I posted an ad once looking for a middle aged man to show me the ropes. I was a first timer and very nervous. After a few drinks I was not even thinking of my girlfriend who lived hours away. I laid in bed toying around with a butt plug I had bought when an ad caught my eye. His name was Steve, about 50 and sexy as hell. Grayish beard, short hair, strong arms and some hair on his chest. RAWR!
We agreed that since I was nervous that we would start with a massage, and I would let him take over from there. He picked me up and we smoked some weed on the way to his place to help me relax. When I got there, he instructed me to strip down to my boxers and lay on the bed, my butt plug was still in. It was a decent sized plug.. not too big, but not tiny. My heart raced with anticipation, and my asshole was tingling. Steve's strong hands began working me over as he stood on the side of the bed, his cock packaged nicely in some tighty whitey underwear just a foot from my face. He was working up and down my legs, and at first he wasn't even paying my ass any attention. It felt nice, and I began to relax. That's when he took his first pass at me.
I felt his hand run up my leg and pass under my boxers, barely grazing my balls. Each pass got more and more touchy feely, and that's when he found my butt plug. He stopped, and took it out saying something like "we won't need this anymore." He then removed my boxers and climbed on top of me. He continued massaging, his hard-on pressing into my ass. He eventually slid lower and lower, until suddenly I felt his tongue prodding my hole. HO-LY SHIT did it feel good to have a hot man's tongue slide deep into my already slightly loosened hole. My thoughts were on anything but my girlfriend at the time.
He kept rimming me and fingering my ass, eventually adding plenty of lube. Then suddenly he stopped, got up, and took off his underwear. His 7" cock sprung to life almost hitting me in the face. I knew what to do. I had been waiting 20 years for this moment................. I dropped to my knees and wrapped my mouth around his cock faster than he expected. I took it as deep as I could, which was surprisingly pretty fucking deep. I blew him like the fucking whore I was. I took him deep and hard, slow and slutty, took both of his massive balls in my mouth, and sucked his tip til he almost came.
Then he took me and laid me down on the bed. He took out a dildo from his dresser drawer and slid it into me. It was tight, but it fit. He laid on top of me, his cock rubbing against my balls and his body weight pressing the dildo in and out of me. It felt amazing, and it was hitting my prostate perfectly. I was moaning. I thought I sounded pretty hot.. that is until what happened next. In one sudden move, he removed the dildo, and pressed his dick against my gaping ass. It hurt, but it slid in. I was moaning "oh my god" over and over again.
Once I got used to the size, he started pounding me pretty hard. It hurt, but his dick was curved and was hitting me just right. I was moaning like a girl. holy shit haha that's all I can remember about parts of it is the sensation of getting fucked, the connection I felt with that man, and the fact that I could not have been quiet even if I wanted to.
Eventually he was jacking me off and I came all over his bed. He pulled out and without a second thought I went ass to mouth and swallowed his huge load. I don't know what it was about this man, but he made me want to be his whore.
After we finished, he drove me home and I sucked his cock on the way home.. finishing him off in my driveway.
I miss Steve. He is still the hottest fuck I've ever had.