r/CrossdressingStories

Okay so story time today I bought some lingerie because it's a weekend so why not I go in guy mode by the lingerie it all goes well. Later I go to a bar and the bartender also worked at said lingerie store and asked did my girlfriend like the set I tell her oh it's for me actually she goes no way I show her the side strap she then goes my boyfriend also crossdresses and proceeds to show me a pic so I showed her this pic and she said wow you're good at make-up and passable. We then talked about lingerie and compared different designs from different companies for 2 hours while I sipped some drinks so I had a pretty good day today girls.

The Thrill of the Heel by Juliet

Closeted is an apt word, seeing as, metaphorically, the things I loved most took place behind closed doors not meant to be opened by just anyone. More literally, though, the closet itself held my favorite things.

In high school, my best friend’s older sister had a closet full of shoes, bras, panties, dresses, stockings, hats, skirts, and more. All the things a boy, according to my family’s unspoken code of conduct, should never be investigating.

But there I was. Not just once, but again and again.

Every time I went to his house, I found myself stepping into her closet. It felt like being transported. Not to Narnia, but somewhere just as magical, mysterious, and somehow made for me.

Any time my friend invited me over, I jumped at the chance and often asked whether his sister would be there too.

He knew why I asked.

In fact, it was because she wasn't there that I was invited. He found her closet alluring too. Two teenage boys rummaging through his sister’s things would not have been acceptable in his household either. Luckily, his parents were usually at work, and she was often out with friends.

Every item held a special appeal, though for different reasons. I loved everything, but the high heels had a peculiar pull.

Putting them on flooded me with euphoria from head to toe.

I was never going to pass as a girl. I looked too boyish for that. But it didn’t stop me from slipping into her four-inch, cream-colored strappy heels, quietly opening the bedroom door, listening for voices, and finally braving the hallway.

The expected clicking and tapping of my steps on the hardwood floor told the story of my racing heart.

At the end of the hall, where the stairwell opened to the downstairs, my pulse quickened even more. The thrill of tempting fate while wearing her heels was beyond sensational. Beyond any sport I had played and pretended to enjoy. Beyond classroom banter, beyond dreams of college or career.

This moment and all its consequences swallowed all of my attention.

Behind me, still in her bedroom, my friend tried on her clothes. I could only guess what he had chosen.

At the top of the stairs, I stood shaking, vibrating with anticipation. Finally, I stepped down. Then another step, gripping the dark wood banister, anchoring myself to reality while drifting through fantasy.

Near the bottom of the stairs, I caught a flash of movement reflected in the window.

Someone outside was closing the door of a parked car.

I didn’t have time to confirm it, but instinct told me everything. His sister had come home early.

I dashed, or rather danced, back up the stairs, careful not to break an ankle. Somewhere in my panic, I vaguely appreciated the irony that sports had somehow prepared me for this moment.

As I reached the top and turned toward her bedroom, I heard the heavy front door shut. There wasn’t time to undo the clasps and remove the shoes properly.

I tried tiptoeing down the hall to silence the tapping, but it was hopeless. Every step betrayed me.

And the silence downstairs betrayed something too.

She knew.

I finally reached her room, slipped inside, nearly shut the door, and collapsed to the floor, fumbling desperately with straps and buckles.

Before long, I heard the floor outside creak. Then another creak. Slow. Uneven. Cautious.

Not casual footsteps. Curious ones.

She knew something was different, and she intended to find out what.

My hope had been to gather my things, ditch hers, and escape before anyone noticed. Now, my best option seemed to involve diving out the dormer window onto the roof and improvising an escape route from there.

Then something else struck me. My friend was gone.

He must have heard me scrambling outside and guessed our predicament, bolting for cover somewhere else in the house. In his hurry, he had abandoned one of her short yellow skirts on the floor and scattered her makeup across the dresser top.

I huffed despite myself, imagining him fleeing while clutching his own clothes in his arms. If I got caught, he would probably find some excuse for himself.

I didn’t blame him. This wasn’t his problem anymore. It was mine.

Finally free from the heels and clutching my own shoes, I leapt toward the window.

Too late!

