Eternal Love
To lick up and down my throbbing shaft occasionally suckling on the head, after about a minute she stopped got up and straddled my lap, she directed my penis towards her moist little hole and sighed in contentment as my length slid into her, i reached her maidenhead
Chapter Seven: Turmoil
Trying to get her pained tail to cover herself, but he held her fast, wiggling his hips again to work her virgin slit open and then with a merciless shove, he pushed her down onto him fully, drawing an ear-splitting cry from her as he tore through her maidenhead
Mateship Prologue: Consummation
He got halfway in when he felt her maidenhead. "okay, dove, i'm going to break your hymen now...are you _sure_ you're ready?" she smiled warmly at him. "i...i want this to happen, bailmont.
Dane, Bertie, and Daria: Three's Company
Taking advantage of a poor, naïve lass, stealing her maidenhead." "honey," dane said wryly, "you lost your maidenhead so long ago, historians couldn't find it."
Two for one...
Dunlup moved his hips around, letting her feel his cock press against different parts of her, and then gently prod her maidenhead. "mmm... oh yeah, i'll pop your cherry, honey."
Trespass
He slid the delicate, flared tip against her lips, adding his pre to her fluids, before sliding it along to her entrance and pressing against her maidenhead.
Pathfinding: An Adult Choose Your Own Adventure, Twenty-Third Entry
It never truly leaves until you have had your inner parts stimulated, and that certainly was not allowed to us - we were required to retain our maidenheads.
The Order of Future: Chapter 4 - Eye of the Storm
In her estrogen clouded mind she noticed that the maidenhead of wyan was as intact as the one of inia. just as this crossed her mind she heard a muffled huffing voice from her own rear.
Commission: Angel of MIne
Folds spread out around him slowly, her maidenhead stretching some before giving way. her legs jerked as her virginity was taken. biting her lip, the human sat herself down, only stopping when she was firmly seated in his lap.
A New Companion and Old Memories
She shook her head and pressed her hips forward on him, forcing his flare to break her maidenhead. she gave out a cry, her fingers clawing at his arms. it hurt more than she had expected, but felt just as good.
Duet of Love
She had let him bed her and take her more precious possession, her maidenhead. then she thought about how he had treated her and decided she wanted to be with him and bear his clutch.
Gryphon's Sonnet
She hadn't done this before for fear of breaking her maidenhead, but now that it was gone she had nothing to fear. her body shuddered as she thought about flint's cock and the brief glimpse she caught of it that morning.