Room and Board Ch. 02

Sunday

The next week was like a blur to Robb. He had a cock in his ass or mouth literally every single day. He loved it and it became a normal part of his daily routine. Part of this normalization, though, led to him no longer being able to cum everytime he got fucked, which resulted in him being horny nonstop.

This served Arnold and Chuck just fine, as Robb was insatiably hungry for cock. This hunger fed their control.

Clothes were back in, but not Robb's clothes. He wore skirts, barely covering his ass, fishnets, blouses, and hot pink slippers. Outside of the house, he wore his usual clothes, but underneath wore thongs and bras.

The sissy videos continued, but the buttplug was always set to low. It was a lot of the same stuff, but Robb really did start feeling more feminine. He grew to like his clothes and accessories. He liked putting his hair in a pony tail, pigtails, or whatever they wanted.

A makeup routine was added to keeping his body shaved. They got him to pierce his ears and wear large hoop earrings and a necklace with a cock pendent. After five pm, he was expected to get dolled up and fun timewould begin. This could mean blowjobs or, if Robb was lucky, a hard ass pounding.

His favorite was when they would double team him with one working his mouth and the other working his ass. It was a near guarantee that he'd cum that way, but it wasn't an everyday thing.

The extreme horniness even had him fantasizing about other men in his life like professors, other students, and Dr. Frederick. He'd grown to anxiously awaitArnold and Chuck coming home each day.

He knew he had to tell Anne, but kept putting it off, trying to justify it as being part of their open relationship deal. Still, he knew it was different because he was the one being fucked and sucking cocks. It was a big part of his life now and she deserved to know. They were going to meet up on break in a few weeks and Robb was growing incredibly nervous about getting out of his cage before then.

Robb decided to test the waters one evening while giving Arnold a blowjob on the couch. After swallowing his load, he lovingly kissed the head before looking up to Arnold.

"Sir?" Robb said, looking up at Robb.

"What do you want? More cum? I'm spent." Arnold laughed

Robb blushed and decided to lean into it.

"Of course I'm interested in that" he said with a smile as he held Arnold's cock and admired it.

"I'm meeting up with Anne in a few weeks and was wondering...if i....you know... coule unlocked during that time" Robb said, lifting the front of his skirt and shaking his hips to make his caged dick wiggle.

"OH yeah, this alleged girlfriend at the other school" Arnold mockingly replied.

"She's.. real sir. I can show you pictures of us together."

"Let's see. Give me your phone."

Robb obediently unlocked his phone, went to his pictures of them, and handed it over.

"Well, I'll be damned. How'd you land her? Know its not your dick." Arnold laughed.

"Ohhh, what are these" he added as he swiped through my phone. "That's definitely not your dick in her mouth...pussy...or ass...dang."

"We have an open kind of thing.." Robb answered, looking down in shame.

"So she knows about you opening your mouth and legs for us?"

"No..not yet, sir."

"Very interesting" Arnold said as his dick grew against Robb's cheeks.

With a few swipes, Arnold synced Robb's phone to the TV and started playing a video of Anne getting fucked from behind.

"Bend over the ottoman, keep your eyes on the screen." Arnold ordered.

Robb complied, incredibly humiliated once again but excited about being fucked.  The line between sexuality and humiliation had been so thoroughly confused for Robb already, but this was yet another depth.

He watched Anne get fucked while she laid out moans and screams that he was incapable or giving her. Meanwhile, Arnold lubed up his cock and started sliding it in.

"Ooomph oh fuck" Robb moaned.

"Yeahhh, bitch. You take it just like her."

"Mmmmm"

"You both love cock" Arnold said, driving his dick all the way in.

"OH fuck yeah...I fucking love it"

"You're a sissy cuck, aren't you?"

"Mmm yes sir" Robb said, finding himself mirroring Anne's hip movements.

"You ready to do whatever it takes to get your faggy dick in your girl?" Arnold said, pulling his dick nearly all of the way out.

"Yes sir...I'll do anything" Robb replied, his knees wobbling in sexual anticipation.

"Good boy" Robb growled as he slammed his cock in.

Arnold studiously copied the moves of the man fucking Anne. Every ass spank, every caress, every hair pull. The effect on Robb was profound as he watched the TV and felt it. He could feel an orgasm building as Arnold's dominance and the humiliation combined was exactly what he craved.

Anne was flipped over and fucked hard while she sucked on the man's fingers. So too with Robb. He could no longer see the screen, but knew from the sounds that Anne was going to cum soon.

