Straight to Sissy Ch. 01

This is the first chapter of a very lengthy story following the adventures of a straight boy who's femininized into a full blown sissy. The first few chapters are based off a real life personal experience which led me to discover the wonderful world of sissies. The story continues into fantasy, revealing darkest desires.

Each chapter will be split up and hopefully able to be read and enjoyed standalone, as well as in a series. Don't hesitate to message me with any feedback or suggestions!

Suddenly, for the first time in my life, I felt slutty. It surprised me, considering how anxious I was, standing there under a street lamp in suburban Connecticut, wearing nothing but a loose pair of sports shorts, waiting for a black dominant man to pick me up. He had told me he likes his subs feeling vulnerable so he instructed me to wear as little as possible. I had asked him to call me when he arrived, but he sternly told me I should always be waiting for him and I was to remain under the closest light to my condo. Briefly, I wondered if women felt this same feeling when about to engage in an equally promiscuous act.

The flicker of headlights coming around the bend quickly jarred me from my thoughts. At first, almost instinctively, I felt the urge to run and jolt back to the safety of my room before someone saw me in my semi-exposed state. Then, I realized it was likely my new master and so I bravely stood there as the unfamiliar car rolled to a stop in front of me. He rolled the window down and simply asked, "Are you ready to be used?"

Maybe my nerves were just frayed at this point, but his appearance startled me a bit. I had been so nervous about what was about to happen, I hardly had a chance to consider what he might actually look like. He was a huge man, seemingly taking up all the possible space in his driver's seat. I couldn't quite tell how tall he was, but he was on the heavy side, with a large belly bulging beneath a dark green t-shirt. He had long, thick, hair, rolled in dreadlocks and hanging in a large ponytail. There was a gruff look to him, a grizzly goatee wrapped around his snickering mouth. I certainly wouldn't have described him as an attractive man, but his domineering attitude made me feel weak in my knees.

I looked down and hesitantly stuttered, "Yes."

He snapped back, "Yes what?"

I looked up, realizing my error and said, "Yes, Sir."

He looked me over and asked, "Will you be completely obedient and do everything I ask?"

Inside, I was unsure if I really could. Only an hour before, out of sheer curiosity, I had replied to a Craigslist ad describing a large, black, dominant man looking for a younger, submissive white male to turn into his cock slut. I had always had a submissive tendency with women, and the few times I had, made me crave giving up control again. Trying to ignore the fact that I'd be giving up control to a man this time, I sent a message describing my inexperience and what I was interested in.

He responded quickly and forcefully. He told me lack of interest in men was irrelevant because my only purpose would be to serve him. My desires and wishes as a slave would simply be ignored. For him, my inexperience was a positive as he'd be able to train and mold me into the perfect slave. Finally, he told me I'd quickly learn to not only love serving cock, but to actually crave it and that I was to meet him tonight to begin my training.

It all seemed so far-fetched to me at the time. How could I know a little experiment would change my life so drastically? Of course, I didn't really believe him, convinced that this experience would be fun, but isolated. It was all dirty talk, right? But, admittedly his outlandish but dominant response really did turn me on. So I went with it and told him I was ready to submit to him and I was eager to serve him.

Standing there, shivering under the streetlamp, it was my last chance to change my destiny, but by then I didn't really feel like I had a choice. Feeling very submissive, I told him I'd be an obedient slave and I'd do anything he asked without hesitation. He smiled and simply said, "Good," while he continued to look me over.

Suddenly, he became stern and told me to remove my shorts and put them in the backseat. I quickly took them off and awkwardly stood there naked awaiting his next order. He knew I was nervous so he made me wait a few seconds, which felt like an eternity, before he finally told me to get in the car.

I quickly climbed in, my skin sticking to the leather seat, reminding me of my vulnerability. He started to drive off and very matter of factly reminded me I was there to simply see to his pleasure. That I would learn to serve him as he saw fit and my blind obedience would be of the utmost importance.

Meekly, I said, "I understand Sir," and I realized I actually meant it. I felt completely helpless sitting there naked next to this large, dominant man in a strange car heading to an unknown destination.

His next order actually startled me, mostly because I hadn't expected it so soon. I figured there would be some small talk or he'd want to get to know me, but he wasn't interested in any of that. He turned to me and smiled and said, "it's time for you to get acquainted with my cock. Come here and suck it."

Somewhat stupidly, my first thought was a realization that I had always fantasized about getting road head from a girl but I had never gotten it. I never dreamed that I'd have to give road head to a man. But I knew I had no choice. I quickly got to my knees in front of the passenger's seat and leaned over the center console to take out his cock.

