A gay story: Room and Board Ch. 01 Saturday 03/04/23
Robb’s keyboard clicked and clacked furiously as he searched nervously for any loophole or exception which would make the news he just received better. He swiveled in his seat, his wide hips guiding the chair into a more comfortable position, typing and whispering “fuck, fuck, fuck” as the realization of how doomed he was sunk in.
The grants which had paid for Robb’s graduate program had evaporated, the funding pulled as a cost cutting measure. If he couldn’t find some workaround or a decent paying job that also allowed him ample time for studies, he was fucked.
He slammed his laptop shut and called Anne, his girlfriend of 5 years, and a graduate student at a school two states over. Her degree focus was not facing the same cuts.
“I’m fucked, there’s nothing I can do!”
“Baby, I’m sure we’ll find something! I’ll help you look!”
“Thanks, babe. I just don’t know….what the hell I’m going to do. All this work for nothing. Fuck!”
“You need to take a break, Robb. I know it sucks. It sucks ass. But, you need to care for yourself too. Please promise me you’ll take a walk or something to clear your head. I’ll touch base with some contacts, ok? I love you.”
“You’re…you’re right, Anne. Thank you. I love you too.”
Robb decided to take a walk, stopping at a park bench to clear his head. Whipping out his phone, he took in pics of Anne nude she had sent him recently. He grew excited and horny until he swiped into the ones of her getting fucked by her graduate advisor. Deflated, he put his phone away and kept walking.
The time and distance apart had been hard for Robb and Anne. Anne’s idea of them having an open relationship while apart hadn’t helped. He enjoyed the pics of her alone but wasn’t too thrilled with seeing the pics of her getting fucked with her instruction to “imagine it’s you that’s fucking me.”
It was what it was. Robb knew Anne loved him. He knew she had a higher sex drive then him. He also recognized she was out of his league and he was basically a cuck. Sometimes, late at night, and especialy when he was drunk, he would think about it and get off on it. He’d feel ashamed after and push it out of his mind most of the time. Gradually, the shame had disapated, but he wasn’t mentally ready to process that.
In as much as he tried, Robb had struck out in his attempts to hook up. He was very self conscious and that type of thing didn’t come easy. His dick was on the smaller side of average and his body was for a lack of a better word, androgynous. Wide birthing hips, thick thighs, a bubble butt, a little paunchy belly contrasted with a flat chest, normal untoned arms and legs, and a face that struggled to grow facial hair. It also didn’t help matters that Robb kept his hair long, because Anne liked it.
Dejected and with no solutions in sight, he went back to his apartment and went to bed.
He was awoken by his phone going off early the next morning. Seeing that it was his graduate advisor, Dr. Frederick, he quickly responded.
“Robb, I know you’ve been stressing. I think I may have found something that could work for you. There’s good and bad news, of course.”
“Dr. Frederick, thank you so much. I’m definitely interested in staying on and continuing my research. What is it?”
“It’s a bit of a work study situation. Your tuition would continue to be paid, but you’d have to room with two underclassmen. Your job would essentially be to assist them in the college transition, helping to keep their room tidy, cooking, errands, etcetera.”
“So…I’d be their maid essentially” Robb answered sadly.
“Look, I’ll level with you. It’s not optimal. However, with sign ups for next semester approaching, it may be your best bet if you’d like to continue. The spots are filling up fast, but I managed to secure one for you temporarily. I’m going to email you the brochure. I’m sorry this is happening, but there’s unfortunately nothing else I can do…”
“Oh, I know, Dr. Frederick. I’m sorry. I do appreciate your assistance and will read over this now.”
“Great! We will need an answer by end of day to secure your spot. I know that’s a tight fit, but..”
“I understand. I’ll get it filled out either way as soon as I can.”
Robb read over the agreement and it appeared to be just as bad as he thought. He’d basically be helping out two freshmen in a three bedroom specialized dorm off campus. His responsibilities included cleaning, cooking, and other domestic tasks. He groaned as he read on.
There was a bonus structure he could earn based on reviews by the freshmen he’d be watching over. On the other end, he would be disqualified and terminated if his reviews were too low. There was boilerplate remarks about bullying, etc and apparently there would be a modified RA in the building to handle disputes.
Robb was in between a rock and a hard place. He spent hours pondering. Finally, after talking again with Anne, he arrived at the conclusion that, while it may suck, it was better than being kicked out of school. Also, he could apply for jobs while enrolled in the program and maybe more grants would open up. He filled out the application and received an approval the next day.
Wednesday 03/08/23
Robb was all moved in. He had a short meet and greet with Derek, the 22 year old RA before the freshmen, Arnold and Chuck, showed up. Both 18 and total jock bros, they seemed nice enough, promising they wouldn’t make too much of a mess.
They asked Robb for some help unpacking, which he agreed to with some hesitation, and he already felt used as the teens took on more of a supervisory role, telling him where things were to be placed.
Following that, Robb got to work on dinner, using a meal plan the teens had provided to Derek. He brought their plates into the living room and was dismayed to see them cracking open some beers.
Recalling from the agreement that he was also to be a monitor of sorts against illegal activity, he cautiously referenced the agreement and asked if they could stop.
“Nine” Arnold, responded.
“Ex..excuse me?” Robb responded.
“Eight”
“Wha..”
“As far as we can tell from the agreement, you gotta keep your review scores up to keep the job, right? Kinda seems like they frown on anything lower than a seven.” Chuck interrupted with a grin. “Maybe let this one go.”
“But..”
“Seven” Arnold continued.
“Probably doesn’t look good if you start your first week off so low” Chuck said with a fake sigh.
“Down to six now for not giving us our food, dude.”
Robb shut his trap and set the plates with utensils down before them.
“I’ll be in the kitchen, if you need anything.” Robb said through gritted teeth.
Sitting at the kitchen table, Robb rubbed his temples and groaned at the predicament he was in. He collected their plates and washed up before spending some time studying and setting an alarm so he’d be up in time to make those idiots breakfast.
