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.