Arnold moved his hand from Robb's mouth to his nipples and fucked hard as he squeezed. Robb seized in sexual pleasure and came hard, with Arnold following moments later, flooding Robb's ass with warm sticky cum.

They laid together on the sizable ottoman, Robb resting his head on Arnold's chest as his ass gaped and spasmed. It was one of the more recent developments that Robb enjoyed. He still felt like a whore, but it was nice.

"Here's what you're gonna do to earn the opportunity to give her your shrimp dick" Arnold said as he caught his breath and squeezed Robb's ass.

"One. We're going to expand your body count. Two more guys. You find one and we'll take care of the other. I don't care if you have to go on grindr or whatever type of app you dudes use. You can get all dolled up like you enjoy doing here, not use your name. Whatever. We're going to need proof, though. Get him to snap a pic or video of you getting plowed."

"Two. We're going to make a video of you and put it on xtube or some shit. Your face, all dolled up, will be in it, with our cocks."

Robb was hit with a high degree of sexual anxiety, growing erect but his brain screaming no. He knew well enough that he was unrecognizable when dressed as he was...but there was always a small chance...but then again, why would anyone wanting to expose him be viewing those types or videos in the first place.

He mindlessly started stroking Arnold off, watching it get hard again. It was crazy to him how much power cock had over him. He leaned his head down, kissing and licking it.

"Good slut" Arnold said, giving Robb a hard slap on the ass.

"We'll have a fuckbuddy set up for you soon. You get cracking on finding your own."

Robb laid in bed fully nude wondering what was next. What had started as a scheme to pass stupid reviews had morphed into a scheme that would allow him to have sex with his own damn girlfriend. He fiddled at the cage, looking for weaknesses on it for the hundredth or so time since it had been placed on him. He stopped, knowing it was useless and he was trapped. He sighed as he felt up his smooth ass and body, already coming to terms with the fact he'd likely be ok so long as his descent wasn't known campus-wide.

He thought about how he'd find someone else to fuck him. Going on Grindr seemed like too big of a risk to him. Little did he know that an important figure in his life would soon be making the decision for him.

--

Robb sat in Dr. Frederick's office, discussing research findings and next steps in the processes they were looking into. With business out of the way, Dr. Frederick asked Robb how looking after Arnold and Chuck was going.

"Oh, you know, rough at first..but we've fallen into a routine now and it's not so bad" Robb replied, hoping the conversation would change.

"Ah, that's good" Dr Frederic replied, putting his arms behind his back and sighing. "Sure there's nothing you want to talk about?"

"Nope! All good"

"They're not making you do anything you don't want to then?"

"Uh..no"

"So you willingly dress like a woman and suck their dicks, then?"

"What...I.." Robb stammered.

"It's funny. I was driving around and I see the three of you get into a car. Windows roll down, and what can only be your ass peaks out. Well it didn't take me long to guess where your head was" he said with a laugh.

"I..I.." Robb began, blushing.

"It's ok, stop yammering, boy" he said, grinning wildly as he pushed his chair back and stood up.

He walked over to where Robb was sitting and stood behind him, massaging his shoulders.

"Nothing wrong with who you are or what you're doing. I had my dick in my roommates holes during college myself." He continued, letting one hand down to stroke Robb's face.

"He liked it as much as I'm guessing you do. You give those boys your ass, Robb?" He asked as his hand moved down to Robb's nipples.

"....yes" Robb replied, head spinning.

"Good. You're a good roommate, Robb. You want to be a good student to?"

"Mmmph...I don't know, Dr. Frederick."

"Hmm, I think you do." He said as he locked the office door and returned to his seat. He unzipped his pants and let it out. It wasn't the longest dick Robb had seen, but the girth was obscene. The true definition of a beer can cock. Robb knew he needed it.

"Choice is yours. You can squeeze your fat ass under my desk and take care of this" he said as he wiggled his cock, "or you can leave now. We'll pretend like this never happened."

Robb's heart was beating a mile a minute as his cock strained in its cage and his ass uncontrollably clenched. Blushing, he stood up and awkwardly walked towards Dr Frederick.

"Not so fast" he said with a smile as he stood and embraced Robb. "Clothes come off" he said as he pulled off Robb's shirt. Robb's pants followed as Dr. Frederick gave a slight chuckle  at Robb's fishnets and thong.

"Mmmm" he moaned as his hard cock pressed into Robb's side as he caressed his curves up and down. "Look at you."

He tugged the front of Robb's thong down, revealing the cage. "Ha, no wonder you're gagging for it," he said as he got Robb's thong and fishnets down.

