“What if you keep the money?” he asked.
And an hour later—and many, many e-mail client refreshes—he received a reply. “No.”
Maybe Tyler and Sheldon were right: maybe it was too good to be true. Maybe it was just some sort of stupid scam. Mark found some solace in this idea. That’s why the poster asked for pictures along with each submission—because he was looking for weak guys, guys who looked like they could easily be manipulated into giving out their credit card info. He probably wanted desperate, submissive guys, and Mark definitely didn’t look desperate or submissive.
So he deleted all the e-mails and he closed the classifieds page. “She’s not that not anyway,” he mumbled to himself, though the image of her mostly-tight naked body remained at the forefront of his mind for the rest of the night. He even had a dream in which he was down on his hands and knees with his face between her legs. He pressed his tongue deep into her slit while she closed her soft thighs against his head. Her skin was slightly oil from moisturizers and treatments, and she smelled like a rose bush. She reached down and pulled his head closer into her snatch, pressing his nose into her clit. She squirted on his face as she moaned. Mark liked the taste of her squirt. He started flicking his tongue harder and faster, making her squirt again.
And then he woke up with a diminishing erection laying in a small pool of warm cum. It was the first wet dream he’d had in five years—and it was the closest he was going to get to the beautiful milf from the mysterious classified posting.
Mark went to school the next morning hoping his friends wouldn’t bring the posting up. But it was the first thing they brought up when they got together between first and second period. “So did they approve your application?” Sheldon asked with a big grin.
Mark rolled his eyes. “No. You guys were right—I think it’s a scam.”
“Did they ask for your credit card information or something?” Tyler asked.
Mark shook his head. “No. They just said that I wasn’t their type, which, let’s be honest, is horseshit.”
“So what’s their type?” Sheldon asked.
And Mark shrugged his shoulders. “Someone who looks like they would fall for a stupid scam.”
It was during lunch when Mark found himself back in the library, searching through classified ads, hoping to find a new ‘fuck my wife’ ad. He figured if there was one, why couldn’t there be another? It was just a bout of hopeless optimism, until he actually found one with the same headline: “Young man wanted. Details within.” He clicked on the ad, and saw a similar post—so similar it was identical. It was posted by the same guy.
But the photo was different. It was the same woman, but now she was in a different pose, on all fours with her head turned away from the camera. Her tits had some stretch marks on them, as if she’d had a child or two, but they still looked firm and fresh. Mark groaned as he stared at the photo, remembering his wet dream, wishing he could have been the mysterious poster’s ‘type’, whatever that was. Mark closed the picture quickly as someone entered the library. But it was just Tyler.
“Looking for more cuckolds looking to whore out their wives?” Tyler asked with heavy sarcasm. Then he laughed. “Oh my God, that is what you’re doing, isn’t it?”
“They posted again. I guess they never found their guy,” Mark said, showing Tyler the new ad and the new photo. Tyler reached over and performed a back-search on the new image. But nothing came up.
“It’s not cropped this time,” he said, pointing to the corners of the picture. “You can see the lens vignette. So these photos must be from this guy’s personal collection.”
“Well maybe you should try applying. Maybe you’ll be their type.”
Tyler laughed and shook his head. “I’m not nearly desperate enough for that.”
Mark shrugged his shoulders. “Suit yourself.” He looked back at the photo and sighed at what could have been had he just been the right ‘type’.
CHAPTER III
It wasn’t long before Tyler found himself looking at that photo of the beautiful milf on her hands and knees once he was home from school.
It was Friday and his sister was out at a friend's house for a sleepover. Tyler was supposed to meet up with Sheldon down at the beach, but it started to rain after school, so those plans were cancelled. So Tyler had nothing to do but stare at that photo.
Again, he tried running it through various image searching programs. But the photo existed nowhere on the Internet, except for in that classified posting. It seemed like someone was whoring out their wife, or some woman they knew intimately, for the sake of some scam. But why? Or was it possible the posting was legitimate? There certainly were guys out there looking for strangers to fuck their wives. According to Tyler’s research, cuckolding was one of the most popular fetishes in the world.