Thursday 03/09/23
“Five!!” Roared Arnold as he woke Robb up.
Rubbing his eyes and noticing he had somehow slept through his alarm, he scrambled to the kitchen to offer breakfast before being rebuffed by both of them as the flatly stated they were running late already.
“We’ll talk about this when we get home” Arnold said as he slammed the door.
Robb dropped to the couch totally deflated. After some brooding, he decided to get the house in order and went to the biology lab to continue his graduate research.
Upon his return to the apartment, he stopped by Derek’s apartment to talk over his experience so far.
“That definitely isn’t how this should work, man, I’m sorry” Derek said as he squeezed a stress ball.
“This program is wonky for sure and I have to level with you. I know you’re in the same boat as a lot of us, needing this to continue being enrolled. These dumb ass freshmen kind of have you in a bind. I can run this up to the program director, but if they get kicked out that kind or fucks you over too because you’ll have no one else to bunk with and therefore not qualify for the program.”
“Think it over and let me know what you want to do. My opinion is that, yeah, let some of the small stuff go so long as it’s happening inside and not causing a ruckus, no one is the wiser.”
“Yeah,” Robb sullenly replied. “OK, I get it. It’s a system like anything else that has to be gamed. I’ll try to ease off and keep the peace.”
“Sounds good. If you need anything else my door is always open.” Derek replied.
—
“Zerrrooooo” Arnold and Chuck bellowed as they came through the door.
Robb was placing their dinner on the table and wondered what the hell he did now.
“You snitched on us!” Arnold said with a wicked smile.
“Yeah man, Derek said you told him about the beer. He told us we needed to abide by the rules like some fucking dork” Chuck laughed.
Robb noticed immediately that they did not seem bothered in the slightest by what had occurred as they threw their bags down and sat down to dinner.
“We’re going to have to think of what, if anything, we can do to get you back up to passing on your review, man” Arnold said with mock concern.
Robb thought carefully about how he should handle this. He knew Derek was just trying to help, but he was annoyed at him and also angry at Chuck and Arnold.
“I’m sorry, guys, but…”
“Call us sir from now on” Arnold snapped.
“Wha..”
“Do you want to get booted out of this program, man? We don’t need it. You do.”
Robb swallowed his pride, feeling incredibly humiliated.
He took a deep breath and restarted, “I’m sorry, sirs, I was a little frustrated and wanted advice from Derek. We both agreed not to report it any further.”
Arnold and Chuck exchanged grins over how much of a pussy Robb was.
“Good, but not good enough. When you apologize to us, you need to get down on your knees as a sign if respect.” Arnold said.
So Robb did it. He meekly got on his knees, repeated his apology, and said it wouldn’t happen again.
“Good boy” Arnold responded. “Now CRAWL to the fridge and get us each a beer.”
Robb opened his mouth to object but was silenced by the knowing looks they gave him. He turned to crawl, cursing his luck at having to deal with these pissant rich kids. As he entered the kitchen he could have swore he overheard them saying something about his “big ole booty” and felt self conscious. He collected the beers, placing them in a bag, and crawled back to them.
“Ah, how clever” Chuck said in mock encouragement as Robb got up to his knees and handed them their beers.
“You got a nice ass, man. I bet you get all sorts of action with the dudes” Arnold added.
Robb’s face reddened and through gritted teeth countered that he wasn’t gay.
“OH, my bad. No need to get testy. Plus, I gave you a compliment. You should thank me.”
Swallowing his pride yet again, Robb mumbled a thank you.
“Thank me for what?”
“Thank you for complimenting my ass” Robb said, completely humiliated and tearing up.
“No problem. You’re gifted. You could be in a rap video, twerking on a Bentley or something” Arnold responded, pushing his plate away and standing up.
He walked behind Robb eyeing him up and down before settling in near the tv. Robb cleared the table, did the dishes and fell asleep angry and humiliated.
Friday 03/10/23
The morning and afternoon passed uneventfully. Robb made them dinner and idled in his room.
“Sup” Arnold said, entering the room.
“Hi sir” Robb mumbled in response.
“Want to get back up to five?”
“Yes sir.”
“Let me spank you.”
“WH-AT?” Robb answered.
“Shh shh shh” Arnold said playfully, putting a finger across Robb’s lips.
“You snitched on us. It’s a big deal. You’re at 0. If you want to get back, you gotta make up for it. You can get kicked out of the program or take five swats against your bare ass and be halfway to 10. Your choice.”
“Sir, I dunno…”
“Yeah, man….your choice, best of luck…” Arnold said as he turned to leave..
“Sir!” Robb said anxiously.
“Yeah?”
“Please…don’t tell anyone…please” Robb said, humiliated once again.
Arnold grinned ear to ear. “Chuck’s gonna know and supervise. Maybe get the last spank, but that’s it.”
Resigned, Robb simply nodded.
“Cool, bend over on the desk”
Robb slowly obeyed, his eyes peering through the blinds as he awaited the next humiliation as Arnold slid down the 23 year olds pants and underwear.
“Mmmhmm, very nice” Arnold said, getting very handsy with Robb’s ass, rubbing it and slightly spreading the cheeks. “Hey Chuck! Quit fucking around and get in here, man!”
Chuck waltzed in, giving a whistle at the sight of Robb’s ass, but not appearing surprised that it was out.
Out the window, Robb noticed a boyfriend and girlfriend saying goodbye. As they parted, the boyfriend gave his girl’s ass a hard squeeze and spank, eliciting a devious smile from her. Robb didn’t think Arnold was gay, but knew that Arnold did have some sexual attraction to his ass and domination.
It was a weird feeling being sexually objectified like this. He never thought of his ass as a sexual object. He was embarrassed and disgusted but also a little flattered.
His thoughts were broken by the first swat. It stung a little but didn’t hurt much.
“Dang, I love how it jiggles” Chuck spoke.
“Yeah, reminds me of Jennifer’s” laughed Arnold.
“Even bigger than hers, I think”
“Definitely, man”
Swats two and three came with more idle chatter and the two spending more time feeling Robb’s ass up than spanking.
