Anal Anxiety (Part One) - Sex Stories

Anal Anxiety (Part One)

... them published on line. “Well, yes, I could do that,” I said, “But…” “But what?” he asked. “You know Jen, the owner of the toy store we shop at?” I asked. “Yes, of course. What about her?” Jimmy inquired. I proceeded to tell him about the conversation that Jen and I had. He laughed about it, but when he saw that I was seriously considering it, he said he would think about it too and let me know. “We would have to do some serious practicing first, though!” He said slyly. “I’m getting hard just thinking about your ass right now!” “Oh…really?” I replied seductively. “We will have to do something about that, then!” I slipped off of the couch and onto the floor. Kneeling between his legs, I reached forward and undid the button on his jeans and pulled down the zipper. Grinning lustfully at me, Jimmy raised his ass up so I could pull off his pants. Tossing them aside, I reached for the growing bulge under his boxers. Sliding my hand in through the fly, I grasped his cock and pulled it out through the opening. I quickly lowered my mouth while gently stroking him. I wanted him rock hard! After a few minutes of savoring his cock, I pulled away. Still kneeling in front of him, I lifted off my tee shirt and tossed it aside. Then I unhooked my bra and sent it flying. Standing up, I faced Jimmy and pulled off my pants, first pulling out the small bottle of lube I had put in my pocket, prepared for what was to come. “Get naked!” I ordered. As Jimmy quickly removed his shirt and socks, I ...

... also stripped off my panties. Going back down on my knees, I tossed the lube to him. I then turned around and went in to the doggy position. Spreading my legs, I lowered my head and shoulders so that they were on the carpet. “There’s no better time than right now,” I said and I wriggled my ass invitingly. Jimmy didn’t say anything, but he certainly knew how to use his tongue. I felt his hands grip my hips and his tongue find its way to my anus. I just closed my eyes and enjoyed him enjoying me! Soon I felt lube all over my pussy and asshole. With one hand he was massaging my pussy, and with the other he was slowly pressing a finger up my ass. As the finger moving in my ass started speeding up, he plunged a couple of fingers into my pussy. One day I would like to try a double penetration with two cocks, but for today… lots of fingers was working just fine! I knew it wouldn’t stay like that for long, though. Sure enough, I felt both hands spreading my ass cheeks apart. As his cock pressed against me, I said a quick prayer that he used enough lube and it wouldn’t hurt. I tried to relax my mind into thinking that it would be fine, and hoped that my body would relax too. It worked! I felt his cock slowly penetrating me. We had done this enough times before; Jimmy knew not to go too quickly. I gasped as his penis worked its way down my channel. With each gentle thrust, he went deeper. I heard him groan in delight when he was fully in me. I could feel the warmth of his body pressed ...