But why offer five grand? Maybe there were strings attached… It would certainly be awkward fucking a woman with another man watching. And he was specifically looking for a young man… Maybe the poster figured a young man would come at a premium. Maybe he was just rich and he didn’t realize people would be willing to screw his wife for free. Hell, he was probably getting fewer replies because of the five thousand dollar offer than he would have gotten had he just posted, ‘Someone please fuck my wife’.
So Tyler found himself considering making a reply. He started writing out an e-mail, but then he became nervous. What if it was an intricate scam? What if they were collecting e-mail addresses for some sort of e-mail virus? So Tyler went to the basement and dug out one of his dad’s old laptops. It was covered in dust, but it still worked.
Tyler’s dad never threw away electronics, even if they were badly out-dated and he never intended on using them again. This particular laptop was so old that it needed to be wired directly into the router to connect to the Internet. The router was in the basement, so that’s where Tyler spent the better half of the next hour. He created a new e-mail account with a fake name, and then he replied to the ad, using the same fake name: Horatio Cummins. He took a fresh picture of himself that wasn’t anywhere on the Internet, and he made sure his face was mostly obscured in the photo, in case the photo ended up on some public shaming website. The photo was a bit blurry and a bit dark because the lighting in the basement was lousy.
He left the computer out and he went upstairs to fix himself a snack. While he was eating, he heard a ding coming from the basement. He rushed downstairs and saw there was a new e-mail in his new e-mail account’s inbox. He quickly opened it and read the message contained within. “Could you please send a clearer photo of your face, a photo of your body (naked), and your clothing sizes, including shoe size?” Tyler’s heart was pounding. He couldn’t believe he actually got a response—and the response appeared to be genuine. It didn’t look like the kind of response a bot would make, seeing as it acknowledged the fact his face was partially obscured in his original photo.
But just because a real human wrote the reply didn’t mean that it wasn’t a scam. Tyler knew better than to send a clear picture of his face and a clear picture of his naked body to some stranger on the Internet. So he closed the computer and put it back in the box where he found it. But his heart continued racing, still high on the excitement from receiving a reply. He wondered if Mark received a reply, or if he was just straight up rejected.
Tyler’s parents came home and they had dinner as a family. Tyler was quiet through dinner as he couldn’t stop thinking about that e-mail that was sitting in his alias’ e-mail inbox. It was around 9:00 PM when his parents left again. They had tickets to see a late-night movie. “We’ll be home late,” Tyler’s dad said before leaving Tyler home along for the night.
And then Tyler remembered that his sister had blue-coloured contacts in her bedroom, which she sometimes wore to school. Tyler figured he could put the contacts in and then he could mess up his hair, which he usually wore parted and pushed back. He wouldn’t look completely unrecognizable, but he would look different
enough if the photo ended up on some humiliating website; people would think they were seeing someone who looked a lot like Tyler, and not Tyler himself.
So Tyler put the contacts in and ruffled up his hair, and then he took multiple pictures in the bathroom mirror. Once he had a face shot he was satisfied with, he took off all his clothes. He could almost see his heart pounding against his scrawny chest. As he held up his arm to take the photo, he started second-guessing himself. Why would anyone want to watch him fuck their wife? He was scrawny and short—his ribs showing and his chest flat. He looked like a young teenager more than he looked like a young man. Surely the poster was looking for some buff, handsome young fellow—though wasn’t that Mark? Mark was buff and handsome and charming, but he apparently wasn’t their type. So maybe they were looking for someone who looked more like Tyler.
Tyler was about to take the photo when he realized his cock was flaccid. Should he be hard for the photo? Would the poster want to see what he had to work with?
