Caught by My Aunt Pt. 02

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A Crossdresser is caught by Auntie.
4.1k words
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Part 2 of the 2 part series

Updated 06/10/2023
Created 02/07/2022
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CAUGHT BY MY AUNT: A NOT SO SHORT STORY ANYMORE

PART TWO

I'm not a prolific writer, so it has taken a while to write this next instalment. Pardon the delay, please. And enjoy!

We last left off with my Aunt Allison catching me in her bedroom wearing her underwear. She'd been shocked and I'd been embarrassed. She was angry. I was ashamed. She had spanked me hard. I had cried.

6.

Afterwards we sat down on the sofa and shared a bottle of wine. She had many questions, and once I started, I couldn't stop talking. I was terribly uncomfortable at first, not just about talking to her, but also because she wouldn't allow me to get changed. She made me sit with her on the sofa in her underwear while she remained fully clothed, and any time she wanted her glass refilled she told me to get up and walk to the kitchen for the wine, refill her glass and put the bottle away again. The humiliation felt never-ending. Several times, I asked her if I could change, but she refused time and again, eventually telling me to stop badgering her lest she get angry. It had been me, after all, that had wanted to wear her lingerie.

She asked me pointed questions, genuinely seeming to be interested in my responses. She asked me about how long I had been feeling like this, this desire to dress up like a girl; she asked me what it was that I liked about girl's clothes, about being a girl; how did I start? Where did I get my hands on clothes? whose? Was I gay? The questions just kept coming, and slowly, hesitantly I opened up, explaining that I had liked girl's clothes for as long as I could remember, how I'd borrow my mum's underwear, that no, I wasn't gay, that I just liked dressing up and looking like a girl. And as we talked, question and answer, question and answer, I started to feel less self-conscious and could almost forget that I was chatting with my aunt while wearing her underwear.

Finally, she had allowed me to change, though I had to keep her knickers on. So far as she was concerned, I had ruined them, and may as well keep them. She sent me home. She didn't want me in her house that night.

7.

I received a text message from her later in the week: "Be at mine at 3 on Saturday. Wear your knickers."

The following day she sent another: "Shave your body. All of it."

Nothing else. Just commands. I didn't want to see her, ever again, but felt I really had no choice in the matter. She had pictures of me and had made it clear she would use them. I belonged to her.

On the Saturday, at three as she'd told me, I arrived at hers. I was trembling with apprehension. I didn't want to be there. I wanted to be anywhere other than here. The far side of the moon perhaps. I sat in my car for several minutes before I could steel myself to get out and knock on the door.

"Come in Mary" she called when I knocked. I opened the door and meekly walked in, my head hanging, not knowing what to expect. She was sitting on the sofa in a t-shirt and skirt. "Are you wearing your knickers?" she asked. I nodded. "Come here and show me, girl." I walked over to her and unzipped my jeans and showed her her, I mean my, lace knickers.

"Did you do as you were told?" I had; I'd spent hours in the bathroom shaving my body. Again, I nodded. It was all I could do. My voice had escaped me. "Come and sit down" she said patting the lounge beside her. "I've been thinking. You can't wear my underwear. I won't have it. Besides they don't fit you. You need your own, so we should go shopping."

First, she got out a tape measure and measured my chest, waist and hips. She went online and wrote numbers down on a stickit note which she gave to me. "Those are your sizes. Memorise them." Then, grabbing her keys, she led me outside and into her car. "This will be so much fun, two girls going shopping."

We drove to a shopping centre nearby, parked and walked in. The centre was busy, people going about their usual business. People wandering aimlessly, browsing, eating in the courtyard. An entirely normal Saturday afternoon. We however were there to buy women's clothes for me. For me! I was excited, I'd never owned any clothes of my own. I was also nervous; we were there after all to buy clothes for me.

There was a well-known lingerie store in the centre, one I'd walked past before. I always stole a glance at the window display, wishing that I could own some of the gorgeous clothes the mannequins wore. I'd even visited their website, thinking that I might order something online. I never went ahead though. Not brave enough, I suppose.

My aunt led me straight to it, but stopped outside, and turned to me. "Do you remember your sizes, Mary?" I was mortified at that. She wouldn't call me that in public, surely? Heat rose into my cheeks; I could feel it. "I do" I stammered.

"I do, what?" she asked sweetly, and I remembered my manners. "I do, Aunt Allison."

