The Shed

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".

I just stood there, Sam hadn't said a word after the smack, and I was afraid to turn around. He took his finger out, I could hear him get up from the stool, opening a drawer and closing it. I was so curious but didn't dare to turn and look. There was no missing the sound of a belt being loosened, a zipper going down and pants hitting the floor.

He kicked his pants off, I caught a glimpse of them on my left. Now I had to look, turning I immediately focused on his cock. It was a hard seven inches, thick, but, overall smaller than I thought.

"Eye's front," Sam barked as he gave my ass another whack.

"Lay face down on the blanket, pillow under you. Lift that ass up."

I didn't own my body; I might as well be a blowup doll. No foreplay, no connection, Sam just wanted to tag my ass.

It was only a few steps to the blanket. I knelt on it and grabbed the pillow. I put it under me and laid down on it. My cock was hard, and I had to adjust it against my stomach so it wouldn't hurt.

When I was ready, I Glanced back and saw Sam standing behind me, watching me set myself up. I saw my ass bubbled out over the pillow; it was asking to be fucked.

"Boy, you got one sweet ass," Sam suddenly blurted out, "damn."

Sam knelt on the blanket behind me. I braced myself for a furious fuck, but nothing happened. I figured he was enjoying the view but soon I felt his hands gently brush over my ass cheeks. I was not expecting tenderness, but what surprised me is when I felt his unshaven face press against my skin. He laid his head on my ass and didn't move. I shifted a little, but he just lay there, using my ass like a pillow.

A few seconds later I felt him moving his unshaven cheeks across my bottom. He began licking me like a dog, lapping up every inch of my ass. His tongue began to trace down between my cheeks, making me squirm in response.

"Oh, that's it, nice," I moaned.

Sam's tongue licked between my cheeks. Whenever he was near my anus, I moved to get his tongue in me, but he expertly avoided touching it. His tongue kept teasing me, nibbling between my cheeks, but no matter how I tried to line up his tongue, he would change direction.

I lay there shaking with anticipation.

I was fighting frustration, when I felt his tongue search the very top of my ass. Slowly he worked his way down, nibbling and licking as he went. The closer he came to my opening, the more my passion grew. The progress was so slow it drove me crazy. I tried to move, bringing it on sooner, but he held me fast.

His tongue hit the very edge of my asshole and within a moment, it was in me. What a rush. He was burying his tongue deep in me and I lost control, surprising myself when I squealed like a girl. The more Sam tongue fucked me, the hotter I got.

Sam stopped and pushed back on his knees. I had to turn around and look at him. He saw me turn, but before he could object again, I said, "please Sam, let me look at you, it's such a turn on."

Sam didn't object, he smiled, picked up the lube and spread it on his fingers. We never broke eye contact as his hand disappeared behind the mounds of my ass. I shivered when I felt his finger against my anus. It went in without a problem. "Oh yes," came out of me.

One, two, three and then four of fingers began stretching my hole. By the fourth finger, I groaned at the feeling, adjusting my ass, teasing him. "Yeah, help me out boy," came out of Sam as he continued finger-fucking me.

Sam kept it up, fingering and fondling my ass, making me wonder when the main event would happen. I would move and wiggle, letting out a small moan now and again. I was enjoying it and my uncontrollable passion was growing. Reaching back, I spread my ass open, tempting him to fist me, pushing back on his hand, but he didn't. Probably a good thing, I'm not sure I could have handled it. All he said was, "that's it sweetheart, want it bad."

Soon Sam withdrew his fingers and squeezed more lube directly into my asshole. I waited nervously.

"Sam, please be a little easy, ok?"

"You're so damn hungry for cock, I can't believe it. Can't wait for this cock, can you?"

I didn't think he was waiting for an answer, but he repeated his question, "well, can you?"

"No, just fuck me." I felt his gland up against my anus.

He began pushing into me, he wasn't ramming it in, but he wasn't letting my asshole get use to him either. As his cockhead began stretching my sphincter, the pain began. "Please, let me get used to it, Sam, let me get used to it."

