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Two Friends Try and Win a Bet

Two Friends Try and Win a Bet

by Sucuoff08
19 min read
4.75 (4300 views)
first timeconvincedstraight tricedbetstraight friends
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Writers note: This is my first story. I might do a second part. I would love feedback. I hope you enjoy.

Two friends try to win a bet

Reggie was searching for a house in the city. He wanted to escape his parents apartment. He had answered an ad that was looking for a roommate. Reggie showed up and Dustin opened the door. Dustin was in his mid-thirties, blue eyes, brown curly hair, pretty face, thick in the waist, just kinda thick everywhere and 6 ft. Nothing exciting, but nothing disgusting. Dustin was excited to greet Reggie and show him around.

It was a ranch house that basically had two sides. There was a master suite that Dustin had, an open concept living room into a kitchen and on the other side was two bedrooms and a bathroom. Dustin was renting one of those rooms. Better yet, he was renting it cheap.

Dustin went through the tour then stopped and asked Reggie, " I know we are going to be roommates, you are ok with me being gay right?"

Reggie was 22, black, wore twists in his hair at the moment, thin and not nearly as many muscles as he would like and 5'10. Reggie thought this guys house was too put together to be straight. Reggie replied, "Well, I'm straight, as long as that isn't going to be a problem."

Dustin smiled, "No, problem at all. I am mostly just renting to help other people and help me save for some vacations. Rent is 400 a month and due on the third. You would get the bedroom and guest bath and we share the living space. I ask that you don't have girls stay more than a night. I don't like girlfriend drama. Any questions?"

400 dollars is the cheapest rent that Reggie had seen in the city. He could cover that and maybe save up to get something better. "Everything sounds good to me."

Dustin smiled again, "Awesome, look forward to you moving in roomie."

The first month went pretty well, Reggie and Dustin got along. They had to have a few discussions about noise, Reggie played his music too loud and Dustin was a little too loud when it came to his alone time. Dustin apologized and was embarrassed because he thought the walls were thicker.

Everything was going great. Reggie asked Dustin if he could have some friends over on Friday for a get together. Dustin said he didn't care, but he was responsible for his friends' messes. Reggie was excited. None of his friends had places away from their parents. He could have them over for some smoke, drinks, and good times. They haven't had a chance to hang out for a while.

Reggie invited Jamal, Marcus, and Miguel over to hang. The guys hung out, smoked, talked about work, Miguel complained about his girlfriend, Marcus complained he couldn't get a girl, and Jamal complained that he needed more money to even date a girl. This catch up was needed and Reggie was happy he could hang with his boys again.

About 11 pm, Dustin came back home, he had a show he saw; some live musical thing that seemed boring to Reggie. He claimed he would make Reggie enjoy musicals, but Reggie wasn't convinced.

Dustin asked how the night had been going and the guys said it had been a good night. Dustin said that he was going to go to bed, He went to his room and shut the door.

Jamal turned to Reggie and asked, "So what's it like living with a gay dude?"

Reggie said, "What do you mean?"

Jamal said, "You know what I mean! Does he like hit on you and stuff?"

"No." Reggie replied.

"He hasn't really said anything like that to me. It's basically just like living with guys, except he's a lot cleaner. He listens to old corny music. He has had some guys over, I'll just say it sounds like they had fun. That was a little weird at first, but I'm sure he thinks the same thing when I bring a girl back here."

" Have you brought a girl back here? I didn't think they liked stick boys." Marcus said. The guys laughed.

"This is the only stick they care about." Reggie said, grabbing his dick.

The other boys laughed.

The next day, Dustin asked how his friends were. Reggie said, they were good.

"That Marcus was really cute. I'll keep my hands off, but I can't promise not to stare." Dustin said.

Reggie laughed. It was not the first time someone had said something about Marcus. Marcus was 23 light-skinned, wore his hair short and always looked like he just left the barber. He was skinny like Reggie, but Marcus had a six pack and some cuts around his muscles that Reggie never seemed to get.

It was about a month later, and what a month it was. Not only did Reggie's alternator go out on his car, but he stopped seeing Lydia, the girl he had been seeing, and he had to replace his phone after he dropped his and it landed on a rock and broke. It was an expensive March, and he didn't get paid for another week. He was starting to stress out a bit, because he didn't know if he was going to be able to pay his rent on time. He didn't want to mess with Dustin and lose his house. It has been great living with Dustin... and cheap.

