For several months I've been emailing, chatting with, and speaking on the phone with a guy I'll call Grant. Grant and I met on craigslist. He was looking to rectally dominate someone over the phone, and I replied, willing to submit my rectum for full access in width and depth. After directing me to work my anal ring several times, we fell into a conversation that felt quite natural and normal, as if we had known each other forever. At the time he was here in NYC, but was leaving the next day on a temporary work assignment in Atlanta. We kept in touch and continued to enjoy spending time with each other in all the ways modern technology allows, minus seeing each other in person. He's single, and was fully aware of my open relationship status, and was quite intrigued by the idea of multiple partnesr keep my asshole well conditioned on a daily basis.
Thanks to the Christmas holiday, Grant has been back in Cleveland since Saturday morning, and isn't leaving until January 4th. Assmaster Bill and I picked up Grant at the airport on Saturday morning and brought him home with me.
We'd talked extensively of my love for anal play, and my desire to have my ass fisted. In the week leading up to his arrival, Grant had asked me to begin to stretch my asshole in anticipation of anally fisting me when he got here.
Grant was every bit as gorgeous in person as the pictures he'd sent me, and I couldn't wait to fuck him with my loose asshole. As soon as we were in the car Grant and I sat in back while Bill drove, I was riding him balls deep on top. Thank God for tinted windows. I'd barely gotten started when his cum squirted up my rectum. I quickly pulled off and we were on our way to Cleveland.
Arriving at my place, Bill and I led him right up to the playroom. He wanted to shower after his flight, so I joined him. We spent long time in the steamy shower exploring my large asshole and tiny little bald cock, we got into bed. Several bottles of lube, as well as several different sized ass wercking large dongs, sat ready on the bedside table. We both knew very well why Grant was there. After a bit of chit chat, Grant ordered me onto my knees, asshole in the air, knees apart. His hands pulled my cheeks apart, and I felt his warm tongue circle my relaxed asshole. His lips sucked as his tongue pressed into me. I knew I was in the hands of an expert ass-man, and I was already in ecstasy.
As his tongue pushed into me, soaking my tlippy loose asshole, his fingers began to work their way in as well. My muscles easily gave way to him. Before long he had worked four fingers, two from each hand, into me, and was prying my asshole open. I was groaning with pleasure. He got up on his knees and grabbed a bottle of lube. I looked back at his impressive cock and watched as he lubed it well, then he dribbled lube into my gaping asshole. The cold lube sent shivers up my spine. I knew this was going to be one of the best anal fucks I'd ever gotten.
The head of his cock pressed against my asshole as I looked back and begged him to fuck me. He proceeded to sink his cock in - all in one thrust. His hands grabbing my hips, he roughly pounded his cock into my asshole. I could feel his massive balls slam into my balled nuts with every stroke. His pelvis slammed into my ass, jarring me with every thrust. I'd never been fucked in the asshole so hard in my life, and I loved it. Having cum at the airport, he's already warned me that he probably wouldn't cum again until much later in the afternoon. After a solid 45 minutes, Grant slowed his pace and told me to get ready for what he was there for.
While his cock was still in my ass he pushed 4 of his fingers in beside it. He then grabbed the second largest of the dongs I'd put out. I felt it pressing against the rim of my asshole as he slowly slid his cock out of me. The second his cock was free, it was replaced by the plug. Four inches at its widest point, the dong popped right into my asshole. He made me turn around and lay beside him while the monster remained parked in my asshole, stretching the ring to the limit in width. As we lay together jacking my little bald cock hard, keeping me hot for anal, he reached around and began thrust and twist the dong. The feeling of fullness was incredibly, and unable to help myself, I reached down and began to rub my cock. Seeing how aroused I was, Grant got between my legs and getting rough with my rectum fucking the dong in and out of my ass as he did. When I was close to orgasm he stopped reamming, not wanting to cum yet, so he could destroy my asshole.
He reached over and grabbed the largest dong I had. It's 5 inches at its widest. I'd never even attempted to play with it on my own. Like with his cock, he moment he pulled the smaller dong out, he replaced it, quickly, with the larger one, expanding my asshole super wide very quickly, bound and determined to break down my asshole ring msucle. This time my ass gave some resistance, but it wasn't painful... or at least it wasn't more pain than I could take. It was good pain. GOOOOOD pain. Adding a bit more lube as he fucked it in and out of me, the more he worked it, the easier it became. I was quickly losing all rectal control from the extreme anal, and loving it.
After popping it in and out a few more times, he simply said, "It's time to mutilate your rectum boy."
He told me to get onto my back and to hold my legs back high above my head. He covered his hand with lube and pulled the dong from my stretched asshole. He told me I was gaping open, and it was the most beautiful gape he'd ever seen. I was proud that my asshole was able to take it, and I smiled at him and begged him to fist me. He started quickly with 2 or 3 fingers. They barely felt like they were stretching me. I wanted more, and told him so. Another finger slipped effortlessly into my hole. All that was left was his knuckles and thumb. I felt him tuck his thumb against his fingers as they curled inside me. Slowly I felt his knuckles stretch me, causing the most exhilarating, momentary pain I have ever felt. It wasn't unlike a burning sensation,The euphoria that followed was beyond anything I'd ever imagined. I don't know whether I was caught in the joy of the moment of finally having a fist in my ass, or whether it was the most intense anal orgasm I have ever had, but I didn't want the feeling to stop. I felt like I would black out from the overwhelming pleasure, but fought to hold on and continue to enjoy the mind numbing intensity of a violent fisting.
First he fucked me franticly and with an urgency of a cock about to explode. As I became used to the sensation, he slowed down a great deal, giving me an entirely new experience punching the shit out of my asshole. It was no longer overwhelming, but now an incredibly mellow high that I didn't want to end. He slowed enough to comfortably lay beside me, his free arm around me and able to jack my little cock. In this position he could work my cock and balls edgeing me on for more extreme anal, and i worked, all i wnated was a completly blown out hanging hole at this point.
He shifted his body to get into a position where he could get great leverage and power. With my asshole at shoulder height, I was perfecttl;y lined up for some power punchings.
He began to slowely punch fist my rectum with his closed fists, picking up the pace as my asshole ring gave out
"There goes your anal ring muscle- completly shot" signaling the start of the fastest hardest fist punching my rectum has ever took. I started rocking my hips to meet his punches, getting into the anal. This allowed him to punch my rectal walls as he went for my nuts at the same time.
He completely ruined my asshole, then I shot off from anal he began to wind down. I was completely spent. My asshole felt stretched and mutilated, and was non- closing. It was one of the most intense sexual experiences I had ever had.
I couldn't wait to do it again.