Jimmy's Dilemma Ch. 07

Jimmy stared at his laptop screen, watching it again. It had been a week since he knelt on the filthy floor of that booth and swallowed unimaginable loads of sperm. But his memory was fresh, and he felt as if he could imagine the taste of every spurt of cum as it flowed across his tongue.

Of course, it was kept fresh by the fact that his tormentors had installed a copy of the video on his computer and instructed him to watch it at least once a day. And they could check on him at anytime as they had access to his webcam 24/7. This realization made Jimmy's cheeks suddenly flush a bright red as he realized they could be watching him now, stroking his cock while he stared at his own humiliation on the screen. His mind flashed back to that night, and he could feel it recoil at the memory of men plunging their cocks into his feeding tube and fucking until they shot their load and watched him helplessly choke it down.

The shameful memory somehow brought his impending orgasm even closer and he felt himself rising to the edge of it just as his cell phone rang, blasting Lady Gaga's "Born This Way". The harsh interruption stopped him just seconds from blowing his load, as he jerked his hand away from his throbbing cock. Jimmy hated that the girls had insisted on the gay anthem as his ringtone, but he knew he had to answer and quickly.

"Hello?" Jimmy knew it was Angela, but didn't want to give her the satisfaction.

Her sultry voice oozed through the phone and into his ear, "Hey bitch, what are you up to?"

"Um, just hanging out. I am about to go get some groceries." He stared down at his aching hard dick, drooling pre-cum from the tip. Angela giggle on the other end of the conversation.

"Really? Were you going to finish jerking off first, or go out with that hard little dick of yours just like that?" Jimmy realized she had been watching him through the camera in his laptop, and his face got hot again with the humiliation. He didn't answer.

"Tell you what, I have a better idea. Let's go out and have some fun. Get ready in your outfit, tits and all. I will pick you up in 45 minutes. And you better be outside waiting for me, with that little dick just as hard as it is now. Get moving sissy!" She disconnected the call and Jimmy moaned in frustration as he headed for the shower.

Forty five minutes later, he stood on the sidewalk in front of his apartment building, dressed in a white tank top with "SLUT" emblazoned on the front and a short cheerleader skirt underneath. Under the shirt, his "tits" had been glued to his bare chest and were stretching the thin fabric of the tank top. Under the skirt, no panties to restrict his raging hard on and so the front of the skirt hung lewdly away from his body as it tented over his dick. A generous coating of red lipstick completed his slutty look.

Jimmy glanced around every few seconds, terrified a neighbor would see him. Why wasn't Angela here yet? His mind screamed at him to go back inside. Just then, he saw Angela's car pull up in front of him with Nancy (his ex-girlfriend and Angela's partner in humiliating him) sitting in the back. She motioned to him that he should jump in the back seat next to Nancy, and he quickly opened the door and climbed inside.

Nancy smiled wickedly at him, her full lips taunting him as she glanced down at his hard-on. "Aww, is Mr. Happy anxious for some fun?" She reached out and flipped his skirt up, to leave his dick bobbing and drooling in the air, then gave the head a hard flick with her finger. Jimmy jumped in pain and surprise, but she just laughed and flicked him again.

"Oww! What the fuck, Nance?" He knew immediately that it was a mistake, as her grin turned to a frown.

"What did you call me? You lost the chance to call me that when we broke up, bitch!" She reached down into the purse next to her feet, and came out with handcuffs dangling from her fingers. "Turn around and put your hands back."

Reluctantly, Jimmy shifted until his back was towards her and placed his hands behind him. As he did so, he glanced left into the rear view mirror and saw Angela staring at him in anticipation. She actually licked her lips. Fuck, what did they have planned now? The cold steel of the cuffs encircled his wrists and Jimmy heard the ratcheting clicks as they tightened. Then, Nancy placed a blindfold over his eyes and the world went dark. He trembled slightly, and she giggled as Angela hit the gas and they pulled away from the curb.

Jimmy started to shift back to a normal sitting position, but Nancy stopped him with a hand on his shoulder. He felt something being wrapped around his neck and clicked snugly in place. As he opened his mouth to ask what was going on, a sudden shock jolted his neck and made him cry out in pain.

"Training collar, to keep a bitch like you quiet." Nancy said. "You speak when spoken to, do you understand?" Jimmy was silent, afraid to open his mouth, and the thing sparked to life again with a stinging shock.

"Yes!" He cried

Nancy giggled again "Yes what, bitch?"

He didn't know what to say "Yes...Ma'am?" Another shock.

"Yes...Mistress?"

"Hmmm, that will do." Nancy guided him back into a forward seated position, then reached down and absentmindedly fondled his dick back into hardness. Jimmy felt the curves of the car turning this way and that through side streets for the next few minutes, feeling completely exposed with his cock out and blindfold on.

