

Jake Returns
Part 5

Even though I felt guilty about being with Jake that afternoon, I fucked Allie that 
evening. She didnt 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 didnt 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 didnt 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. Its really sensitive isnt 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. Jakes 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 didnt 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 Thats 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 Jakes 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 Jakes cum oozing from 
my asshole. During the first commercial that came along, Jake told me that it wouldnt 
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 didnt 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 hadnt offered me a blow job or hand job in 
years, so refusing her offer was killing me, but I knew that I wouldnt be unable to 
perform. 


Continued in Part 6

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