Caught by My Aunt Pt. 01

Story Info
A Crossdresser is caught by Auntie.
2.7k words
4.51
55.7k
38

Part 1 of the 2 part series

Updated 06/10/2023
Created 02/07/2022
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1.

Knowing she wouldn't be home from work for several hours, I entered her bedroom. I'd walked past the master bedroom plenty of times, and she usually left the door opened, so I knew how it looked, but I'd never been inside. The room was as you'd expect a woman's bedroom, lots of pastel colours. Beams of sunlight shone through the venetians lighting up the space. A queen-sized bed dominated the room, made up with a white floral cover with matching pillows and a few pink cushions. There was a makeup table with a mirror against the wall where she would sit and do her makeup. Opposite the bed there was a double sliding cupboard with mirrored doors. Up against the far wall there was a chest of drawers, and that was where I headed.

I opened the top drawer. It was full of underwear: bras, knickers, tights. I rifled through it, hoping to find what I was searching for. After a bit of fumbling around, I found them, right at the bottom of the drawer: a few pairs of stockings and a couple of suspender belts, in black and cream. Elatedly, I picked out a pair of nude stockings and the cream suspenders. I frantically went through her bras and knickers, trying to find a matching pair, a pair that would also match the suspenders. Happily, I found just the right set. I was excited now, my heart racing.

I turned to her bed and started undressing. Off came my t-shirt, my jeans, sneakers and socks. My hands were shaking as I tried to put on her bra, trying to clasp it behind my back. Eventually I managed. It was tight against my body, obviously too small for me. Next, I put on her knickers, a beautiful lacy pair. I could feel the soft lace against my body, against my cock. My erection struggled to fit, but somehow, I made it fit. I stepped into her suspenders and pulled them up to my waist, surprised to find they fit quite neatly. I sat down on the bed to put on the stockings, rolling one up and slowly pulling it up my right leg. With shaking hands, I fumbled to fit the suspenders to the top of the stocking. It took forever to fasten them, especially the back one. Then I tried to do the same with the other. Gently rolling it up and slowly pulling it up my left leg. One of my fingernails must have snagged in my haste. As I rolled the stocking up my leg, I put a big ladder in it, running almost the length my leg. Cursing my carelessness, I almost went to fetch another stocking, but decided against it.

I stood up and eyed myself in the mirror. Small by male standards, I didn't have broad shoulders or muscled biceps. My waist was small and I had no hips to speak of. I wasn't particularly hairy, but the hair on my chest did look faintly ridiculous, as did my hairy legs. Perhaps, I thought, I should have gone with a black ensemble rather than this light one. The bra was digging into my upper body, it really was too tight for me. My knickers were also too small, they struggled to hold in my erection, and the suspender belt was slowly sliding down my waist. Nothing really seemed to fit. I didn't care too much; I wouldn't be wearing them for too long. I just wanted to admire myself and, perhaps, masturbate. I went to the cupboard looking for a pair of shoes, choosing a nice pair of black pumps that might fit.

It was as I was sitting on the bed to attempting to squeeze my feet in when I heard a voice: "what on earth do you think you're doing?"

2.

She was standing in the doorway, with her hands on her hips, and an angry look on her face. I felt the blood rushing to my face, a heat that was almost unbearable. My mouth was doing its best to mimic a gulping fish. I uttered some nonsense that sounded no more than a string of vowels vainly attempting to form words. My mind had simply stopped working. I lost control of my arms as well, trying to cover my whole body at once. "Well?" she asked caustically. I swallowed a couple of times and somewhat managed to gain control of my voice. "I'm sorry" I said in a trembling, small voice. I didn't dare look her in the eye, focusing on the carpet in front of me instead, searching for a hole to crawl into. "Sorry? Is that all you can say?" There was a sting in her voice that I flinched from. "I'm sorry" I stammered again, unable to think properly. I'd never been so embarrassed, and simply did not know what else to say.

"You'd best come into the kitchen" she said, and I felt as if some of her ire had waned. I reached for my clothes in a heap on the floor. "No." Like the crack of a whip. She pointed at the pair of heels that I'd been trying to squeeze my feet in. "Put those on" I tried, but they were simply too small for me and after a couple of attempts I gave up. "They won't fit." I said meekly. I felt I was close to tears now. "Then come as you are," she replied, and turned away. Slowly I stood up and my head hanging sadly, I followed her down the hallway into the kitchen.

