A Bet's a Bet Ch. 02

Story Info
James and Chris continue their adventures.
2.5k words
4.85
15.8k
64

Part 2 of the 2 part series

Updated 06/16/2023
Created 11/01/2022
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

A week had passed since Chris had sucked off James, and neither had even acknowledged the night even happened. They didn't speak to each other at all the day after, but the following day Chris was back to normal, acting like nothing had happened, and James had followed suit.

Despite this, James did notice that Chris was a bit off a couple of times, but not in a way he could identify. He had asked him if something was wrong, but Chris just looked confused, as if he didn't understand why he would be asked such a question. James put the matter to rest, as well as the blowjob, accepting that it was a one-and-done, never speak of it affair. Until the next Saturday.

James planned to go out to town, but he missed the bus off campus, so he slowly trudged back to his dorm room. By instinct, he slid a key into the slot and unlocked it, only then realising how odd it was that Chris would lock the room when he was in it. Pushing open the door, he saw Chris sitting at his desk, watching his computer.

Chris jumped at the noise and spun around, an earphone in one ear, the other dangling from a cord. He slammed the laptop shut, but not before James saw what was on the screen: a closeup of a rock hard erection, being expertly fellated by another man. The fear in Chris' eyes was like that of a man about to be shot. "What are you doing home?" He blurted out.

"I missed the bus."

Chris nodded, his head bobbing too fast and too small to be natural. "Oh, that's cool. So um, what are you-"

He was cut off by James speaking over him. "You don't have to hide that stuff man, I'm not gonna judge you."

Chris' eyes went wide for a moment, apparently deciding if he would choose denial or acceptance. He went with acceptance. "You...you won't?"

James shrugged. "Mate, you gave me the best head I've ever had, and I'm pretty sure your dick was harder than mine. Makes sense you'd watch this stuff."

Chris looked down, embarrassed. "I'm...I'm not gay though. I don't think guys are hot. I just...I don't know. I just liked it and I don't know why. And watching it is the same. I don't like watching when they kiss, but when they...the blowjobs." His face was crimson. Then he looked up. "The best you've ever had?" He asked, surprised.

James shrugged and nodded, a little embarrassed himself now. "Well...yeah. If I'm gonna be honest, it started out pretty bad, but once you got into it...holy fuck dude. If I could have any woman who sucked like that, I'd marry her."

"A guy doing it doesn't weird you out?" Chris asked, with an interesting look on his face.

"I mean, yeah. At first anyway. When it got good I didn't care. When I say best ever, I mean it. And...to be honest, when we didn't talk about it, I thought we were just gonna pretend it never happened, and I got a bit bummed."

Chris' mouth adopted the faintest smile, seemingly finding this amusing. "Why, did you want me to do it again?"

James was now as embarrassed as Chris was before. "Oh, no. I mean, I dunno, yeah? But, you know, it was..." his incoherent babbling trailed off into silence.

Chris looked down. "I want to" he said quietly.

James couldn't believe what he heard. "You want to? What, you want to suck me off again?"

Chris shrugged, then nodded slightly. "If you want to."

"What, like...now? Cos, I mean. Yeah."

The combined nervousness of the two was bringing time to a standstill. Both wanted it, both had admitted to wanting it...but who would take the first step to making it actually happen?

Chris would. He slowly lowered himself to his knees in front of James, and tugged at his pant legs, pulling them down. James' briefs immediately tented, his cock already on its way upward. A finger from each hand in the waistband, and the underwear was with his pants on the floor.

James was completely silent except for his breathing as he looked down at Chris, who unlike last time, did not hesitate. He opened his mouth, leaned forward, and enveloped James' cock. Also unlike last time, it was immediate bliss.

Chris' tongue swirled around, his lips wetly gliding over the head and along the shaft, then backwards, only to repeat the pattern. James couldn't believe he was here again, but he was more than happy that he was. He breath jumped when he felt fingers running up the back of his bare legs, the gentle tickling accentuating the heavenly sucking.

It was only a few minutes into it, much quicker than last time, when he felt the telltale signs. "I'm gonna cum soon" he warned in a hoarse voice, the pleasure overriding his ability to speak properly. Chris continued as if nothing had been said, not even slightly changing his technique. Seconds later, James groaned as Chris made him orgasm, cum shooting into his mouth. Just like last time, Chris didn't spill a drop.

