Bailey’s Butthole

Bailey had finally decided that she wanted dick. She was 22 years old and had never had sex. She wanted to save her pussy for marriage. The closest she came to having sex was one time when she was on all fours on her roommate Cole's bed, jeans and panties down to knees. Right before Cole could enter her, she pulled her underwear and pants up and said that she wanted to save herself for marriage. Cole understood and had no hard feelings, but she knew by the way he looked at her that he wanted her badly.

She was very pretty, with brown eyes to match her silky hair that reached just below her shoulders. Her small titties complemented her thin overall build. What she lacked in breasts she made up for with what many a man would call the fattest ass they've ever seen, especially given how slim the rest of her was. It wasn't so enormous that it looked ridiculous, but the roundness of it made it impossible for a man to take his eyes off it whenever she walked by.

All her closest friends had been fucking anything that walked during their last year of university. They would tell each other about their escapades and mishaps, and Bailey would laugh along with them. One time, a friend of hers told her that her boyfriend has fucked her in the ass. Bailey was originally disgusted, but when her friend told her it felt good she had an idea.

***

"Hey, I know last time I kinda blue-balled you, but I wanna make it up to you," she neevously told Cole as they sat beside each other on her bed.

Cole's dick instantly went hard, flattering Bailey. "How?" he asked excitedly.

"Well, I'm not gonna let you fuck my pussy, I'm still saving that. However," she comtinued, drawing out the -er sound, "I'll let you put it up my butt as long as you don't tell anyone." She said the last part really quickly to quell any doubts she might have.

"Uh..." was all Cole could muster. He couldn't believe that Bailey really just offered to give up her ass to him. Wasn't her butthole a step beyond her pussy?

Bailey almost immediately felt a sense of dread. How could she just offer her butt like that? She had seen Cole's dick before. She knew that anal sex wasn't anything crazy, but she never imagined that she would ever take a finger up there, nevermind having a dick 6 inches up her bum. Worst of all, it was such a taboo and dirty thing to do. Bailey had never thought about her butthole as an entrance. That was where she...

Regardless, within a few minutes she was on all fours with Cole positioned behind her. He reached around her to unbutton her jeans, slowly pulling them down over her round bum and toned thighs. Next he grabbed her white cotton panties and pulled them down to her knees as well.

Bailey let out a gasp when Cole's tongue began swirling around her backdoor. She was equal parts surprised that he would lick her starfish and that it felt so good. Something about Cole licking a place she considered off-limits and dirty for so long turned her on to no end. After a few minutes of her anus being moistened by his tongue, her pussy was soaked (not that this would help her ass). Bailey wanted to badly have her pussy penetrated from behind, but she knew that she wanted to keep herself pure even more.

Cole placed his finger right on her tight asshole, lustfully tracing every ridge in and around her brown ring. Bailey was nervous. This was the first time something would be going in her bum instead of out. Judging by how long Cole had been putting pressure on her anus without entering it, she knew it was incredibly tight. Eventually, it went in.

Bailey squealed as soon as her pooper was breached by Cole's finger. He heard her breathing heavily as he explored the walls of her rectum with his finger. He couldn't wait to explore the depths of her ass with his dick. Eventually, he removed his finger and placed the head of his dick against her brown butthole.

"Go slow," she said.

She let out an even louder gasp that turned into a full blown moan when Cole penetrated Bailey's ass. Her eyes rolled back into her head as he slowly buried his cock deeper and deeper in her backside. She had never felt so full, couldn't believe how turned on she was from having her sphincter stretched like that.

When he finally was balls deep, Cole let put a groan. The tightness of Bailey's anus was a preview of her insides. Her rectum hugged his cock tightly as he slid it in, he couldn't believe how good it felt physically. He was also even more turned on that he was now balls deep in the ass of the biggest prude he knew. He couldn't brag about it and wouldn't, but it didn't matter. He knew that his dick had been deep in Bailey's bum.

He began to slowly thrust, going halfway in and out every time. Her poopchute provided immense pleasure, tightly surrounding the dick that probed Bailey's insides with every movement.

Bailey let out squeals and moans with every thrust. She couldn't believe that her ass was being fucked. She wondered if being fucked in the pussy would feel this exciting. She was ashamed that her backdoor was such a huge source of pleasure. The shame only increased when Cole began spanking her white cheeks as he plowed into her butt.

"Where is my dick?" he demanded.

"In my butt," Bailey obediently moaned in reply. "I've never had-," she gasped, "I've never had anything up there before."

Cole gripped one of Bailey's ass cheeks hard and spread it. He loved the feel of her soft ass in his hands, loved the feel of her rectum around his dick. He let go and gave her a quick and stern spank, eliciting a moan in return.

Bailey's moans alone were almost enough to bring Cole to the brink of cumming. Hearing her talk about how much she liked it in her backside was even hotter. Eventually, the time came.

"I'm gonna-" was all he managed to say before he released several spurts of cum deep into Bailey's bowels.

***

Later that night, Bailey thought about the what happened to her ass earlier. She initially thought that it would only be a one time thing, but the pleasure was just too great. Cole would have her butt again, very soon.