I am engaged to a wonderful girl, who if you met "nice girl" is the term that would come to mind right away.
I knew her when I was younger, but she was not my speed, or so I thought. I always considered myself a player, and after years of not knowing her, we reconnected so I thought to take it slow at first.
Our first date, she drank a little more than she could handle and I did the gentlemenly like thing and just put her to bed that night. She woke me with a great blowjob and then we had sex, which was great but a little lack luster due to both of our hangovers.
The second date is why I needed to write this story! We went out and had a blast in town, laughing and partying it up. I drove her to her house and she invited me in. As soon as we got into her house we made out like kids during there first time, really going at each other. She put her hand down my pants right away desperately trying to get my cock out. I was trying to slow her down, not yet realizing what a vixen I had managed to get, and how horny she is!
As soon as she got my cock out, she dropped to her knees and sucked me like no one ever has. I truely was thinking how this girl wants my cum, just wants cum just wants cum in her mouth right away. I pull her away, still trying to keep the image as a player and not wanting to cum in two minutes like a high school boy. I try and slow her down by going down on her and relaxing my cock as I eat her out. She is soaked and I have her girl juice all over my face, she gets really wet ( is a squirter for another story though).
I now decide that I want to fuck her because I have gotten her off once with my mouth and feel that I can now cum without feeling selfish. She knows what I am doing and bends over the bed. I grab her hips and slide right into her wet pussy. I love the feeling of her pussy as it pulls my cock into her tighter, almost like her mouth an hour before. I am loving the feeling, but now she is slowly pulling away as I slip out. I put my cock back in and it happens again, as I put it back in her butt moves lower so I go lower and put it back into her pussy. It happens again, and I slowly catch on to what she wants. I take my cock and slide it between her cheeks, she moves her ass in an up and down movement. Is this really the prude that I know from high school, begging for it in her ass on our second date. Unsure, I put my hand on her ass with my thumb at her bud and she pushes back trying to get my thumb to enter her anus. I can not believe my luck and put my cockhead at her inviting ass. I take it slow, but she does not as soon as my fat head is into her ass she is fucking me back slamming her ass so that my cock goes deeper and deeper into her. Now that I know this is no accident, I pound her ass as hard as I can. In only minutes I am cumming all the way into her ass, I take my cock and put it as far into her ass as possible and try to get my cum all the way into her. When I finish cumming I hold my cock into her til it slowly deflates and pops out of her ass.
I fall on top of her, both of us are out of breath, sweating and satisfied. She looks back at me and tells me that was a first. I say that was the first time you had anal sex, she hesitates and says "no". She tells me "it was the first time someone had cum in her ass". She then confessed that her ex husband had always begged for her to give him the ass, but she never had. She also then told me after they seperated she had gone away on a buisness trip and she had hooked up and had let the man do anything he wanted to her and that is when she had realized that she might like it!
This was only my second date, I have many more stories already and hope to have many more to cum...