Adventures of a Craigslist Whore

By Joe Whitfield

Published on Jul 7, 2024

Gay

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This is the first story I've written about my adventures as a craigslist whore. I am wanting to put a book together from the many stories I have. But this encounter was probably one of the most memorable. It is a true story, slightly embellished for readability.This is my first effort, hopefully someone will provide feedback.

Adventures of a Craigslist Whore

Jesse slid off of the bed and wobbled toward the motel toilet as the pain seared through his rectum with blood and semen oozing down his hamstrings. He glanced into the mirror and noticed his mussed gingery blonde hair before his eyes opened wide when saw the dark bruise along his left jaw and a purple hickey on his neck just below the bruise. He rubbed the hickey and softly touched his bruised face as he recalled what had just happened.

"How am I gonna explain this at work in the morning," Jesse thought. "Gonna make a lot of sales looking like this," he told himself sarcastically.

Around midnight, Jesse had given up on more sex and snuggled up in his bed at the Super 8 motel in Macon, Georgia. He had spent most of the night answering emails from men who answered his craigslist sex ad. Five hours of emails led to two quick encounters with anonymous men and that was a little disappointing. That was a pretty regular night for Jesse, especially when he moved into a new town. Macon was a regular stop for Jesse with his work and he did have a couple of regulars that would visit each time he came into town.

But this was not regular. The telephone jarred him awake around two in the morning. The phone display read unknown number, but Jesse was intrigued. He answered and heard "You still up?," the caller asked. "I am now," Jesse responded with a yawn. "I'm gone fuck you now, be there in a minute."

Jesse tried to remember who he was talking to. It was obviously someone who he had been interested in and had actually given the guy his phone number and location. It was definitely a black man but most of those who answered the ads in Macon were black. It could have been one of several of men he had flirted with online. He couldn't remember much about the guy he actually sent his location and phone number. There were a couple he thought was coming earlier, but never showed. This is obviously one of those guys.

Anxiousness swept over Jesse as the visitor knocked on the door four times. He tried to look out the widow without disturbing the curtains to get a look at the man but he could not see him. He then peaked through the peep hole and saw an attractive bald black man that looked mid-thirties, maybe fortyish. When he opened the door Jesse first saw biceps that strained the man's long-sleeve button down. The buttons holding the shirt together also strained by the bulk of the man's pecs. A short beard covered the man's milk chocolate complexion. His skin-tight jeans stretched over huge thighs and a obvious bulge in the middle showed the visitor was ready to have some fun. He was slightly taller than Jesse's 5'10 frame and in much better physical shape than Jesse's middle-aged, overweight condition.

Jesse's anxiousness vanished as he welcomed the handsome man into his room.

"I'm Jesse, what's your name?," asked Jesse. "Hawk," the confident black man said as Jesse recognized the smell of whiskey from the man's breath as he spoke. Jesse moved to unbutton the stud's shirt, but he pushed Jesse's hand away roughly.

"Get naked and get in da bed," the man said gruffly. "This ain't no romantic thang bitch. I'm gone get get my dick off. That's all."

Jesse smiled nervously and pulled his t-shirt over his head before pushing his briefs to the floor. He stepped out of the briefs and crawled back into the bed. The truth be told, Jesse liked a man that was in charge and took control of the encounter, but it still made Jesse a little edgy.

He watched as Hawk took of his shirt to reveal a dingy white wife-beater t-shirt underneath that was stretched to its max and it's length was not enough to hide a firm, flat stomach covered in a black hair that disappeared into the man's sky blue boxer briefs. As Jesse's eyes focused on every move, Hawk shimmied out of the tight jeans to reveal those huge muscular thighs and a massive protrusion from his crotch. When Hawk turned around to put his jeans on the nearby chair, Jesse got a quick look at a near-perfect backside.

"Damn," thought Jesse as he licked his lips. "How did I get so lucky tonight?"

Before he could answer his own thoughts, Hawk moved into the bed next to Jesse and pushed Jesse's head into his boxer briefs and pushed him as deep as he could with a firm strong hand on Jesse's neck.

"That's what you want ain't it bitch?," Hawk growled. "That's good, ' cause what I need is a whore to use."

