*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.
