dress in her hands, wiggled it down my chest and down off my body. We hugged and kissed again, and then we slid each other’s slips off, followed by our bras. I was ready to explode. I slid my pantyhose down to my hips, releasing my huge erection, and then put my hands on her buttocks and pulled her to me, grinding my big hard dick against her. She broke away and pulled her hose down, then sat down on the bed and said, “Take off my heels.”

I unbuckled them and took them off, and she slid one leg out of her pantyhose. She laid down on the bed and I reached over and got a condom. “Here, let me put it on you,” she whispered. I handed it to her, and she tore open the package and while I laid next to her. She put it on the head of my dick and rolled it down my shaft. “I can’t believe how big your…. thing gets,” she giggled. Still in my hose and high heels, I crawled between her legs as she spread them wide. She wrapped her arms around me and pulled me close, and I guided my dick into her crotch and entered her slowly and carefully as she groaned in pleasure. We saved sex for special occasions, and she was still so tight, I didn’t want to hurt her. We both needed release so badly. We fucked slowly and deliberately, enjoying it fully since we didn’t get the chance very often. As I moved around, my high heels kept hitting the bottom headboard of the bed, and it was so hot, fucking this beautiful girl while I had hose and high heels on. We both went over the edge at nearly the same time, thrusting deeply.

We both fell asleep briefly, and waking up, we kissed and smiled. “Wow,” she said. “Wait till we can do this all the time.”

“Ummm-hmmm,” I agreed. I carefully sat up so I didn’t hit her with my high heels. She sat up and pulled her pantyhose back on, and then we sat next to each other, touching and feeling each other’s warmth. “What do you want to wear now? Jeans and heels?”

“Mmmm, that would be great,” I said. I took off my heels and pulled up the wrinkles out of my pantyhose. I reached in my closet and got out my girl jeans and my lacy beige top. Becky had been wearing one of her favorite tops, an opaque silk shirt, and she put it on without a bra underneath, her nipples showing through.

“Mmmm, very daring,” I said.

“I like wearing this without a bra,” she said, slyly. “I love how it feels on my boobies.” As conservative as she was, it was a real sexual statement for her. We went back out in the family room and watched TV and played games the rest of the afternoon, feeling so girly. Every time we sat together we crossed our legs and put our feet together, showing off our high heels and our perfect pantyhosed feet.

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!”

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

Sunday morning, I saw Tina at church, and she smiled at me when our eyes met. After church, she stayed a few minutes after the choir dispersed, and came up to me in the choir room.

“So are you feeling better today?” she asked. “Did you get your constipation problem taken care of?”

“Mmmm-hmmm,” I replied, blushing.

She continued, “I was going to ask you if you’d like to get…. dressed up and go shopping. Erin is going to be at a friend’s house all day Tuesday. I thought maybe we could go shopping and then maybe do lunch.”

I tingled with excitement at the thought. “Sure,” I said. “Where do you want to meet?”

“Why don’t I just pick you up?” she asked. “You live on Applewood Street, right? That’s not very far out of the way. Ten o’clock alright?”

“Sure,” I smiled. “I can’t wait.”

On Tuesday morning, I got up early and shaved my legs. I got out my new K-Mart Soft Smooth and Sheer pantyhose and put them on. I was going to wear my macramé wedge sandals and they were the only nylons I had that were sandalfoot. After putting them on, I put on my robe and went in the kitchen and had a bowl of bran cereal for breakfast.

Afterward, I went back in the bedroom and was admiring my smooth, sexy nyloned legs and feet in the full length mirror. I pulled my black pinstripe slacks on over my hose, followed by my black sweater. I stood up and got my beige macramé sandals out of the closet, and sat back down on the bed. Slipping them on my hosed feet, I did up the buckles, and then stood up and modeled in front of the mirror again. My feet looked so smooth and perfect in my sandals and sandalfoot hose!

I went out in the living room, turned on the TV and sat on the couch, enjoying the feeling of being all dressed up in girl clothes. A little while later, Tina pulled up in the driveway. I saw her walk around to the front door and I opened it before she got there. She had on a brown sweater, denim miniskirt, tan hose, and brown clogs. She looked so hot!

“Hi,” she said as she came in the door. “Ready to go shopping?”

“Of course,” I said. “Wow, you look great!” I said, staring at her gorgeous legs.

“So do you,” she said, staring at my feet. “Those sandals are cute. I wore my clogs cause I thought they would be easier to slip in and out of when we’re trying on shoes.”

“Let me get my purse and some money and I’ll be ready.” Grabbing my purse and my wallet and keys, I walked back into the living room as I stuffed them in my purse. We walked out the front door and I locked the door behind me.

We got into her car, and I couldn’t help staring as I watched her fold her shapely nyloned legs under the steering wheel. As we drove off, she said, “I didn’t know what to wear. I didn’t want to ask you what you were going to wear at church in case someone overheard us. I thought I’d wear a skirt in case you did too.”

“Well, actually, I don’t have any skirts of my own, just slacks. I guess I could have borrowed one of Becky’s though. It didn’t occur to me. I’m not that brave yet,” I giggled.

“That’s OK,” she said, patting my knee, “whatever you’re comfortable with. So you got your poo problems resolved?”

“Mmm-hmmm. My boyfriend came over that afternoon, and sensed that I wasn’t feeling well. I told him I had bought some Correctol because I was constipated, and wondered if I shouldn’t have gotten an enema instead. He suggested that maybe it would help me go if we had,” I said, blushing, “sex in my butt. So he gave me an enema with his wee-wee,” I giggled.

“Did that work?” Tina asked.

“Yes,” I replied. “I had a HUGE BM afterward, and it was really easy. His semen made it really slippery and slide out really easily.”

Tina smiled. “Tom and I have done it that way before and it had the same effect on me. Back when we were still having sex,” she added, sadly. She smiled and said, “So you’ve got a boyfriend, huh?”

“I guess, since we had sex, that probably makes him my boyfriend,” I giggled. “We were kissing and petting too, though. I just hadn’t thought about it that way. I mean, I wasn’t really looking for a boyfriend. We just had sex because of my poo problem.”

“Well, whose idea was it?” Tina laughed.

“His,” I said.

“I’m sure he had another motive in mind when he suggested it. Guys will do about anything to talk you into sex.”

“I know,” I said. “Actually, I really liked the way it felt, and not just cause it made me poop. When we were doing it, we were spooning and he had his arms around me and I felt so close to him. When he came in me, it just felt incredible. After we were done, and I had my BM, we started petting again, and he gave me a blow job. I can’t believe I’m telling you this,” I said, smiling.

“It’s OK,” she said. “Most girls like to talk about their experiences. I just want you to know that you can confide in me if you want and I will take it to the grave.”

“Thanks, I appreciate that. Actually I don’t have any one else to confide in, especially a girl.” I paused, then said, “I really liked it though. It felt so good, especially when he ejaculated into me. It felt so warm and intimate.”

“Isn’t it just the greatest feeling when he ejaculates? You can actually feel it coming up his dick before he squirts.”

“I know! It felt so cool. I’m getting hard again just thinking about it.”

“Sounds like you like having long thick things up in your bottom.”

I blushed again. “I guess I do.” I paused. “A lot of times, when I’m doing my push job and it’s part way out and big and really stretching me out, I get a boner,” I blushed.

“Mmmm,” she said. “When I give myself an enema, I use the douche nozzle instead of the rectal tip. I just love the feeling of it stretching me out as it goes in. You should try it sometime, I bet you’ll like it too. So, if you don’t mind me asking, how did you get started wearing women’s clothes?”

“Well, I’ve always liked wearing pantyhose. When I was in seventh grade my mom started buying them for me to wear them under my slacks when I got dressed up, like for church. Then when I was in ninth grade, I joined the Young Organist’s Society. We went out and gave concerts for nursing homes and places like that. The uniform for the girls was white skirts and white pumps with a red blazer. I was the only boy, and the other moms suggested to my mom that I wear white pumps too with my white slacks so I would match them. We had to go to the bridal department at Wards to get them because they were the only place that had white shoes in the middle of winter. After we bought the shoes, she got me nude sheer to the waist pantyhose to wear with them underneath my slacks, so I looked grown up and wouldn’t have underwear lines showing. She said I needed to have a ‘smooth line’. I always felt so sleek and pretty when I wore them. I loved wearing the uniform and always looked forward to the concerts so I could get dressed up. ”

“I’m sure they did. Nylons and high heels are supposed to make you sleek and pretty,” she said. “I couldn’t believe how fascinated I was when I saw you wearing nylons and flats that day in Target, trying on women’s shoes. Then when you walked ahead of me in the mall, I saw you had women’s slacks on, and you didn’t have panty lines. I knew you were either going commando or had pantyhose on. You were smooth in the front so I figured it was pantyhose, but I couldn’t believe it, I had to ask. I hope you weren’t too embarrassed.”

“Not at all,” I said. “It turned me on when you asked.”

“It turned ME on when you said yes,” she blushed. “I couldn’t believe how excited it got me, watching you sashay ahead of me. I was SO attracted to you right then.”

I realized that she probably didn’t know that I wore hose to church every Sunday. I said, coyly, “You do know I wear panty hose to church every Sunday? Whenever you’re seen me at church I’ve had hose on under my slacks.”

“Really?” she said. “Your wife is OK with that?”

“Mmmm-hmmm. I came out to her after we’d been dating a few years. Every time she buys nylons she always gets me some.”

“How long have you been doing that?”

“Since seventh grade. My mom caught me wearing her pantyhose once. After talking to the doctor about it, and he told her it was OK and something some boys need to do, she actually encouraged it. It was her idea to wear them to church the first time. She said it would make my pants fit better and slide over my legs better when I stood up and sat down, and she was right. Ever since then I always put panty hose on whenever I dress up.”

“Wow,” she said. “You’re right, I had no idea. I would never have known if I hadn’t seen you in Ayr-Way that day trying on girl shoes with hose on.”

“Well I’m glad we met like that that day. I would never have come out to you otherwise. I was really embarrassed at first when you saw me, but then I figured, ‘what the heck’. Lots of people saw me in high heels and nylons at the Young Organist concerts and nobody said a thing. The girls all treated me like one of them.”

“That’s so cool that you got to be all grown up like that,” she said. “It’s a major day in a girl’s life when she gets her first pair of heels. It’s great that you got to practice being a woman in an accepting environment. You didn’t have to be embarrassed or anything.”

“Well,” I paused, smiling, “I was a little at first. The tough part about wearing the concert uniform was hiding my erection. When I’d get dressed and put on the pantyhose I always got a huge boner. I’d have to force myself to think about something else for a while so it would go down and I could tuck it down in the hose so I could finish getting dressed. I remember the first time I performed in that uniform. I walked across the floor after they announced my name and I could feel everyone’s eyes on me and I hoped they wouldn’t laugh at a boy in high heels. It felt like I had to walk a mile to get to the organ. I was reminding myself to walk heel-to-toe like a girl, and trying to remember the first few notes of my music so I could get started. You could hear my high heels clicking across the floor as I walked and I could feel my slacks sliding over my panty hose and I got a HUGE hard on. I was so glad the blazer was buttoned so no one could see it! I could barely keep my mind on playing.”

“Wow,” she said. “I wish I could have seen you. A cute girly boy in high heels and a shimmy in his walk! And hose on! I bet you were gorgeous, you were such a girl! Did your Mom get you a bra too?”

“No, but I didn’t need one, since I don’t have anything to hold up.”

“Too bad. She could have gotten you a training bra. You don’t need to have anything to hold it up. I would have gotten you a white skirt instead of the slacks, though. What would they have done? Not let you perform? You would have looked great, showing your legs off in your pantyhose and your white heels,” she said. “Did you do anything else girly then?”

“I noticed at the first concert that everyone else had painted nails except me. After we went back to the prep room after the concert for our business meeting, the other girls took off their shoes and were lounging around in their stocking feet, so I did too. We were noticing and comparing who had reinforced toe nylons and who had sandalfoot. A couple of the other girls had painted toes and they looked so hot through their nylons. That night I went through my mom’s nail polish and found some that matched the blazer pretty close, and before the next concert, I painted my nails. The next time we had our shoes off and I saw my painted toes through my sandalfoot nylons, and the other girls complemented me, I got so aroused. I was concentrating on looking at my nylon feet during the meeting and I actually ejaculated. I had to excuse myself and go to the bathroom quickly and clean up the semen so it didn’t stain my slacks.”

“Mmmm,” Tina said, shifting around in her seat.

“Is there something the matter?” I asked.

“No, not at all,” she said, blushing. “I’m just getting so hot. I wish I could have seen the look on your face when you had your orgasm. I bet it was priceless!”

“I remember turning really red,” I said, giggling.

We turned into the K-Mart parking lot. Tina said, ”OK if we start at K-Mart? They’re having a shoe sale.”

When we got out of the car, Tina took my hand as we were walking into the store, and it really started to get me aroused. We walked right to the shoe section. It was spring, and they had all their white shoes out. I saw a pair of high heeled stiletto slide sandals, and grabbed a pair in size 9.

