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!