Becoming My Sister Pt. 04

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A boy’s obsession with his sister changes his life forever.
2.9k words
4.62
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Part 4 of the 10 part series

Updated 01/21/2024
Created 11/30/2023
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Part 4

Chapter 7

I moaned out loud as I felt his hard cock pull out of me and then his warm cum run down my ass, pooling on my sisters bed sheets. I collapsed on the bed, feeling the pain in my pussy from her boyfriend's big thick dick which had just roughly taken my virginity. There was also the most amazing feeling of pleasure washing over me...I now felt like a 'real' girl! I had actually been fucked by a man! I couldn't get the thought out of my head...a man had just fucked me and had loved it as much as I had! I could feel his cum inside me! Oh god is this how amazing being a 'real' girl is? Is this what it feels like to know you've just turned him on enough to get him rock hard and then make him cum? If it is I never want to go back to being a boy I thought! I want to feel like this every day! I prayed that this wasn't a one time thing and that Brad would want to do it again. I hoped that my sister would continue to be 'frigid' so that her boyfriend would have to turn to me to get the satisfaction he needed.

"Going so soon?" I said with disappointment in my voice as I watched him dress, admiring his beautiful manly body and the way his defined muscles moved and flexed.

"Sorry, Princess but I'm meeting my buddies to watch the game. Write your cell number down for me and I'll give you a call?" he said with a questioning tone in his voice.

My heart skipped a beat as I moved to my sister's dresser purposely keeping my back to him so he didn't see my small dick. I wanted to preserve the illusion that I was a real girl as I was unsure how Brad saw me. Did he want to see my dick or would that be too much like him being 'gay'? Did the fact that I dressed and looked like a girl mean that in his eyes what we did wasn't 'gay'? I had no idea but I was just so desperate to do this again and be his 'Princess'. I scribbled my number down for him and laid back down on my front on the bed. I looked up at him, my legs bent at the knee so he could get a good view of the 4 inch red high heels I was still wearing for him.

"Thanks," he said smiling as he tried to pull the piece of paper from my fingers.

I resisted and looked up and said in my best girly voice, "Promise you will call me?"

He grinned and said, "Of course. See you later," as I watched him pu the paper in his wallet and left the room without looking back. I wasn't convinced he would call as I knew the way guys often treated girls once they had got what they wanted. He probably thought I was just another 'slut' and it was my own fault for being so dumb to put out so quickly. But then again I think my circumstances were a little different and if I hadn't done what he had wanted everyone would have known about my secret by the end of the day!

As my parents were not due back until Sunday evening I still had almost 2 days of being 'Aimee' and I intended to make the most of it! I took the heels off, tied my hair up and ran a big warm bubble bath surrounded by candles...just like my sister did regularly. I luxuriated in the feeling of the warm water and bubbles on my soft skin. I shaved myself all over again and then used her cocoa butter moisturizer over my whole body as I wanted my skin to be as soft and feminine as possible for Brad if he did call me again.

After I dried myself I went through Aimee's closet and picked out a set of her silky pink pyjamas...I loved the way the material felt on my skin and thought the shorts and thin shoulder straps looked so incredibly sexy. I closed my eyes and imagined Brad coming up to me from behind, his hand lifting my long blonde hair, kissing my neck and ordering me to get on the bed...my dick stiffened for the first time since Brad had caught me earlier that evening. It was weird that I didn't get hard when he was around and I hoped that was how it would always be!

I fell into Aimee's bed and my red nailed fingers slid inside my silky pink shorts. I moaned as I felt how hard I was. Gripping my self gently I began to stroke slowly up and down, my eyes closed as I thought about what I had done this evening. How it felt to have a man's rock hard dick in my mouth, how it smelt, the moans of pleasure my mouth caused Brad to make, the feeling of his hands in my long blonde hair, the quickening of his breathing as he began to cum and then the delicious, precious, sweet nectar that filled my mouth and flowed down my throat! And, OMFG, the way he called me 'Princess!!!' That was the thought that drove me over the edge...the thought of dressing up for him, being called 'Princess' and then pleasing him in bed way better than my sister ever had!

I moaned out loud as I felt my orgasm crash thorough me and my warm cum flowing over my fingers, staining Aimee's pink silk pajama shorts and her bed sheets. My whole body was bucking wildly as my increasingly feminine mind fantasied about my dream life as a real girl...images and scenarios flashed through my mind...me being dressed in a thousand different sexy outfits, taken out to bars and restaurants as Brad's girlfriend and being treated 100% like a real girl by bar men, waitresses, taxi drivers, by everybody! Going to the ladies bathroom and touching up my makeup in the mirror along with all the other girls, all of us making sure we looked perfect for our men. Idle chat with the other girls in the bathroom who would, in my wild fantasies, compliment me on my outfit, my makeup and my long blonde hair. Then at the end of a wonderful evening being taken home, making out in the back of a taxi, Brad's hands all over me so eager and hungry for me...barely making it to his bed where he would fuck me over and over and over again until we were both spent and I fell asleep in his strong arms...

