Room and Board Ch. 01

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.