“Tina, look at these. Aren’t they cute?”

“They really are,” she said. “What are you waiting for? Try them on!”

I took them over to a stool and sat down. Crossing my legs, I pulled up my pantleg and unbuckled my sandals and took them off. Standing up, I stepped into the white sandals and started to walk around in them. They fit really well, and were comfortable. I walked over to the mirror and admired myself. Tina said, “Wow! Those would look so cute with your white slacks!”

“I was just thinking that,” I admitted. “I think I’m going to get them.”

I left them on and walked around in them while we looked at shoes. Tina found a pair of wood soled platform sandals. I said,” Try those on! Those would go really well with what you’ve got on.”

“Think so?” she smiled. She stepped out of her clogs, and, sitting down, strapped on the sandals. Walking around in them, she looked even hotter than she had before. I found myself really desiring her, and wondered where things would go between us. She stopped in front of the mirror and looked at them from every angle.

“You’re right,” she said. “I think I’ll get them.”

We looked at a few more pairs, and I found some low-heeled beige Rapallo slides that were great for dates with Jake – they weren’t so high that I would be taller than him. As we were putting our shoes back on to go, she said, “I love your macramé sandals. I’ve been thinking about getting a pair but don’t know how they would fit. We’re about the same size, could I wear them for a while?”

“Sure,” I said. I watched her strap them on, my dick getting harder all the time, especially when I walked over and stepped into her clogs, and we walked out of the store wearing each other’s shoes.

We went over to the mall and looked around, but didn’t find anything that suited us. Tina said, “I’m getting hungry. How about lunch at Farrell’s?”

“Sure,” I said.

We walked up to Farrell’s, and stood in line for a table. We got one that was in a corner, so we could sit close together and talk discreetly. After the waiter took our orders and our menus, Tina reached down and took my hand again, and we started stroking each other’s fingers.

“This is so neat,” I said. “I can’t believe I’m sitting here with you, all dressed up in high heels and nylons, having lunch out in public. I feel so comfortable and natural.” And I can’t believe I’m wearing your shoes, I thought. God I’m so hard.

“We’ve got to do this again soon,” she said. “I know what would help with your constipation problem! How would you like to come to my exercise class tomorrow? My doctor suggested that I take up some exercise when I was complaining that I was constipated. It would probably help you too. It’s here at the mall, and it’s a women’s group, but there is a…. kindof sissy guy in it that doesn’t want to be in the men’s group, and the other women don’t mind. Why don’t you come along? We can bring guests.”

“That would be neat, but I don’t have any exercise wear,” I said.

“That’s OK. I’ve got a leotard you can borrow. We wear leotards with sheer to the waist pantyhose instead of tights, since it’s cooler, and footie socks and tennis shoes. Do you still have your sheer to the waist pantyhose?” she asked.

“No,” I said, “I’d have to get some. I bought some K-Mart Soft Smooth and Sheer pantyhose the other day, and they’re sandalfoot, but have a reinforced panty. I’m wearing them right now,” I added, giggling.

“You need something with a sheer panty, else it would show below the leotard. We’ll stop at Osco’s after lunch and get you some.”

After lunch, we went into Osco Drug and Tina led the way to the No Nonsense Pantyhose display. She picked out two pairs of Size B Suntan Sheer To Waist and handed them to me. She looked around to make sure we were alone, then lowered her voice and said, “Do you shave your legs all the way up? You’ll need to if you don’t.”

“I haven’t,” I admitted. “I was thinking of getting some Nair and using that, so I’ll be really smooth.”

I picked up some Nair with Baby Oil, and then we checked out, and walked out to her car. As we drove back to my house, we made small talk, and when we pulled into the driveway, she parked the car and shut off the engine. Turning to me, she put her hand on my shoulder, and said, “I haven’t had this much fun in a while. I can’t wait for tomorrow.”

She pulled my face to hers and we shared a quick kiss.

After I went back in the house, I laid around for while, basking in the great time that Tina and I had, and thinking about going in the bedroom and jacking off again, when I heard a car pull up in the driveway. I looked out the window, and it was Jake. A few seconds later I heard a knock on the door. I walked through the kitchen and opened the door for him. As soon as he got in, we were in each other’s arms, kissing deeply. As we broke apart, he asked, smiling, “Are you as horny as I am?”

“Mmmm-hmmm,” I giggled, coyly.

“How come?” he asked.

“Because I haven’t had sex for a week cause Becky’s having her period and I’ve had hose and high heels on all day and I feel so sexy and you’re so cute and I’m so horny and I can’t wait any more,” I said breathlessly, grabbing him and French kissing him again. Breaking apart, we giggled, and as we spun around, we knocked the cereal box off the counter. I squatted down to pick it up, and as I stood up, he said, “Mmmm, you are wearing pantyhose again.”

“Of course,” I replied. His hand grazed my derriere, copping a feel of my smooth curves, and then he grabbed my hand and we took off at a run for the bedroom.

This time, he undressed me. Sitting down on the bed, he grabbed my feet and brought them up into his lap. He took off my sandals, then my sweater, and then undid my button and unzipped my pants. I laid down and raised my hips and he slid my slacks off of me, then started caressing my nyloned legs.

I giggled, “So am I Soft Smooth and Sheer?”

“Oh, God, yes,” he said, putting his mouth on mine and French kissing me.

“I got so turned on this morning every time I looked down and could see my pretty toes in my sandalfoot hose in my sandals.” I French kissed him back. “Oh, baby,” I moaned, “play with my feet.”

He did, running his fingers all around my toes, and then tracing the toe seam of my pantyhose, which drove me mad. He brought my feet up to his face and started sucking my toes through my nylons.

“Your feet are so pretty. You have the cutest toes. I see why you need sandalfoot hose,” hepanted. My dick was so hard it hurt. I slid my pantyhose down to my thighs, and started to play with my huge erection. He quickly undressed, and as he turned back to me, I grabbed ahold of him and pushed him over on his back. I mounted him, and reached down and laid our dicks side-by-side.

As I laid back down on him, I kissed him deeply and started to hump him. When our lips broke apart, he said, “God, I’m so turned on. I want in your sissy pussy so bad.”

“Well, come on,” I said, smiling. I rolled on to my left side and bent my right leg, assuming the Fleet enema position, and reached back and pulled my butt cheeks apart with my right hand. He opened the Vaseline and lubed himself and then me, penetrating my anus with his lubed finger, and then guided his dick to me and gently pushed. I relaxed and he entered me. I gasped in pleasure as his big hard dick dilated me. I couldn’t believe how easily he got in me this time – it felt so natural. We immediately started thrusting together and Jake said, “Talk dirty to me.”

“Mmmmm, it feels so good with you up in my boi pussy.”

“I LOVE having long thick things up in my butt.”

“God, you’re so big and my pussy ass is so stretched out.”

That pushed us both over the edge. We came together, quickly and hard.

After we rolled apart, we snuggled back together. “I can’t believe this is happening,” he said. “You are SO hot. When I was here last time, and saw you wearing hose, it made me so aroused, but I thought I better not show it because it might turn you off. Then, when you said you were constipated, I knew that was my opportunity to get in your pants, er, pantyhose…..”

I wrapped my arms around him and said, “You can get in my pantyhose anytime.”

After he left, I slid my black slacks back on and laid around the house in my hosed feet.

When Becky came home, she said, “Wow! You look really nice. Did you have fun shopping with Tina? Did you get anything?”

“I got some white high heeled slide sandals. I also got some other things I need to ask you about.”

“Like what?”

“Well, Tina invited me to go to her exercise class with her tomorrow, if it’s OK with you. It’s a women’s class, so I’ll be with a bunch of women.”

“Okay, go on……..”

“They normally wear leotards with sheer to the waist pantyhose instead of tights, since they’re not as hot. Tina is going to loan me a leotard, and I bought some No Nonsense sheer to the waist pantyhose. I need to shave my legs all the way up since I’ll be wearing a leotard.”

“Okay,” she giggled. “I can’t wait to see you in a leotard.”

“Actually, I don’t have it. We’re getting dressed at Tina’s house before we go over there.”

To be continued................

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 morning, I lazed around the house until Becky left for school. Before she left, she said, “I got you out a gym bag to put your exercise things in. I put a towel in for you.”

“Thanks,” I said. “I need to borrow a pair of your footies too, to wear over my hose.”

“Sure,” she said, reaching into her drawer and getting out a pair and putting it in my bag. “What shoes were you going to wear?” she asked. “If you’re going to have hose on, you should wear your new clogs, since you’ll be kind of dressed up anyway.”

“Good idea,” I said, “actually that’s what I was thinking of wearing.”

She left for school, and I went back in our room to get dressed. Every time I moved around, I couldn’t believe how smooth I was! I picked up the bottle of Nair and was looking at it, remembering how erotic it was having Becky help me shave my legs. I started reading the package out loud, getting myself so aroused in the process. “Not for use on underarms or the perianal area.” I knew that meant around the anus. I put my fingers in my crack and felt around my anus. I did have some hair down there, which I didn’t like since I was so smooth everywhere else. I wanted to be clean shaven down there for Jake. I took my razor and squatted down on the floor, and carefully shaved around inside my crack.

After my shower, I dried off and put on the sheer to the waist pantyhose that Tina had bought for me, then put my tightest girl jeans on over them. As I was putting on my bra and my deodorant, I raised my arms and admired my nice smooth bare underarms in the mirror! I wore my beige knit sweater, and my new high heeled brown clogs. After a little while I started to feel the urge for a bowel movement. I went and sat on the toilet and had a nice, easy, satisfying BM. Finally, it was time to go. I drove on over to Tina’s and sauntered up and knocked on the door.

She opened the door wearing a striped blue leotard and STW pantyhose. She closed the door behind me, and gave me a hug. “Ready to get girly?” she asked.

Stepping out of my clogs, I said, “I already am.” Wiggling my pantyhosed toes, I added, “I Naired my legs yesterday and I’m sooo smooth. I’ve had the hose on all morning under my jeans, and I feel SO sexy!” I whispered.

She smiled. “Isn’t that the greatest feeling, feeling your nylons rubbing against your slacks? It’s almost as good as feeling the wind on your legs when you’ve got a skirt on,” she smiled.
She started back to her bedroom. “C’mon, let’s get dressed,” she called.

I followed her back to the room, enjoying the view of her sexy derriere in the close-fitting nylon. She pointed to a brown leotard laying on her bed. “There’s your leotard,” she said.

I unfastened my jeans and wiggled them down. I took off the sweater and pulled the wrinkles up out of my hose. I put on the leotard and fastened the snaps as she was searching her closet for something to wear. She pulled out a blue wrap skirt and put it on.

“How’s this?” she asked, waving a hand by her skirt.

“Hot,” I smiled, and she stuck her tongue out at me. I saw the denim miniskirt she had on yesterday laying on the dirty clothes pile, and immediately wondered what it would be like to wear it.

She read my mind. “Too bad that skirt is dirty or I’d loan it to you,” she said, wickedly.

I said, “Can’t I wear it anyway? Especially since it smells like you?”

“Sure, if you don’t mind it being dirty.”

I picked it up and wrapped it around me. Walking over to her full-length mirror, I struck a pose, and she came over and wrapped her arms around me. I responded in kind, and we stood there with our noses pressed into each other for what seemed like an eternity. She rubbed her hand over my back, and said, “So did you do your push job today, or do you need to try before we go to class?”

“I had one this morning. It was a good big one. About a half hour after I put the hose on,” I giggled. “How about you?”

“I had a really big BM a little while ago. I had a big bowl of bran cereal this morning for breakfast and then went in and put my hose on. I went and sat on the pot and it came right out. It felt soooo good,” she moaned. “Are your sneakers and socks in the car?”

“Yes,” I replied. “I really wanted to wear my clogs.”

“In that case, I’ll wear dress shoes too,” she said. She dug out a pair of footies out of her underwear drawer and put them in her sneakers. She sat down on the bed and put on the new sandals she bought on our shopping trip yesterday. I walked out to the door and stepped into my clogs. I felt so sexy, and scared, walking out in public in a leotard and a skirt. She walked up to me, and, putting her arm around me, said, “Let’s go!”

We parked at the Target end of the mall and walked up to the meeting room on the second floor where the class was, my clogs clicking on the hard floor, and I hoped my erection wouldn’t show and give me away.

We had a great time. The other women didn’t even give me a second glance after Tina introduced me as Brie. Trying to act as nonchalant as possible, I stepped out of my clogs and skirt like I’d been doing it for years. I put Becky’s footies on over my nyloned feet, slid them into my sneakers, grabbed my towel out of the bag that Becky had gotten for me, and we all walked into the classroom. I tried to remember to walk like a girl. After the class, Tina said, “How about lunch again?”

We changed clothes and went back to Farrells, and even got the same table again. We sat as close together as we could, and I could feel her nyloned legs rubbing against mine.

We shared a lot of girly small talk, and then she said, “I just can’t get over how what a natural girl you are.”

“Like I said, I’ve been doing it for a long time. Since before I was a teenager.”

Slyly, she said, “It’s so sexy that your mom feminized you like that.”