The thought of being out in public as a girl terrified and thrilled me in equal measure...I knew I looked good as a girl and that I was much more feminine than masculine looking. I knew just what I needed to do to look better and even more convincing. I needed to grow out my blonde hair more, I needed to diet and exercise more, I needed to practice my girly voice more. I needed to have permanent hair removal. I needed to take female hormones. Oh god, I wish I had real breasts! As I lay in Aimee's bed I imagined all those other men looking at me and thinking I was a real girl. All the things they would be thinking as they looked at my hot slim body in a beautiful tight, short, sexy dress and high heels with my long hair like a blonde waterfall flowing down my back. The fact that I would be on Brad's arm would add another layer of confirmation that I was indeed a real girl. Just thinking about that made my dick hard again and I couldn't help but jerk off and cum again as I imagined other men checking me out and flirting with me! Oh fuck, yes! For some reason I imagined it would mainly be much older men, men of my father's age who would be the ones flirting with me and that made me shiver with excitement! Much older men with beautiful young girls was always a big turn on for me. i wondered if Brad would like that? Would he be proud of me knowing i was hot enough that other men flirted with me or would he be jealous and angry with me? I wasn't sure which reaction I'd like more!

Chapter 8

I was woken the next morning by the ping of a WhatsApp message on my phone. It was an invite message from Brad asking me to connect with him. I feel my heart soar as I quickly replied asking him how he was. He said, "I'm good, Princess. Just a little hungover! What are you up to today? I hope you can make yourself free if you do have plans?"

"Of course! Anything for you," I replied then panicked in case I appeared to be too eager. But then I thought I was probably a refreshing change from my sister. She thought the world revolves around her and I knew that Brad didn't like that and thought that the man should be in control. I was determined to play the submissive girl to his dominant male...the thought turned me on so much! I hoped it would also make him want me more than my sister, beautiful and perfect though she was. I would show him just why he would be better off with me or least that he should continue to see me behind my sister's back while she was away at college! I'd make sure his attention was focused on me and not any other girl. I'd be surprised if any of Aimee's friends could please him as much as I could! And I had a million things I wanted to do with him!

"Great, get ready. I'll be round about 11.00am. We're going out for lunch! And I want you looking hot! Speak soon!" said his message, I felt my legs almost buckle as I re-read his message about 10 times. OMFG! Was he serious? No, surely he must be joking and had mistakenly messaged me and not the 'real' Aimee. I thought back to what I jerked off thinking about doing last night. Jesus, maybe I'd better stop fantasising as they were starting to come true! Or fantasise about winning the Lottery instead! That was something I'd like to come true!

I was almost paralysed as I thought about what I should do. Maybe I should just hide in my room and pretend I wasn't in when he showed up? But then what if that made Brad angry and he told everyone about my secret? No one would believe me if I told them he liked it and had forced himself on me. If I did that then I'd be admitting my secret and I'd be humiliated! There was no way out of this was there? I had to go out in public with Brad pretending to be my sister!!!

As I started to get ready I found myself becoming even more scared and anxious as I showered, dried off and started to do my makeup. My hands were shaking as I knew I had to do the best job ever so no one would suspect I wasn't a real girl. I made sure my foundation was flawless, my eye liner dark black to make my eyes really big and wide just like Aimee's. As it was day time I didn't think my eye shadow should be too dramatic but then remembered Brad told me to look 'hot'. Fuck it, I thought as I reached for a set of my sister's false eye lashes and then used some of her rose gold metallic looking eye shadow which I'd always loved on her. Wow! It looked great, I thought as I looked at myself in the mirror. Of course I went for a red lipstick, not the very very bright shade I'd worn for Brad last night but still red enough that it would attract male attention. If there was one thing I'd learned from my sister is that red lipstick was like kryptonite for most men and they became putty in a girl's hand more often than not! I clipped on the big silver hoop ear rings, a thin silver necklace with a 2 hearts entwined charm and then my long blonde wig which basically transformed me into a real girl! It was so amazing and when I caught myself in the mirror I had to do a double take as I looked so damn good! Or at least I thought I did!

