CHALLENGED


POSTED:   August 22, 2009

Jesse was lying out at the city park and enjoying the summer sun before it became too unbearable.  He had his shades and shorts on with his leather flip flops resting near his side.  He saw two guys that looked to be a few years older than his 20 years.  His ears perked up overhearing them speak about a party.  He saw one peer over his shoulder and shake his head.  He knew they were speaking directly about him.  He listened closely and heard something about he won’t.

“Ummm… excuse me but I won’t what?” Jesse spoke up.

“Oh nothing dude,” a blond stated. “Nosey.”

“We could at least ask,” the other one said.

“Go ahead.  The worst that could happen is I kick your ass,” Jesse laughed.

“See what I was talking about,” the blond guy said.

“We were talking about a 25th birthday for one of our friends.  I just heard the guy we had lined up backed out,” the other one boldly stated. “We were just looking around and trying to get some sort of idea what type we would be interested in next.”

“I don’t even have to ask what kind of ‘party’ this is, do I?” Jesse said.

“See he’s not interested and totally straight.  We’ll find someone who is perfect.  I’m sure there are lots of guys willing to host a bunch of hot sexy guys,” the blond said smartly and tossed his nose high in the air.

“You aren’t interested in taking off your clothes for a group of guys, are you?” the other asked.

“Depends on what kind of money we’re talking about here,” Jesse said with his interest perked.

“Well... we were paying $250 but everything had to come off and stay off,” the blond said.

“OOOO… now that’s different especially around a bunch of… guys… Girls I would say yes in a heartbeat,” Jesse smiled.

“The offers there for the taking unless you’re…” the blond said with his fingers inches apart in reference to penis size.

“I’m not the biggest guy ever but I don’t hear any bitching either for the females,” Jesse said.

“So is it a yes or no?” the other guy asked.

“Before he agrees, we need to see what lurks under those shorts before we agree to a pee-wee here,” the blond said. “Your body is smoking hot but you are rather short, so I have my doubts.”

“Fuck it,” Jesse said in disgust. “Thanks anyway!”

“See Chase everytime we try to be normal you fuck things up,” the guy said to the blond. “I think he would be perfect.  A straight boy teasing us all night.”

“Damn Taylor, he’s not doing it.  He’s way too straight to even consider fagging out for us,” Chase said and swept back his blond hair as he argued with his friend.

“Hey $250 is a lot of money though,” Jesse interrupted. “I’m always up for a challenge. I’ll do it for that kind of cash.”

“Fine, let’s see the goods then,” Chase said.

“Follow me then,” Jesse stood.  He was short and barely 5’6” if that.  He had a great body and had always been vertically challenged his entire life.  He loved it when people doubted his ability due to his size.  He made varsity football when others said he had no business playing.  He wasn’t a star but hustled and hit whatever moved.  He did excel at baseball and was all conference at second base.  His speed and size was used to his advantage whenever possible. 

Jesse was followed by Chase and Taylor to the closest bathroom at the park.  It felt a tad dirty but Jesse didn’t want to flash the two in plain sight just in case some sensitive parents or older folks show him.

“Drop em,” Chase said once inside.

Jesse had no qualms and dropped his shorts and boxers.  He stood with his hands on his hips with his cock flopping out and balls hanging low.  “Well?”

“Looks great to me,” Taylor stated.

“Any dick looks great to you,” Chase said. “How big do you get?”

“Hell if I know,” Jesse said. “Bigger but I’ve never measured.”

“Jerk it a little and show us,” Chase said.

“Hell no! So what is it?” Jesse said firmly and his hands on his hips.

“He looks good to me,” Taylor said. “We are almost desperate at this moment, Chase.”

“Fine then,” Chase said.

Jesse pulled up his shorts.  They walked back to where they were sitting.  Chase gave explicit instructions and guidelines for the party.  Jesse’s main duty was to strip for the guest and serve the others while naked for one hour. 

“Sex?” Jesse asked. “What about if some guy asks to blow me or some shit like that?”

“I thought you said you were straight,” Chase looked at Jesse.

“Hey, I’ll take a free head job wherever my ass can get it,” Jesse smiled.

