The Anonymous Visit

It was a fateful day, the day Kyle discovered Craigslist. He had heard of the site and heard stories about people listing things for sale, looking for roommates, etc. Kyle did not, however, realize it had a personals section. *This was before personals went bye bye*

Kyle had always had a higher than normal sex drive, even for a male in his early twenties, but did consider himself to be straight.

When he discovered the personals section he saw lots of categories: w4m, m4w, ww4m, and on and on it went. He felt it best to stick to the basics...w4m. Surely there was at least one woman in his city looking for a hookup?

He began browsing the posts and quickly became discouraged. Most were clearly fake. He did happen to come across one that showed some promise. It was just a simple post that was looking for an anonymous gettogether. That in and of itself struck Kyle as odd, but the rest of the post did not have the broken English, the fake contact information, or anything else that the rest of the fake posts typically included.

Kyle honestly didn't even know what was meant by an anonymous encounter. He searched the term and quickly learned that both parties could remain unidentified. There would be no meeting up to chit chat. No drama. Just a no-strings hookup. It was exactly what Kyle was looking for.

Kyle responded to the post, and within a couple of minutes had a reply in his inbox. He quickly looked it over and to his amazement it actually seemed to be a real reply. No redirect request, no asking him to sign up for some random site, just an honest to goodness real person.

He figured he might as well shoot his shot, so he asked what the woman was looking for, and for her location. She responded plainly that she was craving a hard cock deep in her pussy. Kyle immediately had doubts: 1) how could he know this woman was clean? 2) what about pregnancy risks? He replied and directly asked these two questions.

The woman responded that she was on birth control, and that she had just gotten her test results back, with no STDs. Then made it abundantly clear he would also be wearing a condom. She then asked if he was going to continue to waste her time now that his concerns had been alleviated.

Kyle had to respect her bluntness. What could go wrong? Kyle replied that he was game. The woman replied back with a list of instructions, as well as her apartment complex's address. Kyle was told he would receive the actual apartment number when he arrived. The other instructions were quite specific:

-when he arrived, let himself in and step into the bedroom

-drop his shorts and wait

-do not turn on any lights

-do not expect any talking

The woman said she would take care of everything. All he would need to do would be stand there and savor it. And to whet his appetite, said that she would chew on his cock with her pussy. Kyle didn't quite understand what that meant, but it was very intriguing. He replied that he would shortly be on his way.

The apartment complex was not too far from his house. He let the woman know he was pulling in, and she responded with her unit number. Kyle's nerves were steadily increasing. What if this was someone looking to rob him? What if she was hideous? Idiot, Kyle thought, it isn't like you'll see her. So why would that matter?

The woman's unit was on the 2nd floor. He reached the door and noticed it was slightly ajar. He pushed it open and stepped into a very dark room. Shutting the door behind him, he was able to make out the bedroom right where the woman said it would be. The apartment was eerily silent.

Kyle slowly made his way to the bedroom and thankfully, noticed a couple of windows with open shades. Moonlight was illuminating part of the bedroom, almost as if directing him where to stand. He was naturally drawn to the spot and made his way into the bedroom.

Kyle did as he had been instructed and dropped his shorts. Out of the darkness he caught motion as a tall and slender figure crawled towards him on her hands and knees. Her face was covered by long dark hair that shined in the moonlight.

It was all incredibly surreal. He was exposed in front of a complete stranger, just waiting for her to have her way with him. The woman did not waste any time.

She knelt up and gently sucked Kyle's flaccid cock into her mouth. Kyle closed his eyes and lost himself in the warm wet sensation. He felt firm but gentle fingers grip his balls. His cock quickly began to stir in the woman's skilled mouth. She had a very tongue-heavy method of cocksucking. Her tongue danced, darted, and swirled all over his cock. Almost as if it were trying to distract him, while her lips inched forward until he was buried in her throat. Holy shit this woman could suck cock, but she had a peculiar way of gripping the base of his cock, almost too hard. It was almost as if she was afraid he'd try to pull out.