I then moved onto my underwear or should I say my beautiful sister's beautiful underwear! I ran my fingers over all the gorgeous, silky, lacy things in her drawers. The feeling of the material on my fingers was amazing and the anticipation of wearing it and feeling it on my skin all day long was so thrilling! I picked out a few pairs of her panties and sniffed them before holding them against me. I picked out a light powder blue lace see through thong. It had tiny thin straps which would be invisible even under a tight dress but would certainly cover my dick which would be tiny and shriveled anyway when with Brad if it reacted the same as it did last night. I slipped it on, tucked my dick between my thighs and adjusted the straps so they sat high on my hips, enjoying the feeling of the lace material between my ass cheeks. I looked in the mirror and it totally looked like I was a girl with a shaved pussy! I found the matching blue lace bra and then the pads which I knew my sister used to give the illusion of bigger breasts. I filled the cups and slipped it on, fastening the hooks and then adjusting the shoulder straps so that it was tight and held my 'breasts' in place. I enjoyed the feeling of the bra slightly digging into my skin. I knew I would have marks on my skin from wearing it for a long time but it was just another delicious reminder of what being a girl was all about. Wearing things that were uncomfortable but made you look hot was all part of being a girl. I fantasized about getting attention from guys and I would put up with any amount of discomfort for that. I just wanted to drown in the feelings that real girls experienced 24/7, 365 days a year!

I then looked through my sister's closet for a dress. It had to be something that covered my top half and couldn't expose the fact that I didn't have any real breasts to speak of. It would be so obvious that I wasn't a girl otherwise. I chose a black high neck tube dress which had a good amount of Lycra so it was quite 'clingy' and showed off my slim figure quite well. The high neck was also sexy but covered my Adams apple too. It was mid thigh length so not too short and had bare arms...fortunately I had very slim feminine arms so was happy to expose them as they were not masculine at all! My small breasts looked amazing and there was no way you could tell that they weren't real! I checked out my ass loving how the tight dress hugged it, satisfied that the material of the dress was thick enough to hide the lines of my thong. As I had no idea where Brad would take me I chose some 4 inch wedge heels instead of stiletto heels...I may have to walk some distance and I think that spike heels may have looked out of place for day time wear. Maybe I should take a pair of stilettos with me for later?

As the clock approached 11.00am I sprayed myself with Aimee's favorite perfume and waited nervously, my anxiety mingling with excitement at the prospect of going out in public as a girl. I kept checking myself out in the mirror and began to be convinced that from a distance and without too much close inspection I would certainly 'pass' as a girl to the casual observer and maybe even a hot one! I think that Brad must have thought I could pass as a girl if he wanted to take me out in public? He did say he wanted to take me out for lunch after all. Or was he going to take me somewhere where we would be alone? But even then we would probably be seen by someone even if we were just in his car? Or would everyone assume he was with my sister given how similar we looked when I was dressed? The thought of being mistaken for my beautiful, perfect sister did turn me on a lot!!! I wonder if she had ever given Brad a blow job while he was driving? Given his comments about her being 'frigid' I think I already knew the answer to that! So another opportunity to show Brad why he should want to see me more than her!

Then the door bell rang, I gave myself one more look in the mirror, took a deep breath and walked over to the door. The butterflies in my stomach were going crazy as I opened the door and gave Brad my best smile and nervously played with my hair exactly as my sister did...

To be continued...

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Robincd1126Robincd11264 months ago

Great story! Well done. I went out alone my first time dressed in public, eight years ago! It was a very intense experience. I have been out many times since that night, alone and with dates. Next part coming soon?

4Leather4Leather4 months ago

The possibility of what might go wrong is heart stopping for the first time out.

SissyBoy1WarszawaSissyBoy1Warszawa4 months ago

@fantasy_writer_2023 you interestingly develop the story of Brad's girlfriend's brother Aimee who wants to be like his sister and even hotter, sexy and girlier...

A meeting with Brad that ends in sex changes his everyday life and he becomes the sister of his own sister Aimee and her name is also Aimee.. . the lack of Aimee's brother's name is treating him impersonally, as if he was just some kind of imagination, and in my opinion this affects the whole story.

Will Aimee's brother manage to create his own female personality and overcome subsequent experiences as his sister, Sissy Aimee? Will Brad become emotionally and not only sexually involved with Aimee's brother and will they become a pair of friends, or will love rule their hearts? Will Aimee herself find out about her brother and her boyfriend? How will he approach the whole matter and maybe join in the feminization of his brother?

ps. Sorry for any errors and linguistic inaccuracies, I don't speak English.

SissyBoy from Warsaw, Poland. 📖👩🏻‍🦳♀️❤️👧🏻⚧️🧒🏻.

AnonymousAnonymous4 months ago

So far so good. This could a lot of different directions

AnonymousAnonymous4 months ago

Love it please keep it going.

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