“You’re on your own after you finished with the party then,” Chase said. “The main thing is be on time.  Oh yea, trim up a little bit or shave your pubes.  Buy some sexy thong or something to really get them going.”

“I’ll do it,” Jesse said and returned to lying out and catching the rays on his body.

Once back at his apartment that he shared with his best friend, Jesse debated on whether telling Marc, his roomie, about his so called job.  He came out and found Marc with his big feet kicked up and watching golf. 

“Dude, you’re getting dark,” Marc stated.

“Thanks,” Jesse replied.  “Let me tell you about what happened to me at the park.  You’re not going to believe this shit…” Jesse told his story to Marc.

“You’re seriously going to fag it out for $250,” Marc scoffed and chuckled.

“The way I look at it, it’s almost rent money for the month.  What’s it going to hurt showing my jewels to bunch of gay guys?”

“For one, it would be totally different if it were girls.  You’re getting fucking naked for a bunch of fags.  Think about it!” Marc said.

“I’m secure in my sexuality and know how to say no,” Jesse said. “Besides I look good and you know it.”

“Hey you are cut and ripped pretty good, but damn!”

“You’ve done it with a guy before,” Jesse said.

“Fuck off!  I told you I was drunk as hell!” Marc said animated.

“There you go.  I’ll get wasted and not give a shit what I’m doing,” Jesse said.

“You’ll end up with a dick in your mouth and one up your ass.  That’s what’s going to happen,” Marc laughed.

“We’ll see,” Jesse said. “It’ll be a challenge.”

“Yea, you say that about everything,” Marc scoffed.

________

Jesse drove to the house as instructed.  He had put in extra time working out and tanning to look his best for his assignment.  He saw a lot of cars parked in and around the nice brick home in the suburbs.  He checked his hair, brown with new highlights and a nice cut for the occasion.  He walked around to the back door just as told by Chase.  He quietly knocked on the door dressed in his tee and shorts. 

Taylor came to the door and let him inside the kitchen.  “Damn, you look even hotter.”

“Thanks, I guess,” Jesse said.

“You nervous about this?” Taylor asked.

“A little.  More of not knowing what to expect than anything,” Jesse replied.

“Wait here.  We’re just about ready for you,” Taylor said.  He left and went into the dining room/living room.  Jesse could hear the voices of many.  Soon Chase came walking back.

“You ready?” Chase asked.

“As ready as I’ll ever be,” Jesse said.

Chase grabbed Jesse by the arm and led him into the room.  Jesse could sense and literally feel every eye gravitate towards him.  He could see a range from younger guy to older gray bearded guys.  Chase found the guest of honor and birthday boy, Jeff. 

“Here’s your present,” Chase said and pulled Jesse forward.

“He’s so cute and young.  Just like I like em,” Jeff said.

Chase leaned over and whispered in Jesse’s ear, “Taylor’s dimming the lights and turning on the music.  Get ready to show your stuff.”

Jesse’s eyes grew wide for he knew it was show time.  He saw the lights dim and some flashlight pointed at him.  He heard the disco type music and froze.

“You look great,” Jeff said quietly and touched Jesse’s arm.

Jesse took a deep breath and started moving.  He knew he wasn’t a good dancer and heard the jeers.  He did his most seductive dance and tried to block everything out including he was about to get naked in front of twenty guys if not more.  He ran his hands through his hair and started to feel the beat with guys crowded around.  He lifted up the front of his shirt and showed them his abs.  He danced around and could hear the jeers change to cheers.  He moved close to Jeff and slowly took off his shirt.  He tossed his shirt in Jeff’s face.  He flexed every muscle he had and heard the roars. 

“For a short shit, he’s hot,” Jesse heard and fueled him even more.  It was just what he needed to hear.  He slowly pulled down his shorts to reveal a red thong he had bought for this act.  He moved close to Jeff.  He leaned over and shook his ass in Jeff’s face before feeling Jeff grab two hand fulls.  He jumped back and danced around in his thongs.

