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Jeff couldn’t believe how good it felt. He had the girl of his dreams here with him and he was free to use her mouth as he pleased. It was even better than he expected. Warmer, more erotic. He closed his eyes tighter and continued to thrust in and out of her open mouth.

He knew that this would feel better than jerking off with his hand but he hadn’t realized how much a nice warm mouth felt around his cock. He didn’t even mind the feel of the teeth against his shaft occasionally.

Every so often a hand would come and press against his pelvis, signally for him to slow down. He reduced his pace but it was hard to contain himself. He wasn’t anywhere close to cumming and this felt so good. If he did this again, he would wear an eye mask instead of squeezing his eyes closed. He could image her nude body below him, her enormous naked breasts heaving up and down.

Suddenly, the warm mouth he had been fucking twisted away and he heard a voice he had been trying to keep out of his mind.

“Dude, you’ve been going for like twenty minutes.” Dante said. The illusion was shattered. His dick deflated a little bit.

***

It was their senior year of school. They both hit campus as virgins and roommates and became fast friends. However, as the years of school rolled on they became more and more despondent about finding a partner.

This weekend, after some beers and some shared porn they came up with hare-brained scheme: A male mouth feels like a female mouth. A butthole feels like a butthole, right? They had both tried fucking things to simulate the feeling of orifice but nothing felt satisfying. Jeff wanted only oral sex to be included but Dante was an ass man and said anal had to be included.

So it was agreed. And they were nerds and so they set up rules. There would be a coin flip. Whoever lost would be the recipient of as much butt and mouth sex as the other wanted until they came.

After that, it would be easy to say the other person has their fun and the call it night. But Dante explained to Jeff a twist. After every sex act, the receiver at all times has the option of fucking the person who just fucked them. And then keeps going. Jeff was fucking Dante’s mouth and afterwards Dante would have the option of fucking Jeff. But after Dante got done fucking Jeff, Jeff would be free to fuck Dante.

Dante explained this means the arrangement would go on until one of them was bored of doing the fucking. You could at all times cease the arrangement by not fucking the person back. Or just welching on the agreement but neither of them wondered the other would do that.

***

“I can’t cum if you keep stopping to complain!” Jeff muttered. “Just stay quiet. It was feeling pretty good.”

“Ok, but not so fast. I feel like I’m gonna throw up.”

“Ugh, gross.”

Jeff closed his eyes and started stroking his penis. After a few seconds he was hard again and he pushed his penis into Dante’s mouth. If anyone had been timing them, they would clocked the entire mouth fucking session, not including short breaks, at twenty seven minutes and thirty six seconds until Jeff finally came. Dante immediately starting coughing and removed himself from Jeff’s rod, as the penis continued to spurt cum in big globs.

Jeff took a moment to let the feeling course through him. It was a powerful orgasm. Strong that he felt part of his life force had left after cumming. He could feel some of the stick on his pelvis.

Dante spat out the cum into his mouth into a nearby towel and took a long gulp from a diet Mountain Dew which he positioned nearby for this expected result. Altogether, it wasn’t that bad and he only had to taste the cum for a short period of time. He could probably just swallow next time and use the Mountain Dew to wash it down.

He watched his friend Jeff sitting there with his pants around his ankles and his slowing deflating dick.

“Ok,” said Dylan. “Strip off. All the clothes. I’ll tell you want I want to happen.”

Jeff sat there for a moment. He had used his friends mouth to edge for so long that he the cumshot took away any feelinngs of horniness or sexuality he had. The wondered of being on the receiving end of gay sex reviled him but he pushed those emotions down.

“Ah, ok. Oh, man. Ok be gentle I guess.” he said and took off his shirt. “Do I have to be all the way naked? What were you thinking of doing?”

“Yeah, all the way. We’re gonna start with oral and I’ll tell you exactly what to do.” Dante replied.

“Ok… how do you want me? Do you want me lying down or…?”

“I want to you strip off, and then I’m gonna sit down and I’ll tell you what to do.”

Dante took off his hoodie and shirt in one swift motion and tossed it on the ground. And then he unbuckled his pants and lower then and his underwear in one motioon. Jeff started his friend, whom he had never seen entirely naked. Dante wasn’t hard and his flaccid penis hung down.

Jeff had asked Dante to remained clothed while he went first because he wondered a naked male body would turn him off. Dante walked over to an office chair and sat down. He spread his legs luridly showing his flaccid penis resting on his balls.

