Sitting in his apartment on a Friday night, Mike stared at the one on the cable sports channels. He felt bored and considered going out to a nearby bar. He knew it was karaoke night at the place. Although not a big fan of karaoke, he remembered from previous visits that there were plenty of women in attendance. His friends were out of town or busy, so he would have to go alone.

Mike pulled into the parking lot and entered. There was a decent crowd that night with plenty of females sitting at the tables. He walked over to the bar and ordered a beer as he stood watching the entertainment. The current karaoke singers were doing a mediocre version of a Neil Diamond song.

He felt someone bump into him.  Turning around, he noticed that a cute young woman was responsible. She was talking to her friends trying to figure out what drinks they wanted to order. He glanced down and noticed that her tight jeans really made her ass look great. She then turned to him.

“Sorry about that,” she said. “It’s my friend’s birthday and we got here three hours ago.”

“No problem,” he said in a smooth tone of voice. “Let me buy your next drink for you.”

She looked at him for a moment and he was thinking she would politely tell him to fuck off. To his surprise, she smiled at him and stuck her hand out.

“Hi, I’m Erin. Come over and sit with us. We’re about to leave soon though.”

He accepted the offer and stood by the attractive brunette after she sat down at the table. The table consisted of two guys and three other women. With the exception of their designated driver, Mike knew all these people were wasted.

More drinks were ordered during the next hour and Mike got to know his new love interest a little better. She had just broken up with her boyfriend of four years because he accepted a new job in a different city. She told him the relationship started to become defective before he moved anyway.

With things going well, Mike knew he could probably at least get this woman’s phone number. Then he thought deeply for a moment as her friends continued their loud, somewhat incoherent conversation.

He hadn’t got laid since his girlfriend dumped him six months ago. About to turn thirty-six years old, he knew opportunities to score a one night stand were slowly slipping away. Especially with a drunk twenty-six year old brunette with a nice body and no kids. So many women on the dating websites he tried were either unattractive as hell or had two kids by age twenty-three. Figuring he had nothing to lose, he turned to Erin and opened his mouth.

“Want to go back to my apartment?” he asked her as confidently as he could.

She looked him and softly said it would be best if she just went home. After a little more persuasion however, the rather drunk Erin finally agreed. She stated that she would just hang out with him and he shouldn’t expect sex.

After another half hour or so, the group of people at the table rose and headed to the parking lot. A sober woman who was set aside to drive everyone home objected to Erin getting into Mike’s car. After a minute of chatting, the driver finally gave up trying to convince her not to leave with the man. The friend figured that although she was drunk, Erin was a grown woman and could do as she pleased.

Mike opened the door to his apartment and Erin walked in. He showed her around and the two sat down on his couch. He grabbed a six pack out of the refrigerator and they started to chug some beers while watching television.

After a while, he started to glide his hand gently over her leg. They kissed passionately for a few minutes and she told him she was going to take a shower and freshen up in his bathroom. He found an oversized T-shirt in his room for her to wear afterwards.

While sitting on the couch listening to the shower running, naughty ideas began to race though the horny man’s head. From how much she had to drink, he knew this petite woman would pass out in another hour or so. With the night going completely the way he wanted, there was one more thing he could do to make it the best night of his life.

He removed a condom and some lubrication from a dresser drawer. Knowing his plan wouldn’t succeed if she saw the lube, he hid it in a reachable location under his bed. He was shaking from how nervous he was now feeling.

Five minutes later, she emerged from his bathroom wearing the T-shirt. She sat down on his bed and they embraced. With the lights still on, he noticed she was wearing only black thong under the shirt. Her hair was still wet from the shower.

While she watched, he put on the condom. Now was the time to put his plan into action. He knew accomplishing what he wanted would require a little luck.

He flipped her over onto her stomach and pulled down the thong. His teeth bit hard into the center of her right buttock and then he started liking her pussy. He stared at her exposed asshole. He grabbed the lube out from under the bed and sneakily started placing it on his cock. Then, in an incredibly risky maneuver, he gently placed a generous portion of lube between her butt cheeks.

Mike had entered unknown territory. He had never got the opportunity to fuck a woman in the ass. Although he asked a couple of his ex-girlfriends, their reply was always a definite no.

While Erin’s pussy was being licked, the effects of the alcohol really started to catch up with her. After the lube was discreetly placed on top of her anus, she felt a cold sensation between her buttocks. Fortunately for Mike, the drunk woman didn’t think too much of it.

“Let’s change positions,” she murmured.

Knowing it was now or never, Mike forcefully pushed his right thumb into the ass of the unsuspecting brunette. To his amazement, she didn’t scream in objection and storm out of his apartment. She just continued laying silently in her current position. He then removed his thumb from her butt.

After feeling the thumb slide into her ass, Erin was speechless for a moment. The intrusion hurt something fierce. She was now a little pissed off at this man she hardly knew.

It also excited her in a strange way. To the best of her recollection, her ex-boyfriend never touched her asshole.

“What the fuck was that?” she said looking over her shoulder.

“Do you trust me?” he replied.

Now spinning from the alcohol, she decided to play along and simply submit to this man’s desires. She got on her knees and stuck her butt into the air.

“Alright,” she said softly.

After straddling her while standing on the bed, he placed his cock against her asshole and slowly slid it in. It was very slow going at first. Then, after about half a minute, the muscles in her ass stretched to better accommodate the meat. He started to pump in and out at a rapid pace.

While this was occurring, she groaned in a strange mix of pain and unexplainable stimulation.

He removed his cock for a moment to look at her now gaping asshole. After catching his breath, his dick plunged back in for one final assault. One minute later, he burst.

Upon knowing he was finished, she let out a sigh of relief. There was no way she could have taken any more. She put the shirt and thong back on and quickly passed out on top in his bed. 

Erin left the apartment early in the morning without hardly saying a word to him.  She never told her friends what happened that night.  When asked, she told them she just slept on his couch.  Nothing more.

Her asshole throbbed unrelentingly with soreness during the following two days. Now having tried it, she knew she would never return to experiment with anal sex.

Mike and Erin never saw each other again. Neither of them would ever forget that awkward one night stand however.