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.
“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.
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