“Strip. Pants, underwear off. I’ve already seen you’re penis and I’ve had in my mouth for, like, four hours.” Dante ordered

Jeff his pants pull halfway down during their sex act. He turned his back to Dante and pulled them off lazily in a post orgasmic haze of reluctance. Dante felt his penis begin to stir and his saw his friend bend over and his exposed bare butt cheeks. Dante had had lots of time to brainstorm all the things he wanted to do given free access to his friend’s body but now he was getting even more ideas.

Jeff turned to him.

“Ok, come down here. Get down below me.” Dante commanded his friend. “Here let me…” Dante spread his legs even wider this time.

Jeff got on his knees his head near Dante’s penis but was unsure what to do because Dante had grabbed his penis in his fist.

“Lick my balls.”

“Oh, man… can we just….”

Dante grabbed Jeff’s hair and pulled him close to his balls.

“Put them in your mouth gentlely and lick them.”

Jeff did has he ordered, putting the balls in his mouth. They had both showered before starting this and balls had a strange taste and texture. Dante’s penis was fully hard and he was slowly moving his hand up and down.

“That feels really good. You’re doing it really good. Ok, now switch.”

Dante took his hand off his penis. Jeff stared up at him and released the testicle that was in his mouth.

“Switch? What?”

“Start sucking.”

“Oh.”

Jeff used his hand to grip the shaft and put his mouth over the end of it. It wasn’t so large that he had difficulty putting it in his mouth and it tasted like weird flesh popsicle. He immediately started to move his head down over the last two inches vigorously, moving up and down and fast as he could muster and attempting to apply as much suction as he could.

“Jesus what the fuck!” Dante said and used one hand to remove Jeff’s off his penis. “Just go slow and curl your lips over your teeth like this.” Dante curled his lips back to showe him what he wanted his mouth to look like.

Jeff started again and Dante immediately stopped him.

“Move your hand away. Just your mouth.” Dante orderd.

Jeff said nothing and set to work again, feeling a little dejected. He worked his mouth over his friend’s penis slowly and deliberately.

“That’s good. Keep going at that pace.” Jeff continued working. He worked short strokes about two inches deep, until the penis was just at the back of his tongue. When he tried to go fast it had gone deeper once and it was slightly uncomfortable. He had a lot of time to look at Dante’s abdomen and pubic hair. He figured he might be down here awhile if Dante lasted as long as he did. He thought if there was a way to speed it up. He tried to move his tongue against the find out of the penis but it was hard to do with his lips curled up. There was definitely an art to giving blowjobs.

Up above his head, Jeff could hear Dante typing something into his phone and then heard some sex noises coming faintly from phone speakers. He took his head off the penis and looked up.

Dante was swift and palmed his head like a basketball to move it toward his penis.

“I’m watching porn, keep sucking.” Jeff went back to company but Dante didn’t remove his hand. He pushed Jeff’s head deeper during a down thrust causing the his penis to venture further back into Jeff’s throat. Jeff sputtered.

“It feels really good when my penis goes further in. Like, where the back of your tongue and the back of your mouth is. Try to go deeper.”

Jeff did as he was told and tried to go deeper. He would go as deep as he could and then pull back to the head slowly trying to build suction with his lips.

“Oh that’s good but use more spit. Make it more sloppy so it make sucking sounds.” Dante ordered. He had seen many, many blowjob porn videos and there was a specific sound he wanted to hear during the blowjob.

Jeff gave him a look and mustered a small spit on his penis. He tried to muster up more saliva and let it drool onto Dante’s penis. He began sucking again and Dante let out a little shudder. He played around with his lips on the penis to see if he get a distant sucking or slurping noise. It was difficult but he managed to get something close to that going.

“Ok try…” Dante voice was labored “Don’t go back all the way and try to go faster.”

Dante grabbed Jeff’s head with both hands to pushed his head up and down to show him the rhythm he wanted. The stroke would take the penis from his mid tongue to all the way down his throad. Jeff tried to move his head in time with the forceful manuevering of Dante’s hands and started gagging and twisted his head off his dick.

“Oh, man… that’s hard. Give me a second.” Jeff said and looked up at Dante’s face for the first time since he started this. Dante looked down at him with an expression Jeff had never seen before, like a wolf looking at a lamb chop. The was a look of pure lust and his gaze seemed to stare into Jeff’s soul.

Jeff stared off into space for awhile. This wasn’t bad but it was tedious. It was also a little degrading but Jeff supposed that was fine. He had gotten to do the same thing to Dante and as long as no one else found out it would be fine.

Jeff swallowed and then tried to muster some saliva. He was ready to plunge back into the deep. He heard Dante begin a new porn video on his phone and started this time going faster and keeping the cock deep in his mouth. The reaction from Dante was visceral and you Jeff could feel his body jerk and twitch.