If I hadn't been bent over the pillow, I would have pulled away from the pain, but he was pushing down and the pillow held me fast. I struggled to get away from the pain and arched my back hoping I could disrupt the assault. My butt tightened up, my muscles flexed trying to keep the intruder at bay, but I could feel through the pain, Sam was steadily pushing his cock into me.

"Oh man what a fucking tight ass, go ahead, tighten up boy, try and keep me out," Sam said with a laugh.

By the time Sam's belly was up against my ass, I had tears in my eyes. Unable to control myself I pleaded, "Damn it Sam, it hurts like hell, give me a minute, will you?

Sam slapped me hard on the ass, I jumped at the sting, "It'll pass pussy, just open up," Sam said unmoved.

I was feeling sorry for myself when I noticed the slap took my mind off my complaining asshole. As the sting subsided, so did the pain of Sam's cock. I relaxed back on the pillow, relieved.

"That's it, relax that little cunt" Sam said, "you wanted this."

Sam was right, with the pain gone, the thought of his cock buried in me was exciting. His little bitch, naked, positioned for his pleasure, his cock buried deep. I could feel it fill my rectum; it made my balls churn.

Sam's penetration and my submissive passion was overwhelming me. I tweaked my asshole just as Sam was starting to slowly fuck me. I couldn't help but moan.

I fell into rhythm with Sam as he continued to fuck me. "My cock feels good inside you, don't it?"

"It feels so good," I replied.

Sam took hold of my hips and began fucking in earnest. "Take my cock, take it boy, nice and easy, back that ass up," Sam repeated with a moan. I moved with him as his thrusts increased. "Yeah, that's it, fuck like a girl, want it."

Oh fuck, the more he talked the hotter I got and more out of control. I turned to look at him as he continued to pound my ass. I loved the feeling; it was just as I imagined. Each time his cock slid in, I shivered all over and moaned. "Come on Sam, fuck me."

It was so fucking hot.

The severe pounding kept up. He had a firm grip on my hips, and I could hear the slap when his belly hit my ass, I loved the sound.

My asshole was beginning to burn from the friction of his dick penetrating me. I adjusted and moved as the pain increased, but the it was not going away. "Sam, more lube, it needs more lube."

Sam didn't skip a beat but did pick up the lube and douse my asshole. The coolness was wonderful, and his dick began sliding in and out with ease.

"That better?" Sam ask.

"Oh, shit yeah, that's much better. You're really reaming me out, geez."

"That's the name of the game, boy. Nothing like a good fucking."

Sam was shuddering now as he rammed in his dick. I felt it and knew he wasn't going to last much longer. I figured I would help along. "Don't cum yet Sam, keep fucking me, I love your dick in me." I followed that up with a louder squeal and a string of moans and shudders that I knew, would take him over the edge. The surprise was that I felt a tightening in my groin. I didn't know what it was, I've never felt it before, but it was incredibly wonderful. It kept growing to the point that I didn't have to act like I was cumming, I was.

I've never cum like this before. As Sam was fucking me, I never touched my cock, in fact it wasn't that hard.

"Sam, I think I'm cumming, damn I'm cumming," I yelled out. "Get that cock up in me, get in me, shit I want to be fucked." I kept building to a convulsion I was almost afraid of, this was a new feeling, and one that might blow my mind.

That set Sam off, "you cunt, you little fucking cunt, tighten that asshole, fuck yeah."

After a few more thrusts, I knew he was there. "I'm cumming, I'm cumming in your ass you little whore."

I couldn't hold out, the feeling overwhelmed me. My groin tightened my cock twitched to a point of being painful. Suddenly my whole body was overtaken by it and I screamed it out, "Sam, what the fuck."

I came with such a rush; I could feel the cum between me and the pillow.

Sam was cumming, his seed flooding my insides, "Take it, take it boy, shit it won't stop cumming." His hands were still gripping my hips and I could feel his fingers dig into my flesh, his thrusts lifting me off the pillow. I was in the middle of a blinding orgasm and was shouting, "fill me, fill my cunt."

Sam wrapped his arms around my stomach and lifted me up. My back was against his chest, his face was against my neck, as he kept repeating, "damn, what a fuck, what a fuck." He hammered his last thrust into me.