Jesse squirmed under Hawk's firm hands as he tried to pull away with little success. Hawk quickly flipped Jesse onto his back and jumped on top of Jesse, straddling Jesse with his knees just under Jesse's arm pits. Jesse opened his eyes to see the stunning black stud towering over him with Hawk's massive member stretching past the band of his boxer briefs and up to his stomach.

Hawk moved even closer and leaned onto the headboard and began rubbing his penis all over Jesse's face. Jesse held onto Hawk's tree-trunk like thighs as he tried to breathe with Hawk's body pressing into his face. He squirmed underneath the muscular hunk, but there was no way to get up and Jesse really didn't want to.

The encounter continued with little resistance from Jesse as Hawk continued to do whatever he wanted and Jesse complied willingly. But as the rendezvous continued, Jesse began to get concerned about the size of Hawk's penis and it penetrating Jesse's backside.

"Hey, listen," Jesse said quietly, "You know I want to make you happy, but there is no way I can take that thing. It is just way too big to go inside me."

"Shut the fuck up," Hawk said as he smacked Jesse's bare ass hard. "You emailed me all night about how you wanted my dick and here it is. You ain't backing out now."

"I really can't," Jesse said with a little whine. "I've never taken anything like that, ever. I'll do whatever else you want, but I just won't be able to handle that."

"Oh, you gone take it," Hawk said. "Whether you can handle it or not, you gone take it."

Jesse pulled away from Hawk and got out of the bed.

"I think you need to leave," Jesse told Hawk as he looked for his t-shirt and briefs. "I enjoyed our time together, but I can't do any more. I need to get some sleep because I have to be at work at eight."

As Jesse bent over to put his underwear on, Hawk grabbed Jesse and pushed him face down onto the bed.

"You ain't done til I say you done," Hawk said. "Stupid old bitch, shut the fuck up now before you get hurt worse than just a good fuck."

Jesse pulled back and tried to get away before Hawk landed a solid punch to Jesse's left jaw. Jesse fell back onto the bed but Hawk grabbed him by his hair and pulled him up to his feet. Jesse pushed at Hawk's massive chest to try and get away, but Hawk was much too strong and determined.

As he held Jesse by the hair, he landed three more hard slaps across Jesse's face.

"Don't fuck with me bitch," Hawk growled. "I came here to fuck and that is what I'm gone do. You can do what you posed to do and enjoy it or not. I don't care if you like it or not, but I'm taking that ass and there ain't nothin you can say or do that is gone stop me. Get on your fat ass stomach now."

Jesse climbed back into the bed. He rubbed his really sore jaw and then noticed his bottle of poppers and thought that might help him escape some of the pain that was about to come his way.

Jesse laid on his stomach and felt Hawk climb on top of him. Jesse opened the bottle and held it up to his left nostril and inhaled deeply. Soon his head began to swim as inhaled through his right nostril as Hawk pushed Jesse's face back into the mattress. Jesse felt the weight of Hawk's body on top of him and his huge penis sliding on his ass, but the poppers had Jesse's head on cloud nine.

Jesse came back to reality as Hawk pushed his monster penis into Jesse and Jesse screamed.

"AAAAAAY, I can't! I can't. Please, I can't. Please," Jesse pleaded. "It's too much. Oooouuu! Please don't."

Hawk put his hand over Jesse's mouth and pushed deeper into Jesse.

"Shut up, whore. This is what you wanted and you know it."

Tears began to swell into Jesse's eyes as Hawk firmly held Jesse in place and began to move in and out of Jesse. The searing pain of assault on his anus was not easing at all as Hawk began to thrust harder and harder with each movement.

"Take it bitch," Hawk growled as he thrust in and out. "This is what whores like you live for. I'm a real man taking your ass and you lovin it. I got you like I want. Ain't nothin you can do but what I tell you."

After several minutes on his stomach, Hawk pulled out and flipped Jesse onto his back. He pushed Jesse's legs back over his head and pushed into Jesse again. Hawk's face was only inches from Jesse's and he could see the pain in Jesse's face as tears rolled down his cheeks.

"Aww the little bitch is cryin," Hawk said. "Here, daddy gone kiss it and make it better."

