James and the Tip

[jbucktown]

James was a good boy.  He was the best boy. 

James was the soccer jock, lgbtq club president, popular, friendly, and at 6'0", 165, blonde hair and blue eyes - gorgeous.  He was the boy everyone wanted.  James breezed through Stanford and then Princeton Law.  His parents gave him a car for high school graduation; a backpacking trip through Europe for college graduation; and a condo for graduating law school.  James new condo was in Chicago as was his new job at a top firm.  James worked a lot, but he still played sports, ran, went to the gym and managed to fuck as much ass as he could find on Grindr.  

James a a wet dream - smart, attractive, educated, good job, gorgeous body, and a top.  James fucked every gorgeous guy between the ages of 18-25 who hit him up on Grindr.  He'd always go to their place.  He'd always use a condom.  He'd always blow his load on the guy's back or face.  Boys fell at his feet and he loved it.  He wasn't conceited, but it felt natural that guys hit on him and he accepted it with grace and a hard cock.  James was picky though.  The guys had to be as hot as him.  He didn't want to grab anyone's soft belly or flabby tits as he fucked them.  He wanted perfect guys.

James also rejected barebackers.  He thought they were stupid and risking their lives for momentary pleasure.  You see, even though James had been fucking guys since he was 15, he had never once fucked a dude without a condom.  James would say, "I'm saving that for the man I love."

Enter...............the Tip

James was out with his gay friends one night.  They'd all been to a fundraiser for a gay rights organization and had a few drinks.  They went out directly afterwards.  James' friends were much like him, athough mostly bottoms and certainly not only have safe sex.  In fact, most of them thought James was kind of pretentious about the safe sex aspect of his life.  But, they never mentioned their dissatisfaction to James or each other.  James' friend, Mike, introduced him to a friend visiting from Spain.  Juan was a bit shorter than James, but he was just as fit.  James thought Juan was the hottest man he had ever seen.  Juan was very attracted to James.  

Mike had met Juan in Madrid.  In fact, Mike had been fucked and bred by Juan many times, including that very morning.  Mike knew not only that James and Juan were both tops, he also knew Juan was an amazing bareback-only top.  Mike had also been fucked by James, who he knew to be a safe sex only top, so Mike thought it'd be interesting to see what developed between the two tops.  

It wasn't long before Juan was touching James all over.  James was getting more girly than any of his friends had ever seen him.  In fact almost everyone was shocked when James went to get drinks and Juan pressed his cock into James' amazing ass and very slowly ground into James.  James was nervous.  He was a top and this guy obviously wanted to fuck him.  He didn't really know what to do.  The guy was so hot that James had to fuck him.  To calm himself, James drank more than usual, with the consequence he was rather drunk by the time he and Juan left the bar.

James broke his first rule, namely he never brought tricks to his condo, but knowing Juan was staying at Mike's place, and as James wasn't interested in Mike being privy to what transpired that night, it seemed James' condo was the best option.  Once in the cab, James finally got a good feel of Juan's amazing nine and a half inch cock.  Now, James' cock was a solid eight incher, eight inches that guys loved, but James found Juan's cock was utterly amazing in both length and girth.  

They kissed in the cab, and Juan, never the shy type, sought-out James' crotch and massaged below James' balls, striving to reach his hole.  James didn't really know why he did so, but almost involuntarily he spread his legs to accommodate Juan's focus of interest - his hole, and when Juan's fingers found that hole, James moaned softly.  

Once upstairs, James made a drink for each, and they enjoyed the amazing view of the Chicago skyline from James' living room.  Not to be outdone by the city scape, Juan pulled his shirt off to afford James another amazing sight.  James followed suit, and the two men resumed making out, as James melted into Juan's nimble fingers and suggestive tongue.  It wasn't long before James and Juan were naked and James hands were braced against the floor to ceiling windows as Juan ate his jock ass.  Even in his drunken haze, James thought several times that Juan ate ass better than he had ever eaten another man's ass, particularly as Juan's tongue reached an amazing depth into James' hole.

Juan knew James was a top, Mike having told him as much, and, to get into James' ass, Juan knew he would need to weaken all of James' defenses, and opening-up James' hole was the best way to ensure James would be fucked at this very window, so Juan kept eating James' ass for quite some time until he got to his feet and asked "Why not grab some lube?"

James returned with both lube and condoms.  Juan pressed James against the window again and jammed his tongue up James' ass, causing James to moan like a whore.  James was sober enough to realize he was begging like most of the bottoms he'd fucked.  James decided right then that he would let Juan fuck him.  It would be the first time James had been fucked his senior year of college.

