Jimmy's Dilemma Ch. 04 - A New Toy

One week.

It had been a week since Jimmy knelt in front of Gary and acknowledged his fate as a cumslut and sissy slave for Nancy and Angela.

The thing is, it had been a normal week since then. And Jimmy was finally starting to relax. He figured maybe they had tired of tormenting him and decided that he had endured enough punishment. He smiled to himself that morning as he woke and looked down at his cock, hard with morning wood.

Jimmy gripped his dick and began slowly stroking it, using his precum to lube the shaft as he allowed his mind to drift off into fantasy. He began by imagining random babes, sucking his cock and offering him their tits. But then Angela slipped into his fantasy, wearing that robe she had on with nothing beneath it but her taut, naked body. The tits that she had made him stare at as he stroked for her, kneeling outside her door. Jimmy didn't understand why, but reimagining the scene made him so horny he moaned softly while jerking his cock.

As the whole scene played out in his mind like a personal porno, he began stroking faster. Soon he was close to cumming, and just as he was about to shoot his load he flashed on that night and the way Angela had laughed as she made him lick his fresh cum from her door. This memory drove him over the edge and he came in heavy spurts, harder than he had in weeks. He opened his mouth in ecstasy as his orgasm boiled out of him, and a warm jet of sperm landed directly on his tongue. Feeling his own cum slide down his throat made him feel dirty and shameful, at the same time that it renewed his hardon and he came even more. A new blob of his slime rained into his open mouth, falling half on his tongue and half on his lower lip. Without thinking, Jimmy licked his lip clean.

As he lay there on his bed, relaxed but somewhat ashamed, his phone dinged with an incoming message. Jimmy rolled onto his side and picked it up. It was from Angela. Shit!

"Hey slut, hope you're feeling horny today! We have a busy day planned for our bitch. Be here, dressed, in 30 minutes."

Jimmy's heart sank as he read the text, and he felt sick to his stomach. He thought about replying that he was sick and couldn't make it today.

As if she read his mind, another text from Angela popped onto his screen. He opened it and was staring at a picture of himself with Gary's cock all the way down his throat. The next message made him nervous "Don't be late. Oh, and you should have an Amazon package outside your door. Make sure you are wearing it when you get here."

A package? Jimmy almost ran to the front door, worried that one of his neighbors might have found it first. When he opened the door, there was a small box right outside. He looked at the label as he picked it up. It was addressed to "C. Slutt". Jimmy quickly closed the door and ran back to his room.

Tearing open the package, he groaned softly. Inside was a type of butt plug and a bottle of lube. The plug was pink and about six inches long and an inch thick at the flared base, with a glass jewel at the end.

Jimmy quickly showered and dressed in his cheerleader outfit, then looked at himself in the mirror. The short pleated skirt barely covered his ass, and he felt even more naked underneath since he was shaved clean. The thin tank top, with the word "SLUT" in bold letters, barely covered his fake tits. He had remembered to put on red lipstick and as he stared at the mirror Jimmy blushed in shame. His cock had once again hardened and was tenting out the front of his skirt!

He was about to leave, when he remembered the plug and his heart sank. Lying on his bed, Jimmy took out the plug and smeared lube generously over it. He got on his hands and knees, figuring that would make it easier, and then reached underneath and behind his ass placing the tip against his tight asshole. The cold lube made him tense up and he told himself to relax. He had read in porn stories that girls pushed to open their asshole when taking a cock there and so he tried that at the same time that he pushed the plug.

It began sliding in, stretching his virgin ass around it, and he felt his cock harden even more. What the fuck? Finally, it seemed like the whole thing was in. Jimmy looked back over his shoulder at the mirror on his wall past the foot of the bed. He could see the pink jewel shining back at him from where his asshole should be.

Looking at his phone, Jimmy realized he had less than 10 minutes left to get to Angela's before the deadline. He grabbed his keys and rushed out the door to jump in his car. During the drive to her apartment, no matter what he did to distract his mind, Jimmy's dick had a mind of its own and stayed at attention. Parallel parking on the street in front of her building, he had no time to wait for his hard on to subside and so he got out of the car and began walking while hoping that nobody he knew would walk by.

