Becoming His Bitch

*This story has been edited from its original published version in order to provide some more detail and clear things up*

Before I begin, this is the real story of my first anonymous encounter with a man. No false details have been added.

I do not consider myself to be a good writer, nor do I aspire to be a good writer either. I simply want to share my story after reading so many others on Literotica.

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This story takes place during my summer break around two years ago.

To provide a bit of backstory, I had previously began messing around with a childhood friend (a story for another time). Even though I was more than ready to go all the way, he always seemed hesitant to fully explore our new found past-time, even to a point where taking all our clothes off made it 'too weird' for him.

Of course, these series of encounters had made me crave for a real man to show me a good time and I quickly fell down a rabbit hole of curiosity, which inevitably led to sissy porn and feminisation. Up until this point, I had no idea how to find real guys to meet up with and so when I finally discovered Craigslist, I plucked up the courage and posted an ad.

I had turned eighteen a few months prior. My slender five-foot-five frame, tanned skin and naturally hairless body left my inbox with a good amount of replies. Years of football (soccer, for some) were evident through my thick thighs and toned butt. Men couldn't wait to meet this 'submissive' teen that was 'looking for a daddy for my first time'.

After a few days or so, I had narrowed down my replies to a couple of guys that I liked. I was too nervous to take the plunge and meet anyone and so I kind of ignored all the emails. At this point, I was your typical 'craigslist flake'.

Fast forward to two weeks later - I was home alone, super bored and watching TV. My phone went off and it was an email notification. One of the guys who I had been exchanging emails with wanted me to know that he was 'free all day' and attached a picture. It was a photo of him in the mirror. Slightly stocky, a real working man's build, and a big beautiful uncut cock dangling down, around 6 inches long with a good thickness.

Looking at the picture alone I could feel myself getting hard. Why not reply and see where this goes? If at the last minute I get scared, I can always flake out again, right?

After exchanging more emails, I was super surprised to find out that he only lived around a five-minute drive away. He kindly offered to pick me up and drop me back home after. This sounded perfect to me and if anything went wrong, I could always leave his house and walk back home.

We agreed to meet in thirty-minutes and I gave him the name of my street. Half an hour was all I needed to take a quick shower and shave. Even though I was naturally smooth, I wanted to feel as sexy as possible for my first meet.

I remember clearly throbbing with excitement as I was preparing. I couldn't believe that I was about to get fucked and live out my fantasy with an older man. I had only played with my ass a handful of times, yet I was about to take a pounding from a real cock.

The thirty-minute wait felt like a lifetime, but I finally received a follow-up message. He was letting me know that he's down the street waiting. I threw my shoes on and left. During the short walk down the street, my heart was beating like crazy. But it was too late to turn back now.

I see a man standing in the distance. A white guy, stocky build, surprisingly taller than I had imagined as he stood at around six-foot-three compared to my boyish size. He looked to be somewhere in his mid-forties. I was relieved to see that he looked as described. I didn't know what to say to him and the whole introduction was quite awkward, but we both agreed we were happy with what we saw. He was leaning against his huge box van and told me to climb into the passenger seat.

The whole ride I could not help myself from admiring his physique. I wanted this big daddy to have his fun with me, but he almost seemed too harmless in our introduction. I was staring at his bulge through his shorts. I so desperately wanted to reach over and tease him, but I didn't know how he would react, and so I decided to sit still and be patient. Trying to strike up conversation, I asked if we were heading back to his place. We had already planned to go back to his house and so I knew the answer would be a yes, but anything was better than sitting in an awkward silence.

He paused for a while before saying, 'No, I have some people staying there, but I've got something better'.

His answer caught me by surprise. I had no clue what this meant, so I kept my eyes glued to my phone, swiping between apps to mask my obvious confusion. I was observing our surrounding and making sure I knew where I was. As a teenager, I already knew my area like the back of my hand and he wasn't really heading out to anywhere suspicious or unfamiliar.

'So, you are eighteen, right?' - He could tell I was nervous by the way I was glued to my phone, and that made him nervous too. I don't blame him, I was eighteen and looked nowhere near old enough to be in a nightclub, let alone take a cock. I assured him of my age and felt at ease knowing that he had no bad intentions.

After around fifteen minutes of driving near enough aimlessly he pulled up in an area not far from where we had originally started. We were in a very quiet housing area that was broken down by plenty of parks and trees.

He turned the engine off - "Alright, get out". He had already mentioned that we were not going back to his house and so I was a little confused about why we were here. Maybe he changed his mind, or maybe this is his friend's house and he's got more guys lined up for me?

I stepped out and studied my surroundings, we had entered a small semi-enclosed woodland area coming off of the side of the road. I had been past this way before as a shortcut to a friend's house but had never entered this clearing. I waited still as he walked around to my side of the van and slid open the side door.

Needless to say, I was slightly taken aback.

I could have never imagined getting fucked for the first time in the back of a van and this was the last scenario that I was expecting. I was shocked, but I was getting aroused by the thought of being used for the first time in such degrading conditions. I inspected the inside of the van for a while before realising that he was waiting for me to get in first. I stepped in.

