Jimmy's Dilemma

Author's note: There are 2 previous chapters to the story, so you might want to read them first.

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It was 6:55pm and Jimmy sat in his car across the street from Angela's place, begging to wake up from this nightmare. He couldn't really be dressed like a slutty cheerleader, wearing fake tits and red lipstick, and about to walk across the street and knock on her door.

But he was, and he knew he didn't dare be late. He thought again about turning back, going home. Then he unlocked his phone and looked for the tenth time at the text she had sent. The picture of him on his knees, a huge black cock filling his mouth. Jimmy whimpered and stepped out of the car.

Two minutes later, he was knocking on Angela's door as he glanced nervously side to side hoping nobody would come along. It seemed to take forever for her to get to the door and while he waited he couldn't help but glance down and remember that not long ago he had been licking his own cum from the bottom of that door.

The door opened a few inches (as much as the chain would allow) and Angela stood there in a sheer silk top and thin shorts that were about two inches too short. Fuck! Now he was hard again under his skirt. Angela smiled.

"Welcome back, slut" she said. "Turn around and put your hands behind you."

Jimmy did as he was told and soon felt the cold steel of handcuffs surround his wrists. The ominous clicking was loud in the hallway. He heard the chain slide from the lock and he was pulled inside as the door swung wide.

Turning around, Jimmy felt his breath catch in his chest and his legs get weak. Panic shivers ran through his body as he stared across the room. Nancy, his ex-girlfriend, was sitting on the couch! She smirked as she watched him standing there, cock rock hard under his skirt. Angela giggled softly behind him.

"Oh, you know Nancy right bitch?"

Jimmy was so stunned he couldn't speak. Then Angela slapped him harshly on the ass. "I said, do you know Nancy bitch?"

Jimmy mumbled a quick "yes" as he dropped his head in shame.

"Good. Well Nancy helped me set up your date with Eric and Bubba. You should thank her." Angela giggled again. "I said, you should thank her slut!"

Thank her? For what? Making him suck cock? Jimmy could not believe what he was hearing! But then Angela stepped in front of him and held up her phone.

On it was another picture of him in the closet, only this time it was Eric's cock Jimmy had in his mouth. She didn't have to say anything more.

"Thank you, Nancy."

"For what, big boy?" Nancy smiled as she said it. He knew she was going to make him say it.

"Thank you for letting me suck cock, Nancy."

"Well, I am glad you liked it so much. I knew you would be a natural."

"Oh, he is indeed a natural born cocksucker" Angela chimed in "but today he gets to choose what kind of cocksucker he wants to be. How exciting!"

Seeing the confused look on his face, she explained "In a minute, we are going to my bedroom. Sitting on my bed is Gary, a friend of mine. Gary is gay...like you." Nancy giggled as Jimmy blushed bright red.

"Well, you aren't just gay" Angela said "you are a sissy cocksucker! And when you walk into that bedroom, you get to choose what kind of sissy you want to be. You can own it and choose to be Gary's girlfriend publicly for the next six months" Jimmy felt his heart racing and thought he might puke.

"Or...you can choose to stay our private sissy cum slave for the next year."

Jimmy began begging "Angela...Nancy, please, those can't be the only two choices. I will do whatever you want today, but this has to stop."

Nancy spoke up now "Well, there is a third choice baby." Jimmy's face brightened at this news "Anything, please"

"Okay, this can all be over today sissy. All you have to do is suck Gary's cock, and then beg us to share the video with all your friends and family." She laughed as Jimmy bowed his head "No? Okay, then you have to choose between girlfriend and slave."

"Now, here is how you will make your choice. When I open that door, Gary will be sitting on the bed. He is blindfolded, so he can't see you yet. If you are choosing to be his obedient gay girlfriend publicly, then you will go kiss him on the mouth and ask him to take off the blindfold, so he can watch as you service him. Then, you and he will leave together to start your new relationship. Gary is a really cool guy and will treat you well. In return, you will be a good girl and service him daily as well as dressing very girly for him when he takes you out on dates." Nancy let this choice sink in for a moment.

"On the other hand, if you are ashamed of who you are, then you can hide it by continuing to be our sissy faggot slave. To choose this option, you will crawl through the door and go straight to Gary's cock. You will suck him, and swallow, then thank him for the cum. After that, Gary will leave, and you will begin your new life as our cum slave. The only promise we make is to never intentionally expose you to anyone you know. But make no mistake, you will be used as a cum dump and whore whenever we choose by whomever we choose. "

Angela walked to the door, giving him no time to think. As she turned the knob, she said "Decision time, slut!" She opened the door wide and Nancy pushed him towards it.

As Jimmy stumbled toward the door, he saw Gary sitting on the bed naked and blindfolded with an erection. His cock was large, probably 8 inches or so. Even from the doorway, Jimmy could see that it was leaking precum in a steady dribble that ran down towards his shaved balls. He stood there trying to decide, his mind paralyzed, as Angela whispered in his ear "Girlfriend? Or gloryholes and gangbangs, whore? Time's up."

Defeated, Jimmy dropped to his knees. He began crawling towards Gary's cock, hearing Angela and Nancy giggling behind him.

Now, kneeling in front of Gary, he realized the dick was even bigger than he thought. As he opened his mouth and felt the soft, slippery head of Gary's penis slide between his lips Jimmy looked up and saw that Nancy held her phone in front of her to get a close-up of him sucking cock.

Jimmy didn't have hands free to help in trying to get Gary off quicker, but he quickly realized that Gary's hands were under no such restriction as they went to the back of Jimmy's head and began forcing him down on the cock till he gagged. Jimmy tried to pull back but he was helpless as Gary gripped his head and began forcing Jimmy further with each stroke until he was throating all 8 inches.

Jimmy panicked as he felt the fat knob of Gary's cockhead slide past the back of his throat, blocking off his airway. And Gary laughed as he felt Jimmy's throat constrict and squeeze his dick, pulling even more precum out to lubricate the sissy's mouth-pussy.

"That's it Gary, fuck this slut. Make her take it all baby." Nancy was enjoying Jimmy's humiliation and panic and though she could see he hated it, she quickly realized something about it was turning him on too. "Look at that, the little bitch is hard." She moved the phone lower to get a close up of Jimmy's rock-hard cock tenting his cheerleader skirt, then panned up his body to capture the thick slime of spit and precum hanging from his lips as Gary continued to use his throat like a Fleshlight.

Just then, Gary began driving Jimmy's head faster up and down the length of his cock and groaning with pleasure "Yeah bitch, get ready for feeding time!" Jimmy felt the head of his tormentor's cock swell as Gary forced it all the way down his throat, and then what seemed like an impossible flood of sperm began jetting in hot spurts directly into his belly. Unable to breathe and helpless to do anything but act as a cum dump, Jimmy felt he would pass out by the time Gary relented and slid his dick back leaving just the head in Jimmy's mouth.

Nancy stepped forward and finished her video by focusing in on Jimmy's lips stretched around the head of Gary's huge penis. She laughed and said "I've always wanted a slave..."

To be continued