Chapter # 11... I got a finger up there...
December 9, 2006. Today marked the 11th time that Jim stopped over for service. And as the title says... I got a finger up there!
Here's the story. Today is Jim's 25th wedding anniversary. I called him yesterday to check in with him and to ask him if he wanted to swing by today. He said "Sure, same time?
"I told him "Yes, 8 o'clock would be fine". Sure enough at 8:00 he rang the doorbell. I went downstairs and opened the door. After stepping in we chatted in the hallway for a bit.
He led the way down the hallway to the bedroom and we chatted some more. We talked about his job, his new grandbaby and his anniversary. It's funny; while we were chatting about all of this he started undressing when we got to the anniversary part. It just struck me as funny, we were talking about his 25th anniversary and he was taking his clothes off so I could suck him off!
He took his sandals and jeans off and lifted his shirt and sat down on the side of the bed just like always and laid back. I took my glasses off, knelt down before him and assumed my favorite position; on my knees servicing his wonderful cock!
I started licking his cock and balls slowly. I wanted to make this service last. After a very short time, his cock was fully hard and he was pumping his hips up and down like he always does.
I slowly started my trek toward his wonderful hairy asshole. I put my arms under his legs and he instinctively lifted his legs with his hands and opened his hole up for me. I gently licked and sucked at his hole. I used my hands to pry his ass cheeks further apart so I could get my entire face buried in there. Just like the last few times, he rocks his hips back and forth like he wants my tongue to be planted deep into his ass. I spent a lot of time on his hole ... licking and sucking deeply trying to get my tongue as far in as I could. I started working my way back up to his balls and cock. I did not allow his legs down.
While leaving his legs up in the air, I worked my mouth on his cock and balls, but was tickling his asshole with my finger. I continued the oral action on his cock, while circling my finger around his hole. I took my mouth off his cock long enough to ask him, "are you sure you don't want a finger up there?" His response gave me hope, he didn't really say anything, and he kind of mumbled "oh, I don't know".
I went back to his hole and licked and sucked some more. Again, I was trying to shove my tongue as deep into his asshole as I could. I know I've felt my tongue break through his ass ring, so now I thought, it's time for a finger. I was thinking, he's not completely against it so now's the time to go for it. While licking and sucking his hole, I stuck my finger into my mouth and got it all wet. I went back up to his cock and balls to continue working them, while my finger began its exploration.
I took my time tickling his hole with my finger again, while sucking his now quickly-hardening cock. I started putting pressure from my finger into his hole and felt it break through. I slowly started pumping my finger back and forth further and further into his ass. At the same time, I'm keeping my pumping action, up and down on his cock. I finger fucked him for a while, and then asked him if it was OK. His response was yes. I made sure that I kept my finger and sucking action in unison. Every time I went down on his cock, I shoved my finger into his hole, and every time I came up on his cock, my finger slid easily out of his hole.
After a while I slid my finger out of his hole, and worked my mouth back to it. I licked and sucked his hole for a while longer and then decided that I couldn't take it any more, I had to have his load.
I let his legs down and started working his extremely hard cock. He never lo st his hardon the entire time I was fingering his hole. I took my time working my way back up from his ass to his balls and finally to his cock. I took his cock into my mouth and worked it up and down in time with his hip pumping action.
It wasn't very long before he was moaning and writhing in anticipation of his release. I took my mouth off his cock and went back to his balls for a while. I wanted his orgasm to wait just a bit longer. I took my time working on his balls and licking my way back up his inner thighs and stomach back to his cock. I took his cock into my mouth one last time. I started frantically pumping up and down on his cock to his similarly-frantic hip pumping action.
Once again, I heard him moaning and felt him writhing in ecstasy. I worked my hands up his stomach to his chest and nipples. While he pumps his hips, I stroke up and down with my mouth and I keep my hands massaging his chest and nips. Soon he moans over and over again, "Oh, yea, Oh, Yea". I feel the first blasts of his cumload hit the back of my throat.
I made sure that he had finished shooting and took my mouth almost all the way off his cock. I left his cock head in my mouth while swallowing the tasty reward. I finished my job of cleaning him up and making sure that I didn't miss a drop. I cleaned his cock; his balls and one last time his asshole.
I licked my way up to his bellybutton and tapped his sides and said "that was awesome". He chuckled as I backed up so he could get up.
He got dressed again and we chatted some more. I took him on a tour of the house, showing him the Christmas decorations and while upstairs, I decided that I was going to address a subject that I've been wanting to since the day I met him. I felt today was a good day to broach the subject, since, just minutes ago; I had been finger fucking him.
I asked him if he has ever fucked anyone in the ass. His response was NO; he's never done that before. I told him that it has been years, since I've experienced it and would really like to feel what its like again. So I told him just to think about it for another day. His response was yes, he would think about it. I truly believe that not too long in the future, Jim's cock and cum will be planted deep inside my ass. I can't wait for the day.