“TAKE IT OFF! TAKE IT OFF! TAKE IT OFF!” the cheers echoed throughout the room.  He spotted Taylor and smiled while dancing and working up a sweat.  He felt a hand grab his thong.  He wheeled around and luckily didn’t rip it off.  He moved in front of Jeff and slowly jerked down the front before bringing back up.  It was just a glimpse.  Now Jesse was into it with the cheers continuing.  He moved like a cat and got in Jeff’s face.  He put Jeff’s hands on his thong.

“Remove em, babe,” Jesse said to Jeff and wondered what came over him.

Jeff jerked down the thong.  Jesse stepped out of it while Jeff twirled the thong in the air to cheers of the gay crowd.  Jesse was now naked and did his best moves.  He moved to Taylor and seductively went up his leg.

Chase stepped in after the music stopped.  Everyone applauded Jesse.  Jesse took his bows with sweat dripping from his forehead.  Jesse and Taylor left the room and headed to the kitchen.

“You were unbelievable,” Taylor said. “Are you sure you’re not a professional?”

Jesse snickered, “Nah, I just kept my eye on the money.”

Chase came in and gave Jesse a nice pat on the ass. “Fucking great.  You really surprised me out there.”

“Thanks, it wasn’t as bad as I thought,” Jesse said.

Chase handed Jesse a beer.  Jesse downed the cold ale in two big drinks.  Chase put the nice birthday cake in Jesse’s arms.  Jesse knew the hardest part was over. 

Jesse walked with the cake covering his crotch.  He was shocked when he felt a big kiss on the cheek from Jeff.

“Just so everyone knows.  Jesse here is not a professional and he claims he’s straight.  We found his hot ass at the park.  So what’d ya think?” Taylor announced to hear a roar from the partiers.

Jeff leaned over to Jesse, “Is he serious?”

“My first time, seriously but it was fun,” Jesse said quietly with a big smile.

They lit the candles, which Jeff blew out, sang ‘Happy Birthday’, popped the bubbly and cut the cake.  Jesse did his assigned duty and passed out the cake to the various guys.  His ego was inflated by all the comments.  Most of the comments were great on how hot Jesse was with the occasional lewd comment on how not straight he was. 

Jesse was beginning to feel comfortable in his own skin.  He was proud of his body and hard work.  He was a little shocked that not once did he get hard while dancing.  Jesse mingled with the guests and proved to be worth every dime Chase and Taylor was willing pay.  He danced with a few guys when the music started.  He disliked all the touching and even a few who grabbed his cock.  He knew it came with the job with a bunch of horny gay men after some young ass. 

After his allotted time was over, Taylor pulled Jesse to the kitchen and handed him an envelope full of cash.  “You were great, Jesse.  Way beyond what I expected,” Taylor commented. “Are you sure…?”

“I’m sure but you know it was a lot of fun,” Jesse smiled and took the envelope. “Now, where’s my clothes?”

“They are in Jeff’s room.  I grabbed them up to make sure they were safe and secure,” Taylor said.

Taylor and Jeff walked back to Jeff’s room.  They opened the door and saw Jeff fucking Chase with all he had.  Taylor found the clothes and quickly exited the room.

“I just knew you and Chase were boyfriends,” Jesse commented.

“Nah, we’re just friends and barely that at times,” Taylor said. “Chase’s a big fucking man whore as you saw.  Knowing him, Jeff won’t be the only one tapping that ass tonight.”

Jesse put on his shorts. “It was fun, really it was.”

“I’m glad it was.  I think you were a big hit with everyone.  I know I’m beyond impressed,” Taylor said.

“I’ll see ya around then,” Jesse stated with his shirt in his hand.

“You’re more than welcome to stay since the crowd is thinning out,” Taylor stated.

“I’ll have a drink and then head out,” Jesse said.

He walked back into the room.  “Damn, what’s this shit?” one guy asked.

“His time is done, Adam,” Taylor said.

“What a shame,” another guy stated. “He’s really a fun guy and probably great in bed.”

Jesse smiled, “I’m straight but I’ll take it as a compliment.”

Adam spoke up, “If you’ll drop those shorts, we’ll pay your ass to stay a little longer.  Who knows we might see how straight you really are?”

Jesse looked around and saw maybe eight guys still remaining. 