Juan recognized the relaxation of ass and back muscles as the other top gave his ass over to him, so he started fingering James.  First, one finger, then two, then twisting and corkscrewing the fingers; then more ass-eating.  Only to repeat the sequence several times.

 After almost an hour of prepping James' ass for this fuck Juan stood up and pressed his cock on James' ass crack, as he simultaneously kissed James and ground his cock into James' crack.  Juan asked James what he wanted.  

"Please fuck me," came the reply.

Juan made James beg to get fucked, and beg James did, realizing to some degree Juan was turning him into his bitch, but James was too drunk and too turned on to care.  James wanted Juan's cock inside him.  He needed it tonight.  James spread his cheeks for Juan, face pressed against the glass.  He shoved his hole back at Juan.  

Juan dribbled lube on James ass and then spread his hand over James hole to rub and finger it in.  Then for the first time since they had been naked, Juan touched James' cock, giving it a thorough lube job.  Juan then lubed James' ass and fingered him again, lubed James' cock again, and then lubed his own cock.  Juan pressed forward on James open hole.

James winced as he felt the cock enter him.  Then he relaxed as the spongy head was pushing inside him.  James knew it would hurt, but he really needed Juan to fuck him tonight.  As Juan was pressing in a bit more, James asked "Are you wearing a condom?"  

"No," Juan replied.

"I never fuck without a condom.  Put one on."  

Juan pressed in a bit more and then pulled back some.  Juan was watching and half his head was inside James now.  Juan said, "I'm not even inside you yet.  Let me just play around with the tip and then I'll put on the condom."  

James reasoned Juan's suggestion was okay as they would fuck bareback only briefly- only a minute or so.

"Okay, but just for a minute.  Then use the condoms on the table."

Juan agreed.  He had this safe sex top exactly where he wanted him.  Juan pushed and pulled a little bit farther inside James' hole with each thrust.  Once half Juan's cock was inside James, Juan asked James how he liked it.  

"It feels really good.  We should put on a condom though."

"Just a bit more.  Your ass feels so amazing wrapped on my cock this way."

Juan continued to lightly play with James' cock and stroke his lean, hot jock body as the former top was giving up his ass.  Juan didn't take long before he was balls-deep in James' hole.  

James could feel Juan's public hair on his ass.  He knew Juan was all the way inside his ass bareback.  James mentioned the condom again.  Juan flexed his cock inside James and James moaned and squeezed his ass on Juan's cock.  'Fuck it' James thought, adding 'I'll live it up.  Just this one time.  I'll let Juan fuck me bareback'.

Juan knew he had James now.  He knew the boy would never mention a condom again tonight.  Juan started fucking James hard.  James was moaning and grunting.  Juan was amazed at how easily this safe sex top had given up his ass bareback.  Juan was chuckling inside.  He thought to himself, "All bottoms just need to be shown they are bottoms."

Juan and James were sweating.  James was getting his ass seriously fucked by the hottest guy ever.  Juan was fucking a seriously hot guy.  James and Juan both knew how amazing this fuck felt.

James was grunting and moaning.  He started imagining what it would be like bent over like this for Juan more often.  James was imaging Juan fucking him everyday.  He thought how lucky he was to have this gorgeous man inside him.  How privileged he felt to be fucked by this big dick.  Wow.  Juan was an amazing fuck.  

Juan was stroking James cock faster and he was fucking with shorter and shorter strokes.  James knew Juan was going to cum.  Juan said, "I'm going to cum."  James reached his hand back, grabbed James ass and pulled him inside him.  James felt his first internal cum shot at that moment.  He felt so hot.  He felt so sexy.  He felt so amazing.  James came all over the rub and window.

Without a thought of condoms, Juan fucked James multiple times a day, every day for the next two weeks before he left to return home.  Juan came in James every time.  Juan eventually started making James beg for the cum to be shot in his ass.  James loved it.

[jbucktown]

The party........Oops, I did it again

A few weeks after Juan left, James felt the need to get fucked.  He never told his friends about this need or what he and Juan had done together.  Mike suspected, but James never confirmed anything.  James also didn't tell his friends about the toys he bought to use on his ass.  He used them every time he jerked off now.  James was starting to think of his ass as a sexual organ that needed attention.