Robb felt his cock, fortunately out of their sight, stiffin. “What the hell is wrong with me?” he thought as he awaited the next one.
This one was harder, jolting his eyes back open and making him lean forward. He stifled any sign of being hurt, not wanting them to see him in pain. Yet, his cock was now fully erect and, had he been able to turn around, he’d notice that theirs were too.
“Alright, Chuck, you got the last one”
Chuck positioned himself behind Robb, palmed his ass, and let fly with the final slap. It was harder than the last, but still nothing to cry over.
“Good boy” Chuck remarked as he softly Rubbed Robb’s ass.
“Arnold is going to take you on a little field trip tomorrow to get some more points.” He added, his hands resting on Robb’s hips. Keep this up and we shouldn’t have any problems.”
The boys left and Robb remained where he was, completely humiliated and waiting for his hard on to go down.
Saturday 03/11/2023
“Up early! Let’s get those points” Arnold triumphantly shouted upon entering Robb’s room and throwing on the lights at 8am.
“Your mission, should you choose to accept it and not be unceremoniously kicked out of school is to walk a lap around campus wearing these!”
Arnold threw a pair of denim booty shorts at Robb.
“Sir, I can’t..” Robb began, rubbing his eyes and still only half awake.
“Yap Yap Yap” Arnold interrupted. “You can and will. I’m being nice about it. It’s Saturday morning, no one is going to he around. And if you hurry up and get them on, you can wear a hat and sunglasses for all I care so no one knows its you. Pick a shirt to go with the shorts, tuck them in, and meet me in the living room.”
Robb, total bitch that he was, obliged. The shorts were a tight fit, but he eventually squeezed his ass into them. A white tee, tucked into them, hat, and pair of shades completed the ensemble. He took a look at the mirror and was horrified by how feminine and slutty he looked. There would be no plausible explanation if he ran into someone he knew.
He walked to meet Arnold in the living room. Arnold, pleased by his continued power over Robb, grunted his approval as his hands traced over Robb’s hips. Robb shuddered as his cock sprang to life.
“No one should be out right now. Get your shoes on and let’s go.”
Unable to shield himself at all, Robb booked it for Arnold’s car and slid into the passenger seat. The leather felt weird on his legs and parts of his ass that were uncovered. He felt like some bimbo who was being driven to the club.
He kept his eyes pointed out the window during the short drive to the campus’ central parking lot, feeling some relief that he hadn’t seen anyone yet.
Arnold parked and hopped out, with Robb slowly following him.
“OK, we’re gonna do a loop until we’re back here, baby” Arnold announced.
“Sir, please…I..I can’t..what if someone sees?”
“Either this or I drive back solo and you walk it. People will definitely see you then, huh? Also don’t see a wallet sticking out of those tight shorts, so, you may have to do something you really don’t want to for a ride.” Arnold replied with a grin.
Robb hung his head, completely defeated.
“Walk, bitch!” Arnold ordered as he aimed his phone camera at Robb’s ass.
Luckily for Robb, it was a Saturday so the campus wasn’t as lively as it would have been. Still, there were still some people and they did notice, most just looking in confusion. One or two whistled and laughed as Robb’s barely covered ass jiggled with each step.
“That’s right, pretend you’re bending over to tie your shoe. Hold that position for a few” Arnold ordered as Robb bent over with his ass facing the street. Several horns beeped as Robb wished he could just disappear.
The rest of the ass parade around campus was uneventful and they got into Arnold’s car and headed home.
“You did good, Robb” Arnold said as he adjusted his shorts.
Robb gulped as he pondered what was next. Of more concern to Robb was the fact that he was completely hard as Arnold felt up his thigh on the ride home.
Back at the apartment, Arnold announced that Robb would be wearing the booty shorts permanently while at home, but said additional points could be awarded if Robb opted to be completely nude.
“Tough, but fair” responded Chuck.
Robb retired to his room, furiously jacking off while trying to think of girls but his mind kept coming back to his recent humiliation, his spanked ass, and the outline of Arnold’s cock after the ass parade.
Sunday 03/12/2023
Robb woke up early, slipped on the booty shorts, and set out to making their breakfast. He set it on the table and waited obediently on his knees until they were done. Once he had finished doing the dishes, he ran some errands and returned to the apartment.
He slipped on the shorts and walked out to do some laundry only to encounter a completely nude Arnold. He gasped in surprise and inadvertently spent too long looking at his flaccid, yet long, cock.
“Whoa, buddy, watch where you’re going” Arnold said playfully.
“I can’t find any boxers, come show me where you put them” he added, guiding a completely mortified Robb into his room.
Wanting to get away from his naked tyrant as quick as possible, got on his hands and knees to root open the bottom drawer, opened it, and was dumbfounded to see there were boxers in plain sight.
“Sir, your boxers are right….” Robb began as he turned to find himself 5 inches away from Arnold’s thick cock.
“OH, that’s right! The bottom drawer” Arnold said.
Eyes down, Robb asked “sir, can I please go? I’m uncomfortable with..”
“OH, my dick?” Arnold said, gripping it and pointing it at Robb. “I guess being in lockerooms all my life has desensitized me.”
The movement brought Robb’s eyes up involuntarily and he noticed Arnold’s cock was plumping up. He couldn’t take his eyes off of it as it grew to 9 inches. His mind was a mess. He was genuinely impressed with how long it looked. He wished his was that big.
“Still there, Robby?” Arnold said, wiggling his hips to make his cock bounce around.
“OH um yes sir”
“If you touch it, you’re guaranteed a good review for next week.”
Robb panicked, stammering over his words and finding none.
“Looks like you want to..” Arnold said as he grazed Robb’s clothed penis with his foot. Being so tight, the shorts showed a tiny bulge.
Without waiting for a response, Arnold took Robb’s right hand and placed it on his shaft. Satisfied that Robb wasn’t pulling back, he guided Robb’s hand up and down the shaft. Keeping a steady rhythm he eventually removed his hand and Robb continued on his own.
