Thank you for finding my story. It is my first time writing so please be nice.
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I started on Lit because I enjoy reading erotic literature. There were stories for each and every fetish or kink. Little did I know that one day I would live out one of these stories in real life.
After a few years of just reading the stories I went down the rabbit hole of the Literotica discussion boards. Again, there was something for everyone. I had a few creepy guys contact me asking me to call them names to help them get off. The amateur picture board always drew me in, how could you not enjoy looking at beautiful women in every shape and form.
One evening, I responded to a lady asking for people to look at her breasts. Being a warm-blooded male I sent her a nicely worded private message asking her to send me her photos. It was very difficult trying not to sound like a pervert when asking a woman you don't know to send you naked photos. Like this would ever work.
To my surprise the next day I had two pictures waiting for me. They were the nicest pair of breasts; big and full, long hard nipples, and in one covered in jam. Boy if only I had some toast and tea. I replied thanking her for the pictures and let her know that I was "a sucker for long beautiful nipples." I had not intended on making the pum but I had and she thought it was funny. Not to bore you with our back and forth but eventually we began communicating on Kik.
Our conversations, although they had a sexual nature, most of the time most were Helen and myself getting to know each other. One afternoon we were discussing our kinks and fetishes. I shared how I enjoyed being a sub and she indicated she enjoyed being a domme. In our discussion we settled down on her giving me challenges.
The first week my challenge was to take a photo out in the snow dressed like I was going to the beach. I was a smart ass to her and she said in passing I should do a naked snow angel instead. Well do not give me a challenge and not expect me to not do it. I went into planning when and where I would accomplish my task. The morning I planned to get my pictures I said to myself "forget going to the beach," and I jumped in head first with the naked snow angel. It was COLD. I jumped out into the snow in my backyard, did my snow angel, took my pictures, then ran back inside to warm up.
My mistress received the photos. Note to self, shrinkage is a thing and it is tough to make your dick look big when you are laying in snow at 20F. The pictures pleased Helen and she gave me my second challenge.
I had to go to a park or the woods wearing a thong and take a picture with my pants down. Thankfully, I live in the country so there were trails and parks I could go where most people never go. That part is done. Now I had to go buy a lace thong. Boy did I get looks buying an XXL thong at the mall. Everything was in place, I just had to figure out when I could do this.
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(I am using this to differentiate between two characters' thoughts)
Things fell into place, and one day I found myself pulling into the parking lot at a local hiking trail. I parked at the far end of the lot even though there were no other cars. I guess it made me feel better. I got out of my car and looked around for any other signs of life and did not see any. No cars, no footprints in the new snow, not even an animal track. Kept thinking to myself "I can do this." Threw on a winter hat and off I went.
As I walked along the trail, I was looking for a spot to take my pictures but also making sure no one else would be able to see me. I do not want to get arrested for this. The trail runs parallel to some train tracks (I guess the trail is the bed for an old train line) and I found my spot. Under a small train bridge I could be out of sight and get this challenge completed. I was so focused at this point I did not look around before I walked under the bridge. If I had, I would have noticed her walking a few hundred yards behind me.
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That man pisses me off. He never wanted to have sex with me anymore. I wonder if he is having an affair? Maybe those lesbians know something I don't. Never mind, I love cock too much. lol.
I needed to clear my head and there is no better place than a nice hike on this beautiful winter day. The sun was shining and there was a new dusting of snow on the ground. Pulling into the lot of my favorite trail I noticed another vehicle. Not completely out of the ordinary but it makes me keep my guard up, never know what people you will run into.
Starting my walk I began thinking "what was wrong with me that he never wanted sex with me anymore?" It had been so long since we had sex, nothing helped my cravings. Not my vibrator, my fingers, or the new shower wand I just had installed. However frustrated I was, this hike was for me to clear my head and get some exercise. As I walked and I worked things out in my mind, I finally decided I needed to look up and enjoy the surrounding snowy scene.
When I did look up I noticed someone walking a few hundred yards in front of me, I assume this is my parking lot friend. I could not tell much about them from being so far away, but they seemed to enjoy the scenery because they were constantly looking around at this winter wonderland around us. Out of the blue, they hung a right and ventured off the trail. What the heck?
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As I veered off the trail to hide out under the bridge and get this over with; I was nervous and excited all at the same time. My hands were shaking so bad. I pulled my pants down to get the shot of the thong going up my backside. This proved more difficult than I had expected and after a few failed attempts I gave up.
My first successful pic was everything tucked neatly in the thong. I took a few and then would check them out. I was completely enveloped in my own little world. Next on my list, per my mistress, was a shot with my cock outside of the thong. Well between nerves and the cold I barely hung out the side. Just my luck.
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What in the world was this person doing? These are the times I regretted hiking along. I hurried up to see what was going on. As I came up to the spot where I watched the person leave the trail I walked slower and tried to be as quiet as possible. As I got closer I saw them under the old train bridge with the pants down. WTF! It was a guy taking selfies in a thong!
Although I should have been mortified, I found the scene to be extremely erotic. Coupled with my current dry spell at home and this scene laid out before me I started getting tingly in all the right places. I watched as he took picture after picture trying to get just the right one. All of a sudden he pulled is cock out taking more pictures. Wow did he have a nice looking package. Even in the cold he was definitely bigger than my husband.
Apparently, he was trying to get a hard on or he was masturbating because he was going to town on himself. I looked around to make sure no one else walked up on me and my voyeuristic scene. With no one else to be seen, my hand had a mind of their own and it found its way into the front of my pants. As he rubbed his cock the head turned purple and it got so veiny. It looked amazing. I wanted it so bad but I did not want to interrupt my show.
I was so turned on and wet. I began rubbing my clit and I was getting close to the finish. I braced myself against a tree as my legs got weaker the closer I got to orgasming. Driving 2 of my fingers into my hungry cunt was all I needed to have my orgasm. It was the best I had in months. In my orgasmic bliss I lost my balance and fell breaking sticks on the way down. I was busted. Or was I?
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Oh shit what the fuck was that?! I quickly tried to grab my pants that were around my ankles.
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