The Challenge

It wasn't until I was 27 years old that I had ever been fucked in the ass by another man. I'd given and received blow jobs, and done my share of jerking off with other guys, but I was totally naive and inexperienced about taking it up the ass. In fact, when I first started going to a local gay porno theater to be fascinated by the images on the screen, I actually thought the films of men getting pounded by other guys were created by trick photography. I just knew that cocks as big as those on the porno stars could not possibly fit into something as small and tight as an asshole.

I'll admit the first time a hard dripping cock broke into my ass it was the most painful thing I had ever experienced. But, just as the guy behind the cock kept telling me, within a couple minutes the pain evaporated into the most pleasurable feeling of my life. Far from being the "sissy" activity we all have been taunted about; taking a big, throbbing, hot cock up the ass is an incredibly masculine experience. From that first time I was hooked and I have certainly had my share of manmeat in my hole.

I do think most gay men, whether they will admit it or not, tend to be "size queens" on occasion - or even all the time. I had always been concerned about my own size until I really started experimenting with men. I never got any complaints. In fact, almost every man I ever had sex with came back for seconds - whether I wanted him to or not. It gave me a lot of confidence socially and sexually with other men.

I'd heard rumors about this guy Gary for quite a while. Guys from the gym had seen him in the locker room and shower. Some guys from the neighborhood gay bar had even gone home with him. Word got around that his cock was so big it was impossible to give him head. Most guys wouldn't even consider letting him try to fuck them because his monster cock could rip them in two. Most often, the men he went home with had to fuck Gary or just jerk him off. Just thinking about it made my butthole wet.

Gary was about 6' 3" with black hair and eyes so dark they almost looked black, too. His hair was medium length, but some of it always was falling down across his forehead. An actor, he tended to dress in his standard drag of faded jeans, a white T-shirt and black leather jacket.

On one typical Saturday night some friends and I went to our usual gay hangout. Standing alone at the bar was Gary, looking kind of like a big "lucky dog" trying to make people think he was a tough guy. He glanced across the room, raised his drink to me and smiled. Little did he know that the friend I was standing with was telling me about going home with him at that precise moment. Tim went on and on about how BIG his cock was and the most amazing thing was it actually got as hard as steel. He commented on how most guys would pass out from that much blood leaving their brain to pump up another body part. It was then that I took Gary's cock as a personal challenge. I wanted that thing in my ass! I raised my glass to Gary and smiled back.

As the evening went on my friends got bored with the bar and wanted to move on. I wanted to stay - and take on my challenge - but I didn't want my friends to know I planned to hit on Gary. He watched as my friends and I left. I winked at him and walked out the door. When we got to the parking lot everyone agreed to meet at another bar. Except me. I lied, saying I had an early morning appointment and had better head home. As soon as my friends' cars left the parking lot I headed back into the bar.

Gary was just walking out the door by himself. He looked surprised to see me coming back in and asked "Oh, did you forget something?"

I explained I really didn't feel like going to another bar with my friends and wasn't quite ready to go home. He immediately asked me if I was ready to go to his home, which was just a few blocks away. Not being a fool, I quickly agreed. Within five minutes we were at his place. As soon as we were in inside he pushed me up against the wall and kissed me roughly. Without speaking we began removing our clothes as he guided me to his bedroom. By the time we were standing by his bed both of us were completely nude with our dicks pointing toward the ceiling.

I couldn't do anything but stare at his cock. The thing was HUGE! It had to be a good 11 1/2 inches long and as big around as my wrist. The purple head looked like the size of a tennis ball. And it was HARD! Most really big cocks I'd had the pleasure of enjoying never got totally hard. This was definitely going to be a challenge.