"Go in there and buy yourself some underwear." I looked at her, horrified. "What?" I almost shouted.

"And I'll meet you at the cafe."

I was gobsmacked. This must be a joke. I stood there looking at her with my mouth wide open, completely at a loss

"No, you can't do this to me." I pleaded, but she simply looked at me like stone.

"Mind your manners girl."

"Sorry Aunt Allison, but I can't go in there by myself, you have to come with me." I sounded weak, like a petulant little boy, but I was determined. No way was I going in there alone. She ignored my pleas.

"You'll need a bra, a padded one. A B cup should work for you."

"And suspenders, and nude stockings."

"And a camisole and french knicker set."

"All in a nice light colour, something like cream, or peach."

She was ticking the items off on her fingers as she spoke, quite unconcerned at my protests.

"If a sales girl asks if she can help you, say yes. And take your time. Browse. Have some fun."

"I'm not going in there," I had to put my foot down. It wasn't happening. I wasn't going in, regardless of what she said, or did.

She simply reached into her purse, pulled out her phone and started dialling.

"I'm calling your mum." I didn't believe her.

And then my mum answered, I heard her voice clearly:

"Hi Allison. What a nice surprise. How are you?"

Aunt Allison looked me in the eye and said:

"Hi Carol. I saw something that made me think of you."

She pointed towards the store and I knew I had lost. She would tell my mum all, I was sure. All the fight went out of me and I turned. I had to take several deep breaths while Aunt Allison and my mum chatted, but I now knew that I had to go inside. I had no option.

8.

Slowly, with my heart pounding in my chest, I walked into the store. It was a small store and there were a few women browsing. One wall was covered with bras and knickers, either hanging by themselves or as a set. In the middle of the store hung all sorts of camisoles and babydoll dresses and other assorted lingerie items. To the left was the counter and more lingerie hanging on the wall. I was overwhelmed. I didn't know where to look. It was such an alien world, and I felt well out of place.

A pretty sales girl behind the counter noticed me standing by the entrance and smiled at me. I didn't know how to take that. Was she smiling at me as she would any customer, or because I didn't belong, or even because she knew why I was there? I blushed again, I'm sure. I walked in and to the right, away from the counter towards what looked like a million different bras. I never truly realised just how much choice women had. I struggled to look up. I didn't know where to look, where to start. I just stood there in front of the wall, lost.

The girl behind the counter came over to me. "Can I help you look for something?" she asked me kindly. I was going to say "No, I'm okay," but Aunt Allison had told me specifically that if I was offered help, I had to accept. So, taking another deep, deep breath, I said "Yes, please." My voice sounded small, and weak to me, and I hoped that she didn't notice just how nervous I was.

"What are you looking for today?" she asked, and I struggled to remember what it was I was supposed to be buying. I hesitated a bit, before quietly saying "A bra, and a few other things." I wanted to run, I wanted to hide. My cheeks were burning, I could feel the heat coming off of me,

But she simply smiled, and waved her hand around the store. "Did you have anything special in mind?" I nodded and told her what kind of bra, and which colour. We walked up and down the store with her showing me my options. I was surprised by just how many there were. After a while she pulled a particularly lovely one off of a hanger. It was a creamy colour with a nice lace detail. I knew at once that that was the one I wanted. I could feel a stir down there. I nodded and told her that I like that one. She asked me what size I wanted, smiled again and found the right one.

"And what else were you looking for?" I was very, very nervous now, and had a mind to simply buy the bra and walk out in the hope that Aunt Allison would be satisfied. I couldn't take the risk that she'd march me right back though, so I rattled off what else I needed. We browsed and found a nice camisole and shorts set and settled on a suspender belt and stockings to go with it. I like to think that I was getting more and more relaxed, but my heart was still in my throat, and my face was burning. The sales girl just kept on smiling and I couldn't help but wonder if she realised that I was buying for myself.

When we had found everything that I needed, we walked up to the counter and she scanned the items. Then she stopped and asked me if they were a present for someone and would I like them gift wrapped. I eagerly said yes. Oh yes, that would help a lot. Now she would think they weren't for me after all and so would the others in the store. I was ever so grateful to her for asking. I felt a million times better.