Suddenly, there was a sharp whistle and Jimmy heard Nancy's voice calling to him. "Hey slut!" his ex-girlfriend yelled from the balcony of Angela's apartment. Jimmy froze and looked up. Nancy leaned over the railing of the balcony, her gorgeous tits nearly falling out of her low blouse.

"Wait for us there. We'll be right down."

Jimmy waited nervously on the sidewalk outside the building for what seemed like ages. Two middle aged women walked by and giggled as they realized he was a guy. One of them said something and Jimmy could only make out the word "cock" as she looked him up and down. They kept on walking but shot glances over their shoulders at him and continued laughing.

Then Jimmy heard male voices approaching and he felt cold with fear.

Jimmy turned away as he saw four men in their twenties walking toward him on the sidewalk. He leaned up against a lamp post and hoped desperately that they would just keep on walking. But he knew he was fucked when he heard them slowing down and their banter take a different turn.

"Bro, look at that! We got a cheerleader here" one of the guys said close behind him. Jimmy felt himself stiffen and freeze in fear.

"Hey babe, nice ass" said the guy "turn around and let me get a look at the rest of you."

Jimmy didn't know what to do, so he just stayed turned away as if he hadn't heard the guy. It didn't matter. The others were starting to walk around him, and as they did he could sense the surprise. They saw his "tits" and then their eyes wandered down to the word SLUT across his white blouse. He could almost feel them drooling. But then in the next moment, one of them saw that Jimmy's short skirt was tented out by his hard cock.

"Dude, what the fuck?" a blonde jock on Jimmy's right yelled out "that's no cheerleader! This is a little faggot!"

Jimmy felt like he was about to cry as the guy behind him grabbed his right arm and spun him around to get a look for himself. The guy was probably 22 or so, taller than Jimmy and had bright blue eyes and dark black hair. He was buff, with muscles bulging under a black tank top over blue basketball shorts. Jimmy dropped his gaze and saw that the shorts were bulging over the dude's half erect dick. He must have gotten hard looking at Jimmy's ass and thinking he was a cheerleader.

"You are a faggot, aren't you?" The other three laughed and pointed as Jimmy's dick bobbed when he was called a faggot. A quarter sized wet spot was appearing at the front of his skirt, from the precum flowing freely.

Jimmy blushed bright red and stared down, trying to think of something to say. He stuttered "N-n-no, this is for a frat dare." He instantly regretted saying anything.

"Really? So what frat is it for? Maybe I know them, and I can shoot them a pic to prove you did as you were told...like a good bitch, hahaha!"

The blonde jock was standing close behind Jimmy now, and spoke softly in his ear "yeah, what else do they make good bitches like you do to get in?" Jimmy felt the guy's breath on his neck, and goosebumps shivered their way up towards his ear.

Just then, Angela and Nancy walked up to the group "Hey boys, how's it hangin'?" Angela laughed as she said it, staring at Jimmy's hard-on. "Looks like somebody is enjoying themselves. Is my sissy bitch getting you guys all worked up?" Now she was staring at the buff jock's basketball shorts and his growing bulge.

"This little sissy is yours? He told us this was for a frat dare."

"Mmmm, the only thing my little sissy would be good for at a frat is taking care of men like you" Angela lightly stroked the buff guy's chest as she said this, and his cock stood at attention. She smiled.

"Tell you what, we have some errands for this slut to run. But maybe later she can be a good girl for you...all of you." As she said this, Angela pulled out her phone "What's your number, baby?"

Jimmy shook as he heard the conversation and watched Angela put the dude's number in her phone. He knew she must be joking, but it still made him scared...and hard. Why wouldn't his erection go away? It was like he was in a cycle of shame and excitement and couldn't stop. The front of his mini-skirt was soaked with a big splotch of precum.

Nancy leaned in close to the blonde one and whispered something in his ear that made him laugh and look at Jimmy, then she slapped Jimmy hard on the ass leaving him stinging.

As the guys walked away, Angela and Nancy each grabbed one of Jimmy's arms and steered him towards Nancy's car. They put him in the back seat and then got in the front. The pink jewel at the base of the plug was pressing it hard into him as he sat there.

