Actually wasn't that long ago. 8 times. Had a friend meet me in a hotel room, during an east coast motorcycle event. She is a neighbor who wanted a weekend away from her husband, and I said I wasn't feeling well. Our group took off, and I ran to get my neighbor. I don't live far away from the hotel in OCMD, and we were in my room, naked within 20 minutes. She brought some toys, and we started screwing immediately. She had cum on my tongue, my cock and my tongue pretty quickly. She kept playing with my cock licking and sucking on it....and she asked....I bet I can make you cum more times today than you ever have. I said....ok...prove it. I was already at twice. Fucking her pussy....and mouth. She sat on my face....and sucked me hard....and said....ok....jack off and cum on my face. Of course I had already spent my cum( had a vasectomy back in the early 90's so I cum a few drops the first couple of times....then that is it....I still cum....but dry ) while she was sucking my balls ...I came #3. I laid back....she set her pussy again on my face....and sucked me hard a 4th time. I then jacked off again....in her face while I licked her wrinkled ass. I relaxed....as she played with her clit while she was on her knees and I felt her pussy cum on my face. We laid back together....and after a while got up to eat a little. She and I had to pee, we got in the shower and washed and peed on each other. What fun. Went to bed for a few hours. I woke up with her sucking my cock, and leaned over and played with her ass. I came in her mouth, and she said....I have never done this with my husband, but I want you to fuck my ass. So here I am on #5, spent, and she asks me to fuck her ass....ok...omg I am hard again immediately. I start by licking, and spitting in her ass....sliding 2, 3 then 4 fingers in her ass....my thumb is in her pussy ... she reaches into her bag, pulls out this amazing lube. Sucks my cock a little then coats my cock with the soft feathery lube....my fat cock has a little trouble getting in....but I take my time....and soon I am fucking her ass with abandon. Ok....I cum a 6th time....I'm so excited fucking her ass....I stay hard....and cum the 7th time in her ass....I'm exhausted. We lay back. ..I didn't know it....but she whispered in my ear....she had made herself cum while I was fucking her ass....and no one had made her cum while a cock was in her ass....another hour goes by....we shower together again...and we climb back into bed. All of my friends have returned to the hotel....it is time I take her back home....but before we leave....she sucks my cock hard again....and looks me in the eye....and tells me that she had had one of the greatest orgasmic moments of her life, and squeezing my balls, sliding a finger in my ass....I cum the 8th time. I get her home before her husband comes home from work....get back to the hotel....and collapse from 6pm until 9am the next morning....