I was impaled on Sam's cock as he held me tight against him. I was exhausted, positive that I had never cum like that in my life. Sam lowered me back down on the pillow. "Nice fuck, wonderful job kid," Sam blurted out. I shivered as he slowly back his cock out.

We both stood up. Sam, dressed only in his shirt, went to the sink and began cleaning up. Over his shoulder he said, "You got a nice body and great ass, glad you came over," then he added, "You really get into it don't you? I like that." Finishing up, he backed away from the sink, "It's yours if you want to clean up."

I said 'thanks' as I walked over to the sink. I saw the shower and decided it would be easier to rinse off then battle with a sink. "Sam, do you mind if I rinse off in the shower?" He answered, "that's what it's there for, go ahead." I reached over and turned the water on, waiting for it to heat up. I turned my head to see what Sam was doing and noticed him watching me. I felt self-conscious, though it didn't make sense with what we had just done. I smiled and turned around as the water was warm enough to step in.

"You really like cock, don't you," Sam said. It surprised me.

I've been conflicted for some time, since I first noticed I enjoyed ass play, but that was all. I spent a great deal of time chasing the girls as you couldn't beat a naked girl moaning to get fucked. I loved every minute of it. But I enjoyed when one or the other girl would play with me and at some point, let her finger linger over my anus. It got so that I would masturbate while playing and fingering my asshole. I graduated to using anything that fit to penetrate me, nothing to big though.

I wasn't gay, I just loved the feeling. My first experience was when I was 23. We were out drinking with some friends and met some other guys, hitting it off. I enjoyed a conversation with one, his name was Jerry. He invited me to come over whenever I could to talk and have a few beers. One evening, I took him up on his invite, he had a nice three-room apartment, neat and clean. We picked up on the conversation we had enjoyed at the bar, when the talk came around to sex. Why I mentioned how I enjoy ass play, I don't know. That is when he confessed, he was bi, more towards the gay side. I had a few beers and didn't react. He ask if it bothered me, being in his apartment with what he just told me. Trying to be macho, I said, 'no way, sex is sex, I guess."

He put his beer down and looked at me, "If I bother you, just tell me to stop." I looked at him Quizzically but didn't say anything. "If you trust me, I could make you feel really good." I still didn't react, so I think he took it as my tacit approval for whatever he had in mind.

It felt surreal as I watched him unbuckle my belt and unzip my pants. When he went to pull them down, I lifted my ass to allow it. He had my pants and underwear down to my knees. I was embarrassed but getting hard. "I see your cock knows when something good is coming its way," Jerry said with a laugh. With his hand he explored my crotch, massaged my balls and pulled on my cock a few times. He knew how to get me hard. He looked up at me, just before he took my cock in his mouth. First time for everything, I thought. Never had a guy blow me off.

He knew how to give head and I relax to enjoy a good blow. This went on for a while, but it was so strange to me, I couldn't reach an orgasm. Jerry stopped and looked up at me, "Does it feel good?"

"Yeah," I replied, I didn't know how to explain my problem.

'Don't worry, you'll cum,' Jerry said as he started on me again. I felt his hand slip between my legs. He move up my inner thigh slowly, rubbing to make sure I knew he was there. His finger reach my ass and I started reacting to the possibilities. His fingers moved between my cheeks, I let out a moan, 'Oh yes,' came out of me.

When his finger touched my asshole, I jerked at the sensation. Wiggling his finger and moving slowly, he entered me. He had only started to finger fuck me, when I immediately exploded in his mouth. I moaned, 'oh damn, what was that?'

From then on, I looked for ways to involve my ass when having sex. With women, it wasn't that easy. Yes, some really enjoyed it, but others were, 'just fuck me'. That's when I began enjoying a few times with men. I never gave head, but many of the men I met enjoy ass play and I enjoyed letting them. Once, while getting rimmed, this guy said, 'I want to fuck you, would you let me?' I didn't reply as he set me up to be fucked. As I mention at the beginning, I was excited to have a cock in my ass, but when he got in, I couldn't feel him, a real disappointment.