A Load of Help Ch. 05

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Drunk and depressed his roommate knows how to cheer him up.
5.9k words
4.57
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Part 5 of the 5 part series

Updated 06/08/2023
Created 11/04/2017
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"Ugh!" Connor said as he sat down at the pub.

"What's up?" Tommy asked. "You act like you got something up your ass!"

Connor blushed, he didn't want to say that he really did have a butt-plug stuck up his ass. Which at the moment was making him very uncomfortable. Despite the loud music, he knew that almost forty-minutes before, he almost got fucked in the ass by his roommate.

Taking a deep breath he spoke. "I need a drink! Use your fake ID fatty and get us some beers!"

Tommy chuckled heartily, then collected some dollars to do just that. Connor looked across the room to see his roommate chatting up a blonde haired kid. He felt no jealously, if anything he felt relieved, it meant he could now focus on Elizabeth.

She hadn't arrived yet, but it didn't bother him, she was a free spirit. Tommy however returned with drinks and the party began quickly!

"Sup boys!" Called out Darterrius as he put his hand on Connor's knee for support as he got into his seat.

"Ah!" Connor cried out, for he instantly had an erection! "Fuckin watch out dude!"

Darterrius had either forgotten, or didn't care, he was already speaking to Tyreese about 'Rodney King'. Connor was shocked, Darterrius was a six foot tall... uh, really white black man, was how he'd describe the person next to him.

Aside from having no desire for dudes, he didn't much like Darterrius as a person... and yet he was rock hard from the brief touch. Connor felt confused, he chugged his beer hoping it'd clear his mind.

"Fool!" Tyreese shouted out, "It ain't the cops, or the jails that will make black men extinct!"

Connor rolled his eyes, then reached for the pitcher to top up his drink. Tyreese and Darterrius argued over the craziest shit, he thought they'd come to blows, and yet... they always still hung out.

"It's black women we need to worry about!" Cried out. "They abort more black people every year than Uncle Sam could ever dream of!"

Connor chugged the second beer, he needed to get away from this noise. Perhaps he could even get rid of the butt-plug which he could feel stretching his asshole wider than Darterrius' mouth.

"Where are you going?" Asked Tommy, as he put a hand on Connor's arm.

Connor leapt so high in the air, he swore that he almost launched himself into orbit! He had had gotten another erection when Tommy touched him! He mumbled something as he ran to the bathroom.

"Hurry back!" He cried out. "The DJ told me he's going to put on some better tunes!"

Connor crashed into the bathroom feeling like a wreck! If his sexuality were a compass, it was spinning! He splashed some water into his face hoping it'd help. Looking back in the mirror he felt better, but the confusion still tickled his tummy.

Feeling a tingle on his back, Connor ran his hand along his back. Unsure what it was, he pulled off his shirt and turned around. In the mirror he could see a hickey on his back! He didn't know who, where or how he got such a mark, his paranoia suddenly exploded again!

He heard some voices coming from outside the door, he quickly pulled on his shirt as several young men came in. One of them, was the blonde-hair boy that Anthony was chatting up.

"Sup." He said to Connor, who then made the same reply.

"I got a question for you." He said brushing a errand strand of hair from his face.

"Sure." Connor replied cautiously.

"Anthony, he's a solid fellow?" He asked.

Connor started sweating again, was this guy asking him if he was a good lover? He looked the kid before him up and down, he was thinner than Connor, with a rough edge about him. He didn't look gay, but than neither did Anthony?

Connor decided to play it safe as he spoke. "He always returned video games on time."

The blonde kid thought this over, smiled than slapped Connor on the arm as he spoke. "Good to hear. Hey if you need a hit, let me know."

When he touched Connor, it gave him the hardest erection yet! Connor swore that the head of his penis was coming out of the top of his pants! He couldn't breath; he was sure that the kid before him just hit on him!

"Sorry?" Connor mumbled.

"Yeah, if you need some weed, or something else..." He said with a wink. "Let your friends know."

With that the blonde haired kid slapped him on the arm again and turned to take a piss. The bathroom was full; Connor forgot about his butt-plug as he made his way back to his friends.

Once at the table, he hammered back a third glass, then belched. The boys cheered loudly, then returned to the debate about the upcoming Tyson-Hollyfield fight.

"Tyson will devour him out in 90 seconds!" Connor shouted.

Everyone exploded in noise at the same time. Tyreese leapt from his seat to speak loudest. "Hollyfield knocked him out last year! He'll cream that washed up goon!"