Robb squeezed under the desk and looked up in anticipation.

"Few ground rules. Suck away, but if I pick up a call you're to lightly suck and lick my sack. Understood?"

"Yes."

"What do those boys have you call them? I was partial to having my roommate call me master" he said.

"I call them sir."

"Hmph. No imagination in this generation. Since I'm old enough, you will call me daddy. Got it?"

"Yes...daddy" Robb replied.

"Good, now suck Daddy's cock, slut" he replied as he scooted in his chair.

Robb hungrily obliged. The cramped space and width of the cock gave Robb some trouble. He could forsee an aching jaw in his figure but he did his best, licking up and down the shaft to get it nice and wet before letting it dip into his throat.

He badly wanted to jack off. As usual, the humiliation factor was driving him over the edge. Here he was, under his fucking graduate advisors desk, sucking cock like he was trying to get a better grade on a term paper.

Just as he managed to get half of in him, the phone rang and he obediently started working Daddy's balls. It was weird to see all the gray pubes and stuff, but they were just as impressive as the cock he had been sucking. The phone call, over some trivial administrative issue, wrapped up quickly and Robb was back on sucking duty.

Robb had 3/4ths of it down his throat before Dr. Frederick tapped him on the head to get his attention.

"Here, work this into your cunt" he said, while passing Robb a sunction dildo and some lube. Struggling with the space, Robb managed to get his ass lubed and the dildo suctioned to the back panel of the desk. Returning Dr. Frederick's member to his mouth, he slowly backed his ass onto the dildo, moaning as he continued to suck.

"Good girl" Dr. Frederick remarked as the phone rang.

"Back to my sack, slut" he added as he picked up the receiver.

"Ah James, how are you, friend?"

Robb took one ball into his mouth at a time, delicately giving each a tongue bath as he slid back and forth on the rubber cock. He felt incredibly used and dirty, but loved it. His mind seemingly filtered out any real negative feelings when he was getting intimate with a cock.

The jovial conversation continued for some time with Robb paying little attention until he became the subject. Of course, Robb could only hear Dr. Frederick's part.

"Ah, speaking of which, I'm getting my balls licked as we speak.....no, its a fag this time, which is just as well, they truly love it. You get a woman down there and they just try to drain your balls in under a minute and get out with their A or letter of recommendation."

Dr. Frederick laughed loudly, likely along with whoever he was talking to.

Robb's face reddened at being referred to as a fag, but he really wasn't in a position to argue considering where he was and what he was doing.

"This weekend? I'll see if I can make it. Bring one of yours and I'm guessing I'll have no problem convincing mine."

More laughter.

"Alright, see you then, goodbye."

Another tap on the head stopped Robb and Dr. Frederick pulled his seat back.

"Let's give that boypussy a spin." He said, helping Robb up, turning him around and making him arch slightly over the desk.

"Mmmm, too bad I didn't know sooner. Would have loved to pop your cherry." He said, landing a hard slap against Robb's ass and watching it jiggle as he lubed his cock.

He returned to a sitting position and brought Robb back slowly, positioning his dick at Robb's hole and drawing him into his lap.

"Ohh..fuck....oomph, oh, daddy" Robb cooed, unable to control his horniness.

"Fuck yeah. You were born for this" Dr Frederick moaned as he grabbed Robb's hair and pulled him lower and lower.

"Now, I'm going to have to ask you to be quieter...unless you want to be overheard and have half of the staff in here waiting for a piece of your fat ass....although, I'm guessing you'd like that," Dr. Frederick laughed as he fully impaled Robb on his cock.

Robb bit his lip to keep quiet as he steadied himself on the desk. He started slowly riding Daddy's dick, slowly swaying his hips as he went up and down. The combination of everything made him feel like he could cum at anytime.

Dr. Frederick bucked right back, ensuring his cock was slamming into Robb's ass hard. His hands alternated from toying with Robb's ass, hair, and nipples as he grunted with each thrust.

Robb's legs began to wiggle as his orgasm built and Dr. Frederick pushed him off momentarily...only to lift him up by his splayed legs and put him back on his dick. It was an impressive feat of strength and turned Robb on even more. Even though, they were alone and the door was locked, something about this position and Robb's caged dick being on display made it feel even dirtier.

"Cum for me," Dr Frederick whispered into Robb's ear. "Just let it out."

"Mmmphhhh ohhhhh fuckkkkkkk fuck" Robb moaned as he went into a bodyshaking orgasm that was soon joined by Daddy blowing his load deep into Robb's well-used ass.

