My ass was sore after my last session with Rich, I loved it and couldn’t wait till Sunday morning to come around. I was a good boy and refrained from jerking off so my balls were full when Sunday morning came around and I was ready to explode. I was also hungover and get very horny when I’m hungover.
I messaged Rich and told him I’d be over after I showered and prepped. I also mentioned that I wanted to really focus on him stretching out my tight little hole rather than a full massage as well. He quickly replied saying he was ready whenever I would love the present he had for me. I was quickly on my way over. When I got there he led me upstairs and I undressed and hopped up on his table.
He started by rubbing my cheeks and gently blowing on my hole which began to build my excitement. He squirted lube all over my ass and began applying pressure to my hole, slowly slipping his pointer finger in. He took his time working that finger in and out of my ass, nice and deep. This already had my cock dripping with precum and I started pushing into his finger thrusts. He soon added a second, then third, and fourth finger and slowly worked them in and out of my ass till I was able to get comfortable with the stretching. Soon enough, I was begging him for more. I couldn’t get enough of the dizzying euphoria I was in while Rich worked his hand in and out of my ass. He increases the speed and my body started to tremble and shake. I was in heaven.
Smiling at me, Rich asked if I was ready for my surprise. Eagerly I nodded my head. Out of his cabinet, he pulled out a beautiful, girthy dildo that had to be 16in long and proportionately wide. I think I gasped when I first saw it and was nervous and excited at the same time. Rich applied lube to the toy and my ass and pressed the tip against my already gaped hole. I’d love to say I took it like a champ but this was definitely painful at first. Rich picked up that I was uncomfortable and slowed down, making sure I was okay before he inserted it further. Eventually he bottomed it out in my ass, I moaned with excitement that I fit all of it in, but I still hadn’t fully loosened to the point where it was comfortable.
I asked him to slowly fuck me with it, wanting to get comfortable as quickly as possible. He obliged, slowly thrusting this monster in and out of my ass, pressing slightly hard when he bottomed it out. I was starting to love it. My dick had grown soft with the pain that I initially felt but was leaking cum. As I moaned more and more, Rich picked up the pace. I was taking this monster dick and I was proud of it. I was still on my hands and knees as I begged Rich to fuck me hard with it.I started to sweat with pleasure and the harder he fucked my ass with it the more I felt like I was leaving my body. This went on for a few minutes and I was starting to feel light headed when all the sudden my whole body spasmed. Cum was shooting out of my dick that had been largely ignored, my arms gave out causing me to collapse on the table, and I remember the grunting coming out of my mouth was all I could get out. I felt amazing but confused.
Rich had me roll over on my back but left the dildo in me. He handed me a glass of water and I chugged it down. He asked me if I was okay and that he hadn’t seen an orgasm like that before. I wasn’t even sure I had had an orgasm but I saw the amount of cum that leaked out of me so I had to have had one without even stimulating my dick. As I came to my senses, I started working the dildo in and out of my ass on my own. Rich stood back and watched me play with a grin. I took the dildo out and stuffed my own hand in my ass, surprised at how much I could fit. I think Rich was over watching because he lubed up his hand and asked if I was ready to go again.
I was.
I was still on my back and he ordered me to hold my legs apart for him. He began to vigorously fuck my ass with 4 fingers and I begged him to stretch me more. With 5 fingers now in my ass, I was rock hard while he pushed me to my limits. I tried hard but I couldn’t get to the point where I could take his whole fist in my ass. I wanted to though.
We had been at it for an hour or so and we’re both starting to get exhausted. Rich decided to send me over the edge By working my cock and ass at the same time. I quickly erupted all over myself in another Instense orgasm. As we cleaned up, I thanked him again for everything. He smirked and said he had a great time doing this with me. I asked him what we should try for next time, he said he’d think about it and send me an email with instructions for our next session. I was instantly hard as a rock and jerked off in the shower while he watched.
I left after that and was consumed thinking about what was going to happen next. I also couldn’t get the thought of me cumming solely from anal stimulation out of my head. It was an amazing experience.
Thanks for all the comments and enthusiasm, I really do enjoy reading and responding to them. I’ve had a lot of fun writing these memories down and will do my best to keep it up if you all continue to enjoy. I think I may have to go take care of the raging boner in my pants that’s grown as I’ve written this story down ;)
Source: reddit.com/r/gonewildstories/comments/yxw2cw/richs_table_part_3_mm