Tyler reached down and started to massage his cock. Maybe he wouldn’t make himself hard, but he could at least get some blood flowing into his member so it wouldn’t look so small…
He gave himself one rub too many, and then he found himself erect in front of the mirror. His cock was throbbing, partially from the rubbing and stroking, and partially from the taboo excitement of what he was doing: sending nudes to a complete stranger for the chance of fucking a beautiful woman who was old enough to be his mother.
He took the photo, making sure his eyes were cropped out in case the photo ended up circulating around the Internet. He sent the photos to his alias’ e-mail account and then he sent them off to the ad poster, along with his clothing sizes (all small) and his shoe size (a men’s 6). It was only fifteen minutes later when that old computer dinged with a reply from the ad poster.
“Perfect. Can you come over now? Our address is 22 Havenhurst Crescent. I have the money for you here, and my wife is already ready.” Now Tyler’s heart was seriously pounding. He didn’t actually think he would pass the test. He didn’t actually think they would look at his scrawny body and say, ‘That’s our guy!’ Now he was actually being invited to a stranger’s house, to fuck a woman he’d never met before, for the large sum of five thousand dollars. He couldn’t say no, but he couldn’t bring himself to move. His joints were suddenly rigid and his hands were trembling. A whole new set of anxieties filled his head—
What if he comes too quickly? What if he can’t come at all? What if he can’t even get it up because of the stress of the situation? What if the whole thing really is just a scam or a setup? What if there is someone waiting at 22 Havenhurst Crescent with a gun? Is it really worth the money and the free pussy?
Tyler took a deep breath and decided it was worth it. “I’m on my way in a ten minutes,” he replied. And then he ran up to his bedroom and dug out his best clothes: a black t-shirt and a grey hoodie. He would have worn a dress shirt and some slacks, but he only owned one dress shirt and it was in dire need of some ironing. His slacks weren’t much better off—so he went with jeans.
Havenhurst Crescent was only a couple of miles from Tyler’s house, so he didn’t bother taking the train or the bus; he just hopped on his bike and he was at the house fifteen minutes later. The windows were lit up but the blinds were all closed. There was a path of solar-powered garden lights leading up the sidewalk to the front door. Tyler looked around, realizing he still had one last chance to go back home and forget any of this ever happened. But he could practically smell the money and the wet pussy waiting for him inside. He left his bike on the front lawn and he walked up to the front door.
CHAPTER IV
Tyler knocked on the door. He waited for a minute, which felt like an hour. His heart wouldn’t stop pounding. He had to consciously control his breathing so that he wouldn’t stop breathing altogether. He knocked again, and then he noticed the doorbell. So he pressed the doorbell, and then he became anxious that he rang the bell too quickly after knocking, making him look embarrassingly desperate.
Then he saw a figure moving through the fogged glass. He perked up and took a half step back, ready to run if whoever answered the door was a total creep. He took a deep breath and found himself clenching his hands into fists, as if he was prepared to fight. He took another half step back and then the door opened.
And then he became frozen and speechless as his gaze fell upon the woman in the doorway: the woman from the pictures, in her early forties, wearing nothing but a red lacy lingerie one-piece. She had long, smooth legs, and she had freckles on her shoulders and arms. She leaned against the doorframe. “Horatio?” she said with a grin that was far too confident for Tyler’s liking.
He cleared his throat. “That’s me,” he said, forcing a smile.
“Tina,” the beautiful woman said, and then she turned and walked casually into her own house, leaving the door open behind her. Tyler looked around to make sure no one was watching, and then he became nervous about the fact that no one was watching. He hadn’t told anyone where he was going. If he went missing, no one would ever find him. He’d even put that old laptop back into the box before leaving the house. Would the police find that old laptop in that old box and then consider searching it for clues?
“Are you coming?” Tina called out. Tyler took a deep breath and went in after her. The house was nice: two stories, fully furnished with antique furniture. The walls were all wainscoted and painted white, and the art on the walls appeared to all be original—or very impressive reproductions.