That Friday was the 2nd of April and he still didn't know what he was going to do about the late rent. He was going to have to talk to Dustin. Marcus had come over and brought some drinks to help solve the problem. He was close and had 300 to pay, but didn't know what he was going to do about the other hundred or money until he got paid. He would have to look at a payday loan or something.

Dustin came back from seeing a movie and greeted the boys. He asked if they minded if he joined them for a minute. They told him to sit and chill with them. They were sitting on the couch watching music videos and chatting. They had a little bit to drink, but had not tied one on.

Small talk was continuing, but then Reggie heard Marcus say something that made him want to hit him.

"Hey Dustin, I know you have this house and everything and you are making money. Is there any chance you could let Reggie slide on the rent this month? He is stressing because he doesn't have it."

Reggie glared at Marcus.

Dustin turned to Reggie, "Is this true?"

"I was planning on going and getting a loan or something tomorrow to pay you. I want to pay you, I like living here. I just had a tough time with the car and phone this month."

"It shouldn't be too big of a problem, but I am going to charge you the 5 dollars a day late fee. Just to make sure we keep it paid."

Reggie sighed and said, that's fine.

"That's bullshit." Marcus said.

Both Reggie and Dustin turned to Marcus.

"Sorry, I just think that it's bullshit that he has to pay more because of him being a little late. You have the money, why not just let him work off the difference or something."

Dustin glared at Marcus, " This is what we have in our lease and I am just making sure that we are following the lease to protect both of us."

"Both of us?" Reggie asked.

"Yes, both of us," Dustin said. The lease makes sure that you have a place to stay and I get paid. It also makes sure I don't ask you to do any ridiculous things.

"What kind of ridiculous things?" Marcus asked.

"You know landlords have asked tenants for sex and things to not pay the rent, this is so I can't offer to... I don't know, watch... you two get each other off in exchange for rent." I have seen weird stuff happen in situations with no leases.

"I don't know, that sounds like a pretty good deal to not pay rent." Marcus looked at me smiling.

"What does?" Reggie asked.

"Getting off instead of paying rent, I would rather have that deal." Marcus smiled.

"Oh really," Dustin said with a glimpse of mischievousness in his eye.

"You couldn't do it anyway." Dustin said. " You are both straight and it's not easy to get another guy off when you're not into it." Dustin said challengingly.

"It wouldn't be that hard," Marcus argued.

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Dustin had a look in his eye that Reggie hadn't seen before. It made him nervous. He was also nervous about what Marcus was saying. He felt like he was getting roped into something that he did not agree to.

"Tell you what, if it's so easy. Let's do it. If you two can get each other off, I won't make Reggie pay rent this month and I will pay you both 100.00."

Marcus and I looked at each other in shock. I don't think that Marcus knew that Dustin was going to double down like this. He got himself together. "What happens if we don't do it?"

"Nothing." Dustin said, "We follow the lease...as I suggested. Honestly if you do try and do it and I get to watch, that will be all the reward I need."

Marcus pulled me aside. "What do you think Reggie?"

"I don't know how to get a guy off Marcus! Do you?" Reggie asked.

"I mean it must be like getting yourself off right?" Marcus said, hesitantly.

Marcus turned to Dustin, "What do you mean by get each other off?"

Dustin smiled, " You can't touch your own dicks at all. It has to be touched by the other person. You can use whatever on your body you want to get the other person off." Dustin grinned even bigger. "Actually let's add this rule, you can only touch your dick if the other person's tongue or dick is on your hole. That is the only exception."

Marcus turned back to Reggie. "I don't know, I could use the money and this seems pretty easy."

Reggie didn't know what to think. One of his best friends was talking about getting him off and solving his financial problems. It seemed easy, but Dustin was still smiling and that worried him.

" I think we should do it, at least try. I could use the money. Hold on. " Marcus turned to Dustin, "We accept your terms, but only if you up it from 100 to 150 a piece.

Dustin smiled, "Deal."

Marcus shook his hand, "Deal."

Reggie didn't know what was going on or how he suddenly got in on this crazy bet, but it was too late to back out now.

Marcus looked at Reggie. "Do you have some porn to help us get through this?"

Reggie told him he did, they finally found something they both liked with some cute mixed girl sucking dick and getting fucked by two guys.

They started the porn then just sat on the couch.

