Brooke's Anal Affair

Brooke's late night phone call had been incredibly odd. Despite the fact that her wedding was less than 24 hours away, he had the tiniest hope that this would be the day he'd finally bang her. The thought of it got him rock hard on the drive over, but he would certainly not be the one to initiate despite the fact that he'd been wanting to bang her for over a decade. Both of them were 30 now, having been friends since 19 when they began working together. Outside of one make out session during a night at the bar, there had never been a real sexual history between them. They had only ever been close friends.

When he got to Brooke's condo, she hugged him and told him to sit at the couch. She was obviously eager to talk about something. She sat beside him and instantly spat it out.

"I'm really nervous," she said. Jake was instantly annoyed as he had nothing to say and really didn't feel like dealing with this shit at 1AM. "I know I love Todd and that he loves me, but I have a nagging feeling that I..." She paused.

"That you what," Jake replied, successfully hiding his irritation.

"That maybe I didn't get *it* all out of my system, you know." Brooke had always been pretty conservative sexually, only ever having fucked two boyfriends and once uncharacteristically giving head to a coworker of theirs. Jake was surprised that she was all of a sudden worried about not fucking enough people before she settled down.

"Well," Jake laughed, "there's not much you can do about it now."

"I know..." she trailed off. She gave Jake a flash of a flirtatious look. He touched her thigh and she instantly jumped on him. They began making out furiously for about a minute before she stopped.

"I can't," she whispered as Jake sighed, "I can't cheat on Todd."

"I know," he replied. Brooke sat there looking about as frustrated as he was. Suddenly, he had an idea. It'd be a huge longshot, but as they say, you miss 100% of the shots you don't take.

"If I fuck you in the ass, it's not technically cheating," he snickered.

"In my bum?" she asked, shocked. "But that's where I-"

"This will be your last chance," Jake interrupted.

"Uhm... alright," she replied after some thought, "but you can only have my butt. My pussy is off limits and I'm not blowing you, either."

"Agreed." Jake's cock was as hard as it ever had been watching Brooke get on all fours and pull down her pants and white panties. He got on his knees behind her, cock throbbing as his hands each gripped one of her plump white ass cheeks, spreading them to fully expose her brown, untouched starfish. He wasted no time, giving her sacred hole a swirling lick.

Brooke gasped when his tongue made contact with her anus. The idea of anal sex had never occurred to her, nevermind someone licking her fartbox. It felt so dirty, but at the same time nothing had aroused her more than the feeling of her forbidden hole getting tongued. Whenever Jake would press his tongue down on her asshole, she would let out a moan of pleasure. She lay flat in a prone position and reached back to grab her ass cheeks, spreading them so that Jake could more thoroughly lick her. After about five minutes of her starfish being moistened, she got on all fours again.

"I'm ready," she begged. "Go slow."

Jake obliged. He pressed the head of his throbbing cock on the entrance of her exposed butthole, already wet with saliva. He slowly began to thrust in, trying to penetrate her tight sphincter.

Brooke's face became a mixture of shock and pleasure when her forbidden exit became an entrance. As Jake pushed his dick further and further into her rectum, her eyes rolled back into her head, showing her pure ecstasy. It was like nothing she had ever experienced. She had been thinking about the probable discomfort she'd experience when her butt finally got stuffed, but that had only lasted for one second. She pushed back, desiring for her rectum to be penetrated by more than the three inches Jake had already inserted. Soon, he was balls deep in her ass, holding his position there for a few seconds. Brooke could not believe how full her bum felt and how much she enjoyed it. Jake gave her bum cheek a firm spank, causing her to moan again.

She felt like such a whore. How could she have let someone take her butthole like that? How could she have let someone enter her through *there*? It was so disgusting. Before tonight, she had never desired or thought of anal sex, but here she was now, five inches of cock in her backdoor and a man's balls slapping against her as he thrust in and out of it and spanked her periodically.

Jake didn't last long with his cock hugged by the snug warmth of Brooke's rectum. He thrust in and out of her for about two or three minutes when he finally felt himself near climax. Part of him wanted to stay in her butthole forever, but the other half realized that taking Brooke in the bum was the single most pleasurable thing he had ever done. He looked down at his cock stretching her anus just as he unleashed his seed into the depths of her ass. Even if this never happened again, Jake was content knowing that he had stretched Brooke's butthole.