She sat down at the kitchen table and crossed her legs, her elbow resting on the table. She drummed her fingers, her nails making little ticking noises. She looked me up and down, and I couldn't tell what she was thinking. She had an odd half smile on her face. "Pour me a drink" she ordered. I hesitated, but obeyed. I reached into the fridge for a bottle of wine and took a glass off the shelf. I started to pour the wine on the kitchen bench, but she stopped me. "No, bring the glass here." Again, I obeyed, walking over and placing the empty glass in front of her. I poured the wine. "Now put it back in the fridge" Once more I walked to the fridge, and replaced the wine in the door. I turned and walked back. "Now, come here, and let me have a look at you", she instructed me. I stood before her; my hands clasped in front of my by now flaccid cock. It certainly fit in her knickers now.

"Hands by your side, please" she said. I hesitated, not wanting her to look at me. I didn't want her looking at me at all, but I definitely didn't want her seeing my cock. "Do it!" there was that sharpness in her voice again, commanding, irresistible. Struggling, I submitted, allowing her to see me all of me. I couldn't look her in the eye, full of shame. I stared straight down, seeing nothing. My eyes were glassy, close to tears. For a full minute she said nothing, but I could feel her appraising me.

"Putting aside, for the moment, that you went into my bedroom and rummaged through my drawers. Why are you wearing my underwear?" It was asked in a questioning voice, without anger. "I don't know," I blurted out without thought. It was all I could think to say. "You're lying to me. Don't lie" there was an annoyance in her voice now. That anger was still there apparently, but she was trying to contain it. I didn't know what to say. I didn't want to say. Felt I couldn't say. "I'm waiting." she said. I realised she was going to make me stand there, in front of her, in her underwear until I started to talk. "I like it" I managed to answer eventually, my voice very small. "What is it you like?" she asked. I thought of how to answer, but she cut me short. "Oh, just say it". I tried to gather my thoughts, thinking of, but before I knew it, I blurted it out: "i like girl's clothes."

3.

There was a silence. From my peripheral vision I could see her lightly swinging her foot, but I didn't dare look up. I'd never told anybody before.

It had been my Great Secret for many years. One of my earliest memories was of stealing into my mum's room when I was home alone, and go through her drawers, exactly as I'd done in this case. I especially loved the feeling of my mum's tights. Any chance I had, I'd be wearing her tights. I'd often steal them and hide them under my mattress, so I had them to myself. I'd often wear her tights under my pants or jeans. Just loved them.

The older I grew the more adventurous I became, trying on her bras and knickers, her heels, and also her clothes like skirts and dresses. At first it was almost like a fetish, ending up with me masturbating, but as I grew, I slowly came to realise that I actually wanted to wear girl's clothes, that I wanted to look like a girl, maybe even be a girl.

So, I had from a very young age realised that I was not like the other boys. Oh, I did love sports, and I didn't play with dolls, but I very much preferred women's wear over my usual jeans and T. The older I grew, the more I knew that that was what I wanted. I never shared this with anyone, fearing embarrassment, humiliation, fearing being ostracised. Yet, the desire, the need even, never left me.

Thankfully, the internet exists. Online, I could be my own self, my own persona, and online I met others that felt the same as I. All of a sudden, I wasn't alone anymore. That was a real eye-opener.

Still, while I was living at home, there really wasn't anything I could do. I didn't dare talk about it with my parents. I couldn't very well buy my own clothes without it being noticed, and the thought of going instore to buy women's wear scared the living daylights out of me. Online shopping was also out, surely mum and dad would find out. And so, I just kept stealing into mum's room and trying on her clothes when I could.

That's why we're here now.

That's why I'm standing in front of my aunt wearing her underwear.

4.

Finally, after what seemed like an eternity, she spoke: "Oookay, well I can see that, Marty. What I want to know is why you like girl's clothes." I supposed that I simply had to tell her the truth. There really wasn't anything else I could do. "I like to look like a girl," I said. I wasn't trembling anymore, but my heart was still racing, my mind was cloudy, and my hands kept trying to cover my crotch. I was still flushed I noticed. All I wanted to do was run away and get changed into my jeans and t-shirt. Perhaps then we could talk about it.

"Can I go change now, please?"

"No. Do you want to be a girl, Marty? Or is it that you just like women's underwear?"

"I just like to look like a girl"

"Is this some kind of fetish, or do you genuinely want to be a girl?'