Dustin had sat in the chair on the side of the room. He wasn't watching the porn. He was watching Reggie and Marcus.

Finally Marcus said, "Come on Reggie, let's get started. Take your clothes off."

Both Reggie and Marcus started taking their clothes off. Both guys were down to their boxers.

"On three" Marcus said, " one, two, three."

Both guys pulled down their pants. It was the first time either of the boys had seen each other's dicks.

Marcus' dick was slightly swollen average width and was about 8 when he was hard. It was impressive, but not as impressive as Reggie's. Reggie's dick was about an inch longer, much darker, and had more girth than Marcus'.

"Damn Reggie, you weren't kidding about that big stick." Marcus said.

Reggie said, "Thanks" flustered by the compliment and the situation.

Dustin was smiling and leaned back in his chair. His dick had started to grow in his pants. He was clearly enjoying the show.

Marcus took a step toward Reggie. "Ok, let's just start by jerking each other off, maybe that will work and it will be quick." He said hoping.

Reggie felt nervous, he had never had another guys dick in his hand, only his own. He had also never had his dick in another guy's hand.

Both Reggie and Marcus reached out. Apprehensively. Marcus loosely grabbed Reggies dick, which started to spring to life. This shocked Reggie. He didn't expect his friend grabbing his dick to get a rise out of him.

Reggie reached over and started to grab Marcus' dick. Marcus dick also sprung to attention.

"Let's just do this and watch the screen. We should be able to get off pretty quick." Marcus said.

The boys started stroking each other, their eyes. Glued to the screen.

Both boys had each other 's hard dicks in their hands. They were both hard, but they both started to realize neither of them were close to cumming.

Marcus looked at Reggie, "I don't think I am going to be able to cum this way. "

"Me neither." Reggie said, disappointed.

Dustin looked at the boys, "Told you it would be harder than you thought.

"What is the rule about us touching ourselves?" Marcus asked.

"You can touch your dick if another person is licking or rubbing their dick on your hole. " Dustin said smugly.

"So if I let you eat my ass, I could jerk off?" Marcus asked.

Dustin looked flustered for a second, he didn't expect the guys to ask him to participate.

" I mean, yes." Now wondering if he was going to get the opportunity to touch the hot straight boy.

"Ok, what happens if only one of us get off?" Marcus asked.

Dustin thought a minute. "Well I think that would be half of the bet, so You would get half the reward." Reggie's rent would be cut in half this month and whoever gets off gets the $150.

Marcus let go of Reggie's dick and stood up.

"Bet. Dustin, you want to eat my ass?" Marcus asked.

Dustin thought about it for a moment. " Tell you what, I will do it. But only for five minutes. I don't want to ruin the process of the bet."

Marcus put his knees on the couch and bent over. He looked at Reggie. "You owe me for this." Reggie was sitting on the couch next to him awestruck. He was about to watch one of his best friends get his ass ate by his roommate right next to him. Reggie was sitting there with his dick still hard. He didn't t know why he started to think this was hot.

"Are you ready?" Dustin asked.

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"Just do it," Marcus said, determined.

"Time starts now." Dustin said then his face dove into Marcus' butt.

"Oh... shit" Marcus said as Dustin's tongue made first impact against his hole. He grabbed the back of the couch trying to become used to the new sensation.

Reggie watched with his mouth open wide. Dustin must have really enjoyed doing this.

Marcus reached under himself and started to stroke his dick. Reggie wanted to stroke his as well, but knew it was against the rules.

"Can I stroke mine as well?" He asked.

Dustin moved away from Marcus hole and looked at Reggie. "No, but if you want I could stroke you while I do this."

"That's fine," Reggie said. I mean, at this point why not. Every line had already been crossed and Reggie was turned on from hearing Marcus' moans as Dustin at his ass.

Dustin was going to town on Marcus' ass and stroking Reggie's dick. You could tell Dustin knew how to make a guy happy, because it felt so much better than when Marcus had a hold of it.

Dustin took his face out of Marcus' ass and looked up at Reggie. "Reggie, go get the lube from my table and bring it in here. "

Reggie listened to him and walked into the bedroom and came back with the red bottle. When he came back in, Marcus was saying. "Fuck yeah, eat that ass, lick my balls"

He then noticed that Dustin was switching between eating his ass and moving down to Marcus' dick.

