Why You Wear Your Sister's Clothes_ 🎀👰‍♀️ (Crossdressing Stories)

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The music started, and as I stood at the head of the aisle waiting, my sister's husband took my arm. Ready. Words failed me, but I managed to nod my head yes, even as I felt the sharp tightness of the corset holding me in. I watched as the bridesmaids started walking down the aisle, one by one, escorted to the altar, until at last it was my turn. 

I looked around, saw the people waiting for me. The flowers in my gloved hand contrasted nicely with my white wedding dress, all satin, lace, and baby pearls. I felt a tug on my arm and took the first step. Mary walked in on me just as I zipped up the dress, each of us staring at the other for a moment before my fear and her shock combined to make us both laugh. "Damn, you look good tonight. Better than the last time I saw you." "Thanks, Mary. Now please leave so I can finish getting dressed."

 She shut the door, her smiling face making me feel real good, but I could hear the laughter as it filled the room below, broken by the sound of glasses clinking, people talking, and music. Mom stood next to me in my room, holding my arm gently. "It's time, dear. You can't put this off any longer."

"Do I have to do this, Mom? I mean, just look at me."

"You look simply wonderful, and you know it."

She was right. Of course, I did look pretty good. But of course, I had spent almost the entire day making sure that I would. And now, all at once, I was scared to death. I didn't want to add to the laughter I heard from below. They'll know the minute they see me. Her only comment was, "It's time to go greet the guests now." I went with her, thinking of the last time I had gone out. A cacophony of noises sprang from the street: people talking, horns blaring, traffic going by, all accented by the flashing neon lights of the city.

 I was as ready as I ever would be, but I savored the jumble of the city for a moment longer before I picked up my purse and quickly stepped out of the car. Alone. I was taking a chance, but nobody knows me here and I felt safe enough. And as I walked down the sidewalk, I felt myself getting primed for the adventure of my life. My name is Jeff. I was 16 then, and I just made my first foray into the outer world dressed as a girl. When my folks left for the weekend, I took the opportunity to dress and go out. I had one extra bag that had all of my feminine clothes in it, and a small vanity case that had my makeup in.

 It tucked deep in my closet. And as I plucked them out of the closet, I found it irresistible and got dressed as Kelly once again. This time I went all out, and without the pressure of hiding, my makeup and hair came out perfectly. The blue sheath dress hugged my now feminine shape nicely, and I had my nerve up. 

I stepped out of the car, my heels clicking on the hard concrete as my feet propelled me down the sidewalk. The sounds and sense of the city were so different from the country, and like a sponge, I absorbed it all. The deli with the aroma of fresh sandwiches, the pizzeria and the smell of cheese as it melted to the thick crust, smog and tires, screeching, people talking, and music from a window. I loved it all. "Hey baby, what you doing?"

 I ignored him and continued my walk until I reached the theater. One ticket, a bucket of popcorn. Then I settled into the seat, the movie. I can't even remember, but that's not important. The fact that I left home dressed as a girl is what's important. After the show, on a whim, I stopped at the deli, let the counterman flirt a bit, and bought a sandwich, which I took home. Back home, I sat by the window and ate, luxuriating in my conquest of the night, and knew I would do it again. And soon. I had been dressing in my sister's clothes for as long as I can remember. Been caught a few times, of course, and now that I'm 16, you would think that I could at least manage to keep it quiet. But Mom had caught me again just last week. I stand five foot seven tall, with brown hair going blonde, blue eyes, and a slim shape. My sister had long ago planned this summer costume party, and when Mom caught me this last time, she insisted that I attend the party, but dressed as a girl. Of course. This will give you a chance to do it right, and of course I'll help you, and maybe Mary will too. 

I wanted to dress as well as I could, but in front of so many of my friends, that had me worried. But Mom had made up her mind, and to her it was a done deal, no matter what. I thought, you have a week to pick out your clothes, Jeffrey, and pick out a girl name for yourself. I already had one but didn't tell her that. Instead, I simply nodded my head yes. My sister Mary let me pick out the clothes I would need from her closet, then insisted that I do it right. "You might as well, Jeff, or everyone will laugh at you. Besides, I'll bet that this is exactly what you wanted to do for a long time, but were just scared to do it." Nobody knew about my trip to the theater, and I didn't tell them either. I picked the clothes off the bed and started to walk out when she asked me if she could help me get ready, but I declined her offer. If I asked anyone at all, it would be mom in my room. I set the clothes out and made a list of the things I knew that I would need. Mom and Mary wanted me to do the best I could, which is what I wanted as well. So the list was very complete. I made sure I had my money and left for the shopping strip. I spent almost 40 bucks buying things I had wanted before, but lacked the courage to buy them now. 