Mesmerized, Robb continued stroking Arnold, marveling at how heavy and warm it was. He liked the veins and how precum was forming at the tip.
“Mmm. Yeah, boy, faster” Arnold moaned.
Robb picked up the pace, oblivious to anything else in the world. He was so enthralled that he only snapped back to reality minutes later when huge, thick streams of cum washed all over him. His hair, face, and chest were all sprayed, with a decent sized glob shooting into his mouth.
“Unghhh sir” Robb whined, trying to wipe cum out of his eyes.
“Hehehe, go wash yourself off. It’ll stop burning in a minute…at least that’s what the other girls say” Arnold said with a grin.
“You know the rules. You’re going to help Chuck out when he gets home, biiiiiiitch!” Arnold laughed as Robb blindly scurried out of the room on his hands and knees, his big ass swinging to and fro.
In the bathroom, he wiped his eyes clear and got a good look at himself in the mirror. He looked like he had just walked off a porn set. He was still hard.
Leaning over to spit the cup out of his mouth, he paused, letting curiosity get the best of him, and swallowed it. He didn’t dislike it…he was still rock hard. He scooped more from his face, licking his fingers, and swallowing more before catching sight of himself in the mirror and feeling extreme shame.
Wiping himself with a towel, he decided to hide out in his room for a while. He made dinner later and everyone was cool, not saying anything until Chuck visited his room before bed.
On his knees, he gave the second handjob of his life, and taking it on the face once more. Once Chuck left, with a “good boy” and swat against Robb’s ass, he jacked off while scooping and eating more cum. He felt possessed and came hard. The post nut clarity hung pretty heavy, but he craved more.
Monday 03/13/2023
“It’s interesting you get hard while stroking us” Chuck said, looking down at Robb. “You can’t really take your eyes off of it.”
Chuck had rested his hand on the back of Robb’s head when he started stroking. Robb didn’t even register it, as obsessed as he was becoming with stroking off big dicks. To tell the truth, he wasn’t really even paying attention to what Chuck was saying until Chuck shook Robb’s hand off of him so he could sit down..
“Rest your arms on my legs and keep stroking”
Robb complied, bringing himself even closer to Chuck’s cock. He could feel the heat of it radiating against his face and looked longingly at the precum pooling at the head.
Chuck reached down, putting a finger at Robb’s slightly parted lips. Unsurprisingly to Chuck, Robb let it enter. He danced around on his tongue for a bit, getting his finger nice and wet before rubbing it on Robb’s lips.
Alarms were going off in Robb’s mind but he was too horny to care.
Chuck repeated the same routine a few times before leaving his finger in Robb’s mouth. Without prompting, Robb began to gently lick and suck it. Chuck added another finger and moved them slowly in and out. Robb’s cheeks reddened as he sucked them while stroking Chuck at the same time.
Chuck appreciated what was happening and grew excited. True, he’d had his cock sucked by countless women before, but he knew confused dudes like Robb had a HUNGER for cock that was unmatched by even the sluttiest chicks he’d bagged. He slowly withdrew his fingers and was gladdened by Robb seemingly sucking harder to keep them in.
Once out, he put both hands on Robb’s head and guided it to his cock. He met no resistance as Robb’s lips parted and accepted Chuck’s cock. He removed his hands, knowing Robb no longer needed coaxing.
Robb closed his eyes and gave Chuck’s cock a tongue bath, slowly sucking and taking more into his mouth while still stroking it with his hand. It felt like he was watching himself do it rather than being an active participant. He always thought that enthusiastic blowjobs in porn were a fake, but he was really enjoying it. He enjoyed it more than when Anne would suck his own cock.
His mouth watered uncontrollably as he took more, feeling it poke at his throat. Chuck let out a loud moan and it made Robb proud. He bobbed his head up and down slowly as Chuck’s hands returned to his head, guiding the older cocksucker’s speed.
“Mmm, you love it, don’t you?”
“Mmmph” Robb moaned in response Chuck’s cock entered his throat.
“Oooh fuck, you’re a natural, baby” Chuck groaned, reaching a hand down to tweak Robb’s nipple.
“Mmmmph mmmph” Robb moaned in response, feeling incredibly turned on. His own tiny cock was leaking precum as he opened his eyes to see Chuck’s pubes coming closer to his nose.
“Fuck…fuck yeah, you slut…take me all the way” Chuck growled pushing Robb’s head all the way down, forcing Robb to gag and dribble spit all over Chuck’s balls ack.
Chuck let him up, but only enough to catch his breath through his nose. Keeping the strokes shallow, he waited a minute before bottoming out again. With his hand holding Robb’s head, he started fucking Robb’s throat.
Robb struggled to catch his breath when he could, but was catching on quickly. The room filled with the sounds of Robb’s gagging, Chuck’s sack slapping Robb’s face, and both of their moans.
“Look me in the eyes as you eat my load, bitch” Chuck said in-between breaths.
“Mmmmmphhh” Robb moaned as he looked up to meet Chuck’s eyes.
“OH fuck yeah, take it you fat slut!” Chuck yelled as his load exploded down Robb’s throat. Holding it there for a few seconds, he slowly snaked it our as residual spurts landed in Robb’s mouth and were quickly swallowed.
Robb continued to lick and suck Chuck’s deflating cock as it was pulled out, leading to a comically loud popping sound as it came out. He even pushed his head forward to get one last lick as it was being pulled away, which elicited a laugh from Chuck.
“Don’t worry, baby. Think you and my dick will he spending a lot of time together moving forward.” Chuck said with a grin as he messed with Robb’s hair.
“Stay right there on your knees. I’ll let Arnold know it’s his turn” He said as he left.
Robb didn’t have to wait long. Less than two minutes later he was laying on his back on the bed with his head hanging off the edge, getting throat fucked while an aggressive Arnold squeezed his nipples and slapped his face with his hands and cock.