I found Aunt Allison sipping coffee in the café. She smiled when she saw me carrying the bag with the logo of the lingerie store on it. "How did you go?" she asked when I sat down opposite her. "I bought everything you wanted me to." I replied happily. I was quite proud of myself. I hadn't thought I could do it, but I managed after all. "Good." she said and finished her coffee. I'd hoped for more, hoped that she would have been pleased. "Let's go home." was all she said.

9.

When we arrived back at her house, she led me straight into her bedroom and had me strip in front of her. She stood in front of me, arms crossed. I took my t-shirt off, revealing my freshly shaven chest. I'd felt silly shaving myself and thought I looked ridiculous afterwards. I just looked like a big baby.

I took my shoes and socks off, but stopped short of taking my jeans off. Up to now I could say I kept some dignity, but I noticed her foot tapping impatiently and she was giving me a dark look. Slowly I unzipped my jeans and pulled them off. Like my chest, my legs were freshly shaven. That had felt even more odd, but I did like how smooth and soft they were, and looking in the mirror after, I had noticed how shapely my legs were. Almost girlish.

I was wearing her lace knickers which were a size or two too small for me. I didn't have an erection though, so my cock more or less fit. It wasn't poking its head out at least. Now I stood before her naked barring her knickers. "You can take those off as well," she said and sat down on the bed. She opened the shopping bag and took out the parcel. "Gift wrapped?" she asked me. I nodded. "Yes, Aunt Allison."

"I didn't tell you to have them gift wrapped, did I?" She seemed annoyed at this. I shook my head. "No Aunt Allison." She unwrapped the box and took each item out one by one and held them up to see. She handed me the bra and told me to put it on. I'd worn my mother's bras and of course Aunt Allison's. Both of theirs' were far too small for me, but I had learnt to fasten a bra at the back. Good practice. This bra fit so much better, the perfect fit and I managed to clasp it easily enough. I liked the padding up front, it looked as if I had a pair of, small, breasts. The B cup seemed to fit me nicely.

Next, she handed me the suspender belt, which was a little tight around my waist, and then a pair of stockings. Sliding those up my smooth legs was very sensual. I loved how they felt as I pulled them up, luxurious almost. I fastened them to the suspenders with some difficulty, and stood up. Aunt Allison passed me the camisole and then the knickers. Both were satin, with a lace trim, and they just felt amazing against my skin.

I turned to the mirror and admired myself. Everything fit, it was the first time I had worn women's underwear that actually fit me. It was amazing. And I have to say, my legs looked fabulous in my stockings. Aunt Allison came up behind me and ran her hands down my waist. "Doesn't that feel better, Mary? Clothes that fit you?" "Yes, Aunt Allison." I replied. "Now there's no reason for you to steal anybody else's. And you never will again, will you?" I shook my head and she slapped me on my arse. "Will you." "No, Aunt Allison, I won't."

"You'd best not, else...I may have forgiven you, but I haven't forgotten, understand?" I nodded. She turned me around to face her. "We do have to talk about that little tantrum in the shopping centre. That kind of behaviour is just not on, little miss, and especially not out in public. Girls who throw tantrums in public are disciplined." and with that she walked out of the bedroom. "Come" she threw over her shoulder as she walked out.

I followed her into the kitchen, thinking I knew what was about to happen, hoping I was wrong. For a brief moment, seeing myself in my new lingerie in the mirror, I had felt quite good. Now I was nervous again. Sure enough, she was standing by the kitchen table, having moved a chair out of the way

"You know what to do, Mary" With trepidation, I leant forward on the table top, resting on my elbows. I arched my back and took a deep breath. I knew what was coming.

The first slap merely stung. The following was worse, and it just escalated from there. Soon she had me in tears. She was spanking me rapidly, barely taking breaths between slaps. She didn't say anything whilst she spanked me, as if there was no need to, and really there wasn't. I knew why she was. I had been a brat, I had had a tantrum in public, and so far as she was concerned that warranted a good spanking.

Eventually she stopped and allowed me to stand up. I faced her, and she wiped away some of my tears. I had been crying quite a bit. "It's okay Mary, it's all over now" she said, brushing her hand along my jaw. "You did well."

10.

She sat down and I got us both a glass of wine. My bum was sore, and I wriggled a bit when I took my seat. I was sure I was red raw. "Have you learned your lesson, Mary?" she asked me as she took a sip of her wine. "Yes, Aunt Allison" I replied. "Good, let's not have that happen again."