I had everything I needed. Back in my room, I used several ideas I had read and a few of the stories I found posted on the internet. Starting with bird seed and some old pantyhose, using a scale and some trial and error, I crafted two small bags of bird seed to use as breast forms. After that, it was three days of excruciating waiting, which gave me plenty of time to envision all sorts of ugly things that could happen to me the minute I appeared at the party as a girl. Finally, on Friday afternoon, and because Mom insisted, she helped me remove all of my body hair with a cream. Up to now, all I had ever done was shave my legs with a razor. But after a shower, I had no hair below my eyebrows. With a towel wrapped around myself, I pulled on the panties, picked up my box of makeup, and went into Mom's room. She watched me as I started my makeup. Then stopped me and showed me how to do it right. Each step of the way, from foundation and powder to eyeshadow and eyeliner. I'll admit that I never looked as good as right then in my room. She sat on the bed as I got dressed. 

Mom wanted to help me get dressed the rest of the way, but I told her I could manage, so she just watched me. I got out my padded panty brief and pulled it on, then the pantyhose, followed by a waist nipper. The dress went over my head easily, and Mom slipped the zipper closed for me. I stepped into the heels and went to the mirror to try my hand at doing my own hair, knowing full well it was hopeless. The best I had ever done was a ponytail. 

"Let me help you, Jeffrey. Come into my room and sit at the vanity." I went with her. Then, with a simple brush, some spray, and two barrettes, she managed to make my hair look very feminine. I added the jewelry Mom gave me and stood in front of the mirror. I looked better than I ever had managed before. Half of me wanted to just charge out of the room and have a good time, while the other half told me I was crazy to even consider it. 

Now, I was completely dressed, wearing a short sheath dress that was all red, black patent leather heels, and my hair, courtesy of mom, was done in a very feminine style. Chandelier earrings, a short necklace, perfect makeup, perfume, and bright red lipstick made it a done deal. And there I stood, ready. Certainly I was ready on the outside, that is. But inside, while that part of me said no before the outer part had a chance, it didn't matter really, because Mom took my arm and I let her, with some reluctance, lead me out of the room, then down the stairs. 

A few people looked at me, some of them my classmates, then they returned to what they were doing, not recognizing me at all. But my sister Mary did, mostly because she was expecting me, and she quickly came over to me. "Holy cow, you look great." Mary had never seen me dressed before, even though she knew I had borrowed her clothes a few times, and she was clearly shaken by the way I looked as her eyes roamed up and down my body. Mom said, "Mary, this is your sister Janet." 

I had not told Mom the name I had picked, which wasn't Janet, so she made this one up on the spot, or else she had planned on it all along before she said a word. And right at that moment, Mary's friend Steve walked over. And who is this delightful young lady? This is my sister Janet, and you keep your hands off. Steve knew perfectly well that Mary did not have a sister, and I watched as his eyes slowly widened when he put it together. I mean, wow, doesn't she look great? His voice was deep and clear as he spoke to me. I'll say, maybe even better than you, Mary. That earned him a frown from my sister and a whack on the arm. Be careful tonight, Janet, he said, or some guy will sweep you away from here. 

Hardly. Mary took my hand and we headed for the punch bowl. Like Mary, I had invited some of my friends to the party, but that was before mom suggested I dress this way. And those were the people I was worried the most about. Ken, my best friend, dressed as a pirate, walked over and casually slipped his arm around me before he asked Mary who I was. This is Janet. 

Janet. This is Ken. Without a pause, he said, "Let's dance." Then all at once, he had swept me into his arms and was leading me around the room. I was afraid to say anything because, well, just because I was worried about this whole thing, of course, but I felt I had to carry on the pretense, so I smiled and let him lead the way, hoping for the best. "You look familiar, Janet. Have we met?" What do I do now? I thought, "Not like this, Ken." It took him a bit longer than Steve, than all at once he figured it out. It must have been my voice or something. "You're Jeff." I nodded my head yes, expecting him to instantly let me go. He didn't. Instead, he pulled me and waited until the music changed. "Then you've done this before, haven't you?" Just, how did he know that? It was hard to smile at him, but I did my best. "What makes you say something like that, Ken?" 