With that Hawk landed his mouth right on top of Jesse's lips and Hawk's tongue started exploring Jesse's mouth. Soon he pulled away from Jesse's lips and his mouth latched onto Jesse's neck and began sucking hard and biting as he continued to slam into Jesse's ass.

"Oh god this is good," Hawk blurted. "This tight ass feels so good. I'm gone leave something inside you to always remember. Damn, damn, damn...ahhhh."

Hawk collapsed fully onto Jesse. He laid there panting heavily with his face next to Jesse's tear-stained face. Jesse could feel Hawk's breath slowing slightly as the two men laid there, one in satisfaction, one in pain.

As Jesse began to squirm to get out from underneath Hawk, Jesse felt Hawk's withdrawing penis leave his ass. He tried to get up, but Jesse held him there.

"Not yet," Hawk said. "Just lay there and be still for a minute. Just enjoy the moment with this man on you."

Moments later and without a word, Hawk rolled off of Jesse and stood up. He pulled on his sky blue boxer briefs, crawled into his jeans and slid on his shoes. He grabbed his shirt, looked back at Jesse still on the bed and walked out of the motel room as he put his shirt on. The door slammed and Jesse rolled to his left side and took a deep breath and released it. He did that several times as he tried to get his wits together to go clean up and take a shower.

Every muscle in his body ached as Jesse moved toward the sink. He looked back at the bed to see blood stains and wet spots on the right side of the bed where he had been with Hawk. Fortunately the left side of the king size bed was still clean and he could crawl back in for a couple of hours of sleep before heading into work.

Jesse edged his way into a hot shower and let the water run over him as he braced himself on the wall to stand up. He lifted his eyes to the shower head and let the water hit him directly into his face and opened his mouth to try and rinse the taste of blood out of his mouth. After he stood in the hot water for a good 20 minutes or so, he grabbed the soap and a cloth to wash. His body was sore as he moved the cloth across his chest and stomach, but the real pain came when he applied the soapy cloth to his ripped anus.

"Aaaaaah, DAMN!," Jesse blurted. "I've never been in so much pain like this," he thought. "My craigslist days are done. Only people I know from now on. I can't do this. He was sexy but it's not worth all of this."

After the hot shower he poured himself a drink with Diet Coke and Jack Daniels in hopes that is would help him get to sleep a little sooner. His mind was racing over the events of the last couple of hours. It was now a little after four and he needed to be at work at eight. But Jesse could not stop thinking about Hawk and what he said. He remembered Hawk saying "I'm gone leave something inside of you to always remember me." What did that mean? Was it just his semen? Did he have a disease? HIV?

Jesse laid down but tossed and turned remembering his encounter with Hawk. He decided he definitely needed to go get tested and he definitely needed to change hotels in case Hawk decided to come back. He wondered what people at work would say about his bruise and the hickey on his neck. What would he tell them? How would he explain. He got up and made a second drink.

The alarm startled Jesse awake at seven. He rolled over to get up and pain shot through his lower back and rectum. He slowly reached the edge of the bed and sat up and put his feet on the cold fake hardwood flooring of the motel room. He reached over to turn up the heat and the pain in his back reared again. As he stood he stumbled, lost his balance and his knees hit the hard floor. He caught himself on the chair next to the bed and kept himself from hitting his face on the heating until by the motel window.

"This is not going to be a good day," Jesse thought as he tried to get off of the floor. "I can't even stand up right now, how am I supposed to do anything?"

Jesse's body had tightened up during the two and half hours of sleep after Hawk stretched him every different way during their sexual tryst. He was paying the price now. He pushed himself up onto the chair and sat there, contemplating how to make things work. When he sat on the chair he felt moistness underneath him and reached back to find blood. His anus was bleeding again.

"Great, just great," Jesse murmured to himself. "Now I have a bruised face, a hickey on my neck and it will look like I'm on my period if I bleed during the day. I can't do it. I just gotta call out today. I can't work like this. I just can't. There goes several hundred dollars. Damn, Jesse you're an idiot."

He called the office and left a message with his boss that he would not be at work and slumped back into the bed.

"Housekeeping," and heavy door-knocking shook Jesse awake around nine a.m.

"I'm still here," Jesse shouted at the door. "I'll be out later."

He heard the motel cleaning cart roll down the sidewalk as he settled back into the warm sheets of the bed. He knew he needed to get up and figure out what was next, but his body was not hurting at that moment so he stayed as still as possible and drifted back to sleep.