The car slowed, and came to a stop as it pulled into a driveway. Jimmy heard Angela and Nancy get out, and their doors slam shut, then felt a breeze on his balls as the door next to him opened. One of the girls grabbed his arm and guided him as he stepped out, his high heels clicking on concrete. They walked him slowly away from the car, wobbling blindly on his heels, his dick losing hardness as he tried to guess what they had in store.

Suddenly, there was knocking at a door and then he could feel the empty space in front of him as it swung open. A male voice chuckled, about a foot behind the door. Jimmy thought it sounded vaguely familiar, but he couldn't place it. Then, they were walking again, heading into the place (house? shed? apartment?).

Stopped abruptly by his waist hitting against something, Jimmy was pushed from behind and bent over at the waist. He guessed it was a table, as he could feel the smooth surface beneath his torso. Then, a tearing sound, and he felt his ankles being bound to the legs of the table with duct tape, leaving him spread wide. His ass was barely covered by the skirt, and his dick hung freely beneath the edge of the table. The cuffs on his wrists were removed, and his captors repositioned his arms in front of him then spread them as they were duct taped to the table legs to either side.

Jimmy was now spread eagled over the tabletop, looking like a slut cheerleader waiting to be used. The side of the table nearest his head ended just under his neck so that he either had to let his head hang down over the edge, or make an effort to hold his head up.

A distinctly masculine hand grabbled Jimmy's ass and then flipped his skirt up, exposing his asshole. Lube was squirted on him and then he felt a butt plug swiftly rammed in place as he yelped. The collar reminded him to be silent unless told otherwise. Angela's voice was the next thing he heard, as she bent down to whisper in his ear.

"Remember those frat boys you were teasing in on the sidewalk the other day?" Her words brought the memory rushing back: Jimmy standing in his skimpy cheerleader outfit, and the boys had come walking up behind him thinking he was some slutty college girl. They soon found out he was a sissy, and Jimmy was terrified until Angela and Nancy saved him. He recalled that Angela had asked one of the boys for his number, saying something about her little sissy being able to please them later. He whimpered helplessly.

"Well, we're in their house now. Not exactly the frat house. One of the boys' has an uncle who owns this house and lets them use it for...parties." She flicked her tongue across Jimmy's ear as she let her words sink in. "Yes, that's right pet. The boys are having a party here tonight, and they needed some entertainment. As you know, its pledge week, and they have way too many horny college boys who would do anything for a spot in this frat."

Nancy pulled the blindfold off Jimmy's head, and he blinked in the light as his eyes adjusted. They were in what looked like a bedroom, but beyond the table he was strapped to, the only other furniture was an old loveseat slightly against the wall on his left and a small end table next to the loveseat. On top of the end table sat a laptop, open with the screen facing him. Next to it, a small tripod held a camera pointed at him. On his right, he could see the door to the hallway.

His gaze was drawn back to the screen of the laptop, as it mirrored back the image of him spread helplessly across the tabletop. Nancy sat on the loveseat, her legs spread lewdly, fingers gently toying with her pussy beneath her short skirt as she stared at Jimmy. One of the frat boys stood next to her, his cargo shorts bulging slightly under the pressure of a half hard cock. Another stood by Angela, and her right hand slowly traced a familiar outline as it grew under his pants.

"Boys, I think we should do a position and height check before your guests get here." It was Nancy who spoke this time, the pressure of her fingers increasing on her pussy lips as her tongue slid over her top lip. Her gaze never left Jimmy.

The boys quickly took their places. The one next to Angela shifted a pace right and forward, so his crotch was directly in front of Jimmy, whose head was starting to fall from the effort of holding it up. Nancy's boy stepped behind Jimmy, and he felt the plug being pulled from his ass.

Both boys unzipped simultaneously, and released their cocks as they continued to harden. The one in front of Jimmy grabbed his head with both hands and lifted it until his mouth was lined up with 8 inches of stiff dick. "Open up, bitch!"

Jimmy knew he had no choice, and obediently parted his lipstick coated lips as the monster began to slide over his tongue. At the same time, he felt the head of the cock behind him press against his asshole and force its way inside. The length of that meaty cock slid slowly past his sphincter and he could feel every inch invading him. In unison, the frat boys began pumping in and out. Jimmy wanted to fade away, wanted everything to just stop. He closed his eyes tightly, then heard Angela. "No, bitch. Open your eyes. I want you to watch that fat cock sliding in and out. Do you think our audience is closing their eyes? No way, they are stroking themselves as they watch you warm up."

Audience?! What was she talking about? Jimmy's panicked mind tried to make sense of Angela's words, even as he had a horrible realization. The dick thrusting in and out of his ass was putting pressure on his prostate and the pleasurable sensation had him leaking a steady stream of sticky fluid from his cock as he got pounded. Angela continued, "Didn't you wonder why it took a week for us to bring you another adventure, sissy?"

