Aunt Lizs Bitch Ch 02

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.

The plug entered my ass relatively easily when I tried to take it in the morning. I put my gaff on, added tight panties to ensure the plug would remain inside me and then dressed. Walking with the plug in was another weird experience, but my body swiftly adjusted to the item in my ass, and I was soon able to ignore it.

Chapter 3.

My Aunt walked in a short time later. It was her only full day off, so she was dressed casually in a white camisole top and white panties. Her cameltoe was delightfully evident against her opaque panties, which caused my typical problem with wearing a gaff. Doing my best to ignore her deliciousness, I made her an acai and fruit bowl and her typical flat white coffee. Taking them over to her, I sat in my usual position on her left. Sitting on the plug caused it to rub against whatever it was inside my ass, and I barely suppressed a low moan.

Aunt Liz grinned wickedly at me but didn't comment. Instead, she opened her tablet and began scrolling through her social media feeds. We ate breakfast in companionable silence with only a few times when Aunt Liz showed me a photo of one of her friends and asked my opinion of them to break it. But then she showed me a picture of someone she'd searched for on Facebook.

"Is this the Bowers boy you had trouble with?" She asked.

I looked at the photo and thought it probably was. His 'about' information said he'd gone to the same school as me, and the years he was there fit. However, the Grant Bowers in the photos was physically quite different from how he was when we were in high school. The Grant that bullied me was a pudgy young man. The man in the photos was leanly muscular. I still thought he was probably the same guy, though. "I think so. Why?" I asked.

"No reason," Aunt Liz dismissed.

I knew there was a reason she'd asked, but if I pushed it, I'd earn her displeasure, if not her wrath, so I wisely said nothing more.

After we'd finished our meal, Mistress Donnelly pushed her chair back, patted her thighs and said, "Lie across my thighs, little one."

Wondering what I'd done wrong, I fearfully obeyed, draping myself across my aunt's firm thighs as gracefully as I could. I'd worn another of my new outfits to breakfast. It was a reasonably conservative, mid-length, pastel-coloured skirt, but I'd paired it with a rather daring steel wire-reinforced top. My top's bra pieces didn't meet. It was held in place by the steel wire supports that looped around my neck instead.

Aunt Liz lifted my skirt above my petite, heart-shaped ass and pulled down my panties and gaff. She then opened her thighs and allowed my rapidly inflating cock to surge between them. My aunt then clenched her thighs around it as she manipulated the butt plug. She seemed to find the pleasure spot in my ass instinctively, and she spun the plug's top across it. Desperately trying not to embarrass myself by having an orgasm from anal stimulation, I groaned. However, my hips were lifting my butt to meet my aunt's thrusts, and I knew I'd lose the battle shortly.

"It's your prostate that I'm rubbing, little one," Aunt Liz informed. "Your P-spot. The male equivalent to a woman's G-spot."

Hearing my aunt speak and concentrating on her words helped me to quell my imminent orgasm, but then Aunt Liz picked up her ruler and brought it down onto my ass stingingly. I yelped because I was surprised by the sudden pain, but I managed to stammer, "One, thank you, Mistress," before the second strike stung my bottom. Then with an expansive groan, my cock spat its liquids on the floor and between Aunt Liz's thighs as a crashing climax shattered my body.

"Good girl," my aunt said happily. "You don't have a pussy. Therefore, if I want to fuck you, and I definitely want to fuck you, then it has to be in your ass. I'll put out a longer and thicker plug every Sunday for you to get used to until I'm happy that your ass can take my cock. Okay, little one?"

Aunt Liz couched it as a question, but I knew a demand when I heard it, so I replied, "Yes, Mistress."

"I'm going to my home gym to exercise, Dylan," my aunt informed me. "You will change and meet me there."

"Into what?" I asked confusedly.

"The yoga gear I bought you yesterday and snuck into your drawers," Aunt Liz grinned.

