(Original author here: I am embarrassed to admit that my first attempt at this story branch was a bit rushed and lacked a lot in some key areas. While I feel like this is in bad form, I have rewritten the branch from here.)
Monica squinted out over the crowd and found exactly what she was looking for. “Him,” she said to Stephan. “I want that kid to fuck me while little boy Damon jerks himself off.”
A moment later Stephan returned with a young man with hair the color of straw and a T-shirt that did little to hide the muscular frame beneath. Monica allowed herself a smile while a strange jealous arousal burned in Damon’s eyes. “Tell us a bit about yourself, sir.” Stephan was eager to get the show on the road, but knew that a proper roadshow needed to be set up to land with the greatest impact.
“Hey, uh,” the boy mumbled, “I’m Jason and I’m a student over at the local college. I’m 18, but… yeah, I haven’t had sex before.”
Monica lifted her eyebrows in surprise, but knew how to best keep Damon on the leash. “A virgin, huh? Damn, boy, how would you like your first time to be with a piece of ass like me?” She turned around to give Jason a view of her heart-shaped butt. “I bet you’re a better fuck than he ever was.”
Damon rose to the bait and grew red in the face, but his cock stiffened as Monica spoke. “H…hey,” he muttered, leaning in closer to Monica to whisper. “I thought I was supposed to be the young guy watching you fuck someone… I don’t know, better at this? Like, older, stronger-”
“More experienced? Babe, I’m going to get fucked by someone who wants to enjoy this pussy like a real man. And you’re going to watch as I cum from a virgin prick while you just sit there and play with yourself knowing that you couldn’t have me. This virgin could fuck me better than you.” She winked at Damon and stuck out her tongue, perhaps enjoying her role as the ‘villain’ of the roleplay. Monica then spun on him with an accusatory finger pointing at his hard member. “And don’t you dare think about touching that useless thing until we get started.”
Damon took a step back, letting his girlfriend undress the teen. Beneath his clothes, his muscles seemed to be even more impressive and his youthful skin had a glow about it. Monica playfully tugged his briefs down to reveal a decently sized cock hiding behind them. Not as big as Damon’s, but not… bad. She looked back to her younger boyfriend and then to Madame Illusia. “I think we’re ready to go, here.”
Madame Illusia shook her head. “This is for Damon’s desires. I wait for his command.”
Damon seemed transfixed as Monica’s hand slowly worked the teen’s cock back and forth. With a start, he nodded absently. “I-I do. I mean, yes, we’re ready. Make me younger.”
Madame Illusia returned to her work, drawing in power from the air around them and redirecting it through the two (former) lovers. Monica was already running her tongue along Jason’s shaft while Damon began to cautiously jerk his cock, occasionally stepping around to get a better look at his girlfriend’s handiwork.
The crowd watched with fascination as the muscles that Damon had once displayed began to melt away much as his waistline had. His hair grew out into a thick, luxurious coif while the rest of his body hair thinned out. While he continued to slim down, Monica began to bulk up. With Jason’ cock in her mouth, she noticed that something was odd when her lips seemed to grow out and over the young boy’s dick and the heat she had felt before returned. The audience let a hush fall over them as the woman’s ass, resting atop her bare feet as she blew the teen, began to plump up and gain the beginning hints of cellulite. Her once perky breasts began to fill up and get larger as she rocked her head back and forth, leaving great big globs of drool cascading down her new ample chest. She pushed the thoughts out of her head and pulled away from Jason’s dick to look back to her wanking boyfriend. She let a laugh fall out from her lips. “Ooh, look at the little man.” Monica worked Jason’s cock with her free hand while her lips were still slick with the teen’s precum. “All of those muscles of yours are starting to disappear.” Damon couldn’t be in his twenties, anymore, she reasoned - again, unaware of her own changes. Still, watching the man playing with his huge cock while he’s supposed to be emasculated rubbed her the wrong way. “Illusia, Madame? I think we have a problem.”
The magic stopped for a moment and Damon and Monica felt their body temperatures return to normal. Stephan gave Monica a signal to “go on” with a wave of his wrist.
“Jason, dear, you’ve got a nice little cock here, you really do.” She stood to her feet, suddenly unsteady as her center of gravity had shifted with her new assets. Monica looked down, confused for a moment. Had her tits always been this heavy? Was her ass always so… wobbly? She felt strange, but pressed on. “The problem is, Damon’s monster dick over there is just going to go to waste if he’s going to end up being a little boy anyway.”
Madame Illusia smirked, knowing where this was going.
Damon looked down at his cock, now with thinner, lighter pubic hairs having replaced what was once a dense thicket. “Oh… oh, yeah… I guess,” he mumbled. He couldn’t stop staring at his girlfriend’s new impressive assets or the fact that even as they spoke she couldn’t stop playing with Jason’s dick.
“You guess?” Monica asked, incredulous. Her new D-cup tits shook as she lifted up Jason’s cock. “I need to get split open by a real fucking dick so I can get that body-shaking orgasm that you used to give me. The kind you won’t give me if you’re just a little boy playing with his prick while a real man fucks me.” She bent low to open her mouth and run the teen’s cock across her tongue and pull it into a sloppy, quick suck while Jason moaned.
Damon blushed again before nodding to Madame Illusia. “Can I do that? Give the kid some of my… uh, cock length?”
“And girth,” Monica chirped as she . “And who are you calling a kid? You’re looking a bit on the young side there, tiny. I’m starting to think that you’re younger than the virgin.”
“Monica is right,” announced Stephan. “Damon is now a strapping lad of 17, while Monica is more than twice that at 37.” The woman stopped, her blood running cold. She ran her hands across her larger bust and down over her soft belly and towards her heaving hips. However, she didn’t let that stop her, and flicked her fingers towards her clit and pulled back a trail of wetness that stretched upwards.
“Mmm… I gotta say, I like the new me as much as you like the new you, Damon. I’m older, but goddamn I look good.” She stuck her wet fingers in her mouth and started working Jason’s cock with her hand. “But you, baby? You’re starting to look like a lost little boy. Now go on, Damon, give this boy some of your cock. I need it more than you do.”
“Ho… how much should I…?” Monica’s annoyed stare cut him off before he turned to the magical host. “Um, just start giving him my length and girth until Monica says to stop.” Damon continued to watch as Monica worked her cunt, leaving drops of wetness on the stage floor.