"Because of the way you look." This didn't happen by accident, kiddo. No guy I know of could look the way you do unless they've had a lot of practice, and I mean a lot of it, or they really want to dress this way. Otherwise, you wouldn't look so good. Hell, look at Marcy over there. You make her look like the boy in a dress. Marcy, while definitely a girl, had a somewhat masculine build, wore her hair cut short, and usually wore slacks, but tonight she was trying hard to look pretty, even though she had on a dress tonight. She was supposed to be Alice in Wonderland, by the way. She didn't quite make it. She still looked uncomfortable and awkward in the dress, like I was supposed to be. She was struggling along in her dress while I was pretending, and Ken knew it, like me. Marcy was stuck with the person she was born with inside, and she didn't like dresses and never had, while I did. She could easily have come dressed as a male character and maybe even looked better. I knew exactly how she felt. "Let's go out on the patio and get some air, Janet." Ken took my arm, and even though I didn't want to leave the house, he held on and led the way with me. Following away from the crowd, I relaxed a little, still unsure why Ken had held me tighter while we danced, especially after he found out who I really was. Several other people were out on the patio. One of them, an old girlfriend of Ken's, Heather, shot daggers at me as we walked by. So obviously she had not yet been told who I was, and in some perverted way, I enjoyed that fact, that being with Ken made her angry. It helped confirm my femininity, at least to myself. Ken sat on the low brick wall and motioned for me to join him. Heather looks angry with you, Ken, because I broke it up, not her. His arm slipped around my waist and he moved over closer to me. 

Not sure what was going on. I sat still. Since we both know that you've been doing this for a long time, just how long have you been dressing as a girl, Janet? That was one question I did not want to answer, but he had figured it out anyway. So a long time, Ken, since I was little. I guess you had me fooled, and I've known you since we were kids, and I never had a clue. That was just about the best compliment I ever got, and savored every syllable. Wanna go to a show tomorrow, Janet? There's a new one at the Rialto. He asked me out. My very best friend asked me for a date. I can, you know that I'm not, I mean I can't, so why ask? He did not say anything right away, but looked around for a moment. But why? I'm not a girl. And you know it because we already know everything there is to know about each other. And you've turned out to be one very hot looking chick, still sitting close to him. Just how many times have you ever been outside dressed this way? A few, I guess. But I'm always very careful, Ken. I don't see why. You look terrific. A few of us are going on a picnic Sunday, Janet, and they asked if you wanted to go. I looked at Ken, who was smiling with that silly grin of his, and while I was ready to say no, she added, Ken, why don't you come too and bring her with you? 

It's going to be at San's Point at one. Before I could object, we'll be there, Mary, and thanks for inviting us. I can't do this, Ken. Sorry, but I'm not that sure of myself yet, especially in a swimsuit. It'll be all right, Janet, and I'll be here at noon to pick you up on Sunday. But why not come to the show with me tomorrow? I'm not sure about this, Ken, so I'll say no. I'll call you tomorrow about going to the show anyway, just in case you change your mind. Now I had one date for sure, maybe another, and I hadn't done a thing to encourage Ken in any way. By then it was too late to become anything but Janet in every way. Some kids had seen Ken kiss me. Now I was in the awkward position of damned if I went anywhere with him. One, because it would only confirm to everyone that I wanted to dress this way, and two, I was damned if I didn't go. All of this ran through my mind in an instant. Then looking at my sister, seeing her smiling, then at Ken with those soft brown eyes of his, I knew it was hopeless. I slowly nodded my head. Yes, great, she said, then went back in the house.

 I can't wait to see you in a swimsuit, Janet. Me either, Ken, me either. My sarcasm went right over his head and he simply smiled at me. Mom wasn't exactly smiling when she heard the news, but then she wasn't frowning either. I told you it would be fine, Janet, and here you are. A date for Sunday afternoon and tomorrow. I said, watching as Mary and Mom both let their mouths drop open. Ken asked me to the show. No, a big deal. Not a big deal. That only means he's very interested in you, Janet. Yeah, but interested in what? He knows that I'm not a girl. He just asked me to be polite. That's all. Then why did he kiss you for that? I had no answer, but Mom had not heard about that until Mary opened her big mouth. Ken kissed you and you let him. Then he asked you out. That's it for today. Hope you have enjoyed it. If you do, then be sure to subscribe for the next part of this story and show your support on Patreon. It looks like no transcription