When Dustin moved down to the balls, Reggie looked and saw Marcus' hole for the first time. He saw it was basically hairless and was just a few shades lighter than Marcus' honey skin. It looked like it was also starting to get relaxed and letting Dustin in to explore

"Pour some on my hand please." Dustin asked

Reggie poured some on his hand, it came out quicker than he expected and started to overflow.

"Oh shit" Reggie said, noticing a spot on the floor.

"Don't worry, a little Dawn will clean that up later. " Dustin said and went back to work on Marcus who was panting and clearly loving this new feeling.

Then Dustin reached up and started stroking Reggie's dick again. Only this time it felt even better. The lube had added a slickness that made the handjob even better. Now Reggie is starting to get into it.

He looked up at the screen, to see the mixed girl getting pounded in the ass by one of the guys. He had almost forgotten the porn was on. He watched. He switched between the TV and the girl getting pounded and looking down and seeing his friend with his ass in the air.

All the sudden, a small beeping noise started going off. Dustin stopped what he was doing and stood up, "Well, that was five minutes."

Reggie was rock hard and felt like he was close to busting. He just needed a little more.

"No way that was five minutes!" Marcus argued "Just a little more, I'm about to bust. It felt good, your tongue in my ass."

"Nope, you two are supposed to get each other off." Dustin said and sat back on the couch.

"Can you eat me Reggie, I'm so close to winning this bet." Marcus asked pleadingly

"I'm not putting my tongue on your butt Marcus." Reggie said sternly.

"Just rub your dick on his ass and hump him. That would solve both your problems. " Dustin suggested

Marcus and Reggie looked at each other. Each one seeing if the other would object. Finally Marcus said, " Fuck it, just don't put your dick in me."

Reggie moved to behind his friend. He put his dick in-between his cheeks and started rubbing his dick. The lube he had on his dick had let it glide easily around his friends ass.

"Ok, we're good" Marcus said. He started to rub his own dick.

Reggie was pushing his cock against his friends ass and was surprised how good it felt. He started to really grind his dick between his friend's cheeks. He looked up to seeing one of the porn guys smacking the mixed girl's ass as he fucked her. Reggie was lost in the grinding of his friends ass and smacked him on his ass.

Marcus made and small moan and pushed his ass back against Reggie. Reggie was entranced watching his dick slide back and forth between his friends' pretty ass. He had never noticed that Marcus had such a pretty ass. He reached over and poured some more lube on his cock and ass.

"I think I might be able to cum like this. " Reggie said.

"Yeah." Marcus responded. "Your dick actually feels kinda good against my hole. "

Dustin watched intently from the side chair. He had no idea the boys would actually take it this far. He was recording every detail in his head to be used in future jerk off sessions.

Reggie was rubbing his dick, and started getting his head and pushing it between Marcus' cheeks which he would squeeze together. It felt good. While doing it, he felt his head start to rub against Marcus' hole. It felt warm against his head. He moved his dick so it started to push against the hole just so slightly.

Marcus moaned involuntary and the new sensation. He felt a pressure that brought a new pleasure he hadn't experienced before.

Reggie noticed that Marcus didn't tell him to stop and was actually moaning. So Reggie started working the tip of his dick around Marcus' inviting hole.

Marcus started to moan and push his ass back. He didn't know why it felt so good to have his friends head against his hole, but he didn't want him to stop.

Reggie was pushing and all the sudden he felt the tip of his dick pop into Marcus' ass.

Marcus gasped and both boys froze. Neither one moved. Neither one knew what to do. Both boys were rock hard. Reggie started moving the tip of his dick in and out of Marcus' hole. Marcus started feeling waves of pleasure.

"Just right there. No more." Marcus said.

Reggie understood and continued.

Both boys were were now close to their goal.

"I'm getting close," Reggie said.

"Me too! Just don't stop, ok," Marcus pleaded.

Reggie was starting to feel the pressure building up in his balls. He started to push his dick in Marcus more.

Marcus was getting a whole new sensation from his friend's dick. It was like there was a pleasure button inside him, that Reggie kept pressing. Marcus started pushing his ass back against Reggie's dick involuntarily. He didn't care if his friend was fucking him. It felt too good for him to tell him to stop.

Reggie continued to pull the length of his dick in and out of Marcus' hole. Now he was driving his full cock in and out of his friend.

"Fuck, your ass feels so good." Reggie said while pushing his dick balls deep.

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