Adam reached in his pocket and pulled out 2 twenty dollar bills. Three others pulled out money and waved it in the air.  Jesse looked at Taylor and smiled.  “I guess I could stay a little while longer as long as I can drink,” Jesse said.

“Only if you drop those shorts,” one guy said. “We love seeing fresh young meat on display.”

Jesse smiled and dropped his shorts.  It wasn’t like they hadn’t seen him naked for over an hour now.  He strutted his cute little muscular ass to find a beer.  He returned with his beer in hand and sat between Adam and another guy with money.  He felt Adam’s hand running up and down his leg.  He stopped him before he grabbed his cock.  “I don’t mind the touching but watch it there,” Jesse said firmly to Adam.  He sat between the two.

Within a few minutes, Jeff and Chase returned still naked.  Both were smiling but everyone knew what had happened.

“In your birthday suit, huh?” the guy next to Jesse commented.

“Yelp and got my birthday fuck from Chase, too,” Jeff smiled.  “Damn Jesse, you’re still here.”

“More money did the trick,” Adam said.

“Fucking whore,” Chase commented loud enough to be heard.

Jesse stood and was outraged.  “I’m not the one getting my ass fucked, bitch!”

“Sit your goddamn ass down.  Jeff will fuck you and show you’re not so straight,” Chase replied all cocky.

“You motherfucker!” Jesse screamed. “I could rip your ass to shreds!”

“Keep talking big faggot boy!” Chase said.

Taylor jumped in and saw a fight about ensue that wouldn’t be pretty either since Chase wasn’t very fit.  He grabbed Jesse by the arm and pulled him away to the kitchen to let Jesse cool off, “This is exactly what he wants.  Calm down for a second!”

“He fucking challenged my ass!” Jesse said.

“So what?  He’s not worth it.  He’s trash,” Taylor said. “You would kill him besides.”

Jesse took a deep breath.  “Okay. I let my temper get the best of me there for a second.  I told myself I could handle anything but…”

“Just drop it, alright,” Taylor said. “There are other guys who really want to get to know you here.”

Jesse stared hard at Chase when he returned.  He sat next to another young guy.  Chase pranced his ass off with Adam out of the room while Jeff grabbed another guy to be alone and have sex.  With a few guys left, Jesse started joking around and was himself.  He mocked his dance moves and kept the other laughing with his humility.  He served the others whatever they requested and accepted a few kisses along the way.

With it getting late, Jesse knew it was past time to go.  He put back on his clothes and headed out the front door.  He was barely outside and heard Taylor yelling his name.  Taylor ran out to Jesse when Jesse stopped in the middle of the yard.

“I didn’t get to say goodbye and thanks again for the best night ever,” Taylor said.

“I’m sorry about that,” Jesse replied.

“There’s no way you would even half way consider…” Taylor tailed off.

“Consider what?”

“I’m just here dreaming some stupid dream,” Taylor said. “I always make a fool of myself in front of hot guys I know I don’t have a shot with.”

“Taylor, you are the only guy here I would even consider doing anything with,” Jesse smiled.

“You would? You wanna follow me to my place?”

“What the hell?” Jesse smiled. “I’ve done shit I’d never dreamed here tonight already.  Why stop now?”

Taylor found his car while Jesse went to his.  Jesse was thankful he wasn’t too drunk.  He followed Taylor down the road to a row of duplexes.  Taylor waited as Jesse parked on the street.

Taylor opened the door and welcomed Jesse into his small place.  He pushed Jesse against the wall and gave him the biggest kiss.

Jesse pushed away, “Wow there Taylor.”

“I want you so fucking bad,” Taylor said. “I’ve been dieing to taste those juicy lips all night.”

“Just slow down for minute,” Jesse said. “Keep that up and I’ll be out of here as quick as I came in.”

“Sorry but I’ve had to eye your hot naked body all night.  Talk about pure unadulterated lust.  That was me and probably a lot of other guys there.  You were a huge hit, Jesse.”

“There you go.  Butter me up.”

“No, I’m stating the truth here,” Taylor said. “I’m the luckiest guy from the party to even be here alone with you.”

