"You sure this won't hurt?" Mary asked again.
"Absolutely. All you have to do is push back, like you are trying to go, and relax. Things will be just fine. I slide in a little, let you have time to get used to it, and take it easy. You'll love it." At least he hoped he wouldn't hurt her. He had used enough K-Y. If she were too tense, it would hurt. If she relaxed and wanted to enjoy this, it wouldn't.
"God I hope so. I've heard about this enough."
"Girlfriends huh?" John said as he moved closer and smeared the lubricant all over his hard and ready cock.
"Yea. A few said there was no way that they would ever let a guy up there, and there were a few who said it was really kinky and they loved it - now and then when they were feeling really nasty or wanted to give their husband or whatever a real treat. Some even claimed they got off doing it."
"And you were just dying to find out who's telling the truth?" he moved closer.
"Well, sorta," she said, waiting for him to either enter her ass and thrill or her, or for the pain. She wasn't sure what to expect. She had her virgin ass up in the air, waiting. Her chest was on the bed. "Mostly I just hope I like it. I hope I can cum. It sounds so nasty." Thank God, this guy wasn't hung like a horse.
John had only met her a couple of hours ago in the motel bar. They were driving in opposite directions and were just here for the night. He had seen her at a table off to the side, almost in a corner and had asked to join her. At first, she was hesitant, but had quickly changed her mind. There had been the usual chitchat, what's your name, where are you going, and so on. Somehow, spouses and sex had come up, and right now, he didn't remember how, but it had eventually gotten around to not only sex, but also anal sex. He loved it, she had never done it, and her husband wanted nothing to do with it. She had professed a real desire to try it. Sometime later, he had asked her to his room, and somewhat to his surprise, she had accepted.
They had started with the usual preliminaries. Being a typical woman, as she got undressed, wished her body looked a lot better, her boobs were a little bigger, and she weighed a little less. And, she hoped he wasn't huge.
John, being a typical man, was happy to have a woman willing to get into bed with him, and as she undressed, was even happier with her body; one he thought was just about perfect! And, of course, wished he was in a little better shape and was hung a little better.
"I hope you like it too." He was right behind her now, and placed the tip of his hard slick cock firmly against her crinkled little anus. Slowly he increased the pressure on it, watched the swollen head flatten a little against her resisting anus, and then watched the lust-swollen cock head slip - almost surge - inside her as that puckered little entrance to heaven relaxed. He just put the head in, just penetrating her tight little sphincter, and stopped. She was tight and it felt so damn good! "There," he said, "I'll hold it right here till you get used to it." He felt her sphincter give his cock-head a good firm squeeze. If he hadn't been pushing slightly, she probably would have forced it out. He needed the rest too or he was going to blow his load way too early. Anal sex with a complete stranger, who really wanted it in her ass, was just way too hot. This was the stuff of dreams!
As the cock tip had touched her, she started pushing back, just like he had told her. She was surprised to feel him slip in there so easily, and it didn't hurt - well, not much anyway. It was a little different, and she was glad he had stopped, or it might have hurt. She felt really stretched back there. Mary lifted a hand between her legs and felt her pussy. This had her dripping wet! Oh, she had been wet and ready for him when they had a short session of missionary sex, but now she was really turned on as he penetrated her virgin ass. A finger started to slowly massage her hard clit. So far, this was great. That initial little pain had quickly subsided. Now, it felt good having John's cock in her ass. Now she wanted more of it. She felt relaxed, it wasn't hurting, and she was ready for some more of him. She wanted to feel him - his hard cock - sliding in and out of her ass. She wanted to be fucked in the ass!
After letting her have a few seconds to get used to something in her backside, John began to push again, and slid most of his cock slowly into Mary's tight little ass. It seemed like she had relaxed now and things would be just fine. He took it easy on her as he started to slowly move his hard cock in and out of her tight little butt. He slowly withdrew until just the swollen head was inside her. Then, he pushed it all the way back into her. He could feel the soft velvety tip just touching the end of her rectum. He just loved the sight of his cock moving in and out of her ass. And, that smooth feeling of being inside her ass, yea, there was nothing quite like it. This was really "doing the nasty!"