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.