Robb stroked his tiny cock to an explosive orgasm as soon as they left. His throat was sore, his nipples stung like crazy, and he had been thoroughly degraded. He could think of nothing else but his continued descent into a cock crazed bitch and he fucking loved it.
—
Tuesday 03/14/2023
Robb found himself alone for most of the day, spending some time at the lab, and busying himself with his household duties.
He also found himself busy in a new activity: stroking and edging to gay porn. He took many breaks during the day to watch blowjob videos, favoring aggressive big dick ones. He subconsciously took mental notes as he stroked himself.
Arnold and Chuck were busy with class and a pickup game of basketball at the gym. Unbeknownst to Robb, his studly masters had done poorly in the game and were beating a path home to get some relief that only Robb could provide.
Arnold walked in first, pulling Robb off the couch and slapping him in the face with his cock until it was fully erect. Robb’s mouth danced around, trying to get hold of if.
“Beg” Arnold said.
“Please sir, let me suck your…mmmph” Robb was interrupted with his pleads answered and started diligently sucking Robb’s cock. Arnold allowed it for a few minutes before taking control.
Arnold slammed his cock into Robb’s mouth over and over while the nude 23 year old tried to keep balance on his swolen red knees. By now, he was bottoming out regularly, his balls slapping against Robb’s chin.
“Chuck, man…fuck…pass me that belt”
Chuck flung it over as Robb looked up wide-eyed at Arnold with as much of a pleading look he could make with a giant dick in his mouth.
Arnold slowed his strokes a bit and laughed at him.
“Don’t worry, not going to beat you. Even though you’d probably like that.” He said as he grabbed Robb’s head and slammed his dick in all the way.
Before Robb could register what was going on, the belt slipped around the back of his head and Arnold’s body before tightening and trapping Arnold’s cock deep in Robb’s throat.
Robb panicked, trying to push himself off of Arnold’s legs to no avail.
“So dramatic” Arnold laughed as he easily swatted away Robb’s hands between moans. “Use your tongue, I’m almost there, cockboy.”
Robb frantically licked Arnold’s shaft while feeling up his sack, putting on a show of moaning and maintaining eye contact until he felt his load shoot down his throat and the belt was released and fell to the ground gasping for breath.
“Good job, slut. When given the choice between oxygen and cock, you chose cock” he laughed.
Just as Robb got his energy back, Chuck stradled his chest and shoved his cock in. Chuck fucked his throat for five minutes before cumming down Robb’s very sour throat.
Robb laid there catching his breath as the boys left. He was a mess. His face and chest covered with slobber and cum. Humiliated and ashamed, he rubbed his little cock until he blew all over himself and passed out nude on the floor.
—
Wednesday 03/15/2023
“Ok, boy, you ready to earn your review for this week?” Arnold asked.
“Yes sir” Robb responded. He could no longer keep track of what his score was. He just need he had to obey and things would be easier.
“Good. It’s makeover day.” He said with a wicked grin. “Chuck’s gonna handle this one.”
Robb dutifully followed Chuck to the bathroom and noticed a razor, electric razor, and bottle of cream stationed by the shower.
“Time to get you nice and smooth” Chuck said with a smile as he maneuvered Robb into a bent over position in the shower.
Robb clutched the shower railing as Chuck parted his cheeks and shaved around his hole.
“Beautiful” Chuck laughed as he lightly slapped Robb’s ass and watched it jiggle.
He turned the 23 year old around and used an electric razor to trim Robb’s pubes into a thin landing strip pattern.
“It’s your responsibility to keep up on this from here on out. It’s gonna be a big deal if not, ok? The difference between getting a perfect 10 or a 4 or 5. Got it?”
“Yes, sir” Robb responded looking down at his body.
“Good. You’re going to shave the rest of the hair on your body and face, which won’t take long, and apply this cream. Let it sit for five minutes then rinse. It’s going to make it grow back slower.”
“We’re gonna do some shopping after you’re done in here. I’ll put some clothes on your bed. If you finish up in here like a good boy, we’ll let you wear sweatpants and a hoodie to the car. Otherwise, it’s going to be the booty shorts again, got it?”
“Yes, sir”
“Good boy, see you soon.” Chuck said as he caressed Robb’s smooth ass.
Robb dutifully shaved his body and face, disappointed in himself once again for letting himself be used like this by two 18 year olds and feeling extreme shame for having a hard on. Though he greedily sucked their cocks at will, this seemed to be a step in a more extreme direction. He rubbed the cream on, wincing at the slight burn, sat for five minutes, and then watched his body hair float down the drain as he showered.
He felt himself get even more turned on as his hands went up and down his silky smooth body. He looked himself over in the mirror, parting his cheeks to see his shaved virgin hole. He wondered how long it would remain virgin.
He toweled off after waiting for his hard on to subside and made his way to his room where Chuck and Arnold were waiting.
“Good job motivating him, Chuck” Arnold said while feeling up Robb’s curves and ass.
“What can I say? I’m good.” Chuck responded as he spread Robb’s cheeks and admired his smooth hole.
“Mmmm, can’t wait til he fucks up again and I get my dick up here” Arnold said, as if Robb wasn’t there.
Robb stood completely still, face beet red, slightly scared but horny.
“Your clothes, madame” Arnold said as he handed Robb a bag. “Your sweatpants and hoodie are in the living room. Throw this on and you can wear that over it on the way to the car” Arnold said to Robb, looking him directly in the eye while his hand rested on Robb’s hip.
Robb dumped the clothes out and felt his heart race as he took in the contents:
* a pink thong
* the booty shorts
* a padded pink bra
* a black crop top that would leave his stomach exposed
* a pink hair tie
Knowing that there was no point in arguing, Robb put on the thong, which was almost entirely swallowed up by his ghetto booty, and squeezed back into the shorts. The padded bra and crop top were easy enough. Finally, he flung his hair back into a ponytail.
He caught a glimpse of himself in the mirror and was dismayed by just how feminine he looked. A little bit of make up and he’d be close to passing. He felt his cock stir and quickly tucked it between his legs as best as he could.