Connor started laughing, for the first time that night, he didn't have an erection! A brand rap song came on and Connor found himself swept onto the dance floor shaking his thing. Darterrius and Tyreese started a dance off, and the boys found themselves clapping along.

After a week of money problems, school work and... he couldn't forget all the sexual encounters he'd had with Anthony, Connor was glad to cut loose. When it was his turn to dance in the centre he did the robot which was greeted with cheers and jeers.

With all the jostling Connor was unable to keep his ragging boner under control. Eventually he gave up trying to rein it in, and fully embraced his sexual arousal, despite not having any real stimulation.

Mid-dance he looked around and saw Anthony with the blonde haired kid again. They were shaking hands; a red-headed Asian girl walked by them. He thought that was a weird combo, but he quickly forgot about that when a hand touched his arm.

"Huh?" Connor said, his erection growing another inch.

"Good to see you!" Yelled a voice in his ear.

Connor was pleasantly pleased to see Elizabeth. She was a short chubby girl with black hair worn loose. She wore a black dress unbuttoned low enough for her ample cleavage to show, over this she had a tanned coloured vest.

For the first time that night Connor was hard, and it felt good. She moved in for a kiss on the cheek; Connor presented the side of his face to her, however when she moved in he pivoted his head over and their lips met. When she didn't break the kiss, Connor pulled her in closer.

When they finally broke for air, she was blushing, his friends were cheering, and Tyreese was gone! Connor didn't care. In moments the two of them were grinding together and his flopping hard on was starting to pay off! Elizabeth cooed the first time he pressed his manhood against her, and didn't say a word of complaint afterwards.

When they sat down together, it was all laughs, Connor felt like the king of the world! His friends were listening to his jokes; and Elizabeth was hanging on his every word! She even had a hand on his knee, which aside from causing his dick to twitch, felt very good.

Tommy and Felicia were however were shooting daggers at him. Tommy of course was a just a jealous fat bastard; Felicia... well Connor had no clue.

A hand moved up his leg to cup his balls, it was Elizabeth, and he didn't try to move it.

She spoke quietly into his ear. "Let's get outta here."

Connor tried to play it cool, but the hand on his sack had him very distracted. "Uh, sure."

They deeply, he even managed to slip a hand into her vest, her tits were huge, and soft under his touch. He fondled her nipple quickly before she pulled away.

"You got any Mary-Jane?" She asked sucking on his ear lobe.

He could have fucked her right on the table, right in front of everyone! He however wiped the sweat from his brow.

"Nah, we don't need that." He said trying to sound cool. "I got something much better."

She gave his family jewels a light squeeze before replying. "I can see!"

They kissed again, this time he slipped his hand into her dress to pinch that nipple. It hardened under his touch, it all felt so good, so normal... so right.

"I have to go to the ladies room." She said into his ear. "Meet me outside."

Connor lost his breath as he pulled his hand out of her dress. She straightened up and left. When she was out of ear shot his friends exploded in joy! Darterrius slapped him on the back which left his dick twitching.

Oliver and Brain seemed happy for him, Tommy however shook his hand vigorously which made his hard cock flop about, while he did this he mouthed the words 'this ain't over yet.' Connor smiled back mouthing a 'bring it on!'

Connor walked across the dancefloor high on life, he saw Tyreese up on the Asian redhead chick and gave him a thumbs up. Tyreese didn't look in his direction, embarrassed he continued outside.

He leaned against a wall and watched people coming and going, hoping she'd be quick.

"Where's your date?" Asked a voice.

Connor turned to see Anthony standing alone, which prompted him to ask. "I could ask you the same."

"He's taking care of some business." Anthony replied. "I guess you get dibs on the room?"

Connor was surprised, he didn't think of that. "Uh yeah, I guess I do."

"Cool," Anthony said. "Make sure you put a coat hanger on the door nob."

Confused Connor asked. "Why?"

"That way I know you're still doing it!" Anthony said.

They both laughed and shook hands. Connor got another bonner, but he was used to it now. Anthony let his hand go and walked away.

"Don't forget!" Anthony called out. "Otherwise we'll have an orgy!"

Connor chuckled long after Anthony disappeared into the dark. After a few minutes he started to get nervous. Elizabeth was taking much too time, Connor was unsure if he should go back in?

"What cha waiting for?" Asked a female voice.

"Elizabeth?" Connor said in a panicked voice.