A loud knock his door woke again a little later.

"I told you I would be out later. Come back later," Jesse shouted. But the knocking continued and Jesse rolled out of the bed to go give the housekeeping person a piece of his mind. He busted open the door to shout at her and saw Hawk.

"What the hell?" Jesse shouted.

Hawks busted through the door and grabbed Jesse's left arm. He shut the motel room door and locked the deadbolt.

"Why are you here?" Jesse cried as the smell of marijuana filled the room."What do you want?"

"That ass was so good, I gotta get another hit," smiled Hawk. "You say you don't want it, but I know you do," he laughed.

Hawk slammed Jesse onto the bed and took off his briefs with his right hand while holding Jesse down on the bed with his left. Jesse was bent over at the waist with his torso and face on the bed and his ass in full view for his aggressor. Hawk kicked Jesse's feet apart and bent down and whispered into Jesse's left ear "Your favorite stud is back, bitch. Did you miss me?"

"No, please, no," Jesse whined as he grabbed the slim cheap motel pillow. "It already hurts too much from last time. You will kill me if you try again."

Hawk leaned over and pushed his still clothed body onto Jesse and humped him repeatedly. Hawk noticed the poppers on the night stand and took a strong sniff up each nostril before putting the battle in front of Jesse. Jesse picked up the bottle and inhaled deeply in his left nostril and then his right. He felt Hawk rubbing lube into his ass as his head began to spin. He hit the poppers again on each side, knowing that it wouldn't really help with what was about to come.

Hawk grabbed Jesse by his hair and pulled his head up before pushing into Jesse's already battered ass. After he pushed inside Hawk took his other hand to cover Jesse's mouth to mute the scream.

"Shut up cunt," Hawk said. "Just do your damn job, shut the fuck up and take it. That's all you're good for anyway. This is what you live for. You dream about this every minute of the day and now you gone whine about it. Shut up."

Hawk released Jesse's hair and landed a stinging slap on Jesse's milky-white backside. He landed another and then another as he thrust in and out of Jesse. Jesse began to feel the sting on his ass just as much as the pain inside as Hawk continued to ride him.

"Just putting a little color in that pale white ass of yours," sneered Hawk. "Gotta make it good and pink" as he landed another series of smacks.

Moments later Hawk began to tremble and grabbed Jesse by his hips and slammed harder and harder into Jesse. His motions were moving faster and faster until he began to moan violently.

Jesse felt his rectum being covered with semen as Hawk climaxed in Jesse again. Hawks slammed in again and then fell on top of Jesse as he fought to catch his breath. Jesse laid there underneath Hawk and waited for Hawk to let him go. With their faces right next to each other, Hawk began to tongue Jesse's ear.

"Damn bitch, that's what I'm talkin about," Hawk whispered. "My dick sure likes your ass. Can't wait to get in there again."

Jesse cringed at the thought and promised himself he would get out before Hawk had the chance to come back. He would change his number and remember details of their online conversations to make sure he never made that mistake with Hawk again.

Slowly Hawk pulled himself off of Jesse pulled up his jeans and walked out the door as Jesse still laid bent across the bed. Gingerly he rolled over to try and stand up and his ass hit the floor. He pushed himself back up to side of the bed and stood holding onto the bed. Gradually he began to edge toward the bathroom again and saw himself in the motel bathroom mirror.

"At least he didn't punch me this time," Jesse thought to himself. "And he didn't create more hickeys or force his tongue down my throat. At least that part was better."

Jesse made his way to the bathroom and got back into the shower. He knew he had to move quickly though because housekeeping would be knocking on the door again shortly and he had to get out of this motel and find a new one. He definitely did not want to be in that room again if Hawk came knocking.

Jesse cleaned up as quickly as he could, moaning and groaning with each movement but he did keep moving. He was putting the last of his personal items into his suitcase when he heard "Housekeeping," and a knock on the door.

"I'm out," Jesse said as he grabbed his bag and walked out of the room, hoping he didn't forget anything. He knew the housekeeper would be wondering what happened with blood and other bodily fluids in the bed. He wanted to get away as quickly as possible to avoid any conversation about what took place.

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