A Load of Help Ch. 04

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His roommate takes advantage of him when he's vulnerable.
2.4k words
4.25
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Part 4 of the 5 part series

Updated 06/08/2023
Created 11/04/2017
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Connor closed his text book and exhaled deeply, he had just finished studying for his last mid-term test. He felt ready to exceed on the test, and that more study time would be pointless.

Standing he stretched his muscles, it was time to relax. He planned on meeting up with his friends for a night of beers and laughs; to forget his woes briefly before facing them all.

Counting his fingers he thought about them in order. First, he was broke, he wasn't getting the hours he needed at the campus coffee shop. Second, he didn't want to tell his parents how poor he was. Third, his roommate tried to help him, but it wasn't enough.

Anthony, his roommate gave him some money, however it came at a cost. For a fist full of cash Connor gave his friend what he craved the most... load after load of anal creampies! As a straight man it was a true chore! The money he received was not nearly enough!

That brought him to his fourth problem. Not only did Anthony want his cum, but he also expected Connor to 'help him' cum first. It started with a dry hump, but since then it had become a pain in the ass...

Connor wiggled his ass thinking about what was still parked in his bum. He knew that eventually it had to come out, but he didn't feel brave enough to do it.

Trying to clear his mind, Connor showered with the butt-plug still inserted. He then dressed in fresh clothes before heading to the vending machine, he needed a pop and chocolate bar to perk himself up.

"Whatcha doing?" Came a soft voice behind Connor as he put coins in the vending machine.

"Huh?" He said spinning around.

"Are you going to that party tonight?" Asked Felicia smiling.

She was a petite, girl next door type from Seattle that Connor made out with once. After that night she got all weird and avoided him, however a few weeks later she acted as if the were BFF's, always asking him intimate and random questions.

Connor wasn't sure how to reply the brown-eyed girl before him, before choosing honesty. "Yeah, I am. I have a sorta date with Elizabeth."

Felicia tried to hold back the disgust in her face, finally forcing a smile on those lips that Connor once kissed.

"She's a pot smoker isn't she?" She asked.

"Uh, I guess. Why?" Connor replied confused.

"No reason." Felicia said turning to walk away, "Bye-bye!"

Connor sipped his pop while watching her small hips sway as she walked away. He very much wanted to screw her, regardless of her hot and cold attitude.

Returning to his room, he saw Anthony still wearing his shirt and looking dishevelled.

"Sup." Connor said.

"Sup." His roommate replied looking up.

Connor took a seat at his desk and began tiding up his books and notes.

Anthony walked over to him, speaking as he brushed a stray strand of blonde hair blocking his face. "Hey man, I just wanted to say thanks for your help this week."

"Yeah, uh, no problemo dude." Connor replied.

"I really kicked ass with the loads you gave me." Anthony said.

"Really? It helped?" Connor asked.

"It sure did! I gives me such a clear mind for when it's game time!" Anthony stated emphatically.

"Wow!" Connor exclaimed, he then remembered the clarity he experienced during his tests after playing with his roommate.

Anthony met his gaze as he spoke. "Anyhow, I just wanted to say you're off the hook."

Connor looked perplexed, he knew Anthony had one more test tomorrow, just like he did.

Pulling a fistful of money from his pocket, Anthony handed it over to him. "Here's the cash I owed you from the last load."

Connor unfolded the bills to see he had more than enough to cover his rent, he could also have some drinks tonight!

"Thanks dude!" Connor said, unsure if he should give Anthony a high-five.

"Don't sweat it." Anthony said smiling. "I also found a stunt-cock to give me the last couple loads I need for tomorrow."

There was no jealousy in Connor, he was happy to put his Gay-Adventure behind him. The last thing he wanted was Anthony thinking they were friends with benefits.

"Dude that's awesome!" Connor said enthusiastically. "Is it Oliver?"

Anthony looked confused as he replied. "Huh, who? I mean, no... not him."

Connor missed the look on Anthony's face, as he was sharpening a pencil. "So who's the lucky fellow?"