James had fucked about four guys in the preceding three weeks, each time using the same approach:  go to the guy's place, use a condom, cum on his back or face.  James enjoyed fucking the guys, but something felt different.  He didn't feel as satisfied.  He needed another cock in his ass.

James went with Mike and a couple of other friends to a party in a lakefront condo.  He knew the guys from the bars, but not very well.  James was wearing a tee shirt that barely touched the top of his jeans and tighter jeans that usual.  The jeans made his ass look amazing.  James was a bit self-conscious about wanting to get his ass fucked so he hung around the bar in the kitchen a lot.  Mike noticed and sent over an acquaintance who had fucked him recently, Dustin.  Dustin was not really James type.  He was short, thin, and nerdy, but he was a solid guy, had a huge cock, and was very sexually aggressive.

Twenty minutes later James was on his knees sucking Dustin's cock in the bathroom, getting him off in a few minutes.  And yes, James swallowed.  James may have hoped he and Dustin could return to the party without anyone noticing, but not so:  the attendees had noticed 'top jock boy James' was acting a bit different.  A few of the guys knew something was up when top boy Dustin and 'top boy' James disappeared into the bathroom together.

An hour later, Dustin had his cock in James and was fucking him in an alley between the party and the bars.  James opened his ass to Dustin as soon as the boy had told him to.  James moaned as he bent over, as Dustin, the ever-so-nerdy guy pummeled his ass.  James loving playing the bottom - he needed and had to get fucked - he had to have the cock in his hole.  

James had condoms in his jeans pockets but none of them were on Dustin's cock.  He was letting another dude he'd just met a couple hours ago fuck him bareback.  James actually didn't care about that right now.  Instead he needed the cock.  He also recognized he wanted the cum in his ass.  It had been weeks since Juan had dumped his cum in James' ass.   Now James needed Dustin's cum.  In fact, he told Dustin "I want you to cum in me.  Don't pull out."  Dustin just pumped harder and in a minute dumped his load in James willing ass.

Dustin and James went to join the others at the bars and dance.  At 4:00 in the morning, James left the bar with Dustin and some of Dustin's friends.  They went to Dustin's house where all four guys fucked former jock top boy James bareback. seeding his hole - and on each occasion James plead for the top's load.

[jbucktown]

Liar, Liar, Pants on Fire

James was busy at work.  He was working on a case and was doing 80 hour weeks.  His hookups were limited to guys in the Loop.  Most of them were out of towners at hotels.  That was fine with James.  He didn't want everyone in town knowing he was getting fucked bareback.  Some of these guys were 20s/30s/hot 40s who James would've checked out at the bars.  Others were guys with really big cocks.  James got so horny at times that he had to have the cock, no matter who it was attached to.

He'd been working like this for months.  He needed a night out.  Mike's birthday was the perfect occasion.  James left work at 8, went home to shower, change, douche, and meet up with the guys.  He met up with them just after they finished dinner.  He apologized to Mike for being late (work....yadda, yadda).  To James surprise, Dustin was at dinner.  He didn't think they knew each other that well.  What James didn't know is that Mike and Dustin had begun to see each other.

Later that evening at the bar, Mike was telling the story of Dustin fucking him for the first time and how great it felt when Dustin's cock exploded.  James looked horrified.  Dustin and Mike looked at James and each other.  Another guy asked what was wrong, James said; "That's gross.  I can't believe you let him fuck you without a condom the first time you fucked."

James walked away.  He was pissed at Mike for being so stupid and unsafe.  He kept telling himself that over and over.  He also knew how jealous he was because he needed a big cock in his ass.  He was looking forward to Dustin exploding inside him that night.  Whatever, Mike's funeral.  James left the bar.

He grabbed a cab and went to his place.  He hopped on Grindr and 10 minutes after he was home the doorman called saying his friend was here.  "Friend, " whatever thought James.  James unlocked the door and went to the bedroom to put on a jock strap.

When the guy showed up he was not what James expected, he was Middle Eastern, kinda fat, greasy hair.  James was standing there only in his blue jockstrap and thinking, "I can't do this."  The guy must've sensed something because he opened his pants and took out a massive cock.  James weakened.  He walked over to the guy, got on his knees and starting sucking his cock.  It grew in his mouth.  It was bigger than Juan's cock and it tasted sour.  Still James sucked the cock.  He wanted it.

