A Hookup Gone Bad (Patreon)

Tyler’s night had started with what he thought was a solid plan for getting laid for the first time in nearly four months. He put on his suit, ditched his glasses in favor of contacts, and headed to the bar full of confidence. He was on a business trip but he had tomorrow off and he was going to make the most of it by charming a woman back to his room for a night of pleasure.

Knowing that he wasn’t the best-looking guy, Tyler was prepared to have to buy drinks to get girls to talk to him. He managed to get a few cute, seemingly willing girls to indulge in conversation over a drink he’d pay for, but by the end of the night he’d run up a $125 tab and had failed to convince anyone to come back to his room.

His suit now hung in the closet and he was in bed with his phone in his hand and a newly-downloaded dating app on screen. He swiped his way through an astonishing collection of beautiful girls, sending quick messages to those that seemed remotely in his league, and thus represented a decent chance of being willing to hook up.

A particularly pretty girl with dark hair, big brown eyes, and what appeared to be a tremendously perky pair of big breasts was the first to message him back. They flirted back and forth until she requested Tyler take a selfie. She wanted to see his face to make sure his profile picture wasn’t a lie. Tyler happily took the picture and sent it along.

“You’re cute,” the girl replied.

“You’re beautiful,” he said. She had a handful of pictures on her profile and she was unquestionably pretty.

“Yeah? You think so?” she messaged.

“Definitely,” he replied.

“What’s your name?” she asked.

“Tyler,” he wrote. “What’s yours?”

“Keri,” she wrote back. “So, do you live in town?”

“No. Here on business,” he said. “I’ll be gone on Tuesday.”

“So you’re looking for a one night stand?” Keri messaged.

Tyler typed out an affirmative response and hesitated with his thumb over the ‘send’ button. He wondered if it was really wise to be so open about his desires. Didn’t girls find it annoying when guys had trouble thinking about anything other than sex? Ultimately, he hit send. It was getting late and he didn’t really have time to mess around. Either she was interested or not.

“Let’s see your cock,” Keri messaged back.

Tyler stared at the message. It was the first time a girl had ever asked to see a picture of his dick. He wrote back, “Hard or soft?”

“Hard,” she replied. “I want to see what you plan on fucking me with.”

Tyler pulled his underwear down and wrapped his fingers around his cock. He stroked as he looked at the cute brunette’s pictures. He imagined her big, beautiful breasts bouncing in his face as she rode him right there in his hotel bed. He imagined how good it would feel to fuck someone after such a long dry spell. In no time at all he was hard. Tyler snapped a picture and sent it to Keri.

“You know that’s not a big cock, right?” she messaged back. “It’s kind of pathetic, in fact.”

For some reason, Tyler’s heart raced as he read the message. He felt a surprising, rather pleasurable sort of tingling between his legs. It was arousal. There was no question about it. The only question was why the insult to his size turned him on.

“Sorry,” Tyler wrote.

“You should be,” she replied. “You should apologize to all the girls you’ve fucked before, too, because there’s no question you’ve disappointed them with that sad dick of yours.”

Tyler read the message over and over as he stroked his cock. He didn’t bother wondering why it turned him on. He chose instead to enjoy the fact that it thrilled him.

“Give me the name of your hotel and your room number,” she demanded.

Tyler gave the information she wanted without thinking about it.

“I’ll be over soon,” she wrote. “Leave the door open. I want you naked and on your hands and knees in the bed when I get there. Make sure you’re facing away from the door or I’m walking out. Do you understand?”

“Yes,” Tyler replied.

“Keep your fucking hands off your little dick, too,” she messaged. “I’ll be in charge of whether or not you get to cum tonight.”

“Okay,” Tyler wrote.

“See you soon,” she replied.

He put his phone down and looked at his cock. It was still hard and now there was a glistening drop of precum at the tip. He had no idea if Keri was going to show up or not. She knew where he was staying, though. She could be at the door in no time if she lived nearby.

Tyler had no idea what she had planned. He assumed she wouldn’t be interested in fucking him. She’d made that perfectly clear. Anything else seemed possible, though. Was he interested in seeing what was possible? Did he want to prop the door open and put his naked body on display? Did he want to risk the embarrassment of a random passerby walking in? Did he want to play with Keri, assuming she showed up?