After emptying his balls down his friend's throat, his legs started to weaken, so he sat down on the bed to catch his breath. Without a word, Chris got up and went into the bathroom. Only a few seconds later, James heard the telltale sounds of a man masturbating. Then only a few seconds after that, the audible grunt of a man cumming. Sucking a dick had made Chris so horny that he was able to jerk off in under a minute.

After exiting the bathroom, Chris looked at James with post-orgasm shame. "Please don't tell anyone about this. I don't know why I like it so much"

James shook his head. "I swear, I'm never telling anyone. We could fuck and I'm not telling anyone." He realised what he'd accidentally implied the moment he said it. And awkward silence was broken by Chris. "Well, I'm gonna play the Xbox. Wanna join?"

"Sure"

------------------

In the following week, James got another two blowjobs. Both were followed by Chris immediately masturbating in the bathroom after. They hadn't spoken about James returning the favour, but as he'd never offered and Chris had never asked, it was an unspoken acceptance that this was a one way street, and Chris seemed fine with it.

The week after that, it was four blowjobs. Each one was less awkward than the last, until it got to the point where it was simply "how bout it?", and the other would nod. Although as much as he enjoyed it, for some reason that James couldn't identify, it always felt like something was missing. He only wished he knew what it was.

Thursday night study finished with a sigh from both. A look at the clock said 10pm, and a look from James got a nod from Chris. Taking his pants off, James sat on the edge of the bed and waited. Chris looked a bit sheepish. "Do you...would you mind if I did it naked?"

James blinked in surprise. He genuinely didn't know how he felt about it, but nodded with the reasoning that if he didn't like it, he could simply close his eyes. After quickly getting undressed, Chris got into position and got to work.

After a minute of paradise, James suddenly realised this was the exact position as the first time, and curiosity got the better of him. He leaned forward and looked down, to see if Chris was hard like the first time.

Chris' concrete boner was pointed up and out, with a small bead of precum right at the tip. As Chris moved back and forth, his cock wobbled slightly. Despite having no attraction to men or dicks, James couldn't take his eyes away. Something about it captivated him. Then, to his surprise, he saw Chris' hand grab it, and begin to stroke it back and forth. Not the rapid jerking to make himself cum, but the slow and methodical jerking to keep himself on edge.

Something about James' dick turning Chris on much that he was edging himself while sucking it sent him to the point of no return, and his breathing quickened. So too did Chris' hand. As James came, so did Chris, and the orgasm from each made it better for the other. It was better for Chris because it turned him on even more, and it was better for James because Chris' orgasm made him take more dick into his mouth.

As they both came down, breathing heavily, James burst out "Jesus Christ that was fucking amazing. You gotta do that every time."

Chris nodded. "Fuck yeah."

------------------

Two weeks later, and James still couldn't place what he was missing. The feeling only ever appeared after Chris sucked him, and it wasn't until a weekend where Chris was away visiting his parents that he figured it out.

Due to regular blowjobs over the last month, James had jerked off at all, and as such, hadn't watched porn at all. Horny, and with no mouth to service him, he pulled up a video and started to take care of himself. And there it was, literally staring him right in the face. Pussy.

When Chris returned, James spoke to him. "Since we started...this, you haven't fucked anyone, have you?"

Chris shook his head. "Nah. I almost hooked up with a chick last week, but she was too drunk, so I just came back here, and...sucked your dick." His face adopted a look of amused annoyance, and they both laughed.

"I haven't either. The whole time you've been sucking me, and I felt like I was missing something, and it turns out it's pussy. Every girlfriend I've had I've always preferred fucking them. A blowjob was just a warmup for me"

Chris raised an eyebrow. "So...what. Do you want to fuck me or something?"

James was surprised, then realised it was a logical thought. "No! No, that's not what I meant haha. I know it sounded like that, but I meant-"

Chris spoke over him. "You can if you want."

James' voice caught in his throat. In fact, he stopped breathing altogether. This had NOT been the outcome he had intended when he started this conversation. But for some reason that he would never be able to explain, he said "ok".

Both boys looked at each other, then Chris slowly began to remove his clothes, and a moment later, James followed suit. A minute later, they were both standing in front of each other naked. Chris lowered himself to his knees and began to suck James off. It felt wetter than usual, far wetter. James knew why.

After a few moments of getting James hard, Chris went and sat on the edge of the bed, just like James would, and James got on his knees in between Chris'. But instead of sucking Chris' dick, he grabbed his own, and guided it forward. Chris lifted his legs and held them in the air, presenting his backdoor.

Placing the head of his cock right at the hole, James began to move his hips back and forth the tiniest amount, just prodding. It was already getting a visible reaction from Chris. James looked at him. "Are you sure?"

