Friends with Benefits Ch. 03
A funny thing happened to Jim when he returned to campus for the few weeks between Halloween and the Thanksgiving break. At first when he returned he felt very horny and a little sexy at having such a wild secret. Knowing what he and Ron had done and how it made him feel made Jim feel like he could conquer anything. He had done something so wild and crazy that it was beyond even his wildest fantasies. The whole thing left him with a huge boost of confidence and self-assuredness. Hell, if he was willing to do that and have it turn out so amazing he felt like there was nothing he couldn’t do.
What surprised Jim was how it seemed others picked up on his new confidence. Suddenly, at parties he was able to approach women who might have intimidated him before. In that short time he even managed to get laid twice. The first was a total one night stand with a hot sorority girl in her room after they both got drunk at a frat party. The next morning he could barely remember her name or much about her beside her knockout looks and how they had fucked each other silly.
The other woman he fucked was someone he knew from his classes and had admired from afar for a while. He had never been able to actually figure out a way to talk with her before, but he finally did it and they had gone out a couple of times. Happily, and very surprisingly, Jim discovered that she was really horny and ready to fuck after their second date. He had assumed she was more conservative based on how she acted and dressed in class, but she was anything but conservative back at his place as she sucked his cock and fucked him.
Through this whole time Jim still thought often about what he and Ron had done. He and Ron talked a lot on the phone and traded e-mails but neither ever directly referenced what they had done. Jim couldn’t get the wild memories out of his mind and he regularly got hard thinking about sucking Ron’s cock or having Ron fuck his ass. One thing that Jim regularly thought about was how it might feel to switch places with Ron and take a turn fucking his ass.
Jim had seen photos and porno movies where men fucked women up the ass, but it wasn’t something he had ever tried. The whole thing made him curious and he spent a while on the internet reading about anal sex. The more he read the more curious and excited he became. As the last days passed before he went home for Thanksgiving break he knew what he wanted. He couldn’t wait to fuck his friend Ron. The very idea of it made Jim’s cock grow and his stomach tingle in anticipation.
Unfortunately, Jim and Ron weren’t able to get together before Thanksgiving. They both traveled home the day before Thanksgiving, but with various family activities and travel plans they couldn’t figure out a way to get together.
Thanksgiving Day itself was busy with family activities. It seemed every living relative of his descended on his house for Thanksgiving. The last of the guests didn’t leave until very late and Jim knew that he’d have to wait at least one more day to see Ron.
He finally made contact with Ron on Friday morning, but he was disappointed to learn that Ron and his family were going to visit some of their relatives. Ron said he expected to be back a little after dinner and would give Jim a call.
Jim spent the day restlessly waiting for what might happen later. Finally, Ron called and not long afterward Jim drove over to Ron’s place.
Ron’s mom greeted Jim when he knocked on the door. Jim chatted with her for a while but was a little disappointed to find her and Ron’s dad still at home. He had no reason to expect them to be gone but he hadn’t really considered what would happen if they were home.
Ron came up from the basement a few moments later and he and Jim chatted with Ron’s parents for a while. Ron’s parents asked Jim all about his school and how his family was doing. Finally, Jim and Ron went downstairs to play some pool while his parents stayed upstairs reading.
As they shot pool they chatted and caught up on what had been going on with each other recently. Jim was again very happy with how normal and relaxed this felt. On some level it seemed like nothing had changed between them. They played pool, trash talked with each other, and joked just like always. And yet things weren’t just like always. On another level Jim felt excited and nervous. He wondered if Ron was curious to continue what they had done or if Ron maybe viewed what had happened as a one time thing. Jim was really curious and eager to continue and he hoped Ron felt the same.
Eventually Ron’s parents called down that they were going upstairs to bed. They exchanged good nights and Ron and Jim heard them walk up the stairs to their bedroom. They played pool a while longer before finally Jim couldn’t wait any longer to find out how Ron felt.
“So, um, I’ve been thinking a lot about Halloween,” Jim started not really sure of what to say.
“Yeah, me too,” Ron said.
For a while neither said anything else and then Ron added, “It’s crazy. I can’t believe ataköy escort we did that, but it’s like I can’t get it out of my head.”
“Me too,” Jim replied.
“Are you sorry it happened?” Ron asked.