Whistles and mock hooting greeted him as he went to the living room. Chuck threw him his sweat pants, hoodie, and regular shoes. Once on, they walked to Arnold’s car.
“Get in the back and ditch the sweats and hoodie” Arnold ordered.
Robb hopped in the back and obeyed. He was quickly joined by Chuck, who quickly whipped his cock out while Arnold rolled down Robb’s window.
“Here’s the deal, you’re going to blow me with your ass peaking out the window. Get on your hands and knees.”
“But…”
“Bitch, no one is going to recognize your fat ass, Jesus Christ!” An exasperated Arnold cut in.
Robb didn’t like it, but conceded he was right. He sucked Chuck’s cock, bringing him to orgasm while the spring breeze blew against his barely covered ass.
They pulled up at the sex shop on the outskirts of town and parked. Robb really didn’t like where this was going and reached for his sweats only to have his hand swatted away by Chuck.
“This is what one would call a judgment free zone. You won’t need these” he said as he pushed a very self concious Robb out of the car.
“Here, let’s get you fixed up” Arnold said as he pulled Robb’s thong strap up so it was readily visible, also hiking up Robb’s shorts s bit so more or his fat ass spilled out the bottom of it.
“Can I help you find anything?” The clerk greeting us by the entrance asked.
“I think we’re good. Just treating our bitch to a little shopping.”
“What a lucky bitch!” The clerk responded with a smile as Robb blushed. “Enjoy!”
“We will!”
Robb obediently held onto a shopping basket while the boys dropped anything their demented minds wanted into it.
In went:
* several thongs and bras
* fishnets
* lube
* lip gloss
* lipstick and mascara
* a dildo set
* a ball gag
* a pair of nipple suckers
* a choker that had “butt slut” written on it
* a pink leash
* books on sex positions and oral techniques
Arnold flagged over the clerk and asked for advice on buttplugs and cock cages, openly telling the clerk they were for “next steps” if Robb “continues not to listen” as he gave Robb a sharp slap on the ass that drew the attention of the four other pervs browsing the store.
The clerk smiled and brought out a few examples of each. The buttplug, with vibration controlled by phone app, was an easy choice. The convo heated up when it came to the chastity cage.
“Well, it all depends on how much your bitch is packing down there.”
“It’s pretty small” Chuck interjected. “He gets hard when he blows us and it’s kind of like this” he continued sticking out his ring finger.
“Yeah. If that..” Arnold added as Robb blushed while his dick grew between his thighs.
“Gotcha. Let me see if I have anything smaller” the Clerk responded, finally producing an XS sized cage that met their approval.
They paid and we returned to the car, this time with Chuck driving while Robb sucked Arnold’s cock. Completely humiliated, he did his best to ignore the cars honking at his ass as he swallowed Arnold’s load.
Fortunately for Robb, they let him get back into his sweats and hoodie before leaving the car and getting back to the apartment.
The rest of the day passed relatively easily, with the boys going to class and Robb catching up on some research in the lab. Once back at the apartment, he donned the booty shorts, cleaned up, and made dinner for everyone. Before bed, Arnold stopped by for yet another blowjob, letting Robb take the lead while he palmed, rubbed, and spanked his fat ass.
Following that, Robb had trouble sleeping. In the back of his mind, he knew he liked and was turned on by a lot of what was happening. He replayed the drive to and from the sex shop and was insatiable in his horniness. His mind went on autopilot, thinking about both of their cocks, how much he liked sucking them, and the surprisingly good taste of cum. He thought especially about how hot it was when they guided his head down while holding on to his pony tail.He marveled, with some anxiety, about what kind of freak he was becoming.
He jacked off twice thinking about it all before passing out.
Thursday-Friday 03/16-03/17
By now, Robb was nude 100% of the time when he was at the house. He did his domestic duties per the program and swallowed their loads on command. The lingering shred of his masculinity told him he should fight, but the growing “bitch” part of his brain was growing used to it and went wild whenever he saw one of their cocks.
Arnold and Chuck ensured that Robb didn’t touch his own cock when servicing them. They also joked that he shouldn’t jack off in private because they liked him when he was horny.
The only thing that caused apprehension and fear for Robb was the continued advances they were making towards his ass. They rubbed it while he sucked him. If they passed him, they squeezed and spanked it.
He knew it was coming. He was afraid. But, another part of him, buried deep inside grew excited.
—
Saturday 03/18/2023
“We’re kicking it up a notch today” Chuck said to Robb.
“You haven’t been keeping up on your shaving so you have to be punished. Understand?”
“Yes sir.” Robb replied, not agreeing but knowing it was futile to argue.
Robb stood in front of the boys nude as they unboxed the buttplug and chastity cage.
They had Robb bend over as Arnold lubed up the plug and slowly maneuvered it into Robb’s hole while Chuck snapped Robb’s pathetic dick into a cage. Robb gritted his teeth and fought the pain as the plug snaked in.
“Please sirs, this is too much” Robb pleaded.
“Oh, we’re just getting started” Arnold cackled, fitting the choker on Robb and grabbing his ass.
A VR headset with noise canceling headphones was placed on the poor guys head and they led him to his bed where they tied his legs and arms to each bed post. They then primed the nipple suckers and attached them to Robb.
“Jeez, training a fag is sure hard work” Arnold said in mock exasperation.
“Truly, but it’s a honest living” Chuck responded as they both laughed.
Chuck queued a video from his phone and cast it to the VR set while Arnold fumbled the remote for the plug and set it to medium.
“Unnngghh, ohhh, ohhhh shit, please, nooo, mmmmphhh” Robb moaned as his body convulsed.
“Yeahhhh, look at him go! He fucking loves this shit!” Chuck laughed as the buttplug vibrated against Robb’s prostate.
“No shit, he’s a total fag. Gonna take advantage of his open hole” Arnold responded while sliding cock into Robb’s eager mouth.
Robb rode the waves of pleasure as the video started. A busty brunette began speaking as TRAINING 1 flashed onto the screen in bold pink.
