Author's note: This is a true story. I might have missed some of the details, but not many.
I had met Ray online many years ago. He said he wasn't gay, but his wife had given up on sex entirely. However, he still wanted physical sex but didn't want to "cheat" on his wife with another woman. He definitely interested me, and he said he would meet me at a sleazy no-tell motel.
I followed his directions to the motel. When I got there I found that the place looked like it had been built in the 1940's or 1950's. It sat under a highway overpass, and there was only one way in and out.
True to his word, Ray was waiting there for me. He'd given me a general description of himself: Late 50's, gray hair and beard, about 6' tall and about 170 pounds. It helped that he was the only person standing in the parking lot when I pulled in. He smiled when he saw me pull in and park next to him.
"I was afraid you wouldn't show up," he said, giving me a hug and rubbing the back of my neck. I felt a large lump in his pants press against me during the hug.
He was nervous when we walked up to the office window to get the room. "My wife thinks I'm going to San Marcos to see friends," he explained. "I'm really worried that someone will recognize me here and tell her. She'd divorce me in a heartbeat if she found out."
The elderly clerk, however, obviously didn't give a shit about what went on at the motel and pointed us in the general direction of room #3 after Ray paid the man for three hours use. We walked over to it.
He unlocked the door and we quickly went inside. The room was as bare-bones as possible for a motel. There was no TV or fridge, only a beat up dresser, a chipped and worn nightstand, and a bed. The tiny bathroom simply had a toilet, sink, and shower.
As soon as we walked in, he closed the door behind us and bent his head down to kiss me. He definitely was a good kisser. As his beard tickled my face and his tongue explored the inside of my mouth, I wasted no time stroking his hard cock through his pants.
He broke the kiss, and stepped back to undress. I quickly stripped my shirt off and then my shoes, pants and underwear. When I glanced back at Ray, he was already nude and waiting for me. I stared in shock at his cock.
I know that most stories always have someone with a big dick in them, but honest to God the man was HUGE! I knew that he had a big dick from the lump in his pants and from stroking it when he was kissing me, but I didn't expect it to be THAT big. It was at least 9" long and super thick. It was easily the biggest dick I had ever seen outside of a porn film. He was hard, but the weight of that thick cock kept it pointed towards the floor.
I looked at him nervously. "I'm not sure I can handle that," I admitted. I couldn't imagine a way to get him in either my mouth or my ass.
He started to get a depressed look on his face, but smiled when I quickly added, "Oh, I'm still going to try!'
He sat on the edge of the bed next to the pile of his clothes, and I knelt down between his legs. I licked my lips nervously, then wrapped my hands around his cock and started giving little kisses to his cockhead. He groaned quietly as I trailed my tongue up and down.
The moment of truth arrived, and I placed my lips against his cockhead. I pushed my mouth onto his cock, feeling my lips stretch. My jaw began hurting even before I get his entire cockhead in my mouth, and there was no room in my mouth for my tongue to do anything to his cock except be pressed against him.
I tried and tried, but I could not get my mouth open wide enough to take him in more than an inch or two. After a few minutes, I gave up. There was simply no way.
I rocked back, pulling his cock from my mouth. "Lets try the other end," I suggested. I was a bit scared, afraid that if I took his monster cock in my ass he would tear my asshole open. Luckily, I was too turned on to not try.
I reached over to my pants, and pulled out a bottle of lubricant that I'd brought. I lathered his cock and my asshole up liberally, then tossed the bottle on the bed. I crawled next to him, ended up on my hands and knees with my ass pointed in his direction. Wordlessly, he moved around behind me and placed the tip of his cock against my asshole.
Ray was turned on and frustrated, but he was surprisingly gentle. He slowly pushed against me, his cockhead spreading my asshole more and more. He pulled back out when a sharp pain made me cry out, then put more lubricant on his cock and started pushing into me again.
It took forever to just get his cockhead inside me but with patience on his part and determination on mine, plus lots and lots of lubricant, it finally nudged past my sphincter. It felt like I had a bowling ball stretching my asshole.
He stopped pushing for a second and I felt him jostling on the bed. I looked over my shoulder at him and saw he had pulled a camera from his pile of clothes. He snapped several pictures of my asshole being stretched by his cockhead, then tossed the camera back onto the bed and began pushing into me again.
I'd never been so full in my life. When I thought I couldn't stand it any more, I'd tell him to stop. He'd wait for me to stretch enough so that it wasn't painful, then resume.
Finally, after what seemed a lifetime, he was fully inside me. Speared by his huge cock, I was afraid to move, but he slowly began to pump his cock in and out of my protesting asshole. The pain from his size was slowly being replaced by the pleasure of his size.
I knew he was really turned on. My asshole wrapped his cock like a vise, and it didn't take him long to cum. He had only fucked me for a few minutes when I felt him shudder and roughly shove his cock as deep into me as it would go. As I yelped in pain, I heard him gasp as his cock throbbed and flooded my bowels with cum.
He stayed pushed inside of me until his cock stopped filling me with his cum. Normally, I like to make it even better for the guy in my ass by flexing my ass muscles and drawing every bit of cum from his balls, but he was so big that I couldn't with him.
I started to pull away from him, but he grabbed my hips to prevent me. I glanced over my shoulder again and saw him grab his camera again. He pulled back from me a bit, enough to see his cock buried in my ass, and snapped several more pictures. Then, he slowly pulled out of me, taking picture after picture of his cock sliding out and the flood of cum that followed.
[Note: He emailed me those pictures later. For years I jerked off reliving that fuck through those pictures, until my computer's hard drive fried and I lost them.]
He laid on the bed next to me, and I climbed out of the bed and got a wet washcloth from the bathroom. I cleaned his cock off, giving it a few kisses in the process, then tossed the washcloth on the floor. I laid next to him with my head on his shoulder.