Looking back, nearly any plan would have been better than this one. I could have borrowed the heels and hidden somewhere else. I could have blamed my missing shoes on her brother. I could have turned around at the stairs instead of pressing my luck.

But none of that mattered now.

She stood in the doorway, while I stood barefoot, one hand on the window, surrounded by her heels, her short, soft yellow skirt, scattered makeup, and a half-open panty drawer.

I was frozen. I was caught. I was ruined.

My worst fears arrived all at once, followed by fears I had never even imagined: police, humiliation, social exile.

Time stretched. She surveyed the room. I stood silent.

Then, unexpectedly, the first words came from me.

“I’m so sorry,” I said. “My curiosity got the better of me. I shouldn’t be here. I’ll leave right away.”

I started toward the door, but she didn’t move.

At eighteen, I was mostly grown and taller than her. Bigger than her, even, but not by much. I could squeeze into her size nine heels and softer stretchy fabrics. But she carried an authority I immediately surrendered to. In her space, my own confidence collapsed to nothing.

I stopped halfway across the room.

“Why are you in such a hurry to leave?” she asked, a strange smile pulling at her face, suggesting we had more to discuss.

My heart stopped. My imagination raced.

“Relax,” she said. “I’ve known for a while. I was just hoping to see it for myself. But it seems I missed the show.”

I stood silent, confused, holding my breath while my future seemed suspended in her next sentence. Was she going to let me off the hook?

One of her hands rested on her hip while the other held the door, like some strange judge deciding my fate.

Door open or door closed. Freedom or punishment.

My mind raced through every possible outcome.

Slowly, she turned away, opened the door slightly, and peeked into the hallway.

Then she turned back.

Quietly, deliberately, she closed the door behind her.

That same smile returned. And the words she spoke next shifted me from dread to confusion and then to something I never expected.

Excitement.

“I’d like to see it,” she said.

“I’d like to see you in my clothes.”

The Thrill of the Heel Part 2

She stood, back to door, not just to get a better look at me, but to also hold the door closed in case I tried to escape or someone else attempted to enter.

I knew I was at her mercy and she knew it too. Lucky for me, she kept that wry smile and playful look.

She repeated herself, sensing my stunned expression, "I'd like to see you in my clothes. I know you've been trying them on already. Now show me."

My panic had transformed to excited disbelief. I never imagined she'd accept the fact I was in her room, let alone encourage me to try on her clothes.

I didn't need encouraging. I was already doing it moments before, just with her heels, despite my attempts to hide it. But the fact she didn't outright charge me out of the room and call her parents and maybe even the police, was the exact opposite of discouragement. She really did want to see me try on her clothes.

My panic/excitement just made me freeze. I didn't know what to trust. Should I take a step toward the heels I'd dropped moments before or try to talk my way out of the whole thing, convincing her to let me go?

She laughed. "I see your'e having trouble. Let me help you." As she said it, she twisted the door lock behind her, ensuring it was secure, then walked over to toward the heels dropped on the floor by me just moments earlier.

She picked them up. Something about the way she picked them up, sparked even more excitement. I could feel my temperature rising. I wanted to move like her, BE like her. But I had to play it cool.

She held out the heels by the straps and quietly demanded I take them. Unsure, but deciding to feel brave, I took them and held them in two hands. She stepped back to the door and, using her eyes alone, suggested I try them on.

I sat on her bed now, glancing back to her and then to the heels, took one deep breath then lifted the first to my right foot.

"Stop!" She exclaimed. "Not like that. You're wearing the wrong clothes."

Up to this point, I had only tried on the heels. The scattered clothes on the floor and scattered makeup on the counter wasn't my doing. It was the mess my friend, her younger brother, had made as he dashed to clean up and escape without sufficient time. Leaving me in this predicament alone.

We'd started this adventure together, but now he'd evaporated, exitng just in time, and I was caught holding my own shoes in a dash for the window. I wasn't about to throw my friendship with him under the bus just to get out of this mess. And, fingers crossed, it may yet become an unexpected adventure.

"What do you mean?" I asked, tentatively.

"Youre wearing jeans and a t-shirt. I want to see you fully dressed." She expressed.