“It wasn’t just her. My sister-in-law got in on it too and was putting me in hose and high heels, then in dresses. I spent a month at her house during the summer between 9th and 10th grade and she dressed me as a girl every day. I went to work with her every day in a skirt and heels! I dressed some in front of a gay friend of mine and then, when he wanted to go to a formal dance and couldn’t find a date, he and his mom asked me to go with him. She took me out and got me a dress and lingerie. I wound up spending the night at their house and sleeping with him. I came out to Becky that I’m a crossdresser and we’ve gotten dressed up and gone out several times as girls. I’ve been doing it so much it just feels natural.”

Talking about it was getting me so hot again. I slid my foot out of my clog and started rubbing my barestockinged toes against her leg. She reached down, slid the strap of her sandal off of her heel, and, pulling her foot out of it, slid her foot up and down against my leg. The sexual tension between us was so thick you could have cut it with a knife.

She finally broke the silence of that beautiful moment, saying, “You look so cute in my skirt. We need to go shopping again and find you a denim mini like that. They go with everything.”

The thought of having a skirt of my own, and wearing it, got me aroused again. I said, “I can’t believe I’m sitting here in public, in a restaurant with you, in a skirt and heels. It’s like a fantasy come true. I don’t want it to end.”

She smiled. “I don’t either. Well, what do you think? Would you like to come to class again next week?”

“Sure,” I said. “Maybe we should go shopping and get me a leotard of my own. I was going to stop at the store and get some footies too, these are Becky’s that I borrowed.”

“Okay, Let’s go down to the Danskin store and we’ll get you one.”

After we paid our bill, we went down to the Danskin store and looked at leotards. She held up a really cute long-sleeved one in teal up to me and said, “You would look so cute in this. Why don’t you try it on?”

I went in the changing room and put it on, then walked back out in the store in just the leotard and pantyhose. Tina saw me and walked over. “Wow, that’s cute on you. How does it fit?”

“Okay,” I said, “about like yours.”

We paid for it and then walked out in the mall. I headed over to Ayr-Way and we went into Women’s Hosiery and I picked out several pairs of footies. As we walked past the shoe department, they had ladie’s sneakers on sale. I picked up some in teal and white that matched the leotard pretty closely.

Back in the mall midway, Tina put her arm around me as we were walking. She asked, “Why don’t we go back to my place?”

“Sure,” I said, wondering what she had in mind. We walked out to her car, and after she unlocked the door, turned to me. She closed her eyes and leaned forward. Our lips met and we kissed for what seemed like another eternity.

“Oh, Tina, I want you so bad,” I whispered.

“Me too. I haven’t fucked in ages,” she whispered back.

We got in the car, and drove back to her house with our hands on each other’s knees. Tina said, “So tell me about your boyfriend. Is he cute?”

“I guess,” I giggled. “A little nerdy, but cute.”

“Does he have a hot bod?”

“Yeah, he does. He is built pretty well. We spent the night together after that formal dance. That was my first gay sex. It made me feel so totally feminine.”

We parked the car and practically ran into the house. As soon as we closed the door, we were in each other’s arms again, French kissing this time. Pausing only long enough to step out of our heels, we kissed again and again. When we got in the bedroom, we took off our skirts and fell on the bed together. We took off our leotards and I began to kiss her lovely breasts. My dick was huge and, trapped in my pantyhose, was really hurting. I slid my hose down to my thighs to release it and she did likewise, pulling one leg out so she could spread her legs all the way. She laid on her back, spread her legs, and started to rub her pussy as she moaned.

“I’m imagining you in your Young Organist’s outfit, but you’re wearing white strappy high heeled sandals with your white slacks, your pantyhosed toes on display for the whole world to see, with your painted toenails showing through your sandalfoot nylons. You are so totally a girl.” She was making me so hard I thought I would cum any moment.

“Mmmm,” I moaned. “When I was wearing the uniform, I noticed people staring at my feet a lot. I always wondered if they were looking at my girl shoes or wondering if I had hose on.”

“They were probably noticing both, and, trust me, they knew you had hose on. They were probably wondering if you had panty hose on or just knee-his.”

I closed my eyes and snuggled up next to her. “They were actually women’s slacks and they were kindof tight. It felt so sexy having pantyhose on underneath them. They were so sheer I had to wear sheer to waist pantyhose. Mom said I needed to have a ‘smooth line’. Now I’m imagining what I would have looked like in strappy white sandals with my pantyhosed toes showing,” I said. I looked down and my dick was so erect and hard it was quivering.

“Your Mom had you wear panty hose so you wouldn’t have panty lines. God, that is so sexy! Oh, Brie,” she panted, “fuck me, fuck me hard.”

I mounted her and we became one, the feeling of our nylons rubbing together as I rode her quickly pushing me over the edge, and I came like never before. Afterward, as we snuggled together, Tina said, “Wow. I can’t wait for class next week,” giggling.

I changed back into my sweater and jeans and clogs to go home. I left them on and when Becky came home, she said, “Well, how did it go?”

“Great,” I said. “I really got a workout. They invited me back next week. Afterwards Tina and I went down to the Danskin store and got me a leotard of my own, and some sneakers and footies. Want to see?”

“Sure,” she said, running her hand over my back. “Mmmmm, you’re still wearing the bra.”

“Mmmm-hmmm,” I blushed. “I haven’t taken the hose off either,” I said, sliding my foot out of my clog and rotating it around, admiring my red nail polished toes showing through my sandalfoot pantyhose. “I wasn’t going to change as long as we’re staying in.”

I got all the new clothes out of the bag and showed it to her. Becky said, “No problem. Mmmm, women’s sneakers even. They match the leotard really well.”

We laid around for the rest of the day, and then after dinner, we were sitting on the couch snuggled together watching TV. Our feet were together on the hassock, and when the show was over, we started playing footsie. She said, “You have always had such pretty feet for a boy.”

I blushed. “I love wearing girl jeans and clogs. I feel so sexy when I’m walking and you can hear them clicking on the concrete and everyone is looking at me. When I’m standing still, I love to slide my foot out of them and show the whole world that I have hose on under my jeans. Whenever I do, I get a… stiffie,” I giggled.

She said, “You look SO cute in girl jeans and clogs.” She turned to me and started tracing the outline of my bra with her finger. “Know what I want to do know?” she asked.

“Mmmmm, what?”

“I want to see what you look like in your bra. Let’s go in the bedroom.”

We did, and reached inside our underwear drawer and got out her really small pink nightie. “I’ll be right back,” she announced. She walked into the bathroom, and I shucked my jeans and sweater, and stretched out on the bed clad only in my bra and nylons. She came out of the bathroom wearing the nightie, put her clothes in the dirty pile, and sat down on the bed next to me. “Mmmm, sheer to the waist. My pretty husband looks so sexy in his bra and his nylons,” she purred. She started running her finger over the lace trim on my bra. “That’s such a feminine bra for you. Did the other ladies make fun of you?”

“No,” I said. “They accepted me. I think they thought I was a girl. They invited me back next week, that’s why I went and bought a leotard of my own.”

“Mmmmm. Would you like to wear your bra to fuck me in, or take it off?”

“I can take it off,” I said, smiling coyly. She reached behind me and unsnapped it, taking it off me and throwing it in the dirty clothes pile. “I’ll wash it when I do mine, so it’ll be ready for your next class.” She went back to tracing her finger over my back where it was. “Mmmm, my pretty husband has bra marks all over his back. Tut, tut. He must have had his bra on all day.” Her hands moved down to my legs. “Mmmm, so smooth. You must use Nair.”

“Mmmm-hmmm,” I replied. “I have to. I have to wear a leotard for class, and it shows off everything,” I giggled. I brought my lips to hers and we kissed deeply.

“I can’t wait to see my pretty husband in his new leotard next week. I expect to see you in it before I leave for school.” She raised her hips and took off her panties. “Now pull down your nylons, sissy boy, and come inside me.”

I climbed on top of her, entered her slowly, and then we started slowly moving together. I remembered how I looked this morning in class, in my leotard, bra, and hose, and my thrusts were getting faster and deeper till I erupted deep into her.

Sunday Morning Pantyhose XX
By
Tracy Davis

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

Tina and I were growing to love both our exercise classes and the time spent together afterwards. We’d usually go shopping and have lunch afterward, followed by a return to her house and some amazing pantyhose sex. One day, we went back to the Danskin store and went leotard shopping, and I got a medium brown one with a scoop neck, along with a pair of brown sheer-to-the-waist No Nonsense pantyhose to go with it. Another time, we went into Ayr-Way and I got a denim miniskirt just like Tina’s to wear to class. It was so sexy wearing a skirt to class over a leotard and nylons!

One day, as we were getting ready to leave her house, she asked me, “Do you think you could do anal on me this time? I just couldn’t get my BM to come out this morning no matter how hard I tried. Either that or it’s going to be the little pink pill tonight before bed.”

“Of course,” I said, wrapping my arms around her and feeling of her sexy nylon-covered bottom. When we got home after lunch, she went in the bathroom to try again for a BM and I got undressed, taking everything off but my panty hose. I walked over to the bathroom door and could hear her grunting, trying to force out her stool. I tapped lightly on the door and opened it, and found her sitting there on the toilet with nothing on but her panty hose, red-faced and grimacing as she was straining to move her bowels. I walked over and squatted down in front of her.

“Don’t strain,” I said. “Let me make it easier for you.”

“Okay,” she agreed. She got up and reached in the medicine cabinet for the Vaseline and handed it to me, and we walked back into the bedroom with her hose still around her thighs. She laid down on the bed in the Fleet enema position, on her left side with her knees bent, and I snuggled up next to her back. I took the cap off the Vaseline and put a gob on my finger, then gently slid my finger into her crack and put some on her anus, rimming her in the process. I got another gob of lube and put my finger back at her anus, whispering “Bear down a little so I can get in.” She did and I penetrated her, feeling her hard stool as I lubed her inside. Then I lubed myself, marveling at her gorgeous body as I lubed my big hard dick.

“Ready, sweetie?” I asked.

“Mmmm-hmmm,” she said, putting her right hand on her derriere and pulling her crack open. I guided my erection into her shapely bottom and up to her anus, pausing briefly before I tried to enter her. I felt her take a breath and hold it, and I pushed forward gently, easily entering her as she moaned, “Mmmmmmmmmm.”

Shifting around to get comfortable, I said, “Sounds like you like having long thick things in your bottom too.”

“Mmmm, I do,” she said. I thrusted gently in her and we quickly picked up each other’s rhythm. Tina really had the moves when we were making love vaginally, but she also did when we buttfucked. It was only a few seconds before our nyloned legs rubbing against each other and her anus contracting against my dick pushed me over the edge and I erupted into her. Within seconds her stool started to advance and pushed me out of her rectum.

“Oh wow, I’ve got to go now,” she said, quickly jumping up and running in the bathroom. Seconds later I heard her stool splash into the water and her giant relieved sigh. A few minutes later she emerged from the bathroom and stretched out next to me on the bed.

“Wow, that didn’t take long,” she giggled.

“No kidding,” I said. “Look at you, you’re gorgeous. My God, if I was married to you and came home every night to you dressed like this, you’d have to beat me off with a stick.” It was true. She was a beautiful woman, even in her mid-thirties. She was a little full-figured, but her breasts were still firm, and her ass looked fantastic, especially with pantyhose giving her a sleek line. I wondered what her husband’s problem was, but was afraid to ask.

“Oh, thanks. You’re too kind. Wish Tom still felt that way about me. I’d be all over you too. I can’t believe how turned on I got that day seeing you at the mall. I didn’t realize that seeing a guy in nylons and skimmers, trying on women’s shoes, would get me so hot.”

“Guess it’s a good thing I decided to get dressed up and go shopping that day.”

As we were snuggling afterwards, I said, “Sooooo….. can I ask you a personal question?”

“Of course,” she giggled, “after all we’ve done together.”

“You are such a hot, vibrant, sexy woman. You said you and Tom weren’t having sex anymore. Can I ask what happened?”

“I caught him fooling around on me. It was partly my fault. I was losing interest in having sex with him. I was starting to realize that I was bisexual. I was noticing that I was getting turned on by other women. And getting really turned on by girly guys,” she giggled. “In case you hadn’t noticed.”

“Thanks, thweetie,” I lisped, kissing her on the lips.

“We’ve decided to stay together for Erin. But he has his girlfriends, and I have mine,” she said, kissing me back. “Hey, I’ve been meaning to ask you if I can borrow your white pumps. I’ve got a wedding to go to this weekend and I wouldn’t have to buy some if I can use yours.”

“Sure,” I replied. The thought of wearing them after a real woman had had her feet in them immediately got me hard again!

Tina followed me home and picked up my white pumps. As she took them, she said, “Next week you’re going to wear these to class so I can see how my girly boi looks in them.”

“Okay,” I blushed, and then we shared a nice deep goodbye kiss.

After she left, I lazed around home in my leotard and denim skirt, wanting Becky to see me in it. A little while later she came home from school, and I met her at the door, but didn’t say anything. She looked at my quizzically and said, “Wow! You’re wearing a skirt! When did you get that?”