"Well, I never realized you were such a flirty little slut!" said Nancy "But look at you, making all those real men hard with your tight ass." She laughed and looked in the rearview mirror as she said it, watching Jimmy's shame spread over his face.

"Please, where are you taking me? Haven't I done enough?" Jimmy whined.

Angela grinned and glanced in the mirror at him as she spoke "Don't worry, slut. Today is going to be a special treat for you."

Jimmy saw that they were heading into a shady area of town, and he became more nervous as they parked in front of an adult bookstore. It was one of the places advertising video arcades and adult toys, and said it was open 24 hrs. Jimmy had read about spots like this but had never had the courage to walk in.

Nancy turned in the front seat and spoke to him "Okay my little bitch, we need to finish your look and get you all gussied up. There is a bag next to you on the left floorboard, open that up and let's get started."

Opening the bag, Jimmy pulled out a long blonde wig and a makeup case. Within minutes, Nancy and Angela had expertly placed the wig and fixed it to his head so it barely moved. Then, they took their time to carefully apply makeup to his face.

"Ooo, you really do make a cute girl" Angela giggled and held up a mirror. Jimmy couldn't believe his eyes! Staring back at him through long fake eyelashes and dark mascara, was a slutty blonde cheerleader.

Not wasting a second, the girls pulled him from the car and marched him across the parking lot to the entrance of the bookstore. As the three of them walked inside, a bell chimed. There were about 4 customers in the store looking around, and they all looked up as Jimmy walked in nervously in front of the other two.

Angela walked straight to the cashier, a chubby brunette with a nose ring. As he got closer, Jimmy could hear them clearly talking about him.

"Yeah, she's ready for her shift" Angela said as she pointed at Jimmy. "What do you think? Do we have a deal?"

Deal? What kind of a deal? Jimmy's mind was racing as he stood there. His hard on had finally subsided a bit, but it threatened to rise back to full attention as he stared around him at all the dildos, butt plugs, posters and sex toys. His mind came back to the moment as Nancy stepped behind him and something cold clamped around his left wrist. Why was she cuffing his hands behind his back? Before he could ask, a blindfold was slipped over his head, cutting off all light. Jimmy began to panic.

The chubby cashier spoke up then "Okay girls, get her into booth #6 and prep her. I will get things started."

Nancy and Angela guided Jimmy to the back of the store and through a black curtain that covered the entrance to a hallway. On either side of the hallway were doors, and Jimmy could hear the sounds of porno vids coming from behind a few of them. They got to #6 and pushed him in the open door ahead of them.

They made Jimmy kneel on some kind of cushion, and then did something with his ankles and his wrists. He quickly realized they had chained them together so that now he had no choice but to kneel there at their feet.

"Please" Jimmy whispered frantically "don't do this. Whatever it is, don't do this. I'll be good for you, I'll do whatever you want."

Nancy laughed softly "Of course you will baby. But it isn't about what we want today. This is all about customer service."

As Jimmy opened his mouth to respond, something was shoved inside. He tried to shut his mouth, but his teeth were stopped by something hard and round, about a half inch wide. He felt it with his tongue and it seemed hollow, like a tube or a pipe. As he tried to wrap his mind around this, something was being fastened at the back of his head, buckled like a belt or strap.

Next, Jimmy felt Nancy place something around his balls and tighten it. He tensed up in panic that she was about to hurt him, but just felt a gentle tug and then tension.

At last, Angela pulled the blindfold from his eyes. Jimmy looked around and took in the scene, trying to figure it out. There was a clear plastic tube about a foot long, stretching from his mouth to another plastic device attached to the wall. The other device was made of transparent plastic and several inches across where it went into the wall, narrowing to just a couple of inches where the tube was attached.

Jimmy tried to look down at his balls, but it was hard because of the tubing. Angela saw him look and said, "Wondering what this is, slut?" Jimmy nodded.

"Well, as you can tell, you are going to stay kneeling there until we decide to let you up. We gave you a cushion because it's going to be a while...and we aren't mean." Nancy giggled at this.

"Your balls are chained to the floor, to make sure you not only stay kneeling, but you stay in your place. The thing you see in the wall? I'm pretty proud of that. You see, I took something old and made it new. Which is really at the heart of being an entrepreneur, isn't it?"

