Milking him Dry
Drake is one of these guys you would consider a “Mans Man”. You know the type- drives a truck, total motorhead, can fix anything, tough as nails- That type. I’ve known him for quite a while because he’s a friend of my older brothers. I was very surprised to see him at my brother’s when I stopped over to visit. He was even sexier than I remembered. I had the biggest crush on him when I was about 14. I was even more surprised when he asked me out for drinks that night. Tonight I’ll be milking him dry!
He took me out to this little sports bar that he liked to go to a lot. We caught up over a few cold beers and then fell into an awkward silence. I couldn’t stand the stagnate feeling. So, feeling a bit buzzed and courageous I said ” I’m just gonna be honest Drake, your even hotter than I remember, and I have absolutely no intentions of going home alone tonight, so if you would kindly escort me to my car, and then drive me home, I think I could make us both very happy”
Walking out to the car, he opened my door for me.
“Sure you wanna do this?” I grabbed his collar, pulled him to me said ” Positive” and kissed him violently. I hopped in, and he circled around to the driver’s side, taking the wheel and we headed for my house. So I knew he was watching my ass as I walked up the porch, I heard him mumble something under his breath.
Once inside, I let my wild wavy red hair down, shaking it and letting it fall loose all over my shoulders. He pushed me against the wall smelling my hair, before returning my violent pre- car kiss. I took his hand and led him into my bedroom. ” Make yourself comfortable” and I left him for the bathroom.I heard things moving around while I was freshening up in the bathroom, I figured he was exploring. I knew I had left my toy box wide open. ~On purpose~
I came out and saw him standing in front of my case of sexual refuge. ” See anything interesting?” – “What are these?” he held up a set of pearlesque beads. ” Those are anal beads, Drake.” – ” And this?” I smiled… ” That’s a Milking toy”
“How do you use it?” he puzzled.
“Well, I used it… on you.” I offered a smirking. I just knew I was going to have to do a lot of explaining and coaxing to even let him get used to the idea of me trying this on HIM. I grabbed hold of the toy gently and looked into his eyes. ” It’s so worth it”
He looked at it and then at me… and I kissed him hard. I reached down and grabbed his cock while I kissed him, squeezing him. I was so hot, and the idea of milking him was making me fucking insane. Then I quickly undid his pants and touched his throbbing cock. ” Do you want to Cum harder than you ever have before Drake?” He couldn’t even get the words out as I gripped and stroked his hot hard stick. ” You have to trust me. get on the bed… bottom-up”
To my surprise, Drake assumed the position.
I lubed the milking toy, and I began massaging his back. I ran my finger from the tip of his ass crack to the underside of his cum-filled balls and then back up. Then I mirrored the path of my finger with the milking toy, stopping just short of his unchartered asshole.
Slowly, I spread his ass cheeks and kissed his asshole with the very tip of the milker. He grew up. I began to pet him again, whispering a breathy “relax, baby”. I slowly started sliding the milker into him, pushing slowly and gently letting him get used to the feeling, letting him open up, and then going a bit deeper. He was quiet, but his body relaxed more and more as I began milking him. The milker slid all the way in, I began to tug on it. He moved with it. I tugged gently with one hand and gripped his hard-on with the other. GOD, he was fucking hard! I gently slid the milking toy out.
He looked back at me over his shoulder.
” I want to feel you,” I said sliding my fingers deep into his slick hole. He moaned out with pleasure. I found his prostate with my fingers and pushed it, like a button of erotica, as I milked that hard rod. I worked him over, milking the cum out of his cock, milking that fucking prostate for all it was worth. The cum began to drip from his slit, like a stripped faucet. I watched as the muscles flexed in his back, and I finger fucked his ass harder. He grunted and tensed, before his earth-shattering spasm of a guy-orgasm.
I milked this ” Mans Man” dry. Cum flooded out of him, and then he just passed out- right there in his own wet spot.