The next thing I knew we were on the bed with Gary deep throating my 8-incher. I had both hands his veiny pole jerking him off. I couldn't begin to get the thing in my mouth. (Have you ever tried to put a tennis ball in your mouth?) However, I did my best licking the thing and mouthing his balls. Both of his hands were deep massaging my ass. Every once in a while a finger would tease my asshole. We were a tangle of arms, legs, fingers, mouths, tongues and cocks. This guy was incredible.

Gary came up for air. "You've got a great ass. I've noticed you down at the beach in your Speedo. I'd really like to fuck you."

He had to know how much I wanted him inside me. I admit the thought terrified me. I really didn't know if I could handle the thing. He must have recognized my hesitation because he began telling me about not many guys allowing him to fuck them because of their fear of being physically hurt. He told me most of them just weren't willing to take the time to truly relax and prepare themselves for an incredible experience. I think his "actor's voice" had a soothing and calming effect on me. I rolled on my stomach and Gary began giving me the most incredible massage I had ever experienced.

He spent a lot of time concentrating on the globes of my ass. I felt him bend down and begin kissing my butt. The kisses were followed by a tongue wetting my crack and circling my asshole. His tongue entering my assring caused a loud moan to come from my lips. He withdrew his tongue and it was replaced by a finger covered with a cold lubricant. The lube seemed to heat up as it was rubbed into my hole. As I got more relaxed I felt another finger enter me. It was followed by a third, and a fourth. It felt as if he was massaging the inside of my ass. My own cock had never been this hard, but I felt so relaxed I didn't even make the effort to reach for it and found myself gently humping his bed.

Gary laid down beside me and rolled me over on my left side. Lifting my leg, he placed his throbbing meat along the crack of my ass. With one hand he kept rubbing my head, my face, my pecs, my abs and my cock. It was an amazing experience. With his other hand he grasped his cock, moving it back and forth across my puckering hole. Each time it moved across the opening he pushed in gently into me a bit more.

He was licking the inside of my ear and whispering "take a deep breath, relax and enjoy" over and over as if it were a mantra. I felt like Jell-O in this man's power and the most relaxed I ever been with another individual.

Suddenly, he pushed hard with his groin and I felt as if all the wind had been knocked out of my lungs. I tried to scream but no sound came from my mouth. The entire time his hands were roaming over my body and he was placing little kisses on my face, neck and back. He began to slowly rock back and forth. With each rocking movement a little more of his flesh disappeared into my ass. The pain was gone. In its place was an intense warmth and feeling of joy. Tears were running down my face. But they weren't tears of pain or sadness. Gary turned my head and licked the saltiness from my cheeks.

I lost all sense of time and surroundings. By this time I could actually feel his wiry pubic hair between my buttcheeks. If this wasn't nirvana I don't know what was. Gary somehow positioned our bodies so I was now getting it up the ass while on all fours. Each thrust was followed by him pulling his cock back out until just the head remained in me. My breathing was in unison with the pounding I was getting from this man.

Concentrating on what was inside of me I had paid no attention to my own rock hard cock. And I didn't need to. The massaging of my prostate by the huge piece of meat inside me set me off without either one of us ever having to touch me. Both of us were completely drenched in sweat, and Gary just kept up a steady pace of moving in and out of me. In a short time I came again. After I came a third time Gary quickened his pace. With both hands on my shoulders he plowed into me again and again. Finally, he let out a scream like that of an injured animal and I could actually feel spurt after spurt of hot liquid deep inside my ass.

Exhausted, we rolled back onto the bed with his semi-hard cock still inside of me. The sun was shining through the blinds when I felt him slowly slide out of me. Having met the challenge, I drifted off to a dream-filled sleep.

When I awoke mid-morning Gary had already left for work. Beside the bed was a note saying he hoped we could do it all again in the near future. I got dressed and walked out his door. As soon as I shut the locked door I realized I had locked my keys inside. With my ass a bit sore, I slowly walked to a nearby coffee shop. That evening I returned to Gary's to get my keys. I also got a repeat of the previous night. I was certainly up to the repeat challenge and enjoyed every minute.