Aunt Liz's Bitch Part 02.
Author Note:
This story finishes with what some will see as a gay sex act between a teenage cross-dresser and her twenty-one-year-old male lover. If this would bother you, please read no more.
Chapter 1.
After my aunt had taken my virginity, our lives fell into a regular pattern. Every time I made an improvement in my transition from an effeminate young man to a pretty young woman, such as improving my voice to sound feminine, Liz would reward me with sex. Of course, getting to have sex with my beautiful dominant aunt meant my transition was happening quickly. My makeup skills became exquisite, and I could readily change my looks to suit my aunt's tastes.
I'd been living with Liz for around six weeks before she trusted me enough to allow me out of her home. It was a Saturday afternoon when she came home from work and told me to freshen up my makeup and put some low heels on because we were going shopping. I was terrified, of course. People would instantly know I was a crossdresser, and they'd poke fun and laugh at me. I tried to protest, but as I've indicated before, my aunt is impossible to refuse, and despite my objections, I was sitting in her car on my way to Westfield Chermside Shopping Centre.
I wore a pastel-coloured top and skirt set and white 4-inch pumps. My Aunt Liz told me to stop being a whiny bitch and walk confidently beside her, or she'd put me over her knee in the shopping centre and spank me. I was terrified Liz would actually do that, so I pulled my shoulders back, straightened my spine, put a smile on my face, and pretended confidence I didn't have.
I was surprised by how few people noticed anything untoward and by the fact that most of the looks I got were appreciative. There seemed little realisation in the people's looks that I was an effeminate man dressed like a young lady. Instead, the men smiled at me, and a few looked at me lustfully.
"Remember to glide," Aunt Liz hissed quietly, and I smoothed my walk out and began placing my heels on the ground virtually in front of my toes. Doing that made my ass swing and sway, and I suddenly felt many men staring at my tiny, heart-shaped ass. I'll admit the feeling was pretty intoxicating because I was used to women ignoring me and disapproving stares from those who thought I was gay.
Liz took me to Bllini Shoes first. The shoes I'd been wearing, including the pair on my feet then, were from the closet in my bedroom. They mostly fit, but I struggled to wear them for more than an hour or so because they were all around a size too small. If the gorgeous shop assistant in the store realised I was a male, she certainly gave no indication she did. However, I did notice that she and my aunt were more than just acquaintances. The hug and kiss they shared when Aunt Liz and I entered the store was as close to sizzling as I'd seen.
Have I mentioned that trying to become erect when your junk is taped away or in a gaff is a bad idea? Yeah, in terms of pain, it's right up there.
Aunt Liz invited the saleswoman, Sienna Muller, to dinner the following night.
After greeting my aunt, Sienna helped me select several pairs of shoes to go with my growing wardrobe. The difficulties started when Aunt Liz insisted I needed several pairs of 7-inch heeled shoes. I could barely stand in them, let alone maintain my typical glide. However, Aunty stood firm, and I picked two pairs of pumps, two pairs of strappy heels, and one pair of platform heels to go with the others. It was a surreal experience to buy something without needing to look at the price and carefully consider my needs before making the purchase. We bought ten pairs of shoes for a total cost of more than two thousand dollars, which only added to the surrealism of the day.
After Sienna had promised to bring my purchases when she came for dinner the following night, my aunt led me to her favourite dress shops. Again, it seemed that Aunt Liz was more than 'just friendly' with the saleswomen she spoke to and got to help me. None of these women took any notice of me being a male either. I doubted that I was so convincing that they didn't know, so I guessed my aunt had feminised several young men before, and they were used to it or perhaps co-conspirators.
When the PA announced the centre was closing, Aunt Liz and I left the stores and stopped at The Elephant and Wheelbarrow Pub for dinner before going home. Several men at the pub tried to engage my aunt in a conversation but she shut them down hard, although if they merely ogled, she would preen for them.
"I like their admiring gazes," Aunt Liz explained. "But I don't want to listen to their inane blather."
I noticed my aunt smiled frequently as we ate. I guessed she was flirting with the ogling men, but her smiles seemed amused rather than flirty, so I wasn't sure. On our way home, Aunt Liz casually said, "You didn't notice the many men ogling and admiring you, did you, little one?"
"Me?" I disbelievingly replied. "They were looking at you, surely. Why would they stare at a man in a dress? Unless it's to point and laugh."
"Because you're a very pretty man in a dress," Aunt Liz grinned as she casually ran her hand over my groin.
Yeah. It's a really bad idea!
Chapter 2.
When we got home, my aunt sent me to change into one of my new outfits.