Robb's legs were released and he just barely caught himself on the desk. In his post orgasm haze, he noticed his phone on the table and knew he wasn't quite done debasing himself.

Grabbing it, he turned his head to Dr. Frederick.

"Da..daddy, can you take a picture of you..inside me?"

"Huh?" He responded, rubbing Robb's ass. "What is this? Some sort of blackmail attempt?" He laughed.

And so Robb explained the assignment Arnold had given him in detail.

Dr. Frederick whistled, "surprised you're even still interested in your girlfriend. I'll do it, but it's going to be my rules and you're gonna owe me."

"Yes, daddy" Robb meekly replied.

Dr. Frederick's dick stiffened in Robb's boypussy as he explained how the video clip would work and what Robb would say and do.

With the phone camera pointed at Robb, he gave the performance he was told to do.

In the most feminine voice he could conjure, he went through a list of absolutely filthy lines as he backed his ass back and forth on daddy's cock.

"Ohhh daddy, it's so big...oh fuck....you're stretching my pussy....oomph"

"Oh God, fill me up....mmmmm...fuck...I want your load, it's all....oh my god...I care about."

"Fuck....daddy, you're making me squirt....oh god"

And so on and so on, all said with Robb's face looking back at the camera with a look of complete lust and obedience.

Dr. Frederick erupted into another orgasm, pulling out and letting some stray shots of cum splash against Robb's ass. He spread Robb's cheeks to show off the cum soaked gape, landed two hard slaps and cut the video off.

"That...is how you are to talk to men from now on." He said as he put his cock away.

"Boy howdy, next time you're bringing a buttplug or a tampon. You're leaking everywhere" he said as he bundled Robb's fishnets up and shoved them into Robb's hole.

Robb slowly got dressed as Dr. Frederick typed away at his computer. It was surreal. It's like he was a cheap escort. Finally dressed, with his fishnets soaking up the cum still leaking out, he turned to leave.

"Hold on." Dr. Frederick interrupted.

"From here on out you will come to our meetings pre-lubed and ready to go. Understood?"

"Yes, daddy.'

"Good. You will also be joining me this Saturday evening. I will pick you up at 8pm. You will be dressed like the whore you are. Understood?"

"Yes...daddy" Robb answered, feeling unsure of what was going to come next.

"Good girl. Until then." He nodded.

Robb booked it home and climbed into the bath tub. Another threshold had been crossed. Another person was fully aware of his exploits. He was painfully horny and ashamed of it all. After a long soak, he shaved his body, got dolled up and sucked Arnold and Chuck off as they watched the video approvingly.  They made it clear this is how Robb would now act and talk like when he was at home.

--

Two Days Later

If Robb thought the boys were going to wait to plan his next exploit, he was damn wrong. He sat in the back of Arnold's car, dolled up, in anticipation as they drove to the promised addition to his bodycount. The boys had left his holes alone for the past two days, ensuring he'd be as horny as possible.

Sure enough, his body was on fire. Chuck was sitting in the back seat, feeling up his ass covered by a miniskirt and tweaking his nipples covered by a see-through blouse. Bringing his finger to Robb's mouth, the grad student eagerly began sucking first one and eventually three fingers while moaning. He wanted Chuck to take him then and there.

Suddenly, the car stopped and the fingers were removed. They were in the driveway of a house.

"Alright,  sissy, let's go" Chuck nodded as he got got out of the car. Robb stepped out, feeling the night air rushing up his skirt.

Chuck guided him to the door and knocked. The door was answered by a scrawny 20 year old named Jake, who Robb knew as being Chuck's weed dealer.

"Chuuuck, right on time" he said as he dropped a bag of weed into his palm.

"Damn, your roommate really cleans up nice, huh?"

"Hell yeah, man. He wanted to make a good impression. He even swore off our cocks and his dildo collection to ensure he'd be tight as can be!" Chuck responded as Robb blushed.

"Excellent" Jake responded. "I'll be sure to take good care of her" he added as his eyes remained glued on Robb.

"Glad to hear it. We'll be back tomorrow at noon."

Robb's eyes widened as he didn't think this would be an overnight deal.

"Have fun" Chuck said, giving Robb's ass a hard slap and hopping back in the car.

"Come on in, babe" Jake said, with Robb dutifully following with his eyes looking down.

With the door closed, the real surprise came. Jake embraced Robb, pushed him against the wall, and started aggressively making out with Robb while feeling him up. Robb was caught completely off guard but his submissive nature and horniness saw him melt into Jake's embrace and feel up his cock through his jeans.