Jill - Sex Stories

Jill

... assisted Carol with her needs, and not as any friend. If she wants to be fucked some more, then I would certainly be of service; but it would be my choice and my way. I flipped Jill over again so she was on her back, and dragged her and the bed sheets down to the end of the bed. Jill said nothing, other than acknowledging with some surprise that I was still hard. She was sweating somewhat, her hair was matted to her cheeks and nose, and she had that dazed look of a woman who had just cum and had not quite recovered. I went over to my bureau and grabbed a tube of K-Y lubrication. As soon as I turned around to face Jill again, she knew what was on my mind. There was a slight look of apprehension in her eyes. Other than that, she did as she was asked and bent her legs back and held them open, exposing her soaked, red, swollen pussy and wet puckered hole. I slid some lubrication on her asshole with my thumb, and some on the head of my cock. Other than my instructions to her, nothing was said other than her simple request. “Go slow.” I didn’t know whether Jill wanted to be fucked in the ass. I didn’t even know whether she had ever been fucked in the ass, although I had guessed that she had. All I knew for sure was that Jill had liked it when Carol shoved a finger up her ass, and that I was going to fuck her in the ass for my own pleasure. I pressed the head of my cock against Jill’s asshole and pushed. There was resistance for sure, but having now cum twice, she was more relaxed ...

... and on about the third push, the head of my cock popped into her star hole. Jill’s subsequent moan was part surprise, part pleasure, and part concern. Where was my t-shirt? In my haste to pull her to the end of the bed, I had left the shirt on the pillow, and it was beyond her reach. I pulled out if her ass, walked to the side of the bed, grabbed the shirt, tossed it to her, made my way back to the end of the bed, put some more lube on the end of my dick, had her pull her kegs back, and popped my cock head back into her ass. “Please go slow,” she asked again, just before reinserting the shirt into her mouth. Jill, it turns out, was a stranger to anal sex. My entire shaft slid effortlessly into her hole, and within a minute or so, I was fucking her ass and she was moaning and staring directly into my eyes. Still, she was very tight, and the friction of her squeezing sphincter on my shaft, was hastening a very large and very intense orgasm on my part. I slid one thumb into her pussy and rubbed her clit up and down with my other thumb in hopes of getting her to cum again. When I needed to hold onto her hips in order to keep steady and slide my shaft deep into her hole, Jill took over the clit massage, rubbing the nub furiously and slapping her clit with an open hand. I stood at the end and edge of the bed slamming my shaft deep into Jill’s ass. Jill, resting her ass on the end of the bed, held her legs back, and her knees by her head, and moaned into the t-shirt. I watched my ...