Tyler’s cock was still hard. More precum had appeared at the tip. He was desperately horny. Four months of masturbation and fantasizing will do that to a guy. He pulled his shirt off. He took his underwear off. He tossed his clothes aside. He got on his hands and knees in the bed to see what it would feel like. He tried to imagine why Keri would possibly want him in that position. Maybe she wanted to 69. Maybe she was just kidding and she was going to get naked, get on her back beneath him, and invite Tyler to fuck her. Maybe his imagination wasn’t strong enough to conjure what she actually intended on doing.

A mixture of curiosity and genuine desperation for an orgasm led Tyler to commit to seeing it through. He backed out of the bed, opened the door, and shut it gently enough that it didn’t lock. All Keri had to do was push it open and she’d be able to walk into his room.

Tyler took a deep breath, spun around, and walked to the bed. He’d made the decision. He was going to go through with it. He was going to do whatever it was that Keri had in mind. His heart pounded relentlessly as he climbed into the bed and waited on his hands and knees.

A minute later he heard footsteps approaching. Tyler’s pulse raced, but whoever it was walked right by, probably on the way to their room. Tyler took a deep breath and told himself to calm down. There was no benefit in freaking out every time it seemed like someone might be coming to his room.

Tyler spent ten minutes on his hands and knees before someone turned the door handle and stepped into his room. He turned his head to look back and was met with a sharp rebuke. “Face forward, Tyler,” a soft, feminine voice said.

“Sorry,” Tyler replied.

“Damn, look at that,” a distinctly male voice said. “I guess you were right. You found a good little beta bitch we can play with.”

A sense of panic rose up in Tyler’s chest. His arms felt weak and his head felt hot. He could hear his heart beating hard enough that it had to be unhealthy. He turned his head to look back again and was greeted with a painful, loud smack on the ass before he could catch a glimpse of Keri or the man she’d brought with her.

“What did I say, Tyler?” she yelled.

“Sorry,” he replied.

She smacked his ass again and he cried out in pain.

“You’re going to do as you’re told, Tyler,” Keri said. “I think we both know that. I think we both know that you’re a little beta bitch at heart. I think we know that you’re naked and on your fucking hands and knees for a total stranger because the idea turned you on so much that you couldn’t resist. I think we both know that you fucking loved when I pointed out that you have a small, worthless cock that has no place inside a woman.”

Keri ran her fingers over Tyler’s ass and lower back and he let out a breath he didn’t even know he’d been holding in. Her gentle touch helped him relax and he apologized once more. “Sorry,” he said.

Keri caressed his balls and offered his stiff cock a few blissful strokes. She collected the precum dripping from the tip and promptly rubbed it over his asshole. An inadvertent moan escaped Tyler’s lips at the unexpected stimulation and Keri laughed.

“I told you,” she said. “I’ve got a sixth sense about these things. I know a little bitch when I meet one, even on a dating app.”

“Look at him open up,” the guy said as Keri’s finger gently penetrated Tyler’s asshole. “It’s like he knows he was meant for this.”

Keri laughed and pushed her finger all the way inside Tyler while he closed his eyes and groaned as a dozen different feelings competed for attention in his head. He’d never had his asshole touched by a girl, let alone penetrated. He’d never been naked and on his hands and knees in a hotel bed. He’d never invited a complete stranger – who brought another stranger with her – into his room. He couldn’t believe he hadn’t kicked Keri out of the room the moment she walked in with someone else. He couldn’t, though.

Tyler wanted to keep going. He wanted to pursue the strange but undeniable sense of desire that had blossomed the moment Keri told him she wanted him naked and on his hands and knees.

“Get your clothes off,” Keri said.

Tyler’s mind raced to figure out what was going to unfold in his hotel room. Was Keri going to fuck the other guy while he watched? Was the anal fingering a sign of things to come? If so, did Tyler want to kick them out before things got completely out of control?

Then Keri walked around the bed and appeared in front of him. She had a smile on her face and she wore a tight, low cut dress that made her breasts look irresistibly sexy. She leaned forward, giving him a spectacular view of her cleavage, and said, “It’s nice to meet you, Tyler.”

“It’s nice to meet you too,” he said.

Keri leaned closer and gave him a soft kiss on the lips. “I’m so glad you were a good little bitch for me,” she whispered. “I figured you’d chicken out and leave the door locked. Imagine my delight when I found it open and saw you on your hands and knees, waiting to be my toy.”