"Humpf, I should hope not!" Replied Felicia snootily.

"Oh?" Asked a confused Connor, "Did you see her?"

"What do you see in her?" Felicia asked.

Connor was perplexed, but he didn't want to have her around for when Elizabeth showed up.

"I dunno," He started to say, "She wants to fuck, and so do I. How's that?"

"Are you sure about that?" She asked with a smart-ass look on her face.

Connor was furious, he wanted to bend her over his knee and spank her until she explained herself. He would have too if he didn't still have an erection from shaking hands with Anthony.

"What's that supposed to mean?" He said trying not to show his anger.

"Well I think she's more interested in getting high." She said.

"Fuck!" Connor hissed. "I bet that fat bastard Tommy scored some for her too!"

Felicia spoke as she rubbed his arm, causing his dick to twitch some more. "Sorry to be the one to tell you."

He looked at her, she had the same 'fuck me' look that Elizabeth gave him just minutes before. It didn't make him feel any better, just more upset.

"I'll wait here and prove you wrong!" He said.

Felicia wondered off into the darkness, the faint smell of her perfume floating in the air. Connor knew Elizabeth was coming! He just knew it! She would come out, she just had too!

Connor lost track of time, it felt like an hour before he finally gave up. He would have stayed longer, but her heard the voices of his friends coming out, he couldn't bear the shame of them seeing him.

Wandering around aimlessly, Connor found himself back at his room. He reached for the nob when he felt a coat hanger stab his hand.

"Shit!" He said, however it was too late, the door was open.

He expected to see Anthony doing 'gay stuff' with the blonde haired kid. Unfortunately he knew too well what those things could be. Instead he saw Anthony sitting at his desk studying with a drink on the table.

"Uh, sorry dude." Connor said.

Anthony turned around equally tired and emotionally drained. Connor assumed that his friend got tricked as well.

"You want a drink?" Anthony asked.

"Fuck yeah!" Connor replied.

Within moments Anthony had a stiff drink for his friend, Connor smashed it back quickly and asked for another. The second drink he sipped as he told his tale. When he was done, Anthony spoke up.

"I feel for you dude." He said putting his hand on top of Connor's.

Connor felt his long forgotten erection returned instantly! He pulled his hands back, and hoped Anthony hadn't noticed that he was not only sexually frustrated, but that his little soldier was standing at attention.

Anthony stood up and paced as he spoke, sipping his drink. "We fooled around some, but his pager went off and he had to leave."

Connor made a polite smile, and didn't mention the lack of sex smell in the air. His roommate came up behind him and started to rub his shoulders, he tried to squirm away, but Anthony was some sort of spider that once it gets you in iitweb there was no escaping!

Anthony continued to rub his shoulders, but some how he managed to push down on Connor's shoulders causing his butt-plug to go deeper, if such a thing were possible. Uncomfortable should be the word to describe how he felt, however he'd experienced this dual pleasure before on both his cock and ass more than few times.

A mixed grunt of pleasure and relaxation escaped from Connor, he quickly covered his mouth. Anthony spoke softly as he rubbed his neck.

"It seems that we have the same problem." Anthony said rubbing Connor's spine.

Connor tried to concentrate, he felt drunk amongst his other ails; through the fog he caught Anthony's words. He didn't want to have sex, or did he? He was expecting to get laid, or at the minimum a blowjob, or even a handjob. Anthony could do that do that... he had before.

"You have a knot in your shoulder," Anthony said. "Let me work it out."

Connor suddenly felt the full weight of his problems, although he was hard, he just wanted sleep.

"Uh yeah, whatever." He said. "I'm going to lie down and get some rest, it's been a shitty night."

Anthony, true to his spider nature, never quite stopped him, nor did he let Connor go. When Connor laid down, Anthony straddled him with his hands under his shirt.

Connor felt more and more relaxed, he easily could have gone to sleep. Anthony shift his weight, causing his butt-plug to depress, it pushed him back into full consciousness, and made him all to aware of he need for sexual release.

Anthony could add slick to his list of talents, in moments he had Connor's shirt off, and was tugging at his friend's belt and trousers. All whilst this occurred Connor stammered excuses, he ran his hands up and down his body.

Connor found himself naked save a pair of socks, and trapped under his roommate. He felt a weird combination of both vulnerability, and comfort at the same time. Mostly this was due to the ever present piece of rubber lodged in his ass. He supposed he could yell and toss him off however he felt like a small mouse hypnotized by the snake the continued to wrap himself around him.

