Editor's note: Is there way to predict how someone will react in a certain situation. You might surprise yourself, Justin did. For the sake of experiencing something different, he answers and ad that, even to an experienced bottom, would be considered a challenge. He was brave to do it, but the reality of true submission can mess with anyone's mind. It did with his.
*****
I scanned through the craiglistings for something new, something I hadn't done before. I was bored and looking.
My sex life went back and forth, hot on women and sometimes hot for some sex with a man. I had sex with men a few times, but it was mild, ass play but little else. I never gave head, though I received oral, and was fucked only once, at least I think I was.
Sometimes you can get uncontrollably horny. When that happens, this can happen.
I stopped at the door and took a moment to look around. It was dusk, but I could see the home was a ranch style, in some need of TLC. It stood on what looked to be two acres of land about 150 feet off the road. There were a lot of brush and trees, which hid it from the road.
I was standing there because of an online ad, that read:
Big mature male 60, 240 dominate daddy, very discreet, seeking discreet submissive men for late night encounters in my backyard work shed, plenty of room, blankets on the floor, private, comfortable, must be able to take a raw, rough, deep, breeding and pounding. I got what you want, all you need to do is give it up.
Now that I stood at the door, I was fighting a growing concern, a fear that I bit off more than I could chew. I was horny as hell when I first read through the ads. It made my balls churn, so in a moment of weakness, I replied.
I've had encounters with other men, but they were mild, I'd get oral and finger fucked, but that was it. Once a guy wanted to fuck me. He was not large, so I went along. Trouble was I hardly felt him, and he came in two minutes.
I fantasized about being worked over, giving my ass up for a pounding. Damn it made me hot with a feeling deep in my groin that made me shiver.
My fingers had a mind of their own as I typed my reply. I gave him my stats, 25 years old, 5'9" 155 pounds, WM, sandy hair slim and toned. Because I was so horny, I added 'with a nice ass and tight, little used hole.'
He replied, we made plans and here I am. I hesitated pushing the doorbell, I was nervous as hell. After all, would he stop if I couldn't take it, what other things were in store? I turned around leave, when the door opened.
The ad he placed had a grainy picture attached, it gave me an idea of what he looked like, so I wasn't surprised. His stats matched the ad. He was wearing shorts with a t-shirt exposing tattooed arms. He was heavy but toned. His short hair and unshaven face gave him an intimidating presence.
He looked me up and down and with a smirk on his face, invited me in.
"Name is Sam, what's yours?"
"Justin," I replied.
"Good to meet you Justin, ready for some fun?"
"Sounds good," is all I said.
He gestured towards a rear hallway, "come with me."
He grabbed my ass and without a word, we started towards the kitchen. We walk through the kitchen to the back door. Opening it, he let go of my ass, took hold on my arm and walked me across the yard to a shed at the back of the property. It was rough treatment, ramping up my nervousness.
Except for exchanging names, he hadn't said a word. We knew why I was here, so there was no need for small talk.
The shed was bigger than it looked from the outside. I could see it was insulated and, thankfully, heated. There was a small air conditioner in one of the four windows, next to it stood a fan. On the right there was a workbench and a small stool. In the left back corner was a sink, toilet and what looked like a shower head cuming out of the wall, but not enclosed. On the back wall were tool chests and shelves filled with the normal workshop wares. Next to them was a single metal bed with a thin mattress on it. On the floor was a very thick blanket about 8 by 12. It could pass for a thin mattress. Laying on it was a large pillow. Overhead were two light bulbs hanging from the ceiling, casting a dim light over the room.
I was still pondering the lights when from behind me Sam said, "strip". I turned to see Sam sitting on the stool looking at me. There was no expression on his face, just a matter-of-fact look that told me how this was going down.
"Strip? Just like that?" I said.
"Listen bud, I don't need conversation or questions, so shut up and listen, don't talk."
"Yes sir, geez," I replied as I started to undress.
It was awkward, I've stripped before, but usually at the same time the other person would. But here I stood, undressing, with this expressionless mountain of a man simply watching me. With shaky hands I continued to undress until only my underwear remained. At this point I looked over at Sam to see if there was any change in his expression. None, he just sat there watching.
I wasn't sure which would be easier, facing him or turning my back. I was getting hard and was embarrassed by my erection. I decided to turn my back to him. Reaching under my waist band I lowered my underwear. I stood there naked; I didn't know what to do next.
"Get over here," Sam commanded.
I turned around but covered my crotch with my hands. I looked up at Sam, he noticed me covering up and said, "embarrassed, cute." I walked over to where he was sitting. He didn't move my hands, just took hold of my hips and turned me around. He ran his hand over my ass for several minutes, feeling me up, before reaching between my legs. I could feel his finger search for my asshole, which he quickly found. Without lubricant, he had trouble working his finger in me. After pushing several times, he said, "spread'em."
I reached back and held my ass open. My anus twitched a few times, as I felt his dry finger working its way in. Once in, Sam said, "squeeze my finger, flex that asshole." I let go of my ass, closing my cheeks around his hand and started flexing my sphincter several times. "Is that the best you can do?"
I took a deep breath and bore down on his finger tightening up my asshole as best I could. This went on for several minutes as I tried to tighten more with each flex. In the middle of one flex, he suddenly smacked my ass hard. I jumped, my whole ass tightened up at the pain, but he kept his finger in. "That's better," he said, "now that's tight".