Ten minutes later, the hairy, fat, older, unattractive man was on his back on James bed.  James was lubing his cock and about to lower himself on the man.  The man said, "Do you want to use a condom?"  James said, "No."  The man smiled.  James lowered himself onto the man's cock and fucked himself on it for about 5-6 minutes until the man said, "I'm going to cum."  James said, "I want it in me."  The man unloaded in James.  The man left.

James rode two other guy's cocks that night.  He purposefully sat down on each of them raw while facing a mirror so he could watch the cock disappear inside him.  He took both those men's loads too.

James woke up around 11, went for a run to the gym and then worked out.  He was ignoring his email because he planned to checking it once he went into the office.  It was a Saturday, so he was going to work only part of the day.  James went home, showered, changed into some casual work clothes and headed to the office.

On the way, he opened his personal email and texts.  His phone had blown up.  People had sent him links and were expressing surprise and calling him a whore.  James opened the link and put in his headphones.  It was a pornhub link.  

It opened with him at Dustin's apartment being spitroasted by Dustin and one of his friends.  The video lasted over 40 minutes.  You could make out, on high volume, James saying, "Fuck me raw."  "Cum in my ass." and "Breed me!"  The most clear shot was of James when he was being fucked up against the bookcase by a dude whose name he didn't remember.  The guy said, "You like getting fucked bareback slut?"  James saw himself say, "Yes please cum in me."

James was dumbfounded.  His life was ruined.  His reputation was ruined.  WTF?  Why would Dustin do this?  Then he read the title, "Safe Sex Jock Boy Taking Raw Cocks"

He knew Mike had done this.  

James was so mad, hurt and ashamed.

[jbucktown]

Finale

James fixed his life over the next few weeks.  He got pornhub and xtube and xvideo to take the video down and then got the tumblr guys to take it down too.  James let a few of the tumblr guys fuck him so they'd take it down.  James even drove to Milwaukee so one guy could fuck him.  The guy lived up to his word and took it down.  James sister had seen the video and called to make sure he was okay.  Fortunately James' parents hadn't seen it, or if they did, they certainly didn't bring it up.  And, as only a few discrete gay boys at the firm saw it before he got it down, it seemed as if both the work environment and his family were okay.  

Of course James' friends had all seen it.  They all knew the safe sex jock top had turned into a slutty bareback bottom.  James had tried to lie his way through it, but he couldn't.  They had all clearly seen his face and heard his voice begging for the top's cum.  A top, who, by the way, whose name James still did not know.  After due thought, James decided to give up on lying and just be himself.  

A few months later, James was now a regular at both Steamworks and Man's Country.  He didn't care who fucked him and preferred they fucked him bareback.  He asked them all to cum inside him.  He liked having it happen in a public spot so guys would watch.  It made him feel even sexier being the center of attention.  

Over the next year, James became the bottom everyone had fucked.  James no longer cared what people thought of him.  He loved taking cocks and their cum in his ass.  

James was happy.

[roguematrix]

Wow great story. Thanks for helping me shoot.

[drscorpio]

Excellent writing as always, jbucktown. 

[TTFN]

On 3/15/2017 at 10:27 PM, jbucktown said:

James was happy.

I'm happy too, it was a great story.

[Jerry1234]

Great story.  Very realistic how some of us start out as condom only to then get turned around and realize bareback is best.

Also liked that he sometimes used a dildo on himself. Now i don't feel so alone in doing that.

[Docebrown]

Excellent story thanks. 

[rawbearfun]

Hashtag never slutshame a fellow manwhore

Just  live and relish in one's truth ?

Now... your stories are rocking my world at the moment ... Fuck how I have yearned to be the an alpha jock stud who now has an endless train of hot devious unapologetic raw fucks to ensure his downward spiral to being a total manwhore is slick with random loads of cum 

I do lust for my alpha jock studs and being a hairy bear usually does not illicit any response until much later... when the jock is delving into his true  inclinations like James. And I begin to dangle the carrot they are after ?

My thick slab of hard poz uncut cock becomes the tipping point for many spun studly james-esque closet btms who would always say to his posse that he would  "never" be into a guy like me etc

But alone with me... how they moan and beg for my cock and tongue once they experienced it especially with me ensuring the proudly and loudly beg for my poz dick and cum load deep in them 

but their deep craving for a big hard dick fucking them raw and breeding them deep always turns them in some deeply satisfying getting even fucks 

[20cmcock]

Fuck that's hot. 

[Tommy Tank]

Loved reading this story - please post more stories soon!!

 

 

[vivaldi82]

Your stories are hot.

[CincyPhil]

Blues

 

[aj99]

I love a happy ending