I giggled. “Tina and I went over to Ayr-Way after exercise class. She had been wearing a skirt to class and said it was a lot cooler after exercising than wearing jeans. We found one on sale so I thought I’d try it.”

“You look great in it. How do you like wearing it? I can’t believe my husband’s wearing a skirt! I might have to borrow it!”

A few days later, Jake invited me on a lunch date, and I decided I was going to wear a skirt and hose. I put on my Sheer Smooth and Silky pantyhose (since they didn’t need to be sheer to the waist), a bra, my pastel print shirt, and my denim miniskirt. I topped if off with my macramé platform sandals. When he knocked on the back door, I pranced through the kitchen in my platforms to answer it. His eyes bugged out when he saw me. “Wow, a skirt! You look so hot!”

We went to the mall for lunch. While we were sitting there eating, Jake asked, “So why are you so dressed up?”

“I got this skirt the other day, and I love it. I wear it to exercise class all the time. I just thought I’d get dressed up and wear a skirt.”

After we got back, we went in the house and sat down on the couch, and I swung my legs over his, still wearing my macramé platforms. He started running his fingertips over my hosed legs, and it was making me so hot.

“I couldn’t stop looking at your legs when we were at the mall. You’ve got such pretty legs. They’re so smooth. Do you shave them?”

“Mmmm-hmmm. I Nair them every week. I’m in that exercise class now, and since we wear leotards and nylons, you’d see my leg hair poking through if I didn’t shave. Every Saturday morning Becky and I Nair our legs and paint each other’s toes,” I said, sissily. “Then we shave our underarms. And I shave my perianal area for you.”

He continued to stroke my legs for a few minutes, then, without warning, slid his hand up my skirt at the same time his mouth came down on mine. I had had an erotic dream about him where he had taken me from behind, with me in really high heels and us standing up and holding each other. When we broke apart, I said, “Hang on. I’ll be right back.”

I jumped up and pranced into the bedroom. I took off my shirt and slid out of my skirt. I got out the Vaseline, and put a big gob on my finger. I pulled my pantyhose away from my bottom with one hand and put my other hand down inside my crack. I rimmed my boy pussy with my lubed finger, and then pushed the rest of the lube into my anus, moaning in pleasure as my dick got SO hard. I pulled my nylons back up, and then wearing just my bra, nylons, and platform sandals, I pranced back out into the hallway and he looked my way. I stuck my arm out and crooked my finger at him in a sexy “come hither” motion. He came to me and took me in his arms. Embracing, we French kissed again, and I said, “Want to fuck me standing up?”

“Mmmm-hmmm,” he agreed. I led him into the bedroom and closed the door so we saw ourselves in the full length mirror. I slid my pantyhose down to my thighs as he watched, and then he started tearing off his clothes. Naked, he approached me from behind and started nuzzling me. I giggled as he ran his hands over me, and then I said, “I lubed up already,” as I slid my hose back down for the second time.

His dick was standing at attention and he guided it into my crack. Sliding it around in the lube, getting more and more aroused, he aimed it into my anus and started to thrust playfully. He put his hands on my bra cups and started to pull me toward him, and I took a deep breath and bore down to open my anus as I bent my right knee, balancing on my other platform and he held me and entered my rectum. We both moaned in pleasure as he gently fucked me. It was so totally erotic as I watched us fucking in the mirror, my sexy legs and feet on display in my platform sandals, my pretty painted toenails showing through my sandalfoot nylons. I took my own dick and started masturbating in time with his thrusts, staring at my pretty feet, and it was only a few seconds before I climaxed, gasping as I shot my wad several feet away from me. As I climaxed my tightened my anus around his dick he came as well, shuddering, and I felt his hot semen fill my bottom. After a few moments, we relaxed and just stood there in each other’s arms, enjoying the post-coital glow.

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.

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.”

Jake called one evening and asked, “I’ve got to go back over to Center City to pick up my paycheck cause they didn’t have it ready when I got off work this morning. I thought you might want to get dressed up and go out. We could have dinner over there somewhere.”

The thought was tantalizing. “Sure. I’ll be over in a little while.”

I went in the bedroom and disrobed. It was really warm out, too hot for pantyhose, but I didn’t want to have panty lines either. I put on knee-high hose and put on my black slacks without underwear. Checking out my rear end in the mirror, it looked pretty good! I was worried about staining them, though, so I went in the linen closet, got one of Becky’s tampons out of the box, and slid my slacks back down and inserted it in my rectum. I put on my purple ribbed turtleneck and my black high-heeled strappy sandals, and left for Jake’s.

As I walked in his front door, he gave me the once over and said, “Mmmmm, you look so elegant in those black pants and sandals. You’ve even got pantyhose on.”

I answered, “Well, don’t tell anyone, but they’re actually just knee-highs. It was too hot for pantyhose, so I went commando.”

He smiled wickedly at me. “Mmmm, kinky. Let’s go.”

As we walked out to his car, I saw a few kids next door looking at me. I put my arm around his waist and walked heel-to-toe beside him, and I felt so sexy! Feeling the tampon in my butt as I walked added to the feeling.

After we got in the car, Jake said, “I need to stop at Jim’s and borrow his work keys. You can come in if you feel up to it, or just wait in the car.”

I was really feeling brave. “I can go in.”

As we walked in their front door, Jake introduced me to Lynn, Jim’s wife, and we sat down on the couch. We were making small talk discussing where we might go for dinner, and Lynn said, “You two look so nice all dressed up.” I saw her looking at my feet, and she said, “Cute shoes!”

I blushed and smiled, pointing my toe at her. “We thought we might go someplace really nice for dinner, so I got REALLY dressed up tonight. I even put on knee-high hose.”

She said, “I was thinking it looked like you had hose on.”

I smiled and blushed, “Mmmm-hmmm.”

We said our goodbyes and left. After we got to the fire station, Jake looked around, and said, “They’re out on a run. You can come in, there’s nobody here to see you.”

All the time we were in there, we were arm-in-arm, and I could feel the sexual tension building between us. After Jake found his paycheck, we got in the car to leave, and we started looking around for a place to eat. It was getting late on a weeknight, though, and everyplace was closed except for Taco Bell. We parked and went in, ordered our food, and then sat down in a booth. The air conditioning was really cranked up, and the plastic bench was freezing. I started to shiver.

“Are you cold?” Jake asked.

“Yes,” I said. “This bench is so cold, and I haven’t got anything on under these slacks.”

“I know,” he smiled wickedly. I crossed my legs and stuck my foot out in the aisle. I noticed people staring at it while we were eating.

After we finished, I cleaned up the table. I got up, pulled my sweater hem down, and strode purposefully across to the trash can, feeling people’s eyes on my derriere as I did so. I felt so attractive!

Back in the car, we headed for home. My feet were pinching, and I reached down and unbuckled my sandals and took them off. I looked at him and said, “Mind if I put my feet in your lap?”

“Sure,” he said. I swung them up and put them in his lap, and he laid his free hand on them, stroking my ankles, and feeling up my legs all the way to the elastic top of my knee-highs. It was so erotic, and I was so aroused. When we got home, he parked and shut off the car. He got out and came around to my side and opened the door for me. I picked up my heels and stepped out into his arms, and we embraced. As we walked arm-in-arm across the grass to the front door, I could feel the damp grass through my nylons. He unlocked the front door, and once inside, we threw our arms around each other, kissing deeply. He took me by the hand and we ran up the stairs to his bedroom. We kissed again, and fell down on his bed together.

His hand went to my crotch, and he started groping around. “Where’s your zipper?” he asked.

I giggled. “In the back, silly. They’re girl pants,” I said, rolling over so he had access to my ass. He found the tab of my zipper and pulled it down. He grabbed the waistband of my pants and pulled them down and off of me. He saw my tampon string hanging out of my crack and said, “You’ve got a tampon in?”

“Mmm-hmmm. I was worried about staining my pants since I’m not wearing underwear.”

“Oh. So are you, um, regular?”

“Mmm-hmmm. I had a BM this morning.”

“In that case, why don’t we suck each other off?”

“Sounds great to me.” We wrestled around till we were in the 69 position, and started giving each other head. The salty taste of his semen aroused me even more, and we frantically sucked at each other, cumming within minutes.

After our next exercise class, we were all hanging around at Orange Julius, having our smoothies, and Melissa, one of the girls in the class, said, “I’ve been thinking. We should all do a dress-up lunch. Is everyone free next Monday? We could go to Café Americain, I’ve heard their food is really great.”

Tina said, “I’ve been wanting to try that place too! I’m in.”

Julie said, “Me too! I got this really cute peach dress I’ve been looking for an excuse to wear.”

Melissa looked at me and said, “How about you, Brie? Are you free Monday?”

I blushed and stammered, “Um, sure. I’d love to come.” I saw Tina look down at her drink and smile.

After we got into Tina’s car, she said, “I can’t wait to see you in a dress! Do you have one? Do you need me to loan you one?”

My head was spinning with the thought. “Um, let me ask Becky first and see if I can wear something of hers.”

Tina laughed, “If she doesn’t have anything, call me. We might have to go dress shopping!”

-----0-----

That night, after dinner, I finally worked up to courage to ask Becky. I said, “Ummm, I need to ask you a question.”

“What, hon?” she asked.

“Today at exercise class, when we went out for smoothies afterward, one of the girls asked if we wanted to do a dress-up lunch next Monday. Everyone said yes, and it sounds like they’re wearing skirts and dresses. They asked me if I wanted to come, and I said yes. Is that OK? What am I going to wear?” I asked, panicky.

Becky giggled. “Well we’ll have to see if I have something that will fit you. Of course you can go. This should be fun,” she laughed, wickedly.

-----0-----

The next morning when Becky was looking through her closet for something to wear, she pulled out her fuchsia sweater dress. “This is what you should wear on Monday!” she said. “It’s stretchy and should fit you okay. You can wear it with your white slide sandals and a white necklace. It’ll be short on you though, you’ll have to keep it pulled down so you’re decent,” she giggled. “You can wear one of your sleeping camis for a slip.”

-----0-----

On Monday, we slept in, and when I got up, I put on a pair of sheer-to-waist pantyhose under my sleeping cami and dressing coat and went out into the kitchen, just like I used to do in junior high. When Becky saw me, she looked at my nyloned legs and sang, “Oooh, you’ve got legs!”

I grabbed the hem of my dressing coat and pranced around, singing, “The super-stretching, super-fitting pantyhose,” and we both laughed. “Actually,” I said, “They’re No Nonsense sheer to the waist,” as I daintily pulled the side of my dressing coat up to my hip and showed off my sheer thigh.

“I know,” Becky laughed. “I just couldn’t resist teasing you.”

“Since I’m going to wear a dress today, I thought I might as well just put hose on instead of underwear,” I replied.

Becky had brought out her fuchsia nail polish, and after breakfast, she did my nails and we let them dry while we had another cup of tea. I went in the bathroom and had my BM while Becky went in the bedroom and got out her makeup, and then she really did me up. I always wore some powder and lipstick to the exercise classes, but Becky went all the way with foundation, blush, lipstick, eyeliner, eye shadow, mascara, the works. I couldn’t believe how pretty I was! Then she took the dress out of the closet and slipped it over my head. It was pretty short. I was glad I went with sheer-to-waist pantyhose.

After parting my hair and putting it in place with a little hair spray, Becky slipped a set of white beads over my head, and handed me a set of matching clip-on earrings and a bracelet. I stepped into my high heeled white slide sandals and walked over to the mirror. I couldn’t believe how pretty I looked.

“You’re going to have to beat the guys off with a stick. What are you going to do if some guy asks you out?” she laughed, wickedly.

“Um, say no,” I replied. “Do you really think someone would?”

“With that short dress and those legs, yes,” she warned.

We went back out in the living room and watched TV until Tina pulled up in the driveway. “Have fun and tell me all the details when you get home,” Becky laughed. “If some guy hits on you I want to know all about it.”
I picked up my purse and walked out the front door. I immediately felt the breeze on my legs and pulled the hem of my dress down. As I got into Tina’s car I carefully folded my legs in while keeping my knees tightly together, but I still felt like I was showing a lot of leg. Tina took one look at me and said. “Wow! Look at you!”

“Thanks,” I blushed. Tina was wearing a short black-and-purple dress with black hose and black pumps. “You look absolutely delicious too.”

“We’ll have to stop back at my place afterwards,” she smiled wickedly.

When we walked into Café Americain, Julie and Melissa were already there. Julie was wearing her peach dress with beige high heeled sandals and nude hose. Melissa had on a short grey pleated dress with taupe hose and black high heeled sandals. It looked like we were all on the prowl! We had a great lunch together. Afterward, we went in the ladie’s room and tinkled and fixed our makeup. When we were standing out in the parking lot afterward, talking, getting ready to leave, I saw the sun was reflecting off my smooth pantyhosed legs and I felt so sexy. It was hard to stop staring at my own legs! Finally we said our good-byes and got in our cars to leave. The minute we got in Tina’s car, we were in each others arms, French kissing with our hands on each other’s legs, feeling each other up under our skirts. Needless to say, we had some awesome pantyhose sex when we got to her house!

