First time getting milked
The guy was from one town over from me. I met him online. We emailed about fucking women, our wives, and jacking off. He said he had a milking machine that could make me cum harder and longer than I ever had before. He told me to come over someday. So I did. I figured we would jack off together and watch each other. He was kind of bossy and said I had to agree to do what he said. I figured, yeah, why not? So I went over. He was dressed in a pair of silk boxers with a hard on. He told me to strip. I got down to my briefs. He then told me to kneel on his bed on all fours. He tied my hands and knees to the bed. He showed me his milking machine. It was pretty cool looking. He pulled my underwear down and grabbed my cock. That was a little weird I thought.
Then he took some lube and showed me. It was that new KY stuff that warms up. I've jacked off with it before and my wife and I have used it too. He put some in his hand and started jacking me off with it. I asked him what the hell he was doing. He told me to shut up. I got really hard from him playing with my cock. I saw his cock was hard and poking out of his boxers. He had a big one.
Then he put this milking machine sleeve thing on my cock and pushed it all the way up. It felt kind of good, wet and warm. He turned on a switch and this thing started milking my cock. No shit, like a cow milker. It felt great. I really liked it and told him so. He shut off the machine and asked if I was ready to do what he ordered. I told him I would if he turned the milker back on. He turned it on. Then he got on the bed in front of me and showed me his hard cock. He told me to kiss it. I said no way. He threatened to turn off the machine. Damn, I was so horny and hot I needed that thing. So I kissed the end of his dick. It was clean and nice looking so I figured why not?
He made me kiss it a few more times. Then he put on a rubber glove. He lubed up the middle finger. I got a little scared by that. I just knew he was going to finger my ass. What the hell did I get myself into? He went behind me. He played with my ass a little and then slid his finger in me real slow. It didn't even hurt. Pretty soon he was gently fucking my ass with his finger. I could feel my dick leaking precum in the milker. Then he hit my prostate. Oh shit. It felt so good. I got really horny then. I needed to cum real bad.
He kept fucking my ass with his finger and massaging my prostate. My cock was running like a faucet. Just before I was ready to cum he stopped. He knelt on the bed again and showed me his cock. He told me to suck it. I said hell no. He asked if I wanted to cum. I said yeah, please, let me cum. He told me he would if I sucked his cock. Damn. He pressed it against my lips and my mouth just opened up. His cock went inside my mouth. Next thing I knew I was sucking his dick. He promised not to cum in my mouth, so that made me feel better. I sucked him for a long time while the milker worked on my cock, almost making me cum but not quite.
All of a sudden he pulled out of my mouth and squirted his cum on the bed in front of me. He came huge. Lucky it wasn't in my mouth. Then he went behind me again. I was so hot. I needed to cum. He stuck his finger back in me and turned the milker machine up. He rubbed my prostate with his finger and fucked my ass with it. The machine sucked my cock.
I exploded into the milker. Oh man, it was so intense. I just blew and blew into it as he kept fucking my ass with his finger. I almost wanted his cock to be in my ass I was so hot and cumming so hard. I just kept cumming and cumming for a long time.
After it was over he told me to get dressed. Now he wants me to come back over. But he told me he wants me to suck him and let him cum in my mouth. And then get him hard again and let him fuck my ass with his cock. I am thinking about it. I need a milker like he has.