A New Life: Prelude

Note: This is my first time publishing here. I've been meaning to write this story out for a while now, but only recently got the courage to do so. This is the first part of a series and everything in this series is true, I have just changed the names to hide my identity.

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My name is Joshua and even as a child, I remember wishing I had been born a girl. Although I only had one older sister, I grew up in a small community and most of the children my age were girls, strange as it was. So at a young age, I often found myself mesmerized by girls' dresses and their makeup. So much so that I would wear my mother's lipstick and walk around pretending to be a model, like those that I saw on TV commercials, whenever no one was at home. However, as I got older, I grew out of those habits and found myself attracted to the girls around me. Every time I thought about the way I had acted, I chalked it up to a childish experimentation phase. It was only when I finished high school and entered the local community college, Highland Collegiate, that those thoughts started returning.

My older sister, Vivian, had always been the rebellious one in our house. While I was nerdy and lanky, she was slim with thick brunette hair. Her breasts were above average size and perky, which definitely made her popular with all the boys at the college, including most of my friends. Her friends were just as hot and their reputation for partying and dressing provocatively had earned them the title, "The Highland Ho's", which they were quite proud of.

It all started one Friday night, when my sister had gone clubbing with her friends and my parents had gone to a party. I found myself scrolling through Facebook and came across a video of my sister chugging from a bottle and grinding on a guy in a club. I couldn't explain it but I found myself fixated on the guy and the way he controlled my sister. The way that he pulled her closer and kissed her neck. I found myself turned on by the thought of being my sister, being controlled by a man much larger than I was. Filled with lust, I decided that I would try to re-enact the video by myself at home.

The first thing that popped into my mind was to break into my parents' liquor cabinet and take some of their booze. I had never drank before, but the lust was too intense and I just craved a release. I grabbed an opened bottle of Black Label and chugged it down like my sister had in the video. I felt the burn go down my throat followed by an intense feeling of warmth. With my newfound courage, I walked into my sister's room, stripped naked and went through her closet and drawers. My 5 inch cock was standing at full attention and I knew that I would need to wear panties to help conceal my erection. I chose a pair of soft silky emerald green panties and a push up bra in the same colour. I crumpled up a pair of socks and inserted them into the 32D bra to give them fullness and slid the panties up my legs. I found the black tight dress that my sister had been wearing in the video and slid it on. I loved the way it gripped every part of my body, while it also left me feeling free. Luckily, my body and legs were naturally hairless and feminine, so looking in the mirror, I found myself mesmerized by how good I looked. With a little bit of mascara and a touch of lipstick, I found myself face to face with someone who could have easily been mistaken for my sister with shorter hair. I grabbed the bottle of Black Label, took another swig and began to grind against the wall; wishing that it was a real man. I was about to burst with sexual frustration, so I pulled the panties down to masturbate, only to hear my phone ring.

The call was from this upper year named Jamal, who had been forcing me to do his assignments. As I looked at the phone ring, it occurred to me that this was my chance to have my fantasies come true. Jamal was a foot taller than me and far more muscular. I had often found myself staring at him in the change room. I knew it was risky but all I could think was "I need someone to dominate me!", so I answered the call.

"Hey faggot, I'm gonna come over and grab that history paper. It better be done," he shouted at me. While I'm sure he intended to come get his paper from me, I knew that he had ulterior motives for coming over. I had caught him talking about how hot my sister was on multiple occasions and knew that he wanted to come over just to spend time staring at her.

"Sure thing!" I replied. I secretly hoped that after realizing that my sister wasn't at home, he would be horny enough to do anything, even consider fooling around with me. He let me know that he'd be over in 10 minutes. I quickly slipped a pair of pyjamas over the dress and wore a hoodie to hide the top part of the dress. I heard the door open downstairs and Jamal walking up the stairs. Just as I was walking out of my room, I realized that I hadn't wiped off my makeup. I felt my heart race and the blood rush to my face as I found myself in front of Jamal, who seemed unfazed.

"Damn, Vivian, you look hot even in pyjamas!" he said looking me up and down, "I came here to grab an assignment from your bro but I'd much rather fuck you like I did last week." He then grabbed the back of my head and kissed me, rolling his tongue inside my mouth. I felt my head swirl from his embrace and the alcohol. I didn't know what was more shocking, the fact that he had completely mistaken me for my sister or the fact that my sister had been fucking my bully. "Viv, what's wrong? Get on your knees and start sucking bitch," he said as he pushed me onto my knees in front of him.

I thought about playing along, but if he brought this up to my sister, they would both realize that it had been me. Despite my fantasy, I told him, "Jamal, it's me, Josh," and anticipated him to be disgusted.

Instead, he looked at me and callously said, "Well, do you think I give a fuck? Unless you want me to tell your sister and all the other guys that you're a little sissy boy, start sucking. I'm sure that your little sissy ass would love that, wouldn't you?"

I was hornier than ever at the thought of being used by my best friend while pretending to be my sister and found myself eagerly responding, "Yes master!"

I unbuckled his pants, as he grinned, and slid his boxers down to his knees. His 9 inch cock sprung out at full attention, practically begging me to suck it. I slowly reached over and wrapped my fingers around the base of his cock. I pulled my mouth to the tip of his cock and give it a lick, not knowing what to expect. I could taste the salty pre-cum as I licked and I slowly took his cock into my mouth. His cock was as large as those I had seen in porn and I struggled to take it all into my mouth. I felt Jamal grip the back of my head as he pushed his cock down my throat. I could feel my eyes tear up as he fucked my face. He continued to move his hips rhythmically for a few minutes until he stopped and said, "I wonder if you're as good a fuck as your sister is".

I gave him a devilish grin and edged him on, "I'm sure I'm better. That's because I live to serve you... master. Anything you say is my command".

Jamal didn't need any more motivation, he lifted me up in his arms and dropped me on my sister's bed. "Pull down your panties Victoria," he said, introducing me to my new alter-ego. As I pulled down my panties, he pulled a bottle of lubricant out of my sister's dressing table and applied it onto his cock. He then walked over and spread my legs even further apart. I felt the head of his cock positioned at the entrance my asshole.

I felt a pressure as he began to push into me. I felt an intense pain as my body tensed up in response to his cock, but as he developed a rhythm, the pain was replaced with a pleasure I had never felt. My moans turned into screams of pleasure as he continued to pound me. I felt him bury his cock deeper and deeper. With each thrust, I found myself thinking about how he had fucked my sister just like this. That very thought filled me with a sense of depravity and disgust in myself but also an immense feeling of lust. I was so lost in the waves of pleasure that I didn't notice his cock spasm inside my ass. I felt the hot cum flood into my ass and slowly drip out onto my sister's bedsheets.

He pulled his cock out and pulled his pants up. He looked at me, a complete mess lying there in utter bliss, and said, "You're a much better fuck than your sister or any of her whore friends. I can't wait until next time. Clean yourself up and I expect you to be ready at any moment to service my needs Victoria. Who knows, maybe your slut sister will want to have a threesome with her new sissy sister."

He walked out of the room and I heard him close the door. I laid there in bed, disgusted with myself for letting my bully fuck me. Until a thought swept the disgust away, "Ugh, I wish he had come in my mouth! I wanted to taste him again! I guess I'll have to wait till next time. Hopefully that's soon!"