A few weeks later, Jake asked me to go to a wedding with him. We had to get REALLY dressed up, and I decided to wear Becky’s fuchsia sweater dress again. She had to work all day so she agreed to let me go with Jake. We moved our weekly Nairing our legs and painting our nails session to Friday night so I’d be ready for Saturday.

After a leisurely sleep-in and breakfast, I went in and took my shower. After I dried off, I went back in the bedroom and got out a new pair of suntan No Nonsense Sheer To Waist Pantyhose out of my drawer. I tore open the package, took them and out stretched them out, slid them on my legs, getting my usual pantyhose erection with the silky feel of them on my legs. I started to feel the urge for my morning BM, so I sat down on the pot and spent some time pushing, but I couldn’t get anything to move, despite the urge getting stronger. I finally gave up and went out into the bedroom and stepped into my high heeled sandals. I went back in the bathroom and sat down on the toilet, and spent about twenty minutes pushing and straining harder to see if I could get anything moving. No luck. Now I started getting worried. I didn’t want to go to a dressy formal affair and try to feel and act pretty with this great big load in my butt. What I needed was Jake’s dick up my butt to get me going.

I sashayed back into the bedroom and picked up the phone and called Jake.

“Hi sweetie,” I purred, trying to sound as sensual as possible. “Do you think you could come over here now?”

“Sure,” he said, eagerly. “What did you have in mind?”

“I really need you up in my butt. I’m constipated. I’ve been trying as hard as I can but my poop just won’t come out.”

“Mmmm,” he moaned. “I’ll be right there.”

Twenty minutes later, there was a knock on the door. I pranced out into the kitchen up on the balls of my feet, with nothing on but my nylons. I peeked around the corner of the kitchen to make sure it was him, and it was. I pranced over to the door and opened it, and jumped into his arms as soon as he got in the door. We shared a nice long kiss, and then he turned me around and put his arms around me as he nuzzled my neck. His hands dropped to my sides and he started to stroke my pantyhosed hips and thighs with his fingertips, and I moaned in pleasure.

“When was your last bowel movement?” he asked.

“Yesterday,” I said. “It really wasn’t very hard. I don’t know why I’m so plugged up this morning. I could have taken my Correctol last night if I had known it was going to be this hard to go.”

“Sounds like you need a good thorough buttfucking.” He brushed my hair out of my eyes. “C’mon, we’ll make it all better for you.” He led me into the bedroom, and I handed him the Vaseline before I pulled my pantyhose down and laid down on the bed. “It’ll be alright,” he whispered. He took the Vaseline and really lubed me up this time. He penetrated my anus with his slippery finger and slowly slid it in and out of me as I writhed and moaned in pleasure.

Finally he lubed himself and he snuggled up to my back, and then guided his erection into my crack and up into my boy pussy. I took a deep breath and bore down to let him enter me. His erection felt so good going up in me, and I relaxed into his arms as he thrusted in me. He gasped as he came in my rectum. Running into the bathroom, I sat down on the pot and finally did my BM. After I flushed, I went back in the bedroom and sat down on the bed. Jake put his arms around me, gently holding me and kissing my hair. “Thanks,” I said. “It was sure nice to move my bowels again.”

Looking down at my feet, he said, “Mmmm, sheer sandalfoot hose. Your toes look delicious.”

“Mmmmm-hmmmm. Like the ad says, they’re sheer from tummy to toes pantyhose,” I giggled, as I rotated my ankle to show off my foot.

While Jake watched, I finished getting dressed, doing my own makeup this time! Finally I stepped back into my high heels and we sashayed out the door.

We had a great time at the wedding, and I danced with several cute guys. As we left the reception, Jake and I put our arms around each other in the parking lot, and he put his hand up my dress and caressed my right butt cheek, exposing it to view through my sheer-to-the-waist pantyhose, but nobody was looking. After we got in the car, I pulled up my skirt and pulled down my pantyhose, releasing my huge erection.

“Oh Jake,” I moaned, “I’ve been so turned on since our fuck session. Suck my dick, and do it now.”

He bent down over me and took my dick in his mouth, sucking me off, and I came seconds later. As we drove home, I put my feet in his lap, and he slid off my high heels and caressed my pretty painted toes all the way home.

-----0-----

After he left, I took off the dress and put girl jeans on over my hose. After Becky got home from work, she said, “Mmmmm, you’ve still got your hose on! So tell me how it went!”

I did, telling her about dancing with the cute guys, but leaving out the part about Jake and I having sex, of course. When I got done, she walked over to the closet, picked up the fuchsia dress on the hanger, and said, “You know, I think this dress just officially became yours,” she giggled.

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

A few other vignettes that I had forgotten about……..

One day when my Mom and I were clothes shopping, she said, “It’s so hard to find jeans that fit you because you’re so slender, how would you like to try a pair of girl’s jeans? You couldn’t wear them to school, but you could wear them on weekends, like on Sundays after church.”

“Mmmm, sure,” I said. We walked over into the teen girl’s section and got a pair of girl’s size 14 Tall jeans off the rack. She looked into the fitting rooms to make sure they were empty, and had me go in and put them on. They fit perfectly! I couldn’t believe how tight and sleek they felt. They had flowers embroidered on the back pockets and they were so cute! I kept turning around and admiring them in the mirrors. “They are so pretty!” I said. “Can we get them?”

Finally Mom said, “Okay, I guess these are keepers. Put your other pants back on and we’ll take them.”

The next Sunday, after we got home from church, I went straight into my room and took off my dress slacks and put on my new jeans, seeing the frilly “Girls Size 14 Tall” tag on the inside, loving the smooth feel as I slid them up over my pantyhosed legs and bottom, admiring my girly bottom in the mirror and my nyloned feet sticking out of the legs.

One morning when Mom was getting ready for work, she came out of her room wearing the prettiest dress I had ever seen her in, asking, “Can you zip me up?”

“Wow!” I said, as I went behind her and zipped her up. “You look beautiful. Why are you so dressed up?”

“I have a lunch party to go to,” she laughed. “One of the other realtors is retiring.”

All day long at school I couldn’t stop thinking about how pretty she looked, and how I wished I could dress up like that. When I was sitting in one of my classes, daydreaming about it, I got an idea.

When I got home, I went in my room, closed the door, and got totally undressed. My weewee was stirring in anticipation. I reached in my underwear drawer and got out a pair of nylons and slid them up my legs. Now my weewee was standing at attention! I put on a white shirt and my best navy blue slacks, then got out “my” white high heeled sandals and put them on.

I went out in the kitchen and did my homework, then picked up the kitchen and set the table, enjoying the feel of walking in heels. I heard my Mom drive up, and when she came in the back door in her pretty dress and saw me, she said, “Oh wow! Why are you so dressed up?”

I blushed and said, “You were so pretty this morning in your dress, I couldn’t stop thinking about you all day, and I wanted to be dressed up and pretty too. Um, I want to ask you something. I thought maybe we could have a dress-up dinner. I cleaned up the kitchen and set the table.”

Mom said, “Well, actually, I was looking forward to getting home so I could get OUT of this dress.” When she saw the disappointed look on my face, she touched my hair and said, “Well, since I’ve had it on all day, I guess I can leave it on a little while longer. Since you’re all dressed up,” she smiled. “Since I need you to unzip me, you’ll probably hold me hostage in my own dress,” she laughed.

I smiled and bobbed in a curtsy. “Thank you, Mommy.”

She went on, “Oh, it’s going to cost you. You’re going to have to help me make dinner.”

“Of course,” I said. “I’d love that.”

We had a wonderful girly time together, making dinner, and she telling me all the compliments she had gotten on her dress. After dinner, we washed the dishes, and when we were done, she said, “Okay, dress-up time’s over. Unzip me so I can get out of this thing.”

She turned around and I unzipped her. Turning back to me, she opened her arms and put them around me and we had a long hug. “This was really nice, to have some dress-up time together. I like doing this too,” she said.

She went in her room and took off her dress and put on a robe over her pantyhose, but I left my good clothes and high heels on till bedtime, then took them off, went straight to bed, and had the most wonderful time pleasuring myself!

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

A few other vignettes that I had forgotten about……..

A few weeks later, Mom came home from work on a Friday night and said, “I really don’t feel like cooking. Let’s go out to for dinner. You should probably wear something nice.”

Great, I can wear nylons! I thought. As I was going to get dressed, Mom said, “You know, it’s dark outside, and it will be dark in the restaurant. How would you like to wear my heels outside? Nobody will notice.”

“Sure,” I said, my heart pounding.

I got dressed, and when I came out of my room, Mom had the high heeled sandals out on her bed already. “Here you go,” she said. “Remember how to walk in them?”

I put them on and we got ready to leave. When we walked out in the garage, I could feel the cold air on my toes, and knew they were on display!

When we got to the restaurant, I walked next to Mom, trying not to be self-conscious. We stood in line to wait to eat, but no one even noticed my heels and hose. I couldn’t believe I was standing there in public in ladie’s high heeled sandals and panty hose! It was a dream come true. My dick was getting so hard, and I forced myself to think about something else so people wouldn’t notice my erection. After we sat down at our table, I noticed a boy that was about my age sitting at the next table. I noticed he was staring at my feet. I wondered what he was thinking?

A little while later, they got up to leave, and his Mom looked at my Mom and said, “Oh hi Ruth, I didn’t realize that was you sitting there!”

Mom said, “Oh, hi Jackie! I didn’t see that you were sitting there either. Guess we had our backs to each other!”

They sat down at our table and started to talk. The boy introduced himself as Jimmy, and we made small talk. They lived in the next city from ours, about twenty miles away. I noticed he kept sneaking glances at my feet, so I decided to put on a show for him, crossing my legs and bobbing my foot up and down in my high heel.

When we got home, we took off our heels, and I handed them to Mom. She said, “You know, why don’t you just keep them in your closet. If I want them, I know where to find them.”

Wow, I thought. My SECOND official pair of high heels!

That summer, my Mom got a call one night from Jackie, the woman that we had met at the restaurant the previous winter with her son Jimmy. After they talked for a while, Mom came into my room and said, “Well, I have an interesting question for you. Jackie’s son Jimmy asked her if he could take ‘my daughter Brian’ to the fair with him.” She sat down on the bed next to me. “I told her that we’d talk about it. I guess we didn’t plan on this happening, did we? What do you think? Would you like to go with him? You don’t have to if you don’t want to. Obviously you’d have to wear girl clothes.”

The thought was so exciting, actually going out on a date! As a girl! “Um, OK, I guess,” I stammered. “What would I wear?”

“Well, it’s informal, so you could wear your girl jeans. And your Mary Jane flats, you wouldn’t want to wear heels to a county fair.”

“What top would I wear?”

She thought for a minute. “You could wear that white bodysuit I gave you. You could wear one of your sleeping camis underneath it, that would make it look like you had a bra on.”

“Wow, OK,” I said, hesitantly.

Mom called Jackie back and said I would go.

The next Tuesday was my ‘date’. When Mom came home from work, she had a package in her hand from the drugstore, and she handed it to me. “Here,” she said, “I got you something for tonight. It’s Secret deodorant. It’s for women. It’ll make you smell more like a girl.”

“Wow, thanks,” I smiled.

An hour before he was supposed to pick me up, I went in my room to get ready, my heart pounding in anticipation. I undressed and put on my Secret deodorant, enjoying the pretty scent. Then I put on pantyhose, a white cami, the white bodysuit, and my girl jeans. I stepped into my black patent Mary Janes and then went out and looked at myself in the mirror. I couldn’t believe how pretty I looked. Mom came out of her room and said, “Wow! Look at you!”

We went in the bathroom and she helped my do my hair, and then handed me a small purse. “Here, put your lipstick in here, along with some tissues. Remember you have to use the ladie’s room if you have to go potty. Remember to sit down to pee.”

“I will,” I said.

“Here, I have something else for you,” she said. She had a bottle of perfume in her hand, and she opened it, dabbed some on her finger, and then touched the sides of my neck. I immediately smelled the scent of the perfume, it was so nice!

“There, now you’ll really smell pretty. You should probably try to do your push job before they get here, so you don’t have to have one when you’re out in public.”

I took one of her women’s magazines into the bathroom with me, and after trying for a few minutes, I was able to have a bowel movement. I called Mom to wipe me, and as she was washing her hands afterward, we heard the doorbell ring.

It was Jackie and Jimmy, and after we said our goodbyes, Jackie drove us to the fair. Jimmy and I sat in the back seat together, awkwardly silent. I saw he kept staring at me. I hoped he liked what he saw!

We had a great time at the fair. First we went and bought tickets for the rides, and went on the grown-up scary ones. I felt afraid, but didn’t want to show it. I sat close to Jimmy. He was my protector, and told me not to be afraid. Then we decided to get ice cream. We sat at a table eating, and I crossed my legs and was bobbing my foot up and down. I saw Jimmy staring at it, and I started rotating my ankle around, making wrinkles in my nylons, showing that I had hose on! Jimmy looked at me and said, “Wow! You look so pretty! I’m really glad you decided to come.”