“Give me the big head, why don’t ya?”

“I’ll give you head alright,” Taylor smiled and reached down to grab Jesse’s crotch.  Jesse stood there and let Taylor feel all he wanted.  “You’re not stopping me?”

“No, it feels too damn good,” Jesse smiled.

“In that case,” Taylor said and pulled Jesse shirt off in one quick motion and dropped his shorts.  The thong was history by now and so uncomfortable for Jesse.  Taylor bent over and kissed Jesse pecs.  He looked up and expected to be stopped at any moment.

“You know this feels kinda nice,” Jesse leaned back.

“I’ll show you nice,” Taylor smiled and worked his way down.  He grabbed Jesse’s cock and held it. “How’s this?”

“Don’t get rough with me,” Jesse replied.

“I won’t.  I leave that up to you, babe,” Taylor said and got on his knees.  He wanted to show this straight boy how a gay boy treated and worshipped cock.  He started with light stroking before taking his time licking every inch of the shaft.  He kept his eyes glued to Jesse and could see a pleased look on his face.

“MMMM, fuck yea!” Jesse moaned and anticipated the rest.

Taylor sucked each of Jesse’s low hangers.  He returned back to Jesse’s cock and put his hand at the base.  He lowered his mouth and tasted his prize for the evening.  He wanted to scream out loud and rub it in Chase’s face since he was the one sucking Jesse’s cock.  He took a few inches and used his tongue to please Jesse. 

“OOOO yes!” Jesse screamed.  He gently pushed the back of Taylor’s dyed black hair. “Please take it!”

Taylor sucked more with his hand at the base.  He pulled back and licked Jesse’s rock hard cock that was now a full 7 inches maybe more.  “Hot dick!” Taylor commented and continued. 

Jesse did something he didn’t dream of and pulled off Taylor’s shirt.  He could see Taylor was about as average as they came with a little tan going.  Taylor pushed down his shorts and exposed his yellow low rise briefs.  Taylor pulled his cock out and returned to sucking Jesse.  He could hear the elevated moans and groans coming from Jesse’s mouth.  He knew he was doing something right.

Jesse stood and watched Taylor bob up and down.  It felt so great and so satisfying.  He pulled Taylor up and gave him a big hug of appreciation.

“OOO Jesse, I need this hot cock in me.  Please fuck me!” Taylor practically begged. “I’m so horny right now to take you.”

“Well… I think I could do that,” Jesse smiled.  He felt Taylor’s lips again and didn’t mind the passion he was receiving.  The two walked briskly to Taylor’s bedroom. 

“This is really not like me,” Taylor said.

“It is me.  I try my fucking hardest to get laid on first dates.  Damn, guys are so much easier,” Jesse stated.

“Yea, we’re both fucking horny as hell to fuck,” Taylor laughed.  He found condoms and lube.

Jesse watched Taylor get on his knees on the edge of the bed.  Taylor lubed up his ass while Jesse donned the snug condom. 

“I hope I’m good,” Jesse stated.

“I know you’ll be great,” Taylor said. 

Jesse got behind Taylor.  He knew this was the moment he experienced fucking a guy.  He never imagined being in this position, let alone being naked and hard with another guy.  He ran his hard cock up down Taylor’s crack.  He could see a little hair around his hole.  He grabbed Taylor’s hips and pushed inward.  He felt his cock slip inside Taylor’s ass. 

“OOOO,” Taylor groaned.

“Does it hurt?”

“Feels great,” Taylor moaned. “Fuck me, Jesse! Fuck me!”

Jesse had heard those same words a few times in his life but without so much desire.  Normally the desire was from Jesse’s girls.  He slid a few inches inside and loved the tightness surrounding his hard cock.  He threw back his head and started slowly fucking. 

“OOO yes,” Taylor moaned.

“OOO fuck yeah!” Jesse screamed.

“You like my ass?”

“Fuck yea, actually it’s hot as hell!”

“Your cock feels so good,” Taylor moaned and jerked his head.