"This is the new version of that old standby, the gloryhole."

Jimmy knew what glory holes were, he had read about them and seen porn videos. But he still didn't see how this was a glory hole.

"That toy going through the wall is a fake pussy, the kind guys use to jerk off when they can't find a willing girl. A little lube and a lot of fun. There are all kinds, but I like this one since it's clear and you can watch the cock as it slides in and out."

"You are about to help us make some fun money...by providing a little fun for customers." Jimmy felt queasy as his brain started to catch on.

"On the other side of that wall is the fun side of that pussy, and a bottle of lube. Oh, and a monitor hooked to that." She pointed and for the first time Jimmy noticed the blinking light of a video camera mounted in the corner to his right. His brain screamed in panic and he began breathing heavily, sucking in the plastic smell of the tubing as he gulped air through the artificial pussy.

Angela giggled at his distress "oh, getting scared now is no use honey. Although it is fun for me!"

"Anyway, I think you can figure out the rest. Jasmine up front has notified a list of her special customers that a new slut is on duty today. For $10, they get to come down here and fuck that pussy while they watch you waiting here like a good cum-slut for their load."

Just then, the door to the booth opened and Jasmine stuck her chubby face in. She smiled when she saw Jimmy on his knees. "Customers are starting to get here" she said as she stared at Jimmy "Is the bitch ready?"

"Whether she is or not doesn't matter" said Nancy and they all laughed.

"I think the Sperm Bank may be coming in today too" said Jasmine. She suddenly sounded excited.

"Really?" Angela's voice got throaty "Should we tell her what to expect?"

"Nah, surprises are fun for sluts like this. Although, come to think of it, maybe thinking about that for the next couple of hours will make it more exciting."

Couple of hours? They couldn't be serious! Jimmy started hyperventilating again. But suddenly, he couldn't get air through the tube. He almost panicked, until he realized he could still breathe through his nose. But why couldn't...? Then he saw it.

The clear plastic of the fake pussy was suddenly darkened by a large black cock filling it as the first customer began stroking into the soft lubed interior. Jimmy froze as the reality of what was about to happen hit him. The girls got quiet for a moment, and all that could be heard was the soft squishing sound of the anonymous dick fucking in and out of the toy.

Jasmine was the first to speak "Looks like your sissy is about to get the first taste of her lunch!"

Just a few seconds later, they all watched as the dark dick seemed to freeze and swell inside the clear plastic of the toy. The huge head was right up to the end of Jimmy's feeding tube when it unleashed jet after jet of thick white cum. Jimmy shook his head, eyes wide, and watched helplessly as the load flowed down the tube and into his mouth. He felt the warmth of it coat his tongue and did his best to shut his throat but that just meant he had to savor the taste longer and so he gave in and swallowed.

Nancy gently patted the back of his head, like you would a good puppy "You know what this reminds me of slut? Remember all those porn videos you used to watch? The ones where girls would drink load after load of cum? Now you are the girl, and you get to live it instead of just watching! That must be so exciting for you."

Jimmy moaned as she rubbed her foot gently across his hard cock, emphasizing that she could see he was turned on by the humiliation. Why was he so hard? He didn't want this. Didn't want to be on his knees, used as a cumdump. Yet his dick was dripping a steady flow of precum that ran down and coated his tied-up balls.

Another customer took their place at the pussy, and a medium sized white cock shoved its way in to begin stroking as Angela spoke up "You know what's interesting? Most guys have no staying power at all. Especially in a situation like this. Jasmine tells me they usually only last a couple of minutes before shooting their load down the tube. A couple of minutes...and you have a long shift ahead of you, bitch."

Jimmy couldn't help himself, he started doing math as soon as she said it: say 3 minutes average per customer. 2 hours was 120 minutes, 120 divided by 3 was...40?!! No! He began shaking his head again, and his whole body quivered as Angela giggled cruelly.

"Well, we are going to go shopping now. See you in a while, slut. Make us a lot of money...and I hope you get to meet Sperm Bank today!"

As the door shut behind them, the second cock plunged all the way into the slick pussy and shot another load into Jimmy's feeding tube.