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Josslyn leaned in, pressing her lips to the rolled condom. It took her a minute to get it started, and doing so involved tonguing the underside of the head of his cock. One of Master Ben’s hands fisted in her hair, halting her. The head of his cock was in her mouth, and she swallowed the spit that already pooled behind her teeth. He cursed when her swallowing action caused her tongue to thrust up and caress his cock.
“Okay, okay,” Master Ben said, and it was the first time he’d sounded rattled. “You can keep going.” He slowly released her hair.
Josslyn continued working the condom down his cock, taking him in her mouth until the head of his dick was hitting the back of her throat and making her gag. She eased back, instead pressing her lips and tongue to first one side of his shaft and then the other, unrolling the condom bit by bit.
Master Ben growled and grabbed her hair, yanking her head back. Her scalp prickled with pain, and she wished she could squeeze her legs together.
“Plug your ass.” Master Ben thrust the plug at her with one hand, his other quickly rolling the last inch of the condom.
Josslyn took the plug and paused, waiting.
“Your pussy is wet, and when you were on your back, it leaked down to your ass. You may fuck yourself with the plug a few times, but I want your ass full in the next minute.
Josslyn didn’t waste time. She thrust her hand holding the plug between her legs. The cold felt good against her still throbbing pussy as she slid the plug down the valley of her sex. Her eyes fluttered closed in pleasure when she thrust the plug into her vagina. It was cool and thick and her body clenched down, desperate to be filled. She thrust it in again, then a third time. Josslyn was tempted to keep going, but any more than this and she’d be disobeying.
Reluctantly, she slid the plug out of her vagina, then reached around behind herself, arching her back. She enjoyed anal but had never plugged herself. It was unexpectedly awkward, especially in this position. After some fumbling and running the tip of the plug up and down the crack of her ass, she got it notched into place. She took a breath, and as she exhaled, she pushed. The plug slid halfway in, her anus stretched around it. She clenched, and the plug slid right back out.
“Shit,” she whispered.
“Problem?”
“I’ve never done this before, Sir.”
“Ah.”
She pushed it in again, trying to relax her muscles. When her body reflexively clenched, she made sure to keep pressure on the plug.
“I didn’t realize how hard you have to hold it,” she whispered.
“Push it in, now.”
Her hand moved, obeying his clear command before she had a chance to really think about, or question, it.
The plug slid in, her ass closing around the narrow neck. Josslyn let her head fall, breathing in and out. It felt so good to be filled, even if it was her ass, not her pussy. Her sex felt empty. Raising her head, Josslyn looked at Master Ben’s cock and imagined what it would feel like inside her.
“Josslyn.” Her name was a reprimand and a reminder.
She jumped, then scrambled to grab the chains dangling from the plug. She pulled one around in front of her. It just barely touched her belly button. She clicked the D-ring on the cuff into the latch on the end of the chain, then reached around for the other one. This time, it was a little more difficult, and as she pulled, the plug shifted inside her. For a moment, it felt like it would slide out. She clenched down as hard as she could, straining to reach across her lower belly to use the already bound hand to fasten the chain to the other cuff. It clicked in, and she sighed, finally relaxing her ass.
Then she remembered the last step of this ritual.
Moving gingerly, she turned her back to Master Ben and bent down. She couldn’t use her hands to brace herself. Scared she’d tip forward and crack her head on the concrete floor, she scooted back until only her knees were on the cushion then sank down into what was essentially a yoga “child’s pose.” With her forehead braced on the cushion, she finally raised her hips, grabbed her ass cheeks, and spread them.
Master Ben hooked a finger into the ring on the base of the plug and pulled it out. Josslyn wasn’t expecting that and yelped. He reinserted the plug with the same casualness, and Josslyn’s anus hummed from the stimulation.
“Up.”
Before she had a chance to obey, his hand was in her hair, dragging her up. He didn’t give her time to turn around, or to prepare herself.
It seemed that Master Ben’s patience had run out. He circled to her front and stepped onto the cushion, hand still in her hair. Her lips were already parted, and he decisively thrust his cock into her open mouth.
Josslyn wasn’t expecting it and pulled back, but he jerked her forward by the hair, forcing more of his cock into her mouth.
“I’m going to fuck your face.” He sounded savage and merciless. It was almost frightening. “You will keep your jaw loose, and swallow when I’m in your throat.”
She couldn’t reply except to obey.
Master Ben cupped her skull in both hands, pulled out until just the head of his cock was in her mouth, and then thrust in. He thrust in all the way, forcing himself past her tongue and into her throat, she gagged, then swallowed to combat the gag reflex.