“You’ve been a naughty little faggot haven’t you?” she said, giggling.
“Do you even think of pussy anymore? Or is it cock which really gets you going?” She continued as scenes of crossdressing sissies sucking cock filled the screen.
“Mmmphh mmmmph mmmmm” Robb moaned into Arnold’s cock.
“You’d do anything for it, little sissy. You love the way it feels, looks, smells, tastes, mmmm”
More cocksucking filled the screen, rhythmic music, and text accompanied with the narrator…
YOU ARE NOT A MAN
– clip of a sissy bringing a hot man a beer and flirting
YOU ARE A SISSY FAGGOT
– the sissy flips their hair back and starts sucking the man’s cock.
Robb found himself really going to town on Arnold’s cock, lovingly slurping, kissing, licking and sucking. It was the loudest blowjob he had given, but he was completely oblivious to it with the headphones.
“But why stop there?” the narrator continued.
– the sissy disrobes and bends over.
“You have more to give”
– the man slides his cock into the sissy’s ass
“You have two holes for a reason, faggot”
– another man enters the scene and shoves his dick into the sissy’s mouth.
TOTAL PLEASURE
On queue, Arnold switched the plug to high.
GIVE IN
YOU ARE NOTHING BUT A FUCKTOY FOR REAL MEN
YOU ARE A COCKSUCKER
YOU TAKE IT IN YOUR BOYPUSSY
YOU SERVE
YOU OBEY
CUM! CUM! CUM!
– a litany of videos of sissies cumming hands free from getting fucked.
It was too much. Robb’s caged cock started squirting as he swallowed Arnold’s cum. Before Robb’s orgasm subsided, Chuck’s cock replaced Arnold’s.
Robb’s entire body shook as he had his first “sissygasm.” Unlike a normal orgasm, he was still super horny and loudly sucked Chuck’s cock to orgasm, swallowing his nut like an obedient cockwhore.
“Mmmm ohhh, more more…I. want…cock” Robb begged to no avail.
The plug’s rumble was set to low and a new video started.
TRAINING 1 ADDENDUM: DIRTY TALK and INITIATIVE
Unbeknownst to Robb, the boys left for the gym. He laid there in sexual agony for two hours while the same narrator taught him how to talk to real men.
BE THANKFUL
– A sissy on her knees debases themselves, saying “thank you, sir, I just love sucking your cock”
MAKE THEM FEEL DESIRED
– A sissy trails after a man getting ready for work, “daddy, can you please fuck my slut pussy before you go? Can I at least suck your yummy cock?”
ALWAYS BE AVAILABLE
– A sleeping sissy awakened by a cock at their lips starts sucking.
TAKE THE INITIATIVE
– A sissy enters a room where her man is hard at work, slides under the table, fishes his cock out and starts sucking.
PRACTICE
– A sissy sucks a dildo while reading a book on cocksucking techniques.
After what seemed like forever of the video repeating, Robb felt the headset lift from his head and noticed Arnold, who started undoing the leg and arm restraints.
“Have fun, baby?” He said with a smirk as he brought the plug half way out before repeatedly sliding it in and out.
“Ooomph, yes sir. Ohhh God”
“Feels good, huh?”
“Yes sir” Robb moaned, unable to lie.
With his free hand, Arnold pulled down his pants, letting his thick dick spring out.
“Oohh fuck” Robb moaned.
“I’m sick of playing the punishment game. We both know you want me inside you” Arnold said as he pulled the plug out.
Robb felt empty and incredibly horny, his mind far past the point of thinking straight. His ass muscles gripped and squeezed at what was no longer there. He looked up at Arnold rubbing lube on his cock and knew he wanted it.
Arnold guided Robb by his hips to the desk, turning the chair sideways so Robb’s torso was slumped over the desk, his knees on the chair, and his big smooth ass pointed up. He reached over and undid the nipple suckers, slightly caressing Robb’s engorged nipples while Robb moaned.
“This is the position I fucked my first girlfriend in.” Arnold said as he parted and massaged Robb’s ass cheeks.
“You want to be my bitch, Robb? You ready to get fucked?”
“Yes…..sir….please” Robb panted as his mind continued to turn to mush.
“You still think this is too much?”
“No sir”
“Mmm, that’s right, bitch. You’re earning your 10 this week. CHUCK, HE’S READY YOOOO” Arnold bellowed.
“Still can’t believe you won the coin toss, you bastard ” Chuck laughed as he walked in naked with his dick dangling and his phone attached to a tripod.
“Tell the camera who you are and what you want, fatty” Arnold said as he lined up his cock with Robb’s hole and pushed.
“Ooomph, my name is….oh. Robb Jones…and I want to be fucked.”
“Ask and you shall receive!” Arnold remarked as he grabbed handfuls of Robb’s ass and rammed his cock in halfway.
“Ohhhh oh God, no, oh, fuck” Robb wailed as his ass jiggled.
Chuck moved to get some views of said ass swallowing Arnold’s cock, making sure to swivel around to get a view of Robb’s caged leaky cock and his puffy nipples.
“As you can see, the North American bitch is in it’s most pleasurable state of existence when fucked” Chuck said in a mock documentarian voice, eliciting a small chuckle from Arnold.
“Unnnghh oh God, it’s too big, sir, please” pleaded Robb, oblivious to Chuck’s jokes.
“God, you seriously can’t stop talking about how big my dick is.” Arnold laughed as he pulled out slightly to begin shallow strokes. Robb heard the lube bottle open again and could feel more dripping onto Arnold’s dick. The pressure built again as Arnold slowly slid it in 3/4ths of the way.
“Wh-wh-whoa…unngh…oooooh” Robb moaned as he was being speared by Arnold’s cock.
“Yeah, you like that, cunt?” Arnold said as he continued to push in.
“Mmmph, sir, it feels so good, ooooh, oh god”
Robb felt Arnold’s balls rub up against his ass as Arnold spread Robb’s fat ass cheeks to squeeze in the final inch of his cock.