I gave him a big smile. “Thank you for asking me! This is really nice. I’ve never been on a date before. I guess this is my first,” I said, looking down and blushing.

After a few more minutes of awkward silence, he said, “Are you done? Let’s go look at the animals.”

“Sure,” I said. I picked up our trash and Jimmy took it and threw it away. When I stood up, I put my purse strap on my right shoulder, and when we walked away, I took his hand. He looked at me and smiled. He squeezed my hand in return, and my heart started beating fast. My dick got so hard, and I was afraid people would notice. I tried to think about something else so it would go down, but it was really difficult. When I looked down at myself and saw my girl clothes and nyloned feet, I got aroused. When I felt Jimmy’s hand, I got aroused. When we were walking and I felt my jeans sliding over my hose, I got aroused. What was a dressed-up sheboi to do? Finally I said I had to go the bathroom, and I went into a stall in the ladie’s bathroom, closed the door, and put my hand down my pants and straightened out my erect dick so it wasn’t in a bind.

We held hands for the rest of the evening and I imagined we were boyfriend and girlfriend! It was such a wonderful evening. On the car ride home, we sat close together in the back seat, holding hands. I laid my free hand on my huge erection in the dark, squeezing it gently so Jimmy wouldn’t notice. I was hoping for a chance to kiss him, but when we got back to my house, we all walked inside together so we didn’t get a chance. Darn!

After they left, I slid out of my Mary Janes, said goodnight to Mom, and went in my room. I slid out of my tight girl jeans and the bodysuit, but left the cami and the pantyhose on and went to bed. I imagined I was snuggled up to Jimmy in bed and we were making out. I started masturbating with one hand while I ran my other hand up and down my pantyhosed leg, imagining it was Jimmy caressing me, and I ejaculated so hard it hurt!

A few days later, Mom ran into Jimmy’s mom at a business meeting, and said that Jimmy just couldn’t stop talking about me on the way home. “She was so pretty and smelled so nice. And she looked so grown up! I saw she was even wearing nylons like you, Mom!”

Tracy Davis

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

Another vignette from my late teens that I had forgotten about, after I came out to Jake……..

The next week, Mom decided to go out with her friends for dinner the following Sunday. I had been thinking about Jake all week, and what he had told me. I really liked him, and I had had the whole gay/not gay argument in my mind many times over the years since I had started dressing. When I was dressed up around a guy, like Jason or Jimmy, and saw them get an erection when they looked at me, it made me feel so sexy and attractive. I started to think I was ready to take it to the next level with him.

Later that week, he called. We made small talk for a while, and after a pause, I said, “I’m going to be alone this Sunday afternoon, why don’t you come over and we’ll hang out?”

“Sure,” he replied.

On Sunday, after church, I left my white turtleneck and nude sheer-to-the-waist pantyhose on, and put my girl jeans on over them, like usual. After Mom left, I put on some understated makeup, just some powder and pale pink lipstick, and put on my white high heeled sandals. I spent some time just walking around in heels and getting in the femme frame of mind.

He arrived about an hour later. As I heard his car pull up, I got so excited and my heart was pounding. He came in the door and I closed it behind him. He looked me over from head to toe, and breathed, “Wow! You look great!”

“Thanks,” I giggled. “Come on in.”

He sat down on the couch and I sat next to him. We made small talk for a while, and then there was an awkward silence between us. I had crossed my legs and was bobbing my foot up and down in my high heel, and I noticed him staring at it. “Wow,” he said, “are you wearing nylons again?”

I knew it was turning him on. “Mmmm-hmmm,” I said. “I got dressed up for church this morning, and I haven’t taken the nylons off yet.” I extended my foot out and pointed my toe. “The…. hose,” I breathed, sensually.

We laid back on the couch, our noses only inches apart. I could feel his heart pounding. I knew he was as nervous as I was. Finally, he said, shyly, “There’s something I’d really like to do.”

“What’s that?” I asked, pretty sure I knew the answer already.

He paused. “I’d really like to…. kiss you,” he said.

I thought you’d never ask! I thought. “I’d like that too,” I breathed. We brought our cheeks together, and both tilted our heads awkwardly the same way twice, giggling. Then I tilted mine opposite his, and our lips met. His lips were warm and soft and dry and felt heavenly. We broke apart after only a few seconds, and he whispered, “Mmmmm, that was nice.” Our lips met again, longer this time. We wrapped our arms around each other and kissed harder and longer the third time. We shifted around as we kissed, and I felt my jeans sliding over my hose, and wiggled my pantyhosed toes in my sandals, feeling so totally feminine as we held each other.

We rolled apart, and I saw him looking at me again. “God, you are so pretty,” he said.

“You make me feel so pretty when you tell me that,” I laughed. I had never felt this way before. I knew what would kick it up another notch. I folded my legs over his, and said, “These heels are starting to pinch me. Would you take off my shoes please?”

“Sure,” he said. He reached down and undid the buckles, and then slid off my sandals. The feel of his fingers on my pantyhosed feet made my dick rock-hard, and it hurt. He said, “You have such pretty feet. Especially when you wear nylons.” As he stroked my feet, his erection was clearly visible through his pants, and he was shifting around on the couch trying to get comfortable. I giggled. I put my lips to his ear and whispered, “Are you getting…….. excited?”

He turned bright red. “Yes,” he hissed back.

“Me too,” I giggled. I reached down and unsnapped my jeans, pulled my pantyhose waistband out with one hand, and reached in my hose with the other and straightened out my erection. I thought his eyes were going to bug out of his head when I did it.

“Okay, now it’s your turn,” I whispered. I reached down and unsnapped his pants, and he sucked in his breath as I did. I slid down off the couch onto my knees as I found the tab and unzipped his zipper. I slowly reached in and pulled his underwear waistband down, then reached in and gently loosened his dick. It immediately sprung to attention.

As I crawled back up next to him, he moaned, “Oh, wow.” I giggled, put my arms around him, and kissed him again. As he put his arms back around me, I reached down and gently fingered his erection as he moaned in pleasure. When we broke apart after the next kiss, I whispered, “I know how to make him feel wonderful,” I cooed.

“How?” he asked, with a quizzical look on his face.

I got up off the couch. “Move back that way a couple of feet, and then put your legs up on the couch,” I motioned. He hesitated, and I said, “Don’t worry, I’ll be right here.” After he got situated, I judged the distance and sat down a few feet from him, bringing my legs up and putting my nyloned feet in his lap. I curled my toes around the head of his dick and started to give him a foot job. He smiled ear-to-ear. “Oh… oh…. oh,” he moaned, as I jacked him off with my pantyhosed toes. Hi dick was quivering, and starting to leak pre-cum. I knew he was ready to go over the edge. Suddenly, he gasped and quivered, and his dick erupted semen all over my nylons.

He totally relaxed back into the couch. Fortunately I had some tissues in my jeans pockets. I pulled them out and reached down and cleaned up my feet and his dick as well as I could. “Wow,” he said, “That was incredible.”

“Glad you liked it,” I grinned. I had never made a boy cum before! The feeling was overwhelming – there was no doubt that I really turned him on! He raised up and came over to me and kissed me again, then pulled back and said, “Okay, now it’s your turn.”

“What did you have in mind, naughty boy?” I asked.

He slid partway down to the floor like I had. He unzipped my zipper and opened my jeans wide. Reaching inside my pantyhose waistband like I had done before, he gently pulled it down and took my dick out. Bending down, he took it in his mouth. Oh my God I’m getting a blow job! I thought as he started to gently suck my dick. Looking around, I saw my pantyhosed feet spread wide, my high heeled sandals off and laying on the floor, and my jeans open and my pantyhose pulled down. A boy undressed me and we’re having sex! was all I could think as I shivered with pleasure and erupted in his mouth. A few seconds later, he rocked back and looked at me with a distressed look on his face, his mouth closed. He started to moan and point toward his mouth.

“Oh yeah, you probably want to spit that out!” I laughed.

“Mmmmm-hmmmm!” he nodded. I took his hand, and we ran to the bathroom with our jeans around our thighs, and he spit my semen into the toilet.

Afterward, we were back on the couch, clothes back on, holding each other, petting, and sharing the occasional kiss. “Wow, this was incredible,” he said, as we quietly held each other.
Gay – or not gay? I couldn’t make up my mind. Back then, I had never heard the term bisexual.

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

Here’s another one I had forgotten about. I must have been around 13 at the time. You girdle lovers will enjoy this one………..

When Mom had worn her really dressy dress, and I was zipping and unzipping her, I noticed she was wearing a girdle. I wondered what it felt like. The next Sunday, when we were sitting at the breakfast table in our robes and our nylons having our usual ‘girl talk’, I said, “Um, can I ask you something?”

“Sure, sweetie,” she said.

“Last week when you were wearing your dressy dress, I saw you were wearing a girdle.”

“Yes,” she laughed, “Most women my age need a little help holding things in.”

“I was just wondering if….” My voice broke off, I was losing my nerve.

Mom finished the question for me. “Would you like to try wearing one, to see what it feels like?”

I relaxed. “Um, yes.”

She smiled, “How would you like to wear one to church this morning?”

“Oh, wow,” I said.

Mom said, “Well, first you need to know the difference between different types of girdles. You can only wear a regular girdle under a dress or skirt. Under slacks, you have to wear a panty girdle. I have one you can borrow.”

“Oh wow,” I repeated.

“You probably won’t like how difficult it makes going to the bathroom, because you have to pull it down and back up. It’s a lot of work. Make sure you tinkle when you do your push job, so you won’t have to go again for a while.”

After breakfast, I went in the bathroom and did my push job. After Mom wiped me, I followed her into her bedroom. She went into her underwear drawer and got out her panty girdle and handed it to me. I took off my robe, then sat down on the bed and put my legs through the legs of the girdle and pulled it up. It was so tight! Mom helped me pull it up all the way. As we stood there, looking at me in the mirror, she said, “Well, what do you think?

“Mmmm, it is tight.” I ran my fingers over it, enjoying the feeling of it.

“Now go back in your room and put on your shirt and slacks.”

I finished getting dressed, and noticed how stiff and confining the girdle was. While we were at church, several people commented that I looked thinner, and I thought, that’s because I’m wearing a girdle! My faucet got so hard, but it was trapped in the girdle. You couldn’t even see that I was getting a stiffie!

When we got in the car to go home, I took off my penny loafers and socks. Mom smiled and asked, “So how do you like wearing a girdle?”

I frowned. “It’s really stiff and confining. I think I prefer just wearing hose.”

At home, I went in my room to change, and after taking my slacks off, I stood there looking at myself in the girdle and pantyhose. I felt so grown up! My faucet was ready to explode! I put my girl jeans on over them and then went out in the kitchen for lunch.

After lunch, I started doing my homework. I saw Mom go into my room, and when she came out, she looked at me, and said, “Do you still have my girdle on?”

“Mmmm-hmmm,” I said. “As long as I was leaving my hose on, I decided to just leave it on too.”

“I thought you were getting tired of it, that’s all. I thought you would have taken it off. It’s okay, you can wear it all day if you want.”

I said, “Okay, I might as well.”

I left it on all day, and found that it really was a pain to pull up and down to go to the bathroom. At bedtime, I took off my jeans, and looked at myself in the mirror in the girdle and nylons. I took a couple of tissues, put my hands inside the girdle and pantyhose, and straightened out my erection. I covered the head with the tissues, and then started to stroke it. It only took a few strokes before I erupted, finally giving my faucet the relief it needed! I took off the girdle and pantyhose and put on my camisole and panties to sleep in. I took the girdle and hose to the laundry room and put it in the basket for soiled delicates. When Mom came in to say goodnight to me, she said, “So I take it you’re not ready to start wearing a girdle all the time.”

I blushed. “No, I really prefer just wearing hose.”

“That’s OK,” Mom said, smiling. “You really don’t need one anyway.”

Postscript: If you had read SMP IV, about my joining Young Organists and Mom buying me a pair of sheer white Misses’ slacks to wear, we had a discussion about what I should wear underneath them so you couldn’t see my pantyhose panty. At one point, she said, “I may have to loan you my panty girdle again to wear under these.” I was SO relieved when we decided to just go with sheer-to-the-waist pantyhose instead!

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

Another little one I had forgotten about………

The fall after spending the month with my sister, dressing every day, I went into tenth grade. My class schedule had me taking gym during the second semester. During the fall semester I Naired my legs, shaved my underarms, and painted my toenails weekly. On the days that I didn’t go out in public, I wore Secret deodorant and the training bra! That Christmas I wore a dress and Char’s beige high heel sandals. Then after Christmas, I had to stop shaving my legs and underarms so I would look like a guy for gym. After a month, I felt so hairy and gross!

One Sunday morning when Mom and I were having our breakfast ‘girl talk’, I crossed my legs, and as my dressing coat fell away, you could see the leg hair under my nylons. “Ugh,” I moaned, “my legs look so gross. I need to shave them so bad.”

