My First Anal Adventure

My first year of college I jumped quickly into a long-term relationship. Sarah was her name, at 5'11" 125 lbs. With creamy white skin beautiful 34c breasts and the longest legs I have ever seen thus far, she needed to do little more than smile seductively to turn me on. Of course being an 18-year-old male probably didn't hurt either.

We had a healthy and very active sex life during our time together and like most couples I'd imagine we had things that we would joke or tease each other with. One of those things for us was anal sex. We had never tried it and at the time when we first discussed it neither of us was terribly interested. It seemed like a lot of work for what we thought would be little gain. Boy were we wrong.

Sometimes when we were fooling around I would gently push the tip of my penis to her ass hole and make some pithy remark about my fucking her ass. Or occasionally she would mock plead with me to take her ass cherry. But of course, this would never result in anything ever happening it was simply a joke. And for a time it remained just that, then I started to realize that all of this teasing had actually piqued my interest. I really wanted to fuck her in the ass.

Shortly after I made this realization I went to the store and picked up some lubricant. That night I was a man driven, I had built the experience up in my mind and I needed to act on it.

That night we were in bed she was lying on her back one hand playing with her breasts and the other with a death grip on my hair as I lapped furiously at her clit.

"Oh god, Oh god yes yes!!" She screamed as I brought her to climax. When the orgasm had faded a bit I pulled away from her wet pussy my face still damp with her dew. I pulled her legs up and rolled her over onto her stomach. She turned her head and looked at me wondering what I was up to now. I showed her by licking up from her throbbing clit, over her swollen lips and hairless taint. I finally came swirl my tongue around her tight pink ass hole. I began to slowly flick my tongue around the edges avoiding the hole at first. She laughed lightly and looked as if she was waiting for the punch line. But I could see in her eyes too that this did feel good.

I decided to take things a bit further my tongue spiraled down to the puckered hole. She gasped slightly when I pushed though with my tongue. At the same time I took my finger and pushed it into her pussy. Her body jolted from the pleasures she felt all at once. I kept doing this for a little bit until I felt that she seemed really comfortable. Then I removed my forefinger from her snatch and inserted the well-lubricated digit in to her ass. She let out an audible groan and then turned and asked me what I was doing. I assured her that everything was fine and that she should just relax and enjoy it. With one last skeptical look she turned back around.

I then proceeded to slowly push my finger in and out. The sounds Sarah was emitting told me everything was going well. So I decided to up the bet, I removed my finger wiped it off with a near by tissue and then inserted two fingers back into her cunt. They slid in very easily, I thought to myself. I realized then that she was really very wet, more than usual it seemed. I smiled to myself as I moved those two fingers from her sopping pussy and slowly pushed them into her puckered hole. This time the groans were a bit louder and hips were moving slightly in rhythm with my thrusting.

With my free hand I reached for the lubricant I had bought. I opened it up and began to rub generous amounts onto my hard cock. When I felt that her sphincters had loosened. I removed my fingers again only this time I replaced it with my dick. Though my penis is considerably larger than two fingers, I was getting anxious. I wanted to take her ass cherry and I wanted it now. I pushed the tip of my head gently into her hole.

She turned around suddenly as if realizing what was happened. She looked as if she was going to say something, but then she just smiled and turned away. Smiling wide I proceeded with the task at hand. It took me some time to finally get my whole head into her ass. I had to push in and out and in and out each time getting only a slight bit further in.

I decided to let her ass get used to what little of my cock was already in her. I waited for a bit then pulled out completely. I applied more lubricant to my cock and this time I put some right in her hole. Then I pushed my head back in her tight pink hole. This time I faced much less resistance. So I pushed forward, I managed to get half of my cock in her ass before pulling out and re-applying lubricant. Then I gripped her hips and plunged my whole seven inched into her. She let out a muffled gasp. I kept myself still insider her, wanting to cause her as little discomfort as possible. Her sphincters adjusted to accommodate my penis as she relaxed her body.

I took this as a cue to begin. In and out of her ass I started piston building up momentum. Sarah was moaning loudly now. One of her hands gripped a bedpost as the other traveled down to her crotch she began masturbating furiously. Her moaning started to build in intensity until they were full-fledged screams. Her usually porcelain white face was now flushed a deep red and her eyes were tightly shut. I could feel the bed starting to soak with her juices. It was more than I could handle I began to cum right there in her ass. I kept pumping until I started to go limp. Then I pulled out, a trail of cum oozed down her crack.

I laid down next to her. She was still breathing heavily, but she reached up and pulled my face to hers roughly and kissed me, teeth biting down on my lips hard enough to draw blood.

"My god that was wonderful. I never thought it would feel like that. I've never cum so many times in my life. I don't even know how many I had." Sarah said to me as she caught her breath.

"I'm glad you liked it, I really did too. We'll have to do it again sometime." I replied.

"We certainly will!"