Y2K-Y Ch. 01

Slowly I pulled my cock from her pussy and planted the head at her tight puckered opening. She looked back with a cool smile.

“Be gentle with me, Jakey. I am going to love you up my ass, but be gentle. You’re a big boy.”

With that, I let her push her ass against me enough to watch my thick head disappear into her smooth tube. She gasped as it entered her, lowering her head to concentrate on getting me totally inside her. As she relaxed she moved against me, withdrew, then swallowed more of my cock into her ass with each cycle. She eventually became accustomed to my width and length and I began to ass fuck her in earnest, being firm but gentle. I gripped each cheek and pulled them apart to reveal her tight anus being invaded. I loved to watch the skin around her asshole stretch outward as I moved out of her. When I pushed it back in, the lines around her anus returned, like the angry furrowed brow of a school marm scolding me for such a naughty act.

The sensation was amazing because of her absolutely tight hole. I re-lubed my cock several times because her ass gripped me so tightly we both would have otherwise been raw after only a minute or so. I took my time and fucked her ass the right way, slow and deliberate. I looked down to see her gray hairs ticking my scrotum with each thrust. We changed positions several times, experiencing totally new sensations with every angle. I put her on her side, which was particularly satisfying because it was so relaxing. I gently kissed her neck and massaged her shoulders while we continued our taboo activities. I got on my back and she mounted me and controlled the tempo. The excitement was so intense that having an orgasm was forbidden by my mind. Ending this was out of the question.

After about 20 minutes she lay down on her tummy and lifted her bottom high. Once again, I pushed into her ring, which was now comfortably stretched. I could feel her fingers on my balls, touching them gently with each thrust. She was stimulating her clit while I fucked her in the ass, feeling my scrotum at the same time. Just the thought of it almost made me come, but I was determined to watch her release before I would.

“Oh, God, I am going to come so hard. You can fuck my ass harder now. Lube us up and fuck me in the ass hard now!” She screamed. I obliged her and could feel her body tensing as she neared orgasm. “I’m coming, keep fucking my ass, keep fucking….”, she said as she was lost. When I felt her spasm, I let go. It was only seconds before I could feel a thick stream of semen pushing through the length of my cock into her incredibly tight rectum. It was so tight that it actually was very painful for me. The act of forcing the viscous semen out of my penis was restricted because of her tightness. But I would be a liar if I didn’t say that the pleasure totally eclipsed the pain.

“I am going to come in your ass, Corinne. It’s going to fill you with sticky seed. You are so tight, and I’m getting thicker and harder!!! I’m coming now!! I am coming!”, I practically yelled out loud as I lost it. It was incredible. I turned her over and gently kissed her lips.

“Well, I guess things will be different at work now, won’t they?” she laughed.

“Not really, maybe just a little. Now I KNOW what it’s like to fuck your little ass!!” She attempted in vain to smother me with a pillow before we fell asleep together laughing.

We worked together for another year or so and had many more “adventures”. I’ll be sending them along if you’d like to hear the rest of the story.