“It’s OK,” Mom consoled me. “No one can see it when you’re wearing slacks.”

“I know,” I moaned. “It just feels gross putting pantyhose on over the hair.”

“Oh well,” Mom laughed. “Only, what, four more months to go? Then you can go back to shaving them again.”

My last gym class was the day before the last day of school. As I was walking home, I was smiling ear-to-ear, and yelled out, “MY LAST GYM CLASS FOR-EVER!!!!!!!!” As soon as I got home, I went in the bathroom and took a shower, Naired my legs, and shaved my armpits. After I dried off, I put on my girl dressing coat and my Secret deodorant, and went into my bedroom and painted my toenails. When they were dry, I put on the training bra, white and red girl’s top, short girl denim shorts, and brown low-heeled woman’s sandals that Char had gotten me the previous summer. I went out into our back yard (behind the privacy fence) and just walked around in the nice warm sunlight, feeling like a girl again, and remembering the previous summer with Char! Marveling at the sun reflecting off my smooth shiny legs!

Late in the afternoon, I set the table for dinner. When Mom got home, I went out in the family room to greet her. “Ta-Da!” I said, extending my arms and legs.

“Wow!” she said. “Looks like someone shaved his legs!”

“And armpits! And painted my toes!” I said. “I am done with gym classes FOREVER! I’ve had my last,” lowering my voice, “damn GYM CLASS!”

“Okay, okay, I get it. I know you’ve never liked gym,” she laughed.

“Maybe if I could have been in the girl’s class, where I was more evenly matched, and not always overpowered, it would have been better,” I said. “And I could have still shaved my legs!”

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

Another little one I had forgotten about……… “My Piano Recital”

I had a piano recital coming up, and one night Mom came into my room with a bag from the mall. She said, “I got you something to wear for your recital. They’re Misses dress shorts. You could wear them with a dress shirt and nylons and high heels. It would show off your legs without wearing a dress.”

The thought was intriguing. She took them out of the bag and handed them to me. They were white with navy blue piping, and the label inside said “Size 0/1”. I took off my pants and put them on. They fit well, and came down to mid-thigh. “Oh, those look really cute on you,” she said. I could hardly wait to wear them out!

The concert was on a Sunday afternoon. I had worn pantyhose to church like always, and after we got home, I took off my church slacks and put on the shorts, then stepped into Mom’s white sandals and fastened the buckles. I walked out into the kitchen where Mom was fixing lunch. I couldn’t stop staring at my pantyhosed legs showing. “Oh, you look adorable!” Mom said.

“Thanks,” I said, blushing.

Mom said, “I got some light pink nail polish to match your light pink lipstick. It’ll make your nails look nice, and you’ll hardly be able to tell you have any on.”

After lunch Mom did my nails, and I had to be careful not to touch anything for a while. Finally, it was time to go. We went out to the car and I opened the door and got in like a lady, sitting first and then pulling my legs in. As we pulled out of the garage, the sun shone on my legs, and you could see the texture of my pantyhose. I wiggled my toes in my sandals, feeling so pretty!

When we got to the concert hall and we got out of the car, I could feel the breeze on my legs as I walked. It felt so strange, and I paused for a minute to get used to the feeling. Mom asked, “Are you OK?”

“Mmmm-hmmm. I can feel the wind on my legs. It feels weird!”

When we got inside, all the girls were wearing dresses, and several of them that also studied with my teacher, Mrs. Gerhold, complimented me on how pretty I looked! When it was my turn to perform, I was so nervous, walking across the stage with my heels clicking. I played my piece nearly flawlessly though, and got a nice round of applause when I finished.

There was a reception afterwards, and we had cake and punch. While I was in the serving line, the lady behind me touched me on the shoulder and said, “Sweetie, you’ve got a run in your hose. You probably want to put some nail polish on it.”

I blushed and stammered, “Um, OK, thanks.” After we got our food, we looked for a place to sit, and we sat down by Ingrid, another one of Mrs. Gerhold’s students that usually had the lesson right after mine.

She said, “You look so cute in your outfit! You have really pretty legs!”

“Thanks,” I giggled. “So do you!”

Mom sat down next to me, and I leaned over to her and whispered, “Someone said I had a run in my hose and I should put some nail polish on it. Do you have any?”

She frowned. “No, I don’t think I do. We’ll have to ask someone.”

After we got done, we got up and put our plates in the trash, and Ingrid said, “How would you like to take a walk and look at some of the artwork?”

“Sure,” I said. We walked toward the gallery, and Ingrid leaned close to me and said, “You know you’ve got a run in your nylons? You should put some nail polish on it.”

“Someone else told me that earlier. I don’t have any nail polish with me.”

“C’mon, lets go in the ladie’s room and I’ll fix it for you.” She took my arm and steered me toward the ladie’s bathroom. When we got inside, she said, “Lean against the couch and put your leg up on it.” I did, and Ingrid rummaged in her purse and produced a bottle of clear nail polish. She opened it, and I could smell the nail polish and felt the cool touch as she put some on the back of my shin. “There,” she said, “now it won’t get any bigger.”

“Thanks.” I said, blushing.

We walked back to the gallery, and spent some time walking around holding hands, looking at the pictures. We sat down to rest after a while, and we both crossed our legs. Looking down at our crossed legs, Ingrid said, “Your legs look so pretty in nylons. How long have you been wearing them?”

I blushed, “Since last fall when I started junior high. Mom said I was old enough to start wearing pantyhose when I dress up. I wear them under my slacks on Sunday mornings for church. This is the first time I’ve worn them out in public where you can see my legs.”

“You look great in them. How do you like wearing them?”

“I really like them. They make me feel really pretty. Especially today, I could feel the wind on my legs when we walked in, and they make my legs so nice and smooth. Just like yours.” After a pause, I added,
“I love how they feel when I cross my legs.” We both giggled.

“Your sandals are really cute. Where did you get them?” she asked.

“My Mom’s closet. She loaned them to me. I think it’s for keeps though since she told me to just hang on to them.”

“That’s great that you and your Mom wear the same size shoes so you can share. My Mom wears a bigger size so we can’t do that.”

Finally it was time to go. As we got into the car to leave, Mom smiled and said, “I had several people tell me how nice you looked! I saw you and Ingrid walking around holding hands.”

“Mmmm-hmmm,” I blushed. “She told me I had a run in my nylons and helped me fix it.” I twisted my leg around and saw the run. My pantyhose were suntan, and you could definitely tell I had hose on from the run!

Mom said, “That’s why you should always have nail polish with you, even if you’re not wearing any, in case you get a run.”

The car ride home was awesome, I felt so good being out wearing pantyhose all day! Finally we got home and pulled in the garage. As soon as Mom shut off the car, she said, “If you’re staying in, you can leave your outfit on the rest of the day if you like.”

“Mmmm, I think I will,” I said.

Afterward, I went in my bedroom and closed the door. I took off my heels and laid down on the bed. My faucet was so hard. I laid there, playing with it, rubbing my pantyhosed legs together, remembering the wonderful afternoon out in public in pantyhose, everyone complimenting me on how pretty I looked, and I erupted a huge wad into my pantyhose panty.

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.”

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.
I had forgotten about this story until the other day, when I saw the obituary for Mrs. Myers, the woman in the story who drove me to her church so I could play on Sunday morning. She lived to the ripe old age of 102. I wonder if, at the end, she still remembered driving a very effeminate teenage boy in women’s slacks and high heels to her church? – Tracy

The summer after tenth grade, I got asked to substitute organist at another church one Sunday when their organist was on vacation. Unfortunately, Mom had planned to go out of town to visit friends, and was trusting me to stay home alone and watch the dog. When we discussed it, Mom said, “I think Doris Myers used to go to that church. Maybe she could drive you over there that Sunday. I’ll call her and ask.”
Mrs. Myers agreed to drive me, so I was able to play. Mom left on vacation on Friday, so we moved our weekly legs-and-underarms shaving party to Thursday night. I was planning to spend the whole time she was gone in girl mode!
On Sunday morning, I got up and put on pantyhose first thing, like always. I was planning to wear my Young Organist’s Association uniform, with high heeled sandals instead of pumps, so I had to wear sandalfoot pantyhose. I found a pair in my lingerie drawer that were sheer-to-the-waist, slid my panties off and put them on, then went out in the kitchen for breakfast in my cami top and robe. After feeding the dog and letting her out, I poured myself a bowl of bran cereal and a glass of orange juice, and added Serutan to my juice. I hadn’t had a BM the previous day, and was feeling gassy and bloated. After breakfast, I went in the bathroom for a BM. I got a magazine, went in the bathroom, pulled down my pantyhose, and sat on the pot to try to go. I took a breath and pushed, but I just could not go. I really wasn’t feeling the urge to evacuate, even though I was so bloated. Finally I gave up and pulled up my pantyhose. I opened my girl drawer in the vanity and got out my Secret deodorant. I stretched my arms up over my head and put it on my nice smooth underarms!
Walking back into my bedroom, I took off my robe and cami, got one of the lacy, frilly bras that Char had bought me the previous summer out of my lingerie drawer, and put it on. I stuffed it with a pair of pantyhose to give me a figure, then put the cami back on. I got my YOA uniform out of the closet, took the white misses’ slacks off the hanger, and slid them slowly and sensually up my pantyhosed legs and bottom. I tucked in the hem of my cami and fastened them, then got out my white turtleneck and put it on. I did my hair and makeup, then put on the blazer. I got my purse and sandals and put them by the chair in the foyer, and got my music together. I went back and put on my sandals just as Mrs. Myers was pulling in the driveway. I locked the house and got in her car. Even though I was wearing slacks, and not a skirt, I got into her car the girl way, sitting down on the seat first and then pulling my legs in. “Wow, you look really nice!” she said as we pulled away.
When we got to the church, I went up to the organ while Mrs. Myers talked to her friends and got caught up. I sat down in a pew, took off my high heels and practiced. When it was about time for church to start, Mrs. Myers came and sat down in the pew next to me. During the sermon, I sat down in the pew next to her. I crossed my legs and started bobbing my pantyhosed foot up and down out of habit, and I saw Mrs. Myers staring at it! I smiled and wondered if she was thinking, Pantyhose or just knee-highs?
After church, I put my heels back on and then Mrs. Myers and I went out to the social hour. Everyone was very complimentary about how I played, and several people told me how nice I looked! When we got in the car to leave, Mrs. Myers said, “If you don’t have any lunch plans, how about if I take you to lunch on the way home?”
“Oh, that would be great. Thanks!” I replied.
We went to Denny’s for lunch. As we sat there perusing the menus, the waitress came over and asked, “So have you decided?”
I responded, “I think I’m just going to have a salad. I really need some fiber,” I added, blushing.
“I will too,” Mrs. Myers responded, and the waitress took our menus.
“Having problems?” Mrs. Myers asked.
“Mmmm-hmmm. I haven’t had a BM lately. I need a push,” I said.

After lunch, Mrs. Myers took me home. On the way home I made a couple of stinkies, and I clenched my bottom tightly and let them out slowly so I wouldn’t embarrass myself. After she dropped my off at my house, I thanked her profusely. I went in the house and let the dog out. I went in my room and took the blazer off and hung it up, and made another stinky. I started to feel the urge to evacuate, so I went in the bathroom in my high heels, and pulled down my slacks and pantyhose and sat down on the toilet. I took a breath and pushed, and pushed, and pushed. My poop was so big and hard. My erection was rock-hard and quivering, and I was afraid I was going to ejaculate. I shifted my weight over to my left butt cheek, reached back with my right hand and pulled my butt cheeks apart while I pushed. “Oh, I should have taken some Correctol last night,” I moaned. I didn’t think my poop was ever going to come out, but it finally did. It was such a relief! I flushed, then pulled up my pantyhose and slacks and washed my hands.
I went in my room and took off the YOA uniform and hung it up, my faucet hardening into an erection again as I slid my ladies slacks down my pantyhosed legs. I reached down into my pantyhose panty and straightened out my big hard erection. I walked over to the mirror and looked at myself in a bra and cami and pantyhose, remember my girly morning out dressed as a woman the whole time. How Mrs. Myers accepted me as a woman. How she was staring at my pantyhosed foot while I was bobbing it up and down on display. Finally I couldn’t stand it any more. I laid down on my bed, raised up my hips, and slid my pantyhose down to my thighs. I ran my hands over my pretty pantyhosed legs, looking at my pretty perfect legs and feet and nail-polished toes, my faucet quivering, ready to explode. I started running my fingertips over my erection, not pumping it, just gently stroking and titillating it, remembering that wonderful morning. “Oh, I got to be a woman out in public all morning,” I cooed. “I had pantyhose and high heels on.” when I suddenly exploded in climax. I didn’t realize it was coming so soon! After wiping up my semen, I rolled onto my side, closed my eyes, and took a nap.
When I woke up, I got up and went in my girl drawer and got out the red short shorts and the white-and-red top that Char had gotten me the previous summer when I stayed with her. I took off the camisole but left the bra and pantyhose on, since they were sheer-to-the-waist, and put the shorts on over them. The flat brown sandals completed the outfit. I looked at myself in the mirror and I was really rocking the ‘Daisy Duke’ look!
When Mom got home later that evening, she said, “Wow! You look nice. I bet you’ve been a girl all weekend!”
“You know it,” I smiled.

