“I only have about an inch in so far. You have a ways to go,” he told her. Killian nodded, clenching her jaw. She was determined, but she already felt like she was impossibly full. “Push back into me. With your hips and your muscles.”
The last thing Killian wanted to do was push back into him for fear of driving his cock deep into her. Counterintuitively, she pressed her hips back a bit and pushed the tight muscles in her sphincter against the invasion of his cock. To her surprise, he did slip in further, meeting less resistance.
“That’s it, Kil,” he said supportively, “you’re doing such a good job. That’s only half but I’ll stop for a minute and let you get used to it.”
She couldn’t believe it was only half. She felt like she was being split in two. Killian looked at Jack, who was watching their progress intently. He had begun to lazily fondle himself while he watched.
“I’m going to bury the rest of my cock in you now,” said Logan. “You ready?”
“Yes,” said Killian, though it turned into a cry as he started to push into her again.
“Play with your clit, princess,” he said soothingly. “It’ll help.”
Killian slid a hand between her legs, only to find her pussy was dripping wet. She rubbed her clit tentatively and moaned loudly. Logan was right. Pleasure mixed with the pain and she started to relax.
“That’s a good girl,” Logan groaned. With a final thrust, Killian felt his hips press against her ass. “Jesus fucking Christ, Killie. You’re so goddamn tight.”
She felt his weight on her, pressing her down on her stomach into the bed. Killian’s eyes were on Jack, who was stroking his hard-on as he watched his stepbrother sodomize her. Logan pushed her hair to the side, kissing her neck and making her shiver as she got used to the feeling of him stretching her out.
“I’m gonna start to move now, okay?” Logan murmured in her ear.
“Yes,” breathed Killian. “Go easy on me?”
“Of course,” he said softly. He pressed his lips to her neck. Her ear. Her cheek. Covering her affectionately in kisses.
He pulled out a bit and slowly pushed himself into her again. She whimpered, fighting back a cry.
“That’s it, sweetheart,” he said reassuringly, stroking her hair. This time he pulled out more and thrust slow and deep into her ass. “You’re doing so good.”
“You feel so big, Logan,” she whimpered.
“Just relax. Let me do all the work.” He was moving with a gentle, deliberate rhythm, getting longer, deeper thrusts each time. “I’m going to make you the best buttslut for my brother.”
Killian bit her lip and focused on relaxing her tense muscles. Logan was being good to her, but she still felt like she was stretched beyond what she thought was possible. It stung a little, but he’d used copious amounts of lube, so his invasion met no resistance. It was the most peculiar sensation to be so full in one hole and so empty in the other.
“Oh my god,” she gasped suddenly, “Logan. Fuck. That feels–oh, fuck.” Killian started to rub herself faster as she felt a foreign pleasure radiating throughout her.
“Starting to feel better?” he asked.
“Yeah.” She nodded, on the edge of delirium with the overwhelming sensation. “Fuck!” She felt on the verge of tears. It hurt so good. “More, Logan.” She pushed her hips back into him wildly. He responded by moving faster.
“You like how Logan is fucking your ass, babe?” asked Jack, smiling at her.
“Mm-hm,” she moaned. “Oh my fucking god. Yes!” It didn’t exactly feel good; she didn’t know how to describe it. But whatever it was, it was starting to drive her insane.
“You feel too good,” groaned Logan, driving his cock into her tender flower. “I’m gonna–”
But Killian cut him off, as she cried, “Fuck my ass, Logan! You’re going to make me cum.”
“Fuck yeah, Killie,” he grunted, pushing into her excitedly. “Cum for me while I fill your tight ass with my load.”
Killian’s eyes locked on Jack who was pumping his cock quickly with his hand. With a loud cry, the pressure became too much for Killian to contain. It overflowed. Her tight ring convulsed around Logan’s cock as she climaxed. She felt Logan twitching inside her as he spilled his hot seed deep into her asshole.
Logan slowly pulled out when his orgasm subsided. “That was fucking incredible, princess.”
“It was so good,” she mumbled deliriously, unable to move.
“That was the hottest fucking thing I have ever seen,” said Jack, still working his hand up and down his cock.
“Yeah?” grinned Killian. “Fill my pussy?” The only way things could be even better was if she had both her holes stuffed with cum.
“Of course,” said Jack, wasting no time. He took Logan’s place, not bothering to move her to a different position, and plunged his cock eagerly into her ready pussy as she lay on her stomach. She mewled as he entered her.
“Holy fuck,” he moaned, glancing over at Logan. “You nailed that ass well, bro. Her pussy is so goddamn wet.” He rammed Killian’s hole excitedly. “Oh fuck, baby girl. You want my cum?”
“Yes! Please fill me. Oh god,” she gasped, thrilled by how fast he was going to climax, “yes, please!” The idea of having cum leaking from both her holes was one of the hottest things she could imagine.
She felt his cock pulsing in her slippery hole as he pumped her full of cum. He collapsed to the side of her, as he caught his breath. Killian finally found the strength to roll on to her back.
Logan leaned in and kissed her. “You were amazing, sweetheart. Thank you.”
“Fucking incredible,” agreed Jack, taking his turn to kiss her too. “I’m proud of you, babe.”
Killian was completely drained. As promised, they had fucked her silly and rocked her world. She slowly drifted into sleep, aware, only of the comforting feeling of Jack’s and Logan’s arms wrapped around her protectively.