"No, no no no. I just want to want to look like a girl"

There was another pause, I suppose while she mulled over that. I noticed that she wasn't angry anymore. She merely sounded inquisitive, and thoughtful.

"Well, okay then. Now we need to talk about the other thing. You've gone into my bedroom, went through my drawer and you're wearing my underwear. You've probably stretched and ruined a nice set. And I see that you've put a massive ladder in my stockings."

"I'm sorry" I replied

"No, that simply won't do"

I looked up for the first time. I only made eye contact for a moment, but I saw that she had an odd half smile on her face. She stood up then, abruptly, as if she'd made her mind up about something. She came to me and put her hands on my hips. She turned me so that I faced the table.

"No, that won't do at all."

I felt a little push on the small of my back.

"Lean forward and put your elbows on the table, hands flat down."

I did as she bade, a faint tremor going through my body. I thought I knew what was to come, but was too shocked to resist.

"No, what you need is to be punished, Marty. You need to be disciplined. You're just sorry that I caught you."

5.

I was leant over the kitchen table with my elbows resting on the table and my hands flat. I was wearing my aunt's underwear; bra, knickers, suspenders and stockings. She was behind me, and she was about to punish me.

My aunt was family of course, but not blood related. She'd married into my family through my uncle. He'd sadly passed away several years before. She hadn't remarried, and so far as I knew she didn't have a boyfriend. She'd had two kids with my uncle, my cousins, but they'd since moved out of home. One was away at university and the other had married her high school sweetheart.

She was a mature woman, but looked pretty good for her age. She hadn't ballooned like so many after childbirth. She still kept her trim figure. She wore her hair quite short and that suited her well, and when she wore makeup, she looked good.

It was how she dressed that really caught my eye. She worked in an office in town, and generally wore a skirt and blouse with heels. At family gatherings she usually dressed nice as well. Fashionable I suppose. She knew how to dress well.

Right now, home from work early as she was, she wore a purplish blouse, a black skirt and black, high heeled ankle boots. I couldn't see them from my position though. All I could see was the wood patterns on the tabletop, from up close.

The first slap came without warning. Although I was almost certain this is what she had in mind, I had hoped she was only trying to scare me. No such luck unfortunately. The first one was a good one, a stinging one, right on my arse. I gasped and cried out.

"Keep it down," she said. "Else I'll just keep going. Take it like a big girl."

She spanked me again, another stinger.

"Now what do you have to say?" she asked loudly.

"I'm sorry." Slap.

"My name is Aunt Allison. Say it." Slap.

"I'm sorry, Aunt Allison."

"For what are you sorry?" Slap.

"I'm sorry for wearing your underwear."

I was panting now, and moaning. She certainly knew what she was doing. She was spanking me just so. With every question, and every answer, another slap. Just enough to hurt, but not enough make me beg her to stop. I'm sure she knew that I could take it, for a little while.

"For ruining my underwear." Slap.

"Yes."

"Yes, what?" Slap.

"Yes, Aunt Allison."

"For going into my bedroom." Slap.

"For going into your bedroom, Aunt Allison."

"For going through my drawers." Slap.

"For going through your drawers, Aunt Allison."

I was close to having enough. I'm sure my backside was terribly red by now, and it was stinging. The slaps were getting more and more painful. Then she stopped.

"Stand up," she ordered. Chastised, I obeyed and turned to face her. She'd stepped back and was holding her phone. "Smile." A flash. She'd taken a photo of me! A photo of me in her underwear! Another flash, another picture.

"Please don't Aunt Allison, please," I begged her. She took no notice and took several more pictures of me.

"Proof," she said, smiling, and put her phone down on the table. She stepped towards me, and lightly brushed her hand against my cheek, and wiped away my tears.

"You belong to me now, Mary"

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14 Comments
AndyPuppyDogAndyPuppyDogabout 1 year ago

I cant wait to see where this goes.

cdCindy1cdCindy1about 1 year ago

great start. I can't wait to read the next chapter.

rushman1ukrushman1ukabout 1 year ago

I was caught by my MIL wearing her undies and heels, sniffing at a pair of her used knickers whilst on her bed, wanking! My cock soon deflated when i heard her voice, I was simply told to finish off what I'd started and to then go downstairs dressed as I was.

AnonymousAnonymousalmost 2 years ago

L loved the story l wish l had a Aunty like that.

billy2002billy2002about 2 years ago

Love to see where Allison takes him/her

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