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By (user no longer on site) OP
over a year ago
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I asked if we could go to his bedroom, and we grabbed the lube on the way. I climbed onto the extra-high bed and, on all fours, put my ass in the air. James put two big pillows under my tummy and helped me relax by straightening my legs a bit. He said doing it right might take a while for me, so I should be comfortable. Having never had any anal play, I felt really vulnerable having this man and his big cock over my tight ass - but it was wonderful.
He spread my legs wider, licking from my balls to the small of my back, making my asshole twitch with excitement. He reached under me and pulled my cock out, pointing it straight down toward the mattress, and massaged it firmly while he licked my balls and ass. Then, through a spurt of lube, James slipped one finger into my ass, working slowly so I could relax.
When my butt was nice and loose around his finger, James reached into a drawer and pulled out a vibrator. It was about six inches or a bit longer, very skinny at the tip, but flaring out much thicker at the base...maybe as thick as James's cock. He slowly worked the vibrator into me, slowing down when I told him the thick base hurt. With a gentle touch, James gradually loosened me to the point where the vibrator could slide all the way in and out with no pain - only pleasure.
I reached back to move James's hand from the vibrator and worked it in and out myself, then pulled it out completely. I put the vibrator aside, and when I reached back to my ass, James's cock was there, lubed, hard, and ready to fuck me. His cock was thicker than the vibrator, but it felt wonderful. I rocked my ass back onto James's hard-on, and he held my ass firmly against him while my tight hole relaxed more. He began to slide in and out very slowly, then gradually with firmer, longer thrusts. I could only moan as he asked how I liked his cock deep in my ass... it was incredibly sexy.
I asked James if I could turn on my back so I could see him fuck me. He slipped out, stepped to the floor, and I turned over. I pulled my legs back, showing my hard cock and what felt like my "pussy". James grabbed my hips and slid my ass to the edge of the bed. The extra mattress put me at the perfect height to fuck - probably not coincidence. Totally in control, and a little more firm now, James worked his cock back in - he was getting close to coming, I think. Once in to the hilt, he leaned over to kiss me while he started to pump my ass again. My legs were in the air, and I felt his strong chest on the backs of my thighs. Our chests pressed together, and I held his shoulders while he kissed me sweetly, and deeply. I knew what I was doing was risky, but it was so beautiful. As we kept holding, kissing, and fucking, my cock kept throbbing. Then, without even touching my cock, I squirted my load of cum between us. The longest shot came above my nipple, and James licked it off me. He hesitated for a second, but seeing my open mouth, he went back to kissing me, sharing the warm, salty cum
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