Anthony walked over to where he kept his liquor, then started making some drinks. Aside from being quiet, it appeared as if he was keeping his back to him purposely, Connor didn't care, he had money, and was now free from any more ass-assaults, which reminded him...

"It's a guy from school, but he wants to keep it on the down low." Anthony said handing Connor a rum and coke.

Connor took a sip, then swore. "Shit man! That's strong!"

"It'll put hair on your chest dude!" Anthony said smiling.

Connor took a huge sip, caught his breath then spoke. "Dude, I need you to get that thing outta my ass!"

Anthony laughed heartily; Connor made a sour face, which set him laughing again. The two men finished their drinks and chatted for a bit, Anthony whipped up a second set of drinks then walked over to his bed.

"Pull down your pants, and bend over the bed stud. I'll take care of it for you." Anthony said setting his drink down.

Connor finished his second drink in one big gulp, he needed all the liquid courage he could find. In all his years he'd never had anything other than toilet paper so close to his asshole. He grabbed some pillows, which he laid on for support.

"You know, you could do this yourself." Anthony said calmly as he ran his hands down Connor's hips.

Connor could feel the goose bumps forming on his body, and although he didn't feel aroused, he noticed that his penis was growing very quickly!

"I didn't want to get shit all over the place." Connor said in a worried tone.

Anthony's hands glided across his friend's body, exploring his legs and ass cheeks. Finally with a hand on Connor's hip to hold him steady, he took a finger to depress the butt-plug.

"Unnnhhh..." Connor cooed, his penis rigid and oozing fluid.

Anthony released the pressed, waited, then pushed it again. The butt-plug was almost a joy button linked to Connor's pleasure centre.

"Stop that..." Connor pleaded weakly.

His roommate did anything but that, he slowly rotated the small piece of rubber lodged in his friends buttocks. Connor could not stop the moans of ecstasy that swept across him.

Connor wriggled his ass in hopes that he'd dislodge it amid the rotations, this had the opposite effect, causing further waves of arousal.

Anthony squeezed his hip as he spoke. "Hold still stud, I'm trying to pull it out."

He then pulled the plug an inch, then pushed it back in. Connor gasped loudly, to which Anthony replied with a swift slap to an ass cheek.

SLAP!

"What was that for?" Connor whined.

"I said hold still!" Anthony replied firmly.

Again Anthony pulled it out half way, then reinserted it fully. Connor groaned, but much quieter this time; he didn't know it, but his man fluid was making a snails trail on the side of the bed. After several movements in and out Anthony fully removed the object that had impaled his friend.

"Is my asshole ok?" A concerned Connor asked.

"What could be wrong with it?" Anthony challenged back.

"Is it... is my asshole stretched out?" Connor asked worriedly.

Anthony smiled an evil smile, then replied. "I'll check for you."

"Thanks dude!" Connor said relieved.

Connor's roommate moved forward, he wanted to inspect his friends anus thoroughly. First he pulled apart his ass cheeks, then placed his nose above the hole.

"What are you doing?" Connor tried to look over his shoulder as he spoke.

SLAP!

Anthony slapped his friend bum harder than before then spoke sternly. "Don't you dare questions my methods."

Connor wanted to laugh, here he was playing doctor with his roommate. "OK, ok, I'll stay quiet."

Having put Connor in his place, Anthony proceeded with his devious plan. Like Moses parting the red sea, he opened his friend's most sensitive area to exposed it. He then brought his head forward, but this time he shot out his tongue.

Connor squirmed then remembered his last slap and forced himself to stay still. His cock ached for attention, he couldn't remember the last time he was this so uncontrollably hard. When Anthony's tongue touched his anus, all he could do was grip the pillows tightly.

Anthony alternated his licks, starting with circles; then running his tongue from the bottom of Connor's crack straight up to the top. He repeated this many times before trying to jam his tongue as far as he could into his friend.

Under this anal onslaught, Connor grunted deeply; his roommates tongue was easier to bear than the object that was planted there earlier. He stifled a yelp when Anthony reached between his legs to pull his penis downwards. Nature did not intend for his pole to point that way, but that did not stop the man kneeling behind him!