Chris nodded quickly, and breathed out the most erotic thing James had ever heard. "Please."

James pushed forward harder, and despite the resistance, his head popped in. Chris arched his back instantly, his head leaning back as he took a deep breath. For James, his eyes rolled so hard they almost fell out of his head. The warmth, the tightness, it was unlike anything he'd ever felt. He began to rock back and forth, only a centimetre or two at a time, revelling in the feeling of Chris' tight ring clamped around his shaft.

Chris' breathing was rapid and thready, and through it he managed to spit out words. "More, more, deep, in." James granted his desire, pushing in deeper with each stroke, before Chris held a hand out, blocking his hip from going forward. "Slow. Go...go slowly. And deeper".

James nodded. He pushed in even more, with roughly 4 of his 6 inches buried inside his friend's arse. He pulled out slowly, then pushed back in at the same speed, gradually increasing his depth until he was balls deep and steadily making love to Chris, whose breathing changed from shallow and rapid to deep sighs. "Ohhhh, ohhhh, fuuuckkkk."

Chris' dick, which had slowly grown this whole time, was now pointing up toward his own face, and every time James pushed in, he saw it throb. A hard throb, the type of tensing that almost causes muscle pain, held for a second, then relaxed, just in time for James to push in again and have it tense up again. Chris' mouth was wide open in a silent moan, and his pelvis was twitching about on the bed, while his stomach muscles would occasionally tense up also. He had never known this level of arousal.

Much like how James enjoyed knowing his dick could turn Chris on during a blowjob, he was ecstatic to see how he was apparently a master at arse fucking. He wanted this to last all night, but Chris hand stopped him. "Wait, stop, stop, no more"

"Oh," James said sadly. "Is it too much?"

Chris shook his head. "No, I mean no more slow. Fuck me." He nodded. "Fuck me."

James nodded, then slowly thrust back in, pulled out, and started going harder every time he went, until he was slamming his hips forward, driving his cock into Chris like it was a railroad spike. Chris threw his head back and groaned in pleasure, then leaned it forward, his face screwed up and going red, then threw it back again. "Oh my god, oh fuck, oh my god it feels so good". His voice had raised an entire octave, and it almost sounded like he was whimpering.

His staccato moans were almost as high as a woman's, and it turned James on even more. His dick throbbed inside Chris, as Chris' own dick flopped like crazy, the hardness of it causing loud smacks as it hit his belly. His moans suddenly grew in pitch, and he gripped the bedsheets tightly and cried out "oh fuck I'm cumming", and cum began to shoot out of his cock, getting thrown all over the place as it swung about wildly.

The sight of this took James to a whole new level of surprise, but the spasms in Chris' anus took him to a new level of pleasure. Chris' arse was literally milking his cock, and he couldn't hold back. Shooting his load deep inside, which caused Chris' to twitch and moan even more, his thrusts began to soften and slow, until he came to a stop.

Chris lay there with his eyes closed and a ditzy smile on his face, basking in the aftermath of the best orgasm he'd ever had. James sat over him, doing the same thing. Chris opened his eyes and looked up him. "Still missing pussy, or was that enough."

James snuffed a laugh. "Not enough. I need more of it."

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
4 Comments
Tripper_DudeTripper_Dude8 months ago

Wow incredibly hot with the natural progression of 2 men exploring and experiencing sex together. James clearly becoming the top and Chris being the bottom both getting pleasure from their place in the sex with each other.

AnonymousAnonymous10 months ago

would like to see Chris become more sub. Some light bondage stuff. Have lay over knees and get spanked.

Xmale06Xmale0611 months ago

Amazing story, but it needs further developments, maybe some deeper submissive vibes from Chris...

MarcLuciFerMarcLuciFer11 months ago

HOT, and the of relationship these two have is really quite beautiful. Would be nice to see James reciprocate if only a little. This was *****s and adding to favorites.

Share this Story

READ MORE OF THIS SERIES

A Bet's a Bet Previous Part

Similar Stories

Slutty Sleepover Two, straight best friends make some discoveries.in Gay Male
Bathing Suit Dilemma Two straight guys get surprisingly horny in the Jacuzzi.in Gay Male
Road Trip with Mike Graduation road trip with my sexy friend takes a turn.in Gay Male
The Arrangement With the lockdown in full swing, two housemates make do.in Gay Male
Backseat Introduction Girlfriend's dad and boyfriend share the back seat.in Gay Male
More Stories