We sat and drank our wine, and she started talking about her week, asking me about mine, quite as if nothing had happened, quite as if I wasn't sitting beside her wearing lingerie. I felt a little awkward, but after the previous week, I really should have been accustomed to that. Then she decided that we should order dinner. When that arrived, she said: "I really should make you answer the door, you know." I was mortified. "But I'm not that cruel. I'll go get it." I sighed a sigh of relief. That truly would have been cruel. We ate.

It was after dinner, whilst I was washing up, that she came up behind me. She cupped my arse and ran her fingers lightly up and down my sides. It was soft and sensual and her touch, through my satin underwear felt especially nice on my skin. I felt a tingle and I shuddered a little. She leant into me, body to body. "I have had an idea, little one." she breathed into my ear. "Come to the bedroom when you're finished."

When I'd done the dishes, I walked to her bedroom and found her sitting on the bed, leaning back, legs crossed, one foot tapping impatiently. She stood up when I came in, and beckoned me over. She took me by the hand and led me to her bed. She held me by my hips and guided me around to face her. Then she ran her hands up my waist and sides and cupped my bra, giving it a slight squeeze. "Do you like your new underwear, Mary?" she asked me in a soft voice. "Yes," I said, and then remembering my manners "Thank you, Aunt Allison."

She bit her lip and suddenly her hand dropped to my crotch. She grabbed my cock and rubbed it up and down. I froze, not knowing what to do. Slowly she caressed my cock through my knickers, never taking her gaze from me, and I felt myself get hard. I must have looked shocked.

"Don't give me that look, Mary. I meant what I said. You belong to me now, I own you. All of you."

Soon I had an erection, my cock bulging from within my knickers, while she continued to rub it. "Take them off." she said huskily. Too stunned to argue I slid them off and let them fall to the ground. She looked down then, and stroked my cock slowly.

She pushed me and I sat down hard on the side of her bed. Stepping towards me, she forced my legs apart. "Take my skirt off," she ordered. My hands trembling, I obeyed, sliding her skirt down her legs. She was wearing a gorgeous lace g-string, one that I had actually seen in her drawer. I had looked at it, but there was no way that I could have fit in it, so I hadn't bothered to try it on. "Do you like it?" she asked me. "Yes, I do" I replied. "Pull them down." Not really knowing what I was doing, I slowly pealed her g-string down, revealing her perfectly clean-shaven pussy. I gazed at it, inches from my face, and looked up. She slowly took off her top, and then unclasped her bra, letting both fall to the ground. For a woman in her forties, she still looked good. Her breasts were no longer perky and she had stretch marks on her belly, but she was in decent shape, and she had curves in all the right places. However, this was my aunt. Family. And she was naked in front of me. I still didn't quite understand what was happening, except I knew that it was all wrong.

She gently put her hand on my head and forced me back. I was leaning on my elbows, with my legs spread and my erection sticking out. "Scoot up." she said casually. "All the way." I wriggled up the bed, still not grasping what was happening, and as I wriggled up, she crawled after me, almost feline, like a cat stalking its prey. I came to the top of the bed, and following, she straddled me. I lay back, my head resting on a pillow. I realised now what was taking place, but a part of me refused to believe it. This was my aunt after all. This couldn't truly be what I thought it was.

She took my hard cock in her hand and stroked it a little. "It isn't very big, is it?" she asked me. I didn't know what to say, my mind was too distressed to function. "Well, we'll just have to make the best of it," and with that she lowered herself onto me. Her pussy was wet and she slid down easily. And just like that, I had my cock inside my aunt. I was too shocked to move, but apparently that was fine with her. "You just lie there and take it like a big girl, Mary." she said, not unkindly.

She slowly started moving her hips, grinding against me. "Wow, you really are small. I can barely feel you." she said. She sounded annoyed and moved a little faster. "Perhaps you really were meant to be a girl." She moved a little faster again. "Your uncle, now he was a proper man" and she moved faster yet. "Oh yes, he was a man, not like you." She was moving her hips backwards and forwards, not bouncing. I could hear her breathing get deeper and deeper as she fucked me. I didn't dare move, couldn't move, I was that distraught. "Don't you dare cum, girl." she ordered, leaning forward and grasping my face. "Don't even think about it. It'll go bad for you." There was no chance of that happening though. I may have been erect, but my mind was far from aroused. I was too scared. Too scared of her and of what was happening.

12