Note: This story was dynamically reformatted for online reading convenience. Jake Returns Part 5 Even though I felt guilty about being with Jake that afternoon, I fucked Allie that evening. She didn't get very excited while I pumped her pussy with my little cock. However, she did get off when I ate her pussy afterwards. Jake and I started spending more time together. Several times a week, we would spend an evening watching sports on ESPN. Allie seemed to approve and could find other things to do when Jake and I got together. Of course she didn't know that watching sports usually involved Jake sitting in his recliner watching his 42 inch plasma TV, while I knelt between his legs sucking his cock. Jake never forgot to make me wear my leash and collar and sometimes he made me suck for more than a hour before he fed me his cum. At first I noticed that my knees were getting rug burned. Then I started applying Vaseline intensive care lotion to my knees before I went to Jakes. It helped a lot. After a couple of weeks, I was getting used to the situation. One evening after Jake collared me and had me servicing him for about ten minutes. Suddenly he pulled out and walked over to the closet and came back with a brown paper bag. He handed me the bag and I looked inside and saw two fleet enemas and a tube of KY. Jake told me to go to the bathroom and clean and lube myself. I felt a sinking feeling in my stomach, but I didn't argue. As I walked into the bathroom, Jake yelled after me to call him when I was done. It took about 15 minutes to flush my ass and lubricate it. I felt like I was an unwilling bride on her wedding night. When I finally finished the disgusting task, I called to Jake. I was surprised when he came into the bathroom wearing a pair of latex surgical gloves carrying a plastic bag full of crushed ice. Jake took hold of my leash and led me over to the vanity where he had me bend at the waist with my legs spread wide and my arms and hand supporting me on the vanity top. After telling me that I was really going to enjoy this, he wrapped the ice in a thin towel and applied it to my scrotum. Reaching around behind me he inserted his middle finger up my ass a short was and started feeling around. Suddenly a wild feeling hit me as his finger hit a certain spot. Jake said "This is your prostate, Joe. It's really sensitive isn't it?" I just moaned and squirmed as I felt him gently stroking on it. Jake told me to take hold of the towel with the ice in it and hold it in place. It was cold but not unbearable. With his now free hand, Jake took hold of my leash where it attached to the collar and used it to hold my head in place close to the counter top. Bent over as I was, I had a clear view of my little cock. The application of the cold pack had made it really tiny. Jake's gentle stroking of my prostate was causing a new and strange sensation. Suddenly, I could tell that there was something strange going on. I looked down at my cock and saw semen dribble out of my piss slit. This kept up for quite a while as Jake worked on me. When the flow stopped, Jake pulled his finger out. Even though I didn't have an orgasm, I felt weak all over especially in the knees. Still holding me by the short leash, Jake showed his superior strength by pulling me off the counter and putting me on my knees. I felt like a wet dishrag as he inserted his half hard cock into my mouth. Jake had made me kneel in the puddle of my own cum. I could feel its slippery texture underneath my knees. I was on autopilot as I started sucking. Jake looked down at me and said "That's a technique called prostate milking, Joe. I learned to use it on the boys that I had after you. I have found that it really relaxes them and makes it easier to take my cock in their asses." It only took a few seconds for Jake's cock to get rock hard. Again using the short leash, Jake put me back in the same position over the vanity top. He slowly worked his big cock into my well lubricated asshole. I was too weak from the prostate milking to put up much of a struggle or for that matter to even squirm around that much. After he got his cock in all the way, he took his time fucking me. While he worked away, he kept complimenting me how tight and smooth my ass felt. It did not feel good to me. It felt like my asshole was on fire and with every stroke I could feel my inner organs being pumbled. But somehow the relaxed feeling from the milking made it not as bad as I had remembered. Jake finally pushed in deep and shot his load while he did a lot of moaning from joy. After he pulled out, he handed me a roll of paper towels and told me to clean up the mess that I had made on the floor. I had cum a lot from the milking and the activity that followed had spread it around. I cleaned my cum off my legs and then cleaned the floor. When I got to the living room, Jake was still naked sprawled out on the couch with his feet on the coffee table. My asshole was really sore. Jake made a comment about how funny I was walking and then told me to get us a couple of beers. We sat on the couch and watched the last few minutes of a football game. I could feel Jake's cum oozing from my asshole. During the first commercial that came along, Jake told me that it wouldn't hurt as much after my ass got broken in. He also told me that he had another, better way to milk my prostate and we would try that soon. I didn't ask any follow up questions. After the game, as I walked home, I felt like I was going from one world into another. Allie was having her period, so there would be no fucking that night. It was a good thing because I could feel that there was no way that I could get a hard on. That evening Allie hinted that although she was having her period she might be willing to take care of me another way. I never inquired whether this meant a hand job or a blow job. I just quickly told her I was tired and could wait. She hadn't offered me a blow job or hand job in years, so refusing her offer was killing me, but I knew that I wouldn't be unable to perform. Continued in Part 6 Please address any comments or encouragements to jcbottom@hotmail.com