My stomach turned. I knew what she meant and did not see it coming. I mean, I secretly began to hope for it, but I thought maybe she'd let me try on the heels and leave it be. It could become a wild story that would one day be comical in retrospect. This was becoming something else, and very quickly.

"I'm not sure I can." I complained. "I mean, I shouldn't be here. I was just curious. I should leave."

"I know," she replied. "I'm curious too. Let's see it. Let's see you try on that yellow skirt you dropped over there. And I have a cute top in mind I can find for you too."

I sat frozen again. Then, after a few short moments, she left her guard at the door again and moved to the skirt on the floor. Picking it up, she made a "mmmmm" kind of noise. Like a small gesture implying that it would do just fine. Then she lifted the skirt, arm outstretched and nodded, suggesting I take it.

I did. I didn't know how not to at this point. My body was not my own. I think she sensed it and leaned into her authority even more.

"Now, go ahead, try it on. I will find the top. I'll even look away while you change."

She turned and walked to her closet with a mission to find me a top she liked. Within a few seconds I felt myself yielding, then unzipping my pants and sliding them off while remaining moslty seated. I pulled the top of the short, lemon-yellow skirt over my feet and up to my knees just as she turned to check on me.

She giggled, then said, "That won't do."

"What?" I barely squeaked.

"You need panties. You can't wear THOSE. You need girl panties. I have just what you need." And she moved to the dresser near the other wall.

My stomach turned again. I'd tried on her panties before, but never imagined being caught. Now, it seems she knew, she always knew, and even more, she wanted to see me in them. But the opportunity to retreat in any form now, seemed unbelievably small.

I felt pulled toward her demands. I felt compelled to respond and I did.

For the first time since our exchange, I braved my own question and asked in a whispered voice, "Can I try on your white, silky thong?"

She looked back at me, eyes wide and grinning. "Of course dear. Great choice! I bet you even know where to find it."

She wasn't wrong and she knew it. I was emotionally beyond reach at this point. A bomb could have gone off and I may not have noticed it. My blood pressure was rising and thats not all that was rising.

She returned to the bed, holding out her white satin thong on her index finger and waited for me to take it from her. I did, and smiled a huge embarrassing, flushed smile.

This time she didn't turn her back to me, she just stepped back, folded her arms, and waited for me to take off my underwear and put hers on.

For the life of me, I can't imagine what forces allowed her to explore this with me and not explode into anger or disgust. But I trusted her somehow and did what she wanted. She was older than me and seemed to be enjoying herself so I let the thought pass.

The obvious thing happened to me. My penis was so enlarged it sorta hopped pr sprung as my underwear band slid down. With fumbly hands pulling at the panties, past my knees and thighs, it sorta folded up toward my belly as the thong slid on.

I couldnt look at her but I felt she was enjoying the whole experience too. The feeling of the thong sliding up and over was enhanced even more than ever before knowing she was watching and wondering what I must be thinking.

"That's much better," she said. "Now the skirt."

My heart was racing. My mind only briefly paused to check the door and wonder where my friend had disappeared to. Perhaps he had crept to the door and pressed his ear to hear everything. Maybe he'd left alotgether and had no idea what fate had become of me. It was a thought for another time.

She seemed to notice my momentary concern and said, "Don't worry, we are alone. And I won't tell anyone."

My trust issues faded another notch and I let the experience begin to unfold even more.

"Now, here is that top I want you to try." She said as she handed me a white short-sleeve top. It was cut higher than normal. Not a crop-top but not cut at the waist either. The fabric was stretchy and easy to imagine slipping on. But as soon as I received it she stopped me again.

"Hold on, we're forgetting something. You need a bra too." She returned to the dresser and came back with a matching satin push up bra. I knew it would stretch to fit. I'd worn it once before.

"This one should do," she explained. "It's a little too big for me now you've been wearing it and stretching it out." Her smile gave way to a playful and accepting giggle and I clumbsly accepted the bra. She had me in her palm.

Once again she stepped back and folded her arms, assuming I'd take off my shirt and replace it with her bra and white top. I did what she wanted..., what I wanted, and when I had, I finally stood. I was still barefoot, but the euphoria had taken hold and, like a girl listening to her favorite song, I was compelled to stand and twirl and move to melody.

