I met a magnificent woman on the internet about 8 years ago who had never had anal sex before, but had wanted to try it just once...a fact that I was unaware of until one incredible night. I ended up coming to town and giving her a Valentine's Day surprise. I decorated my hotel room for Valentine's Day, with candles and chocolates and hearts all over. First I performed oral sex on her...making her cum twice. The first time I had her in a chair with a towel under her and licked and sucked wine from her pussy. The second time she came I had her on the bed while I knelt on the floor and just totally enjoyed myself while she almost pulled my hair out with her fingers during orgasm. It was then that she shared her fantasy about anal sex with me. I always brought lubricant for our encounters...and gently massaged her ass and anus with my hands. Then after putting on a condom with plenty of lubricant, I had her kneel on her elbows and knees at the end of the bed with her legs spread a little. I came up behind her, placing the tip of my penis right on her anus and moving it slowly around. I told Vanessa that this was totally going to be under her control, and told her she would always control the contact and amount of penetration. She was very tentative at first, and after about a minute had the head of my cock into her ass. I remained totally still...lightly rubbing my hands over her ass and lower back to keep her relaxed. After about 10 or 15 seconds...she slowly began pushing herself back onto my cock. I told her to take it very slowly...rocking up and back very gently. (I was very careful to make sure I was very well lubricated the full length of my cock) After about two minutes of this kind of gentle rocking up and back...she had the full length of my shaft buried in her ass. I still didn't initiate any movement, but told her to begin moving when she was ready. To this point she had been gasping and moaning as each inch of my cock went into her. Now, with me fully embedded in her ass, she slowly moved forward until only the head of my cock remained...then she came back on me, gasping and moaning as I filled her again. I moved my hands forward, leaning a little now and cupped her breasts with my hands and began to massage her nipples, which by now were very stiff and firm. She immediately began to move faster and faster now, until she was almost slamming her ass up and down the length of my cock...it was all I could do to keep from exploding myself. It only took her about two minutes until she was overcome with an anal orgasm that left her almost convulsing. Her voice was so loud now I was sure that if there was anyone next door they would hear her, but I didn't care, and neither did she as she almost screamed through the orgasm that lasted for about a minute. By then, I too was a lost cause, and emptied my load of cum into the deeply buried condom, holding onto her breasts for dear life. I realized as I was cumming that I had pushed her forward and I had crawled onto the bed with my knees and now her head was down on the bed as I pumped my load into her as she continued gasping and moaning. After about three minutes of thrusting and flexing and making sure I had expelled as much cum as I could, i collapsed onto Van's back and we slowly rolled onto our left sides, with my cock still planted up her ass and one of my legs between hers, both of my arms around her tightly. We laid there for about ten minutes, breathing heavily as she thanked me over and over again for being so gentle with her and making sure she was in control. We spent about three more hours that night making love. I realized when the night was over Van had made a fantasy cum true for me, too...by pleasing her as she had never been pleased before.