I walked upstairs, wondering how I'd missed her purchasing them. I guessed it must have been while I was changing. Opening my drawers, I found the outfit and put it on.

It fit perfectly, and I was about to walk to my aunt's gym when I saw a note in the drawer. It read, "You won't be able to exercise effectively with your ugly boy thing tucked away. So, I will pretend I do not see it, and you will not do anything to draw my attention to the disgusting thing. You'll need to remove your butt plug, too. I do not want you to wear it for more than an hour each day. You will practice with it before you go to bed and then wear it during breakfast the following day."

I took the yoga pants off, removed my gaff to free my cock and balls, pulled the plug out, washed and sterilised it, and then put the pants back on. I joined my aunt in her gym a little later.

She put me through a series of exercises designed to lean my body further and add some much-needed shape. If I did them religiously every day, Aunt Liz assured me I'd develop a narrower waist and a larger, more muscular butt. I'd never done much in the way of exercise before, and I quickly wore out what fitness I had. I knew I'd ache the following day.

"Go shower and change," Aunt Liz told me. "You'll find a corset hanging in your closet. Bring that back to the kitchen and wait for me."

Chapter 4.

I left, shaking my head and wondering what else my aunt had secretly bought for me. I showered and changed before putting on the same outfit from breakfast. Of course, I taped my cock and balls away so as not to offend Aunt Liz. I found the corset hanging where my aunt said it would be and took it to the kitchen.

It was another hour before Aunt Liz returned. She was dressed elegantly as usual in green trousers and a white, plunging neck top.

Aunt Liz helped me into the corset and tightened the laces until I could barely breathe. She sat at the table while I made coffee. We shared them, and conversation before my aunt said she was meeting some friends for lunch and asked, "Would you like to come too?" I was nervous about going out in public again, but I knew she wasn't asking, so I nodded with fake eagerness.

We got in Mistress' BMW X4 M SUV and drove into town, where we met five of Aunt Liz's friends. There was one friend, a stunningly beautiful, stacked woman probably a little older than my aunt. I kept glancing at her surreptitiously because I was sure I knew her. Aunt introduced her friends as Juana, Penny, Caoimhe, Maddison (Maddie), and Kate. The names clicked in my mind, and I realised I was lunching with some of the stars of The Adventures of a Slut Mommie. Kate was Kate Muggleton, the author of the series.

It was weird to think I was eating with five women I'd masturbated over when I read Kate's stories. I also realised that the four women other than Kate were the confirmed lesbians in Kate's stories. It made me feel even more inadequate than before entering the restaurant. These women, with the exception of the diminutive Caoimhe, were all amazons. They were big-chested, with narrow waists, pronounced bottoms and shapely legs. I was a skinny, titty-less male with little, if any, shape.

However, the inimitable Kate swept me into a conversation, and before I knew it, we were chatting as if we'd been friends forever. I asked about her onyx necklace and its matching ankle chain, and Kate proudly explained they indicated she was owned by her husband and son. She showed me the inscriptions that confirmed this. I then noticed that Caoimhe had a similar necklace and ankle arrangement and guessed that Maddison owned her based on how they interacted.

Talking with Mrs Muggleton allowed me to relax, and I soon joined in with several other conversations. I immediately knew I needed to thank my aunt for insisting that I took an interest in current world events. Juana fled Venezuela just before an arrest warrant for her anti-government newspaper articles. Because Aunt Liz had questioned me about President Nicolas Maduro and what his regime was doing in Venezuela, I could ask insightful questions and contribute to the conversation. I was happy when I saw that my aunt was smiling at me happily. She was proud I could fit in with her friends so readily.

After a pleasant meal and company, my aunt drove us home. She helped me remove the corset and told me to shower, do my makeup, and dress in the outfit she'd bring me while I was showering. When I exited my en suite, I found only a red hair band that had hair extensions similar to Princess Leia's in Star Wars and a tiny white thong. There was a note attached saying my aunt wanted my 'disgusting thing showing and not to tuck because it would please Sienna'.