Here was the moment Jim had been waiting for. He still wasn’t sure exactly how Ron felt and now he had to decide if he should be honest and risk being rejected by Ron or play it cool until he knew how Ron felt. However, what if Ron was waiting to find out how Jim felt? If Jim played it cool maybe Ron would think he wasn’t interested in continuing.
Jim summoned his nerve and said, “No, it felt so…so…” he struggled to find the right word.
“I know,” Ron said. “I can’t believe how good it felt.” It seemed like Ron’s guard dropped slightly and he added, “Hell, I’m not sure I’ve ever quite felt anything like when I fucked your…” suddenly his voice trailed off as if the realization of what he was about to say was too much for him to complete his thought.
Jim walked over so he was standing right beside Ron and said only, “I loved it too.”
They made eye contact briefly before they leaned in together for what turned out to be a long kiss. The kiss quickly became deep as their tongues danced and wrestled back and forth between their mouths. The kiss and Jim’s own lust were more than he could control any longer. He parted the kiss and moaned, “I want to suck your cock.”
“My parents are upstairs,” Ron meekly protested, “dude, if they find us like this they’ll fucking kill me.” However Jim was too far gone in his own lust to think rationally now.
He dropped to his knees in front of Ron and quickly opened Ron’s jeans. He soon had Ron’s pants and boxers pushed down around his ankles and Jim turned his attention fully on Ron’s already hard cock. For weeks Jim had been fantasizing about Ron’s cock and he couldn’t wait to feel it inside his mouth again and taste his friend completely. Jim wrapped his lips around Ron’s shaft as Ron let out a long, deep moan.
Jim immediately started sucking and playing with Ron’s cock excitedly. He had been anticipating this moment for so long that he didn’t want to prolong it any longer. He hoped there would be time for teasing and exploration later, but for right now he just wanted to make Ron cum. It seemed Ron’s excitement matched his own and it wasn’t too much longer before Ron was clearly on the verge of cumming.
Jim’s fantasies of this moment always ended one of two ways. He either imagined taking Ron’s cum fully in his mouth and drinking it down or pulling Ron’s cock out of his mouth at the last minute and letting his cum land all over his face and chest. He knew Ron’s orgasm was only seconds away and still he didn’t know what to do.
Ultimately, Ron started cumming even sooner than Jim imagined and Jim ended up taking two huge jets of Ron’s cum directly into his mouth. The first jet was so hard and so heavy that it was already seeping down the back of Jim’s throat when he finally pulled Ron’s cock out of his mouth and stroked it excitedly. The rest of Ron’s cum flew out and landed on his cheeks, neck, and chest. As Ron’s orgasm finished Jim felt like a total slut. Here he was kneeling in front of his friend with his face and t-shirt now coated in cum and with a mouthful of warm cum. He slowly stroked his friend’s cock and loved every moment of it.
When Ron finished cumming he looked down at Jim and pulled Jim up to his feet. Jim wasn’t sure if Ron realized he still had a mouthful of his cum when he leaned forward to kiss him, but the idea that Ron was about to taste his own cum out of Jim’s mouth made Jim wildly excited.
As soon as their lips met Jim eagerly drove his tongue into Ron’s mouth. Ron’s tongue immediately greeted his and they stood for many long minutes kissing deeply while they swapped Ron’s cum back and forth between their mouths. When they finally parted their kiss Jim swallowed the cum that was left in his mouth. Maybe it was because he knew what to expect, but the taste wasn’t nearly as bad this time. In fact, there was almost something exciting about the taste.
Ron also swallowed the cum in his mouth before he looked at Jim and said, “My turn.” He led Jim over to the couch and pulled off Jim’s jeans and boxers. He then had Jim sit down. Jim’s cock was rock hard and its tip was already glistening with pre-cum before Ron even touched it.
When Ron finally did lean down and engulf Jim’s cock there was a similar urgency and desire to what Jim had just had. Clearly Ron wasn’t interested in prolonging the moment or teasing as he hungrily and wantonly sucked Jim’s cock. Jim simply leaned back and completely gave himself over to his friend and his amazing mouth.
Jim didn’t try to hold himself back and only gasped to let Ron know he was about to cum before his cock erupted in orgasm. Ron kept his lips firmly wrapped around Jim’s cock even as Jim shot long, heavy jets of cum into his mouth. Ron moved his mouth so only the tip of Jim’s cock was still inside and avcılar escort stroked his shaft wildly with his hand until Jim was done cumming.