It was dark and cold inside. There was just enough space to move around. The floor was scattered with empty boxes and some small items of furniture. I shuffled over to the far corner to make space for him as he joined me inside.

He slid the door shut behind him and his demeanour had changed entirely. He had now taken a more assertive tone - "Take your clothes off". As I began undressing, he moved some of the empty boxes around, revealing a single-sized mattress on the floor.

By the time he had turned around, I was standing there in my underwear awaiting his next order. He looked at me head to toe, unimpressed that I was not fully nude.

"I said everything."

I felt uncomfortable being completely nude for the first time in front of anyone, let alone a fully clothed man, but I did not want to anger him. I removed my underwear and without a word, he walked over to me. He came behind me, towering over me and began rubbing his cock through his shorts onto my bare ass. He couldn't keep his hands off me, feeling all over my body. I could hardly stop myself and began massaging his cock over his shorts from behind my back.

After a few minutes of touching, he instructed me to sit down on the mattress that was laid across the floor. I watched as he dropped his shorts to his ankles and pulled off his shirt. He still had his boxers on and he positioned himself right in front of my face. "Suck it" he demanded.

I slowly pulled down his underwear revealing his already erect cock. I was in awe. I was instantly turned on by the sight of his big heavy balls, his thick, white shaft and red, swollen head. It was already oozing out a speckle of precum from all the rubbing he was doing against my ass. Not to mention the smell. It wasn't dirty or unpleasant, but more of the musky scent of a real man that had been working a long day.

I instantly took the head into my mouth and began working away at it, sucking on it as I pulled back his foreskin to ensure that I was pleasuring under the head as best as possible. I was still nervous and so I hesitated to go any deeper, but I kept sucking away.

"Any deeper?" he questioned. I was too shy to admit that I couldn't and instead gave a half-hearted head shake. This did not please him. He put his hand on the back of my head and moved his pelvis closer to my face. He began fucking my mouth roughly to satisfy himself.

I was trying my best to please him as my spit was beginning to bubble around the seal between my mouth and his cock. His unkempt pubes making their way around my nose and lips every time he shoved his cock to the hilt in my mouth. I was trying my hardest to control my gag-reflex which had never been put to the test before.

Eventually he had enough and told me to stand up, I pulled my mouth away from his cock, stings of spit keeping us together. He instructed me to turn around and go on all fours. I complied and waited in that position as he was getting ready behind me.

"Did you bring lube?" I whimpered, I turned around and there was not a bottle in sight. He spread my ass cheeks and spat on my tight little hole. "No, I didn't. The thing is... I like to use my spit instead". I knew this was going to hurt but the anticipation only made me want him more, I was ready to do anything he wanted. Without awaiting any sort of approval, he slapped his cock onto my hole a few times before slowly forcing the head inside of me, once it found its way in, he began slowly pushing deeper and deeper inside. It hurt so bad, but after a bit of time and a few gentle thrusts, my body relaxed, and I gave in to him.

Upon realising that my ass had opened, he readjusted himself on his knees and began pounding my ass. His cock massaging my prostate with every single powerful thrust. I arched my back and let him have me. I was in pure ecstasy. I had never experienced such pleasure and at this point, I knew that being a man's fucktoy was my calling.

My back arched deeper and my arms were extending in front of me, I wasn't even interested in touching my cock and yet it was flapping erect between my legs, dribbling precum onto the mattress below. He was gripping my hips tightly and pulling me onto his cock every time he thrust forward, my ass acting as cushioning so that he can go in with his full force.

We kept in this position for almost an hour, my ass was sore and back was aching, but I wanted to please him. He had no interest in me whatsoever, no care to change position or anything. I was his toy and I was there to help him cum. Eventually, he pulled out, I snapped back into reality, turning my head to see what the problem was. He was ripping open a condom packet. He was ready to cum and I assume he didn't want to make a mess inside of me, although I wouldn't have complained. He applied the condom and went back in full force, maintaining his previous pace. I reached underneath me to massage his balls and thighs to try and bring him to climax. It had worked and suddenly, his thrusts became much harder and more intense, his pelvis clapping off my ass with every shove. I knew what was coming and he began moaning behind me, his grip on my hips tightening up and his thrust become one final balls-deep push which forced my face down into the mattress.

He stayed on top of me for a while as he was out of breath. He was panting in my ear and was resting his full weight on my back. I could feel his cock and balls throbbing and the warmth of his cum-filled condom had completely taken over the inside of my ass.

Minutes later, still inside of me, he gave another 10 pumps to completely drain his balls and then pulled out. He polished his cock off with a tissue, "Get dressed", he said as he threw that same cum soaked tissue at me to clean myself up.

We both got dressed and he escorted me back into the cabin of the van. Again, it was a silent drive back to my street. Before I got out, he let me know that he would likely be free next week for another session.

"I'd love to meet again, you have my email."

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Thanks soooo much for reading everyone, like I said, I'm not a writer but I wanted to share this with you all.

Me and Daddy still meet up and so I have more real-life stories to come!