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Chapter 21
by
magictcg
Pick your prize young lady
Anal with Alex
As the competition winds down, a new energy fills the room. Your body still tingling from the powerful orgasm, you glance over at Alex and Jen, who are catching their breath on the opposite couch.
"Let's switch things up," you suggest, your newfound confidence propelling your words. "I'd like to try Alex now. And I want to do anal."
The room falls silent for a moment. Brett chuckles, sliding out from under you and wiping his chest with a nearby towel.
"I was wondering when you'd get around to that," Alex says, his eyes darkening with desire. He gives Jen a gentle kiss before disengaging from her. "You've been practicing?"
"Jen gave me a tutorial this morning," you admit, feeling heat rise to your cheeks despite everything you've already done today.
"She's a quick study," Jen adds with a proud smile, stretching languorously before turning her attention to Brett. "Looks like you're with me now, big boy."
Brett grins appreciatively, his impressive member already responding to Jen's attention. "I'm not complaining."
Alex approaches you, his familiar hands caressing your still-sensitive skin. "How do you want to do this?"
"I think hands and knees would be easiest for the first time," you reply, recalling what you learned from both Jen's tutorial and your earlier research.
You position yourself on the soft sheets, feeling **** yet excited as you present yourself to Alex. Behind you, Jen arranges the camera for a better angle, ever the professional even as Brett begins kissing his way down her neck.
"We need lube," Alex says, retrieving a bottle from his duffel bag. "Lots of it."
The cool sensation of the lubricant makes you gasp as Alex applies it generously, his fingers gently preparing you. Each careful stroke sends strange new sensations through your body discomfort mixed with unexpected pleasure.
"Relax," he whispers, leaning over to kiss your shoulder. "Breathe out when I push in."
You nod, focusing on your breathing as Alex positions himself. The pressure is intense as he begins to enter you a burning stretch that makes you bite your lip.
"Too much?" he asks, freezing in place.
"No," you manage, though your voice sounds strained even to your own ears. "Just... go slow."
Across the room, Jen has mounted Brett, her small frame bouncing enthusiastically on his massive member. The sight of her pleasure helps distract you as Alex pushes deeper, inch by careful inch.
"You're doing amazing," Alex encourages, one hand reaching around to stimulate your clit. "Let me know when you're ready for more."
The dual stimulation begins to transform the discomfort into something more complex a fullness that borders on pleasure. You push back slightly, taking more of him.
"That's it," he groans, his free hand gripping your hip. "You feel incredible."
As your body adjusts to the unfamiliar intrusion, the pleasure gradually overtakes the pain. Your moans join the symphony of sounds filling the apartment Brett's deep grunts, Jen's high-pitched gasps, and Alex's encouraging whispers creating an erotic soundtrack to your exploration.
Can this get any better?
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After Hours Video
Save your job with porn.
The job market has been brutal. After months of applications and rejections, you finally landed a position at After Hours Video, a small adult store on the edge of town. The pay isn't great, but it's money in your pocket and the hours fit around your community college schedule. The owner, Mr. Keller, is rarely around, leaving the store in the hands of his 18-year-old kid and you, his newest hire. The arrangement worked fine until today, when disaster struck. A major shipment of adult videos arrived completely blank and your coworker, who was supposed to check them before shelving, didn't bother. Mr. Keller is furious and threatens to close the store unless you can replace the missing content within two weeks. With rent due and no other job prospects, you're to keep this position.
Updated on Jun 11, 2026
by magictcg
Created on Sep 4, 2025
by magictcg
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