The stroking and anal licks continued for what seemed like an eternity, Connor didn't want to cum so soon. He had plans for a date with Elizabeth, he wanted to blast her womb with jizz... not to leave a stain on Anthony's bedsheets. He didn't know how to ask his friend to stop, nor was he sure he wanted him to.

Once Anthony felt that Connor's surrender was complete did he temporarily halt his two pronged assault. Like any good pincer attack, it was all about timing. Reaching under the bed, he squirted a liberal amount of sexual lubricant into his hand.

"What are you doing back there?" Connor said before yelping!

SLAP!

Anthony's reply was a sharp and direct smack on his friend's bare ass. The blows he reined upon it had changed Connor's once pale white full moon ass to a reddening harvest moon.

It was times like this that Connor swore his roommate had three or more hands. In a very short period of time he felt a slap on his ass with a dry hand, then a slick, wet hand grasping his penis, which stroked it.

Anthony then smeared more of the cold fluid on Connor's asshole. Goosebumps appeared again across his body, Connor didn't know what to expect next, his fight or flight instincts were confused by the pleasure and anticipation he was feeling.

Anthony stood up, and pressed his body against him. Connor could feel his roommates leg hairs coming into contact with his, followed by cold skin pressing against his warm flesh. He inhaled deeply, he was both worried and very excited for what was to happen next.

When he felt the pressing against his tight knot of flesh that was his gateway to his bowels his breath left him completely. As if he were on the surface of Mars he couldn't breath.

Like the French army, his well lubricated anus put up only a token resistance before complete surrender to the invader. He could feel his sphincter dilating to receive it's new guest. Despite the lack of oxygen he wondered why he felt only pleasure and not pain as he took inch after inch inside himself.

After what felt like an eternity Connor could feel Anthony's pubes against his ass cheeks, and something else poking into his testicles. He took a shallow breath, exhaled, then took another.

"How is that?" Asked Anthony.

"Uh, it's ok, but its bigger than what was in there earlier." Connor replied.

KNOCK KNOCK KNOCK

Connor didn't hear the noise, he was in his own world as he adjusted to the visitor in his ass. It felt bearable, it felt good! He felt Anthony stroking him again, which felt very good as well!

KNOCK KNOCK KNOCK

This time Connor thought he heard something through the fog of joy. The banging on the door was a like a distant storm, something he should be concerned about while he was bent over a bed with his roommate behind him.

"Come on you faggots!" Called a loud and deep voice, "Get your dicks out of each other's mouths and open the door!!"

At that Anthony stepped away from Connor. Spinning around to look at the closed door; Connor was thoroughly confused! Anthony had his pants down around his ankles, just like he did, however he still had something in his ass! It wasn't Anthony balls deep in him, but... something else?

"What's inside me?" A panicked Connor asked standing with an aching erection.

"It's another butt-plug, it's bigger than I am!" Anthony said doing up his belt. "Now get dressed, I'm opening the door!"

Connor had mere moments to pull up his pants, he could now make out the voices of his friends outside the door. They were laughing loudly as they banged away.

Anthony opened the door to their room; Connor was relieved that he was now fully dressed, but his hair was a mess.

"What took you homos so long?" Chirped Tommy.

Anthony looked at Connor who was fixing his hair, then got an idea. "I shot a load in his hair, and he got fussy about it.

Everyone laughed, after a moment Connor did too, it was all he could do amid the sexual tension! Tommy poured himself a drink then joined Connor by the mirror to prune his own hair.

"Did you get it all out?" Tommy said laughing.

"At least I got hair!" Connor said taking Tommy's drink and having a sip.

Tommy blushed, his hair-line was indeed starting to retreat. Connor gave him back his drink which he slugged back in one gulp. After a loud burp he started to laugh too.

"Come on guys!" Tyreese stated loudly, "Let's go party!"

The group of men cheered loudly at this. Connor fixed his pants one last time, the butt-plug tickled his insides with each step, send pleasure throughout his body. He remembered that he had a date with Elizabeth, but wasn't sure when, how, or even where he'd pull that object out of himself!

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