She stepped back and beckoned for the man standing behind Tyler to join her. Soon enough a tall, exceptionally fit, remarkably well-hung man joined her. He was naked as she’d requested and it seemed that he was already half hard in anticipation of what was about to unfold.

“Tyler, I’d like you to meet Mark,” Keri said.

“Nice to meet you, Mark,” Tyler said.

“We’ll see,” Mark replied.

Keri fell to her knees in front of the man she’d brought and took him into her mouth. She offered the kind of blowjob Tyler had hoped to receive that night. She sucked with the kind of wild abandon he’d only seen in porn videos, though he suspected that was the point. Keri was putting on a show as she orchestrated the evening to be exactly as she wanted it to be.

“Isn’t his cock beautiful?” she asked while her fingers moved up and down the slick, stiff shaft.

Tyler nodded, though he felt a little weird judging the beauty of another man’s cock.

“This is what a real man’s cock looks like, Tyler. I’m sure you’ve noticed that he’s quite a bit more impressive than you, that he’s longer and thicker and that his body is far more arousing than yours is. That’s why he’ll be doing the fucking tonight and while you’ll remain on your hands and knees like a good little bitch. Do you understand that, Tyler?” Keri asked.

Tyler nodded as an unfamiliar kind of arousal enveloped him. He still had no idea what Keri wanted from him, but it didn’t matter. He wanted to do whatever she desired.

Keri stood, looked at Mark as she continued to stroke him, and said, “Fuck him.”

“With pleasure,” Mark said.

“What?” Tyler asked. He watched Mark move around the foot of the bed and behind him.

Keri grabbed a handful of his hair and pulled Tyler’s attention her way. She bent over and he stared at her cleavage before she directed his gaze to her eyes. “Mark’s going to fuck you like the little beta bitch that you are,” she said. “If your cock wasn’t so pathetic you’d probably be in my mouth right now. You’d probably be enjoying the kind of blowjob I just gave him. Then I’d climb in your lap and take you into my perfect, tight little pussy and ride you until you fucking exploded. If your dick wasn’t so small I’d have given you the orgasm of your life, Tyler. Instead, Mark’s going to use your beta ass for his pleasure and you’re going to take it like a good bitch.”

“But…Keri…please,” Tyler said.

Keri tightened her grip on his hair and slapped Tyler in the face. His ears rung for a few moments before she pulled hard on his hair, leaned closer, and spit on him. Her warm fluid dripped down his forehead and over his eyelid before dropping to the comforter.

“Mark loves using beta bitches like you,” she said. “He loves putting you in your place. He really loves doing it while I watch. He loves showing guys like you how fucking pathetic you are by using your asses for his pleasure. Most of all, he loves showing guys like you what you really want. I love it too, Tyler. I love seeing him break a little beta bitch like you. I love seeing him pound a bitch like you until you’re begging him to fuck you harder and dump his load in your ass. I’m fucking wet just thinking about it.”

Keri worked the bottom of her tight dress over her hips and plunged two fingers into her pussy. They emerged slick with her juices and she licked them clean as Tyler watched.

From behind him Tyler heard Mark spit. He felt two fingers against his asshole. Mark was rough. He worked his fingers in hard and deep. He used them to stretch Tyler and the moment they departed they were replaced by the head of his thick cock.

“Fuck…fuck…fuck,” Tyler said between hurried breaths. He wasn’t sure what he wanted. His cock was still hard and his body hummed with desire. He was deeply afraid, though. Anal sex was going to hurt. Of course it was going to hurt. But the look in Keri’s eyes was one of wild desire. She was turned on. She was wet. She wanted to see Mark fuck him and for some reason Tyler wanted to do as Keri desired.

“Fuck him,” Keri said. “Stretch his ass. Take it. Fuck it. Destroy it.”

Tyler gritted his teeth and tried not to scream as Mark penetrated his ass. The pain was intense, but the look on Keri’s face seemed to signal an unexpected level of pleasure as she watched him suffer. She released her grip on his hair and reached between her legs. Her finger moved furiously over her clit and she moaned like a woman in the middle of a truly great fuck.

“Fuck him, Mark. Fuck his little beta ass. Fuck this bitch like he deserves,” Keri said.

Mark placed a hand on Tyler’s lower back and pushed down hard. “Arch your back, bitch,” he demanded.