She raised her arms away from her chest and placed her hands against her mouth in an "oh my" kind of gesture and her eyes grew bigger. She stood silent apart from a giggle and gleeful breath here and there.

Finally, she broke the silence, and my own magic moment, with a reminder to put on the heels she had given me in the beginning.

What had come first was about to come last. I sat again and placed each foot gently into the heels, tightened the straps and then sat back and flattened the skirt over my legs. I glanced up at her and asked breathlessly, "Now what?"

"Now stand." She replied. "I want to see you walk and move. I want to see the girl you are. I want to see what I've been missing and suspecting all along. And after, if we have time, I want to try on some makeup with you. Can you do that for me?" She asked.

"I'd love that soooo much." I said, with another nervous smile, and stood to model as she desired.

The Thrill of the Heel Part 3

How long could I stand the pressures? They seemed to stack. First, was the pressure or desire to try on her heels and walk through her house. That part was fun. Next, was the pressure to race back to her bedroom at the sound of her car arriving home too early. Then came the pressure of actually being caught. And finally, the excitement and pressure of being surprised by her reaction and also slowly becoming feminized into a girl from head to toe.

This day was not turning out as planned but it wasn't bad. It was in fact, beyond exciting. I stood next to her now, wearing her short yellow skirt, white, short sleeve top, white satin thong underneath, which barely contained my erection. I wore creamy strappy heels pressed against the floor, and sported a heart rate that mirrored an athlete in motion.

She stood, happy and supportive, playful and kind, warm and inviting. She was natually pretty in her own right and casual in her outfit choice compared to mine. Simple blue jeans, short black boots, and a soft, over the shoulder, pink top.

We stood at her shared upstairs bathroom sink, just across the hall from her room. Both staring at the makeup products she intended to put on my face.

Crossing the hall at her request was just one more event stacked on. Somewhere in the house, probably nearby, was her brother, my friend, but I assumed I'd eventually get a chance to explain what happened in private. I knew he'd understand, even be excited for me, being he was part of this adventure from the start. Not that she knew that. But for now, it was a time to live in the moment.

She reached for me and turned me away from the counter and toward her, then began to apply a sponge full of foundation to my cheeks, nose, and chin.

Before long, my erection faded and my heart slowed. I felt myself sort of fall, not physically, but emotionally. Not in a bad way either. In a calm, quiet way. Like exiting a loud school hallway and entering a quiet library.

My experince changed from excitement and high blood pressure, events stacking higher, to calm euphoria. To zen. Slowly, almost imperceptively, time escaped me. The sponge became a brush, then a lipstick tube, then an eyeliner pencil, then another brush, and so on, until finally, she dropped her hands to her side, stepped back and examined her work.

I hadn't been allowed to look myself. And then, with her smile and nod of approval, I turned to the mirror. I had indeed transformed. I couldn't believe my eyes. I couldn't believe it was really me. She reached for my shoulder as I stood, shocked and amazed. Her touch amplified my senses and I began to feel the blood leave my head again and travel south.

She interrupted my hot flash, if you can call it that, and asked if I wanted to try on a wig?

"I didn't know you had one." I said.

"I dont. At least its not mine." She replied. "It belongs to my mom. She has a few costume wigs for parties. They won't be perfect or natural but it could be fun."

"YES!" I exclaimed. It was almost too loud. She giggled again. Okay, give me a moment. Wait in the bedroom, if you like.

I peaked into the hall and then danced across the wooden floor to her room. I knew my friend knew what was happening but I was afraid to let him see me like this. Moslty because it seemed too weird I was getring all this attention from his sister. I didn't ever imagine being feminized by her. I just liked trying on her clothes when she was gone. He like it too. We'd both tried on her clothes many times and loved the giddy feelings it brought as we imagined becoming girls.

Now I was being transformed and felt he deserved that chance too, but not by her. It was too strange and even stranger, was the feelings I was developing about her. She had expressed her desire to see me dressed in her clothes. She somehow knew Id done it before and wanted to catch me in the act. She wanted this too. I wonder if Id missed something. Or many things.

Soon, I heard her footsteps on the stairs, climbing toward the top and toward me. In moments id see her again and respond to her every request. It had become our quiet little secret and I was excited to see what came next.