“Nice place,” Tyler said, his voice cracking slightly as he looked back at Tina. He couldn’t believe she was offering her body to him. He couldn’t believe that she would be spreading her legs for him, or even letting him touch her perfect body. She was radiant and confident. And her lingerie was sexy as hell. Tyler tried not to look at her exposed butt as she walked to the bar to pour herself a drink.
“Do you want a drink? Are you old enough?”
“I’m eighteen,” Tyler said.
“Well one drink won’t hurt you, but it’s up to you.”
“Okay,” Tyler said, still standing near the door, still ready to turn around and run away.
“Close that door. We don’t want the neighbours peeking in,” Tina said. So Tyler closed the door. As he turned to look back at Tina, he noticed a man sitting on a nearby couch. The man was staring at Tyler with a grin. Tyler jumped back and grabbed at his heart. Had that man been sitting there motionlessly this whole time?
“That’s my husband, who you were corresponding with over e-mail,” Tina said. She took a sip from her drink and then she walked a drink over to Tyler. “It’s strong but it will help you relax.”
Tyler smelled the drink. He couldn’t tell if it was whiskey or brandy or vodka or all three combined into one glass. He took a sip. Tina wasn’t lying—it was strong. But strong was exactly what he needed. He took a deep breath. “Hello,” he said to the man on the couch. But the man didn’t reply.
“Just pretend like he’s not there. He would prefer it that way,” Tina said. So Tyler tried not to look at the man on the couch as he sat creepily in the corner of his eye. “You’ll just be dealing with me tonight. I’ll help you get ready and then we’ll fuck in the bedroom. My husband will come in to watch, but just do your best to ignore him. He won’t try to touch you—don’t worry about that.”
“O—Okay,” Tyler said, forcing a smile. The whole thing was incredibly uncomfortable, until Tina pulled a wad of cash out from behind the bar.
“Five thousand—as promised. It’s all yours once we’re done here tonight.” She placed it down on the bar. Tyler casually meandered over to the wad of cash and he looked down at it. It was real—each bill crisp and ready to belong to Tyler.
“Thanks,” Tyler said, his voice cracking again.
Tina walked around Tyler and put her hands on his shoulders. She was wearing an expensive perfume that reminded Tyler of the lingerie store at the mal
l. She snuggled up close behind him, pressing her lace-clad breasts against his back. “We’re going to have fun tonight. Just relax.”
“Yeah. It should be fun,” Tyler said, forcing a smile while trying not to look over at the man on the couch.
“But first we need to get you ready. We left out a small detail in our posting—I hope you don’t mind. We didn’t want to scare people off. But it really isn’t so bad. Can you follow me? Bring your drink. We have all night. There’s no rush. We’re going to have fun tonight, Horatio.”
Tyler nodded his head and forced a big, awkward smile. What did she mean, there was a detail they left out? What detail? What strange thing were they expecting him to do for five thousand dollars?
Tina led Tyler down a long hallway towards a closed door. She opened the door and then flicked on a light, illuminating a large walk-in closet, stocked full of women’s clothing and shoes. “So tonight, you will be a woman. And in here, we’re going to find your identity.” She looked at Tyler with that big, confident, beautiful grin. And suddenly, Tyler wasn’t able to force that smile. He found himself rigid with locked joints, trying to remain calm while his brain was screaming at him to get the hell out of there.
CHAPTER V
Mark was becoming frustrated with Sheldon and Tyler. Neither of them was answering their text messages, leaving Mark home alone and bored on a Friday night. He paced his bedroom and then he sent another round of text messages, which he once again received no replies to. He went onto Facebook and saw that Sheldon was out with his friends from his hockey team. Mark hated Sheldon’s hockey team because they were always stealing Sheldon away from the best parties and the most boring Friday nights.
But what was Tyler’s excuse? Tyler wasn’t the kind of guy to go off on his own to any parties, and he didn’t have many other friends besides Mark and Sheldon. So why wasn’t he answering his text messages? Was he asleep? No, no—it was too early on a Friday night to be asleep. It would be a damned shame if he were asleep.
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