The Best Fucking Of My Life

It was right at the start of my last semester of college when a friend told me about an amazing gay bar about 15 minutes from campus. I had been out of the closet since the day I moved in, but this was the first time I had heard about the bar. I decided one night to go check it out. It was still early in the semester so I knew I would have a free weekend to have fun. Ever since my boyfriend and I had broken up the summer before I hadn't had sex, let alone gone on a date so I was really looking forward to meeting some new guys.

Finally Friday night came and I got ready to go out. I showered, shaved everything, and made sure my body was ready for whatever was going to happen. I put on a pair of black skinny jeans that made my ass and bulge stand out. I decided to skip the underwear to make things a little more interesting. Then I put on a skin tight purple v-neck t-shirt, a black vest, and boots. I made sure my hair looked perfect all pushed off to one side and I headed out.

Luckily it wasn't too cold out so I was able to show off my sexy outfit. My dick felt strange rubbing on the inside of my jeans but I didn't care. After about 20 minutes of walking I was at the bar. For the life of me I can't remember the name, but I do remember seeing crowds of hot men. As I made my way inside I started looking around for guys I would be interested in dancing with. It was a little overwhelming at first but once I made my way to the bar I started to relax. I hadn't even ordered a drink yet when I saw someone out of the corner of my eye approach me. I turned around and standing there was this huge, gorgeous man. He looked to be about 40 and he was covered in hair. His muscles were bigger than any I had seen before. I was pretty tall at 6'1" and 135 lbs, but him standing next to me made me look like a child. All he was wearing was a pair of tight basketball shorts that perfectly outlined his dick. It looked huge even soft and that got me very excited. He was the perfect bear and I instantly wanted to bend over and let him fuck me right then and there, but I contained myself.

"Can I buy you a drink?" he asked in a deep, sexy voice.

"Absolutely!" I replied.

"My name's Scott," he said as he held out one of his huge hands.

I shook it and said "I'm Nick."

We sat at the bar for a while making small talk while I downed my free drinks. Before I knew it I had had 5 beers and I was starting to feel willing.

"Do you want to go somewhere a little more fun?" Scott asked me.

At this point I was starting to think about what was going to happen tonight. Scott grabbed my hand and began to lead me through the crowd of sweaty, drunken, horny guys. As we made our way to the back of the club I felt numerous hands grab my stiffening cock. Scott brought me to a stairway at the far side of the club that led to a lower floor. There was a bright neon sign above the doorway that said "DUNGEON." I felt my stomach drop. I thought about trying to pull away but I knew I wouldn't be able to escape Scott's grip.

As we walked down the dark stairs my heart began beating faster and faster. When we got to the bottom there was a long hallway with six rooms on each side. It was dark, hot, and smelled like a mix of sweat and cum. I could hear moaning coming from the rooms and occasionally the sound of leather hitting skin resonated through the hall. We walked past several rooms before going into the third on the right. I glanced into the rooms on the way and I could see men of all ages and sizes having sex. Some were in sex swings, some were tied up, and I even saw one guy with another man's arm up his ass.

All of a sudden I knew why he was taking me down here and what this place was for. As he led me into the empty room thoughts started to race through my head. The room came equipped with a bed, a sex swing, and a whole wall dedicated to sex toys. There were whips, chains, dildos of all shapes and sizes, handcuffs, rope, duct tape, and even some things that I had never seen before.

I think Scott could sense my nervousness because he said "Don't worry, this will be fun."

He started rubbing my semi hard cock through my jeans and I started to loosen up.

"Have you ever been fucked by an older man?" he asked me.

"No, never," I replied.

"Well you're in for a real treat tonight you little cock sucker," he threatened. "From now on you will refer to me as sir, got it?"

"Yes sir," I said as I started to get more excited.

"The safe word is blueberry, got it? No matter what else you say I won't stop. And only say it if you're about to pass out. Actually you know what, don't even say it then. I wouldn't mind fucking an unconscious fag."

I really liked the rules of this game, but I could also feel my stomach churning. My boyfriend and I had never had sex like this. It had always been sweet, loving sex. I could tell that kindness was out of the question tonight.

"Take your clothes off bitch," he yelled at me.

I immediately started stripping. He was pretty surprised when I took off my pants and my cock fell out. He took off his pants and I got my first look at the monster hanging between his legs. He grabbed my shoulders and pushed me down onto my knees so his 9 inch cock was right in my face.

"You wanna suck my cock fag?" he asked me.

"Yes sir. Please let me suck it," I begged.

I opened my mouth as wide as I could and he set his dick on my tongue. It felt so soft against the inside of my mouth. I started to go to town sucking and licking his thick cock. I only took it about half way at first because it was so massive. I kept twisting my mouth all around his dick while I licked the head with my tongue. Once I had warmed up to it he grabbed the back of my head and began to force his dick further and further into my throat.

"You're gonna take it all the way you little faggot," he said as he got more aggressive.