Ron gulped a few times and tried to swallow Jim’s cum as quickly as it filled his mouth. The realization that Ron was eating his cum sent chills down Jim’s back and brought his orgasm to a new peak as he continued to fill Ron’s mouth with the last jets of his cum. In the end Ron wasn’t able to take all of Jim’s cum and some seeped back out of Ron’s mouth. Soon Jim’s cock and Ron’s hand were both coated in a thick layer of Jim’s cum. When Jim finished cumming Ron released him from his mouth, but he continued to fondle Jim’s sticky cock for many long minutes.
“Holy fuck,” Jim sighed.
“I know,” Ron replied as he released Jim’s cock and crawled onto the couch beside him, “I can’t believe how good this feels.”
In this intense moment Jim finally had the courage to say what had been on his mind for weeks. He looked at Ron and said, “I want to fuck you.”
Ron smiled and said, “Good, I want to fuck you too.” Jim’s heart beat wildly at the idea that he was about to make his fantasy come true but then Ron added, “But not tonight, if my parents caught us doing that I don’t even want to think about what they would do. Besides, the lube is upstairs and I don’t want to risk them catching me getting it.”
Jim was disappointed but he and Ron talked and quickly discovered that neither of them had any plans or commitments for the next night. They didn’t know yet exactly how or where it would happen, but they both agreed that they would do it the next night.
They pulled their pants back on and Jim cleaned Ron’s cum off his t-shirt the best he could. Jim asked, “So, I’ve been meaning to ask you. The lube and dildo, where the hell did you get those things?”
Ron replied that they could thank Charlie for that. Charlie was Ron’s older brother. He had recently graduated college and was currently working a prestigious internship nearly halfway across the country. Ron’s parents hadn’t changed Charlie’s room much at all as if they were still expecting him to move back in with them someday and so his bedroom still looked much like it did when Charlie was living there.
Ron said that Charlie had once told him about how he had a girlfriend who had a real thing for getting fucked up the ass. Charlie said that at first he just fucked her ass all the time, but then she wanted even more so he bought the dildo so she could use the dildo in either her ass or pussy while Charlie fucked the other.
At first Ron hadn’t believed the story so Charlie produced the tube of lube and the dildo as proof. For whatever reason Charlie had left them in his dresser in the same secret hiding place he where used to keep his porno collection. “Sometimes I use the lube to jerk off,” Ron admitted, “so I knew that stuff was still there.”
They hung out for a while longer before Jim left to go home. He could barely sleep that night thinking about what he and Ron were planning to do the next day.
When he awoke the next morning he asked his parents about their plan for the day. He crossed his fingers hoping that they would say they were going out or doing something and at first it looked like he was out of luck. His parents said they were thinking about heading up to the big Christmas tree festival opening a few towns over. For years the town made a tradition of decorating a bunch of different trees in the styles of different countries and cultures. They always lit the trees the Saturday evening after Thanksgiving. For years it had been a family tradition to go but when Jim got old enough he stayed home while his parents went.
“We haven’t gone in a few years,” his mom said, “and Sally and Bob are going and want us to come along.” Sally and Bob lived a few houses down and were his parent’s best friends in the neighborhood. Jim tried to conceal his joy when they finally decided they would go and his mom gave Sally a call.
“Do you want to come along?” his dad asked.
Jim replied no and shared a laugh with his dad when his dad replied, “Can you get me out of it too? I’m sure you and Ron will have a lot more fun hanging out.”
“Sorry dad but I think you’re stuck,” Jim answered.
A little while later Jim called Ron and told him the good news. They agreed to meet up in the early part of the afternoon, catch a matinee movie, and then head back to Jim’s place after his parents left. Jim knew from past years that his parents would likely be at the festival for a long time. They usually left in the late afternoon and wouldn’t return until sometimes as late as 10pm. At least that was the schedule they used to keep when Jim was in high school. He hoped they wouldn’t surprise him by returning early tonight.
His parents ended up deciding to catch dinner with Sally and Bob before going to the festival so they left the house a little after 5pm. Jim and Ron did catch a movie, but they made sure to go see one that started plenty beylikdüzü escort early enough that they would be back at Jim’s house right at 5pm. They didn’t want to waste a single minute of time.