“Oh fuck, oh fuck, oh fuck” He heard his friend say.

Dante grabbed his head and pushed Jeff off his penis.

“Ok… haha, that feels good but let’s just… I don’t want to cum just yet.” Dante said.

“Wait, what? Why?” Jeff asked

“Cuz I want to do butt stuff.” Dante said

Jeff shot him a crestfallen look.

“I only did oral with you. Can’t you just cum and we’re done?” He said.

“Ah, no, that’s kinda the way I made the agreement the way I did to make sure it all went the way I want it to.” Dante said.

***

Dante had typed out and printed a long agreement. Jeff wondered it was unneccessary and Dante was being too particular about it. But Dante had insisted and carefully went through each point on the agreement with Jeff to make sure they find out what was happening before having them both sign with a fountain pen he bought specially from Amazon for this occasion.

One of the points he went over was the “Neverending Orgasm” clause, which Dante had prided him self with. It gave the right of whoever was just fucked to be able to fuck the person who just gone done fucking them.

“Which means sex goes on until someone gets fucked but doesn’t want to fuck back.” Dante had explained “Ok, cuz let’s say you cum in me. Like, you really give my ass a good pounding right? Ok so I have the option of fucking you. But if I do, after I get done you have the option of fucking me. But after you’re done I have the option of fucking you. Do you see? So that way we can make sure we both go until we’re done.”

Jeff had wondered the excessive rules and formal contract was unnecessary but he knew Dante was just like this sometimes. He was fine with all of the points in the contract and he understood them just fine and had patiently listened to Jeff’s labored explanations.

***

“I really really want to try to butt stuff and see how an asshole feels around my dick.” Dante said, his voice filled with excitement. Jeff one time snooped on Dante’s computer and found his porn stash, filled with anal porn and so this shouldn’t have been a big surprise.

“Ok… do you want me to continue sucking you?” Jeff asked, wearily.

“No, let’s switch. Get on the bed.”

Jeff got up and positioned himself on the bed on all fours. His body was stiff and he was nervous.

“No,” said Dante “let’s actually do it another way. Lie down on your back..” Jeff moved so he was laying down and felt ludriciously embarassed that his naked body and penis were exposed to his friend despite the circumstances.

Dante got up “Ok but move closer to me and move your butt towards edge of the bed. Yeah, but instead of your legs hanging down put them in the air.”

Jeff did what he was told as Dante directed him until we laying back on the bed, legs in the air with this penis and butthole exposed.

Dante moved forward and Jeff felt a surge of anxiety. The positioning was such that Dante could stand on the ground near the edge of the bed and his penis was at the same height as Jeff’s butthole.

Dante grabbed both of Jeff’s legs for stability and started pushing his penis into Jeff’s hole. Jeff could feel the hard object pressing against of his hole and trying to burrow closer into him. He started to breathing slow and delibrately to calm his nerves.

As Dante’s hard member burrowed closer Jeff felt a sharp pain as it pressed against his anal ring. Dante started to push hard to get it inside and Jeff had a suddenly pain like his anus was gonna break.

“Holy shit ow. Wait, hold on. Do you have some lube? Holy shit.” Jeff claimed with a little bit of panic in his voice.

“Uh yeah.” Dante replied.

A short trip to the bathroom and one container of vaseline and they were back at it. Dante dipped two fingers of Vaseline and smeared some over his penis. He dipped the fingers back in and took another dollop.

He pressed his fingers against Jeff’s hole.

“Ahh Fuck!” Jeff exclaimed and Dante crudely forced his two fingers insde.

jeff squirmed and his face contorted as Dante pushed his fingers in and out of him.

“Oh it’s definitely tight…” Dante’s voice had a hint of wonder as if he was adventurer that had found the lost city of Atlantis.

Dante moved his greased cock back in position and rammed through the entrance in one quick brutal thurst.

“Ahhh! Take it out! Take it out!” Jeff cried his eyes wide.

Dante held his penis, which was inside his friend’s anus.

“Oh that feels good. Just hold on relax…”

Jeff grabbed the bed sheets with one hand, scrunching it up.

“Oh fuck it hurts. Oh fuck, oh fuck. Just hold it…. don’t move forward.” Jeff asshole felt like it was being torn asunder and there was an uncomfortable feeling inside him.

“Ok, take it out. Please take it out.” He begged.

Dante withdrew his penis and jeff’s anus sealed shut behind it, winking few times as it spasmed.

Dante held in position stroking his penis. “It feels really good, really tight,” explained Dante. “I’ll go slow this time.”

