The Summer Falls
He drove his paws on, now that her maidenhead had been stolen enough for his slick fingers to truly get in and please her, the vulpine returning to his careful exploring, gauging just where to rub his digits to get the best reaction from her.
Chapter Six: Loss
Kiku's scream was heard throughout the prison as her maidenhead was obliterated. as the scream died off, anyone who heard knew she had passed out.
Chapter 15: Adorable Denial
"this is why your maidenhead remains unbroken. you wait for him." "what! no! never. i will never let yato touch me there!" she squeezed her thighs shut just thinking about it. yatokya's big fingers had always been so gentle and firm . . . no, no!
The Cadmean Vixen
Her maidenhead never stood a chance against the hound's prodigious member, and if the panting female under him felt any pain at its tearing it didn't show in her face.
To breed a dragon
In the eternity of her mind, less than a second passed before the dragon had slid himself forward, and in a mighty thrust, he ripped past her maidenhead, and caused her to bite her lip, stifling a scream.
Exodus Pt. 1
Just when she thought it couldn't get worse, he forced his way through her maidenhead. her cries turned to a scream, and the rope tightened around her throat, cutting off her air supply.
Daydreams 06 - Let Loose
Her crotch was sore, but she felt tight, and something told her that her maidenhead was intact. that seemed monumentally important; she couldn't quite recall why, but she just knew that preserving her virginity was vital.
Chapter 18: Juicy Cock
He wanted to know if she still had her maidenhead . . . and if anyone had done anything to her penis. tala closed her eyes. no one had touched her penis before yatokya. the lone wolves had been too horrified . . . but the arrow wolves had tried.
A Night At The Knocksbury
He'd pushed past my maidenhead without even noticing, and in the euphoric haze i had, i didn't either. and i didn't care.
Twisted Fairy Tales - Little Red
She gave one last squeak before the wolf humped upwards while lowering her down, his thick shaft spearing her virgin cunt, her maidenhead giving only the briefest of resistance before breaking.
Chapter 31: That First Time
Hard and strong, he plunged slowly through her juices, and she felt her innocence, her maidenhead tear around him. the sudden pain made her eyes flutter open wide. she tore her lips away and arched her back. "ah!" yatokya stopped at once. "tala?
Patreon Reward - Family Ties
It didn't hurt more than the tiniest pinch as she broke his maidenhead, deflowering her brother and officially being his first.