After a few more minutes the woman stood, keeping her face turned downwards, and led Kyle by his cock over to the edge of the bed. They stepped out of the moonlight that was shining on the floor, and into darkness as they approached the bed. There was a little light but Kyle could barely make out anything. The woman got on all fours in front of him, exposing her corset-covered torso and thigh high leggings that led to crotch-less panties. Kyle was able to make out that she reached behind and appeared to be playing with her asshole. Slick and wet sounds were coming from it as she appeared to be rubbing in some lube. Odd, he thought, but he was soon distracted by her other hand reaching for his cock. She had poured lube on it and was now stroking and rubbing it on his cock.

Kyle thought it strange that someone would lube a cock BEFORE putting on a condom, but was enjoying the sensation all the same. He stood there and let the woman slicken up his cock.

The next chain of events unfolded quickly. The woman again gripped the base of his cock firmly, holding Kyle in place. She raised her ass and backed up, guiding Kyle's bare cock towards her asshole. Mental alarms started sounding for Kyle, as they had not talked about doing anal, much less doing it bare. So taken back was he by the quick turn of events though, Kyle could not react in time. Kyle had fucked plenty of asses, and he knew instantly that this was an ass that had taken plenty of cocks.

He felt the asshole spread across the head of his cock, and quickly travel down the length until he was balls deep inside of it. This was not an ass that took time to adapt to his girth. This was a well-used ass that greedily gulped down his cock.

The woman let out a low guttural moan as she clamped her ass down on his cock, and began to slide it up and down the length. The woman's hands disappeared underneath her body. Kyle tried to pull back but she quickly reached underneath her legs and grabbed his balls. She meant for him to stay right where he was.

Kyle relaxed and decided it wasn't that bad. She must just want to get her ass stretched before taking him into her pussy. But the longer he was captive in her ass, the more he realized she was intent on getting him to cum bare inside it. Her hand kept massaging his balls, almost as if she were trying to coax them into cumming. Her wet and loose ass continued to stroke his cock.

Her other hand was moving furiously underneath her, evident as Kyle could see her arm moving rapidly. Stroking her clit, Kyle assumed. The longer she kept this up the more aroused he became. Suddenly he felt her ass begin to contract. Holy shit she was cumming and her ass was squeezing his cock. This was too much for Kyle and pushed him over the edge.

The woman tightened her grip on his balls as she felt them contract, and pressed her ass back to take Kyle deep. Kyle began to shoot his cum deep into her ass. She moaned deeply as she worked her ass to wring out every last drop.

Kyle heard a soft SCHHLOOOOP as she pulled forward and off his cock. She reached up from under her legs and handed Kyle a wet washcloth. Kyle realized this was her plan all along. Kyle took the cloth and absentmindedly cleaned his cock. The woman was strumming her fingers on the bed, as if telling him to pick up the pace. Kyle lifted his shorts and quickly exited the apartment.

Driving back home he couldn't get over what had just happened. He didn't know what to think. He had almost pulled into his driveway when his phone dinged. It was another email from the mystery woman. Kyle pulled into his garage and opened the email. His jaw dropped. There was an up close picture of an ass that had clearly been cummed inside, and as he scrolled further down, a set of balls and a cock lowly hanging. There was a caption that read "Thanks so much for the creampie in my sissy-pussy! :) You'll have to come visit me again!"

Kyle quickly replied that he wasn't into men, not even those that passed for women. The woman, well, the stranger replied: "Funny, your cock didn't seem to mind as my pussy was chewing on it."

Kyle responded that he didn't appreciate being tricked like that and that they would not be seeing each other again.

"I've heard that before...night!"

Kyle was shaken to his core. A few days passed and try as he might, he kept jerking himself off to the memory of the stranger's loose ass. He could not get the memory out of his head. Before he knew it, he had messaged the stranger again.

"Took you long enough. My pussy has been waiting for you to breed it again..."

Like a moth to a flame, Kyle the 2nd of many trips to the strangers apartment.