“Mmm fuck, this bitch is so tight” Arnold moaned.
“Well hurry up, man. And don’t rip it. I gotta get mine too” Chuck laughed as he set up the tripod on Robb’s bedside table, angling it at the desk.
“No promises” Arnold laughed as he pulled his cock out to the tip and slowly slid it back in.
“Ohhhh ohhh my God, sir!” Robb moaned as his cock leaked pre cum onto his chair.
Arnold grabbed hold of Robb’s thunder thighs and picked up the pace, slamming him with long dicking thrusts as Robb held onto the back of the desk for dear life to steady himself.
“Tell me how much you love it, piggy” Arnold said between breaths as he bottomed out over and over into Robb’s hole.
Robb felt pleasure incomparable to anything he had ever felt before. The humiliation was making it that much better. His mind defaulted to the training videos, knowing it would make Arnold happy. He felt, very deeply, that making Arnold and his cock happy was good.
“Ohhhh, I love it…ungh…omph..I love your cock…I love…ahhhh shit…being fucked by you, sir…please don’t stop…I’ll do anything….just please don’t stop” Robb said, using his knees to push his ass back to meet Arnold’s thrusts.
Arnold, immensely pleased at himself, went into overdrive rendering Robb unable to speak, barring glutteral moans and grunts. He fucked the 23 year old hard, sending his ass jiggling and bouncing, before grabbing and pulling Robb’s hair to go for the killshot, maneuvering his leg around Robb’s ass and placing it on the chair to give him more leverage.
Meanwhile, Robb convulsed into his second sissygasm of the day, which caused his ass to spasm all over Arnold’s cock. A minute later, Arnold was triumphantly cumming deep in Robb’s ass with loud moans and a kung-fu grip on Robb’s hair.
Arnold caught his breath, hunched over Robb’s back. “No going back from this, cockboy” he grunted into Robb’s ear before sliding out and wiping his dick off on Robb’s ass.
“Damn, you gaped the slut” Chuck said as he exchanged high fives with Arnold.
Chuck helped Robb stand and guided him back to the bed, placing him on his back. Grabbing his belt, he held Robb’s legs together and tightened the belf around Robb’s thighs so he couldn’t spread his legs.
“Ahaha, didn’t you do this when you had sloppy seconds on Vanessa’s hoe pussy?” Arnold said while redirecting the camera.
“Yeah, man. Worked then and it’ll work now.” Chuck replied.
Placing Robb on his side, Chuck got behind him in a spooning position and slid his cock into Robb’s well used hole.
“Unggghh…oh God, yes” Robb moaned as Chuck slid in and out. Without prompting, he reached a hand back and spread his cheeks for Chuck.
Chuck alternated between pinching Robb’s nipples and holding onto his gut as he speared him over and over.
“Fuck yeah, bitch, you were born for this” Chuck grunted as he kept up the pace.
Robb mindlessly reached down for his own cock to give it a tug before remembering he was caged.
“Silly silly” Chuck said into Robb’s ear while dragging Robb’s hands up and ensuring he continued to spread his cheeks.
“You don’t need to worry about that anymore. Bitches like you can cum from big dicks in their pussy. You can either hold your cheeks apart or play with your sissy nips” Chuck added as he flicked Robb’s left nipple.
Robb mindlessly tweaked his nipples as Chuck fucked him. Because Chuck had less leverage on his side, if was a different type of fucking but still immeasurably pleasurable. Chuck’s cock slid and out slowly, teasing Robb’s prostate and driving him crazy.
Chuck’s pace picked up and he grew impatient with the position, flipping Robb on his back while throwing his bound legs over his shoulder without removing his cock.
Robb looked up at him expectedly, his entire body enflamed in passion. He squeezed his nipples as Chuck leaned in and started with fast strokes, longdicking the poor grad student over and over until he blew deep into Robb’s bowels and collapsed on top of him.
Despite cumming just recently with Arnold, Robb was still incredibly horny and felt like a bitch in heat, disappointed that he didn’t cum again with Chuck. He squeezed in earnest as Chuck pulled out, making a popping sound as it did.
“Dang man, his hole is winking at you” laughed Arnold, filming it all. “Guess you weren’t studly enough to make the bitch cum like I did” he laughed.
“Fuck you” Chuck replied with a laugh. He picked up the dildo set they had purchased and undid Robb’s legs.
“You want to cum, piggy? He asked as he suctioned one of the dildos to a chair and lubed it up.
“Yes, sir” Robb pleaded, eying both of their cocks and the dildo hungrily.
Arnold placed the tripod on the desk and they both picked Robb up, lowering him slowly on the dildo until it was all of the way in.
“Ommmphhh” Robb moaned, happy to be filled again.
They lifted him up until just the tip was in and brought him down again, repeating it several times as Robb’s breathing picked up and his cock strained against his cage. They set him all the way down and let go.
“Wiggle your pussy on it and ride it, girl” Arnold said. “We’re not going to always want to do all of the work!” Arnold added in mock seriousness.
They sat back watching, and filming, as Robb gyrated his hips on the dildo, rising slightly up and down on it, wiggling his ass on the descent to hit his g spot. It didn’t take long until Robb came for the third time that day.
“Mmmphh oh god, fuck yes” Robb moaned as his balls drained.
“Good girl” Chuck remarked, helping Robb off the chair.
“Hit the showers, hoe” Arnold added. “You’ve earned a night off.”
Robb struggled to walk, feeling their loads slide down his legs. His hole and cheeks were a creamy mess. He sat in the shower, letting warm water rush over him while mindlessly rubbing his freshly fucked ass. It was too much to process for right now. He had sucked cock. He had been fucked like a cheap whore. He had been embarrassed in private and in public.
So why was his dick still hard?
Why did he love it so much?
He laid down in bed that night unsure of anything. His mind drifted from the anxiety of when he would inevitably have to tell Anne about everything to the warm feeling of holding a cock in his hand and going to town on it. He fell asleep, dreaming about dozens of nude men surrounding him while trying to service them all.