While I was still in college I had a boy friend, we will call him Jim. Jim and I dated for almost a year. About 3 or 4 months into our relationship, we were alone in his apartment making out and getting ready to have a great night of sex. We were on the sofa and both naked. He went down and began licking my pussy as he usually did, but this time he licked my ass too. I had never had that done before and never really expected it out of him. He had been acting kind of weird all day and I knew there was something on his mind, so I thought he was thinking of how to get me to let him fuck my ass. The truth was all he had to do was ask, or just try because I was dying to have his cock in my ass anyway. I had only had a cock in my ass a couple times before and had enjoyed it very much. Jim did not have what I would call a large cock, but it was not small really and was very pretty to look at. It was very smooth and straight and was just plain pretty to look at. Anyway….after getting my ass wet with his spit and my juices, he slipped a finger in and began working it slowly in and out, asking me how it felt and things like that. He nibbled on my clit and worked his middle finger in and out of my ass and his index finger in and out of my pussy until I came. Then he sat down beside me and I got on my knees in front of him and began to suck his beautiful cock. As I sucked his cock and balls he lifted his legs high and wide. I was not sure at first what it was he wanted. I thought maybe he was offering his ass for me to lick, but was not sure how to take that. He began pushing my head lower and arching his hips to get me to lick his ass. I was not sure how to feel about doing that, I had never done anything like that before, but the more I thought about it the hotter I got. So I thought what the hell and swiped my tongue over his asshole. The pungent taste was different than I thought it would be and it made me tingle all over. I could not believe how turned on I was by licking someone’s ass. I began to lick his ass more eagerly until I was absolutely eating his ass out. He was moaning his approval and I was just about to stop and shove his hard cock in my throbbing pussy, when he asked me to slip a finger into his ass. You could have knocked me over with a feather; I was so shocked by hearing him say that. I thought that I had heard wrong and asked him to repeat it. He told me again to slip a finger in his ass. I had wanted to do it anyway, but was afraid of how he would react, so hearing him ask for it was wonderful.
I began to push my finger into his ass and he pulled his legs as far apart as he could get them to go as my finger began to slide easier into his wet asshole. The feeling of his asshole tight around my finger was unbelievable to me and I could not keep from sliding a finger into my wet pussy and finger fucking my pussy in time with my finger in his ass. He was moaning about how much he had dreamed about me doing this to him, but I was lost in my own world, swooning over the new joys that I had found. I started sucking his cock while sliding my finger as deep as I could get it to go in his ass and I started to cum very hard. As my orgasm rolled over my body and I began to regain control of my self, Jim was shifting around on the sofa strangely and I could not figure out what it was that he was doing. He was reaching for something in the sofa cushions, I asked him what he was doing and he pulled out a medium sized red jelly type dildo and asked me if I would use it on him. I thought about how my finger looked sliding in his ass and just knew I had to see that dildo in his ass. He reached over into the end table drawer and produced a tube of KY jelly and squirted it into his hand and began to stroke the dildo, getting it all greasy and ready to be inserted in his ass. The feeling of being in control was great. I had fantasized before of doing all these things, but had never verbalized it and never thought that it would actually happen. I could not wait to push that rubber cock into his tight ass and make him squirm with the feelings that I know I felt when I had been fucked hard in the ass before. I took the dildo from him and looked into his eyes and told him that I would only do it if he promised that when I was done fucking his ass with it, then he would use it on my ass. Of course he agreed to this. I began to tease his ass with the tip of the dildo as I sucked his cock. It took some effort to get the dildo to slip into his ass, but once it got started it was much easier to push than I expected. I was not sure if I would hurt him or anything but he seemed to really enjoy it so I pushed it further and further in his ass until it was in as far as it would go. I was not really sure what he wanted so I just did what I wanted to do. I slide the dildo slowly in and out of his ass while I sucked his cock as deep as I could. I could feel his cock throb and could taste the pre cum oozing out. My pussy was doing back flips now wanting his cock to fuck me but I was having much fun pushing that rubber cock in his ass. We swung around so that we were in a 69 position and he started eating my pussy and I came almost immediately. As I started to cum, Jim pushed both his index fingers into my ass and pulled it apart and sucked hard on my clit as he began to cum in my throat; driving me to the most intense orgasm I had ever had. As soon as Jim quit coming, he flipped us over and began kissing me hard and deep and telling me that he loved the taste of his cum on my lips and in my mouth. I almost started to cum again from his kisses. I had never before been so horny in my life. Jim positioned me on the edge of the sofa again and started eating my pussy and playing with my ass with his dildo. It was not long before he had me begging to be fucked. I told him to fuck my pussy doggie and fuck my ass with that dildo. He turned me over and fucked me hard for a long time as he pushed that dildo deep in my ass. I came several more times and just could not seem to get enough of him. We left the sofa and went to his bedroom and got on the bed. On the way there, he got a towel out of the hall closet and brought it to the bed room with him. He got on his knees on the bed and asked me to fuck his ass with the dildo some more. I began to slip the dildo in and out of his ass, after awhile I held the dildo against my pubic bone and pretended it was my dick and I was fucking him with it. We did this for a few minutes and then he rolled over on his back and took that towel that he had and rolled it up and positioned it so that it would hold the dildo in his ass and told me to get on top of him so that he could fuck me while rocking on his dildo. I straddled him reverse cowgirl so that I could watch that dildo slide in and out of him as he fucked me. It was not long before he came again and we both collapsed from exhaustion and fell asleep with him still inside me and the dildo still inside him.