When I returned, we sat in the lounge and talked about current events. The war in Ukraine had settled into a stalemate, and there wasn't much news coming from that part of the world anymore. The press continued to push the Covid barrow, but given deaths from that disease were next to zero, I couldn't understand why. Of course, it appeared that Donald Trump would win the upcoming US election, which sparked some lively debate. Aunt Liz was quite pessimistic about what a returned President Trump would do. But I argued having a megalomaniac in The White House would probably make the likes of Kim Jong Un reconsider their actions. I also thought a war with China and/or Russia was less likely under President Trump than under President Harris.
The debate seemed to stimulate my aunt, and she moved so she could sit beside me and run her fingers under my short skirt. I'd removed my tucking tape and replaced it with a gaff, but let me assure you--trying to become erect when your cock is tucked into a gaff is equally as painful as when taped away. Nevertheless, or perhaps because of my discomfort, my aunt's fingers continued to stroke over my 'pussy'. After another round of exchanges, Aunt Liz took my hand and guided it onto her pussy. She then showed me how to straddle her clit with my first two fingers and stroke along her slit until I could plunge them into her slippery pussy.
It didn't take long before my aunt grabbed my wrist and shuddered as she orgasmed. Her heavy pussy fluids flowed over my fingers as she smiled happily at me. Unfortunately, she didn't offer me any relief, and we separated and went to bed not long afterwards.
I found a black rubber item on my dresser when I got to my room. I picked it up, wondering what it was. As I held it, I read the note. It said, "My darling girl, you need to begin preparing yourself to lose your 'girl virginity'. This is a butt plug, and although I'm sure it looks huge now you know what it is, it is actually less than four inches long and quite thin when compared to a cock. The narrow part of the plug after the widest point is designed to make it easy for you to hold the plug inside you. It will hurt to take that, so be my brave girl and accept the pain until it is fully inserted. You'll find lube in your top drawer, and I want to see you wearing this when you serve my breakfast in the morning."
Well, my aunt commanded, and it was mine to obey. I took the lube from the drawer and placed it beside the butt plug. Then I picked the plug up and compared it to my cock. As my aunt said, it was significantly smaller than my flaccid penis. My poor ass clenched at the thought of the plug going in there, but I wanted to please my Mistress, so I stripped naked and covered the plug with lube. Then, I squatted and applied lube to my back passage. I tried to insert my finger to lubricate inside me, but even that was painful to do. Next, I lay on the bed, pulled my knees up and apart and tried to insert the plug. But I wasn't brave enough to force the plug far enough into my ass for the wide part to go through my knot.
I tried to force it part way in and hold still, hoping the pain would lessen, but the awkward angle and slipperiness of the oiled object meant it constantly slid out. Frustrated, I sat up and considered my options. Thinking that it would be easier to insert it if I squatted, I tried that, but I was without success. My ass was simply too tight to accept the plug into it. Close to crying with frustration, I dropped onto my vanity stool. The pain when my stretched ass hit the stool gave me an idea. I put the plug on the stool and sat on it. It almost worked because the plug entered deeper than before with very little increased pain. However, the seat was too soft, and my weight forced the plug too far into it for the plug to slide entirely into my ass.
I knew what to do now, so I walked into my en suite and put the commode lid down. I placed the plug on the lid and then sat on it. With only a soft yelp when the broad piece parted my knot and slid through it, I was able to accept the entire plug inside my ass. I immediately noticed that I had little to no pain now that my sphincter wasn't being stretched.
It felt strange to have something in my ass. It wasn't precisely painful, but it was uncomfortable. I felt full, almost as if I was constipated and needed to take a dump. I rocked back and forth, thinking the plug might move and perhaps sit more snugly and less uncomfortably. However, when I moved, the plug's tip hit something inside my colon that felt delicious. My cock roared to life, and I took it in my hand as I wriggled on the plug. I came only seconds later, spurting huge globules of cum onto the floor.
After my orgasm finished, I pushed the plug out, cleaned and sterilised it, and then oiled it again. Then, I cleaned up my mess and tried to reinsert the plug into my ass. It went in easier than before, so I pushed it out and tried again. After four or five attempts, the plug slid into my ass without any pain, so I decided that was enough for the night. I cleaned and sterilised the plug before getting in the shower and washing my makeup off. Then, setting my alarm fifteen minutes earlier in case I had trouble taking the plug, I dropped off to sleep.
Strangely, my dreams were filled with my bully, Grant Bowers, sitting on my upper chest. Only this time, we were naked, and I knew I'd suck his cock when it loomed above my lips. I woke up from this dream (nightmare? Subconscious desire?) several times before finally settling for the night.