"We spent the week setting up an account on a private porn site Jasmine turned us on to. You remember Jasmine, right?" How could he forget her? Jasmine was the cashier at the porn shop where Jimmy had been chained to the floor and forced to swallow load after load of cum from customers. He saw Angela grin out of the corner of his eye.

"That's right, her. She told us about this site where we could make money from a slut like you. Tonight's party is going to be streamed to paying customers who get off on watching a sissy whore being broken in. Some paid for VIP access, so they could watch the warm-up session." She laughed that throaty laugh "Nancy, how many viewers right now?"

Nancy looked at an app on her phone, then grinned "Seventy five." Jimmy writhed in place on the tabletop as the frat boys continued to stroke in and out of his mouth and ass. His body desperately wanted a way out, and his brain was begging him to do something. But the duct tape held tight, and his abusers just laughed as he trembled. Suddenly, the boy in his mouth gripped Jimmy's head more firmly and slammed the entire length of his cock down Jimmy's throat. His dick pulsed and his balls emptied a huge load directly into the sissy's gullet. Jimmy swallowed reflexively, and this coaxed even more cum from the boy as his victim's throat massaged the head of his cock.

Pulling slowly out, the boy deposited one last jet of sperm onto Jimmy's tongue. Nancy let out a soft moan as she came in her panties, frantically rubbing her pussy. The boy fucking Jimmy's ass pulled free as well. Angela motioned him to step around and take the other boy's place. He did so and no sooner had Jimmy's mouth been emptied, than it was filled with a second cock. Only this one smelled of ass and Jimmy retched and gagged as it was forced between his lips. He could taste his own ass juices on it as the boy began throat fucking him.

Angela giggled "Awww, is my little bitch not a fan of ass-to-mouth? Nancy, I thought you said that was some of his favorite porn to watch?"

Nancy, bit her lip as she came again from watching her former boyfriend slurp a thick syrup of ass juice and precum from the cock thrusting in and out of his mouth "He loves jerking off to that shit. I figured he would be grateful for the chance to live out the fantasy."

The boy in his mouth could last no longer, and suddenly stiffened as jets of slime pumped from his balls into the sissy mouth. Where the other boy had thrust all the way into Jimmy's throat, this fucker had pulled back till only the engorged head of his cock sat between the sissy's lips, forcing Jimmy to savor the sperm as it filled his mouth before swallowing.

A doorbell rang, and Angela hurried Nancy into action. "Come on, time to greet our customers, babe."

As she walked into the hallway with Nancy, Jimmy could hear several male voices at the front door. His heart dropped as he recognized the deep baritone of his best friend, Billy, among them!

"Alright boys" Angela raised her voice "there are going to be a lot of you here tonight, so we need everyone to be orderly. Get naked here in the living room, put your clothes in one of these bags. Put on your blindfold, and my beautiful friend will lead you to the room where our slut is waiting. You will fuck her in the ass" a cheer went up from the boys, "but when you feel like you are about to cum, I want you to pull out and Nancy will lead you to her mouth so you can finish." The boys cheered again, and Jimmy whimpered.

A minute later, Nancy led the first boy into the room. She was stroking him slowly, leading him by his cock. Placing it against Jimmy's anus, she let go and the boy began fucking in and out of the sissy. Within three or four minutes, he shakily pulled his dick free and followed as Nancy led him around to Jimmy's mouth. Once he was sliding into Jimmy's lips, she quickly brought the next boy in line and slid him into the waiting ass of the helpless sissy.

Jimmy sucked resignedly at the cock in his mouth, and heard a muttered "fuck, this is awesome" from behind. His face flushed hot with shame as he realized his best friend was fucking him in the ass while Jimmy deep throated another boy's cock.

Minutes later, the third load of the night was sliding into Jimmy's belly and Billy's cock was being pulled from his ass and brought to his lips for servicing. Jimmy opened his eyes and saw that Billy had a massive member, streaked with precum, lube, and ass. Humiliation welled over him as he obediently opened wide. Nancy grinned at him while feeding Billy's cock slowly into his friend's sissy mouth.

Before turning to guide the next customer to Jimmy's ass, she whispered in his ear "We made sure tickets were cheap, and it worked. Twenty five customers in line tonight. Gonna be a long night, bitch."

When Billy finished in Jimmy's mouth, he grunted and withdrew slowly. A long strand of cum and saliva hung from Jimmy's lips to the floor. Jimmy turned left and looked at the image of himself in the screen of the laptop, seeing how the boy behind him thrust eagerly into his ass.

Suddenly, he realized he was staring not just at the camera but at who knows how many perverts who were watching at home as he got fucked again and again. Then, his head was being turned forward and yet another cock was placed at his mouth, ready to force feed him the next portion of dinner....