Tyler did as he was told and Mark’s cock moved deeper inside him.

“That’s a good bitch,” he said. Mark grabbed Tyler’s hips and began to fuck him. He spit on his cock several times to provide lube and eventually worked his way up to a vigorous rhythm.

“How does it feel?” Keri asked.

A dozen different answers leapt to Tyler’s mind. It felt like the most insane thing he’d ever done. His night had begun with a quest to get laid at the bar and now he was on his hands and knees on the receiving end of the exact kind of fucking he’d hoped to give that night. The girl he’d hoped to fuck was standing in front of him and masturbating furiously as she watched Tyler lose his anal virginity. It felt painful. It felt humiliating. Oddly, it felt hugely arousing in a way he’d never experienced.

“It feels good,” Tyler answered.

“I fucking knew it,” Keri said. “Every small-dicked bitch like you loves being put in his place. You fucking love being shown that you’re nothing more than a toy to be used for the pleasure of your superiors. Mark is your superior. I’m your superior. You’re just an inferior little sex toy.”

Tyler was equal parts confused and delighted that he felt such overwhelming arousal while suffering through the pain and humiliation of being fucked by a man for the first time in his life. It certainly helped that Keri seemed so completely lost in her pleasure. Her finger danced over her clit with such speed that he was certain she’d cum quickly.

“Flip him over,” Keri said. “I want to sit on his face while you cum in his ass.”

Mark pulled out and flipped Tyler over like he was light as a feather. Suddenly he was on his back with his ass right at the edge of the bed. Mark slid inside him again and buried his cock balls deep. A moment later he’d resumed the rhythmic anal fucking, only now it felt far more pleasurable. Tyler didn’t understand why, but he couldn’t help but moan.

Keri climbed into the bed, stood above his head, and sat on his face. Her pussy hovered a few inches above his mouth and Tyler extended his tongue in hopes of tasting her.

“It feels good, doesn’t it?” she asked.

Tyler nodded.

“It’s because he’s hitting your prostate. He’s fucking your man pussy and hitting your man clit,” she said. “If he lasts long enough he might even make you cum like a true fucking faggot.”

Keri sat on Tyler’s face and began to ride it with her pussy. She wasn’t interested in him eating her out. She just wanted to smother him with her slippery flesh and stimulate her clit at the same time.

Tyler laid there as let them use his body. Mark fucked his ass and rubbed his prostate with the head of his cock. Keri rubbed her labia and clit all over Tyler’s face as she reached up to play with her beautiful breasts in the tight dress. Her moans rang out, joining Mark’s grunts as they both barreled towards their respective climaxes.

“Cum inside him,” Keri said. “Cum in his little bitch ass. Flood his asshole with your fucking load. Breed this little faggot.”

Mark fucked him harder and Tyler groaned into Keri’s pussy. He groaned at the idea of another man cumming inside him. He felt the intense sense of humiliation and the confusing arousal that came with it.

“Fuck!” Mark screamed.

Tyler felt the big cock swell up in his asshole. It stopped moving. It was cumming. Mark was cumming in his ass. A man was cumming in his ass.

Keri reached down and grabbed a handful of Tyler’s hair. Her screams joined Mark’s as she climaxed. Her thighs trembled wildly on either side of Tyler’s head and juices gushed from her pussy and dripped down his face.

“Fuck,” she said. “That was fucking incredible. God damn I love using a naughty little bitch like you. That was so much better than a hard fucking from any cock would have been.”

She climbed off his face and Mark pulled out of his ass. Tyler felt sore and humiliated and completely used as he felt Keri’s juices dripping down his chin, cheeks and neck and Mark’s cum leaking from his ass.

“If you wanna do this again before you leave, just let me know,” Keri said as she fixed her dress while Mark put his clothes back on. “I’m sure Mark would be happy to join us for another round.”

“Absolutely,” Mark said as he pulled his shirt over his head and buttoned up his pants.

“If you really wanna have fun, use the cum leaking out of your ass as lube when you jerk off,” Keri said. “It will help you think of the fucking you just took while you have your orgasm, and I think we both know that’s exactly what you want to think about.”

Tyler watched them leave the room. He wasn’t going to do what Keri suggested while they were still there, but he was absolutely going to do it once she’d left. His head was still spinning with intense desire and he was going to see it through to the end and the beautiful orgasm that would follow.