Anal Stories: Lily

This was Lily’s first time doing anal, and she expected it to hurt, she was surprised though when he began to work her open and it felt pleasurable. Of course, Jackson was using plenty of lube, they couldn’t really do it without it.

Many of the anal lubes they had tried before hadn’t worked had smelled weird or didn’t last long enough, but this one was fine, and she was surprised by how much she was liking the experience.

After a bit of time working her open, she pushed back on his fingers, he looked at her and smirked she was close to ready. “Do you want me, Lily?” He asked her, slipping a third finger inside of her, he wanted to make sure that she was fully prepared for this. Jackson didn’t want the experience to hurt her as he wanted to do this again in the future.

She nodded at his question and he slowly knelt behind her, lubing up his cock before he pushed slowly inside of her. He groaned at how tight it felt, but it was also nice and wet from how much he had worked her open, he continued to push and listened for any sign that she might be in pain when he heard a moan of pleasure he responded by rolling his hips. “You like me filling this whole, baby?”

“Fuck, yes I do,” the words came out breathy as she pushed back on to his cock, it was such a different sensation to be filled this way, one that she was finding she quite enjoyed more than she thought she would at least.

Jackson moved his fingers so that he could work on flicking her clit as he fucked her, he knew that bringing her pleasure like this would make her want it again. She whimpered as he started, and she began to move her hips faster and he obliged her obvious want by fucking her faster and just a bit harder.

He groaned as she clenched around him, his hips rolling to push his cock as deeply into her as possible. “You feel so good, do you think you can come like this?” He asked her curiously, and when she nodded he stepped up his efforts, he plunged a couple of his fingers into her cunt as he flicked her clit and soon enough she was coming, clenching around his cock tighter than he had ever felt and he came as well.