Sunday Morning Pantyhose XXXIII

By

Tracy Davis

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 bought me pantyhose and started encouraging me to wear them, and then it was all downhill from there. -- Tracy

Later that summer, I got a call from Jimmy, the boy I had gone to the fair with several years before. He asked me on a dinner-and-movie date. I was so flattered, but I also had so many questions. This is unchaperoned! What if he wants to make out? What if he finds out I’m really a boy? I said, “I’ll have to check with my mom. Why don’t you call me back later tonight?”
During dinner, I brought up the subject to Mom. She smiled and asked, “Are you really ready to go out by yourself as a girl?”
I said, “I think so. I’m just so nervous. What if he figures out I’m a boy?”
“Good question,” Mom replied. “You’ll just have to look as convincing as possible. And make sure he keeps his hands to himself.” After a pause, she said, “You know, it’s probably time we had a talk about what to expect on a date.”
“OK, go ahead,” I said.
“Well, you already know how to have sex with a girl. It’s going to be different when you’re the girl. As you know, girls have three holes that boys want to stick their faucet in – their vagina, their rectum, and their mouth.” She paused, and then said, “And since you don’t have a vagina, its going to be your mouth or your rectum.”

When he called back later that night, I got so excited, and had to work to keep my voice calm. We agreed to go out the following Saturday night.

When Saturday afternoon came, I got out my girl jeans and my white turtleneck top. I decided to wear my white high heeled sandals, so I put on sheer-to-the-waist pantyhose. After I got dressed, I walked into Mom’s room and put on a little of her perfume. When Jimmy rang the doorbell, I sashayed to the front door and opened it, feeling so excited! We walked into the family room, my high heels clicking on the tile floor. After he met my Mom again, we chatted for a few minutes, then Mom said, “Have fun you two. Be home by eleven.”
Jimmy said, “Of course. Nice seeing you again, Mrs. Carson.”

We had a great time at dinner and the movie. After the movie let out, I went to the ladie’s room and tinkled and refreshed my lipstick. When I came out, as we were walking to the car, he put his arm around my waist and I reciprocated. I saw him staring at my pantyhosed feet in my sandals. My faucet started to harden into an erection, and I hoped it wasn’t noticeable. After we got in his car, we just sat there and talked. I had never been out on an unchaperoned date before and wasn’t sure what to expect.
He finally broke the ice. “Brian, you are just so pretty. I’d love to go out with you again.”
We drove around for a while, and then he drove into an out-of-the-way parking lot and parked. “C’mon, let’s get in the back,” he smiled.
We got into the back, and he took me in his arms. I looked up at him, and we shared an awkward kiss. “Mmmm, that was nice,” I smiled.
We kissed again, and again, and then I felt the tip of his tongue penetrate my lips. I opened my teeth to let him in, and the feel of his tongue sliding in and out of my mouth was so sensual. The next time, I put my tongue through his lips, and he admitted me, and I explored his mouth with my tongue. Oh my God, this is heavenly. The next thing I knew, he had his hand on my breast, and was starting to squeeze.
Gulp. Oh no. Has he ever squeezed a real girl’s breast before? Does he know how it feels? Can he tell that my breasts aren’t real?
What should I tell him? I swallowed the lump in my throat, and wondered what to do. About that time, he let go of me, shifted around in his seat, and reached down in his pants. “Sorry,” he said, “I’m getting……… really hard and its starting to hurt. Just let me straighten it out.”
“Um, sure, no problem,” I giggled. Good thing you don’t know I’m having the same problem, I just can’t fix it like you did. I decided to push his hand away if he went toward my crotch, but he didn’t. We just kissed and necked, with his hand on my breasts. Finally, we ran out of time, and he took me home. He walked me to the door and I wrapped my arms around his neck, and we shared a nice long good-night kiss.
After I got inside, Mom said, “Wow, I guess things went well on your date. Are you going out again?”
“He’d like to. I’ve got a big problem though. We were making out tonight, and we didn’t go very far, but I started to panic when I realized what would happen when he figured out that I’m not a real girl. Then what do I do?”
“That’s a good question. If he is at all homophobic, he might react negatively, and we don’t want you to get hurt. You may just want to make an excuse the next time he asks you out if you don’t want to be around him if something bad happens.”
I started to tear up. “I know. I like going out with boys, but I really feel more comfortable around girls. Like Norma. And Char. And you,” I added.
Mom came over and sat down next to me. “That’s really sweet,” she said.
“Tonight after the movie, we were in the back seat of the car, and we were kissing and making out, and I started to get really hard,” I admitted. “I was afraid he’d notice. It was really pinching in my tight jeans, but I couldn’t do anything about it.”
Mom reached up and touched my hair lightly. “Sounds like you need to relieve some tension,” she said, smiling.
I smiled back, “I bet you do too.”
“Mmmmm,” she agreed. She took my hand and I stood up, and we walked back into her bedroom. I sat down on the bed and took off my high heels, then stood up, unbuttoned my tight jeans, and wiggled them down my pantyhosed legs. Mom shrugged off her dressing coat and we fell into each other’s arms, kissing, and then collapsed on the bed I pulled my pantyhose down to my thighs and mounted her, and we made slow, passionate love.

The next month was Christmas, and Char came to visit for a week. Since the spare bedroom was in ‘my’ end of the house, I was hoping maybe we could sleep together. When she arrived, I helped her get her suitcase into the spare bedroom. She was really chatty and touchy-feely like during the month we had spent together. She opened her suitcase and took out a really sexy lacy nightie, and held it up to her. “What do you think of this? I bought it just for this trip,” she purred. “I was hoping that you could sleep in my room.”
“Mmmm, that would be heavenly,” I smiled back. She put her hands on my waist, and I reciprocated, putting my arms around her neck. We pulled each other close and our lips met. We kissed, once, twice, and the third time was French. Our tongues danced in each other’s mouths, and my faucet hardened into an erection. When we broke apart, she pushed the door shut, then took my hand and led me to the bed. We stripped off our clothes and stood there facing each other in just our bras and panties. Looking down at my groin, she said, “Ooh, pretty panties,” with my hardening erection straining against the lace. She started running her fingertips over my bra, and said, “I think this is one of the bras I got you last summer.”
“Mmmm, it is,” I cooed.
“You wear it well,” she smiled. We stepped into each other’s arms for another hug and kiss, and then I felt her hands go up to my bra clasp and unsnap it. I reached back and unsnapped hers as well, like we always did the previous summer before we had sex. We broke apart and shucked off our bras, and pulled our panties down and off. We dived onto the bed, and she spread her legs wide. She pulled me on top of her, moaning, “Oh God I need it so bad. It’s been so long.”
I entered her, and we started to thrust together when Mom tapped on the door and opened it. “Oh!” she said, surprised. “I guess you two are getting reacquainted.” She pulled the door back shut and we resumed our efforts, hardly missing a beat. We fucked hard and fast, and quickly climaxed together.
After we got done, relaxing in the post-coital glow, she asked, “So do you have a boyfriend yet?”
“No,” I admitted. “I’ve been out on a date, but I was afraid he would freak out when he discovered I was a really a boy.”
She laughed. “You know what the solution to that is? Get him so turned on that he wants to fuck so bad that he doesn’t care that you’re a boy.”
I smiled. “OK, I’ll think about it.”
She said, “The reason I asked is that I got you a present to….. help when you start dating.”
“Now I can’t wait till Christmas morning.” I giggled.
“Well, I didn’t wrap it. It’s not something that you’ll want to open up under the tree in front of Mom, probably.” We got up and put our clothes back on, then she reached in her suitcase and got out a package. She handed it to me and said, “Here you go.”
I started to open the box, and she said, “It’s a dildo. Do you know what a dildo is?”
“Um, no,” I said as I took it out of the package.
“It’s a prosthetic rubber penis. It’s like a sex toy. Women use them to masturbate, when they don’t have a man around, to make it seem like they’re having sex with a man. You can put it up in your rectum to experience what it feels like when a boy sticks his penis up into your bottom. It will also dilate your anus to allow a boy to get inside you easier. I thought it would also help with your constipation problem. It’ll help open you up so you can pass a large hard stool easier.”
“Oh wow,” I breathed, as I looked at it. It did look just like an erect penis. Even after just having sex with Char, I started to get hard again from looking at it.
“After while, we’ll get out some lube and you can try it out. Do you have any lube?”
“Yes, Mom got me some. It’s in my purse. She also got me condoms.”

Later that evening, I saw Char and Mom whispering about something. A little while later, Char came up to me and said, “Why don’t you put your nightie on and come into my room. Bring your lube with you. Did you have a BM today?”
“Yes, this morning.”
“Good. I was going to have you go sit on the toilet and try to go if you hadn’t, so you’re empty inside.”
My heart starting to beat fast. I went in my room and got ready for bed, taking off my clothes and putting my nightie on over my panties. I got my purse and went back into the spare bedroom, where Char and Mom were waiting.
Mom said, “You’re really going to experience being a woman now. Lay down on the bed in the enema position. Pull down your panties, and lay on your left side. Bend your right knee up to open up your bottom.” I did, and then she handed me the dildo.
“You need to use LOTS of lube. Put some on your finger and lube your anus really well.”
I opened my purse and got out the tube of K-Y, opened it, and squirted some on my finger. I put my finger in my crack, located my anus, and rimmed it with the lube. I could feel my pubes stirring as I started to get an erection.
“Now, put some up inside you.” I squirted some more jelly on my fingertip, and located my anus again. This time, I relaxed and pushed my finger up inside my rectum and moved it around to distribute the lube. My dick hardened into a full-on erection.
“Now, lube up the dildo.” I squeezed the tube again, and smeared a bog gob of lube onto the head of the fake penis.
“Now, put the head of it inside your crack. Just get used to feeling it in there.” I maneuvered it slowly into my crack, steering it around until the tip was resting against my anus.
“Now, just relax. Imagine your boyfriend is spooning behind you, and he’s holding you and kissing your neck.” I closed my eyes and imagined making out with Jimmy, my date from several weeks before. I wonder what he’s doing tonight, I thought.
Char’s voice brought me back out of my reverie. “Now, gently push against your anus with the tip.” I did, and felt it start to open me up. It actually felt good! “Go slow. If it starts to hurt, stop. You might try releasing the pressure and then trying again, that may help spread the lube around.” I did, and then resumed slow pressure. I wanted it in me so bad! I felt myself opening up wider and wider, and then suddenly, it popped inside me all the way, with a little pain. “Oh! I think it’s all the way in!” I gasped.
“Not really,” Mom said. “You’ve got a few inches to go.”
I resumed gently pushing, and it slid farther and farther in me. Finally, the base was resting against my anus. “There!” Char said. “Now you’re in all the way. How does it feel?”
“Wow, it’s so big. It feels like I’m really constipated.”
“I bet,” Mom laughed. “It’s like having a really big hard BM.”
I relaxed and took a breath. The discomfort was passing. I playfully clenched my anus around it, and it started to feel sexual! “Mmmm, it’s actually starting to feel good!”
Char giggled, “Judging from that great big boner you have, I would say so!”
As I released my fingertips, I felt it start to slide back out of me, then I pushed it back in. I did that several times, and then said, “Wow, is this what it feels like to have sex?”
“Mmm-hmmm,” Mom and Char answered in unison, and we all giggled. Char said, “Now, roll back onto your back and take your hand away, and it will stay inside you so you can pleasure yourself.”
I did, and my hard-on was standing straight up! I took it in my hand and started masturbating, while Mom and Char watched. It felt SO incredible!
“You have such a pretty cock,” Char said. “Here, let me help you.” She bent down over me, taking my cock in her mouth, and went down on me. I was in sexual overload! It was only seconds before I climaxed, my anus contracting against the dildo, and then I collapsed into the bed, exhausted.
After a few minutes, Mom went into the bathroom and got some tissues. When she same back, she said, “OK, now push it out slowly.” I rolled back onto my side, grabbed the base, and pulled while I bore down and pushed it out of my rectum. I looked at it after it came out, and Mom wiped it off with one of the tissues.
“You need to wipe your bottom. Do you want me to do it?”
“Yes please,” I said. She put the other tissue and her finger into my crack and wiped me, cleaning the remaining lube off my anus.

After we cleaned off the dildo, Char said, “OK, here’s some sex basics for you. If you’re going on a date that you think might lead to sex, make sure you have a BM that day. Your boyfriend isn’t going to want to run into your stool with his dick. You may want to take a laxative the night before to just to make sure you go. Before you go on the date, lube yourself up well and put the dildo in your bottom for a while. That will get you opened up, and make sure you’re lubed inside. It’ll also get you in the mood for sex. And be sure and take lube! Offer to lube up your boyfriend before you begin. It’s a great opportuning for foreplay!” After a pause, she added, “And we’re going to want to hear all the details after you get home!”