Jeff took short haggred breaths. His asshole felt sore and his nerves were on edge. He knew he could probably get up and get dressed and leave. There was nothing stopping him. Dante couldn’t overpower him and the contract wasn’t exactly legally enforcable.

But he did like seeing the delight in his friend’s eyes. He wondered all the hot colleges he had seen around campus. The hot teachers and the hot barista he saw at Starbucks at earlier today. His friend Tabitha. He wished one of them would just once let them him fuck them. Maybe this could be his act of karma. He could clench his teeth and endure this butt fucking and one day a big tittied wench will look at him and say “Fuck me. Do whatever you want. Put it in my ass or my mouth. Cum on my fat tits.”

The wondered of this gave Jeff renewed vigor. Especially though of Tabitha in the same position he was, her legs pushed up and her butthole and pussy exposed.

“Ok,” said Jef “Just do it. Just fuck me.”

“Ok!” Dante said, delighted. He pushed his penis back against Jeff’s tight hole and slowly started working it in.

Jeff’s face contorted as he felt his tight anal ring expand to accomadate Dante’s rock hard penis. Dante forced the penis in further. His face was a mask of determination and he was breathing hard and he has thrusted in his face was getting closer to Jeff.

“Oh your asshole feels so good.” he said lowly, breathing heavily.

Jeff clenched and unclenched his toes. As the intruding penis went further into his there was uncomfortable feeling inside him. A deep psychological feeling that something is not where it should be. Jeff Closed his eyes and turned his face away so he wouldn’t have to awkwardly look at Dante while Dante was using his hole for sex.

Dante had gotten far enough in and started to thrust back in forth with caused Jeff considerable discomfort.

“Ah! Ah!” Jeff cried through clenched teeth. “Oh. Ah!” His breath came out in little sighing hisses and Dante picked up the pace.

Dante reached behind and grabbed Jeff’s buttocks to help him. He began thrusting FAST and Jeff’s anus was an explosion of pain.

“OW FUCK THAT HURTS OW STOP” Jeff cried out frantically but Danted held him in place and continued his pace. Dante was in the last throes of attaining and orgasms and he could feel it coming through his body.

Jeff tried to push Dante off him and began squeeling and crying in desperation. Dante felt a rush of semen leaving him in large spurts and into his friend’s warm orifice. He bottomed out as deep as he could go and felt waves of escatasy wash over him and he emptied out.

“Ow oh god it hurts please pull out. Are you done? Did you cum? Are you finished? Oh god oh fuck.” Jeff asked frantically.

Dante mouth hung open slackily, dimly aware of his friends cry but not eager to move. Eventually he pulled his penis out of Jeff’s ass. Jeff let out a little suprised “Oof” as the sudden withdrawel caused sharp pain in him.

Jeff reached down to feel his asshole. He could feel warm liquid burbling out of him and he felt like his ring has been distorted almost like something was still in it. He touched his hole to make sure it was still there and it felt the same as it at all times did.

“Uh thanks.” said Dante in haze. “That was great. Uh, how’s your butt feel?”

“It’s ok” said Jeff. “You gotta give me a minute.” He glanced over at his dante standing over the bed still in the same position looknig dazed. he looked at his friend’s still hard penis and wondered ‘that was in me. that was in my mouth and my anus. He fucked my ass with that thing.’

“That was… good.” Dante said. “It was definitely different.”

Jeff swung off the bed and grabbed his boxers. “Yeah, different is one word for it.” He laughed “I’m gonna have trouble sitting down for a week.”

Dante looked around for his boxer and couldn’t see them. “Yeah well the Mountain doesn’t exactly wash the taste of your cum out of my mouth.” He smirked and retorted.

Jeff was putting on his pants. “I hope it does. And every time you see me you think of my cum in your mouth.”

“But, honestly,” Dante said looking on the other side of the bed for his underwear. “It was pretty fun. That last part was… Man.”

Jeff was fully dressed. “Uh, yeah. My asshole is so sore now. I hope it didn’t get hurt or anything…. it feels like kinda open.”

“Oh sorry man. I got a little possesed at the end. It was just really good you know.” Dante found his underwear which was bunched up with his pants. He bent down pick them up. Jeff watched his slightly hairy ass and thought if, when he was horny, if he would be as willing to fuck his friend and wondered about the “Neverending Orgasm Clause”

“It’s cool. Honestly, I’m glad you enjoyed it.”

They finished dressing and reassured each other that they would never tell anyone about this and parted methods. They were too spent to discuss doing it again at that moment.

NSFW: yes

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