It was already rock hard. I also hadn't expected it to be so big. I could barely fit my hand around it and it was about 8 inches long. I had never sucked a cock before so I was hesitant at first. I began licking the head and the sensitive area under it. I was surprised how quickly I could taste his precum leaking out.

I sort of liked the taste and I realized he liked what I was doing. I started to take him fully in my mouth, struggling to open wide enough. He started to push my head further down, forcing his cock into my mouth. There wasn't much room for movement with the steering wheel above my head, so I sort of let him keep his cock in my mouth as I swirled my tongue around the underside.

As I knelt there, I couldn't believe I was committing such a slutty act with a man I had hardly even met. It felt so dirty and like I was just being taken advantage of, which I guess I was. It sounded like we were on the highway now, and I wondered where he was taking me. I could hear him groan every once and a while while I nursed his tool. I was just starting to get used to the invasion in my mouth when I could feel our speed slow and eventually pull into a driveway. The car came to a halt and I heard him turn the engine off as he leaned back to enjoy my service. Feeling a little more comfortable now that we were stationary, I started to increase my vigor a bit. He moaned again and patted my head saying, "oh you're going to be a good slave."

He grabbed my hair and pulled me off his cock to look me in the face.

The stranger smiled again and said, "we haven't even gotten started."

I shuddered and nodded my head.

He began zippering up his pants and told me to get out of the car and stand in front of the hood with my hands behind my head and my legs spread. I quickly scurried out and got into position realizing the headlights were still on. I began to take in my surroundings. I was at the end of a short driveway of a small suburban house, with a small yard and many other houses around within sight. It was late November and it was cold, my little penis felt shriveled and I could see my breath in the car lights as I tried my best not to shake. Suddenly a car went by and I realized to make matters worse we were on a relatively busy road. It was a late hour so I hoped nobody was up to see me standing out there.

As I was just getting my bearings, he clicked the brights on, fully blinding me and surely bringing more attention to my embarrassing state. I realized he was inspecting me, and in a very humiliating way. As I heard cars drive by, I realized if anyone did get a glance, I would clearly be seen, spread for all to see, while he was anonymous and hidden in the car, enjoying the spectacle.

I had been standing there for a few minutes when he finally rolled the window down. I hoped he would tell me to run along inside or at least back to the relative safety of the car but to my dismay he ordered, "turn around!"

I quietly obeyed and turned the other direction. The traffic on the street was sporadic but every time I heard a car approaching, my heart seemed to beat stronger. I felt like my senses were over heightened as my eyes readjusted to the darkness. To my horror, I realized several lights were on in the house in front of me. I quickly scanned the windows as an attractive blonde who looked to be in her thirties came to view in what appeared to be a kitchen. It looked like she was talking to someone in another room as she opened a refrigerator obscuring her from view.

At that moment I sensed movement in my peripheral view and I jerked my head to the left. Was it just a squirrel or some other animal? A light was on in a second story window and I could swear I could see the curtain still moving. Or was my mind just playing tricks on me?

Perhaps sensing my discomfort, I heard my new Master lean out the window and say, "now bend over and spread those cheeks!"

I took a deep breath and closed my eyes and did as he said. I stood there terrified as the seconds ticked by. Finally I heard the lights go off and his car door shut. I opened my eyes and heard him coming towards me as I held my position. I didn't know what to expect at this point. I thought maybe he'd break me in over the hood of his car, but thought this was far too risky of a place, especially considering he had put me on display for the last ten or so minutes for the neighbors.

I felt him grab my shoulder as he grabbed my hair with his other hand and he spun me around and bent me over the hood of the car pushing my hands together behind my back. The metal felt icy against my bare skin as he pushed my head down. He groped my ass, grabbing it roughly and slapping it. I could feel him playing with my tight hole and I heard him mutter, "I'm gonna make you a little bitch."

He licked his fingers and started to push them into my ass. I moaned into the hood and tried to get used to the feeling, knowing I'd have plenty more up there in a very short time, ready or not.

He gave me another slap and laughed a little, "ooh you're so tight!"

At this point I felt like I had already been through so much, and I realized I was totally fucked. I guess I had thought there would be more of a game to this, maybe more foreplay so to speak. But I realized I was just there to get used by this guy, and not only that, he intended to make it a long term thing. I wasn't really sure what to do, but thinking about how I didn't have a choice re-sparked the submissive in me and I felt ready for what was to come.

He pulled me off the car and roughly grabbed my balls and began leading me towards the house.