With every thrust he pushed his dick farther down my throat and every time I gagged. When he finally got it all the way down my throat he kept it there for a few seconds. I couldn't breathe and I tried to pull away but his grip was too tight. Finally he let my head go. As he pulled out I coughed up a huge amount of saliva which ran out of my mouth and down my chest. He did that again several more times, each time holding my head there longer and longer. At one point he had his cock jammed down my throat for 15 seconds without letting me breathe. I was worried that I was going to throw up.

After the last time he pulled out I kneeled on the floor gasping for air with my spit covering my chest and stomach.

"Get up bitch," he ordered, "Get on all fours on the bed."

I immediately did what he said. I was just happy that the throat fucking was over. Scott walked over to the wall of toys and picked up a leather whip. For some reason my cock twitched and got a little harder.

"I hope you like pain, boy."

"Yes sir. I want you to teach me who's boss."

"That's right faggot. You'll never forget me."

He started rubbing my ass cheeks and slapping then lightly. Then all of a sudden he hit me with the whip. I immediately jumped from the sting.

"Don't move boy. You need to learn to take it," Scott said.

He hit me again and I tried not to move but the stinging was worse the second time.

"What did I tell you? Don't fucking move."

I could tell Scott was getting angry, and I didn't want to see him angry.

After about 5 hits I started to be able to control myself, but each hit was getting harder and harder. I looked in the mirror on the far wall and I could see my ass was turning bright red. I could also see little lines of blood all across my cheeks.

He hit me again right on the same spot as before.

"Thank you sir," I said as he hit me again. I could feel tears gathering at the corner of my eyes.

"You gonna cry fag?" Scott asked. "If you cry a single tear I will whip you even harder."

I fought back the tears as best as I could. Again the whip made contact with my raw ass cheeks. I was starting to wish I was still suffocating on his cock. I thought about saying blueberry, but a part of me didn't want this to end. Plus I knew Scott would be furious.

"Last time before I fuck your asshole boy," Scott said as the whip made contact with my ass one final time.

I was so relieved when he put the whip back up on the wall. He then grabbed me off the bed and threw me into the sex swing. He lifted me up and set me into position. My ass stung as I sat there. He spread my legs open and began to tease my hole with his cock.

"You wanna get fucked faggot?" he asked.

"Yes sir, please fuck me raw," I was getting so turned on knowing I was finally going to be fucked.

He pushed the head of his cock into my waiting hole and I could feel it stretching to allow it inside.

"Holy shit," I yelled, "It hurts so fucking much."

"Shut up and take it boy."

I had never had something this big up my ass and I could feel my hole being stretched beyond its limit.

"Stop please I can't take it," I begged, knowing he would just push further.

Sure enough he ignored my begging. He pushed in another inch before pulling all the way out. My hole stayed open even with the absence of his cock. It was only empty for a second because he pushed his cock right back into my hole. This time the pleasure outweighed the pain. He slid his cock all the way up my hole and I could feel his balls against my ass.

"Oh my god, you're so fucking big," I said trying to ignore the fire I felt in my hole.

"You like having a cock shoved up your ass you little slut?" Scott asked.

"Yes sir, it feels so fucking good. I want you to destroy my hole."

"Well since you insist," Scott replied as he started to frantically fuck my hole. Over and over he forced his throbbing dick into my tight little hole. Each time his balls slapped against my ass.

"Yeah, fuck me hard sir. I don't want to be able to walk right."

The talking was turning us both on so much. I looked down at his cock as it went in and out of my hole. I could see a little blood on his dick from my hole being stretched out. Finally his cock was starting to feel really good rubbing against my prostate. I looked down at my own cock and it looked like it was ready to burst. It was almost sore from being so hard for so long. I reached down to start massaging it for some relief but Scott slapped my hand away.

"You don't get to cum until I want you to. I'll decide when you get to feel relief, got it?" he asked.

"Yes sir, but please hurry. My cock is begging for attention."

"What do you want boy?"

"I want to cum sir, please?" I replied.

"What do you want from me?"

"I want you to breed my ass sir."

As soon as I said that he started fucking me even harder. My swinging back and forth added to the force behind his thrusts. I felt like his cock was in my stomach. He grabbed my dick in his hand and began massaging it frantically. It didn't take long for the pressure in my balls to release.

"I'm cumming!" I moaned as I shot a huge load all over my chest. Some even got on my face. I wiped it up with my fingers and licked them clean.

"You ready for my load fag?" Scott asked?

"Yes sir, shoot it up my ass. I'm ready for it."

"Ahhh," Scott moaned as I felt his dick twitch and release its load into my hole.

"Fuck yeah," he said as he let his cock empty into me.

We both stayed frozen as we tried to catch our breaths. That was by far the best fucking I had ever had.

"Don't let any of my cum fall out of your ass boy. I want you to leave it in your ass for awhile," he said as he carefully pulled out of my used hole.

We both got cleaned up and I gathered my clothes. As I was getting dressed I felt so much pain from both the whipping and the fucking. Scott slipped a piece of paper in my pocket with his number on it in case I wanted to meet up again. I had to call a cab to take me home because there was no way I would have been able to walk. When I got back to my apartment I took off my pants and noticed a mixture of blood and cum leaking out of my hole. I immediately got hard again. I spent a significant part of the night jacking off to the memory of what had just happened before I fell asleep hoping to feel better in the morning.