Jesse pulled back and felt his cock slip out.  He stuck it right back in and leaned on Taylor’s back.  He could feel his cock going deep in Taylor and enjoyed the stimulation he was receiving.  He could hear the moans and purrs coming from Taylor as he started driving his cock in and out.  Jesse wrapped his strong arms around him and pumped a little harder.

“Is this okay?” Jesse asked.

“OOO is it ever.  Feels so fucking good!” Taylor replied.

“You know this is actually fucking hot as hell!” Jesse said and felt his cock slip out again.  He reached for more lube.

“Try fucking me on my back.  I want to see your face while you use my ass,” Taylor said.  Jesse leaned up and allowed Taylor to get on his back.  He watched him spread his legs and put them on his strong shoulders. 

Jesse reentered the hot hole and closed his eyes to take in all the sensations flooding his senses.  He opened his eyes while fucking Taylor at a nice pace.  He saw Taylor’s hard cock and him jacking it.  He saw Taylor’s pleased expression and how tempting his lips were.  He leaned forward to taste them.   A loud smack followed when their lips collided. This heightens Jesse’s drive to give his partner what he wanted.  He pulled up and fucked Taylor with all he had.  He loved hearing the screams and heaving breathing along with his balls slapping against Taylor.  He pushed Taylor’s knees forward and continued to hear the screams along with ‘fuck me’ mixed in.  

“Oh shit!” Taylor screamed.  Jesse could feel the tightness on his cock.  He watched Taylor’s cock explode with streams of white cum.  Jesse too knew he was close and pulled out.  He tossed the condom aside and showered Taylor’s lower body with his overdue load.  The release caused a great feeling of satisfaction and relief.  He lay beside Taylor and felt the kisses of appreciation.

“You were incredible.  Are you sure you’re not…?” Taylor asked.

“No but it was fucking great though,” Jesse said. “That was a hell of a finish to one different night for me.”

Taylor petted and stroked Jesse’s body.  “Please stay with me.”

“Taylor, I seriously need to get back.  I’ll have to practically sneak inside as it is right now,” Jesse said.

“Well okay,” Taylor said and knew he was asking a lot. 

Jesse rose from the bed and found his clothes.  He gave Taylor a hot kiss.

“Can I call you or was this a one-time deal?” Taylor asked.

“I don’t know truthfully but call me.  Who knows?  I’m always up for a challenge,” Jesse smiled.   He headed to his car and saw it was well past 2.   He drove and replayed the events of the night over in his head.  He could do nothing but smile.  He parked at his apartment and quietly walked inside.  He breathed a sigh of relief seeing Marc his roommate was in bed.  He went to his room and crawled into bed.

Jesse was on his side and just about asleep when he heard his door open.  “How was it?” Marc asked.

“What the fuck dude?  Can’t it wait?” Jesse rolled over and saw Marc standing in the doorway naked. 

“No it can’t,” Marc said and pushed Jesse over to lay next to him. “I heard you trying to sneak in and had to find out.”

“Seriously what the fuck is going on here?” Jesse asked and was a little disgusted.

“I want to hear how my friend did and if he got to taste some gay action along the way,” Marc said.

“Everything was actually better than expected.  Now leave me alone so I can sleep,” Jesse sharply stated.

“Did you get any action?  You had to being so late,” Marc stated.

“Yes I got a blow job and then fucked a guy.  Now there you got it.  Leave!” Jesse spilled his guts.

“MMM hot.  Did you kiss any guys?” Marc asked and continued to pester his roommate for details.

Jesse sat up, “What’s with you?  I don’t get it.”

“Well did you?”

“Yes I did.”

“Did you like it?”

“Fuck! I guess I did.”

Marc leaned over and pulled Jesse to him.  He kissed Jesse squarely on the mouth.  Marc pulled off, “Am I better?”

“What is this about, Marc?  First you’re in here naked and then kiss me.  Is there some message in all this shit?”

“Ummm… maybe I want your hot little ass and jealous I wasn’t your first fuck,” Marc said.

“Damn, my roommate has been in the closet this entire time,” Jesse said.

“Well… yea,” Marc stated.

“How would you like to be the second guy I fuck?  I have experience now and will be better,” Jesse smiled and saw Marc’s face light up in the darkness.

THE END…

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