As they watched the movie Jim thought about how crazy it was that he was essentially on a date with his best friend. The movie was good but he was distracted the whole time thinking about what he and Ron would be doing later. Usually he was distracted by trying to catch a quick grope of his date’s tits or thigh during the show and with wondering how far he might be able to get with her later. This was much different because he already knew how far he and Ron planned to go and that was what was driving him wild.
They ended up returning to Jim’s house a few minutes before his parents left. “Don’t get into any trouble,” Jim’s dad teased as they left.
“We probably won’t be back until late,” his mom added, “Sally and Bob want to go out for drinks after the festival.”
They watched his parents walk down to Sally and Bob’s house and Jim briefly wondered if they should order a pizza for dinner. However, when he looked at Ron he knew right away that food would have to wait. It was clear from the look on Ron’s face that he was as excited and anxious as Jim about what they were planning to do.
Without a word they went upstairs to Jim’s bedroom. Once there they met in a long kiss that, by the time it finished, left Jim’s cock rock hard and straining to get out of his jeans. They parted the kiss and removed their clothes before Jim pulled back the covers of his bed. Once he had them pulled down he turned and saw Ron pulling the dildo and lube out of the backpack he had brought with him. Just seeing the lube again made Jim very excited and his cock twitch.
He and Ron climbed into bed together and resumed their excited kiss. Their hard cocks rubbed together in a kinky duel under the sheets as they fondled each other while they kissed. Jim longed to feel Ron’s cock in his mouth again but there was something else he wanted much more than that. He parted the kiss and rolled over so he could pick up the tube of lube off the bedside table where Ron had set it.
When he rolled back he found Ron already had rolled over and was positioning himself on his hands and knees. Jim moved behind Ron and squeezed a big drop of the lube on his index finger. He cautiously found Ron’s asshole and for a while he just explored it with his finger. Its puckered surface felt new and kinky under his finger. He applied more lube and eventually brought his finger to the entrance of Ron’s ass.
To his great excitement he felt Ron pushing back against his finger as he started to apply pressure. Knowing that Ron was so eager for this drove Jim wild. He continued applying steady pressure until finally his finger slipped inside Ron’s ass. Ron stopped and groaned and Jim also stopped not sure if he was hurting Ron. “More,” Ron moaned after a few moments and Jim steadily pushed his finger deeper until it was inside Ron’s ass to the second knuckle. Jim’s cock was now throbbing from anticipation.
Ron told Jim to apply more lube and soon Jim was able to push his whole index finger up Ron’s ass as far as it would reach. The feeling was unbelievable and Jim couldn’t wait to replace his finger with his cock. He knew, however, that he still had some work to prepare Ron’s ass and so he reached over and picked up the dildo. He coated it heavily with lube and placed it at the entrance to Ron’s ass.
While he pushed forward Ron pushed back and after a while longer Jim was able to fuck Ron’s ass with the dildo fairly easily. Jim remembered what Ron had said before about having one of his girlfriends fuck his ass while she sucked his cock. As he continued fucking him with the dildo Jim asked, “Did your girlfriend ever do this to you?”
Ron moaned and said, “No, just her finger.” Jim continued fucking Ron’s ass slowly with the dildo until Ron gasped, “Fuck me.”
Jim excitedly pulled the dildo out and quickly smeared a huge load of the lube all over his cock. He took hold of Ron’s hips and moved behind his best friend. He positioned the tip of his cock at the entrance to Ron’s ass. Jim pushed forward and Ron again pushed himself back. Jim kept pushing forward and at one point the pressure was so great he was worried that either he was going to hurt Ron or that his own cock might bend painfully. Just moments later Ron groaned loudly and Jim felt his cock slide past the entrance to Ron’s asshole.
“Fuck, wait,” Ron gasped once Jim was partway inside him. Jim remembered exactly what Ron was feeling and waited until Ron’s ass had a chance to get used to him being inside. The way Ron’s ass squeezed his cock was unlike anything Jim had felt before. He had heard about how some women had “tight” pussies but nothing he had ever experienced was even close to the way Ron’s ass squeezed him.
He slowly worked his cock deeper and deeper and paused for a long time with his cock all the way inside Ron. He just wanted to savor the amazingly tight sensation. He started to very slowly fuck Ron and his friend let out a long, deep moan. Jim had to concentrate hard to not end the fuck before it had really even started by cumming. The whole scene was so exciting that Jim could easily have cum if he allowed himself.