Bailey's First Anal
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Bailey's boyfriend Tyler has been riding her ass - figuratively - for months, trying to get her to try anal, but she's afraid that it will be dirty and painful. She finally comes around and agrees to let him pop her anal cherry when he promises to take it slow and do everything by the book. Will she come to regret her decision to give up her tight ass? Adults only. More
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Bailey paged through the book she had picked up. Maybe this doctor lady knew the right way to do anal so that it felt good. She knew that Tyler wanted it so bad, and she definitely wanted to keep him happy. She didn’t want anyone to think that she was a slut, but she didn’t want to be a prude either.
Tyler could see that she was softening.
“This can be your present to me, okay?” he asked her.
“I already gave you your present,” Bailey responded weakly. She had gotten him tickets to a concert he wanted to see.
“This is what I really, really want though,” Tyler countered. “Something for both of us.”
Bailey knew that anal sex would be for him, not them, but he had won her over.
“Okay, we can try,” she conceded. “But we have to do exactly what these books say.”
Tyler was absolutely elated and could already feel himself getting hard.
“Thank you, baby, I knew you would try this because you love me!”
Tyler kissed Bailey, who was still pouting a bit. He didn’t mind, though, because he was finally going to get to fuck her in the ass. He only wished that he could somehow record it. For the moment, though, he was satisfied with her agreement to just do it without recording it.
“Look,” Tyler indicated his crotch.
Bailey could see from the bulge in his jeans that his dick was already hard. The fact that this turned him on so much made her feel sexy and powerful. She rubbed him over his jeans.
Tyler wanted to get started right away. Bailey still lived with her parents, who would be home from work in a few hours. He didn’t want them ruining his plans. He also didn’t want to give Bailey a chance to change her mind. He unbuckled his pants and released his swollen cock.
“Look what you do to me,” he said softly. Bailey stroked him a little bit as he pinched one of her little cherry nipples through her tank top. She could feel herself beginning to get wet. Being the object of Tyler’s desires totally turned her on. She leaned into his lap and licked the head of his cock.
“Hold on, babe, I’m going to get the supplies I brought.” Tyler held up his pants with one hand and ran to the door to grab his backpack. He had brought the lube and toys, but he hadn’t bothered to wrap them.