"What's this stud?" Anthony asked touching his shoulder blade.

Connor had a minor freak out as he rolled over and spoke harshly. "I don't know how I got it, but I bet you do!"

"It looks like my handiwork!" Anthony said with a chuckle, "Hey, thanks for rolling over, I can do your front now."

Connor felt like he'd been cheated or at least tricked, then he realized... "Dude! Where's your clothes!"

Anthony howled with loud laughter. "The best massages are done in the buff."

Connor chuckled too, he needed a good laugh. He noticed that Anthony wasn't hard, but it was growing. He wasn't smarter, or any stronger than his auburn haired roommate, but he did have him beat in the measurement department. Anthony a good inch or two shorter than him. Connor didn't want a poke in the bum, but if he did get one from Anthony he knew he wouldn't have to worry about his asshole being stretched out.

Anthony shifted lower on Connor's body to rub his chest. Connor could feel Anthony's ass hairs pressing down on his stiff cock; then he felt the butt-plug.

"You still have that thing in... your ass?" Connor asked.

"Yeah, I love the filled sensation it gives me!" Anthony said. "I see that you have yours in still?"

"I almost pulled it out, but someone came into the bathroom." Connor said.

They both chuckled at this before Connor continued. "I didn't want it in for when I fucked Elizabeth."

Anthony spoke between laughs. "Poor boy, that must explain why you've been aching."

Connor was going to mention that he'd had a boner almost non-stop since the larger butt-plug was pushed in, however he decided to keep that to himself.

"Consider me a good friend." Anthony said moving on the bed.

"Uh, sure." Connor said confused. "You did help me out when I needed some cash."

"I did." Anthony said standing up and turning around. "Let me relieve some pressure for you."

"You don't have too..." Connor started to say before. "Ah! Fuck!"

Anthony had laid down on his friend in a perfect 69! Connor wriggled as Anthony's growing wiener slapped his face. He went to push his roommate away until Anthony got his penis in his mouth, it had an almost magical calming affect upon him.

This was Connor's first 69, and it was not the way he imagined it. He turned his face sideways to get his roommate's nuts off his face, however the ended up on his ear. Escape crossed his mind wen he felt a hard cock on his cheek, but Anthony seemed to have locked him in a human jail using his legs, hands, and most importantly his mouth.

Anthony had his penis pointing straight up, and held it with one hand, licking it like an ice cream cone. When he placed it inside his mouth, it made Connor gasp loudly before going quiet.

"Dude, don't expect me to repay the favour!" Connor said amid the cock slaps he was receiving.

"Hmmmmm..." Was Anthony's reply.

The humming had a toxic affect on Connor, he could feel that his time was limited. He then realized that all he had to do was blow his load, then he could go to sleep!

"Dude, I'm going to cum soon if you keep that up!" Connor warned.

Anthony hummed longer and harder on Connor's mushroom cap, it was as if he wanted this over with just as quickly! Connor could almost start a mental count down to blast off when Anthony halted abruptly. He then felt something slide down his penis to the base, and then the same feeling around his testicles. This was followed by a tightening sensation.

"What the fuck dude, I'm about to cum!" Connor said whilst dick dodging.

Anthony had resumed his cock sucking, and stopped long enough for a breath and a quick comment. "Not yet you aren't!"

Connor felt like a volcano that rumbled and shook, but was unable to explode! He debated making grumbling noises, but with a face full of balls he didn't want speak unnecessarily.

What happened next was as equally odd, as Anthony pulled Connor's full six inches out of his mouth. The cool air on his sausage was a odd contrast from the warm mouth bathing it moments before. He then gripped Connor's body tightly.

"Hold on!" Anthony said as he started to roll.

Connor did as he was instructed as he found himself being pulled on top of his roommate. Propping himself up on knees and elbows, Connor was relieved at not having a dick slapping his face any more.

Anthony wasted little time after the flip, holding Connor in place with one hand, he then used the other to re-insert his friends cock into his mouth. Gurgles and gags filled the room as Anthony tried to ram Connor's cock into his throat.

Despite being on top, Connor still felt trapped, not only was he held in place by a squeezing hand on his hip, but he was also still unable to cum. His embarrassment was only equalled by his unreleasable pleasure! He struggled in vain as his roommate stopped stroking his cock and moved his hand to play with the butt-plug lodged in his ass.

"Ugh..." Connor moaned. "Stop doing that..."

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